CA2537157C - Flame retardant compositions - Google Patents
Flame retardant compositions Download PDFInfo
- Publication number
- CA2537157C CA2537157C CA2537157A CA2537157A CA2537157C CA 2537157 C CA2537157 C CA 2537157C CA 2537157 A CA2537157 A CA 2537157A CA 2537157 A CA2537157 A CA 2537157A CA 2537157 C CA2537157 C CA 2537157C
- Authority
- CA
- Canada
- Prior art keywords
- compound
- compounds
- flame retardant
- tert
- bis
- 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
Links
- 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 title claims abstract description 118
- 239000003063 flame retardant Substances 0.000 title claims abstract description 110
- 239000000203 mixture Substances 0.000 title claims abstract description 87
- 150000001875 compounds Chemical class 0.000 claims abstract description 171
- 239000000758 substrate Substances 0.000 claims abstract description 79
- -1 phosphorus compound Chemical class 0.000 claims description 98
- 125000004432 carbon atom Chemical group C* 0.000 claims description 73
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 32
- 150000001412 amines Chemical class 0.000 claims description 19
- 239000000654 additive Substances 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 12
- 239000002184 metal Substances 0.000 claims description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 12
- 229920000877 Melamine resin Polymers 0.000 claims description 10
- 229910044991 metal oxide Inorganic materials 0.000 claims description 8
- 150000004706 metal oxides Chemical class 0.000 claims description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 8
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 7
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 7
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 claims description 6
- 239000004611 light stabiliser Substances 0.000 claims description 6
- 239000006096 absorbing agent Substances 0.000 claims description 5
- 239000003963 antioxidant agent Substances 0.000 claims description 5
- 150000001639 boron compounds Chemical class 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 230000002195 synergetic effect Effects 0.000 claims description 5
- 150000001399 aluminium compounds Chemical class 0.000 claims description 4
- 150000001463 antimony compounds Chemical class 0.000 claims description 4
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 4
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 3
- 239000000347 magnesium hydroxide Substances 0.000 claims description 3
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 3
- 150000004692 metal hydroxides Chemical class 0.000 claims description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 2
- 239000000049 pigment Substances 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 229940077746 antacid containing aluminium compound Drugs 0.000 claims 1
- 230000003078 antioxidant effect Effects 0.000 claims 1
- 150000002903 organophosphorus compounds Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 24
- 230000000979 retarding effect Effects 0.000 abstract description 18
- 150000002978 peroxides Chemical class 0.000 abstract description 4
- 229920006395 saturated elastomer Polymers 0.000 description 48
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 47
- 229920001577 copolymer Polymers 0.000 description 46
- 125000003118 aryl group Chemical group 0.000 description 41
- 125000000217 alkyl group Chemical group 0.000 description 33
- 229920000642 polymer Polymers 0.000 description 33
- 125000004122 cyclic group Chemical group 0.000 description 30
- 125000002947 alkylene group Chemical group 0.000 description 29
- 125000002950 monocyclic group Chemical group 0.000 description 29
- 229910052757 nitrogen Inorganic materials 0.000 description 27
- 125000001424 substituent group Chemical group 0.000 description 26
- 125000003342 alkenyl group Chemical group 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 18
- 125000006413 ring segment Chemical group 0.000 description 18
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
- 150000002148 esters Chemical class 0.000 description 17
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 16
- 239000004743 Polypropylene Substances 0.000 description 16
- 125000002993 cycloalkylene group Chemical group 0.000 description 16
- 229920001155 polypropylene Polymers 0.000 description 16
