WO2023286283A1 - Fire retardant and simultaneously dyeing method for polyester-based textile - Google Patents
Fire retardant and simultaneously dyeing method for polyester-based textile Download PDFInfo
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- WO2023286283A1 WO2023286283A1 PCT/JP2021/026875 JP2021026875W WO2023286283A1 WO 2023286283 A1 WO2023286283 A1 WO 2023286283A1 JP 2021026875 W JP2021026875 W JP 2021026875W WO 2023286283 A1 WO2023286283 A1 WO 2023286283A1
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- WIPO (PCT)
- Prior art keywords
- represented
- formula
- dyeing
- disperse dye
- polyester fiber
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- 239000003063 flame retardant Substances 0.000 title claims abstract description 148
- 238000004043 dyeing Methods 0.000 title claims abstract description 130
- 229920000728 polyester Polymers 0.000 title claims abstract description 87
- 238000000034 method Methods 0.000 title claims abstract description 34
- 239000004753 textile Substances 0.000 title claims abstract description 24
- 239000000986 disperse dye Substances 0.000 claims abstract description 205
- -1 phosphoric acid ester amide Chemical class 0.000 claims abstract description 61
- 238000012545 processing Methods 0.000 claims abstract description 35
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 116
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 82
- 239000000835 fiber Substances 0.000 claims description 64
- 239000002245 particle Substances 0.000 claims description 40
- 229910019142 PO4 Inorganic materials 0.000 claims description 26
- 239000000975 dye Substances 0.000 claims description 26
- 239000010452 phosphate Substances 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 6
- 238000003672 processing method Methods 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 239000004744 fabric Substances 0.000 description 71
- 230000000052 comparative effect Effects 0.000 description 48
- 238000011156 evaluation Methods 0.000 description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 8
- 239000003086 colorant Substances 0.000 description 8
- 238000004737 colorimetric analysis Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 4
- 239000003945 anionic surfactant Substances 0.000 description 4
- 239000002736 nonionic surfactant Substances 0.000 description 4
- 239000004745 nonwoven fabric Substances 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 230000000979 retarding effect Effects 0.000 description 4
- 239000002759 woven fabric Substances 0.000 description 4
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229920001610 polycaprolactone Polymers 0.000 description 3
- RLLPVAHGXHCWKJ-IEBWSBKVSA-N (3-phenoxyphenyl)methyl (1s,3s)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-IEBWSBKVSA-N 0.000 description 2
- NZUPFZNVGSWLQC-UHFFFAOYSA-N 1,3,5-tris(2,3-dibromopropyl)-1,3,5-triazinane-2,4,6-trione Chemical compound BrCC(Br)CN1C(=O)N(CC(Br)CBr)C(=O)N(CC(Br)CBr)C1=O NZUPFZNVGSWLQC-UHFFFAOYSA-N 0.000 description 2
- JRHWHSJDIILJAT-UHFFFAOYSA-N 2-hydroxypentanoic acid Chemical compound CCCC(O)C(O)=O JRHWHSJDIILJAT-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 229930182843 D-Lactic acid Natural products 0.000 description 2
- JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical compound C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-N 0.000 description 2
- 229920005682 EO-PO block copolymer Polymers 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 229940022769 d- lactic acid Drugs 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 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 2
- VSXGXPNADZQTGQ-UHFFFAOYSA-N oxirane;phenol Chemical class C1CO1.OC1=CC=CC=C1 VSXGXPNADZQTGQ-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 229920002961 polybutylene succinate Polymers 0.000 description 2
- 239000004631 polybutylene succinate Substances 0.000 description 2
- 229920001707 polybutylene terephthalate Polymers 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- JNUCNIFVQZYOCP-UHFFFAOYSA-N (4-methylphenyl) dihydrogen phosphate Chemical compound CC1=CC=C(OP(O)(O)=O)C=C1 JNUCNIFVQZYOCP-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
- CRMKCODPIHHCGA-UHFFFAOYSA-N 1-amino-4-hydroxy-2-[2-(2-methoxyethoxy)ethoxy]anthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(OCCOCCOC)=CC(O)=C3C(=O)C2=C1 CRMKCODPIHHCGA-UHFFFAOYSA-N 0.000 description 1
- 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 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
- JSRUDOBCTLPTFO-UHFFFAOYSA-N 2-[5-acetamido-n-(2-acetyloxyethyl)-4-[(2-bromo-4,6-dinitrophenyl)diazenyl]-2-methoxyanilino]ethyl acetate Chemical compound C1=C(N(CCOC(C)=O)CCOC(C)=O)C(OC)=CC(N=NC=2C(=CC(=CC=2Br)[N+]([O-])=O)[N+]([O-])=O)=C1NC(C)=O JSRUDOBCTLPTFO-UHFFFAOYSA-N 0.000 description 1
- ZDORFLXCSSFUIE-UHFFFAOYSA-N 2-[n-(2-acetyloxyethyl)-4-[(2-chloro-4-nitrophenyl)diazenyl]-3-(propanoylamino)anilino]ethyl acetate Chemical compound CCC(=O)NC1=CC(N(CCOC(C)=O)CCOC(C)=O)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1Cl ZDORFLXCSSFUIE-UHFFFAOYSA-N 0.000 description 1
- 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 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
- SYRYUHDADMGBEC-UHFFFAOYSA-N 2-phenoxyethyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OCCOC1=CC=CC=C1 SYRYUHDADMGBEC-UHFFFAOYSA-N 0.000 description 1
- MUERWWKQVXXPML-UHFFFAOYSA-N 3-[n-(2-cyanoethyl)-4-[(2,6-dichloro-4-nitrophenyl)diazenyl]anilino]propanenitrile Chemical compound ClC1=CC([N+](=O)[O-])=CC(Cl)=C1N=NC1=CC=C(N(CCC#N)CCC#N)C=C1 MUERWWKQVXXPML-UHFFFAOYSA-N 0.000 description 1
- PTIVACHGVHIMMK-UHFFFAOYSA-N 4-[[2-methoxy-4-[(4-nitrophenyl)diazenyl]phenyl]diazenyl]phenol Chemical compound COC1=CC(N=NC=2C=CC(=CC=2)[N+]([O-])=O)=CC=C1N=NC1=CC=C(O)C=C1 PTIVACHGVHIMMK-UHFFFAOYSA-N 0.000 description 1
- OUPCDFWTGHUQRO-UHFFFAOYSA-N 5,5-dimethyl-2-(2-phenylphenoxy)-1,3,2$l^{5}-dioxaphosphinane 2-oxide Chemical compound O1CC(C)(C)COP1(=O)OC1=CC=CC=C1C1=CC=CC=C1 OUPCDFWTGHUQRO-UHFFFAOYSA-N 0.000 description 1
- JRCVADPCCJEFEK-UHFFFAOYSA-N 6-benzylbenzo[c][2,1]benzoxaphosphinine 6-oxide Chemical compound O1C2=CC=CC=C2C2=CC=CC=C2P1(=O)CC1=CC=CC=C1 JRCVADPCCJEFEK-UHFFFAOYSA-N 0.000 description 1
- 235000006173 Larrea tridentata Nutrition 0.000 description 1
- 244000073231 Larrea tridentata Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XREZMAAQVYVESP-UHFFFAOYSA-N acetyloxymethyl 2-[n-[2-(acetyloxymethoxy)-2-oxoethyl]-2-[2-[2-[bis[2-(acetyloxymethoxy)-2-oxoethyl]amino]-4-fluorophenoxy]ethoxy]-5-fluoroanilino]acetate Chemical compound CC(=O)OCOC(=O)CN(CC(=O)OCOC(C)=O)C1=CC(F)=CC=C1OCCOC1=CC=C(F)C=C1N(CC(=O)OCOC(C)=O)CC(=O)OCOC(C)=O XREZMAAQVYVESP-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 208000018747 cerebellar ataxia with neuropathy and bilateral vestibular areflexia syndrome Diseases 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229960002126 creosote Drugs 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- TUXJTJITXCHUEL-UHFFFAOYSA-N disperse red 11 Chemical compound C1=CC=C2C(=O)C3=C(N)C(OC)=CC(N)=C3C(=O)C2=C1 TUXJTJITXCHUEL-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 208000016253 exhaustion Diseases 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000009981 jet dyeing Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- LEGWLJGBFZBZSC-UHFFFAOYSA-N n-[2-[(2,6-dicyano-4-nitrophenyl)diazenyl]-5-(diethylamino)phenyl]acetamide Chemical compound CC(=O)NC1=CC(N(CC)CC)=CC=C1N=NC1=C(C#N)C=C([N+]([O-])=O)C=C1C#N LEGWLJGBFZBZSC-UHFFFAOYSA-N 0.000 description 1
- 229920000118 poly(D-lactic acid) Polymers 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920009537 polybutylene succinate adipate Polymers 0.000 description 1
- 239000004630 polybutylene succinate adipate Substances 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
- D06P1/18—Azo 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
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
- D06P1/20—Anthraquinone 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
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/667—Organo-phosphorus compounds
Definitions
- the present invention relates to a method for dyeing and simultaneously flame-retarding a polyester fiber product, and more specifically, immersing a polyester fiber product in a processing bath containing a specific azo disperse dye and a specific flame retardant, heating the polyester fiber, and
- the present invention relates to a method for simultaneously dyeing and flame-retarding a polyester fiber product, which can obtain a dyed and flame-retardant polyester fiber product with good dyeing reproducibility.
- the present invention relates to dyed, flame-retardant polyester fiber articles thus obtained.
- Azo disperse dyes are known to be inferior to quinone disperse dyes in light fastness, but to have strong coloring power. Among them, the following formula (I)
- the azo disperse dye represented by is also known to be a disperse dye suitable for dyeing polyester fiber products. (See Patent Document 2)
- quinone-based disperse dyes are generally known to give dyes with excellent light fastness.
- the following formula (V) is a quinone-based disperse dye.
- a quinone-based disperse dye represented by is known (see Patent Documents 1, 3 and 4).
- red, yellow and blue disperse dyes as the three primary colors according to the desired color tone, and to mix these colors.
- the dyeing characteristics of these red, yellow and blue disperse dyes, particularly the dyeing speed, that is, the rate of increase in the amount of dyeing accompanying the temperature rise during dyeing are uniform, the dyeing conditions, such as Even if the dyeing temperature fluctuates to a certain extent, the resulting dyed goods have little effect on the shade. That is, the disperse dyes of the three primary colors with uniform dyeing speeds are excellent in reproducibility of dyeing of polyester fiber products.
- the polyester fiber product is immersed in a processing bath containing a flame retardant together with each of the yellow disperse dye, the red disperse dye, and the blue disperse dye, and heated to dye the polyester fiber product.
- a processing bath containing a flame retardant together with each of the yellow disperse dye, the red disperse dye, and the blue disperse dye, and heated to dye the polyester fiber product.
- polyester fiber products are dyed at the same time as being flame-retardant to obtain a flame-retardant dyed product with good dyeing reproducibility.
- the flame retardant used must not interfere with the excellent dyeing reproducibility of the disperse dyes used in combination.
- the present invention uses the azo disperse dye represented by the above formulas (I) to (IV) in the case of dyeing and simultaneously flame retarding polyester textiles in a processing bath containing a flame retardant together with an azo disperse dye. At least one selected from, or from at least one selected from the azo disperse dyes represented by the formulas (I) to (IV) and the quinone disperse dyes represented by the formulas (V) to (VII) It is an object of the present invention to provide a method for simultaneously dyeing and flame-retarding polyester textiles to obtain dyed flame-retardant polyester textiles with good dyeing reproducibility by using at least one selected flame retardant and using a specific flame retardant. and
- a method for simultaneously dyeing and flame-retarding a polyester fiber article comprising immersing the polyester fiber article in a processing bath containing a phosphoric acid ester amide represented by and heating the polyester fiber article.
- the above method may be referred to as the first method.
- a simultaneous dyeing flame retardant processing method is provided.
- the above method may be referred to as the second method.
- the polyester fiber product is immersed in the processing bath and heated to 105° C. or higher, and the processing bath preferably contains the above formula (I) At least one of the azo disperse dyes represented by (IV) from 0.05 to 5% wf, and the phosphoric acid ester amide represented by the above formula (VIII) at a concentration of 0.5 to It has in the range of 10% ⁇ wf.
- the polyester fiber product is immersed in the processing bath and heated to 105° C. or higher, and the processing bath preferably contains the above formula (I) At least one of the azo disperse dyes represented by (IV) and at least one of the quinone disperse dyes represented by the above formulas (V) to (VII) in a total concentration range of 0.05 to 5% wf and the concentration of the phosphate ester amide represented by the above formula (VIII) is in the range of 0.5 to 10% wf.
- both the azo-based and quinone-based disperse dyes and the phosphoric acid ester amide used preferably have an average particle size in the range of 0.2 to 2.0 ⁇ m.
- the flame retardant treatment method simultaneously with dyeing of polyester fiber products according to the present invention includes, together with the flame retardant phosphate ester amide represented by the formula (VIII), At least one selected from the group consisting of the azo disperse dyes represented by the formulas (I) to (IV), or from the group consisting of the azo disperse dyes represented by the formulas (I) to (IV) Using at least one selected and at least one selected from the group consisting of the quinone disperse dyes represented by the formulas (V) to (VII), polyester textiles are dyed and flame retarded at the same time. be.
- a polyester fiber product is subjected to flame retardant treatment at the same time as dyeing in a processing bath containing at least one selected from Since the azo disperse dye and the quinone disperse dye both have small changes in dyeing speed, it is possible to obtain dyed flame-retardant polyester textiles with good dyeing reproducibility.
- the method for dyeing and simultaneously flame retarding polyester textiles according to the present invention is at least one selected from the group consisting of azo disperse dyes represented by the above formulas (I) to (IV), or the above formula (I) at least one selected from the group consisting of azo disperse dyes represented by (IV) and at least one selected from the group consisting of quinone disperse dyes represented by formulas (V) to (VII);
- a polyester fiber product is immersed in a processing bath containing a phosphoric acid ester amide represented by formula (VIII), heated, and flame-retardant processed at the same time as dyeing.
- a dyed, flame-retardant polyester fiber product can be obtained with high efficiency.
- At least one selected from the group consisting of azo disperse dyes represented by the above formulas (I) to (IV) is added to the processing bath, Or at least one selected from the group consisting of azo disperse dyes represented by formulas (I) to (IV) and the group consisting of quinone disperse dyes represented by formulas (V) to (VII). and at least one phosphoric acid ester amide represented by the above formula (VIII).
- the azo disperse dye represented by the above formula (I) is C.I. I. Disperse Yellow 163.
- the azo disperse dye represented by the above formula (II) is C.I. I. Disperse Red 167:1, and the azo disperse dye represented by the above formula (III) is C.I. I. Disperse Blue 165, and the azo disperse dye represented by the above formula (IV) is C.I. I. Disperse Blue 79:1.
- quinone-based disperse dye represented by the formula (V) is C.I. I. Disperse Blue 56
- the quinone-based disperse dye represented by the formula (VI) is C.I. I. Disperse Blue 60
- the quinone-based disperse dye represented by the formula (VII) is C.I. I. Disperse Blue 77.
- the azo disperse dye, or the azo disperse dye and the quinone disperse dye together with the flame retardant phosphoric acid ester amide is used to subject the polyester fiber product to flame retardant treatment at the same time as dyeing
- Both the disperse dye and the phosphate ester amide have an average particle size of 0.2 to 2.0 ⁇ m so that the disperse dye and the flame retardant phosphate ester amide can sufficiently diffuse and adhere to the interior of the polyester fiber product. It preferably has a diameter. However, the disperse dye and the flame retardant phosphate ester amide need not have the same average particle size.
- the disperse dye and phosphate ester amide having an average particle size within the range described above can be obtained, for example, by pulverizing each of the disperse dye and phosphate ester amide in advance with a sand mill or ball mill in water containing a surfactant. can be obtained by
- Surfactants used for refining the azo disperse dyes and quinone disperse dyes include, for example, formalin condensates of naphthalenesulfonic acid and alkylbenzenesulfonic acid, formalin condensates of naphthalenesulfonic acid, cresol and 2-naphthol.
- -6-formalin condensate of sulfonic acid formalin condensate of alkylnaphthalenesulfonic acid, formalin condensate of creosote oil sulfonic acid, anionic surfactants such as ligninsulfonic acid, block copolymers of ethylene oxide and propylene oxide, Nonionic surfactants such as ethylene oxide adducts of alkylphenols and ethylene oxide adducts of polystyrenated phenols, and mixtures of these anionic surfactants and nonionic surfactants are preferred.
- surfactants used for refining the phosphoric acid ester amide include anionic surfactants such as sulfuric acid ester salts of arylated phenol ethylene oxide adducts and sulfosuccinic acid ester salts of styrenated phenol ethylene oxide adducts.
- anionic surfactants such as sulfuric acid ester salts of arylated phenol ethylene oxide adducts and sulfosuccinic acid ester salts of styrenated phenol ethylene oxide adducts.
- nonionic surfactants such as agents, block copolymers of ethylene oxide and propylene oxide, ethylene oxide adducts of alkylphenols, ethylene oxide adducts of polystyrenated phenols, or combinations of these anionic surfactants and nonionic surfactants Mixtures are preferred.
- the method for dyeing and simultaneously flame retarding polyester textiles according to the present invention includes a specific azo disperse dye, and when used in combination with the azo disperse dye, a specific quinone disperse dye, and a specific are wet pulverized in the presence of the surfactant, respectively, to form a dispersion containing fine particles of the disperse dye and the flame retardant, and these are added to a bath containing water to obtain a predetermined bath ratio.
- a bath is constructed, and a polyester fiber product is immersed in this processing bath, and the temperature is 105° C. or higher, preferably in the range of 105 to 140° C., particularly preferably in the range of 110 to 140° C., for 30 to 60 minutes.
- the treated polyester fiber product is removed from the processing bath, treated with soaping, washed with water, dehydrated and dried to obtain a dyed flame-retardant polyester fiber product. be able to.
- the polyester fiber product is immersed in the processing bath in the dyeing machine, heated to 105 ° C. or higher, and exhausted in the bath. is in the range of 0.1-0.5 MPa.
- the dye when the azo disperse dye or the quinone disperse dye is used in combination, the dye is dyed with the azo disperse dye and the quinone disperse dye. , a polyester fiber article flame-retardant treated with the flame retardant can be obtained.
- the amounts of the azo disperse dye and the flame retardant phosphate ester amide used are not particularly limited, but the amount of the azo disperse dye used is usually from 0.05 to It is in the range of 5%owf, preferably in the range of 0.1 to 5%owf, more preferably in the range of 0.3 to 3.0%owf.
- the total amount of the azo disperse dye and the quinone disperse dye is usually It is in the range of 0.05 to 5%owf, preferably in the range of 0.1 to 5%owf, and more preferably in the range of 0.3 to 3.0%owf.
- the amount of the flame retardant phosphate ester amide used is usually preferably in the range of 0.5 to 10% owf in order to impart sufficient flame retardancy to polyester textiles to be dyed. It is more preferably in the range of .5 to 8.0%owf, most preferably in the range of 1.0 to 8.0%owf.
