GB873492A - Cross-linked cellulosic fibrous products and methods of making them - Google Patents
Cross-linked cellulosic fibrous products and methods of making themInfo
- Publication number
- GB873492A GB873492A GB1557/58A GB155758A GB873492A GB 873492 A GB873492 A GB 873492A GB 1557/58 A GB1557/58 A GB 1557/58A GB 155758 A GB155758 A GB 155758A GB 873492 A GB873492 A GB 873492A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acids
- amine
- salt
- fibres
- vinyl
- 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
Links
- -1 nitric Chemical class 0.000 abstract 8
- 150000003839 salts Chemical class 0.000 abstract 8
- 150000001412 amines Chemical class 0.000 abstract 6
- 229920000297 Rayon Polymers 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- 239000007864 aqueous solution Substances 0.000 abstract 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 2
- 240000008564 Boehmeria nivea Species 0.000 abstract 2
- 229920000742 Cotton Polymers 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Chemical group 0.000 abstract 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 229920002678 cellulose Polymers 0.000 abstract 2
- 239000001913 cellulose Substances 0.000 abstract 2
- 238000004132 cross linking Methods 0.000 abstract 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 235000019253 formic acid Nutrition 0.000 abstract 2
- 125000005395 methacrylic acid group Chemical group 0.000 abstract 2
- 150000007522 mineralic acids Chemical class 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 239000004745 nonwoven fabric Substances 0.000 abstract 2
- 150000007524 organic acids Chemical class 0.000 abstract 2
- 235000005985 organic acids Nutrition 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract 2
- 239000002964 rayon Substances 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- 235000002906 tartaric acid Nutrition 0.000 abstract 2
- PUMIBBNWDCWIKR-UHFFFAOYSA-M 1-(octadecoxymethyl)pyridin-1-ium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCOC[N+]1=CC=CC=C1 PUMIBBNWDCWIKR-UHFFFAOYSA-M 0.000 abstract 1
- WJDJWDHXZBNQNE-UHFFFAOYSA-M 1-octadecylpyridin-1-ium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 WJDJWDHXZBNQNE-UHFFFAOYSA-M 0.000 abstract 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 abstract 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical group C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 abstract 1
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 abstract 1
- VJOWMORERYNYON-UHFFFAOYSA-N 5-ethenyl-2-methylpyridine Chemical compound CC1=CC=C(C=C)C=N1 VJOWMORERYNYON-UHFFFAOYSA-N 0.000 abstract 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- 229920003043 Cellulose fiber Polymers 0.000 abstract 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 abstract 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 abstract 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 abstract 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000980 acid dye Substances 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical class OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 239000000982 direct dye Substances 0.000 abstract 1
- 239000002270 dispersing agent Substances 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical class OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 abstract 1
- 239000003607 modifier Substances 0.000 abstract 1
- 239000000178 monomer Substances 0.000 abstract 1
- 239000000049 pigment Substances 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 abstract 1
- 239000005871 repellent Substances 0.000 abstract 1
- 229920001567 vinyl ester resin Polymers 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
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
- 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
- D06M13/165—Ethers
- D06M13/175—Unsaturated ethers, e.g. vinylethers
-
- 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
- Y10S8/02—Vinyl sulfones and precursors thereof
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
The cellulose fibres in fibrous products in which more than 50% by weight of the fibres are cellulosic are cross-linked by reaction with a salt of an amine of the formula: R3-nN(-AXCH=CH2)n in which n is 2 or 3, R is a cyclohexyl, benzyl or C1-C8 alkyl group, A is an alkylene group having 2-4 carbon atoms and providing at least two carbon atoms between the X and N atoms and X is oxygen or sulphur. The salts of the amine may be formed from inorganic acids, e.g. nitric, sulphuric, fluoboric and perchloric acids, or organic acids, e.g. formic, acetic, propionic, maleic, fumaric, succinic, citric, adipic, sebacic, oxalic, phthalic and tartaric acids, or from mixtures of acids, e.g. a mixture of formic and sulphuric acids. The salt may be applied to the fibrous product as an aqueous solution containing 5%-20% by weight of the salt and the fibrous product may then be dried and heated to 250 DEG -400 DEG F. for a period of one-half minute to an hour to cause reaction of the amine with the cellulose. The cellulosic fibres may be cotton, viscose rayon, cuprammonium rayon, linen or ramie and may be in the form of woven, knitted or non-woven fabrics, yarns, threads or other plied structures or fibres or filaments in loose or bulk masses or webbing, matting or batting. Specifications 873,802, 838,020 and 839,561 are referred