US2347001A - Dyeing cellulose esters - Google Patents
Dyeing cellulose esters Download PDFInfo
- Publication number
- US2347001A US2347001A US358667A US35866740A US2347001A US 2347001 A US2347001 A US 2347001A US 358667 A US358667 A US 358667A US 35866740 A US35866740 A US 35866740A US 2347001 A US2347001 A US 2347001A
- Authority
- US
- United States
- Prior art keywords
- fibres
- articles
- dyed
- dyestuffs
- wool
- 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
- 238000004043 dyeing Methods 0.000 title description 29
- 229920002678 cellulose Polymers 0.000 title description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 44
- 229920002301 cellulose acetate Polymers 0.000 description 25
- 239000003795 chemical substances by application Substances 0.000 description 25
- 210000002268 wool Anatomy 0.000 description 25
- 206010042674 Swelling Diseases 0.000 description 17
- 230000008961 swelling Effects 0.000 description 17
- 239000002253 acid Substances 0.000 description 16
- 235000002639 sodium chloride Nutrition 0.000 description 16
- 229960000583 acetic acid Drugs 0.000 description 15
- 238000000034 method Methods 0.000 description 14
- 150000003839 salts Chemical class 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 13
- 239000000975 dye Substances 0.000 description 13
- 229920002955 Art silk Polymers 0.000 description 9
- 239000000080 wetting agent Substances 0.000 description 9
- 229920002284 Cellulose triacetate Polymers 0.000 description 8
- 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 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000004359 castor oil Substances 0.000 description 5
- 235000019438 castor oil Nutrition 0.000 description 5
- 239000001913 cellulose Substances 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 5
- 229940055577 oleyl alcohol Drugs 0.000 description 5
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000009963 fulling Methods 0.000 description 4
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 3
- 229920002994 synthetic fiber Polymers 0.000 description 3
- 238000002166 wet spinning Methods 0.000 description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- QMMMCTXNYMSXLI-UHFFFAOYSA-N fast blue B Chemical compound C1=C([N+]#N)C(OC)=CC(C=2C=C(OC)C([N+]#N)=CC=2)=C1 QMMMCTXNYMSXLI-UHFFFAOYSA-N 0.000 description 2
- -1 furthermore Inorganic materials 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- RNTNZRPCYDDMIA-UHFFFAOYSA-M 4478-76-6 Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(C)=CC=C1NC1=CC=C2C3=C1C(=O)C1=CC=CC=C1C3=CC(=O)N2C RNTNZRPCYDDMIA-UHFFFAOYSA-M 0.000 description 1
- PIEQFSVTZMAUJA-UHFFFAOYSA-N 7-hydroxy-8-{[4-(phenyldiazenyl)phenyl]diazenyl}naphthalene-1,3-disulfonic acid Chemical compound OC1=CC=C2C=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=C1N=NC(C=C1)=CC=C1N=NC1=CC=CC=C1 PIEQFSVTZMAUJA-UHFFFAOYSA-N 0.000 description 1
- KKBFCPLWFWQNFB-UHFFFAOYSA-M CI Acid Orange 3 Chemical compound [Na+].[O-][N+](=O)C1=CC([N+](=O)[O-])=CC=C1NC(C=C1S([O-])(=O)=O)=CC=C1NC1=CC=CC=C1 KKBFCPLWFWQNFB-UHFFFAOYSA-M 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical class O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001845 chromium compounds Chemical class 0.000 description 1
- WYYQVWLEPYFFLP-UHFFFAOYSA-K chromium(3+);triacetate Chemical compound [Cr+3].CC([O-])=O.CC([O-])=O.CC([O-])=O WYYQVWLEPYFFLP-UHFFFAOYSA-K 0.000 description 1
- 239000007859 condensation product Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 238000000578 dry spinning Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- KQSBZNJFKWOQQK-UHFFFAOYSA-N hystazarin Natural products O=C1C2=CC=CC=C2C(=O)C2=C1C=C(O)C(O)=C2 KQSBZNJFKWOQQK-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- FJIKWRGCXUCUIG-UHFFFAOYSA-N lormetazepam Chemical compound N=1C(O)C(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1Cl FJIKWRGCXUCUIG-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- VENDXQNWODZJGB-UHFFFAOYSA-N n-(4-amino-5-methoxy-2-methylphenyl)benzamide Chemical compound C1=C(N)C(OC)=CC(NC(=O)C=2C=CC=CC=2)=C1C VENDXQNWODZJGB-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229940051201 quinoline yellow Drugs 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 235000012752 quinoline yellow Nutrition 0.000 description 1
