JPS62205141A - Stabilizer for use in synthetic polymeric material - Google Patents
Stabilizer for use in synthetic polymeric materialInfo
- Publication number
- JPS62205141A JPS62205141A JP4668886A JP4668886A JPS62205141A JP S62205141 A JPS62205141 A JP S62205141A JP 4668886 A JP4668886 A JP 4668886A JP 4668886 A JP4668886 A JP 4668886A JP S62205141 A JPS62205141 A JP S62205141A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- formulas
- tables
- carbon atoms
- 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.)
- Pending
Links
- 239000003381 stabilizer Substances 0.000 title claims abstract description 15
- 239000000463 material Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000004480 active ingredient Substances 0.000 claims abstract description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 239000011593 sulfur Substances 0.000 claims abstract description 5
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229920001059 synthetic polymer Polymers 0.000 claims description 4
- 239000002861 polymer material Substances 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 11
- 125000004429 atom Chemical group 0.000 claims 1
- 125000005936 piperidyl group Chemical group 0.000 claims 1
- 150000003918 triazines Chemical class 0.000 claims 1
- -1 polyethylene Polymers 0.000 abstract description 34
- 229920000642 polymer Polymers 0.000 abstract description 17
- WUCDQLRTWMSFBP-UHFFFAOYSA-N 4-piperidin-1-yltriazine Chemical class C1CCCCN1C1=CC=NN=N1 WUCDQLRTWMSFBP-UHFFFAOYSA-N 0.000 abstract description 6
- 230000003078 antioxidant effect Effects 0.000 abstract description 4
- 239000004698 Polyethylene Substances 0.000 abstract description 3
- 229920000573 polyethylene Polymers 0.000 abstract description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract description 2
- 239000005977 Ethylene Substances 0.000 abstract description 2
- 239000004793 Polystyrene Substances 0.000 abstract description 2
- 229920002223 polystyrene Polymers 0.000 abstract description 2
- 235000006708 antioxidants Nutrition 0.000 abstract 2
- 238000002845 discoloration Methods 0.000 abstract 1
- 230000002349 favourable effect Effects 0.000 abstract 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 15
- 229920001577 copolymer Polymers 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 12
- 239000000203 mixture Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 7
- 239000004743 Polypropylene Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 229920001155 polypropylene Polymers 0.000 description 6
- 150000001993 dienes Chemical class 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229920000877 Melamine resin Polymers 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- 229920002367 Polyisobutene Polymers 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 150000002148 esters Chemical group 0.000 description 3
- 229920000578 graft copolymer Polymers 0.000 description 3
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229920002857 polybutadiene Polymers 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- 229910052793 cadmium Inorganic materials 0.000 description 2
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229920006037 cross link polymer Polymers 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 2
- 239000012760 heat stabilizer Substances 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 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
- 229920002647 polyamide Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- 229920006337 unsaturated polyester resin Polymers 0.000 description 2
- 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
- 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
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- ZMWRRFHBXARRRT-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(N2N=C3C=CC=CC3=N2)=C1O ZMWRRFHBXARRRT-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- BHIIOLWIZLICII-UHFFFAOYSA-N 2-butyl-5-methylphenol Chemical compound CCCCC1=CC=C(C)C=C1O BHIIOLWIZLICII-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- BSUSTMZYGQTETC-UHFFFAOYSA-N CCC(CO)(CO)CO.CCCCCCCCCCCCCCCCCCCCC(O)=S.CCCCCCCCCCCCCCCCCCCCC(O)=S.CCCCCCCCCCCCCCCCCCCCC(O)=S Chemical compound CCC(CO)(CO)CO.CCCCCCCCCCCCCCCCCCCCC(O)=S.CCCCCCCCCCCCCCCCCCCCC(O)=S.CCCCCCCCCCCCCCCCCCCCC(O)=S BSUSTMZYGQTETC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920001634 Copolyester Polymers 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 1
- 229920002943 EPDM rubber Polymers 0.000 description 1
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- 229920000571 Nylon 11 Polymers 0.000 description 1
- 229920000299 Nylon 12 Polymers 0.000 description 1
- HQWYNVPBMRPJKR-UHFFFAOYSA-N O-[2,3-di(pentadecanethioyloxy)propyl] pentadecanethioate Chemical compound C(CCCCCCCCCCC)CCC(=S)OCC(OC(CCCCCCCCCCCCCC)=S)COC(CCCCCCCCCCCCCC)=S HQWYNVPBMRPJKR-UHFFFAOYSA-N 0.000 description 1
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241001483078 Phyto Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 241000555745 Sciuridae Species 0.000 description 1
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- OCWYEMOEOGEQAN-UHFFFAOYSA-N bumetrizole Chemical compound CC(C)(C)C1=CC(C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O OCWYEMOEOGEQAN-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- KRGNPJFAKZHQPS-UHFFFAOYSA-N chloroethene;ethene Chemical group C=C.ClC=C KRGNPJFAKZHQPS-UHFFFAOYSA-N 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920003020 cross-linked polyethylene Polymers 0.000 description 1
- 239000004703 cross-linked polyethylene Substances 0.000 description 1
- UQLDLKMNUJERMK-UHFFFAOYSA-L di(octadecanoyloxy)lead Chemical compound [Pb+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O UQLDLKMNUJERMK-UHFFFAOYSA-L 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 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
