US2546168A - Emulsions of water-insoluble organic acid-fading inhibitors dissolved in water-insoluble organic solvents - Google Patents
Emulsions of water-insoluble organic acid-fading inhibitors dissolved in water-insoluble organic solvents Download PDFInfo
- Publication number
- US2546168A US2546168A US37094A US3709448A US2546168A US 2546168 A US2546168 A US 2546168A US 37094 A US37094 A US 37094A US 3709448 A US3709448 A US 3709448A US 2546168 A US2546168 A US 2546168A
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- United States
- Prior art keywords
- water
- organic
- dyed
- emulsion
- acid
- 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
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- 239000000839 emulsion Substances 0.000 title claims description 40
- 238000005562 fading Methods 0.000 title claims description 38
- 239000003960 organic solvent Substances 0.000 title claims description 11
- 239000003112 inhibitor Substances 0.000 title description 7
- 239000000463 material Substances 0.000 claims description 37
- 239000002253 acid Substances 0.000 claims description 32
- 239000003795 chemical substances by application Substances 0.000 claims description 32
- 239000004753 textile Substances 0.000 claims description 31
- 230000002401 inhibitory effect Effects 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 229920002678 cellulose Polymers 0.000 claims description 22
- 239000001913 cellulose Substances 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 15
- 239000004094 surface-active agent Substances 0.000 claims description 13
- 239000002270 dispersing agent Substances 0.000 claims description 12
- 150000007524 organic acids Chemical class 0.000 claims description 10
- 239000006185 dispersion Substances 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 239000004744 fabric Substances 0.000 description 20
- 229920002301 cellulose acetate Polymers 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 239000002202 Polyethylene glycol Substances 0.000 description 11
- 229920001223 polyethylene glycol Polymers 0.000 description 11
- 239000003086 colorant Substances 0.000 description 7
- 239000003517 fume Substances 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- 125000000129 anionic group Chemical group 0.000 description 6
- 238000005108 dry cleaning Methods 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- -1 fatty acid ester Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- WYEYGPJVIZYKNM-UHFFFAOYSA-N 1,3-diphenylimidazolidine Chemical compound C1CN(C=2C=CC=CC=2)CN1C1=CC=CC=C1 WYEYGPJVIZYKNM-UHFFFAOYSA-N 0.000 description 2
- CLCMSGXEVLGRNG-UHFFFAOYSA-N 2,2-diphenylethanimidamide Chemical compound C=1C=CC=CC=1C(C(=N)N)C1=CC=CC=C1 CLCMSGXEVLGRNG-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HDIFHQMREAYYJW-XGXNLDPDSA-N Glyceryl Ricinoleate Chemical class CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OCC(O)CO HDIFHQMREAYYJW-XGXNLDPDSA-N 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- ZEMPKEQAKRGZGQ-VBJOUPRGSA-N triricinolein Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/C[C@H](O)CCCCCC)COC(=O)CCCCCCC\C=C/C[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-VBJOUPRGSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 1
- FCWBHVZCSYIWHX-UHFFFAOYSA-N 1-(dimethylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N(C)C FCWBHVZCSYIWHX-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- BPIUIOXAFBGMNB-UHFFFAOYSA-N 1-hexoxyhexane Chemical compound CCCCCCOCCCCCC BPIUIOXAFBGMNB-UHFFFAOYSA-N 0.000 description 1
- BTHVTFPYYDKBKD-UHFFFAOYSA-N 2,3-diphenylbenzenecarboximidamide Chemical compound C=1C=CC=CC=1C=1C(C(=N)N)=CC=CC=1C1=CC=CC=C1 BTHVTFPYYDKBKD-UHFFFAOYSA-N 0.000 description 1
- GRWKNBPOGBTZMN-UHFFFAOYSA-N 2-benzyl-3-phenylpropane-1,2-diamine Chemical compound C=1C=CC=CC=1CC(N)(CN)CC1=CC=CC=C1 GRWKNBPOGBTZMN-UHFFFAOYSA-N 0.000 description 1
- JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-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
- FHQRDEDZJIFJAL-UHFFFAOYSA-N 4-phenylmorpholine Chemical compound C1COCCN1C1=CC=CC=C1 FHQRDEDZJIFJAL-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 229920008347 Cellulose acetate propionate Polymers 0.000 description 1
- DQEFEBPAPFSJLV-UHFFFAOYSA-N Cellulose propionate Chemical compound CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 DQEFEBPAPFSJLV-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 1
- 229920001727 cellulose butyrate Polymers 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 229920006218 cellulose propionate Polymers 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- PONXTPCRRASWKW-KBPBESRZSA-N diphenylethylenediamine Chemical compound C1([C@H](N)[C@@H](N)C=2C=CC=CC=2)=CC=CC=C1 PONXTPCRRASWKW-KBPBESRZSA-N 0.000 description 1
- WRZXKWFJEFFURH-UHFFFAOYSA-N dodecaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO WRZXKWFJEFFURH-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- HSZCJVZRHXPCIA-UHFFFAOYSA-N n-benzyl-n-ethylaniline Chemical compound C=1C=CC=CC=1N(CC)CC1=CC=CC=C1 HSZCJVZRHXPCIA-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000003799 water insoluble solvent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/017—Mixtures of compounds
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/02—After-treatment
- D06P5/04—After-treatment with organic compounds
- D06P5/06—After-treatment with organic compounds containing nitrogen
-
- 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
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/03—Organic sulfoxy compound containing
- Y10S516/04—Protein or carboxylic compound containing
-
- 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
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/03—Organic sulfoxy compound containing
- Y10S516/05—Organic amine, amide, or n-base containing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/907—Nonionic emulsifiers for dyeing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/908—Anionic emulsifiers for dyeing
- Y10S8/909—Sulfonated or sulfated alphatic hydrocarbons
Definitions
- This invention relates to the treatment of dyed organic derivatives of cellulose textile materials, and relates more particularly to a novel treatment for organic derivative of cellulose textile materials dyed with dyestuffs having a tendency to fade when expos d to an acid atmosphere, whereby said fading is inhibited.