- 239000004172 quinoline yellow Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- KIEOKOFEPABQKJ-UHFFFAOYSA-N sodium dichromate Chemical compound [Na+].[Na+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KIEOKOFEPABQKJ-UHFFFAOYSA-N 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000002522 swelling effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- MPCYPRXRVWZKGF-UHFFFAOYSA-J tetrasodium 5-amino-3-[[4-[4-[(8-amino-1-hydroxy-3,6-disulfonatonaphthalen-2-yl)diazenyl]phenyl]phenyl]diazenyl]-4-hydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(N=NC3=CC=C(C=C3)C3=CC=C(C=C3)N=NC3=C(C=C4C=C(C=C(C4=C3O)N)S([O-])(=O)=O)S([O-])(=O)=O)=C(O)C2=C1N MPCYPRXRVWZKGF-UHFFFAOYSA-J 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- 150000004764 thiosulfuric acid derivatives Chemical class 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- 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
- D06P3/40—Cellulose acetate
- D06P3/46—Cellulose triacetate
- D06P3/48—Cellulose triacetate using dispersed dyestuffs
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F2/00—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof
- D01F2/24—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from cellulose derivatives
- D01F2/28—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from cellulose derivatives from organic cellulose esters or ethers, e.g. cellulose acetate
-
- 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
- D06P1/6133—Addition products of hydroxyl groups-containing compounds with oxiranes from araliphatic or aliphatic alcohols
-
- 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
- D06P1/6136—Condensation products of esters, acids, oils, oxyacids 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
- D06P1/653—Nitrogen-free carboxylic acids or their salts
- D06P1/6533—Aliphatic, araliphatic or cycloaliphatic
-
- 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
- D06P1/673—Inorganic compounds
- D06P1/67333—Salts or hydroxides
- D06P1/6735—Salts or hydroxides of alkaline or alkaline-earth metals with anions different from those provided for in D06P1/67341
-
- 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
- D06P3/40—Cellulose acetate
- D06P3/42—Cellulose acetate using dispersed dyestuffs
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- 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
- D06P3/40—Cellulose acetate
- D06P3/46—Cellulose triacetate
-
- 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
- D06P3/40—Cellulose acetate
- D06P3/46—Cellulose triacetate
- D06P3/461—Cellulose triacetate using acid dyes
Definitions
- the present invention relates to the art of dyeing cellulose esters, and more especially, to a process for dyeing shaped articles like fibres, films, bands, and so on of highly acetylated cellulose, i. e. cellulose acetate having an acetate content of above 59%; such cellulose acetates are for the most part soluble in chloroform.
- highly acetylated cellulose i. e. cellulose acetate having an acetate content of above 59%; such cellulose acetates are for the most part soluble in chloroform.
- the articles After the treatment with one of the swelling agents, the articles can be dyed directly in deep and full shades; the dyeings so obtained have good fastness properties. It is especially possible to dye animalized articles after the said swelling treatment with acid wool dyestuffs and to obtain dyeings of excellent fastness.
- the swelling agent Before dyeing, the swelling agent may be removed from the articles by washing with water, without practically losing the property of being easily dyed. This property is only lost when the articles are dried before dyeing.
- the process according to my invention is of special value in dyeing animalized material of highly esterifiecl cellulose acetate with acid wool dyestufis.
- animalized material of highly esterifiecl cellulose acetate with acid wool dyestufis.
