EP0057398A2 - Procédé pour le post-traitement de teintures de matière fibreuse rendue résistant au feutrage par un apprêt - Google Patents
Procédé pour le post-traitement de teintures de matière fibreuse rendue résistant au feutrage par un apprêt Download PDFInfo
- Publication number
- EP0057398A2 EP0057398A2 EP82100485A EP82100485A EP0057398A2 EP 0057398 A2 EP0057398 A2 EP 0057398A2 EP 82100485 A EP82100485 A EP 82100485A EP 82100485 A EP82100485 A EP 82100485A EP 0057398 A2 EP0057398 A2 EP 0057398A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- polyether
- der
- hydroxyalkylamines
- alkyl
- parts
- 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
- 239000002657 fibrous material Substances 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 title claims description 17
- 229920000570 polyether Polymers 0.000 claims abstract description 80
- -1 aromatic radical Chemical class 0.000 claims abstract description 31
- 238000005956 quaternization reaction Methods 0.000 claims abstract description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000009833 condensation Methods 0.000 claims abstract description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 6
- 229920005862 polyol Polymers 0.000 claims abstract description 6
- 150000003077 polyols Chemical class 0.000 claims abstract description 6
- 102000011782 Keratins Human genes 0.000 claims abstract description 5
- 108010076876 Keratins Proteins 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
- 150000005840 aryl radicals Chemical class 0.000 claims abstract description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 57
- 210000002268 wool Anatomy 0.000 claims description 7
- 230000005494 condensation Effects 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 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
- 125000002091 cationic group Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000004043 dyeing Methods 0.000 abstract description 17
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 235000020357 syrup Nutrition 0.000 description 13
- 125000003277 amino group Chemical group 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000006188 syrup Substances 0.000 description 10
- 239000000975 dye Substances 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- 239000000470 constituent Substances 0.000 description 7
- HHPDFYDITNAMAM-UHFFFAOYSA-N 2-[cyclohexyl(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(CCO)C1CCCCC1 HHPDFYDITNAMAM-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 150000004072 triols Chemical class 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- UUAGPGQUHZVJBQ-UHFFFAOYSA-N Bisphenol A bis(2-hydroxyethyl)ether Chemical compound C=1C=C(OCCO)C=CC=1C(C)(C)C1=CC=C(OCCO)C=C1 UUAGPGQUHZVJBQ-UHFFFAOYSA-N 0.000 description 3
- 101100476962 Drosophila melanogaster Sirup gene Proteins 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- QAVIDTFGPNJCCX-UHFFFAOYSA-N n'-(2-aminoethyl)ethane-1,2-diamine;2-(chloromethyl)oxirane;hexanedioic acid Chemical compound ClCC1CO1.NCCNCCN.OC(=O)CCCCC(O)=O QAVIDTFGPNJCCX-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- XKQMKMVTDKYWOX-UHFFFAOYSA-N 1-[2-hydroxypropyl(methyl)amino]propan-2-ol Chemical compound CC(O)CN(C)CC(C)O XKQMKMVTDKYWOX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- BWVAOONFBYYRHY-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(CO)C=C1 BWVAOONFBYYRHY-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 210000004243 sweat Anatomy 0.000 description 2
- 125000001302 tertiary amino group Chemical group 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000005023 xylyl group Chemical group 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- BFIAIMMAHAIVFT-UHFFFAOYSA-N 1-[bis(2-hydroxybutyl)amino]butan-2-ol Chemical compound CCC(O)CN(CC(O)CC)CC(O)CC BFIAIMMAHAIVFT-UHFFFAOYSA-N 0.000 description 1
- IEXYKOLCMBHVMG-UHFFFAOYSA-N 2-[4-tert-butyl-n-(2-hydroxyethyl)anilino]ethanol Chemical compound CC(C)(C)C1=CC=C(N(CCO)CCO)C=C1 IEXYKOLCMBHVMG-UHFFFAOYSA-N 0.000 description 1
