US3391985A - Process for pad-dyeing and printing wool and synthetic textile fibers in carrier compositions - Google Patents
Process for pad-dyeing and printing wool and synthetic textile fibers in carrier compositions Download PDFInfo
- Publication number
- US3391985A US3391985A US409349A US40934964A US3391985A US 3391985 A US3391985 A US 3391985A US 409349 A US409349 A US 409349A US 40934964 A US40934964 A US 40934964A US 3391985 A US3391985 A US 3391985A
- Authority
- US
- United States
- Prior art keywords
- parts
- carbon atoms
- sulfated
- fibers
- liquor
- 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.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims description 137
- 239000000835 fiber Substances 0.000 title claims description 89
- 238000000034 method Methods 0.000 title claims description 81
- 230000008569 process Effects 0.000 title claims description 36
- 238000009980 pad dyeing Methods 0.000 title claims description 7
- 210000002268 wool Anatomy 0.000 title description 44
- 238000007639 printing Methods 0.000 title description 7
- 229920002994 synthetic fiber Polymers 0.000 title 1
- 239000004758 synthetic textile Substances 0.000 title 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 140
- 239000000975 dye Substances 0.000 claims description 55
- -1 POLYETHYLENE Polymers 0.000 claims description 35
- 150000001408 amides Chemical class 0.000 claims description 28
- 239000002562 thickening agent Substances 0.000 claims description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 239000007859 condensation product Substances 0.000 claims description 20
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 19
- 239000004952 Polyamide Substances 0.000 claims description 18
- 229920002647 polyamide Polymers 0.000 claims description 17
- 229920000728 polyester Polymers 0.000 claims description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims description 10
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 10
- 239000004753 textile Substances 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 7
- 150000001340 alkali metals Chemical class 0.000 claims description 7
- 239000004615 ingredient Substances 0.000 claims description 7
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 148
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- 239000000243 solution Substances 0.000 description 94
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- 235000014113 dietary fatty acids Nutrition 0.000 description 63
- 239000000194 fatty acid Substances 0.000 description 63
- 229930195729 fatty acid Natural products 0.000 description 63
- 150000004665 fatty acids Chemical class 0.000 description 61
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- 125000004432 carbon atom Chemical group C* 0.000 description 58
- 235000019864 coconut oil Nutrition 0.000 description 54
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- 239000002253 acid Substances 0.000 description 34
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 31
- 229910052804 chromium Inorganic materials 0.000 description 29
- 239000011651 chromium Substances 0.000 description 28
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 26
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 25
- 230000000694 effects Effects 0.000 description 24
- 239000007864 aqueous solution Substances 0.000 description 22
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 22
- 229920006395 saturated elastomer Polymers 0.000 description 22
- 238000003756 stirring Methods 0.000 description 22
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 21
- 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 20
- 235000019253 formic acid Nutrition 0.000 description 20
- NISAHDHKGPWBEM-UHFFFAOYSA-N 2-(4-nonylphenoxy)acetic acid Chemical compound CCCCCCCCCC1=CC=C(OCC(O)=O)C=C1 NISAHDHKGPWBEM-UHFFFAOYSA-N 0.000 description 19
- 125000000217 alkyl group Chemical group 0.000 description 19
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 19
- PIWQVBDRRFMUIB-UHFFFAOYSA-N 2-phenoxyundecanoic acid Chemical class CCCCCCCCCC(C(O)=O)OC1=CC=CC=C1 PIWQVBDRRFMUIB-UHFFFAOYSA-N 0.000 description 18
- 238000010025 steaming Methods 0.000 description 17
- 150000003863 ammonium salts Chemical class 0.000 description 15
- 244000046052 Phaseolus vulgaris Species 0.000 description 12
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 235000013312 flour Nutrition 0.000 description 11
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- 125000005210 alkyl ammonium group Chemical group 0.000 description 9
- 239000000969 carrier Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 9
- 229920002972 Acrylic fiber Polymers 0.000 description 8
- 229920000926 Galactomannan Polymers 0.000 description 8
- 150000002170 ethers Chemical class 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- OMDQUFIYNPYJFM-XKDAHURESA-N (2r,3r,4s,5r,6s)-2-(hydroxymethyl)-6-[[(2r,3s,4r,5s,6r)-4,5,6-trihydroxy-3-[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O[C@H]2[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@H](O)[C@H](O)O1 OMDQUFIYNPYJFM-XKDAHURESA-N 0.000 description 7
- 240000008886 Ceratonia siliqua Species 0.000 description 7
- 235000013912 Ceratonia siliqua Nutrition 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000000661 sodium alginate Substances 0.000 description 7
- 229940005550 sodium alginate Drugs 0.000 description 7
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 7
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 6
- 150000000218 1-tetradecanols Chemical class 0.000 description 5
- NHRQAWMMMLTYNZ-UHFFFAOYSA-N 3-(2-nonylphenoxy)propane-1,2-diol Chemical class CCCCCCCCCC1=CC=CC=C1OCC(O)CO NHRQAWMMMLTYNZ-UHFFFAOYSA-N 0.000 description 5
- 229920002284 Cellulose triacetate Polymers 0.000 description 5
- 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 5
- 239000004677 Nylon Substances 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 238000004090 dissolution Methods 0.000 description 5
- 229920001778 nylon Polymers 0.000 description 5
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 5
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 description 5
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 4
- ULUIMLJNTCECJU-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonate;hydron Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1O ULUIMLJNTCECJU-UHFFFAOYSA-N 0.000 description 4
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
- 229920002292 Nylon 6 Polymers 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 4
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 4
- 150000004056 anthraquinones Chemical class 0.000 description 4
- SXYCCJAPZKHOLS-UHFFFAOYSA-N chembl2008674 Chemical compound [O-][N+](=O)C1=CC=C2C(N=NC3=C4C=CC=CC4=CC=C3O)=C(O)C=C(S(O)(=O)=O)C2=C1 SXYCCJAPZKHOLS-UHFFFAOYSA-N 0.000 description 4
- 229910021563 chromium fluoride Inorganic materials 0.000 description 4
- 239000008395 clarifying agent Substances 0.000 description 4
- 229910017052 cobalt Inorganic materials 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N methyl undecanoic acid Natural products CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- RQNVIKXOOKXAJQ-UHFFFAOYSA-N naphthazarin Chemical compound O=C1C=CC(=O)C2=C1C(O)=CC=C2O RQNVIKXOOKXAJQ-UHFFFAOYSA-N 0.000 description 4
- 238000005191 phase separation Methods 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 235000010413 sodium alginate Nutrition 0.000 description 4
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 4
- 240000007817 Olea europaea Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
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- 238000011001 backwashing Methods 0.000 description 3
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- FPVGTPBMTFTMRT-UHFFFAOYSA-L disodium;2-amino-5-[(4-sulfonatophenyl)diazenyl]benzenesulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-UHFFFAOYSA-L 0.000 description 3
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- DOPJTDJKZNWLRB-UHFFFAOYSA-N 2-Amino-5-nitrophenol Chemical compound NC1=CC=C([N+]([O-])=O)C=C1O DOPJTDJKZNWLRB-UHFFFAOYSA-N 0.000 description 2
- YVPCXPUYVWWSFM-UHFFFAOYSA-N 4-amino-3-hydroxy-7-nitronaphthalene-1-sulfonic acid;naphthalen-2-ol Chemical compound C1=CC=CC2=CC(O)=CC=C21.[O-][N+](=O)C1=CC=C2C(N)=C(O)C=C(S(O)(=O)=O)C2=C1 YVPCXPUYVWWSFM-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
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- UHUFTBALEZWWIH-UHFFFAOYSA-N myristic aldehyde Natural products CCCCCCCCCCCCCC=O UHUFTBALEZWWIH-UHFFFAOYSA-N 0.000 description 2
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
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- 229910052700 potassium Inorganic materials 0.000 description 2
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- 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 2
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- DXRWYIKGBIPGAG-UHFFFAOYSA-N sodium 3-hydroxy-4-[(2-hydroxynaphthalen-1-yl)diazenyl]-7-nitronaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(=C1)C=CC(=C2N=NC3=C4C=CC(=CC4=C(C=C3O)S(=O)(=O)O)[N+](=O)[O-])O.[Na+] DXRWYIKGBIPGAG-UHFFFAOYSA-N 0.000 description 1
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- WBPFVHVTNAEJCX-UHFFFAOYSA-M sodium;2-[[4-(dimethylamino)phenyl]-(4-dimethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)methyl]-5-[ethyl-[(3-sulfonatophenyl)methyl]amino]benzenesulfonate Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(C)C)C(S([O-])(=O)=O)=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 WBPFVHVTNAEJCX-UHFFFAOYSA-M 0.000 description 1
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- NMGNJWORLGLLHQ-UHFFFAOYSA-M sulcofuron-sodium Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1NC(=O)NC1=CC=C(Cl)C(Cl)=C1 NMGNJWORLGLLHQ-UHFFFAOYSA-M 0.000 description 1
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Classifications
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- 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)
- D06P1/6496—Condensation products from carboxylic acids and hydroxyalkyl amine (Kritchewski bases)
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06B—TREATING TEXTILE MATERIALS USING LIQUIDS, GASES OR VAPOURS
- D06B17/00—Storing of textile materials in association with the treatment of the materials by liquids, gases or vapours
- D06B17/02—Storing of textile materials in association with the treatment of the materials by liquids, gases or vapours in superimposed, i.e. stack-packed, form; J-boxes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06B—TREATING TEXTILE MATERIALS USING LIQUIDS, GASES OR VAPOURS
- D06B3/00—Passing of textile materials through liquids, gases or vapours to effect treatment, e.g. washing, dyeing, bleaching, sizing, impregnating
- D06B3/10—Passing of textile materials through liquids, gases or vapours to effect treatment, e.g. washing, dyeing, bleaching, sizing, impregnating of fabrics
- D06B3/16—Passing of textile materials through liquids, gases or vapours to effect treatment, e.g. washing, dyeing, bleaching, sizing, impregnating of fabrics in superimposed, i.e. stack-packed, form
-
- 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
-
- 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
-
- 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
- D06P1/62—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 with sulfate, sulfonate, sulfenic or sulfinic groups
- D06P1/621—Compounds without nitrogen
- D06P1/627—Sulfates
-
- 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
- D06P1/62—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 with sulfate, sulfonate, sulfenic or sulfinic groups
- D06P1/628—Compounds containing nitrogen
-
- 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
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06B—TREATING TEXTILE MATERIALS USING LIQUIDS, GASES OR VAPOURS
- D06B2700/00—Treating of textile materials, e.g. bleaching, dyeing, mercerising, impregnating, washing; Fulling of fabrics
- D06B2700/09—Apparatus for passing open width fabrics through bleaching, washing or dyeing liquid
- D06B2700/095—Apparatus for passing open width fabrics through bleaching, washing or dyeing liquid for continuous treatment of open width fabrics, in which the fabric is guided without tension, e.g. superimposed or festooned, in order to extend the duration of treatment
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/904—Mixed anionic and nonionic emulsifiers for dyeing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/907—Nonionic emulsifiers for dyeing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/908—Anionic emulsifiers for dyeing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
Definitions
- This invention relates to a process for the continuous pad-dyeing of natural and synthetic polyamide and other textile fibers, as well as pad liquors and novel carriers suitable for use in this process.
