JP4324940B2 - ヒドロキシルアミンエステル含有難燃性ポリマー組成物 - Google Patents

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Publication number

JP4324940B2

JP4324940B2 JP2003584163A JP2003584163A JP4324940B2 JP 4324940 B2 JP4324940 B2 JP 4324940B2 JP 2003584163 A JP2003584163 A JP 2003584163A JP 2003584163 A JP2003584163 A JP 2003584163A JP 4324940 B2 JP4324940 B2 JP 4324940B2

Authority

JP

Japan

Prior art keywords

group

carbon atoms

tert

bis

butyl

Prior art date

2002-04-17

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Lifetime

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• -1 hydroxylamine ester Chemical class 0.000 title claims abstract description 194
• 239000003063 flame retardant Substances 0.000 title claims abstract description 29
• 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 25
• 239000000203 mixture Substances 0.000 title claims description 67
• 229920000642 polymer Polymers 0.000 title description 50
• 229920001169 thermoplastic Polymers 0.000 claims abstract description 14
• 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 8
• 125000004432 carbon atom Chemical group C* 0.000 claims description 217
• 125000000217 alkyl group Chemical group 0.000 claims description 64
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 35
• 125000002947 alkylene group Chemical group 0.000 claims description 33
• 239000000654 additive Substances 0.000 claims description 32
• 125000003118 aryl group Chemical group 0.000 claims description 32
• 150000001875 compounds Chemical class 0.000 claims description 20
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
• 150000001412 amines Chemical class 0.000 claims description 15
• 229910052751 metal Inorganic materials 0.000 claims description 14
• 239000002184 metal Substances 0.000 claims description 14
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 10
• 230000000996 additive effect Effects 0.000 claims description 10
• 229910052698 phosphorus Inorganic materials 0.000 claims description 10
• 239000011574 phosphorus Substances 0.000 claims description 10
• 229910052799 carbon Inorganic materials 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 125000004429 atom Chemical group 0.000 claims description 8
• 229910044991 metal oxide Inorganic materials 0.000 claims description 8
• 150000004706 metal oxides Chemical class 0.000 claims description 8
• 229910000000 metal hydroxide Inorganic materials 0.000 claims description 7
• ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 6
• XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 6
• 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 claims description 6
• 150000001463 antimony compounds Chemical class 0.000 claims description 6
• 229910052796 boron Inorganic materials 0.000 claims description 6
• 150000004677 hydrates Chemical class 0.000 claims description 6
• 150000004692 metal hydroxides Chemical class 0.000 claims description 6
• 229910052710 silicon Inorganic materials 0.000 claims description 6
• 239000010703 silicon Substances 0.000 claims description 6
• 239000000758 substrate Substances 0.000 claims description 6
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 238000002156 mixing Methods 0.000 claims description 4
• AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 4
• ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical class C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 claims description 3
• 239000006096 absorbing agent Substances 0.000 claims description 3
• JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical class C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 3
• XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 3
• 239000002530 phenolic antioxidant Substances 0.000 claims description 2
• GGZAHARVCVECSS-UHFFFAOYSA-N (9-acetyloxy-3,8,10-triethyl-8,10,11-trimethyl-1,5-dioxa-9-azaspiro[5.5]undecan-3-yl)methyl octadecanoate Chemical compound O1CC(COC(=O)CCCCCCCCCCCCCCCCC)(CC)COC11C(C)C(C)(CC)N(OC(C)=O)C(C)(CC)C1 GGZAHARVCVECSS-UHFFFAOYSA-N 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 13
• 150000002443 hydroxylamines Chemical class 0.000 abstract description 8
• 229920000620 organic polymer Polymers 0.000 abstract description 4
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical class C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 56
• 229920001577 copolymer Polymers 0.000 description 42
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 25
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 24
• 239000002253 acid Substances 0.000 description 23
• 238000012360 testing method Methods 0.000 description 22
• 229910052757 nitrogen Inorganic materials 0.000 description 19
• 239000004793 Polystyrene Substances 0.000 description 17
• 239000000463 material Substances 0.000 description 17
• 229920002223 polystyrene Polymers 0.000 description 17
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 15
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 14
• 239000005977 Ethylene Substances 0.000 description 14
• 125000001931 aliphatic group Chemical group 0.000 description 14
• 125000003342 alkenyl group Chemical group 0.000 description 13
• 239000000243 solution Substances 0.000 description 13
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 12
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
