JP2004168736A - Cleansing agent - Google Patents
Cleansing agent Download PDFInfo
- Publication number
- JP2004168736A JP2004168736A JP2002339277A JP2002339277A JP2004168736A JP 2004168736 A JP2004168736 A JP 2004168736A JP 2002339277 A JP2002339277 A JP 2002339277A JP 2002339277 A JP2002339277 A JP 2002339277A JP 2004168736 A JP2004168736 A JP 2004168736A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- group
- cleansing agent
- chain
- general formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 239000003599 detergent Substances 0.000 title claims abstract description 74
- 150000001875 compounds Chemical class 0.000 claims abstract description 66
- 239000004094 surface-active agent Substances 0.000 claims abstract description 63
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 23
- 239000000203 mixture Substances 0.000 claims description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 125000002252 acyl group Chemical group 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 125000001165 hydrophobic group Chemical group 0.000 claims description 14
- 229910019142 PO4 Inorganic materials 0.000 claims description 12
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- 125000000524 functional group Chemical group 0.000 claims description 11
- 239000012071 phase Substances 0.000 claims description 11
- 125000006850 spacer group Chemical group 0.000 claims description 10
- 239000010452 phosphate Substances 0.000 claims description 9
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 7
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 7
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000003945 anionic surfactant Substances 0.000 claims description 6
- 125000000539 amino acid group Chemical group 0.000 claims description 4
- 239000008346 aqueous phase Substances 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 2
- 239000003349 gelling agent Substances 0.000 abstract description 5
- -1 n-octyl Chemical group 0.000 description 109
- 239000002253 acid Substances 0.000 description 60
- 235000014113 dietary fatty acids Nutrition 0.000 description 30
- 229930195729 fatty acid Natural products 0.000 description 30
- 239000000194 fatty acid Substances 0.000 description 30
- 239000003921 oil Substances 0.000 description 26
- 239000000499 gel Substances 0.000 description 25
- 235000019198 oils Nutrition 0.000 description 25
- 229940024606 amino acid Drugs 0.000 description 24
- 235000001014 amino acid Nutrition 0.000 description 22
- 150000004665 fatty acids Chemical class 0.000 description 21
- 235000000346 sugar Nutrition 0.000 description 18
- 150000001413 amino acids Chemical class 0.000 description 16
- 125000003277 amino group Chemical group 0.000 description 14
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 12
- 235000021317 phosphate Nutrition 0.000 description 11
- 125000003396 thiol group Chemical group [H]S* 0.000 description 11
- 239000002537 cosmetic Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 230000002378 acidificating effect Effects 0.000 description 8
- 239000004166 Lanolin Substances 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 235000019388 lanolin Nutrition 0.000 description 7
- 229940039717 lanolin Drugs 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 7
- 235000007586 terpenes Nutrition 0.000 description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 5
- MUPFEKGTMRGPLJ-UHFFFAOYSA-N UNPD196149 Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC2C(C(O)C(O)C(CO)O2)O)O1 MUPFEKGTMRGPLJ-UHFFFAOYSA-N 0.000 description 5
- 125000004442 acylamino group Chemical group 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000006071 cream Substances 0.000 description 5
- 229920006295 polythiol Polymers 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 4
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 4
- OYIFNHCXNCRBQI-UHFFFAOYSA-N 2-aminoadipic acid Chemical compound OC(=O)C(N)CCCC(O)=O OYIFNHCXNCRBQI-UHFFFAOYSA-N 0.000 description 4
- DZAUWHJDUNRCTF-UHFFFAOYSA-N 3-(3,4-dihydroxyphenyl)propanoic acid Chemical compound OC(=O)CCC1=CC=C(O)C(O)=C1 DZAUWHJDUNRCTF-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000004475 Arginine Substances 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- WQZGKKKJIJFFOK-WHZQZERISA-N D-aldose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-WHZQZERISA-N 0.000 description 4
- WQZGKKKJIJFFOK-IVMDWMLBSA-N D-allopyranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@H](O)[C@@H]1O WQZGKKKJIJFFOK-IVMDWMLBSA-N 0.000 description 4
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 4
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 4
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 4
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 4
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 4
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 4
- 239000004472 Lysine Substances 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical compound NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 description 4
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 4
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 4
- 235000003704 aspartic acid Nutrition 0.000 description 4
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- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 4
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- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- KHAVLLBUVKBTBG-UHFFFAOYSA-N dec-9-enoic acid Chemical compound OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 4
- 239000003925 fat Substances 0.000 description 4
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- 239000004220 glutamic acid Substances 0.000 description 4
- 235000013922 glutamic acid Nutrition 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
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- 238000000034 method Methods 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
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Landscapes
- Cosmetics (AREA)
Abstract
Description
【0001】
【発明の属する技術分野】
本発明はクレンジング剤に関し、特に、安定性に優れ、またティッシュオフなしに水のみで完全に除去でき、使用感に優れるクレンジングゲルまたはクリーム、マッサージクリーム等の化粧料として有用な透明〜半透明・乳濁状のクレンジング剤に関する。
【0002】
【従来の技術】
皮膚の汚れやメイクアップ化粧料を落とす目的で、または皮膚をマッサージする目的で使用される化粧料としてクレンジングまたはマッサージ化粧料等があり、これらは本来、皮膚に塗布して使用した後、皮膚から除去されるものである。こういった化粧料として、油性成分を水性溶媒に配合し、その剤型をゲル状に調製した各種のゲル状化粧料がある。しかし、これらの化粧料は使用時および/または使用後にべとつきがあったり、保存安定性が悪かったりする等の問題点があった。ここで、ゲルとは例えばコロイド化学の基礎(大日本図書(株)、1976年発行)の245頁に記載されているようなペースト、クリーム、ゼリー等液体含有量の広範囲なものを指す。
【0003】
例えば、油性成分を水性溶媒中に配合した、その剤型をゲル状に調製したもので、ゲル化剤として知られる水溶性高分子化合物を添加することが一般的に行われている。このように水溶性高分子で形成したゲル状組成物をクレンジング化粧料に用いた場合には、伸びが悪くなったり、汚れ落ちに問題があったり、水洗いした後にべたつく物もあるとともに、この場合には上記のように経時的な安定性に乏しいという問題点がある。
【0004】
一方、油をゲル化剤でゲル化させたオイルゲルがあるが、これは生成するゲル状組成物の粘度の調整が難しく、またメイク落とし等のクレンジング剤として用いた場合に水で洗い流すことができず、使用後にティッシュペーパー等で拭き取り、更に洗顔料等で再洗浄する必要がある。同様に、油中水型に乳化させたゲル状組成物があるが、この場合も油相を連続相とするためオイルゲルと同様にクレンジング剤として用いた場合、使用後に再洗浄が必要である。いずれも、油性成分が手にべたつき使用感が好ましくない。
【0005】
また、水中油型の乳化型ゲル状組成物も知られており、これは前記のような拭き取り操作なしに水で洗い流すことが可能であるが、油性成分が皮膚状に残留することが多く、水による洗浄のみでは不十分である。また、油汚れとのなじみが悪く、クレンジング性が不十分である。そのため、油性成分や界面活性剤の種類や量を変化させたものが数多く検討されているが、安定性や使用感などの点で充分満足できるものではない。また乳化型組成物では外観を透明にすることは困難である。
【0006】
また、特開平10−219278号公報にアシル基2長鎖2極性基含有陰イオン界面活性剤の組成物が開示され、メイク汚れ等を除去できる組成物であり、所望によりゲル状、ペースト状にできるとの記載がある。しかしながら実施例は全て洗浄剤組成物の水溶液を用いた例しかなく、油性ゲル状にしたクレンジング剤に関しては何ら記されていない。
【0007】
【特許文献1】
特開平10−219278号公報
【0008】
【発明が解決しようとする課題】