- 150000003254 radicals Chemical class 0.000 description 16
- 239000005977 Ethylene Substances 0.000 description 15
- 229940093470 ethylene Drugs 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 125000003710 aryl alkyl group Chemical group 0.000 description 14
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 13
- 125000000304 alkynyl group Chemical group 0.000 description 13
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 13
- 125000000623 heterocyclic group Chemical group 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000007983 Tris buffer Substances 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
- 125000000732 arylene group Chemical group 0.000 description 11
- 239000012964 benzotriazole Substances 0.000 description 11
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 10
- 239000004952 Polyamide Substances 0.000 description 10
- BJFLSHMHTPAZHO-UHFFFAOYSA-N benzotriazole Chemical compound [CH]1C=CC=C2N=NN=C21 BJFLSHMHTPAZHO-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000005062 Polybutadiene Substances 0.000 description 9
- 229920002647 polyamide Polymers 0.000 description 9
- 125000002619 bicyclic group Chemical group 0.000 description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 8
- 229920001684 low density polyethylene Polymers 0.000 description 8
- 239000004702 low-density polyethylene Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 229920002857 polybutadiene Polymers 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 239000004698 Polyethylene Substances 0.000 description 7
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 7
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 7
- 150000001408 amides Chemical class 0.000 description 7
- 125000004956 cyclohexylene group Chemical group 0.000 description 7
- 150000001993 dienes Chemical class 0.000 description 7
- 150000002367 halogens Chemical group 0.000 description 7
- 239000004700 high-density polyethylene Substances 0.000 description 7
- 239000004417 polycarbonate Substances 0.000 description 7
- 229920006324 polyoxymethylene Polymers 0.000 description 7
- 239000004800 polyvinyl chloride Substances 0.000 description 7
- 229920000915 polyvinyl chloride Polymers 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 6
- 150000002429 hydrazines Chemical class 0.000 description 6
- 229920000573 polyethylene Polymers 0.000 description 6
- 229920000098 polyolefin Polymers 0.000 description 6
- 229920002223 polystyrene Polymers 0.000 description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
- 125000000547 substituted alkyl group Chemical group 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 125000002015 acyclic group Chemical group 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229920001903 high density polyethylene Polymers 0.000 description 5
- 150000007857 hydrazones Chemical class 0.000 description 5
- 229940063557 methacrylate Drugs 0.000 description 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 5
- 229920006380 polyphenylene oxide Polymers 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 5
- 150000005846 sugar alcohols Polymers 0.000 description 5
- 125000004434 sulfur atom Chemical group 0.000 description 5
- AYNNSCRYTDRFCP-UHFFFAOYSA-N triazene Chemical compound NN=N AYNNSCRYTDRFCP-UHFFFAOYSA-N 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
- RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 4
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 4
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
- KXPXKNBDCUOENF-UHFFFAOYSA-N 2-(Octylthio)ethanol Chemical compound CCCCCCCCSCCO KXPXKNBDCUOENF-UHFFFAOYSA-N 0.000 description 4
- ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-UHFFFAOYSA-N 0.000 description 4
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 4
- CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 235000006708 antioxidants Nutrition 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- QKFKIYMZKDAJOR-UHFFFAOYSA-N cyclohexyl(hexadecyl)diazene Chemical compound CCCCCCCCCCCCCCCCN=NC1CCCCC1 QKFKIYMZKDAJOR-UHFFFAOYSA-N 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- 150000002815 nickel Chemical class 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- 235000019260 propionic acid Nutrition 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000005717 substituted cycloalkylene group Chemical group 0.000 description 4