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 229920000092 linear low density polyethylene Polymers 0.000 description 1
- 239000004707 linear low-density polyethylene Substances 0.000 description 1
- 229920001684 low density polyethylene Polymers 0.000 description 1
- 239000004702 low-density polyethylene Substances 0.000 description 1
- 239000000314 lubricant Substances 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
- 238000004519 manufacturing process Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- JMWUYEFBFUCSAK-UHFFFAOYSA-L nickel(2+);octadecanoate Chemical compound [Ni+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O JMWUYEFBFUCSAK-UHFFFAOYSA-L 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- XKIVKIIBCJIWNU-UHFFFAOYSA-N o-[3-pentadecanethioyloxy-2,2-bis(pentadecanethioyloxymethyl)propyl] pentadecanethioate Chemical compound CCCCCCCCCCCCCCC(=S)OCC(COC(=S)CCCCCCCCCCCCCC)(COC(=S)CCCCCCCCCCCCCC)COC(=S)CCCCCCCCCCCCCC XKIVKIIBCJIWNU-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- 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
- RQKYHDHLEMEVDR-UHFFFAOYSA-N oxo-bis(phenylmethoxy)phosphanium Chemical compound C=1C=CC=CC=1CO[P+](=O)OCC1=CC=CC=C1 RQKYHDHLEMEVDR-UHFFFAOYSA-N 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
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 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
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 229960000969 phenyl salicylate Drugs 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
- 239000000049 pigment Substances 0.000 description 1
- YPSLATCYOGSFDU-UHFFFAOYSA-N piperidine;triazine Chemical class C1CCNCC1.C1=CN=NN=C1 YPSLATCYOGSFDU-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000004014 plasticizer Chemical class 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920000580 poly(melamine) Polymers 0.000 description 1
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 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
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920002620 polyvinyl fluoride Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000010454 slate Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 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
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-UHFFFAOYSA-N 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- 150000003606 tin compounds Chemical class 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
- 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
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229920001959 vinylidene polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229940098697 zinc laurate Drugs 0.000 description 1
- GPYYEEJOMCKTPR-UHFFFAOYSA-L zinc;dodecanoate Chemical compound [Zn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O GPYYEEJOMCKTPR-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
(目的)
本願発明は、ピペリジル−トリアジン誘導体及び硫黄系
酸化防止剤を有効成分として含有することを特徴とする
合成高分子材料用安定剤に関するものである。DETAILED DESCRIPTION OF THE INVENTION (Objective) The present invention relates to a stabilizer for synthetic polymer materials, which is characterized by containing a piperidyl-triazine derivative and a sulfur-based antioxidant as active ingredients.
ポリエチレン、ポリプロビレン、塩化ビニル、ポリウレ
タン等の合成烏分子は、光、熱、酸素等の影響により劣
化を受は易い。これらの劣化を防止する丸め、各種の光
安定剤、熱安定剤、酸化防止剤が使用されている。Synthetic materials such as polyethylene, polypropylene, vinyl chloride, and polyurethane are susceptible to deterioration due to the effects of light, heat, oxygen, and the like. To prevent these deteriorations, various light stabilizers, heat stabilizers, and antioxidants are used.
従来知られている光安定剤のうち、2.2.6.6−チ
トラメチルピベリジル基を部分構造として有するピペリ
ジン系化合物は、優れた光安定効果を有するが、十分な
熱安定効果を有さないため、各種の熱安定剤との配合が
検討されているが、光安定性、熱安定性及び耐着色性の
点で必ずしも満足できる効果は、得られていない。Among conventionally known photostabilizers, piperidine compounds having a 2.2.6.6-titramethylpiveridyl group as a partial structure have an excellent photostabilizing effect, but do not have sufficient thermal stabilizing effects. Therefore, the combination with various heat stabilizers has been studied, but satisfactory effects have not been obtained in terms of light stability, heat stability, and coloring resistance.
本願発明者らは、光安定性、熱安定性及び耐着色性の点
で、十分な効果を有する高分子安定剤の開発を目的とし
て、長年に亘り鋭意検討を行った結果、ピペリジル−ト
リアジン構造を有する特定のピペリジン化合物と硫黄系
酸化防止剤を組合せることによって、すぐれた光安定効
果、熱安定効果及び耐着色効果、特に相剰的な熱安定効
果を有する高分子安定剤を見出して、本願発明を完成し
た。The inventors of the present application have conducted intensive studies over many years with the aim of developing a polymer stabilizer that has sufficient effects in terms of photostability, thermal stability, and coloring resistance. As a result, the piperidyl-triazine structure By combining a specific piperidine compound having The invention of the present application has been completed.
(構成)
本願発明の合成高分子材料安定剤は、下記一般式Cl5
L)〜CIC)を有するピペリジン−トリアジン誘導体
の少なくとも一種及び下記一般式(Ha)〜(lc)を
有する硫黄系酸化防止剤の少なくとも一種を有効成分と
する。(Structure) The synthetic polymer material stabilizer of the present invention has the following general formula Cl5
The active ingredients include at least one piperidine-triazine derivative having the formulas (L) to CIC) and at least one sulfur-based antioxidant having the following general formulas (Ha) to (lc).
上記式中、
を有する基〔式中、R4は、水素原子、炭素原子1乃至
18個を有するアルキル基、屍素原子3乃至22個を有
するアルコキシアルキル基、置換されていてもよいアラ
ルキル基又は式Rは、後述するR2と同意義を示す。)
を示し、R2は、水素原子、炭素原子1個乃至18個を
有するアルキル基又は置換されていてもよいアラルキル
基を示す。〕を示し、
Yは、モルホリノ基又は 式 −NHR4を有する基〔
式中、R4は、炭素原子1個乃至18個を有するアルキ
ル基又は式
は、前述したものと同意義を示す。)を示し、nは、2
乃至20の整数を示す。In the above formula, a group having Formula R has the same meaning as R2 described below. )
and R2 represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, or an optionally substituted aralkyl group. ], Y is a morpholino group or a group having the formula -NHR4 [
In the formula, R4 is an alkyl group having 1 to 18 carbon atoms or the formula has the same meaning as described above. ), and n is 2
Indicates an integer between 20 and 20.
