JPH0450922B2 - - Google Patents
Info
- Publication number
- JPH0450922B2 JPH0450922B2 JP59236829A JP23682984A JPH0450922B2 JP H0450922 B2 JPH0450922 B2 JP H0450922B2 JP 59236829 A JP59236829 A JP 59236829A JP 23682984 A JP23682984 A JP 23682984A JP H0450922 B2 JPH0450922 B2 JP H0450922B2
- Authority
- JP
- Japan
- Prior art keywords
- tert
- butyl
- ethylene
- hydrogen
- new polymer
- 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.)
- Expired - Lifetime
Links
- 229920000642 polymer Polymers 0.000 claims description 33
- 239000000178 monomer Substances 0.000 claims description 31
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 17
- 239000005977 Ethylene Substances 0.000 claims description 17
- 125000003367 polycyclic group Chemical group 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims description 6
- 229920005604 random copolymer Polymers 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- -1 polyethylene terephthalate Polymers 0.000 description 30
- 229920001577 copolymer Polymers 0.000 description 16
- 239000011777 magnesium Substances 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 10
- 229910052749 magnesium Inorganic materials 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 238000007334 copolymerization reaction Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 150000003682 vanadium compounds Chemical class 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002131 composite material Substances 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 239000010936 titanium Substances 0.000 description 6
- 229910052719 titanium Inorganic materials 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 229910052720 vanadium Inorganic materials 0.000 description 5
- 239000001993 wax Substances 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 230000032683 aging Effects 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 150000002681 magnesium compounds Chemical class 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 229920000098 polyolefin Polymers 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 150000003609 titanium compounds Chemical class 0.000 description 4
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- PFANXOISJYKQRP-UHFFFAOYSA-N 2-tert-butyl-4-[1-(5-tert-butyl-4-hydroxy-2-methylphenyl)butyl]-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(CCC)C1=CC(C(C)(C)C)=C(O)C=C1C PFANXOISJYKQRP-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 229920006324 polyoxymethylene Polymers 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 239000005060 rubber Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 229920003002 synthetic resin Polymers 0.000 description 3
- 239000000057 synthetic resin Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- JYFCQYQQTDXYSP-UHFFFAOYSA-N ClC(CO[V]=O)Cl Chemical compound ClC(CO[V]=O)Cl JYFCQYQQTDXYSP-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 125000005234 alkyl aluminium group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000002667 nucleating agent Substances 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229920002601 oligoester Polymers 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000012766 organic filler Substances 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 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 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OJOWICOBYCXEKR-APPZFPTMSA-N (1S,4R)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound CC=C1C[C@@H]2C[C@@H]1C=C2 OJOWICOBYCXEKR-APPZFPTMSA-N 0.000 description 1
- KJYSXRBJOSZLEL-UHFFFAOYSA-N (2,4-ditert-butylphenyl) 3,5-ditert-butyl-4-hydroxybenzoate Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 KJYSXRBJOSZLEL-UHFFFAOYSA-N 0.000 description 1
- OLGRFMBKPOZZHR-UHFFFAOYSA-N (2-hydroxy-4-methoxyphenyl)-(2-hydroxyphenyl)methanone;(2-hydroxy-4-octoxyphenyl)-phenylmethanone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1O.OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 OLGRFMBKPOZZHR-UHFFFAOYSA-N 0.000 description 1
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- WBSRIXCTCFFHEF-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methyl-ethoxyphosphinic acid Chemical compound CCOP(O)(=O)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 WBSRIXCTCFFHEF-UHFFFAOYSA-N 0.000 description 1
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 1
- HUURUXFGQMRTPV-UHFFFAOYSA-N 1,1-dichlorohex-1-ene Chemical compound CCCCC=C(Cl)Cl HUURUXFGQMRTPV-UHFFFAOYSA-N 0.000 description 1
- PIBKGXNSYQOGKL-UHFFFAOYSA-N 1,3,5-tribenzyl-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC=2C=CC=CC=2)C(=O)N(CC=2C=CC=CC=2)C(=O)N1CC1=CC=CC=C1 PIBKGXNSYQOGKL-UHFFFAOYSA-N 0.000 description 1
- VNQNXQYZMPJLQX-UHFFFAOYSA-N 1,3,5-tris[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2C(N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C(=O)N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C2=O)=O)=C1 VNQNXQYZMPJLQX-UHFFFAOYSA-N 0.000 description 1
- MADORZDTLHDDEN-UHFFFAOYSA-N 1-piperidin-1-ylethanol Chemical compound CC(O)N1CCCCC1 MADORZDTLHDDEN-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- TUYBEVLJKZQJPO-UHFFFAOYSA-N 19-(3,5-ditert-butyl-4-hydroxyphenyl)heptatriacontan-19-ylphosphonic acid Chemical compound CCCCCCCCCCCCCCCCCCC(CCCCCCCCCCCCCCCCCC)(P(O)(O)=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 TUYBEVLJKZQJPO-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- GXURZKWLMYOCDX-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.OCC(CO)(CO)CO GXURZKWLMYOCDX-UHFFFAOYSA-N 0.000 description 1
- JAFWYPBFIGXMLO-UHFFFAOYSA-N 2-(2H-benzotriazol-4-yl)-4,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)c1cc(c(O)c(c1)C(C)(C)CC)-c1cccc2[nH]nnc12 JAFWYPBFIGXMLO-UHFFFAOYSA-N 0.000 description 1
- GGINXIIPQOLTOB-UHFFFAOYSA-N 2-(4-methylpent-3-enyl)-3,4-dihydro-2h-chromen-6-ol Chemical compound OC1=CC=C2OC(CCC=C(C)C)CCC2=C1 GGINXIIPQOLTOB-UHFFFAOYSA-N 0.000 description 1
- WQYFETFRIRDUPJ-UHFFFAOYSA-N 2-[2-hydroxy-5-(2,4,4-trimethylpentan-2-yl)phenyl]sulfanyl-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(SC=2C(=CC=C(C=2)C(C)(C)CC(C)(C)C)O)=C1 WQYFETFRIRDUPJ-UHFFFAOYSA-N 0.000 description 1
- MQRCHVBRBGNZGJ-UHFFFAOYSA-N 2-[3,5-bis[2-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]ethyl]-2,4,6-trioxo-1,3,5-triazinan-1-yl]ethyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCCN2C(N(CCOC(=O)CCC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C(=O)N(CCOC(=O)CCC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C2=O)=O)=C1 MQRCHVBRBGNZGJ-UHFFFAOYSA-N 0.000 description 1
- PHXLONCQBNATSL-UHFFFAOYSA-N 2-[[2-hydroxy-5-methyl-3-(1-methylcyclohexyl)phenyl]methyl]-4-methyl-6-(1-methylcyclohexyl)phenol Chemical compound OC=1C(C2(C)CCCCC2)=CC(C)=CC=1CC(C=1O)=CC(C)=CC=1C1(C)CCCCC1 PHXLONCQBNATSL-UHFFFAOYSA-N 0.000 description 1
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- AQBTWPYGBZJMLL-UHFFFAOYSA-N cyclohexane;terephthalic acid Chemical compound C1CCCCC1.OC(=O)C1=CC=C(C(O)=O)C=C1 AQBTWPYGBZJMLL-UHFFFAOYSA-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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- TUTWLYPCGCUWQI-UHFFFAOYSA-N decanamide Chemical compound CCCCCCCCCC(N)=O TUTWLYPCGCUWQI-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- NJLLQSBAHIKGKF-UHFFFAOYSA-N dipotassium dioxido(oxo)titanium Chemical compound [K+].[K+].[O-][Ti]([O-])=O NJLLQSBAHIKGKF-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- ILRSCQWREDREME-UHFFFAOYSA-N dodecanamide Chemical compound CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 239000012772 electrical insulation material Substances 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000012765 fibrous filler Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 238000005338 heat storage Methods 0.000 description 1
- AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 1
- HSEMFIZWXHQJAE-UHFFFAOYSA-N hexadecanamide Chemical compound CCCCCCCCCCCCCCCC(N)=O HSEMFIZWXHQJAE-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 235000000396 iron Nutrition 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000004761 kevlar Substances 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 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
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- QEALYLRSRQDCRA-UHFFFAOYSA-N myristamide Chemical compound CCCCCCCCCCCCCC(N)=O QEALYLRSRQDCRA-UHFFFAOYSA-N 0.000 description 1
- YDHLKLICOYJGND-UHFFFAOYSA-N n'-ethoxy-n-ethyl-n,n'-diphenyloxamide Chemical compound C=1C=CC=CC=1N(OCC)C(=O)C(=O)N(CC)C1=CC=CC=C1 YDHLKLICOYJGND-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- VLCWFGZZAJZBLO-UHFFFAOYSA-L nickel(2+);2-[2-oxido-5-(2,4,4-trimethylpentan-2-yl)phenyl]sulfanyl-4-(2,4,4-trimethylpentan-2-yl)phenolate Chemical class [Ni+2].CC(C)(C)CC(C)(C)C1=CC=C([O-])C(SC=2C(=CC=C(C=2)C(C)(C)CC(C)(C)C)[O-])=C1 VLCWFGZZAJZBLO-UHFFFAOYSA-L 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
- 150000002848 norbornenes Chemical class 0.000 description 1
