US3199942A - Divinyl sulfone, diisocyanate, dicarboxylic acid or dihydroxysulfide reaction products with polyethylene ethers in high temperature pad dyeing and printing - Google Patents
Divinyl sulfone, diisocyanate, dicarboxylic acid or dihydroxysulfide reaction products with polyethylene ethers in high temperature pad dyeing and printing Download PDFInfo
- Publication number
- US3199942A US3199942A US179245A US17924562A US3199942A US 3199942 A US3199942 A US 3199942A US 179245 A US179245 A US 179245A US 17924562 A US17924562 A US 17924562A US 3199942 A US3199942 A US 3199942A
- Authority
- US
- United States
- Prior art keywords
- dyeing
- diisocyanate
- polyether
- textile materials
- group
- 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
- 239000007795 chemical reaction product Substances 0.000 title claims description 11
- -1 polyethylene Polymers 0.000 title claims description 10
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 title claims description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 title claims description 4
- 239000004698 Polyethylene Substances 0.000 title description 3
- 229920000573 polyethylene Polymers 0.000 title description 3
- HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical compound OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 title description 2
- 150000002170 ethers Chemical class 0.000 title description 2
- 238000009980 pad dyeing Methods 0.000 title description 2
- 125000005442 diisocyanate group Chemical group 0.000 title 1
- 229920000570 polyether Polymers 0.000 claims description 38
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 30
- 238000004043 dyeing Methods 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 22
- 239000000463 material Substances 0.000 claims description 13
- 239000000047 product Substances 0.000 claims description 10
- 239000004753 textile Substances 0.000 claims description 10
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000007859 condensation product Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 229920002994 synthetic fiber Polymers 0.000 claims description 4
- 239000000835 fiber Substances 0.000 claims description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims description 2
- 229920000056 polyoxyethylene ether Polymers 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000004758 synthetic textile Substances 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000004744 fabric Substances 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 description 8
- 239000000975 dye Substances 0.000 description 8
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 5
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 5
- 229950006389 thiodiglycol Drugs 0.000 description 5
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 210000002268 wool Anatomy 0.000 description 4
- BMRVLXHIZWDOOK-UHFFFAOYSA-N 2-butylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(CCCC)=CC=C21 BMRVLXHIZWDOOK-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000007046 ethoxylation reaction Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 229920002239 polyacrylonitrile Polymers 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229940117927 ethylene oxide Drugs 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 230000009183 running Effects 0.000 description 2
- 125000003375 sulfoxide group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical class CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- LCVCUJWKJNFDMY-UHFFFAOYSA-N 2,2-diphenylpropane-1,1-diol Chemical compound C=1C=CC=CC=1C(C(O)O)(C)C1=CC=CC=C1 LCVCUJWKJNFDMY-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- GVNHOISKXMSMPX-UHFFFAOYSA-N 2-[butyl(2-hydroxyethyl)amino]ethanol Chemical class CCCCN(CCO)CCO GVNHOISKXMSMPX-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- SGHZXLIDFTYFHQ-UHFFFAOYSA-L Brilliant Blue Chemical compound [Na+].[Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 SGHZXLIDFTYFHQ-UHFFFAOYSA-L 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical class CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920001727 cellulose butyrate Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940043237 diethanolamine Drugs 0.000 description 1
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 description 1
- DWHOIYXAMUMQTI-UHFFFAOYSA-L disodium;2-[(1-sulfonatonaphthalen-2-yl)methyl]naphthalene-1-sulfonate Chemical compound [Na+].[Na+].C1=CC2=CC=CC=C2C(S(=O)(=O)[O-])=C1CC1=CC=C(C=CC=C2)C2=C1S([O-])(=O)=O DWHOIYXAMUMQTI-UHFFFAOYSA-L 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 229940031098 ethanolamine Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007970 homogeneous dispersion Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- ARZLUCYKIWYSHR-UHFFFAOYSA-N hydroxymethoxymethanol Chemical group OCOCO ARZLUCYKIWYSHR-UHFFFAOYSA-N 0.000 description 1
- GLZWNFNQMJAZGY-UHFFFAOYSA-N octaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCOCCOCCO GLZWNFNQMJAZGY-UHFFFAOYSA-N 0.000 description 1
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 description 1
- 229950005308 oxymethurea Drugs 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920005586 poly(adipic acid) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- AFTOVGIFYVNBID-UHFFFAOYSA-M sodium;2-butylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=CC2=C(S([O-])(=O)=O)C(CCCC)=CC=C21 AFTOVGIFYVNBID-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/70—Material containing nitrile groups
- D06P3/72—Material containing nitrile groups using dispersed dyestuffs
-
- D—TEXTILES; PAPER
- D02—YARNS; MECHANICAL FINISHING OF YARNS OR ROPES; WARPING OR BEAMING
- D02J—FINISHING OR DRESSING OF FILAMENTS, YARNS, THREADS, CORDS, ROPES OR THE LIKE
- D02J1/00—Modifying the structure or properties resulting from a particular structure; Modifying, retaining, or restoring the physical form or cross-sectional shape, e.g. by use of dies or squeeze rollers
- D02J1/22—Stretching or tensioning, shrinking or relaxing, e.g. by use of overfeed and underfeed apparatus, or preventing stretch
- D02J1/229—Relaxing
-
- 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
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
- D06P3/245—Polyamides; Polyurethanes using metallisable or mordant dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/54—Polyesters using dispersed dyestuffs
-
- 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
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/922—Polyester fiber
Definitions
- polyethers there may be mentioned, for example, the condensation products obtainable, on the one hand, from polyethylene glycols, ethoxylated diand polyalcohols, ethoxylated diand polyphenols, ethoxylated monoand polyamines or ethoxylated diand polycarboxylic acids, and, on theother hand, from aliphatic, cycloaliphatic or aromatic dicarboxylic acids, thiodiglycol or other fl,fi'-dihydroxy-alkyl sulfides described, for example, in French patent specification No. 1,201,171.
