US3644272A - Modacrylic fibers containing compounds of the azulene series - Google Patents
Modacrylic fibers containing compounds of the azulene series Download PDFInfo
- Publication number
- US3644272A US3644272A US54600A US3644272DA US3644272A US 3644272 A US3644272 A US 3644272A US 54600 A US54600 A US 54600A US 3644272D A US3644272D A US 3644272DA US 3644272 A US3644272 A US 3644272A
- Authority
- US
- United States
- Prior art keywords
- fiber
- weight percent
- weight
- polymer
- whitening agent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000835 fiber Substances 0.000 title claims abstract description 74
- 229920002821 Modacrylic Polymers 0.000 title abstract description 27
- 150000001545 azulenes Chemical class 0.000 title abstract description 14
- 150000001875 compounds Chemical class 0.000 title description 10
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 25
- 230000002087 whitening effect Effects 0.000 claims abstract description 25
- 229920000642 polymer Polymers 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 claims description 15
- 238000009987 spinning Methods 0.000 claims description 15
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 239000004753 textile Substances 0.000 abstract description 7
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 16
- -1 alkoxy radical Chemical class 0.000 description 15
- 239000007844 bleaching agent Substances 0.000 description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 238000009998 heat setting Methods 0.000 description 4
- FWKQNCXZGNBPFD-UHFFFAOYSA-N Guaiazulene Chemical compound CC(C)C1=CC=C(C)C2=CC=C(C)C2=C1 FWKQNCXZGNBPFD-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 2
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical class C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000005840 aryl radicals Chemical group 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- DFQUBYCHLQAFOW-IHWYPQMZSA-N (z)-4-(methylamino)-4-oxobut-2-enoic acid Chemical compound CNC(=O)\C=C/C(O)=O DFQUBYCHLQAFOW-IHWYPQMZSA-N 0.000 description 1
- JJIWDEGOZQOSJU-UHFFFAOYSA-N 1-ethylazulene Chemical compound C1=CC=CC=C2C(CC)=CC=C21 JJIWDEGOZQOSJU-UHFFFAOYSA-N 0.000 description 1
- PGMUWFCRDIIWCB-UHFFFAOYSA-N 1-propan-2-ylazulene Chemical compound C1=CC=CC=C2C(C(C)C)=CC=C21 PGMUWFCRDIIWCB-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- FZURFZSOULAQJQ-UHFFFAOYSA-N 2-ethyl-4-methoxy-8-methylazulene Chemical compound C(C)C1=CC2=C(C=CC=C(C2=C1)C)OC FZURFZSOULAQJQ-UHFFFAOYSA-N 0.000 description 1
- UFBYZINNXJQMJP-UHFFFAOYSA-N 2-ethyl-4-methylazulene Chemical compound C(C)C1=CC2=CC=CC=C(C2=C1)C UFBYZINNXJQMJP-UHFFFAOYSA-N 0.000 description 1
- VJOWMORERYNYON-UHFFFAOYSA-N 5-ethenyl-2-methylpyridine Chemical compound CC1=CC=C(C=C)C=N1 VJOWMORERYNYON-UHFFFAOYSA-N 0.000 description 1
- CWHRICSNFORDHK-UHFFFAOYSA-N 5-methyl-2-propan-2-ylazulene Chemical compound C(C)(C)C1=CC2=CC=CC(=CC2=C1)C CWHRICSNFORDHK-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 1
- HPJYKMSFRBJOSW-JHSUYXJUSA-N Damsin Chemical compound C[C@H]1CC[C@H]2C(=C)C(=O)O[C@H]2[C@]2(C)C(=O)CC[C@@H]12 HPJYKMSFRBJOSW-JHSUYXJUSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- HETCEOQFVDFGSY-UHFFFAOYSA-N Isopropenyl acetate Chemical compound CC(=C)OC(C)=O HETCEOQFVDFGSY-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 241001246312 Otis Species 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000003828 azulenyl group Chemical group 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000001071 guaiazulene group Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- WFKDPJRCBCBQNT-UHFFFAOYSA-N n,2-dimethylprop-2-enamide Chemical compound CNC(=O)C(C)=C WFKDPJRCBCBQNT-UHFFFAOYSA-N 0.000 description 1
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F1/00—General methods for the manufacture of artificial filaments or the like
- D01F1/02—Addition of substances to the spinning solution or to the melt
- D01F1/10—Other agents for modifying properties
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/01—Hydrocarbons
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/28—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D01F6/40—Modacrylic fibres, i.e. containing 35 to 85% acrylonitrile
Definitions
- This invention relates to a modacrylic textile fiber having uniformly dispersed therein an acetone-soluble whitening agent of the azulene series.