上記式(置a)〜(IC)中、
R5は、炭素原子4乃至18個を有するアルキル基を示
し、
mは、2乃至4の整数を示し、
mが2のとき、2は、エチレン基を示し、mが3のとき
、2は、式 −CH−(1’H−(1’H2−又はを有
する基を示す。In the above formulas (a) to (IC), R5 represents an alkyl group having 4 to 18 carbon atoms, m represents an integer of 2 to 4, and when m is 2, 2 is an ethylene group. and when m is 3, 2 represents a group having the formula -CH-(1'H-(1'H2-) or.
ピペリジル−トリアジン(Ia)〜(IC)において、
R1が示す炭素原子1乃至18個を有するアルキル基は
、直鎖又は分校でもよく、例えば、メチル、エチル、l
1l−7’ロビル、イソプロピル、n−ブチル、n−ヘ
キシル、n−オクチル、2−エチルヘキシル、n−デシ
ル、n−ドデシル、n−オクタデシルであり得、好適に
は炭素原子4乃至8個を有するアルキル基、例えばn−
ブチル、n−ヘキシル、n−オクチル、2−エチルヘキ
シルである。In piperidyl-triazines (Ia) to (IC), the alkyl group having 1 to 18 carbon atoms represented by R1 may be linear or branched, such as methyl, ethyl, l
1l-7' lobil, isopropyl, n-butyl, n-hexyl, n-octyl, 2-ethylhexyl, n-decyl, n-dodecyl, n-octadecyl, preferably having 4 to 8 carbon atoms. Alkyl groups, e.g. n-
Butyl, n-hexyl, n-octyl, and 2-ethylhexyl.
R1が示す炭素原子3乃至22個を有するアルコキシア
ルキル基は、炭素原子1乃至18個を有するアルコキシ
基を有する炭素原子2乃至4個を有するアルキル基であ
り得る。炭素原子1乃至18個を有するアルコキシ部分
は上記R1に例示するアルキル基を有するアルコキシで
あり得、好適には炭素原子1乃至8個を有するアルコキ
シ、例えば、メトキシ、エトキシ、n−プロボギシ、イ
ンプロポキシ、n−ブトキシ、D−へキトキシ、n−オ
クトキシである。炭素原子2乃至4個を有するアルキル
部分は、例えばエチル、n−プロピル、イソプロピル、
n−ブチル、インブチルであり得、好適にはn−プロピ
ルである。The alkoxyalkyl group having 3 to 22 carbon atoms represented by R1 can be an alkyl group having 2 to 4 carbon atoms with an alkoxy group having 1 to 18 carbon atoms. The alkoxy moiety having 1 to 18 carbon atoms may be an alkoxy having an alkyl group as exemplified in R1 above, preferably an alkoxy having 1 to 8 carbon atoms, such as methoxy, ethoxy, n-probogyoxy, impropoxy. , n-butoxy, D-hectoxy, and n-octoxy. Alkyl moieties having 2 to 4 carbon atoms are, for example, ethyl, n-propyl, isopropyl,
It can be n-butyl, inbutyl, preferably n-propyl.
R1,R2又はR5が示す置換されていてもよいアラル
キル基は、例えばベンジル、フェネチル、p−Ifルベ
ンジル、p−クロロベンジルテアり得、好適にはベンジ
ルである。The optionally substituted aralkyl group represented by R1, R2 or R5 can be, for example, benzyl, phenethyl, p-If rubenzyl, p-chlorobenzylthea, preferably benzyl.
R2,R3又はR4が示す炭素原子1乃至18個を有す
るアルキル基は、前述のR1に例示するアルキルと同様
のものであり得る。The alkyl group having 1 to 18 carbon atoms represented by R2, R3 or R4 may be the same as the alkyl group exemplified for R1 above.
R2又はR5は、好適には、炭素原子1乃至4個を有す
るアルキル基、例えば、メチル、エチル、In−プロピ
ル、イソプロピル、n−7”チルであり、特に好適には
メチルであり、R4は好適には、炭素原子4乃至3個を
有するアルキル基、例えば、n−ブチル、t−ブチル、
t−ペンチル、t−オクチルであり、特に好適には、t
−オクチルである。R2 or R5 is preferably an alkyl group having 1 to 4 carbon atoms, such as methyl, ethyl, In-propyl, isopropyl, n-7''yl, particularly preferably methyl, and R4 is Preferably, alkyl groups having 4 to 3 carbon atoms, such as n-butyl, t-butyl,
t-pentyl, t-octyl, particularly preferably t-pentyl, t-octyl;
-It is octyl.
R5が示す炭素原子4乃至18個を有するアルキル基は
、前述のR1に例示する炭素原子1乃至18個を有する
アルキル基のうち、炭素原子4乃至18個を有するアル
キル基と同様の基であり得、好適には、炭素原子10乃
至18個を有するアルキル基である。The alkyl group having 4 to 18 carbon atoms represented by R5 is the same group as the alkyl group having 4 to 18 carbon atoms among the alkyl groups having 1 to 18 carbon atoms exemplified in R1 above. It is preferably an alkyl group having 10 to 18 carbon atoms.
又、ピペリジル−トリアジン誘導体のうち、好適には、
式(Ia)又は式(Ib)を有する化合物であり、特に
好適には、式(1)を有する基Xにおいて、R1が炭素
原子4乃至8個を有するアルキル基であり、R2が水素
原子、メチル基又はベンジル基である化合物である。Also, among the piperidyl-triazine derivatives, preferably:
A compound having formula (Ia) or formula (Ib), particularly preferably a group X having formula (1) in which R1 is an alkyl group having 4 to 8 carbon atoms, R2 is a hydrogen atom, A compound that is a methyl group or a benzyl group.
