US3167448A - Process of treating fabrics with ethylene carbonate and article produced therefrom - Google Patents
Process of treating fabrics with ethylene carbonate and article produced therefrom Download PDFInfo
- Publication number
- US3167448A US3167448A US133299A US13329961A US3167448A US 3167448 A US3167448 A US 3167448A US 133299 A US133299 A US 133299A US 13329961 A US13329961 A US 13329961A US 3167448 A US3167448 A US 3167448A
- Authority
- US
- United States
- Prior art keywords
- percent
- acrylonitrile
- ethylene carbonate
- fabrics
- fabric
- 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
- 239000004744 fabric Substances 0.000 title claims description 49
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 title claims description 28
- 238000000034 method Methods 0.000 title claims description 17
- 230000008569 process Effects 0.000 title description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 41
- 239000000835 fiber Substances 0.000 claims description 26
- 239000000243 solution Substances 0.000 claims description 14
- 239000007864 aqueous solution Substances 0.000 claims description 13
- 238000001035 drying Methods 0.000 claims description 11
- 229920000642 polymer Polymers 0.000 claims description 11
- 229920002050 silicone resin Polymers 0.000 claims description 11
- 230000000087 stabilizing effect Effects 0.000 claims description 8
- 239000007767 bonding agent Substances 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 description 13
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000000839 emulsion Substances 0.000 description 11
- 239000000178 monomer Substances 0.000 description 10
- 238000004900 laundering Methods 0.000 description 9
- 229920002994 synthetic fiber Polymers 0.000 description 9
- 229920001296 polysiloxane Polymers 0.000 description 7
- 239000004758 synthetic textile Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 229910001868 water Inorganic materials 0.000 description 7
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical class C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 6
- 229920002239 polyacrylonitrile Polymers 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- SMTDFMMXJHYDDE-UHFFFAOYSA-N 2-prop-1-enylpyridine Chemical compound CC=CC1=CC=CC=N1 SMTDFMMXJHYDDE-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- -1 heterocyclic amines Chemical group 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229920002972 Acrylic fiber Polymers 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 239000004902 Softening Agent Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 2
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- VOCDJQSAMZARGX-UHFFFAOYSA-N 1-ethenylpyrrolidine-2,5-dione Chemical compound C=CN1C(=O)CCC1=O VOCDJQSAMZARGX-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- SZTBMYHIYNGYIA-UHFFFAOYSA-N 2-chloroacrylic acid Chemical class OC(=O)C(Cl)=C SZTBMYHIYNGYIA-UHFFFAOYSA-N 0.000 description 1
- GPOGMJLHWQHEGF-UHFFFAOYSA-N 2-chloroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCl GPOGMJLHWQHEGF-UHFFFAOYSA-N 0.000 description 1
- YBXYCBGDIALKAK-UHFFFAOYSA-N 2-chloroprop-2-enamide Chemical compound NC(=O)C(Cl)=C YBXYCBGDIALKAK-UHFFFAOYSA-N 0.000 description 1
- QQBUHYQVKJQAOB-UHFFFAOYSA-N 2-ethenylfuran Chemical compound C=CC1=CC=CO1 QQBUHYQVKJQAOB-UHFFFAOYSA-N 0.000 description 1
- IGDLZDCWMRPMGL-UHFFFAOYSA-N 2-ethenylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(C=C)C(=O)C2=C1 IGDLZDCWMRPMGL-UHFFFAOYSA-N 0.000 description 1
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-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
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical compound BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- YPTLFOZCUOHVFO-VOTSOKGWSA-N diethyl (e)-2-methylbut-2-enedioate Chemical compound CCOC(=O)\C=C(/C)C(=O)OCC YPTLFOZCUOHVFO-VOTSOKGWSA-N 0.000 description 1
- YPTLFOZCUOHVFO-SREVYHEPSA-N diethyl (z)-2-methylbut-2-enedioate Chemical compound CCOC(=O)\C=C(\C)C(=O)OCC YPTLFOZCUOHVFO-SREVYHEPSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- XJELOQYISYPGDX-UHFFFAOYSA-N ethenyl 2-chloroacetate Chemical compound ClCC(=O)OC=C XJELOQYISYPGDX-UHFFFAOYSA-N 0.000 description 1
- AFSIMBWBBOJPJG-UHFFFAOYSA-N ethenyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC=C AFSIMBWBBOJPJG-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000005395 methacrylic acid group Chemical class 0.000 description 1
- LVQPBIMCRZQQBC-UHFFFAOYSA-N methoxymethyl 2-methylprop-2-enoate Chemical compound COCOC(=O)C(C)=C LVQPBIMCRZQQBC-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Images
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
- D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
- D06M13/232—Organic carbonates
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/23907—Pile or nap type surface or component
- Y10T428/2395—Nap type surface
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/23907—Pile or nap type surface or component
- Y10T428/23986—With coating, impregnation, or bond
Definitions
- This invention is concerned with the treatment of the raised surface of woven, non-woven and knitted synthetic fabrics to prevent distortion of the raised surface due to normal wearing and laundering conditions. More specifically, this invention is concerned with preventing the matting, shedding and pilling of the nap of acrylic fabrics after subjecting these fabrics to normal laundering and wearing conditions, as well as preserving a soft hand.
