JP5507848B2 - 剛性ポリウレタンフォームに用いられる非ハロゲン難燃剤 - Google Patents
剛性ポリウレタンフォームに用いられる非ハロゲン難燃剤 Download PDFInfo
- Publication number
- JP5507848B2 JP5507848B2 JP2008549600A JP2008549600A JP5507848B2 JP 5507848 B2 JP5507848 B2 JP 5507848B2 JP 2008549600 A JP2008549600 A JP 2008549600A JP 2008549600 A JP2008549600 A JP 2008549600A JP 5507848 B2 JP5507848 B2 JP 5507848B2
- Authority
- JP
- Japan
- Prior art keywords
- phosphate
- polyurethane foam
- flame retardant
- group
- phenyl
- 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 - Fee Related
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- 229920005830 Polyurethane Foam Polymers 0.000 title claims abstract description 49
- 239000011496 polyurethane foam Substances 0.000 title claims abstract description 49
- 239000003063 flame retardant Substances 0.000 title claims description 74
- 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 description 60
- 229910052736 halogen Inorganic materials 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 70
- -1 phosphate ester Chemical class 0.000 claims abstract description 53
- 229920005862 polyol Polymers 0.000 claims abstract description 51
- 150000003077 polyols Chemical class 0.000 claims abstract description 50
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 44
- 239000010452 phosphate Substances 0.000 claims abstract description 43
- 239000012948 isocyanate Substances 0.000 claims abstract description 39
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 37
- 229920002635 polyurethane Polymers 0.000 claims abstract description 18
- 239000004814 polyurethane Substances 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 239000006260 foam Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 17
- 239000004604 Blowing Agent Substances 0.000 claims description 13
- 239000000654 additive Substances 0.000 claims description 13
- 230000000996 additive effect Effects 0.000 claims description 12
- 238000002485 combustion reaction Methods 0.000 claims description 11
- YGZXVFAXIZVTTH-UHFFFAOYSA-N 2-methylpropyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCC(C)C)OC1=CC=CC=C1 YGZXVFAXIZVTTH-UHFFFAOYSA-N 0.000 claims description 9
- TZOHKIXYILEQDW-UHFFFAOYSA-N bis(2-methylpropyl) phenyl phosphate Chemical compound CC(C)COP(=O)(OCC(C)C)OC1=CC=CC=C1 TZOHKIXYILEQDW-UHFFFAOYSA-N 0.000 claims description 9
- 239000004094 surface-active agent Substances 0.000 claims description 9
- DIBUFQMCUZYQKN-UHFFFAOYSA-N butyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCCC)OC1=CC=CC=C1 DIBUFQMCUZYQKN-UHFFFAOYSA-N 0.000 claims description 7
- YICSVBJRVMLQNS-UHFFFAOYSA-N dibutyl phenyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OC1=CC=CC=C1 YICSVBJRVMLQNS-UHFFFAOYSA-N 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000003431 cross linking reagent Substances 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 4