化合物(Ia)〜(IC)は、例えば、次に例示する化
合物を具体的にあげることができる。Examples of the compounds (Ia) to (IC) include the following compounds.
H−X
16
4〜518
4〜5硫黄系酸化防止剤のうち、
好適には、式(Ha)を有する化合物であり、特に好適
には、R5が炭素原子10乃至18個を有する化合物で
ある。H-X 16
4-518
Among 4-5 sulfur antioxidants,
Preferred are compounds having the formula (Ha), particularly preferred are compounds in which R5 has 10 to 18 carbon atoms.
化合物C11a)〜(IC)は、例えば1次に例示する
化合物を具体的にあげることができる。Compounds C11a) to (IC) can be specifically exemplified by the following compounds.
19 ジ−ラウリル チオ−ジ−プロピオネート
20 ジ−ミリスチル チオ−ジ−プロピオネート
21 ジ−ステアリル チオ−ジ−プロピオネート
22 グリセロール トリス(3−ドデシルチオプロ
ピオネート)
23トリメチロールプロパン トリス(3−オクタデシ
ルチオプロピオネート)
24 ペンタエリスリトール テトラキス(3−ドデ
シルチオプロピオネート)
25 3.9−ヒx(2−)”fシルチオエチル)−2
,4,8,10−テトラオキサスピロ〔5゜5〕ウンデ
カン
この方法により安定化される合成高分子には次のものが
含まれる。19 Di-lauryl thio-di-propionate 20 Di-myristyl thio-di-propionate 21 Di-stearyl thio-di-propionate 22 Glycerol Tris(3-dodecylthiopropionate) 23 Trimethylolpropane Tris(3-octadecylthiopropionate) 24 Pentaerythritol Tetrakis(3-dodecylthiopropionate) 25 3.9-hyx(2-)”f-sylthioethyl)-2
, 4,8,10-tetraoxaspiro[5°5]undecane.Synthetic polymers stabilized by this method include:
オレフィン及びジエンポリマー
オレフィン及びジエンのホモポリマー(例工ば、低密度
、直鎖状低密度、高密度及び架橋ポリエチレン、ポリプ
ロピレン、ポリイソブチレン、ポリメチルブテン−1、
ポリメチルペンテン−1、ポリイソプレン及びポリブタ
ジェン)、そのようなホモポリマーの混合物(例えば、
ポリプロピレンとポリエチレン、ポリプロピレンとポリ
ブテン−1、又はポリプロピレンとポリイソブチレンの
混合物)、オレフィンのコポリ”−C例、tばエチレン
−プロピレン コポリマー、プロピレン−ブテン−1コ
ポリマー、フロピレン−イソブチン コポリマー、エチ
レン−ブテン−1コポリマー)、及びオレフィンとジエ
ンのコーポリマー(例えば、エチレン及びプロピレンと
ブタジェン、ヘキサジエン、ジシクロペンタジェン又は
エチリデンノルボルネンのようなジエンとのターポリマ
ー):スチレンポリマー
ポリスチレン、スチレンまたはα−メチルスチレンのコ
ーポリマー(例えば、スチレン−無水マレイン酸コポリ
マー、スチレン−ブタジェン コポリマー、スチレンー
アクリロニ) IJ ルコボリマー、スチレン−アクリ
ロニトリル−メチルメタクリレート コポリマー、スチ
レン−アクリロニトリル−アクリル酸エステル コポリ
マー、衝撃強度を与えるためにアクリル酸エステルポリ
マーで変性されたスチレン−アクリロニトリル コポリ
マー、および衝撃強度を与えるためにEPDMで変性さ
れたスチレンポリマー)、及びスチレンのグラフト コ
ポリマー(例えば、ポリブタジェンに対するスチレンの
グラフトポリマー、通常アクリロニトリル−ブタジェン
−スチレン又はAE8プラスチックスといわれるポリブ
タジェンに対するスチレンおよびアクリロニトリルのグ
ラフトポリマー及び上記スチレン コポリマーとこれと
の混合物):ハロゲン化ビニル及びビニリデンポリマー
ポリ塩化ビニル、ポリ、塩化ビニリデン、ポリフッ化ビ
ニル、ポリクロロプレン、a素化ゴム、塩化ビニル−塩
化ビニリデン コポリマー、塩化ビニル−酢酸ビニル
コポリマー、塩化ビニル−エチレンコポリマー、塩化ヒ
ニI)!:/−6酸ビニル コポリマー:
ポリアクリル酸エステル及びポリメタクリル酸エステル
、ポリアクリルアミド及びポリアクリロニトリル:
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、ポリフタル酸アリル、ポリ
メラミンアリル及び前記単量体と他種のビニル化合物と
のコポリマー(flJ、tハエチレンー酢酸ビニル コ
ポリマー):エポキシポリマー
エボ中シ化合物のホモポリマー及びコポリマー(例えば
、ポリエチレ゛ンオ中シト)及びビスグリシジルエーテ
ル化合物のポリマー:ポリオキシメチレン、オキシメチ
レン−エチレンオキシド コポリマー、ポリオキシエチ
レン、ポリプロピレンオキシド、ポリイソブチレンオキ
シド及びポリフェニレンオキシド:ジアミンと脂肪族又
は芳香族ジカルボン酸から誘導される、及び/又はアミ
ノカルボン酸又はそれに対応するラクタムから誘導され
るポリアミド及びコポリアミド:例えば、ナイロン−6
、ナイロン−6/6、ナイロン−6710,ナイロン−
11、ナイロン12:
ポリエステル
ジカルボン酸とジアルコールとから、及び/又はオキシ
酸マたはそれに対応するラクトンから誘導されるポリエ
ステル:例えば、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−シクロヘキサン−1,4
−ジメチレ□ ンテレフタレート:
架橋ポリマー
一方がアルデヒド、他方がフェノール、尿素又はメラミ
ンとから誘導される架橋ポリマー :例えば、フェノー
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゛及びジアリール
フタレート樹脂:
アルキド樹脂
例えば、グリセロール−フタル酸樹脂、及びこれとメラ
ミン−ホルムアルデヒド樹脂との混合物:
不飽和ポリエステル樹脂
飽和及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
用いて得られた不飽和ポリエステル樹脂、及びそれを塩
素化して難燃化変性を施したもの。Olefin and diene polymers Homopolymers of olefins and dienes (e.g., low density, linear low density, high density and crosslinked polyethylene, polypropylene, polyisobutylene, polymethylbutene-1,
polymethylpentene-1, polyisoprene and polybutadiene), mixtures of such homopolymers (e.g.