- An object of this invention is to provide a method by which the nap of synthetic fabrics are stabilized against normal wearing and laundering conditions.
- Another object of this invention is to provide a stabilizing agent to prevent excessive matting, pilling and shedding of the nap of synthetic fabrics.
- Another object of this invention is to provide a stabilizing agent for the nap of synthetic fabrics which gives a soft hand.
- Another object of this invention is to provide a stabilizing agent for the nap of synthetic fabrics which does not deleteriously affect the color.
- Another object of this invention is to provide a stabilizing agent for the nap of acrylonitrile fabrics which renders the fabrics free of excessive matting, pilling and shedding under normal laundering conditions as well as normal wearing conditions.
- Another object of this invention is to provide permanent stability of high pile fabrics against matting, pilling and shedding.
- the objects of this invention are generally accomplished by applying an aqueous solution of ethylene carbonate to the nap or raised surface of synthetic fabrics, either woven, non-woven or knitted. Thiscompound is applied by the conventional padding method.
- a silicone emulsion is also padded into the fabrics. The use of the silicone' emulsion results in an acceptable soft hand when used in conjunction with the ethylene carbonate.
- an anti-static agent such as Aston 108, which is a polyamine resin such as diethylenetriamine crossed-linked with polyethylene glycol diiodide or an epoxy resin, may be used inv conjunction with the silicone emulsion and ethylene carbonate which will give excellent protection against static electricity.
- the fabric maybe treated with the above agents and a water repellent-agent such as Phobotex F.T.C., a melamine derivative, which will not afiect the hand or color and will give excellent resistance to water penetration.
- a water repellent-agent such as Phobotex F.T.C., a melamine derivative, which will not afiect the hand or color and will give excellent resistance to water penetration.
- Phobotex F.T.C. a melamine derivative
- the synthetic fabrics were mapped and then treated with an aqueous solution of ethylene carbonate in the range of a 0.05 percent solution to a 50 percent solution with the preferred solution being a 0.5 percent to a 2.0 percent solution.
- R and R being generally aliphatic radicals and n being from 1 to oowere added to improve the hand of the treated and napped synthetic fabric.
- An aqueous emulsion of the silicone of from 0.2 percent to 5 percent may be used with the preferred being a 1 percent to a 2 percent emulsion. More than a 5 percent emulsion may be used, but there is no improvement in the hand above the 5 percent emulsion and only increases the cost.
- the napped and treated fabrics were then heated in a conventional fabric drying apparatus, such as a chain dryer, to evaporate the water and to cure the softening agent-the silicone; in addition, this stabilizing compound, ethylene carbonate, is concentrated at the points of intersection of the fibers in the nap to form a durable bond between and among themselves.
- the period of time the fabrics were heated ranged from 5 minutes to 60 minutes, with the preferred being 20 minutes, at a temperature of 240 F. to 300 F., with the preferred temperature being 280 F. If an aqueous ethylene carbonate solution is used alone. then the exact temperature is immaterial as long as the fabrics so treated are dried; however, the temperature must not go to the degradation point of the acrylic fibers, 350 F.
- the napped fabrics were then withdrawn from the drying apparatus, and it was found that the hand was of acceptable softness and the color was unaffected.
- the stabilizing compound and softening agent were added onto the nap by the conventional padding method which is known in the textile field.
- Other agents such as water repellents and anti-static agents may have been added to the original padding bathwhich would have resulted in giving the mapped fabric, not only stability to laundering and wearing, but a softhand and permanent anti-static and water repellent properties.
- the polymeric materials which may be employed in the practice of the present invention, are polyacrylonitrile, copolymers, including binary and ternary polymers containing at least percent by weight of acrylonitrile in the polymer molecule, or a blend comprising polyacrylonitrile or copolymers comprising acrylonitrile with from 2 to 50 percentof another polymeric material, the blend having an overall polymerized acrylonitrile content of at least 80 percent by weight.
- the preferred polymers employed in the instant invention are those containing at least 80 percent of acrylonitrile, generally recognized as the fiber-forming acrylonitrile polymers, it will be understood that the invention is likewise applicable to polymers containing less than 80 percent acrylonitrile.
- the acrylonitrile polymers containing less than 80 percent acrylonitrile are useful in forming films, coating compositions, molding operations, lacquers, etc., in all of which applications the alleviation of undesirable color is extremely important.
- the polymer may be a copolymer of from 80 to 98 percent acrylonitrile and from 2 to 20 percent 7 tion.
- Suitable mono-olefinic monomers include acrylic, alpha-chloroacrylic and methacrylic acids; the acrylates, such as methylmethacrylate, ethylmethacrylate, butylmethacrylate, methoxymethyl methacrylate, beta-chloroethyl methacrylate, and the corresponding esters of acrylic and alpha-chloroacrylic acids; vinyl chloride, vinyl fiuoride, vinyl bromide, vinylidene chloride, l-chloro-l-brmo-ethylene; methacrylonitrile; acrylamide and methacrylarnide; alpha-chloroacrylamide; or monoalkyl substitution products thereof; methylvinyl ketone; vinyl carboxylates, such as vinyl acetate, vinyl chloroacetate, vinyl propionate, and vinyl stearate; N-vinylimides, such as N-vinylphthalimidiol, ethylene, ethylene ethylene, and the corresponding esters of acrylic and al
- the polymer may be a ternary or higher interpolymer, for example, products obtained by the interpolymerization of acrylonitrile and two or more of any of the monomers, other than acrylonitrile, enumerated above. More specifically, and preferably, the ternary polymer comprises acrylonitrile, methacrylonitrile, and 2-vinylpyridine.
