JPH0249070A - Dye-dispersing agent - Google Patents
Dye-dispersing agentInfo
- Publication number
- JPH0249070A JPH0249070A JP63201116A JP20111688A JPH0249070A JP H0249070 A JPH0249070 A JP H0249070A JP 63201116 A JP63201116 A JP 63201116A JP 20111688 A JP20111688 A JP 20111688A JP H0249070 A JPH0249070 A JP H0249070A
- Authority
- JP
- Japan
- Prior art keywords
- dye
- parts
- sodium
- dispersing agent
- oil
- 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.)
- Granted
Links
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 21
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims abstract description 18
- CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 claims abstract description 12
- -1 aliphatic aldehyde Chemical class 0.000 claims abstract description 10
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000004821 distillation Methods 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 abstract description 20
- 239000000047 product Substances 0.000 abstract description 16
- 229910000019 calcium carbonate Inorganic materials 0.000 abstract description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 9
- 238000006482 condensation reaction Methods 0.000 abstract description 7
- 230000003472 neutralizing effect Effects 0.000 abstract description 3
- 239000007795 chemical reaction product Substances 0.000 abstract description 2
- 238000010298 pulverizing process Methods 0.000 abstract description 2
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 46
- 239000000975 dye Substances 0.000 description 44
- 239000006185 dispersion Substances 0.000 description 15
- 238000003756 stirring Methods 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000004043 dyeing Methods 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 229910052708 sodium Inorganic materials 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 8
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 8
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 5
- 239000000920 calcium hydroxide Substances 0.000 description 5
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 5
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 4
- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229930003836 cresol Natural products 0.000 description 4
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 235000010265 sodium sulphite Nutrition 0.000 description 4
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 4
- WHRZCXAVMTUTDD-UHFFFAOYSA-N 1h-furo[2,3-d]pyrimidin-2-one Chemical compound N1C(=O)N=C2OC=CC2=C1 WHRZCXAVMTUTDD-UHFFFAOYSA-N 0.000 description 3
- 244000073231 Larrea tridentata Species 0.000 description 3
- 235000006173 Larrea tridentata Nutrition 0.000 description 3
- 238000000889 atomisation Methods 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 229960002126 creosote Drugs 0.000 description 3
- 239000010419 fine particle Substances 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- VVPHSMHEYVOVLH-UHFFFAOYSA-N 6-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(O)=CC=C21 VVPHSMHEYVOVLH-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000000986 disperse dye Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 2
- 229910001948 sodium oxide Inorganic materials 0.000 description 2
- GCNLRNBDDUYJMP-UHFFFAOYSA-M sodium;2-methylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=CC2=C(S([O-])(=O)=O)C(C)=CC=C21 GCNLRNBDDUYJMP-UHFFFAOYSA-M 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 244000241257 Cucumis melo Species 0.000 description 1
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000013590 bulk material Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- HOPIDIRJCBJLSF-UHFFFAOYSA-N methyl naphthalene-1-sulfonate;sodium Chemical compound [Na].C1=CC=C2C(S(=O)(=O)OC)=CC=CC2=C1 HOPIDIRJCBJLSF-UHFFFAOYSA-N 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
Landscapes
- Coloring (AREA)
Abstract
Description
従来の水に不溶性あるいは難溶性染料の分散剤としては
１例えばナフタリンスルホン酸ソーダのホルマリン縮合
物、メチルナフタリンスルホン酸ソーダのホルマリン縮
合物、リグニンスルホン酸ソーダ、クレゾール、シェフ
ァ酸ソーダ、亜硫酸ソーダ、水酸化ナトリウムおよびホ
ルマリンからなる縮合物、さらにクレオソート油スルホ
ン酸ソーダのホルマリン綜合物等が挙げられる。Conventional dispersants for dyes that are insoluble or sparingly soluble in water include 1, for example, formalin condensate of sodium naphthalene sulfonate, formalin condensate of sodium methylnaphthalene sulfonate, sodium lignin sulfonate, cresol, sodium Scheffa's acid, sodium sulfite, and water. Examples include a condensate of sodium oxide and formalin, and a formalin composite of creosote oil and sodium sulfonate.