- the bath ratio of the working bath is not particularly limited, but is usually in the range of 1:3 to 1:30, preferably in the range of 1:5 to 1:20. If the bath ratio is lower than 1:3, uneven dyeing may occur because the polyester fiber product is not sufficiently immersed in the processing bath. It is uneconomical because the amount of water used for processing is unnecessarily large.
- the polyester fiber product refers to a fiber containing at least polyester fiber, yarn containing such fiber, cotton, fabric such as woven fabric and non-woven fabric, preferably polyester fiber. Fabrics such as threads, cotton, woven fabrics and non-woven fabrics. Further, the fabric such as a woven fabric or a non-woven fabric may be a single layer or a laminate of two or more layers, or may be a composite made of yarn, cotton, a woven fabric, a non-woven fabric, or the like.
- the polyester fiber is, for example, polyethylene terephthalate, polypropylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polybutylene naphthalate, polyethylene terephthalate/isophthalate, polyethylene terephthalate/5-sulfoisophthalate, polyethylene terephthalate/polyoxy benzoyl, polybutylene terephthalate/isophthalate, poly(D-lactic acid), poly(L-lactic acid), copolymers of D-lactic acid and L-lactic acid, copolymers of D-lactic acid and aliphatic hydroxycarboxylic acids, Copolymers of L-lactic acid and aliphatic hydroxycarboxylic acids, polycaprolactones such as poly- ⁇ -caprolactone (PCL), polymalic acid, polyhydroxycarboxylic butyric acid, polyhydroxyvaleric acid, ⁇ -hydroxybutyric acid (3HB)-3 - Polyaliphatic
- the dyed flame-retardant polyester fiber product obtained by the method of the present invention is suitably used for, for example, seat sheets, seat covers, curtains, wallpapers, ceiling cloths, carpets, drop curtains, architectural protection sheets, tents, canvases, and the like.
- disperse dyes examples include C.I. I. Red disperse dyes such as Disperse Red 53, 60, 86, 92, C.I. I. Disperse Yellow 71, 42, 51, C.I. I. Yellow disperse dyes such as Solvent Yellow 163, C.I. I. Blue disperse dyes such as Disperse Blue 54, C.I. I. Orange disperse dyes such as Disperse Orange 29 and 155 can be used, but the dyes are not limited to these.
- azo-based disperse dye, quinone-based disperse dye, and average particle size of flame retardant are each measured using a mill filled with glass beads having a diameter of 0.5 mm so as to have a predetermined average particle size in the presence of a surfactant. It was wet pulverized and used as an aqueous dispersion.
- the average particle size of each of the azo disperse dye, the quinone disperse dye, and the flame retardant is obtained by measuring the particle size distribution of each dispersion with a laser diffraction particle size distribution analyzer SALD-2000J manufactured by Shimadzu Corporation. , refers to the volume-based median diameter obtained based on this.
- CM-600d manufactured by Konica Minolta, Inc.
- a polyester double picket (basis weight of 240 g/m 2 ) was used as a fabric to be treated, and this was obtained by dyeing with a disperse dye at a temperature of 100 ° C. in the absence of a flame retardant.
- the color difference ⁇ E 100° C.
- a dyed product obtained by dyeing a fabric with a disperse dye in the absence of a flame retardant at a temperature of 130 ° C. and a dyed product obtained by dyeing with the same disperse dye as above in the presence of a flame retardant were measured.
- the color difference .DELTA.E 130.degree. C.
- the color difference ⁇ E (dye + flame retardant) of the dyed product obtained by dyeing with each disperse dye at °C was determined.
- the L * a * b * color specification formulated by the International Commission on Illumination (CIE) in 1974 According to the color space by the system.
- CIE International Commission on Illumination
- the L * value is called a lightness index, and a larger value indicates a brighter color, and a smaller value indicates a darker color.
- White has an L * value of 100 and black has an L * value of 0.
- the a * and b* values represent hue and saturation and are called chromaticity indices.
- Example 1 The fabric to be treated (polyester double picket (basis weight: 240 g/m 2 )) is added, and the temperature is raised from 40°C to 100°C at a rate of 2°C per minute for exhaustion treatment in the bath, followed by soaping treatment and water washing treatment, dehydration drying, and dyeing. I got the fabric. This dyed fabric was colorimetrically measured to determine L * (100), a * (100) and b * (100).
- the same treated fabric as above is put into a processing bath having the same structure as above, and the temperature is raised from 40 ° C. to 130 ° C. at a rate of 2 ° C. per minute, and held at that temperature for 30 minutes. It was exhausted in a bath, then soaped and washed with water, and then dehydrated and dried to obtain a dyed fabric. This dyed fabric was measured in the same manner as above to determine L * (130), a * (130) and b * (130).
- the dyed fabric was measured in the same manner as described above to determine L * (100 flame retardant), a * (100 flame retardant) and b * (100 flame retardant).
- the same treated fabric as above is put into a processing bath having the same structure as above, and the temperature is raised from 40 ° C. to 130 ° C. at a rate of 2 ° C. per minute, and held at that temperature for 30 minutes. It was exhausted in a bath, then soaped and washed with water, and then dehydrated and dried to obtain a dyed fabric.
- the dyed fabric was measured in the same manner as above to determine L * (130 flame retardant), a * (130 flame retardant) and b * (130 flame retardant).
- the color difference ⁇ E (100 ° C.) from the dyed fabric obtained by the formula ⁇ E (100 ° C.) [(L * (100) - L * (100 flame retardant)) 2 + (a * (100) - a * (100 flame retardant)) 2 + (b * (100) - b * (100 flame retardant)) 2 ] 1/2 .
- the color difference ⁇ E (130 ° C.) from the dyed fabric obtained by the formula ⁇ E (130 ° C.) [(L * (130) - L * (130 flame retardant)) 2 + (a * (130) - a * (130 flame retardant)) 2 + (b * (130) - b * (130 flame retardant)) 2 ] 1/2 .
- ⁇ E (100° C.) was evaluated as ⁇ (appropriate) when less than 5.00 and x (unsuitable) when 5.00 or more.
- ⁇ E (130° C.) was evaluated as ⁇ (appropriate) when less than 5.00 and x (unsuitable) when 5.00 or more.
- the dyeing speed change rate value exceeds 100 when ⁇ E (dye) is greater than ⁇ E (dye + flame retardant). That is, it can be said that the dyeing speed was increased by using the flame retardant together with the disperse dye.
- ⁇ E(dye) is less than ⁇ E(dye+flame retardant)
- the value is 100 or less. That is, it can be said that the dyeing speed is slowed down by using the flame retardant together with the disperse dye, so it can be said that the flame retardant inhibits the dyeing.
- Example 2 instead of the azo disperse dye having an average particle size of 0.8 ⁇ m represented by the formula (I), any of the formulas (II) to (IV) having an average particle size of 0.8 ⁇ m A dyed fabric was obtained in the same manner except that each of the azo disperse dyes was used.
- Examples 5-8 In Examples 1 to 4, instead of 0.3% owf of the azo disperse dye having an average particle size of 0.8 ⁇ m represented by the formula (I), the respective formulas (I) to (IV) A dyed fabric was obtained in the same manner except that 3.0% owf of an azo disperse dye having an average particle size of 0.8 ⁇ m was used.
- Examples 9-12 In Examples 1 to 4, instead of the flame retardant phosphoric acid ester amide 4.0% owf having an average particle size of 0.6 ⁇ m represented by the formula (VIII), the average particle size represented by the formula (VIII) In the same manner as in Examples 1 to 4, except that 8.0% owf of 0.6 ⁇ m flame retardant phosphoric acid ester amide was used, each of the average particle sizes represented by the above formulas (I) to (IV) A dyed fabric was similarly obtained using 0.3% owf of azo disperse dye of 0.8 ⁇ m.
- Examples 13-16 In Examples 1 to 4, instead of the flame retardant phosphoric acid ester amide 4.0% owf having an average particle size of 0.6 ⁇ m represented by the formula (VIII), the average particle size represented by the formula (VIII) In the same manner as in Examples 1 to 4, except that 0.6 ⁇ m flame retardant phosphate ester amide 1.0% owf was used, the average particle size of each of the above formulas (I) to (IV) A dyed fabric was similarly obtained using 0.3% owf of azo disperse dye of 0.8 ⁇ m.
- Example 17-19 an azo disperse dye having an average particle size of 0.8 ⁇ m represented by the formula (III) and an average particle size of 0.8 ⁇ m represented by the formulas (V) to (VII) A dyed fabric was obtained in the same manner as in Example 1, except that any of the quinone-based disperse dyes was used.
- Example 1 instead of the flame retardant phosphate amide represented by the formula (VIII), the following formula (IX) having an average particle size of 0.6 ⁇ m was used as a flame retardant.
- a dyed fabric was obtained in the same manner except that resorcinol bis (2,6-dixylenyl phosphate) represented by was used.
- Example 2 instead of the flame retardant phosphate amide represented by the formula (VIII), the following formula (X) having an average particle size of 0.6 ⁇ m was used as the flame retardant.
- a dyed fabric was obtained in the same manner except that 10-benzyl-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide represented by was used.
- Example 3 instead of the flame retardant phosphate amide represented by the formula (VIII), the following formula (XI) having an average particle size of 0.6 ⁇ m was used as the flame retardant.
- a dyed fabric was obtained in the same manner except that 2-phenoxyethyl diphenyl phosphate represented by was used.
- a dyed fabric was obtained in the same manner except that 5,5-dimethyl-2-(2'-phenylphenoxy)-1,3,2-dioxaphosphorinane-2-oxide represented by was used.
- Example 1 instead of the flame retardant phosphate amide represented by the formula (VIII), the following formula (XIII) having an average particle size of 0.6 ⁇ m was used as a flame retardant.
- the flame retardant phosphate amide represented by the formula (VIII) instead of the flame retardant phosphate amide represented by the formula (VIII), the following formula (XIII) having an average particle size of 0.6 ⁇ m was used as a flame retardant.
- a dyed fabric was obtained in the same manner except that p-cresyl phosphate represented by was used.
- Example 6 instead of the flame retardant phosphate amide represented by the formula (VIII), the following formula (XIV) having an average particle size of 0.6 ⁇ m was used as the flame retardant.
- a dyed fabric was obtained in the same manner except that tris (2,3-dibromopropyl) isocyanurate represented by was used.
- Comparative Examples 7-12 Dyed fabrics were obtained in the same manner as in Comparative Examples 1 to 6, except that the azo disperse dyes represented by formula (II) were used instead of the azo disperse dyes represented by formula (I). .
- Comparative Examples 13-18 Dyed fabrics were obtained in the same manner as in Comparative Examples 1 to 6, except that the azo disperse dyes represented by formula (III) were used instead of the azo disperse dyes represented by formula (I). .
- Comparative Examples 19-24 Dyed fabrics were obtained in the same manner as in Comparative Examples 1 to 6, except that the azo disperse dyes represented by formula (IV) were used instead of the azo disperse dyes represented by formula (I). .
- Comparative example 25 In Example 1, 3.0% owf of the azo disperse dye having an average particle size of 0.8 ⁇ m represented by the formula (I) was used, and instead of the flame retardant represented by the formula (VIII), the formula A dyed fabric was obtained in the same manner except that resorcinol bis(2,6-dixylenyl phosphate) having an average particle size of 0.6 ⁇ m represented by (IX) was used.
- Comparative example 26 In Example 1, instead of the azo disperse dye represented by the formula (I), 3.0% owf of the azo disperse dye having an average particle size of 0.8 ⁇ m represented by the formula (III) was used, 5,5-dimethyl-2-(2′-phenylphenoxy)-1,3 with an average particle size of 0.6 ⁇ m represented by the formula (XII) instead of the flame retardant represented by the formula (VIII) ,2-dioxaphosphorinane-2-oxide was used to obtain a dyed fabric.
- the azo disperse dye represented by the formula (I) 3.0% owf of the azo disperse dye having an average particle size of 0.8 ⁇ m represented by the formula (III) was used, 5,5-dimethyl-2-(2′-phenylphenoxy)-1,3 with an average particle size of 0.6 ⁇ m represented by the formula (XII) instead of the flame retardant represented by the formula (VIII) ,2-dioxaphosphor
- Comparative example 27 In Example 1, instead of the azo disperse dye represented by the formula (I), 3.0% owf of the azo disperse dye having an average particle size of 0.8 ⁇ m represented by the formula (III) was used, In the same manner, except that tris(2,3-dibromopropyl)isocyanurate having an average particle size of 0.6 ⁇ m represented by the formula (XIV) was used instead of the flame retardant represented by the formula (VIII). , to obtain a dyed fabric.
- a dyed fabric was obtained in the same manner except that an azo disperse dye having an average particle size of 0.8 ⁇ m represented by was used.
- the azo disperse dye represented by the above formula (XV) is C.I. I. Disperse Red 258, which is not an azo disperse dye specified for use in the present invention.
- Table 1 shows that any of the disperse dyes represented by the formulas (I) to (IV) in the presence of 4.0% wf amount of the flame retardant represented by the formula (VIII) with a 0.3% wf amount Even if it is used, when a treated fabric made of polyester fiber is dyed, both the color difference ⁇ E (100 ° C.) and ⁇ E (130 ° C.) are small and appropriate, and the dyeing speed change rate is also appropriate. indicates
- the fabric to be treated is dyed with the disperse dyes represented by the formulas (I) to (IV) in the absence of the flame retardant represented by the formula (VIII).
- the color difference between the dyed fabric obtained by and the dyed fabric obtained by dyeing the treated fabric with the disperse dye in the presence of the flame retardant is small, and the above-mentioned dyeing speed change rate is appropriate. Therefore, it can be said that even if the flame retardant is used in combination with the disperse dye, the rate of change in dyeing speed is small compared to the case of dyeing using the disperse dye in the absence of the flame retardant.
- Table 2 shows any of the disperse dyes represented by formulas (I) to (IV) in the presence of 4.0% of the flame retardant represented by formula (VIII) at 100 ° C. and 130 ° C. Even if it is used in an amount of 3.0% wf, the resulting dyed product has both small color differences ⁇ E (100°C) and ⁇ E (130°C) and is appropriate, and the rate of change in dyeing speed is also appropriate. indicates
- Table 3 shows that any of the disperse dyes represented by the formulas (I) to (IV) in the presence of 8.0% of the flame retardant represented by the formula (VIII) at 100 ° C. and 130 ° C. Even if it is used in an amount of 0.3% wf, the obtained dyed product has both small color difference ⁇ E (100°C) and ⁇ E (130°C) and is appropriate, and the dyeing speed change rate is also appropriate. indicates
- Table 4 shows any of the disperse dyes represented by formulas (I) to (IV) in the presence of 1.0% of the flame retardant represented by formula (VIII) at 100 ° C. and 130 ° C. Even if it is used in an amount of 0.3% wf, the obtained dyed product has both small color difference ⁇ E (100°C) and ⁇ E (130°C) and is appropriate, and the dyeing speed change rate is also appropriate. indicates
- Table 5 shows that at 100 ° C. and 130 ° C., in the presence of 4.0% of the flame retardant represented by the formula (VIII) and 0.3% of the disperse dye represented by the formula (III). Even if any of the disperse dyes represented by the above formulas (V) to (VII) is used in an amount of 0.3%, the obtained dyed product has a color difference ⁇ E (100° C.) and ⁇ E (130° C.) Both are small and correct, indicating that the dyeing speed change rate is also correct.
- the present invention at least one selected from the azo disperse dyes represented by the formulas (I) to (IV) and the flame retardant phosphate ester amide represented by the formula (VIII)
- the temperature At 100 ° C. and 130 ° C.
- the amounts of the azo disperse dye and the flame retardant used are variously changed, and the treated fabric is subjected to flame retardant treatment at the same time as dyeing. (130° C.) are both small and appropriate, and the dyeing speed change rate is also appropriate.
- the present invention it is possible to simultaneously dye and flame retard polyester textiles with good dyeing reproducibility.
- At least one selected from the azo disperse dyes represented by the formulas (I) to (IV) and the quinone disperse dyes represented by the formulas (V) to (VII) According to the dyeing and simultaneous flame retardant processing method in which a polyester textile is immersed in a processing bath containing at least one flame retardant phosphate ester amide represented by the formula (VIII) and heated, the flame retardant is not present. Compared to the case of dyeing a polyester fiber product with the above azo disperse dye and the above quinone disperse dye, even if the treated fabric is dyed and flame retarded at a temperature of 100 ° C.
- Table 6 shows the presence of conventionally known representative flame retardants represented by the formulas (IX) to (XIV) instead of the flame retardant represented by the formula (VIII).
- Table 6 shows the presence of conventionally known representative flame retardants represented by the formulas (IX) to (XIV) instead of the flame retardant represented by the formula (VIII).
- Table 7 shows, in Comparative Examples 7 to 12, instead of the flame retardant represented by the formula (VIII), conventionally known representatives represented by the formulas (IX) to (XIV) The results of dyeing polyester textiles with each of the azo disperse dyes represented by the formula (II) in the presence of a flame retardant are shown.
- Table 8 shows typical conventionally known flame retardants represented by the formulas (IX) to (XIV) instead of the flame retardant represented by the formula (VIII) in Comparative Examples 13 to 18.
- Table 8 shows typical conventionally known flame retardants represented by the formulas (IX) to (XIV) instead of the flame retardant represented by the formula (VIII) in Comparative Examples 13 to 18.
- the results of dyeing a polyester fiber product are shown.
- Comparative Examples 13, 14, 15 and 17 at least one of the color difference ⁇ E (100°C) and the dyeing speed change rate was unsuitable, but in Comparative Examples 16 and 18, the color difference ⁇ E (100°C), ⁇ E (130° C.) and dyeing rate change were all correct. Other results for Comparative Examples 16 and 18 are shown later.
- Table 9 shows typical conventionally known flame retardants represented by the formulas (IX) to (XIV) instead of the flame retardant represented by the formula (VIII) in Comparative Examples 19 to 24.
- the results of dyeing a polyester fiber product are shown.
- Comparative Example 25 is a combination of the disperse dye represented by the formula (I) and the flame retardant represented by the formula (IX), and Comparative Example 26 is the disperse dye represented by the formula (III). and the flame retardant represented by the formula (XII), Comparative Example 27 uses the disperse dye represented by the formula (III) and the flame retardant represented by the formula (XIV) in combination, respectively , shows the results of dyeing and simultaneous flame retardant processing of polyester fiber products.
- the disperse dye has an average particle size of 0.8 ⁇ m and the amount used is 3.0%owf
- the flame retardant has an average particle size of 0.6 ⁇ m and is used in an amount of 4.0%owf. is.
- Comparative Examples 25 to 27 the combination of the azo disperse dye and the flame retardant corresponds to those in Comparative Examples 1, 16 and 18 described above, but the amount of the azo disperse dye used is the same as in Comparative Examples 1, 16 and In Comparative Examples 25 to 27, the amount of owf was 0.3%, whereas in Comparative Examples 25 to 27, the amount of owf was 3.0%.
