JP2012512942A - 脂肪族結合した臭素を含有するポリマーのための安定剤 - Google Patents
脂肪族結合した臭素を含有するポリマーのための安定剤 Download PDFInfo
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- JP2012512942A JP2012512942A JP2011542234A JP2011542234A JP2012512942A JP 2012512942 A JP2012512942 A JP 2012512942A JP 2011542234 A JP2011542234 A JP 2011542234A JP 2011542234 A JP2011542234 A JP 2011542234A JP 2012512942 A JP2012512942 A JP 2012512942A
- Authority
- JP
- Japan
- Prior art keywords
- polymer
- aliphatic
- bromine
- alkyl phosphite
- epoxy compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 229920000642 polymer Polymers 0.000 title claims abstract description 204
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 title claims abstract description 104
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 title claims abstract description 102
- 229910052794 bromium Inorganic materials 0.000 title claims abstract description 102
- 125000001931 aliphatic group Chemical group 0.000 title claims abstract description 95
- 239000003381 stabilizer Substances 0.000 title abstract description 21
- -1 alkyl phosphite Chemical compound 0.000 claims abstract description 81
- 239000000203 mixture Substances 0.000 claims abstract description 72
- 150000001875 compounds Chemical class 0.000 claims abstract description 60
- 239000004593 Epoxy Substances 0.000 claims abstract description 57
- 238000010128 melt processing Methods 0.000 claims abstract description 31
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 39
- 229920001577 copolymer Polymers 0.000 claims description 36
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 33
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 claims description 27
- 239000006260 foam Substances 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 229920003986 novolac Polymers 0.000 claims description 17
- 229920005989 resin Polymers 0.000 claims description 17
- 239000011347 resin Substances 0.000 claims description 17
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical class C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 claims description 11
- ZCEFNLGIBZAQMM-UHFFFAOYSA-N C=CCC1=CC(=O)NC1=O Chemical compound C=CCC1=CC(=O)NC1=O ZCEFNLGIBZAQMM-UHFFFAOYSA-N 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 229920001400 block copolymer Polymers 0.000 claims description 8
- PZRWFKGUFWPFID-UHFFFAOYSA-N 3,9-dioctadecoxy-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C1OP(OCCCCCCCCCCCCCCCCCC)OCC21COP(OCCCCCCCCCCCCCCCCCC)OC2 PZRWFKGUFWPFID-UHFFFAOYSA-N 0.000 claims description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims description 6
- 229920006305 unsaturated polyester Polymers 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- RGASRBUYZODJTG-UHFFFAOYSA-N 1,1-bis(2,4-ditert-butylphenyl)-2,2-bis(hydroxymethyl)propane-1,3-diol dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.C(C)(C)(C)C1=C(C=CC(=C1)C(C)(C)C)C(O)(C(CO)(CO)CO)C1=C(C=C(C=C1)C(C)(C)C)C(C)(C)C RGASRBUYZODJTG-UHFFFAOYSA-N 0.000 claims description 4