しかしながら、このような従来の染料分散剤にあっては
１次に示すような欠点がある。
ナフタリンスルホン酸ソーダホルマリン縮合物およびメ
チルナフタリンスルホン酸ソーダホルマリン縮合物は染
料の湿式微粉砕時および低温域での分散性は良いが、８
０℃以上の高温域では分散性が劣り、特にポリエステル
繊維の染色時の１３０℃位では分散性が極度に低下し、
染料凝集によるターリング、染めむら等のトラブルの原
因となる。
またリグニンスルホン酸ソーダ、クレオソート油スルホ
ン酸ソーダホルマリン縮合物は、ナフタリンスルホン酸
ソーダホルマリン縮合物より高温城での分散性能は、い
くぶん改良されているが。
未だ十分でなく、逆に低温分散性が劣る。製品色相の悪
さによる淡色染料の色のくすみ、山場汚染等の問題点を
有している。
クレゾール、シェファー酸ソーダ、亜硫酸ソーダ、水酸
化ナトリウム、およびホルマリンからなる縮合物は高温
分散性は良いが、低温分散性が劣り、しかも起泡性が大
きくコストも高い等の問題点があった。However, such conventional dye dispersants have the following drawbacks. Naphthalene sulfonate soda formalin condensate and methylnaphthalene sulfonate sodium formalin condensate have good dispersibility during wet pulverization of dyes and in low temperature range, but 8
Dispersibility is poor in the high temperature range of 0°C or higher, and especially at around 130°C when dyeing polyester fibers, dispersibility is extremely reduced.
This can cause problems such as tarring and uneven dyeing due to dye aggregation. Furthermore, the dispersion performance of sodium lignin sulfonate and creosote oil and sodium sulfonate formalin condensate at high temperatures is somewhat improved compared to that of naphthalene sulfonate sodium formalin condensate. This is still not sufficient, and on the contrary, the low-temperature dispersibility is poor. There are problems such as dullness of the color of light-colored dyes due to poor product hue and pollution of piles. A condensate consisting of cresol, Schaffer's acid sodium, sodium sulfite, sodium hydroxide, and formalin has good high-temperature dispersibility, but has problems such as poor low-temperature dispersibility, high foaming property, and high cost.
【課題を解決するための１段】
この発明は、このような従来の問題点に着目してなされ
たものである。すなわち、本発明は。
！、タール蒸留より得られる中間留分（以下ＡＤＦ油と
略称する）の部分スルホン化物の脂肪族アルデヒド縮合
物又はその水溶性塩を主成分として含有することを特徴
とする染料分散剤、および２、ＡＤＦ油が、アセナフテ
ン１０〜５０重量％、ジフェニレンオキシド１０〜５０
瓜■％、およびフルオレン１０〜５０重厘％を含有する
ことを特徴とする請求項第１項記載の染料分散剤を提供
するものであり１本発明品は低温域および高温域での分
散性が優れ、しかも低泡性である。
（手段を構成する要件）
本発明に使用する染料分散剤は、ＡＤＦ油の部分スルホ
ン化物を脂肪族アルデヒドで縮合させることにより容易
に製造することができる。ここで使用されるＡＤＦ油と
は、タール蒸留より（優られる中間留分の混合物で、主
な成分としては、ナフタリン、メチルナフタリン、ジメ
チルナフタリン、ジフェニール、アセナフテン、ジフェ
ニレンオキシド、フルオレン、アントラセン、フェナン
トレン、フルオランテン、カルバゾール、ピレンである
。
本発明において重要なことは、ＡＤＦ油を構成する多種
成分の巾で７セナフテンが１０〜５０重量パーセント、
ジフェニレンオキシドが１０〜５０ ｆｆｉ １１ バ
ーセント、フルオレンが１０〜ｓｏｉ［１パーセントを
含有することが重要である。
又、脂肪族アルデヒドとしては、具体的には、ホルムア
ルデヒド、アセトアルデヒドのような低級脂肪族アルデ
ヒドが挙げられるが、中でもホルムアルデヒドを使用す
るのが好ましい。
本発明に係る染ネ１分散剤の製造の一例を示すと下記の
通りである。
ＡＤＦ油を先ず硫酸でスルホン化を行い、該原才１のス
ルホン化物又は部分スルホン化物を得る。
次に全仕込量に対し、０．５〜１．０倍モルの脂肪族ア
ルデヒドを添加し、硫酸性下で１００”Ｃ前後の温度で
縮合反応を行う、得られた縮合反応生成物は、炭酸カル
シウム又は水酸化カルシウムで中和し、析出した硫酸カ
ルシウムを濾別した後、濾液に炭酸ナトリウム又は炭酸
アンモニウムを加えてナトリウム塩又はアンモニウム塩
とするか。
縮合反応生成物を直接炭酸ナトリウム、水酸化ナトリウ
ム又は、炭酸アンモニラノーで中和して縮合物をナトリ
ウム！Ｕ又はンモニウム塩とした後、１：Ｉ縮又は濃縮
乾固して製品とする。
木１５ｉ５明で使用する染料は、水に不溶、または難溶
性のすべての染料であり、例えば、７ゾ系、アントラキ
ノン系、キノフタリン系、その他の分散染料で、いわゆ
る蛍光染料も含む。
本発明に、使用する染料分散剤の使用量は、染料に対し
て１〜２００％好ましくは３〜１００％である。
また本発明染料分散剤は、ｎ独使用だけでなく、ナフタ
リンスルホン酸ソーダのホルマリン縮合物、メチルナフ
タリンスルホン酸ソーダのホルマリン縮合物、リグニン
スルホン酸ソーダ、クレゾール、シェファー酸ソーダ、
亜硫酸ソーダ、水酸化ナトリウムおよびホルマリンから
なる縮合生成物、クレオシート油スルホン醜ソーダのホ
ルマリン綜合物、その他の界面活性剤を併用しても良い
本発明の染料分散剤の調整は、Ｗ通の手段に従い、染料
の水性分散液を連続的または非連続的に混練し、そして
ボールミル、ザンドミルその他の湿式粉砕装置中で粉砕
することにより行われる。
本発明に使用する染料分散剤は、染料に限らず、顔料、
塗料、農薬、ｅｋ業、コンクリート、石炭等の各種の鉱
