EP0414631A1 - Mélange d'agents auxiliaires et son utilisation pendant la teinture de matériaux fibreux en polyesters - Google Patents
Mélange d'agents auxiliaires et son utilisation pendant la teinture de matériaux fibreux en polyesters Download PDFInfo
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- EP0414631A1 EP0414631A1 EP90810099A EP90810099A EP0414631A1 EP 0414631 A1 EP0414631 A1 EP 0414631A1 EP 90810099 A EP90810099 A EP 90810099A EP 90810099 A EP90810099 A EP 90810099A EP 0414631 A1 EP0414631 A1 EP 0414631A1
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- European Patent Office
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- carbon atoms
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- 238000004043 dyeing Methods 0.000 title claims abstract description 35
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- 239000000835 fiber Substances 0.000 title claims abstract description 14
- 239000000463 material Substances 0.000 title claims abstract description 14
- 239000012752 auxiliary agent Substances 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 38
- 239000002253 acid Substances 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 18
- 150000002148 esters Chemical class 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 11
- 239000000986 disperse dye Substances 0.000 claims abstract description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 8
- 239000004753 textile Substances 0.000 claims abstract description 8
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- 239000001257 hydrogen Substances 0.000 claims abstract description 5
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
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- LNPDTAQEAXGQSK-UHFFFAOYSA-N 2-ethylhexyl 2-(1,3-dioxoisoindol-2-yl)hexanoate Chemical compound C1(C=2C(C(N1C(C(=O)OCC(CCCC)CC)CCCC)=O)=CC=CC2)=O LNPDTAQEAXGQSK-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
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- 125000005843 halogen group Chemical group 0.000 claims 2
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- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 claims 1
- 238000013508 migration Methods 0.000 abstract description 5
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- 239000005977 Ethylene Substances 0.000 abstract description 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
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- 239000000975 dye Substances 0.000 description 29
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- 239000000047 product Substances 0.000 description 19
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- 239000002270 dispersing agent Substances 0.000 description 8
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- 239000002657 fibrous material Substances 0.000 description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 5
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 4
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 4
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 4
- 235000011130 ammonium sulphate Nutrition 0.000 description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 235000011007 phosphoric acid Nutrition 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
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- 229910052783 alkali metal Inorganic materials 0.000 description 3
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- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical class OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- NEISHALDHGTVPL-UHFFFAOYSA-N 2-[1-(2-methylphenyl)ethyl]phenol Chemical compound C=1C=CC=C(O)C=1C(C)C1=CC=CC=C1C NEISHALDHGTVPL-UHFFFAOYSA-N 0.000 description 2
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- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000001005 nitro dye Substances 0.000 description 1
- GVRNEIKWGDQKPS-UHFFFAOYSA-N nonyl benzenesulfonate Chemical group CCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVRNEIKWGDQKPS-UHFFFAOYSA-N 0.000 description 1
- FFQLQBKXOPDGSG-UHFFFAOYSA-N octadecyl benzenesulfonate Chemical compound CCCCCCCCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 FFQLQBKXOPDGSG-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- JNYAEWCLZODPBN-CTQIIAAMSA-N sorbitan Polymers OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([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
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229920006304 triacetate fiber Polymers 0.000 description 1
- HLXQFVXURMXRPU-UHFFFAOYSA-L trimethyl-[10-(trimethylazaniumyl)decyl]azanium;dibromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCCCCCCC[N+](C)(C)C HLXQFVXURMXRPU-UHFFFAOYSA-L 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/54—Polyesters using dispersed dyestuffs
-
- 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
- D06P1/60—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 polyethers
- D06P1/613—Polyethers without nitrogen
- D06P1/6131—Addition products of hydroxyl groups-containing compounds with oxiranes
- D06P1/6135—Addition products of hydroxyl groups-containing compounds with oxiranes from aromatic alcohols or from phenols, naphthols
-
- 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)
Definitions
- the present invention relates to a new auxiliary mixture and its use in dyeing polyester fiber materials.
- the auxiliary mixture according to the invention advantageously contains 20 to 70 percent by weight of component (A) 15 to 40 percent by weight of component (B) and 15 to 40 weight percent of component (C).
- Components (A), (B) and (C) can be present as individual compounds or in the form of a mixture of two or more compounds.