- NNIJZQYSYZQFDZ-UHFFFAOYSA-N (2,3-dibutylphenyl) dihydrogen phosphate Chemical group CCCCC1=CC=CC(OP(O)(O)=O)=C1CCCC NNIJZQYSYZQFDZ-UHFFFAOYSA-N 0.000 claims description 3
- RVQOXEIOIUDSFU-UHFFFAOYSA-N (2,3-dipentylphenyl) dihydrogen phosphate Chemical compound CCCCCC1=CC=CC(OP(O)(O)=O)=C1CCCCC RVQOXEIOIUDSFU-UHFFFAOYSA-N 0.000 claims description 3
- ZSQQSVWGVBGFPJ-UHFFFAOYSA-N CCCCCCC1=CC=CC(OP(O)(O)=O)=C1CCCCCC Chemical compound CCCCCCC1=CC=CC(OP(O)(O)=O)=C1CCCCCC ZSQQSVWGVBGFPJ-UHFFFAOYSA-N 0.000 claims description 3
- DHTQKXHLXVUBCF-UHFFFAOYSA-N diethyl phenyl phosphate Chemical group CCOP(=O)(OCC)OC1=CC=CC=C1 DHTQKXHLXVUBCF-UHFFFAOYSA-N 0.000 claims description 3
- NODGGJKZBPRISK-UHFFFAOYSA-N diphenyl propyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCC)OC1=CC=CC=C1 NODGGJKZBPRISK-UHFFFAOYSA-N 0.000 claims description 3
- JSPBAVGTJNAVBJ-UHFFFAOYSA-N ethyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCC)OC1=CC=CC=C1 JSPBAVGTJNAVBJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- VUTSVIHQBJIUOS-UHFFFAOYSA-N phenyl dipropyl phosphate Chemical compound CCCOP(=O)(OCCC)OC1=CC=CC=C1 VUTSVIHQBJIUOS-UHFFFAOYSA-N 0.000 claims description 3
- 229920001228 polyisocyanate Polymers 0.000 claims description 3
- 239000005056 polyisocyanate Substances 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims 1
- KMSNCDKFBPJXRF-UHFFFAOYSA-N hexyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCCCCC)OC1=CC=CC=C1 KMSNCDKFBPJXRF-UHFFFAOYSA-N 0.000 claims 1
- 235000021317 phosphate Nutrition 0.000 description 24
- 239000002253 acid Substances 0.000 description 16
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 9
- 229920005906 polyester polyol Polymers 0.000 description 9
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 8
- 125000005037 alkyl phenyl group Chemical group 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 7
- 238000005187 foaming Methods 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 7
- 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 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- 229920000570 polyether Polymers 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- 239000002666 chemical blowing agent Substances 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 150000003512 tertiary amines Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical compound CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 239000004088 foaming agent Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 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
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 229920000582 polyisocyanurate Polymers 0.000 description 3
- 239000011495 polyisocyanurate Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 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 3
- DXZMANYCMVCPIM-UHFFFAOYSA-L zinc;diethylphosphinate Chemical compound [Zn+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC DXZMANYCMVCPIM-UHFFFAOYSA-L 0.000 description 3
