US3870771A - Dialkyl alkyl and aromatic sulfonamidomethyl phosphonates - Google Patents
Dialkyl alkyl and aromatic sulfonamidomethyl phosphonates Download PDFInfo
- Publication number
- US3870771A US3870771A US239757A US23975772A US3870771A US 3870771 A US3870771 A US 3870771A US 239757 A US239757 A US 239757A US 23975772 A US23975772 A US 23975772A US 3870771 A US3870771 A US 3870771A
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- US
- United States
- Prior art keywords
- phenyl
- flame
- compounds
- polymers
- flame retardant
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 125000000217 alkyl group Chemical group 0.000 title abstract description 20
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 title 1
- 125000003118 aryl group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- 239000000463 material Substances 0.000 abstract description 32
- 239000004753 textile Substances 0.000 abstract description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 18
- 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 abstract description 17
- 239000003063 flame retardant Substances 0.000 abstract description 16
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 13
- 229920000642 polymer Polymers 0.000 abstract description 13
- 229920001577 copolymer Polymers 0.000 abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 abstract description 6
- 229910052736 halogen Chemical group 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000003340 retarding agent Substances 0.000 abstract description 3
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229920005989 resin Polymers 0.000 description 19
- 239000011347 resin Substances 0.000 description 19
- 238000000034 method Methods 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 229920001971 elastomer Polymers 0.000 description 12
- -1 ethylene, propylene, butene Chemical class 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
- 239000005060 rubber Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 239000000654 additive Substances 0.000 description 8
- 229920002678 cellulose Polymers 0.000 description 8
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- 239000000835 fiber Substances 0.000 description 7
- 229920001187 thermosetting polymer Polymers 0.000 description 7
- 239000004416 thermosoftening plastic Substances 0.000 description 7
- 230000000996 additive effect Effects 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
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- 239000004033 plastic Substances 0.000 description 6
- 239000011342 resin composition Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- 229920000297 Rayon Polymers 0.000 description 5
- 150000002367 halogens Chemical group 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
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- 239000011541 reaction mixture Substances 0.000 description 5
- 210000002268 wool Anatomy 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 4
- 229910000410 antimony oxide Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 4
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- 238000002360 preparation method Methods 0.000 description 4
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- 239000004743 Polypropylene Substances 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
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 229920000578 graft copolymer Polymers 0.000 description 3
- RBGJDWWIQLEBFF-UHFFFAOYSA-N n-(hydroxymethyl)-4-methylbenzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)NCO)C=C1 RBGJDWWIQLEBFF-UHFFFAOYSA-N 0.000 description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 3
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- 230000000979 retarding effect Effects 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 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
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-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
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical group O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 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
- 230000015556 catabolic process Effects 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 239000012757 flame retardant agent Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010348 incorporation Methods 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
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
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- 229920001021 polysulfide Polymers 0.000 description 2
- 239000005077 polysulfide Substances 0.000 description 2
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- 238000012545 processing Methods 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 description 1
- DAXJNUBSBFUTRP-RTQNCGMRSA-N (8r,9s,10r,13s,14s)-6-(hydroxymethyl)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthrene-3,17-dione Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(CO)C2=C1 DAXJNUBSBFUTRP-RTQNCGMRSA-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
- 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
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- DGXAGETVRDOQFP-UHFFFAOYSA-N 2,6-dihydroxybenzaldehyde Chemical compound OC1=CC=CC(O)=C1C=O DGXAGETVRDOQFP-UHFFFAOYSA-N 0.000 description 1