本発明は、ゲル化剤を含有していなくとも油性成分を安定にゲル状に配合し経時的な安定性にも優れるとともに、塗布した時の伸び等使用感がよく、使用後感触もよい透明〜半透明・乳濁状のクレンジング剤を提供することを目的とするものである。
【0009】
【課題を解決するための手段】
本発明者らは、前記課題を解決すべく鋭意検討を重ねた結果、特定の界面活性剤、即ち、分子内に長鎖疎水基と親水基とを2個以上づつ有する多鎖多親水基型界面活性剤を用いることで、ゲル化剤を用いることなく油性成分を安定にゲル状に配合し、その経時安定性にも優れるとともに、ペースト状から固体状態まで任意の固さのゲル状組成物を得られることを突き止めた。また驚くべきことに、こうして得られたゲル状組成物のうちでもある粘度範囲のものは皮膚等に塗布した場合の伸びに優れること、またこの組成物は水への分散性に極めて優れることから、本発明者らはこのゲル状組成物が、皮膚等に塗布した後に水で容易に洗い流せるタイプのクレンジング剤として提供できることを見出して、本発明を完成するに至った。
さらには、このゲル状組成物は、界面活性剤、ポリヒドロキシル化合物、および水からなる水相と、油性成分からなる油相との20℃における屈折率の差を小さくするほど該ゲル状組成物の外観が透明になることを見出して、本発明を完成するに至った。
【0010】
即ち本発明は、下記の通りである。
1.長鎖疎水基と親水基とを分子内に2個以上づつ有する多鎖多親水基型界面活性剤の1種または2種以上、分子内に水酸基を2個以上有するポリヒドロキシル化合物の1種または2種以上、および油性成分の1種または2種以上を含有することを特徴とするクレンジング剤。
2.クレンジング剤中の水分含量が50重量%以下であり、かつ、水分を含めたクレンジング剤組成物中の組成が、1)界面活性剤成分の総量が0.1〜40重量%、2)ポリヒドロキシル化合物の総量が1〜60重量%、3)油性成分の総量が1〜95重量%、であることを特徴とする1.に記載のクレンジング剤。
3.クレンジング剤中の多鎖多親水基型界面活性剤の少なくとも1種が、その長鎖疎水基が長鎖アシル基であり、親水基がカルボキシル基、スルホン酸基、硫酸エステル基、リン酸エステル基および/またはそれらの塩であるアニオン性界面活性剤であることを特徴とする1.または2.に記載のクレンジング剤。
4.クレンジング剤多鎖多親水基型界面活性剤の少なくとも1種が、分子内にアミノ酸残基を有するものであることを特徴とする1.〜3.のいずれかに記載のクレンジング剤。
5.クレンジング剤中の多鎖多親水基型界面活性剤の少なくとも1種が一般式(1)に示す化合物であることを特徴とする1.〜4.のいずれかに記載のクレンジング剤。
【0011】
【化3】
【0012】
(一般式(1)において、n個のZはXに置換したm個(m≧n)の官能基に由来する結合部であり、それぞれ独立で、すなわち、同一でも異なっていてもよく、Xは前記官能基以外の置換基を有していてもよい分子量100万以下の直鎖または分枝鎖または環状鎖または芳香族炭化水素鎖であるスペーサーであり、Zを介してXに付くn個の一般式(2)で表される置換基はそれぞれ独立で、すなわち、同一でも異なっていてもよく、
R1COは炭素原子数28〜20の飽和または不飽和の脂肪酸から誘導される長鎖アシル基を示し、R2は水素であるか、またはヒドロキシル基またはカルボキシル基が置換していてもよい炭素原子数1〜3の低級アルキル基を示し、Yはカルボキシル基、スルホン酸基、硫酸エステル基、リン酸エステル基および/またはそれらの塩を示し、j、kはそれぞれ独立に0,1,2のいずれかであり、かつj、kは同時に0ではなく、nは2〜20の整数を示す)
【0013】
【化4】
【0014】
6. クレンジング剤中の多鎖多親水基型界面活性剤の少なくとも1種が一般式(1)に示す化合物であって、一般式(1)において、Xは前記官能基以外の置換基を有していてもよい炭素数1〜40の直鎖または分枝鎖または環状鎖または芳香族炭化水素鎖であるスペーサーであることを特徴とする1.〜5.のいずれかに記載のクレンジング剤。
7.クレンジング剤中の界面活性剤、ポリヒドロキシル化合物、および水からなる水相と、油性成分からなる油相との20℃における屈折率の差が±0.05以下であることを特徴とする1.〜6.のいずれかに記載のクレンジング剤。
8.25℃における粘度が1000から200,000mPa・sである1.〜7.のいずれかに記載のクレンジング剤。
【0015】
【発明の実施の形態】
以下、本発明を、特にその実施態様を中心に、詳細に説明する。
本発明でいうクレンジング剤は、多鎖多親水基型界面活性剤の1種または2種以上、分子内に水酸基を2個以上有するポリヒドロキシル化合物の1種または2種以上、および油性成分の1種または2種以上を含有する物であり、少なくとも該界面活性剤の1種は多鎖多親水基型界面活性剤であるクレンジング剤である。本発明において、多鎖多親水基型界面活性剤としては、長鎖疎水基としてはそれぞれ独立に、炭素数8〜20個の飽和または不飽和の直鎖、分枝鎖、環状鎖からなる疎水基を有し、親水基としてはそれぞれ独立に、カルボキシル基、スルホン酸基、硫酸残基、リン酸残基またはそれらの塩等、あるいはオキシアルキレン基、ポリエチレングリコール基等、またはアミノ基、4級アンモニウム基、ピリジニウム基、スルホニウム基またはそれらの塩等を有するものである。
【0016】
例えば、多鎖多親水基型界面活性剤の長鎖疎水基としては、例えば、n−オクチル、n−ノニル、n−デシル、n−ウンデシル、n−ドデシル、n−トリデシル、n−テトラデシル、n−ペンタデシル、n−ヘキサデシル、n−ヘプタデシル、n−オクタデシル、n−ノナデシル、n−エイコシル等の各残基とこれらの分枝鎖異性体、ならびにこれらに対応した、1カ所、2カ所または3カ所に不飽和部分を有する不飽和残基等が挙げられる。
【0017】
また、多鎖多親水基型界面活性剤の長鎖疎水基としては、炭素原子数8〜20の飽和または不飽和の脂肪酸から誘導される長鎖アシル基であり、
例えばカプリル酸、ペラルゴン酸、カプリン酸、ウンデカン酸、ラウリン酸、トリデカン酸、ミリスチン酸、ペンタデカン酸、パルミチン酸、マルガリン酸、ステアリン酸、ノナデカン酸、アラキン酸のような直鎖脂肪酸;
2−ブチル−5−メチルペンタン酸、2−イソブチル−5−メチルペンタン酸、ジメチルオクタン酸、ジメチルノナン酸、2−ブチル−5−メチルヘキサン酸、メチルウンデカン酸、ジメチルデカン酸、2−エチル−3−メチルノナン酸、2,2−ジメチル−4−エチルオクタン酸、メチルドコサン酸、2−プロピル−3−メチルノナン酸、
メチルトリデカン酸、ジメチルドデカン酸、2−ブチル−3−メチルノナン酸、メチルテトラデカン酸、エチルトリデカン酸、プロピルドデカン酸、ブチルウンデカン酸、ペンチルデカン酸、ヘキシルノナン酸、2−(3−メチルブチル)−3−メチルノナン酸、2−(2−メチルブチル)−3−メチルノナン酸、ブチルエチルノナン酸、
【0018】
メチルペンタデカン酸、エチルテトラデカン酸、プロピルトリデカン酸、ブチルドデカン酸、ペンチルウンデカン酸、ヘキシルデカン酸、ヘプチルノナン酸、ジメチルテトラデカン酸、ブチルペンチルヘプタン酸、トリメチルトリデカン酸、メチルヘキサデカン酸、エチルペンタデカン酸、プロピルテトラデカン酸、ブチルトリデカン酸、ペンチルドデカン酸、ヘキシルウンデカン酸、ヘプチルデカン酸、メチルヘプチルノナン酸、
ジペンチルヘプタン酸、メチルヘプタデカン酸、エチルヘキサデカン酸、エチルヘキサデカン酸、プロピルペンタデカン酸、ブチルテトラデカン酸、ペンチルトリデカン酸、ヘキシルドデカン酸、ヘプチルウンデカン酸、オクチルデカン酸、ジメチルヘキサデカン酸、
メチルオクチルノナン酸、メチルオクタデカン酸、エチルヘプタデカン酸、ジメチルヘプタデカン酸、メチルオクチルデカン酸、メチルノナデカン酸、メチルノナデカン酸、ジメチルオクタデカン酸、ブチルヘプチルノナン酸のような分岐脂肪酸;
【0019】
オクテン酸、ノネン酸、デセン酸、カプロレイン酸、ウンデシレン酸、リンデル酸、トウハク酸、ラウロレイン酸、トリデセン酸、ツズ酸、ミリストレイン酸、ペンタデセン酸、ヘキセデセン酸、パルミトレイン酸、ヘプタデセン酸、オクタデセン酸、オレイン酸、ノナデセン酸、ゴンドイン酸のような直鎖モノエン酸;
メチルヘプテン酸、
メチルノネン酸、メチルウンデセン酸、ジメチルデセン酸、メチルドデセン酸、メチルトリデセン酸、ジメチルドデセン酸、ジメチルトリデセン酸、メチルオクタデセン酸、ジメチルヘプタデセン酸、エチルオクタデセン酸のような分岐モノエン酸;
リノール酸、リノエライジン酸、エレオステアリン酸、リノレン酸、リノレンエライジン酸、プソイドエレオステアリン酸、パリナリン酸、アラキドン酸のようなジまたはトリエン酸;
オクチン酸、ノニン酸、デシン酸、ウンデシン酸、ドデシン酸、トリデシン酸、テトラデシン酸、ペンタデシン酸、ヘプタデシン酸、オクタデシン酸、ノナデシン酸、ジメチルオクタデシン酸のようなアセチレン酸;
メチレンオクタデセン酸、メチレンオクタデカン酸、アレプロール酸、アレプレスチン酸、アレプリル酸、アレプリン酸、ヒドノカルプン酸、ショールムーグリン酸、ゴルリン酸、α−シクロペンチル酸、α−シクロヘキシル酸、α−シクロペンチルエチル酸のような環状酸から誘導されるアシル基等があげられる。
【0020】
また天然油脂から得られる脂肪酸由来のアシル基でも良く、上記の炭素原子数8〜20の飽和または不飽和脂肪酸を80%以上含む混合脂肪酸由来のアシル基であれば良い。例えば、ヤシ油脂肪酸、パーム油脂肪酸、アマニ油脂肪酸、ヒマワリ油脂肪酸、大豆油脂肪酸、ゴマ油脂肪酸、ヒマシ油脂肪酸、オリーブ油脂肪酸、ツバキ油脂肪酸、菜種油脂肪酸、パーム核油脂肪酸等から誘導されるアシル基等が挙げられる。長鎖疎水基は、長鎖アシル基で、分子中の長鎖疎水基は同一であるのが好ましい。これら多鎖多親水基型界面活性剤は2種以上組み合わせて用いても良い。
【0021】
本発明のクレンジング剤において、多鎖多親水基型界面活性剤の例を挙げると、構造的には、分子内に長鎖疎水基と親水基をそれぞれ少なくとも1個以上有する界面活性剤を適当なスペーサーで連結した構造のものであり、この構造であればよく、これまで公知になっている化合物でよい。スペーサーとしては、置換基を有していてもよい分子量100万以下の直鎖または分枝鎖または環状鎖または芳香族炭化水素鎖がよい。より好ましくは、炭素数1〜40の直鎖または分枝鎖または環状鎖または芳香族炭化水素鎖であるスペーサーがよい。
【0022】
本発明のクレンジング剤において、多鎖多親水基型界面活性剤の親水基はそれぞれ独立に、カルボキシル基、スルホン酸基、硫酸エステル基、リン酸エステル基および/またはそれらの塩であることが好ましい。ここで塩としては、例えばアルカリ金属塩、アルカリ土類金属塩、アンモニウム塩、有機アミン塩、塩基性アミノ酸塩等が挙げられ、具体的には、ナトリウム、カリウム、リチウム等のアルカリ金属、カルシウム、マグネシウム等のアルカリ土類金属、アルミニウム、亜鉛等の金属、アンモニア、モノエタノールアミン、ジエタノールアミン、トリエタノールアミン、トリイソプロパノールアミン等の有機アミン、アルギニン、リジン等の塩基性アミノ酸等から任意に選ばれる1種または2種以上との塩である。これらの中でも、ナトリウム塩、カリウム塩、有機アミン塩、塩基性アミノ酸塩が特に好ましい。
【0023】
本発明のクレンジング剤において、多鎖多親水基型界面活性剤の少なくとも1種が、分子内にアミノ酸残基を有する界面活性剤であることが、生分解性の点、またクレンジング剤の皮膚外用剤等へ用いたときの低刺激性の点から好ましい。さらには、多鎖多親水基型界面活性剤の少なくとも1種が一般式(1)で示される化合物であることが、さらに好ましい。
一般式(1)中、R1COで示される長鎖アシル基は独立して、すなわち、それぞれ異なっても同一でもよく、上記したように炭素原子数8〜20の飽和または不飽和の脂肪酸から誘導されるものであれば何でも良く、直鎖、分岐、環状を問わない。また、分子中のR1COは、同一であるのが反応条件等からみても好ましい。
【0024】
一般式(1)中、R2は水素であるか、またはヒドロキシル基またはカルボキシル基、スルホン酸基、硫酸エステル基、リン酸エステル基またはそれらの塩等が置換していてもよい炭素原子数1〜3の低級アルキル基を示し、例えば、メチル基、エチル基、プロピル基、イソプロピル基、ヒドロキシメチル基、ヒドロキシエチル基、ヒドロキシ(イソ)プロピル基、ジヒドロキシ(イソ)プロピル基、カルボキシメチル基、カルボキシエチル基、カルボキシプロピル基、スルホエチル基等が挙げられる。
一般式(1)中、Xに付くn個の置換基(式(2))は独立して、すなわち、それぞれ異なっても同一でもよい。また、式(2)は、いわゆる酸性アミノ酸がN−アシル化されたものを示すものであり、それらは光学異性体例えばD−体、L−体、ラセミ体であるかは問わない。
【0025】
酸性アミノ酸は、分子中に存在するカルボキシル基とアミノ基の数がそれぞれ2個と1個のモノアミノジカルボン酸であり、アミノ基はN−メチル基またはN−エチル基でもかまわない。また光学異性体例えばD−体、L−体、ラセミ体であるかは問わない。酸性アミノ酸としては、例えばグルタミン酸、アスパラギン酸、ランチオニン、β−メチルランチオニン、シスタチオニン、ジエンコール酸、フェリニン、アミノマロン酸、β−オキシアスパラギン酸、α−アミノ−α−メチルコハク酸、β−オキシグルタミン酸、γ−オキシグルタミン酸、γ−メチルグルタミン酸、γ−メチレングルタミン酸、γ−メチル−γ−オキシグルタミン酸、α−アミノアジピン酸、α−アミノ−γ−オキシアジピン酸、α−アミノピメリン酸、α−アミノ−γ−オキシピメリン酸、β−アミノピメリン酸、α−アミノスベリン酸、α−アミノセバシン酸、パントテン酸等が挙げられる。
【0026】
Xに付くn個の置換基(式(2))は、酸性アミノ酸がL−酸性アミノ酸分子である場合が、生分解性に優れることから好ましい。それらの中でも、置換基は同一である方が好ましい。
一般式(1)中、Xに付くn個のZは、Xに置換したm個(m≧n、かつ、2〜20の整数)の官能基(ヒドロキシル基、アミノ基、チオール基)に由来する結合部(−O−、−NR3−、−S−)であり、それぞれ独立で、すなわち、同一でも異なっていてもよい。ここで、R3は水素、または炭素原子数1〜10のアルキル基またはアルケニル基またはアリール基またはアルキルアリール基である。
【0027】
一般式(1)中、Xはヒドロキシル基、アミノ基、チオール基から選ばれる1種または2種以上からなるm個の官能基を有する分子量100万以下の直鎖または分枝鎖または環状鎖または芳香族炭化水素鎖であるスペーサーであり、Xは、前記ヒドロキシル基、アミノ基、チオール基以外の置換基を有していてもよい。一般式(1)中、Xは好ましくはヒドロキシル基、アミノ基、チオール基から選ばれる1種または2種以上の官能基をm個有する分子量100万以下のm価の化合物の残基であって、ヒドロキシル基、アミノ基、チオール基以外の置換基を有していてもよい化合物残基である。ここで、m価の上記化合物は、m個の官能基に由来する結合を作りうることを意味する。それらは光学異性体例えばD−体、L−体、ラセミ体であるかは問わない。
【0028】
このようなm価の化合物としては、例えば、セリン、トレオニン、システイン、シスチン、シスチンジスルホキシド、シスタチオニン、メチオニン、アルギニン、リジン、チロシン、ヒスチジン、トリプトファン、オキシプロリン等のアミノ酸類;
アミノエタノール、アミノプロパノール、アミノブタノール、アミノペンタノール、アミノヘキサノール、アミノプロパンジオール、アミノエチルエタノールアミン、アミノエチルアミノエタノール、アミノクレゾール、アミノナフトール、アミノナフトールスルホン酸、
アミノヒドロキシ安息香酸、アミノヒドロキシブタン酸、アミノフェノール、アミノフェネチルアルコール、グルコサミン等の分子内にアミノ基とヒドロキシル基を有する化合物類;
メルカプトエタノール、メルカプトフェノール、メルカプトプロパンジオール、グルコチオース等の分子内にチオール基とヒドロキシル基を有する化合物類;
アミノチオフェノール、アミノトリアゾールチオール等の分子内にチオール基とアミノ基を有する化合物類;が挙げられる。また、タンパク質やペプチド等、またはそれらを加水分解したもの等でも良い。
【0029】
Xはこのような化合物の残基の中でも、炭素数1〜40の場合が好ましい、さらに好ましくは、Xは炭素数1〜20である。特に好ましいのは炭素数1〜10である。さらには、Xが分子内にヒドロキシル基、アミノ基、チオール基以外の置換基として、少なくとも1個以上のそれぞれ独立なカルボキシル基、スルホン酸基、硫酸エステル基、リン酸エステル基またはそれらの塩等を含有する場合、一般式(1)で示される多鎖多親水基型界面活性剤が弱酸性での溶解性に優れる点で好ましい。また、Xは天然に存在する型である場合の方が、生分解性に優れるという点で好ましい。
【0030】
