GB984278A - New organic phosphoric amido compounds for use as cross-linking agents, compositions containing them and materials cross-linked by them - Google Patents
New organic phosphoric amido compounds for use as cross-linking agents, compositions containing them and materials cross-linked by themInfo
- Publication number
- GB984278A GB984278A GB11392/61A GB1139261A GB984278A GB 984278 A GB984278 A GB 984278A GB 11392/61 A GB11392/61 A GB 11392/61A GB 1139261 A GB1139261 A GB 1139261A GB 984278 A GB984278 A GB 984278A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cross
- alkyl
- sulphur
- hydrogen
- hydrocarbon radical
- 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
- 239000003431 cross linking reagent Substances 0.000 title abstract 10
- 239000000203 mixture Substances 0.000 title abstract 3
- 125000003368 amide group Chemical group 0.000 title 1
- 239000000463 material Substances 0.000 title 1
- -1 aliphatic hydrocarbon radical Chemical class 0.000 abstract 14
- 125000000217 alkyl group Chemical group 0.000 abstract 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 11
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract 11
- 239000005864 Sulphur Substances 0.000 abstract 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 8
- 239000004744 fabric Substances 0.000 abstract 8
- 239000001257 hydrogen Substances 0.000 abstract 8
- 229910052739 hydrogen Inorganic materials 0.000 abstract 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 7
- 239000001301 oxygen Substances 0.000 abstract 7
- 229910052760 oxygen Inorganic materials 0.000 abstract 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 6
- 229920000126 latex Polymers 0.000 abstract 6
- 239000004816 latex Substances 0.000 abstract 6
- 229920000459 Nitrile rubber Polymers 0.000 abstract 5
- 239000004372 Polyvinyl alcohol Substances 0.000 abstract 5
- 229920000297 Rayon Polymers 0.000 abstract 5
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 abstract 5
- 244000144992 flock Species 0.000 abstract 5
- 229920002451 polyvinyl alcohol Polymers 0.000 abstract 5
- 235000019422 polyvinyl alcohol Nutrition 0.000 abstract 5
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 abstract 4
- 239000004215 Carbon black (E152) Substances 0.000 abstract 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 abstract 4
- 239000006185 dispersion Substances 0.000 abstract 4
- 125000005842 heteroatom Chemical group 0.000 abstract 4
- 229930195733 hydrocarbon Natural products 0.000 abstract 4
- 229920002521 macromolecule Polymers 0.000 abstract 4
- 150000002903 organophosphorus compounds Chemical class 0.000 abstract 4
- 239000000049 pigment Substances 0.000 abstract 4
- 239000000853 adhesive Substances 0.000 abstract 3
- 230000001070 adhesive effect Effects 0.000 abstract 3
- 229920001577 copolymer Polymers 0.000 abstract 3
- 229920001971 elastomer Polymers 0.000 abstract 3
- 239000000839 emulsion Substances 0.000 abstract 3
- 239000004745 nonwoven fabric Substances 0.000 abstract 3
- 229920002689 polyvinyl acetate Polymers 0.000 abstract 3
- 239000011118 polyvinyl acetate Substances 0.000 abstract 3
- 239000005060 rubber Substances 0.000 abstract 3
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 abstract 2
- 229920000742 Cotton Polymers 0.000 abstract 2
- 229910018894 PSCl3 Inorganic materials 0.000 abstract 2
- 229920006322 acrylamide copolymer Polymers 0.000 abstract 2
- 229920000180 alkyd Polymers 0.000 abstract 2
- 239000008199 coating composition Substances 0.000 abstract 2
- 229960002380 dibutyl phthalate Drugs 0.000 abstract 2
- 230000005686 electrostatic field Effects 0.000 abstract 2
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 229920000609 methyl cellulose Polymers 0.000 abstract 2
- 239000001923 methylcellulose Substances 0.000 abstract 2
- 239000011707 mineral Substances 0.000 abstract 2
- 235000010755 mineral Nutrition 0.000 abstract 2
- 229920006173 natural rubber latex Polymers 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- 229920000728 polyester Polymers 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- 239000000243 solution Substances 0.000 abstract 2
- WQYSXVGEZYESBR-UHFFFAOYSA-N thiophosphoryl chloride Chemical compound ClP(Cl)(Cl)=S WQYSXVGEZYESBR-UHFFFAOYSA-N 0.000 abstract 2
- 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
- 229920003043 Cellulose fiber Polymers 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 108010010803 Gelatin Proteins 0.000 abstract 1
- 244000043261 Hevea brasiliensis Species 0.000 abstract 1
- VGGLHLAESQEWCR-UHFFFAOYSA-N N-(hydroxymethyl)urea Chemical compound NC(=O)NCO VGGLHLAESQEWCR-UHFFFAOYSA-N 0.000 abstract 1
