CA2428758A1 - Composition for dyeing material of synthetic aromatic polyamide fibers comprising a cationic dye - Google Patents
Composition for dyeing material of synthetic aromatic polyamide fibers comprising a cationic dye Download PDFInfo
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- CA2428758A1 CA2428758A1 CA002428758A CA2428758A CA2428758A1 CA 2428758 A1 CA2428758 A1 CA 2428758A1 CA 002428758 A CA002428758 A CA 002428758A CA 2428758 A CA2428758 A CA 2428758A CA 2428758 A1 CA2428758 A1 CA 2428758A1
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- composition
- dye
- approximately
- assistant
- dye assistant
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- 239000000203 mixture Substances 0.000 title claims abstract description 88
- 238000004043 dyeing Methods 0.000 title claims abstract description 28
- 239000000463 material Substances 0.000 title claims abstract description 20
- 239000004760 aramid Substances 0.000 title claims abstract description 17
- 229920003235 aromatic polyamide Polymers 0.000 title claims abstract description 17
- 125000002091 cationic group Chemical group 0.000 title claims abstract description 15
- 239000000835 fiber Substances 0.000 title abstract description 8
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 claims abstract description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 48
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 36
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 claims description 28
- 239000004317 sodium nitrate Substances 0.000 claims description 14
- 235000010344 sodium nitrate Nutrition 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- -1 dodecylbenzene sulfonic acid amine salt Chemical class 0.000 claims description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 8
- 239000003995 emulsifying agent Substances 0.000 claims description 8
- 230000000147 hypnotic effect Effects 0.000 claims description 8
- 239000004094 surface-active agent Substances 0.000 claims description 8
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000003945 anionic surfactant Substances 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- 230000008020 evaporation Effects 0.000 claims description 5
- 238000001704 evaporation Methods 0.000 claims description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 4
- 229920001400 block copolymer Polymers 0.000 claims description 4
- 239000003093 cationic surfactant Substances 0.000 claims description 4
- VNLZLLDMKRKVEX-UHFFFAOYSA-N cyclohex-3-enone Chemical compound O=C1CCC=CC1 VNLZLLDMKRKVEX-UHFFFAOYSA-N 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 239000002736 nonionic surfactant Substances 0.000 claims description 3
- DSZCWNRVMXBILR-UHFFFAOYSA-M (2z)-1,3,3-trimethyl-2-[2-(2-methyl-2,3-dihydroindol-1-ium-1-ylidene)ethylidene]indole;chloride Chemical compound [Cl-].CN/1C2=CC=CC=C2C(C)(C)C\1=C/C=[N+]1C2=CC=CC=C2CC1C DSZCWNRVMXBILR-UHFFFAOYSA-M 0.000 claims description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 claims description 2
- 229940008406 diethyl sulfate Drugs 0.000 claims description 2
- 239000002270 dispersing agent Substances 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- FDZZZRQASAIRJF-UHFFFAOYSA-M malachite green Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 FDZZZRQASAIRJF-UHFFFAOYSA-M 0.000 claims description 2
- 229920001451 polypropylene glycol Polymers 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 claims 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 2
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 claims 2
- 229920000847 nonoxynol Polymers 0.000 claims 2
- 159000000000 sodium salts Chemical class 0.000 claims 2
- 230000008023 solidification Effects 0.000 claims 2
- 238000007711 solidification Methods 0.000 claims 2
- MHOFGBJTSNWTDT-UHFFFAOYSA-M 2-[n-ethyl-4-[(6-methoxy-3-methyl-1,3-benzothiazol-3-ium-2-yl)diazenyl]anilino]ethanol;methyl sulfate Chemical compound COS([O-])(=O)=O.C1=CC(N(CCO)CC)=CC=C1N=NC1=[N+](C)C2=CC=C(OC)C=C2S1 MHOFGBJTSNWTDT-UHFFFAOYSA-M 0.000 claims 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 claims 1
- OJFRRQVRALQLCT-UHFFFAOYSA-N ethoxy-nonyl-phenoxyazanium;sulfate Chemical compound [O-]S([O-])(=O)=O.CCCCCCCCC[NH+](OCC)OC1=CC=CC=C1.CCCCCCCCC[NH+](OCC)OC1=CC=CC=C1 OJFRRQVRALQLCT-UHFFFAOYSA-N 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 description 71
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 30
- 229920000784 Nomex Polymers 0.000 description 14
- 239000004763 nomex Substances 0.000 description 14
- 239000004744 fabric Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229920001993 poloxamer 188 Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZOMLUNRKXJYKPD-UHFFFAOYSA-N 1,3,3-trimethyl-2-[2-(2-methylindol-3-ylidene)ethylidene]indole;hydrochloride Chemical compound [Cl-].C1=CC=C2C(C)(C)C(/C=C/C=3C4=CC=CC=C4NC=3C)=[N+](C)C2=C1 ZOMLUNRKXJYKPD-UHFFFAOYSA-N 0.000 description 1
- DLKDEVCJRCPTLN-UHFFFAOYSA-N 2-butylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCC)C(=O)C2=C1 DLKDEVCJRCPTLN-UHFFFAOYSA-N 0.000 description 1
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 description 1
- 241001550224 Apha Species 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000008821 health effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229940072395 n-butylphthalimide Drugs 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000000007 visual effect Effects 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0075—Preparations with cationic dyes
-
- 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
- Y10S8/924—Polyamide fiber
- Y10S8/925—Aromatic polyamide
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
A composition for dyeing material of synthetic aromatic polyamide fibers, said composition containing a mixture of (a) a cationic dye and (b) a cyclohexenone as a dye assistant. Preferably, 2-cyclohexen-1-one,3,5,5-trimethyl is the dye assistant.
