JP2018009118A - Temperature sensitive phase separation liquid - Google Patents
Temperature sensitive phase separation liquid Download PDFInfo
- Publication number
- JP2018009118A JP2018009118A JP2016139935A JP2016139935A JP2018009118A JP 2018009118 A JP2018009118 A JP 2018009118A JP 2016139935 A JP2016139935 A JP 2016139935A JP 2016139935 A JP2016139935 A JP 2016139935A JP 2018009118 A JP2018009118 A JP 2018009118A
- Authority
- JP
- Japan
- Prior art keywords
- temperature
- phase separation
- water
- sensitive phase
- liquid
- 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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- 239000007788 liquid Substances 0.000 title claims abstract description 173
- 238000005191 phase separation Methods 0.000 title claims abstract description 156
- 239000011557 critical solution Substances 0.000 claims abstract description 76
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 46
- 239000000126 substance Substances 0.000 claims abstract description 32
- 239000000243 solution Substances 0.000 claims abstract description 15
- 239000007787 solid Substances 0.000 claims abstract description 14
- -1 glycol alkyl ethers Chemical class 0.000 claims description 64
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 43
- 239000007864 aqueous solution Substances 0.000 claims description 32
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 25
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 23
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 14
- 239000000194 fatty acid Substances 0.000 claims description 14
- 229930195729 fatty acid Natural products 0.000 claims description 14
- 150000001298 alcohols Chemical class 0.000 claims description 10
- 229920001451 polypropylene glycol Polymers 0.000 claims description 9
- 150000002334 glycols Chemical class 0.000 claims description 8
- SNAQINZKMQFYFV-UHFFFAOYSA-N 1-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]butane Chemical compound CCCCOCCOCCOCCOC SNAQINZKMQFYFV-UHFFFAOYSA-N 0.000 claims description 7
- RJBIZCOYFBKBIM-UHFFFAOYSA-N 2-[2-(2-methoxyethoxy)ethoxy]propane Chemical compound COCCOCCOC(C)C RJBIZCOYFBKBIM-UHFFFAOYSA-N 0.000 claims description 7
- 230000001747 exhibiting effect Effects 0.000 claims description 6
- 150000002366 halogen compounds Chemical class 0.000 claims description 4
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 claims description 3
- 229940054273 1-propoxy-2-propanol Drugs 0.000 claims description 3
- FENFUOGYJVOCRY-UHFFFAOYSA-N 1-propoxypropan-2-ol Chemical compound CCCOCC(C)O FENFUOGYJVOCRY-UHFFFAOYSA-N 0.000 claims description 3
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 claims description 3
- HHAPGMVKBLELOE-UHFFFAOYSA-N 2-(2-methylpropoxy)ethanol Chemical compound CC(C)COCCO HHAPGMVKBLELOE-UHFFFAOYSA-N 0.000 claims description 3
- LJVNVNLFZQFJHU-UHFFFAOYSA-N 2-(2-phenylmethoxyethoxy)ethanol Chemical compound OCCOCCOCC1=CC=CC=C1 LJVNVNLFZQFJHU-UHFFFAOYSA-N 0.000 claims description 3
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 3
- 150000001720 carbohydrates Chemical class 0.000 claims description 3
- ZSUUCLLIOSUIFH-UHFFFAOYSA-N n,n-di(propan-2-yl)acetamide Chemical compound CC(C)N(C(C)C)C(C)=O ZSUUCLLIOSUIFH-UHFFFAOYSA-N 0.000 claims description 3
- CDQSTBHGKNNPSY-UHFFFAOYSA-N n,n-diethylbutanamide Chemical compound CCCC(=O)N(CC)CC CDQSTBHGKNNPSY-UHFFFAOYSA-N 0.000 claims description 3
- OAERLTPBKQBWHJ-UHFFFAOYSA-N n,n-dimethylhexanamide Chemical compound CCCCCC(=O)N(C)C OAERLTPBKQBWHJ-UHFFFAOYSA-N 0.000 claims description 3
- KYKDOARTYFGHPC-UHFFFAOYSA-N n-propan-2-ylpropanamide Chemical compound CCC(=O)NC(C)C KYKDOARTYFGHPC-UHFFFAOYSA-N 0.000 claims description 3
- YUMCRXLLWKQDJY-UHFFFAOYSA-N n-propylpropanamide Chemical compound CCCNC(=O)CC YUMCRXLLWKQDJY-UHFFFAOYSA-N 0.000 claims description 3
- 230000035945 sensitivity Effects 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 16
- 239000000203 mixture Substances 0.000 abstract description 15
- 238000000926 separation method Methods 0.000 abstract description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- 125000001033 ether group Chemical group 0.000 description 13
- 239000011259 mixed solution Substances 0.000 description 12
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- 238000010438 heat treatment Methods 0.000 description 10
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- 239000002994 raw material Substances 0.000 description 6
- 230000003204 osmotic effect Effects 0.000 description 5
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- 230000002209 hydrophobic effect Effects 0.000 description 4
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
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- HYLLZXPMJRMUHH-UHFFFAOYSA-N 1-[2-(2-methoxyethoxy)ethoxy]butane Chemical compound CCCCOCCOCCOC HYLLZXPMJRMUHH-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Extraction Or Liquid Replacement (AREA)
Abstract
Description
下限臨界溶液温度を調節した感温相分離液体に関する。 The present invention relates to a temperature-sensitive phase separation liquid in which the lower critical solution temperature is adjusted.
室温あるいは低温では水に溶解し、高温で水と相分離する感温相分離物質、すなわち下限臨界溶液温度（ＬＣＳＴ）を有する物質として、ポリＮ−イソプロピルアクリルアミドなどのポリマーが知られている（特許文献１）。
特許文献１に記載された技術では、ポリマーのモノマー組成比を変えることでＬＣＳＴを調節している。しかしながら、得られる溶液は高粘度のポリマー溶液で、相分離後はゲル状となり、液体−液体の分液による分離は困難であった。
Polymers such as poly-N-isopropylacrylamide are known as temperature-sensitive phase-separating substances that dissolve in water at room temperature or low temperature and phase-separate with water at high temperature, that is, substances having a lower critical solution temperature (LCST) (patent) Reference 1).
In the technique described in Patent Document 1, LCST is adjusted by changing the monomer composition ratio of the polymer. However, the resulting solution is a high-viscosity polymer solution that becomes a gel after phase separation, and separation by liquid-liquid separation was difficult.
本発明者は、ＬＣＳＴを有する低分子水溶性液体化合物を正浸透ドロー溶液として用いる技術を出願しており（特許文献２）、感温相分離物質は低粘度高浸透圧の正浸透水処理法ドロー溶液、低粘度感温相分離抽出、容易に水分を分離できる低粘度吸収液などに用いられる。 The present inventor has applied for a technique using a low-molecular water-soluble liquid compound having LCST as a forward osmotic draw solution (Patent Document 2), and a temperature-sensitive phase separation substance is a forward osmotic water treatment method having a low viscosity and a high osmotic pressure. Used for draw solutions, low-viscosity temperature-sensitive phase separation extraction, low-viscosity absorption liquids that can easily separate water.
特許文献２に記載された技術では、水溶液がＬＣＳＴ以上になると液体−液体の二層分離となり分液による分離は容易であるが、感温相分離物質と水との比率が決まればＬＣＳＴは一義的に定まり調節することはできなかった。また感温相分離物質と水との比率を変えればＬＣＳＴを変えることはできるが、感温相分離物質と水との比率が２：８〜８：２の範囲ではＬＣＳＴは大きく変化しない。また感温相分離物質と水との比率が大きく変化すると、その水溶液の浸透圧、水吸収力、抽出性などに大きな影響を及ぼし、期待する性能を発現できなくなる。 In the technique described in Patent Document 2, when the aqueous solution becomes LCST or higher, liquid-liquid two-layer separation is performed and separation by liquid separation is easy. However, LCST is unambiguous if the ratio of the temperature-sensitive phase separation substance and water is determined. Could not be adjusted. In addition, the LCST can be changed by changing the ratio of the temperature-sensitive phase separation substance and water, but the LCST does not change greatly when the ratio of the temperature-sensitive phase separation substance and water is in the range of 2: 8 to 8: 2. In addition, if the ratio between the temperature-sensitive phase separation substance and water changes greatly, the osmotic pressure, water absorbability, extractability, etc. of the aqueous solution will be greatly affected, and the expected performance cannot be expressed.