- polystyrene foams for example hexamethylene-diisocyanate, toluylene-diisocyanate, 4,4'-diisocyanate-diphenyl-methane, 4,4 diisocyanato-dicyclohexylmethane or w,w'-diisocyanatoxylene, or divinyl sulfones.
- polyethylene glycols or of ethoxylation products of the aforesaid kind and diand polyisocyanates for example hexamethylene-diisocyanate, toluylene-diisocyanate, 4,4'-diisocyanate-diphenyl-methane, 4,4 diisocyanato-dicyclohexylmethane or w,w'-diisocyanatoxylene, or divinyl sulfones.
- the mixed polymerisates may be taken into consideration which are obtainable from ethylene-oxide and cyclohexene-oxide or styrene oxide, optionally with the addition of propylene oxide, as well as the mixed polymerisates which are obtain-able from ethylene oxide and phenyl-glycide ether, ,cresyl-glycide ether, methoxy-phenyl-glycide ether or por mphenylene diglycide ether.
- polyethers obtained from the ethoxylation products of diphenols in the first instance from the ethoxylation products from resorcinol, hydroquinone, 4,4'-dihydroxy-diphenyl-methane, 4,4 dihydroxy-diphenyl-propane and 4,4'-dihydroxy-diphenyl-sulfone.
- polyethers which yield at least 1% solutions in water at room temperature.
- the water-solubility of polyethers increases with the increasing content of ether oxygen atoms and/ or hydrophilic groups such as hydroxyl groups, amino groups, ammonium groups, sulfoxide groups, sulfone groups, sulfonic acid groups or carboxylic groups.
- the textile materials to be dyed with the aid of the process according to the invention may be based on a great variety of synthetic products such as, for example, polyacrylonitrile, the mixed polymerisates of acrylonitrile with other vinyl compounds as, e.g., acrylic esters, acryl amides, vinyl-pyridine, vinyl chloride or vinylidene chloride, polyamides as, e.g., polycaprolactam, polyadipic acid hexamethylene amide, poly-w-amino-undecanic acid, or polyurethanes or polyesters as, e.g., those from terephthalic acid and ethylene glycol or 1,4-dimethylol-cyclohexane.
- synthetic products such as, for example, polyacrylonitrile, the mixed polymerisates of acrylonitrile with other vinyl compounds as, e.g., acrylic esters, acryl amides, vinyl-pyridine, vinyl chloride or vinylidene chloride, polyamides as,
- the process according to the present invention also comprises the dyeing of textile materials which are produced from cellulose esters, for example, from cellulose triacetate or butyrate.
- the process according to the invention may also be applied to mixed fabrics of synthetic fibres, or mixed fabrics of synthetic fibres and fibres of natu'ralorigin such aswool o'r cotton.
- dyestulis of a most varied type may also be used in the present a es); example, disperse dyestuffs, vat dyestulfs, acid wool "dyestuffs, metal complex dyestuffs or basic dyestufls.
- Mixed fabrics can be dyed by appropriate choice of the dy'es't'ulf from one or more baths, possibly by inserting an exhaust process, and also selectively, if desired.
- the polyethers to be used according to the invention are generally employed in quantities of 0.210%, preferably O.54%, referred to the padding solution or printing paste used. In general, they are added to the final pad ding solution or printing paste, but they may also be admixed to the dyestuifs.
- the process according to the invention ensures a completely homogeneous dispersion of the dyestuffs before or after fixing.