- CBECDWUDYQOTSW-UHFFFAOYSA-N 2-ethylbut-3-enal Chemical compound CCC(C=C)C=O CBECDWUDYQOTSW-UHFFFAOYSA-N 0.000 description 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- HAEFDDOAYBQRGK-UHFFFAOYSA-N 2-methylpropylphosphonic acid Chemical compound CC(C)CP(O)(O)=O HAEFDDOAYBQRGK-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- BBDKZWKEPDTENS-UHFFFAOYSA-N 4-Vinylcyclohexene Chemical compound C=CC1CCC=CC1 BBDKZWKEPDTENS-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
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- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- NANYUVCTNRQETR-UHFFFAOYSA-N n-(dimethoxyphosphorylmethyl)-4-methylbenzenesulfonamide Chemical compound COP(=O)(OC)CNS(=O)(=O)C1=CC=C(C)C=C1 NANYUVCTNRQETR-UHFFFAOYSA-N 0.000 description 1
- JTHNLKXLWOXOQK-UHFFFAOYSA-N n-propyl vinyl ketone Natural products CCCC(=O)C=C JTHNLKXLWOXOQK-UHFFFAOYSA-N 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Chemical compound CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- LIYKJALVRPGQTR-UHFFFAOYSA-M oxostibanylium;chloride Chemical compound [Cl-].[Sb+]=O LIYKJALVRPGQTR-UHFFFAOYSA-M 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 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
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KJWHEZXBZQXVSA-UHFFFAOYSA-N tris(prop-2-enyl) phosphite Chemical compound C=CCOP(OCC=C)OCC=C KJWHEZXBZQXVSA-UHFFFAOYSA-N 0.000 description 1
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 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
-
- 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
-
- 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
- C08K5/5373—Esters of phosphonic acids containing heterocyclic rings not representing cyclic esters of phosphonic acids
Definitions
- ABSTRACT New compounds are disclosed of the formula:
- R is selected from the group consisting of lower alkyl of 1-6 carbon atoms, phenyl and alkyl substituted phenyl and R is selected from the group consisting of phenyl, lower alkenyl and halogen substituted and unsubstituted lower alkyl of 1-6 carbon atoms.
- the compounds of this invention are useful as flame retarding agents for textile materials and in the production of polymers and copolymers which possess flame retardant properties 6 Claims, No Drawings DIALKYL ALKYL AND AROMATIC SULFONAMIDOMETHYL PHOSPHONATES FIELD OF INVENTION
- This invention relates to novel compounds of the formula wherein R is selected from the group consisting of lower alkyl of l-6 carbon atoms, phenyl and alkyl substituted phenyl and R is selected from the group consisting of phenyl, lower alkenyl and halogen substituted and unsubstituted lower alkyl of 1-6 carbon atoms.
- the invention includes methods of applying the above novel compounds to normally flammable textiles and thermoplastic or thermosetting resin compositions so as to render them flame retardant.
- Flame retardant textiles have been produced by depositing metal oxides, within or on the textile fibers, by the successive precipitation of ferric oxides and a mixture of tungstic acid and stannic oxide or by successive deposition of antimony trioxide and titanium dioxide.
- Such processes require plural treatment baths in which strongly acidic solutions are employed thus posing the problem of possible textile degradation.
- metal oxide coatings on textile materials create difficulties in subsequent dyeing processes which deleteriously affect the hand of the finished product.
- Another process involves the use of a single processing bath wherein a dispersion of a chlorinated hydrocarbon and finely divided antimony oxide is padded on the textile material.
- antimony oxide will react with hydrogen chloride, generated by degradation of the chlorinated hydrocarbon, to form antimony oxychloride which acts to suppress flame.
- This combination of a chlorinated hydrocarbon and finely divided antimony oxide are not acceptable finishes for closely woven textiles as they deleteriously affect the hand of the finished product.
- a further process for imparting flame resistance to cellulosic materials is by the esterification of the cellulose with diammonium hydrogen orthophosphate. Textile products so treated however are subjected to metathesis reaction with cations during washing, and must be regenerated by reacting the wash product with an ammonium chloride solution.
- thermoplastic resin compositions which are flame retardant are of considerable commercial importance.
- articles as castings I
- the present invention relates to a group of compounds which may be added to thermoplastic resins in relatively small amounts and still.produce'satisfactory flame retardant compositions which will not crystallize nor oil out of the resin after incorporation therein.
- R is selected from the group consisting of lower alkyl of 1-6 carbon atoms, phenyl and alkyl substituted phenyl and R is selected from the group consisting of phenyl, lower alkenyl and halogen substituted and unsubstituted lower alkyl of l-6 carbon atoms.
- novel compounds for imparting flame retardancy to textiles and thermoplastic or thermosetting resin materials, of the formula II R s OzNHCHgP (o R):
- R is selected from the group consisting of lower alkyl of l-6 carbon atoms, phenyl and alkyl substituted phenyl and R is selected from the group consisting of phenyl, lower alkenyl and halogen substituted and unsubstituted lower alkyl of l-6 carbon atoms. More specifically, the preferred compounds of the present invention include these compounds wherein R and R are lower alkyl of 1-6 carbon atoms.