- W means, for example, a divalent aliphatic, cycloaliphatic or aromatic radical which is linked to the carboxyl groups of the imide group.
- W advantageously represents a halogen-substituted, straight-chain or branched hydrocarbon radical of a saturated or ethylenically unsaturated dicarboxylic acid having 4 to 10 carbon atoms.
- aliphatic saturated dicarboxylic acids are Succinic and glutaric acid.
- Ethylenically unsaturated dicarboxylic acids are preferably maleic, dimethyl maleic, dichloromaleic, citraconic, glutaconic or itaconic acid.
- W represents in particular the radical of a tetrahydro- or hexahydrophthalic acid.
- W preferably represents the divalent radical of an aromatic dicarboxylic acid, such as, for example, a naphthalenedicarboxylic acid or phthalic acid.
- W is preferably a phenylene radical which is substituted with halogen, e.g. Chlorine or bromine, C1-C4-alkyl such as methyl, tert-butyl or C1-C4-alkoxy such as methoxy can be substituted.
- W in particular denotes an unsubstituted phenylene radical.
- R can be saturated or unsaturated, straight-chain or branched.
- R is advantageously an alkyl radical having 1 to 24, preferably 1 to 12, carbon atoms.
- alkyl radicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, pentyl, n-hexyl, 2-ethyl-hexyl, 1,1,3,3-tetramethylbutyl, n-octyl, n-dodecyl, myristyl, octadecyl, arachidyl or behenyl.
- R is in particular a cyclopentyl or, above all, a cyclohexyl radical.
- the benzyl radical as R is particularly suitable as an araliphatic radical.
- n is preferably 5.
- dicarboxyimido esters of the formula (1) correspond to the formula wherein W1 alkylene or alkenylene having 2 to 4 carbon atoms, cyclohexylene or phenylene, which is unsubstituted or substituted by halogen, such as chlorine or bromine, methyl or methoxy, and R1 alkyl having 1 to 12 carbon atoms, preferably 3 to 8 carbon atoms, cyclohexyl or benzyl mean.
- Typical representatives of the dicarboxyimido esters used according to the invention are Phthalimido-hexanoic acid methyl ester, Phthalimido-hexanoic acid ethyl ester, Phthalimido-hexanoic acid propyl ester, N-butyl phthalimido-hexanoate, 2-ethylhexyl phthalimido-hexanoate, Hexahydrophthalimido-hexanoic acid n-butyl ester, 2-ethylhexyl hexahydrophthalimido-hexanoate, Tetrahydrophthalimido-hexanoic acid n-butyl ester, N-butyl tetrachlorophthalimido-hexanoate, 2-ethylhexyl tetrachlorophthalimido-hexanoate, N-butyl succinimido hexanoate and
- phthalimido-hexanoic acid C1-C8-alkyl esters and especially phthalimido-hexanoic acid-C3-C8-alkyl esters such as in particular the phthalimido-hexanoic acid-2-ethylhexyl ester.
- the compounds of the formulas (1) and (3) are prepared in a manner known per se.
- the preparation can preferably be carried out by using a dicarboxylic anhydride of the formula with a compound of the formula in the presence of an alcohol of formula (1c) R-OH.
- starting materials of the formula (1a) are maleic anhydride, dimethylmaleic anhydride, dichloromaleic anhydride, succinic anhydride, dimethylsuccinic anhydride, citraconic anhydride, glutaric anhydride, itaconic anhydride, glutaconic anhydride, phthalic anhydride, tetrachlorophthalic anhydride, tetrahydrophthalic anhydride or hexahydrophthalic anhydride.
- starting materials of the formula (1b) are ⁇ -pyrrolidone, ⁇ -piperidone or preferably ⁇ -caprolactam.
- alcohols of the formula (1c) are methanol, ethanol, n-butanol, sec-butanol, tert-butanol, amyl alcohol, hexanols, 2-ethylhexanol, octyl alcohols, decyl alcohols, dodecyl alcohols, cyclohexanol or benzyl alcohol. These alcohols can be used alone or as mixtures.
- the substituent Y in formula (2) advantageously has 8 to 12 carbon atoms and is in particular ⁇ -methylbenzyl, ⁇ , ⁇ -dimethylbenzyl, ⁇ -tolylethyl or ⁇ -xylylethyl.
- ⁇ -Methylbenzyl is particularly preferred.
