JP2016500663A - 難燃性ポリウレタンフォーム用の有機リン化合物 - Google Patents
難燃性ポリウレタンフォーム用の有機リン化合物 Download PDFInfo
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- JP2016500663A JP2016500663A JP2015534898A JP2015534898A JP2016500663A JP 2016500663 A JP2016500663 A JP 2016500663A JP 2015534898 A JP2015534898 A JP 2015534898A JP 2015534898 A JP2015534898 A JP 2015534898A JP 2016500663 A JP2016500663 A JP 2016500663A
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- flame retardant
- formula
- carbon atoms
- organophosphorus compound
- Prior art date
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- 239000003063 flame retardant Substances 0.000 title claims abstract description 109
- 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 76
- 229920005830 Polyurethane Foam Polymers 0.000 title claims abstract description 58
- 150000002903 organophosphorus compounds Chemical class 0.000 title claims abstract description 58
- 239000011496 polyurethane foam Substances 0.000 title claims abstract description 45
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 54
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 41
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 40
- 239000011574 phosphorus Substances 0.000 claims abstract description 40
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 39
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 14
- 229920005862 polyol Polymers 0.000 claims description 70
- 150000003077 polyols Chemical class 0.000 claims description 70
- 150000002513 isocyanates Chemical class 0.000 claims description 38
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
- 239000012948 isocyanate Substances 0.000 claims description 25
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 150000003457 sulfones Chemical class 0.000 claims description 6
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 229910052711 selenium Inorganic materials 0.000 claims description 5
- 150000003462 sulfoxides Chemical class 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 239000004088 foaming agent Substances 0.000 claims description 3
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 abstract 1
- 101150035983 str1 gene Proteins 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 52
- -1 —N (R 4 ) — group Chemical group 0.000 description 41
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- 239000006260 foam Substances 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 26
- 238000000034 method Methods 0.000 description 19
- 239000004814 polyurethane Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000000047 product Substances 0.000 description 18
- 229920002635 polyurethane Polymers 0.000 description 17
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 16
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- 239000011541 reaction mixture Substances 0.000 description 15
- 239000003054 catalyst Substances 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- 239000004604 Blowing Agent Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 12
- 229920013701 VORANOL™ Polymers 0.000 description 12
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- LOOCNDFTHKSTFY-UHFFFAOYSA-N 1,1,2-trichloropropyl dihydrogen phosphate Chemical compound CC(Cl)C(Cl)(Cl)OP(O)(O)=O LOOCNDFTHKSTFY-UHFFFAOYSA-N 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
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- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 10
- 239000005056 polyisocyanate Chemical group 0.000 description 9
- 229920001228 polyisocyanate Chemical group 0.000 description 9