- polyamide fibers can be pad-dyed by continuous processes.
- a known process of this type comprises impregnating wool with an aqueous, thickened solution of acid wool dyestuffs (pad liquor) at temperatures below the drawing temperature of these dyestuffs, then drying the goods and fixing the dyestuif by passing the goods through a hot acid bath (so-called acid shock), and rinsing.
- acid shock hot acid bath
- the stable pad-liquors thus obtained require a pH above 5.0 and preferably a neutral to alkaline pH range in order to remain homogeneous.
- This is disadvantageous for the dyeing of polyamide fibers and particularly of wool, and undesirable because it excludes the use of certain commercially valuable wool dyestuffs which require after-chrom- 'ice ing in a pH range below 5.0 such as Eriochrome Black
- the process according to the invention comprises:
- the above-mentioned dyestuif carrier upon the composition of which the successful dyeing according to the invention depends, consists essentially of a mixture of (A) an unsulfated amide or a mixture of unsulfated amides of a substantially saturated aliphatic monocarboxylic, i.e., fatty acid from 10 to 14 carbon atoms in the lipophilic radical, which fatty acid may also be substituted by higher alkyl-phenoxy wherein the higher alkyl moiety has from 8 to 12 and preferably 9 carbon atoms, or of a mixture of such fatty acids of from 8 to 14 carbon atoms which mixture of acids has preferably an average number of more than 10, and preferably 12 carbon atoms, amidified with primary or sec ondary amines containing at least one hydroxy-lower alkyl group which may be etherified; more specifically, unsulfonated amides defined under (A) supra, which can be used in the pad liquors according to the invention are derived from,
- bis-(hydroxyalkyl)-amines preferably of a total of from 4 to 6 carbon atoms such as bis-(flhydroxyethyl) amine, bis ('y hydroxypropyl)- amine, bisa-methyl-fi-hydroxyethyl) -amine;
- N-alkyl-N-(hydroxyalkyl)-amines preferably N-methyl-N-w-hydroxyalkylamines of from 3 to 4 carbon atoms, or the corresponding N-ethylsubstituted amines of from 4 to 5 carbon atoms such as N-methylor N-ethyl-N-(,B-hydroxyethyD- amine, or N-methylor N-ethyl-N-(y-hydroxypropyl)-amine;
- amino-lower alkyl ethers especially mono- (w-alkoxy-alkyD-amines of a total of from 3 to 5 carbon atoms, at least two of which pertain to the 3 alkyl moiety, such as B-methoxyor fi-ethoxyethylamine or v-methoxyor 'y-ethoxypropylamine;
- polyglycol ether is the condensation product of an alkanol or a higher alkyl phenol with ethylene oxide or propylene oxide in molar ratios ranging from 1 to 20, the terminal hydroxy group of which condensation product has been sulfated, such sulfated polyglycol ether being more in particular (i) a sulfated condensation product of an alkancl of 8 to 14 carbon atoms, with ethylene oxide condensed with each other in a molar ratio of from 1:1 to 1:20, and preferably from 1:2 to 1:5,
- a sulfated condensation product of alkylphenol the alkyl moiety of which has from 8 to 12 carbon atoms, with ethylene oxide, in a molar ratio of from 1:1 to 1:20, and preferably 1:2 to 1:3, e.g., sulfated glycol ethers of octyl phenol or nonyl phenol, or
- the ratio of acid amides (A) to the sulfated polyglycol ethers (B) ranges from about 2:1 to 1:2, and preferably 3:2 to 1:15, and, when the above-mentioned clarifying agent is present in order to ensure homogeneity of the carrier mixture for a period of several months and even a year or more, the proportions by weight of (A) to (B) also range from about 2:1 to 1:2, and preferably 3:2 to 1:15, and the content of said clarifying agent ranges from 4 to 20% by weight, calculated on the total weight of said mixture.
- the pad liquors can also be prepared, shortly prior to use, from the individual constituents (A) and (B) of the above-described carrier mixture in the proportions given, in which case the addition of component (C), the clarifying agent is superfluous.
- the amide (A) is heated to render the same readily flowing and is added with stirring to an aqueous solution of the constituent (B).
- isopropanol assists flowability of the carrier mixture, but does not affect the color depth of the dyeing obtained in the process according to the invention.
- the bis-(hydroxyalkyl)-amides mainly those having hydroxyalkyl radicals containing two or three carbon atoms are preferred, such as bis-(fi-hydroxyethyl)-amides or bis-('y-hydroxypropyl) amides of the fatty acids described above, because they produce good color yields.
- the amides described under (A) above are obtained by reacting the esters of suitable fatty acids with lower alkanols, e.g., reacting the fatty acid methyl or ethyl ester with the desired amine in the presence of sodium or potassium alcoholate, for example, by one of the processes described in British Patent N0. 631,367.
- Sulfated polyglycol ethers of lauryl alcohol having, in particular, 2 to 3 ether oxygen atoms are preferred as components (B), as these compounds produce particularly level dyeings of good color strength.
- the sulfated surface-active polyglycol ether compounds defined under (B) are generally used in the form of their soluble salts; in particular the alkali metal or ammonium salts, but also the alkyl and hydroxyalkyl ammonium salts can be used.
- these salts are usually saponified so that the respective free polyglycol ether sulfuric acids, are present therein.
- sulfated surface-active polyglycol ethers used in preparing the carrier mixture are produced in a conventional manner by first condensing a suitable alkanol or alkylphenol falling under the definition given hereinbefore, with the corresponding number of ethylene oxide moles in the presence of a suitable alkaline catalyst such as sodium ethylate or caustic soda, and subsequent sulfation with chlorosulfonic acid and, finally, neutralization with a suitable cation donor to form the desired salts of the respective sulfated polyglycol ether.
- a suitable alkaline catalyst such as sodium ethylate or caustic soda
- the dyestuff carrier consists essentially of a mixture of an unsulfonated amide as defined under (A), supra, and (C) a sulfated amide of an aliphatic monocarboxylic acid, which is optionally substituted and has at least one lipophilic radical, with primary or secondary amines having at least one lower hydroxyalkyl group, and more particularly, sulfated fatty acid mono-B-hydroxyethyl-amides the fatty acid radicals of which have 8 to 14, preferably.
- the sulfated compounds defined under (C) are usually employed in the form of their soluble salts, in particular their alkaline, ammonium, lower alkyl or hydroxy-alkylammonium salts, in the latter case the dior tri-(flhydroxyethyl-amine -salts.
- the above-mentioned dyestuif carrier can also consist essentially of an unsulfated amide as defined under (A), supra and (D) a sulfated (alkylphenyl)-(2,3-dihydroxypropyl)-ether the alkyl radical of which has 8 to 12, preferably 9 carbon atoms or a mixture of the sulfated amide mentioned under (C) with a sulfated ether as defined under (D) or of the soluble salts of these sulfated compounds, respectively.
- Sulfated ('alkylphenyl) (2,3-dihydroxypropyl)ethers usable according to the invention are primarily sulfated (nonylphenyl) 2,3-dihydroxypropyl) -ether.
- Such ethers are obtained by the reaction of glycol chlorohydrin or l-chloro-2,3-dihydroxy-propane with the corresponding alkylphenols and sulfating the resulting dihydroxy compounds by methods known per se.
- Organic fibers which are dyed according to the invention are, among others, polyester fibers such as cellulose dito tri-acet-ate, especially, however, also high-molecular esters of aromatic polycarboxylic acids with polyfunctional alcohols, e.g., polyterephthalic acid glycol esters, or polyurethanes, as well as polymeric and copolyrneric acrylonitrile and methacrylonitrile, polyolefine, chiefly however, synthetic and natural polyarnide fibers such as nylon, Wool or silk.
- polyester fibers such as cellulose dito tri-acet-ate
- high-molecular esters of aromatic polycarboxylic acids with polyfunctional alcohols e.g., polyterephthalic acid glycol esters, or polyurethanes
- polymeric and copolyrneric acrylonitrile and methacrylonitrile polyolefine, chiefly however, synthetic and natural polyarnide fibers such as nylon, Wool or silk.
- the process of the invention yields uniform dyeings also with material of great yardage.
- the drawing temperature of the dyestuffs used i.e., the temperature at which the dycstuff draws within about a minute upon the fiber, is usually about 70 C. or more. Impregnating according to the invention has to be effected below this drawing temperature.
- Non-cationic dyestuffs capable of drawing on fibers falling under the above-described group under the conditions given, are monoand poly-, preferably dis, azo dyestuffs, namely metal-free, metallizable and heavymetal-containing, in particular chromiurn-, cobalt, nickeland copper complex azo dyes which comprise also the formazane dyes, furthermore, anthraquinone, nitro and methine dyes, acid triphenylmethane and xanthone dyes, naphthazarine dyes and quinophthalone dyes, and also copper phthalocyanine dyes.