- Such material is produced in known manner, for instance, by incorporating basic substances like nitrogen bases with the material, for instance, by adding a suitable nitrogen base to a spinning solution for artificial fibres from highly acetylated cellulose. It is possible in this way, for example, to prepare artificial fibres from cellulose having an acetate content of above 59% which can be 'dyed alone or together with wool in equal shades as wool.
- cellulose triacetate fibres are prepared which contain a basic nitrogen containing resin, the fibres are treated with at least 40% aqueous acetic acid or a swelling agent of similar strength, are then treated with one of the above mentioned fixing agents and thereupon dyed with an acid wool dyestuff.
- the fibres may then be worked up into a mixed fabric together with wool and, by aftertreating with the same dyestuif, may be uniformly dyed. It is self-understood that in a similar way two-colored effects may be produced. It is furthermore possible to work up animalized cellulose triacetate fibres together with wool to slivers, yarns, skeins, fabrics and so on, and to treat these materials with a swelling agent which will not impair the wool.
- the materials may be dyed in one or the same bath in uniform shades with acid wool dyestuffs.
- acid wool dyestuffs As above mentioned the fastness of the dyeings on the cellulose acetate articles surpasses that of the same dyeings on wool, especially as regards the fastness to washing and fulling.
- a fabric from cellulose triacetate fibres or animalized cellulose triacetate fibres may be printed with one of the above strong swelling agents and thereupon may be dyed with a suitable dyestuif, if desired, after having been treated with one of the said fixing agents. In both cases dyed patterns on a white ground or vice versa may be obtained.
- Example 1 Fibres which have been prepared from chloroform-soluble cellulose acetate (acetate content: 59-61%) according to a wet-spinning process are continuously passed through a bath containing 60% aqueous acetic acid. The fibres swell strongly. Thereupon the fibre bundle is deacidified by washing with water and dyed with a water insoluble cellulose acetate dyestuff. By using, for instance, Cellit Fast Blue B (Schultz, Dyestuffs Tables, 1st suppl. vol., 1934, page 75), a deep blue shade is obtained whereas without the said swelling treatment the fibres are practically not dyed.
- Cellit Fast Blue B Schotz, Dyestuffs Tables, 1st suppl. vol., 1934, page 75
- Example 2 Fibres swollen and washed as described in Example 1 are cut into staples and brought into a bath containing -30% of an inorganic or organic salt.
- the following salts may be used: chlorides, bromides, iodides, sulfates, nitrates, borates, phosphates, sulfites, thiosulfates, thiocyanates of the alkali and alkaline-earth metals, furthermore, alkali and alkaline-earth metal salts of the lower fatty acids, and mixtures of the said salts.
- the swollen fibres After the swollen fibres have been treated for 5-10 minutes in a salt bath, for instance, a solution of common salt, they are centrifuged and dried. After shortly washing the fibres are dyed as usual with cellulose acetate dyestuffs, for instance, Celliton Fast Black BTN (Schultz, Dyestuif Tables, lst-suppl. vol., 1934, page 76). Contrary to the untreated fibres, they are dyed in deep and full shades.
- cellulose acetate dyestuffs for instance, Celliton Fast Black BTN (Schultz, Dyestuif Tables, lst-suppl. vol., 1934, page 76). Contrary to the untreated fibres, they are dyed in deep and full shades.
- the usual softening and finishing agents may be added to the salt bath.
- Example 3 instead of a salt bath as described in the foregoing example, there may be used an aqueous solution of 5-50 g. per litre of a wetting agent which is free from sulphonic acid groups, for instance, a reaction product of a reactive tertiary amine with the anhydride of a substituted succinic acid, or a condensation product of oleyl alcohol or of castor oil with an excess of ethylene oxide.
- a wetting agent which is free from sulphonic acid groups
- a reaction product of a reactive tertiary amine with the anhydride of a substituted succinic acid or a condensation product of oleyl alcohol or of castor oil with an excess of ethylene oxide.
- Example 4 Fibres having been subjected to a swelling treatment as described in Example 1 are aftertreated with a bath containing 2-10% of a salt and 0.050.5% of wetting agent which is free of sulphonic acid groups. The results are similar to those obtained according to Example 1-3.
