DE2316043A1 - Phosphonsaeureverbindungen, verfahren zu deren herstellung und deren verwendung als flammschutzmittel fuer textilien und thermoplastische, hitzehaertbare oder elastomere kunstharze - Google Patents
Phosphonsaeureverbindungen, verfahren zu deren herstellung und deren verwendung als flammschutzmittel fuer textilien und thermoplastische, hitzehaertbare oder elastomere kunstharzeInfo
- Publication number
- DE2316043A1 DE2316043A1 DE2316043A DE2316043A DE2316043A1 DE 2316043 A1 DE2316043 A1 DE 2316043A1 DE 2316043 A DE2316043 A DE 2316043A DE 2316043 A DE2316043 A DE 2316043A DE 2316043 A1 DE2316043 A1 DE 2316043A1
- Authority
- DE
- Germany
- Prior art keywords
- och
- cnhch
- mol
- flame
- textiles
- 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.)
- Pending
Links
- 239000004753 textile Substances 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 10
- 229920001169 thermoplastic Polymers 0.000 title claims description 9
- 239000004416 thermosoftening plastic Substances 0.000 title claims description 8
- 150000003009 phosphonic acids Chemical class 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 19
- 229920005989 resin Polymers 0.000 title description 11
- 239000011347 resin Substances 0.000 title description 11
- 239000011814 protection agent Substances 0.000 title 1
- 239000003063 flame retardant Substances 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 26
- -1 phenoxymethylene group Chemical group 0.000 claims description 22
- 229920003002 synthetic resin Polymers 0.000 claims description 17
- 239000000057 synthetic resin Substances 0.000 claims description 17
- 229920001971 elastomer Polymers 0.000 claims description 15
- 239000000835 fiber Substances 0.000 claims description 14
- 229920002678 cellulose Polymers 0.000 claims description 12
- 239000001913 cellulose Substances 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 7
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 6
- 229920001187 thermosetting polymer Polymers 0.000 claims description 5
- 239000000806 elastomer Substances 0.000 claims description 4
- 108090000623 proteins and genes Proteins 0.000 claims description 4
- 102000004169 proteins and genes Human genes 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical compound NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000012360 testing method Methods 0.000 description 29
- 239000000243 solution Substances 0.000 description 21
- 239000000203 mixture Substances 0.000 description 19
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 18
- 238000005406 washing Methods 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 17
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 15
- 239000007788 liquid Substances 0.000 description 14
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
- 238000000921 elemental analysis Methods 0.000 description 12
- 239000004744 fabric Substances 0.000 description 12
- 238000002329 infrared spectrum Methods 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 11
- 239000005060 rubber Substances 0.000 description 11
- 238000010521 absorption reaction Methods 0.000 description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 10
- 239000001301 oxygen Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 239000003599 detergent Substances 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 8
- 210000002268 wool Anatomy 0.000 description 8
- 229920000742 Cotton Polymers 0.000 description 7
- 239000004793 Polystyrene Substances 0.000 description 7
- 239000003822 epoxy resin Substances 0.000 description 7
- 229920000647 polyepoxide Polymers 0.000 description 7
- 229920002223 polystyrene Polymers 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 6
- 235000019270 ammonium chloride Nutrition 0.000 description 6
- 229920003023 plastic Polymers 0.000 description 6
- 239000004033 plastic Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 229920000297 Rayon Polymers 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 239000002964 rayon Substances 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 239000004677 Nylon Substances 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 4
- 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 description 4
- 229910000410 antimony oxide Inorganic materials 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 229920001778 nylon Polymers 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 229920002857 polybutadiene Polymers 0.000 description 4
- 229920000573 polyethylene Polymers 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000003039 volatile agent Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 3
- USDJGQLNFPZEON-UHFFFAOYSA-N [[4,6-bis(hydroxymethylamino)-1,3,5-triazin-2-yl]amino]methanol Chemical compound OCNC1=NC(NCO)=NC(NCO)=N1 USDJGQLNFPZEON-UHFFFAOYSA-N 0.000 description 3
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 3
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 3
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229920000578 graft copolymer Polymers 0.000 description 3
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 3