to.ALSO:The crease-resistance, shrink-resistance and receptivity to acid and direct dyes of fibrous products in which more than 50% by weight of the fibres are cellulosic are improved by cross-linking the cellulosic fibres by reaction with a salt of an amine of the formula:- R3-nN(-AX CH=CH2)n in which n is 2 or 3, R is a cyclohexyl, benzyl or C1-C8 alkyl group, A is an alkylene group having 2-4 carbon atoms and providing at least two carbon atoms between the X and N atoms and X is oxygen or sulphur. The salts of the amine may be formed from inorganic acids, e.g. nitric, sulphuric, fluoboric and perchloric acids, or organic acids, e.g. formic, acetic, propionic, maleic, fumaric, succinic, citric, adipic, sebacic, oxalic, phthalic and tartaric acids, or from mixtures of acids, e.g. a mixture of formic and sulphuric acids. The salt may be applied to the fibrous product as an aqueous solution containing 5-20% by weight of the salt, and the fibrous product may then be dried and heated to 250 DEG -400 DEG F. for a period of one-half minute to an hour to cause reaction of the amine with the cellulose. The treatment with the amine salt may be supplemented by treatment with a hand-modifier or builder, softener or water-repellent agent, e.g. quaternary ammonium compounds having a long-chain hydrocarbon group such as stearyl pyridinium chloride and octadecyl oxymethylpyridinium chloride, or materials which enhance the crease resistance, e.g. aqueous dispersions of water-insoluble linear addition polymers of monoethylenically unsaturated monomers such as acrylic, methacrylic and itaconic acids and copolymers thereof with esters of acrylic, methacrylic, itaconic, maleic, fumaric or citraconic acids with monohydric alcohols, vinyl esters of carboxylic acids, vinyloxyalkyl esters, vinyl ethers, methacrylonitrile, acrylonitrile, acrylamide, methacrylamide, vinyl chloride or bromide, vinylidene chloride, fluoride or cyanide, 1-chloro-1-fluoroethylene, ethylene, styrene, 2-vinyl- or 4-vinyl pyridine or 2-methyl-5-vinyl pyridine dispersed by means of non-ionic dispersing agents, which may be applied simultaneously with or before or after the amine salt. The cellulosic fibres may be cotton, viscose rayon, cuprammonium rayon, linen or ramie and may be in the form of woven, knitted or non-woven fabrics, yarns, threads or other plied structures or fibres or filaments in loose or bulk masses or webbing, matting or batting. Pigments and/or dyes may be included in the aqueous solution used to apply the amine salt or the fibrous products may be printed or dyed after the cross-linking treatment. Specifications 837,802, 838,020 and 839,561 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US636852A US2940817A (en) | 1957-01-29 | 1957-01-29 | Crease-proofing cellulosic fabrics, the fabrics obtained and methods of making them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB873492A true GB873492A (en) | 1961-07-26 |
Family
ID=24553602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1557/58A Expired GB873492A (en) | 1957-01-29 | 1958-01-16 | Cross-linked cellulosic fibrous products and methods of making them |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US2940817A (en) |
| FR (1) | FR1198604A (en) |
| GB (1) | GB873492A (en) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3044843A (en) * | 1959-05-13 | 1962-07-17 | Du Pont | Fiber dyeing process |
| GB879980A (en) * | 1959-08-04 | 1961-10-11 | Ici Ltd | Textile colouration process |
| US3115383A (en) * | 1960-04-12 | 1963-12-24 | Stevens & Co Inc J P | Process for reacting cellulosic material with polyquaternary ammonium derivatives of bis halomethyl ethers and products resulting therefrom |
| US3097910A (en) * | 1960-06-29 | 1963-07-16 | Ici Ltd | Process for dyeing textiles with dyestuffs containing pyrimidine ring |
| US3400127A (en) * | 1963-08-22 | 1968-09-03 | Stevens & Co Inc J P | Triazine compounds for modifying polymers |
| US3335163A (en) * | 1963-08-30 | 1967-08-08 | Stevens & Co Inc J P | Fluoro-sulfur containing compounds |
| US3414367A (en) * | 1963-11-06 | 1968-12-03 | Agriculture Usa | Process for making n-substituted aminoethylsulfonylethyl ethers of cellulose |
| US3932209A (en) * | 1969-02-24 | 1976-01-13 | Personal Products Company | Low hemicellulose, dry crosslinked cellulosic absorbent materials |
| US4026807A (en) * | 1974-08-09 | 1977-05-31 | Petrolite Corporation | Alkynoxymethyl amines |
| US4026946A (en) * | 1975-03-07 | 1977-05-31 | Petrolite Corporation | Halogen derivatives of alkynoxymethyl amines |
| CN113338033B (en) * | 2021-06-16 | 2022-04-05 | 江苏华佳丝绸股份有限公司 | A kind of silk anti-wrinkle fabric and preparation method thereof |
| CN119553505B (en) * | 2024-10-31 | 2025-07-08 | 广东群豪服饰有限公司 | Preparation method of crease-resistant comfortable fabric |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2734890A (en) * | 1956-02-14 | Ureidoalkyl vinyl ethers | ||
| NL200174A (en) * | 1952-04-16 | |||
| GB763635A (en) * | 1953-04-10 |
-
1957
- 1957-01-29 US US636852A patent/US2940817A/en not_active Expired - Lifetime
-
1958
- 1958-01-16 GB GB1557/58A patent/GB873492A/en not_active Expired
- 1958-01-28 FR FR1198604D patent/FR1198604A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US2940817A (en) | 1960-06-14 |
| FR1198604A (en) | 1959-12-08 |
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