工業の分野にも適用される。[First Step to Solve the Problems] The present invention has been made by focusing on such conventional problems. That is, the present invention. ! 2. A dye dispersant containing as a main component an aliphatic aldehyde condensate of a partially sulfonated middle distillate obtained by tar distillation (hereinafter referred to as ADF oil) or a water-soluble salt thereof; and 2. ADF oil contains 10-50% by weight of acenaphthene and 10-50% by weight of diphenylene oxide.
The present invention provides a dye dispersant according to claim 1, characterized in that it contains 10% by weight of melon, and 10 to 50% by weight of fluorene. It has excellent properties and low foaming properties. (Requirements constituting the means) The dye dispersant used in the present invention can be easily produced by condensing a partially sulfonated ADF oil with an aliphatic aldehyde. The ADF oil used here is a mixture of middle distillates (superior to tar distillation), including naphthalene, methylnaphthalene, dimethylnaphthalene, diphenyl, acenaphthene, diphenylene oxide, fluorene, anthracene, and phenanthrene. , fluoranthene, carbazole, and pyrene.What is important in the present invention is that 7-cenaphthene is 10 to 50% by weight of the various components constituting the ADF oil,
It is important that the diphenylene oxide contains 10 to 50 ffi 11 percent and the fluorene 10 to soi [1 percent]. Further, specific examples of the aliphatic aldehyde include lower aliphatic aldehydes such as formaldehyde and acetaldehyde, and among them, it is preferable to use formaldehyde. An example of the production of the dye 1 dispersant according to the present invention is as follows. ADF oil is first sulfonated with sulfuric acid to obtain the sulfonated product or partially sulfonated product of Gensai 1. Next, 0.5 to 1.0 times the mole of aliphatic aldehyde is added to the total amount charged, and a condensation reaction is carried out at a temperature of around 100"C under sulfuric acid. The resulting condensation reaction product is After neutralizing with calcium carbonate or calcium hydroxide and filtering out the precipitated calcium sulfate, add sodium carbonate or ammonium carbonate to the filtrate to obtain a sodium salt or ammonium salt. After neutralizing with sodium oxide or ammonyl carbonate to make the condensate into a sodium!U or ammonium salt, the product is produced by 1:1 condensation or concentration to dryness. or all poorly soluble dyes, such as 7zo-based, anthraquinone-based, quinophthalic-based, and other disperse dyes, including so-called fluorescent dyes.In the present invention, the amount of the dye dispersant used is The dye dispersant of the present invention can be used not only for n-only use, but also for formalin condensation of sodium naphthalene sulfonate, formalin condensation of sodium methylnaphthalene sulfonate, Sodium lignin sulfonate, cresol, sodium Schaffer's acid,
The dye dispersant of the present invention, which may be used in combination with a condensation product consisting of sodium sulfite, sodium hydroxide, and formalin, a formalin composite of creosite oil sulfone soda, and other surfactants, can be prepared by conventional methods. According to the method, an aqueous dispersion of the dye is continuously or discontinuously kneaded and ground in a ball mill, sand mill or other wet grinding apparatus. The dye dispersant used in the present invention is not limited to dyes, but also pigments,
It is also applied to various mining and industrial fields such as paint, agricultural chemicals, ek industry, concrete, and coal.
