CN1234418A - 分散性染料 - Google Patents
分散性染料 Download PDFInfo
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- CN1234418A CN1234418A CN99107401A CN99107401A CN1234418A CN 1234418 A CN1234418 A CN 1234418A CN 99107401 A CN99107401 A CN 99107401A CN 99107401 A CN99107401 A CN 99107401A CN 1234418 A CN1234418 A CN 1234418A
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- 239000000986 disperse dye Substances 0.000 title abstract 2
- 239000000975 dye Substances 0.000 claims abstract description 52
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 30
- 239000000463 material Substances 0.000 claims abstract description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 15
- 239000004753 textile Substances 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 150000002367 halogens Chemical group 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 21
- 239000000460 chlorine Substances 0.000 claims description 20
- 238000005859 coupling reaction Methods 0.000 claims description 16
- 230000008878 coupling Effects 0.000 claims description 15
- 238000010168 coupling process Methods 0.000 claims description 15
- 238000006193 diazotization reaction Methods 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 230000002209 hydrophobic effect Effects 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 230000002194 synthesizing effect Effects 0.000 claims description 5
- PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229920004935 Trevira® Polymers 0.000 claims description 2
- 150000001989 diazonium salts Chemical class 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 abstract description 12
- 229920000728 polyester Polymers 0.000 abstract description 8
- 238000007639 printing Methods 0.000 abstract description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- -1 isobutyl- Chemical group 0.000 description 3
- 210000004243 sweat Anatomy 0.000 description 3
- GAWAYYRQGQZKCR-UHFFFAOYSA-N 2-chloropropionic acid Chemical compound CC(Cl)C(O)=O GAWAYYRQGQZKCR-UHFFFAOYSA-N 0.000 description 2
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000002657 fibrous material Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 235000006491 Acacia senegal Nutrition 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000305 astragalus gummifer gum Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010018 discharge printing Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical class COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical group O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000012451 post-reaction mixture Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/42—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/43—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- 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
