JP2014508841A - ポリウレタンフォームのためのリン含有難燃剤 - Google Patents
ポリウレタンフォームのためのリン含有難燃剤 Download PDFInfo
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- JP2014508841A JP2014508841A JP2014500227A JP2014500227A JP2014508841A JP 2014508841 A JP2014508841 A JP 2014508841A JP 2014500227 A JP2014500227 A JP 2014500227A JP 2014500227 A JP2014500227 A JP 2014500227A JP 2014508841 A JP2014508841 A JP 2014508841A
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- JP
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- Prior art keywords
- phosphorus
- polyol
- flame retardant
- containing flame
- containing compound
- 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.)
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- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 229910052698 phosphorus Inorganic materials 0.000 title claims abstract description 60
- 239000011574 phosphorus Substances 0.000 title claims abstract description 60
- 239000003063 flame retardant Substances 0.000 title claims abstract description 57
- 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 45
- 229920005830 Polyurethane Foam Polymers 0.000 title description 17
- 239000011496 polyurethane foam Substances 0.000 title description 14
- 229920005862 polyol Polymers 0.000 claims abstract description 112
- 150000003077 polyols Chemical class 0.000 claims abstract description 105
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- 239000011541 reaction mixture Substances 0.000 claims abstract description 11
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 57
- -1 propylene, 2-methylpropylene, neopentylene Chemical group 0.000 claims description 38
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 29
- 239000004814 polyurethane Substances 0.000 claims description 20
- 229920002635 polyurethane Polymers 0.000 claims description 19
- 239000012948 isocyanate Substances 0.000 claims description 18
- 239000000047 product Substances 0.000 claims description 18
- 150000002513 isocyanates Chemical class 0.000 claims description 15
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 13
- 238000012360 testing method Methods 0.000 claims description 12
- 229920001451 polypropylene glycol Polymers 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 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 claims description 9
- 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 claims description 9
- 239000000600 sorbitol Substances 0.000 claims description 9
- 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 claims description 7
- 229930006000 Sucrose Natural products 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 239000005720 sucrose Substances 0.000 claims description 7
- RAOZVFGTRXLBTA-UHFFFAOYSA-N 2-chloro-5,5-dimethyl-1,3,2-dioxaphosphinane Chemical compound CC1(C)COP(Cl)OC1 RAOZVFGTRXLBTA-UHFFFAOYSA-N 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 125000004971 nitroalkyl group Chemical group 0.000 claims description 5
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 claims description 5
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 239000006260 foam Substances 0.000 description 22
- 229920013701 VORANOL™ Polymers 0.000 description 19
- 239000003054 catalyst Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 238000009472 formulation Methods 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- 239000000126 substance Substances 0.000 description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 11
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000005056 polyisocyanate Substances 0.000 description 9
