IL33535A - Phosphorus compounds,their manufacture and their use for the flameproofing and crease-proofing of cellulose-containing fibre materials - Google Patents
Phosphorus compounds,their manufacture and their use for the flameproofing and crease-proofing of cellulose-containing fibre materialsInfo
- Publication number
- IL33535A IL33535A IL33535A IL3353569A IL33535A IL 33535 A IL33535 A IL 33535A IL 33535 A IL33535 A IL 33535A IL 3353569 A IL3353569 A IL 3353569A IL 33535 A IL33535 A IL 33535A
- Authority
- IL
- Israel
- Prior art keywords
- residue
- carbon atoms
- formula
- process according
- alkyl
- Prior art date
Links
- 239000000463 material Substances 0.000 title claims description 22
- 150000003018 phosphorus compounds Chemical class 0.000 title claims description 17
- 239000000835 fiber Substances 0.000 title claims description 11
- 229920002678 cellulose Polymers 0.000 title claims description 8
- 239000001913 cellulose Substances 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 238000004855 creaseproofing Methods 0.000 title claims description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 90
- 125000004432 carbon atom Chemical group C* 0.000 claims description 63
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 239000000047 product Substances 0.000 claims description 26
- 238000002360 preparation method Methods 0.000 claims description 24
- 125000001188 haloalkyl group Chemical group 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
- -1 phosphorus compound Chemical class 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 12
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 11
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 229920002866 paraformaldehyde Polymers 0.000 claims description 11
- 229910052698 phosphorus Inorganic materials 0.000 claims description 10
- 239000011574 phosphorus Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 229920003180 amino resin Polymers 0.000 claims description 9
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 5
- 239000003377 acid catalyst Substances 0.000 claims description 4
- VNVRRNRPVIZREH-UHFFFAOYSA-N carbamoylphosphonic acid Chemical compound NC(=O)P(O)(O)=O VNVRRNRPVIZREH-UHFFFAOYSA-N 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229920000877 Melamine resin Polymers 0.000 claims description 3
- 239000007859 condensation product Substances 0.000 claims description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 2
- 239000005871 repellent Substances 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000005741 alkyl alkenyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000009877 rendering Methods 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 239000004744 fabric Substances 0.000 description 8
- 239000000395 magnesium oxide Substances 0.000 description 8
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 8
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
- 239000002759 woven fabric Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000000470 constituent Substances 0.000 description 5
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 5
- LSCSYJWMZUCJDW-UHFFFAOYSA-N 3-dimethoxyphosphorylpropanamide Chemical compound COP(=O)(OC)CCC(N)=O LSCSYJWMZUCJDW-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000000875 corresponding effect Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 235000011007 phosphoric acid Nutrition 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 229940077445 dimethyl ether Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- LJZOTLVPIGKBBG-UHFFFAOYSA-N 2-(dimethoxyphosphorylmethyl)-3-hydroxypropanamide Chemical compound COP(=O)(OC)CC(C(=O)N)CO LJZOTLVPIGKBBG-UHFFFAOYSA-N 0.000 description 2
- BTDQXGUEVVTAMD-UHFFFAOYSA-N 2-hydroxyethyl carbamate Chemical compound NC(=O)OCCO BTDQXGUEVVTAMD-UHFFFAOYSA-N 0.000 description 2
- NNTWKXKLHMTGBU-UHFFFAOYSA-N 4,5-dihydroxyimidazolidin-2-one Chemical compound OC1NC(=O)NC1O NNTWKXKLHMTGBU-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000006266 etherification reaction Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 2
- BXXLBMBLLVIOKO-UHFFFAOYSA-N octadecylcarbamic acid Chemical compound CCCCCCCCCCCCCCCCCCNC(O)=O BXXLBMBLLVIOKO-UHFFFAOYSA-N 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
