WO2009009006A1 - Flame retardant composition and flexible polyurethane foam prepared therewith - Google Patents
Flame retardant composition and flexible polyurethane foam prepared therewith Download PDFInfo
- Publication number
- WO2009009006A1 WO2009009006A1 PCT/US2008/008281 US2008008281W WO2009009006A1 WO 2009009006 A1 WO2009009006 A1 WO 2009009006A1 US 2008008281 W US2008008281 W US 2008008281W WO 2009009006 A1 WO2009009006 A1 WO 2009009006A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- flame retardant
- weight percent
- polyurethane foam
- retardant composition
- amount
- Prior art date
Links
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 title claims abstract description 128
- 239000003063 flame retardant Substances 0.000 title claims abstract description 114
- 239000000203 mixture Substances 0.000 title claims abstract description 95
- 229920005830 Polyurethane Foam Polymers 0.000 title claims description 18
- 239000011496 polyurethane foam Substances 0.000 title claims description 18
- 239000003381 stabilizer Substances 0.000 claims abstract description 80
- 150000002596 lactones Chemical class 0.000 claims abstract description 35
- 150000002118 epoxides Chemical class 0.000 claims abstract description 25
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000003623 enhancer Substances 0.000 claims abstract description 14
- 239000004814 polyurethane Substances 0.000 claims description 53
- 229920002635 polyurethane Polymers 0.000 claims description 49
- 229920005862 polyol Polymers 0.000 claims description 45
- 150000003077 polyols Chemical class 0.000 claims description 45
- 239000005056 polyisocyanate Substances 0.000 claims description 41
- 229920001228 polyisocyanate Polymers 0.000 claims description 41
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 40
- 239000004604 Blowing Agent Substances 0.000 claims description 35
- 239000006260 foam Substances 0.000 claims description 31
- 229920000570 polyether Polymers 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 22
- -1 chlorinated phosphate ester Chemical class 0.000 claims description 22
- 239000001569 carbon dioxide Substances 0.000 claims description 20
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 20
- 239000004215 Carbon black (E152) Substances 0.000 claims description 19
- 125000005442 diisocyanate group Chemical group 0.000 claims description 19
- 229930195733 hydrocarbon Natural products 0.000 claims description 19
- 150000002430 hydrocarbons Chemical class 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 13
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 12
- 239000004593 Epoxy Substances 0.000 claims description 10
- 150000002989 phenols Chemical class 0.000 claims description 9
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- WOURXYYHORRGQO-UHFFFAOYSA-N Tri(3-chloropropyl) phosphate Chemical compound ClCCCOP(=O)(OCCCCl)OCCCCl WOURXYYHORRGQO-UHFFFAOYSA-N 0.000 claims description 4
- 150000004982 aromatic amines Chemical class 0.000 claims description 4
- 150000005846 sugar alcohols Polymers 0.000 claims description 4
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 claims description 4
- YQKGJRGUAQVYNL-UHFFFAOYSA-N tris(1,2-dichloropropan-2-yl) phosphate Chemical compound ClCC(Cl)(C)OP(=O)(OC(C)(Cl)CCl)OC(C)(Cl)CCl YQKGJRGUAQVYNL-UHFFFAOYSA-N 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims 29
- 150000002009 diols Chemical class 0.000 claims 18
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 3
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims 3
- ZGHUDSLVQAGWEY-UHFFFAOYSA-N [2-[bis(2-chloroethoxy)phosphoryloxymethyl]-3-chloro-2-(chloromethyl)propyl] bis(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCC(CCl)(CCl)COP(=O)(OCCCl)OCCCl ZGHUDSLVQAGWEY-UHFFFAOYSA-N 0.000 claims 2
- NANGQJICIOUURV-UHFFFAOYSA-N 3-phenyl-3h-1-benzofuran-2-one Chemical compound O=C1OC2=CC=CC=C2C1C1=CC=CC=C1 NANGQJICIOUURV-UHFFFAOYSA-N 0.000 claims 1
- 241000237519 Bivalvia Species 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 235000020639 clam Nutrition 0.000 claims 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 150000003014 phosphoric acid esters Chemical class 0.000 description 3
- 229920005906 polyester polyol Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
- JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-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
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-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
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
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- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
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- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 1
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- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229930006000 Sucrose Natural products 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- NBJODVYWAQLZOC-UHFFFAOYSA-L [dibutyl(octanoyloxy)stannyl] octanoate Chemical compound CCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCC NBJODVYWAQLZOC-UHFFFAOYSA-L 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- ZEFSGHVBJCEKAZ-UHFFFAOYSA-N bis(2,4-ditert-butyl-6-methylphenyl) ethyl phosphite Chemical compound CC=1C=C(C(C)(C)C)C=C(C(C)(C)C)C=1OP(OCC)OC1=C(C)C=C(C(C)(C)C)C=C1C(C)(C)C ZEFSGHVBJCEKAZ-UHFFFAOYSA-N 0.000 description 1
- YTKWTCYBDMELQK-UHFFFAOYSA-N bis(2,4-ditert-butyl-6-methylphenyl)methyl dihydrogen phosphite Chemical compound CC1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1C(OP(O)O)C1=C(C)C=C(C(C)(C)C)C=C1C(C)(C)C YTKWTCYBDMELQK-UHFFFAOYSA-N 0.000 description 1
- SXXILWLQSQDLDL-UHFFFAOYSA-N bis(8-methylnonyl) phenyl phosphite Chemical compound CC(C)CCCCCCCOP(OCCCCCCCC(C)C)OC1=CC=CC=C1 SXXILWLQSQDLDL-UHFFFAOYSA-N 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000002666 chemical blowing agent Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004965 chloroalkyl group Chemical group 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 229940113120 dipropylene glycol Drugs 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical class C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000001282 iso-butane Substances 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
- 239000004611 light stabiliser Substances 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
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ASHGTJPOSUFTGB-UHFFFAOYSA-N methyl resorcinol Natural products COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- QRWZCJXEAOZAAW-UHFFFAOYSA-N n,n,2-trimethylprop-2-enamide Chemical compound CN(C)C(=O)C(C)=C QRWZCJXEAOZAAW-UHFFFAOYSA-N 0.000 description 1
- DFENKTCEEGOWLB-UHFFFAOYSA-N n,n-bis(methylamino)-2-methylidenepentanamide Chemical compound CCCC(=C)C(=O)N(NC)NC DFENKTCEEGOWLB-UHFFFAOYSA-N 0.000 description 1
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- QYZLKGVUSQXAMU-UHFFFAOYSA-N penta-1,4-diene Chemical compound C=CCC=C QYZLKGVUSQXAMU-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 238000006068 polycondensation reaction Methods 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
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 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 1
- 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 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- 239000000326 ultraviolet stabilizing agent Substances 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0066—Flame-proofing or flame-retarding additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1535—Five-membered rings
-
- 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
- C08K2201/00—Specific properties of additives
- C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- 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
- C08L75/08—Polyurethanes from polyethers
Definitions
- This invention relates to flame retardant compositions based on phosphate esters and to flexible polyurethane foams prepared therewith.
- Flexible polyurethane foams are typically formed by reaction of a polyol and a diisocyanate employing water as a chemical blowing agent.
- the foam-forming reaction is highly exothermic, all the more so as the amount of water used in the production of a foam is increased.