また、一般式(1)中、Xは好ましくはヒドロキシル基以外の置換基を有していてもよい分子量100万以下のm価(m≧n)のポリヒドロキシル化合物残基である。ここで、m価のポリヒドロキシル化合物は、m個のエステル結合を作りうることを意味する。それらは光学異性体例えばD−体、L−体、ラセミ体であるかは問わない。
このようなm価のポリヒドロキシル化合物としては、例えばエチレングリコール、1,2−プロパンジオール、1,3−プロパンジオール、1,2−ブタンジオール、1,3−ブタンジオール、1,4−ブタンジオール、ペンタンジオール、1,6−ヘキサンジオール、シクロヘキサンジオール、ジメチロールシクロヘキサン、ネオペンチルグリコール、1,8−オクタンジオール、
2,2,4−トリメチル−1,3−ペンタンジオール、イソプレングリコール、3−メチル−1,5−ペンタンジオール、ソルバイト、カテコール、レゾルシン、ヒドロキノン、ビスフェノールA、ビスフェノールF、水添ビスフェノールA、水添ビスフェノールF、
ダイマージオール、ジメチロールプロピオン酸、ジメチロールブタン酸、酒石酸、ジヒドロキシ酒石酸、メバロン酸、3,4−ジヒドロキシけい皮酸、3,4−ジヒドロキシヒドロけい皮酸、ヒドロキシ安息香酸、ジヒドロキシステアリン酸、ジヒドロキシフェニルアラニン等およびこれらの各異性体等の2価ヒドロキシル化合物;
【0031】
グリセリン、トリオキシイソブタン、1,2,3−ブタントリオール、1,2,3−ペンタントリオール、2−メチル−1,2,3−プロパントリオール、2−メチル−2,3,4−ブタントリオール、2−エチル−1,2,3−ブタントリオール、2,3,4−ペンタントリオール、
2,3,4−ヘキサントリオール、4−プロピル−3,4,5−ヘプタントリオール、2,4−ジメチル−2,3,4−ペンタントリオール、1,2,4−ブタントリオール、1,2,4−ペンタントリオール、トリメチロールエタン、トリメチロールプロパン、ジエタノールアミン、トリエタノールアミン、トリヒドロキシステアリン酸等の3価ポリヒドロキシル化合物;
ペンタエリスリトール、エリスリトール、1,2,3,4−ペンタンテトロール、2,3,4,5−ヘキサンテトロール、1,2,4,5−ペンタンテトロール、1,3,4,5−ヘキサンテトロール、ジグリセリン、ソルビタン等の4価ポリヒドロキシル化合物;
アドニトール、アラビトール、キシリトール、トリグリセリン等の5価ポリヒドロキシル化合物;
ジペンタエリスリトール、ソルビトール、マンニトール、イジトール、イノシトール、ダルシトール、タロース、アロース等の6価ポリヒドロキシル化合物;
またはこれらの脱水縮合物、ポリグリセリン等が挙げられる。
【0032】
また、糖類、例えばエリスロース、スレオース、エリスルロース等のテトロース;
リボース、アラビノース、キシロース、リクソース、キシルロース、リブロース等のペントース;アロース、アルトロース、グルコース、マンノース、ギューロース、イドース、ガラクトース、タロース、フラクトース、ソルボース、プシコース、タガトース等のヘキソース等の単糖類;
マルトース、イソマルトース、セロビオース、ゲンチオビオース、メリビオース、ラクトース、ツラノース、トレハロース、サッカロース、マンニトリオース、セロトリオース、ゲンチアノース、ラフィノース、メレチトース、セロテトロース、スタキオース等のオリゴ糖類が挙げられる。
【0033】
また、その他の糖類、例えばヘプトース、デオキシ糖、アミノ糖、チオ糖、セレノ糖、アルドン糖、ウロン酸、糖酸、ケトアルドン酸、アンヒドロ糖、不飽和糖、糖エステル、糖エーテル、グリコシド等の残基でもよく、デンプン、グリコーゲン、セルロース、キチン、キトサン等の多糖類またはそれらを加水分解したものでもよい。
Xは、このような化合物の残基の中でも、炭素数1〜40の場合が好ましい、さらに好ましくはXは炭素数1〜20である。特に好ましいのは炭素数1〜10である。
さらには、Xが、置換基として少なくとも1個以上のそれぞれ独立なカルボキシル基、スルホン酸基、硫酸エステル基、リン酸エステル基またはそれらの塩等を含有する場合、一般式(1)で示される多鎖多親水基型界面活性剤が弱酸性での溶解性に優れる点で好ましい。また、Xは天然に存在する型である場合の方が、生分解性に優れるという点で好ましい。
【0034】
また、一般式(2)中、Xは好ましくはアミノ基以外の置換基を有していてもよい分子量100万以下のm価のポリアミノ化合物残基である。ここで、m価のポリアミノ化合物は、m個の酸アミド結合を作りうることを意味する。それらは光学異性体例えばD−体、L−体、ラセミ体であるかは問わない。
このようなm価のポリアミノ化合物としては、例えばN,N’−ジメチルヒドラジン、エチレンジアミン、N,N’−ジメチルエチレンジアミン、ジアミノプロパン、ジアミノブタン、ジアミノペンタン、ジアミノヘキサン、ジアミノヘプタン、ジアミノオクタン、ジアミノノナン、ジアミノデカン、ジアミノドデカン、ジアミノアジピン酸、ジアミノプロパン酸、ジアミノブタン酸およびこれらの各異性体等の脂肪族ジアミン類;
ジエチレントリアミン、トリアミノヘキサン、トリアミノドデカン、1,8−ジアミノ−4−アミノメチル−オクタン、2,6−ジアミノカプリン酸−2−アミノエチルエステル、1,3,6−トリアミノヘキサン、1,6,11−トリアミノウンデカン、ジ(アミノエチル)アミンおよびこれらの各異性体等の脂肪族トリアミン類;
【0035】
ジアミノシクロブタン、ジアミノシクロヘキサン、3−アミノメチル−3,5,5−トリメチルシクロヘキシルアミン、トリアミノシクロヘキサン等の脂環族ポリアミン類;
ジアミノベンゼン、ジアミノトルエン、ジアミノ安息香酸、ジアミノアントラキノン、ジアミノベンゼンスルホン酸、ジアミノ安息香酸、およびこれらの各異性体等の芳香族ポリアミン類;
ジアミノキシレン、ジ(アミノメチル)ベンゼン、ジ(アミノメチル)ピリジン、ジ(アミノメチル)ナフタレン、およびこれらの各異性体等の芳香脂肪族ポリアミン類;
ジアミノヒドロキシプロパンおよびこれらの各異性体等のヒドロキシル基が置換したポリアミン類等が挙げられる。
【0036】
Xは、このような化合物の残基の中でも、炭素数1〜40の場合が好ましい、さらに好ましくはXは炭素数1〜20である。特に好ましいのは炭素数1〜10である。
さらには、Xが置換基として少なくとも1個以上のそれぞれ独立なカルボキシル基、スルホン酸基、硫酸エステル基、リン酸エステル基またはそれらの塩等を含有する場合、一般式(1)で示される界面活性剤が弱酸性での溶解性に優れる点で好ましい。また、Xは天然に存在する型である場合の方が、生分解性に優れるという点で好ましい。
【0037】
また、一般式(1)中、Xは好ましくはチオール基以外の置換基を有していてもよい分子量100万以下のm価のポリチオール化合物残基である。ここで、m価のポリチオール化合物は、m個のチオエステル結合を作りうることを意味する。それらは光学異性体例えばD−体、L−体、ラセミ体であるかは問わない。
このようなm価のポリチオール化合物としては、例えば、ジチオエチレングリコール、ジチオエリトリトール、ジチオトレイトール等のジチオール化合物類等が挙げられる。Xはこのような化合物の残基の中でも、炭素数1〜40の場合が好ましい、さらに好ましくはXは炭素数1〜20である。特に好ましいのは炭素数1〜10である。
さらには、Xが置換基として1〜10個のそれぞれ独立なカルボキシル基、スルホン酸基、硫酸エステル基、リン酸エステル基またはそれらの塩等を含有する場合、一般式(1)で示される多鎖多親水基型界面活性剤が弱酸性での溶解性に優れる点で好ましい。また、Xは天然に存在する型である場合の方が、生分解性に優れるという点で好ましい。
【0038】
一般式(2)中、Yで示されるカルボキシル基、スルホン酸基、硫酸エステル基、リン酸エステル基およびX中に含まれうるカルボキシル基、スルホン酸基、硫酸エステル基、リン酸エステル基等は、種々の塩基性物質との間に塩を形成し得る。
かかる塩としては、例えばアルカリ金属塩、アルカリ土類金属塩、アンモニウム塩、有機アミン塩、塩基性アミノ酸塩等が挙げられ、具体的には、ナトリウム、カリウム、リチウム等のアルカリ金属、カルシウム、マグネシウム等のアルカリ土類金属、アルミニウム、亜鉛等の金属、アンモニア、モノエタノールアミン、ジエタノールアミン、トリエタノールアミン、トリイソプロパノールアミン等の有機アミン、アルギニン、リジン等の塩基性アミノ酸等から任意に選ばれる1種または2種以上との塩である。これらの中でも、ナトリウム塩、カリウム塩、有機アミン塩、塩基性アミノ酸塩が好ましい。
【0039】
このような一般式(1)で示される多鎖多親水基型界面活性剤の製造方法としては、一般式(3)で示されるN−長鎖アシル酸性アミノ酸無水物と分子内にヒドロキシル基、アミノ基、チオール基から選ばれる1種または2種以上のm個の官能基を有する化合物とを、水および/または水と有機溶媒との混合溶媒中で反応させることによって得ることができる。
【0040】
【化5】
【0041】
あるいは、一般式(1)で示される多鎖多親水基型界面活性剤は、一般式(3)で示されるN−長鎖アシル酸性アミノ酸無水物とポリヒドロキシル化合物またはポリアミノ化合物またはポリチオール化合物、または分子内にヒドロキシル基、アミノ基、チオール基のうちいずれか2種または3種を有する化合物とをいずれかの融点以上の温度で、またはテトラヒドロフラン、ベンゼン、トルエン、キシレン、四塩化炭素、クロロホルム、アセトン等の不活性溶媒を使用して−5〜200℃で混合することで得ることができる。
【0042】
または、一般式(1)で示される多鎖多親水基型界面活性剤は、N−長鎖アシル酸性アミノ酸モノ低級エステル(例えば、メチルエステル、エチルエステル)とポリヒドロキシル化合物またはポリアミノ化合物またはポリチオール化合物、または分子内にヒドロキシル基、アミノ基、チオール基のうちいずれか2種または3種を有する化合物とをジメチルホルムアミド等の適当な溶媒中に溶解し、炭酸カリウム等の触媒を加え、減圧下に−5℃〜250℃で加熱反応させた後反応溶媒を除去することで得ることができる。あるいは、無溶媒で加熱溶融し、水酸化ナトリウム等の触媒を加えて室温〜250℃でエステル交換反応させて本発明の界面活性剤を得ることができる。
【0043】
本発明のクレンジング剤において、界面活性剤として、多鎖多親水基型界面活性剤以外にも、本発明の目的が損なわれない限り、その他の界面活性剤を含むことができる。こうした界面活性剤としては、例えば、分子内に長鎖疎水基および/または親水基が1個である構造のアニオン性界面活性剤、ノニオン性界面活性剤、カチオン性界面活性剤、両性界面活性剤等である。中でも該水溶液中にアニオン性界面活性剤としてN−長鎖アシルアミノ酸型界面活性剤またはアシルペプチド型界面活性剤を含有したものが好ましい。
【0044】
ここでいうN−長鎖アシルアミノ酸とは、アミノ酸のアミノ基に、炭素数8〜20の飽和または不飽和の脂肪酸から誘導されるアシル基を導入したものである。N−長鎖アシルアミノ酸中のアミノ酸残基はα−アミノ酸、β−アミノ酸、γ−アミノ酸やω−アミノ酸等各種アミノ酸であり、アミノ基はN−メチル体、N−エチル体であってもかまわない。また光学異性体すなわちD−体、L−体、ラセミ体であるかは問わない。
【0045】
例えば、グルタミン酸、アスパラギン酸、グリシン、アラニン、バリイン、ロイシン、イソロイシン、セリン、トレオニン、システイン、システイン、シスチン、メチオニン、リジン、アルギニン、フェニルアラニン、チロシン、ヒスチジン、トリプトファン、プロリン、オキシプロリン、ランチオニン、β−メチルランチオニン、シスタチオニン、ジエンコール酸、フェリニン、アミノマロン酸、β−オキシアスパラギン酸、α−アミノ−α−メチルコハク酸、β−オキシグルタミン酸、γ−オキシグルタミン酸、γ−メチルグルタミン酸、γ−メチレングルタミン酸、γ−メチル−γ−オキシグルタミン酸、α−アミノアジピン酸、α,α’−ジアミノアジピン酸、β,β’−ジアミノアジピン酸、α−アミノ−γ−オキシアジピン酸、α−アミノピメリン酸、α−アミノ−γ−オキシピメリン酸、β−アミノピメリン酸、α−アミノスベリン酸、α−アミノセバシン酸、パントテン酸、サルコシン、タウリン、メチルタウリン等である。
【0046】
アシル基としては、炭素原子数8〜20の飽和または不飽和の脂肪酸から誘導されるものであれば何でも良く、直鎖、分岐、環状を問わない。N−長鎖アシルアミノ酸がN−長鎖アシル−L−アミノ酸であることが生分解性の点から好ましい。
また、ここでいうアシルペプチドとは、タンパク質を加水分解した後、アシル化して得られるものである。
【0047】
本発明のクレンジング剤において、分子内に水酸基を2個以上有するポリヒドロキシル化合物としては、例えばエチレングリコール、1,2−プロパンジオール、1,3−プロパンジオール、1,2−ブタンジオール、1,3−ブタンジオール、1,4−ブタンジオール、ペンタンジオール、1,6−ヘキサンジオール、シクロヘキサンジオール、ジメチロールシクロヘキサン、ネオペンチルグリコール、1,8−オクタンジオール、
2,2,4−トリメチル−1,3−ペンタンジオール、イソプレングリコール、3−メチル−1,5−ペンタンジオール、ソルバイト、カテコール、レゾルシン、ヒドロキノン、ビスフェノールA、ビスフェノールF、水添ビスフェノールA、水添ビスフェノールF、
ダイマージオール、ジメチロールプロピオン酸、ジメチロールブタン酸、酒石酸、ジヒドロキシ酒石酸、メバロン酸、3,4−ジヒドロキシけい皮酸、3,4−ジヒドロキシヒドロけい皮酸、ヒドロキシ安息香酸、ジヒドロキシステアリン酸、ジヒドロキシフェニルアラニン等およびこれらの各異性体等の2価ヒドロキシル化合物;
【0048】
グリセリン、トリオキシイソブタン、1,2,3−ブタントリオール、1,2,3−ペンタントリオール、2−メチル−1,2,3−プロパントリオール、2−メチル−2,3,4−ブタントリオール、2−エチル−1,2,3−ブタントリオール、2,3,4−ペンタントリオール、
2,3,4−ヘキサントリオール、4−プロピル−3,4,5−ヘプタントリオール、2,4−ジメチル−2,3,4−ペンタントリオール、1,2,4−ブタントリオール、1,2,4−ペンタントリオール、トリメチロールエタン、トリメチロールプロパン、ジエタノールアミン、トリエタノールアミン、トリヒドロキシステアリン酸等の3価ポリヒドロキシル化合物;
ペンタエリスリトール、エリスリトール、1,2,3,4−ペンタンテトロール、2,3,4,5−ヘキサンテトロール、1,2,4,5−ペンタンテトロール、1,3,4,5−ヘキサンテトロール、ジグリセリン、ソルビタン等の4価ポリヒドロキシル化合物;
アドニトール、アラビトール、キシリトール、トリグリセリン等の5価ポリヒドロキシル化合物;
ジペンタエリスリトール、ソルビトール、マンニトール、イジトール、イノシトール、ダルシトール、タロース、アロース等の6価ポリヒドロキシル化合物;
またはこれらの脱水縮合物、ポリグリセリン等が挙げられる。
【0049】
また、糖類、例えばエリスロース、スレオース、エリスルロース等のテトロース;
リボース、アラビノース、キシロース、リクソース、キシルロース、リブロース等のペントース;アロース、アルトロース、グルコース、マンノース、ギューロース、イドース、ガラクトース、タロース、フラクトース、ソルボース、プシコース、タガトース等のヘキソース等の単糖類;
マルトース、イソマルトース、セロビオース、ゲンチオビオース、メリビオース、ラクトース、ツラノース、トレハロース、サッカロース、マンニトリオース、セロトリオース、ゲンチアノース、ラフィノース、メレチトース、セロテトロース、スタキオース等のオリゴ糖類が挙げられる。
【0050】
また、その他の糖類、例えばヘプトース、デオキシ糖、アミノ糖、チオ糖、セレノ糖、アルドン糖、ウロン酸、糖酸、ケトアルドン酸、アンヒドロ糖、不飽和糖、糖エステル、糖エーテル、グリコシド等の残基でもよく、デンプン、グリコーゲン、セルロース、キチン、キトサン等の多糖類またはそれらを加水分解したものでもよい。これらポリヒドロキシル化合物は2種以上組み合わせて用いても良い。ポリヒドロキシル化合物として好ましくは、3価以上のポリヒドロキシル化合物がよい。
【0051】
本発明のクレンジング剤において、油性成分としては、液状油または固体脂のいずれをも使用することができ、化粧料や外用の医薬品などの成分として慣用されている油性成分でもよい。
例えば、アボガド油、アーモンド油、オリーブ油、カカオ油、ゴマ油、サフラワー油、大豆油、ツバキ油、パーシック油、ひまし油、ぶどう種子油、マカデミアナッツ油、ミンク油、綿実油、モクロウ、ヤシ油、卵黄油、パーム油、パーム核油、トリイソオクタン酸グリセリル、トリ2−エチルヘキサン酸グリセリルコレステロール脂肪酸エステル等の油脂、
鯨ロウ、カルナバロウ、キャンデリラロウ、ホホバ油、ミツロウ、ラノリン等およびその誘導体等のロウ類、
流動パラフィン、パラフィン、ワセリン、セレシン、マイクロクリスタリンワックス、スクワラン、スクアレン等の炭化水素、
【0052】