- LTHCSWBWNVGEFE-UHFFFAOYSA-N octanamide Chemical compound CCCCCCCC(N)=O LTHCSWBWNVGEFE-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- AXRSHKZFNKUGQB-UHFFFAOYSA-N octyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCCCCCCCC)OC1=CC=CC=C1 AXRSHKZFNKUGQB-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
- 239000013307 optical fiber Substances 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229960000969 phenyl salicylate Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- ZDCHZHDOCCIZIY-UHFFFAOYSA-N phthalic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.OC(=O)C1=CC=CC=C1C(O)=O ZDCHZHDOCCIZIY-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229920002620 polyvinyl fluoride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000012254 powdered material Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000012748 slip agent Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229940012831 stearyl alcohol Drugs 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
- 238000003756 stirring Methods 0.000 description 1
- 239000011232 storage material Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229940071127 thioglycolate Drugs 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- QOQNJVLFFRMJTQ-UHFFFAOYSA-N trioctyl phosphite Chemical compound CCCCCCCCOP(OCCCCCCCC)OCCCCCCCC QOQNJVLFFRMJTQ-UHFFFAOYSA-N 0.000 description 1
- URRFGQHFJDWCFM-UHFFFAOYSA-N tris(2-butoxyethyl) phosphite Chemical compound CCCCOCCOP(OCCOCCCC)OCCOCCCC URRFGQHFJDWCFM-UHFFFAOYSA-N 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
- LUUMBHMWFNNZPH-UHFFFAOYSA-N tris(3,5-ditert-butyl-4-hydroxyphenyl) phosphite Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(OP(OC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)OC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 LUUMBHMWFNNZPH-UHFFFAOYSA-N 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000004078 waterproofing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymerization Catalysts (AREA)
Description
〔産業上の利用分野〕
本発明は透明性に優れかつ耐熱性、耐熱老化
性、耐薬品性、耐溶剤性、誘電持性及び剛性など
の機械的性質のバランスのとれた新重合体を提供
することを目的とし、更に詳しくはエチレンと下
記一般式で示される多環式モノマーとのランダム
共重合体である新重合体を提供することを目的と
する。
(ここでR1〜R12は水素、アルキル基又はハロ
ゲンであつて各同一又は異なつていてもよく、ま
たR9又はR10とR11又はR12とは互に環を形成して
いてもよい。更にR9又はR10及びR11又はR12が水
素であつて残基が環を形成しないときは、R1〜
R8のうち少なくとも1個は水素以外の基であ
る。)
〔従来技術〕
透明性に優れた合成樹脂としては、ポリカーボ
ネートやポリメタクリル酸メチルあるいはポリエ
チレンテレフタレートなどが知られている。たと
えばポリカーボネートは透明性と共に耐熱性、耐
熱老化性、耐衝撃性にも優れた樹脂である。しか
し強アルカリに対しては容易に侵されて耐薬品性
に劣るという問題がある。ポリメタクリル酸メチ
ルは酢酸エチルやアセトンなどに侵され易く又エ
ーテル中で膨潤を起こすので耐溶剤性に劣り、更
に耐熱性も低いという問題がある。ポリエチレン
テレフタレートは耐熱性や機械的性質に優れるも
のの強酸やアルカリに弱く、加水分解を受け易い
という問題がある。
一方、汎用樹脂として有名なポリオレフイン
は、耐薬品性、耐溶剤性に優れ、また機械的性質
に優れたものが多いが、耐熱性の乏しいものが多
く、結晶性樹脂であるが故に透明性に劣る。一般
にポリオレフインの透明性改善には造核剤をを添
加して結晶構造を微細化するか、若しくは急冷を
行つて結晶の成長を止める方法が用いられるが、
その効果は十分とは言い難い。むしろ造核剤のよ
うな第3成分を添加することはポリオレフインが
本来有している優れた諸性質を損なう虞もあり、
又急冷は装置が大掛かりになるほか、結晶化度の
低下に伴つて耐熱性や剛性なども低下する虞があ
る。
〔発明の目的〕
そこで本出願人は、透明性を有しながら耐熱
性、耐熱老化性、耐溶剤性、誘電持性、機械的性
質のバランスのとれた合成樹脂が得られないか研
究を重ねた結果、エチレンと特定の崇高なモノマ
ー成分すなわち1,4,5,8−ジメタノ−1,
2,3,4,4a,5,8,8a−オクタヒドロナ
フタレン類(又はテトラシクロ〔4,4,0,
12.5,17.10〕ドデセン−3類ともいう:以下
DMON類と省略する)との共重合体が目的を達
成できることを見い出し、特願昭59−16995号に
おいてその技術内容を開示した。
本発明は前記の出願において提案した技術の改
良に関するものである。
なお、本発明において「重合」という語は、単
独重合だけでなく、共重合をも包含した意味で用
いられることがあり、また「重合体」という語
は、単独重合体だけでなく、共重合体をも包含し
た意味で用いられることがある。
〔問題を解決するための手段〕
すなわち本発明は、
(A) エチレンと上記一般式()で示される多環
式モノマーとから得られるランダム共重合体で
あつて、
(B) エチレン単位/多環式モノマー単位(モル
比)が90/10〜10/90であり、
(C) エチレン単位が下記式で示されるとともに、
(−CH2−CH2)−
多環式モノマー単位が主として下記一般式
()で示す構造をとり、
(D) 135℃、デカリン中で測定した極限粘度〔η〕
が、0.3〜20dl/gで定義づけられる新重合体
に関する。
〔新重合体の概要〕
本発明の新重合体は、実質的にエチレンと多環
式モノマーとのランダム共重合体である。しかし
ながら本発明の目的を損わない範囲で、他の共重
合可能なモノマー成分をたとえば多環式モノマー
成分単位の50モル%以下の範囲で共重合させてい
てもかまわない。かかる共重合可能なモノマーの
具体例としては、たとえばプロピレン、1−ブテ
ン、3−メチル−1−ブテン、1−ペンテン、4
−メチル−1−ペンテン、1−ヘキセン、1−デ
センなどの炭素原子数3以上のα−オレフイン、
シクロペンテン、ジクロヘキセン、3−メチルシ
クロヘキセンなどのシクロオレフイン、スチレ
ン、α−メチルスチレンなどのスチレン類、ノル
ボルネン、メチルノルボルネン、エチルノルボル
ネン、イソブチルノルボルネンなどのノルボルネ
ン類、2,3,3a,7a−テトラヒドロ−4,7
−メタノ−1H−インデン(一般式(イ))、3a,
5,6,7a−テトラヒドロ4,7−メタノ−1H
−インデン(一般式(ロ))などの本発明の一般
式()に含まれないエンドメチレン系化合物あ
るいは1,4−ヘキサジエン、ジシクロペンタジ
エン、5−エチリデン−2−ノルボルネンなどの
ポリエンを挙げることができる。
[Industrial Application Field] The present invention provides a new polymer with excellent transparency and well-balanced mechanical properties such as heat resistance, heat aging resistance, chemical resistance, solvent resistance, dielectric retention, and rigidity. More specifically, the purpose is to provide a new polymer that is a random copolymer of ethylene and a polycyclic monomer represented by the following general formula. (Here, R 1 to R 12 are hydrogen, an alkyl group, or a halogen, and may be the same or different, and R 9 or R 10 and R 11 or R 12 mutually form a ring. Furthermore, when R 9 or R 10 and R 11 or R 12 are hydrogen and the residues do not form a ring, R 1 to
At least one of R 8 is a group other than hydrogen. ) [Prior Art] Polycarbonate, polymethyl methacrylate, polyethylene terephthalate, and the like are known as synthetic resins with excellent transparency. For example, polycarbonate is a resin that has excellent heat resistance, heat aging resistance, and impact resistance as well as transparency. However, there is a problem that it is easily attacked by strong alkalis and has poor chemical resistance. Polymethyl methacrylate is easily attacked by ethyl acetate, acetone, etc., and swells in ether, so it has poor solvent resistance and also has low heat resistance. Although polyethylene terephthalate has excellent heat resistance and mechanical properties, it is susceptible to strong acids and alkalis and is susceptible to hydrolysis. On the other hand, many polyolefins, which are famous as general-purpose resins, have excellent chemical resistance, solvent resistance, and mechanical properties, but many have poor heat resistance, and because they are crystalline resins, they lack transparency. Inferior. Generally, to improve the transparency of polyolefins, methods are used to refine the crystal structure by adding a nucleating agent, or to stop crystal growth by rapid cooling.
It is hard to say that the effect is sufficient. On the contrary, adding a third component such as a nucleating agent may impair the excellent properties that polyolefin originally has.
In addition, rapid cooling requires a large-scale apparatus, and there is also a risk that heat resistance and rigidity may decrease as the degree of crystallinity decreases. [Purpose of the Invention] Therefore, the applicant has conducted repeated research to find out whether it is possible to obtain a synthetic resin that is transparent, yet has a good balance of heat resistance, heat aging resistance, solvent resistance, dielectric retention, and mechanical properties. As a result, ethylene and certain noble monomer components, namely 1,4,5,8-dimethano-1,
2,3,4,4a,5,8,8a-octahydronaphthalenes (or tetracyclo[4,4,0,
1 2.5 , 1 7.10 ] Also referred to as dodecene-3 class: below
It was discovered that a copolymer with DMON (abbreviated as "DMON") could achieve the objective, and the technical details thereof were disclosed in Japanese Patent Application No. 16995-1983. The present invention relates to an improvement of the technique proposed in the above-mentioned application. In addition, in the present invention, the word "polymerization" is sometimes used to include not only homopolymerization but also copolymerization, and the word "polymer" refers not only to homopolymerization but also to copolymerization. It is sometimes used in a sense that also includes union. [Means for solving the problem] That is, the present invention provides a random copolymer obtained from (A) ethylene and a polycyclic monomer represented by the above general formula (), and (B) a random copolymer obtained from ethylene units/polycyclic monomers. Cyclic monomer units (molar ratio) are 90/10 to 10/90, (C) ethylene units are represented by the following formula, and (-CH 2 - CH 2 )- polycyclic monomer units are mainly the following general Takes the structure shown in formula (), (D) Intrinsic viscosity [η] measured in decalin at 135℃
is defined as 0.3 to 20 dl/g. [Outline of new polymer] The new polymer of the present invention is substantially a random copolymer of ethylene and a polycyclic monomer. However, other copolymerizable monomer components may be copolymerized, for example, within a range of 50 mol % or less of the polycyclic monomer component units, as long as the object of the present invention is not impaired. Specific examples of such copolymerizable monomers include propylene, 1-butene, 3-methyl-1-butene, 1-pentene, 4
- α-olefin having 3 or more carbon atoms such as methyl-1-pentene, 1-hexene, 1-decene,
Cycloolefins such as cyclopentene, dichlorohexene, and 3-methylcyclohexene; styrenes such as styrene and α-methylstyrene; norbornenes such as norbornene, methylnorbornene, ethylnorbornene, and isobutylnorbornene; 2,3,3a,7a-tetrahydro-4 ,7
-methano-1H-indene (general formula (a)), 3a,
5,6,7a-tetrahydro4,7-methano-1H
- Mention endomethylene compounds not included in the general formula () of the present invention such as indene (general formula (b)) or polyenes such as 1,4-hexadiene, dicyclopentadiene, and 5-ethylidene-2-norbornene. Can be done.