- 229910019213 POCl3 Inorganic materials 0.000 abstract 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 abstract 1
- 239000004952 Polyamide Substances 0.000 abstract 1
- 239000004159 Potassium persulphate Substances 0.000 abstract 1
- 229920002472 Starch Polymers 0.000 abstract 1
- MBHRHUJRKGNOKX-UHFFFAOYSA-N [(4,6-diamino-1,3,5-triazin-2-yl)amino]methanol Chemical compound NC1=NC(N)=NC(NCO)=N1 MBHRHUJRKGNOKX-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000000980 acid dye Substances 0.000 abstract 1
- 230000032683 aging Effects 0.000 abstract 1
- 229920000615 alginic acid Polymers 0.000 abstract 1
- 239000000783 alginic acid Substances 0.000 abstract 1
- 235000010443 alginic acid Nutrition 0.000 abstract 1
- 229960001126 alginic acid Drugs 0.000 abstract 1
- 150000004781 alginic acids Chemical class 0.000 abstract 1
- 150000005215 alkyl ethers Chemical class 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 239000007900 aqueous suspension Substances 0.000 abstract 1
- 239000000981 basic dye Substances 0.000 abstract 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 229920002678 cellulose Polymers 0.000 abstract 1
- 229920003086 cellulose ether Polymers 0.000 abstract 1
- JZGWEIPJUAIDHM-UHFFFAOYSA-N chembl2007771 Chemical compound C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S(O)(=O)=O)S(O)(=O)=O)=CC=C(S(O)(=O)=O)C2=C1 JZGWEIPJUAIDHM-UHFFFAOYSA-N 0.000 abstract 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 abstract 1
- 238000004132 cross linking Methods 0.000 abstract 1
- 239000000982 direct dye Substances 0.000 abstract 1
- 239000003822 epoxy resin Substances 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 239000000835 fiber Substances 0.000 abstract 1
- 229920000159 gelatin Polymers 0.000 abstract 1
- 239000008273 gelatin Substances 0.000 abstract 1
- 235000019322 gelatine Nutrition 0.000 abstract 1
- 235000011852 gelatine desserts Nutrition 0.000 abstract 1
- 239000004519 grease Substances 0.000 abstract 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000010985 leather Substances 0.000 abstract 1
- 229920003052 natural elastomer Polymers 0.000 abstract 1
- 229920001194 natural rubber Polymers 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000000123 paper Substances 0.000 abstract 1
- 238000005325 percolation Methods 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- 229920002647 polyamide Polymers 0.000 abstract 1
- 229920000647 polyepoxide Polymers 0.000 abstract 1
- 229920001195 polyisoprene Polymers 0.000 abstract 1
- 229920002635 polyurethane Polymers 0.000 abstract 1
- 239000004814 polyurethane Substances 0.000 abstract 1
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 1
- 239000004800 polyvinyl chloride Substances 0.000 abstract 1
- 235000012731 ponceau 4R Nutrition 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- 235000015320 potassium carbonate Nutrition 0.000 abstract 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 abstract 1
- 235000019394 potassium persulphate Nutrition 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000002964 rayon Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 238000002791 soaking Methods 0.000 abstract 1
- 239000008107 starch Substances 0.000 abstract 1
- 235000019698 starch Nutrition 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
- 239000004094 surface-active agent Substances 0.000 abstract 1
- 229920003051 synthetic elastomer Polymers 0.000 abstract 1
- 229920002994 synthetic fiber Polymers 0.000 abstract 1
- 239000005061 synthetic rubber Substances 0.000 abstract 1
- 229920001187 thermosetting polymer Polymers 0.000 abstract 1
- 229920006305 unsaturated polyester Polymers 0.000 abstract 1
- 235000013311 vegetables Nutrition 0.000 abstract 1
- 238000004073 vulcanization Methods 0.000 abstract 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/564—Three-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0246—Polyamines containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
-
- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/5399—Phosphorus bound to nitrogen
-
- D—TEXTILES; PAPER
- D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
- D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
- D04H1/00—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres
- D04H1/40—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties
- D04H1/58—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties by applying, incorporating or activating chemical or thermoplastic bonding agents, e.g. adhesives
- D04H1/587—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties by applying, incorporating or activating chemical or thermoplastic bonding agents, e.g. adhesives characterised by the bonding agents used
-
- D—TEXTILES; PAPER