- An object of this invention is to provide an improved process for the treatment of colored cellulose acetate or other organic derivative of cellulose textile materials which .have been dyed with colors which are ot ordinarily fast to acid fumes whereby the resistance of said dyed textile materials to acid fading is substantially improved.
- Another object of this invention is the provision of dyed c llulose acetate or other organic derivative of cellulose textile materials which are highly resistant to acid fading. and whose acid fading resistance is substantially permanent to Washing and dry cleaning.
- the stable aqueous emulsion We employ consists of a solution of said inhibiting agent in a water-insoluble organic solvent, said solution being dispersed in water with the aid of suitable dispersing agents, so that in the emulsion formed the droplets of the water-insoluble solvent solution of the inhibiting agent comprise the disperse phase and the water comprises the continuous phase of said emulsion.
- inhibiting agents which we may employ in practicing the process of our invention, there may be mentioned diphenylethylene dianiine, NN-diphenylacetamidine, N methyl- NN' diphenylacetamidine, N e ethyl NN die phenylacetamidine, benzyl ethyl aniline, "phenyl morpholine, diphenyl guanidine, dibenzylethylenediamine, diphenylbenzamidine, benzimidoazole, 2-methyl-benzimidoazole and 1,3-diphenylimidazolidine.
- the aqueous emulsions employed in accordance with our novel process preferably contain from 0.3 to 2.0% by weight of said inhibiting agent.
- the emulsion is preferably applied to the dyed organic derivative of cellulose textile material by padding operations, the nip of the padding mangle being so adjusted that sufficient liquid is retained on the fabric to deposit in a uniform fashion thereon from 0.3 to 2.0% on the weight of the fabric of the inhibiting agent after the organic liquid solvent and Water in which the latter is dispersed are removed and the treated fabric is dried. Drying of the padded fabric may be conveniently efiected at a temperature. of 570 to 150 C., the treated fabric being exposed to said temperature until the liquid present is evaporated, usually in from about 5 to about 20 minutes.
- the inhibiting agent'which is employed is dissolved in a water-insoluble organic liquid solvent therefor containing a plurality of dispersing agents, at least one of which is a water-soluble anionic surface active agent and one which is a waterinsoluble, but oil-soluble, non-ionic surface active agent, and the organic solution obtained then dispersed in water with agitation to form the desirzd stabl aqueous emulsion.
- the emulsion thus obtained comprises a dispersion of droplets of an organic solution'of the inhibitor in water.
- the water-insoluble but oil-soluble 'the emulsion and acts as an auxiliary solvent for the amine inhibitor in the organic solv'nt while the water-soluble, anionic surface active agent stabilizes the emulsion of the water-insoluble droplets in the aqueous, continuous phase.
- the aqueous emulsion is preferably applied, as stated, by padding operations, although any other con venient method of application may be employed.
- a water-soluble anionic surface active agent consisting, for example, of a highly sulfonated fatty acid ester, such as sulfcnated glyceryl triricinoleate, and from about 5 to 15 parts by weight of a non-ionic water-insoluble, but oil-soluble, surface active agent, such as the condensate of a polyethylene glycol, -i. e.
- n is an integer of from 2 to 10
- a long chain fatty ac d for example, oleic acid
- a water-insoluble organic solvent such as toluene, xylene, isopropyl ether, dibutyl ether, dihexyl ether, beta-beta'-dichlor-diethyl ether, glycol dioleate or benzene, for example.