ラウリン酸、ミリスチン酸、パルミチン酸、ステアリン酸、イソステアリン、オレイン酸、ベヘニン酸、ウンデシレン酸、ラノリン脂肪酸、硬質ラノリン脂肪酸、軟質ラノリン脂肪酸酸等の高級脂肪酸、
ラウリルアルコール、セチルアルコール、セトステアリルアルコール、ステアリルアルコール、イソステアリルアルコール、2−オクチルドデカノール、オレイルアルコール、ベヘニルアルコール、ラノリンアルコール、水添ラノリンアルコール、へキシルデカノール等の高級アルコール、
ミリスチン酸イソピロピル、ミリスチン酸オクタデシル、ミリスチン酸2−オクチルドデシル、2−エチルヘキサン酸セチル、リンゴ酸ジイソステアリル、イソステアリン酸イソステアリル、イソステアリルコレステリルエステル、ステアリン酸ブチル等の高級アルコール脂肪酸エステル、
メチルポリシロキサン、メチルフェニルポリシロキサン等のシリコーン油等の揮発性および不揮発性の油性成分が挙げられる。これら油性成分は2種以上組み合わせて用いても良い。
【0053】
本発明のクレンジング剤は、界面活性剤の1種または2種以上、分子内に水酸基を2個以上有するポリヒドロキシル化合物の1種または2種以上、および油性成分の1種または2種以上を含有するクレンジング剤であって、該組成物中の水分含量が50重量%以下であり、かつ水分を含めたクレンジング剤組成物中の組成が、1)界面活性剤の総量が0.1〜40重量%、2)ポリヒドロキシル化合物の総量が1〜60重量%、3)油性成分の総量が1〜95重量%、とすることが好ましい。ここで、界面活性剤、ポリヒドロキシル化合物、油性成分のそれぞれの総量は、それぞれに該当する成分の総和である。各成分の組成がこの範囲外であってもゲル状の剤型になることはあるが皮膚等に塗布した場合に伸びが悪くなったり、油性成分が分離して安定性に乏しかったり、ゲル形成力が不十分であったり、目的によっては汚れの洗浄力が低下したり、伸びが悪くなる等使用感が好ましくなくなることがある。
【0054】
本発明のクレンジング剤においては、界面活性剤、ポリヒドロキシル化合物、油性成分の各成分組成は、好ましくは、該組成物中の組成が、1)界面活性剤の総量が1〜25重量%、2)ポリヒドロキシル化合物の総量が5〜40重量%、3)油性成分の総量が20〜80重量%、とする。さらに好ましくは、1)界面活性剤の総量が3〜15重量%、2)ポリヒドロキシル化合物の総量が5〜30重量%、3)油性成分の総量が30〜70重量%、とする。
【0055】
本発明のクレンジング剤において、水分含量は50重量%以下が好ましい。この範囲外ではゲル状を安定に保持しにくい場合がある。水分含量はより好ましくは、30重量%以下である。さらに好ましくは、20重量%以下とする。
本発明のクレンジング剤においては、25℃における粘度が1000〜2000000mPa・sの範囲のものが皮膚等に塗布した時の伸びに優れるので好ましい。さらに好ましくは、25℃における粘度が、3000〜60000mPa・sの範囲のものがよい。
【0056】
本発明のクレンジング剤において、外観が透明なクレンジング剤を得るためには該組成物中の界面活性剤、ポリヒドロキシル化合物、および水からなる水相と、油性成分からなる油相との20℃における屈折率の差を±0.05以下とすることが好ましい。両相の屈折率の差がこの範囲を外れると、外観の透明な組成物を得にくく、両相の屈折率差は0に近づける方がよい。より好ましくは、両相の屈折率の差を±0.03以下とする。さらに好ましくは、両相の屈折率差を±0.01以下とする。
【0057】
本発明のクレンジング剤を製造するには、界面活性剤、ポリヒドロキシル化合物、油性成分および場合によっては水を高専断力の下で攪拌・混合することにより製造される。好ましい製造方法としては、油性成分以外の成分を十分に攪拌・混合し、これに油性成分を添加していく方法がよい。
【0058】
かくして得られる本発明のクレンジング剤の特徴は、
1)ゲル形成力が高く、経時的にも非常に安定なゲルを保つ、2)皮膚に塗布した時の伸びに優れ、また塗布後水を添加すると極めて容易にエマルジョン状態に微分散する、3)容易に水で洗い流すことができ、後に残らずさっぱり感があるという特徴があり、これまでの課題を解決するものである。
本発明のクレンジング剤は、例えばクレンジングクリーム、クレンジングゲル、マッサージクリーム、マッサージゲル等、皮膚等に塗布して使用した後洗い落とすことを目的とする用途に対して適用することができるものをいう。
本発明のクレンジング剤においては、本発明の目的が損なわれない限り、通常香粧品やトイレタリー製品等に用いられる各種の基材と併用することができる。また、本発明のクレンジング剤は、所望によりゲル状の他、ペースト状、液状、フォーム状等にすることができる。
【0059】
具体的には、脂肪酸塩(石鹸)、アルキル硫酸エステル塩(AS)、ポリオキシエチレンアルキルエーテル硫酸エステル塩(AES)、アルファ−オレフィンスルホン酸塩(AOS)、アルキルベンゼンスルホン酸塩、アルキルナフタレンスルホン酸塩、アルキルスルホン酸塩(SAS)、ジアルキルスルホコハク酸塩、アルファースルホン化脂肪酸塩、N−長鎖アシルアミノ酸塩、N−アシル−N−メチルタウリン塩、硫酸化油脂、ポリオキシエチレンスチレン化フェニルエーテル硫酸塩、アルキルリン酸塩、ポリオキシエチレンアルキルエーテルリン酸塩、ポリオキシエチレンアルキルフェニルエーテルリン酸塩、ナフタリンスルフォン酸塩ホルマリン縮合物などのアニオン性界面活性剤;
アルキルベタイン類、アルキルアミドベタイン類、アルキルスルホベタイン類、アルキルヒドロキシスルホベタイン類、アルキルアミドヒドロキシスルホベタイン類、アルキルアミドアミン型ベタイン類、イミダゾリニウムベタイン類などの両性界面活性剤;
【0060】
脂肪酸アルキロールアミド、アルキルアミンオキサイド、ポリオキシエチレンアルキルエーテル(AE)、ポリオキシエチレンアルキルフェニルエーテル、ポリオキシエチレンポリスチリルフェニルエーテル、ポリオキシエチレンポリオキシプロピレングリコール、ポリオキシエチレンポリオキシプロピレンアルキルエーテル、
多価アルコール脂肪酸部分エステル、ポリオキシエチレン多価アルコール脂肪酸部分エステル、ポリオキシエチレン脂肪酸エステル、ポリグリセリン脂肪酸エステル、ポリオキシエチレン硬化ひまし油、ポリオキシエチレンアルキルアミン、トリエタノールアミン脂肪酸部分エステルなどのノニオン性界面活性剤;
第1〜第3級脂肪アミン塩、塩化アルキルアンモニウム塩、テトラアルキルアンモニウム塩、トリアルキルベンジルアンモニウム塩、アルキルピリジニウム塩、アルキルヒドロキシエチルイミダゾリニウム塩、ジアルキルモルフォリニウム塩などのカチオン性界面活性剤;
アルギン酸ナトリウム、デンプン誘導体、トラガントゴムなどの高分子界面活性剤;
【0061】
レシチン、ラノリン、コレステロール、サポニンなどの天然界面活性剤;
トリメチルグリシン、ソルビトール、ラフィノース、ピロリドンカルボン酸塩類、乳酸塩類、ヒアルロン酸塩類、セラミド、擬セラミド、尿素類などの保湿剤;
ヒドロキシエチルセルロース、カルボキシメチルセルロース、ヒドロキシエチルセルロースヒドロキシプロピルトリメチルアンモニウムクロリドエーテル、メチルセルロース、エチルセルロース、ヒドロキシプロピルセルロース、メチルヒドロキシプロピルセルロース、可溶性デンプン、カルボキシメチルデンプン、メチルデンプン、
アルギン酸プロピレングリコールエステル、ポリビニルアルコール、ポリビニルピロリドン、ポリビニルメチルエーテル、カルボキシビニルポリマー、ポリアクリル酸塩、グアーガム、ローカストビンガム、クインスシード、カラギーナン、ガラクタン、
アラビアガム、ペクチン、マンナン、デンプン、キサンタンガム、デキストラン、サクシノグルカン、カードラン、ヒアルロン酸、ゼラチン、カゼイン、アルブミン、コラーゲン、メトキシエチレン無水マレイン酸共重合体、両性メタクリル酸エステル共重合体、ポリ塩化ジメチルメチレンピペリジニウム、ポリアクリル酸エステル共重合体、ポリ酢酸ビニル、ニトロセルロース、シリコーンレジン等の水溶性および油溶性高分子;
【0062】
ポリエチレングリコール脂肪酸エステル、ポリオキシエチレン脂肪酸エステルメチルグリコシド、テトラデセンスルホン酸塩等の増粘、増泡成分;
ギ酸、酢酸等の物モノカルボン酸とその塩類、シュウ酸、マロン酸、コハク酸等のジカルボン酸とその塩類、トリカルバリル酸、プロパン−1,1,2,3−テトラカルボン酸等のポリカルボン酸とその塩類、グリコール酸、酒石酸、クエン酸、オキサル酸、グルコン酸等のオキシまたはケトカルボン酸とその塩類、フタル酸等の芳香族カルボン酸とその塩類、エチレンジアミン、N−エチルエチレンジアミン等のアミンおよびその誘導体類、イミノジ酢酸、イミノジプロピオン酸、フェニルイミノジ酢酸、ヒドロキシエチルイミノジ酢酸、メルカプトエチルイミノジ酢酸等のイミノジ酢酸とその塩類、ニトリロトリ酢酸、カルボキシエチルイミノジ酢酸等のニトリロ酢酸とその塩類、N,N−エチレンジアミンジ酢酸等の誘導体、エチレンジアミンテトラ酢酸、ジエチレントリアミ ンペンタ酢酸、トリメチレンテトラアミンヘキサ酢酸等 のアミノポリ酢酸とその塩類、グリシン、アラニン、グルタミン 酸、アスパラギン酸等のアミノ酸とその塩類等、トリポリリン酸、フチン酸、1,1−ヒドロキシエタン−1,2−ジ ホスホン酸、ポリリン酸、メタリン酸塩等のリン酸とその塩類;その他、アスコルビン酸、ヒノキチール類などの金属イオン封鎖剤;
【0063】
安息香酸およびその塩類、パラオキシ安息香酸イソプロピル、バラオキシ安息香酸イソプロピル、パラオキシ安息香酸エチル、パラオキシ安息香酸メチル、パラオキシ安息香酸ブチル、パラ オキシ安息香酸プロピル等の安息香酸系防腐剤類、ソルビン酸、ソルビン酸カリウム等のソルビン酸系防
腐剤 類、デヒドロ酢酸類、プロピオン酸類、ジフェニル、オ ルトフェニルフェノール及びナトリウム等のジフェニル類、チアベンゾール、イマザリル、フェノキシエタノール、ヒノキチオール等の防腐剤;
クエン酸、リンゴ酸、アジピン酸、グルタミン酸、アスパラギン酸等のpH調整剤;
その他トリクロロルカルバニリド、サリチル酸、ジンクピリチオン、イソプロピルメチルフェノールなどのふけ・かゆみ防止剤;
ベンゾフェノン誘導体、パラアミノ安息香酸誘導体、パラメトキシ桂皮酸誘導体、サリチル酸誘導体その他の紫外線吸収剤;
アルブチン、コウジ酸、アスコルビン酸、ヒノキチールおよびその誘導体などの美白剤;
【0064】
センブリエキス、セファランチン、ビタミンEおよびその誘導体、ガンマーオリザノールなどの血行促進剤;
トウガラシチンキ、ショオウキョウチンキ、カンタリスチンキ、ニコチン酸ベンジルエステルなどの局所刺激剤;
各種ビタミンやアミノ酸などの栄養剤;
女性ホルモン剤;
毛根賦活剤;
グリチルレチン酸、グリチルリチン酸誘導体、アラントイン、アズレン、アミノカプロン酸、ヒドロコルチゾンなどの抗炎症剤;
酸化亜鉛、硫酸亜鉛、アラントインヒドロキシアルミニウム、塩化アルミニウム、スルホ石炭酸亜鉛、タンニン酸などの収斂剤;
メントール、カンフルなどの清涼剤;
抗ヒスタミン剤;
高分子シリコーン、環状シリコーン等のシリコーン系物質、トコフェロール類、BHA、BHT、没食子酸、NDGAなどの酸化防止剤;
【0065】
脂肪族炭化水素、テルペン炭化水素、芳香族炭化水素等の炭化水素類、脂肪族アルコール、テルペンアルコール、芳香族アルコール等のアルコール類、脂肪族エーテル、芳香族エーテル等のエーテル類、脂肪族オキサイド、テルペン類のオキサイド等のオキサイド類、脂肪族 アルデヒド、テルペン系アルデヒド、水素化芳香族アル デヒド、チオアルデヒド、芳香族アルデヒド等のアルデ ヒド類、脂肪族ケトン、テルペンケトン、水素化芳香族 ケトン、脂肪族環状ケトン、非ベンゼン系芳香族ケトン、芳香族ケトン等のケトン類、アセタール類、ケタール頼、フェノール類、フェノールエーテル類、脂肪酸、 テルペン系カルボン酸、水素化芳香族カルボン酸、芳香 族カルボン酸等の酸類、酸アマイド類、脂肪族ラクトン、大環状ラクトン、テルペン系ラクトン、水素化芳香 族ラクトン、芳香族ラクトン等のラクトン類、脂肪族エ ステル、フラン系カルボン酸エステル、脂肪族環
状カルボン酸エステル、シクロヘキシルカルボン酸族エステ ル、テルペン系カルボン酸エステル、芳香族カルボン酸 エステル等のエステル類、ニトロムスク類、ニトリル、 アミン、ピリジン類、キノリン類、ピロール、インドール等の含窒素化合物等々の合成香料及び植物からの天然香料;
精製水等などを含むことができる。また必要に応じて粘度低減剤等も使用できる。
特に、各両イオン性界面活性剤との併用は刺激性を一層低減させるという点に於いてきわめて有用である。
【0066】
以下で、本発明を実施例等を用いてさらに具体的に説明するが、本発明はこれら実施例等により何ら限定させるものではない。
以下、実施例に従って本発明の方法を詳細に説明する。
本発明の実施例等で用いる評価手段などは以下の通りである。
(安定性)
各クレンジング剤を40℃で保存して、1か月後における状態を観察し、安定性を下記基準に従い評価した。
○:状態変化がなく良好
△:わずかに分離が見られる
×:明らかに分離がみられる。
(粘度)
B型粘度計で25℃でクレンジング剤の製造直後の粘度を測定した。
(屈折率)
屈折率計により、各相の20℃における屈折率を測定した。
【0067】
(使用感)
パネラー5人により、クレンジング剤の使用感・水で洗い流した後の使用感を下記基準に従い官能評価した。
○:べとつきがなく、使用感が良好と感じた人が、3人以上
△: 〃 、1または2人
×: 〃 、0人
(使用時の伸び易さ)
パネラー5人により、クレンジング剤の使用持の伸び易さを下記基準に従い官能評価した。
○:良好と感じた人が、3人以上
△: 〃 、1または2人
×: 〃 、0人
(外観)
各クレンジング組成物を目視にて評価した。
【0068】
(多鎖多親水基型界面活性剤の製造例1)
L−リジン塩酸塩9.1g(0.05mol)を水57gと混合した。この液を25%水酸化ナトリウム水溶液でpH範囲を10〜11に調整しながら、また反応温度を5℃に維持しながら、攪拌下にN−ラウロイル−L−グルタミン酸無水物31.1g(0.1mol)を2時間を要して添加し、反応を実施した。さらに30分攪拌を続けた後、ターシャリーブタノールを液中濃度20重量%となるように添加した後、75%硫酸を滴下して液のpH値を2に、また液の温度を65℃に調整した。滴下終了後、攪拌を停止し、20分間65℃で静置すると有機層と水層とに分層し、これから有機層を分離した。分離した有機層にターシャリーブタノールおよび水を添加して、温度を65℃にして20分攪拌した。攪拌停止後、静置すると有機層と水層とに分層した。得られた有機層に対して、同じ水洗操作をくり返した後、得られた有機層から溶媒を除去し、水酸化ナトリウムで固形分30重量%でpH6.5(25℃)に中和した後乾燥して多鎖多親水基型界面活性剤を得た。
【0069】
(多鎖多親水基型界面活性剤の製造例2)
製造例1において、反応条件をL−リシン塩酸塩9.1g(0.05mol)をエチレンジアミン3.0g(0.05g)とし、中和条件を固形分30重量%でpH7.5(25℃)とした以外は製造例1と同じ条件で実施し、多鎖多親水基型界面活性剤を得た。
【0070】
【実施例1〜7、比較例1〜3】
表1に示す組成のクレンジング剤を製造し、それぞれについて、安定性、使用感を評価した。結果を表1に示す。
(製法)いずれのクレンジング剤も下記の方法で調製した。
油性成分以外の成分を70℃で攪拌しながら混合する。これに、攪拌しながら油性成分をゆっくりと滴下し、更に攪拌した後、冷却してゲル状のクレンジング剤を得た。
【0071】
【表1】
【0072】
【発明の効果】
本発明のクレンジング剤は、長鎖疎水基と親水基とを分子内に2個以上づつ有する界面活性剤を含有するものであるが、実施例にも示すようにこの界面活性剤を用いて製造したクレンジング剤は、他のいずれの界面活性剤を用いた場合に比し、非常に安定性に優れるものである。また、得られたクレンジング剤は、極めて容易に水洗いが可能であり、使用感に優れたものであることが、明らかである。[0001]
TECHNICAL FIELD OF THE INVENTION
The present invention relates to a cleansing agent, in particular, it is excellent in stability and can be completely removed only with water without tissue off, and is a transparent to translucent, which is useful as a cosmetic such as a cleansing gel or cream, massage cream, etc., which has excellent usability. It relates to an emulsified cleansing agent.