- the color difference ⁇ E (100°C) and ⁇ E (130°C) and at least one of the rate of change in dyeing speed corresponds to those in Comparative Examples 1, 16 and 18 described above, but the amount of the azo disperse dye used is the same as in Comparative Examples 1, 16 and In Comparative Examples 25 to 27, the amount of owf was 0.3%, whereas in Comparative Examples 25 to 27, the amount of owf was 3.0%.
- the color difference ⁇ E (100°C) and ⁇ E (130°C) and at least one of the rate of change in dyeing speed corresponds to those in Comparative Examples 1, 16 and 18 described above,
- Comparative Example 28 is the same as Example 1 except that in Example 1, the azo disperse dye represented by the formula (I) was replaced with the azo disperse dye represented by the formula (XV). Similarly, the results of dyeing and flame-retardant treatment of polyester fiber products are shown, but the rate of change in dyeing speed is excessive and unsuitable.
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Abstract
According to the present invention, there is provided a fire retardant and simultaneously dyeing method for polyester-based textiles, the method comprising immersing a polyester-based textile in a processing bath containing a specific azo disperse dye and fire retardant phosphoric acid ester amide represented by formula (VIII), and heating the textile. According to this method, it is possible to obtain a dyed fire-retardant polyester-based textile having excellent reproducibility because the change in the dyeing speed of the azo disperse dye is small despite the presence of the fire retardant.
Description
本発明はポリエステル系繊維品の染色同時難燃加工方法に関し、詳しくは、特定のアゾ系分散染料と特定の難燃剤を含む加工浴にポリエステル系繊維品を浸漬し、加熱して、ポリエステル系繊維品を染色同時難燃加工することによって、染色再現性よく、染色難燃加工ポリエステル系繊維品を得ることができる、ポリエステル系繊維品の染色同時難燃加工方法に関する。更に、本発明は、そのようにして得られる染色難燃加工ポリエステル系繊維品に関する。
The present invention relates to a method for dyeing and simultaneously flame-retarding a polyester fiber product, and more specifically, immersing a polyester fiber product in a processing bath containing a specific azo disperse dye and a specific flame retardant, heating the polyester fiber, and The present invention relates to a method for simultaneously dyeing and flame-retarding a polyester fiber product, which can obtain a dyed and flame-retardant polyester fiber product with good dyeing reproducibility. Furthermore, the present invention relates to dyed, flame-retardant polyester fiber articles thus obtained.
アゾ系分散染料は、耐光堅牢度はキノン系分散染料より劣るが、着色力が強いことが知られている。なかでも、下記式（Ｉ）
Azo disperse dyes are known to be inferior to quinone disperse dyes in light fastness, but to have strong coloring power. Among them, the following formula (I)
、
,
下記式（ＩＩ）
Formula (II) below
、
,
及び下記式（ＩＩＩ）
and the following formula (III)
で表されるアゾ系分散染料は特定のキノン系分散染料と組み合わせることによって着色力と共に耐光堅牢度にもすぐれる分散染料組成物を与えることが知られている。(特許文献１参照)
It is known that the azo disperse dye represented by is combined with a specific quinone disperse dye to give a disperse dye composition excellent in both coloring power and light fastness. (See Patent Document 1)
また、下記式（ＩＶ）
Also, the following formula (IV)
で表されるアゾ系分散染料もポリエステル系繊維製品の染色に適した分散染料であることが知られている。(特許文献２参照)
The azo disperse dye represented by is also known to be a disperse dye suitable for dyeing polyester fiber products. (See Patent Document 2)
一方、キノン系分散染料は、一般的に、耐光堅牢度にすぐれる染色物を与えることが知られている。そのようなキノン系分散染料として、下記式（Ｖ）
On the other hand, quinone-based disperse dyes are generally known to give dyes with excellent light fastness. As such a quinone-based disperse dye, the following formula (V)
で表されるキノン系分散染料、
下記式（ＶＩ） A quinone-based disperse dye represented by
Formula (VI) below
下記式（ＶＩ） A quinone-based disperse dye represented by
Formula (VI) below
で表されるキノン系分散染料、及び
下記式（ＶＩＩ） A quinone-based disperse dye represented by the following formula (VII)
下記式（ＶＩＩ） A quinone-based disperse dye represented by the following formula (VII)
で表されるキノン系分散染料が知られている（特許文献１、３及び４参照）。
A quinone-based disperse dye represented by is known (see Patent Documents 1, 3 and 4).
そして、従来、ポリエステル系繊維品を染色する場合、求める色調に応じて、赤色、黄色及び青色の分散染料を三原色として用いて、これらの混色によるのが一般的である。このような場合、これら赤色、黄色及び青色の分散染料の染色特性、特に、染色速度、即ち、染色時の温度上昇に伴う染着量の増加率が揃っているときは、染色条件、例えば、染色温度がある程度、変動しても、得られる染色物が色調において受ける影響は少ない。即ち、上記染色速度が揃っている三原色の分散染料は、ポリエステル系繊維品の染色の再現性にすぐれている。
Conventionally, when dyeing polyester textiles, it is common to use red, yellow and blue disperse dyes as the three primary colors according to the desired color tone, and to mix these colors. In such a case, when the dyeing characteristics of these red, yellow and blue disperse dyes, particularly the dyeing speed, that is, the rate of increase in the amount of dyeing accompanying the temperature rise during dyeing, are uniform, the dyeing conditions, such as Even if the dyeing temperature fluctuates to a certain extent, the resulting dyed goods have little effect on the shade. That is, the disperse dyes of the three primary colors with uniform dyeing speeds are excellent in reproducibility of dyeing of polyester fiber products.
反対に、赤色、黄色及び青色の三原色の分散染料の染色速度が揃っていないときは、染色条件の僅かな変動によっても、得られる染色物の色調のみならず、色濃度も大幅に変化する。
On the contrary, when the dyeing speeds of the disperse dyes of the three primary colors of red, yellow and blue are not uniform, not only the color tone of the dyed material obtained but also the color density will change significantly even with a slight change in the dyeing conditions.
かくして、ポリエステル系繊維品を分散染料にて染色する場合、赤色、黄色及び青色の三原色の分散染料の染色速度が揃っていることが求められる。そこで、染色再現性よく、ポリエステル系繊維品を染色するために、赤色、黄色及び青色の三原色の分散染料について、それぞれ特定の構造を有する染料の組み合わせを用いることが提案されている（特許文献４及び５参照）。
Thus, when polyester textiles are dyed with disperse dyes, it is required that the disperse dyes of the three primary colors of red, yellow and blue have uniform dyeing speeds. Therefore, in order to dye polyester textiles with good dyeing reproducibility, it has been proposed to use a combination of three primary color disperse dyes of red, yellow and blue, each of which has a specific structure (Patent Document 4). and 5).
上述したポリエステル系繊維品の染色におけると同様に、黄色分散染料、赤色分散染料、青色分散染料各々と共に難燃剤を含む加工浴にポリエステル系繊維品を浸漬し、加熱して、ポリエステル系繊維品を染色すると同時に、難燃剤によって難燃加工を施す場合においても、用いる難燃剤によっては、同じ条件下に染色しても、難燃剤の不存在下に黄色分散染料、赤色分散染料、青色分散染料各々にてポリエステル系繊維品を染色する場合に比較して、上記各々の分散染料の染色速度が変動し、得られる染色物における色調や色濃度が大幅に変化する結果、染色再現性よく、ポリエステル系繊維品を染色同時難燃加工することができないことがある。
In the same manner as in the dyeing of the polyester fiber product described above, the polyester fiber product is immersed in a processing bath containing a flame retardant together with each of the yellow disperse dye, the red disperse dye, and the blue disperse dye, and heated to dye the polyester fiber product. Even when flame retardant processing is applied at the same time as dyeing, depending on the flame retardant used, yellow disperse dyes, red disperse dyes, and blue disperse dyes can be obtained in the absence of flame retardants even if dyeing is performed under the same conditions. As a result, the dyeing speed of each of the above disperse dyes fluctuates, and the color tone and color density of the resulting dyed product change significantly, resulting in good dyeing reproducibility and polyester fiber In some cases, textiles cannot be dyed and flame-retardant at the same time.
従って、黄色分散染料、赤色分散染料、青色分散染料各々を用いて、ポリエステル系繊維品を染色すると同時に難燃加工して、染色再現性よく、難燃加工染色物を得るには、用いる染料が染色再現性にすぐれるのみならず、用いる難燃剤もまた、併用する分散染料のすぐれた染色再現性を阻害するものであってはならない。
Therefore, using yellow disperse dyes, red disperse dyes, and blue disperse dyes, polyester fiber products are dyed at the same time as being flame-retardant to obtain a flame-retardant dyed product with good dyeing reproducibility. In addition to excellent dyeing reproducibility, the flame retardant used must not interfere with the excellent dyeing reproducibility of the disperse dyes used in combination.
本発明は、アゾ系分散染料と共に難燃剤を含む加工浴中にてポリエステル系繊維品を染色同時難燃加工する場合において、前記式（Ｉ）～（ＩＶ）で表されるアゾ系分散染料から選ばれる少なくとも１種か、又は前記式（Ｉ）～（ＩＶ）で表されるアゾ系分散染料から選ばれる少なくとも１種と前記式（Ｖ）～（ＶＩＩ）で表されるキノン系分散染料から選ばれる少なくとも１種を用いると共に、特定の難燃剤を用いることによって、染色再現性よく、染色難燃加工ポリエステル系繊維品を得るポリエステル系繊維品の染色同時難燃加工方法を提供することを目的とする。
The present invention uses the azo disperse dye represented by the above formulas (I) to (IV) in the case of dyeing and simultaneously flame retarding polyester textiles in a processing bath containing a flame retardant together with an azo disperse dye. At least one selected from, or from at least one selected from the azo disperse dyes represented by the formulas (I) to (IV) and the quinone disperse dyes represented by the formulas (V) to (VII) It is an object of the present invention to provide a method for simultaneously dyeing and flame-retarding polyester textiles to obtain dyed flame-retardant polyester textiles with good dyeing reproducibility by using at least one selected flame retardant and using a specific flame retardant. and
更に、本発明によれば、上記染色同時難燃加工方法によって得られた染色難燃加工ポリエステル系繊維品を提供することを目的とする。
Furthermore, according to the present invention, it is an object to provide a dyed flame-retardant polyester fiber product obtained by the method for flame-retardant treatment at the same time as dyeing.
本発明によれば、
（Ａ）（１）下記式（Ｉ） According to the invention,
(A) (1) Formula (I) below
（Ａ）（１）下記式（Ｉ） According to the invention,
(A) (1) Formula (I) below
で表されるアゾ系分散染料、
（２）下記式（ＩＩ） Azo disperse dye represented by
(2) Formula (II) below
（２）下記式（ＩＩ） Azo disperse dye represented by
(2) Formula (II) below
で表されるアゾ系分散染料、
（３）下記式（ＩＩＩ） Azo disperse dye represented by
(3) the following formula (III)
（３）下記式（ＩＩＩ） Azo disperse dye represented by
(3) the following formula (III)
で表されるアゾ系分散染料、及び
（４）下記式（ＩＶ） and (4) an azo disperse dye represented by the following formula (IV)
（４）下記式（ＩＶ） and (4) an azo disperse dye represented by the following formula (IV)
で表されるアゾ系分散染料から選ばれる少なくとも１種と、
（Ｂ）下記式（ＶＩＩＩ） At least one selected from azo disperse dyes represented by
(B) Formula (VIII) below
（Ｂ）下記式（ＶＩＩＩ） At least one selected from azo disperse dyes represented by
(B) Formula (VIII) below
で表されるリン酸エステルアミドを含む加工浴中にポリエステル系繊維品を浸漬し、加熱するポリエステル系繊維品の染色同時難燃加工方法が提供される。
Provided is a method for simultaneously dyeing and flame-retarding a polyester fiber article, comprising immersing the polyester fiber article in a processing bath containing a phosphoric acid ester amide represented by and heating the polyester fiber article.
以下、本発明において、上記方法を第１の方法ということがある。
Hereinafter, in the present invention, the above method may be referred to as the first method.
更に、本発明によれば、上記式（Ｉ）～（ＩＶ）で表されるアゾ系分散染料よりなる群から選ばれる少なくとも１種と、
下記式（Ｖ） Furthermore, according to the present invention, at least one selected from the group consisting of azo disperse dyes represented by the above formulas (I) to (IV);
Formula (V) below
下記式（Ｖ） Furthermore, according to the present invention, at least one selected from the group consisting of azo disperse dyes represented by the above formulas (I) to (IV);
Formula (V) below
で表されるキノン系分散染料、
下記式（ＶＩ） A quinone-based disperse dye represented by
Formula (VI) below
下記式（ＶＩ） A quinone-based disperse dye represented by
Formula (VI) below
で表されるキノン系分散染料、及び
下記式（ＶＩＩ） and a quinone-based disperse dye represented by the following formula (VII)
下記式（ＶＩＩ） and a quinone-based disperse dye represented by the following formula (VII)
で表されるキノン系分散染料から選ばれる少なくとも１種と、前記式（ＶＩＩＩ）で表されるリン酸エステルアミドを含む加工浴中にポリエステル系繊維品を浸漬し、加熱するポリエステル系繊維品の染色同時難燃加工方法が提供される。
At least one selected from quinone disperse dyes represented by and immersing a polyester fiber product in a processing bath containing a phosphoric acid ester amide represented by the formula (VIII), and heating the polyester fiber product. A simultaneous dyeing flame retardant processing method is provided.
以下、本発明において、上記方法を第２の方法ということがある。
Hereinafter, in the present invention, the above method may be referred to as the second method.
本発明による上述した第１の方法においては、詳しくは、上記加工浴中にポリエステル系繊維品を浸漬し、１０５℃以上に加熱し、また、上記加工浴は、好ましくは、上記式（Ｉ）から（ＩＶ）で表されるアゾ系分散染料の少なくとも１種を濃度０．０５～５％оｗｆの範囲で有し、上記式（ＶＩＩＩ）で表されるリン酸エステルアミドを濃度０．５～１０％оｗｆの範囲で有する。
Specifically, in the above-described first method according to the present invention, the polyester fiber product is immersed in the processing bath and heated to 105° C. or higher, and the processing bath preferably contains the above formula (I) At least one of the azo disperse dyes represented by (IV) from 0.05 to 5% wf, and the phosphoric acid ester amide represented by the above formula (VIII) at a concentration of 0.5 to It has in the range of 10% Ωwf.
本発明による上述した第２の方法においては、詳しくは、上記加工浴中にポリエステル系繊維品を浸漬し、１０５℃以上に加熱し、また、上記加工浴は、好ましくは、上記式（Ｉ）から（ＩＶ）で表されるアゾ系分散染料の少なくとも１種と上記式（Ｖ）から（ＶＩＩ）で表されるキノン系分散染料の少なくとも１種を合計濃度０．０５～５％оｗｆの範囲で有し、上記式（ＶＩＩＩ）で表されるリン酸エステルアミドを濃度０．５～１０％оｗｆの範囲で有する。
Specifically, in the above-described second method according to the present invention, the polyester fiber product is immersed in the processing bath and heated to 105° C. or higher, and the processing bath preferably contains the above formula (I) At least one of the azo disperse dyes represented by (IV) and at least one of the quinone disperse dyes represented by the above formulas (V) to (VII) in a total concentration range of 0.05 to 5% wf and the concentration of the phosphate ester amide represented by the above formula (VIII) is in the range of 0.5 to 10% wf.
また、本発明によれば、用いる前記アゾ系及びキノン系分散染料と前記リン酸エステルアミドはいずれも、平均粒子径０．２～２．０μｍの範囲にあるものであることが好ましい。
Further, according to the present invention, both the azo-based and quinone-based disperse dyes and the phosphoric acid ester amide used preferably have an average particle size in the range of 0.2 to 2.0 μm.
本発明によるポリエステル系繊維品の染色同時難燃加工方法は、前記式（ＶＩＩＩ）で表される難燃剤リン酸エステルアミドと共に、
前記式（Ｉ）～（ＩＶ）で表されるアゾ系分散染料よりなる群から選ばれる少なくとも１種か、又は
前記式（Ｉ）～（ＩＶ）で表されるアゾ系分散染料よりなる群から選ばれる少なくとも１種と前記式（Ｖ）～（ＶＩＩ）で表されるキノン系分散染料よりなる群から選ばれる少なくとも１種
を用いて、ポリエステル系繊維品を染色すると同時に難燃加工するものである。 The flame retardant treatment method simultaneously with dyeing of polyester fiber products according to the present invention includes, together with the flame retardant phosphate ester amide represented by the formula (VIII),
At least one selected from the group consisting of the azo disperse dyes represented by the formulas (I) to (IV), or from the group consisting of the azo disperse dyes represented by the formulas (I) to (IV) Using at least one selected and at least one selected from the group consisting of the quinone disperse dyes represented by the formulas (V) to (VII), polyester textiles are dyed and flame retarded at the same time. be.
前記式（Ｉ）～（ＩＶ）で表されるアゾ系分散染料よりなる群から選ばれる少なくとも１種か、又は
前記式（Ｉ）～（ＩＶ）で表されるアゾ系分散染料よりなる群から選ばれる少なくとも１種と前記式（Ｖ）～（ＶＩＩ）で表されるキノン系分散染料よりなる群から選ばれる少なくとも１種
を用いて、ポリエステル系繊維品を染色すると同時に難燃加工するものである。 The flame retardant treatment method simultaneously with dyeing of polyester fiber products according to the present invention includes, together with the flame retardant phosphate ester amide represented by the formula (VIII),
At least one selected from the group consisting of the azo disperse dyes represented by the formulas (I) to (IV), or from the group consisting of the azo disperse dyes represented by the formulas (I) to (IV) Using at least one selected and at least one selected from the group consisting of the quinone disperse dyes represented by the formulas (V) to (VII), polyester textiles are dyed and flame retarded at the same time. be.
従来、知られている難燃剤とアゾ系分散染料を含む加工浴にてポリエステル系繊維品を染色同時難燃加工した場合、上記難燃剤の不存在下に上記アゾ系分散染料にて染色した場合と比較して、上記アゾ系分散染料の染色速度が大きく変化するために、染色再現性よく染色難燃加工ポリエステル系繊維品を得ることができない。
Conventionally, when a polyester fiber product is dyed and simultaneously flame retarded in a processing bath containing a known flame retardant and an azo disperse dye, when dyeing with the azo disperse dye in the absence of the flame retardant. Since the dyeing speed of the azo disperse dye changes greatly compared to the above, it is not possible to obtain a flame-retardant polyester fiber product with good dyeing reproducibility.