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 4
- 239000011732 tocopherol Substances 0.000 description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
- 229940113165 trimethylolpropane Drugs 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 3
- DYIZJUDNMOIZQO-UHFFFAOYSA-N 4,5,6,7-tetrabromo-2-[2-(4,5,6,7-tetrabromo-1,3-dioxoisoindol-2-yl)ethyl]isoindole-1,3-dione Chemical compound O=C1C(C(=C(Br)C(Br)=C2Br)Br)=C2C(=O)N1CCN1C(=O)C2=C(Br)C(Br)=C(Br)C(Br)=C2C1=O DYIZJUDNMOIZQO-UHFFFAOYSA-N 0.000 description 3
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 3
- 229920002943 EPDM rubber Polymers 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 229920002367 Polyisobutene Polymers 0.000 description 3
- 229920002396 Polyurea Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000005250 alkyl acrylate group Chemical group 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 229920001276 ammonium polyphosphate Polymers 0.000 description 3
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 3
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Inorganic materials O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 3
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical class [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- 239000000806 elastomer Substances 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 3
- 229920006242 ethylene acrylic acid copolymer Polymers 0.000 description 3
- 239000005038 ethylene vinyl acetate Substances 0.000 description 3
- 229920005669 high impact polystyrene Polymers 0.000 description 3
- 239000004797 high-impact polystyrene Substances 0.000 description 3
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 229920000554 ionomer Polymers 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 150000005673 monoalkenes Chemical class 0.000 description 3
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- NSOSZGZQAADACF-UHFFFAOYSA-N n-(hexadecylsulfamoyl)cyclohexanamine Chemical compound CCCCCCCCCCCCCCCCNS(=O)(=O)NC1CCCCC1 NSOSZGZQAADACF-UHFFFAOYSA-N 0.000 description 3
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- XZTOTRSSGPPNTB-UHFFFAOYSA-N phosphono dihydrogen phosphate;1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(N)=N1.OP(O)(=O)OP(O)(O)=O XZTOTRSSGPPNTB-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- XFZRQAZGUOTJCS-UHFFFAOYSA-N phosphoric acid;1,3,5-triazine-2,4,6-triamine Chemical group OP(O)(O)=O.NC1=NC(N)=NC(N)=N1 XFZRQAZGUOTJCS-UHFFFAOYSA-N 0.000 description 1
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- ZRXDBIJHYWJRMT-UHFFFAOYSA-N piperidine-1,4-diamine Chemical compound NC1CCN(N)CC1 ZRXDBIJHYWJRMT-UHFFFAOYSA-N 0.000 description 1
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- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- MQOCIYICOGDBSG-UHFFFAOYSA-M potassium;hexadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCC([O-])=O MQOCIYICOGDBSG-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- KZNICNPSHKQLFF-HOSYLAQJSA-N pyrrolidine-2,5-dione Chemical compound O=C1CCC(=O)[15NH]1 KZNICNPSHKQLFF-HOSYLAQJSA-N 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
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- 239000000741 silica gel Substances 0.000 description 1
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- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- IJRHDFLHUATAOS-DPMBMXLASA-M sodium ricinoleate Chemical compound [Na+].CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O IJRHDFLHUATAOS-DPMBMXLASA-M 0.000 description 1
- 229940074404 sodium succinate Drugs 0.000 description 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
- UOULCEYHQNCFFH-UHFFFAOYSA-M sodium;hydroxymethanesulfonate Chemical compound [Na+].OCS([O-])(=O)=O UOULCEYHQNCFFH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
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- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- AVIZTSRRMBGYCJ-UHFFFAOYSA-N tetraazanium phosphonato phosphate 1,3,5-triazine-2,4,6-triamine Chemical compound [NH4+].[NH4+].[NH4+].[NH4+].NC1=NC(N)=NC(N)=N1.[O-]P([O-])(=O)OP([O-])([O-])=O AVIZTSRRMBGYCJ-UHFFFAOYSA-N 0.000 description 1
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- 235000010215 titanium dioxide Nutrition 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