- dioxan ethyl alcohol
- diacetone alcohol or acetone may then be added thereto to increase the solvent power of the mixture for the inhibiting agent.
- a watermiscible condensate of a polyethyltne glycol with a long chain aliphatic alcohol, such as laur'yl alcohol may also be added to the organic solvent solution to aid in stabilizing the emulsion.
- About 10 to 20 parts by weight of the desiredinhibiting agent are then dissolved in about 30 parts by weight of the organic solution of dispersing agents thus formed by adding the amine to the solution and heating the mixture to about '75 to 80 C.
- the solution of the amine thus obtai-nedis then dispersed with stirring in about 1000*parts by weight of water so as to form-the desired aqueous emulsion which is applied to the dyed textile material.
- Example I A solution of dispersing agents is formed by dissolving 10 parts by weight of completely sulfonatad glyceryl triricinoleate, 10 parts by weight of the monolauryl ether of a polyethylene glycol 0f the general formula HOCHiCHP-O (CI-ICHzO) nC1zH25 wherein n is 2, 10 parts by weight of the dioleate of a polyethylene glycol, such as dodecaethylene glycol, and 10 parts by weight of dioxan in 60 parts by weight of toluene. 10 parts by weight of diphenylethylenediamine are dissolved in 30 parts by weight of the above solution by warming the latter to to C. and the resulting solution then poured into 970 parts by weight of water with stirring. An emulsion of organic liquid droplets in water is formed by further stirring at high speed. The average particle size of the amine is thus reduced to about 1 micron or less.
- a cellulose acetate fabric dyed in a blue shade with 1:4 dimethylamino anthraquinone is padded with the above emulsion, the nip of the padding mangle being so adjusted that the fabric retains an equal weight of liquid.
- the impregnated fabric is then dried by heating at 80 to C. for about l5 minutes. About 1% on the weight ofthe dyed fabric of diplienylethylenediamine is thus deposited thereon.
- the treated dyed fabric has a resistance to acid fading of 2 units in accordance with the standard A. A. T. C. 0. test while untreated dyed fabric has an acid fading resistance of only 0 units. The treated fabric retains its resistance to acid fading even after being washed or dry cleaned.
- Example II An aqueous emulsion containing 1% by weight of diphenylacetarnidine is prepared in the man ner described in Example I.
- the treated dyed fabric obtained exhibits a resistance to acid fading of 1.5 units in accordance with the standard A. A. T. C. C. test.
- .untreated dyed fabric has a resistance to acid fading of but 0 units.
- Example III An aqueous emulsion containing 1% by weight of 1,3-diphenylimidazolidine is prepared in the manner described in Examplelfi
- th treated dyed fabric exhibits an acid fading resistance of 2 units in accordance with the standard A.
- Untreated dyed fabric has a resistance of 0 units. While our invention has been more particularly described.
- Process for improving the fastness of colorations on dyed organic derivative of cellulose textile material to acid fading which comprises treating said dyed organic derivative of cellulose textile material with a stable emulsion comprising a dispersion in Water of a solution in a waterinsoluble organic solvent of a water-insoluble organic acid fading inhibiting agent, said emulsion being formed by dissolving a plurality of dispersing agents in the organic solvent employed, at least one of which dispersing agents is a watersoluble anionic surface active agent and one a water-insoluble but oil-soluble non-ionic surface active agent, adding the inhibiting agent thereto, dissolving it therein and dispersing the resulting organic solution in water.
- Process for improving the fastness of colorations on dyed cellulose acetate textile material to acid fading which comprises treating said dyed cellulose acetate textile material with a stable emulsion comprising a dispersion in water of a solution in a water-insoluble organic solvent of a water-insoluble organic acid fading inhibiting agent, said emulsion being formed by dissolving a plurality of dispersing agents in the organic solvent employed, at least one of which dispersing agents is a water-soluble anionic surface active agent and one a water-insoluble but oil-solublenondonic surface active agent, adding the inhibiting agent thereto, dissolving it therein and dispersing the resulting organic solution in water.
- Process for improving the fastness of colorations on dyed organic derivative of cellulose textile materials to acid fading which comprises treating said dyed organic derivative of cellulose textile materials with a stable emulsion comprising a dispersion in water of a solution of a water-insoluble organic acid fading inhibiting agent in toluene, said emulsion being prepared by dissolving a plurality of dispersing agents in toluene, at least one of which dispersing agents is a water-soluble anionic surface active agent and one a water-insoluble but oil-soluble non-ionic surface active agent, adding the inhibiting agent thereto, dissolving it therein and dispersing the resulting organic solution in water.