- (Alkylene-O) ⁇ Chains are preferably of the ethylene glycol, propylene ethylene glycol or ethylene propylene glycol type; the former is particularly preferred.
- n 1 is preferably 4 to 40.
- the acid residue X is derived, for example, from low molecular weight dicarboxylic acids, such as of maleic acid, succinic acid or sulfosuccinic acid, and is connected to the alkyleneoxy part of the molecule via an ester bridge.
- X is derived from inorganic polybasic acids, such as sulfuric acid or orthophosphoric acid.
- the acid residue X can be in the form of a free acid or in salt form, i.e. e.g. as an alkali metal, ammonium or amine salt.
- alkali metal, ammonium or amine salts are lithium, sodium, potassium, ammonium, trimethylamine, diethylamine, ethanolamine, diethanolamine or triethanolamine salts.
- Alkali metal salts or triethanolamine salts are preferred.
- the mono- or diethanolamine salts can be etherified further with 1 to 4 oxethylene units.
- Preferred acid esters of component (B) correspond to the formula where Y1 is ⁇ -methylbenzyl, ⁇ , ⁇ -dimethylbenzyl or ⁇ -tolylethyl, X1 is an acid residue which is derived from sulfuric acid or preferably o-phosphoric acid, and m are 1 to 3 and n2 are 4 to 40.
- acidic esters are preferably in the form of sodium, potassium, ammonium, diethylamine, triethylamine, diethanolamine or triethanolamine salts.
- the acidic esters of formula (2) or (4) which are suitable as components (B) are prepared by adding alkylene oxide (ethylene oxide or propylene oxide) to a phenol compound which is substituted by definition and the adduct with a polybasic oxygen acid or a functional derivative of this acid , such as Acid anhydrides, acid halides, acid esters or acid amides are converted into the acidic esters and, if appropriate, the acidic ester obtained into the abovementioned salts.
- these functional derivatives are phosphorus pentoxide, phosphorus oxytrichloride, chlorosulfonic acid or sulfamic acid. Both the alkylene oxide addition and the esterification can be carried out by known methods.
- Highly suitable components (B) are acidic esters or their salts of a polyadduct of 4 to 40 moles of ethylene oxide with 1 mole of a phenol which has at least one ⁇ -tolylethyl group, an ⁇ -methylbenzyl group or an ⁇ , ⁇ -dimethylbenzyl group, e.g. ⁇ -Tolylethylphenol, ⁇ -methylbenzylphenol, bis- ( ⁇ -methylbenzyl) -phenol or tris- ⁇ - (methylbenzyl) -phenol, whereby these acidic esters can be used individually or in a mixture.
- the styrene addition products are prepared in a known manner, preferably in the presence of catalysts, such as sulfuric acid, p-toluenesulfonic acid or zinc chloride.
- catalysts such as sulfuric acid, p-toluenesulfonic acid or zinc chloride.
- Suitable styrenes are suitably styrene, ⁇ -methylstyrene or vinyltoluene (4-methylstyrene).
- the phenols are phenol, cresols or xylenols.
- Acidic phosphoric acid esters (mono- and diesters) or sulfuric acid esters or their salts of oxyalkylation products of the formula are very particularly preferred wherein m is 1 to 3 and n3 12 to 30.
- oxyalkylation products of the formulas (4) and (5) - Oxalkylation product with 18 ethylene oxide units of the adduct of 2 moles of styrene and 1 mole of phenol - Oxalkylation product with 18 ethylene oxide units of the adduct of 3 moles of styrene with 1 mole of phenol - Oxalkylation product with 27 ethylene oxide units of the adduct of 2 moles of 4-methylstyrene with 1 mole of phenol - Oxalkylation product with 17 ethylene oxide units of the adduct of 3 moles of 4-methylstyrene with 1 mole of phenol - Oxalkylation product with 18 ethylene oxide units of the mixture of an adduct of 2 moles of styrene with 1 mole of phenol and an adduct of 3 moles of styrene with 1 mole of phenol Oxyalkylation product of 13 ethylene oxide units of the mixture of an adduct of 2 moles
- the nonionic surfactant used as component (C) is advantageously an alkylene oxide addition product of 2 to 100 moles of alkylene oxide, for example ethylene oxide and / or propylene oxide, on 1 mole of an aliphatic Monoalcohol with at least 4 carbon atoms, a 3- to 6-valent aliphatic alcohol with preferably 3 to 6 carbon atoms, one optionally substituted by C4-C12-alkyl, phenyl, ⁇ -tolylethyl, benzyl, ⁇ -methylbenzyl or ⁇ , ⁇ -dimethylbenzyl or a fatty acid with 8 to 22 carbon atoms.