本発明の新重合体の具体的な利用分野の一例を
示すと、その優れた物理的諸性質を生かして、低
分子量体の場合には通常合成ワツクスで利用でき
る分野すなわちロウソク用途、マツチ軸木含侵
剤、紙加工剤、サイズ剤、ゴム老化防止剤、段ボ
ール耐水化剤、化成肥料遅効化剤、蓄熱材、セラ
ミツクバインダー、紙コンデンサー・電線・ケー
ブル等の電気絶縁材、中性子減速材、繊維加工助
剤、建材発水剤、塗料保護剤、つや出し剤、チク
ソトロピー付与剤、鉛筆・クレヨンの芯硬度付与
剤、カーボンインキ基剤、静電複写用トナー、合
成樹脂成形用滑剤、離型剤、樹脂着色剤、ホツト
メルト接着剤、潤滑用グリースなどを挙げること
ができる。また高分子量体の場合には、プラスチ
ツクレンズ、光デイスク、光フアイバー、ガラス
窓用途等の光学分野、透明導電性フイルム・シー
ト、液晶表示基板、高周波用回路基板、電気アイ
ロンの水タンク、電子レンジ用品等の電気分野、
注射器、ピペツト、アニマルゲージ等の医療、化
学分野、カメラボデイ、各種計器類ハウジング、
プラスチツク磁石、フイルム、シート、ヘルメツ
トなど種々の分野に利用できる。
〔成形加工及び安定剤〕
本発明の新重合体は周知の方法によつて成形加
工される。たとえば単軸押出機、ベント式押出
機、二本スクリユー押出機、円錐二本スクリユー
押出機、コニーダー、プラテイフイケーター、ミ
クストルーダー、二軸コニカルスクリユー押出
機、遊星ねじ押出機、歯車型押出機、スクリユー
レス押出機などを用いて押出成形、射出成形、ブ
ロー成形、回転成形などを行う。また成形加工に
あたつては、必要に応じて周知の添加剤すなわち
耐熱安定剤、光安定剤、帯電防止剤、スリツプ
剤、アンチブロツキング剤、防曇剤、滑剤、合成
油、天然油、無機および有機の充填剤、染料、顔
料などを添加してもよい。
このような添加剤としては、たとえばフエノー
ル系または硫黄系酸化防止剤が例示できる。フエ
ノール系酸化防止剤としては、たとえば2,6−
ジ−tert−ブチル−p−クレゾール、ステアリル
(3,3−ジメチル−4−ヒドロキシベンジル)
チオグリコレート、ステアリル−β−(4−ヒド
ロキシ−3,5−ジ−tert−ブチルフエノール)
プロピオネート、ジステアリル−3,5−ジ−
tert−ブチル−4−ヒドロキシベンジルホスホネ
ート、2、4,6−トリス(3′,5′−ジ−tert−
ブチル−4′−ヒドロキシベンジルチオ)−1,3,
5−トリアジン、ジステアリル(4−ヒドロキシ
−3−メチル−5−tert−ブチルベンジル)マロ
ネート、2,2′−メチレンビス(4−メチル−6
−tert−ブチルフエノール)、4,4′−メチレンビ
ス(2,6−ジ−tert−ブチルフエノール)、2,
2′−メチレンビス〔6−(1−メチルシクロヘキ
シル)p−クレゾール〕、ビス〔3,5−ビス
(4−ヒドロキシ−3−tert−ブチルフエニル)
ブチリツクアシド〕グリコールエステル、4,
4′−ブチリデンビス(6−tert−ブチル−m−ク
レゾール)、1,1,3−トリス(2−メチル−
4−ヒドロキシ−5−tert−ブチルフエニル)ブ
タン、ビス〔2−tert−ブチル−4−メチル−6
−(2−ヒドロキシ−3−tert−ブチル−5−メ
チルベンジル)フエニル〕テレフタレート、1,
3,5−トリス(2,6−ジメチル−3−ヒドロ
キシ−4−tert−ブチル)ベンジルイソシアヌレ
ート、1,3,5−トリス(3,5−ジ−tert−
ブチル−4−ヒドロキシベンジル)−2,4,6
−トリメチルベンゼン、テトラキス〔メチレン−
3−(3,5−ジ−tert−ブチル−4−ヒドロキ
シフエニル)プロピオネート〕メタン、1,3,
5−トリス(3,5−ジ−tert−ブチル−4−ヒ
ドロキシベンジル)イソシアヌレート、1,3,
5−トリス〔(3,5−ジ−tert−ブチル−4−
ヒドロキシフエニル)プロピオニルオキシエチ
ル〕イソシアヌレート、2−オクチルチオ−4,
6−ジ(4−ヒドロキシ−3,5−ジ−tert−ブ
チル)フエノキシ−1,3,5−トリアジン、
4,4′−チオビス(6−tert−ブチル−m−クレ
ゾール)などのフエノール類及び4,4′−ブチリ
デンビス(2−tert−ブチル−5−メチルフエノ
ール)の炭酸オリゴエステル(例えば重合度2,
3,4,5,6,7,8,9,10など)などの多
価フエノール炭酸オリゴエステル類が挙げられ
る。
硫黄系酸化防止剤としてはたとえばジラウリル
ー、ジミリスチルー、ジステアリルーなどのジア
ルキルチオジプロピオネート及びブチルー、オク
チルー、ラウリルー、ステアリルーなどのアルキ
ルチオプロピオン酸の多価アルコール(例えばグ
リセリン、トリメチロールエタン、トリメチロー
ルプロパン、ペンタエリスリトール、トリスヒド
ロキシイソシアヌレート)のエステル(例えばペ
ンタエリスリトールテトララウリルチオプロピオ
ネート)が挙げられる。
また別には含リン化合物を配合してもよく、た
とえばトリオクチルホスフアイト、トリラウリル
ホスフアイト、トリデシルホスフアイト、オクチ
ル−ジフエニルホスフアイト、トリス(2,4−
ジ−tert−ブチルフエニル)ホスフアイト、トリ
フエニルホスフアイト、トリス(ブトキシエチ
ル)ホスフアイト、トリス(ノニルフエニル)ホ
スフアイト、ジステアリルペンタエリスリトール
ジホスフアイト、テトラ(トリデシル)−1,1,
3−トリス(2−メチル−5−tert−ブチル−4
−ヒドロキシフエニル)ブタンジホスフアイト、
テトラ(C12〜C15配合アルキル−4,4′−イソプ
ロピリデンジフエニルホスフアイト、テトラ(ト
リデシル)−4,4′−ブチリデンビス(3−メチ
ル−6−tert−ブチルフエノール)ジホスフアイ
ト、トリス(3,5−ジ−tert−ブチル−4−ヒ
ドロキシフエニル)ホスフアイト、トリス(モ
ノ・ジ混合ノニルフエニル)ホスフアイト、水素
化−4,4′−イソプロピリデンジフエノールポリ
ホスフアイト、ビス(オクチルフエニル)・ビス
〔4,4′−ブチリデンビス(3−メチル−6−tert
−ブチルフエノール)〕・1,6−ヘキサンジオー
ルジホスフアイト、フエニル・4,4′−イソプロ
ピリデンジフエノール・ペンタエリスリトールジ
ホスフアイト、ビス(2,4−ジ−tert−ブチル
フエニル)ペンタエリスリトールジホスフアイ
ト、ビス(2,6−ジ−tert−ブチル−4−メチ
ルフエニル)ペンタエリスリトールジホスフアイ
ト、トリス〔4,4′−イソプロピリデンビス(2
−tert−ブチルフエノール)〕ホスフアイト、フ
エニル・ジイソデシルホスフアイト、ジ(ノニル
フエニル)ペンタエリスリトールジホスフアイ
ト、トリス(1,3−ジ−ステアロイルオキシイ
ソプロピル)ホスフアイト、4,4′−イソプロピ
リデンビス(2−tert−ブチルフエノール)・ジ
(ノニルフエニル)ホスフアイト、9,10−ジ−
ヒドロ−9−オキサ−10−ホスフアフエナンスレ
ン−10−オキサイド、テトラキス(2,4−ジ−
tert−ブチルフエニル)4,4′−ビフエニレンジ
ホスホナイトなどが挙げられる。
また6−ヒドロキシクロマン誘導体たとえば
α、β、γ、δの各種トコフエロールやこれらの
混合物、2−(4−メチル−ペンタ−3−エニル)
−6−ヒドロキシクロマンの2,5−ジメチル置
換体、2,5,8−トリメチル置換体、2、5,
7,8−テトラメチル置換体、2,2,7−トリ
メチル−5−tert−ブチル−6−ヒドロキシクロ
マン、2、2,5−トリメチル−7−tert−ブチ
ル−6−ヒドロキシクロマン、2,2,5−トリ
メチル−6−tert−ブチル−6−ヒドロキシクロ
マン、2,2−ジメチル−5−tert−ブチル−6
−ヒドロキシクロマンなど、
また別には一般式
MxAly(OH)2x+3y−2z(A)z・aH2O
(ここでMはMg、CaまたはZn、Aは水酸基以
外のアニオン、x,yおよびzは正数、aは0ま
たは正数をあらわす)で示される複化合物、たと
えば
Mg6Al2(OH)16CO3・4H2O、
Mg8Al2(OH)20CO3・5H2O、
Mg5Al2(OH)14CO3・4H2O、
Mg10Al2(OH)22(CO3)2・4H2O、
Mg6Al2(OH)16HPO4・4H2O、
Ca6Al2(OH)16CO3・4H2O、
Zn6Al2(OH)16CO3・4H2O、
Zn6Al2(OH)16SO4・4H2O、
Mg6Al2(OH)16SO4・4H2O、
Mg6Al2(OH)12CO3・3H2O,などを配合して
もよい。
また特表昭55−501181号に開示されている2−
ベンゾフラノン系化合物、たとえば3−フエニル
−2−ベンゾフラノン、3−フエニル−5,7−
ジ−t−ブチル−2−ベンゾフラノンなどを配合
してもよい。
光安定剤としてはたとえば2−ヒドロキシ−4
−メトキシベンゾフエノン、2−ヒドロキシ−4
−n−オクトキシベンゾフエノン−2,2′−ジ−
ヒドロキシ−4−メトキシベンゾフエノン、2,
4−ジヒドロキシベンゾフエノンなどのヒドロキ
シベンゾフエノン類、2−(2′−ヒドロキシ−
3′−tert−ブチル−5′−メチルフエニル−5−ク
ロロベンゾトリアゾール、2−(2′−ヒドロキシ
−3′,5′−ジ−tert−ブチルフエニル)−5−クロ
ロベンゾトリアゾール、2−(2′−ヒドロキシ−
5′−メチルフエニル)ベンゾトリアゾール、2−
(2′−ヒドロキシ−3′,5′−ジ−tert−アミルフエ
ニル)ベンゾトリアゾールなどのベンゾトリアゾ
ール類、フエニルサリシレート、p−tert−ブチ
ルフエニルサリシレート、2,4−ジ−tert−ブ
チルフエニル−3,5−ジ−tert−ブチル−4−
ヒドロキシベンゾエート、ヘキサデシル−3,5
−ジ−tert−ブチル−4−ヒドロキシベンゾエー
トなどのベンゾエート類、2,2′−チオビス(4
−tert−オクチルフエノール)Ni塩、〔2,2′−
チオビス(4−tert−オクチルフエノラート)〕−
n−ブチルアミンNi、(3,5−ジ−tert−ブチ
ル−4−ヒドロキシベンジル)ホスホン酸モノエ
チルエステルNi塩などのニツケル化合物類、α
−シアノ−β−メチル−β−(p−メトキシフエ
ニル)アクリル酸メチルなどの置換アクリロニト
リル類及びN′−2−メチルフエニル−N−2−
エトキシ−5−tert−ブチルフエニルシユウ酸ジ
アミド、N−2−エチルフエニル−N′−2−エ
トキシフエニルシユウ酸ジアミドなどのシユウ酸
ジアニリド類、ビス(2,2,6,6−テトラメ