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- 235000019149 tocopherols Nutrition 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 description 1
- BHYQWBKCXBXPKM-UHFFFAOYSA-N tris[3-bromo-2,2-bis(bromomethyl)propyl] phosphate Chemical compound BrCC(CBr)(CBr)COP(=O)(OCC(CBr)(CBr)CBr)OCC(CBr)(CBr)CBr BHYQWBKCXBXPKM-UHFFFAOYSA-N 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
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- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
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- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
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Classifications
-
- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0066—Flame-proofing or flame-retarding additives
-
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
- C08K5/23—Azo-compounds
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Fireproofing Substances (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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| EP03396092 | 2003-10-01 | ||
| PCT/EP2004/052271 WO2005030852A2 (en) | 2003-10-01 | 2004-09-22 | Flame retardant compositions |
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| CA2537157A1 CA2537157A1 (en) | 2005-04-07 |
| CA2537157C true CA2537157C (en) | 2014-03-25 |
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| EP (1) | EP1668073B1 (enExample) |
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| ZA (1) | ZA200601503B (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101151282B (zh) * | 2005-04-06 | 2011-09-14 | 西巴特殊化学品控股有限公司 | 用于聚丙烯降解的偶氮化合物 |
| US20080179360A1 (en) * | 2006-10-23 | 2008-07-31 | Lowe Michael V | Top lock security holster ii |
| US8202449B2 (en) * | 2006-10-31 | 2012-06-19 | Icl Performance Products, Lp | Corrosion-inhibited ammonium polyphosphate fire retardant compositions |
| ATE539059T1 (de) | 2007-02-21 | 2012-01-15 | Basf Se | Symmetrische azoverbindungen in flammverzögerungszusammensetzungen |
| KR20110138263A (ko) | 2009-03-30 | 2011-12-26 | 바스프 에스이 | 중합성 조성물 |
| WO2011035357A1 (de) * | 2009-09-24 | 2011-03-31 | Sunpor Kunststoff Ges.M.B.H. | Flammgeschützte expandierbare polymerisate |
| WO2012083426A1 (en) * | 2010-12-20 | 2012-06-28 | Cantech Industrial Research Corporation | Improved fire resistant coatings |
| SK5976Y1 (sk) * | 2011-02-24 | 2011-12-05 | Moles Technology A S | Fireproof paint coat matter |
| WO2012116886A1 (en) * | 2011-03-02 | 2012-09-07 | Huntsman International Llc | Flame retardant composition for thermoplastic polyurethane polymers |
| CN102532662A (zh) * | 2011-12-31 | 2012-07-04 | 潘雪峰 | 一种聚乙烯复合材料的制备方法 |
| CN104903070B (zh) * | 2012-12-27 | 2018-05-01 | 陶氏环球技术有限责任公司 | 通过反向旋转挤压制造热塑性聚烯烃屋顶膜 |
| US9926491B2 (en) | 2013-02-06 | 2018-03-27 | X'aan Innovations Inc. | Ammonium polyphosphate based fire-retardant compositions |
| EP2871208A1 (en) | 2013-11-08 | 2015-05-13 | Carl-Eric Wilen | Sulfenamides, sulfinamides and sulfonamides as flame retardants |
| DE102014218810B3 (de) | 2014-09-18 | 2016-01-28 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Verwendung von organischen Oxyimidsalzen als Flammschutzmittel, flammengeschützte Kunststoffzusammensetzung, Verfahren zur ihrer Herstellung sowie Formteil, Lack oder Beschichtung |
| DE102014218811A1 (de) | 2014-09-18 | 2016-03-24 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Verwendung von phosphorhaltigen organischen Oxyimiden als Flammschutzmittel, Radikalgeneratoren und/oder als Stabilisatoren für Kunststoffe, flammgeschützte Kunststoffzusammensetzung, Verfahren zu deren Herstellung sowie Formteile, Lacke und Beschichtungen |
| JP6563016B2 (ja) * | 2015-06-24 | 2019-08-21 | 株式会社フジクラ | 難燃性樹脂組成物、及び、これを用いたケーブル並びに光ファイバケーブル |
| CN105114612B (zh) * | 2015-09-18 | 2017-11-24 | 宁波明佳汽车内饰有限公司 | 换挡杆护套总成 |
| CN108003899A (zh) * | 2017-12-01 | 2018-05-08 | 宁波甬凌新材料科技有限公司 | 一种强度高的阻燃材料及其制备方法和应用 |
| CN109524162B (zh) * | 2018-11-23 | 2019-06-18 | 廊坊江海洋线缆有限公司 | 一种超高阻燃耐候性电缆 |
| FR3104593B1 (fr) * | 2019-12-12 | 2021-12-03 | Michelin & Cie | Système de réticulation et composition de caoutchouc diénique le comprenant |
| EP4097176A1 (en) | 2020-01-30 | 2022-12-07 | Nordtreat Finland OY | Flame retardant chemical compositions |
| CN112831117A (zh) * | 2021-02-26 | 2021-05-25 | 江西洪茂线缆有限公司 | 一种阻燃型交联聚乙烯电缆料及其制备方法 |
