US3043646A - Dyeing of artificial fibers - Google Patents
Dyeing of artificial fibers Download PDFInfo
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- US3043646A US3043646A US799442A US79944259A US3043646A US 3043646 A US3043646 A US 3043646A US 799442 A US799442 A US 799442A US 79944259 A US79944259 A US 79944259A US 3043646 A US3043646 A US 3043646A
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- dyeing
- hydroxy
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- fibers
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- 238000004043 dyeing Methods 0.000 title claims description 33
- 229920002994 synthetic fiber Polymers 0.000 title claims description 8
- -1 POLYETHYLENE TEREPHTHALATE Polymers 0.000 claims description 21
- 239000000835 fiber Substances 0.000 claims description 18
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 13
- 229920002301 cellulose acetate Polymers 0.000 claims description 11
- 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 claims description 10
- 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 claims description 10
- 150000004056 anthraquinones Chemical class 0.000 claims description 10
- 239000006185 dispersion Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 229920002284 Cellulose triacetate Polymers 0.000 claims description 9
- 239000002657 fibrous material Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 6
- 239000000975 dye Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000005406 washing Methods 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
- 229920004934 Dacron® Polymers 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 239000004952 Polyamide Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000009998 heat setting Methods 0.000 description 5
- 229920002647 polyamide Polymers 0.000 description 5
- 229920002678 cellulose Polymers 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 210000002268 wool Anatomy 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229920000297 Rayon Polymers 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000003517 fume Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000009736 wetting Methods 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- 229920002302 Nylon 6,6 Polymers 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000000843 powder Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- ZHQJVZLJDXWFFX-RPDRRWSUSA-N (6R)-L-erythro-6,7-dihydrobiopterin Chemical compound N1C(N)=NC(=O)C2=N[C@@H]([C@@H](O)[C@@H](O)C)CN=C21 ZHQJVZLJDXWFFX-RPDRRWSUSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- RSQFCTICSPONJS-UHFFFAOYSA-N 1-(4-hydroxyphenyl)anthracene-9,10-dione Chemical compound C1=CC(O)=CC=C1C1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O RSQFCTICSPONJS-UHFFFAOYSA-N 0.000 description 1
- NETIXPOFUYPXNI-UHFFFAOYSA-N 2-aminopropane-2-sulfonic acid Chemical compound CC(C)(N)S(O)(=O)=O NETIXPOFUYPXNI-UHFFFAOYSA-N 0.000 description 1
- DIUJNXCPDGGFQD-UHFFFAOYSA-N 2-ethoxyethoxybenzene Chemical compound CCOCCOC1=CC=CC=C1 DIUJNXCPDGGFQD-UHFFFAOYSA-N 0.000 description 1
- MEEKGULDSDXFCN-UHFFFAOYSA-N 2-pentylphenol Chemical compound CCCCCC1=CC=CC=C1O MEEKGULDSDXFCN-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920003620 Grilon® Polymers 0.000 description 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004959 Rilsan Substances 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229920004933 Terylene® Polymers 0.000 description 1
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- PHHWLDOIMGFHOZ-UHFFFAOYSA-L disodium;dinaphthalen-1-ylmethanedisulfonate Chemical compound [Na+].[Na+].C1=CC=C2C(C(C=3C4=CC=CC=C4C=CC=3)(S(=O)(=O)[O-])S([O-])(=O)=O)=CC=CC2=C1 PHHWLDOIMGFHOZ-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 1
- MHMQGJBUQUDINX-UHFFFAOYSA-N ethoxybenzene Chemical compound [CH2]COC1=CC=CC=C1 MHMQGJBUQUDINX-UHFFFAOYSA-N 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
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- NKAAEMMYHLFEFN-UHFFFAOYSA-M monosodium tartrate Chemical compound [Na+].OC(=O)C(O)C(O)C([O-])=O NKAAEMMYHLFEFN-UHFFFAOYSA-M 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229930015698 phenylpropene Natural products 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- IZWPGJFSBABFGL-GMFCBQQYSA-M sodium;2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS([O-])(=O)=O IZWPGJFSBABFGL-GMFCBQQYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- RUVINXPYWBROJD-ONEGZZNKSA-N trans-anethole Chemical compound COC1=CC=C(\C=C\C)C=C1 RUVINXPYWBROJD-ONEGZZNKSA-N 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/503—Amino-hydroxy-anthraquinones; Ethers and esters thereof unsubstituted amino-hydroxy anthraquinone
-
- 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
- D06P3/26—Polyamides; Polyurethanes 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
- D06P3/36—Material containing ester groups 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
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/921—Cellulose ester or ether
-
- 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
Description
nite States 3,043,646 DYEING F ARTIFICIAL FIBERS Paul Buecheler, Reinach, Switzerland, assignor to Sandoz Ltd., Basel, Switzerland No Drawing. Filed Mar. 16, 1959, Ser. No. 799,442
Claims priority, application Switzerland Mar. 19, 1958 6 Claims.- (Cl. 840) It has been found that the anthraquinone dyestuffs of the formula atent 0 "ice aryl radical which may be further substituted, used alone or in mixtures with each other are eminently suitable for the dyeing of cellulose ester, synthetic polyamide and polyester fibers from aqueous suspension.