[0002]
[Prior art]
There are cleansing or massage cosmetics as cosmetics used for the purpose of removing skin stains and makeup cosmetics or for the purpose of massaging the skin. It will be removed. As such cosmetics, there are various gel cosmetics in which an oil component is mixed with an aqueous solvent and the dosage form is prepared in a gel form. However, these cosmetics have problems such as stickiness at the time of use and / or after use and poor storage stability. Here, the gel refers to a wide range of liquid contents such as paste, cream, and jelly as described on page 245 of the basics of colloid chemistry (Dainihon Tosho Co., Ltd., issued in 1976).
[0003]
For example, an oil component is mixed in an aqueous solvent, and its dosage form is prepared in a gel form, and a water-soluble polymer compound known as a gelling agent is generally added. When the gel composition thus formed with a water-soluble polymer is used for a cleansing cosmetic, the elongation is poor, or there is a problem with dirt removal, and there are also sticky things after washing with water. Has a problem of poor stability over time as described above.
[0004]
On the other hand, there is an oil gel obtained by gelling an oil with a gelling agent, but it is difficult to adjust the viscosity of the resulting gel composition, and it can be washed away with water when used as a cleansing agent such as makeup remover. Instead, after use, it is necessary to wipe it off with tissue paper or the like, and then re-wash it with a face wash or the like. Similarly, there is a gel composition emulsified in a water-in-oil type. In this case, when used as a cleansing agent in the same manner as an oil gel in order to make the oil phase a continuous phase, re-washing is required after use. In all cases, the oily components are sticky to the hands and the feeling of use is not preferred.
[0005]
Also, an oil-in-water emulsified gel composition is known, which can be washed away with water without the wiping operation as described above, but an oily component often remains on the skin, Washing with water alone is not sufficient. In addition, it is poorly compatible with oil stains and has insufficient cleansing properties. For this reason, many types in which the type and amount of the oil component and the surfactant are changed have been studied, but they are not sufficiently satisfactory in terms of stability, feeling of use, and the like. Further, it is difficult to make the appearance of the emulsion type composition transparent.
[0006]
Further, JP-A-10-219278 discloses a composition of an anionic surfactant containing an acyl group 2 long chain dipolar group, which is a composition capable of removing makeup stains and the like. There is a statement that it can be done. However, all of the examples are only examples using an aqueous solution of the cleaning composition, and nothing is described about a cleansing agent in the form of an oily gel.
[0007]
[Patent Document 1]
JP-A-10-219278
[Problems to be solved by the invention]
The present invention has a stable gel composition containing an oily component without containing a gelling agent, has excellent stability over time, has a good feeling of use such as elongation when applied, and has a good feel after use. The purpose of the present invention is to provide a translucent / emulsified cleansing agent.
[0009]
[Means for Solving the Problems]
The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, a specific surfactant, that is, a multi-chain poly-hydrophilic group type having two or more long-chain hydrophobic groups and two or more hydrophilic groups in the molecule. By using a surfactant, the oily component is stably compounded in a gel form without using a gelling agent, and has excellent stability over time, and a gel composition of any hardness from a paste state to a solid state. I found that I could get. Also, surprisingly, among the gel compositions thus obtained, those having a certain viscosity range are excellent in elongation when applied to the skin or the like, and the composition is extremely excellent in dispersibility in water. The present inventors have found that this gel composition can be provided as a type of cleansing agent that can be easily washed off with water after being applied to the skin or the like, and have completed the present invention.
Further, the gel composition is such that the difference in the refractive index at 20 ° C. between an aqueous phase composed of a surfactant, a polyhydroxyl compound and water and an oil phase composed of an oily component is reduced. Have been found to have a transparent appearance, and have completed the present invention.
[0010]
That is, the present invention is as follows.
1. One or more polychain polyhydrophilic surfactants having two or more long-chain hydrophobic groups and hydrophilic groups in the molecule, and one or more polyhydroxyl compounds having two or more hydroxyl groups in the molecule or A cleansing agent comprising two or more types and one or more oily components.
2. The water content in the cleansing agent is 50% by weight or less, and the composition in the cleansing agent composition including water is such that 1) the total amount of the surfactant component is 0.1 to 40% by weight, and 2) polyhydroxyl. The total amount of the compound is 1 to 60% by weight, and 3) the total amount of the oil component is 1 to 95% by weight. The cleansing agent according to 1.
3. At least one of the multi-chain and poly-hydrophilic surfactants in the cleansing agent has a long-chain hydrophobic group as a long-chain acyl group, and a hydrophilic group as a carboxyl group, a sulfonic group, a sulfate group, or a phosphate group. And / or a salt thereof, which is an anionic surfactant. Or 2. The cleansing agent according to 1.
4. Cleansing agent At least one of the multi-chain and multi-hydrophilic surfactants has an amino acid residue in the molecule. ~ 3. The cleansing agent according to any one of the above.
5. At least one of the multi-chain and multi-hydrophilic surfactants in the cleansing agent is a compound represented by the general formula (1). ~ 4. The cleansing agent according to any one of the above.
[0011]
Embedded image
[0012]
(In the general formula (1), n Zs are bonding parts derived from m (m ≧ n) functional groups substituted by X, and each is independently, that is, may be the same or different; Is a spacer which may have a substituent other than the functional group and is a linear, branched, or cyclic chain or an aromatic hydrocarbon chain having a molecular weight of 1,000,000 or less, and n spacers attached to X via Z The substituents represented by the general formula (2) are each independently, that is, may be the same or different,
R 1 CO represents a long-chain acyl group derived from a saturated or unsaturated fatty acid having 28 to 20 carbon atoms, and R 2 represents hydrogen or a carbon atom which may be substituted by a hydroxyl group or a carboxyl group. Y represents a lower alkyl group having 1 to 3 atoms, Y represents a carboxyl group, a sulfonic acid group, a sulfate ester group, a phosphate ester group and / or a salt thereof, and j and k each independently represent 0, 1, 2, or 3. And j and k are not simultaneously 0 and n represents an integer of 2 to 20)
[0013]
Embedded image
[0014]
6. At least one of the multi-chain and poly-hydrophilic surfactants in the cleansing agent is a compound represented by the general formula (1), and in the general formula (1), X has a substituent other than the functional group. 1. A spacer which is a linear, branched, or cyclic chain having 1 to 40 carbon atoms, or an aromatic hydrocarbon chain. ~ 5. The cleansing agent according to any one of the above.
7. The difference in refractive index at 20 ° C. between an aqueous phase comprising a surfactant, a polyhydroxyl compound and water in a cleansing agent and an oil phase comprising an oily component is ± 0.05 or less. ~ 6. The cleansing agent according to any one of the above.
8. The viscosity at 25 ° C. is from 1,000 to 200,000 mPa · s. ~ 7. The cleansing agent according to any one of the above.
[0015]
BEST MODE FOR CARRYING OUT THE INVENTION
Hereinafter, the present invention will be described in detail with particular emphasis on its embodiments.
The cleansing agent referred to in the present invention is one or more of a multi-chain and multi-hydrophilic group type surfactant, one or more of a polyhydroxyl compound having two or more hydroxyl groups in a molecule, and one of an oily component. And at least one of the surfactants is a cleansing agent that is a multi-chain and multi-hydrophilic group type surfactant. In the present invention, the multi-chain poly-hydrophilic group type surfactant includes, independently as the long-chain hydrophobic group, a hydrophobic group composed of a saturated or unsaturated linear, branched or cyclic chain having 8 to 20 carbon atoms. Having a carboxyl group, a sulfonic acid group, a sulfuric acid residue, a phosphoric acid residue or a salt thereof, or an oxyalkylene group, a polyethylene glycol group, or the like; It has an ammonium group, a pyridinium group, a sulfonium group or a salt thereof.
[0016]
For example, examples of the long-chain hydrophobic group of the multi-chain poly-hydrophilic group type surfactant include n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n Residues such as pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl and their branched-chain isomers, and one, two or three corresponding to these And an unsaturated residue having an unsaturated moiety.
[0017]
The long-chain hydrophobic group of the multi-chain poly-hydrophilic surfactant is a long-chain acyl group derived from a saturated or unsaturated fatty acid having 8 to 20 carbon atoms,
Straight chain fatty acids such as, for example, caprylic acid, pelargonic acid, capric acid, undecanoic acid, lauric acid, tridecanoic acid, myristic acid, pentadecanoic acid, palmitic acid, margaric acid, stearic acid, nonadecanoic acid, arachinic acid;
2-butyl-5-methylpentanoic acid, 2-isobutyl-5-methylpentanoic acid, dimethyloctanoic acid, dimethylnonanoic acid, 2-butyl-5-methylhexanoic acid, methylundecanoic acid, dimethyldecanoic acid, 2-ethyl- 3-methylnonanoic acid, 2,2-dimethyl-4-ethyloctanoic acid, methyldocosanoic acid, 2-propyl-3-methylnonanoic acid,
Methyltridecanoic acid, dimethyldodecanoic acid, 2-butyl-3-methylnonanoic acid, methyltetradecanoic acid, ethyltridecanoic acid, propyldodecanoic acid, butylundecanoic acid, pentyldecanoic acid, hexylnonanoic acid, 2- (3-methylbutyl)- 3-methylnonanoic acid, 2- (2-methylbutyl) -3-methylnonanoic acid, butylethylnonanoic acid,
[0018]
Methylpentadecanoic acid, ethyltetradecanoic acid, propyltridecanoic acid, butyldodecanoic acid, pentylundecanoic acid, hexyldecanoic acid, heptylnonanoic acid, dimethyltetradecanoic acid, butylpentylheptanoic acid, trimethyltridecanoic acid, methylhexadecanoic acid, ethylpentadecanoic acid, propyl Tetradecanoic acid, butyltridecanoic acid, pentyldodecanoic acid, hexylundecanoic acid, heptyldecanoic acid, methylheptylnonanoic acid,
Dipentylheptanoic acid, methylheptadecanoic acid, ethylhexadecanoic acid, ethylhexadecanoic acid, propylpentadecanoic acid, butyltetradecanoic acid, pentyltridecanoic acid, hexyldecanoic acid, heptylundecanoic acid, octyldecanoic acid, dimethylhexadecanoic acid,
Branched fatty acids such as methyl octyl nonanoic acid, methyl octadecanoic acid, ethyl heptadecanoic acid, dimethyl heptadecanoic acid, methyl octyl decanoic acid, methyl nonadecanoic acid, methyl nona decanoic acid, dimethyl octa decanoic acid, butyl heptyl nonanoic acid;
[0019]
Octenoic acid, nonenoic acid, decenoic acid, caproleic acid, undecylenic acid, lindelic acid, succinic acid, lauroleic acid, tridecenoic acid, tuzunic acid, myristoleic acid, pentadecenoic acid, hexedesenoic acid, palmitoleic acid, heptadecenoic acid, octadecenoic acid, Linear monoenoic acids such as oleic acid, nonadenoic acid, gondic acid;
Methylheptenoic acid,
Branched monoenoic acids such as methylnonenoic acid, methylundecenoic acid, dimethyldecenoic acid, methyldodecenoic acid, methyltridecenoic acid, dimethyldodecenoic acid, dimethyltridecenoic acid, methyloctadecenoic acid, dimethylheptadecenoic acid, and ethyloctadecenoic acid ;
Di- or trienoic acids such as linoleic acid, linoleic acid, eleostearic acid, linolenic acid, linolenic elaidic acid, pseudo eleostearic acid, parinaric acid, arachidonic acid;
Acetylenic acid such as octic acid, noninic acid, decinic acid, undesic acid, dodecic acid, tridesic acid, tetradecinic acid, pentadecinic acid, heptadecinic acid, octadecinic acid, nonadecinic acid, dimethyloctadecinic acid;
Methylene octadecenoic acid, methylene octadecanoic acid, aleprolic acid, alepresic acid, aleprilic acid, alepic acid, hydnocapric acid, scholmoog acid, gorlic acid, α-cyclopentylic acid, α-cyclohexylic acid, α-cyclopentylethyl acid And acyl groups derived from such cyclic acids.