- MIZIOHLLYXVEHJ-UHFFFAOYSA-N 2-[benzyl(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(CCO)CC1=CC=CC=C1 MIZIOHLLYXVEHJ-UHFFFAOYSA-N 0.000 description 1
- VMNDRLYLEVCGAG-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)-3-methylanilino]ethanol Chemical compound CC1=CC=CC(N(CCO)CCO)=C1 VMNDRLYLEVCGAG-UHFFFAOYSA-N 0.000 description 1
- OJPDDQSCZGTACX-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)anilino]ethanol Chemical compound OCCN(CCO)C1=CC=CC=C1 OJPDDQSCZGTACX-UHFFFAOYSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical class CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000000853 cresyl group Chemical group C1(=CC=C(C=C1)C)* 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000002704 decyl group Chemical group [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])* 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- GDNCXORZAMVMIW-UHFFFAOYSA-N dodecane Chemical compound [CH2]CCCCCCCCCCC GDNCXORZAMVMIW-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 239000000434 metal complex dye Substances 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-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
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000000985 reactive dye Substances 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
- 238000005507 spraying Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 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
- D06P1/60—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
- D06P1/607—Nitrogen-containing polyethers or their quaternary derivatives
-
- 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
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/02—After-treatment
- D06P5/04—After-treatment with organic compounds
- D06P5/06—After-treatment with organic compounds containing nitrogen
Definitions
- R 1 and R 2 the methyl, ethyl, propyl, n - butyl and sec-butyl radicals may be mentioned as C 1 -C 4 alkyl radicals.
- R is C 1 -C 4 alkyl or cyclohexyl and R 1 and R 2 are hydrogen or methyl.
- Preferred cycloaliphatic, araliphatic and aromatic radicals A are derived from the radicals mentioned as examples under R.
- the average molecular weight of the polyethers to be used according to the invention should be between 500 and 20,000, preferably 1,000 to 15,000.
- the polyethers to be used according to the invention are linear or slightly branched poly ether.
- the linear polyethers can be obtained by known processes by condensation of N-2-hydroxyalkylamines of the formula I in the presence of acidic catalysts, for example H 3 PO 3 , at elevated temperatures, for example 150-280 ° C.
- acidic catalysts for example H 3 PO 3
- the diols containing tertiary amino groups are condensed together with triols containing tertiary amino groups, ie N-2-hydroxyalkylamines of the formula I in which R represents one of the ⁇ -hydroxyalkyl groups indicated.
- the amount of triols in the condensation mixture should not be more than 20 percent by weight, preferably 2-15 percent by weight.
- the polyethers to be used according to the invention are known, for example, from GB-PS 1 107 819 and DE-OS 2 060 572.
- ß-hydroxyalkylamines of the formula (I) which may be mentioned are the N-di- (2-hydroxyalkyl) amines as used in the addition of ethylene, propylene and butylene oxide or mixtures of these alkylene oxides to primary aliphatic, cycloaliphatic, araliphatic and aromatic amines are formed.
- N-bi- (2-hydroxyalkyl) amines are, for example: N, N-bis (2-hydroxyethyl) -N-methylamine, N, N-bis-L2-hydroxypropyl- (117-methylamine, N, N -Bis [2-hydroxy-butyl- (1)] methylamine, N, N-bis (2-hydroxyethyl) -N-isopropyl amine, N, N-bis- (2-hydroxyethyl) -Nn-butylamine, N, N-bis-L2-hydroxypropyl- (117-N-sec.-butylamine, N, N-bis- (2-hydroxyethyl) - cyclohexylamine; N, N-bis (2-hydroxyethyl) -N-benzylamine, N, N-bis (2-hydroxyethyl) -N- (4-methylbenzyl) amine, N, N-bis (2-hydroxyethyl ) -aniline, N, N, N-
- Triethanolamine, triisopropanolamine and tributanolamine may be mentioned in particular as representatives of the triols used to prepare the branched polyethers.
