EP0379954A2 - Agent véhiculaire pour la teinture de matériaux fibreux hydrophobes - Google Patents
Agent véhiculaire pour la teinture de matériaux fibreux hydrophobes Download PDFInfo
- Publication number
- EP0379954A2 EP0379954A2 EP90100893A EP90100893A EP0379954A2 EP 0379954 A2 EP0379954 A2 EP 0379954A2 EP 90100893 A EP90100893 A EP 90100893A EP 90100893 A EP90100893 A EP 90100893A EP 0379954 A2 EP0379954 A2 EP 0379954A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- carrier
- weight
- esters
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000004043 dyeing Methods 0.000 title claims abstract description 23
- 230000002209 hydrophobic effect Effects 0.000 title claims 3
- 239000000835 fiber Substances 0.000 title description 8
- 239000000463 material Substances 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 34
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 239000000969 carrier Substances 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 13
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000001424 substituent group Chemical group 0.000 claims abstract description 4
- 239000004753 textile Substances 0.000 claims abstract description 4
- 150000007860 aryl ester derivatives Chemical class 0.000 claims abstract 2
- 239000003995 emulsifying agent Substances 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000005543 phthalimide group Chemical class 0.000 claims description 3
- 239000002657 fibrous material Substances 0.000 claims 2
- 229920000728 polyester Polymers 0.000 abstract description 13
- 125000005907 alkyl ester group Chemical group 0.000 abstract description 4
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 21
- YVJJTEADFAZYEE-UHFFFAOYSA-N 2,3,4-tris(2-phenylpropyl)phenol Chemical compound C=1C=CC=CC=1C(C)CC(C=1CC(C)C=2C=CC=CC=2)=CC=C(O)C=1CC(C)C1=CC=CC=C1 YVJJTEADFAZYEE-UHFFFAOYSA-N 0.000 description 19
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 150000002169 ethanolamines Chemical class 0.000 description 11
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 239000000986 disperse dye Substances 0.000 description 8
- 239000000975 dye Substances 0.000 description 7
- -1 halogen toluenes Chemical class 0.000 description 7
- DLKDEVCJRCPTLN-UHFFFAOYSA-N 2-butylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCC)C(=O)C2=C1 DLKDEVCJRCPTLN-UHFFFAOYSA-N 0.000 description 6
- FHUODBDRWMIBQP-UHFFFAOYSA-N Ethyl p-anisate Chemical compound CCOC(=O)C1=CC=C(OC)C=C1 FHUODBDRWMIBQP-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 239000004359 castor oil Substances 0.000 description 4
- 235000019438 castor oil Nutrition 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 4
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 4
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 3
- 235000019799 monosodium phosphate Nutrition 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229940072395 n-butylphthalimide Drugs 0.000 description 3
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 3
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- DMAXMXPDVWTIRV-UHFFFAOYSA-N 2-(2-phenylethyl)phenol Chemical compound OC1=CC=CC=C1CCC1=CC=CC=C1 DMAXMXPDVWTIRV-UHFFFAOYSA-N 0.000 description 2
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PFYHAAAQPNMZHO-UHFFFAOYSA-N Methyl 2-methoxybenzoate Chemical compound COC(=O)C1=CC=CC=C1OC PFYHAAAQPNMZHO-UHFFFAOYSA-N 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- FNODWEPAWIJGPM-UHFFFAOYSA-N ethyl o-methoxybenzoate Natural products CCOC(=O)C1=CC=CC=C1OC FNODWEPAWIJGPM-UHFFFAOYSA-N 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- QLIQIXIBZLTPGQ-UHFFFAOYSA-N 4-(2-hydroxyethoxy)benzoic acid Chemical compound OCCOC1=CC=C(C(O)=O)C=C1 QLIQIXIBZLTPGQ-UHFFFAOYSA-N 0.000 description 1
- HRAQMGWTPNOILP-UHFFFAOYSA-N 4-Ethoxy ethylbenzoate Chemical compound CCOC(=O)C1=CC=C(OCC)C=C1 HRAQMGWTPNOILP-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 240000000528 Ricinus communis Species 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- FPRPQIKQCRLLLT-UHFFFAOYSA-N butyl 4-ethoxybenzoate Chemical compound CCCCOC(=O)C1=CC=C(OCC)C=C1 FPRPQIKQCRLLLT-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical compound CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 description 1