Description
~ ~ _ . . . ~.._. .,_...___... . . ~ 02428758 2003-05-15 Atty. Dkt No. 1179115 JLSlsed -1- 'Express Maa' malrNg number EK5802B8493115 Date of l7aposlt - D~n I
I hereby ceAi<y that this paper a ( is ng deposited with the Unhed states Postal 5ervbe "Express Ma8 host Otfioe to Addresses' service under 37 C.F.R. 1.10 on the data ind'~cated above and ~ addressed to fhe t.ormrtssloner of Patents and Tradenmrks, W0.C. .20291 Nina K Tew Description COMPOSITION FOR DYEING MATERIAL OF SYNTHETIC AROMATIC
POLYAMIDE FIBERS COMPRISING A CATIONIC DYE AND NOVEL DYE
ASSISTANT
Technical Field The present invention relates, in general, to a composition for dyeing material of synthetic aromatic polyamide fibers. More particularly, the present invention relates to such a dyeing composition comprising a cationic dye and a cyclohexenone, such as 2-cyclohexen-1-one,3,5,5-trimethyl.
Background of the Invention Aromatic polyamides have become important synthetic fibers. More specifically, fabrics made of such fibers have long been recognized for their excellent fire retardancy characteristics in that the fabrics have very high melting points and do not ignite at temperatures above their char points.
Accordingly, such fabrics are the primary material used byfire fighters, race car drivers, astronauts, and others who may be subjected to fire or to high temperatures.
The aromatic polyamides are the resultant, for example, of , a , t~ndensation product of an aromatic diamine with an aromatic diacid halide.
I hereby ceAi<y that this paper a ( is ng deposited with the Unhed states Postal 5ervbe "Express Ma8 host Otfioe to Addresses' service under 37 C.F.R. 1.10 on the data ind'~cated above and ~ addressed to fhe t.ormrtssloner of Patents and Tradenmrks, W0.C. .20291 Nina K Tew Description COMPOSITION FOR DYEING MATERIAL OF SYNTHETIC AROMATIC
POLYAMIDE FIBERS COMPRISING A CATIONIC DYE AND NOVEL DYE
ASSISTANT
Technical Field The present invention relates, in general, to a composition for dyeing material of synthetic aromatic polyamide fibers. More particularly, the present invention relates to such a dyeing composition comprising a cationic dye and a cyclohexenone, such as 2-cyclohexen-1-one,3,5,5-trimethyl.
Background of the Invention Aromatic polyamides have become important synthetic fibers. More specifically, fabrics made of such fibers have long been recognized for their excellent fire retardancy characteristics in that the fabrics have very high melting points and do not ignite at temperatures above their char points.
Accordingly, such fabrics are the primary material used byfire fighters, race car drivers, astronauts, and others who may be subjected to fire or to high temperatures.
The aromatic polyamides are the resultant, for example, of , a , t~ndensation product of an aromatic diamine with an aromatic diacid halide.
Examples of such condensation products are. sold under the NOMEX trade name, such as NOMF~C 430, NOMEX 450, and NOMEX 455, by E.I. du Pont de Nemours 8~ Co.
However, satisfactory dyeing of such aromatic polyamide materials has been difficult. As a result, a dye assistant has been used in conjunction with a cationic dye. For quite some time, the primary commercial dyeing method employed acetophenone as the dye assistant.
The use of acetophenone as a phenyl alkyl ketone dye assistant, as well as the use of cyGohexanone as a cycloalkyl ketone dye assistant, in the dyeing of fabrics such as NOMEX with a cationic dye, is disclosed in U.S. Patent No.
However, satisfactory dyeing of such aromatic polyamide materials has been difficult. As a result, a dye assistant has been used in conjunction with a cationic dye. For quite some time, the primary commercial dyeing method employed acetophenone as the dye assistant.
The use of acetophenone as a phenyl alkyl ketone dye assistant, as well as the use of cyGohexanone as a cycloalkyl ketone dye assistant, in the dyeing of fabrics such as NOMEX with a cationic dye, is disclosed in U.S. Patent No.
3,674,420 issued in 1972 to Sapers, assignor to Arkansas Company, Inc.
Sapers also discloses that the dye assistant is admixed with a surfactant, such as a block copolymer of propylene oxide and ethylene oxide (sold as PLURONIC F-68).
Nevertheless, acetophenone, which has been commercialized, is objectionable as a dye assistant not only because of its health effects on personnel (acetophenone is classified as hypnotic), but also because of its strong odor that permeates the dye house and imparts a residual odor to the dyed fabric. Moreover, acetophenone corrodes equipment and pollutes water.
An improved dye assistant is disclosed in U.S. Patent No. 4,780,105 issued in 1988 to White, Ensley, and Dalton, assignors to Stockhausen, Inc.
More specifically, the '105 patent describes a composition for dyeing material of synthetic aromatic polyamide fibers, where the composition includes (1) a . _ cationic dye and (2) a dye assistant that is N-substituted phthalimide.
The N-_3_ substituted phthalimide is admixed with an emulsifier, and preferably, the N-substituted phthalimide is a 2:1 mole ratio of N-butyl phthalimide and N-isopropyl phthaiimide. Also preferably, the emulsifier is propylene oxide and ethylene oxide block polymer, and an anionic surfactant blend, and an anionidcationic surfactant blend.
The disclosures of all of the mentioned patents are incorporated by .
v reference.