- the absorptioriof the padding liquor which is very difiicult when hydrophobic fibres are concerned, is improved; thus the otherwise required use of thickening agents which frequently retain the dyestutf, often entail the formation of dyestufi? conglomerates and give rise to a blocking of the dyeing apparatus becomes unnecessary.
- the polyethers appreciably improve the dyestutf yield, but above all they bring about unobjectionable dyeings even when several dyestuffs are used. Two-sidedness and runnings of the dyestuff at the selvedges of the dye ing are prevented. Moreover, the polyethers canbe washed out, and resist natural fibres where present.
- auxiliaries may also be used, for example softening agents in order to improve the handle of the textile materials, bydrotropic substances to increase the solubility of the dyestuffs in an aqueous bath,.or carrier to increase the penetration of the dyestuffs into the fibres.
- a special method of carrying out the present invention consists in adding to the dyeing liquor in addition to polyethers containing groups condensable with formaldehyde such. as, for example resorcinol, hydroquinone, phenol or aniline groups, foifmaldehydeor compounds splitting off formaldehydeor methylol groups or methylol ether group-containing compounds.
- formaldehyde such as, for example resorcinol, hydroquinone, phenol or aniline groups, foifmaldehydeor compounds splitting off formaldehydeor methylol groups or methylol ether group-containing compounds.
- EXAMPLE 1 A fabric of polyethylene ter ephthalate fibers is impregnated on a foulard with a liquor containing per litre 20 g. of the dyestuli (a) and 20 g. of the polyether described below. The fabric is then squeezed to a weight increase of about 70% and dried at-10D? C.'in a suspension nozzle drier. For fixing the dyeing, the fabric is subsequently treated for 60 seconds at 190', C. withhot air in the same apparatus or in a tentering frame, then rinsed and washedwith hot water. g I 1 The fabric shows an entirely uniform and unobjectionable fixed yellow dyeing. The shade is fuller than that of a dyeing which can be attained with the use of the same dyestufi amount (referred to the fabric) according to the polyether described in Example 1.
- the polyether used is obtained as follows: Ethoxylated resorcinol of molecular weight 1100 is condensed with thiodiglycol in a molecular ratio of 111.8 in the presence of 1 percent by weight of phosphoric acid at a temperature of 180-185" C., first under normal pressure, then in a vacuum at to mm. Hg, until a hydroxyl number of to 22 is obtained.
- EXAMPLE 2 As described in Example 1 a fabric of polyethylene terephthalate fibres is treated with a liquor containing per litre g. of the dyestuif (a), 5 g. of the dyestutf (b), and 3 g. of the dyestutf (c) as well as 20 g. of
- the so-treated fabric shows an entirely even brown shade. Without using the polyether an uneven dyeing is obtained on which the individual dyestuff components are distinctly to be seen.
- EXAMPLE 3 A fabric of polyacrylonitrile filaments is treated, as described in Example 1, with a liquor containing per litre 3 g. of the dyestutf (a), 20 g. of the polyether described in Example 1, 8 g. of the condensation product from octaethylene glycol and dimethylol urea as well as 2 g. of butyl-naphthalene sulfonic acid.
- the fabric shows an even blue shade, and it possesses morover an antistatic finish which is fast to washing. Even after 10 washings with conventional mild detergents the surface resistance is 10 times lower than that of untreated fabric.
- EXAMPLE 4 A fabric of polyacrylonitrile filaments is treated with a liquor containing per-litre 2.5 g. of the dyestutf (d), 20 g. of the polyether described below and 2.7 g. of ethoxylated oleyl alcohol. The fabric is subsequently heated to 180 C. for 1 minute in order to fix the dyeing. The red pastel shade obtained is entirely even, and the fabric possesses a full soft handle.
- the polyether used is prepared by addition of ethoxylated resorcinol of molecular weight 1250 to divinyl sulphone in a molecular ratio of 7:6 in the presence of sodium methylate as catalyst.
- EXAMPLE 5 A fabric of polycaprolactam is treated with a solution containing per litre g. of the chromium complex of the dyestuff (e) and 25 g. of the polyether described below. For fixing of the dyeing, the fabric is heated to 192 C. for 70 seconds. Colorimetric analysis shows that the dyestuff yield is higher by 40% than that obtained with the use of a solution containing no polyether.
- the polyether used is produced by addition of ethoxylated resorcinol of molecular weight 1300 to hexamethylene diisocyanate in a molecular ratio of 7: 6.
- EXAMPLE 6 A mixed fabric of polyethylene tercphthalate fibres and 45% wool is dyed as described in Example 1,
- the polyether used is produced by oxidation'of the polyether described in Example 1 with 1 mol of the hydrogen peroxide per mol of the thiodiglycol contained in the polyether.