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- RJHVQEGGSIHMMG-UHFFFAOYSA-N 2-[2,2-bis(methylamino)ethoxy]-1-n,1-n'-dimethylethane-1,1-diamine Chemical compound CNC(NC)COCC(NC)NC RJHVQEGGSIHMMG-UHFFFAOYSA-N 0.000 description 2
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 2
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Natural products CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 2
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 2
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N Alanine Chemical compound CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 239000004970 Chain extender Substances 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-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
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-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
- 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 2
- 229930006000 Sucrose Natural products 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WOURXYYHORRGQO-UHFFFAOYSA-N Tri(3-chloropropyl) phosphate Chemical compound ClCCCOP(=O)(OCCCCl)OCCCCl WOURXYYHORRGQO-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000007824 aliphatic compounds Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 238000011021 bench scale process Methods 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-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
- 239000004566 building material Substances 0.000 description 2
- 239000001273 butane Substances 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
- 229920001577 copolymer Polymers 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 239000001282 iso-butane Substances 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
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
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- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
- 150000004707 phenolate Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- DYFXGORUJGZJCA-UHFFFAOYSA-N phenylmethanediamine Chemical compound NC(N)C1=CC=CC=C1 DYFXGORUJGZJCA-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000036314 physical performance Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- BPELEZSCHIEMAE-UHFFFAOYSA-N salicylaldehyde imine Chemical compound OC1=CC=CC=C1C=N BPELEZSCHIEMAE-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical group [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002937 thermal insulation foam Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000006269 thermoset foam Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-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
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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
- C08K5/49—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
- 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
- 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
-
- 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
- C08K5/523—Esters of phosphoric acids, e.g. of H3PO4 with hydroxyaryl compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
-
- 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
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
-
- 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
- C08K2201/00—Specific properties of additives
- C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
本発明では、様々な有機イソシアネートを出発材として使用できる。イソシアネートは、公知の脂肪族、脂環式及び芳香族のいずれのタイプでもよく、これらのタイプのうちの少なくとも2つの混合物であってもよく、また、当該有機イソシアネートを単独若しくは2つ以上を組み合わせてもよく、それらは同じタイプであっても、異なるタイプであってもよい。すなわち、ポリウレタンの調製において従来使用されているイソシアネートを使用できる。本発明に用いられる適切なイソシアネートの非限定的な例として、芳香族ジイソシアネート(例えば2,4−トリレンジイソシアネート、2,6−トリレンジイソシアネート、粗製のトリレンジイソシアネート、ジフェニルメタンジイソシアネート及び粗製のジフェニルメタンジイソシアネート)、芳香族トリイソシアネート(例えば4,4’,4”−トリフェニルメタントリイソシアネート及び2,2’,6−トリレントリイソシアネート)、芳香族性テトライソシアネート(例えば4,4’−ジメチルジフェニルメタン−2,2’,5,5’−テトライソシアネート)、脂肪族のイソシアネート(例えばヘキサメチレン−1,6−ジイソシアネート)、脂環式イソシアネート(例えば水素化ジフェニルメタンジイソシアネート)、並びに他のジイソシアネート(例えばm−フェニレンジイソシアネート、ナフチルエン−1,5−ジイソシアネート、1−メトキシフェニル−2,4−ジイソシアネート、4,4’−ビフェニルジイソシアネート、3,3’−ジメトキシ−4,4’−ビフェニルジイソシアネート及び3,3’−ジメチルジフェニルメタン−4,4’−ジイソシアネート)が挙げられる。使用できる様々なイソシアネートの中で、好適なものとしては、2,4−トリレンジイソシアネート、2,6−トリレンジイソシアネート、粗製トリレンジイソシアネート、ジフェニルメタンジイソシアネート、粗製ジフェニルメタンジイソシアネート、ヘキサメチレン−1,6−ジイソシアネート及び水素化ジフェニルメタンジイソシアネートが挙げられる。
本発明の実施において使用するポリオールは、イソシアネートと反応してポリイソシアヌレートを形成できる少なくとも2つの官能基を含有するいかなる化合物であってもよい。これらの官能基は少なくとも1つの活性水素原子を含有し、例えばZerewittinoff反応により定義される。活性水素原子は通常、酸素、窒素又は硫黄原子に結合している水素原子であり、好ましくは水酸基の水素原子である。
本発明の触媒には、標準的な第三級アミン及び有機金属ポリウレタン触媒の組合せが包含される。多くの種類のポリウレタン触媒のいずれであっても、ポリウレタンフォームの調製に利用できる。典型的な添加量は、反応混合物の重量に対して約0.001〜5%まである。通常は約0.001〜約2%の添加量である。相対的な比率は当業者に公知である。本願明細書において用いられる適切な第三級アミン触媒としては、ビス(2,2’−ジメチルアミノエチル)エーテル、トリメチルアミン、N−メチルモルホリン、N,N−エチルモルホリニウム、N,N−ジメチルベンジルアミン、N,N−ジメチルエタノールアミン、N,N,N’,N’−テトラメチル−1,3−ブタンジアミン、ペンタメチルジプロピレントリアミン、トリエチレンジアミン、酸化ピリジンなどが挙げられる。典型的な本発明のアミン触媒は、ビス(2,2’−ジメチルアミノエチル)エーテル及びトリエチレンジアミンである。
本発明のポリウレタンの調製において、発泡剤を用いることができる。かかる発泡剤としては、限定されないが例えば炭化水素系発泡剤(例えば直鎖状若しくは分枝状アルカン炭化水素、ブタン、イソブタン、2,3−ジメチルブタン、n−及びイソペンタン及び工業用グレードのペンタン混合物、n−及びイソヘキサン、並びにn−及びイソヘプタン)が挙げられる。1つ以上の炭化水素発泡剤と、他の発泡剤とを組み合わせて用いてもよく、かかる他の発泡剤は、化学的発泡剤(イソシアネート又は他の成分と化学的に反応してガスを放出させて発泡させる成分)と、物理的発泡剤(発熱発泡温度若しくはそれ以下の温度でガス状であり、発泡ガスの発生の際に気泡成分と化学的に反応する必要のない成分)に大別される。熱的に不安定で、高温で分解するガスは、上記の物理的発泡剤の範疇に包含される。化学的発泡剤の例としては、好ましくはイソシアネートと反応してガス(例えばCO2)を発生させる物質である。好適な、化学的発泡剤としては、水、46〜300の分子量を有するモノ−及びポリカルボン酸、これらの酸の塩、及び第三級アルコールが挙げられるが、これらに限定されない。
本発明のハロゲンフリーの難燃性ポリウレタンフォーム組成物の調製では、リン酸エステル難燃剤を利用する。本発明の難燃性ポリウレタンフォーム組成物に用いられる難燃性剤添加剤はハロゲンフリーのリン酸エステル化合物であり、イソシアネートと実質的に反応しない(すなわち、いかなる活性水素含有基(例えばヒドロキシル、メルカプト、アミノ及びカルボン酸基)も有しない)。
(R1O)nP(O)(OR2)3-n
式中、nは1又は2であり、R1はアルキル基であり、R2はアリール基である。本発明の一態様では、当該難燃性リン酸エステルは、一般式:
(R1O)nP(O)(OR2)3-n
で表され、式中、nは1又は2であり、R1は約1〜約6の炭素原子数のアルキル基であり、R2はフェニル基である。本発明の更に別の態様では、当該難燃性リン酸エステルは、一般式:
(R1O)nP(O)(OR2)3-n