Thus, a need still exists to find a dye assistant that is free from hypnotic effects (unlike acetophenone which is hypnotic), and yet is comparable to acetophenone. ~ .
Surnmar~and Objects of the Invention Accordingly, the present invention provides a dyeing composition for dyeing material of synthetic aromatic polyamide materials, where the composition comprises (a) a cationic dye and (b) a cyclohexenone as a dye assistant. Preferably, the cyclohexenone dye assistant comprises a substituted cyclohexenone, more preferably, an alkyl-substituted cyclohexenone, even more preferably, a trialkyl-substituted cyclohexenone, and most preferably, 2-cydohexen=1-one,3,5,5-trimethyl. The dye assistant may further comprise 3-cyclohexen-1-one,3,5,5-trimethyl.
While it is not intended to be bound to any theory, it is believed that the dye assistant operates via a mechanism that swells the synthetic aromatic polyamide materials. ' Hence, it is an object of the present invention to provide a dyeing composition that employs a dye assistant that exhibits a satisfactory color yield andlor a color transfer.
Also, it is another object of the present invention to provide a dyeing composition that is free from hypnotic effects.
. . Some of the objects of the invention having been stated, other objects will become evident as the description proceeds, when taken in connection with the laboratory examples described below.
Detailed Description of the Invention . The dyeing composition of the present invention is useful for dyeing synthetic aromatic polyamide materials, such as those made from fibers such as those sold under the trade name NOMEX, for instance, NOMEX 430, NOMEX 450, and NOMEX 455. NOMEX is a manufactured fiber in which the fiber forming substance is a long chain synthetic polyaramide in which at least . 15 85 % of the amide linkages, namely -C(O~NH-, are attached directly to 2 aromatic rings, for instance, phenyl rings.
Any cationic dye may be employed in the present invention.
Suitable cationic dyes are those mentioned in the above-noted patent to Sapers, such as Astrazon Olive Green Bl_ and Astrazon Orange 3RL (also known; respectively, as Basic Green 6 and Basic Orange 27, and both formerly manufactured by Verona Dyestuffs) and those mentioned in the above-noted patent to White, Ensley, and Dalton, such as Basic Yellow 21, Basib Blue 41, and Basic Red 18 (further identified in the color index, third edition, published by the Society of Dyers and Colourists, Dean House, Piccadilly Bradford, t _: . ,. _ .
'.-' . : : ~ ' ~ .
_5_ Yorkshire, England). Also useful as cationic dyes are Red GL, Yellow SGL, Blue X 3GL-300, and Red FB, sold underthe trade name BASACRYL by BASF
Corporation.
In order to improve the leveling of the dye upon the polyamide material, a dispersing agent selected from surfactants and/or emulsifiers may be employed, including those mentioned in the above-noted patent to Sapers and patent to White, Ensley, and Dalton.
For instance, the patent to Sapers mentions that the surfactant used can be either a cationic surfactant, a blend of a nonionic surtactant plus an anionic surfactant, or a blend of a .nonionic surfactant plus a cationic surfactant.
An example of a cationic surfactant that can be employed is a coconut trimethyl ammonium chloride. An example of an anionic surfactant that can be employed is a nonyl pherioxy ethanoxy ammonium sulfate. Examples of nonionic surfactants that can be employed are a nonyt phenol reacted with 30 ~. 15 moll of ethylene oxide and PLURONIC F-68 which is a block copolymer of polypropylene oxide and ethylene oxide.
Also, as mentioned in the patent to White, Ensley, and Dalton, the emulsifier may be a block polymer of propylene oxide and ethylene oxide. As also mentioned the surfactant may be an anionic surfactant, such as a blend of a diethyl sulfate quaternary of a fatty tertiary amine, ethoxyfated nonyl Furthermore, a very suitable emulsifier useful in the present invention is available under the trade name WITCOMUL 1305 from Witco Chemical.
WITCOMUL 1305 is a modified ethoxyiated fatty acid.
The dye assistant useful in the present invention comprises a cyclohexenone.
.. Preferably, the dye assistant comprises a substituted cyclohexenone, more preferably, an alkyl-substituted cyclohexenone, even more preferably, a trialkyl-substituted cyclohexenone, and most preferably, 2-cyclahexen-1-one,3,5,5-trimethyl. The last is available commercially from Creanova, Inc. as ISOPHORONE, which is a blend of two isomers, namely 98 weight % of 2-cyciohexen-1-one,3,5,5-trimethyl as the major isomer and 2 weight % of 3-cyclohexen-1-one,3,5,5-trimethyl as the minor isomer.
According to product infom~ation provided by Creanova, Inc., ISOPHORONE has the following properties in accordance with the Table below.
. -. ._..---.. _.. . _ .. _._._.._. . .-_... .... .~ 02428758 2003-05-15 . - -Table of ISOPHORONE Properties Property Value Unit Test Method Appearance ~ clear visual Colour (APHA) s50 mg Pt/l DIN ISO 6271 Purity 298.0 % by weightgas (isomer mixture) chromatographic Water content ~ s0.1 % by weightASTM D 760 .
Acid content s0.01 % by weightASTM D 1613 (calculated as acetic acid) Molecular weight 138.21 glmol (CgH~4p) _ Solidifcation pointapprox. 'C DIN ISO 3016 Viscosity @ 20'C approx. mPa s 2.6 Solubility parameterapprox. (J/cm~)'~
@ 17.9 25'C
Heat of evaporationapprox. kJ/mol @ 42.4 b.p.
Vapour pressure 0.4 hl'a @
20'C
Evaporation numberapprox.