- EXAMPLE 7 A polyethylene terephthalate band such as is used for safety belts, is dyed with a liquor. containing per litre 30 g. of the dyestutf (c), 3.5 g. of the dyestuif (d), 13 g. of the dyestuff (e), 20 g. of the polyether described below, and 2 g. of butyl-naphthalene-sulfonic acid.
- the dyeing method corresponds to the mode of operation indicated in Example 1, with the exception that the band is squeezed to a weight increase of 30%.
- a grey dyeing is obtained which, after a reductive after-treatment, is distinguished by good fastuess properties and an especially good penetration.
- the polyether used is produced by condensing ethoxylated resorcinol of molecular weight 1700 with di-(B- hydroxypropyl)-sulfide in a molecular ratio of 1:3 until a molecular weight of 6400 is attained.
- Example 8 -A fabric of polyethyleneterephthalate fibres is impregnated on the foulard with a liquor containing per litre g. of the dyestutf (c), 30 g. of the polyether described below, and 3 g. of methylene-bis-naphthalene sulfonic acid sodium salt.
- the fabric After squeezing the material to a weight increase of about 70%, the fabric is dried as described in Example 1, and the dyeing subsequently fixed.
- An unobjectionably fixed, brilliantblue dyeing is obtained which, after a reductive after-treatment with a liquor containing per litre 3 g. of a sodium hydroxide solution and 2 g. of hydrosulfite, has an outstanding fastness to rubbing.
- the dyestutf yield is higher by about 50% than that obtained by a control experiment carried out in the absence of the polyether according to the invention;
- the polyether used is obtained by heating to C. for four hours ethoxylated N-methyl-ethanol-amine of molecular weight 1000, with hexamethylene-di-isocyanate in a molecular ratio of 100:92.
- polyether obtained by heating ethoxylated N-butyl-diethanol-amine of molecular weight 1200 with sebacic acid until thernolecular weight of the product formed amounts to 5000.
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Description
nited States DIVINYL SULFONE, DIISOCYANATE, DICARBOX- YLIC ACID R DIHYDROXYSULFIDE REAC- TION PRODUCTS WITH POLYETHYLENE ETHERS IN HIGH TEMPERATURE PAD DYEING AND PRHJTING y s Robert Kuth and Hunswilli von Brachel, Cologne-Sulz, Germany, assignors to Farbenfabriken Bayer Aktie'ngesellschaft, Leverkusen, Germany, a German corporation s r No Drawing Filed Mar. 12, 19 62, Ser. No, 179,245
Claims priority, application Germany, Mar. 14, 1961,
9 Claims. (Cl. 8-55) five carbon atoms directly linked with one another.
As suitable polyethers there may be mentioned, for example, the condensation products obtainable, on the one hand, from polyethylene glycols, ethoxylated diand polyalcohols, ethoxylated diand polyphenols, ethoxylated monoand polyamines or ethoxylated diand polycarboxylic acids, and, on theother hand, from aliphatic, cycloaliphatic or aromatic dicarboxylic acids, thiodiglycol or other fl,fi'-dihydroxy-alkyl sulfides described, for example, in French patent specification No. 1,201,171. Furthermore, there may be mentioned the poly-addition products of polyethylene glycols or of ethoxylation products of the aforesaid kind and diand polyisocyanates, for example hexamethylene-diisocyanate, toluylene-diisocyanate, 4,4'-diisocyanate-diphenyl-methane, 4,4 diisocyanato-dicyclohexylmethane or w,w'-diisocyanatoxylene, or divinyl sulfones. Moreover, the mixed polymerisates may be taken into consideration which are obtainable from ethylene-oxide and cyclohexene-oxide or styrene oxide, optionally with the addition of propylene oxide, as well as the mixed polymerisates which are obtain-able from ethylene oxide and phenyl-glycide ether, ,cresyl-glycide ether, methoxy-phenyl-glycide ether or por mphenylene diglycide ether. Especially suitable are the polyethers obtained from the ethoxylation products of diphenols, in the first instance from the ethoxylation products from resorcinol, hydroquinone, 4,4'-dihydroxy-diphenyl-methane, 4,4 dihydroxy-diphenyl-propane and 4,4'-dihydroxy-diphenyl-sulfone.
In general, it is advantageous to use those polyethers which yield at least 1% solutions in water at room temperature. The water-solubility of polyethers increases with the increasing content of ether oxygen atoms and/ or hydrophilic groups such as hydroxyl groups, amino groups, ammonium groups, sulfoxide groups, sulfone groups, sulfonic acid groups or carboxylic groups.
