JP2016102177A - ポリウレタン樹脂の難燃化方法 - Google Patents
ポリウレタン樹脂の難燃化方法 Download PDFInfo
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- JP2016102177A JP2016102177A JP2014242324A JP2014242324A JP2016102177A JP 2016102177 A JP2016102177 A JP 2016102177A JP 2014242324 A JP2014242324 A JP 2014242324A JP 2014242324 A JP2014242324 A JP 2014242324A JP 2016102177 A JP2016102177 A JP 2016102177A
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- 239000000314 lubricant Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 125000002960 margaryl 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])[H] 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 238000002074 melt spinning Methods 0.000 description 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- CAAULPUQFIIOTL-UHFFFAOYSA-N methyl dihydrogen phosphate Chemical compound COP(O)(O)=O CAAULPUQFIIOTL-UHFFFAOYSA-N 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- KSEMETYAQIUBQB-UHFFFAOYSA-N n,n-diethylmethanesulfonamide Chemical compound CCN(CC)S(C)(=O)=O KSEMETYAQIUBQB-UHFFFAOYSA-N 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- MORLSCQKZAPYFM-UHFFFAOYSA-N n,n-dimethylethanesulfonamide Chemical compound CCS(=O)(=O)N(C)C MORLSCQKZAPYFM-UHFFFAOYSA-N 0.000 description 1
- WCFDSGHAIGTEKL-UHFFFAOYSA-N n,n-dimethylmethanesulfonamide Chemical compound CN(C)S(C)(=O)=O WCFDSGHAIGTEKL-UHFFFAOYSA-N 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- MBMOGJGVYAHBLN-UHFFFAOYSA-N n-cyclohexylbutane-1-sulfonamide Chemical compound CCCCS(=O)(=O)NC1CCCCC1 MBMOGJGVYAHBLN-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- CLXHPJUNPZCTCP-UHFFFAOYSA-N n-methoxymethanesulfonamide Chemical compound CONS(C)(=O)=O CLXHPJUNPZCTCP-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- ZFIFHAKCBWOSRN-UHFFFAOYSA-N naphthalene-1-sulfonamide Chemical compound C1=CC=C2C(S(=O)(=O)N)=CC=CC2=C1 ZFIFHAKCBWOSRN-UHFFFAOYSA-N 0.000 description 1
- UIEKYBOPAVTZKW-UHFFFAOYSA-L naphthalene-2-carboxylate;nickel(2+) Chemical compound [Ni+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 UIEKYBOPAVTZKW-UHFFFAOYSA-L 0.000 description 1
- SWBLLSQMOMPTMC-UHFFFAOYSA-N naphthalene-2-sulfonamide Chemical compound C1=CC=CC2=CC(S(=O)(=O)N)=CC=C21 SWBLLSQMOMPTMC-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005933 neopentyloxycarbonyl group Chemical group 0.000 description 1
- 150000002816 nickel compounds Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001196 nonadecyl 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])C([H])([H])[H] 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- MBAUOPQYSQVYJV-UHFFFAOYSA-N octyl 3-[4-hydroxy-3,5-di(propan-2-yl)phenyl]propanoate Chemical compound OC1=C(C=C(C=C1C(C)C)CCC(=O)OCCCCCCCC)C(C)C MBAUOPQYSQVYJV-UHFFFAOYSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- HXSACZWWBYWLIS-UHFFFAOYSA-N oxadiazine-4,5,6-trione Chemical compound O=C1ON=NC(=O)C1=O HXSACZWWBYWLIS-UHFFFAOYSA-N 0.000 description 1
- KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000000913 palmityl 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])[H] 0.000 description 1
- 125000002958 pentadecyl 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])[H] 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- 239000013500 performance material Substances 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- OXQKEKGBFMQTML-BIVRFLNRSA-N perseitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO OXQKEKGBFMQTML-BIVRFLNRSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920000582 polyisocyanurate Polymers 0.000 description 1
- 239000011495 polyisocyanurate Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920003225 polyurethane elastomer Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- OQZCJRJRGMMSGK-UHFFFAOYSA-M potassium metaphosphate Chemical compound [K+].[O-]P(=O)=O OQZCJRJRGMMSGK-UHFFFAOYSA-M 0.000 description 1
- 229940099402 potassium metaphosphate Drugs 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- RLEFZEWKMQQZOA-UHFFFAOYSA-M potassium;octanoate Chemical compound [K+].CCCCCCCC([O-])=O RLEFZEWKMQQZOA-UHFFFAOYSA-M 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229940066675 ricinoleate Drugs 0.000 description 1
- 238000001175 rotational moulding Methods 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000019983 sodium metaphosphate Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007921 spray Substances 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
- 239000005720 sucrose Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- MWKHJNIZZGJMLC-UHFFFAOYSA-M tetrakis[[tris(diethylamino)-$l^{5}-phosphanylidene]amino]phosphanium;chloride Chemical compound [Cl-].CCN(CC)P(N(CC)CC)(N(CC)CC)=N[P+](N=P(N(CC)CC)(N(CC)CC)N(CC)CC)(N=P(N(CC)CC)(N(CC)CC)N(CC)CC)N=P(N(CC)CC)(N(CC)CC)N(CC)CC MWKHJNIZZGJMLC-UHFFFAOYSA-M 0.000 description 1
- HNGAMVUMMCAKST-UHFFFAOYSA-M tetrakis[[tris(dimethylamino)-$l^{5}-phosphanylidene]amino]phosphanium;bromide Chemical compound [Br-].CN(C)P(N(C)C)(N(C)C)=N[P+](N=P(N(C)C)(N(C)C)N(C)C)(N=P(N(C)C)(N(C)C)N(C)C)N=P(N(C)C)(N(C)C)N(C)C HNGAMVUMMCAKST-UHFFFAOYSA-M 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003606 tin compounds Chemical class 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
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- SBUXRMKDJWEXRL-ZWKOTPCHSA-N trans-body Chemical compound O=C([C@@H]1N(C2=O)[C@H](C3=C(C4=CC=CC=C4N3)C1)CC)N2C1=CC=C(F)C=C1 SBUXRMKDJWEXRL-ZWKOTPCHSA-N 0.000 description 1
- YJGJRYWNNHUESM-UHFFFAOYSA-J triacetyloxystannyl acetate Chemical compound [Sn+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O YJGJRYWNNHUESM-UHFFFAOYSA-J 0.000 description 1
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- YAHWUJOBZVKEGY-UHFFFAOYSA-N tridecane-1-sulfonamide Chemical compound CCCCCCCCCCCCCS(N)(=O)=O YAHWUJOBZVKEGY-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- QOPBTFMUVTXWFF-UHFFFAOYSA-N tripropyl phosphite Chemical compound CCCOP(OCCC)OCCC QOPBTFMUVTXWFF-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-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
- ILLOBGFGKYTZRO-UHFFFAOYSA-N tris(2-ethylhexyl) phosphite Chemical compound CCCCC(CC)COP(OCC(CC)CCCC)OCC(CC)CCCC ILLOBGFGKYTZRO-UHFFFAOYSA-N 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Fireproofing Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
本発明のポリウレタン樹脂の難燃化方法では、前記難燃剤が、下記式(2)で示されることが好適である。
本発明のポリウレタン樹脂の難燃化方法では、前記難燃剤が、下記式(3)で示されることが好適である。
本発明のポリウレタン樹脂の難燃化方法では、前記ポリウレタン樹脂が、ポリオール成分とポリイソシアネート成分との反応により得られ、前記ポリオール成分に、前記難燃剤を、5ppm以上20000ppm以下で含有させることが好適である。
上記式(1)において、Rが、部分構造式(A)で示される場合、難燃剤は、下記式(2)で示される化合物である。
上記部分構造式(A)および式(2)において、R1は、互いに同一または相異なって、水素原子または炭素数1〜20の炭化水素基を示す。
上記部分構造式(B)および上記式(3)において、R2は、互いに同一または相異なって、水素原子または炭素数1〜20の炭化水素基を示す。
<原料の説明>
TTGPC:テトラキス(1,1,3,3−テトラメチルグアニジノ)ホスホニウムクロライド(上記式(2)において、R1がメチル基であり、X−が塩化物イオンである化合物。)
PZN:テトラキス[トリス(ジメチルアミノ)ホスホラニリデンアミノ]ホスホニウムドデシルベンゼンスルホニル(上記式(3)において、R2がメチル基であり、X−が直鎖型ドデシルベンゼンスルホン酸アニオンである化合物。)
ラビトルFP−110:2,2,4,4,6,6−ヘキサフェノキシシクロトリホスファゼン(ホスファゼン化合物、株式会社伏見製作所製)
TCPP:トリス(クロロプロピル)ホスフェート、(商品名:TMCPP、大八化学工業社製)
EP330N;アクトコールEP−330N(ポリオキシアルキレンポリオール(プロピレンオキサイド−エチレンオキサイドのブロック共重合体)、エチレンオキサイド含有量(末端オキシエチレン基含有量):15質量%、数平均分子量:5000、平均官能基数:3、水酸基価:34mgKOH/g、三井化学社製)
EP828;アクトコールEP−828(ポリオキシアルキレンポリオール(プロピレンオキサイド−エチレンオキサイドのブロック共重合体)、エチレンオキサイド含有量(末端オキシエチレン基含有量):15質量%、数平均分子量:6000、平均官能基数:3、水酸基価:28mgKOH/g、三井化学社製)
EP3033;アクトコールEP−3033(ポリオキシアルキレンポリオール(プロピレンオキサイド−エチレンオキサイドのブロック共重合体)、エチレンオキサイド含有量(末端オキシエチレン基含有量):16質量%、数平均分子量:6600、平均官能基数:4、水酸基価:34mgKOH/g、三井化学社製)
POP3628;アクトコールPOP−3628(ポリマーポリオール、水酸基価:28mgKOH/g、三井化学社製)
POP3123;アクトコールPOP−3123(ポリマーポリオール、水酸基価:23mgKOH/g、三井化学社製)
33LV;DABCO 33LV(アミン触媒、トリエチレンジアミンの33質量%ジエチレングリコール溶液、エア・プロダクツジャパン社製)
A1;Niax A−1(アミン触媒、モメンティブ社製)
No.25;カオーライザー No.25(アミン触媒、花王社製)
NCE;TOYOCAT−NCE(アミン触媒、東ソー社製)
KL210;アクトコールKL−210(架橋剤、平均官能基数:3.75、水酸基価:840mgKOH/g、三井化学社製)
DEOA;ジエタノールアミン(架橋剤、官能基数:3、水酸基価:1600mgKOH/g)
EP505S;アクトコールEP−505S(連通化剤、ポリエーテルポリオール(ポリオキシアルキレンポリオール(プロピレンオキサイド−エチレンオキサイドのランダム共重合体))、エチレンオキサイド含有量:70質量%、数平均分子量:3300、平均官能基数:3、水酸基価:52mgKOH/g、三井化学社製)
DC6070;DC−6070(シリコーン整泡剤、エア・プロダクツジャパン社製)
B8715LF2;B−8715LF2(シリコーン整泡剤、エヴォニック社製)
L5309;L−5309(シリコーン整泡剤、モメンティブ社製)
L3601;L−3601(シリコーン整泡剤、東レ・ダウコーニング社製)
DC2525;DC−2525(シリコーン整泡剤、エア・プロダクツジャパン社製)
TM20;コスモネートTM−20(ポリイソシアネート(2,4−トリレンジイソシアネートと2,6−トリレンジイソシアネートとの80:20質量比の混合物(TDI)80質量%と、ジフェニルメタンジイソシネート(MDI)20質量%の混合物)、イソシアネート基含有量:45質量%、三井化学社製)
TM50;コスモネートTM−50(ポリイソシアネート(2,4−トリレンジイソシアネートと2,6−トリレンジイソシアネートとの80:20質量比の混合物(TDI)50質量%と、ジフェニルメタンジイソシネート(MDI)50質量%の混合物)、イソシアネート基含有量:40質量%、三井化学社製)
<ポリウレタン樹脂(ポリウレタンフォーム)の製造>
(実施例1)
EP330N(ポリオキシアルキレンポリオール)50質量部と、POP3628(ポリマーポリオール)50質量部と、33LV(アミン触媒)0.4質量部と、A1(アミン触媒)0.08質量部と、水(発泡剤)4.6質量部と、KL210(架橋剤)1.5質量部と、EP505S(連通化剤)1.0質量部と、DC6070(整泡剤)1.0質量部と、B8715LF2(整泡剤)0.5質量部と、テトラキス(1,1,3,3−テトラメチルグアニジノ)ホスホニウムクロライド(難燃剤)0.05質量部とを配合し、それらを混合して、レジンプレミックスを調製した。
(実施例2〜実施例27および比較例1〜比較例9)
表1〜表4に記載の配合処方に従って、実施例1と同様にして、軟質ポリウレタンフォームを製造した。
<ポリウレタンフォームの物性測定>
実施例1〜実施例27および比較例1〜比較例9で製造したポリウレタンフォームの物性を、それぞれ、下記の測定方法で測定し、それぞれのポリウレタンフォームの密度、各物性(硬さ、伸び、引裂強度、熱圧縮永久歪み、コア部の反発弾性)および燃焼性の評価について結果を得た。
<測定方法>
(1)ポリウレタンフォームの硬度(以下の表中、「25%ILD」とする。)
JIS K−6400(1997)に記載のA法に準拠して、厚さ100mmのポリウレタンフォームについて、その硬さを測定した。
(2)ポリウレタンフォームの伸び
JIS K−6400(1997)に記載の方法に準拠して、伸びを測定した。
(3)ポリウレタンフォームの引裂強度
JIS K−6400(1997)に記載の方法に準拠して、引裂強度を測定した。
(4)ポリウレタンフォームの熱圧縮永久歪み(以下の表中、「Dryset」とする。)
JIS K−6400(1997)に記載の方法に準拠して、熱圧縮永久歪みを測定した。
(5)ポリウレタンフォームのコア部の反発弾性(以下の表中、「反発弾性core」とする。)
JIS K−6400(1997)に記載の方法に準拠して、反発弾性を測定した。
(6)燃焼試験(下記の表中、「燃焼性」とする。)
FMVSS−302(2005)に記載の方法に準拠して、水平法により燃焼試験をした。
EP:ポリオキシアルキレンポリオール(ポリエーテルポリオール)
POP:ポリマーポリオール
なお、上記の原料の説明で記載したものの説明は省略している。
<考察>
他の成分が同組成であるレジンプレミックスにおいて、難燃剤であるTTGPCおよびPZNが、それぞれ458ppm含まれている実施例14および実施例25のポリウレタンフォームと、難燃剤が含まれていない比較例1のポリウレタンフォームとを比較すると、実施例14および実施例25のポリウレタンフォームでは、比較例1のポリウレタンフォームに比べて、その硬さ、伸びおよび熱圧縮永久歪みが向上し、その引裂強度および反発弾性は維持されている上に、その難燃性も向上していることがわかる。
Claims (5)
- ポリウレタン樹脂に下記式(1)で示される難燃剤を含有させることにより、ポリウレタン樹脂を難燃化させることを特徴とする、ポリウレタン樹脂の難燃化方法。
(式中、R1は、互いに同一または相異なって、水素原子または炭素数1〜20の炭化水素基を示し、R1同士が、互いに結合して環構造を形成してもよい。)
(式中、R2は、互いに同一または相異なって、水素原子または炭素数1〜20の炭化水素基を示す。ただし、R2同士が、互いに結合して環構造を形成してもよい。また、nは、0〜3の整数を示す。ただし、式(1)中の4つのRのうちの少なくとも1つのRに対応するnは0ではない。) - 前記ポリウレタン樹脂が、ポリオール成分とポリイソシアネート成分との反応により得られ、
前記ポリオール成分に、前記難燃剤を、5ppm以上20000ppm以下で含有させることを特徴とする、請求項1〜3のいずれか一項に記載のポリウレタン樹脂の難燃化方法。 - 前記ポリウレタン樹脂が、ポリウレタンフォームであることを特徴とする、請求項1〜4のいずれか一項に記載のポリウレタン樹脂の難燃化方法。
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