- this invention relates to a process for producing modacrylic fibers of improved whiteness by spinning the fibers from a solution containing acetone and an acetone-soluble whitening agent of the azulene series.
- Modacrylic fibers have become a significant commercial fiber in recent years. Presently modacrylic fibers enjoy popularity for a variety of uses such as carpets, drapes, wigs, and the like.
- modacrylic fibers are desirable for many applications, a significant problem exists in that the fibers tend to yellow after heat setting.
- This invention provides a valuable contribution to the art in that according to this invention a modacrylic fiber of improved whiteness can be produced.
- one embodiment of this invention relates to a modacrylic textile fiber of improved whiteness having an acetone-soluble whitening agent of the azulene series uniformly dispersed throughout the fiber.
- another embodiment of this invention relates to a process for producing a modacrylic fiber of improved whiteness comprising the steps of l) preparing a spinning dope solution containing a fiber-forming modacrylic polymer, acetone and an acetone-soluble whitening agent of the azulene series, (2) spinning a fiber from the spinning dope and (3) heat setting the spun fiber.
- an object of this invention is to provide a modacrylic textile fiber of improved whiteness.
- Another object of this invention is to provide a process for producing a modacrylic textile fiber of improved whiteness.
- the whitening agents of this invention are compounds of the azulene series and correspond to the general formula wherein R is hydrogen or an alkyl, aryl, alkaryltaralkyl or alkoxy radical.
- R can be an alkyl radical containing from one to 20 carbon atoms.
- the compound when R is hydrogen in the above formula, the compound is often called azulene.
- the carbon atoms contain substituents such as alkyl, the compounds are often named as an azulene derivative.
- azulene series means the compounds corresponding to the above general formula.
- Suitable members of the azulene series include 2-isopropyl-4,8- dimethylazylene, 2-isopropyl-5-methylazulene, 1,3,5- trimethylazulene 1,3,5-trimethoxyazulene, 2-ethyl-8-methoxy-4-methylazulene, 2-ethyl-4-methylazulene, 2-phenylazu- 5- lene, 2-(octylphenyl)-azulene, S-benzylazulene, isopropylazulene, Z-ethylazulene, 2-laurylazulene, 5-octadecylazulene, 6-naphthylazulene.
- any of the above-described compounds that act as whitening agents in modacrylic fibers can be used.
- whitening agent means any compound corresponding to the above general formula that when dispersed throughoutthe fiber will produce a modacrylic fiber whiter than a corresponding modacrylic fiber that has had the whitening agent omitted.
- the whitening agent is uniformly dispersed throughout the fiber.
- the whitening agent can be placed in the fiber in any manner that will produce the fiber of this invention, in one embodiment the whitening agent is dissolved in the spinning dope solution and a fiber spun from the dope.
- the spinning dope can contain materials other than the solvent such as lubricants, dye promoters, viscosity modifiers and the like.
- the whitening agent is acetone soluble and thus dissolves in a spinning dope containing acetone.
- the whitening agent can, based on the weight of the fiber, comprise from about 0.00l to about 0.01 weight percent of the fiber and inanother embodiment can comprise from about 0.003 to about 0.008 weight percent of the fiber.
