TW527401B - Disperse dyes - Google Patents
Disperse dyes Download PDFInfo
- Publication number
- TW527401B TW527401B TW087111307A TW87111307A TW527401B TW 527401 B TW527401 B TW 527401B TW 087111307 A TW087111307 A TW 087111307A TW 87111307 A TW87111307 A TW 87111307A TW 527401 B TW527401 B TW 527401B
- Authority
- TW
- Taiwan
- Prior art keywords
- methyl
- ethyl
- formula
- scope
- patent application
- Prior art date
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- 239000000986 disperse dye Substances 0.000 title abstract description 5
- 239000000975 dye Substances 0.000 claims abstract description 49
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 45
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 32
- 239000000463 material Substances 0.000 claims abstract description 21
- 238000004043 dyeing Methods 0.000 claims abstract description 11
- 229920000728 polyester Polymers 0.000 claims abstract description 11
- 238000007639 printing Methods 0.000 claims abstract description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
- 239000000460 chlorine Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- 230000008878 coupling Effects 0.000 claims description 12
- 238000010168 coupling process Methods 0.000 claims description 12
- 238000005859 coupling reaction Methods 0.000 claims description 12
- 230000002209 hydrophobic effect Effects 0.000 claims description 10
- 239000002270 dispersing agent Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000002657 fibrous material Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- -1 3-amino-4-methoxyacetamidobenzene Chemical compound 0.000 claims description 4
- 150000008049 diazo compounds Chemical class 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000004753 textile Substances 0.000 abstract description 12
- 229910052736 halogen Inorganic materials 0.000 abstract description 9
- 150000002367 halogens Chemical group 0.000 abstract description 9
- 239000001257 hydrogen Substances 0.000 abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
- 150000002431 hydrogen Chemical group 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 239000004744 fabric Substances 0.000 description 5
- 238000013508 migration Methods 0.000 description 5
- 230000005012 migration Effects 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 230000002079 cooperative effect Effects 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 238000006193 diazotization reaction Methods 0.000 description 3
- 210000004243 sweat Anatomy 0.000 description 3
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 229920002284 Cellulose triacetate Chemical group 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 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 group 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
- 150000007513 acids Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229920001577 copolymer 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
- 239000012943 hotmelt Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 238000002360 preparation method Methods 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
- 239000000758 substrate Substances 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- QOSTVEDABRQTSU-UHFFFAOYSA-N 1,4-bis(methylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(NC)=CC=C2NC QOSTVEDABRQTSU-UHFFFAOYSA-N 0.000 description 1
- MUHLVSZIVTURCZ-UHFFFAOYSA-N 2-amino-3-bromo-5-nitrobenzonitrile Chemical compound NC1=C(Br)C=C([N+]([O-])=O)C=C1C#N MUHLVSZIVTURCZ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 229920001612 Hydroxyethyl starch Polymers 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 244000042295 Vigna mungo Species 0.000 description 1
- 235000010716 Vigna mungo Nutrition 0.000 description 1
- 235000011453 Vigna umbellata Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000000305 astragalus gummifer gum Substances 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
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000010018 discharge printing Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010016 exhaust dyeing Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229920000591 gum Polymers 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 229940050526 hydroxyethylstarch Drugs 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- SJWQCBCAGCEWCV-UHFFFAOYSA-N n-(3-amino-4-methoxyphenyl)acetamide Chemical compound COC1=CC=C(NC(C)=O)C=C1N SJWQCBCAGCEWCV-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 239000012074 organic phase Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001155 polypropylene Polymers 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
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 150000005599 propionic acid derivatives Chemical class 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007787 solid 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
- 125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229940061610 sulfonated phenol Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
Classifications
-
- 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
- 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
- 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
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/004—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated using dispersed 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)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
Description
527401 A7 B7 五、發明說明（/) 本發明係關於分散性染料、其製備方法、以及其用於 半合成或合成之疏水性纖維材料之染色或印刷上之用途。 分散性染料，即不包含任何水溶性基團之染料，係已久 爲人知者，用以染疏水性紡織材料。然而，其所得之染色物耐 熱遷移不足，且其某些性質亦不佳，尤其是色耐洗度和色耐汗 度。藍色與深藍色色澤特別容易發生此問題。 本發明係關於分散性染料，藉其可得到極耐熱遷移以及 耐洗和耐汗的染色物，且除此之外，其在盡染與熱熔法以及織 物印刷上具有良好的深染性能。該等染料亦適合用於拔染 印刷。 該等新穎染料相當於下式 --------------裝--- (請先閱讀背面之注意事項再本頁) .