本発明に係る染料分散剤は１分散染料製造時で染Ｊ１ケ
ーキの微粒子化に際し、優れた微粒子化促進能を発揮し
、得られた分散液は極めて良好な分散安定性を示す、又
高温高圧染料のような比較的高い温度においても優れた
分散能を発揮する。更にｐ）（依存性が小さいため、ｐ
ｔｉが低下しても分散染料製品のゲル化は起きず、染浴
での分散低下は極めて小さい、又、起泡性が小さく、染
色時の泡のトラブルも極めて少ない。
このように優れた染料分散剤の出現によって。
染ネ１製造時の界面活性剤の削減、微粒化時間の短縮に
よる生産性の向上、省資源、省エネルギー及び染料製品
中の界面活性剤の削減による染料製品の小型化、それに
よる運搬、貯蔵経費の低減、染色廃負荷の減少及び染、
？７率の向上による染ネ１有効利用など工業的価値の高
い染料分散剤を得ることができる。
次に本発明を製造例、実施例により具体的に説明する。
（％１部はｔｎ量基準を示す）製造例−１
アセナフテン１ｏｚＨパーセント、ジフェニレンオキシ
ｌ’ｌｏｆｆｃｍパーセント、フルオレン１０重量バー
セントその他の成分７０重量パーセントのＡＤＦ油１１
３４部を８０℃に加熱し、攪拌下に濃硫酸１５７部を８
０−１００℃で３０分を要し添加後、１２０〜１３０℃
で７時間反応を行ってＡＤＦ油の部分スルホン化物を得
る０次いでこれに木１００部を加え、９０℃に只温し、
３７％ホルマリン４３部を９０〜１００℃に保ちながら
１時間を要し添加し、１００〜１０５℃で１５時間縮合
反応を行った０次いでこれに水２００部を加え、室温下
で水酸化カルシウム４４部及び炭酸カルシウム２５ａｌ
ｌを添加し約３０分攪拌した後、生成した硫酸カルシウ
ムを濾別した。この濾液に炭酸ナトリウム６４７！′Ｉ
Ｓを添加してｐＨ８〜１０とし、約３０分攪拌して生成
した炭酸カルシウムを濾別後、ｔｉ！液を濃縮乾固して
生成物２７０部得九０製造例−２
アセナフテン５０．ｌｌパーセント、ジフェニレンオキ
シド１０１ｉパーセント、フルオレン１゜ｆｆ！量バー
セント、その他の成分３０ｆｆｉ３１パーセントのＡＤ
Ｆ油１６４部を８０℃に加熱し、Ｗｌ拌下ニ汝硫ａＩ１
５７部を８０〜Ｚｏｏ℃で３０分ヲ！し添加後、１２０
〜！３０℃で７１！？間反応を行ってＡＤＦ油の部分ス
ルホン化物を得る。
次いでこれに木１００部を加え、９０℃に昇温し、３７
％ホルマリン３５部を９Ｏ−１００℃に保ちながら１時
間を要し添加し、１００〜１０５℃で１５時間縮合反応
を行なった０次いでこれに水２００部を加え、室温下で
水酸化カルシウム４４部及び炭酸カルシウム２５部を添
加し、約３０分攪拌した後、生成した硫酸カルシウムを
濾別した。この濾液に炭酸ナトリウム６４部を添加して
ｐＨ８〜１０とし、約３０分攪拌して生成した炭酸カル
シウムを濾別後、濾液を濃縮乾固して生成物２６０部得
部得
製造例−３
アセナフテン１０重ｆｆ１ｚで一セント、ジフェニレン
オキシ）’５０ｆｆｌｌｕバーセント、フルオレン１０
！１ＫＩｉパーセント、その他の成分３ｏｆｆｉｆｆｉ
バーセントのＡＤＦ油１６４部を８０℃に加熱し、攪拌
下に濃硫酸１５７部をａｏ−ｔｏｏ℃で３０分を要し添
加後、１２０〜１３０℃で７時間反応を行ってＡＤＦ油
の部分スルホン化物を得る。
次いでこれに氷１００部を加え、９０℃に４温し、３７
％ホルマリン５０部を９０〜１００℃に保ちながら１峙
間を要し添加し、１００〜１０５℃で１５時間縮合反応
を行なった０次いでこれに水２００部を加え、室温下で
水酸化カルシウム４４部及び炭酸カルシウム２５７！′
ｌｌを添加し、約３０分攪拌した後、生成した硫触カル
シウムを濾別した。この濾液にＩＲ酸ナナトリウム６４
部添加してｐＨ８〜１０とし、約３０分攪拌して生成し
た炭酸カルシウ、ムを濾別後、濾液を濃縮乾固して生成
物２８０部得九０
製造例−４
アセナフテン１ｏｚＨパーセント、ジフェニレンオキシ
ドｔｏｍｍパーセント、フルオレン５０重量パーセント
、その他の成分３０．ｌ量パーセントのＡＤＦ油１６４
部を８０℃に加熱し、攪拌下に濃硫酸１５７部を８Ｏ−
１００℃で３０分を要し添加後、１２０〜１３０℃で７
時間反応を行ってＡＤＦ油の部分スルホン化物を得る。
次いでこれに水１００部を加え、９０℃に昇温し、３７
％ホルマリン４３部を９０〜１００℃に保ちながら１時
間を要し添加し、Ｚｏｏ−１０５℃で１５時間縮合反応
を行なった０次いでこれに水２００部を加え、室温下で
水酸化カルシウム４４部及び炭酸カルシウム２５部を添
加し約３０分攪拌した後、生成したｉ酸カルシウムを濾
別した、この濾液に炭酸ナトリウム６４部を添加してｐ
Ｈ８〜１０とし、約３０分攪拌して生成した炭酸カルシ
ウムを濾別後、濾液を濃縮乾固して生成物２７０部得九
０
実施例−１
前記製造例で製造した本発明試料１０部にＣ０１、Ｄｉ
ｓｐｅｒＳｅ Ｂｌｕｅ、６０の２０部相ちを含む？
Ｓ！潤原体を投入し、さらに水を加えて１００部に調整
し、ガラスピーズ２００部を用いて、サンドグラインダ
ー（五十嵐機械＊Ｔ１ｃ株）製）にて微粒子化を行ない
、液状の染料分散物を得た。
比較サンプルとして、ナフタリンスルホン酸ソーダのホ
ルマリン縮合物（以下ＮＳＦと略称する）、リグニンス
ルホン酸ソーダ、クレゾール、シェファ酸ソーダ、亜硫
酸ソーダ、水酸化ナトリウムおよびホルマリンからなる
縮合生成物（以下ＣｒＮＦと略称する）およびクレオソ
ート油スルホン酸ソーダのホルマリン縮合物（以下ＣＳ
Ｆ略称する）を使用して上記と同様に実施した。
このときの微粒子化の際の見かけ比重の時間的変化と、
微粒子化速度についての結果を第１表に示す。
（以下余白）
江）微粒子化度の評価方法
東洋濾紙’Ｎ ｏ ５ＩＳを用い、染料分散液０．５Ｓ
ｏ１ｊｄ％、水分散液１００ｃｃを吸引濾過し。
濾紙上に残存する染料の量で評価した。
０：染料がほとんど通過し、はとんど残っていない。
△：染料が一部濾紙、１；に残っている。
×：染料の大部分が濾紙１−に残っている。
実施例−２
実施例−■で得られた染料分散物について、高温染色機
カラーベット１２を使用して、ポリエステルジャージＩ
Ｏｇ、染料濃度２ｇ／ｌ２（６％Ｏｗｆ） ％浴比１
： ：Ｓ ０１ｐ１１５、染色温度１；３゜”０１０分
間の条件で高温染色試験を実施し、繊維上のターリング
について検討した結果を第２表に示す。
（以下余白）
実施例−３
前記！２造例で製造した本発明試料１５部に０゜１、Ｄ
ｉｓｐｅｒｓｅ ｌ１ｌｕａ、９２の１５部相当を含
む湿潤原体を投入し、さらに水を加えて１００部に２整
し、実施例−１と同様の方法で４時間微粒子化を行ない
、液状の染料分散物を得た、この染料分散物を用いて、
実施例−２と同じ条件にて、高温分散性の評価を実施し
、結果を第３表に示す。
（以下余白）The dye dispersant according to the present invention exhibits an excellent ability to promote microparticulation when producing Dye J1 cake into microparticles, and the resulting dispersion exhibits extremely good dispersion stability. It exhibits excellent dispersion ability even at relatively high temperatures like dyes. Furthermore, p) (because the dependence is small, p
Even if the ti decreases, gelation of the disperse dye product does not occur, and the decrease in dispersion in the dye bath is extremely small.Furthermore, the foaming property is small, and problems caused by foam during dyeing are extremely small. With the advent of such excellent dye dispersants. Reducing the amount of surfactant used in dyeing 1 production, improving productivity by shortening atomization time, saving resources and energy, and reducing the size of dye products by reducing the amount of surfactants in dye products, resulting in transportation and storage costs. reduction, reduction in dyeing waste load and dyeing,
? It is possible to obtain a dye dispersant with high industrial value such as effective utilization of dye dye 1 by improving the dye dispersion ratio. Next, the present invention will be specifically explained with reference to manufacturing examples and examples. (% 1 part indicates tn amount basis) Production example-1 ADF oil 11 with 1 ozH percent acenaphthene, 10 percent diphenyleneoxy l'loffcm, 10 weight percent fluorene, and 70 weight percent other components.
34 parts was heated to 80°C, and 157 parts of concentrated sulfuric acid was added to 80 parts while stirring.
It takes 30 minutes at 0-100℃, and after addition, the temperature rises to 120-130℃.
The reaction was carried out for 7 hours to obtain a partially sulfonated product of ADF oil.Next, 100 parts of wood was added to this and heated to 90°C.
43 parts of 37% formalin was added over 1 hour while maintaining the temperature at 90-100°C, and a condensation reaction was carried out at 100-105°C for 15 hours.Next, 200 parts of water was added to this, and 44 parts of calcium hydroxide was added at room temperature. part and calcium carbonate 25al
After stirring for about 30 minutes, the produced calcium sulfate was filtered off. This filtrate contains 647 sodium carbonate! 'I
S was added to adjust the pH to 8 to 10, and after stirring for about 30 minutes and filtering off the produced calcium carbonate, ti! The liquid was concentrated to dryness to obtain 270 parts of the product. 90 Production Example-2 Acenaphthene 50. ll percent, diphenylene oxide 101i percent, fluorene 1°ff! Volume percent, other ingredients 30ffi 31% AD
164 parts of F oil was heated to 80°C, and while stirring Wl, 164 parts of sulfur aI1
57 parts at 80~Zoo℃ for 30 minutes! After addition, 120
~! 71 at 30℃! ? A partially sulfonated product of ADF oil is obtained by performing an intermediate reaction. Next, 100 parts of wood was added to this, the temperature was raised to 90℃, and 37
% formalin was added over 1 hour while maintaining the temperature at 90-100°C, and a condensation reaction was carried out at 100-105°C for 15 hours.Next, 200 parts of water was added to this, and 44 parts of calcium hydroxide was added at room temperature. After adding 25 parts of calcium carbonate and stirring for about 30 minutes, the produced calcium sulfate was filtered off. 64 parts of sodium carbonate was added to this filtrate to adjust the pH to 8 to 10, and the resulting calcium carbonate was filtered off by stirring for about 30 minutes.The filtrate was concentrated to dryness to yield 260 parts of product.Production Example-3 Acenaphthene 1 cent for 10 weight ff1z, diphenyleneoxy) '50 ffllu percent, fluorene 10
! 1KIi percent, other ingredients 3offiffi
164 parts of Bercent ADF oil was heated to 80°C, 157 parts of concentrated sulfuric acid was added with stirring at ao-too°C over 30 minutes, and the reaction was carried out at 120-130°C for 7 hours to partially sulfonate the ADF oil. Get a monster. Next, 100 parts of ice was added to this, heated to 90°C for 4 hours, and heated to 37°C.