- Process for improving the fastness of colorations on dyed organic derivative of cellulose textile materials to acid fading which comprises treating said dyed organic derivative of cellulose textile materials with a stable emulsion comprising a dispersion in water of a solution of a water-insoluble organic acid fading inhibiting agent in toluene, said emulsion being prepared by dissolving sulfonated glyceryl riclnoleate, a water-insoluble, oil-soluble dioleate of a polyethylene glycol and the mono-lauryl ether of a polyethylene glycol in toluene, adding the inhibiting agent thereto, dissolving it therein, and dispersing the resulting organic solution in water.
- Process for improving the fastness of colorations on dyed cellulose acetate textile materials to acid fading which comprises treating said dyed cellulose acetate textile materials with a stable emulsion comprising a dispersion in water of a solution of a water-insoluble organic acid fading inhibiting agent in toluene and dioxan, said emulsion being prepared by dissolving sulfonated glyceryl ricinoleate, a water-insoluble, oil-soluble dioleate of a polyethylene glycol and the mono-lauryl ether of a polyethylene glycol in a mixture of toluene and dioxan, adding the inhibiting agent thereto, dissolving it therein, and dispersing the resulting organic solution in water.
- Process for improving the fastness of colorations on dyed cellulose acetate textile materials to acid fading which comprises treating said dyed cellulose acetate materials with a stable emulsion comprising a dispersion in water of a solution of a water-insoluble organic acid fading inhibiting agent in toluene and ethyl alcohol, said emulsion being prepared by dissolving sulfonated glyceryl ricinoleate, a water-insoluble, oilsoluble dioleate of a polyethylene glycol and the mono-lauryl ether of a polyethylene glycol in a mixture of toluene and ethyl alcohol, adding the inhibiting agent thereto, dissolving it therein, and dispersing the resulting organic solution in water.
- Process for improving the fastness of colorations on dyed cellulose acetate textile materials to acid fading which comprises treating said dyed cellulose acetat materials with a suitable emulsion comprising a dispersion in water of a solution of a' water-insoluble organic acid fading inhibiting agent, in toluene and ethyl alcohol, said emulsion being prepared by dissolving 5 to 15 parts by weight of sulfonated glyceryl triric- 'inoleate, 5 to 15 parts by weight of a waterinsoluble, oil-soluble dioleate of a polyethylene glycol and 10 to 20 parts by weight of the-monolauryl ether of a polyethylene glycol in a mixture of 50 to parts by weight of toluene containing 10 to 20 parts by weight of ethyl alcohol, adding 10 to 20 parts by weight of the desired inhibiting agent thereto, dissolving it therein and dispersing the resulting organic solution in water.
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Description
Patented Mar. 27, 1951 EMULSIONS OF WATER-INSOLUBLE OR- GANIC ACID-FADING INHIBITORS DIS- SOLVED IN WATER-INSOLUBLE ORGANIC SOLVENTS 'William 1. Hart, Dover, and Victor S. Salvin,
Irvington, N. 1., assignors to Celanese Corporation of America, a corporation of Delaware No Drawing. Application .luly'3,1'94 8, Serial No. 37,094
7 Claims.
This invention relates to the treatment of dyed organic derivatives of cellulose textile materials, and relates more particularly to a novel treatment for organic derivative of cellulose textile materials dyed with dyestuffs having a tendency to fade when expos d to an acid atmosphere, whereby said fading is inhibited.
An object of this invention is to provide an improved process for the treatment of colored cellulose acetate or other organic derivative of cellulose textile materials which .have been dyed with colors which are ot ordinarily fast to acid fumes whereby the resistance of said dyed textile materials to acid fading is substantially improved.
Another object of this invention is the provision of dyed c llulose acetate or other organic derivative of cellulose textile materials which are highly resistant to acid fading. and whose acid fading resistance is substantially permanent to Washing and dry cleaning.
Other objects of this invention will appear from the following detailed description.
In the coloration of textile materials it is very desirable that the colors produced on the materials be as fast as possible to light, washing and to other agencies such as acid fumes. Many dyestuifs yield on organic derivative of cellulose materials desirable colors which are fast to Washing but these colors often suffer from a lack of fastness to acid fumes. 'When fabrics to which these dyestuffs have been applied are exposed to acid fumes, such as, for example, the products of combustion of coal, gas, etc., the color undergoes a change in shade. This change is usually referred to as acid fading. The change which occurs may be a dulling of the brightness of the shade in some instances, and in others there may be a definite change in color. This undesirable effect is frequently observed in the case of many anthraquinone dyestuffs which yield valuable blue colors on organic derivative of cellulose materials. When fabrics dyed with these colors are exposed to acid fumes the colors change from a pure blue shade to one having a reddish cast. On continued exposure to the acid fumes the blue color may even change to a pink color. Such changes naturally restrict the range of usefulness of these dyestuffs. In order to overcome this tendency toward acid fading, the usegi various protective or acid-fading inhibiting agents has been suggested. While many of the agents do impart an appreciable degree of protection, the effect is usually not completely permanent since washing or dry-cleaning elimihates in. whole or in part the protective effect achieved. This appears to be due to the fact that by the usual methods of applying said organic acid fading inhibiting agents only a surface applicaton is realized and washing or dry cleaning remove said agents. Accordingly, more effective methods of increasing the resistance of these dyes to acid fading are of great commercial importance.
