JP5955224B2 - Disperse dye and method for dyeing hydrophobic fiber material using the same - Google Patents
Disperse dye and method for dyeing hydrophobic fiber material using the same Download PDFInfo
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- JP5955224B2 JP5955224B2 JP2012546763A JP2012546763A JP5955224B2 JP 5955224 B2 JP5955224 B2 JP 5955224B2 JP 2012546763 A JP2012546763 A JP 2012546763A JP 2012546763 A JP2012546763 A JP 2012546763A JP 5955224 B2 JP5955224 B2 JP 5955224B2
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- 239000000986 disperse dye Substances 0.000 title claims description 188
- 238000004043 dyeing Methods 0.000 title claims description 59
- 238000000034 method Methods 0.000 title claims description 14
- 239000002657 fibrous material Substances 0.000 title claims description 8
- 230000002209 hydrophobic effect Effects 0.000 title description 6
- 239000000203 mixture Substances 0.000 claims description 122
- 239000000975 dye Substances 0.000 claims description 36
- 238000010186 staining Methods 0.000 claims description 10
- 239000006185 dispersion Substances 0.000 claims description 8
- 239000000835 fiber Substances 0.000 description 18
- 239000000843 powder Substances 0.000 description 17
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 14
- 239000002270 dispersing agent Substances 0.000 description 13
- 239000000463 material Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- MTZWHHIREPJPTG-UHFFFAOYSA-N phorone Chemical compound CC(C)=CC(=O)C=C(C)C MTZWHHIREPJPTG-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000004744 fabric Substances 0.000 description 5
- 239000010419 fine particle Substances 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- 239000001045 blue dye Substances 0.000 description 4
- 239000001044 red dye Substances 0.000 description 4
- 229920002994 synthetic fiber Polymers 0.000 description 4
- 239000012209 synthetic fiber Substances 0.000 description 4
- 239000001043 yellow dye Substances 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 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 3
- DYALWCKAJBVSBZ-UHFFFAOYSA-N 1-anilino-4,5-dihydroxy-8-nitroanthracene-9,10-dione Chemical compound C1=2C(=O)C(C(=CC=C3O)[N+]([O-])=O)=C3C(=O)C=2C(O)=CC=C1NC1=CC=CC=C1 DYALWCKAJBVSBZ-UHFFFAOYSA-N 0.000 description 2
- VGKYEIFFSOPYEW-UHFFFAOYSA-N 2-methyl-4-[(4-phenyldiazenylphenyl)diazenyl]phenol Chemical compound Cc1cc(ccc1O)N=Nc1ccc(cc1)N=Nc1ccccc1 VGKYEIFFSOPYEW-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229920000161 Locust bean gum Polymers 0.000 description 2
- NZBSAAMEZYOGBA-UHFFFAOYSA-N O=C(c1cccc2cccc-3c12)[n]1c-3nc2c1cccc2 Chemical compound O=C(c1cccc2cccc-3c12)[n]1c-3nc2c1cccc2 NZBSAAMEZYOGBA-UHFFFAOYSA-N 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000000711 locust bean gum Substances 0.000 description 2
- 235000010420 locust bean gum Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- BXIGAWRFDMDLTL-UHFFFAOYSA-N n-(4-amino-3-methoxy-9,10-dioxoanthracen-1-yl)-4-methylbenzenesulfonamide Chemical compound C=12C(=O)C3=CC=CC=C3C(=O)C2=C(N)C(OC)=CC=1NS(=O)(=O)C1=CC=C(C)C=C1 BXIGAWRFDMDLTL-UHFFFAOYSA-N 0.000 description 2
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- CNRPDCKHCGUKDK-UHFFFAOYSA-N 1,8-bis(phenylsulfanyl)anthracene-9,10-dione Chemical compound C=12C(=O)C3=C(SC=4C=CC=CC=4)C=CC=C3C(=O)C2=CC=CC=1SC1=CC=CC=C1 CNRPDCKHCGUKDK-UHFFFAOYSA-N 0.000 description 1
- RQLMZSLFKGNXTO-UHFFFAOYSA-N 1-amino-4-hydroxy-2-(6-hydroxyhexoxy)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC(OCCCCCCO)=C2N RQLMZSLFKGNXTO-UHFFFAOYSA-N 0.000 description 1
- 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 1
- CZNYJWQJSGRKRA-UHFFFAOYSA-N 2-[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]aniline Chemical compound NC1=CC=CC=C1C1=NN=C(C=2C=CC(Cl)=CC=2)O1 CZNYJWQJSGRKRA-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
- BZOVBIIWPDQIHF-UHFFFAOYSA-N 3-hydroxy-2-methylbenzenesulfonic acid Chemical compound CC1=C(O)C=CC=C1S(O)(=O)=O BZOVBIIWPDQIHF-UHFFFAOYSA-N 0.000 description 1
- BBFRYSKTTHYWQZ-UHFFFAOYSA-N 4-anilino-3-nitro-n-phenylbenzenesulfonamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC=2C=CC=CC=2)=CC=C1NC1=CC=CC=C1 BBFRYSKTTHYWQZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 229920002907 Guar gum Polymers 0.000 description 1
- 244000073231 Larrea tridentata Species 0.000 description 1
- 235000006173 Larrea tridentata Nutrition 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 0 [O-][N+](c(cc(*c1ccccc1)cc1)c1Nc1ccccc1)=O Chemical compound [O-][N+](c(cc(*c1ccccc1)cc1)c1Nc1ccccc1)=O 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000009835 boiling Methods 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
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229960002126 creosote Drugs 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 229920006239 diacetate fiber Polymers 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000007447 staining method Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920006304 triacetate fiber Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/08—Naphthalimide dyes; Phthalimide dyes
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/51—N-substituted amino-hydroxy anthraquinone
- C09B1/514—N-aryl derivatives
- C09B1/5145—N-aryl derivatives only amino and hydroxy groups
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/54—Amino-hydroxy-anthraquinones; Ethers and esters thereof etherified
- C09B1/545—Anthraquinones with aliphatic, cycloaliphatic or araliphatic ether groups
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/56—Mercapto-anthraquinones
- C09B1/58—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals
- C09B1/585—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals substituted by aryl radicals
-
- 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
- C09B25/00—Quinophthalones
-
- 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
- C09B51/00—Nitro or nitroso dyes
-
- 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
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
Description
本発明は、染料組成物及びそれを用いる染色法に関する。更に詳しくは、特定の染料を含有した黄色系、赤色系及び青色系分散染料組成物、並びにそれを用いる疎水性繊維材料の染色法に関する。 The present invention relates to a dye composition and a dyeing method using the same. More specifically, the present invention relates to a yellow, red and blue disperse dye composition containing a specific dye, and a method for dyeing a hydrophobic fiber material using the same.
自動車内装材料に用いられる合成繊維材料は、自動車内が高温多湿になることや、太陽光に露光される時間が他の一般衣料繊維材料に較べ格段に長いため、強い耐温度性能や耐光性能を要求される。これを解決するために、耐光堅牢度の強い染料を用いて繊維材料を染色する方法がとられている。しかしながら、黄色染料、赤色染料、青色染料の各々の耐光堅牢度のバランスが異なっていると、長時間の露光により一部の色の染料だけが褪色を起こし当初の色と異なってくるため、染色当初に比べて色変色がより大きく見えるという欠点が有る。このため使用される黄色染料、赤色染料、青色染料には、同じように褪色してゆくバランスの取れた耐光堅牢度が要求される。 Synthetic fiber materials used for automobile interior materials have strong temperature resistance and light resistance because the interior of automobiles is hot and humid and the exposure time to sunlight is much longer than other general textile materials. Required. In order to solve this, a method of dyeing a fiber material using a dye having strong light fastness has been taken. However, if the light fastness balance of the yellow dye, red dye, and blue dye is different, only a part of the color dyes will fade and become different from the original color due to long exposure. There is a drawback that the color change looks larger than the original. For this reason, the yellow dye, the red dye, and the blue dye to be used are required to have balanced light fastness that is similarly faded.
また、これらの合成繊維材料の糸の太さや、糸の形状の違い、使われるポリエステル繊維に他の繊維材料を混紡した混紡繊維等の違いにより、同じ染色方法においても染色濃度、染色色調等が異なってくる。このように形状、性質の異なる合成繊維材料を毎回同じように染色加工するためには、各種染色条件でも染色再現性に優れた染料が要求される。
自動車内装材料を染色するときには出来るだけ耐光堅牢度の強い分散染料を使用して染色を行うが、これに加えて、黄色染料、赤色染料、青色染料の染色特性（染色速度等）が揃っていないと、染色された合成繊維材料の染色再現性に違いが出てしまう。そのため、三原色の染料間で染色特性が揃っていることが要求される。In addition, due to differences in yarn thickness of these synthetic fiber materials, yarn shapes, blended fibers in which other fiber materials are blended with the polyester fibers used, the dyeing density, dyeing color tone, etc. are the same in the same dyeing method. Come different. Thus, in order to dye the synthetic fiber materials having different shapes and properties in the same manner every time, a dye having excellent dye reproducibility is required even under various dyeing conditions.
When dyeing automobile interior materials, disperse dyes with as much light fastness as possible are used for dyeing, but in addition to this, the dyeing characteristics (dyeing speed, etc.) of yellow, red, and blue dyes are not complete. And the dyeing reproducibility of the dyed synthetic fiber material is different. Therefore, it is required that the dyeing characteristics are uniform among the three primary color dyes.
これらの問題点を解決するために、黄色染料、赤色染料、青色染料の各色の耐光堅牢度が強く且つその強度が揃っていて、各色の染色再現性がよい分散染料組成物が求められている。 In order to solve these problems, there is a need for a disperse dye composition having strong light fastness and uniform strength for each color of yellow, red, and blue dyes and good color reproducibility for each color. .
本発明者等は前記課題を解決すべく鋭意研究の結果、各種分散染料の成分を適宜組みあわせることにより、各色の耐光堅牢度が強いだけでなく三原色のバランスよい耐光堅牢度を持ち、且つ、染色時の染色特性が揃った混合分散染料組成物を与えることができる特定の分散染料組成物、該混合分散染料組成物、それを用いた染色方法を見出し、本発明を完成させるに至った。 As a result of diligent research to solve the above problems, the present inventors have appropriately combined the components of various disperse dyes, so that not only the light fastness of each color is strong but also the light fastness with a good balance of the three primary colors, and The inventors have found a specific disperse dye composition capable of providing a mixed disperse dye composition having uniform dyeing characteristics at the time of dyeing, the mixed disperse dye composition, and a dyeing method using the same, thereby completing the present invention.
即ち、本発明の諸態様は、以下の１）から１０）に関する。
１）式（１）で表される分散染料、
式（２）で表される分散染料、並びに、
式（３）で表される分散染料、式（４）で表される分散染料及び式（５）で表される分散染料からなる群から選ばれる１〜３の分散染料からなる染料を含有する黄色系分散染料組成物。
1) a disperse dye represented by the formula (1),
A disperse dye represented by formula (2), and
Contains a disperse dye represented by formula (3), a disperse dye represented by formula (4), and a dye comprising 1 to 3 disperse dyes selected from the group consisting of a disperse dye represented by formula (5) Yellow disperse dye composition.
２）黄色系分散染料組成物の全重量に対して、式（１）で表される分散染料を１．０〜２０．０重量％、式（２）で表される分散染料を１．０〜２０．０重量％、並びに、式（３）で表される分散染料を１０．０〜４０．０重量％、及び／又は式（４）で表される分散染料を５．０〜３０．０重量％、及び／又は式（５）で表される分散染料を１．０〜２０．０重量％の割合で含有する前記１）に記載の黄色系分散染料組成物。 2) 1.0-20.0% by weight of the disperse dye represented by the formula (1) and 1.0% of the disperse dye represented by the formula (2) with respect to the total weight of the yellow disperse dye composition. To 20.0% by weight, 10.0 to 40.0% by weight of the disperse dye represented by the formula (3), and / or 5.0 to 30.30% of the disperse dye represented by the formula (4). The yellow disperse dye composition as described in 1) above, containing 0% by weight and / or the disperse dye represented by the formula (5) at a ratio of 1.0 to 20.0% by weight.