- D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
- D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
- D04H1/00—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres
- D04H1/40—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties
- D04H1/58—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties by applying, incorporating or activating chemical or thermoplastic bonding agents, e.g. adhesives
- D04H1/64—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties by applying, incorporating or activating chemical or thermoplastic bonding agents, e.g. adhesives the bonding agent being applied in wet state, e.g. chemical agents in dispersions or solutions
-
- 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
- D06M13/322—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 nitrogen
- D06M13/487—Aziridinylphosphines; Aziridinylphosphine-oxides or sulfides; Carbonylaziridinyl or carbonylbisaziridinyl compounds; Sulfonylaziridinyl or sulfonylbisaziridinyl compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Textile Engineering (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Dispersion Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention comprises compounds of formula <FORM:0984278/C2/1> where A is a bivalent aliphatic hydrocarbon radical, a cycloaliphatic hydrocarbon radical, or a bivalent aliphatic radical interrupted by a hetero atom, e.g. oxygen or sulphur, X1 and X2 are each oxygen or sulphur, R and R1 are each hydrogen or alkyl and Y1 and Y2 are each -OR11 or <FORM:0984278/C2/2> where R1 and R2 are each hydrogen or alkyl and R11 is alkyl. They are prepared by reacting HO-A-OH and PSCl3 or POCl3 to give Cl2P(X2)-O-A-O-P(X2)Cl2 and then reacting this with an ethyleneimine in the presence of K2CO3, or first with the theoretical amount of an alcohol R11OH and then with the ethyleneimine. The products are used to cross-link natural and synthetic macro-molecular compounds (see Divisions B2, B6, C3 and D1). The compound Cl2P(S)-OCH2CH2-O-CH2CH2O -P(S)Cl2 is obtained from diethylene glycol and PSCl3.ALSO:Natural and synthetic macromolecular substances are cross-linked by means of an organophosphorus compound of formula <FORM:0984278/C3/1> where A is a bivalent aliphatic hydrocarbon radical, a cycloaliphatic hydrocarbon radical, or a bivalent aliphatic radical interrupted by a hetero atom, e.g. oxygen or sulphur, R and R1 are each hydrogen or alkyl and Y1 and Y2 are each -OR11 or <FORM:0984278/C3/2> where R1 and R2 are each hydrogen or alkyl and R11 is alkyl (for preparation see Division C2). Specified macromolecular substances include starch, alginic acid, gelatin, cellulose fibres, cellulose esters and ethers, polyesters, alkyd resins, polyamides, polyurethanes, polyacrylic compounds, polyvinylacetate, polyvinylalcohol, polyvinylchloride and copolymers thereof, natural rubber and synthetic rubbers such as butadiene-styrene copolymers, butadiene-acrylonitrile copolymers and polyisoprene. Cross-linking may be effected at 100-200 DEG C., preferably 130-150 DEG C. using 1-15% by weight of cross-linking agent. The cross-linking agent is suitably added to an aqueous solution or dispersion of the macromolecular substance. Plasticizers, epoxy resins, unsaturated polyesters, alkyd resins and/or precondensates of thermosetting resins, e.g. etherified methylol urea or etherified methylol melamine may also be added. The following compositions which contain in addition a cross-linking agent of the above type are prepared in examples: (2) a printing paste by homogenizing a butyl acrylate-acrylonitrile-acrylamide copolymer latex, methylcellulose, ammonium nitrate, mineral spirit, pigment and water; (3) an adhesive for preparing non-woven fabric from the above latex and water; (4) an adhesive for preparing non-woven fabric from a butadiene-acrylonitrile copolymer latex, polyvinylalcohol and water; (5) a paste for sticking flocks to rubber sheet from natural rubber latex, polyvinyl alcohol, colloidal sulphur, a vulcanization promoter, an ageing retardant and water; (6) a paste for sticking flock to fabric from polyvinylacetate emulsion, butyl phthalate, ammonium nitrate, pigment and water; and (7) a coating composition from butadiene-acrylonitrile copolymer, sulphur and methylethylketone. The latex used in Examples 2 and 3 is prepared by copolymerizing butyl acrylate, acrylonitrile and acrylamide (78 : 20 : 2 weight ratio) in aqueous suspension using potassium persulphate as catalyst.ALSO:Polmeric coating compositions contain as cross-linking agent an organophosphorus compound of formula: <FORM:0984278/B1-B2/1> where A is a bivalent aliphatic hydrocarbon radical, a cycloaliphatic hydrocarbon radical, or a bivalent radical