The textile materials to be dyed with the aid of the process according to the invention may be based on a great variety of synthetic products such as, for example, polyacrylonitrile, the mixed polymerisates of acrylonitrile with other vinyl compounds as, e.g., acrylic esters, acryl amides, vinyl-pyridine, vinyl chloride or vinylidene chloride, polyamides as, e.g., polycaprolactam, polyadipic acid hexamethylene amide, poly-w-amino-undecanic acid, or polyurethanes or polyesters as, e.g., those from terephthalic acid and ethylene glycol or 1,4-dimethylol-cyclohexane.
I Par-sates Aug. 10, 1965 Furthermore, the process according to the present invention also comprises the dyeing of textile materials which are produced from cellulose esters, for example, from cellulose triacetate or butyrate. The process according to the invention may also be applied to mixed fabrics of synthetic fibres, or mixed fabrics of synthetic fibres and fibres of natu'ralorigin such aswool o'r cotton.
As with the known dyeing process mentioned above, dyestulis of a most varied type may also be used in the present a es); example, disperse dyestuffs, vat dyestulfs, acid wool "dyestuffs, metal complex dyestuffs or basic dyestufls. Mixed fabrics can be dyed by appropriate choice of the dy'es't'ulf from one or more baths, possibly by inserting an exhaust process, and also selectively, if desired. v
The polyethers to be used according to the invention are generally employed in quantities of 0.210%, preferably O.54%, referred to the padding solution or printing paste used. In general, they are added to the final pad ding solution or printing paste, but they may also be admixed to the dyestuifs The process according to the invention ensures a completely homogeneous dispersion of the dyestuffs before or after fixing. The absorptioriof the padding liquor, which is very difiicult when hydrophobic fibres are concerned, is improved; thus the otherwise required use of thickening agents which frequently retain the dyestutf, often entail the formation of dyestufi? conglomerates and give rise to a blocking of the dyeing apparatus becomes unnecessary. The polyethers appreciably improve the dyestutf yield, but above all they bring about unobjectionable dyeings even when several dyestuffs are used. Two-sidedness and runnings of the dyestuff at the selvedges of the dye ing are prevented. Moreover, the polyethers canbe washed out, and resist natural fibres where present.
In the process according to the invention other auxiliaries may also be used, for example softening agents in order to improve the handle of the textile materials, bydrotropic substances to increase the solubility of the dyestuffs in an aqueous bath,.or carrier to increase the penetration of the dyestuffs into the fibres.
A special method of carrying out the present invention consists in adding to the dyeing liquor in addition to polyethers containing groups condensable with formaldehyde such. as, for example resorcinol, hydroquinone, phenol or aniline groups, foifmaldehydeor compounds splitting off formaldehydeor methylol groups or methylol ether group-containing compounds. In this way the textile materials can be dyed in one bath and obtain an antistatic finish fast to washing.
The aforesaid satisfactory results cannot be attained to the same extent with the auxiliaries which have previously been proposed for the dyeing process concerned.
The following examples serve to illustrate the invention without, however, limiting tli'escope thereof. The dyestuffs designated in the examples by (a) to (e) are'explained in the list at the end of the description.
EXAMPLE 1 A fabric of polyethylene ter ephthalate fibers is impregnated on a foulard with a liquor containing per litre 20 g. of the dyestuli (a) and 20 g. of the polyether described below. The fabric is then squeezed to a weight increase of about 70% and dried at-10D? C.'in a suspension nozzle drier. For fixing the dyeing, the fabric is subsequently treated for 60 seconds at 190', C. withhot air in the same apparatus or in a tentering frame, then rinsed and washedwith hot water. g I 1 The fabric shows an entirely uniform and unobjectionable fixed yellow dyeing. The shade is fuller than that of a dyeing which can be attained with the use of the same dyestufi amount (referred to the fabric) according to the polyether described in Example 1.
the known therrriosol process or to the exhaust process while using commercial carriers.
The polyether used is obtained as follows: Ethoxylated resorcinol of molecular weight 1100 is condensed with thiodiglycol in a molecular ratio of 111.8 in the presence of 1 percent by weight of phosphoric acid at a temperature of 180-185" C., first under normal pressure, then in a vacuum at to mm. Hg, until a hydroxyl number of to 22 is obtained.
EXAMPLE 2 As described in Example 1 a fabric of polyethylene terephthalate fibres is treated with a liquor containing per litre g. of the dyestuif (a), 5 g. of the dyestutf (b), and 3 g. of the dyestutf (c) as well as 20 g. of
After the customary finish the so-treated fabric shows an entirely even brown shade. Without using the polyether an uneven dyeing is obtained on which the individual dyestuff components are distinctly to be seen.
EXAMPLE 3 A fabric of polyacrylonitrile filaments is treated, as described in Example 1, with a liquor containing per litre 3 g. of the dyestutf (a), 20 g. of the polyether described in Example 1, 8 g. of the condensation product from octaethylene glycol and dimethylol urea as well as 2 g. of butyl-naphthalene sulfonic acid.