- nonionic surfactants are: - Addition products of preferably 2 to 80 mol of alkylene oxide, in particular ethylene oxide, it being possible for individual ethylene oxide units to be replaced by substituted epoxides, such as styrene oxide and / or propylene oxide, with higher unsaturated or saturated monoalcohols, fatty acids, fatty amines or fatty amides each having 8 to 22 carbon atoms or to benzyl alcohols, phenylphenols, benzylphenols, ⁇ -phenethylphenols, ⁇ -methylbenzylphenols, ⁇ , ⁇ -dimethylbenzylphenols, ⁇ -tolylethylphenols or alkylphenols, the alkyl radicals of which have at least 4 carbon atoms; - Alkylene oxide, in particular ethylene oxide and / or propylene oxide condensation products (block polymers); - Ethylene oxide-propylene oxide adducts with fatty amine
- oxyalkylation products of the formula (5) derived from styrene addition products are particularly preferred as nonionic surfactants.
- nonionic surfactants can be represented by the formula or by the formula are shown in what R 'is an alkyl or alkenyl radical each having 8 to 24 carbon atoms or a radical of the formula T is an aliphatic radical with 8 to 30 carbon atoms and z mean 1 to 25 and Y, m, n1 and "alkylene" have the meaning given above.
- the compounds of formula (6) can by reacting the adduct of the formula with a fatty acid T-COOH or by reacting an alcoholic or phenolic compound R'-OH with a fatty acid ester of the formula getting produced.
- the compounds of the formula (7) are reaction products from addition products of the formula Formaldehyde or a formaldehyde-releasing compound, for example paraformaldehyde and a fatty acid ester of the formula T-CO-O ( ⁇ CH2CH2O) ⁇ H and are partially described in Japanese Patent Application Laid-Open No. 83-18486.
- Compounds which are not mentioned there and fall under formula (7) can be prepared accordingly, the reaction conditions mentioned in the Japanese laid-open publication leading to the desired products of the formula (7).
- Well-suited components (C) also correspond to the formula wherein R1 alkyl or alkenyl each having 8 to 22 carbon atoms, of Z1 and Z2 a phenyl and the other hydrogen and s mean 4 to 80.
- the compounds of formula (8) are prepared by adding styrene oxide to the polyethylene glycol ether of the formula R ⁇ -O ( ⁇ CH2CH2O) ⁇ H attaches.
- the new auxiliary preparations can be prepared by simply stirring the components (A), (B), (C) and, if appropriate, together with water, giving homogeneous, clear mixtures which are notable for good transport and storage stability.
- the auxiliary mixtures according to the invention are particularly very stable at higher temperatures up to 130 ° C. when they are used in dye baths. They increase the rate of diffusion of the dyes when dyeing polyester fiber materials, preferably linear polyester fibers.
- the present invention accordingly also relates to a process for dyeing polyester fiber material with disperse dyes, which is characterized in that this material is dyed in the presence of the auxiliary mixture according to the invention.
- the amounts used in which the auxiliary combination according to the invention is added to the dyebaths range from 0.3 to 6 g, preferably 0.5 to 4 g, per liter of dye liquor.
- polyester fiber material in particular textile material, which can be dyed in the presence of the new auxiliary mixture, e.g. Cellulose ester fibers, such as cellulose-2 1 ⁇ 2 acetate fibers and triacetate fibers and particularly linear polyester fibers, should be mentioned.
- Linear polyester fibers are to be understood as synthetic fibers which are obtained, for example, by condensation of terephthalic acid with ethylene glycol or of isophthalic acid or terephthalic acid with 1,4-bis (hydroxymethyl) cyclohexane, as well as copolymers of terephthalic and isophthalic acid and ethylene glycol.
- the linear polyester used almost exclusively in the textile industry so far consists of terephthalic acid and ethylene glycol.
- the fiber materials can also be used as a mixed fabric among themselves or with other fibers, e.g. Mixtures of polyacrylonitrile / polyester, polyamide / polyester, polyester / cotton, polyester / viscose and polyester / wool can be used.