- Illustrative examples of compounds of the present invention include, for instance, compounds of the general formula such as H on? s Oz-NII-CHz-P 0 GHQ-CH3);
- compositions of the present invention is accomplished by reacting an N- hydroxymethyl sulfonamide of the formula R SO NHCH OH with a trialkyl phosphite of the formula wherein R and R are as previously described in a suitable solvent. with an excess of the phosphite. or without solvent. Typically. the reaction is continued for about 1 to about l2 hours. Temperatures are generally about 50C to about 160C. Preferably reaction is continued from about 3 to about 6 hours at a temperature CHzBr 2
- One or more of the novel compounds of this invention may be applied to textile materials by conventional finishing techniques such as by thermal curing so as to incorporate into the textile a flame retardant amount thereof.
- the compounds of this invention have advantages over the flame retardant agents of the prior art in that they may be used on a variety of textile materials of different chemical composition, and they may be applied by a variety of methods. They may be applied to materials in either the fiber or fabric form to give flame retarding materials with minimum detectable physical changes in the quality or hand of the textile material.
- Cellulosic textile materials may be made flame retardantby way of a variety of methods.
- the cellulose products of this invention may be applied to cellulosic materials in several ways to give a durable flame retardant treatment.
- the products of this invention may be reacted with formaldehyde to give N- hydroxymethyl derivatives which can react with cellulosic materials in a known manner.
- aqueous mixtures of the products with formaldehyde, urea, trimethylol melamine orother known cellulose cross linking agents may be applied to a cellulose substrate with the acid of an acidic catalyst by pad dry process.
- N-hydroxymethyl derivative of the products of this invention prepared by the condensation of the products with formaldehyde, are mixedin an aqueous medium with trimethylol melamine and a Lewis acid catalyst such as NH,Cl or Zn(NO;,) -6H O.
- the cellulosic material is immersed in a aqueous solution of the methylol derivative, trimethylol melamine, and Zn(NO '6H O and squeezed on a two roll padder to 70-90 percent wet weight pick-up.
- the material is dried at 220-270F for 1-3 minutes and cured at 300-370F for l-6 minutes in a circulating air oven.
- the samples are then washed in hot water and dried.
- the finishedsamples have a flame retardant add-on of about 5 to about 40 percent and preferably about 10 to about 25 percent by weight.
- the flame retardant agents of this invention may be applied to various textiles such as cellulosic materials, proteinaceous materials and blends of cellulosic or proteinaceous materials.
- cellulosic materials applicant intends to embrace cotton, rayon, paper, regenerated cellulose and cellulose derivatives which retain a cellulose backbone of at least one hydroxy substituent per repeating glucose unit.
- proteinaceous material applicant intends to embrace those textile materials comprising the functional groups of proteins such as the various animal wools, hairs and furs.
- the flame retardant compounds or additives of the invention may be incorporated into thermoplastic or thermosetting resin compositions by any known method.
- the flame retardant additive may be added to the resin by milling the resin and the additive on, for example, a two-roll mill. or in a Banbury mixer etc., or it may be added by molding or extruding the additive and resin simultaneously, or by merely blending it with the resin in powder form and thereafter forming the desired article. Additionally, the flame-retardant may be added during the resin manufacture, i.e., during the polymer-- have been found sufficient.
- thermoplastic resin embraced within the scope of this invention include the homopolymers and copolymers of unsaturated aliphatic, alicyclic, and aromatic hydrocarbons. Suitable monomers are ethylene, propylene, butene, pentene, hexene, heptene, octene, Z-methylpropene-l, 3-methylbutene-l, 4-methylpentene-l, 4-methylhexene-l,5-methylhexene-l, bicyclo- (2.2.l)-2-heptene, butadiene, pentadiene, hexadiene, isoprene, 2,3-dimethylbutadiene-1,3, 2-methylpentadien-l,3 4-vinylcyclohexene, vinylcyclohexene, cyclopentadiene, styrene and methylstyrene, and the like.