- 229920001451 polypropylene glycol Polymers 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 229920000570 polyether Polymers 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 238000005187 foaming Methods 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000012973 diazabicyclooctane Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 235000011187 glycerol Nutrition 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 239000013518 molded foam Substances 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 239000004970 Chain extender Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 5
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 5
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 5
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 5
- 239000012346 acetyl chloride Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 239000000600 sorbitol Substances 0.000 description 5
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 5
- 239000011592 zinc chloride Substances 0.000 description 5
- 235000005074 zinc chloride Nutrition 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 239000004971 Cross linker Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
- 229930006000 Sucrose Natural products 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-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
- 230000032683 aging Effects 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000005720 sucrose Substances 0.000 description 4
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 4
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 3
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
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- 229920013708 Dow VORANOL™ CP 1421 Polyol Polymers 0.000 description 3
- 238000000023 Kugelrohr distillation Methods 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 229960001701 chloroform Drugs 0.000 description 3
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 3
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- 125000003118 aryl group Chemical group 0.000 description 2
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- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
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- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 1
- XXNPWUCSMZUOOC-UHFFFAOYSA-N 2-butyl-2-ethylpentanedioic acid Chemical compound CCCCC(CC)(C(O)=O)CCC(O)=O XXNPWUCSMZUOOC-UHFFFAOYSA-N 0.000 description 1
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- BTQLWKNIJDKIAB-UHFFFAOYSA-N 6-methylidene-n-phenylcyclohexa-2,4-dien-1-amine Chemical compound C=C1C=CC=CC1NC1=CC=CC=C1 BTQLWKNIJDKIAB-UHFFFAOYSA-N 0.000 description 1
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- 229910015900 BF3 Inorganic materials 0.000 description 1
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- QHWKHLYUUZGSCW-UHFFFAOYSA-N Tetrabromophthalic anhydride Chemical compound BrC1=C(Br)C(Br)=C2C(=O)OC(=O)C2=C1Br QHWKHLYUUZGSCW-UHFFFAOYSA-N 0.000 description 1
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- 230000001070 adhesive effect Effects 0.000 description 1
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- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
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- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
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- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
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- 125000001033 ether group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