- the textile material to be dyed can be in various stages of processing. Examples include: loose material, piece goods, such as knitted or woven fabrics, yarn in the form of a wrap or muff.
- the latter can have winding densities of 200 to 600 g / cm3, in particular 400 to 450 g / cm3.
- the disperse dyes to be used which are only sparingly soluble in water and are present in the dyeing liquor for the most part in the form of a fine dispersion, can belong to a wide variety of dye classes, for example the acridone, azo, anthraquinone, coumarin, methine, Perinone, quinophthalone, naphthoquinoneimine, styryl or nitro dyes.
- Mixtures of disperse dyes can also be used according to the invention.
- the mixtures are used in particular for the production of level mixed tone dyeings, including a dichromatic or trichromatic dyeing.
- Trichromatic is primarily understood to mean a three-way combination of the basic colors yellow (or orange), red and blue.
- the amount of dyes to be added to the liquor depends on the desired color strength; In general, amounts of 0.01 to 10, preferably 0.05 to 5 percent by weight, based on the textile material used, have proven successful.
- the auxiliaries to be used according to the invention can also be mixed with known carriers based on e.g. Di- or trichlorobenzene, methyl- or ethylbenzene, o-phenylphenol, benzylphenol, diphenyl ether, chlorodiphenyl, methyldiphenyl, cyclohexanone, acetophenone, alkylphenoxyethanol, mono-, di- or trichlorophenoxyethanol or propanol, pentachlorophenoxyethene, or in particular, based on methyl, from phenhenyl or Dibenzyl ether can be used.
- the carriers are preferably used in an amount of 0.5 g to 2 g / l of liquor or 10 to 60 percent by weight, based on the auxiliary preparation.
- the dyebaths can also contain oligomer inhibitors, anti-foaming agents (e.g. silicone oils or ethylene bis fatty acid amides), wrinkle-free agents and preferably dispersants, in addition to the dyes and the auxiliary mixture according to the invention.
- anti-foaming agents e.g. silicone oils or ethylene bis fatty acid amides
- wrinkle-free agents e.g. wrinkle-free agents
- dispersants e.g. silicone oils or ethylene bis fatty acid amides
- the dispersants are used primarily to achieve a good fine distribution of the disperse dyes.
- the dispersants generally used for dyeing with disperse dyes can be used.
- the dispersants used are preferably sulfated or phosphated adducts of 15 to 100 moles of ethylene oxide or preferably propylene oxide with polyhydric aliphatic alcohols having 2 to 6 carbon atoms, such as ethylene glycol, glycerol or pentaerythritol or with at least two amino groups or one amino group and one hydroxyl group with amines having 2 up to 9 carbon atoms as well
- Alkyl sulfonates with 10 to 20 carbon atoms in the alkyl chain, alkylbenzenesulfonates with straight-chain or branched alkyl chain with 8 to 20 carbon atoms in the alkyl chain, such as, for example, nonyl- or dodecylbenzenesulfonate, 1,3,5,7-tetramethyloctylbenzenesulfonate or octadecylbenzenesulfonate, such as alkylnaphthalene acid
- Lignin sulfonates polyphosphates and preferably formaldehyde condensation products of aromatic sulfonic acids, formaldehyde and optionally mono- or bifunctional phenols, such as e.g. from cresol, ⁇ -naphtholsulfonic acid and formaldehyde, from benzenesulfonic acid, formaldehyde and naphthalenesulfonic acid, from naphthalenesulfonic acid and formaldehyde or from naphthalenesulfonic acid, dihydroxydiphenyl sulfone and formaldehyde.
- the disodium salt of di- or tri- (6-sulfonaphthyl-2-) methane is preferred.
- anionic dispersants can also be used.
- the anionic dispersants are normally in the form of their alkali metal salts, ammonium salts or amine salts. These dispersants are preferably used in an amount of 0.5 to 8 g / l of liquor.
- the dye baths can also contain a water-soluble alkaline earth metal, aluminum or organic ammonium salt of a mono- or polyvalent aliphatic carboxylic acid or a mono- or polyvalent inorganic acid.
- a water-soluble alkaline earth metal, aluminum or organic ammonium salt of a mono- or polyvalent aliphatic carboxylic acid or a mono- or polyvalent inorganic acid can greatly improve the dispersion stability in the dyebath, depending on the type of dye used, especially when dyeing polyester bobbins with a very high winding density. Dye deposits can thus be prevented or significantly reduced.