-丨線· 其中 R爲硝基或氧基， 經濟部智慧財產局員工消費合作社印製
Ri爲鹵素， R2爲未被取代或被CVC3烷氧基、鹵素、氰基或苯基 取代之烷基， R3爲C1-C4院基， R4爲甲基或乙基， R5爲氫、甲基或乙基，且 R6爲甲基或乙基，但若R爲硝基，Ri爲鹵素，且r2爲 3 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 527401 A7 B7 五、發明說明（>〇 Q-C4烷基，則115不爲氫。 界定爲鹵素之Ri爲溴、氯或碘。 界定爲CrC4烷基之R2與R3典型地各別獨立爲甲基 、乙基、正丙基、異丙基、正丁基、二級丁基、三級丁基 、以及異丁基。 心爲氯或溴。以氯爲佳。 r2爲乙基或甲基。以甲基爲佳。 R3爲乙基或甲基。以甲基爲佳。
Rs爲氫或甲基。以甲基爲佳。 式（1)之染料可由本身已知之方法製備。例如可由下式 化合物之重氮化， --------------裝—— (請先閱讀背面之注意事項再ΐϋΙ本頁)
R
經濟部智慧財產局員工消費合作社印製 以及使所得之重氮化合物偶合至一下式之偶合組分而 得致
R，R,，R2, Rs，R4, R5與R6具有與式⑴中者相同之意義 本紙張尺度適用中國國家標準（CNS)A4規格（21〇 X 297公釐） 527401 A7 B7 經濟部智慧財產局員工消費合作社印製 五、發明說明（ 式(2)化合物之重氮化係以本身已知之方式進行，利如利 用典型上如氫氯酸或硫酸等酸水性介質中之亞硝酸鈉。然 而，該重氮化亦可以其它重氮化劑進行，以使用亞硝醯基硫酸 爲便。該重氮化之反應介質可包含另一種酸，典型上爲磷酸 、硫酸、醋酸、丙酸、氫氯酸、或這些酸的混合物，例如磷 酸與醋酸之混合物。該重氮化方便於-10到30°C，較佳從-l〇°C到室溫之溫度範圍下進行。 式(2)重氮化合物偶合至式(3)偶合組分同樣以已知方法 進行，方便於酸、水或水-有機介質中，較佳於-10到，30°C， 最佳於l〇°C以下之溫度範圍下進行。適合的酸包括氫氯酸 、醋酸、硫酸或磷酸。重氮化與偶合典型上可於相同反應 介質中進行。 ‘ 某些式（2)之重氮組分與式（3)之偶合組分爲已知，或可 以本身上已知之方式製備。 下式之偶合組分爲新穎的，且亦爲本發明之一目的 och3 CH(CH3)COOR6 NHCOCH. (3a), 其中R4與R6具有與式（1)中者相同之意義。 該式(3a)之偶合組分，舉例而言係藉由首先使3-胺基_4_ 甲氧基乙醯苯胺與一式CH3-CHCl-COOR6之化合物反應，接 --------------裝--- (請先閱讀背面之注意事項再本頁) . -·線· 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 527401 A7 ___ B7 五、發明說明（） 著與一式CH2Cl-COOR4之化合物反應而製備。 (請先閱讀背面之注意事項再 該式（1)之新穎染料可用以染色或印刷半合成及較佳合 成之疏水性纖維材料，特別是紡織材料。由包含該半合成或 合成之疏水性纖維材料之混合物所製之紡織材料，亦可以該 等新穎染料染色或印刷。 特別適合之半合成紡織材料爲纖維素二級醋酸酯與纖 維素三醋酸酯。
I 合成疏水性紡織材料主要包括線性芳香族聚酯，典型上 爲對酞酸與二醇（尤其是乙二醇）者，或爲對肽酸與i，4_雙( 羥基甲基)環己烷之縮合物;聚碳酸酯，典型上爲α，α-二甲基_ 4,4’-二羥基二苯基甲烷與光氣者，或以聚氯乙烯與聚烯胺爲 基礎之纖維。 經濟部智慧財產局員工消費合作社印制衣 該等新穎染料以已知之染色方法應用至紡織材料上。 典型上，，於慣用之陰離子或非離子分散劑存在下，且有或無 慣用之膨潤劑(載劑)存在下，於80至140°C之溫度範圍內， 利用盡染法，由一水性分散液對聚酯纖維材料進行染色。纖 維素二級醋酸酯較佳於約65至85°C之溫度下染色，而纖維 素三醋酸酯則於至多115°C之溫度下染色。 該等新穎染料不使同時存在於染浴中之羊毛與棉染色， 或僅有些微的染色(抗性極佳)，故其可輕易用以染聚酯/羊毛 與聚酯/纖維素混紡紗。 該等新穎染料適合於藉由熱熔法染色，適合於盡染與連 續法及適合印刷。較佳爲盡染染色法。該液體比例視所使 用之裝置、基質與呈現之形式而定。然而，其可選自一廣範 6 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 527401 Α7 Β7 五 發明說明（f) 圍，如1:4至1:100,但以1:6至1:25爲佳。 