- NSRLIMVWJNHWJW-UHFFFAOYSA-N ethyl 2-hydroxy-3-methylbenzoate Chemical compound CCOC(=O)C1=CC=CC(C)=C1O NSRLIMVWJNHWJW-UHFFFAOYSA-N 0.000 description 1
- GSQLMBQLTPEPHD-UHFFFAOYSA-N ethyl 3-methoxybenzoate Chemical compound CCOC(=O)C1=CC=CC(OC)=C1 GSQLMBQLTPEPHD-UHFFFAOYSA-N 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- RNHXTCZZACTEMK-UHFFFAOYSA-N methyl 4-ethoxybenzoate Chemical compound CCOC1=CC=C(C(=O)OC)C=C1 RNHXTCZZACTEMK-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- LZRFQYZCMVMADF-UHFFFAOYSA-N phenyl 2-methoxybenzoate Chemical compound COC1=CC=CC=C1C(=O)OC1=CC=CC=C1 LZRFQYZCMVMADF-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- WEHMFTWWOGBHCR-UHFFFAOYSA-N propyl 4-methoxybenzoate Chemical compound CCCOC(=O)C1=CC=C(OC)C=C1 WEHMFTWWOGBHCR-UHFFFAOYSA-N 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 150000003460 sulfonic acids Chemical class 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
- D06P1/44—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
- D06P1/64—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 using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
- D06P1/649—Compounds containing carbonamide, thiocarbonamide or guanyl groups
- D06P1/6495—Compounds containing carbonamide -RCON= (R=H or hydrocarbons)
- D06P1/6498—Compounds containing -CONCO-, e.g. phthalimides, hydantoine; Compounds containing RCONHSO2R (R=H or hydrocarbon)
-
- 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
- D06P1/64—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 using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/651—Compounds without nitrogen
- D06P1/65106—Oxygen-containing compounds
- D06P1/65125—Compounds containing ester groups
Definitions
- the invention relates to carriers, their preparations and processes for dyeing preferably polyester materials with disperse dyes in the presence of these carriers.
- Known carriers used in textile practice in dyeing polyester include halogenobenzenes, halogen toluenes, N-alkylphthalimides, aromatic carboxylic esters, methylnaphthalene, diphenyl, diphenyl ether, naphthol ether, phenol ether and oxydiphenyls.
- these connections have disadvantages.
- the carrier types mentioned - with the exception of N-alkylphthalimides - have a strong intrinsic odor. Methylnaphthalene and the oxydiphenyls adversely affect the lightfastness of the dyeings.
- Diphenyl ether has the disadvantage that its carrier activity depends strongly on the constitution of the disperse dye used and therefore often no reproducible colorations are obtained.
- N-alkylphthalimides show a strong drop in the carrier effect at dyeing temperatures below 98 ° C., which indicates their use in higher regions, in the open regions Dyeing equipment limits this temperature is not reached.
- Phthalic acid esters and benzoic acid esters have only a limited carrier effect and a limited leveling capacity and therefore require high amounts.
- the object of the present invention is to provide highly effective, halogen-free carriers which bring about the most level possible coloring with a small amount used.
- the dyeing achieved should meet high authenticity standards, and when dyeing mixed fibers, the accompanying fiber should not be soiled.
- Suitable alkoxybenzoic acid esters are those of the formula wherein R C1-C7-alkyl, which may be substituted by phenyl, or phenyl, which may be substituted by C1-C4-alkyl, C1-C4-alkoxy or C1-C4-alkoxycarbonyl and R1 is C1-C4 alkyl, which may be substituted by OH.
- the substituent -OR1 is preferably in the o- or p-position.
- Suitable phthalimides are those of the formula wherein X is C1-C7 alkyl.
- the preferred weight ratio of N-alkylphthalimides to the benzoic acid esters is 0.5-12: 1.
- the carriers according to the invention are water-insoluble, they are preferably added to the dyeing liquors in the form of preparations which contain emulsifiers or dispersants and, if appropriate, solvents.
- components 1.) - 4.) can also be used as mixtures.
- Examples of preferred compounds (I) are: o / p-methoxybenzoic acid-n-C1-C4-alkyl esters, o / p-ethoxybenzoic acid-n-C1-C4-alkyl esters and o / p-Hydroxyethoxybenzoic acid n-C1-C4 alkyl ester.
- Examples of preferred compounds (II) are straight-chain or branched C3-C5-N-alkylphthalimides.