- 229920001228 polyisocyanate Polymers 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- HHDUMDVQUCBCEY-UHFFFAOYSA-N 4-[10,15,20-tris(4-carboxyphenyl)-21,23-dihydroporphyrin-5-yl]benzoic acid Chemical compound OC(=O)c1ccc(cc1)-c1c2ccc(n2)c(-c2ccc(cc2)C(O)=O)c2ccc([nH]2)c(-c2ccc(cc2)C(O)=O)c2ccc(n2)c(-c2ccc(cc2)C(O)=O)c2ccc1[nH]2 HHDUMDVQUCBCEY-UHFFFAOYSA-N 0.000 description 8
- 235000011187 glycerol Nutrition 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 238000002156 mixing Methods 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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 229920000570 polyether Polymers 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 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
- 239000013518 molded foam Substances 0.000 description 6
- 239000004970 Chain extender Substances 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000007792 addition Methods 0.000 description 5
- 239000003431 cross linking reagent Substances 0.000 description 5
- 238000005187 foaming Methods 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 150000003018 phosphorus compounds Chemical class 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 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
- 239000003999 initiator Substances 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 4
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 4
- 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 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000004604 Blowing Agent Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-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
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 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
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920005906 polyester polyol Polymers 0.000 description 3
- 238000007614 solvation Methods 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical class CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 2
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920002396 Polyurea Polymers 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Chemical compound [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000013500 performance material Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
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- 239000008096 xylene Substances 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- XVOUMQNXTGKGMA-OWOJBTEDSA-N (E)-glutaconic acid Chemical compound OC(=O)C\C=C\C(O)=O XVOUMQNXTGKGMA-OWOJBTEDSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- PFUKECZPRROVOD-UHFFFAOYSA-N 1,3,5-triisocyanato-2-methylbenzene Chemical compound CC1=C(N=C=O)C=C(N=C=O)C=C1N=C=O PFUKECZPRROVOD-UHFFFAOYSA-N 0.000 description 1
- XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- ROHUXHMNZLHBSF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCC(CN=C=O)CC1 ROHUXHMNZLHBSF-UHFFFAOYSA-N 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/524—Esters of phosphorous acids, e.g. of H3PO3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657154—Cyclic esteramides of oxyacids of 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65742—Esters of oxyacids of phosphorus non-condensed with carbocyclic rings or heterocyclic rings or ring systems
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65746—Esters of oxyacids of phosphorus the molecule containing more than one cyclic phosphorus atom
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3878—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus
- C08G18/3882—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus having phosphorus bound to oxygen only