所提之紡織材料可以任何形式呈現，如孅維、 布、或織物或編結物。， ^ 較合宜者爲於使用前，將該等新穎染料轉化爲一染料 配方。此可藉由將染料硏磨成平均粒徑〇·；[至1〇微米之大 小而爲之。硏磨可在分散劑存在下進行。典型上;> 乾燥的 染料與分散劑硏磨，或與分散劑以糊狀形式揉製’ 於 真空下乾燥或噴霧乾燥。加水至所得配方中可^得^卩刷糊 狀物與染浴。 本發明亦關於染料配方，其包括 以該染料配方之組總重爲基準，30至5〇%重量之下式 染料作爲染料組分 ---------------- (請先閱讀背面之注意事項再jR本頁)
經濟部智慧財產局員工消費合作社印製 其中R爲硝基或氰基，Ri爲鹵素，R2爲未被取代或被 Ci-Ca烷氧基、鹵素、氰基或苯基取代之（^-(：4烷基，R3爲 CVC4烷基，114爲甲基或乙基，r5爲氫、甲基或乙基，而R6 爲甲基或乙基，以及 以該染料組成物之組總重爲基準，50至70%重量之分 散劑。 適合的分散劑舉例而言爲陰離子分散劑，如芳香族磺 7 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 527401 A7 B7 五、發明說明（έ) 酸/甲醛縮合物、磺化雜酚油/甲醛縮合物、木質素磺酸酉旨或 丙嫌酸衍生物之共聚物與苯乙烯衍生物之共聚物，較隹爲 芳香族磺酸/甲醛縮合物或木質素磺酸酯，或以聚環氧化物 爲基礎之非離子性分散劑，舉例而言可由環氧乙烷或瓌氧 丙烷之聚合加成反應而得。 本發明之染料配方較佳爲固態。 該等新穎染料配方因易於轉化爲其欲施用之形式，例 如轉化爲成品印刷糊狀物或染浴之形式，而性質卓越。 習用的增稠劑將用於印刷，例如經改質或未經改質之 天然產物，典型上有藻酸鹽、不列顛膠、阿拉伯膠、結晶 膠、稻子豆膠、西黃耆膠、羧基甲基纖維素、羥基乙棊纖 維素、澱粉，或合成產物，典型上有聚丙烯醯胺、聚芮烯 Λ 酸或其共聚物、或聚乙烯醇。 ' 經濟部智慧財產局員工消費合作社印製 -------------裝---- 广請先間讀背面之注意事頊存Hi本頁) 丨線- 該等新穎染料使得所述材料，特別是聚酯材料，有極 好之最終用途性質（良好之耐光堅牢度及耐昇華堅牢度）之 均勻藍到深藍程度之色澤。特別値得一提者爲優異的色耐 洗度及色耐汗度，尤其是耐熱遷轉堅牢度有優異的固定性 。該等新穎染料進一步因良好的盡染與染深(build-up)而顯 卓越。 該等新穎染料亦可極佳地用於彼此或與其它染料混合 之混合色澤的製備。 本發明關於上述新穎染料之用途，並關於對半合成或 合成疏水性纖維材料，尤其是紡織材料，進行染色或印刷 之方法，該方法包括將一或多種該等新穎染料用至或倂入 8 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 527401 A7 B7 五、發明說明（ 所述材料中。該所述疏水性纖維材料較佳爲紡織聚酯材料 。其匕可以本發明方法以及較佳條件處理之基材於以上言亥 等新穎染料用途之詳細說明中可發現。 在其另一方面，本發明係關於該疏水性纖維材料，較 佳爲經所述方法染色或印刷之聚酯紡織材料。 式（1)之新穎染料亦適用於現代記錄方法，如熱轉印刷 Ο 本發明藉以下實例加以說明。除非另有指明，否則份 數與百分比係以重量爲單位，而溫度係指攝氏度數。重量 份數及體積份數間之關係與克及立方公分間之關係相周。 (請先閱讀背面之注意事項再一||1本頁)
I 經濟部智慧財產局員工消費合作社印製 奮例1 在反應瓶中，60.0份重量之3:胺基-4-甲氧基乙醯苯胺 在20至30°C之溫度下加入200份重量之氯乙酸甲酯中。 然後將60份重量之碳酸鈉加至此混合物中。所得懸浮液在 伴隨恆定的攪拌下均勻加熱至115°C，並於此溫度下維持6 小時。在反應完全後，將混合物冷卻至室溫，充入330份 重量之水，攪拌30分鐘，直到鹽完全溶解。在靜置一小段 時間後，於反應瓶中形成兩相。將下層有機相分離出，利 用於旋轉蒸發器中之蒸餾自其中除去過量氯乙酸甲酯。此 得致105份重量之下式化合物， OCH.