- Example 5 Cellulose acetate artificial silk (acetate content: 59%) prepared by a dry spinning process is treated in skein form for 15-120 seconds at a temperature of 30 C. in a 50% aqueous acetic acid. After having been washed with water, the silk is dyed with Celliton Fast Black BTN in a deep black shade, whereas the untreated silk is hardly dyed. Of course, it is possible to add an aftertreatment of the swollen fibres as described in Examples 24.
- Example 6 To a raw solution of cellulose triacetate, there are added 545% (calculated on cellulose acetate) of a reaction product of starch benzene sulfonate with an amine as described in the application Ser. No. 180,157, filed December 16, 1937, and the solution is spun into fibres. In spite of the presence of the nitrogenous compounds, these fibres are but scarcely dyed with acid wool dyestuffs.
- the fibres are then continuously passed through a bath containing 60% aqueous acetic acid at a temperature of 20 C. for 15-120 seconds, thereupon washed with water and are dyed, while still wet, with acid wool dyestuffs, for instance, Amido Yellow E (Schultz, Dyestuffs Tables, vol. 1, 1931, No. 16).
- acid wool dyestuffs for instance, Amido Yellow E (Schultz, Dyestuffs Tables, vol. 1, 1931, No. 16).
- the deep dyeings obtained in this manner are especially distinguished by their fastness. For example, the fastness against fulling is 4-5 (Normen der Deutschen Echtheitskommission 1935), whereas a corresponding dyeing on wool has a fastness against fulling of 1-2.
- a series of other acid wool dyestuffs act in the same way, for instance, Quinoline Yellow (Schultz, Dyestuffs Tables, vol. I, 1931, No. 918, Brilliant Crocein B (Schultz, Dyestuff Tables, 1st suppl., vol., 1934, No. 539), Alizarine Rubinol R (Schultz, Dyestuff Tables, vol. I, 1931, No. 1210), Wool Fast Violet B (Schultz, Dyestuif Tables, vol. I, 1931, No. 974), Alizarine Direct Blue A (Schultz, Dyestuif Tables, vol. II, 1932, page 9), A20 Acid Black 3 BL special (Schultz, Dyestulf Tables, 1st suppl. vol., 1934, page and so on.
- Example 7 A solution of cellulose triacetate in glacial acetic acid is mixed with an animalizing agent, for instance, a reaction product of chlorinated paraffin with ethylene diamine, and is spun by the wetspinning process; the fibres obtained therefrom are swollen in a 60% aqueous acetic acid at 60 C. for 15 seconds washed with water, and treated for 5 minutes in a salt bath containing 5% sodium acetate, 2% ammonium thiocyanate, 2% of a finishing agent and 0.5% isododecenyl-succinic acid-diethyl amino-methyl ester. The centrifuged and dried fibre is excellently dyed by acid wool dyestuffs.
- an animalizing agent for instance, a reaction product of chlorinated paraffin with ethylene diamine
- Example 8 A fibre bundle of cellulose triacetate being animalized as described in Example 6 is swollen for 30 seconds at a temperature of C. in a 65% aqueous acetic acid which contains about 2% of a chromium compound, for instance, sodium bichromate or chromium acetate and, if desired, a reduction agent like formaldehyde or glucose. The bundle is freed from acid and cut into staples.
- the fibres are after-treated in a salt bath (containing 8% sodium acetate, 1% of a wetting agent free of sulfo groups and 2% of a usual preparation), dried and worked up with wool to a yarn or textile fabric.
- the mixture is uniformly dyed with acid wool dyestuffs.
- chromable dyestuffs are Especially suitable.
- the dyeings on the artificial fibres are not only of the same fastness to washing, fulllng and perspiration, but are equal to the dyeings on pure wool regarding the fastness to light.
- Example 9 Triacetate artificial silk containing an animalizing agent is worked up with wool in the relative proportion 1:1.