- polymers in addition to the above-described olefin polymers that are useful in the invention include polyindene, indenecoumarone resins; polymers of acrylate esters and polymers of methacrylate esters, acrylate and methacrylate resins such as ethyl acrylate, nbutyl methacrylate, isobutyl methacrylate, ethyl methacrylate and methyl methacrylate; alkyd resins and paint vehicles, such as bodied linseed oil; cellulose derivatives such as cellulose acetate, cellulose'acetate butyrate, cellulose nitrate, ethyl cellulose, hydroxyethyl cellulose, methyl cellulose and sodium carboxymethyl celurated polyesters of dibasic acids and dihydroxy compounds, and polyester elastomer and resorcinol resins such as resorcinol-formaldehyde, resorcinol-furfural, resorcinol-
- the polymers ofthe invention can be in various physical forms, such as shaped articles, for example, moldings, sheets, rods, and the like; fibers, coatings, films and fabrics, and the like.
- the compounds of this invention have been found to have particular utility in ABS resins and in elastomeric materials such as acrylic rubber; acrylonitrilebutadiene styrene terpolymers; butadieneacrylonitrile copolymers; butyl rubber; chlorinated rubbers, e.g., polyvinyl chloride resins, chloroprene rubber, chlorosulfonated polyethylene; ethylene polymers, e.g., ethylene-propylene copolymers, ethylene-propylene terpolymers; fluorinated rubbers, butadiene rubbers, e.g., styrene-butadiene rubber, isobutylene polymers, polybutadiene polymers, polyisobutylene rubbers, polyisoprene rubbers; polysulfide rubbers; silicon rubbers; urethane rubbers; high styrene resins latices, high styrene resins, vinyl resins;
- ASTM Test D2863-70 used in accordance with the following examples, generally provides for the comparison of relative flammability of self-supporting plastics by measuring the minimum concentration of oxygen in a slowly rising mixture of oxygen and nitrogen that will support combustion.
- the procedure encompasses supporting cylindrical test specimens 70-150 mm in length X 8.0 mm in diameter vertically in a glass tube fitted with controlled upward oxygen/nitrogen gas flow. The top of the specimen is ignited and oxygen flow is adjusted until it reaches that minimum rate at which the specimen is extinguished before burning 3 minutes or 50 mm whichever happens first.
- the oxygen index(n) is then calculated as follows:
- O is the volumetric flow of oxygen, at the minimal rate and N is the corresponding volumetric flow rate of nitrogen.
- a modification of ASTM Test D635-68 used in accordance with the following examples, generally provides for the comparison of burning rates, selfextinguishment and non-burning characteristics of plastics in the form of sheets, bars, plates or panels.
- the procedure encompasses preparing 150200 mm X 8 mm cylindrical plastic test samples with an without the subject flame retardant additive. Each sample is marked at points 1 inch and 4 inches from its end and held, marked end in the flame, at a 45 angle in a controlled burner flame (1 inch flame length) for two 30 second attempts. The movement of the flame up the length of the sample through the two points is measured for rate of burning, non-burning or selfextinguishing characteristics.
- a sample is rated SE(selfextinguishing) if the flame burns through the first point but extinguishes before reaching the second point.
- a sample is rated NB(non-burning) if, upon ignition it does not burn to the first point.
- the vertical Char Test used in accordance with the following examples, generally provides for the comparison of relative flammability of 2% inch X l inch fabric test specimens when exposed to a controlled burner flame, under controlled conditions, for periods of 12.0 and 3.0 seconds. Charred specimens are thereafter subjected to controlled tearing tests, using tabulated weights, to determine the average tear length as representing the char length of the fabric. in addition, samples which are wholly consumed by the flame are rated (B) and samples which do not burn are rated (NB). For comparison purposes, it should be noted that untreated samples of the fabrics used in the examples of this case would be consumed for this test.
- reaction solution was heated at reflux for 15 hours and then cooled to room temperature. On standing, colorless crystals separated from the solution. The crystals were filtered off the solution and dried resulting in a yield of 179g. A further concentration of the mother liquor, after filtration, yielded a further 40g. ofcrystalline material. Total yield of product was 219g. of a colorless cyrstallinc solid analyzed as essentially pure N-dimethyl phosphonomethyl-p-toluene sulfonamide.