感温相分離物質のＬＣＳＴを所望の温度に設定することができれば、排熱利用、環境温度の影響などを考慮したプロセス設計に大きな利点があるが、従来技術では、ＬＣＳＴを任意に調節することが、難しかった。 If the LCST of the temperature-sensitive phase separation material can be set to a desired temperature, there is a great advantage in the process design considering the use of exhaust heat, the influence of the environmental temperature, etc., but in the conventional technology, the LCST can be arbitrarily adjusted But it was difficult.
本発明の目的は、プロセス条件に合わせて任意にＬＣＳＴを調節可能で、なおかつ低粘度でＬＣＳＴ以上では液体−液体の二層分離となり分液による分離が容易な感温相分離液体を提供することである。 An object of the present invention is to provide a temperature-sensitive phase separation liquid that can arbitrarily adjust LCST according to process conditions, and has a low viscosity and liquid-liquid two-layer separation above LCST, and can be easily separated by liquid separation. It is.
上記課題を解決するために、本発明者は鋭意検討を行った結果、本発明を完成した。すなわち、本発明は、以下の技術的手段から構成される。
〔１〕 下限臨界溶液温度が異なる２種類以上の感温相分離液体を混合した、前記複数の感温相分離液体の最高下限臨界溶液温度と最低下限臨界溶液温度の中間の下限臨界溶液温度を示す感温相分離液体。
〔２〕 感温相分離液体と、水溶性アルコール類、水溶性グリコール類、水溶性グリコールアルキルエーテル類、水溶性グリコールアルキルエーテルエステル類、水溶性ジエチレングリコールジエステル類及び水溶性アルキル脂肪酸アミド類のうちの１つ以上から選ばれた感温相分離性を示さない水溶性液体、とを混合した前記感温相分離液体の下限臨界溶液温度より高い下限臨界溶液温度を示す感温相分離液体。
〔３〕 感温相分離液体と、非水溶性アルコール類、非水溶性グリコール類、非水溶性グリコールアルキルエーテル類、非水溶性グリコールアルキルエーテルエステル類及び非水溶性アルキル脂肪酸アミド類のうちの１つ以上から選ばれた体積比１：１で水と混和しない非水溶性液体、とを混合した前記感温相分離液体の下限臨界溶液温度より低い下限臨界溶液温度を示す感温相分離液体。
〔４〕 感温相分離液体と、感温相分離性を示さない無機ハロゲン化合物及び／又は糖類からなる水溶性固体物質の水溶液、とを混合した前記感温相分離液体の下限臨界溶液温度より低い下限臨界溶液温度を示す感温相分離液体。
〔５〕 前記感温相分離液体が、２‐ブトキシエタノール、２‐イソブトキシエタノール、２‐［２‐（ベンジルオキシ）エトキシ］エタノール、１‐エトキシ‐２−（２‐エトキシエトキシ）エタン、２‐［２‐（２‐メトキシエトキシ）エトキシ］プロパン、１−アセトキシ‐２‐（２‐エトキシエトキシ）エタン、２，５，８，１１‐テトラオキサペンタデカン、１‐プロポキシ‐２‐プロパノール、平均分子量４００から７００のポリプロピレングリコール、Ｎ，Ｎ−ジイソプロピルアセトアミド、Ｎ−プロピルプロパンアミド、Ｎ−イソプロピルプロパンアミド、Ｎ，Ｎ−ジエチルブタンアミド及びＮ，Ｎ−ジメチルヘキサンアミドのうちの１つ以上である前記〔１〕〜〔４〕のいずれかに記載の感温相分離液体。
In order to solve the above-mentioned problems, the present inventors have intensively studied and as a result, completed the present invention. That is, the present invention comprises the following technical means.
[1] A lower critical solution temperature intermediate between the highest lower critical solution temperature and the lowest lower critical solution temperature of the plurality of temperature sensitive phase separation liquids obtained by mixing two or more types of temperature sensitive phase separation liquids having different lower critical solution temperatures. Temperature sensitive phase separation liquid shown.
[2] Of the temperature-sensitive phase separation liquid and water-soluble alcohols, water-soluble glycols, water-soluble glycol alkyl ethers, water-soluble glycol alkyl ether esters, water-soluble diethylene glycol diesters and water-soluble alkyl fatty acid amides A temperature-sensitive phase separation liquid that exhibits a lower critical solution temperature that is higher than the lower critical solution temperature of the temperature-sensitive phase separation liquid obtained by mixing one or more water-soluble liquids that do not exhibit temperature-sensitive phase separation.
[3] Temperature-sensitive phase separation liquid and one of water-insoluble alcohols, water-insoluble glycols, water-insoluble glycol alkyl ethers, water-insoluble glycol alkyl ether esters and water-insoluble alkyl fatty acid amides A temperature-sensitive phase separation liquid exhibiting a lower critical solution temperature lower than the lower critical solution temperature of the temperature-sensitive phase separation liquid obtained by mixing a water-insoluble liquid immiscible with water at a volume ratio of 1: 1 selected from one or more.
[4] From the lower critical solution temperature of the temperature-sensitive phase separation liquid obtained by mixing a temperature-sensitive phase separation liquid and an aqueous solution of a water-soluble solid substance composed of an inorganic halogen compound and / or saccharide that does not exhibit temperature-sensitive phase separation. A temperature-sensitive phase separation liquid that exhibits a low lower critical solution temperature.
[5] The temperature-sensitive phase separation liquid is 2-butoxyethanol, 2-isobutoxyethanol, 2- [2- (benzyloxy) ethoxy] ethanol, 1-ethoxy-2- (2-ethoxyethoxy) ethane, 2 -[2- (2-methoxyethoxy) ethoxy] propane, 1-acetoxy-2- (2-ethoxyethoxy) ethane, 2,5,8,11-tetraoxapentadecane, 1-propoxy-2-propanol, average molecular weight Said one or more of 400 to 700 polypropylene glycol, N, N-diisopropylacetamide, N-propylpropanamide, N-isopropylpropanamide, N, N-diethylbutanamide and N, N-dimethylhexanamide The temperature-sensitive phase separation liquid according to any one of [1] to [4].
本発明によれば、プロセス条件に合わせて任意にＬＣＳＴを調節可能で、なおかつ低粘度でＬＣＳＴ以上では液体−液体の二層分離となり分液による分離が容易な感温相分離液体を提供することが可能である。 According to the present invention, it is possible to provide a temperature-sensitive phase separation liquid capable of arbitrarily adjusting LCST according to process conditions, and having a low viscosity and liquid-liquid two-layer separation at LCST or higher and easy separation by liquid separation. Is possible.
本発明の第１の感温相分離液体は、下限臨界溶液温度が異なる２種類以上の感温相分離液体を混合した、前記複数の感温相分離液体の最高下限臨界溶液温度と最低下限臨界溶液温度の中間の下限臨界溶液温度を示す感温相分離液体である。 The first temperature-sensitive phase separation liquid of the present invention is a mixture of two or more types of temperature-sensitive phase separation liquids having different lower critical solution temperatures. It is a temperature-sensitive phase separation liquid that exhibits a lower critical solution temperature in the middle of the solution temperature.
前記第１の感温相分離液体は、下限臨界溶液温度が異なる２種類以上の感温相分離液体を混合することにより得ることができる。混合は、常温で通常の混合方法で行えばよい。すなわち、容器に対象の感温相分離液体を入れて、撹拌機で撹拌して混合することができる。 The first temperature-sensitive phase separation liquid can be obtained by mixing two or more types of temperature-sensitive phase separation liquids having different lower critical solution temperatures. Mixing may be performed by a normal mixing method at room temperature. That is, the target temperature-sensitive phase separation liquid can be placed in a container and mixed by stirring with a stirrer.