しかしながら、本発明に従って、前記式（ＶＩＩＩ）で表される難燃剤リン酸エステルアミドと共に、前記式（Ｉ）から（ＩＶ）で表されるアゾ系分散染料よりなる群から選ばれる少なくとも１種か、又は前記式（Ｉ）から（ＩＶ）で表されるアゾ系分散染料よりなる群から選ばれる少なくとも１種と前記式（Ｖ）から（ＶＩＩ）で表されるキノン系分散染料よりなる群から選ばれる少なくとも１種とを含む加工浴中にてポリエステル系繊維品を染色同時難燃加工した場合、上記アゾ系分散染料の染色速度の変化が小さく、また、上記キノン系分散染料を併用した場合は、上記アゾ系分散染料と上記キノン系分散染料の染色速度の変化が共に小さいことから、染色再現性よく、染色難燃加工ポリエステル系繊維品を得ることができる。
However, according to the present invention, at least one selected from the group consisting of the azo disperse dyes represented by the formulas (I) to (IV) together with the flame retardant phosphate ester amide represented by the formula (VIII) , or from the group consisting of at least one selected from the group consisting of the azo disperse dyes represented by the formulas (I) to (IV) and the quinone disperse dyes represented by the formulas (V) to (VII) When a polyester fiber product is subjected to flame retardant treatment at the same time as dyeing in a processing bath containing at least one selected from Since the azo disperse dye and the quinone disperse dye both have small changes in dyeing speed, it is possible to obtain dyed flame-retardant polyester textiles with good dyeing reproducibility.
本発明によるポリエステル系繊維品の染色同時難燃加工方法は、前記式（Ｉ）～（ＩＶ）で表されるアゾ系分散染料よりなる群から選ばれる少なくとも１種か、又は前記式（Ｉ）～（ＩＶ）で表されるアゾ系分散染料よりなる群から選ばれる少なくとも１種と前記式（Ｖ）～（ＶＩＩ）で表されるキノン系分散染料よりなる群から選ばれる少なくとも１種と前記式（ＶＩＩＩ）で表されるリン酸エステルアミドを含む加工浴中にポリエステル系繊維品を浸漬し、加熱して、染色同時難燃加工するものであり、このような方法によれば、染色再現性よく、染色難燃加工ポリエステル系繊維品を得ることができる。
The method for dyeing and simultaneously flame retarding polyester textiles according to the present invention is at least one selected from the group consisting of azo disperse dyes represented by the above formulas (I) to (IV), or the above formula (I) at least one selected from the group consisting of azo disperse dyes represented by (IV) and at least one selected from the group consisting of quinone disperse dyes represented by formulas (V) to (VII); A polyester fiber product is immersed in a processing bath containing a phosphoric acid ester amide represented by formula (VIII), heated, and flame-retardant processed at the same time as dyeing. A dyed, flame-retardant polyester fiber product can be obtained with high efficiency.
即ち、本発明によるポリエステル系繊維品の染色同時難燃加工方法は、その加工浴に前記式（Ｉ）～（ＩＶ）で表されるアゾ系分散染料よりなる群から選ばれる少なくとも１種か、又は前記式（Ｉ）～（ＩＶ）で表されるアゾ系分散染料よりなる群から選ばれる少なくとも１種と前記式（Ｖ）～（ＶＩＩ）で表されるキノン系分散染料よりなる群から選ばれる少なくとも１種と上記式（ＶＩＩＩ）で表されるリン酸エステルアミドを含む。
That is, in the method for simultaneously dyeing and flame-retarding polyester fiber products according to the present invention, at least one selected from the group consisting of azo disperse dyes represented by the above formulas (I) to (IV) is added to the processing bath, Or at least one selected from the group consisting of azo disperse dyes represented by formulas (I) to (IV) and the group consisting of quinone disperse dyes represented by formulas (V) to (VII). and at least one phosphoric acid ester amide represented by the above formula (VIII).
上記式（Ｉ）～（ＩＶ）で表されるアゾ系分散染料はいずれも既に知られており、本発明の方法においては、いずれも市販品を用いることができる。
All of the azo disperse dyes represented by formulas (I) to (IV) are already known, and commercial products can be used in the method of the present invention.
上記式（Ｉ）で表されるアゾ系分散染料は、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ Ｙｅｌｌｏｗ １６３である。
The azo disperse dye represented by the above formula (I) is C.I. I. Disperse Yellow 163.
上記式（ＩＩ）で表されるアゾ系分散染料は、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ Ｒｅｄ １６７：１であり、上記式（ＩＩＩ）で表されるアゾ系分散染料は、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ Ｂｌｕｅ １６５であり、上記式（ＩＶ）で表されるアゾ系分散染料は、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ Ｂｌｕｅ ７９：１である。
The azo disperse dye represented by the above formula (II) is C.I. I. Disperse Red 167:1, and the azo disperse dye represented by the above formula (III) is C.I. I. Disperse Blue 165, and the azo disperse dye represented by the above formula (IV) is C.I. I. Disperse Blue 79:1.
また、前記式（Ｖ）で表されるキノン系分散染料は、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ Ｂｌｕｅ ５６であり、前記式（ＶＩ）で表されるキノン系分散染料は、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ Ｂｌｕｅ ６０であり、前記式（ＶＩＩ）で表されるキノン系分散染料は、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ Ｂｌｕｅ ７７である。
In addition, the quinone-based disperse dye represented by the formula (V) is C.I. I. Disperse Blue 56, and the quinone-based disperse dye represented by the formula (VI) is C.I. I. Disperse Blue 60, and the quinone-based disperse dye represented by the formula (VII) is C.I. I. Disperse Blue 77.
本発明においては、上記アゾ系分散染料か、又は上記アゾ系分散染料とキノン系分散染料と共に、前記難燃剤リン酸エステルアミドを用いて、ポリエステル系繊維品に染色同時難燃加工を施すに際して、上記分散染料と難燃剤リン酸エステルアミドがポリエステル系繊維品の内部に十分に拡散し、付着するように、上記分散染料とリン酸エステルアミドはいずれも、０．２～２．０μｍの平均粒子径を有するものであることが好ましい。但し、上記分散染料と難燃剤リン酸エステルアミドが同じ平均粒子径を有する必要はない。
In the present invention, the azo disperse dye, or the azo disperse dye and the quinone disperse dye together with the flame retardant phosphoric acid ester amide is used to subject the polyester fiber product to flame retardant treatment at the same time as dyeing, Both the disperse dye and the phosphate ester amide have an average particle size of 0.2 to 2.0 μm so that the disperse dye and the flame retardant phosphate ester amide can sufficiently diffuse and adhere to the interior of the polyester fiber product. It preferably has a diameter. However, the disperse dye and the flame retardant phosphate ester amide need not have the same average particle size.
上述した範囲の平均粒子径を有する前記分散染料とリン酸エステルアミドは、例えば、前記系分散染料とリン酸エステルアミドをそれぞれ、予め、界面活性剤を含む水中でサンドミルやボールミルで微細化することによって得ることができる。
The disperse dye and phosphate ester amide having an average particle size within the range described above can be obtained, for example, by pulverizing each of the disperse dye and phosphate ester amide in advance with a sand mill or ball mill in water containing a surfactant. can be obtained by
前記アゾ系分散染料とキノン系分散染料を微細化する際に用いる界面活性剤としては、例えば、ナフタリ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界面活性剤、エチレンオキサイドとプロピレンオキサイド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ノニオン界面活性剤や、これらのアニオン界面活性剤とノニオン界面活性剤との混合物が好ましい。
Surfactants used for refining the azo disperse dyes and quinone disperse dyes include, for example, formalin condensates of naphthalenesulfonic acid and alkylbenzenesulfonic acid, formalin condensates of naphthalenesulfonic acid, cresol and 2-naphthol. -6-formalin condensate of sulfonic acid, formalin condensate of alkylnaphthalenesulfonic acid, formalin condensate of creosote oil sulfonic acid, anionic surfactants such as ligninsulfonic acid, block copolymers of ethylene oxide and propylene oxide, Nonionic surfactants such as ethylene oxide adducts of alkylphenols and ethylene oxide adducts of polystyrenated phenols, and mixtures of these anionic surfactants and nonionic surfactants are preferred.
前記リン酸エステルアミドを微細化する際に用いる界面活性剤としては、例えば、アリール化フェノールエチレンオキサイド付加物の硫酸エステル塩、スチレン化フェノールエチレンオキサイド付加物のスルホ琥珀酸エステル塩等のアニオン界面活性剤、エチレンオキサイドとプロピレンオキサイド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ノニオン界面活性剤、又は、これらのアニオン界面活性剤とノニオン界面活性剤との混合物が好ましい。
Examples of surfactants used for refining the phosphoric acid ester amide include anionic surfactants such as sulfuric acid ester salts of arylated phenol ethylene oxide adducts and sulfosuccinic acid ester salts of styrenated phenol ethylene oxide adducts. nonionic surfactants such as agents, block copolymers of ethylene oxide and propylene oxide, ethylene oxide adducts of alkylphenols, ethylene oxide adducts of polystyrenated phenols, or combinations of these anionic surfactants and nonionic surfactants Mixtures are preferred.
本発明によるポリエステル系繊維品の染色同時難燃加工方法は、上述したように、特定のアゾ系分散染料と、そして、アゾ系分散染料と併用する場合は、特定のキノン系分散染料と、特定の難燃剤をそれぞれ上記界面活性剤の存在下に湿式粉砕して、それぞれ上記分散染料と難燃剤の微粒子を含む分散液とし、これらを水を含む浴に加えて、所定の浴比を有する加工浴を構成し、この加工浴にポリエステル系繊維品を浸漬し、１０５℃以上、好ましくは、１０５～１４０℃の範囲の温度、特に好ましくは、１１０～１４０℃の範囲の温度で３０～６０分間、浴中吸尽処理し、この後、このように処理したポリエステル系繊維品を加工浴から取り出し、ソーピング処理、水洗処理した後、脱水乾燥すれば、染色難燃加工したポリエステル系繊維品を得ることができる。
As described above, the method for dyeing and simultaneously flame retarding polyester textiles according to the present invention includes a specific azo disperse dye, and when used in combination with the azo disperse dye, a specific quinone disperse dye, and a specific are wet pulverized in the presence of the surfactant, respectively, to form a dispersion containing fine particles of the disperse dye and the flame retardant, and these are added to a bath containing water to obtain a predetermined bath ratio. A bath is constructed, and a polyester fiber product is immersed in this processing bath, and the temperature is 105° C. or higher, preferably in the range of 105 to 140° C., particularly preferably in the range of 110 to 140° C., for 30 to 60 minutes. Then, the treated polyester fiber product is removed from the processing bath, treated with soaping, washed with water, dehydrated and dried to obtain a dyed flame-retardant polyester fiber product. be able to.
本発明において、例えば、液流染色機を用いて、染色機内の加工浴にポリエステル系繊維品を浸漬し、１０５℃以上に加熱して、浴中吸尽処理する際、通常、染色機内の圧力は、０．１～０．５ＭＰａの範囲である。
In the present invention, for example, using a liquid jet dyeing machine, the polyester fiber product is immersed in the processing bath in the dyeing machine, heated to 105 ° C. or higher, and exhausted in the bath. is in the range of 0.1-0.5 MPa.
このようにして、本発明によれば、上記アゾ系分散染料にて、又は上記キノン系分散染料を併用した場合には、上記アゾ系分散染料と上記キノン系分散染料にて染色されていると共に、上記難燃剤にて難燃加工されているポリエステル系繊維品を得ることができる。
Thus, according to the present invention, when the azo disperse dye or the quinone disperse dye is used in combination, the dye is dyed with the azo disperse dye and the quinone disperse dye. , a polyester fiber article flame-retardant treated with the flame retardant can be obtained.
本発明による第１の方法において、前記アゾ系分散染料と難燃剤リン酸エステルアミドの使用量は、特に限定されるものではないが、アゾ系分散染料の使用量は、通常、０．０５～５％ｏｗｆの範囲であり、好ましくは、０．１～５％ｏｗｆの範囲であり、更に好ましくは、０．３～３．０％ｏｗｆの範囲である。
In the first method according to the present invention, the amounts of the azo disperse dye and the flame retardant phosphate ester amide used are not particularly limited, but the amount of the azo disperse dye used is usually from 0.05 to It is in the range of 5%owf, preferably in the range of 0.1 to 5%owf, more preferably in the range of 0.3 to 3.0%owf.
本発明による第２の方法において、前記アゾ系分散染料と共に前記キノン系分散染料を併用した場合には、前記アゾ系分散染料と前記キノン系分散染料の使用量は、合計量にて、通常、０．０５～５％ｏｗｆの範囲であり、好ましくは、０．１～５％ｏｗｆの範囲であり、更に好ましくは、０．３～３．０％ｏｗｆの範囲である。
In the second method according to the present invention, when the quinone disperse dye is used together with the azo disperse dye, the total amount of the azo disperse dye and the quinone disperse dye is usually It is in the range of 0.05 to 5%owf, preferably in the range of 0.1 to 5%owf, and more preferably in the range of 0.3 to 3.0%owf.
また、前記難燃剤リン酸エステルアミドの使用量は、通常、染色するポリエステル系繊維品に十分な難燃性能を付与するために、０．５～１０％ｏｗｆの範囲であることが好ましく、０．５～８．０％ｏｗｆの範囲であることがより好ましく、１．０～８．０％ｏｗｆの範囲であることが最も好ましい。
In addition, the amount of the flame retardant phosphate ester amide used is usually preferably in the range of 0.5 to 10% owf in order to impart sufficient flame retardancy to polyester textiles to be dyed. It is more preferably in the range of .5 to 8.0%owf, most preferably in the range of 1.0 to 8.0%owf.
また、加工浴の浴比は、特に制限されるものではないが、通常、１：３～１：３０の範囲であり、好ましくは、１：５～１：２０の範囲である。浴比が１：３よりも低い場合は、ポリエステル系繊維品が加工浴に十分に浸漬されないために染色むらが発生するおそれがあり、他方、１：３０よりも高い場合は、染色難燃同時加工に用いる水量が徒に多くなるので不経済である。
Also, the bath ratio of the working bath is not particularly limited, but is usually in the range of 1:3 to 1:30, preferably in the range of 1:5 to 1:20. If the bath ratio is lower than 1:3, uneven dyeing may occur because the polyester fiber product is not sufficiently immersed in the processing bath. It is uneconomical because the amount of water used for processing is unnecessarily large.
本発明の方法において、ポリエステル系繊維品とは、少なくともポリエステル繊維を含む繊維と、そのような繊維を含む糸、綿、編織布や不織布等の布帛をいい、好ましくは、ポリエステル繊維、これよりなる糸、綿、編織布や不織布等の布帛をいう。更に、編織布や不織布等の布帛は単層であっても二層以上の積層体であってもよく、糸、綿、編織布や不織布等からなる複合体であってもよい。
In the method of the present invention, the polyester fiber product refers to a fiber containing at least polyester fiber, yarn containing such fiber, cotton, fabric such as woven fabric and non-woven fabric, preferably polyester fiber. Fabrics such as threads, cotton, woven fabrics and non-woven fabrics. Further, the fabric such as a woven fabric or a non-woven fabric may be a single layer or a laminate of two or more layers, or may be a composite made of yarn, cotton, a woven fabric, a non-woven fabric, or the like.
本発明において、上記ポリエステル繊維は、例えば、ポリエチレンテレフタレート、ポリプロピレンテレフタレート、ポリブチレンテレフタレート、ポリエチレンナフタレート、ポリブチレンナフタレート、ポリエチレンテレフタレート／イソフタレート、ポリエチレンテレフタレート／５－スルホイソフタレート、ポリエチレンテレフタレート／ポリオキシベンゾイル、ポリブチレンテレフタレート／イソフタレート、ポリ（Ｄ－乳酸）、ポリ（Ｌ－乳酸）、Ｄ－乳酸とＬ－乳酸の共重合体、Ｄ－乳酸と脂肪族ヒドロキシカルボン酸との共重合体、Ｌ－乳酸と脂肪族ヒドロキシカルボン酸との共重合体、ポリ－ε－カプロラクトン（ＰＣＬ）等のポリカプロラクトン、ポリリンゴ酸、ポリヒドロキシカルボン酪酸、ポリヒドロキシ吉草酸、β－ヒドロキシ酪酸（３ＨＢ）－３－ヒドロキシ吉草酸（３ＨＶ）ランダム共重合体等のポリ脂肪族ヒドロキシカルボン酸、ポリエチレンサクシネート（ＰＥＳ）、ポリブチレンサクシネート（ＰＢＳ）、ポリブチレンアジペート、ポリブチレンサクシネート－アジペート共重合体等のグリコールと脂肪族ジカルボン酸とのポリエステル等を挙げることができるが、これら例示されたものに限定されない。
In the present invention, the polyester fiber is, for example, polyethylene terephthalate, polypropylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polybutylene naphthalate, polyethylene terephthalate/isophthalate, polyethylene terephthalate/5-sulfoisophthalate, polyethylene terephthalate/polyoxy benzoyl, polybutylene terephthalate/isophthalate, poly(D-lactic acid), poly(L-lactic acid), copolymers of D-lactic acid and L-lactic acid, copolymers of D-lactic acid and aliphatic hydroxycarboxylic acids, Copolymers of L-lactic acid and aliphatic hydroxycarboxylic acids, polycaprolactones such as poly-ε-caprolactone (PCL), polymalic acid, polyhydroxycarboxylic butyric acid, polyhydroxyvaleric acid, β-hydroxybutyric acid (3HB)-3 - Polyaliphatic hydroxycarboxylic acids such as hydroxyvaleric acid (3HV) random copolymers, polyethylene succinate (PES), polybutylene succinate (PBS), polybutylene adipate, polybutylene succinate-adipate copolymers, etc. Examples include polyesters of glycol and aliphatic dicarboxylic acid, but are not limited to these examples.
本発明の方法によって得られる染色難燃加工ポリエステル系繊維品は、例えば、座席シート、シートカバー、カーテン、壁紙、天井クロス、カーペット、緞帳、建築養生シート、テント、帆布等に好適に用いられる。
The dyed flame-retardant polyester fiber product obtained by the method of the present invention is suitably used for, for example, seat sheets, seat covers, curtains, wallpapers, ceiling cloths, carpets, drop curtains, architectural protection sheets, tents, canvases, and the like.
本発明の方法においては、本発明によるポリエステル系繊維品の染色同時難燃加工方法による染色再現性が阻害されない限り、従来から既に知られているその他の分散染料を併用することができる。そのような分散染料としては、例えば、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ Ｒｅｄ ５３、６０、８６、９２等の赤色分散染料、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ Ｙｅｌｌｏｗ ７１、４２、５１、Ｃ．Ｉ．Ｓｏｌｖｅｎｔ Ｙｅｌｌｏｗ １６３等の黄色分散染料、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ Ｂｌｕｅ ５４等の青色分散染料、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ Ｏｒａｎｇｅ ２９、１５５等の橙色分散染料等を挙げることができるが、これらに限定されるものではない。
In the method of the present invention, other conventionally known disperse dyes can be used in combination as long as the dyeing reproducibility by the method of flame retardant processing simultaneously with dyeing of polyester fiber products according to the present invention is not hindered. Examples of such disperse dyes include C.I. I. Red disperse dyes such as Disperse Red 53, 60, 86, 92, C.I. I. Disperse Yellow 71, 42, 51, C.I. I. Yellow disperse dyes such as Solvent Yellow 163, C.I. I. Blue disperse dyes such as Disperse Blue 54, C.I. I. Orange disperse dyes such as Disperse Orange 29 and 155 can be used, but the dyes are not limited to these.