- EXAMPLE VI A padding solution was prepared by mixing N- dimethylphosphonomethyl-p-toluenesulfonamide. (400g) with 60.0g of 40 percent formalin solution of a pH of 9-10 and stirring overnight. The pH was adjusted to 7.0 with hydrochloric acid and 23g. of a 50 l was added to the hydroxymethyl compound 201g. percentsolutipln oga ntijejthdylolated melamine and g of (0 1 mole) in a round bottomed flask and warmed to ammonium c on e a e d It b t 125C f i h Th 6.0 oz. sq. yd.
- wool textile material was padded f d I b or a 3 through the above mixture and the excess squeezed out f f gf, en fi g by means ofa two roll laboratory padder at 60 lb. gauge 34 s fi 1 f f g pressure to a wet pickup ofabout 130 percent.
- the texuc i or ebb lqul w Ose h S tile'material was dried at about 250F for about 2 mineonflrmed by mtrared and nuclear magnetic resonance 0 I I utes, and cured at about 350 F for about 4 minutes in spectroscopy and elemental analysis to be that of the claimed mduct a circulating an oven.
- N-Hydroxymethyl-p-toluene sulfonamide was pre- Cloth 9 qy was "h with the abofle pared as in Example I.
- Example VI wlth 20.1g. (0.1 mole) was then added to 27g. (0.! mole) of results 88 lndlcaled Table ltris-Z-chloroethyl phosphite and warmed to 120C.
- the reaction mixture was held at 120C for two hours and EXAMPLE VIII then stripped at 100C and 0.5 mm Hg to give the de- 6.0 02. sq. yd. wool textile material was treated and sired product.
- a viscous yellow liquid was obtained in quantitative yield. with elemental ples thereof in a controlled burner flame for 2 seconds then removing and observing for self-extinguishment (SE).
- SE self-extinguishment
- EXAMPLE X 30 parts of N-dimethyl phosphonomethyl-p-toluene sulfonamide was mixed with 70 parts of polypropylene and dry blended for about minutes. This composition was then heated to a melt and mixed in the molten state for about 15 minutes. The composition was allowed to cool and solidify after which it was cut into small pieces. These small composition pieces were then 2.
- a compound of claim 1 of the formula II 5 om-@-sogNucul 1 001m;
- lower alkyl of l-6 carbon atoms phenyl and alkyl substituted phenyl and R is selected from the group consisting of phenyl, lower alkenyl and halogen substituted and unsubstituted lower alkyl of 1-6 carbon atoms.
- a compound of claim 1 of the formula 1.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Textile Engineering (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Fireproofing Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Priority Applications (12)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US239757A US3870771A (en) | 1972-03-30 | 1972-03-30 | Dialkyl alkyl and aromatic sulfonamidomethyl phosphonates |
US00239799A US3812218A (en) | 1972-03-30 | 1972-03-30 | Diakyl alkyl and cyclic phosporamidomethyl phosphonates |
GB1390773A GB1418775A (en) | 1972-03-30 | 1973-03-22 | Phosphonate ester derivatives having flame-retardant properties |
FR7310953A FR2187802B1 (fr) | 1972-03-30 | 1973-03-27 | |
BE129396A BE797476A (fr) | 1972-03-30 | 1973-03-28 | Nouveaux adjuvants retardant l'inflammation contenant du phospore |
CA167,352A CA1004227A (en) | 1972-03-30 | 1973-03-28 | Phosphorus containing fire retardant additives |
DE2315493A DE2315493A1 (de) | 1972-03-30 | 1973-03-28 | Phosphonsaeureverbindungen, verfahren zu deren herstellung und deren verwendung als flammschutzmittel fuer textilien und thermoplastische, hitzehaertbare oder elastomere kunstharze |
JP48036575A JPS4916735A (fr) | 1972-03-30 | 1973-03-30 | |