- the modacrylic fibers useful in this invention can comprise any modacrylic fiber suitable for use in the invention.
- the polymer which forms the modacrylic fiber can be comprised of, based on the weight of the polymer, from about 30 to about 70 weight percent acrylonitrile and from about 70 to about 30 weight percent vinyl chloride or vinylidene chloride.
- the fiber-forming polymer can comprise, based on the weight of the polymer, from 35 to 60 weight percent acrylonitrile and from 65 to 40 weight percent vinyl chloride or vinylidene chloride.
- the fiber-forming polymer can contain other polymers.
- the acrylonitrile/vinyl chloride or vinylidene chloride polymer can be admixed with other dissimilar polymers such as polymers of acrylamides, methacrylamides, fumaramides, citraconamides, vinyl pyridines, styrene, itaconamides, maleamates, fumaramates, itaconamates, citraconamates, vinyl esters, substituted 'sytrenes, polymerizable unsaturated acids, vinylic ketones,
- vinylic ethers and similar well-known polymerizable monomers containing a single ethylenic unsaturation.
- typical monomers which are suitably employed to form these polymers include acrylamide, N-methyl methacrylamide, N-isopropyl acrylamide, vinyl acetate, styrene, butyl acrylate, methyl acrylate, methyl methacrylate, N-methyl fumaramide, N-methyl maleamate, N-methyl citraconamate, a-methylstyrene, methyl vinyl ketone, ethyl vinyl ketone, isopropenyl acetate, 2-methyl-5-vinyl pyridine, 2-vinyl pyridine, ethylene, acrylic acid, and methacrylic acid.
- the amount of acrylonitrile/vinyl chloride or vinylidene chloride polymer can vary from about 95 to about weight percent, and the amount of the dissimilar polymer can vary from about 5 to about 20 weight percent.
- Other materials such as stabilizers, inhibitors, catalysts, activators, and surfactants can be added to the polymer.
- the fiber can contain materials other than the fiber-forming polymer such as stabilizers, dye promoters, lubricants, optical brighteners and the like.
- the fibers of this invention are spun from a spinning dope solution and heatset according to methods well known in the art.
- EXAMPLE 1 Several runs are made to illustrate the practice of the invention wherein the whitening agent is azulene. In these runs various quantities of azulene are uniformly dispersed in a l6-denier/filament modacrylic fiber useful in this invention. In these runs the fiber was spun from an acetone containing spinning dope and heat set according to methods well known in the art. Specifically, in a first run, based on the weight of the fiber, about 0.001 weight percent azulene is used, and in a second run about 0.005 weight percent azulene is used and in a third run about 0.01 weight percent azulene is used. After heat setting, fibers from all three runs are whiter than fibers of the same modacrylic composition but without the whitening agents of this invention.
- EXAMPLE 2 Several more runs are made to illustrate the practice of the invention when the whitening agent is 1,4-dimethyl-7- isopropylazulene.
- l6-denier/filament fibers were spun containing, based on the weight of the fiber, about 0.005 weight percent l,4-dimethul-7-isopropylazulene and in a second run the amount of l,4-dimethyl-7-isopropylazulene in the fiber was 0.01 weight percent.
- Heat set fibers from both runs are whiter than fibers of the same modacrylic fiber without the whitening agents of this invention.
- a textile fiber comprising A. a fiber-forming polymer comprised of, based on the weight of the polymer,
- R attached to carbon atom number 4 is methyl
- R attached to carbon atom number 7 is isopropyl.
- the fiber of claim 1 wherein the fiber-forming polymer comprises from 35 to 60 weight percent acrylonitrile and from 65 to 40 weight percent vinyl chloride or vinylidene chloride.
- the fiber of claim 1 wherein the fiber-forming polymer comprises, based on the weight of the polymer, an admixture of from about 95 to about weight percent of a polymer of acrylonitrile and vinylidene chloride and from about 5 to about 20 weight percent ofa dissimilar polymer.