- the ternary polymers preferably contain from 80 to 98 percent of acrylonitrile, from 1 to percent of a vinylpyridine or a l-vinylimidazole, and from 1 to 18 percent of another substance such as methacrylonitrile or vinyl V chloride.
- the polymeric material when it comprises a blend, it will be a blend of a copolymer of 90 to 98 percent acrylonitrile and from 2 to 10 percent of another monomer-olefinic monomer, such as vinyl acetate, which is not receptive to dyestuff, with a sufficient amount of a copolymer of from 10 to 70 percent of acrylonitrile and from 30 to 90 percent of a vinylsubstituted tertiary heterocyclic amine, such as vinylpyridine or l-vinylimidazole, to give a dyeable blend having an overall vinyl-substituted tertiary heterocyclic amine content of from 2 to 10 percent, based on the weight of the blend.
- a copolymer of 90 to 98 percent acrylonitrile and from 2 to 10 percent of another monomer-olefinic monomer such as vinyl acetate, which is not receptive to dyestuff
- Example 1 A swatch of nappedfabric composed of synthetic, linear acrylonitrile polymers was padded with an aqueous solu- Example 2
- Example 3 A swatch of napped acrylic fabric composed of fibers of a blend of 88 percent or one copolymer of 94percent acrylonitrile and 6 percent vinyl acetate and 12' percent of another copolym er composed of 5 0 percent acrylonitrile and percent methyl vinyl pyridine was padded with a 0.50 percent aqueous solution of ethylene carbonate.
- Example 4 A swatch of napped fabric composed of fibers of 92 percent acrylonitrile and 8 percent vinyl acetate was padded with a 0.25 percent aqueous solution of ethylene carbonate. 1 The swatch was then placed in a drying oven and heated for 20 minutes at 220 F. It was then removed and allowed to cool, after which the swatch was laundered five consecutive times under normal laundering conditions. The hand remained very soft and the color was not affected. In addition there was no excessive amount of matting, pilling or shedding.
- Example 5 A swatch of napped fabric composed of fibers of 92 percent acrylonitrile and 8 percent vinyl acetate was padded with a 0.10 percent aqueous solution of. ethylene carbonate. The swatch was then placed in a drying oven and heated for 20 minutes at 220 F. It was then removed and allowed to dry, after which the swatch was laundered. five consecutive times under normal laundering conditions. The hand remained very soft and the color was not affected. :In addition there was no exces .sive amount of matting,pilling' or shedding.
- Example 6 percent of sodium bisulfate, a catalyst.
- the swatch was then placed in a drying oven and heated for 20 minutes at 220 F. The temperature was then raised to 280 F. for ten minutes to cure the silicone. It was then removed and allowed to cool, after which the swatch was laun dered for five consecutive times under normal laundering It was then removed and allowed to cool, after conditions. The hand remained very soft and the color was not affected. In addition there was no excessive amount of matting, pillingor shedding.
- Example 7 A swatch of napped fabric composed of fibers of 92 percent acrylonitrile and 8 percent vinyl acetate was padded with an aqueous solution composed of 0.5 percent ethylene carbonate, 2.0 percent silicone resin and 0.2 7
- the swatch' was then placed in a drying, oven where it was heated for 20 minutes at 220 F. The temperature of the oven was then raised to 280 F. for minutes to cure the silicone resin. It was then removed from the oven and allowed to cool, after which the swatch was laundered five consecutive times under normal laundering conditions. The hand remained very soft and the color was not affected. In addition there was no excessive amount of matting, pilling or shedding.
- the stabilizing compound of this invention it is possible to treat napped fabrics composed of acrylic fibers so that they may be laundered many times and their hand, color and physical properties, such as matting, pilling and shedding will not be appreciably changed from their original conditions.
- An article composed of the napped fabric of fibers of synthetic linear acrylonitrile, ethylene carbonate as a bonding agent at the point of intersection of the fibers in the nap and a silicone resin as a softening agent.
- the article of claim 1 in which the fabric is composed of fibers of at least 80 percent acrylonitrile and up to 20 percent of another copolymerizable mono-olefinic monomer.
- a method of stabilizing the nap of fabrics composed of fibers of synthetic linear polymers of acrylonitrile comprising impregnating the napped fabric with an aqueous solution of ethylene carbonate and a silicone resin in which the ethylene carbonate as a bonding agent is used in an amount of from 0.05 percent to 50 percent by weight of the solution, drying said fabric and curing the silicone resin by heating said fabric at a temperature of from 240 F. to 300 F. for 5 to 60 minutes.