We have now found that the acid fading characteristics of dyed cellulose acetate or other organic derivative of cellulose textile materials which have been dyed with dyestuffs having a tendency to fade when exposed to the action of acid fumes may be substantially improved and the resistance to acid fading thus imparted is rendered substantially permanent to washing and dry cleaning if said dyed cellulose acetate or other organic derivative of cellulose textile material is treated with a stable aqueous emulsion of an organic acid fading inhibiting agent, which emulsion is formulated in a particular manner. In accordance with our novel process the stable aqueous emulsion We employ consists of a solution of said inhibiting agent in a water-insoluble organic solvent, said solution being dispersed in water with the aid of suitable dispersing agents, so that in the emulsion formed the droplets of the water-insoluble solvent solution of the inhibiting agent comprise the disperse phase and the water comprises the continuous phase of said emulsion.
As examples of inhibiting agents which we may employ in practicing the process of our invention, there may be mentioned diphenylethylene dianiine, NN-diphenylacetamidine, N methyl- NN' diphenylacetamidine, N e ethyl NN die phenylacetamidine, benzyl ethyl aniline, "phenyl morpholine, diphenyl guanidine, dibenzylethylenediamine, diphenylbenzamidine, benzimidoazole, 2-methyl-benzimidoazole and 1,3-diphenylimidazolidine.
The aqueous emulsions employed in accordance with our novel process preferably contain from 0.3 to 2.0% by weight of said inhibiting agent. The emulsion is preferably applied to the dyed organic derivative of cellulose textile material by padding operations, the nip of the padding mangle being so adjusted that sufficient liquid is retained on the fabric to deposit in a uniform fashion thereon from 0.3 to 2.0% on the weight of the fabric of the inhibiting agent after the organic liquid solvent and Water in which the latter is dispersed are removed and the treated fabric is dried. Drying of the padded fabric may be conveniently efiected at a temperature. of 570 to 150 C., the treated fabric being exposed to said temperature until the liquid present is evaporated, usually in from about 5 to about 20 minutes.
In order to form the aqueous emulsion which is applied to the dyed textile material, the inhibiting agent'which is employed is dissolved in a water-insoluble organic liquid solvent therefor containing a plurality of dispersing agents, at least one of which is a water-soluble anionic surface active agent and one which is a waterinsoluble, but oil-soluble, non-ionic surface active agent, and the organic solution obtained then dispersed in water with agitation to form the desirzd stabl aqueous emulsion. The emulsion thus obtained comprises a dispersion of droplets of an organic solution'of the inhibitor in water. The water-insoluble but oil-soluble 'the emulsion and acts as an auxiliary solvent for the amine inhibitor in the organic solv'nt while the water-soluble, anionic surface active agent stabilizes the emulsion of the water-insoluble droplets in the aqueous, continuous phase. In treating the textile material, the aqueous emulsion is preferably applied, as stated, by padding operations, although any other con venient method of application may be employed. 'When forming the emulsion, optimum results are obtained when the organic solution which is dispersed in water is formed by dissolving from about 5 to parts by weight of a water-soluble anionic surface active agent consisting, for example, of a highly sulfonated fatty acid ester, such as sulfcnated glyceryl triricinoleate, and from about 5 to 15 parts by weight of a non-ionic water-insoluble, but oil-soluble, surface active agent, such as the condensate of a polyethylene glycol, -i. e. a compound of the formula HO' (CH2CH2O)1LOH, wherein n is an integer of from 2 to 10, with a long chain fatty ac d, for example, oleic acid, in 50 to 90 parts by weight of a water-insoluble organic solvent such as toluene, xylene, isopropyl ether, dibutyl ether, dihexyl ether, beta-beta'-dichlor-diethyl ether, glycol dioleate or benzene, for example. From 10 to 20 parts by weight of dioxan, ethyl alcohol,
diacetone alcohol or acetone may then be added thereto to increase the solvent power of the mixture for the inhibiting agent. Advantageously, from about 10 to 20 parts by weight of a watermiscible condensate of a polyethyltne glycol with a long chain aliphatic alcohol, such as laur'yl alcohol, may also be added to the organic solvent solution to aid in stabilizing the emulsion. About 10 to 20 parts by weight of the desiredinhibiting agent are then dissolved in about 30 parts by weight of the organic solution of dispersing agents thus formed by adding the amine to the solution and heating the mixture to about '75 to 80 C. The solution of the amine thus obtai-nedis then dispersed with stirring in about 1000*parts by weight of water so as to form-the desired aqueous emulsion which is applied to the dyed textile material.