- Nonionic and anionic emulsifiers are preferred as emulsifiers 3.).
- emulsifiers are mixtures of a) ethoxylated oils, such as castor oil or soybean oil, ethoxylated alcohols, alkylphenol polyglycol ethers or phenylalkylphenol polyglycol ethers, b) alkali metal, alkaline earth metal and / or ammonium salts of organic sulfonic acids containing at least 10 carbon atoms, such as dodecylbenzenesulfonic acid, Sulfo fatty acids and ricinoleyl methyl tauride.
- ethoxylated oils such as castor oil or soybean oil, ethoxylated alcohols, alkylphenol polyglycol ethers or phenylalkylphenol polyglycol ethers
- z. B. alkanols, glycols, ketones, N-substituted caprolactams or ethers can be used.
- the carrier mixtures according to the invention are well compatible with other carriers, they can also be used in a mixture with known other carriers.
- the disperse dyes used for dyeing are the disperse dyes usually used for dyeing polyesters, as described, for example, in "Color Index” Vol. 2, pp. 2483-2741, 3rd edition (1971).
- the dyeing in the presence of the carriers according to the invention is carried out according to the batchwise methods customary for dyeing with disperse dyes; the usual process operating at 98 ° C. and the high-temperature process may be mentioned as such.
- the carrier blends according to the invention are also suitable for dyeing polyester / wool and polyester / cotton blended fabrics, because when they are used the soiling of the wool and cotton content is avoided by the disperse dyes.
- the coloring can be carried out at temperatures of 90-140 ° C, the preferred industrial use being at 90-105 ° C.
- An additional advantage of the carrier settings described is the very good effectiveness below the cooking temperature, which pure N-alkylphthalimide carriers do not show, e.g. B. at 95 ° C, which are often not exceeded under practical conditions with open dyeing equipment.
- the amounts of the mixture of carriers (I) and (II) required to carry out the dyeing can easily be determined from case to case by preliminary tests. In general, amounts of 1 to 7 g per liter of dye liquor have proven themselves in the usual liquor ratios of 1: 5 to 1:40.
- N-alkylphthalimides as carriers in dyeing polyester is known and is described in DE-PS 1 769 210.
- DE-PS 1 769 210 also discloses the use of mixtures of N-alkylphthalimides with disubstituted benzoic acid esters.
- the mixtures according to the invention have a higher color-accelerating effect than the sum of the individual effects.
- This synergistic increase in the effectiveness is not shown by the mixtures known hitherto (for example the mixtures of N-alkylphthalimides with alkyl group-containing salicylic acid compounds described in DE-PS 1 769 210).
- the mixing ratio at which the synergistic optimum is present depends on the components of the carrier mixtures and can easily be determined in individual cases by preliminary tests.
- Yarns made of polyester fibers are placed in a liquor ratio of 1:40 in a bath heated to 60 ° C, containing 0.25 g of a dye of the formula per liter 2 g of a condensation product of naphthalene sulfonate and formaldehyde, 2 g of sodium dihydrogen phosphate and 3 g of a carrier setting contains the following composition: 2.55 g of ethyl 4-methoxybenzoate 0.25 g tri- (methylphenylethyl) phenol with approx. 15 mol EO 0.20 g monoethanolamine salt of dodecylbenzenesulfonic acid.
- the pH of the bath is adjusted to pH 4.5-5 with acetic acid.
- the bath is then heated to 98 ° C. and held at this temperature for 60 minutes. A uniform blue color is obtained.
- the carrier effectiveness of the carrier mixtures of Examples 6-11 is determined by comparing the color depths achieved.
- the small amounts of the mixtures demonstrate their more advantageous carrier activity compared to the individual components. example % By weight of the components in the mixture required amount of mixture Component I 6 30 I 80 90 55 II 7 35 I 90 120 50 II 8th 35 I 90 120 50 II 9 17 I 90 100 68 II 10th 35 I 90 100 50 II 11 52 I 80 90 40 II
- Example 12 comparative example to DE-PS 1 769 210)
- this mixture shows no synergistic increase in carrier effectiveness compared to the individual components.
- the pH of the bath is adjusted to pH 4.5-5 with acetic acid.
- the dye liquor is then brought to the boiling temperature and held at this temperature for one hour. A full, even red color is achieved.