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• 239000004743 Polypropylene Substances 0.000 description 12
• 229920002647 polyamide Polymers 0.000 description 12
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 11
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 11
• 125000002252 acyl group Chemical group 0.000 description 10
• 230000000052 comparative effect Effects 0.000 description 10
• 125000000753 cycloalkyl group Chemical group 0.000 description 10
• 229920006248 expandable polystyrene Polymers 0.000 description 10
• 239000006260 foam Substances 0.000 description 10
• 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 9
• 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 9
• 125000003710 aryl alkyl group Chemical group 0.000 description 8
• 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 8
• KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
• 239000003054 catalyst Substances 0.000 description 8
• 229920001684 low density polyethylene Polymers 0.000 description 8
• 239000004702 low-density polyethylene Substances 0.000 description 8
• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
• 229920002857 polybutadiene Polymers 0.000 description 8
• 239000004417 polycarbonate Substances 0.000 description 8
• 229920000728 polyester Polymers 0.000 description 8
• 229920001155 polypropylene Polymers 0.000 description 8
• 238000012545 processing Methods 0.000 description 8
• 239000000047 product Substances 0.000 description 8
• 238000010561 standard procedure Methods 0.000 description 8
• 229920002554 vinyl polymer Polymers 0.000 description 8
• 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 7
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 7
• 239000005062 Polybutadiene Substances 0.000 description 7
• KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 7
• 150000001993 dienes Chemical class 0.000 description 7
• 150000002148 esters Chemical class 0.000 description 7
• 239000004700 high-density polyethylene Substances 0.000 description 7
• 239000000178 monomer Substances 0.000 description 7
• 229920000098 polyolefin Polymers 0.000 description 7
• 229920006324 polyoxymethylene Polymers 0.000 description 7
• 239000004800 polyvinyl chloride Substances 0.000 description 7
• 229920000915 polyvinyl chloride Polymers 0.000 description 7
• 239000000126 substance Substances 0.000 description 7
• XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
• 239000004721 Polyphenylene oxide Substances 0.000 description 6
• 239000007983 Tris buffer Substances 0.000 description 6
• WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
• 125000002723 alicyclic group Chemical group 0.000 description 6
• 125000000304 alkynyl group Chemical group 0.000 description 6
• 238000002485 combustion reaction Methods 0.000 description 6
• 150000001991 dicarboxylic acids Chemical class 0.000 description 6
• 239000000539 dimer Substances 0.000 description 6
• DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 6
• 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 6
• 229920001903 high density polyethylene Polymers 0.000 description 6
• 229920001519 homopolymer Polymers 0.000 description 6
• 239000007924 injection Substances 0.000 description 6
• 238000002347 injection Methods 0.000 description 6
• QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
• 239000002245 particle Substances 0.000 description 6
• 239000008188 pellet Substances 0.000 description 6
• 239000004814 polyurethane Substances 0.000 description 6
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
• 229930185605 Bisphenol Natural products 0.000 description 5
• 229920000089 Cyclic olefin copolymer Polymers 0.000 description 5
• 229910019142 PO4 Inorganic materials 0.000 description 5
• 239000004698 Polyethylene Substances 0.000 description 5
• 150000007513 acids Chemical class 0.000 description 5
• 125000004450 alkenylene group Chemical group 0.000 description 5
• QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 5
• 239000012964 benzotriazole Substances 0.000 description 5
• 230000006835 compression Effects 0.000 description 5
• 238000007906 compression Methods 0.000 description 5
• 229920001971 elastomer Polymers 0.000 description 5
• XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 5
• 239000004615 ingredient Substances 0.000 description 5
• FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical compound C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 description 5
• SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 5
• 150000002978 peroxides Chemical class 0.000 description 5
• 235000021317 phosphate Nutrition 0.000 description 5
• 229920000573 polyethylene Polymers 0.000 description 5
• 238000006116 polymerization reaction Methods 0.000 description 5
• 229920006380 polyphenylene oxide Polymers 0.000 description 5
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
• 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 5
• ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 5
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• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
• DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
• 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 4
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