interrupted by a hetero atom, e.g. oxygen or sulphur, X1 and X2 are each oxygen or sulphur, R and R1 are each hydrogen or alkyl, and Y1 and Y2 are each -OR11 or <FORM:0984278/B1-B2/2> where R1 and R2 are each hydrogen or alkyl and R11 is alkyl. The composition may be in the form of a printing paste for fabrics or may be used to stick flock on to flexible substrates such as fabrics, rubbers, leather, paper or metal. In examples: (2) cotton and rayon cloths are printed with a paste prepared by homogenizing a butyl acrylate-acrylonitrile-acrylamide copolymer latex, methylcellulose, copper phthalocyanin pigment, ammonium nitrate and one of the above cross-linking agents; the print is fixed by heating at 130 DEG C.; (5) a rubber sheet is treated with a paste prepared from a natural rubber latex, polyvinyl alcohol, colloidal sulphur, water and one of the above cross-linking agents, exposed in a wet state to viscose rayon flocks in an electrostatic field, dried, and heated at 130 DEG C.; (6) cotton fabric is printed with a paste comprising polyvinylacetate emulsion, butyl phthalate, ammonium nitrate, pigment, water and one of the above cross-linking agents, treated while wet with viscose rayon flocks in an electrostatic field, dried, and heated at 130 DEG C.; (7) a metal surface cleaned by removal of grease followed by acid percolation is brushed or sprayed with a methyl ethyl ketone solution containing butadiene-acrylonitrile copolymer, sulphur and one of the above cross-linking agents, dried and heated at 130 DEG C. under 100-1000 p.s.i. pressure.ALSO:A treatment for imparting crease resistance to fabrics made of natural and synthetic fibres and for increasing their affinity to direct and basic dyes comprises soaking the fabric with an aqueous dispersion or organic solvent solution of an organophosphorus compound of formula <FORM:0984278/D1-D2/1> where A is a bivalent aliphatic hydrocarbon radical, a cycloaliphatic hydrocarbon radical, or a bivalent radical interrupted by a hetero atom, e.g. oxygen or sulphur, X1 and X2 are each oxygen or sulphur, R and R1 are each hydrogen or alkyl, and Y1 and Y2 are each -OR11 or <FORM:0984278/D1-D2/2> where R1 and R2 are each hydrogen or alkyl and R11 is alkyl. The fabric is then dried and heated. In Example 1 an aqueous emulsion comprising a polyoxyethylene alkyl ether surface active agent and the compound <FORM:0984278/D1-D2/3> is padded on to viscose rayon cloth, which is dried and thermally set at 150 DEG C. It is then dyed with Brilliant Scarlet 3R (acid dye). Non-woven fabrics are prepared by using as adhesive a macromolecular substance together with one of the above organophosphorus compounds as cross-linking agent. Various fibres of animal, vegetable, mineral and synthetic origin are specified. In examples: (3) a random web of polyester fibre is sprayed with and then dipped in an aqueous dispersion of a butylacrylate-acrylonitrileacrylamide copolymer latex and the compound <FORM:0984278/D1-D2/4> squeezed between rollers, dried and heated at 150 DEG C.; (4) a viscose rayon random web is similarly treated with an aqueous dispersion of a butadiene-acrylonitrile copolymer and polyvinyl alcohol containing the same phosphorus compound as (3).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1040260 | 1960-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB984278A true GB984278A (en) | 1965-02-24 |
Family
ID=11749131
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB11392/61A Expired GB984278A (en) | 1960-03-31 | 1961-03-28 | New organic phosphoric amido compounds for use as cross-linking agents, compositions containing them and materials cross-linked by them |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1263291B (en) |
| GB (1) | GB984278A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3507839A (en) * | 1965-10-05 | 1970-04-21 | Thiokol Chemical Corp | Curing process for carboxyl polymers using tetraimines |
| GB2358830A (en) * | 1999-12-13 | 2001-08-08 | Fuji Spinning Co Ltd | Regenerated cellulose fibre |
-
1961
- 1961-03-28 GB GB11392/61A patent/GB984278A/en not_active Expired
- 1961-03-30 DE DEH42168A patent/DE1263291B/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3507839A (en) * | 1965-10-05 | 1970-04-21 | Thiokol Chemical Corp | Curing process for carboxyl polymers using tetraimines |
| GB2358830A (en) * | 1999-12-13 | 2001-08-08 | Fuji Spinning Co Ltd | Regenerated cellulose fibre |
| GB2358830B (en) * | 1999-12-13 | 2003-10-08 | Fuji Spinning Co Ltd | A method for manufacturing improved regenerated cellulose fiber |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1263291B (en) | 1968-03-14 |
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