チル−4−ピペリジン)セバシエート、ポリ
〔{(6−(1,1,3,3−テトラメチルブチル)
イミノ}−1,3,5−トリアジン−2,4−ジ
イル{4−(2,2,6,6−テトラメチルピペ
リジル)イミノ}ヘキサメチレン〕、2−(4−ヒ
ドロキシ−2,2,6,6−テトラメチル−1−
ピペリジル)エタノールとコハク酸ジメチルとの
縮合物などのヒンダードアミン化合物類が挙げら
れる。
滑剤としてはたとえばパラフインワツクス、ポ
リエチレンワツクス、ポリプロピレンワツクスな
どの脂肪族炭化水素類、カプリン類、ラウリン
酸、ミリスチン酸、パルミチン酸、マーガリン
酸、ステアリン酸、アラキジン酸、ベヘニン酸な
どの高級脂肪酸類またはこれらの金属塩類、すな
わちリチウム塩、カルシウム塩、ナトリウム塩、
マグネシウム塩、カリウム塩など、パルミチルア
ルコール、セチルアルコール、ステアリルアルコ
ールなとの脂肪族アルコール類、カプロン酸アミ
ド、カプリル酸アミド、カプリン酸アミド、ラウ
リル酸アミド、ミリスチン酸アミド、パルミチン
酸アミド、ステアリン酸アミドなどの脂肪族アミ
ド類、脂肪酸とアルコールとのエステル類、フル
オロアルキルカルボン酸またはその金属塩、フル
オロアルキルスルホン酸金属塩などのフツ素化合
物類が挙げられる。
充填剤としては、ガラス繊維、銀又はアルミニ
ウムコートガラス繊維、ステンレス繊維、アルミ
ニウム繊維、チタン酸カリウム繊維、炭素繊維、
ケブラー繊維、超高弾性ポリエチレン繊維など
の無機または有機の繊維状充填剤、タルク、炭酸
カルシウム、水酸化マグネシウム、酸化カルシウ
ム、硫酸マグネシウム、グラフアイト、ニツケル
粉、銀粉、銅粉、カーボンブラツク、銀コートガ
ラスビーズ、アルミニウムコートガラスビーズ、
アルミニウムフレーク、ステンレスフレーク、ニ
ツケルコートグラフアイトなどの粉末状、粒状、
フレーク状の無機または有機の充填剤が例示でき
る。
〔他の重合体とのブレンド〕
さらに本発明の新重合体は公知の種々の高分子
量又は低分子量の重合体と配合して使用すること
も可能である。かかる重合体の例としては、
(イ) 1個または2個の不飽和結合を有する炭化水
素から誘導される重合体、
具体的にはポリオレフインたとえば架橋構造
を有していてもよいポリエチレン、ポリプロピ
レン、ポリイソブチレン、ポリメチルブテン−
1、ポリ4−メチルペンテン−1、ポリブテン
−1、ポリイソプレン、ポリブタジエン、ポリ
スチレン、
または前記の重合体を構造するモノマー同志
の共重合体たとえばエチレン・プロピレン共重
合体、プロピレン・ブテン−1共重合体、ブロ
ピレン・イソブチレン共重合体、スチレン・イ
ソブチレン共重合体、スチレン・ブタジエン共
重合体、エチレンおよびプロピレンとジエンた
とえばヘキサジエン、シクロペンタジエン、エ
チリデンノルボルネンなどとの3元共重合体、
あるいはこれらの重合体のブレンド物、グラ
フト重合体、ブロツク共重合など、
(ロ) ハロゲン含有ビニル重合体、
具体的にはポリ塩化ビニル、ポリ塩化ビニリ
デン、ポリフツ化ビニル、ポリクロロプレン、
塩素化ゴムなど、
(ハ) α,β−不飽和酸とその誘導体から誘導され
る重合体、
具体的にはポリアクリレート、ポリメタクリ
レート、ポリアクリルアミド、ポリアクリロニ
トリル、
または前記の重合体を構成するモノマーとそ
の他の共重合可能なモノマーとの共重合体たと
えば、アクニロニトリル・ブタジエン・スチレ
ン共重合体、アクリロニトリル・スチレン共重
合体、アクリロニトリル・スチレン・アクリル
酸エステル共重合など、
(ニ) 不飽和アルコールおよびアミンまたはそのア
シル誘導体またはアセタールから誘導された重
合体、
具体的にはポリビニルアルコール、ポリ酢酸
ビニル、ポリステアリン酸ビニル、ポリ安息香
酸ビニル、ポリマレイン酸ビニル、ポリビニル
ブチラール、ポリアリルフタレート、ポリアリ
ルメラミン、
または前記重合体を構成するモノマーとその
他の共重合可能なモノマーとの共重合体たとえ
ばエチレン・酢酸ビニル共重合体など、
(ホ) エポキシドから誘導された重合体、
具体的にはポリエチレンオキシドまたはビス
グシジルエーテルから誘導された重合体など、
(ヘ) ポリアセタール、
具体的にはポリオキシメチレン、ポリオキシ
エチレン、コモノマーとしてエチレンオキシド
を含むようなポリオキシメチレンなど、
(ト) ポリフエニレンオキシド、
(チ) ポリカーボネート、
(リ) ポリスルフオン、
(ヌ) ポリウレタンおよび尿素樹脂、
(ル) ジアミンおよびジカルボン酸および/ま
たはアミノカルボン酸または相応するラクタム
から誘導されたポリアミドおよびコポリアミ
ド、
具体的にはナイロン6、ナイロン66、ナイロ
ン11、ナイロン12など、
(ヲ) ジカルボン酸およびジアルコールおよ
び/またはオキシカルボン酸または相応するラ
クトンから誘導されたポリエステル、
具体的にはポリエチレンテレフタレート、ポ
リブチレンテレフタレート、ポリ1,4−ジメ
チロール・シクロヘキサンテレフタレートな
ど、
(ワ) アルデヒドとフエノール、尿素またはメ
ラミンから誘導された架橋構造を有した重合
体、具体的にはフエノール・ホルムアルデヒド
樹脂、尿素・ホルムアルデヒド樹脂、メラミ
ン・ホルムアルデヒド樹脂など、
(カ) アルキド樹脂、
具体的にはグリセリン・フタル酸樹脂など、
(ヨ) 飽和および不飽和ジカルボン酸と多価ア
ルコールとのコポリエステルから誘導され、架
橋剤としてビニル化合物を使用して得られる不
飽和ポリエステル樹脂ならびにハロゲン含有改
質樹脂、
(タ) 天然重合体、
具体的にはセルロース、ゴム、蛋白質、
あるいはそれらの誘導体たとえば酢酸セルロ
ース、プロピオン酸セルロース、セルロースエ
ーテルなど、
が例示できる。または合成ワツクスとして用い
る際には公知の種々のワツクスを混合してよい
ことは勿論である。
更には本発明の新重合体の分子量の異なるも
の同志を混合してもよい。
〔モノマー成分〕
本発明の新重合体を構成するモノマー成分とし
ては、前述の一般式()で示される多環式モノ
マーおよびエチレンが用いられる。
多環式モノマー成分を表わす一般式において
は、R1〜R12は水素、アルキル基すなわちメチ
ル、エチル、プロピル、イソプロピル、ブチル、
tert−ブチル等の鎖状アルキル、シクロペンチ
ル、シクロヘキシル等のシクロアルキル、あるい
はフツ素、塩素、臭素、ヨウ素等のハロゲンであ
つて各同一又は異なつていてもよい。またR9又
はR10とR11又はR12とは互いに環を形成していて
もよく、たとえば一般式()、()
(ここでR1〜R20は水素又はアルキル基であつ
て各同一または異なつていてもよい。)などが例
示できる。
更にR9又はR10及びR11又はR12が水素であつ
て、残基が環を形成しないときすなわちDMON
類の構造を採るときはR1〜R8のうち少なくとも
1個は水素以外の基である。
かかる多環式モノマー成分の具体例としては、
次表の如きものを例示することができる。
To give an example of a specific field of application of the new polymer of the present invention, by taking advantage of its excellent physical properties, in the case of a low-molecular weight polymer, it can be used in fields where it can normally be used for synthetic waxes, such as candle applications, pine tree stems, etc. Impregnating agents, paper processing agents, sizing agents, rubber anti-aging agents, cardboard waterproofing agents, chemical fertilizer slowing agents, heat storage materials, ceramic binders, electrical insulation materials such as paper capacitors, electric wires and cables, neutron moderators, fibers Processing aids, water repellents for building materials, paint protectants, polishing agents, thixotropy imparting agents, lead hardening agents for pencils and crayons, carbon ink bases, toners for electrostatic copying, lubricants for synthetic resin molding, mold release agents, Examples include resin colorants, hot melt adhesives, and lubricating greases. In addition, in the case of high molecular weight substances, plastic lenses, optical disks, optical fibers, optical fields such as glass window applications, transparent conductive films and sheets, liquid crystal display substrates, high frequency circuit boards, water tanks of electric irons, microwave ovens, etc. Electrical field such as supplies,
Medical and chemical fields such as syringes, pipettes, animal gauges, camera bodies, housings for various instruments, etc.