(diethyl ether 330 = 1 ) Flash point approx. 'C DIN 51758 Refractive index approx. DIN 51423 @ 1.477 20'C
Relative density approx. glml DIN 51757 @ 0.918 -20'C 0.923 Boiling range @ 210 - 216 'C ASTM D 1078 10.13 hPa Suitably, the proportion of dye assistant to fabric ranges from about 2 to about 50 weight %. Additionally, a small amount, such as about 1 to about 2 weight %, of a salt, such as sodium nitrate is recommended in the dye bath.
Also, the pH of the dye bath is adjusted with acid to a range from about 2.5 to about 4.0, more preferably from about 2.6 to about 3.5, with a pH of about 3.0 being preferred. Suitable acids for the pH adjustment are formic acid, acetic acid, and citric acid.
The dye bath is heated, as is typical in the dyeing process, and the . ~ ~ temperature may be in a range from about 270° Fahrenheit (about 132°.
Celsius) to about 250° I=ahrenheit (about 121 ° Celsius). Also, as is typical during the dyeing process, after 1 or 2 hours at this high temperature, the temperature of the dye bath may be lowered to a temperature in a range from about 190° Fahrenheit (about 88° Celsius) to about 140°
Fahrenheit (about 60°
Celsius). As is well known, the dye bath may be pressurized, and the time and temperature varied, depending on the desired intensity of color.
The following examples are intended to illustrate further the invention, and the invention is not to be limited by these examples. Each % in the following examples is a weight %, as on the weight of the fabric (OWF).
Laboratory Exam,~les xam le I.
_9_ dye mixture together with a dye assistant, where the pH of the composition was adjusted to 3.0 with acetic acid, as follows:
Bath 1 (comparison).
30 % acetophenone 15 % sodium nitrate 5 ml of stock dye mixture acetic acid to adjust pH to 3.0 Bath 2 (the invention).
30 % ISOPHORONE
15 % sodium nitrate 5 ml of stock dye mixture .. acetic acid to adjust pH to 3.0 Bath 3 (the invention).
% ISOPHORONE
15 15 % sodium nitrate 5 ml of stock dye mixture acetic acid to adjust pH to 3.0 Bath 4 (the invention)y 10 % ISOPHORONE ' . 20 15 % sodium nitrate 5 ml of stock dye mixture acetic acid to adjust pH to 3.0 _10_ For each of the 4 dye baths, a sample of NOMEX 455 fabric was dyed at about 265° Fahrenheit (about 129° Celsius) for about 1 hour.
The results were that the composition with ISOPHORONE as the dye assistant yielded equal color on NOMEX 455 as compared to the composition with acetophenone as the dye assistant.
Example II.
The dyeing procedure of Example I was repeated for 6 additional aqueous dye. baths prepared from compositions of dye assistant and stock dye mixture for dyeing NOMEX 455 fabric for about 1 hour at about 265°
Fahrenheit (about 129° Celsius).
The following 6 dye baths prepared from compositions of dye assistant and stock dye mixture were employed:
Bath 1 (comparison).
30 % acetophenone 15 % sodium nitrate 5 ml of stock dye mixture acetic acid to adjust pH to 3.0 _11-Bath 3 (comparison).
% acetophenone % sodium nitrate 5 ml of stock dye mixture 5 , acetic acid to adjust pH to 3.0 . Bath 4 (the invention).
30 % IS.OPHORONE
15 % sodium nitrate 5 ml of stock dye mixture 10 ' acetic acid to adjust pH to 3.0 _ - ~ Bath 5 (the invention).
% ISOPHORONE
15 % sodium nitrate 5 ml of stock dye mixture , 15 acetic acid to adjust pH to 3.0 Bath 6 (the invention).
10 % ISOPHORONE ' 15 % sodium nitrate 5 ml of stock dye mixture 20 acetic acid to adjust pH to 3.0 _12_ Compositions with ISOPHORONE as the dye assistant yielded comparably on NOMEX 455 as compared to compositions with acetophenone as the dye assistant.
Example III.
For 2 additional dye baths prepared from compositions of dye assistant and dye mixture, the procedure of Example I was repeated, except that this time, color transfer was evaluated rather than dye yield as .follows.
Afterdyeing, a colortransfertestwas performed in the following manner.
A dyed fabric sample and an undyed fabric sample were heated together in a bath with the respective dyeing assistant and_sodium nitrate (15 % OWF) with acetic acid at pH 3 to about 265° Fahrenheit (about 129°
Celsius) far about 1 hour. The amount of color transfer from each dyed sample to its respective undyed sample was evaluated.
The following 2 dye bath compositions were evaluated for color transfer:
Bath 1 (comparison).
30 % acetophenone 15 % sodium nitrate 5 ml of stock dye mixture acetic acid to adjust pH to 3.0 Bath 2 (the invention).
% ISOPHORONE
15 % sodium nitrate 5 ml of stock dye mixture acetic acid to adjust~pH to 3.0 : ;;;_.~;.:,;
CA 02428758 2003-05-15, The results were that the composition with ISOPHORONE as the dye assistant was comparable to the composition with acetophenone as the dye assistant with respect to color transfer.
- Example IV.
The procedure of Example I was repeated for Bath 1 (comparison with acetophenone), and for Bath 2 (the invention with ISOPHORONE), except that this time ISOPHORONE was emulsified with 18.9 % of WITCOMUL 1305 prior to admixing with the stock dye mixture to form a dye bath prepared from a composition of dye assistant, emulsifier, and stock dye mixture.