- the quaternization is carried out in a manner known per se by reacting the polyethers optionally dissolved or suspended in alcohol or alcohol / water mixtures with known alkylating agents, such as dimethyl sulfate or diethyl sulfate; p-toluenesulfonic acid alkyl esters, e.g. p-toluenesulfonic acid methyl ester; Alkyl halides, e.g. Methyl iodide or ethyl bromide; Chloroacetamide, halocarboxylic acid salts, halocarboxylic acid esters, alkanesulfones or benzyl chloride.
- alkylating agents such as dimethyl sulfate or diethyl sulfate; p-toluenesulfonic acid alkyl esters, e.g. p-toluenesulfonic acid methyl ester; Alky
- the amounts in which the polyethers to be used according to the invention are added to the aftertreatment baths can vary within wide limits. In general, an addition of 0.05-2%, preferably 0.1-1%, by weight, based on the weight of the fiber materials, has proven useful.
- the aftertreatment of the textile material is expediently carried out in such a way that the material which has already been finished and dyed in a felt-free manner is introduced into an aqueous liquor which contains the polyethers to be used according to the invention and has a pH between 6 and 9, preferably 7- 8.
- the temperature of the treatment bath is raised to 50-80 ° C. in the course of 20-30 minutes and left there for 5-15 minutes.
- the material is then rinsed with cold water, dewatered and dried.
- the aftertreatment can, as described above, be carried out using the pull-out method or continuously or semi-continuously by padding or spraying with subsequent exposure to heat.
- the felt-free finish can be done by various known methods, e.g. according to the HERCOSETT process. These processes, also known as superwashing equipment, are chlorination processes and. processes in which the fiber is coated with a resin, e.g. a polyurethane, polyacrylic, melamine, polyalkyleneimine / epichlorohydrin or polyamide / epichlorohydrin resin is treated.
- a resin e.g. a polyurethane, polyacrylic, melamine, polyalkyleneimine / epichlorohydrin or polyamide / epichlorohydrin resin is treated.
- polyethers to be used according to the invention can be increased from case to case by using non-ionic, cation-active or amphoteric, surface-active substances.
- non-ionic, cation-active or amphoteric, surface-active substances are, for example, ethylene and / or propylene oxide adducts of fatty amines, which can be quaternized and / or sulfated. They are known to those skilled in the art as leveling aids for wool dyes.
- the amount of such products used is 50-100, preferably 70-80%, the amount of the polyethers to be used according to the invention.
- the fastness properties in particular the wet fastnesses such as sweat fastness according to IWS-TM 174 (test method for alkaline sweat fastness) and the wash fastness according to IWS-TM 193 (test method for fastness to washing) are considerably improved.
- Suitable dyes are the dyes usually used for dyeing keratin-containing fibers, e.g. Acid dyes, 1: 2 metal complex dyes which may contain water-solubilizing groups such as sulfonic acid or carboxylic acid groups or also sulfonamide or alkyl sulfone residues, and reactive dyes. They are described in more detail in the Color Index. Dyes of this type, which otherwise have good fastness properties, result in less real dyeings on materials which have been treated with keratin and contain no felt, particularly in the case of deep shades.
- Polyether C was prepared analogously to polyether B, except that only 54 parts of dimethyl sulfate (0.5 mol of dimethyl sulfate per mole of basic amino group) were used instead of the 82 parts of dimethyl sulfate for the quaternization.
- the quaternization product remains as a yellow water-soluble syrup.
- the polyether can be represented by the formula describe.
- Yarns made of wool which have been equipped with HERCOSETT 57 "Superwash” chlorination and treatment with an adipic acid / diethylenetriamine-epichlorohydrin reaction product) are treated in a liquor ratio of 1:20 at room temperature for 15 minutes with a dye liquor which is in liters contains.
- the dyebath is heated to boiling within 60 minutes and dyed at this temperature for 60 minutes.