[0020]
An acyl group derived from a fatty acid obtained from natural fats and oils may be used, and any acyl group derived from a mixed fatty acid containing 80% or more of the above-mentioned saturated or unsaturated fatty acid having 8 to 20 carbon atoms may be used. For example, acyl groups derived from coconut oil fatty acids, palm oil fatty acids, linseed oil fatty acids, sunflower oil fatty acids, soybean oil fatty acids, sesame oil fatty acids, castor oil fatty acids, olive oil fatty acids, camellia oil fatty acids, rapeseed oil fatty acids, palm kernel oil fatty acids, etc. And the like. The long-chain hydrophobic group is a long-chain acyl group, and the long-chain hydrophobic groups in the molecule are preferably the same. These multi-chain / multi-hydrophilic group type surfactants may be used in combination of two or more.
[0021]
In the cleansing agent of the present invention, examples of the multi-chain poly-hydrophilic group type surfactant include structurally, a surfactant having at least one long-chain hydrophobic group and at least one hydrophilic group in the molecule is suitable. It has a structure linked by a spacer, and any structure may be used as long as it has this structure, and a conventionally known compound may be used. As the spacer, a linear, branched or cyclic chain or an aromatic hydrocarbon chain having a molecular weight of 1,000,000 or less which may have a substituent is preferable. More preferably, the spacer is a linear, branched, or cyclic chain having 1 to 40 carbon atoms or an aromatic hydrocarbon chain.
[0022]
In the cleansing agent of the present invention, it is preferable that the hydrophilic groups of the multi-chain polyhydrophilic group type surfactant are each independently a carboxyl group, a sulfonic group, a sulfate group, a phosphate group and / or a salt thereof. . Here, examples of the salt include an alkali metal salt, an alkaline earth metal salt, an ammonium salt, an organic amine salt, a basic amino acid salt and the like.Specifically, alkali metals such as sodium, potassium and lithium, calcium, Any one selected from alkaline earth metals such as magnesium, metals such as aluminum and zinc, ammonia, organic amines such as monoethanolamine, diethanolamine, triethanolamine and triisopropanolamine, and basic amino acids such as arginine and lysine. A salt with one or more species. Among these, sodium salts, potassium salts, organic amine salts and basic amino acid salts are particularly preferred.
[0023]
In the cleansing agent of the present invention, it is preferable that at least one of the multi-chain and poly-hydrophilic group type surfactants is a surfactant having an amino acid residue in a molecule. It is preferable from the viewpoint of low irritation when used in preparations and the like. Further, it is more preferable that at least one kind of the multi-chain / multi-hydrophilic group type surfactant is a compound represented by the general formula (1).
In the general formula (1), the long-chain acyl groups represented by R 1 CO are independently, that is, they may be different or the same, and as described above, a saturated or unsaturated fatty acid having 8 to 20 carbon atoms. Any derivative may be used as long as it is linear, branched or cyclic. Further, it is preferable that R 1 CO in the molecule is the same in view of reaction conditions and the like.
[0024]
In the general formula (1), R 2 is hydrogen or has 1 carbon atom which may be substituted by a hydroxyl group or a carboxyl group, a sulfonic acid group, a sulfate ester group, a phosphate ester group or a salt thereof. Represents a lower alkyl group of 3 to 3, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a hydroxymethyl group, a hydroxyethyl group, a hydroxy (iso) propyl group, a dihydroxy (iso) propyl group, a carboxymethyl group, and a carboxymethyl group. Examples include an ethyl group, a carboxypropyl group, and a sulfoethyl group.
In the general formula (1), the n substituents (formula (2)) attached to X are independent, that is, they may be different or the same. Formula (2) shows a so-called acidic amino acid which is N-acylated, and it does not matter whether the amino acid is an optical isomer, for example, a D-form, an L-form, or a racemic form.
[0025]
The acidic amino acid is a monoaminodicarboxylic acid having two and one carboxyl groups and one amino group, respectively, in the molecule, and the amino group may be an N-methyl group or an N-ethyl group. It does not matter whether it is an optical isomer, for example, D-form, L-form, or racemic form. Examples of the acidic amino acids include glutamic acid, aspartic acid, lanthionine, β-methyllanthionine, cystathionine, diencholate, ferrinine, aminomalonic acid, β-oxyaspartic acid, α-amino-α-methylsuccinic acid, and β-oxyglutamic acid. , Γ-oxyglutamic acid, γ-methylglutamic acid, γ-methyleneglutamic acid, γ-methyl-γ-oxyglutamic acid, α-aminoadipic acid, α-amino-γ-oxyadipic acid, α-aminopimelic acid, α-amino- γ-oxypimelic acid, β-aminopimelic acid, α-aminosuberic acid, α-aminosebacic acid, pantothenic acid and the like.
[0026]
The n substituents (formula (2)) attached to X are preferable when the acidic amino acid is an L-acidic amino acid molecule because of its excellent biodegradability. Among them, the substituents are preferably the same.
In the general formula (1), n Zs attached to X are derived from m (m ≧ n and an integer of 2 to 20) functional groups (hydroxyl, amino, thiol) substituted for X. binding portion of (-O -, - NR 3 - , - S-) are, each independently, i.e., may be the same or different. Here, R 3 is hydrogen, an alkyl group or alkenyl group having 1 to 10 carbon atoms, an aryl group, or an alkylaryl group.
[0027]
In the general formula (1), X is a linear or branched or cyclic chain having a molecular weight of 1,000,000 or less and having m functional groups of one or more selected from a hydroxyl group, an amino group, and a thiol group; It is a spacer which is an aromatic hydrocarbon chain, and X may have a substituent other than the above-mentioned hydroxyl group, amino group and thiol group. In the general formula (1), X is preferably a residue of an m-valent compound having a molecular weight of 1,000,000 or less and having one or more m functional groups selected from a hydroxyl group, an amino group and a thiol group. , A compound residue which may have a substituent other than a hydroxyl group, an amino group and a thiol group. Here, the m-valent compound means that a bond derived from m functional groups can be formed. They may be optical isomers such as D-form, L-form and racemic form.
[0028]
Such m-valent compounds include, for example, amino acids such as serine, threonine, cysteine, cystine, cystine disulfoxide, cystathionine, methionine, arginine, lysine, tyrosine, histidine, tryptophan, oxyproline;
Aminoethanol, aminopropanol, aminobutanol, aminopentanol, aminohexanol, aminopropanediol, aminoethylethanolamine, aminoethylaminoethanol, aminocresol, aminonaphthol, aminonaphtholsulfonic acid,
Compounds having an amino group and a hydroxyl group in a molecule, such as aminohydroxybenzoic acid, aminohydroxybutanoic acid, aminophenol, aminophenethyl alcohol, and glucosamine;
Compounds having a thiol group and a hydroxyl group in a molecule, such as mercaptoethanol, mercaptophenol, mercaptopropanediol, and glucothiose;
Compounds having a thiol group and an amino group in the molecule, such as aminothiophenol and aminotriazole thiol. Further, proteins, peptides, etc., or those obtained by hydrolyzing them may be used.
[0029]
X preferably has 1 to 40 carbon atoms among the residues of such a compound, and more preferably X has 1 to 20 carbon atoms. Particularly preferred are those having 1 to 10 carbon atoms. Further, X is a substituent other than a hydroxyl group, an amino group, and a thiol group in the molecule, and at least one or more independent carboxyl groups, sulfonic groups, sulfate groups, phosphate groups, or salts thereof. Is preferable because the multi-chain / poly-hydrophilic group type surfactant represented by the general formula (1) is excellent in solubility in weak acidity. Further, it is preferable that X is a naturally-occurring type in that it is excellent in biodegradability.
[0030]
In the general formula (1), X is preferably an m-valent (m ≧ n) polyhydroxyl compound residue having a molecular weight of 1,000,000 or less, which may have a substituent other than a hydroxyl group. Here, an m-valent polyhydroxyl compound means that m ester bonds can be formed. They may be optical isomers such as D-form, L-form and racemic form.
Examples of such m-valent polyhydroxyl compounds include ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, and 1,4-butanediol. , Pentanediol, 1,6-hexanediol, cyclohexanediol, dimethylolcyclohexane, neopentyl glycol, 1,8-octanediol,
2,2,4-trimethyl-1,3-pentanediol, isoprene glycol, 3-methyl-1,5-pentanediol, sorbite, catechol, resorcin, hydroquinone, bisphenol A, bisphenol F, hydrogenated bisphenol A, hydrogenated Bisphenol F,
Dimer diol, dimethylolpropionic acid, dimethylolbutanoic acid, tartaric acid, dihydroxytartaric acid, mevalonic acid, 3,4-dihydroxycinnamic acid, 3,4-dihydroxyhydrocinnamic acid, hydroxybenzoic acid, dihydroxystearic acid, dihydroxyphenylalanine And a divalent hydroxyl compound such as each isomer thereof;
[0031]
Glycerin, trioxyisobutane, 1,2,3-butanetriol, 1,2,3-pentanetriol, 2-methyl-1,2,3-propanetriol, 2-methyl-2,3,4-butanetriol, 2-ethyl-1,2,3-butanetriol, 2,3,4-pentanetriol,
2,3,4-hexanetriol, 4-propyl-3,4,5-heptanetriol, 2,4-dimethyl-2,3,4-pentanetriol, 1,2,4-butanetriol, 1,2,2 Trivalent polyhydroxyl compounds such as 4-pentanetriol, trimethylolethane, trimethylolpropane, diethanolamine, triethanolamine, trihydroxystearic acid;
Pentaerythritol, erythritol, 1,2,3,4-pentane tetrol, 2,3,4,5-hexane tetrol, 1,2,4,5-pentane tetrol, 1,3,4,5-hexane Tetravalent polyhydroxyl compounds such as tetrol, diglycerin and sorbitan;
Pentavalent polyhydroxyl compounds such as adonitol, arabitol, xylitol, triglycerin;
Hexavalent polyhydroxyl compounds such as dipentaerythritol, sorbitol, mannitol, iditol, inositol, darcitol, talose, allose;
Or a dehydration condensate of these, polyglycerin and the like.
[0032]
Saccharides, for example tetroses such as erythrose, threose, erythrulose;
Pentoses such as ribose, arabinose, xylose, lixose, xylulose and ribulose; monosaccharides such as hexoses such as allose, altrose, glucose, mannose, gulose, idose, galactose, talose, fructose, sorbose, psicose, tagatose;
Oligosaccharides such as maltose, isomaltose, cellobiose, gentiobiose, melibiose, lactose, turanose, trehalose, saccharose, mannitolose, cellotriose, gentianose, raffinose, meletitose, cellotetroose and stachyose.
[0033]
In addition, other sugars such as heptose, deoxy sugar, amino sugar, thio sugar, seleno sugar, aldone sugar, uronic acid, sugar acid, ketoaldonic acid, anhydro sugar, unsaturated sugar, sugar ester, sugar ether, glycoside, etc. Or a polysaccharide such as starch, glycogen, cellulose, chitin, chitosan, or a hydrolyzed product thereof.
X preferably has 1 to 40 carbon atoms among the residues of such a compound, and more preferably X has 1 to 20 carbon atoms. Particularly preferred are those having 1 to 10 carbon atoms.
Further, when X contains at least one or more independent carboxyl groups, sulfonic acid groups, sulfate ester groups, phosphate ester groups or salts thereof as substituents, it is represented by the general formula (1). Multi-chain and poly-hydrophilic group type surfactants are preferred because they are excellent in solubility in weak acidity. Further, it is preferable that X is a naturally-occurring type in that it is excellent in biodegradability.
[0034]
In the general formula (2), X is preferably an m-valent polyamino compound residue having a molecular weight of 1,000,000 or less which may have a substituent other than an amino group. Here, an m-valent polyamino compound means that m acid amide bonds can be formed. They may be optical isomers such as D-form, L-form and racemic form.
Examples of such m-valent polyamino compounds include N, N′-dimethylhydrazine, ethylenediamine, N, N′-dimethylethylenediamine, diaminopropane, diaminobutane, diaminopentane, diaminohexane, diaminoheptane, diaminooctane, diaminononane, Aliphatic diamines such as diaminodecane, diaminododecane, diaminoadipic acid, diaminopropanoic acid, diaminobutanoic acid and their isomers;
Diethylenetriamine, triaminohexane, triaminododecane, 1,8-diamino-4-aminomethyl-octane, 2,6-diaminocapric acid-2-aminoethyl ester, 1,3,6-triaminohexane, 1,6 Aliphatic triamines such as, 11-triaminoundecane, di (aminoethyl) amine and isomers thereof;
[0035]
Alicyclic polyamines such as diaminocyclobutane, diaminocyclohexane, 3-aminomethyl-3,5,5-trimethylcyclohexylamine and triaminocyclohexane;
Aromatic polyamines such as diaminobenzene, diaminotoluene, diaminobenzoic acid, diaminoanthraquinone, diaminobenzenesulfonic acid, diaminobenzoic acid and isomers thereof;
Araliphatic polyamines such as diaminoxylene, di (aminomethyl) benzene, di (aminomethyl) pyridine, di (aminomethyl) naphthalene, and their isomers;
Examples thereof include polyamines substituted with a hydroxyl group such as diaminohydroxypropane and isomers thereof.
[0036]
X preferably has 1 to 40 carbon atoms among the residues of such a compound, and more preferably X has 1 to 20 carbon atoms. Particularly preferred are those having 1 to 10 carbon atoms.
Further, when X contains at least one or more independent carboxyl groups, sulfonic acid groups, sulfate ester groups, phosphate ester groups or salts thereof as substituents, the interface represented by the general formula (1) The activator is preferable in that it has excellent solubility in weak acidity. Further, it is preferable that X is a naturally-occurring type in that it is excellent in biodegradability.
[0037]
In the general formula (1), X is preferably an m-valent polythiol compound residue having a molecular weight of 1,000,000 or less which may have a substituent other than a thiol group. Here, an m-valent polythiol compound means that m thioester bonds can be formed. They may be optical isomers such as D-form, L-form and racemic form.
Examples of such m-valent polythiol compounds include dithiol compounds such as dithioethylene glycol, dithioerythritol, and dithiothreitol. X preferably has 1 to 40 carbon atoms among the residues of such a compound, and more preferably X has 1 to 20 carbon atoms. Particularly preferred are those having 1 to 10 carbon atoms.