IT22420/73A IT982664B (it) | 1972-03-30 | 1973-03-30 | Additivi anti incendio contenenti fosforo |
NL7304503A NL7304503A (fr) | 1972-03-30 | 1973-03-30 | |
FR7333434A FR2196341B1 (fr) | 1972-03-30 | 1973-09-18 | |
US05/537,721 US3959551A (en) | 1972-03-30 | 1974-12-31 | Dialkyl alkyl and aromatic sulfonamidomethyl phosphonates |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US239757A US3870771A (en) | 1972-03-30 | 1972-03-30 | Dialkyl alkyl and aromatic sulfonamidomethyl phosphonates |
US00239799A US3812218A (en) | 1972-03-30 | 1972-03-30 | Diakyl alkyl and cyclic phosporamidomethyl phosphonates |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US05/537,721 Division US3959551A (en) | 1972-03-30 | 1974-12-31 | Dialkyl alkyl and aromatic sulfonamidomethyl phosphonates |
Publications (1)
Publication Number | Publication Date |
---|---|
US3870771A true US3870771A (en) | 1975-03-11 |
Family
ID=26932840
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US239757A Expired - Lifetime US3870771A (en) | 1972-03-30 | 1972-03-30 | Dialkyl alkyl and aromatic sulfonamidomethyl phosphonates |
US00239799A Expired - Lifetime US3812218A (en) | 1972-03-30 | 1972-03-30 | Diakyl alkyl and cyclic phosporamidomethyl phosphonates |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US00239799A Expired - Lifetime US3812218A (en) | 1972-03-30 | 1972-03-30 | Diakyl alkyl and cyclic phosporamidomethyl phosphonates |
Country Status (9)
Country | Link |
---|---|
US (2) | US3870771A (fr) |
JP (1) | JPS4916735A (fr) |
BE (1) | BE797476A (fr) |
CA (1) | CA1004227A (fr) |
DE (1) | DE2315493A1 (fr) |
FR (2) | FR2187802B1 (fr) |
GB (1) | GB1418775A (fr) |
IT (1) | IT982664B (fr) |
NL (1) | NL7304503A (fr) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3959551A (en) * | 1972-03-30 | 1976-05-25 | Hooker Chemicals & Plastics Corporation | Dialkyl alkyl and aromatic sulfonamidomethyl phosphonates |
US3970586A (en) * | 1974-05-18 | 1976-07-20 | Bayer Aktiengesellschaft | Perfluoroalkane sulfonamido-alkane phosphonic and phosphonic acid derivatives |
US4031170A (en) * | 1973-08-06 | 1977-06-21 | Monsanto Company | Phosphorus compounds |
US4032601A (en) * | 1973-08-06 | 1977-06-28 | Monsanto Company | Process for the production of sulfonamide phosphonates |
US4202706A (en) * | 1979-03-12 | 1980-05-13 | Minnesota Mining And Manufacturing Company | Corrosion resistance treatment of aluminum with N-alkyl-fluoroaliphaticsulfonamidophosphonic acids and salts thereof |
US6472406B1 (en) | 1999-07-06 | 2002-10-29 | Methylgene, Inc. | Sulfonamidomethyl phosphonate inhibitors of beta-lactamase |
US20040082546A1 (en) * | 1999-07-06 | 2004-04-29 | Methylgene, Inc. | Novel Inhibitors of beta-lactamase |
US20050043276A1 (en) * | 1999-07-06 | 2005-02-24 | Methylgene, Inc. | Novel inhibitors of beta-lactamase |
US20050054553A1 (en) * | 2003-06-27 | 2005-03-10 | The Procter & Gamble Company | Liquid fabric softening compositions comprising flame retardant |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2555452A1 (de) * | 1974-12-18 | 1976-06-24 | Ciba Geigy Ag | Flammschutzmittel fuer kunststoffe |
JPS5610500A (en) * | 1979-07-09 | 1981-02-02 | Hiroyasu Hanawa | Automatic punchinggmachine |
US6221939B1 (en) | 1998-08-31 | 2001-04-24 | General Electric Company | Flame retardant resin compositions containing phosphoramides, and method for making |
US6433046B1 (en) | 1999-01-22 | 2002-08-13 | General Electric Company | Flame retardant resin compositions containing phosphoramides, and method of making |