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- SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012796 inorganic flame retardant Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000013035 low temperature curing Methods 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- ZQKXQUJXLSSJCH-UHFFFAOYSA-N melamine cyanurate Chemical compound NC1=NC(N)=NC(N)=N1.O=C1NC(=O)NC(=O)N1 ZQKXQUJXLSSJCH-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- HOVAGTYPODGVJG-ZFYZTMLRSA-N methyl alpha-D-glucopyranoside Chemical compound CO[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HOVAGTYPODGVJG-ZFYZTMLRSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- RCZLVPFECJNLMZ-UHFFFAOYSA-N n,n,n',n'-tetraethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN(CC)CC RCZLVPFECJNLMZ-UHFFFAOYSA-N 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
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- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
- RUOPINZRYMFPBF-UHFFFAOYSA-N pentane-1,3-diol Chemical compound CCC(O)CCO RUOPINZRYMFPBF-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- XFZRQAZGUOTJCS-UHFFFAOYSA-N phosphoric acid;1,3,5-triazine-2,4,6-triamine Chemical compound OP(O)(O)=O.NC1=NC(N)=NC(N)=N1 XFZRQAZGUOTJCS-UHFFFAOYSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920003226 polyurethane urea Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- 150000003141 primary amines Chemical group 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
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
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- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical group 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000011145 styrene acrylonitrile resin Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-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
- XKCQNWLQCXDVOP-UHFFFAOYSA-N tris(2-chloropropan-2-yl) phosphate Chemical compound CC(C)(Cl)OP(=O)(OC(C)(C)Cl)OC(C)(C)Cl XKCQNWLQCXDVOP-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
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000003190 viscoelastic substance Substances 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/0014—Use of organic additives
- C08J9/0038—Use of organic additives containing phosphorus
-
- 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
- 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
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Abstract
Description
HmA−(CH2)n−N(R)−(CH2)P−AHm
上式において、nとpは互いに独立して2〜6の整数であり、それぞれに位置するAは互いに独立して酸素または窒素であり、mは、Aが酸素のときに1に等しく、Aが窒素のときに2である。
VORANOL 3010(ポリオール)、公称官能価3、ポリオキシエチレンパーセンテージ約8%、OH価56mg KOH/gを有した等価重量が約994のグリセロール開始化ポリオキシエチレン/ポリオキシプロピレンキャップドポリオキシプロピレンポリオール。Dow Chemical社から入手可能。
OPC EX1を生産するための反応は下記式:
OPC EX2を生産するための反応は下記式:
OPC EX3を生産するための反応は下記式:
OPC EX4を生産する反応は下記式:
防火性ポリウレタンフォーム実施例(FR PU フォーム Ex)6−9と比較例A
FR PU フォーム Ex6−9と比較例Aを次の通り生産した。FR PU フォーム Ex6−9と比較例Aは、プラスチックカップ中で手混合によって生産した。表1に示した量に従って、OPC EX1〜OPC EX4(FR PU フォーム Ex6−9の場合)、TCPP(比較例Aの場合)を、高速混合機(HSIANG TAI MACHINERY INDUSTRY CO., LTD製DC−CH40RM)によって毎分3000回転(rpm)でVORANOL 3010と混合した。各々の混合物に、表1で示した量に従って、3:1の比率のDABCO 33LVとNIAX Al、水、Niax L620、DABCO T−9を加え、毎分3000rpmで混合した。約6秒間の高速混合(約3000−4000rpm)下で、表1に示した量に従って、各々混合物にVORANATE T−80を加えた。得られた組成物は、発泡用の開放箱に注入した。
FR PU フォーム Ex10−14と比較例Bを次の通り生産した。FR PU フォーム Ex10−14と比較例Bは、プラスチックカップ中で手混合によって生産した。表2に示した量に従って、OPC EX1〜OPC EX4(FR PU フォーム Ex10−14の場合)、TCPP(比較例Bの場合)を、高速混合機(HSIANG TAI MACHINERY INDUSTRY CO., LTD製DC−CH40RM)によって毎分3000回転(rpm)で、VORALUX HF505HA、VORANOL CP1421と混合した。各々の混合物に、表2で示した量に従って、DEOA、TEGOSTAB B8681、3:1の比率のDABCO 33−LVとNIAX Al、水、 DABCO T−9を加え、毎分3000rpmで混合した。約6秒間の高速混合(約3000−4000rpm)下で、表2に示した量に従って、各々の混合物にVORANATE T−80を加えた。得られた組成物は、発泡用の開放箱に注入した。
Claims (19)
- 式(I):
Yは、R3が1〜10の炭素原子を持つ1価ヒドロカルビル基である場合に−OH基、−NH2基、−NHR3基および−SH基からなる基から選択され、;
Rは2価ヒドロカルビルであり;
Xはヘテロ原子基であり;