で表され、式中、R1はn−ブチル又はイソブチル基であり、R2はフェニル基である。
必要に応じて、界面活性剤を発泡安定剤として使用してもよい。本発明に包含される界面活性剤は、非イオン系界面活性剤(例えばオルガノシロキサン−ポリオキシアルキレンコポリマー又はシリコーン−グリースコポリマー又はその混合物)などの、従来公知の有機シリコンタイプ界面活性剤である。かかる界面活性剤の量は通常、ポリオール100重量%に対して0.1〜10重量%である。
必要に応じて、架橋剤又は連鎖延長剤を添加してもよい。架橋剤又は連鎖延長剤は、エチレングリコール、1,4−ブタンジオール又はグリセロールなどの低分子量ポリオール、ジエタノールアミン又はトリエタノールアミンなどの低分子量アミンポリオール、又はエチレンジアミン、キシリレンジアミン又はメチレンビスオルトクロロアニリンなどのポリアミンであってもよい。
2Dabco TMR−30(触媒、Air Products And Chemicals社製のトリ−2,4,6−ジメチルアミノメチルフェノール、〜90%)。
3Tegostab B8512(界面活性剤、Degussa Goldshmidt Chemical社製のポリエーテルポリジメチルシロキサン)。
4Kosmos64(触媒、Degussa社製の酢酸カリウム)。
5MDI(ダウ・ケミカル社製のポリメチレンポリフェニルイソシアネート)。
7Pel−cat9529(Pelron社製の酢酸カリウム)。
8Polycat−5(発泡触媒、Air Products and Chemicals社製のペンタメチルジエチレントリアミン)。
9MDI PAPI 580N(ダウケミカル社製のポリメチレンポリフェニルイソシアネート)。
Claims (25)
- 少なくとも1つのリン酸エステル添加剤を燃焼防止にとり有効量で含有する難燃性ポリウレタンフォーム組成物であって、
前記リン酸エステル添加剤が下記の一般式で表され、
(R1O)nP(O)(OR2)3−n
(式中、nは1又は2であり、R1は1〜6の炭素原子数のアルキル基であり、R2はフェニル基である。)
前記フォームが少なくとも100のイソシアネートインデックスである、前記難燃性ポリウレタンフォーム組成物。 - R1がn−ブチル又はイソブチル基であり、R2がフェニル基である、請求項1記載の難燃性ポリウレタンフォーム組成物。
- 前記リン酸エステルが、ジエチルフェニルホスフェート、エチルジフェニルホスフェート、ジ−n−プロピルフェニルホスフェート、n−プロピルジフェニルホスフェート、ジ−n−ブチルフェニルホスフェート、n−ブチルジフェニルホスフェート、ジイソブチルフェニルホスフェート、イソブチルジフェニルホスフェート、ジ−n−ペンチルフェニルホスフェート、n−ペンチルジフェニルホスフェート、ジ−n−ヘキシルフェニルホスフェート、n−ヘキシルジフェニルホスフェート及びそれらの混合物からなる群から選択される、請求項1記載の難燃性ポリウレタンフォーム組成物。
- 前記リン酸エステルが、n−ブチルジフェニルホスフェート、ジ−n−ブチルフェニルホスフェート及びそれらの混合物からなる群から選択される、請求項3記載の難燃性ポリウレタンフォーム組成物。
- 前記リン酸エステルが、イソブチルジフェニルホスフェート、ジイソブチルフェニルホスフェート及びそれらの混合物からなる群から選択される、請求項3記載の難燃性ポリウレタンフォーム組成物。
- 前記リン酸エステルが、ジ−n−ブチルフェニルホスフェート、n−ブチルジフェニルホスフェート及びそれらの混合物からなる群から選択される、請求項3記載の難燃性ポリウレタンフォーム組成物。
- 前記リン酸エステルが、ジイソブチルフェニルホスフェート、イソブチルジフェニルホスフェート及びそれらの混合物からなる群から選択される、請求項3記載の難燃性ポリウレタンフォーム組成物。
- ポリウレタンフォーム形成用組成物中のリン酸エステル含量が、ポリウレタンフォーム成分の合計量に対して1〜6重量%の量である、請求項1記載の難燃性ポリウレタンフォーム組成物。
- ポリウレタンフォーム形成用組成物中のリン酸エステル含量が、ポリウレタンフォーム成分の合計量に対して2〜4重量%の量である、請求項8記載の難燃性ポリウレタンフォーム組成物。
- 40kg/m3(2.50ポンド/ft3)以下の密度である、請求項1記載の難燃性ポリウレタンフォーム組成物。
- 20kg/m3(1.25ポンド/ft3)超の密度である、請求項10記載の難燃性ポリウレタンフォーム組成物。
- 有機イソシアネート及びポリオール成分の指数が少なくとも200である、請求項1記載の難燃性ポリウレタンフォーム組成物。
- 前記イソシアネートインデックスが100〜400であり、ポリイソシアネート、ポリオール、触媒、発泡剤、界面活性剤及び架橋剤からなる群から選択される少なくとも1つの成分を更に含有し、かつ、ハロゲンフリーである、請求項1記載の難燃性ポリウレタンフォーム組成物。
- 燃焼防止にとり有効量の少なくとも1つのリン酸エステル添加剤の存在下で、ポリオールと有機イソシアネートとを反応させることを含んでなり、前記リン酸エステルが下記の一般式で表され、
(R1O)nP(O)(OR2)3−n
(式中、nは1又は2であり、R1は1〜6の炭素原子数のアルキル基であり、R2はアリール基である。)
有機イソシアネート及びポリオール成分のインデックスが少なくとも100である、難燃性ポリウレタンフォームの調製方法。 - R1がn−ブチル又はイソブチル基であり、R2がフェニル基である、請求項14記載の方法。
- 前記リン酸エステルが、ジエチルフェニルホスフェート、エチルジフェニルホスフェート、ジ−n−プロピルフェニルホスフェート、n−プロピルジフェニルホスフェート、ジ−n−ブチルフェニルホスフェート、n−ブチルジフェニルホスフェート、ジイソブチルフェニルホスフェート、イソブチルジフェニルホスフェート、ジ−n−ペンチルフェニルホスフェート、n−ペンチルジフェニルホスフェート、ジ−n−ヘキシルフェニルホスフェート、n−ヘキシルジフェニルホスフェート及びそれらの混合物からなる群から選択される、請求項14記載の方法。
- 前記リン酸エステルが、n−ブチルジフェニルホスフェート、ジ−n−ブチルフェニルホスフェート及びそれらの混合物からなる群から選択される、請求項16記載の方法。
- 前記リン酸エステルが、イソブチルジフェニルホスフェート、ジイソブチルフェニルホスフェート及びそれらの混合物からなる群から選択される、請求項16記載の方法。
- 前記リン酸エステルが、ジ−n−ブチルフェニルホスフェート、n−ブチルジフェニルホスフェート及びそれらの混合物からなる群から選択される、請求項16記載の方法。