- azo dyestuffs namely metal-free, metallizable and heavymetal-containing, in particular chromiurn-, cobalt, nickeland copper complex azo dyes which comprise also the formazane dyes, furthermore, anthraquinone, nitro and methine dyes, acid triphenylmethane and xanthone dyes, naphth
- dyestuffs which are soluble in neutral, acid, or basic medium, within the pH range specified above, and, on the other hand, dyestuffs which are dispersible in water.
- suitable dyestuffs for natural and synthetic polyamide fibers are the so-called acid wool dyes which comprise the above-listed azo, anthraquinone, triphenylmethane and xanthone dyes, and, in particular, also those containing fiber-reactive groups, i.e., so-calied reactive wool and cotton dyes, derived from azo, anthraquinone or phthalocyanine dyes.
- the impregnating liquor used in the invention can also contain bactericidal and fungicidal compounds as well as agents which protect against insects, i.e., moth-proofing agents such as the compounds of the formulas SOSH and
- the water-soluble so-called acid wool dyestuffs particularly also heavymetal-containing, i.e., chromium-, cobaltor copper-containing, azo dyestuffs, including formazane dyestuffs, especially metallized monoazo dyestuffs which contain one metal atom to two molecules of azo dyestuffs are preferred.
- Chrome dyestuffs are also suitable for these fibers, particularly chromable azo dyestuffs, which latter are used with chromium (III) salts or soluble chromates, preferably in acid medium.
- polyester polyacrylonitrile and especially modified, in particular vinyl-pyridine-modified copolymers of acrylonitrile and methacrylonitrile fibers as well as polyolefine, in particular polypropylene fibers
- azo, anthraquinone, nitro and methine dyestuffs free from water-solubilizing groups, naphthazarine and quinophthalone dyes while polyurethane fibers as well as synthetic polyamide fibers such as the various types of nylon can be dyed satisfactorily with the aforesaid water-soluble dyestuffs, and also with disperse dyes of the group listed above.
- thickeners those products which are conventional in textile printing are used, e.g., carob bean flour, galactomannan, tragacanth, dextrin, British gum or-in alkaline medium-also the water-soluble salts of alginic acid.
- Cellulose derivatives such as methyl cellulose or soluble salts of carboxymethyl cellulose can also be used.
- the thickeners must not cause the formation of precipitates in the pad liquor under the conditions of the above-described dyeing method.
- the organic fibers to be dyed according to the invention can be in any form desired.
- they can be in the form of flocks, slubbing, yarn or fabrics.
- the material to be dyed can also be in the form of mixed fibers which can cousst, for example, of poly-amide fibers and incrusted cellulose fibers, or in the form of blended fabrics, particularly from wool and polyester fibers such as cellulose acetate, cellulose triacetate and, particularly, polyterephthalic acid glycol ester fibers.
- wool and polyester fibers such as cellulose acetate, cellulose triacetate and, particularly, polyterephthalic acid glycol ester fibers.
- only the polyamide (e.g., the wool) or also the polyamide and polyester components can be dyed simultaneously with dyestuffs suitable therefor.
- the fibers are impregnated, for example, by printing, in which case wool can be previously chlorinated, as is conventionally the case prior to printing thereon, or the fibers can be impregnated by coating or spraying, preferably, however, by padding.
- the impregnating solution (pad liquor) according to the invention is advantageously prepared by mixing warm aqueous dycstuff solutions or dispersions of suitable concentration, which contain thickeners, with the desired amount of carrier mixture according to the invention, as defined herebefore, as well as, optionally, other additives.
- the polyamide fibers are impregnated advantageously at 30 to 70 C. and then equeezed out to the desired content of impregnating liquor which is about 40 to 130%, and preferably 50 to 100%, of the weight of the fiber (400 grams to 1,300 grams per kilogram of goods).
- the impregnated fibers are then steamed by the usual methods, advantageously with neutral saturated steam.
- the dyestufi is preferably fixed on the fibers by treatment in a hot acid bath by known methods (acid shock).
- the acid content is advantageously about 9 to 10 grams per liter.
- the goods are introduced into the acid bath at to 98 C.
- inorganic and organic acids are suitable, e.g., sulfuric, phosphoric or hydrochloric acid or formic or acetic acid.
- Organic acids are preferred, in particular formic acid.
- water-soluble salts preferably water-soluble calcium salts to the acid bath. Development can also be performed by continued steaming as well as, in the case of polyamide and polyacrylonitrile fibers, with hot dilute acid.
- the fixed goods are then advantageously rinsed, e.g., with cold or warm water which can contain the auxiliaries usual in the dyeing industry, e.g., formic acid or acetic acid or also wetting or detergent substances.
- the auxiliaries usual in the dyeing industry, e.g., formic acid or acetic acid or also wetting or detergent substances.
- Pad liquors suitable for carrying out the padding process according to the invention can also be prepared from pre-mixed pastes which contain as the essential ingredients:
- acid or alkaline agents such as, in particular, acetic acid, formic cid, sulfuric acid, phosphoric acid, sodium or potassium carbonate or bicarbonate, sodium or potassium acetate, or sodium or potassium hydroxide, in amounts sufficient to adjust the pH of the paste to a value most compatible with the dyestuif and with the maintenance of a satisfactory homogeneity of the paste, and, optionally of,
- a homogeneity-enchancing and/ or preserving agent such as isopropanol or one of the other compounds mentioned hereinbefore of the here-employed carriers according to the invention, is especially present in the paste in those cases where the latter is prepared from carriers listed above which contain such ingredient.
- Pad liquors for use in the method according to the invention are prepared from these pastes by diluting the latter with water, preferably in such proportions that 1 kg. of pad liquor is obtained from every 100 to 400 kg. of paste, depending on the desired depth of shade of the resulting dyeings.
- the process according to the invention for the dyeing of organic fibers has remarkable advantages over similar known processes.
- the main advantage consists in the pH range which stretches very far and deep into the acid region at which dyeing can be performed, so that the most favorable dyeing conditions can be chosen without the pH of the liquor being taken into consideration.
- certain chromable dyestuffs such as Eriochrome Black T can be used with chromium (III) salts.
- Another advantage of the process according to the invention is that the pad liquors are homogeneous under the conditions of the above-described dyeing method and remain so for a long time, as mentioned hereinbefore.
- pad liquors especially those consisting of two phase emulsions, which form a so-called coacervate suffer easily phase separation within a relatively short time, require special adjuvants such as alginates to postpone this separation, and, once such separation has occurred, yield spotty, unlevel dyeings
- the pad liquors according to the invention need no such stabilizing adjuvants and remain stable since they are one-phase systems They thus do not require such careful adjustment of the proportions of the ingredients, are simpler to prepare, and do not require special stabilizing adjuvants but can be used with satisfactory results, after standing for weeks or even months.
- Dyeings obtained with the pad liquors according to the invention show good dyestuff yields and particularly good fixability of the dyestutf on the fibers after padding, without any special further adjuvants.
- dyed fibers and filaments padded according to the process of the invention are, to our knowledge, the first that permit: successful fixation of the fiber by steaming directly following padding.
- steaming for instance, fibers or slubbing
- these goods are given a fluffy texture blowing up the space occupied by the padded goods by just the right amount, namely about three to seven times the original volume, but not further so that no entanglement of the fibers occurs which might disturb passage of the material through the steaming apparatus, whereby a rapidly fixable material is obtained.
- dyeing with pad liquors hereemployed permits much shorter steaming times, for instance, depending on the nature and concentration of the dyestuffs, only 20 minutes, where, with the same dyestuff in the same concentration, use of a known carrier would require 40 minutes of steaming.
- Carrier as used in this specification and the appended claims means a color transfer agent which assists in carrying the dyestulf from a pad liquor or ink on to and into the fiber to be printed.
- EXAMPLE 1 40 parts of the commercial form of the chromium complex compound of the monoazo dyestuff Z-aminophenol 4-methylsulfonee1-phenyl-3-methyl-pyrazolone (molar ratio of dyestuff: chromium is 2:1)containing about 50% of sodium sulfate as diluting agentare dissolved in a 60-warm mixture of 300 parts of an aqueous 2.5%-solution of carob bean flour and 30 parts of a carrier mixture consisting of the sodium salt of sulfated lauryl alcohol diglycol ether coconut oil fatty acid, N,N-bis-(B-hydroxyethyD-amide and isopropanol in a weight ratio of 9:9:2, and 250 parts of water.
- a carrier mixture consisting of the sodium salt of sulfated lauryl alcohol diglycol ether coconut oil fatty acid, N,N-bis-(B-hydroxyethyD-amide and isopropanol in a weight ratio of 9:9:
- the resulting solution is diluted to 900 parts with warm water (60 C.) and the pH is adjusted to about 2.5 with formic acid. The temperature of the mixture should then be about 50. This solution is then diluted with water to 1000 parts. Wool flannel is impregnated at 50 With this liquor, squeezed out to a liquor content of about 100% calculated on the dry weight of the fibers and steamed with saturated steam for 15 minutes at 98.
- the goods are then washed first with a solution containing 1 gram (g.) per liter of nonylphenolpolyglycol ether condensation product (molar ratio about 1:12), then rinsed with water and then washed with an aqueous solution containing 2 milliliters (ml.), per liter, of formic acid and again rinsed with water.
- a level, well penetrated orange wool dyeing is obtained which has no so-called sandwich efiect.
- chromium-containing monoazo dyestuffs of the type containing 2 dyestuff molecules per chromium atom (2:1 complexes) which contain no sulfonic acid groups but which are substituted by lower alkylsulfonyl groups or which contain sulfonic acid amide groups which may be substituted at the nitrogen atom by alkyl groups
- the chromium-containing dyestutf 2-aminophenol-S-sulfonic acid an1ide l-phenyl-3- methyl-pyrazolone
- diand tri-ethanolamine salts of sulfated lauryltriglycol ether can be used instead of the ammonium salt.