- additional salts are water-soluble salts, for example the magnesium, calcium, barium, strontium, aluminum or organic ammonium salts of mono- or polyvalent inorganic acids or mono- or polyvalent aliphatic carboxylic acids such as hydrochloric acid, hydrobromic acid , Hydrofluoric acid, nitric acid, sulfuric acid, phosphoric acid or formic acid, acetic acid and rhodanhydric acid.
- magnesium, calcium, barium, strontium, aluminum or organic ammonium salts of mono- or polyvalent inorganic acids or mono- or polyvalent aliphatic carboxylic acids such as hydrochloric acid, hydrobromic acid , Hydrofluoric acid, nitric acid, sulfuric acid, phosphoric acid or formic acid, acetic acid and rhodanhydric acid.
- Salts are possible, for example: calcium nitrate, magnesium nitrate, aluminum nitrate, calcium chloride, magnesium chloride, magnesium thiocyanate, calcium thiocyanate or organic ammonium chlorides, bromides or iodides, such as, for example, methonium salts (alkane-bis-trimethylammonium salts).
- methonium salts alkane-bis-trimethylammonium salts.
- suitable methonium salts are pentamethonium iodide, decamethonium bromide and in particular hexamethonium chloride.
- These salts are preferably used in an amount of 0.1 to 3 g per liter of dye liquor or 0.2 to 5 percent by weight, based on the fiber material.
- the dyebaths can also contain conventional additives, suitably electrolytes, such as salts, e.g. Sodium sulfate, ammonium sulfate, sodium or ammonium phosphates or polyphosphates, ammonium acetate or sodium acetate and / or acids, e.g. Mineral acids, such as sulfuric acid or phosphoric acid, or organic acids, suitably contain lower aliphatic carboxylic acids, such as formic, acetic, oxalic or citric acid.
- the acids primarily serve to adjust the pH of the liquors used according to the invention, which is generally 4 to 6.5, preferably 4.5 to 6.
- the dyeings are advantageously carried out from an aqueous liquor using the exhaust process.
- the liquor ratio can accordingly be chosen within a wide range, e.g. 1: 3 to 1: 100, preferably 1: 7 to 1:50.
- the temperature at which dyeing is carried out is at least 70 ° C and usually it is not higher than 140 ° C. It is preferably in the range from 80 to 135 ° C.
- Linear polyester fibers and cellulose triacetate fibers are preferably dyed according to the so-called high-temperature process in closed and expediently also pressure-resistant apparatus at temperatures above 100 ° C., preferably between 110 and 135 ° C., under pressure.
- closed vessels for example, circulation apparatuses such as cross-wound or tree dyeing machines, reel runners, jet or drum dyeing machines, jet or muff dyeing machines, paddles or jiggers are suitable.
- Cellulose-2 1/2 acetate fibers are preferably dyed at temperatures of 80-85 ° C.
- the dyeing process can be carried out by either briefly treating the material to be dyed first with the auxiliary mixture and then dyeing it, or preferably treating it simultaneously with the auxiliary mixture and the dye.
- the material to be dyed is preferably allowed to run for 5-10 minutes at 40-80 ° C. in a bath which contains the dye, the auxiliary mixture and, if appropriate, further additives and is adjusted to a pH of 4.5 to 6, the temperature increases within 15 to 30 minutes to 110 to 135 ° C, preferably 125-130 ° C and leaves the dye liquor at this temperature for 15 to 30 minutes, preferably 15 to 20 minutes.
- the dyeings are completed by cooling the dye liquor to 60 to 80 ° C., rinsing the dyeings with water and, if appropriate, cleaning in a conventional manner in an alkaline medium under reductive conditions.
- the dyeings are then rinsed again and dried. Uniform and vivid colorations are obtained on synthetic fiber material, in particular on linear polyester fibers, which are furthermore distinguished by good light fastness and rub fastness.
- the dyeing liquor remains stable and there are no deposits inside the dyeing equipment.
- the process according to the invention is distinguished by a shortened heating phase and by the possibility of adding the dye to the liquor at any temperature.
- the migration of disperse dyes can be improved by using the auxiliary mixture used according to the invention. Due to the improved migration capacity of the dyes, any unevenness in the dipping phase of the dyes in the dwell phase at the final temperature can be compensated for by subsequent migration.