CHXOOCH. CHXOOCH, NHCOCH。 (10) Γ 9 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 527401 A7 B7 五、發明說明（沴） 其形式爲樹脂狀殘餘物，接著溶於195份重量之乙酸 中。 _ 2 在反應瓶中，將72.6份重量之2-胺基-3_溴-5-硝基苄 腈於35°C之最大溫度下溶於107份重量之98%硫酸中。在 40分鐘內逐滴加入1〇4份重量之40%亞硝醯基硫酸至此反 應混合物中，然後於25°C下攪拌12〇分鐘。接著將所得偶 氮溶液於〇至5°C下60分鐘內逐滴加入300份重量之實例 1偶合組分之35%溶液中，並加入200份重量之冰，反應 溫度藉由加入冰維持在最多5°C。在該偶氮溶液加入完成 後，攪拌混合物2小時，溫度升至2〇°C。 過濾收集所得沉澱物，以水淸洗並乾燥之，得到153 份重量之下式染料， 經濟部智慧財產局員工消費合作社印製 ---— II---— — — — — · 11 (請先閱讀背面之注意事項再H本頁) --線· CN OCH3 - CH2COOCH3 (100)
Br NHCOCH3 其將聚酯紡織材料染成具有良好堅牢度性質之藍色色 10 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 527401 A7 B7 q 五、發明說明（ ) 澤，特別是具有良好耐熱遷移堅牢度。 實例3-22 列於表1之式（101)至（12〇)染料可以寶例 般類似方法加以製備。其亦將聚酯紡織材觀Μ所指示之一 k成具有良好 堅牛度性質之丨朱監與監色色澤，特別是具有良好耐熱遷移 堅牢度和色耐洗度。 --------------裝·！ (請先閱讀背面之注意事項再hi本頁)
訂---------線 經濟部智慧財產局員工消費合作社印製 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公爱） 527401
7 7 A B 五、發明說明（/〇)表1 02n
OCH. N = N
CH9COOR4 CHRXOORg NHCOCH3 經濟部智慧財產局員工消費合作社印製 實例號/式號 R Ri r4 Rs R6 色度 3/(101) N〇2 Br ch3 ch3 ch3 深藍 4/(102) N〇2 Br CH2CH3 ch3 ch3 深藍 5/(103) N〇2 Br ch3 ch3 CH2CH3 深藍 6/(104) N〇2 Br CH2CH3 ch3 CH2CH3 深藍 7/(105) N〇2 Cl ch3 ch3 ch3 深藍 8/(106) N〇2 Cl ch3 ch3 CH2CH3 深藍 9/(107) N〇2 Cl CH2CH3 ch3 ch3 深藍 10/(108) N〇2 Cl CH2CH3 ch3 CH2CH3 深藍 11/(109) CN Br CH2CH3 H CH2CH3 藍 12/(110) CN Br ch3 ch3 ch3 藍 13/(111) CN Br ch3 ch3 CH2CH3 藍 14/(112) CN Br ch2ch3 ch3 ch3 藍 15/(113) CN Br CH2CH3 ch3 CH2CH3 藍 16/(114) CN Cl ch3 H ch3 藍 17/(115) CN Cl CH2CH3 H ch3 藍 18/(116) CN Cl CH2CH3 H CH2CH3 藍 19/(117) CN Cl ch3 ch3 ch3 藍 20/(118) CN Cl CH2CH3 ch3 ch3 藍 21/(119) CN Cl ch3 ch3 CH2CH3 藍 22/(120) CN Cl CH2CH3 ch3 CH2CH3 藍 較佳之染料爲式（101)至（108)、（110)至（113)、與（117) 至（120)者。尤佳之染料爲式（106)、（108)、（110)、（117)與 (119)者。 12 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） ------I I I I I--I --- (請先閱讀背面之注意事項再^^|本頁) .. 線-
Claims (1)