After the customary finish, the fabric shows an even blue shade, and it possesses morover an antistatic finish which is fast to washing. Even after 10 washings with conventional mild detergents the surface resistance is 10 times lower than that of untreated fabric.
EXAMPLE 4 A fabric of polyacrylonitrile filaments is treated with a liquor containing per-litre 2.5 g. of the dyestutf (d), 20 g. of the polyether described below and 2.7 g. of ethoxylated oleyl alcohol. The fabric is subsequently heated to 180 C. for 1 minute in order to fix the dyeing. The red pastel shade obtained is entirely even, and the fabric possesses a full soft handle. The polyether used is prepared by addition of ethoxylated resorcinol of molecular weight 1250 to divinyl sulphone in a molecular ratio of 7:6 in the presence of sodium methylate as catalyst.
EXAMPLE 5 A fabric of polycaprolactam is treated with a solution containing per litre g. of the chromium complex of the dyestuff (e) and 25 g. of the polyether described below. For fixing of the dyeing, the fabric is heated to 192 C. for 70 seconds. Colorimetric analysis shows that the dyestuff yield is higher by 40% than that obtained with the use of a solution containing no polyether.
The polyether used is produced by addition of ethoxylated resorcinol of molecular weight 1300 to hexamethylene diisocyanate in a molecular ratio of 7: 6.
EXAMPLE 6 A mixed fabric of polyethylene tercphthalate fibres and 45% wool is dyed as described in Example 1,
with a liquor containing per litre 25 g. of the dyestuff (c), 4 g. of the dyestufii (d), 3 g. of the dyestuff (e), 20 g. of the sulfoxide group-containing polyether described below, 4 g. of butyl-naphthalene-sulfonic acid sodium salt and 4 g. of butyl-naphthalene-sulfonic acid. The navy blue dyeing obtained on the polyester portion of the fabric shows no runnings at the selvedges or ends, the wool portion which is not stained is subsequently dyed on the winch in known manner with usual wool dyestuffs also yielding a navy blue dyeing so that an evenly dyed navy blue cloth is obtained. After working up 400 metres of the fabric there are not to be found any sublimed or mechanically rubbed off dyestutf particles neither on the suspension nozzle drier nor in the pin beds of the tendering frame.
The polyether used is produced by oxidation'of the polyether described in Example 1 with 1 mol of the hydrogen peroxide per mol of the thiodiglycol contained in the polyether.
EXAMPLE 7 A polyethylene terephthalate band such as is used for safety belts, is dyed with a liquor. containing per litre 30 g. of the dyestutf (c), 3.5 g. of the dyestuif (d), 13 g. of the dyestuff (e), 20 g. of the polyether described below, and 2 g. of butyl-naphthalene-sulfonic acid. The dyeing method corresponds to the mode of operation indicated in Example 1, with the exception that the band is squeezed to a weight increase of 30%. A grey dyeing is obtained which, after a reductive after-treatment, is distinguished by good fastuess properties and an especially good penetration.
The polyether used is produced by condensing ethoxylated resorcinol of molecular weight 1700 with di-(B- hydroxypropyl)-sulfide in a molecular ratio of 1:3 until a molecular weight of 6400 is attained.
Example 8 -A fabric of polyethyleneterephthalate fibres is impregnated on the foulard with a liquor containing per litre g. of the dyestutf (c), 30 g. of the polyether described below, and 3 g. of methylene-bis-naphthalene sulfonic acid sodium salt.
After squeezing the material to a weight increase of about 70%, the fabric is dried as described in Example 1, and the dyeing subsequently fixed. An unobjectionably fixed, brilliantblue dyeing is obtained which, after a reductive after-treatment with a liquor containing per litre 3 g. of a sodium hydroxide solution and 2 g. of hydrosulfite, has an outstanding fastness to rubbing. The dyestutf yield is higher by about 50% than that obtained by a control experiment carried out in the absence of the polyether according to the invention;
The polyether used is obtained by heating to C. for four hours ethoxylated N-methyl-ethanol-amine of molecular weight 1000, with hexamethylene-di-isocyanate in a molecular ratio of 100:92.
Instead of the polyether described above, there can be used with the same good result a polyether obtained by heating ethoxylated N-butyl-diethanol-amine of molecular weight 1200 with sebacic acid until thernolecular weight of the product formed amounts to 5000.