- 前記リン酸エステルが、ジイソブチルフェニルホスフェート、イソブチルジフェニルホスフェート及びそれらの混合物からなる群から選択される、請求項16記載の方法。
- ポリウレタンフォーム形成用組成物中のリン酸エステル含量が、ポリウレタンフォーム成分の合計量に対して1〜6重量%の量である、請求項14記載の方法。
- ポリウレタンフォーム形成用組成物中のリン酸エステル含量が、ポリウレタンフォーム成分の合計量に対して2〜4重量%の量である、請求項14記載の方法。
- ポリウレタンフォーム組成物が、40kg/m3(2.50ポンド/ft3)以下の密度である、請求項14記載の方法。
- ポリウレタンフォーム組成物が、20kg/m3(1.25ポンド/ft3)超の密度である、請求項23記載の方法。
- 前記イソシアネートインデックスが100〜400であり、ポリイソシアネート、ポリオール、触媒、発泡剤、界面活性剤及び架橋剤からなる群から選択される少なくとも1つの成分を更に含有し、かつ、ハロゲンフリーである、請求項14記載の方法。
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US75706406P | 2006-01-06 | 2006-01-06 | |
US60/757,064 | 2006-01-06 | ||
PCT/US2007/000443 WO2007081903A1 (en) | 2006-01-06 | 2007-01-05 | Non-halogen flame retardant additives for use in rigid polyurethane foam |
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US (1) | US20090156704A1 (ja) |
EP (1) | EP1973965B1 (ja) |
JP (1) | JP5507848B2 (ja) |
KR (1) | KR20080113344A (ja) |
CN (1) | CN101395209B (ja) |
AT (1) | ATE440894T1 (ja) |
CA (1) | CA2636108C (ja) |
DE (1) | DE602007002161D1 (ja) |
ES (1) | ES2332294T3 (ja) |
PL (1) | PL1973965T3 (ja) |
TW (1) | TW200738800A (ja) |
WO (1) | WO2007081903A1 (ja) |
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ES2672975T3 (es) * | 2007-01-30 | 2018-06-19 | Dow Global Technologies Llc | Polioles iniciados con amina y espuma rígida de poliuretano obtenida a partir de ellos |
US9725555B2 (en) | 2010-09-09 | 2017-08-08 | Innovative Urethane, Llc | Sugar-based polyurethanes, methods for their preparation, and methods of use thereof |
US9676896B2 (en) | 2010-09-09 | 2017-06-13 | Innovative Urethane, Llc | Sugar-based polyurethanes, methods for their preparation, and methods of use thereof |
CN102516484A (zh) * | 2011-12-15 | 2012-06-27 | 温州市登达化工有限公司 | 节能保温纳米墙体用聚氨酯原液合成工艺 |
US10428170B1 (en) * | 2012-07-31 | 2019-10-01 | Huntsman International Llc | Hydrocarbon blown polyurethane foam formulation giving desirable thermal insulation properties |
US20140066532A1 (en) * | 2012-09-06 | 2014-03-06 | Bayer Materialscience Llc | Rigid foams suitable for wall insulation |
US9522973B2 (en) | 2012-10-02 | 2016-12-20 | Covestro Llc | Polyurethane and polyisocyanurate rigid foams for roofing insulation |
EP2931779B1 (en) | 2012-12-14 | 2017-08-30 | Dow Global Technologies LLC | Flame retardant foam formulations |
CN103059249A (zh) * | 2013-01-04 | 2013-04-24 | 安徽大学 | 一种零臭氧损耗潜势且无卤阻燃型聚氨酯硬泡的制备方法 |
US10323116B2 (en) | 2013-03-15 | 2019-06-18 | Imperial Sugar Company | Polyurethanes, polyurethane foams and methods for their manufacture |
TW201546174A (zh) * | 2014-02-27 | 2015-12-16 | Sekisui Chemical Co Ltd | 配管用或機器用耐火性絕熱被覆材 |
US9523195B2 (en) * | 2014-06-09 | 2016-12-20 | Johns Manville | Wall insulation boards with non-halogenated fire retardant and insulated wall systems |
EP3374410B1 (en) * | 2015-11-13 | 2021-01-06 | ICL-IP America Inc. | Reactive flame retardants for polyurethane and polyisocyanurate foams |