- EXAMPLE 2 Woolen slubbing is padded with the liquor described in the first part of Example 1, the pH of which, however, has been adjusted to 4 with acetic acid instead of formic acid, and the procedure given in the first part of Example 1 is followed.
- Turquoise dyeings of similarly good qualities are obtained by repeating Example 2, but using, instead of the 40 parts of dyestufi used therein, 20 parts of the corn conciseally available dyestufi Solophenyl Turquoise Blue GL (C1. Direct Blue 86), and otherwise following the same method as given in Example 2.
- EXAMPLE 3 By repeating the above Example 2, but using, instead of the last-mentioned dyestuffs, 20 g. of the copper complex of the dyestufl of the formula COOH produced as described in Example 2 of the US. Patent 2,839,521 to Schetty, issued June 17, 1958, wool slubbings of very fast, light brown shades are obtained.
- EXAMPLE 4 By repeating the above Example 2, but using, instead of the last-mentioned dyestufl 18 g. of the commercial dyestuff Reacton Brilliant Red BGL (Color Index, 2nd Edition, Reactive Red 20) wool slubbings of particularly brilliant red shades are obtained.
- EXAMPLE 5 W001 flannel is impregnated at 60 with pad liquor prepared as described in the first part of Example 1 and squeezed out to a liquor content of about 100%.
- the padded fabric is introduced into a 98-warm aqueous bath which contains 8 cc./liter of 85% formic acid, and is left in this bath for 5 minutes.
- the wool flannel so dyed is then washed with a 45-warm aqueous solution of 0.5 g./ liter of nonylphenol polyglycol ether for 5 minutes, whereupon it is rinsed with cold water.
- the resulting orange dyeing is well penetrated and has no sandwich effect.
- potassium salt of sulfated myristal alcohol pentaglycol ether instead of the potassium salt of sulfated myristal alcohol pentaglycol ether, also the potassium or sodium salt of sulfated octylphenol diglycol ether [CSHITQ (O CzHr) 2-0 S 03K] can be used.
- EXAMPLE 6 Woolen slubbing is impregnated at 40 on a pad mangle with an impregnating liquor which contains the dyestutf Acid Red 133 (Color Index, 2nd Edition) instead of the azo dyestuff mentioned in the first part of Example 1 and which is otherwise prepared as described in Example 1.
- the slubbing is squeezed out to 100% content.
- the goods are then steamed under slight excess pressure for 15 minutes at 98. They are then washed first with a solution containing 1 g. per liter of nonylphenol polyglycol ether, then rinsed with water, then washed with an aqueous solution containing 2 ml. per liter of aqueous 85%-formic acid and, optionally, rinsed with water.
- the disazo dyestuff coupling in an acid medium according to the formula or the chromium-containing (chromium to dyestuif ratio 1:1) dyestufi Neolan Yellow 8 GE (Acid Yellow 101 of the Color Index, 2nd Edition), and otherwise following the procedure given in the above example then equally well penetrated and level red or yellow colored material, respectively, is obtained.
- EXAMPLE 7 parts of Eriochrome Black T (Mordant Black 11 of the Color Index, 2nd Edition) and 5 parts of aqueous 25%-ammonia solution are dissolved in hot water, 100 parts of an aqueous 2.5 %-carob bean flour solution and 30 parts of a mixture produced by mixing with each other 13.5 parts of the sodium salt of sulfated lauryl alcohol ether [C12H25(OC2H4)2-OS3N3.], parts of coconut oil fatty acid N,N-bis-(fihydroxyethyl)amide, 1.5 parts of fi-methoxy-methanol, and 1.5 parts of isopropanol, which 30 parts have been dissolved in 500 parts of .'arm water, are added to the solution.
- the temperature of the ready solution should be about 50.
- the slubbing is then rinsed in a first bath in a backwashing machine at 40 and then treated for 15 to 30 seconds in a second back-washing machine bath in an aqueous solution containing 10 g./liter of sodium bichromate, and 8 mL/liter of aqueous 85%-formic acid, at a temperature of 70.
- the slubbing is then rinsed in further back-washing machine baths with water of about 40.
- Slubbing dyed evenly black is obtained which can be readily combed and spun.
- EXAMPLE 8 Grained silk is impregnated at 40 with an impregnating liquor produced according to the first part of Example 1, squeezed out to a liquor content of 80% and introduced into a 98 warm aqueous bath which contains 8 cc./liter of 85 %-formic acid. It is kept in this bath for 5 minutes. The grained silk is then washed with a 45-Warm aqueous solution of 0.5 g./liter of nonylphenol polyglycol ether and then rinsed with cold water.
- the fabric is then squeezed out to a liquor content of 50% calculated on the weight of the fibers, introduced into a 98-warm aqueous bath containing 4 ml. per liter of aqueous 85 %-formic acid and treated in this bath for 4 minutes.
- the fabric is then rinsed first with Warm and then cold water; it is well and evenly dyed olive.
- EXAMPLE 11 A plain-woven fabric made from poly-e-aminocaprolactam (nylon 66) is padded at 40 with an impregnating liquor produced according to Example 8. The fabric is squeezed out to a liquor content of 50% calculated on the weight of the fibers and then dried under thermofixing conditions for seconds at 190.
- the Perlon fabric thus treated is introduced into a 98- Warm aqueous bath which contains 4 ml. per liter of aqueous 85%-formic acid, and is boiled in this bath for 4 minutes. It is then rinsed with warm and cold water.
- the solution is adjusted to a pH of 4 with aqueous 80%-acetic acid, and diluted up to :1000 parts. Woolen slubbing is impregnated at 40 with this liquor, squeezed out to a liquor content of about 100% (calculated on the weight of the fibers) and steamed for 15 minutes at 98 with saturated steam.
- the goods are then washed with a solution containing 1 g./liter of n-onylphenol polyglycol ether and 1 ml./liter of concentrated ammonia solution, then rinsed with water, washed with aqueous solution containing 2 ml./liter of aqueous 85%-formic acid and again rinsed with water.
- the orange-yellow slubbing so obtained is well penetrated and very level.
- the touch of the goods is very loose and voluminous and the material can be readily combed and spun.
- the solution obtained is made up to 1000 parts with water.
- the temperature of the solution should be 60.
- Wool flannel is impregnated with this liquor at 60 and squeezed out to a liquor content of about
- the padded fabric is introduced into a 98-Warm aqueous bath which contains 8 ml./liter of aqueous %-formic acid, and is kept in this bath for 5 minutes.
- the grey-colored wool flannel is then Washed with a 45-warm aqueous solution of 0.5 g./ liter of nonylphenol polyglycol ether and then rinsed with cold Water.
- a wellpenetrated grey Wool flannel of level shade Without a sandwich effect is obtained.
- EXAMPLE 14 40 parts of the commercial form of the dyestufif 'EriochromeCyanine R (Acid Blue 13 of Color Index, 2nd
- the pH of the resulting solution is adjusted, if necessary, to 7.5 to 8, with acetic acid and brought up to 1000 parts with water.
- the temperature should be 50.
- Wool flannel is padded with this liquor at 60 and squeezed out to a liquor content of about 100%.
- the padded fabric is then steamed with saturated steam for 30 minutes.
- the resulting blue-colored wool flannel is then washed with a 45 -warm aqueous solution of 0.5 g./liter of nonylphenol polyglycol ether, treated in an acid bath which contains ml./liter of 85%-formic acid for 15 to 30 seconds at 70 and then rinsed with 50-warm water.
- a well-penetrated, very level blue wool flannel is obtained which is free from a sandwich effect.
- EXAMPLE 15 By using, instead of the pad liquors described in Example 14, similar liquors, the pH of which has been adjusted to 3.5 to 4 with aqueous 80%-acetic acid and which contain, instead of sodium alginate, methyl cellulose and, instead of potassium chromate, 30 parts of chromium fluoride as agent afiording chromium, and Wool flannel is padded therewith at 50, squeezed out to a liquor take up of about 100% calculated on the weight of the goods and steamed with saturated steam for 30 minutes at 90, then blue, yellow or red-colored wool flannel, respectively, is obtained.
- the dyeings have equally good penetration and evenness. If the steaming time is raised from 30 to 45 or 60 minutes, then dyeings of somewhat more color strength are obtained.
- EXAMPLE 16 A fabric consisting of 45 parts of wool and 55 parts of polyglycol terephthalate fiber is impregnated and steamed in accordance with the first part of Example 1. The Wool portion is dyed orange while the polyester portion remains practically undyed.
- EXAMPLE 17 A mixed fabric of wool and cellulose triacetate (weight ratio 1:1) is impregnated and steamed as described in the first part of Example 1. The wool portion is dyed orange, while the triacetate portion remains practically undyed.
- EXAMPLE 18 11 parts of the chromium-containing monoazo dyestutf 2-aminophenol-4-sulfonic acid N,N dimethylamide 1- (3'-chlorophenyl)-3-methyl-5-pyrazolone, 1 part of the chromium-containing monoazo dyestuif 2-amino-4-methylsulfonyl-benzene carboxylic acid- 1 phenyl-3-methyl-5- pyrazolone and 0.5 part of the mixed chromium-containing dyestuff 2-amino-4-methylsulfonyl-benzene l-methylsulfonylamino-7-hydroxynaphthalene 1-(4'-chlorophenyl)-3-methylpyrazolone (the overall molar ratio of dyestufizchromium being 2:1) are dissolved in a 50-warm mixture of 300 parts of an aqueous 2.5 %-carob bean flour solution and 30 parts of a carrier mixture consisting of: di-(B-hydroxy
- the pH of the solution ready for use should be about 3.5 and the temperature should be about 50.
- Woolen slubbing is padded with this liquor at 50, squeezed out to a liquor content of about calculated on the weight of the goods, and steamed with saturated steam for 15 minutes at 98".
- the goods are then washed with a solution containing 1 g./liter of nonylphenol polyglycol ether, rinsed with water, washed with an aqueous solution containing 2 nil/liter of aqueous 85%formic acid and again rinsed with water. Thereby, a level and well-penetrated moth-proof wool dyeing is obtained which shows no sandwich effect.