前記第１の感温相分離液体の原料となる前記感温相分離液体は、１５〜２０℃では体積比１：１で水と混和し均一な水溶液となり高温で水と相分離する感温相分離物質であれば限定されないが、２‐ブトキシエタノール、２‐イソブトキシエタノール、２‐［２‐（ベンジルオキシ）エトキシ］エタノール、１‐エトキシ‐２−（２‐エトキシエトキシ）エタン、２‐［２‐（２‐メトキシエトキシ）エトキシ］プロパン、１−アセトキシ‐２‐（２‐エトキシエトキシ）エタン、２，５，８，１１‐テトラオキサペンタデカン、１‐プロポキシ‐２‐プロパノール、平均分子量４００から７００のポリプロピレングリコール、Ｎ，Ｎ−ジイソプロピルアセトアミド、Ｎ−プロピルプロパンアミド、Ｎ−イソプロピルプロパンアミド、Ｎ，Ｎ−ジエチルブタンアミド及びＮ，Ｎ−ジメチルヘキサンアミドを例示することができる。 The temperature-sensitive phase separation liquid that is the raw material of the first temperature-sensitive phase separation liquid is a temperature-sensitive phase that mixes with water at a volume ratio of 1: 1 at 15 to 20 ° C. to form a uniform aqueous solution and phase separates from water at a high temperature. Although it will not be limited if it is a separated substance, 2-butoxyethanol, 2-isobutoxyethanol, 2- [2- (benzyloxy) ethoxy] ethanol, 1-ethoxy-2- (2-ethoxyethoxy) ethane, 2- [ 2- (2-methoxyethoxy) ethoxy] propane, 1-acetoxy-2- (2-ethoxyethoxy) ethane, 2,5,8,11-tetraoxapentadecane, 1-propoxy-2-propanol, average molecular weight 400 700 polypropylene glycol, N, N-diisopropylacetamide, N-propylpropanamide, N-isopropylpropanamide, N, N Diethyl butanamide and N, N- dimethyl hexanamide can be exemplified.
前記第１の感温相分離液体のＬＣＳＴを所望の調節する方法の一つとしては、希望のＬＣＳＴよりも高いＬＣＳＴの感温相分離液体と低いＬＣＳＴの感温相分離液体を少なくとも２種類以上選定し、所定の割合で混合してＬＣＳＴ測定して目的とするＬＣＳＴを有する感温相分離液体の混合割合を決定する方法がある。 As one method for adjusting the LCST of the first temperature-sensitive phase separation liquid as desired, at least two kinds of LCST temperature-sensitive phase separation liquid higher than the desired LCST and low LCST temperature-sensitive phase separation liquid are used. There is a method of selecting, mixing at a predetermined ratio, and performing LCST measurement to determine the mixing ratio of the temperature-sensitive phase separation liquid having the target LCST.
本発明の第２の感温相分離液体は、感温相分離液体と、水溶性アルコール類、水溶性グリコール類、水溶性グリコールアルキルエーテル類、水溶性グリコールアルキルエーテルエステル類、水溶性ジエチレングリコールジエステル類及び水溶性アルキル脂肪酸アミド類のうちの１つ以上から選ばれた感温相分離性を示さない水溶性液体、とを混合した前記感温相分離液体の下限臨界溶液温度より高い下限臨界溶液温度を示す感温相分離液体である。 The second temperature-sensitive phase separation liquid of the present invention includes a temperature-sensitive phase separation liquid, a water-soluble alcohol, a water-soluble glycol, a water-soluble glycol alkyl ether, a water-soluble glycol alkyl ether ester, and a water-soluble diethylene glycol diester. And a water-soluble liquid that does not exhibit temperature-sensitive phase separation selected from one or more of water-soluble alkyl fatty acid amides, and a lower critical solution temperature higher than a lower critical solution temperature of the temperature-sensitive phase separation liquid Is a temperature-sensitive phase separation liquid.
前記第２の感温相分離液体は、既知の感温相分離液体と、前記感温相分離性を示さない水溶性液体、とを混合することにより、既知の感温相分離液体の下限臨界溶液温度より高い下限臨界溶液温度を示す感温相分離液体を得ることができる。 The second temperature-sensitive phase separation liquid is mixed with a known temperature-sensitive phase separation liquid and a water-soluble liquid that does not exhibit the temperature-sensitive phase separation property, thereby lowering the lower criticality of the known temperature-sensitive phase separation liquid. A temperature-sensitive phase separation liquid exhibiting a lower critical solution temperature higher than the solution temperature can be obtained.
既知の感温相分離液体と前記感温相分離性を示さない水溶性液体の混合の方法は、第１の感温相分離液体を生成するときの方法と同様の方法により行うことができる。 The mixing method of the known temperature-sensitive phase separation liquid and the water-soluble liquid that does not exhibit the temperature-sensitive phase separation property can be performed by the same method as the method for producing the first temperature-sensitive phase separation liquid.
前記混合により下限臨界溶液温度（ＬＣＳＴ）が高くなることは、以下の理由であると推察される。一般に感温相分離液体においてはＬＣＳＴが高いものは親水性すなわち高溶解性で低いものは疎水性すなわち低溶解性である。感温相分離性を示さない水溶性液体は感温相分離液体よりも親水性すなわち高溶解性である。感温相分離液体に感温相分離性を示さない水溶性液体を混合すると感温相分離液体はより親水性すなわち高溶解性となりＬＣＳＴが高くなるものと推察される。 It is surmised that the lower critical solution temperature (LCST) is increased by the mixing because of the following reason. In general, a temperature-sensitive phase separation liquid having a high LCST is hydrophilic, that is, a high solubility, and a liquid having a low LCST is hydrophobic, that is, a low solubility. A water-soluble liquid that does not exhibit temperature-sensitive phase separation is more hydrophilic or more soluble than a temperature-sensitive phase separation liquid. When a water-soluble liquid that does not exhibit temperature-sensitive phase separation is mixed with the temperature-sensitive phase separation liquid, it is presumed that the temperature-sensitive phase separation liquid becomes more hydrophilic, that is, has a higher solubility and LCST becomes higher.
前記第２の感温相分離液体の原料となる前記感温相分離液体は、前記第１の感温相分離液体及び前記前記第１の感温相分離液体の原料として示した感温相分離液体のいずれかである。 The temperature-sensitive phase separation liquid that is the raw material of the second temperature-sensitive phase separation liquid is the temperature-sensitive phase separation shown as the raw material of the first temperature-sensitive phase separation liquid and the first temperature-sensitive phase separation liquid. One of the liquids.
前記水溶性アルコール類、水溶性グリコール類、水溶性グリコールアルキルエーテル類、水溶性グリコールアルキルエーテルエステル類、水溶性ジエチレングリコールジエステル類及び水溶性アルキル脂肪酸アミド類のうちの１つ以上から選ばれた感温相分離性を示さない水溶性液体は、最も混和しづらいとされる体積比１：１で水と混和し均一な水溶液となり加熱しても相分離しない、なおかつ前記に記載の既知の感温相分離液体と室温で任意の割合で混和し均一な溶液となる物質であれば限定されない。 Temperature sensitivity selected from one or more of the water-soluble alcohols, water-soluble glycols, water-soluble glycol alkyl ethers, water-soluble glycol alkyl ether esters, water-soluble diethylene glycol diesters and water-soluble alkyl fatty acid amides. A water-soluble liquid that does not exhibit phase separation is mixed with water at a volume ratio of 1: 1, which is most difficult to mix, becomes a uniform aqueous solution, and does not phase separate even when heated. The substance is not limited as long as it is a substance that is mixed with the separation liquid at an arbitrary ratio at room temperature to form a uniform solution.
水溶性アルコール類の好ましい例としては、炭素数が１〜３のアルコール類、具体的にはメタノール、エタノール、１−プロパノール、２−プロパノール、および炭素数が４の三級アルコール２‐メチル−２−プロパノールを例示することができる。 Preferable examples of water-soluble alcohols include alcohols having 1 to 3 carbon atoms, specifically, methanol, ethanol, 1-propanol, 2-propanol, and tertiary alcohol 2-methyl-2 having 4 carbon atoms. -Propanol can be exemplified.
また、水溶性グリコール類の好ましい例としては、具体的にはエチレングリコール、ジエチレングリコール、トリエチレングリコール、プロピレングリコール、ジプロピレングリコール、トリプロピレングリコール、１，３‐プロパンジオール、１，４−ブタンジオール、１，３−ブタンジオール、１，２−ブタンジオール、２，３−ブタンジオール、１，５−ペンタンジオール、１，２−ペンタンジオール、１，６−ヘキサンジオール、２−メチルー２，４−ペンタンジオール、平均分子量３００以下のポリプロピレングリコール、を例示することができる。 Specific examples of water-soluble glycols include ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, 1,3-propanediol, 1,4-butanediol, 1,3-butanediol, 1,2-butanediol, 2,3-butanediol, 1,5-pentanediol, 1,2-pentanediol, 1,6-hexanediol, 2-methyl-2,4-pentane Examples thereof include diol and polypropylene glycol having an average molecular weight of 300 or less.