- 527401 A8 B8 C8 D8 申請專利範圍、:: 1. 一種下式之染料，⑴ 其中R爲硝基或氰基，Ri爲氯或溴，R2爲甲基或乙基， R3爲甲基或乙基，R4爲甲基或乙基，R5爲甲基，而R6爲甲 基或乙基。 2. 根據申請專利範圍第1項之染料，其中R爲氰基，I 爲氯或溴，R2與R3各別獨立爲甲基或乙基，R4爲甲基或乙 基，R5爲甲基，而R>6爲甲基或乙基。 3. —種如申請專利範圍第1項之式（1)染料之製備方法， 其包括使下式化合物重氮化， ON(2) 以及使所得之重氮化合物偶合至一下式之偶合組分NHCOR. (3) — (請先閲讀背面之注意事項再填寫本頁) 訂： 本紙張尺度適用中國國家標準（CNS)A4規格(210 X 297公釐) 527401 (3a) A8 B8 C8 D8 、申請專利範圍 其中R，Ri，R2, r3, r4, r5與尺6具有與式（1)中者相同之 意義。 4· 一種染色或印刷半合成或合成之疏水性纖維材料之 方法，包括將一或多種根據申請專利範圍第1項之染料用至 或倂入所提材料中。 5·根據申請專利範圍第4項之方法，其中該疏水性材料， 係由聚酯纖維所構成。 6·—種由根據申請專利範圍第4項或第5項方法所染 色或印刷之材料。 7· —種下式之偶合組分， och3 CH(CH3)C00R6 NHCOCH. 其中R4爲甲基或乙基，且R6爲甲基或乙基。 8·—種根據申請專利範圍第7項之式(3a)偶合組分之製 備方法，其包括首先使3-胺基-4-甲氧基乙醯胺苯與一式 CH3-CHCl-COOR6之化合物反應，接著與一式CH2Cl-COOR4 之化合物反應，R4與R6具有與式(3a)中者相同之意義。 9. 一種染料組成物，包括 a)以該染料組成物之總重爲基準，3〇至50%重量之下式 染料作爲染料組分 16 本紙張尺度適用中國國家標準(CNS)A4規格(210 X 297公釐） -------------------........·!訂----------------· (請先閲讀背面之注意事項再塡寫本頁) 527401 A8 B8 C8 D8 ολν申請專利範圍 ⑴ 其中R爲硝基或氰基，Κ爲氯或溴，R2爲甲基或乙基， R3爲甲基或乙基，R4爲甲基或乙基，R5爲甲基，而爲甲 基或乙基，以及 b)以該染料組成物之總重爲基準，50至70%重量之分 散劑。 ------------------------— (請先閲讀背面之注意事項再塡寫本頁) '1T·— 本紙張尺度適用中國國家標準（CNS)A4規格(210 X 297公釐)
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|---|---|---|---|---|
| US2373700A (en) * | 1940-06-29 | 1945-04-17 | Eastman Kodak Co | Azo compounds and material colored therewith |
| US3178405A (en) * | 1956-07-25 | 1965-04-13 | Merian Ernest | Water-insoluble monoazo dyestuffs |
| US3637652A (en) * | 1962-09-24 | 1972-01-25 | Ici Ltd | Disperse monoazo dyestuffs |
| FR1377496A (fr) | 1963-09-24 | 1964-11-06 | Ici Ltd | Nouveaux colorants dispersés |
| US4210586A (en) * | 1978-06-23 | 1980-07-01 | Eastman Kodak Company | Disperse dyes from 2-bromo, chloro, or cyano-4,6-dinitroaniline and selected alkyl-3-(2'-alkoxy-5-alkanoylaminoanilino)butyrate or alkyl-4-(2'-alkoxy-5'-alkanoylaminoanilino)valerate |
| JPS55115853A (en) * | 1979-03-02 | 1980-09-06 | Mitsui Toatsu Chem Inc | Preparation of aromatic amine |
| JPS55116754A (en) | 1979-03-05 | 1980-09-08 | Mitsui Toatsu Chem Inc | Monoazo compound, its preparation, and dyeing of synthetic fiber |