It can be used in various fields such as plastic magnets, films, sheets, and helmets. [Molding Process and Stabilizer] The new polymer of the present invention is molded by a well-known method. For example, single-screw extruder, vented extruder, twin-screw extruder, conical twin-screw extruder, co-kneader, plateificator, mixtruder, twin-screw conical screw extruder, planetary screw extruder, gear type extruder. Extrusion molding, injection molding, blow molding, rotary molding, etc. are performed using machines, screwless extruders, etc. In addition, during the molding process, well-known additives such as heat stabilizers, light stabilizers, antistatic agents, slip agents, anti-blocking agents, antifogging agents, lubricants, synthetic oils, and natural oils are added as necessary. , inorganic and organic fillers, dyes, pigments, etc. may be added. Examples of such additives include phenolic or sulfur antioxidants. Examples of phenolic antioxidants include 2,6-
Di-tert-butyl-p-cresol, stearyl (3,3-dimethyl-4-hydroxybenzyl)
Thioglycolate, stearyl-β-(4-hydroxy-3,5-di-tert-butylphenol)
Propionate, distearyl-3,5-di-
tert-butyl-4-hydroxybenzylphosphonate, 2,4,6-tris(3',5'-di-tert-
Butyl-4'-hydroxybenzylthio)-1,3,
5-triazine, distearyl (4-hydroxy-3-methyl-5-tert-butylbenzyl) malonate, 2,2'-methylenebis(4-methyl-6
-tert-butylphenol), 4,4'-methylenebis(2,6-di-tert-butylphenol), 2,
2'-methylenebis[6-(1-methylcyclohexyl)p-cresol], bis[3,5-bis(4-hydroxy-3-tert-butylphenyl)
Butiric acid] glycol ester, 4,
4'-Butylidenebis(6-tert-butyl-m-cresol), 1,1,3-tris(2-methyl-
4-Hydroxy-5-tert-butylphenyl)butane, bis[2-tert-butyl-4-methyl-6
-(2-hydroxy-3-tert-butyl-5-methylbenzyl)phenyl]terephthalate, 1,
3,5-tris(2,6-dimethyl-3-hydroxy-4-tert-butyl)benzyl isocyanurate, 1,3,5-tris(3,5-di-tert-
Butyl-4-hydroxybenzyl)-2,4,6
-trimethylbenzene, tetrakis[methylene-
3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]methane, 1,3,
5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate, 1,3,
5-Tris [(3,5-di-tert-butyl-4-
hydroxyphenyl)propionyloxyethyl]isocyanurate, 2-octylthio-4,
6-di(4-hydroxy-3,5-di-tert-butyl)phenoxy-1,3,5-triazine,
Phenols such as 4,4'-thiobis(6-tert-butyl-m-cresol) and carbonic acid oligoesters of 4,4'-butylidenebis(2-tert-butyl-5-methylphenol) (for example, polymerization degree 2,
Examples include polyhydric phenol carbonate oligoesters such as 3, 4, 5, 6, 7, 8, 9, 10, etc.). Examples of sulfur-based antioxidants include dialkylthiodipropionates such as dilauryl, dimyristyl, and distearyl; and polyhydric alcohols of alkylthiopropionic acids such as butyl, octyl, lauryl, and stearyl (e.g., glycerin, trimethylolethane, trimethylolpropane, and pentyl). Erythritol, trishydroxyisocyanurate) esters (eg, pentaerythritol tetralauryl thiopropionate). Alternatively, phosphorus-containing compounds may be added, such as trioctyl phosphite, trilauryl phosphite, tridecyl phosphite, octyl-diphenyl phosphite, tris(2,4-
di-tert-butylphenyl) phosphite, triphenyl phosphite, tris(butoxyethyl) phosphite, tris(nonylphenyl) phosphite, distearylpentaerythritol diphosphite, tetra(tridecyl)-1,1,
3-tris(2-methyl-5-tert-butyl-4
-hydroxyphenyl)butane diphosphite,
Tetra( C12 - C15 compounded alkyl-4,4'-isopropylidene diphenyl phosphite, Tetra(tridecyl)-4,4'-butylidenebis(3-methyl-6-tert-butylphenol) diphosphite, Tris(3 , 5-di-tert-butyl-4-hydroxyphenyl) phosphite, tris(mono-dimixed nonylphenyl) phosphite, hydrogenated-4,4'-isopropylidene diphenol polyphosphite, bis(octylphenyl), Bis[4,4'-butylidene bis(3-methyl-6-tert
-butylphenol)]・1,6-hexanediol diphosphite, phenyl・4,4′-isopropylidene diphenol・pentaerythritol diphosphite, bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite, tris[4,4'-isopropylidene bis(2
-tert-butylphenol)] phosphite, phenyl diisodecyl phosphite, di(nonylphenyl) pentaerythritol diphosphite, tris(1,3-di-stearoyloxyisopropyl) phosphite, 4,4'-isopropylidene bis(2- tert-butylphenol) di(nonylphenyl) phosphite, 9,10-di-
Hydro-9-oxa-10-phosphaphenanthrene-10-oxide, tetrakis(2,4-di-
(tert-butylphenyl) 4,4'-biphenylene diphosphonite and the like. Also, 6-hydroxychroman derivatives such as various tocopherols α, β, γ, δ and mixtures thereof, 2-(4-methyl-pent-3-enyl)
-6-hydroxychroman with 2,5-dimethyl substitution, 2,5,8-trimethyl substitution, 2,5,
7,8-tetramethyl substituted product, 2,2,7-trimethyl-5-tert-butyl-6-hydroxychroman, 2,2,5-trimethyl-7-tert-butyl-6-hydroxychroman, 2,2 , 5-trimethyl-6-tert-butyl-6-hydroxychroman, 2,2-dimethyl-5-tert-butyl-6
-Hydroxychroman, etc. Alternatively, the general formula MxAly(OH)2x+3y-2z(A)z・aH 2 O (where M is Mg, Ca or Zn, A is an anion other than a hydroxyl group, x, y and z are positive (a represents 0 or a positive number), such as Mg 6 Al 2 (OH) 16 CO 3・4H 2 O, Mg 8 Al 2 (OH) 20 CO 3・5H 2 O, Mg 5 Al 2 (OH) 14 CO 3・4H 2 O, Mg 10 Al 2 (OH) 22 (CO 3 ) 2・4H 2 O, Mg 6 Al 2 (OH) 16 HPO 4・4H 2 O, Ca 6 Al 2 (OH) 16 CO 3・4H 2 O, Zn 6 Al 2 (OH) 16 CO 3・4H 2 O, Zn 6 Al 2 (OH) 16 SO 4・4H 2 O, Mg 6 Al 2 (OH) 16 SO 4.4H 2 O, Mg 6 Al 2 (OH) 12 CO 3.3H 2 O, etc. may be blended. In addition, 2-
Benzofuranone compounds, such as 3-phenyl-2-benzofuranone, 3-phenyl-5,7-
Di-t-butyl-2-benzofuranone or the like may also be blended. Examples of light stabilizers include 2-hydroxy-4
-methoxybenzophenone, 2-hydroxy-4
-n-octoxybenzophenone-2,2'-di-
Hydroxy-4-methoxybenzophenone, 2,
Hydroxybenzophenones such as 4-dihydroxybenzophenone, 2-(2'-hydroxy-
3'-tert-butyl-5'-methylphenyl-5-chlorobenzotriazole, 2-(2'-hydroxy-3',5'-di-tert-butylphenyl)-5-chlorobenzotriazole, 2-(2' -Hydroxy-
5′-methylphenyl)benzotriazole, 2-
Benzotriazoles such as (2'-hydroxy-3',5'-di-tert-amyl phenyl)benzotriazole, phenyl salicylate, p-tert-butylphenyl salicylate, 2,4-di-tert-butylphenyl-3 ,5-di-tert-butyl-4-
Hydroxybenzoate, hexadecyl-3,5
Benzoates such as -di-tert-butyl-4-hydroxybenzoate, 2,2'-thiobis(4
-tert-octylphenol) Ni salt, [2,2'-
Thiobis(4-tert-octylphenolate)]-
Nickel compounds such as n-butylamine Ni, (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonic acid monoethyl ester Ni salt, α
Substituted acrylonitriles such as -cyano-β-methyl-β-(p-methoxyphenyl)methyl acrylate and N'-2-methylphenyl-N-2-
Oxalic acid dianilides such as ethoxy-5-tert-butylphenyl oxalic acid diamide, N-2-ethylphenyl-N'-2-ethoxyphenyl oxalic acid diamide, bis(2,2,6,6-tetramethyl- 4-piperidine) sebaciate, poly[{(6-(1,1,3,3-tetramethylbutyl)
imino}-1,3,5-triazine-2,4-diyl{4-(2,2,6,6-tetramethylpiperidyl)imino}hexamethylene], 2-(4-hydroxy-2,2,6 ,6-tetramethyl-1-
Examples include hindered amine compounds such as a condensate of (piperidyl)ethanol and dimethyl succinate. Examples of lubricants include aliphatic hydrocarbons such as paraffin wax, polyethylene wax, and polypropylene wax, higher fatty acids such as capric acid, lauric acid, myristic acid, palmitic acid, margaric acid, stearic acid, arachidic acid, and behenic acid. or their metal salts, i.e. lithium salts, calcium salts, sodium salts,
Magnesium salts, potassium salts, aliphatic alcohols such as palmityl alcohol, cetyl alcohol, stearyl alcohol, caproic acid amide, caprylic acid amide, capric acid amide, lauric acid amide, myristic acid amide, palmitic acid amide, stearic acid Examples include aliphatic amides such as amides, esters of fatty acids and alcohols, fluorine compounds such as fluoroalkylcarboxylic acids or their metal salts, and fluoroalkylsulfonic acid metal salts. Fillers include glass fiber, silver or aluminum coated glass fiber, stainless steel fiber, aluminum fiber, potassium titanate fiber, carbon fiber,
Inorganic or organic fibrous fillers such as Kevlar fibers and ultra-high elastic polyethylene fibers, talc, calcium carbonate, magnesium hydroxide, calcium oxide, magnesium sulfate, graphite, nickel powder, silver powder, copper powder, carbon black, silver coat glass beads, aluminum coated glass beads,
Powdered and granular materials such as aluminum flakes, stainless steel flakes, and nickel-coated graphite,
