TWI507486B - 分散偶氮染料、分散染料組成物、經染色物質以及製備分散偶氮染料的方法 - Google Patents
分散偶氮染料、分散染料組成物、經染色物質以及製備分散偶氮染料的方法 Download PDFInfo
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- TWI507486B TWI507486B TW099145552A TW99145552A TWI507486B TW I507486 B TWI507486 B TW I507486B TW 099145552 A TW099145552 A TW 099145552A TW 99145552 A TW99145552 A TW 99145552A TW I507486 B TWI507486 B TW I507486B
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- 239000000203 mixture Substances 0.000 title claims description 20
- 239000000987 azo dye Substances 0.000 title claims description 17
- 239000000986 disperse dye Substances 0.000 title claims description 14
- 239000000463 material Substances 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 239000000975 dye Substances 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 238000005859 coupling reaction Methods 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 230000008878 coupling Effects 0.000 claims description 9
- 238000010168 coupling process Methods 0.000 claims description 9
- 239000002270 dispersing agent Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 239000000080 wetting agent Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000012954 diazonium Substances 0.000 claims description 3
- 150000001989 diazonium salts Chemical class 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 3
- 238000000227 grinding Methods 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 150000004982 aromatic amines Chemical class 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 239000012190 activator Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 239000013530 defoamer Substances 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 238000009736 wetting Methods 0.000 claims 1
- 239000000835 fiber Substances 0.000 description 15
- 238000004043 dyeing Methods 0.000 description 13
- 238000000859 sublimation Methods 0.000 description 12
- 230000008022 sublimation Effects 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 238000005406 washing Methods 0.000 description 10
- 229920000728 polyester Polymers 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 238000007639 printing Methods 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- -1 fluorosulfonyl group Chemical group 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229920002994 synthetic fiber Polymers 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- 239000002759 woven fabric Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000012790 confirmation Methods 0.000 description 2
- 238000010014 continuous dyeing Methods 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- LXQOQPGNCGEELI-UHFFFAOYSA-N 2,4-dinitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O LXQOQPGNCGEELI-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000010420 art technique Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000010017 direct printing Methods 0.000 description 1
- 238000010018 discharge printing Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
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- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
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- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0059—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only sulfur as heteroatom