The results were that compositions with emulsified ISOPHORONE as the dye assistant yielded on NOMEX 455 comparably to compositions with acetophenone as the dye assistant.
It will be understood that various details of the invention may be _ changed without departing from the scope of the invention. Furthermore, the foregoing description is for the purpose of illustration only, and not for the purpose of limitation - the invention being defined by the claims.
Sapers also discloses that the dye assistant is admixed with a surfactant, such as a block copolymer of propylene oxide and ethylene oxide (sold as PLURONIC F-68).
Nevertheless, acetophenone, which has been commercialized, is objectionable as a dye assistant not only because of its health effects on personnel (acetophenone is classified as hypnotic), but also because of its strong odor that permeates the dye house and imparts a residual odor to the dyed fabric. Moreover, acetophenone corrodes equipment and pollutes water.
An improved dye assistant is disclosed in U.S. Patent No. 4,780,105 issued in 1988 to White, Ensley, and Dalton, assignors to Stockhausen, Inc.
More specifically, the '105 patent describes a composition for dyeing material of synthetic aromatic polyamide fibers, where the composition includes (1) a . _ cationic dye and (2) a dye assistant that is N-substituted phthalimide.
The N-_3_ substituted phthalimide is admixed with an emulsifier, and preferably, the N-substituted phthalimide is a 2:1 mole ratio of N-butyl phthalimide and N-isopropyl phthaiimide. Also preferably, the emulsifier is propylene oxide and ethylene oxide block polymer, and an anionic surfactant blend, and an anionidcationic surfactant blend.
The disclosures of all of the mentioned patents are incorporated by .
v reference.
Thus, a need still exists to find a dye assistant that is free from hypnotic effects (unlike acetophenone which is hypnotic), and yet is comparable to acetophenone. ~ .
Surnmar~and Objects of the Invention Accordingly, the present invention provides a dyeing composition for dyeing material of synthetic aromatic polyamide materials, where the composition comprises (a) a cationic dye and (b) a cyclohexenone as a dye assistant. Preferably, the cyclohexenone dye assistant comprises a substituted cyclohexenone, more preferably, an alkyl-substituted cyclohexenone, even more preferably, a trialkyl-substituted cyclohexenone, and most preferably, 2-cydohexen=1-one,3,5,5-trimethyl. The dye assistant may further comprise 3-cyclohexen-1-one,3,5,5-trimethyl.
While it is not intended to be bound to any theory, it is believed that the dye assistant operates via a mechanism that swells the synthetic aromatic polyamide materials. ' Hence, it is an object of the present invention to provide a dyeing composition that employs a dye assistant that exhibits a satisfactory color yield andlor a color transfer.
Also, it is another object of the present invention to provide a dyeing composition that is free from hypnotic effects.
. . Some of the objects of the invention having been stated, other objects will become evident as the description proceeds, when taken in connection with the laboratory examples described below.
Detailed Description of the Invention . The dyeing composition of the present invention is useful for dyeing synthetic aromatic polyamide materials, such as those made from fibers such as those sold under the trade name NOMEX, for instance, NOMEX 430, NOMEX 450, and NOMEX 455. NOMEX is a manufactured fiber in which the fiber forming substance is a long chain synthetic polyaramide in which at least . 15 85 % of the amide linkages, namely -C(O~NH-, are attached directly to 2 aromatic rings, for instance, phenyl rings.
Any cationic dye may be employed in the present invention.
Suitable cationic dyes are those mentioned in the above-noted patent to Sapers, such as Astrazon Olive Green Bl_ and Astrazon Orange 3RL (also known; respectively, as Basic Green 6 and Basic Orange 27, and both formerly manufactured by Verona Dyestuffs) and those mentioned in the above-noted patent to White, Ensley, and Dalton, such as Basic Yellow 21, Basib Blue 41, and Basic Red 18 (further identified in the color index, third edition, published by the Society of Dyers and Colourists, Dean House, Piccadilly Bradford, t _: . ,. _ .
'.-' . : : ~ ' ~ .
_5_ Yorkshire, England). Also useful as cationic dyes are Red GL, Yellow SGL, Blue X 3GL-300, and Red FB, sold underthe trade name BASACRYL by BASF
Corporation.
In order to improve the leveling of the dye upon the polyamide material, a dispersing agent selected from surfactants and/or emulsifiers may be employed, including those mentioned in the above-noted patent to Sapers and patent to White, Ensley, and Dalton.
For instance, the patent to Sapers mentions that the surfactant used can be either a cationic surfactant, a blend of a nonionic surtactant plus an anionic surfactant, or a blend of a .nonionic surfactant plus a cationic surfactant.
An example of a cationic surfactant that can be employed is a coconut trimethyl ammonium chloride. An example of an anionic surfactant that can be employed is a nonyl pherioxy ethanoxy ammonium sulfate. Examples of nonionic surfactants that can be employed are a nonyt phenol reacted with 30 ~. 15 moll of ethylene oxide and PLURONIC F-68 which is a block copolymer of polypropylene oxide and ethylene oxide.
Also, as mentioned in the patent to White, Ensley, and Dalton, the emulsifier may be a block polymer of propylene oxide and ethylene oxide. As also mentioned the surfactant may be an anionic surfactant, such as a blend of a diethyl sulfate quaternary of a fatty tertiary amine, ethoxyfated nonyl Furthermore, a very suitable emulsifier useful in the present invention is available under the trade name WITCOMUL 1305 from Witco Chemical.
WITCOMUL 1305 is a modified ethoxyiated fatty acid.
The dye assistant useful in the present invention comprises a cyclohexenone.