また、水溶性グリコールアルキルエーテル類の好ましい例としては、エーテル置換基の炭素数が１〜４のエチレングリコールモノアルキルエーテル類、具体的には２−メトキシエタノール、２−エトキシエタノール、２−プロポキシエタノール、２−イソプロポキシエタノール、２−（２−メチル−２−プロポキシ）エタノール、また、エーテル置換基の炭素数が１〜４のジエチレングリコールモノアルキルエーテル類、具体的には２−（２−メトキシエトキシ）エタノール、２−（２−エトキシエトキシ）エタノール、２−（２−プロポキシエトキシ）エタノール、２−（２−イソプロポキシエトキシ）エタノール、２−（２−ブトキシエトキシ）エタノール、２−（２−イソブトキシエトキシ）エタノール、２−（２−（（１−メチルプロポキシ）エトキシ）エタノール、２−（２−（２−メチル−２−プロポキシ）エトキシ）エタノール、また、エーテル置換基の炭素数が１〜４のトリエチレングリコールモノアルキルエーテル類、具体的には２−（２−（２−メトキシエトキシ）エトキシ）エタノール、２−（２−（２−エトキシエトキシ）エトキシ）エタノール、２−（２−（２−プロポキシエトキシ）エトキシ）エタノール、２−（２−（２−イソプロポキシエトキシ）エトキシ）エタノール、２−（２−（２−ブトキシエトキシ）エトキシ）エタノール、２−（２−（２−イソブトキシエトキシ）エトキシ）エタノール、２−（２−（２−（（１−メチルプロポキシ）エトキシ）エトキシ）エタノール、２−（２−（２−（２−メチル−２−プロポキシ）エトキシ）エトキシ）エタノール、また、エーテル置換基の炭素数の和が２〜４のエチレングリコールジアルキルエーテル類、具体的には１，２−ジメトキシエタン、１，２−ジエトキシエタン、また、エーテル置換基の炭素数の和が２〜４のジエチレングリコールジアルキルエーテル類、具体的には１‐メトキシ‐２−（２‐メトキシエトキシ）エタン、１‐エトキシ‐２−（２‐メトキシエトキシ）エタンを例示することができる。また、エーテル置換基の炭素数の和が２〜４のトリエチレングリコールジアルキルエーテル類またはテトラエチレングリコールジアルキルエーテル類、具体的には１，２−ビス（２−メトキシエトキシ）エタン、１，２−ビス（２−エトキシエトキシ）エタン、ビス(２−（２−メトキシエトキシ)エチルエーテルを例示することができる。また、エーテル置換基の炭素数が１〜２のプロピレングリコールモノアルキルエーテル類またはジプロピレングリコールモノアルキルエーテル類またはトリプロピレングリコールモノアルキルエーテル類、具体的にはプロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、ジプロピレングリコールモノメチルエーテル、トリプロピレングリコールモノメチルエーテルを例示することができる。 Further, preferable examples of water-soluble glycol alkyl ethers include ethylene glycol monoalkyl ethers having 1 to 4 carbon atoms in the ether substituent, specifically 2-methoxyethanol, 2-ethoxyethanol, 2-propoxyethanol. , 2-isopropoxyethanol, 2- (2-methyl-2-propoxy) ethanol, and diethylene glycol monoalkyl ethers having 1 to 4 carbon atoms in the ether substituent, specifically 2- (2-methoxyethoxy ) Ethanol, 2- (2-ethoxyethoxy) ethanol, 2- (2-propoxyethoxy) ethanol, 2- (2-isopropoxyethoxy) ethanol, 2- (2-butoxyethoxy) ethanol, 2- (2-iso Butoxyethoxy) ethanol, 2- (2-((1-methylpropyl) Poxy) ethoxy) ethanol, 2- (2- (2-methyl-2-propoxy) ethoxy) ethanol, and triethylene glycol monoalkyl ethers having 1 to 4 carbon atoms in the ether substituent, specifically 2 -(2- (2-methoxyethoxy) ethoxy) ethanol, 2- (2- (2-ethoxyethoxy) ethoxy) ethanol, 2- (2- (2-propoxyethoxy) ethoxy) ethanol, 2- (2- ( 2-isopropoxyethoxy) ethoxy) ethanol, 2- (2- (2-butoxyethoxy) ethoxy) ethanol, 2- (2- (2-isobutoxyethoxy) ethoxy) ethanol, 2- (2- (2- (2- ( (1-Methylpropoxy) ethoxy) ethoxy) ethanol, 2- (2- (2- (2-methyl-2-propoxy) ethoxy) Toxi) ethanol, and ethylene glycol dialkyl ethers having 2 to 4 carbon atoms in the ether substituent, specifically 1,2-dimethoxyethane, 1,2-diethoxyethane, and ether substituents. Examples include diethylene glycol dialkyl ethers having 2 to 4 carbon atoms, specifically 1-methoxy-2- (2-methoxyethoxy) ethane and 1-ethoxy-2- (2-methoxyethoxy) ethane. In addition, triethylene glycol dialkyl ethers or tetraethylene glycol dialkyl ethers having 2 to 4 carbon atoms in the ether substituent, specifically 1,2-bis (2-methoxyethoxy) ethane, 1, Examples of 2-bis (2-ethoxyethoxy) ethane and bis (2- (2-methoxyethoxy) ethyl ether Rukoto can. Also, propylene glycol monoalkyl ethers or dipropylene glycol monoalkyl ethers or tripropylene glycol monoalkyl ethers having an ether substituent of 1 to 2 carbon atoms, specifically, propylene glycol monomethyl ether, propylene glycol monoethyl ether And dipropylene glycol monomethyl ether and tripropylene glycol monomethyl ether.
また、水溶性グリコールアルキルエーテルエステル類の好ましい例としては、エーテル置換基およびアシル置換基の炭素数の和が３〜４のジエチレングリコールモノアルキルエーテルエステル類、具体的には１‐アセトキシ‐２−（２‐メトキシエトキシ）エタンを例示することができる。 Further, preferable examples of the water-soluble glycol alkyl ether esters include diethylene glycol monoalkyl ether esters having 3 to 4 carbon atoms in total of the ether substituent and the acyl substituent, specifically, 1-acetoxy-2- ( An example is 2-methoxyethoxy) ethane.
また、水溶性ジエチレングリコールジエステル類の好ましい例としては、１‐アセトキシ‐２−（２‐アセトキシエトキシ）エタンを例示することができる。 Moreover, 1-acetoxy-2- (2-acetoxyethoxy) ethane can be illustrated as a preferable example of water-soluble diethylene glycol diesters.
また、水溶性アルキル脂肪酸アミド類の好ましい例としては、炭素数の和が７以下のＮ−アルキル脂肪酸アミド類またはＮ，Ｎ−ジアルキル脂肪酸アミド類、具体的にはＮ，Ｎ−ジエチルアセトアミド、Ｎ−プロピルアセトアミド、Ｎ−イソプロピルアセトアミド、Ｎ−ブチルアセトアミド、Ｎ，Ｎ−ジエチルプロパンアミド、Ｎ−メチルブタンアミド、Ｎ，Ｎ−ジメチルブタンアミドを例示することができる。
そして、前記に例示した物質のうちのいずれか１つの物質又は１つ以上の物質を混合して前記感温相分離性を示さない水溶性液体とすることができる。
Preferred examples of the water-soluble alkyl fatty acid amides include N-alkyl fatty acid amides or N, N-dialkyl fatty acid amides having a sum of 7 or less carbon atoms, specifically N, N-diethylacetamide, N Examples thereof include -propylacetamide, N-isopropylacetamide, N-butylacetamide, N, N-diethylpropanamide, N-methylbutanamide, and N, N-dimethylbutanamide.
Then, any one of the substances exemplified above or one or more substances can be mixed to form a water-soluble liquid that does not exhibit the temperature-sensitive phase separation property.
本発明の第３の感温相分離液体は、感温相分離液体と、非水溶性アルコール類、非水溶性グリコール類、非水溶性グリコールアルキルエーテル類、非水溶性グリコールアルキルエーテルエステル類及び非水溶性アルキル脂肪酸アミド類のうちの１つ以上から選ばれた体積比１：１で水と混和しない非水溶性液体、とを混合した前記感温相分離液体の下限臨界溶液温度より低い下限臨界溶液温度を示す感温相分離液体である。 The third temperature-sensitive phase separation liquid of the present invention includes a temperature-sensitive phase separation liquid, a water-insoluble alcohol, a water-insoluble glycol, a water-insoluble glycol alkyl ether, a water-insoluble glycol alkyl ether ester and a non-water-soluble glycol alkyl ether ester. A lower criticality lower than the lower critical solution temperature of the temperature-sensitive phase separation liquid mixed with a water-insoluble liquid immiscible with water at a volume ratio of 1: 1 selected from one or more of water-soluble alkyl fatty acid amides A temperature-sensitive phase separation liquid indicating the solution temperature.