- the HERCOSETT-finished wool yarns are dyed as described in Example 1 and then treated at 50 ° C. for 15 minutes with a liquor in liters contains. The dyeing is then rinsed, dewatered and dried.
- Wool ridges previously equipped with HERCOSETT 57 were placed in a liquor ratio of 1:10 at room temperature in a dye bath in liters contains. The dye liquor is then heated to boiling within 60 minutes and kept at this temperature for 60 minutes. After rinsing, the dyeing is aftertreated at 50 ° C for 15 minutes with a liquor in liters contains. The dyeing is then rinsed, dewatered and dried. The staining has a significantly increased level of authenticity.
- Wool yarn finished on bobbins and equipped with a felt-free finish is used in a liquor ratio of 1:15, as in Example 1 described, colored, but using a dye liquor, which is in liters contains.
- Wool yarn skeins equipped with HERCOSETT 57 are placed at room temperature in a liquor ratio of 1:25 in a dyeing liquor, in liters contains. Both dyeing and post-treatment are carried out as described in Example 1, with the difference that 0.14 g of polyether K is used in the after-treatment instead of the polyether B.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Coloring (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3103815 | 1981-02-04 | ||
| DE19813103815 DE3103815A1 (de) | 1981-02-04 | 1981-02-04 | Verfahren zur nachbehandlung von gefaerbten, filzfrei ausgeruesteten fasermaterialien |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0057398A2 true EP0057398A2 (fr) | 1982-08-11 |
| EP0057398A3 EP0057398A3 (en) | 1982-08-25 |
| EP0057398B1 EP0057398B1 (fr) | 1984-06-13 |
Family
ID=6124040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP82100485A Expired EP0057398B1 (fr) | 1981-02-04 | 1982-01-25 | Procédé pour le post-traitement de teintures de matière fibreuse rendue résistant au feutrage par un apprêt |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0057398B1 (fr) |
| JP (1) | JPS57149561A (fr) |
| AU (1) | AU540907B2 (fr) |
| DE (2) | DE3103815A1 (fr) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4629468A (en) * | 1984-05-05 | 1986-12-16 | Bayer Aktiengesellschaft | Process for treating cellulosic fibre material |
| EP0432686A1 (fr) * | 1989-12-11 | 1991-06-19 | Nihon Surfactant Kogyo K.K. | Adjuvants de teinture pour cuir |
| WO2001041718A1 (fr) * | 1999-12-08 | 2001-06-14 | L'oreal | Composition de teinture directe pour fibres keratiniques comprenant un polymere epaississant a squelette aminoplaste-ether |
| WO2009060060A1 (fr) * | 2007-11-09 | 2009-05-14 | Basf Se | Polyalcanolamines alcoxylés |
| EP2199315A1 (fr) | 2008-12-19 | 2010-06-23 | Basf Se | Composition comprenant un agent égalisant pour électrodeposition |
| US8097577B2 (en) | 2007-11-09 | 2012-01-17 | The Procter & Gamble Company | Cleaning compositions with alkoxylated polyalkanolamines |
| WO2022129368A1 (fr) | 2020-12-16 | 2022-06-23 | Basf Se | N-(hydroxyalkyl)amine polymère alcoxylée utilisée comme agents mouillants et comme constituant de compositions antimousse |
| EP4067410A1 (fr) | 2021-03-29 | 2022-10-05 | Evonik Operations GmbH | Utilisation de dérivés d'acide carbonique à base de polyamine et/ou de polyalkanolamine dans des dispersions aqueuses de polyuréthane |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1469737A1 (de) * | 1965-09-30 | 1969-01-02 | Bayer Ag | Verfahren zum Faerben von Polyacrylnitrilgebilden |
| BE710180A (fr) * | 1967-02-01 | 1968-05-30 | ||