- WBWXVCMXGYSMQA-UHFFFAOYSA-N 3,9-bis[2,4-bis(2-phenylpropan-2-yl)phenoxy]-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical group C=1C=C(OP2OCC3(CO2)COP(OC=2C(=CC(=CC=2)C(C)(C)C=2C=CC=CC=2)C(C)(C)C=2C=CC=CC=2)OC3)C(C(C)(C)C=2C=CC=CC=2)=CC=1C(C)(C)C1=CC=CC=C1 WBWXVCMXGYSMQA-UHFFFAOYSA-N 0.000 claims description 3
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 claims description 3
- 238000004132 cross linking Methods 0.000 abstract description 8
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- 239000003063 flame retardant Substances 0.000 abstract description 4
- 229920006327 polystyrene foam Polymers 0.000 abstract description 3
- 239000000463 material Substances 0.000 description 30
- 239000000499 gel Substances 0.000 description 22
- 239000000654 additive Substances 0.000 description 21
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 21
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 13
- 238000005893 bromination reaction Methods 0.000 description 13
- 239000000178 monomer Substances 0.000 description 13
- 229920002554 vinyl polymer Polymers 0.000 description 13
- 230000000996 additive effect Effects 0.000 description 11
- 230000031709 bromination Effects 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 238000001125 extrusion Methods 0.000 description 9
- 238000001879 gelation Methods 0.000 description 9
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 8
- 229920001519 homopolymer Polymers 0.000 description 8
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 7
- 239000004793 Polystyrene Substances 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 229930003836 cresol Natural products 0.000 description 7
- 239000003822 epoxy resin Substances 0.000 description 7
- 238000005187 foaming Methods 0.000 description 7
- 229920000647 polyepoxide Polymers 0.000 description 7
- 229920002223 polystyrene Polymers 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 239000004604 Blowing Agent Substances 0.000 description 6
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical group CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 125000001453 quaternary ammonium group Chemical group 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 241000894007 species Species 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical group Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 230000002411 adverse Effects 0.000 description 4
- 125000000746 allylic group Chemical group 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 150000002009 diols Chemical group 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 230000004580 weight loss Effects 0.000 description 4
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 3