mixtures of polypropylene and polyethylene, polypropylene and polybutene-1, or polypropylene and polyisobutylene), olefin copolymers, ethylene-propylene copolymers, propylene-butene-1 copolymers, propylene-isobutene copolymers, ethylene-butene-1 1 copolymer), and copolymers of olefins and dienes (e.g. terpolymers of ethylene and propylene with dienes such as butadiene, hexadiene, dicyclopentadiene or ethylidene norbornene): styrene polymers of polystyrene, styrene or α-methylstyrene. Copolymers (e.g. styrene-maleic anhydride copolymers, styrene-butadiene copolymers, styrene-acryloni) IJ lucopolymers, styrene-acrylonitrile-methyl methacrylate copolymers, styrene-acrylonitrile-acrylic ester copolymers, acrylic acid to provide impact strength styrene-acrylonitrile copolymers modified with ester polymers and styrene polymers modified with EPDM to provide impact strength), and graft copolymers of styrene (e.g., graft polymers of styrene to polybutadiene, usually acrylonitrile-butadiene-styrene or AE8 Graft polymers of styrene and acrylonitrile on polybutadiene (referred to as plastics) and mixtures thereof with the above styrene copolymers): vinyl halide and vinylidene polymers polyvinyl chloride, poly, vinylidene chloride, polyvinyl fluoride, polychloroprene, a-base rubber, Vinyl chloride-vinylidene chloride copolymer, vinyl chloride-vinyl acetate
copolymer, vinyl chloride-ethylene copolymer, hinichloride I)! :/-vinyl hexate copolymers: polyacrylic and polymethacrylic esters, polyacrylamides and polyacrylonitrile: polyvinyl alcohol, polyvinyl acetate, polyvinyl stearate, polyvinyl benzoate, polyvinyl maleate, polyvinyl butyral, polyphthalic acid Copolymers of allyl, polymelamine allyl, and the above monomers with other types of vinyl compounds (flJ, t-ethylene-vinyl acetate copolymers): homopolymers and copolymers of vinyl compounds in epoxy polymers (e.g., polyethylene-vinyl acetate); Polymers of bisglycidyl ether compounds: polyoxymethylene, oxymethylene-ethylene oxide copolymers, polyoxyethylene, polypropylene oxide, polyisobutylene oxide and polyphenylene oxide: derived from diamines and aliphatic or aromatic dicarboxylic acids, and/or aminocarboxylic Polyamides and copolyamides derived from acids or the corresponding lactams: e.g. nylon-6
, nylon-6/6, nylon-6710, nylon-
11, Nylon 12: Polyesters derived from dicarboxylic acids and dialcohols and/or from oxyacids or their corresponding lactones: for example, polyethylene terephthalate, polybutylene terephthalate, polycyclohexane-1,4
- Dimethylene terephthalate: Crosslinked polymers Crosslinked polymers derived from aldehyde on one side and phenol, urea or melamine on the other side: For example, phenol-formaldehyde resins, urea-formaldehyde resins, melamine-formaldehyde resins and diaryl phthalate resins: Alkyds Resins such as glycerol-phthalic acid resins and their mixtures with melamine-formaldehyde resins: unsaturated polyester resins derived from copolyesters of saturated and unsaturated dicarboxylic acids and polyhydric alcohols, using vinyl compounds as crosslinkers The obtained unsaturated polyester resin and its flame-retardant modified product by chlorination.
高分子の効果的安定化に必要な本発明の化合物(Ia)
〜(Ic)及び化合物(Ila) 〜(IC) ノJ
ia、種々の要因、例えば対象となるポリマーの種類及
び性質、その使用目的、及び他の安定剤の存在等に依存
する。通常、高分子の重■を基準にして本発明の安定剤
を001乃至5重fi%用いると充分であるが、最も有
効な範囲はポリマーの種類により変る:即ち、オレフィ
ン、ジエンおよびスチレンポリマーについては001乃
至2.0重散慢、好ましくは0.02乃至1.0重金%
:塩化ビニルおよび頃化ビニルデンポリマーについては
α01乃至1,0重機チ、好ましくは0.02乃至15
重量%:そして、ポリウレタン及びポリアミドについて
は001乃至5,0重音チ、好ましくは002乃至2.