| DE2060572A1 (de) * | 1970-12-09 | 1972-06-22 | Bayer Ag | Verfahren zum Herabsetzen der Farbstoffaffinitaet von Fasermaterialien aus Polyacrylnitril |
| CH589168B5 (fr) * | 1975-04-14 | 1977-06-30 | Ciba Geigy Ag | |
| FR2377474A1 (fr) * | 1977-01-18 | 1978-08-11 | Ciba Geigy Ag | Procede pour le post-traitement de teintures de matiere fibreuse rendue resistante au feutrage par un appret |
| JPS5571884A (en) * | 1978-11-27 | 1980-05-30 | Nippon Senka Kogyo Kk | Enhancing of dye fastness |
| DE2949510A1 (de) * | 1978-12-18 | 1980-06-26 | Sandoz Ag | Verfahren zur herstellung von gefaerbten, filzfest ausgeruesteten, textilen materialien |
| JPS55152881A (en) * | 1979-05-11 | 1980-11-28 | Nitto Boseki Co Ltd | Enhancement of dye fastness |
-
1981
- 1981-02-04 DE DE19813103815 patent/DE3103815A1/de not_active Withdrawn
-
1982
- 1982-01-20 AU AU79649/82A patent/AU540907B2/en not_active Ceased
- 1982-01-25 EP EP82100485A patent/EP0057398B1/fr not_active Expired
- 1982-01-25 DE DE8282100485T patent/DE3260219D1/de not_active Expired
- 1982-02-02 JP JP57014412A patent/JPS57149561A/ja active Pending
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4629468A (en) * | 1984-05-05 | 1986-12-16 | Bayer Aktiengesellschaft | Process for treating cellulosic fibre material |
| EP0160872A3 (en) * | 1984-05-05 | 1987-05-20 | Bayer Ag | Process for treating cellulosic fibrous materials |
| EP0432686A1 (fr) * | 1989-12-11 | 1991-06-19 | Nihon Surfactant Kogyo K.K. | Adjuvants de teinture pour cuir |
| WO2001041718A1 (fr) * | 1999-12-08 | 2001-06-14 | L'oreal | Composition de teinture directe pour fibres keratiniques comprenant un polymere epaississant a squelette aminoplaste-ether |
| FR2802090A1 (fr) * | 1999-12-08 | 2001-06-15 | Oreal | Composition de teinture directe pour fibres keratiniques comprenant un polymere epaississant a squelette aminoplaste-ether |
| US6916344B1 (en) | 1999-12-08 | 2005-07-12 | L'oreal S.A. | Direct dyeing composition for keratinic fibers containing a thickening polymer with an ether plastic skeleton |
| WO2009060060A1 (fr) * | 2007-11-09 | 2009-05-14 | Basf Se | Polyalcanolamines alcoxylés |
| US8097577B2 (en) | 2007-11-09 | 2012-01-17 | The Procter & Gamble Company | Cleaning compositions with alkoxylated polyalkanolamines |
| US8129326B2 (en) | 2007-11-09 | 2012-03-06 | Basf Se | Alkoxylated polyalkanolamines |
| EP2199315A1 (fr) | 2008-12-19 | 2010-06-23 | Basf Se | Composition comprenant un agent égalisant pour électrodeposition |
| US9011666B2 (en) | 2008-12-19 | 2015-04-21 | Basf Se | Composition for metal electroplating comprising leveling agent |
| WO2022129368A1 (fr) | 2020-12-16 | 2022-06-23 | Basf Se | N-(hydroxyalkyl)amine polymère alcoxylée utilisée comme agents mouillants et comme constituant de compositions antimousse |
| EP4067410A1 (fr) | 2021-03-29 | 2022-10-05 | Evonik Operations GmbH | Utilisation de dérivés d'acide carbonique à base de polyamine et/ou de polyalkanolamine dans des dispersions aqueuses de polyuréthane |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0057398A3 (en) | 1982-08-25 |
| AU540907B2 (en) | 1984-12-06 |
| DE3103815A1 (de) | 1982-09-09 |
| DE3260219D1 (en) | 1984-07-19 |
| JPS57149561A (en) | 1982-09-16 |
| EP0057398B1 (fr) | 1984-06-13 |
| AU7964982A (en) | 1982-08-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0089004B1 (fr) | Procédé de teinture de matière fibreuse de polyamides naturels | |
| DE2633615C3 (de) | Verfahren zum Färben von synthetischen Polyamid-Fasermaterialien | |