Further, when X contains from 1 to 10 independent carboxyl groups, sulfonic acid groups, sulfate ester groups, phosphate ester groups or salts thereof as substituents, the compound represented by the general formula (1) A chain polyhydrophilic surfactant is preferred in that it has excellent solubility in weakly acidic. Further, it is preferable that X is a naturally-occurring type in that it is excellent in biodegradability.
[0038]
In the general formula (2), a carboxyl group, a sulfonic acid group, a sulfate ester group, a phosphate ester group represented by Y and a carboxyl group, a sulfonic acid group, a sulfate ester group, a phosphate ester group, etc. which can be contained in X are May form salts with various basic substances.
Such salts include, for example, alkali metal salts, alkaline earth metal salts, ammonium salts, organic amine salts, basic amino acid salts, and the like.Specifically, alkali metals such as sodium, potassium, and lithium, calcium, and magnesium One selected from alkaline earth metals such as aluminum, zinc and other metals, ammonia, organic amines such as monoethanolamine, diethanolamine, triethanolamine and triisopropanolamine, and basic amino acids such as arginine and lysine. Or a salt with two or more kinds. Among these, sodium salts, potassium salts, organic amine salts and basic amino acid salts are preferred.
[0039]
As a method for producing such a multi-chain polyhydrophilic group-type surfactant represented by the general formula (1), an N-long-chain acyl acidic amino acid anhydride represented by the general formula (3) and a hydroxyl group in the molecule are used. It can be obtained by reacting one or more compounds having m functional groups selected from an amino group and a thiol group in water and / or a mixed solvent of water and an organic solvent.
[0040]
Embedded image
[0041]
Alternatively, the multi-chain poly-hydrophilic group type surfactant represented by the general formula (1) may be an N-long-chain acyl acidic amino acid anhydride represented by the general formula (3) and a polyhydroxyl compound, a polyamino compound or a polythiol compound, or Compounds having two or three of hydroxyl, amino, and thiol groups in the molecule at a temperature not lower than any melting point, or tetrahydrofuran, benzene, toluene, xylene, carbon tetrachloride, chloroform, acetone And by mixing at -5 to 200 ° C using an inert solvent such as
[0042]
Alternatively, the multi-chain poly-hydrophilic group-type surfactant represented by the general formula (1) may be an N-long-chain acyl acidic amino acid mono-lower ester (eg, methyl ester, ethyl ester) and a polyhydroxyl compound, a polyamino compound, or a polythiol compound. Or a compound having any two or three of a hydroxyl group, an amino group, and a thiol group in a molecule is dissolved in an appropriate solvent such as dimethylformamide, and a catalyst such as potassium carbonate is added thereto. It can be obtained by removing the reaction solvent after performing a heating reaction at −5 ° C. to 250 ° C. Alternatively, the surfactant of the present invention can be obtained by heating and melting without a solvent, adding a catalyst such as sodium hydroxide, and performing a transesterification reaction at room temperature to 250 ° C.
[0043]
In the cleansing agent of the present invention, other surfactants can be contained as the surfactant in addition to the multi-chain and multi-hydrophilic group type surfactant as long as the object of the present invention is not impaired. Examples of such a surfactant include an anionic surfactant having a structure having one long-chain hydrophobic group and / or a hydrophilic group in a molecule, a nonionic surfactant, a cationic surfactant, and an amphoteric surfactant. And so on. Among them, those containing an N-long-chain acylamino acid type surfactant or an acyl peptide type surfactant as an anionic surfactant in the aqueous solution are preferable.
[0044]
The N-long-chain acylamino acid herein refers to an amino group of an amino acid into which an acyl group derived from a saturated or unsaturated fatty acid having 8 to 20 carbon atoms has been introduced. The amino acid residues in N-long chain acyl amino acids are various amino acids such as α-amino acids, β-amino acids, γ-amino acids and ω-amino acids, and the amino groups may be in N-methyl form or N-ethyl form. Absent. It does not matter whether it is an optical isomer, that is, a D-form, an L-form, or a racemic form.
[0045]
For example, glutamic acid, aspartic acid, glycine, alanine, baryin, leucine, isoleucine, serine, threonine, cysteine, cysteine, cystine, methionine, lysine, arginine, phenylalanine, tyrosine, histidine, tryptophan, proline, oxyproline, lanthionine, β- Methyllanthionine, cystathionine, diencholic acid, ferrinin, aminomalonic acid, β-oxyaspartic acid, α-amino-α-methylsuccinic acid, β-oxyglutamic acid, γ-oxyglutamic acid, γ-methylglutamic acid, γ-methyleneglutamic acid Γ-methyl-γ-oxyglutamic acid, α-aminoadipic acid, α, α′-diaminoadipic acid, β, β′-diaminoadipic acid, α-amino-γ-oxyadipic acid, α-aminopime Phosphate, alpha-amino -γ- Okishipimerin acid, beta-aminopimelic acid, alpha-aminosuberic acid, alpha-Aminosebashin acid, pantothenic acid, sarcosine, taurine, methyl taurine.
[0046]
The acyl group may be any one derived from a saturated or unsaturated fatty acid having 8 to 20 carbon atoms, and may be linear, branched or cyclic. It is preferable that the N-long-chain acyl amino acid is an N-long-chain acyl-L-amino acid from the viewpoint of biodegradability.
The term "acyl peptide" used herein refers to one obtained by hydrolyzing a protein and then acylating the protein.
[0047]
In the cleansing agent of the present invention, examples of the polyhydroxyl compound having two or more hydroxyl groups in a molecule include ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, and 1,3. -Butanediol, 1,4-butanediol, pentanediol, 1,6-hexanediol, cyclohexanediol, dimethylolcyclohexane, neopentylglycol, 1,8-octanediol,
2,2,4-trimethyl-1,3-pentanediol, isoprene glycol, 3-methyl-1,5-pentanediol, sorbite, catechol, resorcin, hydroquinone, bisphenol A, bisphenol F, hydrogenated bisphenol A, hydrogenated Bisphenol F,
Dimer diol, dimethylolpropionic acid, dimethylolbutanoic acid, tartaric acid, dihydroxytartaric acid, mevalonic acid, 3,4-dihydroxycinnamic acid, 3,4-dihydroxyhydrocinnamic acid, hydroxybenzoic acid, dihydroxystearic acid, dihydroxyphenylalanine And a divalent hydroxyl compound such as each isomer thereof;
[0048]
Glycerin, trioxyisobutane, 1,2,3-butanetriol, 1,2,3-pentanetriol, 2-methyl-1,2,3-propanetriol, 2-methyl-2,3,4-butanetriol, 2-ethyl-1,2,3-butanetriol, 2,3,4-pentanetriol,
2,3,4-hexanetriol, 4-propyl-3,4,5-heptanetriol, 2,4-dimethyl-2,3,4-pentanetriol, 1,2,4-butanetriol, 1,2,2 Trivalent polyhydroxyl compounds such as 4-pentanetriol, trimethylolethane, trimethylolpropane, diethanolamine, triethanolamine, trihydroxystearic acid;
Pentaerythritol, erythritol, 1,2,3,4-pentane tetrol, 2,3,4,5-hexane tetrol, 1,2,4,5-pentane tetrol, 1,3,4,5-hexane Tetravalent polyhydroxyl compounds such as tetrol, diglycerin and sorbitan;
Pentavalent polyhydroxyl compounds such as adonitol, arabitol, xylitol, triglycerin;
Hexavalent polyhydroxyl compounds such as dipentaerythritol, sorbitol, mannitol, iditol, inositol, darcitol, talose, allose;
Or a dehydration condensate of these, polyglycerin and the like.
[0049]
Saccharides, for example tetroses such as erythrose, threose, erythrulose;
Pentoses such as ribose, arabinose, xylose, lixose, xylulose and ribulose; monosaccharides such as hexoses such as allose, altrose, glucose, mannose, gulose, idose, galactose, talose, fructose, sorbose, psicose, tagatose;
Oligosaccharides such as maltose, isomaltose, cellobiose, gentiobiose, melibiose, lactose, turanose, trehalose, saccharose, mannitolose, cellotriose, gentianose, raffinose, meletitose, cellotetroose and stachyose.
[0050]
In addition, other sugars such as heptose, deoxy sugar, amino sugar, thio sugar, seleno sugar, aldone sugar, uronic acid, sugar acid, ketoaldonic acid, anhydro sugar, unsaturated sugar, sugar ester, sugar ether, glycoside, etc. Or a polysaccharide such as starch, glycogen, cellulose, chitin, chitosan, or a hydrolyzed product thereof. These polyhydroxyl compounds may be used in combination of two or more. The polyhydroxyl compound is preferably a trivalent or higher valent polyhydroxyl compound.
[0051]
In the cleansing agent of the present invention, as the oily component, either a liquid oil or a solid fat can be used, and an oily component which is commonly used as a component of cosmetics or external medicines may be used.
For example, avocado oil, almond oil, olive oil, cocoa oil, sesame oil, safflower oil, soybean oil, camellia oil, persic oil, castor oil, grape seed oil, macadamia nut oil, mink oil, cottonseed oil, mocro, palm oil, egg yolk oil, Fats and oils such as palm oil, palm kernel oil, glyceryl triisooctanoate, glyceryl tri-2-ethylhexanoate cholesterol fatty acid ester,
Waxes such as whale wax, carnauba wax, candelilla wax, jojoba oil, beeswax, lanolin and derivatives thereof,
Liquid paraffin, paraffin, vaseline, ceresin, microcrystalline wax, squalane, squalene and other hydrocarbons,
[0052]
Higher fatty acids such as lauric acid, myristic acid, palmitic acid, stearic acid, isostearin, oleic acid, behenic acid, undecylenic acid, lanolin fatty acid, hard lanolin fatty acid, and soft lanolin fatty acid,
Higher alcohols such as lauryl alcohol, cetyl alcohol, cetostearyl alcohol, stearyl alcohol, isostearyl alcohol, 2-octyldodecanol, oleyl alcohol, behenyl alcohol, lanolin alcohol, hydrogenated lanolin alcohol, hexyldecanol,
Higher alcohol fatty acid esters such as isopropylidyl myristate, octadecyl myristate, 2-octyldodecyl myristate, cetyl 2-ethylhexanoate, diisostearyl malate, isostearyl isostearate, isostearyl cholesteryl ester and butyl stearate;
Examples include volatile and nonvolatile oily components such as silicone oils such as methylpolysiloxane and methylphenylpolysiloxane. These oil components may be used in combination of two or more.
[0053]
The cleansing agent of the present invention contains one or more surfactants, one or more polyhydroxyl compounds having two or more hydroxyl groups in the molecule, and one or more oil components. A cleansing agent having a water content of 50% by weight or less in the composition and a composition in the cleansing agent composition including water, wherein 1) the total amount of the surfactant is 0.1 to 40% by weight. %, 2) the total amount of the polyhydroxyl compound is 1 to 60% by weight, and 3) the total amount of the oily component is preferably 1 to 95% by weight. Here, the total amount of each of the surfactant, the polyhydroxyl compound, and the oily component is the total of the corresponding components. Even if the composition of each component is out of this range, it may be a gel dosage form, but when applied to the skin etc., the elongation is poor, the oily component is separated and the stability is poor, gel formation Depending on the purpose, the feeling of use may be unfavorable, for example, the strength may be insufficient, the cleaning power for dirt may be reduced, or the elongation may be poor.
[0054]
In the cleansing agent of the present invention, the composition of each of the surfactant, the polyhydroxyl compound, and the oily component is preferably such that: 1) the total amount of the surfactant is 1 to 25% by weight; 3) The total amount of polyhydroxyl compounds is 5 to 40% by weight, and 3) The total amount of oily components is 20 to 80% by weight. More preferably, 1) the total amount of the surfactant is 3 to 15% by weight, 2) the total amount of the polyhydroxyl compound is 5 to 30% by weight, and 3) the total amount of the oil component is 30 to 70% by weight.
[0055]
In the cleansing agent of the present invention, the water content is preferably 50% by weight or less. Outside this range, it may be difficult to stably maintain the gel state. The water content is more preferably 30% by weight or less. More preferably, the content is 20% by weight or less.
In the cleansing agent of the present invention, those having a viscosity at 25 ° C. in the range of 1,000 to 2,000,000 mPa · s are preferable because they have excellent elongation when applied to skin or the like. More preferably, the viscosity at 25 ° C. is in the range of 3000 to 60000 mPa · s.
[0056]
In the cleansing agent of the present invention, in order to obtain a cleansing agent having a transparent appearance, a surfactant in the composition, an aqueous phase comprising a polyhydroxyl compound and water, and an oil phase comprising an oil component at 20 ° C. It is preferable that the difference in the refractive index be ± 0.05 or less. If the difference between the refractive indices of the two phases is out of this range, it is difficult to obtain a transparent composition having an external appearance, and the difference between the refractive indices of the two phases should be closer to zero. More preferably, the difference between the refractive indices of the two phases is ± 0.03 or less. More preferably, the difference in refractive index between the two phases is ± 0.01 or less.
[0057]
In order to produce the cleansing agent of the present invention, it is produced by stirring and mixing a surfactant, a polyhydroxyl compound, an oily component and optionally water under a high shear force. As a preferable production method, a method in which components other than the oily component are sufficiently stirred and mixed, and the oily component is added thereto is good.
[0058]
The characteristics of the cleansing agent of the present invention thus obtained are
1) High gel-forming power, keeps very stable gel over time 2) Excellent in elongation when applied to skin, and very easily finely dispersed in emulsion state when water is added after application 3 ) It has a feature that it can be easily washed off with water and has a refreshing feeling without being left behind, which solves the problems so far.
The cleansing agent of the present invention refers to, for example, a cleansing cream, a cleansing gel, a massage cream, a massage gel, and the like that can be applied to applications intended to be washed off after being applied to the skin and used.
The cleansing agent of the present invention can be used in combination with various base materials usually used for cosmetics and toiletry products, as long as the object of the present invention is not impaired. In addition, the cleansing agent of the present invention can be in the form of a paste, a liquid, a foam, or the like, if desired, in addition to a gel.