以下に実施例と共に比較例を挙げて、本発明を詳細に説明するが、本発明はそれら実施例によって何ら限定されるものではない。
The present invention will be described in detail below with examples and comparative examples, but the present invention is not limited by these examples.
（アゾ系分散染料及びキノン系分散染料と難燃剤の平均粒子径）
以下において、アゾ系分散染料とキノン系分散染料と難燃剤はいずれも、直径０．５ｍｍのガラスビーズを充填したミルを用いて、それぞれ界面活性剤の存在下に所定の平均粒子径を有するように湿式粉砕し、水分散液として用いた。 (Azo-based disperse dye, quinone-based disperse dye, and average particle size of flame retardant)
In the following, azo disperse dyes, quinone disperse dyes, and flame retardants are each measured using a mill filled with glass beads having a diameter of 0.5 mm so as to have a predetermined average particle size in the presence of a surfactant. It was wet pulverized and used as an aqueous dispersion.
以下において、アゾ系分散染料とキノン系分散染料と難燃剤はいずれも、直径０．５ｍｍのガラスビーズを充填したミルを用いて、それぞれ界面活性剤の存在下に所定の平均粒子径を有するように湿式粉砕し、水分散液として用いた。 (Azo-based disperse dye, quinone-based disperse dye, and average particle size of flame retardant)
In the following, azo disperse dyes, quinone disperse dyes, and flame retardants are each measured using a mill filled with glass beads having a diameter of 0.5 mm so as to have a predetermined average particle size in the presence of a surfactant. It was wet pulverized and used as an aqueous dispersion.
また、アゾ系分散染料とキノン系分散染料と難燃剤の平均粒子径はいずれも、それぞれの分散液について（株）島津製作所製レーザー回折式粒度分布測定装置ＳＡＬＤ－２０００Ｊによって粒度分布を測定して、これに基づいて求めた体積基準のメディアン径をいう。
In addition, the average particle size of each of the azo disperse dye, the quinone disperse dye, and the flame retardant is obtained by measuring the particle size distribution of each dispersion with a laser diffraction particle size distribution analyzer SALD-2000J manufactured by Shimadzu Corporation. , refers to the volume-based median diameter obtained based on this.
（染色物の測色）
以下において、得られた染色物の測色は、分光測色計ＣＭ－６００ｄ（コニカミノルタ（株）製）を用いた。 (Color measurement of dyeing)
In the following, a spectrophotometer CM-600d (manufactured by Konica Minolta, Inc.) was used to measure the color of the obtained dyed material.
以下において、得られた染色物の測色は、分光測色計ＣＭ－６００ｄ（コニカミノルタ（株）製）を用いた。 (Color measurement of dyeing)
In the following, a spectrophotometer CM-600d (manufactured by Konica Minolta, Inc.) was used to measure the color of the obtained dyed material.
以下の実施例及び比較例においては、先ず、ポリエステルダブルピケ（目付重量２４０ｇ／ｍ２）を被処理布帛とし、これを温度１００℃において難燃剤の不存在下に分散染料で染色して得た染色物と、難燃剤の存在下に上記と同じ分散染料で染色して得た染色物のそれぞれについて測色して得たそれら染色物の間の色差△Ｅ（１００℃）と、上記被処理布帛を温度１３０℃において難燃剤の不存在下に分散染料で染色して得た染色物と、難燃剤の存在下に上記と同じ分散染料で染色して得た染色物のそれぞれについて測色して得たそれら染色物の間の色差△Ｅ（１３０℃）を求めた。
In the following examples and comparative examples, first, a polyester double picket (basis weight of 240 g/m 2 ) was used as a fabric to be treated, and this was obtained by dyeing with a disperse dye at a temperature of 100 ° C. in the absence of a flame retardant. The color difference ΔE (100° C.) between the dyed article and the dyed article obtained by dyeing with the same disperse dye as above in the presence of a flame retardant, and the above treated A dyed product obtained by dyeing a fabric with a disperse dye in the absence of a flame retardant at a temperature of 130 ° C. and a dyed product obtained by dyeing with the same disperse dye as above in the presence of a flame retardant were measured. The color difference .DELTA.E (130.degree. C.) between the dyeings obtained by
次に、難燃剤の不存在下に温度１００℃と温度１３０℃でそれぞれ分散染料で染色して得た染色物の色差△Ｅ（染料）と、難燃剤の存在下に温度１００℃と温度１３０℃でそれぞれ分散染料で染色して得た染色物の色差△Ｅ（染料＋難燃剤）を求めた。
Next, the color difference ΔE (dye) of the dyed product obtained by dyeing with a disperse dye at a temperature of 100 ° C. and a temperature of 130 ° C. in the absence of a flame retardant, and the temperature of 100 ° C. and the temperature of 130 ° C. in the presence of a flame retardant. The color difference ΔE (dye + flame retardant) of the dyed product obtained by dyeing with each disperse dye at °C was determined.
次いで、上記色差△Ｅ（染料）と色差△Ｅ（染料＋難燃剤）より、式（△Ｅ（染料）／△Ｅ（染料＋難燃剤））×１００の値を求め、この値を難燃剤の存在下に分散染料にて上記被処理布帛を染色したときの染色速度変化率とした。
Next, from the color difference ΔE (dye) and the color difference ΔE (dye + flame retardant), the value of the formula (ΔE (dye) / ΔE (dye + flame retardant)) × 100 is obtained, and this value is used as the flame retardant. The rate of change in dyeing speed when the treated fabric was dyed with a disperse dye in the presence of .
本発明については、後述するように、上記△Ｅ（１００℃）、△Ｅ（１３０℃）及び（△Ｅ（染料）／△Ｅ（染料＋難燃剤））×１００の値、即ち、染色速度変化率のすべてが一定の範囲にある場合を染色再現性がすぐれるとした。
Regarding the present invention, as described later, the values of ΔE (100 ° C.), ΔE (130 ° C.) and (ΔE (dye) / ΔE (dye + flame retardant)) × 100, that is, the dyeing speed Staining reproducibility was judged to be excellent when all of the rate of change was within a certain range.
本発明においては、上記被処理布帛を染色同時難燃加工して得られた染色物の色調を評価するに際して、国際照明委員会（ＣＩＥ）が１９７４年に策定したＬ*ａ*ｂ* 表色系による色空間によった。上記Ｌ*ａ*ｂ* 表色系において、Ｌ* 値は明度指数と呼ばれており、値が大きい程、明るいことを示し、値が小さい程、暗いことを示す。白色のＬ* 値は１００であり、黒色のＬ* 値は０である。ａ* 値とｂ* 値は色調と彩度を表し、クロマティクス指数と呼ばれている。ａ* 値が正の値方向に大きくなるほど、赤味が強くなり、負方向に大きくなるほど、緑味が強くなる。ｂ* 値が正の値方向に大きくなるほど、黄味が強くなり、負方向に大きくなるほど、青味が強くなる。
In the present invention, when evaluating the color tone of the dyed product obtained by flame retarding the treated fabric at the same time as dyeing, the L * a * b * color specification formulated by the International Commission on Illumination (CIE) in 1974 According to the color space by the system. In the L * a * b * color system, the L * value is called a lightness index, and a larger value indicates a brighter color, and a smaller value indicates a darker color. White has an L * value of 100 and black has an L * value of 0. The a * and b* values represent hue and saturation and are called chromaticity indices. As the a * value increases in the positive direction, the color becomes reddish, and as the a* value increases in the negative direction, the color becomes greenish. As the b * value increases in the positive direction, the color becomes more yellowish, and as the b* value increases in the negative direction, the color becomes more bluish.
このようなＬ*ａ*ｂ* 表色系において、２つの色の差、即ち、色差△Ｅは、色空間における上記２つの色の座標間の距離で表される。即ち、
△Ｅ＝[(△Ｌ*)２＋(△ａ*)２＋(△ｂ*)２]１／２ In such an L * a * b * color system, the difference between two colors, ie, the color difference ΔE, is represented by the distance between the coordinates of the two colors in the color space. Namely
ΔE=[(ΔL * ) 2 +(Δa * ) 2 +(Δb * ) 2 ] 1/2
△Ｅ＝[(△Ｌ*)２＋(△ａ*)２＋(△ｂ*)２]１／２ In such an L * a * b * color system, the difference between two colors, ie, the color difference ΔE, is represented by the distance between the coordinates of the two colors in the color space. Namely
ΔE=[(ΔL * ) 2 +(Δa * ) 2 +(Δb * ) 2 ] 1/2
実施例１
前記式（Ｉ）で表される平均粒子径０．８μｍのアゾ系分散染料０．３％ｏｗｆを含む浴比１：１０の加工浴へ被処理布帛（ポリエステルダブルピケ（目付重量２４０ｇ／ｍ２））を投入し、４０℃から毎分２℃の昇温速度で１００℃まで昇温して浴中吸尽処理し、次いで、ソーピング処理と水洗処理を行った後、脱水乾燥して、染色布帛を得た。この染色布帛を測色して、Ｌ*(100）、ａ*(100)及びｂ*(100)を求めた。 Example 1
The fabric to be treated (polyester double picket (basis weight: 240 g/m 2 )) is added, and the temperature is raised from 40°C to 100°C at a rate of 2°C per minute for exhaustion treatment in the bath, followed by soaping treatment and water washing treatment, dehydration drying, and dyeing. I got the fabric. This dyed fabric was colorimetrically measured to determine L * (100), a * (100) and b * (100).
前記式（Ｉ）で表される平均粒子径０．８μｍのアゾ系分散染料０．３％ｏｗｆを含む浴比１：１０の加工浴へ被処理布帛（ポリエステルダブルピケ（目付重量２４０ｇ／ｍ２））を投入し、４０℃から毎分２℃の昇温速度で１００℃まで昇温して浴中吸尽処理し、次いで、ソーピング処理と水洗処理を行った後、脱水乾燥して、染色布帛を得た。この染色布帛を測色して、Ｌ*(100）、ａ*(100)及びｂ*(100)を求めた。 Example 1
The fabric to be treated (polyester double picket (basis weight: 240 g/m 2 )) is added, and the temperature is raised from 40°C to 100°C at a rate of 2°C per minute for exhaustion treatment in the bath, followed by soaping treatment and water washing treatment, dehydration drying, and dyeing. I got the fabric. This dyed fabric was colorimetrically measured to determine L * (100), a * (100) and b * (100).
次に、上記と同じ構成にした加工浴へ上記と同じ被処理布帛を投入し、４０℃から毎分２℃の昇温速度で１３０℃まで昇温し、その温度で３０分間保持して、浴中吸尽処理し、次いで、ソーピング処理と水洗処理を行った後、脱水乾燥して、染色布帛を得た。この染色布帛を上記と同様に測色して、Ｌ*(130）、ａ*(130) 及びｂ*(130)を求めた。
Next, the same treated fabric as above is put into a processing bath having the same structure as above, and the temperature is raised from 40 ° C. to 130 ° C. at a rate of 2 ° C. per minute, and held at that temperature for 30 minutes. It was exhausted in a bath, then soaped and washed with water, and then dehydrated and dried to obtain a dyed fabric. This dyed fabric was measured in the same manner as above to determine L * (130), a * (130) and b * (130).
別に、前記式（Ｉ）で表される平均粒子径０．８μｍのアゾ系分散染料０．３％ｏｗｆと共に前記式（ＶＩＩＩ）で表される平均粒子径０．６μｍの難燃剤リン酸エステルアミド４．０％ｏｗｆを含む浴比１：１０の加工浴に上記と同じ被処理布帛を投入し、４０℃から毎分２℃の昇温速度で１００℃まで昇温して浴中吸尽処理し、次いで、ソーピング処理と水洗処理を行った後、脱水乾燥して、染色布帛を得た。
Separately, 0.3% owf of an azo disperse dye having an average particle size of 0.8 µm represented by the formula (I) and a flame retardant phosphate ester amide having an average particle size of 0.6 µm represented by the formula (VIII) The same treated fabric as above is put into a processing bath containing 4.0% owf at a bath ratio of 1:10, and the temperature is raised from 40 ° C. to 100 ° C. at a rate of 2 ° C. per minute to perform in-bath exhaust treatment. Then, after performing a soaping treatment and a water washing treatment, the fabric was dehydrated and dried to obtain a dyed fabric.
上記染色布帛を前記と同様に測色して、Ｌ*(100難燃剤)、ａ*(100難燃剤)及びｂ*(100難燃剤) を求めた。
The dyed fabric was measured in the same manner as described above to determine L * (100 flame retardant), a * (100 flame retardant) and b * (100 flame retardant).
次に、上記と同じ構成にした加工浴へ上記と同じ被処理布帛を投入し、４０℃から毎分２℃の昇温速度で１３０℃まで昇温し、その温度で３０分間保持して、浴中吸尽処理し、次いで、ソーピング処理と水洗処理を行った後、脱水乾燥して、染色布帛を得た。上記染色布帛を上記と同様に測色して、Ｌ*(130難燃剤)、ａ*(130難燃剤)及びｂ*(130難燃剤) を求めた。
Next, the same treated fabric as above is put into a processing bath having the same structure as above, and the temperature is raised from 40 ° C. to 130 ° C. at a rate of 2 ° C. per minute, and held at that temperature for 30 minutes. It was exhausted in a bath, then soaped and washed with water, and then dehydrated and dried to obtain a dyed fabric. The dyed fabric was measured in the same manner as above to determine L * (130 flame retardant), a * (130 flame retardant) and b * (130 flame retardant).
このようにして得られた測色結果に基づいて以下の数値を求めた。
The following numerical values were obtained based on the colorimetric results obtained in this way.
（１）１００℃において、上記難燃剤の不存在下に上記分散染料にて被処理布帛を染色して得た染色布帛と、上記難燃剤の存在下に上記分散染料にて被処理布帛を染色して得た染色布帛との色差△Ｅ（１００℃）を式
△Ｅ(１００℃)＝［（Ｌ*(100)－Ｌ*(100難燃剤))２＋（ａ*(100)－ａ*(100難燃剤))２＋（ｂ*(100)－ｂ*(100難燃剤)) ２]１／２ から求めた。 (1) A dyed fabric obtained by dyeing a treated fabric with the disperse dye in the absence of the flame retardant at 100 ° C., and a treated fabric with the disperse dye in the presence of the flame retardant. The color difference ΔE (100 ° C.) from the dyed fabric obtained by the formula ΔE (100 ° C.) = [(L * (100) - L * (100 flame retardant)) 2 + (a * (100) - a * (100 flame retardant)) 2 + (b * (100) - b * (100 flame retardant)) 2 ] 1/2 .
△Ｅ(１００℃)＝［（Ｌ*(100)－Ｌ*(100難燃剤))２＋（ａ*(100)－ａ*(100難燃剤))２＋（ｂ*(100)－ｂ*(100難燃剤)) ２]１／２ から求めた。 (1) A dyed fabric obtained by dyeing a treated fabric with the disperse dye in the absence of the flame retardant at 100 ° C., and a treated fabric with the disperse dye in the presence of the flame retardant. The color difference ΔE (100 ° C.) from the dyed fabric obtained by the formula ΔE (100 ° C.) = [(L * (100) - L * (100 flame retardant)) 2 + (a * (100) - a * (100 flame retardant)) 2 + (b * (100) - b * (100 flame retardant)) 2 ] 1/2 .
（２）１３０℃において、上記難燃剤の不存在下に上記分散染料にて被処理布帛を染色して得た染色布帛と、上記難燃剤の存在下に上記分散染料にて被処理布帛を染色して得た染色布帛との色差△Ｅ（１３０℃）を式
△Ｅ(１３０℃)＝［（Ｌ*(130)－Ｌ*(130難燃剤)）２＋（ａ*(130)－ａ*(130難燃剤)）２＋（ｂ*(130)－ｂ*(130難燃剤)) ２]１／２ から求めた。 (2) A dyed fabric obtained by dyeing a treated fabric with the disperse dye in the absence of the flame retardant at 130 ° C., and a treated fabric with the disperse dye in the presence of the flame retardant. The color difference ΔE (130 ° C.) from the dyed fabric obtained by the formula ΔE (130 ° C.) = [(L * (130) - L * (130 flame retardant)) 2 + (a * (130) - a * (130 flame retardant)) 2 + (b * (130) - b * (130 flame retardant)) 2 ] 1/2 .
△Ｅ(１３０℃)＝［（Ｌ*(130)－Ｌ*(130難燃剤)）２＋（ａ*(130)－ａ*(130難燃剤)）２＋（ｂ*(130)－ｂ*(130難燃剤)) ２]１／２ から求めた。 (2) A dyed fabric obtained by dyeing a treated fabric with the disperse dye in the absence of the flame retardant at 130 ° C., and a treated fabric with the disperse dye in the presence of the flame retardant. The color difference ΔE (130 ° C.) from the dyed fabric obtained by the formula ΔE (130 ° C.) = [(L * (130) - L * (130 flame retardant)) 2 + (a * (130) - a * (130 flame retardant)) 2 + (b * (130) - b * (130 flame retardant)) 2 ] 1/2 .
（３）上記難燃剤の不存在下に上記分散染料にて、１００℃において被処理布帛を染色して得た染色布帛と、１３０℃において被処理布帛を染色して得た染色布帛との色差△Ｅ（染料）を式
△Ｅ(染料)＝［（Ｌ*(100)－Ｌ*(130)）２＋（ａ*(100)－ａ*(130)）２＋（ｂ*(100)－ｂ*(130) ）２]１／２から求めた。 (3) Color difference between the dyed fabric obtained by dyeing the treated fabric at 100 ° C. with the disperse dye in the absence of the flame retardant and the dyed fabric obtained by dyeing the treated fabric at 130 ° C. ΔE (dye) is expressed by the formula ΔE (dye) = [(L * (100) - L * (130)) 2 + (a * (100) - a * (130)) 2 + (b * (100) − b * (130) ) 2 ] 1/2 .
△Ｅ(染料)＝［（Ｌ*(100)－Ｌ*(130)）２＋（ａ*(100)－ａ*(130)）２＋（ｂ*(100)－ｂ*(130) ）２]１／２から求めた。 (3) Color difference between the dyed fabric obtained by dyeing the treated fabric at 100 ° C. with the disperse dye in the absence of the flame retardant and the dyed fabric obtained by dyeing the treated fabric at 130 ° C. ΔE (dye) is expressed by the formula ΔE (dye) = [(L * (100) - L * (130)) 2 + (a * (100) - a * (130)) 2 + (b * (100) − b * (130) ) 2 ] 1/2 .