- the fibers are selected from the group consisting of a fiber of 94 percent acrylonitrile and 6 percent vinyl acetate and a blend of 88 percent of one copolymer of 94 percent acrylonitrile and 6 percent vinyl acetate and 12 percent of another copolymer composed of 50 percent acrylonitrile and 50 percent methyl vinyl pyridine.
- a method of stabilizing the nap of fabrics composed of fibers of at least 80 percent acrylonitrile and up to 20 percent of another copolymerizable mono-olefinic monomer comprising impregnating the napped fabric with an aqueous solution of ethylene carbonate in which ethylene carbonate acts as a bonding agent at the point of intersection of the fibers in the nap to form a durable bond, with the amount of ethylene carbonate being 0.5 percent to 2.0 percent by weight of the solution, and drying said fabric.
- a method of stabilizing the nap of fabrics composed of fibers of at least 80 percent acrylonitrile and up to 20 percent of another copolymerizable mono-olefinic monomer comprising impregnating the napped fabric with an aqueous solution of ethylene carbonate, in the range of a 0.05 percent to a 50 percent solution, with ethylene carbonate acting as a bonding agent at the point of intersection of the fibers in the nap to form a durable bond, and a silicone resin emulsion in the range of 0.2 percent to 5 percent solution, drying said fabric and ouring the silicone resin by heating said fabric to 280 F. for 10 minutes.
Description
Jan. 26, 1965 J. J. HIRSHFELD 3,167,448
PROCESS OF TREATING FABRICS WITH ETI-IYLENE CARBONATE AND ARTICLE PRODUCED THEREFROM Filed Aug. 23, 1961 NA PPED FABRIC COMPOSED OF. FIBERS OF AT LEAST 809/0 ACRYLONITRILE.
IMPREGNATE NAP WITH AQUEOUS ETHYLENE CARBONATE AND SILICONE RESIN EMULSION.
DRY TO EVAPORATE WATER AND CURE THE SILICONE RESIN.
FIG. I.
ETHYLENE CARBONATE BOND k mmymmwm NAP rV/ /?\-FABRIC F l INVENTOR.
JULIAN J. HIRSI-IFELD 3,167,448 Patented Jan. 26., 1965 Deiaware Filed Aug. 23, 1961, Ser. No. 133,299 16 Claims. (Cl. 117138.8)
This invention is concerned with the treatment of the raised surface of woven, non-woven and knitted synthetic fabrics to prevent distortion of the raised surface due to normal wearing and laundering conditions. More specifically, this invention is concerned with preventing the matting, shedding and pilling of the nap of acrylic fabrics after subjecting these fabrics to normal laundering and wearing conditions, as well as preserving a soft hand.
In the past the raised surfaces of fabrics composed of synthetic fibers have been stabilized by the use of salts which were toxic and corrosive; therefore, special and expensive production equipment was necessary to apply these salts, usually as a solution, to the raised surface of the fabrics. Some of the salts were the pure metal halides such as zinc chloride, lithium bromide and water soluble thiocyanates. These salts were very corrosive to the standard finishing mill equipment. In addition. these salts gave the fabrics a harsh hand which was very undesirable and affected the color to such an extent that the fabrics were unacceptable. While this harsh or crisp hand could be softened, this entailed additional chemical and physical treatments which added to its cost.
An object of this invention is to provide a method by which the nap of synthetic fabrics are stabilized against normal wearing and laundering conditions.
Another object of this invention is to provide a stabilizing agent to prevent excessive matting, pilling and shedding of the nap of synthetic fabrics.
Another object of this invention is to provide a stabilizing agent for the nap of synthetic fabrics which gives a soft hand.
Another object of this invention is to provide a stabilizing agent for the nap of synthetic fabrics which does not deleteriously affect the color.
Another object of this invention is to provide a stabilizing agent for the nap of acrylonitrile fabrics which renders the fabrics free of excessive matting, pilling and shedding under normal laundering conditions as well as normal wearing conditions.
Another object of this invention is to provide permanent stability of high pile fabrics against matting, pilling and shedding.
Other objects and advantages of this invention will become apparent from the hereinafter detailed description.
The objects of this invention are generally accomplished by applying an aqueous solution of ethylene carbonate to the nap or raised surface of synthetic fabrics, either woven, non-woven or knitted. Thiscompound is applied by the conventional padding method. In addition to the ethylene carbonate, a silicone emulsion is also padded into the fabrics. The use of the silicone' emulsion results in an acceptable soft hand when used in conjunction with the ethylene carbonate. In addition an anti-static agent such as Aston 108, which is a polyamine resin such as diethylenetriamine crossed-linked with polyethylene glycol diiodide or an epoxy resin, may be used inv conjunction with the silicone emulsion and ethylene carbonate which will give excellent protection against static electricity. Also, the fabric maybe treated with the above agents and a water repellent-agent such as Phobotex F.T.C., a melamine derivative, which will not afiect the hand or color and will give excellent resistance to water penetration. The use of these additional agents give additional useful properties to the fabrics without affecting the hand and color.