- 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 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- XAQKFOUWWAKVCH-UHFFFAOYSA-N OP(O)OP(O)O.C(C)(C)(C1=CC=CC=C1)C1=C(C=CC(=C1)C(C)(C)C1=CC=CC=C1)C(O)C(CO)(CO)CO Chemical compound OP(O)OP(O)O.C(C)(C)(C1=CC=CC=C1)C1=C(C=CC(=C1)C(C)(C)C1=CC=CC=C1)C(O)C(CO)(CO)CO XAQKFOUWWAKVCH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 3
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- 0 *P(OC1)OCC11COP(*)OC1 Chemical compound *P(OC1)OCC11COP(*)OC1 0.000 description 2
- DEIGXXQKDWULML-UHFFFAOYSA-N 1,2,5,6,9,10-hexabromocyclododecane Chemical compound BrC1CCC(Br)C(Br)CCC(Br)C(Br)CCC1Br DEIGXXQKDWULML-UHFFFAOYSA-N 0.000 description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
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- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
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- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 1
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- 238000011156 evaluation Methods 0.000 description 1
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- 150000002367 halogens Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
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- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000004570 mortar (masonry) Substances 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- SFBTTWXNCQVIEC-UHFFFAOYSA-N o-Vinylanisole Chemical compound COC1=CC=CC=C1C=C SFBTTWXNCQVIEC-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl 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])[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
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004597 plastic additive Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
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- 229920002959 polymer blend Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
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- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
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- 230000001105 regulatory effect Effects 0.000 description 1
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
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- 239000012312 sodium hydride Substances 0.000 description 1
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- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material 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
- 229920006132 styrene block copolymer Polymers 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 238000003878 thermal aging Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 229920000428 triblock copolymer Polymers 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
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Abstract
Description