50 parts of formalin was added over a period of time while maintaining the temperature at 90 to 100°C, and a condensation reaction was carried out at 100 to 105°C for 15 hours. Then, 200 parts of water was added to this, and 44 parts of calcium hydroxide was added at room temperature. Part and calcium carbonate 257! ′
After stirring for about 30 minutes, the produced calcium sulfate was filtered off. To this filtrate, IR acid sodium 64
After stirring for about 30 minutes and filtering out the produced calcium carbonate, the filtrate was concentrated to dryness to obtain 280 parts of the product.Production Example-4 Acenaphthene 1ozH%, Diphenylene Oxide tomm percent, fluorene 50 weight percent, other ingredients 30. l volume percent ADF oil 164
was heated to 80°C, and 157 parts of concentrated sulfuric acid was added to 8O-
It took 30 minutes at 100℃, and after addition, it was heated to 120-130℃ for 7 minutes.
A partial sulfonated product of ADF oil is obtained by performing a time reaction. Next, 100 parts of water was added to this, the temperature was raised to 90°C, and 37
% formalin was added over 1 hour while maintaining the temperature at 90 to 100°C, and a condensation reaction was performed at Zoo-105°C for 15 hours. Then, 200 parts of water was added to this, and 44 parts of calcium hydroxide was added at room temperature. After adding 25 parts of calcium carbonate and stirring for about 30 minutes, the produced calcium chloride was filtered off. To this filtrate, 64 parts of sodium carbonate was added.
After stirring for about 30 minutes and filtering out the produced calcium carbonate, the filtrate was concentrated to dryness to obtain 270 parts of the product. C01, Di
superSe Blue, including 20 copies of 60?
S! A liquid dye dispersion was obtained by adding the hydrant, adjusting the volume to 100 parts by adding water, and using 200 parts of glass beads to make fine particles with a sand grinder (manufactured by Igarashi Kikai *T1c Co., Ltd.). Obtained. As comparative samples, a formalin condensate of sodium naphthalene sulfonate (hereinafter abbreviated as NSF), a condensation product consisting of sodium lignin sulfonate, cresol, sodium shephaate, sodium sulfite, sodium hydroxide, and formalin (hereinafter abbreviated as CrNF) were used. ) and formalin condensate of creosote oil and sodium sulfonate (hereinafter referred to as CS
It was carried out in the same manner as above using F. Temporal changes in apparent specific gravity during atomization at this time,
Table 1 shows the results regarding the rate of atomization. (Left below) E) Method for evaluating the degree of micronization Using Toyo Roshi 'N o 5IS, dye dispersion 0.5S
100 cc of the aqueous dispersion was suction filtered. Evaluation was made based on the amount of dye remaining on the filter paper. 0: Most of the dye passes through, and almost no dye remains. Δ: Part of the dye remained on the filter paper, 1; ×: Most of the dye remains on the filter paper 1-. Example-2 The dye dispersion obtained in Example-■ was used to dye polyester jersey I using a high-temperature dyeing machine Colorbet 12.
Og, dye concentration 2g/l2 (6%Owf) % bath ratio 1
: : S 01p115, a high temperature dyeing test was carried out under the conditions of dyeing temperature 1; 3°'' for 10 minutes, and the results of examining tarring on the fibers are shown in Table 2. (Margins below) Example-3 Above! 0°1, D to 15 parts of the sample of the present invention manufactured in 2 examples.
A wet bulk material containing the equivalent of 15 parts of isperse l1lua. Using this dye dispersion obtained,
High-temperature dispersibility was evaluated under the same conditions as in Example-2, and the results are shown in Table 3. (Margin below)
１、本発明の染料分散物は、微粒子化時における泡◇〕
ちが少ないため、染料分散液の比１ｎが大きく、また短
い時間で染料粒子が微粒子化されている。［ｉｉｊ記第
１表、第３表参照）
２、本発明の染料分散物は、高温における分散性が極め
て優れている。［ｉ）？Ｉ記第２表、第：３表参照〕
特許出願人 第−Ｉ′業製薬株式会社1. The dye dispersion of the present invention has no bubbles ◇ when it is made into fine particles.
Since the difference is small, the ratio 1n of the dye dispersion is large, and the dye particles are made into fine particles in a short period of time. [See Tables 1 and 3 in Iij.] 2. The dye dispersion of the present invention has extremely excellent dispersibility at high temperatures. [i)? Refer to Table I, Table 2 and Table 3] Patent Applicant No. I' Industry Pharmaceutical Co., Ltd.
Claims (1)
略称する）の部分スルホン化物の脂肪族アルデヒド縮合
物又はその水溶性塩を主成分として含有することを特徴
とする染料分散剤。 ２、ＡＤＦ油が、アセナフテン１０〜５０重量％、ジフ
ェニレンオキシド１０〜５０重量％、およびフルオレン
１０〜５０重量％を含有することを特徴とする請求項第
１項記載の染料分散剤。[Claims] 1. It is characterized by containing as a main component an aliphatic aldehyde condensate of a partially sulfonated middle distillate obtained by tar distillation (hereinafter referred to as ADF oil) or a water-soluble salt thereof Dye dispersant. 2. The dye dispersant according to claim 1, wherein the ADF oil contains 10 to 50% by weight of acenaphthene, 10 to 50% by weight of diphenylene oxide, and 10 to 50% by weight of fluorene.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63201116A JPH0621423B2 (en) | 1988-08-11 | 1988-08-11 | Dye dispersant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63201116A JPH0621423B2 (en) | 1988-08-11 | 1988-08-11 | Dye dispersant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0249070A true JPH0249070A (en) | 1990-02-19 |
| JPH0621423B2 JPH0621423B2 (en) | 1994-03-23 |
Family
ID=16435668
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63201116A Expired - Fee Related JPH0621423B2 (en) | 1988-08-11 | 1988-08-11 | Dye dispersant |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0621423B2 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9302468B1 (en) | 2014-11-14 | 2016-04-05 | Ming Xu | Digital customizer system and method |
| US9781307B2 (en) | 2014-11-14 | 2017-10-03 | Sawgrass Technologies, Inc. | Networked digital imaging customization |
| US10419644B2 (en) | 2014-11-14 | 2019-09-17 | Sawgrass Technologies, Inc. | Digital image processing network |
| US10827097B2 (en) | 2015-11-02 | 2020-11-03 | Sawgrass Technologies, Inc. | Product imaging |
| US10827098B2 (en) | 2015-11-02 | 2020-11-03 | Sawgrass Technologies, Inc. | Custom product imaging method |
-
1988
- 1988-08-11 JP JP63201116A patent/JPH0621423B2/en not_active Expired - Fee Related
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9302468B1 (en) | 2014-11-14 | 2016-04-05 | Ming Xu | Digital customizer system and method |
| US9781307B2 (en) | 2014-11-14 | 2017-10-03 | Sawgrass Technologies, Inc. | Networked digital imaging customization |
| US10075619B2 (en) | 2014-11-14 | 2018-09-11 | Sawgrass Technologies, Inc. | Networked digital imaging customization |
| US10419644B2 (en) | 2014-11-14 | 2019-09-17 | Sawgrass Technologies, Inc. | Digital image processing network |
| US10587777B2 (en) | 2014-11-14 | 2020-03-10 | Sawgrass Technologies, Inc. | Digital image processing network |
| US10827097B2 (en) | 2015-11-02 | 2020-11-03 | Sawgrass Technologies, Inc. | Product imaging |
| US10827098B2 (en) | 2015-11-02 | 2020-11-03 | Sawgrass Technologies, Inc. | Custom product imaging method |
| US11503187B2 (en) | 2015-11-02 | 2022-11-15 | Sawgrass Technologies, Inc. | Custom product imaging method |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0621423B2 (en) | 1994-03-23 |
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| LAPS | Cancellation because of no payment of annual fees |