- the mixture is treated in a bath containing 60% aqueous acetic acid and 2% glucose for seconds at C., centrifuged, washed and dyed in the wet state with wool dyestuffs such as, for example, Anthralane Blue B (Schultz, Dyestuff Tables 1st suppL, vol., 1934, page 68).
- the dyeings obtained are uniform on both kinds of fibres.
- Dyeings of particular fastness are obtained by using salts of the acid sulfuric acid esters of leuco vat dyes, which also dye both kinds of fibres equally and with the same fastness properties.
- Example 10 On working as described in Example 9, but inserting, after the swelling, a salt treatment, similar dyeings are obtained as those of Example 9.
- Example 11 A fibre produced as described in Example 8 is dyed with a water-insoluble cellulose acetate dyestuff, for instance, a Celliton Fast Dyestuff.
- a water-insoluble cellulose acetate dyestuff for instance, a Celliton Fast Dyestuff.
- Example 12 Fibres of chloroform-soluble cellulose acetate produced by the dryor wet-spinning process are locally printed with 60% aqueous acetic acid, if desired, in the presence of a thickenin agent and thereupon dyed, or treated with salt and after drying dyed with cellulose acetate dyestuffs at 70-80 C. Thereby fibres are obtained which show interesting two-colour effects, because the untreated places do not or practically not absorb the dyestuff, whereas the treated fibres absorb the same very strongly.
- Example 13 Fibres of triacetate having incorporated therewith an animalizing agent are spun and treated as described in Example 12. Flamed fibres may be obtained with cellulose acetate dyestuffs or with acid wool dyestuffs, chrome dyestuffs and so on.
- Example 14 A fabric prepared of cellulose triacetate fibres is printed in patterns with a paste containing 65% aqueous acetic acid, washed and dyed, or washed, treated with a salt as described in Example 7 and then dyed. With suitable dyestuffs, for instance, with Cellit Fast Blue B, dark patterns on a white ground are obtained.
- Example 15 A fabric of triacetate artificial silk having incorporated an animalizing agent is printed as described in Example 14. On dyeing with cellulose acetate dyestuffs, similar effects as in Example 14 are obtained. By dyeing with acid wool dyestuffs or with chrome dyestuffs which reserve acetate silk, coloured patterns on a white ground are obtained.
- a process for improving articles of cellulose acetate having an acetate content of at least 59 per cent which comprises treating the articles with aqueous acetic acid of at least 40 per cent strength, as a swelling agent, treating the swollen articles with an aqueous solution of a wetting agent comprising the reaction product of an excess of ethylene oxide upon an alcohol selected from the class consisting of oleyl alcohol and castor oil, to fix the swollen condition of the articles, and drying the articles.
- a process for improving articles of cellulose acetate having an acetate content of at least 59 per cent which comprises treating the articles with aqueous acetic acid of at least 40 per cent strength, as a swelling agent, treating the swollen articles with an aqueous solution of a wetting agent containing about 5 to 50 grams per liter of the reaction product of an excess of ethylene oxide upon an alcohol selected from the class consisting of oleyl alcohol and castor oil to fix the swollen condition of the articles, and drying the articles.
- a process for improving articles of chloroform-soluble cellulose acetate having an acetate content of 59 to 61 per cent which comprises treating the articles with aqueous acetic acid of 60 per cent strength, as a swelling agent, treating the swollen articles with an aqueous solution of a wetting agent comprising the reaction product of an excess of ethylene oxide upon an alcohol selected from the class consisting of oleyl alcohol and castor oil to fix the swollen condition of the articles, and drying the articles.
- wetting agent comprises the reaction product of an excess of ethylene oxide upon oleyl alcohol.
- wetting agent comprises the reaction product of an excess of ethylene oxide upon castor oil.