- a process comprising A. preparing a spinning dope solution comprising acetone and a fiber-forming olymer of, 1. based on the weig t ofthe polymer,
- R attached to carbon atom number 4 is methyl
- R attached to carbon atom number 7 is isopropyl.
- the fiber-forming polymer comprises from 35 to 60 weight percent acrylonitrile and from 65 to 40 weight percent vinyl chloride or vinylidene chloride.
- the fiber-forming polymer comprises, based on the weight of the polymer, an admixture of from about to about 80 weight percent of a polymer of acrylonitrile and vinylidene chloride and from about 5 to about 20 weight percent ofa dissimilar polymer.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Textile Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Artificial Filaments (AREA)
Abstract
A modacrylic textile fiber having uniformly dispersed therein, based on the weight of the fiber, from about 0.001 to about 0.01 weight percent of an acetone-soluble whitening agent of the azulene series.
Description
United States Patent Otis Feb. 22, 1972 [54] MODACRYLIC FIBERS CONTAINING 2,823,239 2/ 1958 Lang et al. ..260/666 A COMPOUNDS OF THE AZULENE 2,838,580 6/1958 Ruzicka et al.. ..260/666 A SERIES 3,002,956 10/1961 Perri ...260/85.5 A X 3,155,737 11/1964 Hafner ..260/666 A [72] Inventor: Marshall V..0tis, Kingsport, Tenn. 3,254,046 5/1966 Mazzolini et al. ..260/4l C 3,288,888 1 1/1966 Wieckowski ...260/85.5 A X 1 Ass1gne= m Kodak Company, Rochester, 3,388,189 6/1968 Mazzolini et al ..260/85.5 A x 2 Filed: July 13 1976 Primary Examiner-Morris Liebman Assistant Examiner-Samuel L. Fox PP 54,600 Attorney-Charles R. Martin and Cecil D. Quillen, Jr.
[52] US. Cl. ..260/4l, 8/1 W, 264/211 51 Int. Cl. ..D06p 3/70, C08f45/l4 [571 ABSTRACT Field of Search ....260/41, 85.5 A modacrylic textile fiber having uniformly dispersed therein, 211 based on the weight of the fiber, from about 0.001 to about 0.0l weight percent of an acetone-soluble whitening agent of [56] References Cited the azulene series.
UNITED STATES PATENTS 13 Claims, N0 Drawings 2,766,304 10/ l956 Ziegler et al. ..260/ 666 A MODACRYLIC FIBERS CONTAINING COMPOUNDS OF THE AZULENE SERIES This invention relates to a modacrylic textile fiber having uniformly dispersed therein an acetone-soluble whitening agent of the azulene series. In another aspect this invention relates to a process for producing modacrylic fibers of improved whiteness by spinning the fibers from a solution containing acetone and an acetone-soluble whitening agent of the azulene series.
Modacrylic fibers have become a significant commercial fiber in recent years. Presently modacrylic fibers enjoy popularity for a variety of uses such as carpets, drapes, wigs, and the like.
Although modacrylic fibers are desirable for many applications, a significant problem exists in that the fibers tend to yellow after heat setting. This invention provides a valuable contribution to the art in that according to this invention a modacrylic fiber of improved whiteness can be produced.
In summary, one embodiment of this invention relates to a modacrylic textile fiber of improved whiteness having an acetone-soluble whitening agent of the azulene series uniformly dispersed throughout the fiber. In summary, another embodiment of this invention relates to a process for producing a modacrylic fiber of improved whiteness comprising the steps of l) preparing a spinning dope solution containing a fiber-forming modacrylic polymer, acetone and an acetone-soluble whitening agent of the azulene series, (2) spinning a fiber from the spinning dope and (3) heat setting the spun fiber.
Accordingly, an object of this invention is to provide a modacrylic textile fiber of improved whiteness.
Another object of this invention is to provide a process for producing a modacrylic textile fiber of improved whiteness.