Examples include flaky inorganic or organic fillers. [Blend with other polymers] Furthermore, the new polymer of the present invention can also be used in combination with various known polymers of high molecular weight or low molecular weight. Examples of such polymers include (a) polymers derived from hydrocarbons having one or two unsaturated bonds, specifically polyolefins such as polyethylene, polypropylene, which may have a crosslinked structure, Polyisobutylene, polymethylbutene
1. Poly-4-methylpentene-1, polybutene-1, polyisoprene, polybutadiene, polystyrene, or copolymers of monomers constituting the above-mentioned polymers, such as ethylene-propylene copolymer, propylene-butene-1 copolymer copolymers, propylene/isobutylene copolymers, styrene/isobutylene copolymers, styrene/butadiene copolymers, terpolymers of ethylene and propylene with dienes such as hexadiene, cyclopentadiene, ethylidene norbornene, or polymers thereof. Blends, graft polymers, block copolymers, etc. (b) Halogen-containing vinyl polymers, specifically polyvinyl chloride, polyvinylidene chloride, polyvinyl fluoride, polychloroprene,
chlorinated rubber, etc. (c) Polymers derived from α,β-unsaturated acids and their derivatives, specifically polyacrylate, polymethacrylate, polyacrylamide, polyacrylonitrile, or monomers constituting the above polymers. and other copolymerizable monomers, such as acrylonitrile/butadiene/styrene copolymers, acrylonitrile/styrene copolymers, acrylonitrile/styrene/acrylic ester copolymers, (d)unsaturated alcohols and amines. or polymers derived from their acyl derivatives or acetals, in particular polyvinyl alcohol, polyvinyl acetate, polyvinyl stearate, polyvinyl benzoate, polyvinyl maleate, polyvinyl butyral, polyallyl phthalate, polyallylmelamine, or Copolymers of the monomers constituting the polymer and other copolymerizable monomers, such as ethylene/vinyl acetate copolymers, (e) Polymers derived from epoxides, specifically polyethylene oxide or bisg Polymers derived from cidyl ethers, (f) Polyacetals, specifically polyoxymethylene, polyoxyethylene, polyoxymethylene containing ethylene oxide as a comonomer, (g) Polyphenylene oxide, (h) Polycarbonates, polysulfones, polyurethanes and urea resins, polyamides and copolyamides derived from diamines and dicarboxylic and/or aminocarboxylic acids or corresponding lactams, in particular nylon 6, nylon 66 , nylon 11, nylon 12, etc. (2) Polyesters derived from dicarboxylic acids and dialcohols and/or oxycarboxylic acids or corresponding lactones, in particular polyethylene terephthalate, polybutylene terephthalate, poly 1,4-dimethylol. Cyclohexane terephthalate, etc. (iv) Polymers with crosslinked structures derived from aldehydes and phenols, urea or melamine, specifically phenol/formaldehyde resins, urea/formaldehyde resins, melamine/formaldehyde resins, etc. (iv) Alkyds resins, specifically glycerin-phthalic acid resins, etc.; Examples include halogen-containing modified resins, (t) natural polymers, specifically cellulose, rubber, protein, or derivatives thereof such as cellulose acetate, cellulose propionate, and cellulose ether. Alternatively, when used as a synthetic wax, it goes without saying that various known waxes may be mixed. Furthermore, the new polymers of the present invention having different molecular weights may be mixed. [Monomer component] As the monomer component constituting the new polymer of the present invention, the polycyclic monomer represented by the above-mentioned general formula () and ethylene are used. In the general formula representing the polycyclic monomer component, R 1 to R 12 are hydrogen, alkyl groups, i.e. methyl, ethyl, propyl, isopropyl, butyl,
Chain alkyl such as tert-butyl, cycloalkyl such as cyclopentyl and cyclohexyl, or halogen such as fluorine, chlorine, bromine and iodine, which may be the same or different. Further, R 9 or R 10 and R 11 or R 12 may mutually form a ring, for example, in the general formula (), () (Here, R 1 to R 20 are hydrogen or alkyl groups, and may be the same or different.). Furthermore, when R 9 or R 10 and R 11 or R 12 are hydrogen and the residues do not form a ring, that is, DMON
When adopting the same structure, at least one of R 1 to R 8 is a group other than hydrogen. Specific examples of such polycyclic monomer components include:
Examples include the following table.
【表】【table】
【表】【table】
本発明の新重合体を製造するには、エチレンと
多環式モノマーとを周知のチーグラー係触媒によ
り重合すればよい。
本発明において使用されるチーグラー系触媒と
は、高活性触媒として知られているマグネシウム
化合物に担持されたチタン化合物、あるいはバナ
ジウム系化合物とアルキルアルミニウム系化合物
のような還元剤とよりなる触媒である。
マグネシウム化合物に担持されたチタン化合物
としては、少なくともマグネシウム、チタンおよ
びハロゲンを含有する複合体であり、マグネシウ
ム化合物とチタン化合物とを加熱もしくは共粉砕
などの手段により密に接触せしめて得られる化合
物で好ましくは該複合体中に含有されるハロゲ
ン/チタンのモル比が約4を越えるもので、常温
におけるヘキサン洗浄手段でチタン化合物を実質
的に脱離しないものをいう。
良好なる複合体は、ハロゲン/チタン(モル
比)が約4を越え、好ましくは約5以上、さらに
好ましくは約8以上、マグネシウム/チタン(モ
ル比)が約3以上、好ましくは約5ないし約50、
複合体に電子供与体を含む場合は電子供与体/チ
タン(モル比)が約0.2ないし約6、好ましくは
約0.4ないし約3、一層好ましくは約0.8ないし約
2であつて、その比表面積が約3m2/g以上、一
層好ましくは約40m2/g以上、さらに好ましくは
約100m2/g以上である。また、複合体のX線ス
ペクトルが、出発マグネシウム化合物の如何にか
かわらず非晶性を示すか、又はマグネシウムジハ
ライドの通常の市販品のそれに比べ、非常に非晶
化された状態にあることが望ましい。
複合体を製造する手段の例として、例えば特開
昭48−16986号、特開昭50−108385号、特開昭50
−12590号、特開昭51−20297号、特開昭51−
28189号、特開昭51−92885号、特開昭51−127185
号、特開昭51−136625号、特開昭52−87489号、
特開昭52−100596号、特開昭52−104593号、特開
昭52−147688号、特開昭53−2580号、1975年11月
21日付イタリア特許出願などに記載の手段を例示
できる。
バナジウム化合物としては、VCl4、VBr4、
VCl3、VBr3等のハロゲン化バナジウム、
VOCl3、VOBr3、VOCl2、VOBr2等のオキシハ
ルゲン化バナジウムあるいはVO(OR)nX3-o(た
だしRは炭化水素基、Xはハロゲン、0<n≦
3)で示されるバナジウム化合物を挙げることが
できる。これらの中では炭化水素可溶性のバナジ
ウム化合物とくにオキシハロゲン化バナジウム又
はVO(OR)nX3-oでしめされる化合物が好適で
ある。前記VO(OR)nX3-oで示される化合物に
おいては、Rは脂肪族、脂環族又は芳香族の炭化
水素基であり、好ましくは脂肪族の炭化水素基で
炭素原子数1〜20、とくには1〜3のものがよ
い。またnは0<n≦3、好ましくは1≦n≦
1.5の範囲である。このようなバナジウム化合物
の例としては、VO(OCH3)Cl2、
VO(OCH3)2Cl、VO(OCH3)3、VO(OC2H5)
Cl2、
VO(OC2H5)1.5Cl1.5、VO(OC2H5)2Cl、
VO(OC2H5)3、VO(OC2H5)1.5Br1.5、
VO(OC3H7)Cl2、VO(OC3H7)1.5Cl1.5、
VO(OC3H7)2Cl、VO(OC3H7)3、
VO(On−C4H9)Cl2、VO(On−C4H9)2Cl、
VO(OisoC4H9)2Cl、VO(OsecC4H9)3、
VO(OC5H11)1.5Cl1.5あるいはこれらの混合物など
を挙げることができる。これらはVOCl3とアルコ
ールを反応させたり、あるいはVOCl3とVO
(OR)3を反応させることによつて容易に得ること
ができる。
チタン系触媒又はバナジウム系化合物と共に使
用するアルキルアルミニウム化合物は、一般式
R′mAlX′3-n(ただしR′は炭化水素基、X′はハル
ゲン、0<m≦3)で示される。このアルキルア
ルミニウム化合物は、たとえばトリアルキルアル
ミニウム、ジアルキルアルミニウムハライド、ア
ルキルアルミニウムジハライドあるいはこれらの
任意の混合物あるいはこれらとアルミニウムトリ
ハライドとの混合物などを例示することができ
る。
以上示した触媒系の中では、重合の行い易さの
面からバナジウム系化合物/アルキルアルミニウ
ム化合物の系が好適である。この系を用いた場合
の両者の使用割合はAl/V(モル比)が1以上、
好ましくは30以下、とくに好ましくは2〜20の範
囲にするとよい。
重合は炭化水素媒体中で行われる。たとえばヘ
キサン、ヘプタン、オクタン、灯油のような脂肪
族炭化水素、シクロヘキサンのような脂環族炭化
水素、ベンゼン、トルエン、キシレンのような芳
香族炭化水素を単独で又は混合して溶媒に用いる
ことができる。
重合体は、バナジウム系化合物/アルキルアル
ミニウム化合物の触媒系を例にとれば、反応媒体
中、前記バナジウム化合物が0.05〜20ミリモル/
、好ましくは0.1〜10ミリモル/の濃度にな
るようにするのが好ましい。またアルキルアルミ
ニウム化合物は、既に述べたようにAl/V(モル
比)が1以上、好ましくは30以下、とくに好まし
くは2〜20となるように調整される。
多環式モノマー成分とエチレンとのランダム共
重合体を製造するに際して両モノマー成分の反応
媒体中への仕込み量は目的とする共重合体の組成
及び反応媒体の種類や重合温度によつても異なる
が、一般に反応媒体中のエチレン/多環式モノマ
ー成分のモル比が1/100〜100/1、好ましくは
1/50〜50/1となるように調節される。
重合温度は−50〜300℃、好ましくは−30〜200
℃、重合圧力は一般には0〜50Kg/cm2、好ましく
は0〜20Kg/cm2に保持される。また重合体の分子
量調整のため適宜、水素のような分子量調整剤を
存在させることができる。
〔実施例〕
本発明の内容を好適な実施例でもつて以下に説
明するが、本発明はこれらの実施例に制限される
ものではなく、その目的が損われない限り如何な
る態様も採り得ることは勿論である。
実施例 1
充分乾燥した500mlのセパラルフラスコに攪拌
羽根、ガス吹込管、温度計及び滴下ロートを取り
付け充分窒素で置換した。
このフラスコにモレキユラーシーブで脱水乾燥
したトルエン250mlを入れた。
窒素流通下フラスコに、表1のアの化合物を
7.5g、エチルアルミニウムセスキクロリドを2.5
ミリモル、滴下ロートにジクロロエトキシオキソ
バナジウムを0.25ミリモル加えた。
ガス吹込管を通じて乾燥したエチレン20/
hr、窒素40/hrの混合ガスを10℃に制御したフ
ラスコに10分間通した。
滴下ロートからジクロロエトキシオキソバナジ
ウムを滴下して共重合反応を開始し、前記の混合
ガスを通しながら10℃で30分間共重合反応を行つ
た。
共重合反応中の溶液は均一透明であり、共重合
体の析出は認められなかつた。
メタノール3mlを重合体溶液に添加して共重合
反応を停止した。
反応停止後の重合液を大量のメタノール中に投
入して共重合体を析出させ、さらにアセトンで洗
浄後、60℃で一昼夜真空乾燥し、共重合体7.2gを
得た。
13C−NMR分析で測定した共重合体のエチレ
ン組成は55モル%、135℃デカリン中で測定した
極限粘度〔η〕は2.1、ヨウ素価は0.7であつた。
また、力学物性を測定するために、230℃
hotpressにより1mm又は2mm厚さのプレス成形シ
ートを作成した。これらのシートを用いて、X線
回析を行つたところ、結晶による散乱は観察され
ず、結晶化度は0%であつた。また、透明性は、
ASTM D 1003−52に準拠した霞度(ヘイズ)
計で1mmシートについて測定したところ8%であ
つた。曲げ弾性率及び曲げ降状強度は、2mm厚プ
レスシートを用い、ASTM D 790に準拠して
測定したところ、それぞれ2.5×104Kg/cm2、850
Kg/cm2であつた。ガラス転移温度Tgは、デユポ
ン社製Dynamic Mechanical Analyser(DMA)
により、損失弾性率E″を5℃/minの昇温速度で
測定し、そのピーク温度から求めたところ149℃
であつた。さらに融点Tmは、デユポン社製990
タイプのDSCにより10℃/minの昇温速度で−
120℃〜400℃の範囲で測定したところ、融解曲線
(ピーク)は観察されなかつた。
電気的性質は、安藤電気製誘電体損測定装置
で、1KHzにて測定したところ、誘電率2.0、誘電
正接(tanδ)が2.8×10-4であつた。さらに、耐
薬品性及び耐溶剤性を調べるため、室温でプレス
成形品を硫酸(97%)、アンモニア水(20%)、ア