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
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Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL51049D NL51049C (d) | 1938-05-28 | ||
BE434596D BE434596A (d) | 1938-05-28 | ||
DEI61483D DE740909C (de) | 1938-05-28 | 1938-05-29 | Verfahren zum Faerben von kuenstlichen Gebilden aus chloroformloeslichem Celluloseacetat |
US275399A US2328682A (en) | 1938-05-28 | 1939-05-24 | Dyeing cellulose esters |
FR866305D FR866305A (fr) | 1938-05-28 | 1939-05-26 | Procédé pour teindre des produits artificiels à partir de cellulose fortement acétylée |
US358667A US2347001A (en) | 1938-05-28 | 1940-09-27 | Dyeing cellulose esters |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2328682X | 1938-05-28 | ||
US275399A US2328682A (en) | 1938-05-28 | 1939-05-24 | Dyeing cellulose esters |
US358667A US2347001A (en) | 1938-05-28 | 1940-09-27 | Dyeing cellulose esters |
Publications (1)
Publication Number | Publication Date |
---|---|
US2347001A true US2347001A (en) | 1944-04-18 |
Family
ID=32096534
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US358667A Expired - Lifetime US2347001A (en) | 1938-05-28 | 1940-09-27 | Dyeing cellulose esters |
Country Status (4)
Country | Link |
---|---|
US (1) | US2347001A (d) |
BE (1) | BE434596A (d) |
FR (1) | FR866305A (d) |
NL (1) | NL51049C (d) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2518644A (en) * | 1947-04-16 | 1950-08-15 | Celanese Corp | Dyeing cellulose derivatives in the presence of inorganic thiocyanates and organic acids |
US3016280A (en) * | 1955-06-30 | 1962-01-09 | Celanese Corp | Textile treatment |
US3022545A (en) * | 1956-09-06 | 1962-02-27 | British Celanese | Process for crimping cellulose triacetate fibers |
US3025129A (en) * | 1953-11-25 | 1962-03-13 | British Celanese | Process for increasing the crystallinity and safe ironing temperature of cellulose triacetate textiles with acetone mixtures |
US3025128A (en) * | 1953-11-25 | 1962-03-13 | British Celanese | Process for increasing the crystallinity and safe ironing temperature of cellulose triacetate textiles with aromatic chemical swelling agents |
US3132919A (en) * | 1956-03-29 | 1964-05-12 | British Celanese | Increasing safe ironing temperatures of cellulsoe triacetate fibers with swelling agents boiling above 190deg. c. |
US3167385A (en) * | 1956-12-07 | 1965-01-26 | British Celanese | Method of improving the safe ironing temperature and crystallinity of cellulose triacetate textile fibres with specific organic media |
-
0
- NL NL51049D patent/NL51049C/xx active
- BE BE434596D patent/BE434596A/fr unknown
-
1939
- 1939-05-26 FR FR866305D patent/FR866305A/fr not_active Expired
-
1940
- 1940-09-27 US US358667A patent/US2347001A/en not_active Expired - Lifetime
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2518644A (en) * | 1947-04-16 | 1950-08-15 | Celanese Corp | Dyeing cellulose derivatives in the presence of inorganic thiocyanates and organic acids |
US3025129A (en) * | 1953-11-25 | 1962-03-13 | British Celanese | Process for increasing the crystallinity and safe ironing temperature of cellulose triacetate textiles with acetone mixtures |
US3025128A (en) * | 1953-11-25 | 1962-03-13 | British Celanese | Process for increasing the crystallinity and safe ironing temperature of cellulose triacetate textiles with aromatic chemical swelling agents |
US3016280A (en) * | 1955-06-30 | 1962-01-09 | Celanese Corp | Textile treatment |
US3132919A (en) * | 1956-03-29 | 1964-05-12 | British Celanese | Increasing safe ironing temperatures of cellulsoe triacetate fibers with swelling agents boiling above 190deg. c. |
US3022545A (en) * | 1956-09-06 | 1962-02-27 | British Celanese | Process for crimping cellulose triacetate fibers |
US3167385A (en) * | 1956-12-07 | 1965-01-26 | British Celanese | Method of improving the safe ironing temperature and crystallinity of cellulose triacetate textile fibres with specific organic media |
Also Published As
Publication number | Publication date |
---|---|
FR866305A (fr) | 1941-07-28 |
NL51049C (d) | |
BE434596A (d) |
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