O7量チである。所望により、本発明の安定剤の2種ま
たはそれ以上を一緒に用いることができる。Compound (Ia) of the present invention necessary for effective stabilization of polymers
~(Ic) and compound (Ila) ~(IC) NoJ
ia depends on various factors, such as the type and nature of the polymer in question, its intended use, and the presence of other stabilizers. Generally, it is sufficient to use the stabilizer of the present invention at 0.001 to 5% by weight, based on the weight of the polymer, but the most effective range varies depending on the type of polymer: i.e., for olefin, diene, and styrene polymers. is 0.001% to 2.0% heavy metal, preferably 0.02% to 1.0% heavy metal.
: For vinyl chloride and vinylene polymers, α01 to 1.0, preferably 0.02 to 15
Weight %: and for polyurethane and polyamide, from 001 to 5.0, preferably from 002 to 2.
The amount of O7 is high. If desired, two or more of the stabilizers of the present invention can be used together.
本発明の安定剤は通常の技術により、成形物品を製造す
る前の都合のよいあらゆる段階で高分子に容易に混入で
きる。The stabilizers of the present invention can be readily incorporated into the polymer by conventional techniques at any convenient stage prior to manufacturing the shaped article.
本発明の高分子用安定剤は、高分子技術の分野で種々の
慣用の添加剤を適宜含ませることができ、例えばそのよ
うな添加剤として
フェノール系抗酸化剤
2.6−ジーt−ブチル−p−クレゾール、ステアリル
−β−(4−ヒドロキシ−3,5−ジ−t−ブチルフェ
ニル)プロピオネート、ジステアリル(4−ヒドロキシ
−3−メチル−S−を−ブチル)ペンジルマロネー)、
12−メチレンビス(4−メチル−8−t−)−f−ル
フェノール)、4.4−メチレンビス(2,6−ジー・
t−ブチルフェノール)、 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〔3,3−ビス(4−ヒドロキシ−3−t−プチルフ
ェニル)ブチリックアシドコグリコールエステル、4.
4−7’チリデンビス(6−1−ブチル−m−クレゾー
ル)、1.1+ 3− )リス(2−メチル−4−ヒド
ロキシ−5−t−ブチルフェニル)ブタン、t、 3.
5−)リス(3,5−ジーt−7”fルー4−ヒドロキ
シベンジル)−λ4.6−ドリメチルベンゼン、3.9
−ビス〔1,1−ジメチル−2−(3,5−ジ−t−ブ
チル−4−ヒドロキシフェニル)エチル]−2,4,8
,10−テトラオキサスピロ〔5,5〕ウンデカン、テ
トラキス〔メチレン−3−(3,5−ジ−t−ブチル−
4−ヒドロキシフェニル)プロピオネートコメタン、1
.3.5− )リス(3,5−ジーt−7”チル−4−
ヒドロキシベンジル)インシアスレート及び1.3.5
− )リス〔3,5−ジーを一ブチルー4−ヒドロキシ
フェニル〕フロピオニルオキシエチル〕イソシアスレー
ト、ビス〔3−C3,S−ジ−t−ブチル−4−ヒドロ
キシフェニル)プロピオニル〕オキサミド
ホスファイト系安定剤
) y ス(2,4−シー t −)fルフェニル)ホ
スファイト、トリフェニルホスファイト、トリス(ノニ
ルフェニル)ホスファイト、シスf7リルベンタエリス
リトール ジホスファイト、4.4−ブチリデンビス(
3−メチル−6−1−ブチルフェニル−ジ−トリデシル
)ホスファイト、ビス(2,4−ジ−t−ブチルフェニ
ル)ペンタエリストール ジホスファイト
□ 紫外線吸収剤
2−ヒドロキシ−4−メトキシベンゾフェノン、2−ヒ
ドロキシ−4−n−オクトキシベンゾフェノン、2.4
−ジヒドロキシベンゾフェノン、2−(2−ヒドロキシ
−3−t−ブチル−5−メチルフェニル)−5−クロロ
ベンゾトリアゾール、2−(2−ヒドロキシ−3,5−
ジ−t−ブチルフェニル)−5−クロ胃ベンツトリアソ
ール、2−(2−ヒドロキシ−5−メチルフェニル)ベ
ンツトリアゾール、2−(2−ヒドロキシ−3,5−ジ
−t−アミルフェニル)ベンゾトリアゾール、フェニル
サリシレート、λ4−ジーt−ブチルフェニルー3.5
−シーt−フチルー4−ヒドロキシベンゾエートニッケ
ル系安定剤
N1−モノエチル−3,5−ジ−t−ブチル−4−とド
ロ中ジベンジルホスホネート、ブチルアミン−Ni −
2,2−チオビス(4−1−オクチルフェルレート)錯
体、N1−ジブチル−ジチオカルバメート、N1−λ5
−ジーt−ブチルー4−ヒドロキシベ/シェード
高級脂肪酸の金属塩
カルシウム、バリウム、亜鉛、カドミウム、鉛若しくは
ニッケルステアレート、カルシウム、カドミウム、バリ
ウム若しくは亜鉛ラウレート。The stabilizer for polymers of the present invention can appropriately contain various additives commonly used in the field of polymer technology, such as the phenolic antioxidant 2,6-di-t-butyl. -p-cresol, stearyl-β-(4-hydroxy-3,5-di-t-butylphenyl)propionate, distearyl (4-hydroxy-3-methyl-S-butyl)penzylmalone),
12-methylenebis(4-methyl-8-t-)-f-ruphenol), 4,4-methylenebis(2,6-di-
t-butylphenol), 2,2-methylenebis[6
-(1-methylcyclohexyl)p-cresol], bis[3,3-bis(4-hydroxy-3-t-butylphenyl)butyric acidocoglycol ester, 4.
4-7' thylidene bis(6-1-butyl-m-cresol), 1.1+ 3-)lis(2-methyl-4-hydroxy-5-t-butylphenyl)butane, t, 3.
5-) Lis(3,5-di-t-7"f-4-hydroxybenzyl)-λ4.6-drimethylbenzene, 3.9
-bis[1,1-dimethyl-2-(3,5-di-t-butyl-4-hydroxyphenyl)ethyl]-2,4,8
, 10-tetraoxaspiro[5,5]undecane, tetrakis[methylene-3-(3,5-di-t-butyl-
4-Hydroxyphenyl)propionate comethane, 1
.. 3.5-) Squirrel (3,5-G-t-7” Chill-4-
hydroxybenzyl) insia slate and 1.3.5
-) Lis[3,5-di-butyl-4-hydroxyphenyl]propionyloxyethyl]isocyanate, bis[3-C3,S-di-t-butyl-4-hydroxyphenyl)propionyl]oxamide phos phyto-based stabilizers) ys(2,4-c-t-)f-ruphenyl) phosphite, triphenyl phosphite, tris(nonylphenyl) phosphite, cis-f7 lylbentaerythritol diphosphite, 4,4-butylidene bis(
3-Methyl-6-1-butylphenyl-di-tridecyl) phosphite, bis(2,4-di-t-butylphenyl)pentaerystol diphosphite □ Ultraviolet absorber 2-hydroxy-4-methoxybenzophenone, 2- Hydroxy-4-n-octoxybenzophenone, 2.4
-dihydroxybenzophenone, 2-(2-hydroxy-3-t-butyl-5-methylphenyl)-5-chlorobenzotriazole, 2-(2-hydroxy-3,5-
di-t-butylphenyl)-5-chlorogastric benztriazole, 2-(2-hydroxy-5-methylphenyl)benztriazole, 2-(2-hydroxy-3,5-di-t-amylphenyl)benzo Triazole, phenyl salicylate, λ4-di-t-butylphenyl-3.5
- Sheet t-phthyl-4-hydroxybenzoate Nickel stabilizer N1-monoethyl-3,5-di-t-butyl-4- and dibenzylphosphonate in the slurry, butylamine-Ni -
2,2-thiobis(4-1-octylferulate) complex, N1-dibutyl-dithiocarbamate, N1-λ5
- di-tert-butyl-4-hydroxybe/shade Metal salts of higher fatty acids calcium, barium, zinc, cadmium, lead or nickel stearate, calcium, cadmium, barium or zinc laurate.
その他必要に応じ、重金属不活性化剤、造核剤、有機錫
化合物、可塑剤、エポキシ化合物、顔料、充填剤、発泡
剤、帯電防止剤、滑剤、加工助剤等と併用することがで
きる。If necessary, it can be used in combination with heavy metal deactivators, nucleating agents, organic tin compounds, plasticizers, epoxy compounds, pigments, fillers, foaming agents, antistatic agents, lubricants, processing aids, and the like.
この様にして安定化されたプラスチックは、非常に広範
な形態で、例えばフィルム、繊細、テープ、圧縮成形材
料、塗料組成物またはペイントとして使用できる。Plastics stabilized in this way can be used in a wide variety of forms, for example as films, delicacies, tapes, compression molding materials, coating compositions or paints.
以下、実施例をもって本発明をさらに詳しく説明する。Hereinafter, the present invention will be explained in more detail with reference to Examples.
実施例1゜
下記配合物をプラベンダー・プラスチコーダー中、20
0℃で10分間混練して均質にした。Example 1゜The following formulation was placed in Prabender Plasticorder for 20 minutes.
The mixture was homogenized by kneading for 10 minutes at 0°C.
得られた塊を実験用プレス機で2〜3am厚のシートに
圧延した。このシートの一部を油圧プレス機で260℃
で6分間加圧し、次いで直ちに冷水中に投入して15m
厚のシートを得た。このシートから、50X10(Is
の試験片を作成し、150℃のオーブン中に経時し、白
化するまでの時間を測定し、熱安定性の指標とした。又
、同時に試験片作成時及び150℃オープン中経時した
後、試験片の外観を肉眼で観察して、耐着色性を測定し
た。The resulting mass was rolled into a 2-3 am thick sheet in a laboratory press. A part of this sheet is heated to 260℃ using a hydraulic press machine.
Pressurized for 6 minutes, then immediately placed in cold water for 15 m
A thick sheet was obtained. From this sheet, 50X10(Is
A test piece was prepared, placed in an oven at 150°C, and the time until whitening was measured, which was used as an index of thermal stability. At the same time, the appearance of the test piece was observed with the naked eye during preparation of the test piece and after being left open at 150° C. to measure the coloring resistance.
なお、光安定性は、上記試験片をサンシャインカーボン
ウェザ−・メーター中黒板温度63±3℃、スプレー1
2分/60分で光に曝し、露光された試料を周期的に引
張試験を行い、伸びが初期の50%に低下する時間で表
わした。The light stability was determined by testing the above test piece in a Sunshine Carbon Weather Meter at a blackboard temperature of 63±3°C and spraying 1
The exposed samples were exposed to light at a rate of 2 minutes/60 minutes and were periodically subjected to a tensile test, expressed as the time for elongation to fall to 50% of the initial value.
〈配 合〉
未安定化ポリプロピレンCMIFR:1.5) 100
重鱈ステアリン酸カルシウム a10ステア
リル 3−(3,5−&ジーを一ブチルー4−ヒドロキ
シフェニル)
プロピオネートa10
テトラヤス−〔メチレン−3−(&5
−シーt−7’チルー4−ヒドロキシフェニル)プロピ
オネートコメタン 110重鱈供試化合物
表 1
*)A:試験片作成時。<Blend> Unstabilized polypropylene CMIFR: 1.5) 100
Heavy cod calcium stearate a10 stearyl 3-(3,5-&di-monobutyl-4-hydroxyphenyl) propionate a10 tetrayasu-[methylene-3-(&5-cyt-7'ty-4-hydroxyphenyl)propionate comethane 110 heavy cod test compound table 1 *) A: At the time of test piece creation.