（４）上記難燃剤の存在下に上記分散染料にて、１００℃において被処理布帛を染色して得た染色布帛と、１３０℃において被処理布帛を染色して得た染色布帛との色差△Ｅ（染料＋難燃剤）を式
△Ｅ(染料＋難燃剤)＝［（Ｌ*(100難燃剤)－Ｌ*(130難燃剤))２＋（ａ*(100難燃剤)－ａ*(130難燃剤))２＋（ｂ*(100難燃剤)－ｂ*(130難燃剤)) ２]１／２から求めた。
から求めた。 (4) Color difference Δ between the dyed fabric obtained by dyeing the treated fabric at 100 ° C. with the disperse dye in the presence of the flame retardant and the dyed fabric obtained by dyeing the treated fabric at 130 ° C. E (dye + flame retardant) is expressed by the formula △ E (dye + flame retardant) = [(L * (100 flame retardant) - L * (130 flame retardant)) 2 + (a * (100 flame retardant) - a * ( 130 flame retardant)) 2 + (b * (100 flame retardant) - b * (130 flame retardant)) 2 ] 1/2 .
requested from
△Ｅ(染料＋難燃剤)＝［（Ｌ*(100難燃剤)－Ｌ*(130難燃剤))２＋（ａ*(100難燃剤)－ａ*(130難燃剤))２＋（ｂ*(100難燃剤)－ｂ*(130難燃剤)) ２]１／２から求めた。
から求めた。 (4) Color difference Δ between the dyed fabric obtained by dyeing the treated fabric at 100 ° C. with the disperse dye in the presence of the flame retardant and the dyed fabric obtained by dyeing the treated fabric at 130 ° C. E (dye + flame retardant) is expressed by the formula △ E (dye + flame retardant) = [(L * (100 flame retardant) - L * (130 flame retardant)) 2 + (a * (100 flame retardant) - a * ( 130 flame retardant)) 2 + (b * (100 flame retardant) - b * (130 flame retardant)) 2 ] 1/2 .
requested from
次に、前述したように、下記式
（△Ｅ（染料）／△Ｅ（染料＋難燃剤））×１００
によって得られる値を上記分散染料を含む加工浴に上記難燃剤を加えた場合の上記分散染料の染色速度変化率とした。 Next, as described above, the following formula (ΔE (dye) / ΔE (dye + flame retardant)) × 100
The value obtained by the disperse dye dyeing speed change rate when the flame retardant was added to the processing bath containing the disperse dye.
（△Ｅ（染料）／△Ｅ（染料＋難燃剤））×１００
によって得られる値を上記分散染料を含む加工浴に上記難燃剤を加えた場合の上記分散染料の染色速度変化率とした。 Next, as described above, the following formula (ΔE (dye) / ΔE (dye + flame retardant)) × 100
The value obtained by the disperse dye dyeing speed change rate when the flame retardant was added to the processing bath containing the disperse dye.
（評価）
△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率の評価基準は下記のとおりである。 (evaluation)
Evaluation criteria for ΔE (100° C.), ΔE (130° C.) and dyeing speed change rate are as follows.
△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率の評価基準は下記のとおりである。 (evaluation)
Evaluation criteria for ΔE (100° C.), ΔE (130° C.) and dyeing speed change rate are as follows.
△Ｅ（１００℃）は５．００未満を〇（適正）、５．００以上を×（不適）とした。
△Ｅ（１３０℃）は５．００未満を〇（適正）、５．００以上を×（不適）とした。 ΔE (100° C.) was evaluated as ◯ (appropriate) when less than 5.00 and x (unsuitable) when 5.00 or more.
ΔE (130° C.) was evaluated as ◯ (appropriate) when less than 5.00 and x (unsuitable) when 5.00 or more.
△Ｅ（１３０℃）は５．００未満を〇（適正）、５．００以上を×（不適）とした。 ΔE (100° C.) was evaluated as ◯ (appropriate) when less than 5.00 and x (unsuitable) when 5.00 or more.
ΔE (130° C.) was evaluated as ◯ (appropriate) when less than 5.00 and x (unsuitable) when 5.00 or more.
染色速度変化率の値は、△Ｅ（染料）が△Ｅ（染料＋難燃剤）よりも大きいとき、１００を超える。即ち、分散染料と共に難燃剤を併用することによって、染色速度が速くなったということができる。△Ｅ（染料）が△Ｅ（染料＋難燃剤）よりも小さいときは、値は１００以下である。即ち、分散染料と共に難燃剤を併用することによって、染色速度が遅くなったということができるから、難燃剤が染料の染着を阻害したということができる。
The dyeing speed change rate value exceeds 100 when ΔE (dye) is greater than ΔE (dye + flame retardant). That is, it can be said that the dyeing speed was increased by using the flame retardant together with the disperse dye. When ΔE(dye) is less than ΔE(dye+flame retardant), the value is 100 or less. That is, it can be said that the dyeing speed is slowed down by using the flame retardant together with the disperse dye, so it can be said that the flame retardant inhibits the dyeing.
染色速度が速すぎるときは染色むらを生じ、遅くなるときは発色不良となることから、本発明においては、上記染色速度変化率が１２０～１００の範囲にあるときを〇（適正）とし、１００未満であるとき及び１２１以上であるときを×（不適）とした。
When the dyeing speed is too fast, uneven dyeing occurs, and when it is too slow, the color development is poor. When it was less than or 121 or more, it was marked as x (unsuitable).
実施例２～４
実施例１において、前記式（Ｉ）で表される平均粒子径０．８μｍのアゾ系分散染料に代えて、前記式（ＩＩ）～（ＩＶ）で表されるいずれも平均粒子径０．８μｍのアゾ系分散染料をそれぞれ用いた以外は同様にして、染色布帛を得た。 Examples 2-4
In Example 1, instead of the azo disperse dye having an average particle size of 0.8 μm represented by the formula (I), any of the formulas (II) to (IV) having an average particle size of 0.8 μm A dyed fabric was obtained in the same manner except that each of the azo disperse dyes was used.
実施例１において、前記式（Ｉ）で表される平均粒子径０．８μｍのアゾ系分散染料に代えて、前記式（ＩＩ）～（ＩＶ）で表されるいずれも平均粒子径０．８μｍのアゾ系分散染料をそれぞれ用いた以外は同様にして、染色布帛を得た。 Examples 2-4
In Example 1, instead of the azo disperse dye having an average particle size of 0.8 μm represented by the formula (I), any of the formulas (II) to (IV) having an average particle size of 0.8 μm A dyed fabric was obtained in the same manner except that each of the azo disperse dyes was used.
上記染色布帛について、実施例１と同様に測色して、△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率を求めた。実施例１から４による評価結果を表１に示す。
For the above dyed fabric, colorimetry was performed in the same manner as in Example 1 to obtain ΔE (100°C), ΔE (130°C), and the rate of change in dyeing speed. Table 1 shows the evaluation results of Examples 1 to 4.
実施例５～８
実施例１～４において、前記式（Ｉ）で表される平均粒子径０．８μｍのアゾ系分散染料０．３％ｏｗｆに代えて、それぞれ前記式（Ｉ）～（ＩＶ）で表される何れも平均粒子径０．８μｍのアゾ系分散染料３．０％ｏｗｆ用いた以外は、同様にして、染色布帛を得た。 Examples 5-8
In Examples 1 to 4, instead of 0.3% owf of the azo disperse dye having an average particle size of 0.8 μm represented by the formula (I), the respective formulas (I) to (IV) A dyed fabric was obtained in the same manner except that 3.0% owf of an azo disperse dye having an average particle size of 0.8 µm was used.
実施例１～４において、前記式（Ｉ）で表される平均粒子径０．８μｍのアゾ系分散染料０．３％ｏｗｆに代えて、それぞれ前記式（Ｉ）～（ＩＶ）で表される何れも平均粒子径０．８μｍのアゾ系分散染料３．０％ｏｗｆ用いた以外は、同様にして、染色布帛を得た。 Examples 5-8
In Examples 1 to 4, instead of 0.3% owf of the azo disperse dye having an average particle size of 0.8 μm represented by the formula (I), the respective formulas (I) to (IV) A dyed fabric was obtained in the same manner except that 3.0% owf of an azo disperse dye having an average particle size of 0.8 µm was used.
上記染色布帛について、実施例１と同様に測色して、△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率を求めた。実施例５から８による評価結果を表２に示す。
For the above dyed fabric, colorimetry was performed in the same manner as in Example 1 to obtain ΔE (100°C), ΔE (130°C), and the rate of change in dyeing speed. Table 2 shows the evaluation results of Examples 5 to 8.
実施例９～１２
実施例１～４において、前記式（ＶＩＩＩ）で表される平均粒子径０．６μｍの難燃剤リン酸エステルアミド４．０％ｏｗｆに代えて、前記式（ＶＩＩＩ）で表される平均粒子径０．６μｍの難燃剤リン酸エステルアミド８．０％ｏｗｆを用いた以外は、実施例１～４におけると同様に、それぞれ前記式（Ｉ）～（ＩＶ）で表されるいずれも平均粒子径０．８μｍのアゾ系分散染料０．３％ｏｗｆを用いて、同様にして染色布帛を得た。 Examples 9-12
In Examples 1 to 4, instead of the flame retardant phosphoric acid ester amide 4.0% owf having an average particle size of 0.6 μm represented by the formula (VIII), the average particle size represented by the formula (VIII) In the same manner as in Examples 1 to 4, except that 8.0% owf of 0.6 μm flame retardant phosphoric acid ester amide was used, each of the average particle sizes represented by the above formulas (I) to (IV) A dyed fabric was similarly obtained using 0.3% owf of azo disperse dye of 0.8 μm.
実施例１～４において、前記式（ＶＩＩＩ）で表される平均粒子径０．６μｍの難燃剤リン酸エステルアミド４．０％ｏｗｆに代えて、前記式（ＶＩＩＩ）で表される平均粒子径０．６μｍの難燃剤リン酸エステルアミド８．０％ｏｗｆを用いた以外は、実施例１～４におけると同様に、それぞれ前記式（Ｉ）～（ＩＶ）で表されるいずれも平均粒子径０．８μｍのアゾ系分散染料０．３％ｏｗｆを用いて、同様にして染色布帛を得た。 Examples 9-12
In Examples 1 to 4, instead of the flame retardant phosphoric acid ester amide 4.0% owf having an average particle size of 0.6 μm represented by the formula (VIII), the average particle size represented by the formula (VIII) In the same manner as in Examples 1 to 4, except that 8.0% owf of 0.6 μm flame retardant phosphoric acid ester amide was used, each of the average particle sizes represented by the above formulas (I) to (IV) A dyed fabric was similarly obtained using 0.3% owf of azo disperse dye of 0.8 μm.
上記染色布帛について、実施例１と同様に測色して、△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率を求めた。実施例９から１２による評価結果を表３に示す。
For the above dyed fabric, colorimetry was performed in the same manner as in Example 1 to obtain ΔE (100°C), ΔE (130°C), and the rate of change in dyeing speed. Table 3 shows the evaluation results of Examples 9 to 12.
実施例１３～１６
実施例１～４において、前記式（ＶＩＩＩ）で表される平均粒子径０．６μｍの難燃剤リン酸エステルアミド４．０％ｏｗｆに代えて、前記式（ＶＩＩＩ）で表される平均粒子径０．６μｍの難燃剤リン酸エステルアミド１．０％ｏｗｆを用いた以外は、実施例１～４におけると同様に、それぞれ前記式（Ｉ）～（ＩＶ）で表されるいずれも平均粒子径０．８μｍのアゾ系分散染料０．３％ｏｗｆを用いて、同様にして染色布帛を得た。 Examples 13-16
In Examples 1 to 4, instead of the flame retardant phosphoric acid ester amide 4.0% owf having an average particle size of 0.6 μm represented by the formula (VIII), the average particle size represented by the formula (VIII) In the same manner as in Examples 1 to 4, except that 0.6 μm flame retardant phosphate ester amide 1.0% owf was used, the average particle size of each of the above formulas (I) to (IV) A dyed fabric was similarly obtained using 0.3% owf of azo disperse dye of 0.8 μm.
実施例１～４において、前記式（ＶＩＩＩ）で表される平均粒子径０．６μｍの難燃剤リン酸エステルアミド４．０％ｏｗｆに代えて、前記式（ＶＩＩＩ）で表される平均粒子径０．６μｍの難燃剤リン酸エステルアミド１．０％ｏｗｆを用いた以外は、実施例１～４におけると同様に、それぞれ前記式（Ｉ）～（ＩＶ）で表されるいずれも平均粒子径０．８μｍのアゾ系分散染料０．３％ｏｗｆを用いて、同様にして染色布帛を得た。 Examples 13-16
In Examples 1 to 4, instead of the flame retardant phosphoric acid ester amide 4.0% owf having an average particle size of 0.6 μm represented by the formula (VIII), the average particle size represented by the formula (VIII) In the same manner as in Examples 1 to 4, except that 0.6 μm flame retardant phosphate ester amide 1.0% owf was used, the average particle size of each of the above formulas (I) to (IV) A dyed fabric was similarly obtained using 0.3% owf of azo disperse dye of 0.8 μm.
上記染色布帛について、実施例１と同様に、測色して、△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率を求めた。実施例１３から１６による評価結果を表４に示す。
For the above dyed fabric, colorimetry was performed in the same manner as in Example 1 to obtain ΔE (100°C), ΔE (130°C) and the rate of change in dyeing speed. Table 4 shows the evaluation results of Examples 13 to 16.
実施例１７～１９
実施例１において、分散染料として、前記式（ＩＩＩ）で表される平均粒子径０．８μｍのアゾ系分散染料と前記式（Ｖ）～（ＶＩＩ）で表される平均粒子径０．８μｍのキノン系分散染料のいずれかを用いた以外は、実施例１におけると同様にして染色布帛を得た。 Examples 17-19
In Example 1, as the disperse dyes, an azo disperse dye having an average particle size of 0.8 μm represented by the formula (III) and an average particle size of 0.8 μm represented by the formulas (V) to (VII) A dyed fabric was obtained in the same manner as in Example 1, except that any of the quinone-based disperse dyes was used.
実施例１において、分散染料として、前記式（ＩＩＩ）で表される平均粒子径０．８μｍのアゾ系分散染料と前記式（Ｖ）～（ＶＩＩ）で表される平均粒子径０．８μｍのキノン系分散染料のいずれかを用いた以外は、実施例１におけると同様にして染色布帛を得た。 Examples 17-19
In Example 1, as the disperse dyes, an azo disperse dye having an average particle size of 0.8 μm represented by the formula (III) and an average particle size of 0.8 μm represented by the formulas (V) to (VII) A dyed fabric was obtained in the same manner as in Example 1, except that any of the quinone-based disperse dyes was used.
上記染色布帛について、実施例１と同様に、測色して、△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率を求めた。実施例１７から１９による評価結果を表５に示す。
For the above dyed fabric, colorimetry was performed in the same manner as in Example 1 to obtain ΔE (100°C), ΔE (130°C) and the rate of change in dyeing speed. Table 5 shows the evaluation results of Examples 17 to 19.
比較例１
実施例１において、前記式（ＶＩＩＩ）で表される難燃剤リン酸エステルアミドに代えて、難燃剤として平均粒子径０．６μｍの下記式（ＩＸ） Comparative example 1
In Example 1, instead of the flame retardant phosphate amide represented by the formula (VIII), the following formula (IX) having an average particle size of 0.6 μm was used as a flame retardant.
実施例１において、前記式（ＶＩＩＩ）で表される難燃剤リン酸エステルアミドに代えて、難燃剤として平均粒子径０．６μｍの下記式（ＩＸ） Comparative example 1
In Example 1, instead of the flame retardant phosphate amide represented by the formula (VIII), the following formula (IX) having an average particle size of 0.6 μm was used as a flame retardant.
で表されるレゾルシノールビス（２，６－ジキシレニルホスフェート）を用いた以外は、同様にして、染色布帛を得た。
A dyed fabric was obtained in the same manner except that resorcinol bis (2,6-dixylenyl phosphate) represented by was used.
比較例２
実施例１において、前記式（ＶＩＩＩ）で表される難燃剤リン酸エステルアミドに代えて、難燃剤として平均粒子径０．６μｍの下記式（Ｘ） Comparative example 2
In Example 1, instead of the flame retardant phosphate amide represented by the formula (VIII), the following formula (X) having an average particle size of 0.6 μm was used as the flame retardant.
実施例１において、前記式（ＶＩＩＩ）で表される難燃剤リン酸エステルアミドに代えて、難燃剤として平均粒子径０．６μｍの下記式（Ｘ） Comparative example 2
In Example 1, instead of the flame retardant phosphate amide represented by the formula (VIII), the following formula (X) having an average particle size of 0.6 μm was used as the flame retardant.
で表される１０－ベンジル－９，１０－ジヒドロ－９－オキサ―１０－ホスファフェナンスレン―１０－オキシドを用いた以外は、同様にして、染色布帛を得た。
A dyed fabric was obtained in the same manner except that 10-benzyl-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide represented by was used.
比較例３
実施例１において、前記式（ＶＩＩＩ）で表される難燃剤リン酸エステルアミドに代えて、難燃剤として平均粒子径０．６μｍの下記式（ＸＩ） Comparative example 3
In Example 1, instead of the flame retardant phosphate amide represented by the formula (VIII), the following formula (XI) having an average particle size of 0.6 μm was used as the flame retardant.
実施例１において、前記式（ＶＩＩＩ）で表される難燃剤リン酸エステルアミドに代えて、難燃剤として平均粒子径０．６μｍの下記式（ＸＩ） Comparative example 3
In Example 1, instead of the flame retardant phosphate amide represented by the formula (VIII), the following formula (XI) having an average particle size of 0.6 μm was used as the flame retardant.
で表される２－フェノキシエチルジフェニルホスフェートを用いた以外は、同様にして、染色布帛を得た。
A dyed fabric was obtained in the same manner except that 2-phenoxyethyl diphenyl phosphate represented by was used.
比較例４
実施例１において、前記式（ＶＩＩＩ）で表される難燃剤リン酸エステルアミドに代えて、難燃剤として平均粒子径０．６μｍの下記式（ＸＩＩ） Comparative example 4
In Example 1, instead of the flame retardant phosphate amide represented by the formula (VIII), the following formula (XII) having an average particle size of 0.6 μm was used as the flame retardant.
実施例１において、前記式（ＶＩＩＩ）で表される難燃剤リン酸エステルアミドに代えて、難燃剤として平均粒子径０．６μｍの下記式（ＸＩＩ） Comparative example 4
In Example 1, instead of the flame retardant phosphate amide represented by the formula (VIII), the following formula (XII) having an average particle size of 0.6 μm was used as the flame retardant.
で表される５，５－ジメチル－２－（２’－フェニルフェノキシ）－１，３，２－ジオキサホスホリナン－２－オキシドを用いた以外は、同様にして、染色布帛を得た。
A dyed fabric was obtained in the same manner except that 5,5-dimethyl-2-(2'-phenylphenoxy)-1,3,2-dioxaphosphorinane-2-oxide represented by was used.
比較例５
実施例１において、前記式（ＶＩＩＩ）で表される難燃剤リン酸エステルアミドに代えて、難燃剤として平均粒子径０．６μｍの下記式（ＸＩＩＩ） Comparative example 5
In Example 1, instead of the flame retardant phosphate amide represented by the formula (VIII), the following formula (XIII) having an average particle size of 0.6 μm was used as a flame retardant.