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/008—Preparations of disperse dyes or solvent dyes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/922—Polyester fiber
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
分散性染料,分子式如下:其中R1是硝基或氰基,R2是卤素,R3是C1－C4烷基,R4和R5各自独立地是甲基或乙基,R6是氢、甲基或乙基,其前提条件是当R1是氰基,R2是卤素,R3是甲基或异丙基时,或者当R1是硝基,R2是卤素,R3是甲基时,R6不是氢。本发明的染料特别适用于印染聚酯纺织材料。
Description
本发明涉及分散性染料、其制备方法以及其在染或印半合成或合成疏水性纤维材料中的应用。
人们很久就认识到分散性染料即不含水溶性基团的染料并且将其应用到印染疏水性纺织材料中。但是，所得到的染色在热徙动中往往不牢固，尤其在耐洗和耐汗方面，许多染料的牢固性能也不能令人满意。特别是在红色调到蓝色调时产生这样的问题。
本发明涉及的分散性染料，该染料得到的染色在热徙动中、在耐洗和耐汗方面都具有很强的牢固性，它还在浸染法、热溶染色法、织物印染法中具有很好的提升性能，它也可适用于拔染印花。
本发明的染料具有下式：
(1)，其中：R1是硝基或氰基，R2是卤素，R3是C1-C4烷基，R4和R5分别独立地是甲基或乙基，R6是氢、甲基或乙基，其前提条件是当R1是氰基，R2是卤素，R3是甲基或异丙基时，或者当R1是硝基，R2是卤素，R3是甲基时，R6不是氢。
R2定义为卤素一般的是氯、溴或碘。
R3定义为C1-C4烷基，例如：甲基，乙基，正丙基，异丙基，正丁基，仲丁基，叔丁基或异丁基。
R2优选为氯或溴，最优选是溴。
R3优选为C1-C3烷基，更优选为甲基、乙基或异丙基，R3特别优选为甲基或乙基，最优选是甲基。
R6优选为甲基或乙基，最优选是甲基。
式(1)的优选的染料是其中：
R1是氰基，R2是氯或溴，R3是C1-C3烷基，更优选为甲基或乙基，最优选是甲基，R4和R5分别独立地是甲基或乙基，更优选为甲基，R6是甲基的那些染料。
式(1)所示染料的制备方法本身是众所周知的，例如，将下式的一种化合物进行重氮化， (2)然后偶合这种重氮化合物就得到一种下式所示的偶合化合物。 (3),其中的R1,R2,R3,R4,R5,R6和式(1)所述的含义相同。
式(2)所示化合物的重氮化是以公知的方式进行，例如，在酸液如盐酸或硫酸含水介质中使用亚硝酸钠，也可用其它的重氮化试剂如亚硝基硫酸进行重氮化。在重氮化过程的反应介质中可以有其它的酸，例如：磷酸、硫酸、醋酸、丙酸、盐酸、或者这些酸的混合物，如磷酸和醋酸的混合物。重氮化反应可在-10-30℃的温度范围内顺利地进行，反应温度最好是在-10℃到室温下进行。
式(2)的重氮化的化合物偶合为式(3)的偶合化合物，偶合也是以公知方式进行，例如在酸、含水或者含水-有机介质中，优选反应温度为-10-30℃，更优选为小于10℃的条件下进行。所用的酸是例如：盐酸、醋酸、硫酸或磷酸。重氮化反应和偶合反应也可在例如同样的反应介质中进行。
式(2)的某些重氮化的化合物与式(3)的某些偶合化合物是公知的或者可用公知的方法制备。
下式所示的偶合化合物是新化合物，是本发明的另一个内容。 (3a),其中R4和P5和式(1)所述的含义相同。
例如，我们可以用3-氨基-N-乙酰苯胺首先与分子式为CH3-CHCl-COOR5的化合物进行反应，然后再与分子式为Cl-CH2-COOR4的化合物进行反应来制得式(3a)所示的偶合化合物。
式(1)所示的新型染料可用于染或印半合成和优选合成疏水性纤维材料，特别是织物材料。由含有这样的半合成或合成疏水性纤维材料的混合纤维组成的织物材料可以用本发明的染料进行染或印。
合适的半合成纺织材料主要是21/2醋酸纤维素和三醋酸纤维素。
合成疏水性纺织材料主要由线性芳香聚酯，例如那些由对苯二甲酸和二醇，特别是乙二醇组成的那些聚脂组成，或者对苯二甲酸和1,4-双(羟甲基)环己烷的缩聚物；还包括聚碳酸脂，例如那些由α,α-二甲基-4,4’-二羟基二苯甲烷和碳酰氯组成的那些聚合物；还包括那些基于聚氯乙烯和聚酰胺的纤维。
用公知的染色方法使用这种新型染料。例如，在传统的阴离子或非离子分散剂存在下(通常分散剂存在于常用的载体上)，以浸染法从含水分散液对聚酯纤维材制进行染色，浸染时的温度为80-140℃,21/2醋酸纤维素的优选染色温度为大约65-85℃，三醋酸纤维素的染色温度可以达到115℃
这种新型染料，对在染浴里同时存在的棉毛材料不同时染色或很少染色(有很好的防染性)，因此，这种新型染料在对聚酯/羊毛和聚酯/纤维素纤维混纺品进行染色时同样非常有用。
这种新型染料适用于热溶染色法、浸染法和连续操作以及印花工艺，尤适用于浸染法。液体的比例取决于所用的设备、被染物及其存在的方式。然而，这种比例可在很宽的范围内进行选择，例如从1∶4到1∶100，优选为从1∶6到1∶25。
所说的纺织材料可以不同的方式存在，例如：纤维状，丝状或粘合纤维织物，机织品或针织品。