B : 150℃、4週間オープン経時後。B: After being opened for 4 weeks at 150°C.
■:無色、0.:はとんど無色、Δ:やや着色、×:着
色。■: Colorless, 0. : Almost colorless, Δ: Slightly colored, ×: Colored.
**)光安定性=450時間
上記表1から分かるように、本願発明の組成物は、耐熱
性についてすぐれた相剰効果を有し耐着色性にもすぐれ
、かつ耐光性についても十分な効果を有するものといえ
る。**) Photostability = 450 hours As can be seen from Table 1 above, the composition of the present invention has an excellent mutual effect on heat resistance, excellent coloring resistance, and sufficient effect on light resistance. It can be said that it has the following.
Claims (1)
トリアジン誘導体の少なくとも一種及び下記一般式(I
Ia)〜(IIc)を有する硫黄系酸化防止剤の少なくと
も一種を有効成分として含有することを特徴とする合成
高分子材料用安定剤。 ▲数式、化学式、表等があります▼( I a) ▲数式、化学式、表等があります▼( I b) ▲数式、化学式、表等があります▼( I c) 上記式( I a)〜( I c)中、 Xは、式 ▲数式、化学式、表等があります▼(III) を有する基〔式中、R_1は、水素原子、炭素原子1乃
至18個を有するアルキル基、炭素原子3乃至22個を
有するアルコキシアルキル基、置換されていてもよいア
ラルキル基又は式 ▲数式、化学式、表等があります▼(IV)を有する基(
式中、 R_3は、後述するR_2と同意義を示す。)を示し、
R_2は、水素原子、炭素原子1個乃至18個を有する
アルキル基又は置換されていてもよいアラルキル基を示
す。〕を示し、 Yは、モルホリノ基又は式−NHR_4を有する基〔式
中、R_4は、炭素原子1個乃至18個を有するアルキ
ル基又は式 ▲数式、化学式、表等があります▼(VI)を有する基(
式中、 R_3は、前述したものと同意義を示す。)を示し、n
は、2乃至20の整数を示す。 ▲数式、化学式、表等があります▼(IIa) ▲数式、化学式、表等があります▼(IIb) ▲数式、化学式、表等があります▼(IIc) 上記式(IIa)〜(IIc)中、 R_5は、炭素原子4乃至18個を有するアルキル基を
示し、 mは、2乃至4の整数を示し、 mが2のとき、Zは、エチレン基を示し、 mが3のとき、Zは、式−CH_2−CH−CH_2−
又は▲数式、化学式、表等があります▼を有する基を示
し、 mが4のとき、Zは、式▲数式、化学式、表等がありま
す▼を有 する基を示す。[Claims] Piperidyl having the following general formulas (Ia) to (Ic)
At least one triazine derivative and the following general formula (I
A stabilizer for synthetic polymer materials, characterized in that it contains at least one of the sulfur-based antioxidants Ia) to (IIc) as an active ingredient. ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ ( I a) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ ( I b) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ ( I c) Above formulas ( I a) ~ ( Ic), where X is a group having the formula ▲A mathematical formula, a chemical formula, a table, etc.▼(III) [wherein R_1 is a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, or a group having 3 to 18 carbon atoms] An alkoxyalkyl group having 22 atoms, an optionally substituted aralkyl group, or a group having the formula ▲Numerical formula, chemical formula, table, etc.▼(IV)
In the formula, R_3 has the same meaning as R_2 described below. ),
R_2 represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, or an optionally substituted aralkyl group. ], Y is a morpholino group or a group having the formula -NHR_4 [wherein R_4 is an alkyl group having 1 to 18 carbon atoms or the formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (VI) The group having (
In the formula, R_3 has the same meaning as described above. ), n
represents an integer from 2 to 20. ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (IIa) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (IIb) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (IIc) In the above formulas (IIa) to (IIc), R_5 represents an alkyl group having 4 to 18 carbon atoms, m represents an integer of 2 to 4, when m is 2, Z represents an ethylene group, and when m is 3, Z represents Formula -CH_2-CH-CH_2-
Or, it indicates a group that has the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and when m is 4, Z indicates a group that has the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP4668886A JPS62205141A (en) | 1986-03-04 | 1986-03-04 | Stabilizer for use in synthetic polymeric material |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP4668886A JPS62205141A (en) | 1986-03-04 | 1986-03-04 | Stabilizer for use in synthetic polymeric material |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS62205141A true JPS62205141A (en) | 1987-09-09 |
Family
ID=12754317
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP4668886A Pending JPS62205141A (en) | 1986-03-04 | 1986-03-04 | Stabilizer for use in synthetic polymeric material |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS62205141A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0225471A (en) * | 1988-05-31 | 1990-01-26 | Ciba Geigy Ag | Polyamines partially substituted with bis-piperidyl-triazines |
JPH0225482A (en) * | 1988-05-31 | 1990-01-26 | Ciba Geigy Ag | Polyamine partially substituted with piperidine-triazine |
-
1986
- 1986-03-04 JP JP4668886A patent/JPS62205141A/en active Pending
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0225471A (en) * | 1988-05-31 | 1990-01-26 | Ciba Geigy Ag | Polyamines partially substituted with bis-piperidyl-triazines |
JPH0225482A (en) * | 1988-05-31 | 1990-01-26 | Ciba Geigy Ag | Polyamine partially substituted with piperidine-triazine |
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