US6569929B2 (en) | 1999-01-22 | 2003-05-27 | General Electric Company | Method to prepare phosphoramides, and resin compositions containing them |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2635112A (en) * | 1949-07-28 | 1953-04-14 | Research Corp | Process for producing aminomethylphosphonic acid compounds |
-
1972
- 1972-03-30 US US239757A patent/US3870771A/en not_active Expired - Lifetime
- 1972-03-30 US US00239799A patent/US3812218A/en not_active Expired - Lifetime
-
1973
- 1973-03-22 GB GB1390773A patent/GB1418775A/en not_active Expired
- 1973-03-27 FR FR7310953A patent/FR2187802B1/fr not_active Expired
- 1973-03-28 BE BE129396A patent/BE797476A/fr unknown
- 1973-03-28 DE DE2315493A patent/DE2315493A1/de active Pending
- 1973-03-28 CA CA167,352A patent/CA1004227A/en not_active Expired
- 1973-03-30 NL NL7304503A patent/NL7304503A/xx unknown
- 1973-03-30 JP JP48036575A patent/JPS4916735A/ja active Pending
- 1973-03-30 IT IT22420/73A patent/IT982664B/it active
- 1973-09-18 FR FR7333434A patent/FR2196341B1/fr not_active Expired
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2635112A (en) * | 1949-07-28 | 1953-04-14 | Research Corp | Process for producing aminomethylphosphonic acid compounds |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3959551A (en) * | 1972-03-30 | 1976-05-25 | Hooker Chemicals & Plastics Corporation | Dialkyl alkyl and aromatic sulfonamidomethyl phosphonates |
US4031170A (en) * | 1973-08-06 | 1977-06-21 | Monsanto Company | Phosphorus compounds |
US4032601A (en) * | 1973-08-06 | 1977-06-28 | Monsanto Company | Process for the production of sulfonamide phosphonates |
US3970586A (en) * | 1974-05-18 | 1976-07-20 | Bayer Aktiengesellschaft | Perfluoroalkane sulfonamido-alkane phosphonic and phosphonic acid derivatives |
US4202706A (en) * | 1979-03-12 | 1980-05-13 | Minnesota Mining And Manufacturing Company | Corrosion resistance treatment of aluminum with N-alkyl-fluoroaliphaticsulfonamidophosphonic acids and salts thereof |
US20040082546A1 (en) * | 1999-07-06 | 2004-04-29 | Methylgene, Inc. | Novel Inhibitors of beta-lactamase |
US6472406B1 (en) | 1999-07-06 | 2002-10-29 | Methylgene, Inc. | Sulfonamidomethyl phosphonate inhibitors of beta-lactamase |
US20050043276A1 (en) * | 1999-07-06 | 2005-02-24 | Methylgene, Inc. | Novel inhibitors of beta-lactamase |
US6884791B2 (en) | 1999-07-06 | 2005-04-26 | Methylgene, Inc. | Inhibitors of β-lactamase |
US6921756B2 (en) | 1999-07-06 | 2005-07-26 | Methylgene, Inc. | Inhibitors of β-lactamase |
US7030103B2 (en) | 1999-07-06 | 2006-04-18 | Methylgene, Inc. | Sulfonamidomethyl phosphonate inhibitors of β-lactamase |
US7259172B2 (en) | 1999-07-06 | 2007-08-21 | Methylgene Inc. | Inhibitors of β-lactamase |
US20070293675A1 (en) * | 1999-07-06 | 2007-12-20 | Methylgene, Inc. | Novel Inhibitors Of Beta-Lactamase |
US7514556B2 (en) | 1999-07-06 | 2009-04-07 | Methylgene Inc. | Inhibitors of β-lactamase |
US20050054553A1 (en) * | 2003-06-27 | 2005-03-10 | The Procter & Gamble Company | Liquid fabric softening compositions comprising flame retardant |
Also Published As
Publication number | Publication date |
---|---|
DE2315493A1 (de) | 1973-10-04 |
IT982664B (it) | 1974-10-21 |
CA1004227A (en) | 1977-01-25 |
NL7304503A (fr) | 1973-10-02 |
GB1418775A (en) | 1975-12-24 |
FR2196341A1 (fr) | 1974-03-15 |
FR2196341B1 (fr) | 1977-03-11 |
FR2187802B1 (fr) | 1976-06-11 |
JPS4916735A (fr) | 1974-02-14 |
BE797476A (fr) | 1973-09-28 |
US3812218A (en) | 1974-05-21 |
FR2187802A1 (fr) | 1974-01-18 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: OCCIDENTAL CHEMICAL CORPORATION Free format text: CHANGE OF NAME;ASSIGNOR:HOOKER CHEMICALS & PLASTICS CORP.;REEL/FRAME:004109/0487 Effective date: 19820330 |