List of the dyestufls We claim: I
1. In a process for dyeing and printing synthetic textile materials and blends thereof with natural fibers by coloring the textile materials with a dyeing member selected from the group consisting of a padding dyebath preparation and dye printing paste, applying the dyeing member to the textile materials and fixing by heating to a temperature of at least C., the improvement consisting in applying to said textile materials and blends thereof, said dyeing member and an active amount of apolyether selected from the group consisting of (I) the reaction product of a first member consisting of a polyethylene oxide ether of dihydroxy benzene with a second member selected from the group consisting of (a) a p,B'-dihydroxy-alkyl-sulfide 6. The process of claim 1 wherein the polyether con- (b) adiisocyanate and sists of the reaction product of ethoxylated resorcinol (c) a divinyl sulfone, and with hexamethylene diisocyanate.
(II) the reaction product of a first member consisting 7. The process of claim 1 wherein the polyether conof polyoxyethylene ethers of polyalkanol amines 5 sists of the oxidation product obtained by means of hywith a second member selected from the group condrogen peroxide from the reaction product of ethoxylated sisting of resorcinol with thiodiglycol.
(a) adiisocyanate, and 8. The process of claim 1 wherein the polyether con- (b) a dicarboxylic acid, said product having at sists of the reaction product of ethoxylated N-inethylleast two hydroxyl groups; said first members 1 ethanolamine with hexamethylene diisocyanate.
repeatedly alternating with the second members 9. The process of claim 1 wherein the polyether conin the condensation product, one of said memsists of the reaction pr d of h ylated N-butylbers containing not less than 5 carbon atoms diethanolam-ine with sebacic acid.
directly linked with one another.-
2. The process of claim 1 wherein the polyether is 15 References Cited by the Examiner employed in a concentration of .2%10% referred to the UNITED STATES PATENTS dyeing component.
3. The process of claim 1 wherein the polyether con- 325823;? a1 X sists of the reaction product of ethoxylated resorcinol 2963513 12/60 Albrecht X with thiodiglycol. 2
4. The process of claim 1 wherein the polyether con- OTHER REFERENCES sists of the ereaction product of ethoxylated resorcinol A i Dyestufi Reporter, 1949, p. 593.
with di-(;8-hydroxypropyl)-sulfide.
5. The process of claim 1 wherein the polyether con- NORMAN TORCHIN Pr'mm Exammer' sists of the reaction product of ethoxylated resorcinol 25 MORRIS O. WOLK, A LOUIS MONACELL, with divinyl sulphone. Examiners.
Claims (1)
1. IN A PROCESS FOR DYEING AND PRINTING SYNTHETIC TEXTILE MATERIALS AND BLENDS THEREOF WITH NATURAL FIBERS BY COLORING THE TEXTILE MATERIALS WITH A DYEING MEMBER SELECTED FROM THE GROUP CONSISTING OF A PADDING DYEBATH PREPARATION AND DYE PRINTING PASTE, APPLYING THE DYEING MEMBER TO THE TEXTILE MATERIALS AND FIXING BY HEATING TO A TEMPERATURE OF AT LEAST 180*C., THE IMPROVEMENT CONSISTING IN APPLYING TO SAID TEXTILE MATERIALS AND BLENDS THEREOF, SAID DYEING MEMBER AND AN ACTIVE AMOUNT OF A POLYETHER SELECTED FROM THE GROUP CONSISTING OF (I) THE REACTION PRODUCT OF A FIRST MEMBER CONSISTING OF A POLYETHYLENE OXIDE ETHER OF DIHYDROXY BENZENE WITH A SECOND MEMBER SELECTED FROM THE GROUP CONSISTING OF (A) A B,B''-DIHYDROXY-ALKYL-SULFIDE (B) A DIISOCYANATE AND (C) A DIVINYL SULFONE, AND (II) THE REACTION PRODUCT OF A FIRST MEMBER CONSISTING OF POLYOXYETHYLENE ETHERS OF POLYALKANOL AMINES WITH A SECOND MEMBER SELECTED FROM THE GROUP CONSISTING OF (A) A DIISOCYANATE, AND (B) A DICARBOXYLIC ACID, SAID PRODUCT HAVING AT LEAST TWO HYDROXYL GROUPS; SAID FIRST MEMBERS REPEATEDLY ALTERNATING WITH THE SECOND MEMBERS IN THE CONDENSATION PRODUCT, ONE OF SAID MEMBERS CONTAINING NOT LESS THAN 5 CARBON ATOMS DIRECTLY LINKED WITH ONE ANOTHER.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF33413A DE1244707B (en) | 1961-03-14 | 1961-03-14 | Process for dyeing or printing textile materials made from synthetic fibers |
Publications (1)
Publication Number | Publication Date |
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US3199942A true US3199942A (en) | 1965-08-10 |
Family
ID=7095085
Family Applications (1)
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---|---|---|---|