.. Preferably, the dye assistant comprises a substituted cyclohexenone, more preferably, an alkyl-substituted cyclohexenone, even more preferably, a trialkyl-substituted cyclohexenone, and most preferably, 2-cyclahexen-1-one,3,5,5-trimethyl. The last is available commercially from Creanova, Inc. as ISOPHORONE, which is a blend of two isomers, namely 98 weight % of 2-cyciohexen-1-one,3,5,5-trimethyl as the major isomer and 2 weight % of 3-cyclohexen-1-one,3,5,5-trimethyl as the minor isomer.
According to product infom~ation provided by Creanova, Inc., ISOPHORONE has the following properties in accordance with the Table below.
. -. ._..---.. _.. . _ .. _._._.._. . .-_... .... .~ 02428758 2003-05-15 . - -Table of ISOPHORONE Properties Property Value Unit Test Method Appearance ~ clear visual Colour (APHA) s50 mg Pt/l DIN ISO 6271 Purity 298.0 % by weightgas (isomer mixture) chromatographic Water content ~ s0.1 % by weightASTM D 760 .
Acid content s0.01 % by weightASTM D 1613 (calculated as acetic acid) Molecular weight 138.21 glmol (CgH~4p) _ Solidifcation pointapprox. 'C DIN ISO 3016 Viscosity @ 20'C approx. mPa s 2.6 Solubility parameterapprox. (J/cm~)'~
@ 17.9 25'C
Heat of evaporationapprox. kJ/mol @ 42.4 b.p.
Vapour pressure 0.4 hl'a @
20'C
Evaporation numberapprox.
(diethyl ether 330 = 1 ) Flash point approx. 'C DIN 51758 Refractive index approx. DIN 51423 @ 1.477 20'C
Relative density approx. glml DIN 51757 @ 0.918 -20'C 0.923 Boiling range @ 210 - 216 'C ASTM D 1078 10.13 hPa Suitably, the proportion of dye assistant to fabric ranges from about 2 to about 50 weight %. Additionally, a small amount, such as about 1 to about 2 weight %, of a salt, such as sodium nitrate is recommended in the dye bath.
Also, the pH of the dye bath is adjusted with acid to a range from about 2.5 to about 4.0, more preferably from about 2.6 to about 3.5, with a pH of about 3.0 being preferred. Suitable acids for the pH adjustment are formic acid, acetic acid, and citric acid.
The dye bath is heated, as is typical in the dyeing process, and the . ~ ~ temperature may be in a range from about 270° Fahrenheit (about 132°.
Celsius) to about 250° I=ahrenheit (about 121 ° Celsius). Also, as is typical during the dyeing process, after 1 or 2 hours at this high temperature, the temperature of the dye bath may be lowered to a temperature in a range from about 190° Fahrenheit (about 88° Celsius) to about 140°
Fahrenheit (about 60°
Celsius). As is well known, the dye bath may be pressurized, and the time and temperature varied, depending on the desired intensity of color.
The following examples are intended to illustrate further the invention, and the invention is not to be limited by these examples. Each % in the following examples is a weight %, as on the weight of the fabric (OWF).
Laboratory Exam,~les xam le I.
_9_ dye mixture together with a dye assistant, where the pH of the composition was adjusted to 3.0 with acetic acid, as follows:
Bath 1 (comparison).
30 % acetophenone 15 % sodium nitrate 5 ml of stock dye mixture acetic acid to adjust pH to 3.0 Bath 2 (the invention).
30 % ISOPHORONE
15 % sodium nitrate 5 ml of stock dye mixture .. acetic acid to adjust pH to 3.0 Bath 3 (the invention).
% ISOPHORONE
15 15 % sodium nitrate 5 ml of stock dye mixture acetic acid to adjust pH to 3.0 Bath 4 (the invention)y 10 % ISOPHORONE ' . 20 15 % sodium nitrate 5 ml of stock dye mixture acetic acid to adjust pH to 3.0 _10_ For each of the 4 dye baths, a sample of NOMEX 455 fabric was dyed at about 265° Fahrenheit (about 129° Celsius) for about 1 hour.
The results were that the composition with ISOPHORONE as the dye assistant yielded equal color on NOMEX 455 as compared to the composition with acetophenone as the dye assistant.
Example II.
The dyeing procedure of Example I was repeated for 6 additional aqueous dye. baths prepared from compositions of dye assistant and stock dye mixture for dyeing NOMEX 455 fabric for about 1 hour at about 265°
Fahrenheit (about 129° Celsius).
The following 6 dye baths prepared from compositions of dye assistant and stock dye mixture were employed:
Bath 1 (comparison).
30 % acetophenone 15 % sodium nitrate 5 ml of stock dye mixture acetic acid to adjust pH to 3.0 _11-Bath 3 (comparison).
% acetophenone % sodium nitrate 5 ml of stock dye mixture 5 , acetic acid to adjust pH to 3.0 . Bath 4 (the invention).
30 % IS.OPHORONE
15 % sodium nitrate 5 ml of stock dye mixture 10 ' acetic acid to adjust pH to 3.0 _ - ~ Bath 5 (the invention).
% ISOPHORONE
15 % sodium nitrate 5 ml of stock dye mixture , 15 acetic acid to adjust pH to 3.0 Bath 6 (the invention).
10 % ISOPHORONE ' 15 % sodium nitrate 5 ml of stock dye mixture 20 acetic acid to adjust pH to 3.0 _12_ Compositions with ISOPHORONE as the dye assistant yielded comparably on NOMEX 455 as compared to compositions with acetophenone as the dye assistant.
Example III.