More specifically, the synthetic fabrics were mapped and then treated with an aqueous solution of ethylene carbonate in the range of a 0.05 percent solution to a 50 percent solution with the preferred solution being a 0.5 percent to a 2.0 percent solution. Along with the ethylene carbonate solution an aqueous non-ionic silicone emulsion of the general formula S1O Li. J.
with R and R being generally aliphatic radicals and n being from 1 to oowere added to improve the hand of the treated and napped synthetic fabric. An aqueous emulsion of the silicone of from 0.2 percent to 5 percent may be used with the preferred being a 1 percent to a 2 percent emulsion. More than a 5 percent emulsion may be used, but there is no improvement in the hand above the 5 percent emulsion and only increases the cost. The napped and treated fabrics were then heated in a conventional fabric drying apparatus, such as a chain dryer, to evaporate the water and to cure the softening agent-the silicone; in addition, this stabilizing compound, ethylene carbonate, is concentrated at the points of intersection of the fibers in the nap to form a durable bond between and among themselves. The period of time the fabrics were heated ranged from 5 minutes to 60 minutes, with the preferred being 20 minutes, at a temperature of 240 F. to 300 F., with the preferred temperature being 280 F. If an aqueous ethylene carbonate solution is used alone. then the exact temperature is immaterial as long as the fabrics so treated are dried; however, the temperature must not go to the degradation point of the acrylic fibers, 350 F. The napped fabrics were then withdrawn from the drying apparatus, and it was found that the hand was of acceptable softness and the color was unaffected. The stabilizing compound and softening agent were added onto the nap by the conventional padding method which is known in the textile field. Other agents such as water repellents and anti-static agents may have been added to the original padding bathwhich would have resulted in giving the mapped fabric, not only stability to laundering and wearing, but a softhand and permanent anti-static and water repellent properties.
While this application has been generally directed to synthetic fabrics, it is'especially useful in the stabilizing of the nap of fabrics made from fibers of acrylic polymers. The polymeric materials, which may be employed in the practice of the present invention, are polyacrylonitrile, copolymers, including binary and ternary polymers containing at least percent by weight of acrylonitrile in the polymer molecule, ora blend comprising polyacrylonitrile or copolymers comprising acrylonitrile with from 2 to 50 percentof another polymeric material, the blend having an overall polymerized acrylonitrile content of at least 80 percent by weight. While the preferred polymers employed in the instant invention are those containing at least 80 percent of acrylonitrile, generally recognized as the fiber-forming acrylonitrile polymers, it will be understood that the invention is likewise applicable to polymers containing less than 80 percent acrylonitrile. The acrylonitrile polymers containing less than 80 percent acrylonitrile are useful in forming films, coating compositions, molding operations, lacquers, etc., in all of which applications the alleviation of undesirable color is extremely important.
For example, the polymer may be a copolymer of from 80 to 98 percent acrylonitrile and from 2 to 20 percent 7 tion.
of another monomer containing the C linkage and copolymerizable with acrylonitrile. Suitable mono-olefinic monomers include acrylic, alpha-chloroacrylic and methacrylic acids; the acrylates, such as methylmethacrylate, ethylmethacrylate, butylmethacrylate, methoxymethyl methacrylate, beta-chloroethyl methacrylate, and the corresponding esters of acrylic and alpha-chloroacrylic acids; vinyl chloride, vinyl fiuoride, vinyl bromide, vinylidene chloride, l-chloro-l-brmo-ethylene; methacrylonitrile; acrylamide and methacrylarnide; alpha-chloroacrylamide; or monoalkyl substitution products thereof; methylvinyl ketone; vinyl carboxylates, such as vinyl acetate, vinyl chloroacetate, vinyl propionate, and vinyl stearate; N-vinylimides, such as N-vinylphthalimide and N-vinylsuccinimide; methylene malonic esters; itaconic acid and itaconic esters; N-vinylcarbazole; vinyl furane; alkyl vinyl esters; vinyl sulfonic acid; ethylene alpha, betadicarboxylic acids or their anhydrides or derivatives, such as diethylcitraconate, diethylmesaconate, styrene, vinyl naphthalene; VinyLsubstituted tertiary heterocyclic amines, such as the vinylpyridines and alkyl-substituted vinylpyridines, for example, 2-vinylpyridine, 4-vinylpyridine, Z-methyl-5-vinylpyridine, etc.; l-vinylimidazole and alkylsubstituted l-vinylimidazoles, such as 2-, 4-, or S-methyll-vinylimida'zole, and other C=C containing polymerizable materials.
The polymer may be a ternary or higher interpolymer, for example, products obtained by the interpolymerization of acrylonitrile and two or more of any of the monomers, other than acrylonitrile, enumerated above. More specifically, and preferably, the ternary polymer comprises acrylonitrile, methacrylonitrile, and 2-vinylpyridine. The ternary polymers preferably contain from 80 to 98 percent of acrylonitrile, from 1 to percent of a vinylpyridine or a l-vinylimidazole, and from 1 to 18 percent of another substance such as methacrylonitrile or vinyl V chloride.