US179245A Expired - Lifetime US3199942A (en) | 1961-03-14 | 1962-03-12 | Divinyl sulfone, diisocyanate, dicarboxylic acid or dihydroxysulfide reaction products with polyethylene ethers in high temperature pad dyeing and printing |
Country Status (7)
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US (1) | US3199942A (en) |
BE (1) | BE615102A (en) |
CH (1) | CH378848A (en) |
DE (1) | DE1244707B (en) |
FR (1) | FR1317644A (en) |
GB (1) | GB962278A (en) |
NL (2) | NL111304C (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3290111A (en) * | 1962-09-18 | 1966-12-06 | Bayer Ag | Process for improving the fastness properties of dyeings |
US3536438A (en) * | 1966-03-11 | 1970-10-27 | Sandoz Ag | Process of dyeing textile fibres using a phenyl sulphone dyeing assistant |
US3807945A (en) * | 1968-10-08 | 1974-04-30 | Hoechst Ag | Process for the dyeing of mixtures of cellulose, polyester and polyacrylonitrile fibers from one bath |
US3859045A (en) * | 1971-07-22 | 1975-01-07 | Allied Chem | Ethoxylated aliphatic tertiary amines to reduce ozone attack on dyes in polyamide fibers |
US3964861A (en) * | 1971-12-23 | 1976-06-22 | Allied Chemical Corporation | Alkoxylated aliphatic amines to inhibit ozone fading of dyed polyamides |
US4185962A (en) * | 1970-02-02 | 1980-01-29 | Sandoz Ltd. | Dyeing with organic dyestuffs dispersed in an organic liquid |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1970578A (en) * | 1930-11-29 | 1934-08-21 | Ig Farbenindustrie Ag | Assistants for the textile and related industries |
US2133480A (en) * | 1932-01-02 | 1938-10-18 | Ig Farbenindustrie Ag | Production of ethers suitable as dispersing agents and of preparations therefrom |
US2963513A (en) * | 1955-11-28 | 1960-12-06 | Ciba Ltd | Polyglycol ether derivatives |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE667744C (en) * | 1930-11-30 | 1938-11-19 | I G Farbenindustrie Akt Ges | Process for the preparation of condensation products which are soluble or easily dispersible in water |
DE694178C (en) * | 1930-11-30 | 1940-07-27 | I G Farbenindustrie Akt Ges | Process for the preparation of condensation products which are soluble or easily dispersible in water |
-
0
- NL NL275947D patent/NL275947A/xx unknown
- NL NL111304D patent/NL111304C/xx active
- FR FR1317644D patent/FR1317644A/fr not_active Expired
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1961
- 1961-03-14 DE DEF33413A patent/DE1244707B/en active Pending
-
1962
- 1962-03-01 CH CH253962A patent/CH378848A/en unknown
- 1962-03-12 US US179245A patent/US3199942A/en not_active Expired - Lifetime
- 1962-03-14 GB GB9880/62A patent/GB962278A/en not_active Expired
- 1962-03-14 BE BE615102A patent/BE615102A/en unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1970578A (en) * | 1930-11-29 | 1934-08-21 | Ig Farbenindustrie Ag | Assistants for the textile and related industries |
US2133480A (en) * | 1932-01-02 | 1938-10-18 | Ig Farbenindustrie Ag | Production of ethers suitable as dispersing agents and of preparations therefrom |
US2963513A (en) * | 1955-11-28 | 1960-12-06 | Ciba Ltd | Polyglycol ether derivatives |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3290111A (en) * | 1962-09-18 | 1966-12-06 | Bayer Ag | Process for improving the fastness properties of dyeings |
US3536438A (en) * | 1966-03-11 | 1970-10-27 | Sandoz Ag | Process of dyeing textile fibres using a phenyl sulphone dyeing assistant |
US3807945A (en) * | 1968-10-08 | 1974-04-30 | Hoechst Ag | Process for the dyeing of mixtures of cellulose, polyester and polyacrylonitrile fibers from one bath |
US4185962A (en) * | 1970-02-02 | 1980-01-29 | Sandoz Ltd. | Dyeing with organic dyestuffs dispersed in an organic liquid |
US3859045A (en) * | 1971-07-22 | 1975-01-07 | Allied Chem | Ethoxylated aliphatic tertiary amines to reduce ozone attack on dyes in polyamide fibers |
US3964861A (en) * | 1971-12-23 | 1976-06-22 | Allied Chemical Corporation | Alkoxylated aliphatic amines to inhibit ozone fading of dyed polyamides |
Also Published As
Publication number | Publication date |
---|---|
BE615102A (en) | 1962-07-02 |
NL111304C (en) | |
NL275947A (en) | |
CH253962A4 (en) | 1964-03-13 |
DE1244707B (en) | 1967-07-20 |
GB962278A (en) | 1964-07-01 |
FR1317644A (en) | 1963-05-08 |
CH378848A (en) | 1964-08-14 |
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