実施例１において、前記式（ＶＩＩＩ）で表される難燃剤リン酸エステルアミドに代えて、難燃剤として平均粒子径０．６μｍの下記式（ＸＩＩＩ） Comparative example 5
In Example 1, instead of the flame retardant phosphate amide represented by the formula (VIII), the following formula (XIII) having an average particle size of 0.6 μm was used as a flame retardant.
で表されるｐ－クレジルホスフェートを用いた以外は、同様にして染色布帛を得た。
A dyed fabric was obtained in the same manner except that p-cresyl phosphate represented by was used.
比較例６
実施例１において、前記式（ＶＩＩＩ）で表される難燃剤リン酸エステルアミドに代えて、難燃剤として平均粒子径０．６μｍの下記式（ＸＩＶ） Comparative example 6
In Example 1, instead of the flame retardant phosphate amide represented by the formula (VIII), the following formula (XIV) having an average particle size of 0.6 μm was used as the flame retardant.
実施例１において、前記式（ＶＩＩＩ）で表される難燃剤リン酸エステルアミドに代えて、難燃剤として平均粒子径０．６μｍの下記式（ＸＩＶ） Comparative example 6
In Example 1, instead of the flame retardant phosphate amide represented by the formula (VIII), the following formula (XIV) having an average particle size of 0.6 μm was used as the flame retardant.
で表されるトリス（２，３－ジブロモプロピル）イソシアヌレートを用いた以外は、同様にして染色布帛を得た。
A dyed fabric was obtained in the same manner except that tris (2,3-dibromopropyl) isocyanurate represented by was used.
上記比較例１～６において得た染色布帛について、実施例１と同様に測色して、△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率を求めた。比較例１から６による評価結果を表６に示す。
For the dyed fabrics obtained in Comparative Examples 1 to 6 above, the colors were measured in the same manner as in Example 1 to determine ΔE (100°C), ΔE (130°C) and the rate of change in dyeing speed. Table 6 shows the evaluation results of Comparative Examples 1 to 6.
比較例７～１２
比較例１～６において、式（Ｉ）で表されるアゾ系分散染料に代えて、それぞれ式（ＩＩ）で表されるアゾ系分散染料を用いた以外は同様にして、染色布帛を得た。 Comparative Examples 7-12
Dyed fabrics were obtained in the same manner as in Comparative Examples 1 to 6, except that the azo disperse dyes represented by formula (II) were used instead of the azo disperse dyes represented by formula (I). .
比較例１～６において、式（Ｉ）で表されるアゾ系分散染料に代えて、それぞれ式（ＩＩ）で表されるアゾ系分散染料を用いた以外は同様にして、染色布帛を得た。 Comparative Examples 7-12
Dyed fabrics were obtained in the same manner as in Comparative Examples 1 to 6, except that the azo disperse dyes represented by formula (II) were used instead of the azo disperse dyes represented by formula (I). .
上記染色布帛について、実施例１と同様に測色して、△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率を求めた。比較例７から１２による評価結果を表７に示す。
For the above dyed fabric, colorimetry was performed in the same manner as in Example 1 to obtain ΔE (100°C), ΔE (130°C), and the rate of change in dyeing speed. Table 7 shows the evaluation results of Comparative Examples 7 to 12.
比較例１３～１８
比較例１～６において、式（Ｉ）で表されるアゾ系分散染料に代えて、それぞれ式（ＩＩＩ）で表されるアゾ系分散染料を用いた以外は同様にして、染色布帛を得た。 Comparative Examples 13-18
Dyed fabrics were obtained in the same manner as in Comparative Examples 1 to 6, except that the azo disperse dyes represented by formula (III) were used instead of the azo disperse dyes represented by formula (I). .
比較例１～６において、式（Ｉ）で表されるアゾ系分散染料に代えて、それぞれ式（ＩＩＩ）で表されるアゾ系分散染料を用いた以外は同様にして、染色布帛を得た。 Comparative Examples 13-18
Dyed fabrics were obtained in the same manner as in Comparative Examples 1 to 6, except that the azo disperse dyes represented by formula (III) were used instead of the azo disperse dyes represented by formula (I). .
上記染色布帛について、実施例１と同様に測色して、△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率を求めた。比較例１３から１８による評価結果を表８に示す。
For the above dyed fabric, colorimetry was performed in the same manner as in Example 1 to obtain ΔE (100°C), ΔE (130°C), and the rate of change in dyeing speed. Table 8 shows the evaluation results of Comparative Examples 13 to 18.
比較例１９～２４
比較例１～６において、式（Ｉ）で表されるアゾ系分散染料に代えて、それぞれ式（ＩＶ）で表されるアゾ系分散染料を用いた以外は同様にして、染色布帛を得た。 Comparative Examples 19-24
Dyed fabrics were obtained in the same manner as in Comparative Examples 1 to 6, except that the azo disperse dyes represented by formula (IV) were used instead of the azo disperse dyes represented by formula (I). .
比較例１～６において、式（Ｉ）で表されるアゾ系分散染料に代えて、それぞれ式（ＩＶ）で表されるアゾ系分散染料を用いた以外は同様にして、染色布帛を得た。 Comparative Examples 19-24
Dyed fabrics were obtained in the same manner as in Comparative Examples 1 to 6, except that the azo disperse dyes represented by formula (IV) were used instead of the azo disperse dyes represented by formula (I). .
上記染色布帛について、実施例１と同様に測色して、△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率を求めた。比較例１９から２４による評価結果を表９に示す。
For the above dyed fabric, colorimetry was performed in the same manner as in Example 1 to obtain ΔE (100°C), ΔE (130°C), and the rate of change in dyeing speed. Table 9 shows the evaluation results of Comparative Examples 19 to 24.
比較例２５
実施例１において、式（Ｉ）で表される平均粒子径０．８μｍのアゾ系分散染料３．０％ｏｗｆを用いると共に、前記式(ＶＩＩＩ）で表される難燃剤に代えて、前記式（ＩＸ）で表される平均粒子径０．６μｍのレゾルシノールビス（２，６－ジキシレニルホスフェート）を用いた以外は同様にして、染色布帛を得た。 Comparative example 25
In Example 1, 3.0% owf of the azo disperse dye having an average particle size of 0.8 μm represented by the formula (I) was used, and instead of the flame retardant represented by the formula (VIII), the formula A dyed fabric was obtained in the same manner except that resorcinol bis(2,6-dixylenyl phosphate) having an average particle size of 0.6 μm represented by (IX) was used.
実施例１において、式（Ｉ）で表される平均粒子径０．８μｍのアゾ系分散染料３．０％ｏｗｆを用いると共に、前記式(ＶＩＩＩ）で表される難燃剤に代えて、前記式（ＩＸ）で表される平均粒子径０．６μｍのレゾルシノールビス（２，６－ジキシレニルホスフェート）を用いた以外は同様にして、染色布帛を得た。 Comparative example 25
In Example 1, 3.0% owf of the azo disperse dye having an average particle size of 0.8 μm represented by the formula (I) was used, and instead of the flame retardant represented by the formula (VIII), the formula A dyed fabric was obtained in the same manner except that resorcinol bis(2,6-dixylenyl phosphate) having an average particle size of 0.6 μm represented by (IX) was used.
比較例２６
実施例１において、式（Ｉ）で表されるアゾ系分散染料に代えて、前記式（ＩＩＩ）で表される平均粒子径０．８μｍのアゾ系分散染料３．０％ｏｗｆを用いると共に、前記式（ＶＩＩＩ）で表される難燃剤に代えて、前記式（ＸＩＩ）で表される平均粒子径０．６μｍの５，５－ジメチル－２－（２’－フェニルフェノキシ）－１，３，２－ジオキサホスホリナン－２－オキシドを用いた以外は同様にして、染色布帛を得た。 Comparative example 26
In Example 1, instead of the azo disperse dye represented by the formula (I), 3.0% owf of the azo disperse dye having an average particle size of 0.8 μm represented by the formula (III) was used, 5,5-dimethyl-2-(2′-phenylphenoxy)-1,3 with an average particle size of 0.6 μm represented by the formula (XII) instead of the flame retardant represented by the formula (VIII) ,2-dioxaphosphorinane-2-oxide was used to obtain a dyed fabric.
実施例１において、式（Ｉ）で表されるアゾ系分散染料に代えて、前記式（ＩＩＩ）で表される平均粒子径０．８μｍのアゾ系分散染料３．０％ｏｗｆを用いると共に、前記式（ＶＩＩＩ）で表される難燃剤に代えて、前記式（ＸＩＩ）で表される平均粒子径０．６μｍの５，５－ジメチル－２－（２’－フェニルフェノキシ）－１，３，２－ジオキサホスホリナン－２－オキシドを用いた以外は同様にして、染色布帛を得た。 Comparative example 26
In Example 1, instead of the azo disperse dye represented by the formula (I), 3.0% owf of the azo disperse dye having an average particle size of 0.8 μm represented by the formula (III) was used, 5,5-dimethyl-2-(2′-phenylphenoxy)-1,3 with an average particle size of 0.6 μm represented by the formula (XII) instead of the flame retardant represented by the formula (VIII) ,2-dioxaphosphorinane-2-oxide was used to obtain a dyed fabric.
比較例２７
実施例１において、式（Ｉ）で表されるアゾ系分散染料に代えて、前記式（ＩＩＩ）で表される平均粒子径０．８μｍのアゾ系分散染料３．０％ｏｗｆを用いると共に、前記式（ＶＩＩＩ）で表される難燃剤に代えて、前記式（ＸＩＶ）で表される平均粒子径０．６μｍのトリス（２，３－ジブロモプロピル）イソシアヌレートを用いた以外は同様にして、染色布帛を得た。 Comparative example 27
In Example 1, instead of the azo disperse dye represented by the formula (I), 3.0% owf of the azo disperse dye having an average particle size of 0.8 μm represented by the formula (III) was used, In the same manner, except that tris(2,3-dibromopropyl)isocyanurate having an average particle size of 0.6 μm represented by the formula (XIV) was used instead of the flame retardant represented by the formula (VIII). , to obtain a dyed fabric.
実施例１において、式（Ｉ）で表されるアゾ系分散染料に代えて、前記式（ＩＩＩ）で表される平均粒子径０．８μｍのアゾ系分散染料３．０％ｏｗｆを用いると共に、前記式（ＶＩＩＩ）で表される難燃剤に代えて、前記式（ＸＩＶ）で表される平均粒子径０．６μｍのトリス（２，３－ジブロモプロピル）イソシアヌレートを用いた以外は同様にして、染色布帛を得た。 Comparative example 27
In Example 1, instead of the azo disperse dye represented by the formula (I), 3.0% owf of the azo disperse dye having an average particle size of 0.8 μm represented by the formula (III) was used, In the same manner, except that tris(2,3-dibromopropyl)isocyanurate having an average particle size of 0.6 μm represented by the formula (XIV) was used instead of the flame retardant represented by the formula (VIII). , to obtain a dyed fabric.
比較例２８
実施例１において、式（Ｉ）で表されるアゾ分散染料に代えて、下記式（ＸＶ） Comparative example 28
In Example 1, instead of the azo disperse dye represented by formula (I), the following formula (XV)
実施例１において、式（Ｉ）で表されるアゾ分散染料に代えて、下記式（ＸＶ） Comparative example 28
In Example 1, instead of the azo disperse dye represented by formula (I), the following formula (XV)
で表される平均粒子径０．８μｍのアゾ分散染料を用いた以外は、同様にして、染色布帛を得た。上記式（ＸＶ）で表されるアゾ系分散染料は、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ Ｒｅｄ ２５８であって、本発明において用いることを規定するアゾ系分散染料ではないものである。
A dyed fabric was obtained in the same manner except that an azo disperse dye having an average particle size of 0.8 μm represented by was used. The azo disperse dye represented by the above formula (XV) is C.I. I. Disperse Red 258, which is not an azo disperse dye specified for use in the present invention.
上記比較例２５～２８において得た染色布帛について、実施例１と同様に測色して、△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率を求めた。比較例２５から２８による評価結果を表１０に示す。
The dyed fabrics obtained in Comparative Examples 25 to 28 were colorimetrically measured in the same manner as in Example 1 to determine ΔE (100°C), ΔE (130°C), and dyeing speed change rate. Table 10 shows the evaluation results of Comparative Examples 25 to 28.
表１は、前記式（ＶＩＩＩ）で表される難燃剤４．０％оｗｆ量の存在下に前記式（Ｉ）～（ＩＶ）で表される分散染料のいずれを０．３％оｗｆ量で用いても、ポリエステル系繊維からなる被処理布帛を染色したとき、色差△Ｅ（１００℃）と△Ｅ（１３０℃）が共に小さく、適正であり、染色速度変化率もまた、適正であることを示す。
Table 1 shows that any of the disperse dyes represented by the formulas (I) to (IV) in the presence of 4.0% wf amount of the flame retardant represented by the formula (VIII) with a 0.3% wf amount Even if it is used, when a treated fabric made of polyester fiber is dyed, both the color difference ΔE (100 ° C.) and ΔE (130 ° C.) are small and appropriate, and the dyeing speed change rate is also appropriate. indicates
即ち、１００℃と１３０℃において、前記式（ＶＩＩＩ）で表される難燃剤の不存在下に、それぞれ前記式（Ｉ）～（ＩＶ）で表される分散染料にて被処理布帛を染色して得られた染色布帛と、上記難燃剤の存在下に上記分散染料にて被処理布帛を染色して得られた染色布帛との色差が小さく、更に、前述した染色速度変化率が適正であることから、上記分散染料に上記難燃剤を併用しても、上記難燃剤の不存在下に上記分散染料を用いて染色する場合に比べて、染色速度変化率が小さいということができる。
That is, at 100 ° C. and 130 ° C., the fabric to be treated is dyed with the disperse dyes represented by the formulas (I) to (IV) in the absence of the flame retardant represented by the formula (VIII). The color difference between the dyed fabric obtained by and the dyed fabric obtained by dyeing the treated fabric with the disperse dye in the presence of the flame retardant is small, and the above-mentioned dyeing speed change rate is appropriate. Therefore, it can be said that even if the flame retardant is used in combination with the disperse dye, the rate of change in dyeing speed is small compared to the case of dyeing using the disperse dye in the absence of the flame retardant.
表２は、１００℃と１３０℃において、前記式（ＶＩＩＩ）で表される難燃剤４．０％оｗｆ量の存在下に前記式（Ｉ）～（ＩＶ）で表される分散染料のいずれを３．０％оｗｆ量で用いても、得られる染色物は、色差△Ｅ（１００℃）と△Ｅ（１３０℃）が共に小さく、適正であり、染色速度変化率もまた、適正であることを示す。
Table 2 shows any of the disperse dyes represented by formulas (I) to (IV) in the presence of 4.0% of the flame retardant represented by formula (VIII) at 100 ° C. and 130 ° C. Even if it is used in an amount of 3.0% wf, the resulting dyed product has both small color differences ΔE (100°C) and ΔE (130°C) and is appropriate, and the rate of change in dyeing speed is also appropriate. indicates
表３は、１００℃と１３０℃において、前記式（ＶＩＩＩ）で表される難燃剤８．０％оｗｆ量の存在下に前記式（Ｉ）～（ＩＶ）で表される分散染料のいずれを０．３％оｗｆ量で用いても、得られる染色物は、色差△Ｅ（１００℃）と△Ｅ（１３０℃）が共に小さく、適正であり、染色速度変化率もまた、適正であることを示す。
Table 3 shows that any of the disperse dyes represented by the formulas (I) to (IV) in the presence of 8.0% of the flame retardant represented by the formula (VIII) at 100 ° C. and 130 ° C. Even if it is used in an amount of 0.3% wf, the obtained dyed product has both small color difference ΔE (100°C) and ΔE (130°C) and is appropriate, and the dyeing speed change rate is also appropriate. indicates
表４は、１００℃と１３０℃において、前記式（ＶＩＩＩ）で表される難燃剤１．０％оｗｆ量の存在下に前記式（Ｉ）～（ＩＶ）で表される分散染料のいずれを０．３％оｗｆ量で用いても、得られる染色物は、色差△Ｅ（１００℃）と△Ｅ（１３０℃）が共に小さく、適正であり、染色速度変化率もまた、適正であることを示す。
Table 4 shows any of the disperse dyes represented by formulas (I) to (IV) in the presence of 1.0% of the flame retardant represented by formula (VIII) at 100 ° C. and 130 ° C. Even if it is used in an amount of 0.3% wf, the obtained dyed product has both small color difference ΔE (100°C) and ΔE (130°C) and is appropriate, and the dyeing speed change rate is also appropriate. indicates
表５は、１００℃と１３０℃において、前記式（ＶＩＩＩ）で表される難燃剤４．０％оｗｆ量の存在下に前記式（ＩＩＩ）で表される分散染料０．３％оｗｆ量と前記式（Ｖ）～（ＶＩＩ）で表される分散染料のいずれを０．３％оｗｆ量で用いても、得られる染色物は、色差△Ｅ（１００℃）と△Ｅ（１３０℃）が共に小さく、適正であり、染色速度変化率もまた、適正であることを示す。
Table 5 shows that at 100 ° C. and 130 ° C., in the presence of 4.0% of the flame retardant represented by the formula (VIII) and 0.3% of the disperse dye represented by the formula (III). Even if any of the disperse dyes represented by the above formulas (V) to (VII) is used in an amount of 0.3%, the obtained dyed product has a color difference ΔE (100° C.) and ΔE (130° C.) Both are small and correct, indicating that the dyeing speed change rate is also correct.
以上のように、本発明に従って、前記式（Ｉ）から（ＩＶ）で表されるアゾ系分散染料から選ばれる少なくとも１種と、前記式（ＶＩＩＩ）で表される難燃剤リン酸エステルアミドを含む加工浴にポリエステル系繊維品を浸漬し、加熱する染色同時難燃加工方法によれば、難燃剤の不存在下にアゾ系分散染料にてポリエステル系繊維品を染色した場合に比べて、温度１００℃と１３０℃において、上記アゾ系分散染料と上記難燃剤の使用量を種々に変化させて、被処理布帛を染色同時難燃加工しても、上記色差△Ｅ（１００℃）と△Ｅ（１３０℃）が共に小さく、適正であると共に、染色速度変化率もまた、適正である。かくして、本発明によれば、染色再現性よく、ポリエステル系繊維品を染色同時難燃加工することができる。
As described above, according to the present invention, at least one selected from the azo disperse dyes represented by the formulas (I) to (IV) and the flame retardant phosphate ester amide represented by the formula (VIII) According to the dyeing simultaneous flame retardant treatment method in which the polyester fiber product is immersed in a processing bath containing and heated, the temperature At 100 ° C. and 130 ° C., the amounts of the azo disperse dye and the flame retardant used are variously changed, and the treated fabric is subjected to flame retardant treatment at the same time as dyeing. (130° C.) are both small and appropriate, and the dyeing speed change rate is also appropriate. Thus, according to the present invention, it is possible to simultaneously dye and flame retard polyester textiles with good dyeing reproducibility.