The application of acid fading inhibitors on dyed textile materials in the specific emulsion form in which we apply said inhibitors yields a degree of protection which is quite outstanding. 1 Textile materials treated by our novel emulsion method retain their resistance to acid fading even after said materials are washed or subjected to dry cleaning operations.
Our novel proclss of applying said inhibiting agents in the specific emulsion form described,
4 acts to cause said inhibiting agents to enter the filaments or fibers comprising the textile material in the manner of dyestuffs. Due to the actual absorption of the inhibiting agents, the protective effect obtained is substantially permanent and unaffected by washing or dry cleaning.
In order further to illustrate our invention, but without being limited thereto, the following examples are given:
Example I A solution of dispersing agents is formed by dissolving 10 parts by weight of completely sulfonatad glyceryl triricinoleate, 10 parts by weight of the monolauryl ether of a polyethylene glycol 0f the general formula HOCHiCHP-O (CI-ICHzO) nC1zH25 wherein n is 2, 10 parts by weight of the dioleate of a polyethylene glycol, such as dodecaethylene glycol, and 10 parts by weight of dioxan in 60 parts by weight of toluene. 10 parts by weight of diphenylethylenediamine are dissolved in 30 parts by weight of the above solution by warming the latter to to C. and the resulting solution then poured into 970 parts by weight of water with stirring. An emulsion of organic liquid droplets in water is formed by further stirring at high speed. The average particle size of the amine is thus reduced to about 1 micron or less.
A cellulose acetate fabric dyed in a blue shade with 1:4 dimethylamino anthraquinone is padded with the above emulsion, the nip of the padding mangle being so adjusted that the fabric retains an equal weight of liquid. The impregnated fabric is then dried by heating at 80 to C. for about l5 minutes. About 1% on the weight ofthe dyed fabric of diplienylethylenediamine is thus deposited thereon. The treated dyed fabric has a resistance to acid fading of 2 units in accordance with the standard A. A. T. C. 0. test while untreated dyed fabric has an acid fading resistance of only 0 units. The treated fabric retains its resistance to acid fading even after being washed or dry cleaned.
Example II An aqueous emulsion containing 1% by weight of diphenylacetarnidine is prepared in the man ner described in Example I. When padded onto a cellulose acetate fabric dyed in a blue shade with 1:e-dimethylamino-anthraquinone so as to deposit uniformly thereon 1% by weight of diphenylacetamidine, the treated dyed fabric obtained exhibits a resistance to acid fading of 1.5 units in accordance with the standard A. A. T. C. C. test. As indicated above, .untreated dyed fabric has a resistance to acid fading of but 0 units.
Example III An aqueous emulsion containing 1% by weight of 1,3-diphenylimidazolidine is prepared in the manner described in Examplelfi When padded on to a fabric dyed in a blue-green shade with lA-diethanolamino 5,8 dihydroxy-anthraquinone so as to deposit 1% by weight of said inhibitor thereon, th treated dyed fabric exhibits an acid fading resistance of 2 units in accordance with the standard A. A. T. C. C. test. Untreated dyed fabric has a resistance of 0 units. While our invention has been more particularly described. in connection with the treatment" of cellulose acetate textile materials, equally satisfactory results are obtained when said textile materials have a basis of other organic derivatives of cellulose such as other organic acid esters and ethers of cellulose. Examples of other organic acids esters of cellulose are cellulose propionate, cellulose butyrate, cellulose acetate propionate and cellulose acetate butyrate, while examples of cellulose ethers are ethyl cellulose and benzyl cellulose.
It is to be understood that the foregoing detailed description is given merely by way of illustration and that many variations may be made therein without departing from the spirit of our invention.
Having described our invention, what we desire to secure by Letters Patent is:
1. Process for improving the fastness of colorations on dyed organic derivative of cellulose textile material to acid fading, which comprises treating said dyed organic derivative of cellulose textile material with a stable emulsion comprising a dispersion in Water of a solution in a waterinsoluble organic solvent of a water-insoluble organic acid fading inhibiting agent, said emulsion being formed by dissolving a plurality of dispersing agents in the organic solvent employed, at least one of which dispersing agents is a watersoluble anionic surface active agent and one a water-insoluble but oil-soluble non-ionic surface active agent, adding the inhibiting agent thereto, dissolving it therein and dispersing the resulting organic solution in water.