- the first essential component of the flame retardant composition of the present invention can be selected from among any of the known and conventional flame retardant compounds heretofore indicated for use in imparting flame retardant properties to synthetic resins in general and to flexible polyurethane foams in particular. Reference may be had in this regard to the classes of flame retardant compounds and individual species thereof disclosed, inter alia, in U.S. Patent No. 7,138,448, the entire contents of which are incorporated by reference herein.
- Representative compounds of this type that can be used herein with generally good results include tris(chloroethyl) phosphate (TCEP), tris(chloropropyl) phosphate (TCPP), tris(dichloroisopropyl) phosphate (TDCP) and 2,2-bis(chloromethyl) trimethylene bis[bis(2-chloroethyl) phosphate] (chlorinated diphosphate or V6 type product) and their mixtures.
- TCEP tris(chloroethyl) phosphate
- TCPP tris(chloropropyl) phosphate
- TDCP tris(dichloroisopropyl) phosphate
- 2,2-bis(chloromethyl) trimethylene bis[bis(2-chloroethyl) phosphate] chlorinated diphosphate or V6 type product
- Mixtures of different organophosphorus compounds are also contemplated, e.g., mixtures of halogenated and non-halogenated
- the organophosphorus flame retardant component can also be an oligomeric organophosphorus flame retardant, preferably one having a phosphorus content of not less than about 5% by weight.
- Flame retardant(s) (i) will typically constitute the major amount of the flame retardant composition herein, e.g., from 75 to 99.5, and preferably from 90 to 99, weight percent thereof.
- the second essential component of the flame retardant composition herein is a lactone stabilizer such as any of those heretofore employed for the stabilization of flame retardants.
- Suitable flame retardants include one or more lactones such as caprolactone, butyrolactone and valerolactone, indolinones such as any of those disclosed in U.S. Patent Nos. 4,325,863 and 4,338,244, the entire contents of which are incorporated by reference herein, and benzofuranones such as any of those disclosed in aforementioned U.S. Patent Nos. 4,325,863, and 4,338,244, and in U.S. Patent Nos. 5,175,312, 5,308,899, 5,807,505 and 5,869,565, the entire contents of which are incorporated by reference herein.
- Preferred benzofuranones are the benzofuran-2-ones.
- the commercially available benzofuranones Irgastab PUR 67 and Irgastab PUR 68 (Ciba Specialty Chemicals) have advantageously been used herein with good results.
- lactone stabilizer (ii) incorporated in the flame retardant composition of the invention can vary considerably depending on the particular stabilizer selected as well as the nature and amounts of the other components of the composition.
- the lactone stabilizer (ii) can be present in the flame retardant composition at a level of from 0.01 to 5, and preferably from 0.02 to 2, weight percent thereof.
- the third essential component of the flame retardant composition of this invention is a phosphite stabilizer, e.g., any of those heretofore employed as stabilizers for flame retardant compositions.
- a phosphite stabilizer e.g., any of those heretofore employed as stabilizers for flame retardant compositions.
- useful phosphite stabilizers which can be incorporated in the flame retardant compositions herein are those described in U.S. Patent No. 7,109,260, the entire contents of which are incorporated by reference herein.
- Some useful phosphite stabilizers herein include triaryl phosphites; diaryl alkyl phosphites; aryl dialkyl phosphites; tris(nonylphenyl)phosphite; trilauryl phosphite; trioctadecyl phosphite; distearyl pentaerythritol diphosphite; tris(2,4-di-tert-butylphenyl)phosphite; diisodecyl phenyl phosphite; diisodecyl pentaerythritol diphosphite; bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite; bis(2,6-di-tert-butyl-4-methylphenyl)-pentaerythritol diphosphite; diisodecyloxy
- 2,2',2"-nitrilo triethyltris(3,3',5,5'-tetra-tert-butyl-l,r-biphe- nyl-2,2'-diyl)phosphite]; 2- ethylhexyl(3,3',5,5'-tetra-tert-butyl-l,r-biphenyl-2,2'-diyl)phosphite; trialkyl phosphites; and, tris(dipropyleneglycol)phosphite.
- phosphite stabilizer (iii) can be present in the flame retardant composition herein at a level of from 0.01 to 10, and preferably from 0.02 to 5, weight percent thereof.
- the fourth essential component of the flame retardant composition of the invention is an epoxide stabilizer.
- Preferred epoxide stabilizers have an epoxide equivalent weight of not greater than 500, more preferably not greater than 300 and preferably not greater than 250.
- Suitable epoxide stabilizers include epoxy carboxylic acids such as epoxy stearic acid; glycidyl ethers of polyhydric alcohols and phenols such as triglycidyl glycerine, diglycidyl ether of diethylene glycol, glycidyl epoxy stearyl ether, l,4-bis(2,3- epoxypropoxy)benzene, 4,4'-bis(2,3-epoxypropoxy) diphenyl ether, l,8-bis(2,3- epoxypropoxy) octane, l,4-bis-(2,3-epoxypropoxy) cyclohexane, tetraglycidyl ether of tetra (parahydroxylphenyl) ethane and l,3-bis(4,5-epoxypentoxy) 5-chlorobenzene; the epoxy polyethers of polyhydric phenols, obtained by reacting a polyhydric phenol with a
- the flame retardant composition can contain epoxide stabilizer (iv) at a level of from 0.01 weight percent to about 10, and preferably from about 0.02 weight percent to about 5 weight percent thereof.
- phenolic alkyl esters and /or arylamines that enhance the performance of the relatively expensive benzofuranone-type stabilizers thus allowing for reduction in the amount of benzofuranone stabilizer without a reduction in stabilizing effectiveness.
- Irgastab PUR 67 and Irgastab PUR 68 both of which are stabilizer packages containing a benzofuranone-type stabilizer, are also believed to contain performance enhancing amounts of ester and amine components.
- a flexible polyurethane foam- forming composition which, under polyurethane foam- forming conditions, provides a flame-retardant flexible polyurethane foam, the composition comprising: a) at least one polyol; b) at least one polyisocyanate; c) at least one blowing agent; d) at least one catalyst for the polyurethane foam-forming reaction; e) at least one flame retardant composition which comprises: (i) at least one flame retardant,
- polyols which can be used include those commonly used in the production of flexible polyurethane foams such as polyether polyols, polyester polyols and polymer polyols.
- polyether polyols include those with a hydroxyl value of from 25 to 70 KOHmg/g which are obtained by the random or block addition of alkylene oxides such as ethylene oxide and propylene oxide to polyfunctional polyols, amine compounds, and the like.
- polyfunctional polyols include glycols such as ethylene glycol and propylene glycol; triols such as glycerol and trimethylolpropane; polyols such as pentaerythritol, sorbitol and sucrose.
- amine compounds include ammonia, triethanolamine, ethylene diamine, diethylene triamine, aminoethyl piperazine and aniline.
- Polyester polyols are compounds having terminal hydroxyl groups obtained by the polycondensation of polyfunctional carboxylic acids and polyfunctional hydroxyl compounds or the ring-opening self-condensation polymerizations of a lactone.
- the polyester polyols preferably have a number average molecular weight of from 500 to 10,000, and more preferably from 1000 to 5000.
- polyfunctional carboxylic acids include adipic acid, phthalic acid, succinic acid, azelaic acid and sebacic acid.
- polyfunctional hydroxy compounds examples include glycols such as ethylene glycol, propylene glycol, butanediol and diethylene glycol, and polyhydric alcohols such as glycerol, trimethylol propane and pentaerythritol.
- polyhydric alcohols such as glycerol, trimethylol propane and pentaerythritol.
- lactones include gamma- butyrolactone and epsilon-caprolactone.
- Polymer polyols can be obtained by mixing a polyether polyol and an ethylenically unsaturated monomer, and, when necessary, adding chain transfer agents, dispersion stabilizers, and the like, to bring about the radical polymerization of the ethylenically unsaturated monomer in the presence of a radical initiator.
- ethylenically unsaturated monomers include monomers containing the cyano group such as acrylonitrile and methacrylonitrile; (meth)acrylic esters such as methyl (meth)acrylate, butyl (meth)acrylate, stearyl (meth)acrylate, hydroxyethyl (meth)acrylate, dimethylaminoethyl (meth)acrylate and dimethylaminopropyl (meth)acrylate; monomers containing carboxyl group such as acrylic acid, methacrylic acid, itaconic acid, maleic acid and fumaric acid; acid anhydride monomers such as maleic anhydride and itaconic anhydride; hydrocarbon compounds such as butadiene, isoprene and 1 ,4-pentadiene; aromatic hydrocarbon compounds such as styrene, alpha-methyl styrene, phenylstyrene and chlorostyrene; halogen-containing monomers such as
- Such ethylenically unsaturated monomers can be used alone or in combinations of two or more.
- the aforementioned polyol components can be used alone or in combinations of two or more depending on the properties required of the flexible polyurethane foam that is to be prepared.
- a flexible polyurethane foam with high elasticity can be obtained when the aforementioned polyether polyol and polymer polyol are used in a proportion, based on the combined weight of the two, of from 30 to 90 weight percent of the former and from 70 to 10 weight percent of the latter, and preferably from 40 to 80 weight percent of the former and from 60 to 20 weight percent of the latter.
- polyisocyanates which can be used include those having two or more isocyanate groups which have heretofore been used for making flexible polyurethane foams.
- polyisocyanate compounds include aromatic polyisocyanates, aliphatic polyisocyanates and alicyclic polyisocyanates, as well as mixtures of two or more of such polyisocyanates, and modified polyisocyanates obtained by the modification of such polyisocyanates.
- polyisocyanates are tolylene diisocyanate, diphenylmethane diisocyanate, polymethylene polyphenylene polyisocyanate (crude MDI), xylylene diisocyanate, isophorone diisocyanate and hexamethylene diisocyanate; and modified products of such polyisocyanates, such as carbodiimide-modified products, biuret-modified products, dimers and trimers.
- Prepolymers with terminal isocyanate groups obtained from such polyisocyanates and active hydrogen-containing compounds can also be used.
- blowing agent in the flexible polyurethane foam-forming composition of the present invention known blowing agents heretofore used in such compositions are suitably selected according to the properties required of the foamed product.
- Water is a typical example of such a blowing agent; other examples include methylene chloride, n-butane, isobutane, n-pentane, isopentane, dimethyl ether, acetone, carbon dioxide, and the like.
- these and other blowing agents can be used alone or in combinations of two or more in a manner known in the art.
- the amount of blowing agent to be used is not particularly limited but will ordinarily range from 0.1 to 40 parts by weight per 100 parts by weight of the polyol component of the foam- forming composition.
- the amount of blowing agent(s) will be such as to provide a foam density of from 0.8 to 2.5 pounds per cubic foot, and preferably from 0.9 to 2.0 pounds per cubic foot.
- the flexible polyurethane foam-forming composition herein can contain any of the catalysts, and combination of catalysts, heretofore known or used for the production of polyurethane foams.
- useful catalysts include sodium hydroxide, sodium acetate, tertiary amines or materials which generate tertiary amines such as trimethylamine, triethylene diamine, N-methyl morpholine, N,N-dimethyl cyclohexylamine, and N,N-dimethyl aminoethanol.
- metal compounds such as hydrocarbon tin alkyl carboxylates, dibutyl tin diacetate, dibutyl tin dioctoate dibutyl tin dilaurate and stannous octoate; as well as other compounds intended to promote trimerization of the polyisocyanate such as, 2,4,6-tris(N,N-dimethylamino- methyl)phenol, 1 ,3 ,5-tris(N,N-dimethyl-3-aminopropyl)-S-hexahydrotriazine, potassium octoate, potassium acetate and catalysts such as DABCO TMR ® and POLYCAT 43 ® .
- catalysts can be substituted for those listed above, if desired.
- the amount of catalyst used can advantageously range from 0.05 to 5 weight percent or more based on the total weight of polyol in the foam-forming mixture.
- Flame retardant composition (e), supra, can be incorporated into the foam- forming composition in widely varying amounts. In general, such amounts can range from 1 to 15, and preferably from 4 to 12, weight percent of the entire foam- forming composition.
- an emulsifier and/or surfactant may be incorporated in therein. These materials are physical in their effect and are not always necessary, especially if denser foams are desired. Any of the many hundreds of conventional surfactants can be used in amounts of up to about 5 weight percent based on the weight of the total polyol component. Suitable surfactants are polydimethylsiloxane and polydimethylsiloxane polyalkylene copolymers, and the like.
- Such components include, without limitation, adhesion promoters, antioxidants, antistatic agents, antimicrobials, dyes, heat stabilizers, light stabilizers, pigments, plasticizers, preservatives, ultraviolet stabilizers, and fillers in the customary amounts.
- a standard flexible polyurethane foam-forming reaction medium was prepared containing individual flame retardant compositions outside the scope of the invention (resulting foams: Comp. Ex. 1-8) and illustrative of the invention (resulting foam: Example 2 containing the flame retardant composition of Example 1). Following foaming, the resulting foams were evaluated for scorch, reported as "b" value, the higher numerical value correlating with a more yellow foam indicating a higher level of scorch. The results of the scorch evaluations are summarized below:
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Abstract
A flame retardant composition comprises: (i) at least one flame retardant; (ii) at least one lactone stabilizer; (iii) at least one phosphite stabilizer; (iv) at least one epoxide stabilizer; and, (v) optionally, at least one stabilizer performance enhancer for lactone stabilizer (ii).
Description
FLAME RETARDANT COMPOSITION AND FLEXIBLE POLYURETHANE FOAM PREPARED THEREWITH
BACKGROUND OF THE INVENTION Field of the Invention
[0001] This invention relates to flame retardant compositions based on phosphate esters and to flexible polyurethane foams prepared therewith.
Description of the Prior Art
[0002] Flexible polyurethane foams are well known to be highly flammable.
They are widely employed as cushioning or padding materials in upholstered furniture, mattresses and automotive seating, as sound insulation in vehicles and for vibration dampening generally. These and similar applications require that they contain an effective flame retardant additive such as a halogenated phosphate ester.
[0003] Flexible polyurethane foams are typically formed by reaction of a polyol and a diisocyanate employing water as a chemical blowing agent. The foam-forming reaction is highly exothermic, all the more so as the amount of water used in the production of a foam is increased.
[0004] Recently, there has been an industry trend toward the production of lower density polyurethane foams, e.g., foams having a density of not greater than about 1.4 lb/ft3. A problem in the manufacture of such foams arises as a result of the relatively large amounts of water that are needed to provide the volumes of carbon dioxide gas (via the highly exothermic reaction of water with isocyanate groups) necessary to achieve the desired low densities. The still higher exotherm associated with the use of relatively large amounts of water can cause core discoloration (referred to as "scorch") in the resulting foams and can also result in some degradation of the polyols from which the polyurethane foams are derived and consequently some degradation in the mechanical properties of the foams.
SUMMARY OF THE INVENTION
[0005] It has now been discovered that the effectiveness of a phosphate ester-type flame retardant for inhibiting or reducing scorch in flexible polyurethane foams can be significantly improved by the addition thereto of a flame retardant-effective amount of a flame retardant composition which comprises:
(i) at least one flame retardant; (ii) at least one lactone stabilizer; (iii) at least one phosphite stabilizer; (iv) at least one epoxide stabilizer; and,
(v) optionally, at least one stabilizer performance enhancer for lactone stabilizer (ii).
[0006] Other than in the working examples or where otherwise indicated, all numbers expressing amounts of materials, properties of materials, and so forth, stated herein are to be understood as being modified in all instances by the term "about."
[0007] Each numerical range recited herein shall be understood to include all subranges within that range.
[0008] Any compound, material or substance which is expressly or implicitly disclosed herein as belonging to a group of structurally, compositionally and/or functionally related compounds, materials or substances shall be understood to include individual members of the group and all combinations thereof.
DETAILED DESCRIPTION OF THE INVENTION
I. THE FLAME RETARDANT COMPOSITION
[0009] Each of components (i)-(v) of the flame retardant composition of the invention and their amounts therein are hereinafter described.
(i) Flame Retardant
[0010] The first essential component of the flame retardant composition of the present invention can be selected from among any of the known and conventional flame retardant compounds heretofore indicated for use in imparting flame retardant properties to synthetic resins in general and to flexible polyurethane foams in particular. Reference may be had in this regard to the classes of flame retardant compounds and individual species thereof disclosed, inter alia, in U.S. Patent No. 7,138,448, the entire contents of which are incorporated by reference herein.
[0011] A preferred class of flame retardant compounds are those of the organophosphorus type, in particular, monomelic phosphate esters of the formula O=P-(OR)3 wherein R is independently selected from alkyl, alkoxyalkyl and haloalkyl containing up to about 8 carbon atoms. Preferred are substitutents that are halogenated, e.g., chloroalkyl containing from 1 to 4 carbon atoms. Representative compounds of this type that can be used herein with generally good results include tris(chloroethyl) phosphate (TCEP), tris(chloropropyl) phosphate (TCPP), tris(dichloroisopropyl) phosphate (TDCP) and 2,2-bis(chloromethyl) trimethylene bis[bis(2-chloroethyl) phosphate] (chlorinated diphosphate or V6 type product) and their mixtures. Mixtures of different organophosphorus compounds are also contemplated, e.g., mixtures of halogenated and non-halogenated phosphate esters.
[0012] The organophosphorus flame retardant component can also be an oligomeric organophosphorus flame retardant, preferably one having a phosphorus content of not less than about 5% by weight.
[0013] Flame retardant(s) (i) will typically constitute the major amount of the flame retardant composition herein, e.g., from 75 to 99.5, and preferably from 90 to 99, weight percent thereof.
(ii) Lactone Stabilizer
[0014] The second essential component of the flame retardant composition herein is a lactone stabilizer such as any of those heretofore employed for the stabilization of flame retardants. Suitable flame retardants include one or more lactones such as caprolactone, butyrolactone and valerolactone, indolinones such as any of those disclosed in U.S. Patent Nos. 4,325,863 and 4,338,244, the entire contents of which are incorporated by reference herein, and benzofuranones such as any of those disclosed in aforementioned U.S. Patent Nos. 4,325,863, and 4,338,244, and in U.S. Patent Nos. 5,175,312, 5,308,899, 5,807,505 and 5,869,565, the entire contents of which are incorporated by reference herein.
[0015] Preferred benzofuranones are the benzofuran-2-ones. The commercially available benzofuranones Irgastab PUR 67 and Irgastab PUR 68 (Ciba Specialty Chemicals) have advantageously been used herein with good results.
[0016] The amounts of lactone stabilizer (ii) incorporated in the flame retardant composition of the invention can vary considerably depending on the particular stabilizer selected as well as the nature and amounts of the other components of the composition. Generally, the lactone stabilizer (ii) can be present in the flame retardant composition at a level of from 0.01 to 5, and preferably from 0.02 to 2, weight percent thereof.
(iii) Phosphite Stabilizer
[0017] The third essential component of the flame retardant composition of this invention is a phosphite stabilizer, e.g., any of those heretofore employed as stabilizers for flame retardant compositions. Among the useful phosphite stabilizers which can be incorporated in the flame retardant compositions herein are those described in U.S. Patent No. 7,109,260, the entire contents of which are incorporated by reference herein.
[0018] Some useful phosphite stabilizers herein include triaryl phosphites; diaryl alkyl phosphites; aryl dialkyl phosphites; tris(nonylphenyl)phosphite; trilauryl phosphite; trioctadecyl phosphite; distearyl pentaerythritol diphosphite; tris(2,4-di-tert-butylphenyl)phosphite; diisodecyl phenyl phosphite; diisodecyl pentaerythritol diphosphite; bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite; bis(2,6-di-tert-butyl-4-methylphenyl)-pentaerythritol diphosphite; diisodecyloxypentaerythritol diphosphite; bis(2,4-di-tert-butyl-6-methylphenyl)pentaerythritol diphosphite; bis(2,4,6-tris(tert-butylphenyl)pentaerythritol diphosphite; tristearyl sorbitol triphosphite; bis(2,4-di-tert-butyl-6-methylphenyl)methyl phosphite; bis(2,4-di-tert-butyl-6-methylphenyl)ethyl phosphite;
2,2',2"-nitrilo[triethyltris(3,3',5,5'-tetra-tert-butyl-l,r-biphe- nyl-2,2'-diyl)phosphite]; 2- ethylhexyl(3,3',5,5'-tetra-tert-butyl-l,r-biphenyl-2,2'-diyl)phosphite; trialkyl phosphites; and, tris(dipropyleneglycol)phosphite.
[0019] hi general, phosphite stabilizer (iii) can be present in the flame retardant composition herein at a level of from 0.01 to 10, and preferably from 0.02 to 5, weight percent thereof.
(iv) Epoxide Stabilizer
[0020] The fourth essential component of the flame retardant composition of the invention is an epoxide stabilizer. Preferred epoxide stabilizers have an epoxide equivalent weight of not greater than 500, more preferably not greater than 300 and preferably not greater than 250.
[0021] Suitable epoxide stabilizers include epoxy carboxylic acids such as epoxy stearic acid; glycidyl ethers of polyhydric alcohols and phenols such as triglycidyl glycerine, diglycidyl ether of diethylene glycol, glycidyl epoxy stearyl ether, l,4-bis(2,3- epoxypropoxy)benzene, 4,4'-bis(2,3-epoxypropoxy) diphenyl ether, l,8-bis(2,3- epoxypropoxy) octane, l,4-bis-(2,3-epoxypropoxy) cyclohexane, tetraglycidyl ether of tetra (parahydroxylphenyl) ethane and l,3-bis(4,5-epoxypentoxy) 5-chlorobenzene; the
epoxy polyethers of polyhydric phenols, obtained by reacting a polyhydric phenol with a halogen-containing epoxide or dihalohydrin such as the reaction products of resorcinol, catechol, hydroquinone, methyl resorcinol or polynuclear phenols such as 2,2'-bis(4- hydroxyphenyl) propane (Bisphenol A), 2,2'-bis (4-hydroxyphenyl) butane, 4,4'- dihydroxy-benzophenone and 1,5-dihydroxy naphthalene with halogen-containing epoxides such as 3-chloro-l,2-epoxybutane, 3-chloro-l,2-epoxyoctane and epichlorohydrin; diepoxides containing two linked cyclohexane groups each of which possesses a fused epoxide ring such as 3,4-epoxycyclohexylmethyl-3,4- epoxycyclohexane carboxylate, bis(3,4-epoxy-6-methylcyclohexyhnethyl adipate and 2(3,4-epoxycyclohexyl)-5,5-spiro(3,4-epoxy)cyclohexane-m-dioxane; and, the diepoxide 7-oxabicyclo[4.1.0]hept-3-ylmethyl 7-oxabicyclo[4.1.0]heptane-3-carboxylate.
[0022] The flame retardant composition can contain epoxide stabilizer (iv) at a level of from 0.01 weight percent to about 10, and preferably from about 0.02 weight percent to about 5 weight percent thereof.
(v) Stabilizer Performance Enhancer for Lactone Stabilizer in (ii)
[0023] In some cases, it may be desirable to include one or more materials such as phenolic alkyl esters and /or arylamines that enhance the performance of the relatively expensive benzofuranone-type stabilizers thus allowing for reduction in the amount of benzofuranone stabilizer without a reduction in stabilizing effectiveness. Thus, e.g., Irgastab PUR 67 and Irgastab PUR 68 (Ciba Specialty Chemicals) both of which are stabilizer packages containing a benzofuranone-type stabilizer, are also believed to contain performance enhancing amounts of ester and amine components.
II. FLEXIBLE POLYURETHANE FOAM
[0024] In accordance with the present invention, there is provided a flexible polyurethane foam- forming composition which, under polyurethane foam- forming conditions, provides a flame-retardant flexible polyurethane foam, the composition comprising:
a) at least one polyol; b) at least one polyisocyanate; c) at least one blowing agent; d) at least one catalyst for the polyurethane foam-forming reaction; e) at least one flame retardant composition which comprises: (i) at least one flame retardant,
(ii) at least one lactone stabilizer,
(iii) at least one phosphite stabilizer,
(iv) at least one epoxide stabilizer and
(v) optionally, at least one stabilizer performance enhancer for lactone stabilizer (ii); and, f) optionally, one or more other components.
[0025] Individual components (a)-(f) of the foregoing polyurethane foam- forming composition will now be described.
(a) Polvol
[0026] Examples of polyols which can be used include those commonly used in the production of flexible polyurethane foams such as polyether polyols, polyester polyols and polymer polyols.
[0027] Examples of polyether polyols include those with a hydroxyl value of from 25 to 70 KOHmg/g which are obtained by the random or block addition of alkylene oxides such as ethylene oxide and propylene oxide to polyfunctional polyols, amine compounds, and the like. Examples of polyfunctional polyols include glycols such as ethylene glycol and propylene glycol; triols such as glycerol and trimethylolpropane; polyols such as pentaerythritol, sorbitol and sucrose. Examples of amine compounds include ammonia, triethanolamine, ethylene diamine, diethylene triamine, aminoethyl piperazine and aniline.
[0028] Polyester polyols are compounds having terminal hydroxyl groups obtained by the polycondensation of polyfunctional carboxylic acids and polyfunctional hydroxyl compounds or the ring-opening self-condensation polymerizations of a lactone. The polyester polyols preferably have a number average molecular weight of from 500 to 10,000, and more preferably from 1000 to 5000. Examples of polyfunctional carboxylic acids include adipic acid, phthalic acid, succinic acid, azelaic acid and sebacic acid. Examples of polyfunctional hydroxy compounds include glycols such as ethylene glycol, propylene glycol, butanediol and diethylene glycol, and polyhydric alcohols such as glycerol, trimethylol propane and pentaerythritol. Examples of lactones include gamma- butyrolactone and epsilon-caprolactone.
[0029] Polymer polyols can be obtained by mixing a polyether polyol and an ethylenically unsaturated monomer, and, when necessary, adding chain transfer agents, dispersion stabilizers, and the like, to bring about the radical polymerization of the ethylenically unsaturated monomer in the presence of a radical initiator. Examples of ethylenically unsaturated monomers include monomers containing the cyano group such as acrylonitrile and methacrylonitrile; (meth)acrylic esters such as methyl (meth)acrylate, butyl (meth)acrylate, stearyl (meth)acrylate, hydroxyethyl (meth)acrylate, dimethylaminoethyl (meth)acrylate and dimethylaminopropyl (meth)acrylate; monomers containing carboxyl group such as acrylic acid, methacrylic acid, itaconic acid, maleic acid and fumaric acid; acid anhydride monomers such as maleic anhydride and itaconic anhydride; hydrocarbon compounds such as butadiene, isoprene and 1 ,4-pentadiene; aromatic hydrocarbon compounds such as styrene, alpha-methyl styrene, phenylstyrene and chlorostyrene; halogen-containing monomers such as vinyl chloride and vinylidene chloride; vinyl ethers such as vinyl ethyl ether and vinyl butyl ether; vinyl ketones such as vinyl ethyl ketone; vinyl esters such as vinyl acetate; acrylamides such as acrylamide, N,N-dimethylacrylamide, N-isopropylamide, N,N-dimethylaminopropyl acrylamide and methylene bisacrylamide; and methacrylamides such as N,N-dimethyl methacrylamide. Such ethylenically unsaturated monomers can be used alone or in combinations of two or more.
[0030] The aforementioned polyol components can be used alone or in combinations of two or more depending on the properties required of the flexible polyurethane foam that is to be prepared.
[0031] For example, a flexible polyurethane foam with high elasticity can be obtained when the aforementioned polyether polyol and polymer polyol are used in a proportion, based on the combined weight of the two, of from 30 to 90 weight percent of the former and from 70 to 10 weight percent of the latter, and preferably from 40 to 80 weight percent of the former and from 60 to 20 weight percent of the latter.
(b) Polvisocyanate
[0032] Examples of polyisocyanates which can be used include those having two or more isocyanate groups which have heretofore been used for making flexible polyurethane foams. Examples of such polyisocyanate compounds include aromatic polyisocyanates, aliphatic polyisocyanates and alicyclic polyisocyanates, as well as mixtures of two or more of such polyisocyanates, and modified polyisocyanates obtained by the modification of such polyisocyanates. Specific examples of such polyisocyanates are tolylene diisocyanate, diphenylmethane diisocyanate, polymethylene polyphenylene polyisocyanate (crude MDI), xylylene diisocyanate, isophorone diisocyanate and hexamethylene diisocyanate; and modified products of such polyisocyanates, such as carbodiimide-modified products, biuret-modified products, dimers and trimers. Prepolymers with terminal isocyanate groups obtained from such polyisocyanates and active hydrogen-containing compounds can also be used.
(c) Blowing Agent
[0033] As the blowing agent in the flexible polyurethane foam-forming composition of the present invention, known blowing agents heretofore used in such compositions are suitably selected according to the properties required of the foamed product.
[0034] Water is a typical example of such a blowing agent; other examples include methylene chloride, n-butane, isobutane, n-pentane, isopentane, dimethyl ether, acetone, carbon dioxide, and the like. Depending on the desired density and other properties of the foamed polyurethane, these and other blowing agents can be used alone or in combinations of two or more in a manner known in the art.
[0035] The amount of blowing agent to be used is not particularly limited but will ordinarily range from 0.1 to 40 parts by weight per 100 parts by weight of the polyol component of the foam- forming composition. Preferably, the amount of blowing agent(s) will be such as to provide a foam density of from 0.8 to 2.5 pounds per cubic foot, and preferably from 0.9 to 2.0 pounds per cubic foot.
(d) Catalyst
[0036] The flexible polyurethane foam-forming composition herein can contain any of the catalysts, and combination of catalysts, heretofore known or used for the production of polyurethane foams. Examples of useful catalysts include sodium hydroxide, sodium acetate, tertiary amines or materials which generate tertiary amines such as trimethylamine, triethylene diamine, N-methyl morpholine, N,N-dimethyl cyclohexylamine, and N,N-dimethyl aminoethanol. Also applicable are metal compounds such as hydrocarbon tin alkyl carboxylates, dibutyl tin diacetate, dibutyl tin dioctoate dibutyl tin dilaurate and stannous octoate; as well as other compounds intended to promote trimerization of the polyisocyanate such as, 2,4,6-tris(N,N-dimethylamino- methyl)phenol, 1 ,3 ,5-tris(N,N-dimethyl-3-aminopropyl)-S-hexahydrotriazine, potassium octoate, potassium acetate and catalysts such as DABCO TMR® and POLYCAT 43®.
[0037] Many other kinds of catalysts can be substituted for those listed above, if desired. The amount of catalyst used can advantageously range from 0.05 to 5 weight percent or more based on the total weight of polyol in the foam-forming mixture.
(e) Flame Retardant Compositions
[0038] Flame retardant composition (e), supra, can be incorporated into the foam- forming composition in widely varying amounts. In general, such amounts can range from 1 to 15, and preferably from 4 to 12, weight percent of the entire foam- forming composition.
(e) Optional Components')
[0039] In order to obtain relatively uniform distribution of the various components of the flexible polyurethane foam-forming composition and to achieve the desired formation of bubbles in the foamed polyurethane, an emulsifier and/or surfactant may be incorporated in therein. These materials are physical in their effect and are not always necessary, especially if denser foams are desired. Any of the many hundreds of conventional surfactants can be used in amounts of up to about 5 weight percent based on the weight of the total polyol component. Suitable surfactants are polydimethylsiloxane and polydimethylsiloxane polyalkylene copolymers, and the like.
[0040] It is also within the scope of the invention to incorporate one or more other optional components in the flexible polyurethane foam-forming composition where one desires to achieve a particular end result. Such components include, without limitation, adhesion promoters, antioxidants, antistatic agents, antimicrobials, dyes, heat stabilizers, light stabilizers, pigments, plasticizers, preservatives, ultraviolet stabilizers, and fillers in the customary amounts.
[0041] The following example is illustrative of the flame retardant composition of the invention:
EXAMPLE l
[0042] The components of a flame retardant composition herein and their amounts identified below were combined to provide a substantially uniform mixture.
COMPARATIVE EXAMPLES 1-8: EXAMPLE 2
[0043] A standard flexible polyurethane foam-forming reaction medium was prepared containing individual flame retardant compositions outside the scope of the invention (resulting foams: Comp. Ex. 1-8) and illustrative of the invention (resulting foam: Example 2 containing the flame retardant composition of Example 1). Following foaming, the resulting foams were evaluated for scorch, reported as "b" value, the higher numerical value correlating with a more yellow foam indicating a higher level of scorch. The results of the scorch evaluations are summarized below:
[0044] As these data show, the foam of Ex. 2 possessed a significantly lower "b" value than any of the "b" values of the foams of Comp. Ex. 1-8 indicating a greater degree of effectiveness for the flame retardant composition herein.
[0045] Other embodiments of the invention will be apparent to those skilled in the art from a consideration of this specification or practice of the invention disclosed herein. It is intended that the specification and examples be considered as exemplary only, with the true scope and spirit of the invention being defined by the following claims.
Claims
1. A flame retardant composition which comprises: (i) at least one flame retardant;
(ii) at least one lactone stabilizer; (iii) at least one phosphite stabilizer; (iv) at least one epoxide stabilizer; and,
(v) optionally, at least one stabilizer performance enhancer for lactone stabilizer (ii).
2. The flame retardant composition of Claim 1 wherein flame retardant (i) includes at least one organophosphorus flame retardant.
3. The flame retardant composition of Claim 1 wherein flame retardant (i) includes at least one phosphate ester flame retardant.
4. The flame retardant composition of Claim 1 wherein flame retardant (i) includes at least one halogenated phosphate ester flame retardant, and optionally, at least one non- halogenated phosphate ester flame retardant.
5. The flame retardant composition of Claim 1 wherein flame retardant (i) includes at least one chlorinated phosphate ester flame retardant.
6. The flame retardant composition of Claim 1 wherein flame retardant (i) includes at least one chlorinated phosphate ester selected from the group consisting of tris(chloroethyl) phosphate, tris(chloropropyl) phosphate, tris(dichloroisopropyl) phosphate and 2,2-bis (chloromethyl) trimethylene bis[bis(2-chloroethyl) phosphate] and their mixtures.
7. The flame retardant composition of Claim 1 wherein lactone stabilizer (ii) includes at least one benzofuran-2-one.
8. The flame retardant composition of Claim 1 wherein lactone stabilizer (ii) includes at least one 3 -phenyl benzofuran-2-one.
9. The flame retardant composition of Claim 1 wherein phosphite stabilizer (iii) includes at least one member selected from the group consisting of triaryl phosphites, diaryl alkyl phosphites, aryl dialkyl phosphites, trialkyl phosphites and mixtures thereof.
10. The flame retardant composition of Claim 1 wherein epoxide stabilizer (iv) includes at least one member selected from the group consisting of epoxy carboxylic acid; glycidyl ethers ofpolyhydric alcohols and phenols; epoxy polyethers ofpolyhydric phenols obtained by reacting a polyhydric phenol with a halogen-containing epoxide or dihalohydrin; and, diepoxides.
11. The flame retardant composition of Claim 1 wherein optional lactone stabilizer performance enhancer (v) includes at least one member selected from the group consisting of phenolic alkyl ester and arylamine.
12. The flame retardant composition of Claim 1 wherein flame retardant (i) includes at least one chlorinated phosphate ester; lactone stabilizer (ii) includes at least one benzofuran-2-one; phosphite stabilizer (iii) includes at least one member selected from the group consisting of triaryl phosphites, diaryl alkyl phosphites, aryl dialkyl phosphites, trialkyl phosphites and mixtures thereof; epoxide stabilizer (iv) includes at least one member selected from the group consisting of epoxy carboxylic acid; glycidyl ethers of polyhydric alcohols and phenols; epoxy polyethers ofpolyhydric phenols obtained by reacting a polyhydric phenol with a halogen-containing epoxide or dihalohydrin; and, diepoxides; and, optional lactone stabilizer performance enhancer (v) includes at least one member selected from the group consisting of phenolic alkyl ester and arylamine.
13. The flame retardant composition of Claim 1 wherein flame retardant (i) includes at least one chlorinated phosphate ester selected from the group consisting of tris(chloroethyl) phosphate, tris(chloropropyl) phosphate, tris(dichloroisopropyl) phosphate and 2,2-bis (chloromethyl) trimethylene bis[bis(2-chloroethyl) phosphate] and their mixtures; lactone stabilizer (ii) includes at least one benzofuran-2-one; phosphite stabilizer (iii) includes at least one member selected from the group consisting of triaryl phosphites, diaryl alkyl phosphites, aryl dialkyl phosphites, trialkyl phosphites and mixtures thereof; epoxide stabilizer includes at least one member selected from the group consisting of epoxy carboxylic acid; glycidyl ethers of polyhydric alcohols and phenols; epoxy polyethers of polyhydric phenols obtained by reacting a polyhydric phenol with a halogen-containing epoxide or dihalohydrin; and, diepoxides; and, optional lactone stabilizer performance enhancer (v) includes at least one member selected from the group consisting of phenolic alkyl ester and arylamine.
14. The flame retardant composition of Claim 1 comprising from 75 to 99.5 weight percent flame retardant (i); from 0.01 to 5 weight percent lactone stabilizer (ii); from 0.01 to 5 weight percent phosphite stabilizer (iii); from 0.01 to 10 weight percent epoxide stabilizer (iv); and, from 0 to 5 weight percent lactone stabilizer performance enhancer (V).
15. The flame retardant composition of Claim 1 comprising from 90 to 99 weight percent flame retardant (i); from 0.02 to 2 weight percent lactone stabilizer (ii); from 0.02 to 2 weight percent phosphite stabilizer (iii); from 0.02 to 5 weight percent epoxide stabilizer (iv); and, from 0 to 2 weight percent lactone stabilizer performance enhancer (V).
16. The flame retardant composition of Claim 12 comprising from 75 to 99.5 weight percent flame retardant (i); from 0.01 to 5 weight percent lactone stabilizer (ii); from 0.01 to 5 weight percent phosphite stabilizer (iii); from 0.01 to 10 weight percent epoxide
stabilizer (iv); and, from O to 5 weight percent lactone stabilizer performance enhancer (V).
17. The flame retardant composition of Claim 12 comprising from 90 to 99 weight percent flame retardant (i); from 0.02 to 2 weight percent lactone stabilizer (ii); from 0.02 to 2 weight percent phosphite stabilizer (iii); from 0.02 to 5 weight percent epoxide stabilizer (iv); and, from 0 to 2 weight percent lactone stabilizer performance enhancer (V).
18. The flame retardant composition of Claim 13 comprising from 75 to 99.5 weight percent flame retardant (i); from 0.01 to 5 weight percent lactone stabilizer (ii); from 0.01 to 5 weight percent phosphite stabilizer (iii); from 0.01 to 10 weight percent epoxide stabilizer (iv); and, from 0 to 5 weight percent lactone stabilizer performance enhancer (V).
19. The flame retardant composition of Claim 13 comprising from 90 to 99 weight percent flame retardant (i); from 0.02 to 2 weight percent lactone stabilizer (ii); from 0.02 to 2 weight percent phosphite stabilizer (iii); from 0.02 to 5 weight percent epoxide stabilizer (iv); and, from 0 to 2 weight percent lactone stabilizer performance enhancer (V).
20. A flexible polyurethane foam- forming reaction mixture which comprises:
(a) at least one polyol;
(b) at least one polyisocyanate;
(c) at least one blowing agent;
(d) at least one catalyst for the polyurethane foam-forming reaction; and,
(e) a flame retardant-effective amount of the flame retardant composition of Claim 1.
21. A flexible polyurethane foam-forming reaction mixture which comprises:
(a) at least one polyol;
(b) at least one polyisocyanate;
(c) at least one blowing agent;
(d) at least one catalyst for the polyurethane foam- forming reaction; and,
(e) a flame retardant-effective amount of the flame retardant composition of Claim 12.
22. A flexible polyurethane foam-forming reaction mixture which comprises:
(a) at least one polyol;
(b) at least one polyisocyanate;
(c) at least one blowing agent;
(d) at least one catalyst for the polyurethane foam-forming reaction; and,
(e) a flame retardant-effective amount of the flame retardant composition of Claim 13.
23. A flexible polyurethane foam-forming reaction mixture which comprises:
(a) at least one polyol;
(b) at least one polyisocyanate;
(c) at least one blowing agent;
(d) at least one catalyst for the polyurethane foam- forming reaction; and,
(e) a flame retardant-effective amount of the flame retardant composition of Claim 14.
24. A flexible polyurethane foam-forming reaction mixture which comprises:
(a) at least one polyol;
(b) at least one polyisocyanate;
(c) at least one blowing agent;
(d) at least one catalyst for the polyurethane foam-forming reaction; and,
(e) a flame retardant-effective amount of the flame retardant composition of Claim 15.
25. A flexible polyurethane foam- forming reaction mixture which comprises:
(a) at least one polyol;
(b) at least one polyisocyanate;
(c) at least one blowing agent;
(d) at least one catalyst for the polyurethane foam-forming reaction; and,
(e) a flame retardant-effective amount of the flame retardant composition of Claim 16.
26. A flexible polyurethane foam-forming reaction mixture which comprises:
(a) at least one polyol;
(b) at least one polyisocyanate;
(c) at least one blowing agent;
(d) at least one catalyst for the polyurethane foam-forming reaction; and,
(e) a flame retardant-effective amount of the flame retardant composition of Claim 17.
27. A flexible polyurethane foam-forming reaction mixture which comprises:
(a) at least one polyol;
(b) at least one polyisocyanate;
(c) at least one blowing agent;
(d) at least one catalyst for the polyurethane foam- forming reaction; and,
(e) a flame retardant-effective amount of the flame retardant composition of Claim 18.
28. A polyurethane foam-forming reaction mixture which comprises:
(a) at least one polyol;
(b) at least one polyisocyanate;
(c) at least one blowing agent;
(d) at least one catalyst for the polyurethane foam- forming reaction; and,
(e) a flame retardant-effective amount of the flame retardant composition of
Claim 19.
29. The flexible polyurethane foam-forming reaction mixture of Claim 20 wherein polyol (a) is a polyether diol; polyisocyanate (b) is a diisocyanate; blowing agent (c) is at least one member selected from the group consisting of water, carbon dioxide and hydrocarbon present in an amount to provide a foam density of from 0.8 to 2.5 pounds per cubic foot; and, flame retardant composition (e) is present in an amount of from 1 to 15 weight percent.
30. The flexible polyurethane foam- forming reaction mixture of Claim 20 wherein polyol (a) is a polyether diol; polyisocyanate (b) is a diisocyanate; blowing agent (c) is at least one member selected from the group consisting of water, carbon dioxide and hydrocarbon present in an amount to provide a foam density from 0.9 to 2.0 pounds per cubic foot; and, flame retardant composition (e) is present in an amount of from 4 to 12 weight percent.
31. The flexible polyurethane foam-forming reaction mixture of Claim 21 wherein polyol (a) is a polyether diol; polyisocyanate (b) is a diisocyanate; blowing agent (c) is at least one member selected from the group consisting of water, carbon dioxide and hydrocarbon present in an amount to provide a foam density from 0.8 to 2.5 pounds per cubic foot; and, flame retardant composition (e) is present in an amount of from 1 to 15 weight percent.
32. The flexible polyurethane foam- forming reaction mixture of Claim 21 wherein polyol (a) is a polyether diol; polyisocyanate (b) is a diisocyanate; blowing agent (c) is at least one member selected from the group consisting of water, carbon dioxide and hydrocarbon present in an amount to provide a foam density from 0.9 to 2.0 pounds per cubic foot; and, flame retardant composition (e) is present in an amount of from 4 to 12 weight percent.
33. The flexible polyurethane foam- forming reaction mixture of Claim 22 wherein polyol (a) is a polyether diol; polyisocyanate (b) is a diisocyanate; blowing agent (c) is at least one member selected from the group consisting of water, carbon dioxide and hydrocarbon present in an amount to provide a foam density of from 0.8 to 2.5 pounds per cubic foot; and, flame retardant composition (e) is present in an amount of from 1 to 15 weight percent.
34. The flexible polyurethane foam- forming reaction mixture of Claim 22 wherein polyol (a) is a polyether diol; polyisocyanate (b) is a diisocyanate; blowing agent (c) is at least one member selected from the group consisting of water, carbon dioxide and hydrocarbon present in an amount to provide a foam density from 0.9 to 2.0 pounds per cubic foot; and, flame retardant composition (e) is present in an amount of from 4 to 12 weight percent.
35. The flexible polyurethane foam-forming reaction mixture of Claim 23 wherein polyol (a) is a polyether diol; polyisocyanate (b) is a diisocyanate; blowing agent (c) is at least one member selected from the group consisting of water, carbon dioxide and hydrocarbon present in an amount to provide a foam density of from 0.8 to 2.5 pounds per cubic foot; and, flame retardant composition (e) is present in an amount of from 1 to 15 weight percent.
36. The flexible polyurethane foam-forming reaction mixture of Claim 23 wherein polyol (a) is a polyether diol; polyisocyanate (b) is a diisocyanate; blowing agent (c) is at least one member selected from the group consisting of water, carbon dioxide and hydrocarbon present in an amount to provide a foam density from 0.9 to 2.0 pounds per cubic foot; and, flame retardant composition (e) is present in an amount of from 4 to 12 weight percent.
37. The flexible polyurethane foam-forming reaction mixture of Claim 24 wherein polyol (a) is a polyether diol; polyisocyanate (b) is a diisocyanate; blowing agent (c) is at least one member selected from the group consisting of water, carbon dioxide and hydrocarbon present in an amount to provide a foam density of from 0.8 to 2.5 pounds per cubic foot; and, flame retardant composition (e) is present in an amount of from 1 to
15 weight percent.
38. The flexible polyurethane foam- forming reaction mixture of Claim 24 wherein polyol (a) is a polyether diol; polyisocyanate (b) is a diisocyanate; blowing agent (c) is at least one member selected from the group consisting of water, carbon dioxide and hydrocarbon present in an amount to provide a foam density from 0.9 to 2.0 pounds per cubic foot; and, flame retardant composition (e) is present in an amount of from 4 to 12 weight percent.
39. The flexible polyurethane foam- forming reaction mixture of Claim 25 wherein polyol (a) is a polyether diol; polyisocyanate (b) is a diisocyanate; blowing agent (c) is at least one member selected from the group consisting of water, carbon dioxide and hydrocarbon present in an amount to provide a foam density of from 0.8 to 2.5 pounds per cubic foot; and, flame retardant composition (e) is present in an amount of from 1 to 15 weight percent.
40. The flexible polyurethane foam- forming reaction mixture of Claim 25 wherein polyol (a) is a polyether diol; polyisocyanate (b) is a diisocyanate; blowing agent (c) is at least one member selected from the group consisting of water, carbon dioxide and hydrocarbon present in an amount to provide a foam density from 0.9 to 2.0 pounds per cubic foot; and, flame retardant composition (e) is present in an amount of from 4 to 12 weight percent.
41. The flexible polyurethane foam-forming reaction mixture of Claim 26 wherein polyol (a) is a polyether diol; polyisocyanate (b) is a diisocyanate; blowing agent (c) is at
least one member selected from the group consisting of water, carbon dioxide and hydrocarbon present in an amount to provide a foam density of from 0.8 to 2.5 pounds per cubic foot; and, flame retardant composition (e) is present in an amount of from 1 to 15 weight percent.
42. The flexible polyurethane foam- forming reaction mixture of Claim 26 wherein polyol (a) is a polyether diol; polyisocyanate (b) is a diisocyanate; blowing agent (c) is at least one member selected from the group consisting of water, carbon dioxide and hydrocarbon present in an amount to provide a foam density from 0.9 to 2.0 pounds per cubic foot; and, flame retardant composition (e) is present in an amount of from 4 to 12 weight percent.
43. The flexible polyurethane foam-forming reaction mixture of Claim 27 wherein polyol (a) is a polyether diol; polyisocyanate (b) is a diisocyanate; blowing agent (c) is at least one member selected from the group consisting of water, carbon dioxide and hydrocarbon present in an amount to provide a foam density of from 0.8 to 2.5 pounds per cubic foot; and, flame retardant composition (e) is present in an amount of from 1 to 15 weight percent.
44. The flexible polyurethane foam-forming reaction mixture of Claim 27 wherein polyol (a) is a polyether diol; polyisocyanate (b) is a diisocyanate; blowing agent (c) is at least one member selected from the group consisting of water, carbon dioxide and hydrocarbon present in an amount to provide a foam density from 0.9 to 2.0 pounds per cubic foot; and, flame retardant composition (e) is present in an amount of from 4 to 12 weight percent.
45. The flexible polyurethane foam-forming reaction mixture of Claim 28 wherein polyol (a) is a polyether diol; polyisocyanate (b) is a diisocyanate; blowing agent (c) is at least one member selected from the group consisting of water, carbon dioxide and hydrocarbon present in an amount to provide a foam density of from 0.8 to 2.5 pounds
per cubic foot; and, flame retardant composition (e) is present in an amount of from 1 to 15 weight percent.
46. The flexible polyurethane foam-forming reaction mixture of Claim 28 wherein polyol (a) is a polyether diol; polyisocyanate (b) is a diisocyanate; blowing agent (c) is at least one member selected from the group consisting of water, carbon dioxide and hydrocarbon present in an amount to provide a foam density from 0.9 to 2.0 pounds per cubic foot; and, flame retardant composition (e) is present in an amount of from 4 to 12 weight percent.
47. The flexible polyurethane foam obtained from the polyurethane foam-forming reaction mixture of Claim 20.
48. The flexible polyurethane foam obtained from the polyurethane foam- forming reaction mixture of Claim 29.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/667,937 US20110046250A1 (en) | 2007-07-06 | 2008-07-02 | Flame retardant composition and flexible polyurethane foam prepared therewith |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US95849407P | 2007-07-06 | 2007-07-06 | |
US60/958,494 | 2007-07-06 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2009009006A1 true WO2009009006A1 (en) | 2009-01-15 |
Family
ID=39760137
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2008/008281 WO2009009006A1 (en) | 2007-07-06 | 2008-07-02 | Flame retardant composition and flexible polyurethane foam prepared therewith |
Country Status (2)
Country | Link |
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US (1) | US20110046250A1 (en) |
WO (1) | WO2009009006A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ITMI20092226A1 (en) * | 2009-12-18 | 2011-06-19 | Dow Global Technologies Inc | RETARDANT MIXTURE OF FLAME FOR POLYURETHANE FOAMS |
Families Citing this family (2)
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US9481775B2 (en) * | 2014-04-28 | 2016-11-01 | Vanderbilt Chemicals, Llc | Polyurethane scorch inhibitor |
US20240182629A1 (en) * | 2022-11-29 | 2024-06-06 | Lear Corporation | Polyurethane foam emissions reduction additive |
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