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- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
- C09B29/0077—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with one nitrogen and one sulfur as heteroatoms
- C09B29/0081—Isothiazoles or condensed isothiazoles
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- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
- C09B29/0077—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with one nitrogen and one sulfur as heteroatoms
- C09B29/0085—Thiazoles or condensed thiazoles
- C09B29/0088—Benzothiazoles
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- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/081—Amino benzenes free of acid groups characterised by the amino group substituted amino group unsubstituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino, aralkylamino or arylamino
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- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
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- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
- C09B29/0813—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by OH, O-C(=X)-R, O-C(=X)-X-R, O-R (X being O,S,NR; R being hydrocarbonyl)
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- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
- C09B29/0815—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by -C(=O)-
- C09B29/0816—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by -C(=O)- substituted by -COOR
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- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
- C09B29/0815—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by -C(=O)-
- C09B29/0816—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by -C(=O)- substituted by -COOR
- C09B29/0817—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by -C(=O)- substituted by -COOR having N(-aliphatic residue-COOR)2 as substituents
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- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
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- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
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- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
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- Textile Engineering (AREA)
- Coloring (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Plural Heterocyclic Compounds (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Description
本發明與一種新穎分散染料及其用途有關。
傳統上，分散染料藉由一般浸染、連續染色及印染技術使用於染色合成纖維及其與其他纖維如纖維素、聚氨基甲酸酯、尼龍及羊毛的掺合物。
近來隨著趨勢變化，掺合織布的樣式及市場需求消耗顯著增加。這些新的織布是使用低丹尼聚酯纖維或是與聚氨基甲酸酯、尼龍及羊毛掺合的纖維而由微米尺寸纖維製造。當使用習知分散染料染色或印染時，這些新上色織布的堅牢度性質在耐光堅牢度及昇華堅牢度方面，特別是在水洗堅牢度方面，變差。堅牢度性質因為使用低丹尼聚酯纖維或是與聚氨基甲酸酯、尼龍及羊毛掺合的纖維而使經染色纖維變薄而變差。在染色及印染領域需要耐受此用途的優秀染料。
IN190551及其分割申請案IN197577與IN196765揭示一種包括氟磺醯基的單偶氮染料。前述印度專利揭示一種合成性織品物質或纖維掺合物的著色方法。
以WO 2008/074719發表的專利申請案2162/KOLNP/2009揭
示一種包括分子式(I)的(一)二或更多分散染料的分散染料混合物。
所以先前技藝揭示偶氮染料化合物及其製備方法，然而未授予優秀的堅牢度性質，特別是耐光堅牢度及水洗堅牢度性質。
發明目的
本發明目的為提供一種黃色、紅色及藍色分散偶氮染料。
本發明另一目的為提供一種合成性織品物質的著色方法。
本發明另一目的為提供一種在聚酯纖維上具有優秀耐光堅牢度及水洗堅牢度性質的分散偶氮染料。
根據本發明一方面提供一種分子式1的分散染料。
其中，R1為氫、甲基、羥基或NHR3；R2為氫、氯或甲氧基；其中，D為分子式(2a)的一基團
其中，X、Y及Z獨立地為氫、甲基、鹵素、氰基或硝基；或是分子式(2b)的一基團，
其中，T1獨立地為氫、鹵素、硝基、-SO2CH3或-SCN；及T2 為氫或鹵素；或是分子式(2c)的一基團，
或是分子式(2d)的一基團，
其中，T3及T4獨立地為硝基、乙醯基、COOR4或氰基；R3為-COCH3、-COC2H5、-SO2CH3或SO2C2H5；R4為C1至C4未經取代烷基；
n及m獨立地為0、1或2。