The polymer may also be a blend of a polyacrylonitrile or of a binary interpolymer of from 80 to 99 percent acrylonitrile and from 1 to 20 percent of at least one other C=C containing substance with from 2 to 50 percent of the weight of the blend of a copolymer of from 10 to 70 percent of acrylonitrile and from to 90 percent of at least one other C=C containing polymerizable monomer. Preferably, when the polymeric material comprises a blend, it will be a blend of a copolymer of 90 to 98 percent acrylonitrile and from 2 to 10 percent of another monomer-olefinic monomer, such as vinyl acetate, which is not receptive to dyestuff, with a sufficient amount of a copolymer of from 10 to 70 percent of acrylonitrile and from 30 to 90 percent of a vinylsubstituted tertiary heterocyclic amine, such as vinylpyridine or l-vinylimidazole, to give a dyeable blend having an overall vinyl-substituted tertiary heterocyclic amine content of from 2 to 10 percent, based on the weight of the blend.
The following examples are cited to illustrate the inven- They are not intended to limit it in any way. Unless otherwise noted, percentages as expressed in the examples indicate percent by weight. 7 r
. Example 1 A swatch of nappedfabric composed of synthetic, linear acrylonitrile polymers was padded with an aqueous solu- Example 2 Example 3 A swatch of napped acrylic fabric composed of fibers of a blend of 88 percent or one copolymer of 94percent acrylonitrile and 6 percent vinyl acetate and 12' percent of another copolym er composed of 5 0 percent acrylonitrile and percent methyl vinyl pyridine was padded with a 0.50 percent aqueous solution of ethylene carbonate. The
swatch was then placed in a drying oven and heated for' 20 minutes at 220 F. It was then removed and allowed to cool, after which the swatch was laundered five consecutive times under normal laundering conditions. There was no appreciable change in the soft hand which would affect its commercial acceptability-and the color was not affected. In addition there was no excessive amount of matting, pilling or shedding.
Example 4 A swatch of napped fabric composed of fibers of 92 percent acrylonitrile and 8 percent vinyl acetate was padded with a 0.25 percent aqueous solution of ethylene carbonate. 1 The swatch was then placed in a drying oven and heated for 20 minutes at 220 F. It was then removed and allowed to cool, after which the swatch was laundered five consecutive times under normal laundering conditions. The hand remained very soft and the color was not affected. In addition there was no excessive amount of matting, pilling or shedding.
Example 5 A swatch of napped fabric composed of fibers of 92 percent acrylonitrile and 8 percent vinyl acetate was padded with a 0.10 percent aqueous solution of. ethylene carbonate. The swatch was then placed in a drying oven and heated for 20 minutes at 220 F. It was then removed and allowed to dry, after which the swatch was laundered. five consecutive times under normal laundering conditions. The hand remained very soft and the color was not affected. :In addition there was no exces .sive amount of matting,pilling' or shedding.
Example 6 percent of sodium bisulfate, a catalyst. The swatch was then placed in a drying oven and heated for 20 minutes at 220 F. The temperature was then raised to 280 F. for ten minutes to cure the silicone. It was then removed and allowed to cool, after which the swatch was laun dered for five consecutive times under normal laundering It was then removed and allowed to cool, after conditions. The hand remained very soft and the color was not affected. In addition there was no excessive amount of matting, pillingor shedding.
Example 7 A swatch of napped fabric composed of fibers of 92 percent acrylonitrile and 8 percent vinyl acetate was padded with an aqueous solution composed of 0.5 percent ethylene carbonate, 2.0 percent silicone resin and 0.2 7
percent sodium bisulfate, a catalyst. The swatch' was then placed in a drying, oven where it was heated for 20 minutes at 220 F. The temperature of the oven was then raised to 280 F. for minutes to cure the silicone resin. It was then removed from the oven and allowed to cool, after which the swatch was laundered five consecutive times under normal laundering conditions. The hand remained very soft and the color was not affected. In addition there was no excessive amount of matting, pilling or shedding.
With the stabilizing compound of this invention, it is possible to treat napped fabrics composed of acrylic fibers so that they may be laundered many times and their hand, color and physical properties, such as matting, pilling and shedding will not be appreciably changed from their original conditions.
Many modifications of the above will be obvious to those skilled in the art without a departure from the inventive concept.
I claim:
1. An article composed of the napped fabric of fibers of synthetic linear acrylonitrile, ethylene carbonate as a bonding agent at the point of intersection of the fibers in the nap and a silicone resin as a softening agent.
2. The article of claim 1 in which the fabric is composed of fibers of at least 80 percent acrylonitrile and up to 20 percent of another copolymerizable mono-olefinic monomer.
3. The article of claim 2 in which the fabric is composed of fibers of 94 percent acrylonitrile and 6 percent vinyl acetate.
4. The article of claim 2 in which the fabric is composed of fibers of a blend of 88 percent of one copolymer of 94 percent acrylonitrile and 6 percent vinyl acetate and 12 percent of another copolymer of 50 percent acrylonitrile and 50 percent methyl vinyl pyridine.
5. An article composed of the napped fabric of fibers of synthetic linear acrylonitrile and ethylene carbonate used as a bonding agent at the point of intersection of the fibers in the nap.
6. A method of stabilizing the nap of fabrics composed of fibers of synthetic linear polymers of acrylonitrile, comprising impregnating the napped fabric with an aqueous solution of ethylene carbonate and a silicone resin in which the ethylene carbonate as a bonding agent is used in an amount of from 0.05 percent to 50 percent by weight of the solution, drying said fabric and curing the silicone resin by heating said fabric at a temperature of from 240 F. to 300 F. for 5 to 60 minutes.