Other objects, advantages, andfeatures of this invention will be readily apparent to those skilled in the art from the following description and appended claims.
The whitening agents of this invention are compounds of the azulene series and correspond to the general formula wherein R is hydrogen or an alkyl, aryl, alkaryltaralkyl or alkoxy radical. I
In one embodiment R can be an alkyl radical containing from one to 20 carbon atoms.
As is well known by those skilled in the art, when R is hydrogen in the above formula, the compound is often called azulene. When the carbon atoms contain substituents such as alkyl, the compounds are often named as an azulene derivative. For example, when methyl radicals are attached to carbon atoms number I and 4 and an isopropyl radical is attached to carbon atom number 7, the resulting compound can be named 1,4-dimethyl-7 -isopropyl azulene. Thus according to this invention the term azulene series means the compounds corresponding to the above general formula. Other suitable members of the azulene series include 2-isopropyl-4,8- dimethylazylene, 2-isopropyl-5-methylazulene, 1,3,5- trimethylazulene 1,3,5-trimethoxyazulene, 2-ethyl-8-methoxy-4-methylazulene, 2-ethyl-4-methylazulene, 2-phenylazu- 5- lene, 2-(octylphenyl)-azulene, S-benzylazulene, isopropylazulene, Z-ethylazulene, 2-laurylazulene, 5-octadecylazulene, 6-naphthylazulene.
The azulene series compounds useful in this invention, as well as methods for their preparation, are well known in the art and are described in U.S. Pat. No. 2,971,034 and the article entitled, The Azulenes, by Maxwell Gordon, Chemical Reviews, Vol. 50, pp. 127-200 1952).
According to this invention, any of the above-described compounds that act as whitening agents in modacrylic fibers can be used. Thus in this application the term whitening agent means any compound corresponding to the above general formula that when dispersed throughoutthe fiber will produce a modacrylic fiber whiter than a corresponding modacrylic fiber that has had the whitening agent omitted.
According to this invention, the whitening agent is uniformly dispersed throughout the fiber. Although the whitening agent can be placed in the fiber in any manner that will produce the fiber of this invention, in one embodiment the whitening agent is dissolved in the spinning dope solution and a fiber spun from the dope. The spinning dope can contain materials other than the solvent such as lubricants, dye promoters, viscosity modifiers and the like.
According to this invention, the whitening agent is acetone soluble and thus dissolves in a spinning dope containing acetone.
According to this invention, the whitening agent can, based on the weight of the fiber, comprise from about 0.00l to about 0.01 weight percent of the fiber and inanother embodiment can comprise from about 0.003 to about 0.008 weight percent of the fiber.
The modacrylic fibers useful in this invention can comprise any modacrylic fiber suitable for use in the invention. In one embodiment, the polymer which forms the modacrylic fiber can be comprised of, based on the weight of the polymer, from about 30 to about 70 weight percent acrylonitrile and from about 70 to about 30 weight percent vinyl chloride or vinylidene chloride. In another embodiment of the invention the fiber-forming polymer can comprise, based on the weight of the polymer, from 35 to 60 weight percent acrylonitrile and from 65 to 40 weight percent vinyl chloride or vinylidene chloride.