For 2 additional dye baths prepared from compositions of dye assistant and dye mixture, the procedure of Example I was repeated, except that this time, color transfer was evaluated rather than dye yield as .follows.
Afterdyeing, a colortransfertestwas performed in the following manner.
A dyed fabric sample and an undyed fabric sample were heated together in a bath with the respective dyeing assistant and_sodium nitrate (15 % OWF) with acetic acid at pH 3 to about 265° Fahrenheit (about 129°
Celsius) far about 1 hour. The amount of color transfer from each dyed sample to its respective undyed sample was evaluated.
The following 2 dye bath compositions were evaluated for color transfer:
Bath 1 (comparison).
30 % acetophenone 15 % sodium nitrate 5 ml of stock dye mixture acetic acid to adjust pH to 3.0 Bath 2 (the invention).
% ISOPHORONE
15 % sodium nitrate 5 ml of stock dye mixture acetic acid to adjust~pH to 3.0 : ;;;_.~;.:,;
CA 02428758 2003-05-15, The results were that the composition with ISOPHORONE as the dye assistant was comparable to the composition with acetophenone as the dye assistant with respect to color transfer.
- Example IV.
The procedure of Example I was repeated for Bath 1 (comparison with acetophenone), and for Bath 2 (the invention with ISOPHORONE), except that this time ISOPHORONE was emulsified with 18.9 % of WITCOMUL 1305 prior to admixing with the stock dye mixture to form a dye bath prepared from a composition of dye assistant, emulsifier, and stock dye mixture.
The results were that compositions with emulsified ISOPHORONE as the dye assistant yielded on NOMEX 455 comparably to compositions with acetophenone as the dye assistant.
It will be understood that various details of the invention may be _ changed without departing from the scope of the invention. Furthermore, the foregoing description is for the purpose of illustration only, and not for the purpose of limitation - the invention being defined by the claims.
Claims (25)
1. A composition for dyeing material of synthetic aromatic polyamide materials, said composition comprising (a) a cationic dye and (b) a cyclohexenone as a dye assistant.
2. The composition of claim 1, wherein the dye assistant comprises a substituted cyclohexenone.
3. The composition of claim 2, wherein the dye assistant comprises an alkyl-substituted cyclohexenone.
4. The composition of claim 3, wherein the dye assistant comprises a trialkyl-substitied cyclohexenone.
5. The composition of claim 4, wherein the dye assistant comprises 2-cyclohexen-1-one,3,5,5-trimethyl.
6. The composition of claim 5, wherein the dye assistant further comprises 3-cyclohexen-1-one,3,5,5-trimethyl.
7. The composition of claim 6, wherein the dye assistant comprises about 98 weight % 2-cyclohexen-1-one,3,5,5-trimethyl and about 2 weight 3-cyclohexen-1-one,3,5,5-trimethyl.
8. The composition of claim 5, further comprising a minor amount of a sodium salt.
9. The composition of claim 8, wherein the sodium salt is selected from the group consisting of sodium chloride, sodium nitrate, and combinations thereof.
10. The composition of claim 5, wherein the composition is pH
adjusted with acid to a pH ranging from about 2.5 to about 4Ø
adjusted with acid to a pH ranging from about 2.5 to about 4Ø
11. The composition of claim 10, where the acid is selected from the group consisting of acetic acid, citric acid, formic acid, and combinations thereof.
12. The composition of claim 5, wherein the cationic dye is selected from the group consisting of Basic Yellow 21, Yellow 5GL, Basic Red 18, Red FB, Red GL, Basic Blue 41, Blue X-3GL-300, Basic Orange 27, Basic Green 6, and combination thereof.
13. The composition of claim 5, further comprising a dispersing agent selected from the group consisting of an emulsifier, a surfactant, and combinations thereof.
14. The composition of claim 13, wherein the surfactant is selected from the group consisting of an anionic surfactant, a cationic surfactant, a nonionic surfactant, and combinations thereof.
15. The composition of claim 14, wherein the surfactant is selected from the group consisting of a nonyl phenoxy ethanoxy ammonium sulfate, a nonyl phenol reacted with 30 mols of ethylene oxide and a block copolymer of polypropylene oxide and ethylene oxide, a blend of a diethyl sulfate quaternary of a fatty tertiary amine, ethoxylated nonyl phenol together with a dodecylbenzene sulfonic acid amine salt, and a blend of dodecylbenzene sulfonic acid amine salt and a low cloud point ethoxylated nonyl phenol.
16. The composition of claim 13, wherein the emulsifier is selected from the group consisting of a modified ethoxylated fatty acid and a block copolymer of propylene oxide and ethylene oxide.
17. The composition of claim 1, wherein the dye assistant is free of hypnotic effects.
18. The composition of claim 5, wherein the dye assistant is free of hypnotic effects.
19. The composition of claim 1, wherein the dye assistant in the composition exhibits at least one of a color yield and a color transfer that is comparable to another dye assistant in another dyeing composition of the same cationic dye and the other dye assistant for dyeing synthetic aromatic polyamide materials, where the other dyeing composition has acetophenone as the other dye assistant and has hypnotic effects.
20. The composition of claim 5, wherein the dye. assistant in the composition exhibits at least one of a color yield and a color transfer that is comparable to another dye assistant in another dyeing composition of the same cationic dye and the other dye assistant for dyeing synthetic aromatic polyamide materials, where the other dyeing composition has acetophenone as the other dye assistant and has hypnotic effects.
21. The composition of claim 1, wherein the dye assistant operates via a mechanism that swells the synthetic aromatic polyamide materials.