セトン、酢酸エチルなどに20時間侵して外観を観
察したところ、色変化、透明性低下、変形、溶
解、クラツク発生などの性状はまつたく見られな
かつた。
また、軟化温度をTMA(Dupon社製)によつ
て測定したところ、138℃であり、熱天秤による
熱分解温度(減量開始温度)が390℃であつた。
密度勾配管法による23℃の密度は、1.025g/cm3、
アツベ屈折計による屈折率nDは1.536であつた。
さらに、表面硬さの指標である鉛筆硬度は、Hで
あつた。
実施例 2〜7
実施例1においてモノマー成分を表1、共重合
条件を表2に記載した如く変える以外は同様な操
作を行い、表3の結果を得た。尚、表2,3には
実施例1の条件および結果を併記する。
In order to produce the new polymer of the present invention, ethylene and a polycyclic monomer may be polymerized using a well-known Ziegler catalyst. The Ziegler catalyst used in the present invention is a titanium compound supported on a magnesium compound, which is known as a highly active catalyst, or a catalyst consisting of a vanadium compound and a reducing agent such as an alkyl aluminum compound. The titanium compound supported on the magnesium compound is preferably a complex containing at least magnesium, titanium and halogen, and is preferably a compound obtained by bringing a magnesium compound and a titanium compound into close contact by means such as heating or co-pulverization. refers to a composite in which the molar ratio of halogen/titanium contained in the composite exceeds about 4, and the titanium compound is not substantially eliminated by hexane washing at room temperature. A good composite has a halogen/titanium (molar ratio) greater than about 4, preferably about 5 or more, more preferably about 8 or more, and a magnesium/titanium (molar ratio) greater than about 3, preferably from about 5 to about 50,
When the composite includes an electron donor, the electron donor/titanium (molar ratio) is about 0.2 to about 6, preferably about 0.4 to about 3, more preferably about 0.8 to about 2, and the specific surface area is It is about 3 m 2 /g or more, more preferably about 40 m 2 /g or more, and even more preferably about 100 m 2 /g or more. In addition, the X-ray spectrum of the composite may be amorphous regardless of the starting magnesium compound, or may be in a highly amorphous state compared to that of ordinary commercially available magnesium dihalides. desirable. Examples of means for producing composites include JP-A-48-16986, JP-A-50-108385, and JP-A-Sho 50.
-12590, JP-A-51-20297, JP-A-51-
No. 28189, JP-A-51-92885, JP-A-51-127185
No., JP-A-51-136625, JP-A-52-87489,
JP 52-100596, JP 52-104593, JP 52-147688, JP 53-2580, November 1975
Examples include the means described in the Italian patent application dated 21st. Vanadium compounds include VCl 4 , VBr 4 ,
Vanadium halides such as VCl 3 and VBr 3 ,
Vanadium oxyhalogenide such as VOCl 3 , VOBr 3 , VOCl 2 , VOBr 2 or VO(OR)nX 3-o (R is a hydrocarbon group, X is a halogen, 0<n≦
Vanadium compounds shown in 3) can be mentioned. Among these, hydrocarbon-soluble vanadium compounds, particularly vanadium oxyhalides or compounds represented by VO(OR)nX 3-o, are preferred. In the compound represented by VO(OR)nX 3-o , R is an aliphatic, alicyclic or aromatic hydrocarbon group, preferably an aliphatic hydrocarbon group having 1 to 20 carbon atoms, Particularly preferred are numbers 1 to 3. Also, n is 0<n≦3, preferably 1≦n≦
It is in the range of 1.5. Examples of such vanadium compounds are VO( OCH3 ) Cl2 , VO( OCH3 ) 2Cl , VO( OCH3 ) 3 , VO( OC2H5 ) .
Cl 2 , VO (OC 2 H 5 ) 1.5 Cl 1.5 , VO (OC 2 H 5 ) 2 Cl, VO (OC 2 H 5 ) 3 , VO (OC 2 H 5 ) 1.5 Br 1.5 , VO (OC 3 H 7 ) Cl2 ,VO( OC3H7 ) 1.5Cl1.5 ,VO( OC3H7 ) 2Cl , VO( OC3H7 ) 3 ,VO(On − C4H9 )Cl2 , VO(On− Examples include C 4 H 9 ) 2 Cl, VO(OisoC 4 H 9 ) 2 Cl, VO(OsecC 4 H 9 ) 3 , VO(OC 5 H 11 ) 1.5 Cl 1.5 or a mixture thereof. These can be done by reacting VOCl 3 with alcohol or by reacting VOCl 3 with VO
It can be easily obtained by reacting (OR) 3 . Alkylaluminum compounds used with titanium-based catalysts or vanadium-based compounds have the general formula
It is represented by R′mAlX′ 3-n (where R′ is a hydrocarbon group, X′ is a halogen, and 0<m≦3). Examples of the alkylaluminum compound include trialkylaluminum, dialkylaluminum halide, alkylaluminum dihalide, any mixture thereof, or a mixture of these and aluminum trihalide. Among the catalyst systems shown above, a vanadium compound/alkyl aluminum compound system is preferred from the viewpoint of ease of polymerization. When using this system, the usage ratio of both is Al/V (molar ratio) of 1 or more,
It is preferably 30 or less, particularly preferably in the range of 2 to 20. Polymerization takes place in a hydrocarbon medium. For example, aliphatic hydrocarbons such as hexane, heptane, octane, and kerosene, alicyclic hydrocarbons such as cyclohexane, and aromatic hydrocarbons such as benzene, toluene, and xylene may be used alone or in combination as a solvent. can. For example, in the case of a vanadium-based compound/alkyl aluminum compound catalyst system, the polymer contains 0.05 to 20 mmol of the vanadium compound in the reaction medium.
, preferably at a concentration of 0.1 to 10 mmol/. Further, the alkylaluminum compound is adjusted so that the Al/V (molar ratio) is 1 or more, preferably 30 or less, and particularly preferably 2 to 20, as described above. When producing a random copolymer of a polycyclic monomer component and ethylene, the amount of both monomer components charged into the reaction medium varies depending on the composition of the desired copolymer, the type of reaction medium, and the polymerization temperature. However, the molar ratio of ethylene/polycyclic monomer component in the reaction medium is generally adjusted to be between 1/100 and 100/1, preferably between 1/50 and 50/1. Polymerization temperature is -50 to 300℃, preferably -30 to 200℃
℃ and the polymerization pressure is generally maintained at 0 to 50 kg/cm 2 , preferably 0 to 20 kg/cm 2 . Furthermore, a molecular weight regulator such as hydrogen may be present as appropriate to adjust the molecular weight of the polymer. [Example] The content of the present invention will be explained below using preferred examples, but the present invention is not limited to these examples, and any embodiment can be adopted as long as the purpose is not impaired. Of course. Example 1 A stirring blade, a gas blowing tube, a thermometer, and a dropping funnel were attached to a thoroughly dried 500 ml sepral flask, and the flask was sufficiently purged with nitrogen. 250 ml of toluene that had been dehydrated and dried using a molecular sieve was placed in this flask. Add compound A in Table 1 to a flask under nitrogen flow.
7.5g, ethylaluminum sesquichloride 2.5g
0.25 mmol of dichloroethoxyoxovanadium was added to the dropping funnel. Ethylene 20/20 dried through the gas blowing pipe
A mixed gas of 40/hr and nitrogen was passed through the flask controlled at 10° C. for 10 minutes. The copolymerization reaction was started by dropping dichloroethoxyoxovanadium from the dropping funnel, and the copolymerization reaction was carried out at 10° C. for 30 minutes while passing the mixed gas. The solution during the copolymerization reaction was homogeneous and transparent, and no copolymer precipitation was observed. The copolymerization reaction was stopped by adding 3 ml of methanol to the polymer solution. After the reaction had been terminated, the polymer solution was poured into a large amount of methanol to precipitate a copolymer, which was further washed with acetone and vacuum-dried at 60° C. overnight to obtain 7.2 g of a copolymer. The ethylene composition of the copolymer measured by 13C-NMR analysis was 55 mol%, the intrinsic viscosity [η] measured in decalin at 135°C was 2.1, and the iodine value was 0.7. In addition, in order to measure mechanical properties,
Press-molded sheets with a thickness of 1 mm or 2 mm were produced by hotpress. When X-ray diffraction was performed using these sheets, no scattering due to crystals was observed, and the crystallinity was 0%. Also, transparency is
Haze according to ASTM D 1003-52
A total of 8% was measured on a 1 mm sheet. The flexural modulus and bending strength were measured in accordance with ASTM D 790 using a 2 mm thick press sheet, and were 2.5 x 10 4 Kg/cm 2 and 850, respectively.