- EXAMPLE 19 20 parts of the commercial form of the dyestutf Setacyl Yellow 2 GN (Disperse Yellow '3 of Color Index, 2nd edition) are dissolved in a 60-Warm mixture of 200 parts of an aqueous 2.5%sodium alginate solution and 35 parts of a carrier mixture consisting of: the tri-(B-hydroxyethyD-amine salt of sulfated octylphenol diglycol ether coconut oil fatty acid-N,N-bis-(fl-hydroxyethyD-amide, and isopropanol, in a weight ratio of 9:9:2, which carrier has been dissolved in 250 parts of water.
- the solution obtained is brought up to about 1000 parts with warm water, whereby the pH should be at about 7 to 8 and, if necessary, this is adjusted with a small amount of acetic acid.
- Polyacrylonitrile ('Orlon) fibers are impregnated at 30 with this solution, squeezed out at about 50%, cal culated on the weight of the goods, and steamed with saturated steam for 30 minutes at 98.
- the goods are then washed with a solution containing 1 g./liter of nonylphenol polyglycol ether and rinsed with cold water. A yellow-colored slubbing is obtained.
- Leacryl or Acrylan Regular can be padded with the same padding liquors in the same manner as described above.
- the slubbing is steamed for 30 minutes at 98 with saturated steam, then washed with a solution containing 1 g./liter of nonylphenol polyglycol ether and rinsed with warm and cold water. A level yellow or red-colored polyester slubbing is obtained.
- Polyglycol terephthalate yarn is then padded with the resulting liquor and squeezed out to a liquor content of 50% calculated on the Weight of the yarn.
- the yarn is then steamed for 30 minutes at 90 with saturated steam, then washed with a solution containing 1 g./liter of nonylphenol polyglycol ether and rinsed with warm and cold water. A level greenish-blue polyester yarn is obtained, which is fast to washing and light.
- EXAMPLE 22 360 parts of "a press cake of Eriochrome Black A (Color Index, 2nd Edition, Mordant Black 1) are introduced in batches into a vessel equipped with a turbomixer of the Homo-Rex type manufactured by Broglie & Co., Basel, Switzerland, having a preferred operational speed in the range of about 3,000 to 5,000 r.p.m., which vessel has been charged with 360 parts of water, and the contents are stirred for one hour at a speed of about 4,000 r.p.m.
- a solution is prepared by mixing 120 parts of a carrier mixture consisting of sodium lauryloxy-ethoxyethyl sulfate (sodium salt of sulfat lauryl alcohol diglycol ether), coconut oil fatty acid N,N-bis-'(,8-hydroxyethyl)-amide and isopropanol, in a weight ratio of 9:9:2, 150 parts of water, and 10 parts of aqueous 80%-acetic acid, whereby the pH of the paste is adjusted to a value below 5.
- a carrier mixture consisting of sodium lauryloxy-ethoxyethyl sulfate (sodium salt of sulfat lauryl alcohol diglycol ether), coconut oil fatty acid N,N-bis-'(,8-hydroxyethyl)-amide and isopropanol, in a weight ratio of 9:9:2, 150 parts of water, and 10 parts of aqueous 80%-acetic acid, whereby the pH of the paste is adjusted to
- This solution is added slowly to the contents of the first vessel while continuing stirring which is terminated minutes after the addition of the solution from the second vessel is complete.
- a pad liquor is prepared from 300 parts of the above paste by stirring the same with 350 parts of 60-warm water and parts of an aqueous 2.5% carob bean flour solution. To the resulting liquor there is added a mixture of 20 parts of chromium trifluoride (Cland 50 parts of an aqueous 20%-chromium acetate solution which has previously been boiled.
- the solution is brought to 900 parts with 60-warm water and 20 cc. of aqueous 85%-formic acid are added to the solution which is then made up to 1000 cc. with water.
- the temperature of the pad liquor ready for use is then approximately 50.
- EXAMPLE 23 (l) parts of myristic acid n-('y-ethoxypropyl)- amide are liquefied by heating and are added slowly to 170 parts of bis-('y-hydroxy-propyl)ammonium salt of sulfated laurylphenolhexaglycol ether [bis-(' -hydroxypropyl)-ammonium laurylphenol hexa oxy-ethyl sulfate] in a turbomixer with stirring at about 4,000 r.p.m., for one hour. The completely homogenized mixture is then dissolved with 2,000 parts of 60-warm water.
- Cellulose acetate or triacetate fabrics or fabrics made of polyvinylalcohol of the Kuralon type (manufactured by Kurashiki Rayon K.K., Japan) or fabrics of polyurethane, of the Lycra-Spandex type of fibers (manufactured by E. I. du Pont de Nemours, Wilmington, Del.) are paddyed in the same manner as described above for Perlon, and similarly good quality blue dyeings are obtained.
- Kuralon type manufactured by Kurashiki Rayon K.K., Japan
- Lycra-Spandex type of fibers manufactured by E. I. du Pont de Nemours, Wilmington, Del.
- EXAMPLE 24 (I) A carrier mixture according to the invention is prepared in the same manner as described in Part I of Example 23, but using, instead of 130 parts of the myristic amide and 170 parts of the sulfated laurylphenol hexaglycol ether salt used therein: parts of capric acid N-ethyl-N-y-hydroxy-propyl-amide, and 200 parts of N- methyl N 'yhydroxy-propylamrnonium p-octylphenyldeca-oxyethyl-sulfate, respectively.
- the fabric is then steamed for 40 minutes in an atmosphere of saturated steam at 98.
- the steamed fabric is then washed in a bath containing 1 gram of nonylphenol polyglycol ether per liter of water, and finally rinsed with water, and dried.
- brown dyeings are obtained by pad-dyeing polyurethane fabrics of the Lycra type (manufactured by E. I. du Pont de Nemours, Wilmington, Del.), 21 vinylpyridine-modified polyacrylonitrile fabric of the Acrilan regular type (manufactured by The Chemstrand Corporation, Decatur, Ala.), or a polyethylene fabric of the Curlin type (manufactured by Courtaulds, Ltd., London, England) according to the method described in this example.
- Lycra type manufactured by E. I. du Pont de Nemours, Wilmington, Del.
- 21 vinylpyridine-modified polyacrylonitrile fabric of the Acrilan regular type manufactured by The Chemstrand Corporation, Decatur, Ala.
- a polyethylene fabric of the Curlin type manufactured by Courtaulds, Ltd., London, England
- capric acid N-(w-hydroxybutyD-amide) 80 parts are liquefied by heating and then added slowly into a turbomixer charged with 100 parts of potassium nonyloxy- (ethoxy) -ethyl sulfate (potassium salt of sulfated octyl alcohol decaglycol ether), and the resulting mixture is stirred at 4,000 rpm. for one hour.
- a thickened dyestutf solution is prepared from 218 parts of the above carrier mixture solution and 205 parts of an aqueous solution of 5 parts of the commercial dyestuff Irgalan Yellow (Color Index, 2nd Edition, Acid Yellow 129), proceeding in the same manner as described in part H of the preceding example.
- Example 25 is repeated, but instead of 8 parts of the capric acid amide used therein, 12 parts of N,N-bis-(fihydroxypropyl)-lauramide are used as the first component, and, instead of the parts of the potassium salt of sulfated octylpolyglycol ether used therein, 14 parts of the potassium salt of sulfated myristyl alcohol tetraglycol ether C H (OC H -OSO K] are used as the second component of the carrier mixture according to the invention, and otherwise following strictly the same procedure as in the preceding example.
- the solution is cooled to about 50, and 30 g. of a carrier mixture are added which mixture consist of 9 parts of nonylphenoxy-acetic acid bis-fi-hydroxyethyl amide, 9 parts of the sodium salt of sulfated lauryl alcohol diethyleneglycol ether and 2 parts of isopropanol. 160 g. of an aqueous solution consisting of 40 g. of formic acid and 120 g. of water are added to this solution.
- the pad liquor thus obtained is used to impregnate woolen slubbing at 50; the slubbing is then squeezed on a pad mangle to a liquor content of about calculated on the dry weight of the goods.
- the slubbing is then steamed for 30 minutes in saturated steam at 100- 102. After steaming, the goods are washed with about 40 warm water, and subsequently, at 40, with an aqueous solution containing 1 gram per liter of nonylphenol polyglycol ether. Then it is rinsed and dried. A bordeauxcolored slubbing is obtained which has no sandwich effect.
- EXAMPLE 28 35 g. of the dyestuff 1-amino-6-nitro-2-hydroxynaphthalene-4-sulfonic acid 2-hydroxynaphthalene are pasted with 60 g. of cold water and dissolved in 770 g. of hot water by heating to the boiling temperature. 50 g. of an aqueous acetic acid solution consisting of 10 g. of 80% acetic acid and 40 g. of water are slowly added to this solution. Then, 14 g. of galactomannan thickening agent pasted with a small amount of ethanol for better solubility, are added while stirring. Upon dissolution of the thickening agent, the mixture is cooled to about 50, and 35 g.
- a carrier mixture consisting of 9 parts of nonylphenoxy acetic acid bis-fi-hydroxyethyl amide, 9 parts of the sodium salt of sulfated lauryl alcohol diglycol ether and 2 parts of isopropanol. 20 g. of 85% formic acid as well as a dispersion consisting of 80 g. of water and 40 g. of chromium fluoride are added to this solution.
- This pad liquor is used to impregnate woolen slubbing at 50 which is squeezed on a pad mangle to a liquor content of about 105% calculated on the dry weight of the goods.
- the slubbing is then steamed at 100 to 102 with saturated steam. After steaming, the goods are washed with about 40 warm water and subsequently, at 40, with an aqueous solution containing 1 g./liter of nonylphenol polyglycol ether; then it is rinsed and dried.
- This pad liquor is used to impregnate woolen slubbing at 50 which is squeezed on a pad mangle to a liquor content of about 110% calculated on the dry weight of the goods.
- the slubbing is then steamed for 15 minutes in saturated steam at to 102. After steaming it is washed in about 40 warm water and then, at 40, in an aqueous solution containing 1 g./liter of nonylphenol polyglycol ether, whereupon it is rinsed and dried. A yellow dyeing is obtained which has no sandwich effect.