- Polyester staple fibers are introduced in a liquor ratio of 1:15 into a dyeing liquor containing 1 g of a disperse dye according to Example 14 per liter, 0.03 g of a dye according to the Color Index, 2nd edition (1956) Volume 3, No. 12790, 2nd g of a condensation product of naphthalene sulfonate and formaldehyde, 2 g of sodium dihydrogen phosphate and 3.5 g of a carrier setting of Example 13.
- the pH of the bath is adjusted to pH 4.5-5 with acetic acid.
- the liquor is slowly heated to 98 ° C. and treated at this temperature for one hour. A dark reddish brown color is obtained.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3902052 | 1989-01-25 | ||
| DE3902052A DE3902052A1 (de) | 1989-01-25 | 1989-01-25 | Carrier fuer das faerben von hydrophoben fasermaterialien |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0379954A2 true EP0379954A2 (fr) | 1990-08-01 |
| EP0379954A3 EP0379954A3 (fr) | 1991-08-14 |
| EP0379954B1 EP0379954B1 (fr) | 1993-08-18 |
Family
ID=6372701
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP90100893A Expired - Lifetime EP0379954B1 (fr) | 1989-01-25 | 1990-01-17 | Agent véhiculaire pour la teinture de matériaux fibreux hydrophobes |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0379954B1 (fr) |
| JP (1) | JP2612945B2 (fr) |
| DE (2) | DE3902052A1 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2247470A (en) * | 1990-08-27 | 1992-03-04 | Sandoz Ltd | N-Alkylphthalimide mixtures for use as carriers in dyeing and optical brightening |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09319104A (ja) * | 1996-05-24 | 1997-12-12 | Ricoh Co Ltd | 電子写真感光体 |
| JP5629104B2 (ja) * | 2010-03-24 | 2014-11-19 | 株式会社クラレ | ポリエーテルイミド繊維の染色方法及びその染色物 |
| EP2760942B1 (fr) * | 2011-09-29 | 2016-03-02 | Dow Global Technologies LLC | Formulations contenant des véhiculeurs de teintures de type benzoate pour articles en méta-aramide |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1140000A (fr) * | 1955-01-05 | 1957-07-09 | Hoechst Ag | Procédé de teinture d'articles en fibres de polyesters à haut degré de polymérisation |
| US2881045A (en) * | 1954-06-17 | 1959-04-07 | American Cyanamid Co | Method of dyeing synthetic fibrous materials |
| GB1193948A (en) * | 1968-04-20 | 1970-06-03 | Bayer Ag | Printing and Dyeing Process |
| LU67468A1 (fr) * | 1972-09-08 | 1973-07-06 |
-
1989
- 1989-01-25 DE DE3902052A patent/DE3902052A1/de not_active Withdrawn
-
1990
- 1990-01-17 EP EP90100893A patent/EP0379954B1/fr not_active Expired - Lifetime
- 1990-01-17 DE DE9090100893T patent/DE59002352D1/de not_active Expired - Fee Related
- 1990-01-22 JP JP2010766A patent/JP2612945B2/ja not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2881045A (en) * | 1954-06-17 | 1959-04-07 | American Cyanamid Co | Method of dyeing synthetic fibrous materials |
| FR1140000A (fr) * | 1955-01-05 | 1957-07-09 | Hoechst Ag | Procédé de teinture d'articles en fibres de polyesters à haut degré de polymérisation |
| GB1193948A (en) * | 1968-04-20 | 1970-06-03 | Bayer Ag | Printing and Dyeing Process |
| LU67468A1 (fr) * | 1972-09-08 | 1973-07-06 |
Non-Patent Citations (2)
| Title |
|---|
| Chemical Abstracts Band 98, Nr.16, 1983, Zusammenfassung Nr. 127634p. * |
| Chemical Abstracts Band 98, Nr.16, 1983, Zusammenfassung Nr.127632m. * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2247470A (en) * | 1990-08-27 | 1992-03-04 | Sandoz Ltd | N-Alkylphthalimide mixtures for use as carriers in dyeing and optical brightening |
| GB2247470B (en) * | 1990-08-27 | 1994-07-13 | Sandoz Ltd | N-Alkylphthalimide mixtures for use as carriers in dyeing and optical brighting |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0379954B1 (fr) | 1993-08-18 |
| JP2612945B2 (ja) | 1997-05-21 |
| JPH02229280A (ja) | 1990-09-12 |
| DE3902052A1 (de) | 1990-07-26 |
| EP0379954A3 (fr) | 1991-08-14 |
| DE59002352D1 (de) | 1993-09-23 |
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