前記第３の感温相分離液体は、既知の感温相分離液体と、前記体積比１：１で水と混和しない非水溶性液体、とを混合することにより、既知の感温相分離液体の下限臨界溶液温度より低い任意の下限臨界溶液温度を示す感温相分離液体を得ることができる。 The third temperature-sensitive phase separation liquid is prepared by mixing a known temperature-sensitive phase separation liquid and a water-insoluble liquid that is immiscible with water at a volume ratio of 1: 1. Thus, a temperature-sensitive phase separation liquid exhibiting an arbitrary lower critical solution temperature lower than the lower critical solution temperature can be obtained.
既知の感温相分離液体と前記体積比１：１で水と混和しない非水溶性液体の混合の方法は、第１の感温相分離液体を生成するときの方法と同様の方法により行うことができる。 The mixing method of the known temperature-sensitive phase separation liquid and the water-insoluble liquid which is not miscible with water at a volume ratio of 1: 1 is performed in the same manner as the method for producing the first temperature-sensitive phase separation liquid. Can do.
前記混合により下限臨界溶液温度（ＬＣＳＴ）が低くなることは、以下の理由であると推察される。一般に感温相分離液体においてはＬＣＳＴが高いものは親水性すなわち高溶解性で低いものは疎水性すなわち低溶解性である。体積比１：１で水と混和しない非水溶性液体は感温相分離液体よりも疎水性すなわち低溶解性である。感温相分離液体に体積比１：１で水と混和しない非水溶性液体を混合すると感温相分離液体はより疎水性すなわち低溶解性となりＬＣＳＴが低くなるものと推察される。 It is assumed that the lower critical solution temperature (LCST) is lowered by the mixing because of the following reason. In general, a temperature-sensitive phase separation liquid having a high LCST is hydrophilic, that is, a high solubility, and a liquid having a low LCST is hydrophobic, that is, a low solubility. A water-insoluble liquid that is immiscible with water at a volume ratio of 1: 1 is more hydrophobic or less soluble than a temperature sensitive phase separation liquid. It is presumed that when a water-insoluble liquid that is immiscible with water at a volume ratio of 1: 1 is mixed with the temperature-sensitive phase separation liquid, the temperature-sensitive phase separation liquid becomes more hydrophobic, that is, has a lower solubility and lowers the LCST.
前記第３の感温相分離液体の原料となる前記感温相分離液体は、前記第１の感温相分離液体、前記第２の感温相分離液体及び前記前記第１の感温相分離液体の原料として示した感温相分離液体のいずれかである。 The temperature-sensitive phase separation liquid that is a raw material for the third temperature-sensitive phase separation liquid is the first temperature-sensitive phase separation liquid, the second temperature-sensitive phase separation liquid, and the first temperature-sensitive phase separation. Any of the temperature-sensitive phase separation liquids indicated as the liquid source.
前記に記載の非水溶性アルコール類、非水溶性グリコール類、非水溶性グリコールアルキルエーテル類、非水溶性グリコールアルキルエーテルエステル類及び非水溶性アルキル脂肪酸アミド類のうちの１つ以上から選ばれた体積比１：１で水と混和しない非水溶性液体は、前記に記載の既知の感温相分離液体と室温で任意の割合で混和し均一な溶液となる物質であれば限定されない。 Selected from one or more of the water-insoluble alcohols, water-insoluble glycols, water-insoluble glycol alkyl ethers, water-insoluble glycol alkyl ether esters and water-insoluble alkyl fatty acid amides described above The water-insoluble liquid that is immiscible with water at a volume ratio of 1: 1 is not limited as long as it is a substance that is mixed with the above-described known temperature-sensitive phase separation liquid at an arbitrary ratio at room temperature to form a uniform solution.
非水溶性アルコール類の好ましい例としては、炭素数が４の一級または二級アルコール類、具体的には１−ブタノール、イソブタノール、２−ブタノール、および炭素数が５以上のアルコール類、具体的には１−ペンタノール、イソペンタノール、１，１−ジメチル−１−プロパノール、１−ヘキサノール、１−ヘプタノール、１−オクタノールが例示される。 Preferred examples of water-insoluble alcohols include primary or secondary alcohols having 4 carbon atoms, specifically 1-butanol, isobutanol, 2-butanol, and alcohols having 5 or more carbon atoms, specifically Examples of 1-pentanol, isopentanol, 1,1-dimethyl-1-propanol, 1-hexanol, 1-heptanol and 1-octanol.
また、非水溶性グリコール類、の好ましい例としては、具体的には１，８−オクタンジオール、２−エチル−１，３−ヘキサンジオール、平均分子量７００以上のポリプロピレングリコールを例示することができる。 Specific examples of the water-insoluble glycols include 1,8-octanediol, 2-ethyl-1,3-hexanediol, and polypropylene glycol having an average molecular weight of 700 or more.
また、非水溶性グリコールアルキルエーテル類、の好ましい例としては、エーテル置換基の炭素数が６以上のエチレングリコールモノアルキルエーテル類またはエチレングリコールモノアラルキルエーテル類またはエチレングリコールモノアリールエーテル類、具体的には２−ヘキシルオキシエタノール、２−フェノキシエタノール、２−ベンジルオキシエタノール、２−（２−エチルヘキシルオキシ）エタノール、また、エーテル置換基の炭素数が６以上のジエチレングリコールモノアルキルエーテル類、またはエチレングリコールモノアリールエーテル類、具体的には２−（２−ヘキシルオキシエトキシ）エタノール、２−（２−フェノキシエトキシ）エタノール、２−（（２−エチルヘキシルオキシ）エトキシ）エタノールを例示することができる。また、エーテル置換基の炭素数の和が５以上のジエチレングリコールジアルキルエーテル類、具体的には１‐ブトキシ‐２−（２‐メトキシエトキシ）エタン、１‐ブトキシ‐２−（２‐ブトキシエトキシ）エタンを例示することができる。また、エーテル置換基の炭素数が３以上のプロピレングリコールモノアルキルエーテル類またはジプロピレングリコールモノアルキルエーテル類またはトリプロピレングリコールモノアルキルエーテル類、具体的にはプロピレングリコールモノブチルエーテル、ジプロピレングリコールモノプロピルエーテル、トリプロピレングリコールモノブチルエーテル、を例示することができる。また、プロピレングリコールジアルキルエーテル類またはプロピレングリコールアルキルエーテルエステル類またはジプロピレングリコールジアルキルエーテル類またはトリプロピレングリコールジアルキルエーテル類、具体的にはプロピレングリコールジメチルエーテル、プロピレングリコールモノメチルエーテルアセテート、ジプロピレングリコールジメチルエーテル、トリプロピレングリコールジメチルエーテル Preferred examples of the water-insoluble glycol alkyl ethers include ethylene glycol monoalkyl ethers, ethylene glycol monoaralkyl ethers or ethylene glycol monoaryl ethers having an ether substituent having 6 or more carbon atoms, specifically, Is 2-hexyloxyethanol, 2-phenoxyethanol, 2-benzyloxyethanol, 2- (2-ethylhexyloxy) ethanol, diethylene glycol monoalkyl ethers having an ether substituent of 6 or more, or ethylene glycol monoaryl Examples of ethers, specifically 2- (2-hexyloxyethoxy) ethanol, 2- (2-phenoxyethoxy) ethanol, 2-((2-ethylhexyloxy) ethoxy) ethanol Door can be. Further, diethylene glycol dialkyl ethers having 5 or more carbon atoms in the ether substituent, specifically, 1-butoxy-2- (2-methoxyethoxy) ethane, 1-butoxy-2- (2-butoxyethoxy) ethane Can be illustrated. Also, propylene glycol monoalkyl ethers or dipropylene glycol monoalkyl ethers or tripropylene glycol monoalkyl ethers having an ether substituent of 3 or more, specifically propylene glycol monobutyl ether, dipropylene glycol monopropyl ether And tripropylene glycol monobutyl ether. Also, propylene glycol dialkyl ethers, propylene glycol alkyl ether esters, dipropylene glycol dialkyl ethers or tripropylene glycol dialkyl ethers, specifically propylene glycol dimethyl ether, propylene glycol monomethyl ether acetate, dipropylene glycol dimethyl ether, tripropylene Glycol dimethyl ether
また、非水溶性グリコールアルキルエーテルエステル類の好ましい例としては、エーテル置換基およびアシル置換基の炭素数の和が６以上のジエチレングリコールモノアルキルエーテルエステル類、具体的には１‐アセトキシ‐２−（２‐ブトキシエトキシ）エタンを例示することができる。 Further, preferable examples of the water-insoluble glycol alkyl ether esters include diethylene glycol monoalkyl ether esters in which the sum of the carbon number of the ether substituent and the acyl substituent is 6 or more, specifically, 1-acetoxy-2- ( An example is 2-butoxyethoxy) ethane.