- EXAMPLE 30 (a) 16 g. of the dyestuff sulfanilic acid 1-hydroxy[(3'- trichloropyrimidylamino) benzoylamino] naphthalene- 3,6-disulfonic acid are pasted with 40 g. of water and dissolved with further heating in 890 g. of hot water. 10 g. of galactomannan as thickening agent pasted with a small amount of ethanol for better solubility, are added to this solution while stirring. After dissolution of the thickening agent, the solution is cooled to 50, and 30 g.
- a carrier mixture consisting of 9 parts of nonylphenoxy acetic acid bis-fl-hydroxyethyl amide, 9 parts of the sodium salt of sulfated lauryl alcohol diglycol ether and 2 parts of isopropanol. Then 10 g. of 85 formic acid and 30 g. of water are added to this solution.
- the pad liquor thus obtained is used to impregnate woolen slubbing at 50 which is squeezed on a pad mangle to a liquor content of about 100% calculated on the dry weight of the goods.
- the slubbing is then steamed for 15 minutes in saturated steam at 100 to 102. After steaming, it is washed with about 40 warm water and then, at 40, with an aqueous solution containing 1 g./liter of nonylphenol polyglycol ether, whereupon it is rinsed and dried.
- a red dyeing is obtained which has no sandwich effect.
- EXAMPLE 31 13 g. of the 1:2 chromium-complex of the dyestuff 2-aminophenol-4-methyl-sulfone 1 acetylamino 7 hydroxy-naphthalene are pasted with 60 g. of cold water and dissolved with further heating in 890 g. of hot water.
- the pad liquor thus obtained is used to impregnate woolen slubbing at 50 which is squeezed on a pad mangle to a liquor content of about 105% calculated on the dry weight of the goods.
- the slubbing is then steamed for 15 minutes in saturated steam at 100 to 102". After steaming, it is washed with about 40 warm water and then, at 40, with an aqueous solution containing 1 g./liter of nonylphenol polyglycol ether, whereupon it is rinsed and dried.
- a grey dyeing is obtained which has no sandwich elfect.
- the pad liquor thus obtained is used to impregnate woolen slubbing at 50 which is squeezed on -a pad mangle to a liquor content of about 105% calculated on the dry weight of the goods.
- the slubbing is then steamed for 10 minutes in saturated steam at 100 to 102. Then it is treated for 5 minutes in an aqueous bath of 95 containing 6 g./liter of 85% formic acid.
- the slubbing treated in this way is washed with 40 warm water, then, at 40, in an aqueous bath containing 1 g./liter of nonylphenol polyglycol ether, and then rinsed and dried.
- a grey dyeing is obtained which has no sandwich effect.
- EXAMPLE 33 37.5 g. of the 1:2 chromium-complex of the monoazo dyestuff Z-carboxy 1 aminobenzene l phenyl 3- methyl-S-pyrazolone and 5.0 g. of the 1:2-chromiumcomplex of the monoazo dyestutf 2-aminophenol-4-sulfonic acid N methyl amide- 1 carbethoxyamino 7- hydroxy-naphthalene are dissolved in an 80-warm mixture of 200 g. of a 2.5% aqueous galactomannan-solution, 270 g. of water and 30 g.
- a carrier mixture consisting of 9 par-ts of nonylphenoxy-acetic acid bis-flhydroxyethyl amide, 9 parts of the sodium salt of sulfated lauryl alcohol diglycol ether and 2 parts of isopropanol.
- the resulting solution is adjusted to a pH- value of 7 and diluted with cold water to 1000 parts.
- the temperature should be about 40.
- This pad liquor is used to impregnate nylon toi-le which is squeezed to a liquor content of 50% of the fiber weight, steamed for 8 minutes at a temperature of 130, and rinsed first in hot and then in cold water.
- EXAMPLE 34 A fabric consisting of 45 g. of wool and 55 g. of a blended fabric of 50% wool and 50% Polyethylene glycol terephthalate fiber is impregnated and steamed analogous to the manner described in Example 31. The woolen fibers of the fabric are dyed grey while the polyester portion remains practically undyed.
- EXAMPLE 3 5 A blended fabric consisting of 50% wool and 50% cellulose triacetate is impregnated and steamed analogous to the manner described in Example 31. The woolen fibers of the fabric are dyed grey while the triacetate portion remains practically undyed.
- EXAMPLE 36 7 g. of the 1:2 chromium-complex of the dyestutf 2- aminophenol 4 methyl-sulfone l acety1amino-7-hydroxynaphthalene are pasted with 60 g. of cold water and dissolved with further heating in 690 g. of hot Water.
- a thickening agent galactomannan pasted with a small amount of ethanol for better solubility 10 g. of a thickening agent galactomannan pasted with a small amount of ethanol for better solubility, are added to this solution while stirring. After dissolution of the thickening agent, the solution is cooled to 50, and 30 g. of a carrier mixture are added consisting of 9 parts of nonylphenoxy acetic acid bis-fl-hydroxyethyl amide, 9 parts of the di-B-hydroxyethyl amine salt of sulfated lauryl alcohol triglycol ether and 2 parts of isopropanol.
- a carrier mixture consisting of 9 parts of nonylphenoxy acetic acid bis-fl-hydroxyethyl amide, 9 parts of the di-B-hydroxyethyl amine salt of sulfated lauryl alcohol triglycol ether and 2 parts of isopropanol.
- the pad liquor thus obtained is used to impregnate woolen slubbing at 50 which is squeezed on a pad mangle to a liquor content of about 105% calculated on the dry weight of the goods.
- the slubbing is then steamed for 15 minutes in saturated steam at to 102. After steaming, it is washed with about 40 warm water and then, at 40, with an aqueous solution containing 1 g./liter of nonylphenol polyglycol ether, whereupon it is rinsed and dried.
- a greydyeing is obtained which does not show a sandwich effect and is well protected against damage by moths.
- EXAMPLE 37 11 g. of the dyestufi of the formula HO (T I i NBC 0 CH CH3 are dispersed in an 80 warm mixture of 200 g. of a 2.5% aqueous sodium alginate solution and 35 g. of a carrier mixture consisting of 9 parts of nonylphenoxy acetic acid bis-,B-hydroxyethyl amide, 9 parts of the sodium salt of sulfated lauryl alcohol diglycol ether and 2 parts of isopropanol. The resulting solution is diluted with warm water to about 1000 g.; the pH-value should be about 7.
- This solution is used to impregnate at 30 slubbing consisting of Orlon type polyacrylonitrile fiber which is squeezed to a liquor content of about 100% calculated on the dry weight of the fibers and steamed for 30 minutes in saturated steam at 98. Then it is washed with an aqueous solution containing 1 g./liter of nonylphenol polyglycol ether and rinsed with cold and warm water. A yellow dyeing is obtained.
- EXAMPLE 3 8 Polyethylene glycol terephthalate slubbing is impregnated at 30 with a pad liquor prepared according to Example 27 and is squeezed to a liquor content of 80%.
- the slubbing is steamed for 30 minutes in saturated steam at 98, then it is washed with an aqueous solution containing 1 g./liter of nonylphenol polyglycol ether and rinsed with warm and cold water. A level yellow or red dyeing, respectively, is obtained.
- EXAMPLE 39 360 g. of the dyestufi. 1-amino-6-nitro-2-hydroxynaphthalene-4-sulfonic acid- 2-hydroxynaphthalene in the form of a press cake are introduced in portions while stirring into a boiler fitted with a turbo-mixer and containing 360 g. of water. The mixture is stirred for one hour.
- 120 g. of a carrier mixture consisting of 9 parts of nonylphenoxy acetic acid bis-B-hydroxyethyl amide, 9 parts of the sodium salt of sulfated lauryl alcohol diglycol ether and 2 parts of isopropanol are mixed with 10 g. of 80% acetic acid in a second mixing vessel. This homogeneous mixture is poured slowly while stirring continuously into the dyestuff suspension, and the whole is stirred for another minutes until a homogeneous brown dyeing preparation is obtained which is ready for use.
- a pad liquor is prepared by stirring 300 g. of this dyeing preparation with 350 g. of 60 warm water and 100 g. of a 2.5% aqueous carob bean flour thickener solution.
- the resulting solution is mixed with 40 g. of chromium trifiuoride and g. of 85% formic acid, and the liquor is then diluted With warm water to 1 liter. This liquor is used to impregnate woolen slubbing in the manner described in Example 18.
- a level black dyeing is obtained, and the slubbing can be well combed and spun.
- the dyeing has good fastness to washing and light.
- a carrier mixture which consists of 16 parts of coconut oil fatty acid bis-fi-hydroxyethyl amide, 8 parts of the sodium salt of sulfated nonylphenoxy acetic acid bisfl-hydroxyethyl amide, 8 parts of water and 3 parts of isopropanol.
- Example 27 This solution is combined as in Example 27, with 160 g. of an aqueous solution consisting of 40 g. of 85% formic acid and 120 g. of water.
- Example 28 is repeated, but in lieu of the 35 g. of the carrier employed therein, 35 g. of a carrier mixture are added which consists of 16 parts of coconut oil fatty acid bis-fl-hydroxyethyl amide, 8 parts of the sodium salt of sulfated nonylphenoxy acetic acid bis-fi-hydroxyethyl amide, 8 parts of water and 30 parts of isopropanol. 20 g. of formic acid as well as a dispersion comprising -80 g. of Water and 40 g. of chromium fluoride are added to this solution.
- a carrier mixture which consists of 16 parts of coconut oil fatty acid bis-fl-hydroxyethyl amide, 8 parts of the sodium salt of sulfated nonylphenoxy acetic acid bis-fi-hydroxyethyl amide, 8 parts of water and 30 parts of isopropanol. 20 g. of formic acid as well as a dispersion comprising -80 g
- a black slubbing is obtained which has no sandwich effect.