３）前記１）又は２）に記載の黄色系分散染料組成物と、式（６）及び／又は式（７）で表される分散染料を含有する赤色系分散染料組成物とからなる混合分散染料組成物。
４）赤色系分散染料組成物の全重量に対して、式（６）で表される分散染料を５．０〜４０．０重量％、及び式（７）で表される分散染料を１０．０〜６０．０重量％の割合で含有する前記３）に記載の混合分散染料組成物。3) A mixed dispersion comprising the yellow disperse dye composition described in 1) or 2) above and a red disperse dye composition containing a disperse dye represented by formula (6) and / or formula (7) Dye composition.
4) 5.0 to 40.0% by weight of the disperse dye represented by the formula (6) and 10% of the disperse dye represented by the formula (7) with respect to the total weight of the red disperse dye composition. The mixed disperse dye composition as described in 3) above, which is contained at a ratio of 0 to 60.0% by weight.
５）前記１）又は２）に記載の黄色系分散染料組成物と、式（８）及び／又は式（９）で表される分散染料を含有する青色系分散染料組成物とからなる混合分散染料組成物。
６）青色系分散染料組成物の全重量に対して、式（８）で表される分散染料を１０．０〜４０．０重量％、及び式（９）で表される分散染料を１．０〜１５．０重量％の割合で含有する前記５）に記載の混合分散染料組成物。5) Mixed dispersion comprising the yellow disperse dye composition described in 1) or 2) above and a blue disperse dye composition containing a disperse dye represented by formula (8) and / or formula (9) Dye composition.
6) 10.0 to 40.0% by weight of the disperse dye represented by Formula (8) and 1. 1 of the disperse dye represented by Formula (9) with respect to the total weight of the blue disperse dye composition. The mixed disperse dye composition as described in 5) above, which is contained at a ratio of 0 to 15.0% by weight.
７）前記３）に記載の式（６）及び／又は式（７）で表される分散染料を含有する赤色系分散染料組成物と、前記５）に記載の式（８）及び／又は式（９）で表される分散染料を含有する青色系分散染料組成物とからなる混合分散染料組成物。
８）前記１）又は２）に記載の黄色系分散染料組成物と、前記７）に記載の混合分散染料組成物とからなる混合分散染料組成物。7) A red disperse dye composition containing the disperse dye represented by formula (6) and / or formula (7) described in 3) above, and formula (8) and / or formula described in 5) above. A mixed disperse dye composition comprising the blue disperse dye composition containing the disperse dye represented by (9).
8) A mixed disperse dye composition comprising the yellow disperse dye composition described in 1) or 2) above and the mixed disperse dye composition described in 7) above.
９）前記１）〜８）のいずれか一項に記載の分散染料組成物を用いることを特徴とする繊維材料の染色法。
１０）前記９）に記載の染色法により染色された繊維材料を含む物品。9) A method for dyeing a fiber material, wherein the disperse dye composition according to any one of 1) to 8) is used.
10) An article comprising a fiber material dyed by the dyeing method described in 9) above.
本発明の黄色系分散染料組成物、赤色系分散染料組成物及び青色系分散染料組成物は、各々強い耐光堅牢度を有する。加えて、それらの所定の組み合わせを含む混合分散染料組成物として用いる際に、各色において、耐光堅牢度が揃っており、且つ、三原色の染色時の再現性がよく染色特性が揃っている。これらの分散染料組成物及び混合分散染料組成物は、特に、高温多湿で耐光性能が要求される自動車内に使用する疎水性繊維の染色に適している。 The yellow disperse dye composition, red disperse dye composition and blue disperse dye composition of the present invention each have a strong light fastness. In addition, when used as a mixed disperse dye composition containing these predetermined combinations, the light fastness is uniform for each color, and the reproducibility during the dyeing of the three primary colors is good and the dyeing characteristics are uniform. These disperse dye compositions and mixed disperse dye compositions are particularly suitable for dyeing hydrophobic fibers used in automobiles that are required to have high temperature and humidity and light resistance.
以下に、本発明を詳細に説明する。
本発明の黄色系分散染料組成物は、前記式（１）で表される分散染料、前記式（２）で表される分散染料、並びに、前記式（３）で表される分散染料、前記式（４）で表される分散染料及び前記式（５）で表される分散染料からなる群から選ばれる１〜３の分散染料とからなる染料を含有する。The present invention is described in detail below.
The yellow disperse dye composition of the present invention includes a disperse dye represented by the formula (1), a disperse dye represented by the formula (2), a disperse dye represented by the formula (3), It contains a dye comprising a disperse dye represented by formula (4) and 1-3 disperse dyes selected from the group consisting of the disperse dye represented by formula (5).
式（１）で表される分散染料は、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ Ｙｅｌｌｏｗ ７１であり、公知文献に基づいて製造することができる。または、市販の染料を使用することもできる。ベンゾイミダゾール構造のフェニル基に置換しているメトキシ基の置換位置は、特に限定されない。
式（２）で表される分散染料は、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ Ｙｅｌｌｏｗ ６４であり、公知文献に基づいて製造することができる。または、市販の染料を使用することもできる。
式（３）で表される分散染料は、Ｃ．Ｉ．Ｓｏｌｖｅｎｔ Ｙｅｌｌｏｗ １６３であり、公知文献に基づいて製造することができる。または、市販の染料を使用することもできる。
式（４）で表される分散染料は、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ Ｙｅｌｌｏｗ ６５であり、公知文献に基づいて製造することができる。または、市販の染料を使用することもできる。
式（５）で表される分散染料は、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ Ｙｅｌｌｏｗ ４２であり、公知文献に基づいて製造することができる。または、市販の染料を使用することもできる。The disperse dye represented by the formula (1) is C.I. I. Disperse Yellow 71, which can be manufactured based on known literature. Alternatively, commercially available dyes can also be used. The substitution position of the methoxy group substituted on the phenyl group of the benzimidazole structure is not particularly limited.
The disperse dye represented by the formula (2) is C.I. I. Disperse Yellow 64, which can be manufactured based on known literature. Alternatively, commercially available dyes can also be used.
The disperse dye represented by the formula (3) is C.I. I. Solvent Yellow 163, which can be manufactured based on known literature. Alternatively, commercially available dyes can also be used.
The disperse dye represented by the formula (4) is C.I. I. Disperse Yellow 65, which can be manufactured based on known literature. Alternatively, commercially available dyes can also be used.