如果在把这种新型染料用作染料配方之前进行加工，其性能将更优越。为了达到这个目的，我们把这种染料研碎至其平均粒度为0.1-10微米，研磨可在分散剂存在下进行。例如，把干燥过的染料与一种分散剂一起研碎或以糊状进行捏合，然后在真空中或者以喷雾法进行干燥，然后加水，这样形成的配方即可用于制备印花浆和染浴。
用于印染时，要使用常用的增稠剂，例如改性或非改性的天然品，如：海藻酸盐，印染胶，阿拉伯树胶，结晶树胶，角豆树豆粉，黄蓍胶，羧甲基纤维素，羟乙基纤维素，淀粉；或者合成产品，如：聚丙烯酰胺，聚丙烯酸或其共聚物，或者聚乙烯醇。
本发明的染料对铁离子和铜离子具有抵抗性，可以使上述材料染上均匀的色调，并且具有很好的牢固性，例如有好的耐光牢固性和耐升华牢固性。需要强调的是其优良的耐洗牢固性和耐汗牢固性，特别是其耐热徙动牢固性方面具有优良的性能，这种新型染料以其好的上染率及提升性能而与众不同。
这些新型染料相互结合或与其它染料结合以制备混合色时，这种新型染料也是非常有用的。
本发明涉及这种新型染料的上述应用及其印染合成或半合成疏水性纤维材料特别是纺织材料的方法，这种方法包括用一种或几种新型染料作用于上述材料，或者这几种染料共同作用。上述疏水性纤维材料优选为纺织聚酯材料。按照本发明的染料的详细使用方法和已知的优选工艺条件也可以处理其它基体材料。
式(1)所示的这种新型染料也适用于新近报道的方法，例如热转移印花法。
下述实施例对本发明进行详尽的阐述。除非另有说明，其中的份数和百分比均为重量份或重量百分比，所给温度为摄氏度。重量份与体积份的关系等同于克与立方厘米的关系。
实施例1：
在反应烧瓶里，把50.0份的3-氨基-N-乙酰苯胺在20-30℃的温度下加入到200份的2-氯丙酸甲脂，然后再加入66份的碳酸钠。在连续的搅拌过程中，把所得到的悬浮液均匀加热到127℃并在此温度下维温5小时。然后在125℃、真空状态下进行蒸馏以除去过量的2-氯丙酸甲脂。反应混合物在115℃维温8小时后，然后把120份氯醋酸甲酯加入反应混合物中，然后把反应后的混合物冷却至室温，加入330份水搅拌30分钟直到盐完全溶解。混合物静置一会儿后，反应烧瓶里就会形成两相，把下层有机相分离出来。在旋转蒸发器里，通过蒸馏把有机相中过量的氯醋酸甲脂除去，这样就得到下式所示的105份化合物，
(100)该化合物以树脂型残余物的形式存在，将其溶解于195份醋酸里。
实施例2：
在一个反应烧瓶里，78.6份2-溴-4,6-二硝基苯胺在最高温度为35℃的情况下溶解于107份98％的硫酸中。在温度为25-28℃时，将104份40％的亚硝基硫酸在40分钟的时间内滴加到反应混合物中，然后将反应混合物在25℃的温度下搅拌120分钟。在0-5℃的温度下，把得到的重氮化溶液在60分钟内滴加到300份浓度为35％的实施例1的偶合化合物溶液中，再加入到200份的冰中，通过加冰，保持反应温度不超过5℃。重氮化溶液滴加完以后，把这种混合物搅拌2小时，温度升到20℃。用过滤法把形成的沉淀物收集起来，水洗后干燥，得到153份下式所示的染料， (101),其最大吸收波长是516nm。这种染料对聚酯纺织材料进行染色时，从红色到紫色都具有很好的牢固性能。
实施例3-27：
用与实施例1和2相类似的反应规程，可以制备表1所列举的从式(102)到式(126)所示的染料。在制备实施例1的偶合化合物中，用等克分子数量的下式所示的化合物替代50份3-氨基-N-乙酰苯胺，该化合物可以首先与分子式为CH3-CHCl-COOP5的化合物进行反应，然后再与分子式为Cl-CH2-COOR4的化合物进行反应；也可以与分子式为Cl-CH2-COOR4和Cl-CH2-COOR5的化合物进行彻底烷基化，式中的R4和R5可以相同也可以不同，并且在根据实施例2进行重氮化和偶合时，用等克分子数量的下式所示的化合物替代78.6份2-溴-4,6-二硝基苯胺，
其中的R1,R2,R3,R4和R5的含义与表1所列举的不同的染料的含义相同。
表1
| 实施例号/分子式号 | R1 | R2 | R3 | R4 | R5 | R6 | λmax[nm] |
| 3/(102) | NO2 | Cl | CH2CH3 | CH3 | CH2CH3 | H | 520 |
| 4/(103) | NO2 | Br | CH2CH3 | CH3 | CH2CH3 | H | 516 |
| 5/(104) | NO2 | Br | CH2CH3 | CH2CH3 | CH2CH3 | H | 516 |
| 6/(105) | NO2 | Br | CH3 | CH2CH3 | CH3 | CH3 | 516 |
| 7/(106) | NO2 | Br | CH3 | CH3 | CH2CH3 | CH3 | 516 |
| 8/(107) | NO2 | Br | CH3 | CH2CH3 | CH2CH3 | CH3 | 516 |
| 9/(108) | NO2 | Cl | CH2CH3 | CH3 | CH3 | H | 521 |
| 10/(109) | NO2 | Cl | CH2CH3 | CH2CH3 | CH2CH3 | H | 520 |
| 11/(110) | NO2 | Cl | CH3 | CH3 | CH3 | CH3 | 519 |
| 12/(111) | NO2 | Cl | CH3 | CH3 | CH2CH3 | CH3 | 521 |
| 13/(112) | NO2 | Cl | CH3 | CH2CH3 | CH3 | CH3 | 519 |
| 14/(113) | NO2 | Cl | CH3 | CH2CH3 | CH2CH3 | CH3 | 520 |
| 15/(114) | CN | Br | CH2CH3 | CH3 | CH3 | H | 544 |
| 16/(115) | CN | Br | CH2CH3 | CH2CH3 | CH2CH3 | H | 546 |