| EP0225281B1 (fr) | Combinaison d'agents auxiliaires et son utilisation comme agent d'ennoblissement | |
| DE1419042A1 (de) | Verfahren zur Ausruestung von geformten Gebilden | |
| DE1940178A1 (de) | AEthansulfonsaeurederivate | |
| DE2645954A1 (de) | Verfahren zur behandlung von faserfoermigen materialien | |
| EP0057398B1 (fr) | Procédé pour le post-traitement de teintures de matière fibreuse rendue résistant au feutrage par un apprêt | |
| EP0160872B1 (fr) | Procédé de traitement de matières fibreuses cellulosiques | |
| DE1619542B1 (de) | Verfahren zum Färben von stickstoffhaltigen Fasermaterialien | |
| EP0342439B1 (fr) | Procédé de posttraitement de matériaux textiles teints | |
| EP0163608B1 (fr) | Procédé de teinture de matières fibreuses en polyamides naturelles ou synthétiques avec des colorants à complexes métallifères 1:1 | |
| DE1921827A1 (de) | Verfahren zur Erzeugung von Faerbungen auf Fasermaterial aus polymerem oder copolymerem Acrylnitril | |
| DE3330120C2 (fr) | ||
| CH629368A5 (en) | Pesticide | |
| DE1469657C3 (de) | Verfahren zum Färben von ungewobener Wolle und zur Durchführung des Verfahrens geeignete Präparate | |
| EP0203890B1 (fr) | Procédé de teinture de matières en polyamides naturels avec des mélanges de colorants | |
| EP0487771B1 (fr) | Emploi de dialkylmonoamines alcoxylées pour réserve de teintures anioniques de produits textiles polyamides | |
| DE4131926A1 (de) | Verfahren zum nachbehandeln von mit anionischen farbstoffen gefaerbten substraten | |
| EP0415279B1 (fr) | Utilisation d'amides d'acides gras éthoxylés comme adoucissants | |
| DE1288066B (fr) | ||
| EP0013540A1 (fr) | Procédé de teinture et d'impression de matières fibreuses avec des sels d'ammonium quaternaire polymères comme agents auxiliaires | |
| EP0305858B1 (fr) | Procédé de teinture de fibres en polyamide | |
| DE2841800C2 (fr) | ||
| CH641874A5 (de) | Luftverdichtende, direkteinspritzende brennkraftmaschine. | |
| DE2744021C3 (de) | Konzentriertes wäßriges Mittel zum Antistatischmachen von synthetischen Fasermaterialien und dessen Verwendung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| PUAL | Search report despatched |
Free format text: ORIGINAL CODE: 0009013 |
|
| 17P | Request for examination filed |
Effective date: 19820125 |
|
| AK | Designated contracting states |
Designated state(s): DE FR GB IT |
|
| AK | Designated contracting states |
Designated state(s): DE FR GB IT |
|
| ITF | It: translation for a ep patent filed | ||
| GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
| AK | Designated contracting states |
Designated state(s): DE FR GB IT |
|
| REF | Corresponds to: |
Ref document number: 3260219 Country of ref document: DE Date of ref document: 19840719 |
|
| ET | Fr: translation filed | ||
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: DE Payment date: 19841218 Year of fee payment: 4 |
|
| PLBE | No opposition filed within time limit |
Free format text: ORIGINAL CODE: 0009261 |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT |
|
| 26N | No opposition filed | ||
| GBPC | Gb: european patent ceased through non-payment of renewal fee | ||
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: FR Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 19880930 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: DE Effective date: 19881001 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: GB Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 19881121 |
|
| REG | Reference to a national code |
Ref country code: FR Ref legal event code: ST |