According to this invention the fiber-forming polymer can contain other polymers. Specifically, the acrylonitrile/vinyl chloride or vinylidene chloride polymer can be admixed with other dissimilar polymers such as polymers of acrylamides, methacrylamides, fumaramides, citraconamides, vinyl pyridines, styrene, itaconamides, maleamates, fumaramates, itaconamates, citraconamates, vinyl esters, substituted 'sytrenes, polymerizable unsaturated acids, vinylic ketones,
vinylic ethers, and similar well-known polymerizable monomers containing a single ethylenic unsaturation. Thus, for example, typical monomers which are suitably employed to form these polymers include acrylamide, N-methyl methacrylamide, N-isopropyl acrylamide, vinyl acetate, styrene, butyl acrylate, methyl acrylate, methyl methacrylate, N-methyl fumaramide, N-methyl maleamate, N-methyl citraconamate, a-methylstyrene, methyl vinyl ketone, ethyl vinyl ketone, isopropenyl acetate, 2-methyl-5-vinyl pyridine, 2-vinyl pyridine, ethylene, acrylic acid, and methacrylic acid. In this embodiment, based on the weight of the fiber forming polymer, the amount of acrylonitrile/vinyl chloride or vinylidene chloride polymer can vary from about 95 to about weight percent, and the amount of the dissimilar polymer can vary from about 5 to about 20 weight percent. Other materials such as stabilizers, inhibitors, catalysts, activators, and surfactants can be added to the polymer.
In this invention the fiber can contain materials other than the fiber-forming polymer such as stabilizers, dye promoters, lubricants, optical brighteners and the like.
The fibers of this invention are spun from a spinning dope solution and heatset according to methods well known in the art.
The following examples are presented to further illustrate the invention and are not to be interpreted as limiting the invention.
EXAMPLE 1 Several runs are made to illustrate the practice of the invention wherein the whitening agent is azulene. In these runs various quantities of azulene are uniformly dispersed in a l6-denier/filament modacrylic fiber useful in this invention. In these runs the fiber was spun from an acetone containing spinning dope and heat set according to methods well known in the art. Specifically, in a first run, based on the weight of the fiber, about 0.001 weight percent azulene is used, and in a second run about 0.005 weight percent azulene is used and in a third run about 0.01 weight percent azulene is used. After heat setting, fibers from all three runs are whiter than fibers of the same modacrylic composition but without the whitening agents of this invention.
This example demonstrates that the whitening agents of the invention, when used in quantities from about 0.001 to about 0.01 weight percent, result in a modacrylic fiber whiter than a corresponding modacrylic fiber that does not contain the whitening agents of this invention.
EXAMPLE 2 Several more runs are made to illustrate the practice of the invention when the whitening agent is 1,4-dimethyl-7- isopropylazulene. In a first run l6-denier/filament fibers were spun containing, based on the weight of the fiber, about 0.005 weight percent l,4-dimethul-7-isopropylazulene and in a second run the amount of l,4-dimethyl-7-isopropylazulene in the fiber was 0.01 weight percent. Heat set fibers from both runs are whiter than fibers of the same modacrylic fiber without the whitening agents of this invention.
This example demonstrates that whitening agents of the azulene series other than azulene can be used in the practice ofthis invention.
The invention has been described in detail with particular reference to preferred embodiments thereof, but it will be understood that variations and modifications can be effected within the spirit and scope ofthe invention.
lclaim:
l. A textile fiber comprising A. a fiber-forming polymer comprised of, based on the weight of the polymer,
1. about 30 to about 70 weight percent acrylonitrile and 2. about 70 to about 30 weight percent vinyl chloride or vinylidene chloride and B. uniformly dispersed throughout the fiber from about 0.001 to about 0.01 weight percent, based on the weight of the fiber, of an acetone-soluble whitening agent of the formula wherein R is hydrogen or an alkyl radical or an aryl radical and at least five of the R's are hydrogen. 2. The fiber of claim 1 wherein R is hydrogen.
3. The fiber of claim 1 wherein R attached to carbon atom number 1 is methyl,
R attached to carbon atom number 4 is methyl, and
R attached to carbon atom number 7 is isopropyl.
4. The fiber of claim 1 wherein the fiber-forming polymer comprises from 35 to 60 weight percent acrylonitrile and from 65 to 40 weight percent vinyl chloride or vinylidene chloride.
5. The fiber of claim 1 wherein the fiber-forming polymer comprises, based on the weight of the polymer, an admixture of from about 95 to about weight percent of a polymer of acrylonitrile and vinylidene chloride and from about 5 to about 20 weight percent ofa dissimilar polymer.