- Example 29 is repeated but instead of the carrier used therein, 30 g. of a carrier mixture are added consisting of 153 parts of coconut oil fatty acid bis-fi-hydroxyethyl amide, 58 parts of the sodium salt of sulfated coconut oil fatty acid mono-fl-hydroxyethyl amide, 95 parts of water and 34 parts of isopropanol. 10 g. of 85% formic acid and 30 g. of water are added to this solution. Padding is then carried out as described in Example 29. A yellow dyed slubbing is obtained which has no sandwich effect.
- a carrier mixture consisting of 153 parts of coconut oil fatty acid bis-fi-hydroxyethyl amide, 58 parts of the sodium salt of sulfated coconut oil fatty acid mono-fl-hydroxyethyl amide, 95 parts of water and 34 parts of isopropanol. 10 g. of 85% formic acid and 30 g. of water are added to this solution. Padding is then carried out as
- Example 30 is repeated but instead of the carrier mixture used therein 30 g. of a carrier mixture are added which consists of 160 parts of coconut oil fatty acid bis-,8- hydroxyethyl amide, 80 parts of the sodium salt of sulfated nonylphenoxy acetic acid bis-B-hydroxyethyl amide, 80 parts of water and 30 parts of isopropanol. 10 g. of 85% formic acid and 30 g. of water are added to this solution.
- a carrier mixture which consists of 160 parts of coconut oil fatty acid bis-,8- hydroxyethyl amide, 80 parts of the sodium salt of sulfated nonylphenoxy acetic acid bis-B-hydroxyethyl amide, 80 parts of water and 30 parts of isopropanol. 10 g. of 85% formic acid and 30 g. of water are added to this solution.
- a red dyeing is obtained which has no sandwic effect.
- a turquoise-blue dyeing is obtained when using instead of the 16 g. of the above dyestuff, g. of sodium-copper phthalocyanin disulfonate, the procedure being otherwise the same as in the above example.
- EXAMPLE 44 (a) Example 31 is repeated but instead of the carrier mixture used therein 30 g. of a carrier mixture are added consisting of 160 parts of coconut oily fatty acid bis-fihydroxyethyl amide, 80 parts of the sodium salt of sulfated nonylphenoxy acetic acid bis-B-hydroxyethyl amide, 80 parts of water and 30 parts of isopropanol.
- a carrier mixture consisting of 160 parts of coconut oily fatty acid bis-fihydroxyethyl amide, 80 parts of the sodium salt of sulfated nonylphenoxy acetic acid bis-B-hydroxyethyl amide, 80 parts of water and 30 parts of isopropanol.
- Example 32 is repeated but instead of the carrier mixture used therein, 30 g. of a carrier mixture are added consisting of 160 parts of coconut oil fatty acid bis-)3- hydroxyethyl amide, 80 parts of the sodium salt of sulfated nonylphenoxy acetic acid bis-B-hydroxyethyl amide, 80 parts of water and 30 parts of isopropanol. 10 g. of
- EXAMPLE 46 5.6 g. of the 1:2 chromium-containing monoazo dyestutf 2 carboxy-l-aminobenzene-e1-phenyl-3-methyl-5- pyrazolone and 5.0 g. of the 1:2 chromium-containing monoazo dyestutf 2-aminophenol-4-sulfonic acid-N-methyl amide 1-carbethoxyamino-7-hydroxynaphthalene are dissolved in an 80 warm mixture of 200 g. of a 2.5% aqueous galactomannan solution and 30 g.
- a carrier mixture consisting of parts of coconut oil fatty acid bis-fl-hydroxyethyl amide, 80 parts of sulfated nonylphenoxy acetic acid bis-B-hydroxyethyl-amide, 30 parts of isopropanol and 350 parts of water.
- the resulting solution is adjusted to a pH-value of 7 and diluted with cold Water to 1000 parts.
- the temperature should be about 40.
- This liquor is used to impregnate nylon toile which is squeezed to a liquor content of 50% of the fiber weight, steamed for 8 minutes at a temperature of 130 and then rinsed first in hot and then in cold Water.
- EXAMPLE 47 A fabric consisting of 45 g. of wool and 55 g. of polyethylene glycol terephthalate is impregnated and steamed in the manner described in Example 44. The woolen fibers of the fabric are dyed grey while the polyester portion remains practically undyed.
- EXAMPLE 48 A blended fabric consisting of 50% of wool and 50% of cellulose triacetate is impregnated and steamed as described irr Example 4-4. The woolen fibers of the fabric are dyed grey while the triacetate portion remains practically undyed.
- Example 36 is repeated but instead of the carrier mixture used therein, 30 g. of a carrier mixture are added consisting of 153 parts of coconut oil fatty acid bis-13- hydroxyethyl amide, 58 parts of sulfated coconut oil fatty acid mono-B-hydroxyethyl amide, 95 parts of water and 34 parts of isopropanol. 10 g. of the moth deterrent used I in Example 36 are added in the same manner.
- the resulting solution is diluted with warm water to about 1000 g.; the pH value should be about 7.
- Orlon-type polyacrylonitrile fiber slubbing is impregnated in the same manner as described in Example 37.
- the same pad liquors and the same methods used for Orlon can be used for dyeing Leacryl-or-Acrilan-type polyacrylonitrile fibers.
- EXAMPLE 51 Polyethylene glycol terephthalate slubbing is impregnated with a pad liquor as prepared in Example 50, and is squeezed to a liquor content of 80%.
- the slubbing is steamed for 30 minutes with saturated steam at 98, washed with an aqueous solution containing 1 g./liter of nonylphenol polyglycol ether and rinsed with warm and cold Water.
- a level yellow or red dyeing, respectively, is obtained.
- Example 39 is repeated, but instead of the carrier used therein, 120 g. of a carrier mixture consisting of 16 parts of coconut oil fatty acid bis-B-hydroxyethyl amide, 8 parts of sulfated nonylphenoxy acetic acid ibis-fi-hydroxyethyl amide, 8 parts of water, and 3 parts of isopropanol, which 120 g. of carrier have been mixed together with 10 g. of 80% acetic acid in a separate mixing vessel, are added under continuous stirring to the dyestufi suspension, and the whole is stirred for another minutes. In this manner, a homogeneous brown dyeing preparation is obtained which is ready for use.
- 120 g. of a carrier mixture consisting of 16 parts of coconut oil fatty acid bis-B-hydroxyethyl amide, 8 parts of sulfated nonylphenoxy acetic acid ibis-fi-hydroxyethyl amide, 8 parts of water, and 3 parts of isopropanol, which
- the pad liquor is obtained by diluting 300 g. of the above dyeing preparation with 350 g. of warm water at 60 and 100 g. of an aqueous 2.5% carob bean flour thickening solution.
- the resulting solution is mixed with 40 g. of chromium trifiuoride and g. of 85% formic acid, and the liquor is diluted to 1 liter with Warm water. This liquor is used to impregnate woolen slubbing in the manner described in Example 41.
- a level black dyed slubbing is obtained which can be well combed and spun.
- the dyeing has good fastness to washing and light.
- a process for pad dyeing textile fibers selected from the group consisting of polyamide, polyester, polyacrylonitrile, polyurethane, polyethylene and polypropylene-type fibers comprising (A) impregnating said fibers at a temperature of about to 70 C.
- aqueous pad liquor having a pH ranging from 2 to 10
- pad liquor contains as essential ingredients a non-cationic dyestufi capable of drawing on said fibers from a pad liquor of a pH in the aforesaid range
- a thickener and a carrier mixture consisting essentially of (a) an unsulfated amide of substantially entirely saturated fatty acid of 8 to 14 carbon atoms substituted by from 0 to 1 higher alkyl-phenoxy radical wherein the higher alkyl moiety has from 8 to not more than 12 carbon atoms, amidified with a member selected from the group consisting of (a) monoto di-hydroxyalky-lamine offrom 2 to 4 carbon atoms, having one hydroxy group in w-position,
- N-ethyl-N-w-hydroxyalkylamine of a total of from 4 to 5 carbon atoms
- a process for pad-dyeing polyamide fibers comprising- (A) impregnating said fibers at a temperature of about 30 to 70 C. with an aqueous pad liquor of a pH ranging from 2 to 10, which pad liquor contains as essential ingredients non-cationic dyes-tufl capable of drawing on said fibers from a pad liquor of a pH in the aforesaid range, a thickener and a carrier mixture consisting essentially of (a) an amide of substantially entirely saturated fatty acid of 8 to 14 carbon atoms amidified with bis-(w-hydroxyalkyl)-amine of a total of from 4 to 6 carbon atoms,
- component under (b) is a sulfated condensation product of alkylphenol the alkyl moiety of which contains from 8 to 12 carbon atoms, with ethylene oxide the molar ratio of alkylphenol to ethylene oxide being from 1:1 to 1:20.
- component under (b) is a sulfated condensation product of an alkanol of from 8 to 14 carbon atoms with ethylene oxide the molar ratio of alkanol to ethylene oxide being from 1:1 to 1:20.
- said padliquor contains a dyestuff carrier consisting essentially of (a) coconut oil fatty acid N,N-'bis-(fl-hydroxyethyl)- amide,
- (c) isopropanol, the proportions by weight of (a) to (b) ranging from about 2:1 to 1:2, and the content of (c) ranging from 4 to 20% by weight calculated on the weight of said mixture.
- said padliquor contains a dyestutf carrier consisting essentially of (a) a coconut oil fatty acid N,N-bit-(w-hydroxyalkyhamide,
- component under (b) is an alkali metal, ammonium, lower alkylammonium or w-hydroxy-lower alkylammonium salt of a sulfated condensation product of alkanol of from 8 to 14 carbon atoms with ethylene oxide the molar ratio of alkanol to ethylene oxide being from 1:1 to 1:20.
- said padliquor contains a dyestufi' carrier consisting essentially of (a) coconut oil fatty acid N,N-bis-(5-hydroxyethyl)- amide,
- (c) a mixture of isopropanol and fi-alkoxy-methanol of from 3 to 8 carbon atoms, of a weight ratio of 1:4 to 4: 1; the proportions by weight of (a) to b) ranging from about 2:1 to 1:2, and the content of (c) ranging from 4 to 20% by weight calculated on the weight of said mixture.