根據本發明另一方面提供一種具於聚酯纖維上優秀水洗堅牢度及耐光堅牢度的分子式(1)分散偶氮染料之製備方法。
本發明提供一種具優秀水洗堅牢度及耐光堅牢度的新穎分
子式(1)分散偶氮染料。
其中，R1為氫、甲基、羥基或NHR3；R2為氫、氯或甲氧基；其中，D為分子式(2a)的一基團
其中，
X、Y及Z獨立地為氫、甲基、鹵素、氰基或硝基；或是分子式(2b)的一基團，
其中，T1獨立地為氫、鹵素、硝基、-SO2CH3或-SCN；及T2為氫或鹵素；或是分子式(2c)的一基團，
或是分子式(2d)的一基團，
其中，T3及T4獨立地為硝基、乙醯基、COOR4或氰基；R3為-COCH3、-COC2H5、-SO2CH3或SO2C2H5；R4為C1至C4未經取代烷基；n及m獨立地為0、1或2。
本發明更敘述一種新穎分散染料的合成方法、染料組成物的製備及施用這些染料於纖維的方法。
分散偶氮染料一般由重氮化一級芳香胺及接著與合適耦合成分耦合而製備。
在適當條件下，一級芳香族或雜芳香族胺可被成功地重氮化並與特別發展的耦合成分耦合，以各自地得到新穎分子式(1)分散染料。這些新穎分散染料擁有優秀水洗堅牢度及耐光堅牢度性質。
本發明更提供一種組成物，該組成物包括本發明分散染料及傳統上用於著色應用的額外至少一種額外成分，如分散劑及選擇性地表面活化劑或潤溼劑。該染料組成物典型上包括從10%至65%，較佳為20%至50%重量的總染料，染料可為單一成分或是於固體介質的混合物。
典型分散劑實例為木質磺酸酯、萘磺酸/甲醛縮合物及酚/甲酚/磺胺酸/甲醛縮合物。典型潤溼劑實例為可磺酸化的烷基芳香基乙醇酯或磷酸酯及可存在的其他成分典型實例為無機鹽、如礦物油或壬醇的消沫劑、有機液體及緩衝劑。分散劑可以80%至400%的染料混合物重量存在。潤溼劑可以0.1%至20%的染料混合物重量使用。
使用於含水介質中的玻璃珠或沙將本發明的分散染料或分散染料混合物與合適分散劑磨製。可更添加分散劑、填料及其他表面活化劑至該組成物並使用如噴霧乾燥的技術將之乾燥，以得到包括從15%至65%重量的染料的固體組成物。
在使用纖維物質染色的情況下，染料以一般方法在水中與分散劑磨製，及完工染料以液體形式用於染色或印染，或是在噴霧乾燥液體後以粉末形式施用。每一個完工染料以單一或是二或更多本發明染料的混合物用於染色及印染。
在浸染的情況下，聚酯纖維、共軛纖維及掺合纖維為藉由高溫染色、導染染色法及連續染色而以優秀堅牢度染色。分子式(1)的染料可以個別或是分子式(1)衍生物的混合物用於染色及印染。
在印染的情況下，聚酯纖維、織品物質藉由直接印染或拔染印花而以優秀堅牢度加工。
可參考下列實例更詳細敘述本發明實施例，其中除非另外說明，分量以重量表示。本發明具體說明如下，但是本發明不限於這些實例。
分子式1染料的製備包括下列步驟：a)耦合成分的合成；b)芳香胺的重氮化；c)重氮鹽與合適耦合成分之耦合；d)使用合適分散劑、填料及選擇性地潤溼劑或表面活化劑磨製。
以液體形式使用或噴霧乾燥以得到最終粉末樣品。
實例-1：
結構分子式(3)
結構分子式(3)的實例1為以下列方法合成。
將丙烯酸20.0公克加至DMF(N,N-二甲替甲醯胺)40.0公克及3-胺基乙醯苯胺15公克的混合物及加熱至80℃並持續攪拌2小時。反應完成後，加入19.4公克氯乙腈(氰基甲基氯)至反應物質及加熱至80℃並持續攪
拌2小時。反應完成時包含35公克此耦合劑的此反應物質用於接下來的耦合反應。
將30毫升的40%亞硝醯硫酸於0-5℃加至19.4公克2,4-二硝基苯胺及50毫升硫酸的混合物並於低於5℃攪拌2小時。2小時後於0-5℃將此重氮鹽溶液加至冰、水及35公克耦合劑，N,N-二氰基甲氧基碳乙基-3-乙醯胺苯胺的預先置入混合物。於低於5℃攪拌反應物質1小時及過濾。接著將結晶型的固體以冰水清洗以得到90%產率的分子式(3)染料。分子式(3)染料的λ max(於丙酮中)為536奈米。
將2.0公克的所得到濕壓濾餅與2.0公克萘磺酸-甲醛縮合物及50公克水及500公克玻璃珠(平均尺寸為直徑0.8毫米)磨製24小時，及在磨製後，過濾物質以分離玻璃珠。
將20公克的所得到完成液體加至100毫升的水及使用醋酸調整pH至4，將10公克聚酯片加至染料浴以進行浸染。
加熱染料浴至135℃及保持40分鐘，在適當潤洗、清洗及乾燥之後，產生深寶紅色並具有優秀水洗堅牢度、耐光堅牢度及昇華堅牢度的經染色物質。
以下列測試方法評估經染色織物的堅牢度性質。
根據測試方法AATCC 61 2A評估水洗堅牢度，根據測試方法ISO 105 B02評估耐光堅牢度及於180度進行昇華測試30秒及於210度進行昇華測試30秒。
實例2
使用與實例-1所述相同的方法合成分子式(4)染料以得到表
中所述下列染料：
實例-3：
使用與實例-1所述相同的方法合成分子式(2)染料以得到表中所述下列染料：
實例4：
使用與實例-1所述相同的方法合成分子式(1)染料以得到表中所述下列染料：
比較實例-1：
比較在WO2008/074719表-1以染料1-5及染料1-38表示的每一個下列染料與本專利中以實例2-1表示的染料的水洗堅牢度及昇華堅牢度，結果如下。
本專利實例2-1的染料與對照染料1-5為非常類似的化學品，差別僅在胺基自由基上的乙基及C2H4COOCH2CN，且實例2-1沒有甲氧基，但是兩者間的品質差異非常大，特別是在水洗堅牢度，於昇華堅牢度及耐光堅牢度的差異亦大。取代WO2008/074719中僅一個C2H4COOCH2CN，此對照實例提供引入兩個C2H4COOCH2CN取代基以改善水洗堅牢度性質的方法之確認。兩個C2H4COOCH2CN取代基之引入提供更
優秀的水洗堅牢度且亦改善昇華堅牢度及耐光堅牢度。
比較實例2
本專利實例2-4的染料與對照染料1-38為非常類似的化學品，差別僅在胺基自由基上的乙基及C2H4COOCH2CN，但是兩者間的品質差異非常大，特別是在水洗堅牢度，於昇華堅牢度及耐光堅牢度的差異亦大。取代WO2008/074719中僅一個C2H4COOCH2CN，此對照實例更提供所採用方法之確認，此方法引入兩個C2H4COOCH2CN取代基以得到具改善水洗堅牢度性質的染料。除了水洗堅牢度的改善，兩個C2H4COOCH2CN取代基之引入提供改善昇華堅牢度及耐光堅牢度的優秀結果。
Claims (10)
- 一種分子式(1)的新穎分散偶氮染料
- 如申請專利範圍第1項所述的新穎分散偶氮染料，其中分子式(1)化合物具有分子式(2)：
- 如申請專利範圍第1項所述的新穎分散偶氮染料，其中分子式(1)化合物具有分子式(4)：
- 如申請專利範圍第1項所述的新穎分散偶氮染料，其中分子式(1)化合物為：
- 一種指定為分子式(3)的如申請專利範圍第1項的新穎分散偶氮染料：
- 一種指定為分子式(5)的如申請專利範圍第1項的新穎分散偶氮染料：
- 一種指定為分子式(6)的如申請專利範圍第1項的新穎分散偶氮染料：
- 一種分散染料組成物，包括：如申請專利範圍第1至7項中任何一項所述的單一成分的分散偶氮染料或是其以10%至65%重量的染料組成物的量與二或更多本發明染料合併，以20%至200%重量的染料化合物的量存在的至少一種分散劑及選擇性地更包括量為0.1%至20%如表面活化劑或潤溼劑的成分，及消沫劑/除灰劑。
- 一種如申請專利範圍第1至7項中任何一項所述的分散偶氮染料的製備方法，包括步驟：a)合成耦合成分；b)重氮化芳香胺； c)將重氮鹽與合適耦合成分耦合；d)與合適分散劑、填料及選擇性地潤溼劑或表面活化劑磨製。
- 一種經染色物質，其使用如申請專利範圍第1至7項中任何一項所述的新穎染料，該新穎染料可為單一成分或是合併二或更多染料。
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| KR20120098917A (ko) | 2012-09-05 |
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