The disperse dye represented by the formula (5) is C.I. I. Disperse Yellow 42, which can be manufactured based on known literature. Alternatively, commercially available dyes can also be used.
該黄色系分散染料組成物は、この組成物の全重量に対して、好ましくは、式（１）で表される分散染料を１．０〜２０．０重量％、式（２）で表される分散染料を１．０〜２０．０重量％、並びに、式（３）で表される分散染料を１０．０〜４０．０重量％、及び／又は式（４）で表される分散染料を５．０〜３０．０重量％、及び／又は式（５）で表される分散染料を１．０〜２０．０重量％の割合で含有する。 The yellow disperse dye composition is preferably 1.0 to 20.0% by weight of the disperse dye represented by the formula (1) and represented by the formula (2) with respect to the total weight of the composition. 1.0 to 20.0 wt% of the disperse dye and 10.0 to 40.0 wt% of the disperse dye represented by the formula (3) and / or the disperse dye represented by the formula (4) Is contained in a proportion of 1.0 to 20.0% by weight, and / or a disperse dye represented by the formula (5).
該黄色系分散染料組成物と、前記式（６）及び／又は前記式（７）で表される分散染料を含有する赤色系分散染料組成物とからなる混合分散染料組成物もまた、好ましく使用される。
式（６）で表される分散染料は、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ Ｒｅｄ ９１であり、公知文献に基づいて製造することができる。または、市販の染料を使用することもできる。
式（７）で表される分散染料は、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ Ｒｅｄ ８６であり、公知文献に基づいて製造することができる。または、市販の染料を使用することもできる。
該赤色系分散染料組成物は、この組成物の全重量に対して、好ましくは、式（６）で表される分散染料を５．０〜４０．０重量％、及び式（７）で表される分散染料を１０．０〜６０．０重量％の割合で含有する。A mixed disperse dye composition comprising the yellow disperse dye composition and the red disperse dye composition containing the disperse dye represented by the formula (6) and / or the formula (7) is also preferably used. Is done.
The disperse dye represented by the formula (6) is C.I. I. Disperse Red 91, which can be manufactured based on known literature. Alternatively, commercially available dyes can also be used.
The disperse dye represented by the formula (7) is C.I. I. Disperse Red 86, which can be manufactured based on known literature. Alternatively, commercially available dyes can also be used.
The red disperse dye composition is preferably 5.0 to 40.0% by weight of the disperse dye represented by the formula (6) and the formula (7) based on the total weight of the composition. The disperse dye to be produced is contained in a proportion of 10.0 to 60.0% by weight.
該黄色系分散染料組成物と、前記式（８）及び／又は前記式（９）で表される分散染料を含有する青色系分散染料組成物とからなる混合分散染料組成物もまた、好ましく使用される。
式（８）で表される分散染料は、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ Ｂｌｕｅ ７７であり、公知文献に基づいて製造することができる。または、市販の染料を使用することもできる。
式（９）で表される分散染料は、フェニル基の置換基がメトキシ基とエトキシ基の等モル程度の混合物である。この分散染料は、特開平４−１６４９６８号公報等の公知文献に記載の染料であり、市販されている染料を使用してもよい。
該青色系分散染料組成物は、この組成物の全重量に対して、好ましくは、式（８）で表される分散染料を１０．０〜４０．０重量％、及び式（９）で表される分散染料を１．０〜１５．０重量％の割合で含有する。A mixed disperse dye composition comprising the yellow disperse dye composition and the blue disperse dye composition containing the disperse dye represented by the formula (8) and / or the formula (9) is also preferably used. Is done.
The disperse dye represented by the formula (8) is C.I. I. Disperse Blue 77, which can be manufactured based on known literature. Alternatively, commercially available dyes can also be used.
The disperse dye represented by the formula (9) is a mixture in which the substituent of the phenyl group is approximately equimolar of a methoxy group and an ethoxy group. This disperse dye is a dye described in a known document such as JP-A-4-164968, and a commercially available dye may be used.
The blue disperse dye composition is preferably 10.0 to 40.0% by weight of the disperse dye represented by the formula (8) and the formula (9) based on the total weight of the composition. The disperse dye to be contained is contained in a proportion of 1.0 to 15.0% by weight.
また、前記式（６）及び／又は前記式（７）で表される分散染料を含有する赤色系分散染料組成物と、前記式（８）及び／又は前記式（９）で表される分散染料を含有する青色系分散染料組成物とからなる混合分散染料組成物もまた、好ましく使用される。この際、赤色系分散染料組成物と青色系分散染料組成物それぞれの好ましい組成も、前記と同様である。一態様として、この混合分散染料組成物は、前記黄色系分散染料組成物と混合せずに使用することもできる。 Moreover, the red disperse dye composition containing the disperse dye represented by the formula (6) and / or the formula (7), and the dispersion represented by the formula (8) and / or the formula (9). A mixed disperse dye composition comprising a blue disperse dye composition containing a dye is also preferably used. At this time, preferred compositions of the red disperse dye composition and the blue disperse dye composition are also the same as described above. As an embodiment, the mixed disperse dye composition can be used without being mixed with the yellow disperse dye composition.
更に、前記の黄色系分散染料組成物、前記の赤色系分散染料組成物、及び前記の青色系分散染料組成物の混合分散染料組成物もまた、好ましく使用される。この場合の各分散染料組成物の好ましい組成も、前記と同様である。 Furthermore, a mixed disperse dye composition of the yellow disperse dye composition, the red disperse dye composition, and the blue disperse dye composition is also preferably used. The preferred composition of each disperse dye composition in this case is also the same as described above.
本発明の分散染料組成物は、前記の分散染料の各原末を適当な配合比率で混合した後に後記の微粒子化（分散化）処理を施して使用してもよいし、又は、前記の分散染料の各原末を別個に微粒子化（分散化）処理を施した後に適当な割合で混合して使用してもよい。後者にあっては、染浴に微粒子化（分散化）処理が施された各分散染料を適当な量で添加し、本発明の分散染料組成物を染浴中にて形成させて使用してもよい。また、微粒子化された分散染料組成物に、必要に応じて分散剤を後から加えてもよい。 The disperse dye composition of the present invention may be used after mixing each raw powder of the disperse dye at an appropriate blending ratio and then subjecting it to the fine particle (dispersion) treatment described later, or the disperse dye composition described above. Each raw powder of the dye may be separately used after being finely divided (dispersed) and mixed at an appropriate ratio. In the latter case, an appropriate amount of each disperse dye that has been finely divided (dispersed) is added to the dye bath, and the disperse dye composition of the present invention is formed in the dye bath and used. Also good. Moreover, you may add a dispersing agent later to the disperse | dyed disperse dye composition as needed.