[0059]
Specifically, fatty acid salt (soap), alkyl sulfate salt (AS), polyoxyethylene alkyl ether sulfate salt (AES), alpha-olefin sulfonate (AOS), alkyl benzene sulfonate, alkyl naphthalene sulfonic acid Salt, alkyl sulfonate (SAS), dialkyl sulfosuccinate, alpha-sulfonated fatty acid salt, N-long chain acyl amino acid salt, N-acyl-N-methyltaurine salt, sulfated oil, polyoxyethylene styrenated phenyl ether Anionic surfactants such as sulfates, alkyl phosphates, polyoxyethylene alkyl ether phosphates, polyoxyethylene alkyl phenyl ether phosphates, and naphthalene sulfonate formalin condensates;
Amphoteric surfactants such as alkyl betaines, alkyl amido betaines, alkyl sulfo betaines, alkyl hydroxy sulfo betaines, alkyl amido hydroxy sulfo betaines, alkyl amidoamine betaines, imidazolinium betaines;
[0060]
Fatty acid alkylolamide, alkylamine oxide, polyoxyethylene alkyl ether (AE), polyoxyethylene alkyl phenyl ether, polyoxyethylene polystyryl phenyl ether, polyoxyethylene polyoxypropylene glycol, polyoxyethylene polyoxypropylene alkyl ether,
Nonionic properties such as polyhydric alcohol fatty acid partial ester, polyoxyethylene polyhydric alcohol fatty acid partial ester, polyoxyethylene fatty acid ester, polyglycerin fatty acid ester, polyoxyethylene hardened castor oil, polyoxyethylene alkylamine, and triethanolamine fatty acid partial ester Surfactant;
Cationic surfactants such as primary to tertiary fatty amine salts, alkyl ammonium chloride salts, tetraalkyl ammonium salts, trialkyl benzyl ammonium salts, alkyl pyridinium salts, alkyl hydroxyethyl imidazolinium salts and dialkyl morpholinium salts ;
Polymeric surfactants such as sodium alginate, starch derivatives, tragacanth gum;
[0061]
Natural surfactants such as lecithin, lanolin, cholesterol, saponin;
Humectants such as trimethylglycine, sorbitol, raffinose, pyrrolidone carboxylate, lactate, hyaluronate, ceramide, pseudoceramide, urea;
Hydroxyethylcellulose, carboxymethylcellulose, hydroxyethylcellulose hydroxypropyltrimethylammonium chloride ether, methylcellulose, ethylcellulose, hydroxypropylcellulose, methylhydroxypropylcellulose, soluble starch, carboxymethylstarch, methylstarch,
Propylene glycol alginate, polyvinyl alcohol, polyvinyl pyrrolidone, polyvinyl methyl ether, carboxyvinyl polymer, polyacrylate, guar gum, locust bingham, quince seed, carrageenan, galactan,
Gum arabic, pectin, mannan, starch, xanthan gum, dextran, succinoglucan, curdlan, hyaluronic acid, gelatin, casein, albumin, collagen, methoxyethylene maleic anhydride copolymer, amphoteric methacrylate copolymer, polychlorinated Water-soluble and oil-soluble polymers such as dimethylmethylenepiperidinium, polyacrylate copolymer, polyvinyl acetate, nitrocellulose, silicone resin;
[0062]
Thickening and foam-increasing components such as polyethylene glycol fatty acid esters, polyoxyethylene fatty acid ester methyl glycosides, and tetradecene sulfonates;
Monocarboxylic acids such as formic acid and acetic acid and salts thereof, dicarboxylic acids and salts thereof such as oxalic acid, malonic acid and succinic acid, and polycarboxylic acids such as tricarballylic acid and propane-1,1,2,3-tetracarboxylic acid Acids and salts thereof, glycolic acid, tartaric acid, citric acid, oxalic acid, oxy or ketocarboxylic acids and salts thereof such as gluconic acid, aromatic carboxylic acids and salts thereof such as phthalic acid, ethylenediamine, amines such as N-ethylethylenediamine and Its derivatives, iminodiacetic acid, iminodipropionic acid, phenyliminodiacetic acid, hydroxyethyliminodiacetic acid, iminodiacetic acid such as mercaptoethyliminodiacetic acid and its salts, nitrilotriacetic acid, nitriloacetic acid such as carboxyethyliminodiacetic acid and the like Salts, derivatives such as N, N-ethylenediaminediacetic acid, ethylene Aminopolyacetic acids and their salts such as aminetetraacetic acid, diethylenetriaminepentaacetic acid, and trimethylenetetraaminehexaacetic acid; amino acids and their salts such as glycine, alanine, glutamic acid, and aspartic acid; and tripolyphosphoric acid, phthalic acid, and 1,1-hydroxy acid Phosphoric acid and its salts such as ethane-1,2-diphosphonic acid, polyphosphoric acid and metaphosphate; and sequestering agents such as ascorbic acid and hinokitol;
[0063]
Benzoic acid and its salts, benzoic acid-based preservatives such as isopropyl parahydroxybenzoate, isopropyl valaoxybenzoate, ethyl paraoxybenzoate, methyl paraoxybenzoate, butyl paraoxybenzoate, propyl paraoxybenzoate, sorbic acid, sorbic acid Sorbic acid preservatives such as potassium, dehydroacetic acids, propionic acids, diphenyls such as diphenyl, orthophenylphenol and sodium; preservatives such as thiazol, imazalil, phenoxyethanol, hinokitiol;
PH adjusters such as citric acid, malic acid, adipic acid, glutamic acid, and aspartic acid;
Other anti-dandruff and itching agents such as trichlorolcarbanilide, salicylic acid, zinc pyrithione, and isopropylmethylphenol;
Benzophenone derivatives, para-aminobenzoic acid derivatives, para-methoxycinnamic acid derivatives, salicylic acid derivatives and other ultraviolet absorbers;
Whitening agents such as arbutin, kojic acid, ascorbic acid, hinokitol and derivatives thereof;
[0064]
Blood circulation promoters such as assembly extract, cepharanthin, vitamin E and its derivatives, gamma-oryzanol;
Topical stimulants such as pepper tincture, show tincture, cantaris tincture, nicotinic acid benzyl ester;
Nutrients such as various vitamins and amino acids;
Female hormone agent;
Hair root activator;
Anti-inflammatory agents such as glycyrrhetinic acid, glycyrrhizic acid derivatives, allantoin, azulene, aminocaproic acid, hydrocortisone;
Astringents such as zinc oxide, zinc sulfate, allantoin hydroxyaluminum, aluminum chloride, zinc sulfocarbonate, tannic acid;
Cooling agents such as menthol and camphor;
Antihistamines;
Antioxidants such as silicone-based substances such as polymer silicone and cyclic silicone, tocopherols, BHA, BHT, gallic acid, and NDGA;
[0065]
Aliphatic hydrocarbons, terpene hydrocarbons, hydrocarbons such as aromatic hydrocarbons, aliphatic alcohols, terpene alcohols, alcohols such as aromatic alcohols, aliphatic ethers, ethers such as aromatic ethers, aliphatic oxides, Oxides such as oxides of terpenes, aliphatic aldehydes, terpene aldehydes, hydrogenated aromatic aldehydes, thioaldehydes, aldehydes such as aromatic aldehydes, aliphatic ketones, terpene ketones, hydrogenated aromatic ketones, fats Ketones such as aromatic cyclic ketones, non-benzene aromatic ketones, aromatic ketones, acetals, ketals, phenols, phenol ethers, fatty acids, terpene carboxylic acids, hydrogenated aromatic carboxylic acids, aromatic carboxylic acids Such as acids, acid amides, aliphatic lactones, macrocyclic lactones, Lactones such as lupen lactones, hydrogenated aromatic lactones, aromatic lactones, aliphatic esters, furan carboxylic esters, aliphatic cyclic carboxylic esters, cyclohexyl carboxylic esters, terpene carboxylic esters, aromatic Synthetic flavors such as esters such as aromatic carboxylic acid esters, nitrogenous compounds such as nitromsks, nitriles, amines, pyridines, quinolines, pyrroles and indoles; and natural flavors from plants;
It can contain purified water and the like. If necessary, a viscosity reducing agent or the like can be used.
In particular, the combined use with each zwitterionic surfactant is extremely useful in that the irritation is further reduced.
[0066]
Hereinafter, the present invention will be described more specifically with reference to Examples and the like, but the present invention is not limited to these Examples and the like.
Hereinafter, the method of the present invention will be described in detail with reference to examples.
The evaluation means used in the examples of the present invention are as follows.
(Stability)
Each cleansing agent was stored at 40 ° C., the state after one month was observed, and the stability was evaluated according to the following criteria.
:: good without state change 状態: slight separation observed ×: separation clearly observed
(viscosity)
The viscosity immediately after production of the cleansing agent was measured at 25 ° C. with a B-type viscometer.
(Refractive index)
The refractive index at 20 ° C. of each phase was measured with a refractometer.
[0067]
(Usability)
Five panelists evaluated the use of the cleansing agent and the use after washing with water according to the following criteria.
:: 3 or more people who felt that there was no stickiness and the feeling of use was good △: 〃, 1 or 2 ×: 、, 0 (ease of use)
Five panelists conducted a sensory evaluation of the elongation of use of the cleansing agent according to the following criteria.
:: 3 or more people who felt good △: 〃, 1 or 2 ×: 、, 0 (appearance)
Each cleansing composition was evaluated visually.
[0068]
(Production example 1 of multi-chain poly-hydrophilic group type surfactant)
9.1 g (0.05 mol) of L-lysine hydrochloride was mixed with 57 g of water. While adjusting the pH range of this solution to 10 to 11 with a 25% aqueous sodium hydroxide solution and maintaining the reaction temperature at 5 ° C, 31.1 g of N-lauroyl-L-glutamic anhydride (0. (1 mol) was added over 2 hours to carry out the reaction. After further stirring for 30 minutes, tertiary butanol was added to a concentration of 20% by weight in the liquid, and then 75% sulfuric acid was added dropwise to adjust the pH of the liquid to 2 and the temperature of the liquid to 65 ° C. It was adjusted. After completion of the dropwise addition, the stirring was stopped, and the mixture was allowed to stand at 65 ° C. for 20 minutes to separate into an organic layer and an aqueous layer, from which the organic layer was separated. Tertiary butanol and water were added to the separated organic layer, and the mixture was stirred at a temperature of 65 ° C. for 20 minutes. After the stirring was stopped, the mixture was allowed to stand and separated into an organic layer and an aqueous layer. After repeating the same washing operation with respect to the obtained organic layer, the solvent was removed from the obtained organic layer, and neutralized with sodium hydroxide to pH 6.5 (25 ° C.) at a solid content of 30% by weight. After drying, a multi-chain poly-hydrophilic group type surfactant was obtained.
[0069]
(Production example 2 of multi-chain poly-hydrophilic group type surfactant)
In Production Example 1, the reaction conditions were 9.1 g (0.05 mol) of L-lysine hydrochloride, 3.0 g (0.05 g) of ethylenediamine, and neutralization conditions were a solid content of 30% by weight and a pH of 7.5 (25 ° C.). The procedure was carried out under the same conditions as in Production Example 1 except that the above-mentioned conditions were used to obtain a multi-chain / multi-hydrophilic group type surfactant.
[0070]
Examples 1 to 7, Comparative Examples 1 to 3
Cleansing agents having the compositions shown in Table 1 were produced, and the stability and feeling of use were evaluated for each. Table 1 shows the results.
(Preparation method) All cleansing agents were prepared by the following methods.
The components other than the oil component are mixed with stirring at 70 ° C. The oily component was slowly dropped into the mixture with stirring, and the mixture was further stirred and cooled to obtain a gel-like cleansing agent.
[0071]
[Table 1]
[0072]
【The invention's effect】
The cleansing agent of the present invention contains a surfactant having two or more long-chain hydrophobic groups and hydrophilic groups in the molecule. As shown in Examples, the cleansing agent is produced using this surfactant. The cleansing agent thus obtained is extremely excellent in stability as compared with the case where any other surfactant is used. Further, it is clear that the obtained cleansing agent can be washed very easily with water and has excellent usability.
Claims (8)
R1COは炭素原子数28〜20の飽和または不飽和の脂肪酸から誘導される長鎖アシル基を示し、R2は水素であるか、またはヒドロキシル基またはカルボキシル基が置換していてもよい炭素原子数1〜3の低級アルキル基を示し、Yはカルボキシル基、スルホン酸基、硫酸エステル基、リン酸エステル基および/またはそれらの塩を示し、j、kはそれぞれ独立に0,1,2のいずれかであり、かつj、kは同時に0ではなく、nは2〜20の整数を示す)
R 1 CO represents a long-chain acyl group derived from a saturated or unsaturated fatty acid having 28 to 20 carbon atoms, and R 2 represents hydrogen or a carbon atom which may be substituted by a hydroxyl group or a carboxyl group. Y represents a lower alkyl group having 1 to 3 atoms, Y represents a carboxyl group, a sulfonic acid group, a sulfate ester group, a phosphate ester group and / or a salt thereof, and j and k each independently represent 0, 1, 2, or 3. And j and k are not simultaneously 0 and n represents an integer of 2 to 20)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
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JP2002339277A JP2004168736A (en) | 2002-11-22 | 2002-11-22 | Cleansing agent |
TW092123488A TW200413283A (en) | 2002-08-27 | 2003-08-26 | Novel composition containing acyl group |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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JP2002339277A JP2004168736A (en) | 2002-11-22 | 2002-11-22 | Cleansing agent |
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006028424A (en) * | 2004-07-20 | 2006-02-02 | Asahi Kasei Chemicals Corp | Creamy detergent |
JP2006225373A (en) * | 2005-09-22 | 2006-08-31 | Asahi Kasei Chemicals Corp | Emulsion |
JP2006225368A (en) * | 2005-06-17 | 2006-08-31 | Asahi Kasei Chemicals Corp | Gel composition and method for preparing the same |
JP2006225403A (en) * | 2005-06-17 | 2006-08-31 | Asahi Kasei Chemicals Corp | Oily gel cleansing cream |
EP1891924A1 (en) * | 2005-06-14 | 2008-02-27 | Asahi Kasei Chemicals Corporation | Composition for protection of body surface |
WO2008129806A1 (en) | 2007-03-29 | 2008-10-30 | Shiseido Company, Ltd. | Oil-in-water type emulsion composition |
JP2010235514A (en) * | 2009-03-31 | 2010-10-21 | Dhc Co | Liquid composition for cleansing |
-
2002
- 2002-11-22 JP JP2002339277A patent/JP2004168736A/en active Pending
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006028424A (en) * | 2004-07-20 | 2006-02-02 | Asahi Kasei Chemicals Corp | Creamy detergent |
EP1891924A1 (en) * | 2005-06-14 | 2008-02-27 | Asahi Kasei Chemicals Corporation | Composition for protection of body surface |
EP1891924A4 (en) * | 2005-06-14 | 2013-07-17 | Asahi Kasei Chemicals Corp | Composition for protection of body surface |
JP2006225368A (en) * | 2005-06-17 | 2006-08-31 | Asahi Kasei Chemicals Corp | Gel composition and method for preparing the same |
JP2006225403A (en) * | 2005-06-17 | 2006-08-31 | Asahi Kasei Chemicals Corp | Oily gel cleansing cream |
JP2006225373A (en) * | 2005-09-22 | 2006-08-31 | Asahi Kasei Chemicals Corp | Emulsion |
WO2008129806A1 (en) | 2007-03-29 | 2008-10-30 | Shiseido Company, Ltd. | Oil-in-water type emulsion composition |
US8034755B2 (en) | 2007-03-29 | 2011-10-11 | Shiseido Company, Ltd. | Oil-in-water type emulsion composition |
CN101631530B (en) * | 2007-03-29 | 2012-07-18 | 株式会社资生堂 | Oil-in-water type emulsion composition |
JP2010235514A (en) * | 2009-03-31 | 2010-10-21 | Dhc Co | Liquid composition for cleansing |
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