- DOMQFIFVDIAOOT-ROUUACIJSA-N (2S,3R)-N-[4-(2,6-dimethoxyphenyl)-5-(5-methylpyridin-3-yl)-1,2,4-triazol-3-yl]-3-(5-methylpyrimidin-2-yl)butane-2-sulfonamide Chemical group COC1=C(C(=CC=C1)OC)N1C(=NN=C1C=1C=NC=C(C=1)C)NS(=O)(=O)[C@@H](C)[C@H](C)C1=NC=C(C=N1)C DOMQFIFVDIAOOT-ROUUACIJSA-N 0.000 description 1
- NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 description 1
- XPGGXNIIXHFGKQ-UHFFFAOYSA-N 2,3-dibromopropyl carbamate Chemical compound NC(=O)OCC(Br)CBr XPGGXNIIXHFGKQ-UHFFFAOYSA-N 0.000 description 1
- CVKGSDYWCFQOKU-UHFFFAOYSA-N 2-n-butyl-1,3,5-triazine-2,4,6-triamine Chemical compound CCCCNC1=NC(N)=NC(N)=N1 CVKGSDYWCFQOKU-UHFFFAOYSA-N 0.000 description 1
- RDXTVDMYEIHLBR-UHFFFAOYSA-N 3-dibutoxyphosphoryl-n-(hydroxymethyl)propanamide Chemical compound CCCCOP(=O)(OCCCC)CCC(=O)NCO RDXTVDMYEIHLBR-UHFFFAOYSA-N 0.000 description 1
- QKVNMODHEHRIMX-UHFFFAOYSA-N 3-dibutoxyphosphorylpropanamide Chemical compound CCCCOP(=O)(CCC(N)=O)OCCCC QKVNMODHEHRIMX-UHFFFAOYSA-N 0.000 description 1
- STZBZWOIMFISKW-UHFFFAOYSA-N 3-diethoxyphosphorylpropanamide Chemical compound CCOP(=O)(OCC)CCC(N)=O STZBZWOIMFISKW-UHFFFAOYSA-N 0.000 description 1
- XMHCHCAKHCZBHU-UHFFFAOYSA-N 3-dimethoxyphosphoryl-2-methylpropanamide Chemical compound COP(=O)(OC)CC(C(=O)N)C XMHCHCAKHCZBHU-UHFFFAOYSA-N 0.000 description 1
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- FVIGODVHAVLZOO-UHFFFAOYSA-N Dixanthogen Chemical compound CCOC(=S)SSC(=S)OCC FVIGODVHAVLZOO-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical class CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- NJYZCEFQAIUHSD-UHFFFAOYSA-N acetoguanamine Chemical compound CC1=NC(N)=NC(N)=N1 NJYZCEFQAIUHSD-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- MASBWURJQFFLOO-UHFFFAOYSA-N ammeline Chemical compound NC1=NC(N)=NC(O)=N1 MASBWURJQFFLOO-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical compound NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N methyl monoether Natural products COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- SXVDZIOMWSPFCO-UHFFFAOYSA-N methyl n,n-bis(hydroxymethyl)carbamate Chemical compound COC(=O)N(CO)CO SXVDZIOMWSPFCO-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- VCSJAJFSKJCWFG-UHFFFAOYSA-N triazin-5-amine Chemical class NC1=CN=NN=C1 VCSJAJFSKJCWFG-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 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
- D06M13/244—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 sulfur or phosphorus
- D06M13/282—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 sulfur or phosphorus with compounds containing phosphorus
- D06M13/288—Phosphonic or phosphonous acids or derivatives thereof
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1923668A CH501095A (de) | 1968-12-24 | 1968-12-24 | Verwendung von Phosphorverbindungen zum Flamm- und Knitterfestmachen von cellulosehaltigem Textilmaterial |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL33535A0 IL33535A0 (en) | 1970-02-19 |
| IL33535A true IL33535A (en) | 1973-02-28 |
Family
ID=4438192
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL33535A IL33535A (en) | 1968-12-24 | 1969-12-14 | Phosphorus compounds,their manufacture and their use for the flameproofing and crease-proofing of cellulose-containing fibre materials |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3679778A (de) |
| AT (1) | AT299891B (de) |
| BE (1) | BE743603A (de) |
| CH (2) | CH1923668A4 (de) |
| CS (1) | CS151536B2 (de) |
| DE (1) | DE1962644A1 (de) |
| FI (1) | FI48209C (de) |
| FR (1) | FR2027004A1 (de) |
| GB (1) | GB1266738A (de) |
| IL (1) | IL33535A (de) |
| NL (1) | NL6919298A (de) |
| NO (1) | NO127764B (de) |
| PL (1) | PL74668B1 (de) |
| SE (1) | SE366563B (de) |
| SU (1) | SU458137A3 (de) |
| YU (1) | YU33215B (de) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH524715A (de) * | 1970-06-11 | 1972-03-15 | Ciba Geigy Ag | Verfahren zum Flammfestmachen von cellulosehaltigen Textilien |
| DE2400393A1 (de) * | 1974-01-05 | 1975-07-24 | Henkel & Cie Gmbh | Dialkylphosphono-acetylharnstoffverbindungen, ihre herstellung sowie deren verwendung zum flammfestmachen |
| DE2402174A1 (de) * | 1974-01-17 | 1975-07-31 | Bayer Ag | Phosphorhaltige dicarbamidsaeurediester |
| US3903337A (en) * | 1974-04-04 | 1975-09-02 | Mitsui Toatsu Chemicals | Method for processing cellulose containing material to impart flame resistance |