また、非水溶性アルキル脂肪酸アミド類の好ましい例としては、炭素数の和が６以上のＮ−アルキル脂肪酸アミドまたはＮ，Ｎ−ジアルキル脂肪酸アミド、具体的にはＮ，Ｎ−ジブチルアセトアミド、Ｎ，Ｎ−ジプロピルプロパンアミド、Ｎ，Ｎ−ジイソプロピルプロパンアミド、Ｎ，Ｎ−ジプロピルブタンアミド、Ｎ，Ｎ−ジイソプロピルブタンアミド、Ｎ−エチルブタンアミド、Ｎ−エチルヘキサンアミド、Ｎ，Ｎ−ジエチルヘキサンアミドを例示することができる。 In addition, preferable examples of the water-insoluble alkyl fatty acid amides include N-alkyl fatty acid amides having a sum of 6 or more carbon atoms or N, N-dialkyl fatty acid amides, specifically N, N-dibutylacetamide, N, N-dipropylpropanamide, N, N-diisopropylpropanamide, N, N-dipropylbutanamide, N, N-diisopropylbutanamide, N-ethylbutanamide, N-ethylhexanamide, N, N-diethylhexane Amides can be exemplified.
そして、前記に例示した物質のうちのいずれか１つの物質又は１つ以上の物質を混合して体積比１：１で水と混和しない非水溶性液体とすることができる。 And any one substance in the substance illustrated above or one or more substances can be mixed, and it can be set as the water-insoluble liquid which is not miscible with water by volume ratio 1: 1.
本発明の第４の感温相分離液体は、感温相分離液体と、感温相分離性を示さない水溶性固体物質の水溶液、とを混合した前記感温相分離液体の下限臨界溶液温度より低い下限臨界溶液温度を示す感温相分離液体である。 The fourth temperature-sensitive phase separation liquid of the present invention is a lower critical solution temperature of the temperature-sensitive phase separation liquid obtained by mixing a temperature-sensitive phase separation liquid and an aqueous solution of a water-soluble solid substance that does not exhibit temperature-sensitive phase separation. A temperature sensitive phase separation liquid that exhibits a lower lower critical solution temperature.
前記第４の感温相分離液体は、既知の感温相分離液体と、感温相分離性を示さない無機ハロゲン化合物及び／又は糖類からなる水溶性固体物質の水溶液、とを混合することにより、既知の感温相分離液体の下限臨界溶液温度より低い下限臨界溶液温度を示す感温相分離液体を得ることができる。 The fourth temperature-sensitive phase separation liquid is obtained by mixing a known temperature-sensitive phase separation liquid and an aqueous solution of a water-soluble solid substance composed of an inorganic halogen compound and / or saccharide that does not exhibit temperature-sensitive phase separation. A temperature-sensitive phase separation liquid having a lower critical solution temperature lower than the lower critical solution temperature of the known temperature-sensitive phase separation liquid can be obtained.
既知の感温相分離液体と感温相分離性を示さない水溶性固体物質の水溶液の混合の方法は、第１の感温相分離液体を生成するときの方法と同様の方法により行うことができる。 The method of mixing the known temperature-sensitive phase separation liquid and the aqueous solution of the water-soluble solid substance that does not exhibit temperature-sensitive phase separation can be performed by the same method as the method for producing the first temperature-sensitive phase separation liquid. it can.
前記混合により下限臨界溶液温度（ＬＣＳＴ）が低くなることは、以下の理由であると推察される。一般に水溶液に水溶性固体を溶解すると塩析効果により溶質の溶解性は小さくなる。感温相分離液体が溶質である水溶液の場合、水溶性固体を溶解すると感温相分離液体は低溶解性となる。感温相分離液体に感温相分離性を示さない水溶性固体物質の水溶液を混合することは、感温相分離液体の水溶液に水溶性固体物質を溶解することと同義であり、感温相分離液体は低溶解性となりＬＣＳＴが低くなるもとと推察される。 It is assumed that the lower critical solution temperature (LCST) is lowered by the mixing because of the following reason. Generally, when a water-soluble solid is dissolved in an aqueous solution, the solubility of the solute becomes small due to the salting out effect. In the case of an aqueous solution in which the temperature-sensitive phase separation liquid is a solute, the temperature-sensitive phase separation liquid becomes lowly soluble when the water-soluble solid is dissolved. Mixing an aqueous solution of a water-soluble solid substance that does not exhibit temperature-sensitive phase separation into the temperature-sensitive phase separation liquid is synonymous with dissolving the water-soluble solid substance in the aqueous solution of the temperature-sensitive phase separation liquid. It is inferred that the separated liquid has a low solubility and a low LCST.
前記第４の感温相分離液体の原料となる前記感温相分離液体は、前記第１の感温相分離液体、前記第２の感温相分離液体、前記第３の感温相分離液体及び前記前記第１の感温相分離液体の原料として示した感温相分離液体のいずれかである。 The temperature-sensitive phase separation liquid that is a raw material of the fourth temperature-sensitive phase separation liquid is the first temperature-sensitive phase separation liquid, the second temperature-sensitive phase separation liquid, and the third temperature-sensitive phase separation liquid. And any one of the temperature-sensitive phase separation liquids shown as the raw material of the first temperature-sensitive phase separation liquid.
前記に記載の水溶液として感温相分離性を示さない水溶性固体物質は、１％以上の濃度で水に溶解し、なおかつその濃度の水溶液と前記に記載の既知の感温相分離液体とが体積比１：１で水と混和し均一な水溶液となる物質であれば限定されないが、無機ハロゲン化合物の好ましい例として、フッ化リチウム、フッ化ナトリウム、フッ化カリウム、フッ化アンモニウム、塩化リチウム、塩化ナトリウム、塩化カリウム、塩化アンモニウム、塩化マグネシウム、塩化カルシウム、臭化リチウム、臭化ナトリウム、臭化カリウム、臭化アンモニウム、臭化マグネシウム、臭化カルシウム、また、糖類の好ましい例として、グルコース、ガラクトース、フルクトース、マルトース、スクロース、トレハロースを例示することができる。
そして、前記に例示した物質のうちのいずれか１つの物質又は１つ以上の物質により感温相分離性を示さない水溶性固体物質の水溶液とすることができる。
The water-soluble solid substance that does not exhibit temperature-sensitive phase separation as the aqueous solution described above is dissolved in water at a concentration of 1% or more, and the aqueous solution having the concentration and the known temperature-sensitive phase separation liquid described above are Although it will not be limited if it is a substance that mixes with water at a volume ratio of 1: 1 to form a uniform aqueous solution, preferred examples of inorganic halogen compounds include lithium fluoride, sodium fluoride, potassium fluoride, ammonium fluoride, lithium chloride, Sodium chloride, potassium chloride, ammonium chloride, magnesium chloride, calcium chloride, lithium bromide, sodium bromide, potassium bromide, ammonium bromide, magnesium bromide, calcium bromide, and preferred examples of sugars include glucose, galactose , Fructose, maltose, sucrose and trehalose.
And it can be set as the aqueous solution of the water-soluble solid substance which does not show temperature-sensitive phase-separation property by any one substance in the substance illustrated above, or one or more substances.
［実施例１］
５０％水溶液の下限臨界溶液温度が３９℃の２，５，８，１１‐テトラオキサペンタデカン５ｍｌ、５０％水溶液の下限臨界溶液温度が４７℃の２‐［２‐（２‐メトキシエトキシ）エトキシ］プロパン５ｍｌ、および水１０ｍｌを３０ｍｌのスクリュー管に入れ、２０℃において手で振り混ぜ混合した。この混合液は流動がおさまった後も均一な外観を維持した。この混合液を加熱しながら外観の変化を観察した。混合溶液が均一な外観を示さなくなる下限臨界溶液温度は、４３℃であった。
[Example 1]
2,5,8,11-tetraoxapentadecane 5 ml with a lower critical solution temperature of 39 ° C. in 50% aqueous solution, 2- [2- (2-methoxyethoxy) ethoxy] with a lower critical solution temperature of 47 ° C. in 50% aqueous solution 5 ml of propane and 10 ml of water were placed in a 30 ml screw tube and shaken and mixed by hand at 20 ° C. This mixed liquid maintained a uniform appearance even after the flow stopped. Changes in the appearance were observed while heating the mixture. The lower critical solution temperature at which the mixed solution did not exhibit a uniform appearance was 43 ° C.