6. The fiber of claim 1 wherein the whitening agent is in the range of 0.003 to 0.008 weight percent.
7. A process comprising A. preparing a spinning dope solution comprising acetone and a fiber-forming olymer of, 1. based on the weig t ofthe polymer,
a. about 30 to about 70 weight percent acrylonitrile and b. about 70 to about 30 weight percent vinyl chloride or vinylidene chloride and 2. uniformly dispersed throughout the spinning dope an acetone soluble whitening agent of the formula R-O2 (IJ 6CR wherein R is hydrogen or an alkyfradical or an aryl radical and at least five of the Rs are hydrogen,
B. spinning a fiber from the spinning dope solution, and
C. heat setting the spun fiber.
8. The process of claim 7 wherein R is hydrogen,
9. The process of claim 7 wherein R attached to carbon atom number 1 is methyl,
R attached to carbon atom number 4 is methyl, and
R attached to carbon atom number 7 is isopropyl.
10. The process of claim 7 wherein the fiber-forming polymer comprises from 35 to 60 weight percent acrylonitrile and from 65 to 40 weight percent vinyl chloride or vinylidene chloride.
11. The process of claim 2 wherein the fiber-forming polymer comprises, based on the weight of the polymer, an admixture of from about to about 80 weight percent of a polymer of acrylonitrile and vinylidene chloride and from about 5 to about 20 weight percent ofa dissimilar polymer.
12. The process of claim 7 wherein the whitening agent is in the range of about 0.001 to about 0.0] weight percent, based on the weight of the fiber.
13. The process of claim 7 wherein the whitening agent is in the range of 0.003 to 0.008 weight percent, based on the weight ofthe fiber.
P(%-/%%F;O UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION 5,644,272 I Dated February 22, 1972 Patent No.
InVntor(s) Marshall V. Otis It is Certified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as shown below:
Claim 11, line 1, "2" should be ---7---,
Signed and sealed this 5th day of September 1972.
(SEAL) Attest:
EDWARD M.FLETCHER,JR. ROBERT GOTTSCHALK Attestlng Officer Commissioner of Patents TEC 1026!
Claims (14)
- 2. about 70 to about 30 weight percent vinyl chloride or vinylidene chloride and B. uniformly dispersed throughout the fiber from about 0.001 to about 0.01 weight percent, based on the weight of the fiber, of an acetone-soluble whitening agent of the formula
- 2. The fiber of claim 1 wherein R is hydrogen.
- 2. uniformly dispersed throughout the spinning dope an acetone soluble whitening agent of the formula
- 3. The fiber of claim 1 wherein R attached to carbon atom number 1 is methyl, R attached to carbon atom number 4 is methyl, and R attached to carbon atom number 7 is isopropyl.
- 4. The fiber of claim 1 wherein the fiber-forming polymer comprises from 35 to 60 weight percent acrylonitrile and from 65 to 40 weight percent vinyl chloride or vinylidene chloride.
- 5. The fiber of claim 1 wherein the fiber-forming polymer comprises, based on the weight of the polymer, an admixture of from about 95 to about 80 weight percent of a polymer of acrylonitrile and vinylidene chloride and from about 5 to about 20 weight percent of a dissimilar polymer.
- 6. The fibEr of claim 1 wherein the whitening agent is in the range of 0.003 to 0.008 weight percent.
- 7. A process comprising A. preparing a spinning dope solution comprising acetone and a fiber-forming polymer of,
- 8. The process of claim 7 wherein R is hydrogen.
- 9. The process of claim 7 wherein R attached to carbon atom number 1 is methyl, R attached to carbon atom number 4 is methyl, and R attached to carbon atom number 7 is isopropyl.
- 10. The process of claim 7 wherein the fiber-forming polymer comprises from 35 to 60 weight percent acrylonitrile and from 65 to 40 weight percent vinyl chloride or vinylidene chloride.