22. The composition of claim 5, wherein the dye assistant operates via a mechanism that swells the synthetic aromatic polyamide materials.
23. The composition of claim 1, wherein the dye assistant has one or more of a solidification point of approximately-8°C, a viscosity of approximately 2.6 .mPa s at 20'C, a solubility parameter of approximately.17.9 (J/cm3)1/2 at 25°C, a heat of evaporation of approximately 42.4 kJ/mol at boiling point, a vapor pressure of approximately 0.4 hPa at 20°C; an, evaporation number of approximately 330 where diethyl ether is 1, a flash point of approximately 85°C, a refractive index of approximately 1.477 at 20°C, a relative density of approximately 0.918 to 0.923 g/ml at 20°C, or a boiling point range of 210 to 216°C at 10.13 hPa.
24. The composition of claim 5, wherein the dye assistant has one or more of a solidification point of approximately-8°C, a viscosity of approximately 2.6 mPa s at 20°C, a solubility parameter of approximately 17.9 (J/cm3)1/2 at
25°C, a heat of evaporation of approximately 42.4 kJ/mol at boiling point, a vapor pressure of approximately 0.4 hPa at 20°C, an evaporation number of approximately 330 where diethyl ether is 1, a flash point of approximately 85°C, a refractive index of approximately 1.477 at 20°C, a relative density of approximately 0.918 to 0.923 g/ml at 20°C, or a boiling point range of 210 to 216°C at 10.13 hPa.
25. A composition for dyeing material of synthetic aromatic polyamide materials, said composition comprising (a) a cationic dye and (b) 2-cyclohexen-1-one,3,5,5-trimethyl as a dye assistant.
25. A composition for dyeing material of synthetic aromatic polyamide materials, said composition comprising (a) a cationic dye and (b) 2-cyclohexen-1-one,3,5,5-trimethyl as a dye assistant.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/776,348 US6551362B2 (en) | 2001-02-02 | 2001-02-02 | Composition for dyeing material of synthetic aromatic polyamide fibers comprising a cationic dye and novel dye assistant |
| PCT/IB2002/003922 WO2002102901A2 (en) | 2001-02-02 | 2002-01-31 | Composition for dyeing material of synthetic aromatic polyamide fibers comprising a cationic dye |
| CA002428758A CA2428758A1 (en) | 2001-02-02 | 2003-05-15 | Composition for dyeing material of synthetic aromatic polyamide fibers comprising a cationic dye |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/776,348 US6551362B2 (en) | 2001-02-02 | 2001-02-02 | Composition for dyeing material of synthetic aromatic polyamide fibers comprising a cationic dye and novel dye assistant |
| CA002428758A CA2428758A1 (en) | 2001-02-02 | 2003-05-15 | Composition for dyeing material of synthetic aromatic polyamide fibers comprising a cationic dye |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2428758A1 true CA2428758A1 (en) | 2004-11-15 |
Family
ID=34064015
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002428758A Abandoned CA2428758A1 (en) | 2001-02-02 | 2003-05-15 | Composition for dyeing material of synthetic aromatic polyamide fibers comprising a cationic dye |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US6551362B2 (en) |
| CA (1) | CA2428758A1 (en) |
| WO (1) | WO2002102901A2 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050005373A1 (en) * | 2003-07-03 | 2005-01-13 | Colortex International, Inc. | Methods for dyeing fibrous material, dyed goods produced by such methods, and a system for operating the method producing the goods |
| US7967873B1 (en) | 2006-03-29 | 2011-06-28 | Bozzetto, Inc. | Dyed textile article and dye bath assistant |
| CN102002868B (en) * | 2010-11-30 | 2012-01-11 | 常熟市宝沣特种纤维有限公司 | Normal-pressure dyeing method of meta-aramid yarn |
| CN103906812B (en) | 2011-09-29 | 2016-05-11 | 陶氏环球技术有限责任公司 | Formulations with benzoate dye carriers for meta-aramid articles |
| EP3336147B1 (en) * | 2016-12-15 | 2019-10-23 | DyStar Colours Distribution GmbH | Basic dye mixtures for aramid fibres |
| CN109853244A (en) * | 2018-12-26 | 2019-06-07 | 蓝星（成都）新材料有限公司 | A kind of preparation method of high-strength aramid Ⅱ |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3674420A (en) | 1969-10-22 | 1972-07-04 | Arkansas Co Inc | Cycloalkanone or alkyl aryl ketone assisting cationic dye and aromatic polyamide dyeing therewith |
| US4780105A (en) | 1987-04-15 | 1988-10-25 | Stockhausen, Inc. | Composition for dyeing material of synthetic aromatic polyamide fibers: cationic dye and n-alkyl phthalimide |
| US5207803A (en) * | 1990-09-28 | 1993-05-04 | Springs Industries | Method for dyeing aromatic polyamide fibrous materials: n,n-diethyl(meta-toluamide) dye carrier |
| US5215545A (en) * | 1990-10-29 | 1993-06-01 | Burlington Industries, Inc. | Process for dyeing or printing/flame retarding aramids with N-octyl-pyrrolidone swelling agent |
-
2001
- 2001-02-02 US US09/776,348 patent/US6551362B2/en not_active Expired - Fee Related
-
2002
- 2002-01-31 WO PCT/IB2002/003922 patent/WO2002102901A2/en not_active Ceased
-
2003
- 2003-05-15 CA CA002428758A patent/CA2428758A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| WO2002102901A2 (en) | 2002-12-27 |
| US20020144362A1 (en) | 2002-10-10 |
| US6551362B2 (en) | 2003-04-22 |
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