- the dyeing process with the auxiliary mixture according to the invention offers the following advantages: - an uncontrolled heating of the liquor to the dyeing temperature without taking into account the significant or critical dyeing speed; - shading under normal HT conditions thanks to the improved migration of the disperse dyes; - an easy, rational and safe implementation; - a simple correction of incorrect stains, since better compensation takes place; - Rapid achievement of level single and in particular mixed tone dyeings including trichromatic dyeings with good fastness properties, such as fastness to light, rubbing and sublimation, while avoiding streakiness and also under difficult circumstances; - a predominant work without the addition of conventional carriers, dispersants and / or leveling agents; - Achieving level colorations for delicate light and medium tones and especially for deep tones using sublimation-resistant dyes.
- 80 parts of a polyester knitted fabric (225 g / m2) are placed in a 70 ° C. bath containing 1000 parts of water, 2 g / l of ammonium sulfate (anhydrous), a dispersed dye mixture of the composition 0.24 g / l of a dye of the formula 0.28 g / l of a dye of the formula 0.19 g / l of a dye of the formula and 1 g / l of an auxiliary formulation consisting of 60% 2-ethylhexyl 6-phthalimido-hexanoate 20% triethanolamine salt of a mixture of mono- and diester phosphate of an oxyalkylation product with 18 ethylene oxide units of the adduct of 3 moles of styrene with 1 mole of phenol and 20% of an oxyalkylation product of 18 moles of ethylene oxide with 1 mole of an adduct of 3 moles of styrene and 1 mole of phenol contains and is
- the liquor is heated, with constant circulation, to 130 ° C. within 20 minutes and dyed at this temperature for 15 minutes.
- the liquor is then cooled, drained and the goods rinsed and dried.
- a level brown color is obtained with a high dye yield and good fastness properties.
- the usual reductive post-cleaning is not necessary.
- the 2-ethylhexyl 6-phthalimido-hexanoate used is prepared as follows.
- 100 parts of a knitted fabric made of textured polyester fibers are placed in a not fully flooded jet dyeing machine, which contains 1000 parts of 60 ° C warm water, 2 parts of ammonium sulfate, a finely dispersed dye mixture of the composition: 0.5 part of the dye Disperse Yellow 23 CI 26070 0.14 parts of the dye of the formula and 0.23 parts of the dye of the formula and 1g / l of the auxiliary formulation according to Example 1 contains and is adjusted to pH 5 with formic acid. The liquor is then increased to 130 ° C. in the course of 30 minutes and dyed at this temperature for 60 minutes. The liquor is then cooled to 90 ° C., drained and the goods are rinsed and dried without reductive post-cleaning. A level brown coloring with good fastness properties is obtained.
- a knitted fabric made of textured polyester fibers 100 parts are placed in a not fully flooded jet dyeing machine, which contains 1000 parts of 60 ° C warm water, 2 parts of ammonium sulfate, 2.5 parts of the contains finely dispersed dye Disperse Yellow 42 CI 10338 and 1.5 parts of the auxiliary formulation according to Example 1 and is adjusted to pH 5 with formic acid.
- the temperature of the liquor is increased to 130 ° C. in the course of 30 minutes and dyeing is carried out at this temperature for 30 minutes. Then 0.1 part of the dye of the formula introduced into the fleet for nuance, after which the goods are dyed for a further 30 minutes at 130 ° C. The liquor is then cooled and the dyeing rinsed and finished as usual. A level, brilliant green dyeing with good fastness properties is obtained.