| CN117720769B (zh) * | 2024-02-07 | 2024-04-30 | 四川兴晶铧科技有限公司 | 一种复合阻燃增效剂以及一种阻燃尼龙材料 |
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| US3058926A (en) * | 1958-07-24 | 1962-10-16 | Dow Chemical Co | Method for making self-extinguishing alkenyl aromatic resin compositions comprising incorporating therein an organic bromine-containing compound and an organic peroxide |
| NL135462C (enExample) * | 1963-03-28 | |||
| US3269962A (en) * | 1963-04-01 | 1966-08-30 | Dow Chemical Co | Self-extinguishing polymer composition containing a halide and a hydrazone |
| US3296340A (en) * | 1963-04-01 | 1967-01-03 | Dow Chemical Co | Self-extinguishing alkenyl aromatic resins containing sulfenamides |
| US3284544A (en) * | 1963-04-01 | 1966-11-08 | Dow Chemical Co | Self-extinguishing alkenyl aromatic resins containing organic polysulfide |
| US3271333A (en) * | 1963-03-28 | 1966-09-06 | Dow Chemical Co | Self-extinguishing alkenyl aromatic polymers |
| NL127714C (enExample) * | 1965-04-01 | |||
| US3862107A (en) * | 1971-10-28 | 1975-01-21 | Pennwalt Corp | Method of curing polymers with azo compounds |
| US3897373A (en) * | 1973-04-21 | 1975-07-29 | Basf Ag | Self-extinguishing thermoplastic molding compositions |
| JPS5025651A (enExample) * | 1973-07-06 | 1975-03-18 | ||
| JPS5135504B2 (enExample) * | 1974-01-25 | 1976-10-02 | ||
| CH618563B (de) * | 1976-08-27 | 1900-01-01 | Ciba Geigy Ag | Verfahren zum flammfestmachen von mit kupfer-komplexazofarbstoffen gefaerbtem, cellulosehaltigem textilmaterial. |
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| US4115344A (en) * | 1977-07-05 | 1978-09-19 | Phillips Petroleum Company | Mold corrosion inhibition in poly(arylene) sulfide processing |
| SU908062A1 (ru) * | 1978-09-18 | 1983-06-07 | Центральный научно-исследовательский институт шерстяной промышленности | Кислотные бромбензолазокрасители дл крашени и одновременно огнезашитной отделки материалов из натуральных полиамидных волокон |
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-
2004
- 2004-09-22 RU RU2006114397/04A patent/RU2372362C2/ru not_active IP Right Cessation
- 2004-09-22 AT AT04787189T patent/ATE430179T1/de not_active IP Right Cessation
- 2004-09-22 ES ES04787189T patent/ES2323176T3/es not_active Expired - Lifetime
- 2004-09-22 US US10/573,850 patent/US20070029531A1/en not_active Abandoned
- 2004-09-22 WO PCT/EP2004/052271 patent/WO2005030852A2/en not_active Ceased
- 2004-09-22 CA CA2537157A patent/CA2537157C/en not_active Expired - Lifetime
- 2004-09-22 AU AU2004276001A patent/AU2004276001B2/en not_active Ceased
- 2004-09-22 CN CN2004800286107A patent/CN1860165B/zh not_active Expired - Fee Related
- 2004-09-22 EP EP04787189A patent/EP1668073B1/en not_active Expired - Lifetime
- 2004-09-22 JP JP2006530250A patent/JP4787160B2/ja not_active Expired - Lifetime
- 2004-09-22 SG SG200702453-2A patent/SG131932A1/en unknown
- 2004-09-22 DE DE602004020903T patent/DE602004020903D1/de not_active Expired - Lifetime
- 2004-09-22 BR BRPI0414992-0A patent/BRPI0414992A/pt not_active IP Right Cessation
- 2004-09-22 KR KR1020067006323A patent/KR101166752B1/ko not_active Expired - Fee Related
- 2004-09-30 TW TW093129611A patent/TWI356071B/zh not_active IP Right Cessation
-
2006
- 2006-02-21 ZA ZA200601503A patent/ZA200601503B/en unknown
-
2009
- 2009-01-09 US US12/319,676 patent/US7691929B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ZA200601503B (en) | 2007-04-25 |
| JP4787160B2 (ja) | 2011-10-05 |
| KR101166752B1 (ko) | 2012-07-27 |
| ATE430179T1 (de) | 2009-05-15 |
| KR20060096479A (ko) | 2006-09-11 |
| CN1860165A (zh) | 2006-11-08 |
| WO2005030852A2 (en) | 2005-04-07 |
| ES2323176T3 (es) | 2009-07-08 |
| RU2372362C2 (ru) | 2009-11-10 |
| DE602004020903D1 (de) | 2009-06-10 |
| SG131932A1 (en) | 2007-05-28 |
| TW200530313A (en) | 2005-09-16 |
| EP1668073A2 (en) | 2006-06-14 |
| US7691929B2 (en) | 2010-04-06 |
| WO2005030852A3 (en) | 2005-11-03 |
| US20070029531A1 (en) | 2007-02-08 |
| RU2006114397A (ru) | 2007-11-20 |
| BRPI0414992A (pt) | 2006-11-21 |
| AU2004276001A1 (en) | 2005-04-07 |
| AU2004276001B2 (en) | 2011-04-28 |
| EP1668073B1 (en) | 2009-04-29 |
| TWI356071B (en) | 2012-01-11 |
| JP2007507571A (ja) | 2007-03-29 |
| CA2537157A1 (en) | 2005-04-07 |
| CN1860165B (zh) | 2010-04-14 |
| US20090186970A1 (en) | 2009-07-23 |
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