2. Process for improving the fastness of colorations on dyed cellulose acetate textile material to acid fading, which comprises treating said dyed cellulose acetate textile material with a stable emulsion comprising a dispersion in water of a solution in a water-insoluble organic solvent of a water-insoluble organic acid fading inhibiting agent, said emulsion being formed by dissolving a plurality of dispersing agents in the organic solvent employed, at least one of which dispersing agents is a water-soluble anionic surface active agent and one a water-insoluble but oil-solublenondonic surface active agent, adding the inhibiting agent thereto, dissolving it therein and dispersing the resulting organic solution in water.
3. Process for improving the fastness of colorations on dyed organic derivative of cellulose textile materials to acid fading, which comprises treating said dyed organic derivative of cellulose textile materials with a stable emulsion comprising a dispersion in water of a solution of a water-insoluble organic acid fading inhibiting agent in toluene, said emulsion being prepared by dissolving a plurality of dispersing agents in toluene, at least one of which dispersing agents is a water-soluble anionic surface active agent and one a water-insoluble but oil-soluble non-ionic surface active agent, adding the inhibiting agent thereto, dissolving it therein and dispersing the resulting organic solution in water.
4. Process for improving the fastness of colorations on dyed organic derivative of cellulose textile materials to acid fading, which comprises treating said dyed organic derivative of cellulose textile materials with a stable emulsion comprising a dispersion in water of a solution of a water-insoluble organic acid fading inhibiting agent in toluene, said emulsion being prepared by dissolving sulfonated glyceryl riclnoleate, a water-insoluble, oil-soluble dioleate of a polyethylene glycol and the mono-lauryl ether of a polyethylene glycol in toluene, adding the inhibiting agent thereto, dissolving it therein, and dispersing the resulting organic solution in water.
5. Process for improving the fastness of colorations on dyed cellulose acetate textile materials to acid fading, which comprises treating said dyed cellulose acetate textile materials with a stable emulsion comprising a dispersion in water of a solution of a water-insoluble organic acid fading inhibiting agent in toluene and dioxan, said emulsion being prepared by dissolving sulfonated glyceryl ricinoleate, a water-insoluble, oil-soluble dioleate of a polyethylene glycol and the mono-lauryl ether of a polyethylene glycol in a mixture of toluene and dioxan, adding the inhibiting agent thereto, dissolving it therein, and dispersing the resulting organic solution in water.
6. Process for improving the fastness of colorations on dyed cellulose acetate textile materials to acid fading, which comprises treating said dyed cellulose acetate materials with a stable emulsion comprising a dispersion in water of a solution of a water-insoluble organic acid fading inhibiting agent in toluene and ethyl alcohol, said emulsion being prepared by dissolving sulfonated glyceryl ricinoleate, a water-insoluble, oilsoluble dioleate of a polyethylene glycol and the mono-lauryl ether of a polyethylene glycol in a mixture of toluene and ethyl alcohol, adding the inhibiting agent thereto, dissolving it therein, and dispersing the resulting organic solution in water.
7. Process for improving the fastness of colorations on dyed cellulose acetate textile materials to acid fading, which comprises treating said dyed cellulose acetat materials with a suitable emulsion comprising a dispersion in water of a solution of a' water-insoluble organic acid fading inhibiting agent, in toluene and ethyl alcohol, said emulsion being prepared by dissolving 5 to 15 parts by weight of sulfonated glyceryl triric- 'inoleate, 5 to 15 parts by weight of a waterinsoluble, oil-soluble dioleate of a polyethylene glycol and 10 to 20 parts by weight of the-monolauryl ether of a polyethylene glycol in a mixture of 50 to parts by weight of toluene containing 10 to 20 parts by weight of ethyl alcohol, adding 10 to 20 parts by weight of the desired inhibiting agent thereto, dissolving it therein and dispersing the resulting organic solution in water.
WILLIAM J. HART. VICTOR S. SALVIN'.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS OTHER REFERENCES Journal of the Am. Pharm. Assoc. (Scientific Edition) for Feb. 1945, pages 56, 5'7, 58.
Atlas Spans and Atlas Tweens, published by Atlas Powder Co., Wilmington, Del., Nov. 1942, pages 5 and 8.