- said padliquor contains a dyestuff carrier consisting essentially of (a) a coconut oil fatty acid N,N-bis-(w-hydroxyalkyD- amide of a total of from 4 to 6 carbon atoms, and
- (c) isopropanol, the proportions by weight of (a) to (b) ranging from about 2:1 to 1:2, and the content of (c) ranging from 4 to 20% by weight calculated on the weight of said mixture.
- said pad-liquor contains a dyestutf carrier consisting essentially of (a) the ammonium salt of sulphated nonylphenol triglycol ether,
- (c) isopropanol, the proportions by weight of (a) to ('b) ranging from about 2:1 to 1:2, and the content of (c) ranging from 4 to 20% by weight calculated on the weight of said mixture.
- a process for printing woolen material comprising (A) printing textile material made from unchlorinated wool at a temperature of about 15 to 55 C. with a printing mixture having a pH ranging from 2 to 10, which mixture contains as essential ingredients, apart from water, a dyestutf capable of drawing on said fibers from a medium of a pH in the aforesaid range, and a thickener, a dyestuff carrier mixture consisting essentially of (a) an unsulfated amide of substantially entirely saturated fatty acid of 8 to 14 carbon atoms substituted by from 0 to 1 higher alkyl-phenoxy radical wherein the higher alkyl moiety has from 8 to not more than 12 carbon atoms, amidified with a member selected from the group consisting of v (a) mono-w-hydroxyalkylamine of from 2 to 4 carbon atoms, (5) bis-(w-hydroxyalkyl)-amine of a total of from 4 to 6 carbon atoms, (7) N-methyl-N-w-hydroxyalky
- (c) a member selected from the group consist ing of isopropanol and a fi-alkoxy-ethanol of a total of from 3 to 8 carbon atoms, the proportions by weight of (a) to (b) ranging from about 2:1 to 1:2, and the content of (c) ranging from '0 to 20% 'by weight, calculated on the total weight of said mixture, the content of said carrier mixture in said pad liquor ranging from about 5 to 100 grams per liter of liquor, and
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH159463A CH413776A (de) | 1963-02-08 | 1963-02-08 | Verfahren zum Färben oder Bedrucken von Textilfasern aus organischem Material |
Publications (1)
Publication Number | Publication Date |
---|---|
US3391985A true US3391985A (en) | 1968-07-09 |
Family
ID=4214057
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US409349A Expired - Lifetime US3391985A (en) | 1963-02-08 | 1964-11-02 | Process for pad-dyeing and printing wool and synthetic textile fibers in carrier compositions |
Country Status (8)
Country | Link |
---|---|
US (1) | US3391985A (de) |
AT (1) | AT254121B (de) |
BE (1) | BE643548A (de) |
CH (1) | CH413776A (de) |
DE (1) | DE1290913B (de) |
ES (1) | ES296220A1 (de) |
GB (1) | GB1017864A (de) |
NL (1) | NL6401027A (de) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3469930A (en) * | 1965-05-25 | 1969-09-30 | Ici Ltd | Wool dyeing process |
US3528761A (en) * | 1966-05-06 | 1970-09-15 | Geigy Ag J R | Continuous dyeing and printing process and dye compositions suitable therefor |
US3619123A (en) * | 1967-08-07 | 1971-11-09 | Bayer Ag | Process for dyeing fiber materials of synthetic polyamides with acid dyestuffs |
US3652200A (en) * | 1969-09-23 | 1972-03-28 | Kazuo Miyasaka | Concentrated sulfuric acid-dye solution dyeing |
US3658460A (en) * | 1968-04-26 | 1972-04-25 | Sandoz Ltd | Process for dyeing synthetic polyamide textiles in the presence of organic sulphonic acids and basic nitrogen compounds |
US3981679A (en) * | 1975-05-21 | 1976-09-21 | Diamond Shamrock Corporation | Method for dyeing the jute backing of multilevel nylon carpet without staining the nylon face fibers |
US4179267A (en) * | 1972-07-14 | 1979-12-18 | Ciba-Geigy Corporation | Stable, highly concentrated dyestuff solutions miscible with water in any proportion |
US4212749A (en) * | 1974-07-05 | 1980-07-15 | Bayer Aktiengesellschaft | Liquid preparation of fatty acid/alkanolamine condensates |
Citations (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2042473A (en) * | 1932-12-09 | 1936-06-02 | Rit Products Corp | Dye preparation |
US2043179A (en) * | 1932-12-09 | 1936-06-02 | Rit Products Corp | Dye preparation |
US2089212A (en) * | 1936-06-08 | 1937-08-10 | Kritchevsky Wolf | Hydrotropic fatty material and method of making same |
US2216617A (en) * | 1938-08-31 | 1940-10-01 | Katz Jacob | Surface active anionic compounds of amino alcohols |
US2383737A (en) * | 1942-02-18 | 1945-08-28 | Procter & Gamble | Detergent composition |
US2527076A (en) * | 1947-02-24 | 1950-10-24 | Procter & Gamble | Detergent composition |
US2607740A (en) * | 1950-05-03 | 1952-08-19 | Colgate Palmolive Peet Co | Liquid anionic-dialkylolamide detergent composition |
US3057674A (en) * | 1960-01-12 | 1962-10-09 | Chicopee Mfg Corp | Dyeing carriers and their use |
US3083069A (en) * | 1959-09-02 | 1963-03-26 | Geigy Ag J R | Process for the dyeing of polypeptide fibres |
US3086832A (en) * | 1958-03-21 | 1963-04-23 | Process for finishing dyeings | |
US3097040A (en) * | 1959-02-19 | 1963-07-09 | Ciba Company Inc | Process for dyeing nitrogenous fibers |
US3097047A (en) * | 1961-04-27 | 1963-07-09 | Tanatex Chemical Corp | Dyeing synthetic fibers with alkyl naphthalene composition |
US3211514A (en) * | 1965-10-12 | Process for dyeing and printing netrugen-containhng fibers |
-
1963
- 1963-02-08 CH CH159463A patent/CH413776A/de unknown
-
1964
- 1964-02-07 DE DEG39794A patent/DE1290913B/de active Pending
- 1964-02-07 AT AT99464A patent/AT254121B/de active
- 1964-02-07 ES ES296220A patent/ES296220A1/es not_active Expired
- 1964-02-07 BE BE643548D patent/BE643548A/xx unknown
- 1964-02-07 GB GB5199/64A patent/GB1017864A/en not_active Expired
- 1964-02-07 NL NL6401027A patent/NL6401027A/xx unknown
- 1964-11-02 US US409349A patent/US3391985A/en not_active Expired - Lifetime
Patent Citations (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3211514A (en) * | 1965-10-12 | Process for dyeing and printing netrugen-containhng fibers | ||
US2043179A (en) * | 1932-12-09 | 1936-06-02 | Rit Products Corp | Dye preparation |
US2042473A (en) * | 1932-12-09 | 1936-06-02 | Rit Products Corp | Dye preparation |
US2089212A (en) * | 1936-06-08 | 1937-08-10 | Kritchevsky Wolf | Hydrotropic fatty material and method of making same |
US2216617A (en) * | 1938-08-31 | 1940-10-01 | Katz Jacob | Surface active anionic compounds of amino alcohols |
US2383737A (en) * | 1942-02-18 | 1945-08-28 | Procter & Gamble | Detergent composition |
US2527076A (en) * | 1947-02-24 | 1950-10-24 | Procter & Gamble | Detergent composition |
US2607740A (en) * | 1950-05-03 | 1952-08-19 | Colgate Palmolive Peet Co | Liquid anionic-dialkylolamide detergent composition |
US3086832A (en) * | 1958-03-21 | 1963-04-23 | Process for finishing dyeings | |
US3097040A (en) * | 1959-02-19 | 1963-07-09 | Ciba Company Inc | Process for dyeing nitrogenous fibers |
US3083069A (en) * | 1959-09-02 | 1963-03-26 | Geigy Ag J R | Process for the dyeing of polypeptide fibres |
US3057674A (en) * | 1960-01-12 | 1962-10-09 | Chicopee Mfg Corp | Dyeing carriers and their use |
US3097047A (en) * | 1961-04-27 | 1963-07-09 | Tanatex Chemical Corp | Dyeing synthetic fibers with alkyl naphthalene composition |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3469930A (en) * | 1965-05-25 | 1969-09-30 | Ici Ltd | Wool dyeing process |
US3528761A (en) * | 1966-05-06 | 1970-09-15 | Geigy Ag J R | Continuous dyeing and printing process and dye compositions suitable therefor |
US3619123A (en) * | 1967-08-07 | 1971-11-09 | Bayer Ag | Process for dyeing fiber materials of synthetic polyamides with acid dyestuffs |
US3658460A (en) * | 1968-04-26 | 1972-04-25 | Sandoz Ltd | Process for dyeing synthetic polyamide textiles in the presence of organic sulphonic acids and basic nitrogen compounds |
US3652200A (en) * | 1969-09-23 | 1972-03-28 | Kazuo Miyasaka | Concentrated sulfuric acid-dye solution dyeing |
US4179267A (en) * | 1972-07-14 | 1979-12-18 | Ciba-Geigy Corporation | Stable, highly concentrated dyestuff solutions miscible with water in any proportion |
US4212749A (en) * | 1974-07-05 | 1980-07-15 | Bayer Aktiengesellschaft | Liquid preparation of fatty acid/alkanolamine condensates |
US3981679A (en) * | 1975-05-21 | 1976-09-21 | Diamond Shamrock Corporation | Method for dyeing the jute backing of multilevel nylon carpet without staining the nylon face fibers |
Also Published As
Publication number | Publication date |
---|---|
CH413776A (de) | 1966-02-15 |
AT254121B (de) | 1967-05-10 |
ES296220A1 (es) | 1964-06-16 |
NL6401027A (de) | 1964-08-10 |
BE643548A (de) | 1964-08-07 |
GB1017864A (en) | 1966-01-19 |
DE1290913B (de) | 1969-03-20 |
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