本発明の分散染料組成物の染料以外の成分としては、後記の分散剤や水等が挙げられる。これらの成分の添加の時点は、特に限定されない。 Examples of components other than the dye of the disperse dye composition of the present invention include a dispersant and water described below. The time of addition of these components is not particularly limited.
本発明における黄色系分散染料組成物、赤色系分散染料組成物、青色系分散染料組成物及びそれらの混合分散染料組成物には色調を調整するため、若しくは、耐光堅牢度、染色特性等を調整するために他の分散染料を混合して使用することが出来る。
また、染色時に他の分散染料を加えて使用することも出来る。同様に分散染料以外の染料を混合して使用することが出来る。また、染色時に他の染料や染色薬剤を加えて使用することも出来る。The yellow disperse dye composition, the red disperse dye composition, the blue disperse dye composition and the mixed disperse dye composition thereof according to the present invention are used to adjust the color tone, or to adjust light fastness, dyeing characteristics, etc. Therefore, other disperse dyes can be mixed and used.
In addition, other disperse dyes can be added during dyeing. Similarly, dyes other than disperse dyes can be mixed and used. Further, other dyes and dyeing agents can be added and used at the time of dyeing.
微粒子化（分散化）処理は、ナフタレンスルホン酸とアルキルベンゼンスルホン酸のホルマリン縮合物、ナフタレンスルホン酸のホルマリン縮合物、クレゾールスルホン酸のホルマリン縮合物、クレゾールと２−ナフトール−６−スルホン酸のホルマリン縮合物、アルキルナフタレンスルホン酸のホルマリン縮合物、クレオソート油スルホン酸のホルマリン縮合物、リグニンスルホン酸等のアニオン分散剤；エチレンオキサイドとプロピレンオキサイドとのブロック共重合物、アルキルフェノールのエチレンオキサイド付加物、ポリスチレン化フェノールのエチレンオキサイド付加物等の非イオン分散剤、又は、これらのアニオン分散剤と非イオン分散剤との混合物、及び、少量の水の存在下に、分散染料の原末を、ボールミルあるいはサンドミル等の粉砕機を用いて通常０．２〜２μ程度になるまで十分に湿式粉砕することにより行なわれる。本発明の分散染料組成物は、微粒子化されたままの液状乃至ペースト状で、あるいは、スプレ−乾燥法等により乾燥して染色に供される。 The micronization (dispersion) treatment includes formalin condensate of naphthalene sulfonic acid and alkylbenzene sulfonic acid, formalin condensate of naphthalene sulfonic acid, formalin condensate of cresol sulfonic acid, and formalin condensation of cresol and 2-naphthol-6-sulfonic acid. , Formalin condensate of alkylnaphthalene sulfonic acid, formalin condensate of creosote oil sulfonic acid, lignin sulfonic acid and other anionic dispersants; block copolymer of ethylene oxide and propylene oxide, ethylene oxide adduct of alkylphenol, polystyrene In the presence of a nonionic dispersant such as an ethylene oxide adduct of fluorinated phenol, or a mixture of these anionic dispersant and nonionic dispersant, and a small amount of water, Carried out by sufficiently wet-milled to a normally about 0.2~2μ using a pulverizer such as a mill. The disperse dye composition of the present invention is used in the form of liquid or paste as it is finely divided, or dried by a spray drying method or the like.
次に、本発明の分散染料組成物を用いる染色方法について説明する。該染色方法により染色し得る疎水性繊維としては、ポリエステル（ＰＥＴ）繊維、トリアセテート繊維、ジアセテート繊維、ポリアミド繊維及びこれら同士の混紡品が挙げられる。これらとレーヨン等の再生繊維あるいは木綿、絹、羊毛等の天然繊維との混紡品であってもよい。また、上記疎水性繊維の太さとしては、平均の太さが０．１〜１０ｄ（デニ−ル）程度が好ましい。 Next, the dyeing | staining method using the disperse dye composition of this invention is demonstrated. Examples of hydrophobic fibers that can be dyed by the dyeing method include polyester (PET) fibers, triacetate fibers, diacetate fibers, polyamide fibers, and blended products of these. A blended product of these and recycled fibers such as rayon or natural fibers such as cotton, silk, wool may be used. The thickness of the hydrophobic fiber is preferably about 0.1 to 10 d (denier) in average thickness.
該繊維を浸漬した水性媒体中で、加圧下１０５℃以上、好ましくは１１０℃〜１４０℃で３０分〜１時間染色を行うのが好ましい。また、ｏ−フェニルフェノールやトリクロロベンゼン等のキャリヤーの存在下に比較的高温、例えば、水の沸騰状態で染色することも出来る。あるいは本発明の分散染料組成物の染料分散液を布にパディングし、１５０〜２３０℃、３０秒〜１分間の乾熱処理を施す所謂サーモゾル方式での染色も可能である。
一方、本発明の分散染料組成物を用いて、天然糊剤（例えば、ローカストビーンガム、グアーガム等）、加工糊剤（例えば、カルボキシメチルセルロース等の繊維素誘導体、加工ローカストビーンガム等）又は合成糊剤（例えば、ポリビニルアルコール、ポリビニル酢酸等）等とともに捺染糊を調製し、布に印捺した後にスチーミング又はサーモゾル処理を施す捺染法による染色を行なってもよい。又、本発明の分散染料組成物にグリセリンあるいはジエチレングリコール等の不乾性剤を添加して得たインクを調製し、パディング等によって予め糊剤等が付与された布にインクジェット方式のプリンターを用いてプリントした後に、スチーミング又はサーモゾル処理するインクジェット捺染法による染色を行ってもよい。It is preferable to perform dyeing in an aqueous medium in which the fibers are immersed at a pressure of 105 ° C. or higher, preferably 110 ° C. to 140 ° C. for 30 minutes to 1 hour. It can also be dyed at a relatively high temperature, for example, in a boiling state of water, in the presence of a carrier such as o-phenylphenol or trichlorobenzene. Alternatively, the dye dispersion of the disperse dye composition of the present invention may be padded on a cloth and dyed by a so-called thermosol method in which a dry heat treatment is performed at 150 to 230 ° C. for 30 seconds to 1 minute.