R1とR2は、それぞれ互いに独立して置換または非置換ヒドロカルビル基であり、R1とR2は任意に結合して環を形成することができるが、Yがヒドロキシル基、Xが酸素原子、Rが−CR5 2−CR5 2−のときに、各々のR5が互いに独立して水素基または1〜4の炭素原子を持つヒドロカルビル基である場合に、次いでR1とR2は結合して環を形成する]の有機リン化合物。 - Rが1〜20の炭素原子を持つ2価ヒドロカルビル基である、請求項1記載の有機リン化合物。
- Xのヘテロ原子基は、R4が置換または非置換ヒドロカルビル基である場合に酸素原子、硫黄原子、−N(R4)−基、セレン原子、−PR4(O)−基、スルホキシド(−S(O)−)基、スルホン(−S(O)2−)基からなる基から選択される、請求項1記載の有機リン化合物。
- R1とR2は、それぞれ互いに独立して1〜10の炭素原子を持つヒドロカルビル基である、請求項1記載の有機リン化合物。
- Yはヒドロキシル基であり;
Xは酸素原子であって、R1とR2は結合して式(II):
の環を形成する、請求項1記載の有機リン化合物。 - 前記Rは2個の炭素原子を持つ2価ヒドロカルビル基であって式(III):
- 各々のR5は水素基であって式(IV):
- 前記Rは3個の炭素原子を持つ2価ヒドロカルビル基であって式(V):
- ポリオール;と
式I:
Yは、R3が1〜10の炭素原子を持つ1価ヒドロカルビル基である場合に−OH基、−NH2基、−NHR3基および−SH基からなる基から選択され;
Rは2価ヒドロカルビル基であり;
Xはヘテロ原子基であり;
R1とR2は、それぞれ互いに独立して置換または非置換ヒドロカルビル基であり、R1とR2は任意に結合して環を形成することができる]の有機リン化合物との混合物を含む、リン含有難燃剤。 - Rは1〜20の炭素原子を持つ2価ヒドロカルビル基である、請求項9記載のリン含有難燃剤。
- Xのヘテロ原子基は、R4が置換または非置換ヒドロカルビル基である場合に酸素原子、硫黄原子、−N(R4)−基、セレン原子、−PR4(O)−基、スルホキシド(−S(O)−)基、スルホン(−S(O)2−)基からなる基から選択される、請求項9記載のリン含有難燃剤。
- R1とR2は、それぞれが互いに独立して1〜10の炭素原子を持つヒドロカルビル基である、請求項9記載のリン含有難燃剤。
- 式(I)の有機リン化合物が請求項5〜9における有機リン化合物のいずれか1つの構造を持つ、請求項9記載のリン含有難燃剤。
- 式Iの有機リン化合物の場合で、
Yはヒドロキシル基であり;
Xは酸素原子であって、R1とR2は結合して式(II);
Rは2つの炭素原子を持つ2価ヒドロカルビル基であって式(IV):
- Yはヒドロキシル基であり;
Rは2つの炭素原子を持つ2価ヒドロカルビル基であり;
Xは酸素原子であって、R1とR2は2つの炭素原子を有して式(VII):
- Yはヒドロキシル基であり;
Rは3つの炭素原子を持つ2価ヒドロカルビル基であり;
Xは酸素原子であって、R1とR2はそれぞれ2つの炭素原子を有して式(VIII):
- ポリオールは、900〜2500の等価重量および2〜10の統合公称官能価を有したポリオキシアルキレンポリオールである、請求項9〜16のいずれか1項に記載のリン含有難燃剤。
- イソシアネート;
請求項9〜17のいずれか1項に記載のリン含有難燃剤;および
起泡剤、の反応生産物を含む難燃性ポリウレタンフォーム。 - 難燃性ポリウレタンフォームは100重量部のポリオール当たり5〜7部のリン含有難燃剤を含む、請求項18記載の難燃性ポリウレタンフォーム。
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US8198341B2 (en) | 2008-12-18 | 2012-06-12 | Icl-Ip America Inc. | Method of making hydroxymethylphosphonate, polyurethane foam-forming compositions, polyurethane foam and articles made therefrom |
PL3553068T3 (pl) | 2012-10-17 | 2021-11-22 | Icl-Ip America Inc. | Hydroksymetylofosfonian, kompozycje tworzące piankę poliuretanową, pianka poliuretanowa oraz wytworzone z niej wyroby |
US9815256B2 (en) | 2014-06-09 | 2017-11-14 | Johns Manville | Foam boards including non-halogenated fire retardants |
US9523195B2 (en) | 2014-06-09 | 2016-12-20 | Johns Manville | Wall insulation boards with non-halogenated fire retardant and insulated wall systems |
US9528269B2 (en) | 2014-06-09 | 2016-12-27 | Johns Manville | Roofing systems and roofing boards with non-halogenated fire retardant |
US9815966B2 (en) | 2014-07-18 | 2017-11-14 | Johns Manville | Spray foams containing non-halogenated fire retardants |
WO2017087298A1 (en) * | 2015-11-18 | 2017-05-26 | Icl-Ip America Inc. | Flame retardant liquid solution, polyurethane foam-forming compositions, polyurethane foam and articles made therefrom |
WO2017136277A1 (en) | 2016-02-04 | 2017-08-10 | University Of Pittsburgh-Of The Commonwealth System Of Higher Education | Molecularly doped piezoelectric foams |
RU2726212C1 (ru) * | 2019-12-17 | 2020-07-09 | Федеральное государственное бюджетное образовательное учреж-дение высшего образования "Волгоградский государственный технический университет" (ВолгГТУ) | Композиция для получения жесткого пенополиуретана пониженной горючести |
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US9738766B2 (en) | 2017-08-22 |
ES2656615T3 (es) | 2018-02-27 |
JP6122960B2 (ja) | 2017-04-26 |
US20150274915A1 (en) | 2015-10-01 |
BR112015007841B1 (pt) | 2020-09-29 |
MX2015004415A (es) | 2016-01-08 |
BR112015007841A2 (pt) | 2017-07-04 |
EP2903994A4 (en) | 2016-07-06 |
EP2903994B1 (en) | 2017-11-22 |
WO2014056138A8 (en) | 2014-07-03 |
PT2903994T (pt) | 2018-01-03 |
EP2903994A1 (en) | 2015-08-12 |
CN104936967B (zh) | 2017-09-29 |
WO2014056138A1 (en) | 2014-04-17 |
CN104936967A (zh) | 2015-09-23 |
PL2903994T3 (pl) | 2018-04-30 |
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