| 17/(116) | CN | Br | CH3 | CH3 | CH3 | CH3 | 544 |
| 18/(117) | CN | Br | CH3 | CH3 | CH2CH3 | CH3 | 545544 |
| 19/(118) | CN | Br | CH3 | CH2CH3 | CH3 | CH3 | |
| 20/(119) | CN | Br | CH3 | CH2CH3 | CH2CH3 | CH3 | 544 |
| 21/(120) | CN | Cl | CH2CH3 | CH3 | CH3 | H | 547 |
| 22/(121) | CN | Cl | CH2CH3 | CH2CH3 | CH3 | H | 544 |
| 23/(122) | CN | Cl | CH2CH3 | CH2CH3 | CH2CH3 | H | 545 |
| 24/(123) | CN | Cl | CH3 | CH3 | CH3 | CH3 | 544 |
| 25/(124) | CN | Cl | CH3 | CH2CH3 | CH3 | CH3 | 546 |
| 26/(125) | CN | Cl | CH3 | CH3 | CH2CH3 | CH3 | 544 |
| 27/(126) | CN | Cl | CH3 | CH2CH3 | CH2CH3 | CH3 | 544 |
同样，表1所列举的染料对聚酯纺织材料进行染色时，其紫色调具有很好的牢固性能。
Claims (13)
1．一种下式所示的染料：
(1)，
其中：R1为硝基或氰基，R2为卤素，R3为C1-C4烷基，R4和R5各自独立地为甲基或乙基，R6为氢、甲基或乙基，其前提条件是当R1是氰基，R2是卤素，R3是甲基或异丙基时，或者当R1是硝基，R2是卤素，R3是甲基时，R6不是氢。
2．根据权利要求1所述的染料，其中R2为氯或溴。
3．根据权利要求1或2所述的染料，其中R2为溴。
4．根据权利要求1-3任一项所述的染料，其中R3为C1-C3烷基，优选为甲基。
5．根据权利要求1-4任一项所述的染料，其中R6为甲基或乙基。
6．根据权利要求1-5任一项所述的染料，其中R6为甲基。
7．根据权利要求1-6任一项所述的染料，其中R1为氰基，R2为氯或溴，R3为C1-C3烷基，R4和R5各自独立地为甲基或乙基，R6为甲基。
8．根据权利要求1-7任一项所述的染料，其中R1为氰基，R2为氯或溴，R3,R4,R5和R6为甲基。
9．制备权利要求1中式(1)所示染料的方法，包括将下式的一种化合物进行重氮化， (2)然后偶合这种重氮化合物就得到一种下式所示的偶合化合物。
(3)，
其中的R1,R2,R3,R4,R5和R6和式(1)所述的含义相同。
10．印染半合成或合成疏水性纤维材料特别是纺织材料的方法，包括把一种或几种根据权利要求1所述的染料用于或加入上述材料。
11．根据权利要求10所述的方法，其中的疏水性材料优选为由聚酯纤维组成的纺织材料。
12、一种偶合化合物如下式所示：
(3a),
其中R4和R5各自独立地是甲基或乙基。
13、一种制备权利要求12中式(3a)所示偶合化合物的方法，包括用3-氨基-N-乙酰苯胺首先与分子式为CH3-CHCl-COOR5的化合物进行反应，然后再与分子式为Cl-CH2-COOR4的化合物进行反应，其中R4和R5的含义同式(3a)。
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| CN103709787A (zh) * | 2013-09-05 | 2014-04-09 | 浙江吉华集团股份有限公司 | 一种偶氮型分散染料组合物的合成方法 |
| CN111320879A (zh) * | 2018-12-14 | 2020-06-23 | 东营安诺其纺织材料有限公司 | 一种分散红染料及其制备方法 |
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| NL295141A (zh) * | 1962-07-11 | |||
| GB1012238A (en) * | 1962-09-24 | 1965-12-08 | Ici Ltd | New disperse dyestuffs of the benzene-azo-benzene series |
| TW223103B (zh) * | 1992-02-03 | 1994-05-01 | Ciba Geigy Ag | |
| JPH06329930A (ja) * | 1993-05-06 | 1994-11-29 | Ciba Geigy Ag | アゾ染料 |
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| CN103709787B (zh) * | 2013-09-05 | 2015-12-23 | 浙江吉华集团股份有限公司 | 一种偶氮型分散染料组合物的合成方法 |
| CN111320879A (zh) * | 2018-12-14 | 2020-06-23 | 东营安诺其纺织材料有限公司 | 一种分散红染料及其制备方法 |
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| JP2000053877A (ja) | 2000-02-22 |
| KR19990083402A (ko) | 1999-11-25 |
| ES2200488T3 (es) | 2004-03-01 |
| TW522163B (en) | 2003-03-01 |
| JP4287947B2 (ja) | 2009-07-01 |
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