On the other hand, using the disperse dye composition of the present invention, natural paste (for example, locust bean gum, guar gum, etc.), processed paste (for example, fiber derivatives such as carboxymethyl cellulose, processed locust bean gum, etc.) or synthetic paste A printing paste may be prepared together with an agent (for example, polyvinyl alcohol, polyvinyl acetic acid, etc.), printed on a cloth, and then dyed by a printing method in which a steaming or thermosol treatment is performed. Also, an ink obtained by adding a non-drying agent such as glycerin or diethylene glycol to the disperse dye composition of the present invention is prepared, and printed using an ink jet printer on a cloth that has been previously provided with a paste or the like by padding or the like. After that, dyeing may be performed by an inkjet printing method in which steaming or thermosol processing is performed.
本発明の分散染料組成物を用いて染色する際の該染料原末としての使用量は任意であるが、好ましい態様において、例えば、３デニ−ルの繊維の場合は０．０５〜２０％ｏ．ｗ．ｆ．（ｏｎ ｗｅｉｇｈｔ ｏｆ ｆｉｂｅｒ：対繊維重量）、好ましくは０．２〜１０％ｏ．ｗ．ｆ．である。 The amount of the dye bulk powder used when dyeing with the disperse dye composition of the present invention is arbitrary, but in a preferred embodiment, for example, 0.05 to 20% o in the case of 3 denier fibers. . w. f. (On weight of fiber: fiber weight), preferably 0.2 to 10% o.d. w. f. It is.
以下の実施例により、本発明を詳細に説明する。実施例において、部は重量部を、％は重量％をそれぞれ意味する。
実施例中の分散剤は、ナフタレンスルホン酸のホルマリン縮合物のナトリウム塩を使用した。The following examples illustrate the invention in detail. In Examples, “part” means “part by weight” and “%” means “% by weight”.
As a dispersant in the examples, a sodium salt of a formalin condensate of naphthalene sulfonic acid was used.
［実施例１］分散染料組成物の製造
式（１）の原末５．０％、式（２）の原末１．６％、式（３）の原末２６．０％に分散剤６７．４％を加え微粒子化処理を行い、黄色分散染料組成物を得た。
式（６）の原末７．５％、式（７）の原末２７．５％に分散剤６５．０％を加え微粒子化処理を行い、赤色分散染料組成物を得た。
式（８）の原末２２．５％、式（９）の原末２．１％に分散剤７５．４％を加え微粒子化処理を行い、青色分散染料組成物を得た。[Example 1] Production of disperse dye composition Dispersant 67 to 5.0% bulk powder of formula (1), 1.6% bulk powder of formula (2), 26.0% bulk powder of formula (3) .4% was added and finely divided to obtain a yellow disperse dye composition.
65.0% of a dispersant was added to 7.5% of the bulk powder of the formula (6) and 27.5% of the bulk powder of the formula (7) for fine particle treatment to obtain a red disperse dye composition.
75.4% of a dispersant was added to 22.5% of the bulk powder of the formula (8) and 2.1% of the bulk powder of the formula (9) to carry out a fine particle treatment to obtain a blue disperse dye composition.
［実施例２］分散染料組成物の製造
式（１）の原末６．０％、式（２）の原末１．６％、式（４）の原末１２．０％、式（５）の原末４．９％に分散剤７５．５％を加え微粒子化処理を行い、黄色分散染料組成物を得た。
式（６）の原末７．５％、式（７）の原末２７．５％に分散剤６５．０％を加え微粒子化処理を行い、赤色分散染料組成物を得た。
式（８）の原末２２．５％、式（９）の原末２．１％に分散剤７５．４％を加え微粒子化処理を行い、青色分散染料組成物を得た。[Example 2] Production of disperse dye composition 6.0% of bulk powder of formula (1), 1.6% of bulk powder of formula (2), 12.0% bulk powder of formula (4), formula (5) ) Was added to 74.9% of a dispersant and finely divided to obtain a yellow disperse dye composition.
65.0% of a dispersant was added to 7.5% of the bulk powder of the formula (6) and 27.5% of the bulk powder of the formula (7) for fine particle treatment to obtain a red disperse dye composition.
75.4% of a dispersant was added to 22.5% of the bulk powder of the formula (8) and 2.1% of the bulk powder of the formula (9) to carry out a fine particle treatment to obtain a blue disperse dye composition.
［実施例３］
実施例１の黄色分散染料組成物０．５７０％ｏ．ｗ．ｆ．、赤色分散染料組成物０．３７０％ｏ．ｗ．ｆ．及び青色分散染料組成物０．４００％ｏ．ｗ．ｆ．を純水中で酢酸と酢酸ナトリウムによりｐＨ４．５に調整し、紫外線吸収剤（サンライフ ＬＰＸ−５０；日華化学（株）製）２．０％ｏ．ｗ．ｆ．を加えて２０００部とした染浴を調製し、ポリエステル繊維起毛織物（表側が０．３デニールと裏側が３デニール糸使用）１００部を浸漬し、１３５℃で３０分間染色後、４５％のカセイソーダ６部、ハイドロサルファイト６部、サンモールＲＣー７００（アニオン性界面活性剤；日華化学（株）製）３部に水を加えて全量３０００部とした浴で、染色物に対して８０℃、１０分間の還元洗浄を施し、水洗後に乾燥してベージュ色の染色物を得た。得られた染色物について後記の耐光堅牢度試験を行い、表裏差を観察した。また、後記の染足試験を行い各条件での色目を観察し比較した。[Example 3]
Yellow disperse dye composition of Example 1 0.570% o.d. w. f. Red disperse dye composition 0.370% o. w. f. And blue disperse dye composition 0.400% o. w. f. Was adjusted to pH 4.5 with acetic acid and sodium acetate in pure water, and UV absorber (Sunlife LPX-50; manufactured by Nikka Chemical Co., Ltd.) 2.0% o. w. f. Is added to prepare a dyeing bath of 2000 parts, 100 parts of a polyester fiber raised fabric (using 0.3 denier on the front side and 3 denier on the back side) is dipped, dyed at 135 ° C. for 30 minutes, and then 45% caustic soda 6 parts, 6 parts hydrosulfite, 3 parts Sanmor RC-700 (anionic surfactant; manufactured by Nikka Chemical Co., Ltd.), water added to a total of 3000 parts, and 80 parts to the dyed product A reduction washing at 10 ° C. for 10 minutes was performed, followed by washing with water and drying to obtain a beige dyeing. The dyeing obtained was subjected to the light fastness test described below, and the difference between the front and the back was observed. In addition, the dyeing foot test described below was performed, and the color of each condition was observed and compared.