［実施例２］
５０％水溶液の下限臨界溶液温度が３９℃の２，５，８，１１‐テトラオキサペンタデカン３ｍｌ、５０％水溶液の下限臨界溶液温度が４７℃の２‐［２‐（２‐メトキシエトキシ）エトキシ］プロパン６ｍｌ、および水９ｍｌを３０ｍｌのスクリュー管に入れ、２０℃において手で振り混ぜ混合した。この混合液は流動がおさまった後も均一な外観を維持した。この混合液を加熱しながら外観の変化を観察した。混合溶液が均一な外観を示さなくなる下限臨界溶液温度は、４５℃であった。
[Example 2]
2,5,8,11-tetraoxapentadecane (3 ml) having a lower critical solution temperature of 39 ° C. in a 50% aqueous solution and 2- [2- (2-methoxyethoxy) ethoxy] having a lower critical solution temperature of 47 ° C. in a 50% aqueous solution 6 ml of propane and 9 ml of water were placed in a 30 ml screw tube and shaken and mixed by hand at 20 ° C. This mixed liquid maintained a uniform appearance even after the flow stopped. Changes in the appearance were observed while heating the mixture. The lower critical solution temperature at which the mixed solution did not show a uniform appearance was 45 ° C.
［実施例３］
５０％水溶液の下限臨界溶液温度が５０℃の平均分子量４００のポリプロピレングリコール５ｍｌ、５０％水溶液の下限臨界溶液温度が３２℃の平均分子量６００のポリプロピレングリコール５ｍｌ、および水１０ｍｌを３０ｍｌのスクリュー管に入れ、２０℃において手で振り混ぜ混合した。この混合液は流動がおさまった後も均一な外観を維持した。この混合液を加熱しながら外観の変化を観察した。混合溶液が均一な外観を示さなくなる下限臨界溶液温度は、４０℃であった。
[Example 3]
5 ml of polypropylene glycol having an average molecular weight of 400 with a lower critical solution temperature of 50 ° C. in 50% aqueous solution, 5 ml of polypropylene glycol with an average molecular weight of 600 having a lower critical solution temperature of 32 ° C. of 50% aqueous solution, and 10 ml of water are placed in a 30 ml screw tube. , Shaken and mixed by hand at 20 ° C. This mixed liquid maintained a uniform appearance even after the flow stopped. Changes in the appearance were observed while heating the mixture. The lower critical solution temperature at which the mixed solution did not exhibit a uniform appearance was 40 ° C.
［実施例４］
５０％水溶液の下限臨界溶液温度が５０℃の平均分子量４００のポリプロピレングリコール７ｍｌ、５０％水溶液の下限臨界溶液温度が３２℃の平均分子量６００のポリプロピレングリコール３ｍｌ、および水１０ｍｌを３０ｍｌのスクリュー管に入れ、２０℃において手で振り混ぜ混合した。この混合液は流動がおさまった後も均一な外観を維持した。この混合液を加熱しながら外観の変化を観察した。混合溶液が均一な外観を示さなくなる下限臨界溶液温度は、３５℃であった。
[Example 4]
7 ml of polypropylene glycol with an average molecular weight of 400 with a lower critical solution temperature of 50 ° C. in 50% aqueous solution, 3 ml of polypropylene glycol with an average molecular weight of 600 with a lower critical solution temperature of 32 ° C. in 50% aqueous solution, and 10 ml of water are placed in a 30 ml screw tube. , Shaken and mixed by hand at 20 ° C. This mixed liquid maintained a uniform appearance even after the flow stopped. Changes in the appearance were observed while heating the mixture. The lower critical solution temperature at which the mixed solution did not exhibit a uniform appearance was 35 ° C.
実施例１〜４に示すように、２種類以上の既知の感温相分離液体同士を混合することにより、その混合比に応じて、既知の感温相分離液体のそれぞれの下限臨界溶液温度のうちの高い方と低い方の間の温度の任意の下限臨界溶液温度を示す感温相分離液体を得ることができた。またこのとき感温相分離液体と水との比率は同じにしたままであった。 As shown in Examples 1 to 4, by mixing two or more types of known temperature-sensitive phase separation liquids, depending on the mixing ratio, each of the lower critical solution temperatures of the known temperature-sensitive phase separation liquids A temperature-sensitive phase separation liquid having an arbitrary lower critical solution temperature between the higher and lower ones was obtained. At this time, the ratio of the temperature-sensitive phase separation liquid and water remained the same.
［実施例５］
５０％水溶液の下限臨界溶液温度が３９℃の２，５，８，１１‐テトラオキサペンタデカン６ｍｌ、水溶性で５０％水溶液が下限臨界溶液温度を有しない１‐メトキシ‐２−（２‐メトキシエトキシ）エタン３ｍｌおよび水９ｍｌを３０ｍｌのスクリュー管に入れ、２０℃において手で振り混ぜ混合した。この混合液は流動がおさまった後も均一な外観を維持した。この混合液を加熱しながら外観の変化を観察した。混合溶液が均一な外観を示さなくなる下限臨界溶液温度は、４６℃であった。
[Example 5]
6 ml of 2,5,8,11-tetraoxapentadecane with a lower critical solution temperature of 39 ° C. in 50% aqueous solution, 1-methoxy-2- (2-methoxyethoxy) which is water soluble and has no lower critical solution temperature ) 3 ml of ethane and 9 ml of water were placed in a 30 ml screw tube and shaken and mixed by hand at 20 ° C. This mixed liquid maintained a uniform appearance even after the flow stopped. Changes in the appearance were observed while heating the mixture. The lower critical solution temperature at which the mixed solution did not exhibit a uniform appearance was 46 ° C.
［実施例６］
５０％水溶液の下限臨界溶液温度が３９℃の２，５，８，１１‐テトラオキサペンタデカン５ｍｌ、水溶性で５０％水溶液が下限臨界溶液温度を有しない１‐メトキシ‐２−（２‐メトキシエトキシ）エタン５ｍｌ、および水１０ｍｌを３０ｍｌのスクリュー管に入れ、２０℃において手で振り混ぜ混合した。この混合液は流動がおさまった後も均一な外観を維持した。この混合液を加熱しながら外観の変化を観察した。混合溶液が均一な外観を示さなくなる下限臨界溶液温度は、５５℃であった。
[Example 6]
5 ml of 2,5,8,11-tetraoxapentadecane with a lower critical solution temperature of 39 ° C. in a 50% aqueous solution, 1-methoxy-2- (2-methoxyethoxy) which is water-soluble and has no lower critical solution temperature ) 5 ml of ethane and 10 ml of water were placed in a 30 ml screw tube and shaken and mixed by hand at 20 ° C. This mixed liquid maintained a uniform appearance even after the flow stopped. Changes in the appearance were observed while heating the mixture. The lower critical solution temperature at which the mixed solution did not exhibit a uniform appearance was 55 ° C.
実施例５、６に示すように、既知の感温相分離液体と、感温相分離性を示さない水溶性液体、とを混合することにより、その混合比に応じて、既知の感温相分離液体の下限臨界溶液温度より高い下限臨界溶液温度を示す感温相分離液体を得ることができた。またこのとき感温相分離液体と水との比率は同じにしたままであった。 As shown in Examples 5 and 6, by mixing a known temperature-sensitive phase separation liquid and a water-soluble liquid that does not exhibit temperature-sensitive phase separation, a known temperature-sensitive phase is obtained depending on the mixing ratio. A temperature-sensitive phase separation liquid having a lower critical solution temperature higher than the lower critical solution temperature of the separation liquid could be obtained. At this time, the ratio of the temperature-sensitive phase separation liquid and water remained the same.