| DE4208235A1 (de) * | 1992-03-14 | 1993-09-16 | Pfersee Chem Fab | Umsetzungsprodukte von phosphiten, chinonen und isocyanaten enthaltende zusammensetzungen |
| FR2795379B3 (fr) | 1999-06-23 | 2001-08-17 | Allibert Ind | Cockpit perfectionne de planche de bord |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH445126A (de) * | 1963-09-18 | 1967-10-15 | Ciba Geigy | Verfahren zur Herstellung Phosphor enthaltender Polymerisate |
-
1968
- 1968-12-24 CH CH1923668D patent/CH1923668A4/xx unknown
- 1968-12-24 CH CH1923668A patent/CH501095A/de not_active IP Right Cessation
-
1969
- 1969-11-27 SE SE16329/69A patent/SE366563B/xx unknown
- 1969-12-04 CS CS7980A patent/CS151536B2/cs unknown
- 1969-12-13 DE DE19691962644 patent/DE1962644A1/de active Pending
- 1969-12-14 IL IL33535A patent/IL33535A/en unknown
- 1969-12-16 US US885645A patent/US3679778A/en not_active Expired - Lifetime
- 1969-12-16 FR FR6943584A patent/FR2027004A1/fr not_active Withdrawn
- 1969-12-16 SU SU1386967A patent/SU458137A3/ru active
- 1969-12-17 GB GB1266738D patent/GB1266738A/en not_active Expired
- 1969-12-18 NO NO05002/69A patent/NO127764B/no unknown
- 1969-12-22 FI FI693713A patent/FI48209C/fi active
- 1969-12-22 YU YU3194/69A patent/YU33215B/xx unknown
- 1969-12-22 PL PL1969137756A patent/PL74668B1/pl unknown
- 1969-12-23 NL NL6919298A patent/NL6919298A/xx unknown
- 1969-12-23 BE BE743603D patent/BE743603A/xx unknown
- 1969-12-23 AT AT1200869A patent/AT299891B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2027004A1 (de) | 1970-09-25 |
| BE743603A (de) | 1970-06-23 |
| CH501095A (de) | 1970-07-15 |
| NL6919298A (de) | 1970-06-26 |
| SE366563B (de) | 1974-04-29 |
| YU33215B (en) | 1976-06-30 |
| CS151536B2 (de) | 1973-10-19 |
| AT299891B (de) | 1972-07-10 |
| US3679778A (en) | 1972-07-25 |
| DE1962644A1 (de) | 1970-07-09 |
| SU458137A3 (ru) | 1975-01-25 |
| NO127764B (de) | 1973-08-13 |
| IL33535A0 (en) | 1970-02-19 |
| FI48209B (de) | 1974-04-01 |
| YU319469A (en) | 1975-12-31 |
| CH1923668A4 (de) | 1970-07-15 |
| GB1266738A (de) | 1972-03-15 |
| FI48209C (fi) | 1974-07-10 |
| PL74668B1 (en) | 1974-12-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3755323A (en) | Triazinylaminoalkyl phosphonates | |
| US3878245A (en) | Process for the manufacture of phosphorus-containing condensation products, the products and their use as flameproofing agents | |
| US3956243A (en) | Process for flameproofing organic fibre material | |
| IL33535A (en) | Phosphorus compounds,their manufacture and their use for the flameproofing and crease-proofing of cellulose-containing fibre materials | |
| US3619113A (en) | Flame-retardant finish for cellulosic textile materials | |
| US4265945A (en) | Quaternary ureidomethyl phosphonium salts | |
| US3639539A (en) | Phosphorus-containing n n-dimethylolcarboxylic acid amides | |
| US3658952A (en) | Bis((dialkyl)phosphonoalkylamido) alkyls | |
| US3644083A (en) | Durable flame retardant finish for cellulosic textile materials | |
| US3669725A (en) | Flameproofing of polyester-cellulose fibre materials | |
| US4162279A (en) | Phosphonoxycarboxamides | |
| US4177300A (en) | Phosphonoxycarboxamide flame retarding compositions | |
| US3671611A (en) | Phosphorus acid esters | |
| US3864076A (en) | Process for flameproofing organic fibers with phosphorus-containing condensation products and the products produced | |
| IL32524A (en) | Phosphorus-containing reaction products of 1,3,5-triazine,process for their manufacture,and their use as flameproofing agents | |
| US3627767A (en) | Certain alkylene urea- or thiourea-containing phosphorus compounds | |
| US3887553A (en) | Process for the manufacture of phosphorus-containing condensation products | |
| US3627784A (en) | Heterocyclic phosphorus compounds and process for their manufacture | |
| CA1076596A (en) | Brominated phosphoramidates | |
| US3754981A (en) | Process for flameproofing cellulose-containing fibre material | |
| US4044006A (en) | Oxazine containing ureidoalkylphosphonates | |
| US3899549A (en) | Poly(dialkylphosphonoalkyl)carbamates | |
| US3721581A (en) | Process for flameproofing treatment | |
| US4059532A (en) | Phosphorus-containing reaction products useful as flameproofing agents | |
| US2822347A (en) | Method of preparing triazinyl compositions and products thereof |