［実施例４］
実施例２の黄色分散染料組成物０．５８８％ｏ．ｗ．ｆ．、赤色分散染料組成物０．４００％ｏ．ｗ．ｆ．及び青色分散染料組成物０．４００％ｏ．ｗ．ｆ．にて、実施例３と同様に染色と後処理を行い、ベージュ色の染色物を得た。得られた染色物について実施例３と同様に耐光堅牢度試験を行い、表裏差を観察した。また、後記の染足試験を行い、各条件での色目を観察し比較した。[Example 4]
Yellow disperse dye composition of Example 2 0.588% o. w. f. Red disperse dye composition 0.400% o. w. f. And blue disperse dye composition 0.400% o. w. f. Then, dyeing and post-treatment were performed in the same manner as in Example 3 to obtain a beige dyeing. About the obtained dyeing | staining, the light fastness test was done like Example 3, and the front and back difference was observed. Moreover, the dyeing | staining foot test of a postscript was done, the color eyes in each condition were observed and compared.
［比較例１］
市販のクラリアントジャパン社の分散染料Ｆｏｒｏｎ Ｙｅｌｌｏｗ ＡＳ−３Ｌ ０．４７６％ｏ．ｗ．ｆ．、Ｆｏｒｏｎ Ｒｅｄ ＡＳ−３Ｌ ０．３４５％ｏ．ｗ．ｆ．及びＦｏｒｏｎ Ｂｌｕｅ ＡＳ−３Ｌ ０．４４６％ｏ．ｗ．ｆ．にて、実施例３と同様に染色と後処理を行い、ベージュ色の染色物を得た。得られた染色物について実施例３と同様に耐光堅牢度試験を行い、表裏差を観察した。また、後記の染足試験を行い、各条件での色目を観察し比較した。[Comparative Example 1]
Commercially available Clariant Japan disperse dye Foron Yellow AS-3L 0.476% o.d. w. f. Foron Red AS-3L 0.345% o. w. f. And Foron Blue AS-3L 0.446% o. w. f. Then, dyeing and post-treatment were performed in the same manner as in Example 3 to obtain a beige dyeing. About the obtained dyeing | staining, the light fastness test was done like Example 3, and the front and back difference was observed. Moreover, the dyeing | staining foot test of a postscript was done, the color eyes in each condition were observed and compared.
［実施例５］
実施例１の黄色分散染料組成物０．３７０％ｏ．ｗ．ｆ．、赤色分散染料組成物０．３４０％ｏ．ｗ．ｆ．及び青色分散染料組成物０．６２０％ｏ．ｗ．ｆ．にて、実施例３と同様に染色と後処理を行い、グレー色の染色物を得た。得られた染色物について実施例３と同様に耐光堅牢度試験を行い、表裏差を観察した。また、後記の染足試験を行い、各条件での色目を観察し比較した。[Example 5]
Yellow disperse dye composition of Example 1 0.370% o.d. w. f. Red disperse dye composition 0.340% o. w. f. And blue disperse dye composition 0.620% o. w. f. Then, dyeing and post-treatment were performed in the same manner as in Example 3 to obtain a gray dyed product. About the obtained dyeing | staining, the light fastness test was done like Example 3, and the front and back difference was observed. Moreover, the dyeing | staining foot test of a postscript was done, the color eyes in each condition were observed and compared.
［実施例６］
実施例２の黄色分散染料組成物０．３６０％ｏ．ｗ．ｆ．、赤色分散染料組成物０．３７０％ｏ．ｗ．ｆ．及び青色分散染料組成物０．６２０％ｏ．ｗ．ｆ．にて、実施例３と同様に染色と後処理を行い、グレー色の染色物を得た。得られた染色物を実施例３と同様に耐光堅牢度試験を行い、表裏差を観察した。また、後記の染足試験を行い、各条件での色目を観察し比較した。[Example 6]
Yellow disperse dye composition of Example 2 0.360% o.d. w. f. Red disperse dye composition 0.370% o. w. f. And blue disperse dye composition 0.620% o. w. f. Then, dyeing and post-treatment were performed in the same manner as in Example 3 to obtain a gray dyed product. The obtained dyed product was subjected to a light fastness test in the same manner as in Example 3, and the difference between the front and the back was observed. Moreover, the dyeing | staining foot test of a postscript was done, the color eyes in each condition were observed and compared.
［比較例２］
市販のクラリアントジャパン社の分散染料Ｆｏｒｏｎ Ｙｅｌｌｏｗ ＡＳ−３Ｌ ０．２７９％ｏ．ｗ．ｆ．、Ｆｏｒｏｎ Ｒｅｄ ＡＳ−３Ｌ ０．２７９％ｏ．ｗ．ｆ．及びＦｏｒｏｎ Ｂｌｕｅ ＡＳ−３Ｌ ０．６１５％ｏ．ｗ．ｆ．にて、実施例３と同様に染色と後処理を行い、グレー色の染色物を得た。得られた染色物について実施例３と同様に耐光堅牢度試験を行い、表裏差を観察した。また、後記の染足試験を行い、各条件での色目を観察し比較した。[Comparative Example 2]
Commercially available Clariant Japan disperse dye Foron Yellow AS-3L 0.279% o.d. w. f. Foron Red AS-3L 0.279% o. w. f. And Foron Blue AS-3L 0.615% o. w. f. Then, dyeing and post-treatment were performed in the same manner as in Example 3 to obtain a gray dyed product. About the obtained dyeing | staining, the light fastness test was done like Example 3, and the front and back difference was observed. Moreover, the dyeing | staining foot test of a postscript was done, the color eyes in each condition were observed and compared.