- 11. The process of claim 2 wherein the fiber-forming polymer comprises, based on the weight of the polymer, an admixture of from about 95 to about 80 weight percent of a polymer of acrylonitrile and vinylidene chloride and from about 5 to about 20 weight percent of a dissimilar polymer.
- 12. The process of claim 7 wherein the whitening agent is in the range of about 0.001 to about 0.01 weight percent, based on the weight of the fiber.
- 13. The process of claim 7 wherein the whitening agent is in the range of 0.003 to 0.008 weight percent, based on the weight of the fiber.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US5460070A | 1970-07-13 | 1970-07-13 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3644272A true US3644272A (en) | 1972-02-22 |
Family
ID=21992216
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US54600A Expired - Lifetime US3644272A (en) | 1970-07-13 | 1970-07-13 | Modacrylic fibers containing compounds of the azulene series |
Country Status (1)
Country | Link |
---|---|
US (1) | US3644272A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5245082A (en) * | 1990-09-06 | 1993-09-14 | Bayer Aktiengesellschaft | Process for the production of di-(4-aminocyclohexyl)-methane containing 15 to 25% by weight of the trans-trans isomer |
-
1970
- 1970-07-13 US US54600A patent/US3644272A/en not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5245082A (en) * | 1990-09-06 | 1993-09-14 | Bayer Aktiengesellschaft | Process for the production of di-(4-aminocyclohexyl)-methane containing 15 to 25% by weight of the trans-trans isomer |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US3399161A (en) | Process for preparing a solution of acrylonitrile polymers | |
US3062792A (en) | Polymers derived from tetraalkyl vinylidenediphosphonates | |
US2878231A (en) | Acrylonitrile polymer composition stabilized with metal formaldehyde sulfoxylate, phosphorus pentroxide, and sulfuric acid and method of making same | |
US2659709A (en) | Stabilized vinylidene chloride compositions | |
US3644272A (en) | Modacrylic fibers containing compounds of the azulene series | |
US2425192A (en) | Polymerization of vinyl acetate alone or in mixtures, and products thereof | |
US2727021A (en) | Polymerizable and polymerized aminoethyl acrylate-acrylonitrile compositions | |
US2993877A (en) | Triazinyl esters and amides and polymerization products thereof | |
US2425191A (en) | Polymerization of acrylates, methacrylates alone or in mixtures, and products thereof | |
US3627717A (en) | Vinyl chloride emulsion polymerization, copolymerization, and product therefrom | |
US2883370A (en) | Copolymer of acrylonitrile, a quaternary ammonium compound and at least one additional comonomer | |
US3300272A (en) | Process for the preparation of dyeable acrylonitrile polymer fibers and compositions thereof | |
US2850487A (en) | Copolymers of acrylonitrile and the mono-amide of guanazole and betacyano-acrylic acid | |
US3281260A (en) | Process for treating acrylonitrile fibers with ultra-violet light stabilizer | |
US2723254A (en) | Copolymers of acrylonitrile and n-substituted sulfonamides | |
US3810878A (en) | Process for preparing polymers | |
JPS5833882B2 (en) | Acrylonitrile/vinyl chloride copolymer with increased viscosity | |
US2854436A (en) | Compositions derived from polymers having a basis of acrylonitrile | |
US2709163A (en) | Acrylonitrile-vinyl pyridine copolymer sulfonic acid reaction product | |
US3784511A (en) | Color stabilization of fibers from acrylonitrile polymers | |
US2878227A (en) | Acrylonitrile polymer compositions stabilized with paraformaldehyde and trialkyl subsituted phosphites, and method of making same | |
US2541011A (en) | Ternary interpolymers comprising acrylonitrile and fumaric acid | |
US3053789A (en) | Solutions of acrylonitrile polymers in phenolsulfonic acids | |
US3213052A (en) | Flame-resistant acrylonitrile polymer compositions containing polybromocyclohexanes and calcium phosphates | |
US3354113A (en) | Color improvement of acrylic spin dopes |