［実施例７］
５０％水溶液の下限臨界溶液温度が４７℃の２‐［２‐（２‐メトキシエトキシ）エトキシ］プロパン７．５ｍｌ、体積比１：１で水と混和しない非水溶性の１‐ブトキシ‐２−（２‐メトキシエトキシ）エタン２．５ｍｌ、および水１０ｍｌを３０ｍｌのスクリュー管に入れ、２０℃において手で振り混ぜ混合した。この混合液は流動がおさまった後も均一な外観を維持した。この混合液を加熱しながら外観の変化を観察した。混合溶液が均一な外観を示さなくなる下限臨界溶液温度は、２５℃であった。
[Example 7]
7.5 ml of 2- [2- (2-methoxyethoxy) ethoxy] propane having a lower critical solution temperature of 47 ° C. in a 50% aqueous solution, water-insoluble 1-butoxy-2-immiscible with water at a volume ratio of 1: 1 2.5 ml of (2-methoxyethoxy) ethane and 10 ml of water were placed in a 30 ml screw tube and shaken and mixed by hand at 20 ° C. This mixed liquid maintained a uniform appearance even after the flow stopped. Changes in the appearance were observed while heating the mixture. The lower critical solution temperature at which the mixed solution did not exhibit a uniform appearance was 25 ° C.
［実施例８］
５０％水溶液の下限臨界溶液温度が４７℃の２‐［２‐（２‐メトキシエトキシ）エトキシ］プロパン８ｍｌ、体積比１：１で水と混和しない非水溶性の１‐ブトキシ‐２−（２‐メトキシエトキシ）エタン２ｍｌ、および水１０ｍｌを３０ｍｌのスクリュー管に入れ、２０℃において手で振り混ぜ混合した。この混合液は流動がおさまった後も均一な外観を維持した。この混合液を加熱しながら外観の変化を観察した。混合溶液が均一な外観を示さなくなる下限臨界溶液温度は、２９℃であった。
[Example 8]
8 ml of 2- [2- (2-methoxyethoxy) ethoxy] propane having a lower critical solution temperature of 47 ° C. in a 50% aqueous solution, water-insoluble 1-butoxy-2- (2 -Methoxyethoxy) ethane (2 ml) and water (10 ml) were placed in a 30 ml screw tube and shaken and mixed by hand at 20 ° C. This mixed liquid maintained a uniform appearance even after the flow stopped. Changes in the appearance were observed while heating the mixture. The lower critical solution temperature at which the mixed solution did not exhibit a uniform appearance was 29 ° C.
実施例７、８に示すように、既知の感温相分離液体と、体積比１：１で水と混和しない非水溶性液体、とを混合することにより、その混合比に応じて、既知の感温相分離液体の下限臨界溶液温度より低い下限臨界溶液温度を示す感温相分離液体を得ることができた。またこのとき感温相分離液体と水との比率は同じにしたままであった。 As shown in Examples 7 and 8, by mixing a known temperature-sensitive phase separation liquid and a water-insoluble liquid that is immiscible with water at a volume ratio of 1: 1, A temperature-sensitive phase separation liquid having a lower critical solution temperature lower than the lower critical solution temperature of the temperature-sensitive phase separation liquid was obtained. At this time, the ratio of the temperature-sensitive phase separation liquid and water remained the same.
［実施例９］
５０％水溶液の下限臨界溶液温度が４７℃の２‐［２‐（２‐メトキシエトキシ）エトキシ］プロパン１０ｍｌ、塩化ナトリウム０．３ｇを水１０ｍｌに溶解した溶液を３０ｍｌのスクリュー管に入れ、２０℃において手で振り混ぜ混合した。この混合液には沈澱は見られずまた、流動がおさまった後も均一な外観を維持した。この混合液を加熱しながら外観の変化を観察した。混合溶液が均一な外観を示さなくなる下限臨界溶液温度は、２９℃であった。
[Example 9]
A solution prepared by dissolving 10 ml of 2- [2- (2-methoxyethoxy) ethoxy] propane having a lower critical solution temperature of 47 ° C. in 50% aqueous solution and 0.3 g of sodium chloride in 10 ml of water was placed in a 30 ml screw tube, and 20 ° C. Shake and mix by hand. No precipitate was observed in this mixed solution, and a uniform appearance was maintained after the flow stopped. Changes in the appearance were observed while heating the mixture. The lower critical solution temperature at which the mixed solution did not exhibit a uniform appearance was 29 ° C.
［実施例１０］
５０％水溶液の下限臨界溶液温度が４７℃の２‐［２‐（２‐メトキシエトキシ）エトキシ］プロパン１０ｍｌ、塩化ナトリウム０．２ｇを水１０ｍｌに溶解した溶液を３０ｍｌのスクリュー管に入れ、２０℃において手で振り混ぜ混合した。この混合液には沈澱は見られずまた、流動がおさまった後も均一な外観を維持した。この混合液を加熱しながら外観の変化を観察した。混合溶液が均一な外観を示さなくなる下限臨界溶液温度は、３３℃であった。
[Example 10]
A solution prepared by dissolving 10 ml of 2- [2- (2-methoxyethoxy) ethoxy] propane having a lower critical solution temperature of 47 ° C. in 50% aqueous solution and 0.2 g of sodium chloride in 10 ml of water was placed in a 30 ml screw tube, and 20 ° C. Shake and mix by hand. No precipitate was observed in this mixed solution, and a uniform appearance was maintained after the flow stopped. Changes in the appearance were observed while heating the mixture. The lower critical solution temperature at which the mixed solution did not exhibit a uniform appearance was 33 ° C.
実施例９、１０に示すように、既知の感温相分離液体と、感温相分離性を示さない水溶性固体物質の水溶液、とを混合することにより、感温相分離性を示さない水溶性固体物質の濃度に応じて、既知の感温相分離液体の下限臨界溶液温度より低い下限臨界溶液温度を示す感温相分離液体を得ることができた。またこのとき感温相分離液体と水との比率は同じにしたままであった。 As shown in Examples 9 and 10, by mixing a known temperature-sensitive phase separation liquid and an aqueous solution of a water-soluble solid substance that does not exhibit temperature-sensitive phase separation, water-soluble that does not exhibit temperature-sensitive phase separation. A temperature-sensitive phase separation liquid having a lower critical solution temperature lower than the lower critical solution temperature of the known temperature-sensitive phase separation liquid can be obtained according to the concentration of the conductive solid substance. At this time, the ratio of the temperature-sensitive phase separation liquid and water remained the same.
本発明により任意に下限臨界溶液温度を調節できる感温相分離液体は、低粘度高浸透圧の正浸透水処理法ドロー溶液、低粘度感温相分離抽出、容易に水分を分離できる低粘度吸収液などに用いられる。
The temperature-sensitive phase separation liquid that can arbitrarily adjust the lower critical solution temperature according to the present invention is a low viscosity high osmotic pressure forward osmosis water treatment draw solution, low viscosity temperature sensitive phase separation extraction, low viscosity absorption that can easily separate water Used for liquids.
Claims (5)
The temperature-sensitive phase separation liquid is 2-butoxyethanol, 2-isobutoxyethanol, 2- [2- (benzyloxy) ethoxy] ethanol, 1-ethoxy-2- (2-ethoxyethoxy) ethane, 2- [2 -(2-methoxyethoxy) ethoxy] propane, 1-acetoxy-2- (2-ethoxyethoxy) ethane, 2,5,8,11-tetraoxapentadecane, 1-propoxy-2-propanol, average molecular weight 400 to 700 One or more of the following: polypropylene glycol, N, N-diisopropylacetamide, N-propylpropanamide, N-isopropylpropanamide, N, N-diethylbutanamide and N, N-dimethylhexanamide 5. The temperature-sensitive phase separation liquid according to any one of 4 above.
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Citations (3)
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| JP2004515570A (en) * | 2000-07-21 | 2004-05-27 | ロレアル | Polymer having water-soluble unit and LCST unit and aqueous composition containing the polymer |
| JP2005261339A (en) * | 2004-03-19 | 2005-09-29 | Atsushi Muraguchi | Method for obtaining biological sample |
| JP2016049500A (en) * | 2014-09-01 | 2016-04-11 | 株式会社Kri | Draw solution and forward osmosis water treatment method |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004515570A (en) * | 2000-07-21 | 2004-05-27 | ロレアル | Polymer having water-soluble unit and LCST unit and aqueous composition containing the polymer |
| JP2005261339A (en) * | 2004-03-19 | 2005-09-29 | Atsushi Muraguchi | Method for obtaining biological sample |
| JP2016049500A (en) * | 2014-09-01 | 2016-04-11 | 株式会社Kri | Draw solution and forward osmosis water treatment method |
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