It was Kg/ cm2 . The glass transition temperature Tg was measured using a Dynamic Mechanical Analyzer (DMA) manufactured by DuPont.
The loss modulus E'' was measured at a heating rate of 5℃/min, and the peak temperature was determined to be 149℃.
It was hot. Furthermore, the melting point Tm is 990 manufactured by Dupont.
- type DSC at a heating rate of 10℃/min.
When measured in the range of 120°C to 400°C, no melting curve (peak) was observed. The electrical properties were measured at 1 KHz using a dielectric loss measuring device manufactured by Ando Electric, and the dielectric constant was 2.0 and the dielectric loss tangent (tan δ) was 2.8×10 -4 . Furthermore, in order to investigate chemical and solvent resistance, press molded products were immersed in sulfuric acid (97%), aqueous ammonia (20%), acetone, ethyl acetate, etc. at room temperature for 20 hours and the appearance was observed. No symptoms such as decreased transparency, deformation, dissolution, or cracking were observed. Further, the softening temperature was measured using TMA (manufactured by Dupon) and was 138°C, and the thermal decomposition temperature (weight loss starting temperature) was 390°C using a thermobalance.
The density at 23°C according to the density gradient tube method is 1.025 g/cm 3 ,
The refractive index nD measured by an Atsube refractometer was 1.536.
Furthermore, the pencil hardness, which is an index of surface hardness, was H. Examples 2 to 7 The same operations as in Example 1 were performed except that the monomer components were changed as shown in Table 1 and the copolymerization conditions were changed as shown in Table 2, and the results shown in Table 3 were obtained. Note that Tables 2 and 3 also show the conditions and results of Example 1.
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
本発明の新重合体は、以上述べて来たように、
従来全く知られていない構造及び組成を採ること
によつて透明性、耐熱性、耐熱老化性、耐薬品
性、耐溶剤性、誘電持性、機械的性質のいずれも
が高いレベルを示し、その利用可能分野も前述し
たように多伎に亘るのであり、産業界に多大の利
益を持たらす。
As mentioned above, the new polymer of the present invention has
By adopting a structure and composition that was completely unknown in the past, it exhibits high levels of transparency, heat resistance, heat aging resistance, chemical resistance, solvent resistance, dielectric retention, and mechanical properties. As mentioned above, the fields in which it can be used are wide-ranging, and it brings great benefits to industry.
Claims (1)
多環式モノマーとから得られるランダム共重合
体であつて、 (ここでR1〜R12は水素、アルキル基又はハ
ロゲンであつて各同一又は異なつていてもよ
く、またR9又はR10とR11又はR12とは互いに環
を形成していてもよい。更にR9又はR10及び
R11又はR12が水素であつて残基が環を形成し
ないときは、R1〜R8のうち少なくとも1個は
水素以外の基である。) (B) エチレン単位/多環式モノマー単位(モル
比)が90/10〜10/90であり、 (C) エチレン単位が下記式で示されるとともに、 (−CH2−CH2)− 多環式モノマー単位が主として下記一般式
()で示される構造をとり、 (D) 135℃、デカリン中で測定した極限粘度〔η〕
が、0.3〜20dl/g、 で定義づけられる新重合体。 2 更に共重合可能な第3モノマー成分を含む特
許請求の範囲第1項記載の新重合体。 3 第3モノマー成分が多環式モノマー成分単位
の50モル%以下である特許請求の範囲第2項記載
の新重合体。[Scope of Claims] 1 (A) A random copolymer obtained from ethylene and a polycyclic monomer represented by the following general formula (), (Here, R 1 to R 12 are hydrogen, an alkyl group, or a halogen, and may be the same or different, and R 9 or R 10 and R 11 or R 12 may mutually form a ring. Good. Also R 9 or R 10 and
When R 11 or R 12 is hydrogen and the residues do not form a ring, at least one of R 1 to R 8 is a group other than hydrogen. ) (B) The ethylene unit/polycyclic monomer unit (molar ratio) is 90/10 to 10/90, (C) The ethylene unit is represented by the following formula, and (-CH 2 - CH 2 )- The cyclic monomer unit mainly has a structure represented by the following general formula (), (D) Intrinsic viscosity [η] measured in decalin at 135℃
A new polymer defined by 0.3 to 20 dl/g. 2. The new polymer according to claim 1, further comprising a copolymerizable third monomer component. 3. The new polymer according to claim 2, wherein the third monomer component accounts for 50 mol% or less of the polycyclic monomer component units.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP59236829A JPS61115916A (en) | 1984-11-12 | 1984-11-12 | Novel polymer |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP59236829A JPS61115916A (en) | 1984-11-12 | 1984-11-12 | Novel polymer |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS61115916A JPS61115916A (en) | 1986-06-03 |
JPH0450922B2 true JPH0450922B2 (en) | 1992-08-17 |
Family
ID=17006395
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP59236829A Granted JPS61115916A (en) | 1984-11-12 | 1984-11-12 | Novel polymer |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS61115916A (en) |
Families Citing this family (29)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0730237B2 (en) * | 1986-08-26 | 1995-04-05 | 日本ゼオン株式会社 | Norbornene-based polymer composition |
JPS6431844A (en) * | 1987-07-27 | 1989-02-02 | Mitsui Petrochemical Ind | Polymer composition for spacer of information recording base plate |
JPH0819292B2 (en) * | 1987-10-08 | 1996-02-28 | 三井石油化学工業株式会社 | Thermoplastic resin composition |
JP2915942B2 (en) * | 1989-01-12 | 1999-07-05 | 三井化学株式会社 | Vinyl chloride resin composition |
EP0652253B1 (en) * | 1989-01-12 | 2000-05-03 | Mitsui Chemicals, Inc. | Cycloolefin resin compositions |
CA2010320C (en) | 1989-02-20 | 2001-04-17 | Yohzoh Yamamoto | Sheet or film of cyclo-olefin polymer |
DE69022016T2 (en) * | 1989-07-07 | 1996-04-25 | Daikin Ind Ltd | FLUORINATED COPOLYMER AND METHOD FOR THE PRODUCTION THEREOF. |
US5229473A (en) * | 1989-07-07 | 1993-07-20 | Daikin Industries Ltd. | Fluorine-containing copolymer and method of preparing the same |
EP0485631B1 (en) * | 1990-06-06 | 1995-11-15 | Mitsui Petrochemical Industries, Ltd. | Polyolefin resin composition |
KR960009295B1 (en) | 1991-09-12 | 1996-07-18 | 미쓰이세끼유 가가꾸고오교오 가부시끼가이샤 | Cycloolefin resin composition |
US5567776A (en) * | 1992-05-26 | 1996-10-22 | Mitsui Petrochemical Industries, Ltd. | Cycloolefin copolymer composition and method for the preperation thereof |
US5494969A (en) * | 1993-01-29 | 1996-02-27 | Mitsui Petrochemical Industries, Ltd. | Cycloolefin polymer composition |
JPH06228323A (en) * | 1993-01-29 | 1994-08-16 | Mitsui Petrochem Ind Ltd | Production of pellet of cycloolefin random copolymer |
EP0671433B1 (en) * | 1994-03-09 | 1998-06-17 | Mitsui Chemicals, Inc. | Polymer composition and core-shell elastomer used therefor |
TW312696B (en) * | 1994-04-22 | 1997-08-11 | Mitsui Petroleum Chemicals Ind | |
JP3341954B2 (en) | 1994-09-26 | 2002-11-05 | 三井化学株式会社 | Resin composition |
WO2005095106A1 (en) | 2004-03-31 | 2005-10-13 | Mitsubishi Plastics, Inc. | Heat-shrinkable layered polyolefin film, heat-shrinkable label, and container with the label attached thereto |
KR100935145B1 (en) | 2005-03-07 | 2010-01-06 | 미쓰이 가가쿠 가부시키가이샤 | Cyclic olefin resin composition, and substrate obtained from said resin composition |
JP4881306B2 (en) | 2005-04-18 | 2012-02-22 | 三井化学株式会社 | Resin composition and optical component |
CN101522813B (en) | 2006-10-17 | 2013-01-30 | 三井化学株式会社 | Resin composition and molded article produced from the composition |
WO2010126088A1 (en) | 2009-04-30 | 2010-11-04 | 三菱樹脂株式会社 | Sheet for solar cell, and solar cell module |
CN103229312B (en) | 2010-11-30 | 2016-09-21 | 大日本印刷株式会社 | Polylayer forest used for solar batteries and use its solar module made |
EP3604434B1 (en) | 2017-03-30 | 2024-04-17 | Mitsui Chemicals, Inc. | Cyclic olefin resin composition for molding, molded body, and resin |
AU2018377771C1 (en) | 2017-11-29 | 2022-12-08 | Mitsui Chemicals, Inc. | Cyclic-olefin-based copolymer, cyclic-olefin-based copolymer composition, molded body, and medical container |
US20210024675A1 (en) | 2018-03-30 | 2021-01-28 | Mitsui Chemicals, Inc. | Optical lens |
JP7080351B2 (en) | 2018-12-27 | 2022-06-03 | 三井化学株式会社 | Cyclic olefin copolymer composition for medical equipment and molded article |
CN113906097B (en) | 2019-05-27 | 2023-07-18 | 三井化学株式会社 | Cyclic olefin resin composition, molded body, and optical member |
JP7451570B2 (en) * | 2020-01-22 | 2024-03-18 | 三井化学株式会社 | optical parts |
JP7362972B1 (en) | 2021-11-29 | 2023-10-17 | 三井化学株式会社 | Resin compositions for forming optical parts, molded bodies, and optical parts |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5088195A (en) * | 1973-12-10 | 1975-07-15 | ||
JPS5334890A (en) * | 1976-09-14 | 1978-03-31 | Japan Synthetic Rubber Co Ltd | Preparation of (co) polymer from norbornene derivative |
-
1984
- 1984-11-12 JP JP59236829A patent/JPS61115916A/en active Granted
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---|---|---|---|---|
JPS5088195A (en) * | 1973-12-10 | 1975-07-15 | ||
JPS5334890A (en) * | 1976-09-14 | 1978-03-31 | Japan Synthetic Rubber Co Ltd | Preparation of (co) polymer from norbornene derivative |
Also Published As
Publication number | Publication date |
---|---|
JPS61115916A (en) | 1986-06-03 |
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