また、本発明に従って、前記式（Ｉ）から（ＩＶ）で表されるアゾ系分散染料から選ばれる少なくとも１種と前記式（Ｖ）から（ＶＩＩ）で表されるキノン系分散染料から選ばれる少なくとも１種と共に、前記式（ＶＩＩＩ）で表される難燃剤リン酸エステルアミドを含む加工浴にポリエステル系繊維品を浸漬し、加熱する染色同時難燃加工方法によれば、難燃剤の不存在下に上記アゾ系分散染料と上記キノン系分散染料にてポリエステル系繊維品を染色した場合に比べて、温度１００℃と１３０℃において、被処理布帛を染色同時難燃加工しても、上記色差△Ｅ（１００℃）と△Ｅ（１３０℃）が共に小さく、適正であると共に、染色速度変化率もまた、適正である。かくして、本発明によれば、染色再現性よく、ポリエステル系繊維品を染色同時難燃加工することができる。
Further, according to the present invention, at least one selected from the azo disperse dyes represented by the formulas (I) to (IV) and the quinone disperse dyes represented by the formulas (V) to (VII) According to the dyeing and simultaneous flame retardant processing method in which a polyester textile is immersed in a processing bath containing at least one flame retardant phosphate ester amide represented by the formula (VIII) and heated, the flame retardant is not present. Compared to the case of dyeing a polyester fiber product with the above azo disperse dye and the above quinone disperse dye, even if the treated fabric is dyed and flame retarded at a temperature of 100 ° C. and 130 ° C., the above color difference Both ΔE (100° C.) and ΔE (130° C.) are small and appropriate, and the rate of change in dyeing speed is also appropriate. Thus, according to the present invention, it is possible to simultaneously dye and flame retard polyester textiles with good dyeing reproducibility.
これに対して、表６は、前記式（ＶＩＩＩ）で表される難燃剤に代えて、前記式（ＩＸ）～（ＸＩＶ）で表される従来から知られている代表的な難燃剤の存在下に、前記式（Ｉ）で表されるアゾ系分散染料を用いて、ポリエステル系繊維品を染色したときの結果を示し、比較例２～６においては、色差△Ｅ（１００℃）及び染色速度変化率の少なくとも１つが不適であったが、比較例１においては、色差△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率のすべてが適正であった。比較例１については後に別の結果を示す。
On the other hand, Table 6 shows the presence of conventionally known representative flame retardants represented by the formulas (IX) to (XIV) instead of the flame retardant represented by the formula (VIII). Below, the results of dyeing polyester textiles using the azo disperse dye represented by formula (I) are shown. In Comparative Examples 2 to 6, color difference ΔE (100 ° C.) and dyeing At least one of the rate of change in speed was unsuitable, but in Comparative Example 1, all of the color differences ΔE (100° C.), ΔE (130° C.) and the rate of change in dyeing speed were appropriate. Another result of Comparative Example 1 will be shown later.
同様に表７は、比較例７～１２において、前記式（ＶＩＩＩ）で表される難燃剤に代えて、前記式（ＩＸ）～（ＸＩＶ）で表される従来から知られている代表的な難燃剤の存在下に、前記式（ＩＩ）で表されるアゾ系分散染料をそれぞれ用いて、ポリエステル系繊維品を染色したときの結果を示す。
Similarly, Table 7 shows, in Comparative Examples 7 to 12, instead of the flame retardant represented by the formula (VIII), conventionally known representatives represented by the formulas (IX) to (XIV) The results of dyeing polyester textiles with each of the azo disperse dyes represented by the formula (II) in the presence of a flame retardant are shown.
比較例７～１２においては、色差△Ｅ（１００℃）及び染色速度変化率の少なくとも１つが不適であった。
In Comparative Examples 7 to 12, at least one of the color difference ΔE (100°C) and the rate of change in dyeing speed was unsuitable.
表８は、比較例１３～１８において、前記式（ＶＩＩＩ）で表される難燃剤に代えて、前記式（ＩＸ）～（ＸＩＶ）で表される従来から知られている代表的な難燃剤の存在下に、前記式（ＩＩＩ）で表されるアゾ系分散染料をそれぞれ用いて、ポリエステル系繊維品を染色したときの結果を示す。
Table 8 shows typical conventionally known flame retardants represented by the formulas (IX) to (XIV) instead of the flame retardant represented by the formula (VIII) in Comparative Examples 13 to 18. In the presence of, using each of the azo disperse dyes represented by the formula (III), the results of dyeing a polyester fiber product are shown.
比較例１３、１４、１５及び１７においては、色差△Ｅ（１００℃）及び染色速度変化率の少なくとも１つが不適であったが、比較例１６及び１８においては、色差△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率のすべてが適正であった。比較例１６及び１８については後に別の結果を示す。
In Comparative Examples 13, 14, 15 and 17, at least one of the color difference ΔE (100°C) and the dyeing speed change rate was unsuitable, but in Comparative Examples 16 and 18, the color difference ΔE (100°C), ΔE (130° C.) and dyeing rate change were all correct. Other results for Comparative Examples 16 and 18 are shown later.
表９は、比較例１９～２４において、前記式（ＶＩＩＩ）で表される難燃剤に代えて、前記式（ＩＸ）～（ＸＩＶ）で表される従来から知られている代表的な難燃剤の存在下に、前記式（ＩＶ）で表されるアゾ系分散染料をそれぞれ用いて、ポリエステル系繊維品を染色したときの結果を示す。
Table 9 shows typical conventionally known flame retardants represented by the formulas (IX) to (XIV) instead of the flame retardant represented by the formula (VIII) in Comparative Examples 19 to 24. In the presence of, using each of the azo disperse dyes represented by the formula (IV), the results of dyeing a polyester fiber product are shown.
比較例１９～２４においては、色差△Ｅ（１００℃）及び染色速度変化率の少なくとも１つが不適であった。
In Comparative Examples 19-24, at least one of the color difference ΔE (100°C) and the rate of change in dyeing speed was unsuitable.
表１０は比較例２５～２８の結果を示す。このうち、比較例２５は前記式（Ｉ）で表される分散染料と前記式（ＩＸ）で表される難燃剤を併用して、比較例２６は前記式（ＩＩＩ）で表される分散染料と前記式（ＸＩＩ）で表される難燃剤を併用して、比較例２７は前記式（ＩＩＩ）で表される分散染料と前記式（ＸＩＶ）で表される難燃剤を併用して、それぞれ、ポリエステル系繊維品を染色同時難燃加工した結果を示す。比較例２５～２７においては、いずれも、分散染料は平均粒子径０．８μｍ、使用量は３．０％ｏｗｆであり、難燃剤は平均粒子径０．６μｍ、使用量は４．０％ｏｗｆである。
Table 10 shows the results of Comparative Examples 25-28. Among these, Comparative Example 25 is a combination of the disperse dye represented by the formula (I) and the flame retardant represented by the formula (IX), and Comparative Example 26 is the disperse dye represented by the formula (III). and the flame retardant represented by the formula (XII), Comparative Example 27 uses the disperse dye represented by the formula (III) and the flame retardant represented by the formula (XIV) in combination, respectively , shows the results of dyeing and simultaneous flame retardant processing of polyester fiber products. In Comparative Examples 25 to 27, the disperse dye has an average particle size of 0.8 μm and the amount used is 3.0%owf, and the flame retardant has an average particle size of 0.6 μm and is used in an amount of 4.0%owf. is.
比較例２５～２７において、アゾ系分散染料と難燃剤の組み合わせは、前述した比較例１、１６及び１８におけるそれらと対応しているが、アゾ系分散染料の使用量が比較例１、１６及び１８においては０．３％оｗｆ量であるところ、比較例２５～２７においては、３．０％оｗｆ量としたものであり、その結果、色差△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率の少なくとも１つにおいて不適である。
In Comparative Examples 25 to 27, the combination of the azo disperse dye and the flame retardant corresponds to those in Comparative Examples 1, 16 and 18 described above, but the amount of the azo disperse dye used is the same as in Comparative Examples 1, 16 and In Comparative Examples 25 to 27, the amount of owf was 0.3%, whereas in Comparative Examples 25 to 27, the amount of owf was 3.0%. As a result, the color difference ΔE (100°C) and ΔE (130°C) and at least one of the rate of change in dyeing speed.
即ち、前記式（ＩＸ）、（ＸＩＩ）及び（ＸＩＶ）で表される難燃剤は、比較例１、１６及び１８にみられるように、これと併用するアゾ系分散染料の使用量が少ないとき（０．３％оｗｆ）は、色差△Ｅ（１００℃）、△Ｅ（１３０℃）及び染色速度変化率のいずれも適正であるが、しかし、併用するアゾ系分散染料の使用量が多いとき（３．０％оｗｆ）は、染色速度変化率が大きくなる。よって、前記式（ＩＸ）、（ＸＩＩ）及び（ＸＩＶ）で表される難燃剤は、前記式（Ｉ）～（ＩＶ）で表される分散染料を用いるポリエステル系繊維品の染色同時難燃加工において、上記分散染料の染色再現性を阻害している。
That is, the flame retardants represented by the formulas (IX), (XII) and (XIV), as seen in Comparative Examples 1, 16 and 18, when the amount of the azo disperse dye used in combination therewith is small (0.3% wf), the color difference ΔE (100° C.), ΔE (130° C.) and the dyeing speed change rate are all appropriate, but when the amount of the azo disperse dye used in combination is large (3.0% wf) increases the rate of change in dyeing speed. Therefore, the flame retardants represented by the formulas (IX), (XII) and (XIV) are dyeing and simultaneous flame retardant processing of polyester textiles using the disperse dyes represented by the formulas (I) to (IV). In the above, the dyeing reproducibility of the disperse dye is inhibited.
比較例２８は、実施例１において、前記式（Ｉ）で表されるアゾ系分散染料に代えて、上記式（ＸＶ）で表されるアゾ系分散染料に代えた以外は、実施例１と同様にポリエステル系繊維品を染色同時難燃加工した結果を示すが、染色速度変化率が過大で、不適である。
Comparative Example 28 is the same as Example 1 except that in Example 1, the azo disperse dye represented by the formula (I) was replaced with the azo disperse dye represented by the formula (XV). Similarly, the results of dyeing and flame-retardant treatment of polyester fiber products are shown, but the rate of change in dyeing speed is excessive and unsuitable.
Comparative Example 28 is the same as Example 1 except that in Example 1, the azo disperse dye represented by the formula (I) was replaced with the azo disperse dye represented by the formula (XV). Similarly, the results of dyeing and flame-retardant treatment of polyester fiber products are shown, but the rate of change in dyeing speed is excessive and unsuitable.
Claims (10)
- （Ａ）（１）下記式（Ｉ）
で表されるアゾ系分散染料、
（２）下記式（ＩＩ）
で表されるアゾ系分散染料、
（３）下記式（ＩＩＩ）
で表されるアゾ系分散染料、及び
（４）下記式（ＩＶ）
で表されるアゾ系分散染料から選ばれる少なくとも１種と、
（Ｂ）下記式（ＶＩＩＩ）
で表されるリン酸エステルアミドを含む加工浴中にポリエステル系繊維品を浸漬し、加熱するポリエステル系繊維品の染色同時難燃加工方法。 (A) (1) Formula (I) below
Azo disperse dye represented by
(2) Formula (II) below
Azo disperse dye represented by
(3) the following formula (III)
and (4) an azo disperse dye represented by the following formula (IV)
At least one selected from azo disperse dyes represented by
(B) Formula (VIII) below
A method for simultaneously dyeing and flame-retarding a polyester fiber product by immersing the polyester fiber product in a processing bath containing a phosphoric acid ester amide represented by and heating. - 前記加工浴中にポリエステル系繊維品を浸漬し、１０５℃以上に加熱する請求項１に記載のポリエステル系繊維品の染色同時難燃加工方法。 The method for simultaneously dyeing and flame-retarding a polyester fiber product according to claim 1, wherein the polyester fiber product is immersed in the processing bath and heated to 105°C or higher.
- 前記加工浴は前記式（Ｉ）から（ＩＶ）で表されるアゾ系分散染料の少なくとも１種を濃度０．０５～５％оｗｆの範囲で有し、前記式（ＶＩＩＩ）で表されるリン酸エステルアミドを濃度０．５～１０％оｗｆの範囲で有する請求項１に記載のポリエステル系繊維品の染色同時難燃加工方法。 The processing bath contains at least one of the azo disperse dyes represented by the formulas (I) to (IV) in a concentration range of 0.05 to 5% wf, and the phosphorus represented by the formula (VIII) 2. The method for simultaneously dyeing and flame-retarding a polyester fiber according to claim 1, wherein the concentration of the acid ester amide is in the range of 0.5 to 10%owf.
- 前記式（Ｉ）から（ＩＶ）で表されるアゾ系分散染料と前記式（ＶＩＩＩ）で表されるリン酸エステルアミドがいずれも、平均粒子径０．２～２．０μｍの範囲にあるものである請求項１に記載のポリエステル系繊維品の染色同時難燃加工方法。 Both the azo disperse dyes represented by the above formulas (I) to (IV) and the phosphate ester amide represented by the above formula (VIII) have an average particle size in the range of 0.2 to 2.0 μm. The method for dyeing and simultaneously flame-retarding polyester fiber products according to claim 1.
- 請求項１に記載の前記式（Ｉ）から（ＩＶ）で表されるアゾ系分散染料よりなる群から選ばれる少なくとも１種と前記式（ＶＩＩＩ）で表されるリン酸エステルアミドを含む染色難燃加工ポリエステル系繊維品。 A dyeing-resistant dye containing at least one selected from the group consisting of the azo disperse dyes represented by the formulas (I) to (IV) according to claim 1 and the phosphate ester amide represented by the formula (VIII) Combustible polyester textiles.
- （Ａ）（１）下記式（Ｉ）
で表されるアゾ系分散染料、
（２）下記式（ＩＩ）
で表されるアゾ系分散染料、
（３）下記式（ＩＩＩ）
で表されるアゾ系分散染料、及び
（４）下記式（ＩＶ）
で表されるアゾ系分散染料から選ばれる少なくとも１種と、
（Ｂ）（１）下記式（Ｖ）
で表されるキノン系分散染料、
（２）下記式（ＶＩ）
で表されるキノン系分散染料、及び
（３）下記式（ＶＩＩ）
で表されるキノン系分散染料から選ばれる少なくとも１種のキノン系分散染料と、
（Ｃ）下記式（ＶＩＩＩ）
で表されるリン酸エステルアミドを含む加工浴中にポリエステル系繊維品を浸漬し、加熱するポリエステル系繊維品の染色同時難燃加工方法。 (A) (1) Formula (I) below
Azo disperse dye represented by
(2) Formula (II) below
Azo disperse dye represented by
(3) the following formula (III)
and (4) an azo disperse dye represented by the following formula (IV)
At least one selected from azo disperse dyes represented by
(B) (1) Formula (V) below
A quinone-based disperse dye represented by
(2) Formula (VI) below
and (3) a quinone-based disperse dye represented by the following formula (VII)
At least one quinone disperse dye selected from quinone disperse dyes represented by
(C) the following formula (VIII)
A method for simultaneously dyeing and flame-retarding a polyester fiber product by immersing the polyester fiber product in a processing bath containing a phosphoric acid ester amide represented by and heating. - 前記加工浴中にポリエステル系繊維品を浸漬し、１０５℃以上に加熱する請求項１に記載のポリエステル系繊維品の染色同時難燃加工方法。 The method for simultaneously dyeing and flame-retarding a polyester fiber product according to claim 1, wherein the polyester fiber product is immersed in the processing bath and heated to 105°C or higher.
- 前記加工浴は前記式（Ｉ）から（ＩＶ）で表されるアゾ系分散染料の少なくとも１種と前記式（Ｖ）から（ＶＩＩ）で表されるキノン系分散染料の少なくとも１種を合計濃度にて０．０５～５％оｗｆの範囲で有し、前記式（ＶＩＩＩ）で表されるリン酸エステルアミドを濃度０．５～１０％оｗｆの範囲で有する請求項１に記載のポリエステル系繊維品の染色同時難燃加工方法。 The processing bath contains at least one azo disperse dye represented by formulas (I) to (IV) and at least one quinone disperse dye represented by formulas (V) to (VII) at a total concentration of The polyester fiber according to claim 1, which has a range of 0.05 to 5% owf in and has a phosphoric ester amide represented by the formula (VIII) in a concentration range of 0.5 to 10% owf Dyeing and simultaneous flame retardant processing method for products.
- 前記式（Ｉ）から（ＩＶ）で表されるアゾ系分散染料と前記式（Ｖ）から（ＶＩＩ）で表されるキノン系分散染料と前記式（ＶＩＩＩ）で表されるリン酸エステルアミドがいずれも、平均粒子径０．２～２．０μｍの範囲にあるものである請求項５に記載のポリエステル系繊維品の染色同時難燃加工方法。 The azo disperse dyes represented by the formulas (I) to (IV), the quinone disperse dyes represented by the formulas (V) to (VII), and the phosphate ester amide represented by the formula (VIII) The method for simultaneously dyeing and flame-retarding a polyester fiber product according to claim 5, wherein both have an average particle size in the range of 0.2 to 2.0 µm.
- 請求項６に記載の前記式（Ｉ）から（ＩＶ）で表されるアゾ系分散染料よりなる群から選ばれる少なくとも１種と前記式（Ｖ）から（ＶＩＩ）で表されるキノン系分散染料よりなる群から選ばれる少なくとも１種と前記式（ＶＩＩＩ）で表されるリン酸エステルアミドを含む染色難燃加工ポリエステル系繊維品。
At least one selected from the group consisting of the azo disperse dyes represented by the formulas (I) to (IV) according to claim 6 and the quinone disperse dyes represented by the formulas (V) to (VII) A dyed, flame-retardant polyester fiber product containing at least one selected from the group consisting of and a phosphate ester amide represented by the formula (VIII).
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04164969A (en) * | 1990-10-30 | 1992-06-10 | Nippon Kayaku Co Ltd | Disperse dye composition and method of dyeing hydrophobic fiber |
| JP2009270213A (en) * | 2008-05-02 | 2009-11-19 | Nicca Chemical Co Ltd | Flame-retardant finishing agent for polyester-based fiber, flame-retardant polyester-based fiber using the same, and method for producing the same |
| JP2012102444A (en) * | 2010-11-12 | 2012-05-31 | Daikyo Kagaku Kk | Scouring agent composition for polyester-based fiber knit and scouring method using the same |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04164969A (en) * | 1990-10-30 | 1992-06-10 | Nippon Kayaku Co Ltd | Disperse dye composition and method of dyeing hydrophobic fiber |
| JP2009270213A (en) * | 2008-05-02 | 2009-11-19 | Nicca Chemical Co Ltd | Flame-retardant finishing agent for polyester-based fiber, flame-retardant polyester-based fiber using the same, and method for producing the same |
| JP2012102444A (en) * | 2010-11-12 | 2012-05-31 | Daikyo Kagaku Kk | Scouring agent composition for polyester-based fiber knit and scouring method using the same |
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