- the liquor does not have to be cooled down before adding the nuance. This way of working can save time and energy.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Coloring (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH641/89 | 1989-02-22 | ||
| CH64189 | 1989-02-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0414631A1 true EP0414631A1 (fr) | 1991-02-27 |
Family
ID=4191747
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP90810099A Withdrawn EP0414631A1 (fr) | 1989-02-22 | 1990-02-13 | Mélange d'agents auxiliaires et son utilisation pendant la teinture de matériaux fibreux en polyesters |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0414631A1 (fr) |
| JP (1) | JPH02259173A (fr) |
| AU (1) | AU605705B2 (fr) |
| CA (1) | CA2010406A1 (fr) |
| IL (1) | IL93450A0 (fr) |
| MX (1) | MX172152B (fr) |
| ZA (1) | ZA901308B (fr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0831167A3 (fr) * | 1996-09-20 | 1998-08-12 | Clariant GmbH | Utilisation des aryloxy polyglykoléthers comme agent d'unisson et dispersant |
| US6159836A (en) * | 1994-09-16 | 2000-12-12 | Stmicroelectronics, Inc. | Method for forming programmable contact structure |
| WO2006100244A3 (fr) * | 2005-03-22 | 2007-01-11 | Basf Ag | Procede pour teindre des textiles avec un colorant de cuve |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0382138B1 (fr) * | 1989-02-08 | 1994-08-24 | Ciba-Geigy Ag | Mélange d'adjuvants et son utilisation pour la teinture de matières fibreuses synthétiques |
| DE59104446D1 (de) * | 1990-02-14 | 1995-03-16 | Ciba Geigy Ag | Verfahren zum Färben von Wolle mit Reaktivfarbstoffen. |
| JP5230338B2 (ja) * | 2008-10-07 | 2013-07-10 | 第一工業製薬株式会社 | ポリエステル繊維用均染剤 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1346622A (fr) * | 1963-01-24 | 1963-12-20 | Bayer Ag | Agents d'unisson |
| GB1193948A (en) * | 1968-04-20 | 1970-06-03 | Bayer Ag | Printing and Dyeing Process |
| GB2001352A (en) * | 1977-07-20 | 1979-01-31 | Bayer Ag | Aqueous dyestuff dispersions |
| EP0033715A1 (fr) * | 1980-01-31 | 1981-08-12 | Ciba-Geigy Ag | Adjuvant et son utilisation pour la teinture ou l'azurage optique de matières textiles en polyester |
| EP0177111A2 (fr) * | 1984-10-01 | 1986-04-09 | Toray Industries, Inc. | Méthode de traitement d'un textile |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS602433B2 (ja) * | 1979-04-28 | 1985-01-21 | 一方社油脂工業株式会社 | ポリエステル系合成繊維の染色方法 |
-
1990
- 1990-02-13 EP EP90810099A patent/EP0414631A1/fr not_active Withdrawn
- 1990-02-20 IL IL93450A patent/IL93450A0/xx not_active IP Right Cessation
- 1990-02-20 CA CA002010406A patent/CA2010406A1/fr not_active Abandoned
- 1990-02-20 MX MX019586A patent/MX172152B/es unknown
- 1990-02-21 ZA ZA901308A patent/ZA901308B/xx unknown
- 1990-02-21 AU AU50025/90A patent/AU605705B2/en not_active Ceased
- 1990-02-22 JP JP2039904A patent/JPH02259173A/ja active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1346622A (fr) * | 1963-01-24 | 1963-12-20 | Bayer Ag | Agents d'unisson |
| GB1193948A (en) * | 1968-04-20 | 1970-06-03 | Bayer Ag | Printing and Dyeing Process |
| GB2001352A (en) * | 1977-07-20 | 1979-01-31 | Bayer Ag | Aqueous dyestuff dispersions |
| EP0033715A1 (fr) * | 1980-01-31 | 1981-08-12 | Ciba-Geigy Ag | Adjuvant et son utilisation pour la teinture ou l'azurage optique de matières textiles en polyester |
| EP0177111A2 (fr) * | 1984-10-01 | 1986-04-09 | Toray Industries, Inc. | Méthode de traitement d'un textile |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6159836A (en) * | 1994-09-16 | 2000-12-12 | Stmicroelectronics, Inc. | Method for forming programmable contact structure |
| EP0831167A3 (fr) * | 1996-09-20 | 1998-08-12 | Clariant GmbH | Utilisation des aryloxy polyglykoléthers comme agent d'unisson et dispersant |
| WO2006100244A3 (fr) * | 2005-03-22 | 2007-01-11 | Basf Ag | Procede pour teindre des textiles avec un colorant de cuve |
Also Published As
| Publication number | Publication date |
|---|---|
| AU5002590A (en) | 1990-08-30 |
| ZA901308B (en) | 1990-10-31 |
| JPH02259173A (ja) | 1990-10-19 |
| AU605705B2 (en) | 1991-01-17 |
| MX172152B (es) | 1993-12-06 |
| CA2010406A1 (fr) | 1990-08-22 |
| IL93450A0 (en) | 1990-11-29 |
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