| US4389531A (en) * | 1980-06-12 | 1983-06-21 | Eastman Kodak Company | Preparation of N-substituted anilines |
| JPS58152056A (ja) * | 1982-03-05 | 1983-09-09 | Sumitomo Chem Co Ltd | モノアゾ化合物の製法 |
| 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 |
-
1998
- 1998-06-19 PL PL326913A patent/PL193092B1/pl not_active IP Right Cessation
- 1998-07-06 US US09/110,595 patent/US5939579A/en not_active Expired - Lifetime
- 1998-07-07 EP EP98810637A patent/EP0894830B1/de not_active Expired - Lifetime
- 1998-07-09 JP JP19425398A patent/JP4287923B2/ja not_active Expired - Fee Related
- 1998-07-10 BR BR9802435A patent/BR9802435A/pt not_active Application Discontinuation
- 1998-07-13 CZ CZ982208A patent/CZ220898A3/cs unknown
- 1998-07-13 TW TW087111307A patent/TW527401B/zh active
- 1998-07-14 KR KR1019980028276A patent/KR100565382B1/ko not_active IP Right Cessation
- 1998-07-14 ID IDP981002A patent/ID20597A/id unknown
- 1998-07-14 CN CN98116047A patent/CN1103798C/zh not_active Expired - Fee Related
-
1999
- 1999-05-13 US US09/311,093 patent/US6034226A/en not_active Expired - Lifetime
-
2005
- 2005-09-30 KR KR1020050092142A patent/KR100692889B1/ko not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CN1208057A (zh) | 1999-02-17 |
| EP0894830A3 (de) | 1999-09-08 |
| EP0894830A2 (de) | 1999-02-03 |
| KR19990013824A (ko) | 1999-02-25 |
| EP0894830B1 (de) | 2011-08-24 |
| ID20597A (id) | 1999-01-21 |
| CZ220898A3 (cs) | 1999-03-17 |
| PL326913A1 (en) | 1999-01-18 |
| KR100565382B1 (ko) | 2006-06-23 |
| PL193092B1 (pl) | 2007-01-31 |
| JPH1171530A (ja) | 1999-03-16 |
| KR20060086813A (ko) | 2006-08-01 |
| US5939579A (en) | 1999-08-17 |
| BR9802435A (pt) | 1999-07-20 |
| US6034226A (en) | 2000-03-07 |
| JP4287923B2 (ja) | 2009-07-01 |
| CN1103798C (zh) | 2003-03-26 |
| KR100692889B1 (ko) | 2007-03-12 |
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| GD4A | Issue of patent certificate for granted invention patent |