US10144798B2 (en) * | 2015-12-21 | 2018-12-04 | Covestro Llc | Methods for designing polyisocyanurate foam-forming compositions, related polyisocyanurate foam-forming compositions, and foams produced thereby |
CN109280350B (zh) * | 2018-08-09 | 2021-08-24 | 束建军 | 一种快速成型可降解复合材料及其制备方法 |
NL2022275B1 (en) | 2018-12-21 | 2020-07-15 | Stahl Int B V | Process to prepare halogen-free, flame-retardant aqueous polyurethane dispersions |
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US3251785A (en) * | 1961-02-14 | 1966-05-17 | Socony Mobil Oil Co Inc | Flame retardant polyurethane foam and method for forming same |
DE2708447A1 (de) * | 1976-03-06 | 1977-09-08 | Ciba Geigy Ag | Flammhemmende polymerzusammensetzungen |
US4169922A (en) * | 1977-12-27 | 1979-10-02 | Monsanto Company | Rigid polyurethane foam-forming compositions |
DE3005477A1 (de) * | 1980-02-14 | 1981-08-20 | Chemische Fabrik Kalk GmbH, 5000 Köln | Brandgeschuetzte polyurethan-integralschaeume |
DE3367782D1 (en) * | 1982-10-12 | 1987-01-08 | Ciba Geigy Ag | Fire-retarding compositions |
DE4121161A1 (de) * | 1991-06-27 | 1993-01-07 | Basf Ag | Verfahren zur herstellung von urethan- oder urethan- und isocyanuratgruppen enthaltenden hartschaumstoffen und treibmittel enthaltende emulsionen hierfuer |
US5457139A (en) * | 1993-07-26 | 1995-10-10 | Monsanto Company | Flexible water-blown polyurethane foams |
GB9416334D0 (en) * | 1994-08-10 | 1994-10-05 | Fmc Corp Uk Ltd | Transesterification process |
US20030216484A1 (en) * | 2002-05-20 | 2003-11-20 | Phillips Matthew D. | Blends of (alkyl substituted) triaryl phosphate esters with phosphorus-containing flame retardants for polyurethane foams |
US20040171722A1 (en) * | 2003-02-28 | 2004-09-02 | Brown William R. | Flame retardant polyurethanes and additive compositions for use in producing them |
US20060111459A9 (en) * | 2003-08-29 | 2006-05-25 | Bradford Larry L | Flame retardant composition and polyurethane foam containing same |
EP1526137A1 (en) * | 2003-10-24 | 2005-04-27 | Akzo Nobel N.V. | Process to prepare alkyl phenyl phosphates |
US7495131B2 (en) * | 2005-03-18 | 2009-02-24 | Air Products And Chemicals, Inc. | Blowing catalyst compositions containing hydroxyl and surface active groups for the production of polyurethane foams |
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CN101395209B (zh) | 2013-06-26 |
US20090156704A1 (en) | 2009-06-18 |
ES2332294T3 (es) | 2010-02-01 |
KR20080113344A (ko) | 2008-12-30 |
PL1973965T3 (pl) | 2010-01-29 |
DE602007002161D1 (de) | 2009-10-08 |
CA2636108C (en) | 2014-10-07 |
WO2007081903A1 (en) | 2007-07-19 |
TW200738800A (en) | 2007-10-16 |
JP2009522432A (ja) | 2009-06-11 |
EP1973965A1 (en) | 2008-10-01 |
CA2636108A1 (en) | 2007-07-19 |
CN101395209A (zh) | 2009-03-25 |
ATE440894T1 (de) | 2009-09-15 |
EP1973965B1 (en) | 2009-08-26 |
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