で表すことができる。上記構造において、スチレンおよびアリルマレイミドのそれぞれの繰返し単位の幾らかまたは全ては交互であることができ、そしてスチレンおよび2,3−ジブロモプロピルマレイミドのそれぞれの繰返し単位の幾らかまたは全ては、同種の2つ以上の連続単位のブロック体を形成できる。出発コポリマー中のアリルマレイミド繰返し単位に対するスチレンのモル比は、95:5から約40:60の範囲であることができるが、アリルマレイミドレベルはこの範囲の上限に向かう方(例えば30〜60モル%の無水マレイン酸)が好ましい。これは、最終製品中のより高い臭素量が得られることを可能にするからである。この種のコポリマーは、スチレン−無水マレイン酸コポリマーから簡便に形成される。スチレン−マレイン酸コポリマーとアリルアミンとの反応は、無水マレイン酸繰返し単位をN−アリルマレイミド繰返し単位に転化させる。臭素化後、アリルマレイミド繰返し単位の少なくとも一部が臭素化され、構造:
を有する臭素化ポリマーが形成される。
で表されるものが挙げられる。これらのポリマーは、多くが市販で入手可能であるノボラックレジンから調製できる。アリルエーテル基は、フェノール性水酸基と水素化ナトリウムとの反応によって導入してアルコキシド基を形成でき、次いでこれはアリルハライド,例えば塩化アリルまたは臭化アリルと反応してエーテルを生成する。
を有する。
スクリーン実験を行って、臭素ブタジエンポリマー中で、熱的に誘導されるゲル化を種々の安定剤が防止する能力を評価する。スクリーニング実験における臭素化ブタジエンポリマーは、臭素化前に60質量%のブタジエンを含有するスチレン/ブタジエン/スチレントリブロックポリマーである。この出発ポリマーを、第WO2008/021418号に記載されるように、元素臭素を臭素化剤として用いて臭素化し、そして得られる臭素化物質は、臭素量62質量%を有する。出発ポリマー中の脂肪族炭素−炭素二重結合の3%が臭素化後に残存する。炭素−臭素 C−Br結合の3.5%は、アリル炭素原子または3級炭素原子に対するものであり、これは熱安定性が構造中の他のC−Br結合よりも小さい。
例8〜17および比較サンプルBは、先の例と同じ方法で形成する。この場合における臭素化ブタジエンポリマーは、臭素化前に60質量%のブタジエンを含有するスチレン/ブタジエン/スチレントリブロックポリマーである。この出発ポリマーは、4級アンモニウムブロミドを臭素化剤として用いて臭素化する(第WO2008021417号に記載する通り)。得られる臭素化物質は、臭素量63%を有する。臭素化ブタジエンポリマーは7%の残存脂肪族炭素−炭素二重結合を含有する。この臭素化ポリマー中の1%よりも少ない炭素−臭素結合は、アリル炭素原子または3級炭素原子である。この組の実験で用いる酸化防止剤パッケージは表3に示す通りである。各々のブレンド物における可溶性の臭素化ブタジエンポリマーの量および各々のブレンド物についての230℃のオンセット時間は、先の例において記載したように評価する。結果は表3に示す通りである。
本発明は以下の態様を有する。
[1] (a)バルクポリマー、(b)脂肪族臭素含有ポリマー、および、(c)少なくとも1種のアルキルホスファイト、少なくとも1種のエポキシ化合物、または少なくとも1種のアルキルホスファイトと少なくとも1種のエポキシ化合物との混合物、を含むポリマー組成物。
[2] 100質量部の脂肪族臭素含有ポリマー当たり1〜40質量部のエポキシ化合物が存在する、上記[1]に記載のポリマー組成物。
[3] 100質量部の脂肪族臭素含有ポリマー当たり1〜40質量部のアルキルホスファイトが存在する、上記[1]に記載のポリマー組成物。
[4] 脂肪族臭素含有ポリマーが、臭素化ブタジエンホモポリマーまたは臭素化スチレン/ブタジエンブロックコポリマーである、上記[1]〜[3]のいずれかに記載のポリマー組成物。
[5] 脂肪族臭素含有ポリマーが、スチレンおよびアリルマレイミドのコポリマー、脂肪族不飽和ポリエステル、ノボラックノボラックレジンのアリルエーテル、またはROMPポリマーもしくはROMPコポリマーである、上記[1]〜[3]のいずれかに記載のポリマー組成物。
[6] バルクポリマーが、スチレンのポリマーまたはコポリマーである、上記[1]〜[5]のいずれかに記載のポリマー組成物。
[7] 発泡体の形状である、上記[1]〜[6]のいずれかに記載のポリマー組成物。
[8] アルキルホスファイトが、少なくとも1種の
(式中、R基は、非置換もしくは置換の、直鎖もしくは分岐のアルキル基であり、または2つのR基が一緒に2価基を形成し、該2価基は置換されていてもよく、隣接−O−基に脂肪族炭素を介して結合して−O−P−O−結合を含む環構造を形成しており、そしてR 1 基は別のR基、またはアリール基もしくは置換アリール基である)
の部分を含有する、前掲の態様のいずれかに記載の方法。
[9] アルキルホスファイトが、構造
(式中、各R 2 は、非置換もしくは置換の、直鎖もしくは分岐の、アルキル基、アリール基または置換アリール基である)
を有するペンタエリスリトールジホスファイト化合物である、前掲の態様のいずれかに記載の方法。
[10] アルキルホスファイトが、ビス(2,4−ジクミルフェニル)ペンタエリスリトールジホスファイト、ジステアリルペンタエリスリトールジホスファイトまたはジ(2,4−ジ−(t−ブチル)フェニル)ペンタエリスリトールジホスファイトである、前掲の態様のいずれかに記載の方法。
[11] 上記[1]〜[10]のいずれかに記載のポリマー組成物を製造する方法であって、溶融バルクポリマーおよび脂肪族臭素含有ポリマーまたは脂肪族臭素含有コポリマーを含有する混合物を、(1)少なくとも1種のアルキルホスファイト、(2)少なくとも1種のエポキシ化合物または(3)少なくとも1種のアルキルホスファイトと少なくとも1種のエポキシ化合物との混合物、の存在下で溶融加工することを含む、方法。
[12] 脂肪族臭素含有ポリマーおよび少なくとも1種のアルキルホスファイト、少なくとも1種のエポキシ化合物または少なくとも1種のアルキルホスファイトと少なくとも1種のエポキシ化合物との混合物を含む、組成物。
[13] 100質量部の脂肪族臭素含有ポリマー当たり1〜40質量部のエポキシ化合物が存在する、上記[12]に記載のポリマー組成物。
[14] 100質量部の脂肪族臭素含有ポリマー当たり1〜40質量部のアルキルホスファイトが存在する、上記[11]または[12]に記載のポリマー組成物。
[15] 脂肪族臭素含有ポリマーが、臭素化ブタジエンホモポリマー、臭素化スチレン/ブタジエンブロックコポリマー、スチレンおよびアリルマレイミドのコポリマー、脂肪族不飽和ポリエステル、ノボラックレジンのアリルエステル、またはROMPポリマーもしくはROMPコポリマーである、上記[11]〜[14]のいずれかに記載のポリマー組成物。
Claims (15)
- (a)バルクポリマー、(b)脂肪族臭素含有ポリマー、および、(c)少なくとも1種のアルキルホスファイト、少なくとも1種のエポキシ化合物、または少なくとも1種のアルキルホスファイトと少なくとも1種のエポキシ化合物との混合物、を含むポリマー組成物。