7. The method of claim 6 in which the napped fabric is treated with an aqueous solution of ethylene carbonate.
8. The method of claim 6 in which the fabric is composed of fibers of at least 80 percent acrylonitrile and up to 20 percent of another copolymerizable mono-olefinic monomer.
9. The method of claim 8 in which the fiber is composed of 94 percent acrylonitrile and 6 percent vinyl acetate.
10. The method of claim 8 in which the fiber is composed of a blend of 88 percent of one copolymer of 94 percent acrylonitrile and 6 percent vinyl acetate and 12 percent of another copolymer composed of 50 percent acrylonitrile and 50 percent methyl vinyl pyridine.
11. The method of claim 7 in which the fabric is composed of fibers of at least percent acrylonitrile and up to 20 percent of another copolymerizable monomer.
12. The method of claim 11 in which the fibers are selected from the group consisting of a fiber of 94 percent acrylonitrile and 6 percent vinyl acetate and a blend of 88 percent of one copolymer of 94 percent acrylonitrile and 6 percent vinyl acetate and 12 percent of another copolymer composed of 50 percent acrylonitrile and 50 percent methyl vinyl pyridine.
13. A method of stabilizing the nap of fabrics composed of fibers of at least 80 percent acrylonitrile and up to 20 percent of another copolymerizable mono-olefinic monomer, comprising impregnating the napped fabric with an aqueous solution of ethylene carbonate in which ethylene carbonate acts as a bonding agent at the point of intersection of the fibers in the nap to form a durable bond, with the amount of ethylene carbonate being 0.5 percent to 2.0 percent by weight of the solution, and drying said fabric.
14. A method of stabilizing the nap of fabrics composed of fibers of at least 80 percent acrylonitrile and up to 20 percent of another copolymerizable mono-olefinic monomer, comprising impregnating the napped fabric with an aqueous solution of ethylene carbonate, in the range of a 0.05 percent to a 50 percent solution, with ethylene carbonate acting as a bonding agent at the point of intersection of the fibers in the nap to form a durable bond, and a silicone resin emulsion in the range of 0.2 percent to 5 percent solution, drying said fabric and ouring the silicone resin by heating said fabric to 280 F. for 10 minutes.
15. The method of claim 13 in which the aqueous solution of ethylene carbonate is a 1 percent solution.
16. The method of claim 14 in which the aqueous solution of ethylene carbonate is a 1 percent solution and the silicon resin is 1 to 2 percent emulsion.
Dennett Mar. 11, 1952 Jones et al Feb. 7, 1956
Claims (1)
- 6. A METHOD OF STABILIZING THE NAP OF FABRICS COMPOSED OF FIBERS OF SYNTHETIC LINEAR POLYMERS OF ACRYLONITRILE, COMPRISING IMPREGNATING THE NAPPED FABRIC WITH AN AQUEOUS SOLUTION OF ETHYLENE CARBONATE AND A SILICONE RESIN IN WHICH THE ETHYLENE CARBONATE AS A BONDING AGENT IS USED IN AN AMOUNT OF FROM 0.05 PERCENT TO 50 PERCENT BY WEIGHT OF THE SOLUTION, DRYING SAID FABRIC AND CURING THE SILICONE RESIN BY HEATING SAID FABRIC AT A TEMPERATURE OF FROM 240*F. TO 300*F. FOR 5 TO 60 MINUTES.
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE621636D BE621636A (en) | 1961-08-23 | ||
NL282288D NL282288A (en) | 1961-08-23 | ||
US133299A US3167448A (en) | 1961-08-23 | 1961-08-23 | Process of treating fabrics with ethylene carbonate and article produced therefrom |
GB31939/62A GB988453A (en) | 1961-08-23 | 1962-08-20 | Improvements in the treatment of napped polyacrylonitrile fabrics |
FR907412A FR1331247A (en) | 1961-08-23 | 1962-08-21 | Improvements in the treatment of synthetic fabrics, in particular acrylic fabrics |
SE9080/62A SE312117B (en) | 1961-08-23 | 1962-08-21 | |
DE19621444093 DE1444093A1 (en) | 1961-08-23 | 1962-08-22 | Process for stabilizing the roughening or the pile of textile goods |
CH1005762A CH392452A (en) | 1961-08-23 | 1962-08-23 | Method of stabilizing the pile layer of acrylic fiber fabrics |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US133299A US3167448A (en) | 1961-08-23 | 1961-08-23 | Process of treating fabrics with ethylene carbonate and article produced therefrom |
Publications (1)
Publication Number | Publication Date |
---|---|
US3167448A true US3167448A (en) | 1965-01-26 |
Family
ID=22457922
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US133299A Expired - Lifetime US3167448A (en) | 1961-08-23 | 1961-08-23 | Process of treating fabrics with ethylene carbonate and article produced therefrom |
Country Status (7)
Country | Link |
---|---|
US (1) | US3167448A (en) |
BE (1) | BE621636A (en) |
CH (1) | CH392452A (en) |
DE (1) | DE1444093A1 (en) |
GB (1) | GB988453A (en) |