Claims (1)
1. PROCESS FOR IMPROVING THE FASTNNESS OF COLORATIONS ON DYED ORGANIC DERIVATIVE OF CELLULOSE TEXTILE. MATERIAL TO ACID FADING, WHICH COMPRISES TREATING SAID DYED ORGANIC DERIVATIVE OF CELLULOSE TEXTILE MATERIAL WITH A STABLE EMULSION COMPRISING A DISPERSION IN WATER OF A SOLUTION IN A WATERINSOLUBLE ORGANIC SOLVENT OF A WATER-INSOLUBLE ORGANIC ACID FADING INHIBITING AGENT, SAID EMULSION BEING FORMED BY DISSOLVING A PLURALITY OF DISPERSING AGENTS IN THE ORGANIC SOLVENT EMPLOYED, AT LEAST ONE OF WHICH DISPERSING AGENTS IS A WATERSOLUBLE ANIONIC SURFACE ACTIVE AGENT AND ONE A WATER-INSOLUBLE BUT OIL-SOLUBLE NON-IONIC SURFACE ACTIVE AGENT, ADDING THE INHIBITING AGENT THERETO, DISSOLVING IT THEREIN AND DISPERSING THE RESULTING ORGANIC SOLUTION IN WATER.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37094A US2546168A (en) | 1948-07-03 | 1948-07-03 | Emulsions of water-insoluble organic acid-fading inhibitors dissolved in water-insoluble organic solvents |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37094A US2546168A (en) | 1948-07-03 | 1948-07-03 | Emulsions of water-insoluble organic acid-fading inhibitors dissolved in water-insoluble organic solvents |
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| Publication Number | Publication Date |
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| US2546168A true US2546168A (en) | 1951-03-27 |
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| US37094A Expired - Lifetime US2546168A (en) | 1948-07-03 | 1948-07-03 | Emulsions of water-insoluble organic acid-fading inhibitors dissolved in water-insoluble organic solvents |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2674516A (en) * | 1951-12-05 | 1954-04-06 | Du Pont | Antifume compositions |
| US2757094A (en) * | 1953-08-07 | 1956-07-31 | Guss Charles | Liquid cleaner and polisher and method of compounding the same |
| US2881045A (en) * | 1954-06-17 | 1959-04-07 | American Cyanamid Co | Method of dyeing synthetic fibrous materials |
| US2953421A (en) * | 1954-08-04 | 1960-09-20 | Gen Aniline & Film Corp | Anthraquinone dyestuffs |
| US3049443A (en) * | 1959-01-07 | 1962-08-14 | American Cyanamid Co | Process of dyeing synthetic fibers with o-hydroxybenzophenones |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1690481A (en) * | 1924-08-14 | 1928-11-06 | Celanese Corp | Dyeing, printing, or stenciling of acetyl cellulose or products made therewith |
| US1723271A (en) * | 1926-10-21 | 1929-08-06 | Celanese Corp | Treatment of cellulose derivatives |
| US1803008A (en) * | 1931-04-28 | Dyeing | ||
| US1883351A (en) * | 1926-10-08 | 1932-10-18 | Dreyfus Henry | Treatment of cellulose derivatives |
| US1914945A (en) * | 1927-08-16 | 1933-06-20 | Celanese Corp | Coloration of materials |
| US2416380A (en) * | 1942-07-18 | 1947-02-25 | Ici Ltd | Inhibition of acid-fading on dyed cellulose acetate with n:n' diphenylethylene diamine |
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1948
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Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1803008A (en) * | 1931-04-28 | Dyeing | ||
| US1690481A (en) * | 1924-08-14 | 1928-11-06 | Celanese Corp | Dyeing, printing, or stenciling of acetyl cellulose or products made therewith |
| US1883351A (en) * | 1926-10-08 | 1932-10-18 | Dreyfus Henry | Treatment of cellulose derivatives |
| US1723271A (en) * | 1926-10-21 | 1929-08-06 | Celanese Corp | Treatment of cellulose derivatives |
| US1914945A (en) * | 1927-08-16 | 1933-06-20 | Celanese Corp | Coloration of materials |
| US2416380A (en) * | 1942-07-18 | 1947-02-25 | Ici Ltd | Inhibition of acid-fading on dyed cellulose acetate with n:n' diphenylethylene diamine |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2674516A (en) * | 1951-12-05 | 1954-04-06 | Du Pont | Antifume compositions |
| US2757094A (en) * | 1953-08-07 | 1956-07-31 | Guss Charles | Liquid cleaner and polisher and method of compounding the same |
| US2881045A (en) * | 1954-06-17 | 1959-04-07 | American Cyanamid Co | Method of dyeing synthetic fibrous materials |
| US2953421A (en) * | 1954-08-04 | 1960-09-20 | Gen Aniline & Film Corp | Anthraquinone dyestuffs |
| US3049443A (en) * | 1959-01-07 | 1962-08-14 | American Cyanamid Co | Process of dyeing synthetic fibers with o-hydroxybenzophenones |
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