［試験法］
・耐光堅牢度試験
染色物にフェードメーター（ブラックパネル温度８９℃±３℃、８４メガジュール）キセノンランプを用いて光照射し、照射部分の変褪色をＪＩＳ Ｌ−０８０４の変褪色用グレースケールにて判定した。その結果を表１に示す。[Test method]
-Light fastness test The dyed product is irradiated with light using a fade meter (black panel temperature 89 ° C ± 3 ° C, 84 megajoule) xenon lamp, and the color change of the irradiated part is changed to the gray scale for color change of JIS L-0804. Was judged. The results are shown in Table 1.
・表裏差
染色されたポリエステル繊維起毛織物（表側が０．３デニールと裏側が３デニール糸使用）の表側と裏側との色相差を、視感で判定した。その結果を表１に示す。-Front / Back Difference The hue difference between the front side and the back side of a dyed polyester fiber raised fabric (using 0.3 denier yarn on the front side and 3 denier yarn on the back side) was determined visually. The results are shown in Table 1.
表１
・染足試験
１３５℃での３０分間の染色処理に代えて、６０℃から１分間毎に１℃の割合で昇温し、１００℃、１１０℃、１２０℃、１３０℃及び１３５℃の各温度の時点で、並びに、１３５℃に達した後に同温度にて３０分処理後の時点で、それぞれ布を取り出す点を除いて、実施例３と同様に染色を実施し、各染色物を得た。各温度で得られた染色物の色目をみることで黄色、赤色、青色分散染料の各温度での染色性の違いが判る。黄色、赤色、青色分散染料の各温度での染色性が揃っているほど、均一に染色する場合に温度コントロールが安易となる。・ Dye foot test Instead of dyeing treatment at 135 ° C. for 30 minutes, the temperature was raised from 60 ° C. at a rate of 1 ° C. every minute, and each temperature of 100 ° C., 110 ° C., 120 ° C., 130 ° C. and 135 ° C. At the point of time, and after reaching 135 ° C. and after 30 minutes of treatment at the same temperature, dyeing was carried out in the same manner as in Example 3 except that the cloths were taken out to obtain each dyed product. . By looking at the color of the dyed product obtained at each temperature, the difference in dyeability at each temperature of yellow, red, and blue disperse dyes can be seen. The more the dyeability at each temperature of yellow, red, and blue disperse dyes, the easier the temperature control is when uniformly dyeing.
表２
以上の結果から明らかなように、本発明の分散染料組成物による染色物は、耐光堅牢度が強く表裏の繊維の太さの違いに拘らず色がほぼ揃っており、また、染色条件に拘らずほぼ三原色の染め足が揃っている。 As is apparent from the above results, the dyed product of the disperse dye composition of the present invention has high light fastness and almost the same color regardless of the difference in the thickness of the front and back fibers, and regardless of the dyeing conditions. There are almost three primary dyed feet.
本発明の黄色系分散染料組成物、赤色系分散染料組成物及び青色系分散染料組成物は、各々強い耐光堅牢度を有し、加えて、それらの所定の組み合わせを含む混合分散染料組成物として用いる際に、各色において、耐光堅牢度が揃っており、且つ、三原色の染色時の再現性がよく染色特性が揃っている。従って、これらの分散染料組成物及び混合分散染料組成物は、特に、高温多湿となる自動車内に使用する疎水性繊維の染色に適している。 The yellow disperse dye composition, the red disperse dye composition and the blue disperse dye composition of the present invention each have a strong light fastness and, in addition, a mixed disperse dye composition containing a predetermined combination thereof. When used, the light fastness is uniform for each color, and the reproducibility at the time of dyeing the three primary colors is good and the dyeing characteristics are uniform. Therefore, these disperse dye compositions and mixed disperse dye compositions are particularly suitable for dyeing hydrophobic fibers used in automobiles that are hot and humid.
Claims (9)
式（２）で表される分散染料、並びに、
式（３）で表される分散染料、式（４）で表される分散染料及び式（５）で表される分散染料からなる群から選ばれる１〜３の分散染料からなる染料を含有する黄色系分散染料組成物。
A disperse dye represented by formula (2), and
Contains a disperse dye represented by formula (3), a disperse dye represented by formula (4), and a dye comprising 1 to 3 disperse dyes selected from the group consisting of a disperse dye represented by formula (5) Yellow disperse dye composition.
The article containing the dyeing | staining of a fiber material containing the disperse dye composition as described in any one of Claims 1-7 .
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| JPH0625311B2 (en) * | 1985-07-09 | 1994-04-06 | 住友化学工業株式会社 | Dispersion type water-insoluble dye composition |
| JP2516785B2 (en) * | 1987-11-02 | 1996-07-24 | ダイスタージャパン株式会社 | Dyeing method for polyester fiber |
| JP2004168950A (en) * | 2002-11-21 | 2004-06-17 | Dystar Japan Ltd | Disperse dye mixture having high color fastness to light |
| PT1879964E (en) * | 2005-05-13 | 2011-09-05 | Huntsman Adv Mat Switzerland | Dye mixtures |
| JP5048479B2 (en) * | 2005-11-16 | 2012-10-17 | 紀和化学工業株式会社 | Disperse dye, disperse dye composition, ink for ink-jet printing, dyeing method and dyed material using these |
-
2011
- 2011-11-16 WO PCT/JP2011/076414 patent/WO2012073696A1/en active Application Filing
- 2011-11-16 CN CN201180057383.0A patent/CN103228741B/en active Active
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61207681A (en) * | 1985-03-07 | 1986-09-16 | 住友化学工業株式会社 | Dyeing of polyester fiber material |
| JP2004067933A (en) * | 2002-08-08 | 2004-03-04 | Dystar Japan Ltd | Yellow disperse dye mixture having high light fastness |
| JP2005023254A (en) * | 2003-07-04 | 2005-01-27 | Dystar Japan Ltd | Disperse dye mixture having high color fastness to light |
| JP2006008871A (en) * | 2004-06-25 | 2006-01-12 | Dystar Japan Ltd | Disperse dye for polylactic acid fiber |
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| Publication number | Publication date |
|---|---|
| CN103228741A (en) | 2013-07-31 |
| CN103228741B (en) | 2015-07-08 |
| JPWO2012073696A1 (en) | 2014-05-19 |
| WO2012073696A1 (en) | 2012-06-07 |
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