NL (1) | NL282288A (en) |
SE (1) | SE312117B (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3399079A (en) * | 1964-09-25 | 1968-08-27 | American Cyanamid Co | Antistatic fiber blend |
US3431159A (en) * | 1964-06-17 | 1969-03-04 | David Gordon | Manufacture of mouldings from acrylonitrile copolymers |
US3488217A (en) * | 1968-02-29 | 1970-01-06 | Du Pont | Process for imparting a soft feel to textile fiber and the resulting fiber |
US3530214A (en) * | 1967-02-24 | 1970-09-22 | Julius Hermes | Method for treating textile materials to uniformly set their shape |
US4290766A (en) * | 1980-09-22 | 1981-09-22 | Milliken Research Corporation | Chemically sculpturing acrylic fabrics and process for preparing same |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2588365A (en) * | 1949-11-10 | 1952-03-11 | Dow Corning | Method of rendering fabrics waterrepellent and product resulting therefrom |
US2734041A (en) * | 1953-03-13 | 1956-02-07 | Compositions of matter comprising |
-
0
- BE BE621636D patent/BE621636A/xx unknown
- NL NL282288D patent/NL282288A/xx unknown
-
1961
- 1961-08-23 US US133299A patent/US3167448A/en not_active Expired - Lifetime
-
1962
- 1962-08-20 GB GB31939/62A patent/GB988453A/en not_active Expired
- 1962-08-21 SE SE9080/62A patent/SE312117B/xx unknown
- 1962-08-22 DE DE19621444093 patent/DE1444093A1/en active Pending
- 1962-08-23 CH CH1005762A patent/CH392452A/en unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2588365A (en) * | 1949-11-10 | 1952-03-11 | Dow Corning | Method of rendering fabrics waterrepellent and product resulting therefrom |
US2734041A (en) * | 1953-03-13 | 1956-02-07 | Compositions of matter comprising |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3431159A (en) * | 1964-06-17 | 1969-03-04 | David Gordon | Manufacture of mouldings from acrylonitrile copolymers |
US3399079A (en) * | 1964-09-25 | 1968-08-27 | American Cyanamid Co | Antistatic fiber blend |
US3530214A (en) * | 1967-02-24 | 1970-09-22 | Julius Hermes | Method for treating textile materials to uniformly set their shape |
US3488217A (en) * | 1968-02-29 | 1970-01-06 | Du Pont | Process for imparting a soft feel to textile fiber and the resulting fiber |
US4290766A (en) * | 1980-09-22 | 1981-09-22 | Milliken Research Corporation | Chemically sculpturing acrylic fabrics and process for preparing same |
Also Published As
Publication number | Publication date |
---|---|
SE312117B (en) | 1969-07-07 |
DE1444093A1 (en) | 1968-11-07 |
GB988453A (en) | 1965-04-07 |
BE621636A (en) | 1900-01-01 |
CH392452A (en) | 1965-02-15 |
NL282288A (en) | 1900-01-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US2955958A (en) | Process of treating woven textile fabric with a vinyl chloride polymer | |
US2403960A (en) | Antistatic treatment of vinyl resin articles | |
NO146527B (en) | DEVICE WITH A NUMBER OF FLUID LOCATED PIPE WORKING STATIONS | |
US3000758A (en) | Process for conferring antistatic properties and the resulting products | |
US3167448A (en) | Process of treating fabrics with ethylene carbonate and article produced therefrom | |
US3137668A (en) | Anti-static coating composition comprising styrene sulfonate-glycidyl methacrylate polymer and sodium bisulfite | |
US3152919A (en) | Stabilized acrylic fabrics and method for treatment of acrylic fabrics | |
US3180913A (en) | Method for producing high shrinkage fibers | |
US3100674A (en) | Process for shrink-proofing proteinaceous textile materials and the product therefrom | |
US3127305A (en) | Stabilized nap fabric | |
US3108356A (en) | Stabilizing agent | |
US2780608A (en) | Protein-containing textiles and stabilization thereof | |
US3186868A (en) | Method of flameproofing acrylic fibers and the resulting product | |
US3281260A (en) | Process for treating acrylonitrile fibers with ultra-violet light stabilizer | |
US3097054A (en) | Method of making high-shrink textile fibers | |
US3034957A (en) | Synthetic fibers and fabrics having microbicidal activity | |
US2961340A (en) | Process for coating hydrophilic films | |
US2740687A (en) | Method of dyeing structures comprising acrylonitrile polymers | |
US3313796A (en) | Process for improving the antistatic properties of synthetic articles | |
US2732317A (en) | Modified cellulose and method of | |
US3088932A (en) | Acrylonitrile polymer composition and stabilized with zinc oxalate, zinc acetate, or chromium acetate | |
US3852102A (en) | Permanent anti-snag finish for fabrics | |
US3241994A (en) | Method for making embossed cellulose triacetate fabrics | |
US3148236A (en) | Creasing process for thermoplastic materials | |
US3320088A (en) | Stereoregular polypropylene coated with an insolubilized ethylene oxide polymer |