- C08G18/3887—Phosphite compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5075—Polyethers having heteroatoms other than oxygen having phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6681—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38
- C08G18/6688—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3271
-
- 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
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
-
- 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
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/527—Cyclic esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2110/00—Foam properties
- C08G2110/0008—Foam properties flexible
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- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Polyurethanes Or Polyureas (AREA)
- Fireproofing Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyethers (AREA)
Abstract
Description
HmA−(CH2)n−N(R)−(CH2)p−AHm
CI=Md/n x Mp
ここで、CIはキャッピング指数であり、Mdは、少なくとも1つのリン含有化合物のモル量であり、Mpは、少なくとも1つのポリオールのモル量であり、nは、少なくとも1つのポリオールの公称OH官能価である。
VORANOL* RN482 当量が117、OH値が480mg KOH/g、公称官能価が6のソルビトール開始ポリオキシプロピレンポリオール。ザ・ダウ・ケミカル・カンパニーより入手可能。
VORANOL* 280 グリセロールとスクロースのブレンドで開始する約1,795当量のポリオキシエチレンポリオキシプロピレンポリオール、公称官能価は約6.9、ポリオキシエチレン率は約25.6%、OH値は280mg KOH/g。ザ・ダウ・ケミカル・カンパニーより入手可能。
VORANOL* 3010 ポリオキシプロピレンポリオールでキャップされ、グリセロールで開始する、約994当量のポリオキシエチレンポリオキシプロピレン、公称官能価は3、ポリオキシエチレン率は約8%、OH値は56mg KOH/g。ザ・ダウ・ケミカル・カンパニーより入手可能。
VORANOL* CP1421 ポリオキシプロピレンポリオールでキャップされ、グリセロールで開始する、約1,675当量のポリオキシエチレン/ポリオキシプロピレン、公称官能価は3、ポリオキシエチレン率は約78%、ヒドロキシル価は約32mg KOH/g。ザ・ダウ・ケミカル・カンパニーより入手可能。
VORALUX* HF505HA ポリオキシプロピレンポリオールでキャップされ、ソルビトールで開始する、約1902当量のポリオキシエチレン、公称官能価は6、ポリオキシエチレン率は約16%、ヒドロキシル価は約29.5mg KOH/g。ザ・ダウ・ケミカル・カンパニーより入手可能。
2−クロロ−5,5−ジメチル−1,3,2−ジオキサホスフィナン シグマアルドリッチより入手可能。
トリエチルアミン シグマアルドリッチより入手可能。
TCPP トリクロロプロピルホスフェート、張家港市常余化工有限公司(Zhangjiagang Changyu Chemical Co., Ltd)製の難燃剤
H2O ザ・ダウ・ケミカル・カンパニーより入手可能な脱イオン水。
DEOA N,N−ジエタノールアミン、OH値1602、常州市宇平化工有限公司(Changzhou Jushun Chemical Company)製
TEGOSTAB B−8681 シリコーン界面活性剤、エボニックインダストリーズより商業的に入手可能。
NIAX L 620 シリコーン界面活性剤、モメンティブ・パフォーマンス・マテリアルズより入手可能。
DABCO 33−LV エアープロダクツ・アンド・ケミカルズ社より入手可能なプロピレングリコール中トリエチレンジアミンの33%溶液。
NIAX A−1 モメンティブ・パフォーマンス・マテリアルズより入手可能な70%ビス(2ジメチルアミノエチル)エーテル及び30%ジプロピレングリコール触媒。
DABCO T−9 エアープロダクツ・アンド・ケミカルズ社より入手可能な第一錫オクトエート触媒。
VORANATE* T−80 トルエンジイソシアネート(80重量%2,4−トルエンジイソシアネート及び20重量%2,6−トルエンジイソシアネート)、ザ・ダウ・ケミカル・カンパニーから入手可能な組成物。
*VORALUX、VORANATE及びVORANOLは、ザ・ダウ・ケミカル・カンパニーの商標である。
VORANOL RN482(210g、0.3mol)、トリエチルアミン(151.5g、1.5mol)及びジクロロメタン(600mL)を、機械攪拌機を装備した三口フラスコに充填した。ジクロロメタン(200mL)中の2−クロロ−5,5−ジメチル−1,3,2−ジオキサホスホリナン(202.3g、1.2mol)を、−10℃〜10℃の温度範囲に維持したフラスコに滴下した。反応をこの温度範囲で2時間保持し、その後トリエチルアミン−HCl塩の副生成物を濾過によって除去した。濾液の溶媒をロータリーエバポレーターによって除去した。残渣を最初に水で洗浄し、その後水を除去した。得られる生成物をジクロロメタン(600mL)に溶解した後、水で洗浄した。水層を除去し、溶媒層を無水MgSO4で一晩さらに乾燥させた。MgSO4を濾過し、ジクロロメタン溶媒を除去して、陽子及びリンNMRにより確認して平均して1分子あたり2個のOH基及び4個のホスファイト含有基を有するFRポリオールAを得た。
表1にCal117試験について示されるように、FR−ポリオールAをPUフォーム系に添加することにより、FR性能は劇的に増加する(実施例1)。8部のFR−ポリオールAを有する実施例1は、15部のTCPPを含む比較例2及び18部のTCPPを含む比較例3よりも良好なFR性能を有する。比較例1〜3の全てがCal117試験に不合格であった。これらの結果は、FR−ポリオールAが、ハロゲンを含有するTCPPと比較して低い添加量で良好なFR性能を与えることを示す。その上、FR−ポリオールAを添加することは、PUフォームの測定した機械的性質に悪影響を及ぼすことはない。
VORANOL 280(136.2g、0.1mol)、トリエチルアミン(104.5g、1.035mol)及びジクロロメタン(600mL)を、機械攪拌機を装備した三口フラスコに充填した。ジクロロメタン(200mL)中の2−クロロ−5,5−ジメチル−1,3,2−ジオキサホスホリナン(116.3g、0.69mol)を、−10℃〜10℃の温度範囲に維持したフラスコに滴下した。反応をこの温度範囲で2時間保持し、その後トリエチルアミン−HCl塩の副生成物を濾過によって除去した。濾液の溶媒をロータリーエバポレーターによって除去した。残渣を最初に水で洗浄し、その後水を除去した。得られる生成物をジクロロメタン(600mL)に溶解した後、水で洗浄した。水層を除去し、溶媒層を無水MgSO4で一晩さらに乾燥させた。MgSO4を濾過し、ジクロロメタン溶媒を除去して、FR Bの前駆体である中間体、非反応性ホスフィットを得た。この前駆体を、攪拌下2時間にわたって滴下した過酸化水素(水中30%)を用いてさらに酸化させてFR Bを得た。陽子及びリンNMRにより、ポリオールOH基の完全な変換を確認した。
Claims (15)
- 第1の反応混合物の反応生成物を含むリン含有難燃剤であって、前記反応混合物が:
少なくとも1つの第1のポリオールと;
一般式(1)、(2)又はそれらの組合せを有する少なくとも1つのリン含有化合物とを含む、リン含有難燃剤:
- リン含有難燃剤を調製する方法であって、前記方法が、
少なくとも:
少なくとも1つの第1のポリオールを;
一般式(1)、(2)又はそれらの組合せを有する少なくとも1つのリン含有化合物:
と反応させることを含む、方法。
- Rが、プロピレン、2−メチルプロピレン、ネオペンチレン、及び2−ブチル−2−エチルプロピレンのうちの少なくとも1つである、請求項1に記載のリン含有難燃剤又は請求項2に記載の方法。
- Xが、Cl−、Br−、及びI−、ならびにスルホン酸塩からなる群から選択される、請求項1又は3に記載のホスホン酸難燃剤あるいは請求項2又は3に記載の方法。
- 前記リン含有化合物が、2−クロロ−5,5−ジメチル−1,3,2−ジオキサホスフィナンである、請求項1に記載のリン含有難燃剤又は請求項2に記載の方法。
- 前記少なくとも1つの第1のポリオールが、約50〜2500当量及び約2〜10の結合した公称官能価を有するポリオキシアルキレン(polyoxalkylene)ポリオールの少なくとも1つを含む、請求項1又は3から5のいずれか一項に記載のリン含有難燃剤、又は請求項2から5のいずれか一項に記載の方法。
- 前記少なくとも1つのポリオキシアルキレン(polyoxalkylene)ポリオールが、グリセロール、スクロース、ソルビトール、又はそれらの組合せで開始され、前記ポリオキシアルキレン(polyoxalkylene)が、ポリオキシエチレン及びポリオキシプロピレンのうちの少なくとも1つを含む、請求項6に記載のリン含有難燃剤又は方法。
- 前記第1のポリオールが、ソルビトールで開始されたポリオキシプロピレンポリオールを約100〜約200の間の当量で含む、請求項1から5のいずれか一項に記載のリン含有難燃剤又は方法。
- 前記第1のポリオールが、グリセロールとスクロースのブレンドで開始された、約1,000〜約2500の間の当量、及び前記ポリオキシエチレンポリオキシプロピレンポリオールの重量に基づいて約15%〜約40%の間のポリオキシエチレン率を有するポリオキシエチレンポリオキシプロピレンポリオールを含む、請求項1から5のいずれか一項に記載のリン含有難燃剤又は方法。
- 前記リン含有難燃剤が、前記少なくとも1つの第1のポリオールが、ポリオールのOH部位と反応した、平均して少なくとも1つのリン含有化合物を有するようなキャッピング指数を有する、請求項1から9のいずれか一項に記載のリン含有難燃剤又は方法。
- 前記リン含有難燃剤が、前記少なくとも1つの第1のポリオールが、前記少なくとも1つのリン含有化合物にキャップされた、平均して少なくとも半分のそのポリオールのOH部位を有するようなキャッピング指数を有する、請求項1から9のいずれか一項に記載のリン含有難燃剤又は方法。
- 前記リン含有難燃剤が、前記少なくとも1つの第1のポリオールが、前記少なくとも1つのリン含有化合物にキャップされた、平均して実質的に全てのそのポリオールのOH部位を有するようなキャッピング指数を有する、請求項1から9のいずれか一項に記載のリン含有難燃剤又は方法。
- 第2の反応混合物の反応生成物を含むポリウレタン生成物であって、前記第2の反応混合物が、
少なくとも1つのイソシアネートと;
ポリオールブレンドを含み、前記ポリオールブレンドが、
請求項1及び3から12のいずれか一項に記載の少なくとも1つのリン含有難燃剤と;
少なくとも1つの第2のポリオールと
を含む、ポリウレタン生成物。 - Cal117試験に合格する、請求項13に記載のポリウレタン生成物。
- 前記リン含有難燃剤が、約0.1重量%〜35重量%の前記ポリオールブレンドを含む、請求項13又は14に記載のポリウレタン生成物。
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- 2011-03-23 JP JP2014500227A patent/JP2014508841A/ja active Pending
- 2011-03-23 WO PCT/CN2011/072072 patent/WO2012126179A1/en active Application Filing
- 2011-03-23 BR BR112013022385A patent/BR112013022385A2/pt not_active IP Right Cessation
- 2011-03-23 AU AU2011362906A patent/AU2011362906A1/en not_active Abandoned
- 2011-03-23 EP EP11861881.8A patent/EP2688898A4/en not_active Withdrawn
- 2011-03-23 RU RU2013147165/04A patent/RU2013147165A/ru not_active Application Discontinuation
- 2011-03-23 MX MX2013010824A patent/MX2013010824A/es unknown
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- 2012-03-22 JP JP2014500241A patent/JP2014515044A/ja active Pending
- 2012-03-22 BR BR112013022426-6A patent/BR112013022426B1/pt not_active IP Right Cessation
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- 2012-03-22 CA CA2830445A patent/CA2830445C/en active Active
- 2012-03-22 MX MX2013010835A patent/MX362285B/es active IP Right Grant
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BR112013022426B1 (pt) | 2020-03-03 |
WO2012126380A1 (en) | 2012-09-27 |
RU2595687C2 (ru) | 2016-08-27 |
RU2013147161A (ru) | 2015-04-27 |
EP2688898A4 (en) | 2014-10-29 |
BR112013022426A2 (pt) | 2016-12-06 |
CA2830446A1 (en) | 2012-09-27 |
EP2688953A4 (en) | 2014-08-27 |
EP2688953B1 (en) | 2019-05-01 |
EP2688898A1 (en) | 2014-01-29 |
BR112013022385A2 (pt) | 2016-12-06 |
AU2012231542A1 (en) | 2013-08-29 |
AU2012231542B2 (en) | 2015-10-01 |
US20140018509A1 (en) | 2014-01-16 |
MX2013010835A (es) | 2013-11-18 |
EP2688953A1 (en) | 2014-01-29 |
MX2013010824A (es) | 2013-10-17 |
US20140058035A1 (en) | 2014-02-27 |
CA2830445C (en) | 2019-04-09 |
JP2014515044A (ja) | 2014-06-26 |
US9023925B2 (en) | 2015-05-05 |
CA2830445A1 (en) | 2012-09-27 |
RU2013147165A (ru) | 2015-04-27 |
MX362285B (es) | 2019-01-10 |
AU2011362906A1 (en) | 2013-08-15 |
WO2012126179A1 (en) | 2012-09-27 |
CN103534263B (zh) | 2016-06-01 |
CN103534263A (zh) | 2014-01-22 |
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