- 229920001084 poly(chloroprene) Polymers 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- XIOUDVJTOYVRTB-UHFFFAOYSA-N 1-(1-adamantyl)-3-aminothiourea Chemical compound C1C(C2)CC3CC2CC1(NC(=S)NN)C3 XIOUDVJTOYVRTB-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- GQVPWBWFLFFKDV-UHFFFAOYSA-N 3-bromo-n-(hydroxymethyl)benzamide Chemical compound OCNC(=O)C1=CC=CC(Br)=C1 GQVPWBWFLFFKDV-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229920000459 Nitrile rubber Polymers 0.000 description 2
- 229920002367 Polyisobutene Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 2
- 229920005549 butyl rubber Polymers 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- MHRYJVFGVZWKLA-UHFFFAOYSA-N n-(dimethoxyphosphorylmethyl)butanamide Chemical compound CCCC(=O)NCP(=O)(OC)OC MHRYJVFGVZWKLA-UHFFFAOYSA-N 0.000 description 2
- CYABWYAZPRBOEJ-UHFFFAOYSA-N n-(dimethoxyphosphorylmethyl)formamide Chemical compound COP(=O)(OC)CNC=O CYABWYAZPRBOEJ-UHFFFAOYSA-N 0.000 description 2
- XXBWKSWPAMJCSC-UHFFFAOYSA-N n-(hydroxymethyl)-2-phenylacetamide Chemical compound OCNC(=O)CC1=CC=CC=C1 XXBWKSWPAMJCSC-UHFFFAOYSA-N 0.000 description 2
- YPWZBEMOZPLXFM-UHFFFAOYSA-N n-(hydroxymethyl)-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NCO)C=C1 YPWZBEMOZPLXFM-UHFFFAOYSA-N 0.000 description 2
- FTRXAEVXVNZEMP-UHFFFAOYSA-N n-(hydroxymethyl)butanamide Chemical compound CCCC(=O)NCO FTRXAEVXVNZEMP-UHFFFAOYSA-N 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
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- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920001021 polysulfide Polymers 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 2
- KJWHEZXBZQXVSA-UHFFFAOYSA-N tris(prop-2-enyl) phosphite Chemical compound C=CCOP(OCC=C)OCC=C KJWHEZXBZQXVSA-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
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- DMYOHQBLOZMDLP-UHFFFAOYSA-N 1-[2-(2-hydroxy-3-piperidin-1-ylpropoxy)phenyl]-3-phenylpropan-1-one Chemical compound C1CCCCN1CC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 DMYOHQBLOZMDLP-UHFFFAOYSA-N 0.000 description 1
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 1
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- FRIWNRRDSXIHFO-UHFFFAOYSA-N 2,4-dichloro-n-(dimethoxyphosphorylmethyl)benzamide Chemical compound COP(=O)(OC)CNC(=O)C1=CC=C(Cl)C=C1Cl FRIWNRRDSXIHFO-UHFFFAOYSA-N 0.000 description 1
- CDWMMXDWPISBSI-UHFFFAOYSA-N 2,4-dichloro-n-(hydroxymethyl)benzamide Chemical compound OCNC(=O)C1=CC=C(Cl)C=C1Cl CDWMMXDWPISBSI-UHFFFAOYSA-N 0.000 description 1
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- IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-UHFFFAOYSA-N 0.000 description 1
- IDMCOIZLZMSKJZ-UHFFFAOYSA-N 2-diethoxyphosphoryl-n-(hydroxymethyl)acetamide Chemical compound CCOP(=O)(OCC)CC(=O)NCO IDMCOIZLZMSKJZ-UHFFFAOYSA-N 0.000 description 1
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
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- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 239000001859 Ethyl hydroxyethyl cellulose Substances 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- HYBBIBNJHNGZAN-UHFFFAOYSA-N Furaldehyde Natural products O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
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- 239000000155 melt Substances 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
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- LBYAIUISWPKTQG-UHFFFAOYSA-N n,n'-bis(hydroxymethyl)butanediamide Chemical compound OCNC(=O)CCC(=O)NCO LBYAIUISWPKTQG-UHFFFAOYSA-N 0.000 description 1
- KVSSQGZBROCKQT-UHFFFAOYSA-N n-(diphenoxyphosphorylmethyl)-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NCP(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 KVSSQGZBROCKQT-UHFFFAOYSA-N 0.000 description 1
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- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
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- 229910052698 phosphorus Inorganic materials 0.000 description 1
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- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
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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
-
- 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
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
-
- 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
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K5/5333—Esters of phosphonic acids
- C08K5/5353—Esters of phosphonic acids containing also nitrogen
-
- 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
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/92—Fire or heat protection feature
- Y10S428/921—Fire or flameproofing
-
- 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
- Y10S521/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S521/906—Polyurethane cellular product containing unreacted flame-retardant material
-
- 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
- Y10S521/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S521/907—Nonurethane flameproofed cellular product
-
- 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