- 100質量部の脂肪族臭素含有ポリマー当たり1〜40質量部のエポキシ化合物が存在する、請求項1に記載のポリマー組成物。
- 100質量部の脂肪族臭素含有ポリマー当たり1〜40質量部のアルキルホスファイトが存在する、請求項1に記載のポリマー組成物。
- 脂肪族臭素含有ポリマーが、臭素化ブタジエンホモポリマーまたは臭素化スチレン/ブタジエンブロックコポリマーである、請求項1〜3のいずれか1項に記載のポリマー組成物。
- 脂肪族臭素含有ポリマーが、スチレンおよびアリルマレイミドのコポリマー、脂肪族不飽和ポリエステル、ノボラックノボラックレジンのアリルエーテル、またはROMPポリマーもしくはROMPコポリマーである、請求項1〜3のいずれか1項に記載のポリマー組成物。
- バルクポリマーが、スチレンのポリマーまたはコポリマーである、請求項1〜5のいずれか1項に記載のポリマー組成物。
- 発泡体の形状である、請求項1〜6のいずれか1項に記載のポリマー組成物。
- アルキルホスファイトが、ビス(2,4−ジクミルフェニル)ペンタエリスリトールジホスファイト、ジステアリルペンタエリスリトールジホスファイトまたはジ(2,4−ジ−(t−ブチル)フェニル)ペンタエリスリトールジホスファイトである、前掲の請求項のいずれかに記載の方法。
- 請求項1〜10のいずれか1項に記載のポリマー組成物を製造する方法であって、溶融バルクポリマーおよび脂肪族臭素含有ポリマーまたは脂肪族臭素含有コポリマーを含有する混合物を、(1)少なくとも1種のアルキルホスファイト、(2)少なくとも1種のエポキシ化合物または(3)少なくとも1種のアルキルホスファイトと少なくとも1種のエポキシ化合物との混合物、の存在下で溶融加工することを含む、方法。
- 脂肪族臭素含有ポリマーおよび少なくとも1種のアルキルホスファイト、少なくとも1種のエポキシ化合物または少なくとも1種のアルキルホスファイトと少なくとも1種のエポキシ化合物との混合物を含む、組成物。
- 100質量部の脂肪族臭素含有ポリマー当たり1〜40質量部のエポキシ化合物が存在する、請求項12に記載のポリマー組成物。
- 100質量部の脂肪族臭素含有ポリマー当たり1〜40質量部のアルキルホスファイトが存在する、請求項11または12に記載のポリマー組成物。
- 脂肪族臭素含有ポリマーが、臭素化ブタジエンホモポリマー、臭素化スチレン/ブタジエンブロックコポリマー、スチレンおよびアリルマレイミドのコポリマー、脂肪族不飽和ポリエステル、ノボラックレジンのアリルエステル、またはROMPポリマーもしくはROMPコポリマーである、請求項11〜14のいずれか1項に記載のポリマー組成物。
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PCT/US2009/067034 WO2010080285A2 (en) | 2008-12-18 | 2009-12-07 | Stabilizers for polymers containing aliphatically-bound bromine |
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EP3301135A1 (en) | 2016-10-03 | 2018-04-04 | Toyo Styrene Co., Ltd. | Flame-retardant resin composition and flame-retardant resin molded article |
KR20180037120A (ko) | 2016-10-03 | 2018-04-11 | 도요 스티렌 가부시키가이샤 | 난연성 수지 조성물 및 난연성 수지 성형체 |
JP2018059041A (ja) * | 2016-10-03 | 2018-04-12 | 東洋スチレン株式会社 | 難燃性樹脂組成物及び難燃性樹脂成形体 |
US10550258B2 (en) | 2016-10-03 | 2020-02-04 | TOYO STYRENE Co., LTD | Flame-retardant resin composition and flame-retardant resin molded article |
US10920039B2 (en) | 2016-10-03 | 2021-02-16 | Toyo Styrene Co., Ltd. | Flame-retardant resin composition and flame-retardant resin molded article |
JP2017149997A (ja) * | 2017-06-13 | 2017-08-31 | 株式会社ジェイエスピー | ポリスチレン系樹脂押出発泡板 |
JP2017149996A (ja) * | 2017-06-13 | 2017-08-31 | 株式会社ジェイエスピー | ポリスチレン系樹脂押出発泡板の製造方法 |
JP2017160461A (ja) * | 2017-06-13 | 2017-09-14 | 株式会社ジェイエスピー | ポリスチレン系樹脂押出発泡板の製造方法 |
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CA2747386A1 (en) | 2010-07-15 |
WO2010080285A2 (en) | 2010-07-15 |
CA2747386C (en) | 2016-12-06 |
CN102257050B (zh) | 2013-09-04 |
US9663649B2 (en) | 2017-05-30 |
WO2010080285A3 (en) | 2010-09-16 |
RU2011129655A (ru) | 2013-01-27 |
US20110240906A1 (en) | 2011-10-06 |
CN102257050A (zh) | 2011-11-23 |
US20160137826A1 (en) | 2016-05-19 |
JP5462278B2 (ja) | 2014-04-02 |
EP2379628B1 (en) | 2013-08-21 |
RU2528677C2 (ru) | 2014-09-20 |
US20170058118A1 (en) | 2017-03-02 |
ES2434120T3 (es) | 2013-12-13 |
EP2379628A2 (en) | 2011-10-26 |
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