In many cases the mixtures of two or more dyestuffs of the Formula I show better building-up properties'than the dye-stuffs used alone.
The dyeing operation is conducted advantageously in presence of wetting, dispersing or emulsifying agents such as Marseilles soap, fatty alcohol sulfonates or sulfates, e.g. sodium lauryl sulfate, or the condensation products of fatty acids, e.g. oleic acid, with the alkali metal salts of aminoand methyl-amino-ethane-sulfonic acid, highly sulfonated castor oil, etc.
The dyeing temperatures and times depend upon the material to be dyed and are correlated with each other. Secondary cellulose acetate can be dyed at temperatures between 75 and 90 0, preferably at 80-85 C., for 45 minutes to 1 /2 hours, preferably for 1 hour. But it is also possible to work at 95 l00 C. e'.g. in the case of blended fabrics containing viscose and acetate, and even at about 120 C. under pressure, with a corresponding reduction of the dyeing time.
Cellulose triacetate and the synthetic polyamide fibers and dyed at 90-l00 C. for 45 minutes to l /zhours, preferably for 1 hour at the boil, or at temperatures between 105 and 120 C. under pressure, whereby the dyeing time can be shortened.
Polyester fibers, when dyed for about 1 hour at 95- 100 C., require thepresence of a carrier: 2-hydroxyl.l-diphenyl, the methyl ester of 2-hydroxybenzene-lcarboxylic acid, benzoic acid or an emulsion of chlorinated benzene, whereas at temperatures higher than 100 0., eg between 110 and 130 C. the addition of a carrier is superfluous.
In any event when the dyeing temperature exceeds 100' C. and in the case of secondary cellulose acetate already when the dyeing temperature amounts to 95 100 C., the dyebath must be maintained neutral in order to prevent saponification of the fibers.
at least one O-X-group in which X' 3,043,646 Patented July 10, 1!)62 To enhance the degree of dispersion, the dry 'dyestulfs may be preliminarily ground with a suitable Wetting or dispersing agent, such as sodium dinaphthylmethanedisulfonate, sodium ligninsulfonate or the dried residue of sulfite waste liquor. The dyestuifsmay also be intimately mixed in the form of an aqueous paste with one of the atorecited wetting or dispersing agents and, if desired, converted into the form of a dyestuff powder by suitable drying.
The dyeings obtained with these dyestuffs on secondary cellulose acetate possess excellent lightfastness and good fastness to washing, perspiration and gas fumes. On cellulose triacetate and polyester fibers they give dyeings of very good fastness to light, heat setting andpleating,
and good fastness to washing and perspiration. The dyestuffs reserve wool, cotton and viscose rayon.
The dyeings on synthetic polyamide fibers are fast to light, washing and perspiration.
In Formula I R preferably represents a mono-, dior trihydroxyphenyl radical, a monohydroxy, monomethoxyor monoethoxynaphthyl radical, a monoor dimethoxyor .-ethoxy-phenyl radical or a monohydroxymonomethoxyor -monoe thoxy-pheny1 radical.
Of the anthraquinone dyestuffs of Formula 1, those of the formula HO NH:
I The dyestuif gives a good reserve of wool. To improve .NH: 2% 01H (II) wherein R stands for a hydroxyphenyl, hydroxynaphthyl, methoxyphenyl or dihydroxyphenyl radical, are already known. They are obtained e.g. by (1) addition of phenol at the boric acid ester of 1.5-dihydroxy-4.8-diaminoanthraquinone-Z.6-disulfonic acid in concentrated sulfuric acid solution (GP 445,268), (2) boiling the addition product in acid aqueous solution or heating it in alkaline solution at 20-60 C. to split off one sulfonic acid group (GP 446,563), (3) reductive splitting off from the latter of the remaining sulfonic acid group (GP 456,235). I
The anthraquinone dyestuffs used in the present process are produced in an analogous manner.
In the following examples the parts and percentages are by weight and the temperatures in degrees centigrade.
Example 1 A dyebath is prepared'with 1 part of the dyestufi 1.5- dihydroxy 4.8 -di-amino 2 (4-hydroxy)-phenylanthraquinone dispersed with Turkey red oil, 6 parts of a sulfonated fatty alcohol, and 3000 parts of water. parts of cellulose triacetate are entered in the bath at room temperature and the temperature is raised to 100 in 1 hour and maintained at 100 for a further hour. After this time the dyeing process is completed. The goods are removed, rinsed and dried. They are dyed a blue shade of good fastness to washing, gas fumes, heat setting and pleating, and very good light fastness.
Example 2v 1 part of 1.5-dihydroxy-4.8-diamino-2-(4'-methoxy)- phenylanthraquinone, 1 part of the sodium salt of di-.
naphthylmethanedisulfouic acid and 8 parts of water are ground together until a fine dispersion is formed. It is run into a dyebath consisting of 3000 parts of-water and 6 parts of Marseilles soap. 100 parts of a cellulose ace--' tate fabric are entered in the dyebath; the temperature is raised to 80 in minutes and this temperature maintained for 1 hour. Then the fabric is removed from the dyebath, rinsed with water and dried. A bright blue dyeing is obtained which has excellent light fastness and goodfa stness towashing, perspiration and gas fumes.
Example 3 100 puarts of ,Dacron polyethylene terephthalate fibers made by the condensation of dimethyl terephthalate and .ethylene glycol, (see Handbook of Material Trade Names, by Zimmermann and Lavoine, 1953 edition, p; 159) are entered in a dyebath at 60 containing 3000 parts of Water, 2 parts of the dyestuifused in Example 1, and 1.5 parts of 2-hydroxy-1.1-diphenyl. The dyebath is brought to the 'boil in 20 minutesand boiled for 1 hour. The goods are then removed, rinsed with, water and dried. The Dacron fabric is dyed an attractive blue shade which is fast to washing and has very good fastness to light, heat setting and pleating. Cotton present in the dyebath is reserved.
Example 4 A fine dyestufl dispersion is prepared with 1 part of 1.5-dihydroxy-4.8-diamino -.2 (4-ethoxy)-phenylanthraquinone, 1 part of sulfite cellulose waste liquor (in powder form) and 8 parts of water. This paste is added to a dyebath of 3000 par-ts of water and 3 parts of Igepon T in a high-temperature dyeing machine. '100 parts of Terylene polyester fiber are added, the machine closed, and the inner temperature increased to 120. After 1 hour at this temperature dyeing is completed. The material is removed, rinsed and dried. It is dyed a blue shade which shows good washing and perspiration fastness and very good fastness to light, heat setting and pleating. Wool present in the dyebath is reserved. Dacron, Dralon and Tergal polyester fibers can be dyed by the same method.
' Example 5 1 part. of. 1.5-dihydroxy-4.8-diamino-2-(4'methoxy)- phenylanthraquinone, 1 part of the sodium salt of dinaphthylme'thanedisulfonic acid and 8 parts of water are,
ground together until a fine dispersion is obtained. It is run into a dyebath containing '4000 parts of water and 4 parts of a highly sulfonated castor oil. 100 parts of a Nylon 66 fabric are entered in the bath and the temperature is increased to 100 in minutes. Dyeing is continued for 1 hour at 95-100? The nylon is then rinsed in warm and cold water and dried. I Itis dyed a bright blue shade which has; very good fastness to Washing and perspiration and good light. fastness.
' With other synthetic polyamide fibers such as Perlon (=Nylon 6), Mirlon, Grilon or Rilsan dyeings of similar fastness properties are obtained.
In thefollowing table, are listediu'rtherdyestulfs of Formula I which are highly suitable for dyeing cellulose acetate, cellulose tn'acetate, and synthetic polyamide polyesterv fibers. They are characterized in the table by the hydrocarbon radical RH forming the basis of the radical R, the dyeing material, and the shade of the dyeing.
Example Dyeing Ma- Shade of No. R-H terial the Dyeing 6 phenoxybenzene Dacron blue l-hydroxy-Z-chlorobenzene do regihsh ue. l-hydroxy-Z-methylbenzene acetate sky- 1-hydroxy-3-rnethylbenzene. l-hydroxy--methylbenzene l-hydroxy-i-ethylbenzene.
l-h ydroxynaph thalene 13 2-hydroxynaphthalene.
14 1-hydroxy-2-amylbenzene 15 1-hydroxy-4-arnylbenzene acetate.
16 l-hydroxyt-octylbenzene d 17 l-hydroxyl-cyelohexylbenzene 18 l-hydroxy-2-phenylbenzene 19 1-hydroxy-4-phenylbenzene 20 1 hydroxy 2.6 di isopropyl benzene. 1 hydroxy 2 tert.buty1 5 methylbenzene. 1hydroxy-2.6-dimethylbenzene Lzdimethoxybenzene lA-dimethoxybenzene. 1-hydroxy-2-n1ethoxybenzene. l-hydroxyi-methoxybenzene...
(2"-hydroxy)-ethoxybenzene cellulose-tri- Do. acetate. 7 L 1.2-dihydroxybenzene Dacron blue- L3-dihydroxybenzene 1.4-dihydroxybenzene l-methoxyi-methylbenzene.
4-amino-phen0xybenzene 1-methoxy-4-propenylbenzene. 1 hy droxy- 2 methoxy 4 allyl benzene.
[2-(2-hydroxy) -ethoxy]ethoxybenzene. 1.3.5-trihydroxybenzene 1 -hydroxy 2 benzoyl 5 methoxybenzene.
2.2 bis(4 hydroxyphenyl) propane.
2-bromethoxybenzene 2-chlorethoxybenzene 3'-methoxypropoxybenzene 2 -ethoxyethoxybenzene l-hydroxyl-ethoxybenzene Nylon 66.. acetate Example 44 boiled for 1 hour. The goods are then removed, rinsed with Water and dried. The Dacron fabric is dyed an attractive blue shade which is fastto washing and has very good fastness to light, heat setting and pleating. Cotton or wool present in the dyebath is reserved.
Other dyestuff mixtures suitable for the dyeing of acetate, triacetate and polyester fibers are e.g. the following: 1.5-dihydroxy-4.S-diamino 2 (4,-methoxy)-phenylan-, thnaquinone and 1.5dihydroxy 4.8 diainino-Z-(Z-hydroXy-S-amyl)rphenylanthraquinone, 1.5 dihydroxy-4-.8- diamino-YZ-( V-methoxy)-phenylanth raquinone and 1.5-dihydroxy 4.8 diamino-2-'(4'-ethoxy)-phenylanthraquinone, 1.5-dihydroxy-4.S-diamino-Z- (4'-ethoxy) -plienylanthraquinone and 1.5-dihydroxy 4.8 diamino-2-(4'-hydroxy)-phenylanthraquinone, etc. When used in equal concentration these mixtures yield stronger dyeings than the dyestuff 1.5dihydroxy 4.8 diamino-2(4-methoxy)- phenylanthraquinone alone. In the case of weak dyeings the exhaust (i.e. the patterns used in the second dyeing proce'ss) remain white,
Having thus disclosed the invention what I claim is:
l. A dyeing process comprising applying to an artificial fiber material selected from the group consisting of secondary cellulose acetate, cellulose triacetate, and polyethylene terephthalate fibers, from an aqueous dispersion,
a member selected from the group consisting of a single anthraquinone dyestufi and a mixture of anthraquinone dyestulfs of the formula OH O NHQ (OX) n Z NHz OH wherein R represents a member selected from the group consisting of radicals of the benzene, diphenyl and naphthalene series,
X represents a member selected from the group consisting of hydrogen, lower alkyl, lower hydroxyalkyl, lower alkoxyalkyl, lower hydroxy-alkoxyalkyl, lower halogeno-alkyl, phenyl and aminophenyl,
Y represents a member selected from the group consisting of hydrogen, alkyl with 1 to 8 carbon atoms, alkoxy with 1 to 2 carbon atoms, alkenyl with 3 carbon atoms, cyclohexyl and chlorine provided that the latter stands in an other than the para-position to the OX-group,
Z represents a member selected from the group consisting of hydrogen, lower alkyl and lower alkoxy,
n represents one of the integers l, 2 and 3.
and
2. A dyeing process comprising applying to an artificial fiber material selected from the group consisting of secondary cellulose acetate, cellulose triacetate, and polyethylene terephthalate fibers, from an aqueous dispersion, the anthraquinone dyestutf of the formula C 5114-0 C H; l NH: Cl H 3. A dyeing process comprising applying to an artificial fiber material selected from the group consisting of secondary cellulose acetate, cellulose triacetate, and poly- 4. A dyeing process comprising applying to an artificial fiber material selected -from the group consisting of second-ary cellulose acetate, cellulose triacetate, and polyethylene terep'hthalate fibers, from an aqueous dispersion, the anthraquinone dyestuff of the formula 5. A dyeing process comprising applying to an artificial fiber material selected from the group consisting of secondary cellulose acetate, cellulose triacetate, and polyethylene terephthalate fibers, from an aqueous dispersion, a mixture of the two dyestuffs of the formulae OH O NHz I l I CBH4OH II I NH2 0 OH and (i)H NHi mOIHAOOHE I ll NH2 0 OH 6. A dyeing process comprising applying to an artificial fiber material selected from the group consisting of secondary cellulose acetate, cellulose triacet-ate, and polyethylene terephthalate fibers, from an aqueous dispersion, the anthraquinone dyestufi of the formula NH; O OH References Cited in the file of this patent UNITED STATES PATENTS 2,922,691 Grossman 'Jan. 26, 1960 2,993,917 Weinstein et a1 July 25, 1961 FOREIGN PATENTS 456,235 Germany Feb. 18, 1928 OTHER REFERENCES Dorm-an: Amer. Dyest Rep., July 5, 1954, pages 426- 429, 437 (esp. p. 428).
Schroeder: Text, Res. 1., vol, 27, No. 4, April 1957, pp. 275-285. 36Ygates: Silk J. and Rayon World, November 1945, pp.
Patent No. 3,043 646 Paul Buecheler Column 5, line 27, before "n" and in italics, insert line 28, strike out "and" Signed and sealed this 16th day of June 1964.
SEAL) I ttest:
ERNEST W. SWIDER EDWARD J. BRENNER testing Officer Commissioner of Patents
Claims (1)
1. A DYEING PROCESS COMPRISING APPLYING TO AN ARTIFICIAL FIBER MATERIAL SELECTED FROM THE GROUP CONSISTING OF SECONDARY CELLULOSE ACETATE, CELLULOSE TRIACETATE, AND POLYETHYLENE TEREPHTHALATE FIBERS, FROM AN AQUEOUS DISPERSION, A MEMBER SELECTED FROM THE GROUP CONSISTING OF A SINGLE ANTHRAQUINONE DYESTUFF AND A MIXTURE OF ANTHRAQUINONE DYESTUFFS OF THE FORMULA
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH894338X | 1958-03-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3043646A true US3043646A (en) | 1962-07-10 |
Family
ID=4546083
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US799442A Expired - Lifetime US3043646A (en) | 1958-03-19 | 1959-03-16 | Dyeing of artificial fibers |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3043646A (en) |
| CH (2) | CH351253A (en) |
| DE (1) | DE1144678B (en) |
| FR (1) | FR1218936A (en) |
| GB (1) | GB894338A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3265460A (en) * | 1960-03-22 | 1966-08-09 | Allied Chem | Dyeing of synthetic fibers |
| US3349104A (en) * | 1962-08-13 | 1967-10-24 | Ici Ltd | 2-acyloxyphenyl-4, 8-diamino-1, 5-dihydroxy-anthraquinones |
| US3549667A (en) * | 1962-01-12 | 1970-12-22 | Bayer Ag | Preparation of aryl substituted hydroxy anthraquinones |
| US3669994A (en) * | 1964-03-25 | 1972-06-13 | Ici Ltd | Anthraquinone dyestuffs |
| EP0063713A1 (en) * | 1981-04-18 | 1982-11-03 | MERCK PATENT GmbH | Dichroic anthraquinone dyes, liquid crystal dielectrics containing them and electro-optical display |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1184878B (en) * | 1961-12-23 | 1965-01-07 | Bayer Ag | Process for the preparation of anthraquinone dyes |
| BE631892A (en) * | 1962-05-11 | |||
| GB1010745A (en) * | 1963-04-10 | 1965-11-24 | Ici Ltd | New water-insoluble anthraquinone dyestuffs |
| DE1228734B (en) * | 1963-07-04 | 1966-11-17 | Bayer Ag | Process for the preparation of anthraquinone dyes |
| DE1266263B (en) * | 1965-06-04 | 1968-04-18 | Hansjoachim Von Hippel Dr Ing | Face conveyor anchoring station with support device for the extension of the line at the passage of the conveyor from the face into the line |
| GB1081890A (en) * | 1965-07-19 | 1967-09-06 | Ici Ltd | Anthraquinone dyestuffs |
| GB1317281A (en) * | 1970-03-04 | 1973-05-16 | Ici Ltd | Colouration of polyesters |
| NL7204838A (en) * | 1971-04-14 | 1972-10-17 | ||
| DE2846229A1 (en) | 1978-10-24 | 1980-05-08 | Bayer Ag | METHOD FOR DYEING AND PRINTING CELLULOSE FIBERS |
| DE3040102A1 (en) * | 1980-10-24 | 1982-06-03 | Merck Patent Gmbh, 6100 Darmstadt | DICHROITIC ANTHRACHINONE DYES, THIS CONTAINING LIQUID CRYSTALINE DIELECTRICS AND ELECTRO-OPTICAL DISPLAY ELEMENT |
| DE19813139C1 (en) | 1998-03-25 | 1999-09-23 | Schober Werkzeug & Maschbau | Work conveyor for punch |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE456235C (en) * | 1925-04-17 | 1928-02-18 | I G Farbenindustrie Akt Ges | Process for the preparation of anthraquinone derivatives |
| US2922691A (en) * | 1955-08-02 | 1960-01-26 | Ciba Ltd | Anthraquinone dyes and polyethylene terephthalate fibers dyed therewith |
| US2993917A (en) * | 1957-12-30 | 1961-07-25 | Cfmc | New anthraquinone dyestuffs and a process for their preparation |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE864425C (en) * | 1951-01-30 | 1953-01-26 | Gen Aniline & Film Corp | Process for the production of anthraquinone dyes which are resistant to gas shrinkage and are particularly suitable for dyeing acetate silk |
| US2773071A (en) * | 1954-01-26 | 1956-12-04 | Interchem Corp | Anthraquinone dyes |
-
1958
- 1958-03-19 CH CH351253D patent/CH351253A/en unknown
-
1959
- 1959-03-09 CH CH355126D patent/CH355126A/en unknown
- 1959-03-16 US US799442A patent/US3043646A/en not_active Expired - Lifetime
- 1959-03-17 FR FR789596A patent/FR1218936A/en not_active Expired
- 1959-03-18 GB GB9446/59A patent/GB894338A/en not_active Expired
- 1959-03-18 DE DES62204A patent/DE1144678B/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE456235C (en) * | 1925-04-17 | 1928-02-18 | I G Farbenindustrie Akt Ges | Process for the preparation of anthraquinone derivatives |
| US2922691A (en) * | 1955-08-02 | 1960-01-26 | Ciba Ltd | Anthraquinone dyes and polyethylene terephthalate fibers dyed therewith |
| US2993917A (en) * | 1957-12-30 | 1961-07-25 | Cfmc | New anthraquinone dyestuffs and a process for their preparation |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3265460A (en) * | 1960-03-22 | 1966-08-09 | Allied Chem | Dyeing of synthetic fibers |
| US3549667A (en) * | 1962-01-12 | 1970-12-22 | Bayer Ag | Preparation of aryl substituted hydroxy anthraquinones |
| US3349104A (en) * | 1962-08-13 | 1967-10-24 | Ici Ltd | 2-acyloxyphenyl-4, 8-diamino-1, 5-dihydroxy-anthraquinones |
| US3669994A (en) * | 1964-03-25 | 1972-06-13 | Ici Ltd | Anthraquinone dyestuffs |
| EP0063713A1 (en) * | 1981-04-18 | 1982-11-03 | MERCK PATENT GmbH | Dichroic anthraquinone dyes, liquid crystal dielectrics containing them and electro-optical display |
Also Published As
| Publication number | Publication date |
|---|---|
| CH351253A (en) | 1961-01-15 |
| CH355126A (en) | 1961-06-30 |
| DE1144678B (en) | 1963-03-07 |
| GB894338A (en) | 1962-04-18 |
| FR1218936A (en) | 1960-05-13 |
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