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/2938—Coating on discrete and individual rods, strands or filaments
-
- 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
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/2631—Coating or impregnation provides heat or fire protection
- Y10T442/2672—Phosphorus containing
- Y10T442/268—Phosphorus and nitrogen containing compound
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Fireproofing Substances (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05239793 US3823206A (en) | 1972-03-30 | 1972-03-30 | N-phosphonomethyl amides |
| US05239784 US3803269A (en) | 1972-03-30 | 1972-03-30 | Dialkyl aromatic amidomethyl phosphonates |
| US37482673 US3901650A (en) | 1972-03-30 | 1973-06-29 | Textile flame retardants |
| US05393868 US3895161A (en) | 1972-03-30 | 1973-09-04 | Flame retardant materials |
| US05/531,646 US3935162A (en) | 1972-03-30 | 1974-12-11 | Dialkyl aromatic amidomethyl phosphonate flame retardants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2316043A1 true DE2316043A1 (de) | 1973-10-18 |
Family
ID=27540127
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2316043A Pending DE2316043A1 (de) | 1972-03-30 | 1973-03-30 | Phosphonsaeureverbindungen, verfahren zu deren herstellung und deren verwendung als flammschutzmittel fuer textilien und thermoplastische, hitzehaertbare oder elastomere kunstharze |
Country Status (8)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3803269A (en) * | 1972-03-30 | 1974-04-09 | Hooker Chemical Corp | Dialkyl aromatic amidomethyl phosphonates |
| US3954860A (en) * | 1973-08-06 | 1976-05-04 | Monsanto Company | Phosphorous compounds |
| IT1019221B (it) * | 1973-09-11 | 1977-11-10 | Sumitomo Bakelite Co | Composizione di resina termoindu rente inifiammabile e procedi mento per produrla |
| DE2351295A1 (de) * | 1973-10-12 | 1975-04-24 | Bayer Ag | N,n-bis-(phosphonomethyl)-acrylamide |
| US4113671A (en) * | 1974-10-17 | 1978-09-12 | Societe Nationale Des Poudres Et Explosifs | Carbamate-phosphonates as flame-proofing agents in polyurethane foam |
| US4003862A (en) * | 1975-10-23 | 1977-01-18 | Michigan Chemical Corporation | N-substituted tetrahalophthalimides as flame retardants |
| IT1060705B (it) * | 1976-05-28 | 1982-08-20 | Montedison Spa | Composizioni polimeriche autoestinguenti |
| GB8321643D0 (en) * | 1983-08-11 | 1983-09-14 | Ici Plc | Fire retardant polyamide compositions |
| US4753972A (en) * | 1985-12-16 | 1988-06-28 | Ciba-Geigy Corporation | Substituted aminoxyethyl phosphonates |
| GB8617861D0 (en) * | 1986-07-22 | 1986-08-28 | Ciba Geigy Ag | Flame retardant compositions |
| FR2818985B1 (fr) * | 2000-12-29 | 2004-02-20 | Nylstar Sa | Procede de fabrication de compositions stabilisees a base de polyamide |
| ITMI20020734A1 (it) * | 2002-04-08 | 2003-10-08 | Eurotecnica Dev & Licensing S | Glicoli e plioli aromatici procedimento di preparazione e loro uso quali monomeri |
| US8247077B2 (en) * | 2008-04-10 | 2012-08-21 | Ansell Protective Solutions Ab | Chemical protective garment with added flash fire protection |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2666078A (en) * | 1952-05-16 | 1954-01-12 | Arvey Corp | Bis-trichloroethyl benzene phosphonate |
| US2867547A (en) * | 1953-09-22 | 1959-01-06 | Victor Chemical Works | Method of flameproofing fibers, compositions used therein and the resulting products |
| US2803562A (en) * | 1955-05-26 | 1957-08-20 | Dow Chemical Co | Treatment of cellulosic materials to impart flame resistance thereto |
| GB1197591A (en) * | 1967-07-28 | 1970-07-08 | Ciba Ltd | Phosphorus-Containing Reaction Products, processes for their production and their Application |
| US3803269A (en) * | 1972-03-30 | 1974-04-09 | Hooker Chemical Corp | Dialkyl aromatic amidomethyl phosphonates |
-
1972
- 1972-03-30 US US05239784 patent/US3803269A/en not_active Expired - Lifetime
- 1972-03-30 US US05239793 patent/US3823206A/en not_active Expired - Lifetime
-
1973
- 1973-03-26 JP JP3443173A patent/JPS499090A/ja active Pending
- 1973-03-28 CA CA167,354A patent/CA1006171A/en not_active Expired
- 1973-03-29 GB GB1518573A patent/GB1432013A/en not_active Expired
- 1973-03-30 NL NL7304500A patent/NL7304500A/xx unknown
- 1973-03-30 BE BE129535A patent/BE797632A/xx unknown
- 1973-03-30 FR FR7311582A patent/FR2178236B1/fr not_active Expired
- 1973-03-30 DE DE2316043A patent/DE2316043A1/de active Pending
- 1973-06-29 US US37482673 patent/US3901650A/en not_active Expired - Lifetime
- 1973-09-04 US US05393868 patent/US3895161A/en not_active Expired - Lifetime
-
1974
- 1974-12-11 US US05/531,646 patent/US3935162A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US3895161A (en) | 1975-07-15 |
| JPS499090A (US07993877-20110809-P00003.png) | 1974-01-26 |
| FR2178236A1 (US07993877-20110809-P00003.png) | 1973-11-09 |
| FR2178236B1 (US07993877-20110809-P00003.png) | 1976-09-10 |
| GB1432013A (en) | 1976-04-14 |
| US3935162A (en) | 1976-01-27 |
| BE797632A (fr) | 1973-10-01 |
| US3803269A (en) | 1974-04-09 |
| US3823206A (en) | 1974-07-09 |
| CA1006171A (en) | 1977-03-01 |
| US3901650A (en) | 1975-08-26 |
| NL7304500A (US07993877-20110809-P00003.png) | 1973-10-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |