TWI453270B

TWI453270B - 聚氨基甲酸乙酯防火組成物

聚氨基甲酸乙酯防火組成物 Download PDF

Info

Publication number: TWI453270B
Authority: TW; Taiwan
Prior art keywords: phosphite; butyl; bis; acid; group
Prior art date: 2005-09-16

Application number

TW095133965A

Other languages

English (en)

Chinese (zh)

Other versions

TW200722508A (en

Inventor

Pierre Rota-Graziosi

Original Assignee

Ciba Sc Holding Ag

Priority date

2005-09-16

Filing date

2006-09-14

Publication date

2014-09-21

2006-09-14 Application filed by Ciba Sc Holding Ag filed Critical Ciba Sc Holding Ag

2007-06-16 Publication of TW200722508A publication Critical patent/TW200722508A/zh

2014-09-21 Application granted granted Critical

2014-09-21 Publication of TWI453270B publication Critical patent/TWI453270B/zh

Links

239000000203 mixture Substances 0.000 title claims abstract description 105
239000003063 flame retardant Substances 0.000 title claims abstract description 41
239000004814 polyurethane Substances 0.000 title claims abstract description 31
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 27
229920002635 polyurethane Polymers 0.000 title claims abstract description 24
-1 melamine cyanurate Chemical class 0.000 claims abstract description 111
150000002148 esters Chemical class 0.000 claims abstract description 26
ZQKXQUJXLSSJCH-UHFFFAOYSA-N melamine cyanurate Chemical compound NC1=NC(N)=NC(N)=N1.O=C1NC(=O)NC(=O)N1 ZQKXQUJXLSSJCH-UHFFFAOYSA-N 0.000 claims abstract description 17
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 claims abstract description 17
229910052698 phosphorus Inorganic materials 0.000 claims abstract description 9
239000011574 phosphorus Substances 0.000 claims abstract description 7
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 6
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 30
229920000307 polymer substrate Polymers 0.000 claims description 26
ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 20
HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 12
238000000034 method Methods 0.000 claims description 12
ADRNSOYXKABLGT-UHFFFAOYSA-N 8-methylnonyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCCCCCCCC(C)C)OC1=CC=CC=C1 ADRNSOYXKABLGT-UHFFFAOYSA-N 0.000 claims description 7
239000004305 biphenyl Substances 0.000 claims description 7
ZMANLGWZVUUVFS-UHFFFAOYSA-N dodecyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCCCCCCCCCCCC)OC1=CC=CC=C1 ZMANLGWZVUUVFS-UHFFFAOYSA-N 0.000 claims description 7
IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 claims description 7
QEDNBHNWMHJNAB-UHFFFAOYSA-N tris(8-methylnonyl) phosphite Chemical compound CC(C)CCCCCCCOP(OCCCCCCCC(C)C)OCCCCCCCC(C)C QEDNBHNWMHJNAB-UHFFFAOYSA-N 0.000 claims description 7
DWSWCPPGLRSPIT-UHFFFAOYSA-N benzo[c][2,1]benzoxaphosphinin-6-ium 6-oxide Chemical compound C1=CC=C2[P+](=O)OC3=CC=CC=C3C2=C1 DWSWCPPGLRSPIT-UHFFFAOYSA-N 0.000 claims description 5
FDBMBOYIVUGUSL-UHFFFAOYSA-N OP(O)OP(O)O.C(C)(C)(C)C1=C(C(=CC(=C1)C)C(C)(C)C)C(O)(C(CO)(CO)CO)C1=C(C=C(C=C1C(C)(C)C)C)C(C)(C)C Chemical compound OP(O)OP(O)O.C(C)(C)(C)C1=C(C(=CC(=C1)C)C(C)(C)C)C(O)(C(CO)(CO)CO)C1=C(C=C(C=C1C(C)(C)C)C)C(C)(C)C FDBMBOYIVUGUSL-UHFFFAOYSA-N 0.000 claims description 3
235000010290 biphenyl Nutrition 0.000 claims description 3
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 claims description 3
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 3
YUYQHJUMEAITFR-UHFFFAOYSA-N (2,3,4-trimethylphenyl) dihydrogen phosphite Chemical compound CC1=CC=C(OP(O)O)C(C)=C1C YUYQHJUMEAITFR-UHFFFAOYSA-N 0.000 claims description 2
RWLRWONNIHIYGR-UHFFFAOYSA-N 18-[[3,5-bis[1-[17-carboxyheptadecyl(methyl)amino]ethyl]-2-hydroxyphenyl]methyl-methylamino]nonadecanoic acid Chemical compound OC(=O)CCCCCCCCCCCCCCCCC(C)N(C)CC1=CC(C(C)N(C)CCCCCCCCCCCCCCCCCC(O)=O)=CC(C(C)N(C)CCCCCCCCCCCCCCCCCC(O)=O)=C1O RWLRWONNIHIYGR-UHFFFAOYSA-N 0.000 claims 1
OOTZLXPWNFDTDM-UHFFFAOYSA-N 3-(1-hydroxypropan-2-yloxy)-1,1,1,2-tetraphenylpropan-2-ol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C(O)(COC(CO)C)C1=CC=CC=C1 OOTZLXPWNFDTDM-UHFFFAOYSA-N 0.000 claims 1
RNNGKNBZYALDNU-UHFFFAOYSA-N phosphoric acid;triphenylene Chemical compound OP(O)(O)=O.C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 RNNGKNBZYALDNU-UHFFFAOYSA-N 0.000 claims 1
NVLRFXKSQQPKAD-UHFFFAOYSA-N tricarbon Chemical compound [C]=C=[C] NVLRFXKSQQPKAD-UHFFFAOYSA-N 0.000 claims 1
229920000642 polymer Polymers 0.000 abstract description 40
229910017464 nitrogen compound Inorganic materials 0.000 abstract description 12
150000002830 nitrogen compounds Chemical class 0.000 abstract description 12
XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 abstract description 3
150000004715 keto acids Chemical class 0.000 abstract 1
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 59
229920001577 copolymer Polymers 0.000 description 42
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 35
239000000654 additive Substances 0.000 description 25
229910052757 nitrogen Inorganic materials 0.000 description 25
239000004433 Thermoplastic polyurethane Substances 0.000 description 21
150000001875 compounds Chemical class 0.000 description 21
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 21
229920002803 thermoplastic polyurethane Polymers 0.000 description 21
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 19
229920001228 polyisocyanate Polymers 0.000 description 19
239000005056 polyisocyanate Substances 0.000 description 19
239000002253 acid Substances 0.000 description 18
239000005977 Ethylene Substances 0.000 description 17
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LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 16
239000001257 hydrogen Substances 0.000 description 16
229910052739 hydrogen Inorganic materials 0.000 description 16
125000001424 substituent group Chemical group 0.000 description 15
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 14
150000001412 amines Chemical class 0.000 description 14
239000004615 ingredient Substances 0.000 description 14
125000003118 aryl group Chemical group 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000004743 Polypropylene Substances 0.000 description 12
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
229920000570 polyether Polymers 0.000 description 12
229920001155 polypropylene Polymers 0.000 description 12
239000003381 stabilizer Substances 0.000 description 12
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 11
230000000996 additive effect Effects 0.000 description 11
150000002431 hydrogen Chemical group 0.000 description 11
239000005062 Polybutadiene Substances 0.000 description 10
239000004721 Polyphenylene oxide Substances 0.000 description 10
239000012964 benzotriazole Substances 0.000 description 10
KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
235000011007 phosphoric acid Nutrition 0.000 description 10
229920000768 polyamine Polymers 0.000 description 10
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
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239000000126 substance Substances 0.000 description 9
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
229920000388 Polyphosphate Polymers 0.000 description 8
150000001993 dienes Chemical class 0.000 description 8
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239000004702 low-density polyethylene Substances 0.000 description 8
229910052751 metal Inorganic materials 0.000 description 8
239000002184 metal Substances 0.000 description 8
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 8
229920006324 polyoxymethylene Polymers 0.000 description 8
239000001205 polyphosphate Substances 0.000 description 8
235000011176 polyphosphates Nutrition 0.000 description 8
238000012360 testing method Methods 0.000 description 8
AIBRSVLEQRWAEG-UHFFFAOYSA-N 3,9-bis(2,4-ditert-butylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP1OCC2(COP(OC=3C(=CC(=CC=3)C(C)(C)C)C(C)(C)C)OC2)CO1 AIBRSVLEQRWAEG-UHFFFAOYSA-N 0.000 description 7
239000004698 Polyethylene Substances 0.000 description 7
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
229910000147 aluminium phosphate Inorganic materials 0.000 description 7
239000003054 catalyst Substances 0.000 description 7
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WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 7
239000000463 material Substances 0.000 description 7
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229920002554 vinyl polymer Polymers 0.000 description 7
BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 6
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
239000004114 Ammonium polyphosphate Substances 0.000 description 6
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
125000004648 C2-C8 alkenyl group Chemical group 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
239000007983 Tris buffer Substances 0.000 description 6
235000019826 ammonium polyphosphate Nutrition 0.000 description 6
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239000007795 chemical reaction product Substances 0.000 description 6
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229910052736 halogen Chemical group 0.000 description 6
150000002367 halogens Chemical group 0.000 description 6
229920001903 high density polyethylene Polymers 0.000 description 6
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 6
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ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
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CDXVUROVRIFQMV-UHFFFAOYSA-N oxo(diphenoxy)phosphanium Chemical compound C=1C=CC=CC=1O[P+](=O)OC1=CC=CC=C1 CDXVUROVRIFQMV-UHFFFAOYSA-N 0.000 description 5
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238000006116 polymerization reaction Methods 0.000 description 5
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229910052759 nickel Inorganic materials 0.000 description 4
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238000002360 preparation method Methods 0.000 description 4
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125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
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PEXOFOFLXOCMDX-UHFFFAOYSA-N tritridecyl phosphite Chemical compound CCCCCCCCCCCCCOP(OCCCCCCCCCCCCC)OCCCCCCCCCCCCC PEXOFOFLXOCMDX-UHFFFAOYSA-N 0.000 description 4
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RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 3
SSADPHQCUURWSW-UHFFFAOYSA-N 3,9-bis(2,6-ditert-butyl-4-methylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound CC(C)(C)C1=CC(C)=CC(C(C)(C)C)=C1OP1OCC2(COP(OC=3C(=CC(C)=CC=3C(C)(C)C)C(C)(C)C)OC2)CO1 SSADPHQCUURWSW-UHFFFAOYSA-N 0.000 description 3
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