JPS63196654A - Stabilized high-molecular material composition - Google Patents
Stabilized high-molecular material compositionInfo
- Publication number
- JPS63196654A JPS63196654A JP2762887A JP2762887A JPS63196654A JP S63196654 A JPS63196654 A JP S63196654A JP 2762887 A JP2762887 A JP 2762887A JP 2762887 A JP2762887 A JP 2762887A JP S63196654 A JPS63196654 A JP S63196654A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- butyl
- tert
- weight
- 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
- 239000000463 material Substances 0.000 title claims abstract description 16
- 239000000203 mixture Substances 0.000 title claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 4
- 125000002252 acyl group Chemical group 0.000 abstract description 4
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 abstract description 4
- DZUAAFRNIXXDCM-UHFFFAOYSA-N 2,2,3,3-tetramethylpiperidin-1-amine Chemical compound CC1(C)CCCN(N)C1(C)C DZUAAFRNIXXDCM-UHFFFAOYSA-N 0.000 abstract description 2
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- -1 polyethylene Polymers 0.000 description 25
- 229920001577 copolymer Polymers 0.000 description 15
- 229920005989 resin Polymers 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- 239000003381 stabilizer Substances 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000003973 paint Substances 0.000 description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- 238000009472 formulation Methods 0.000 description 5
- 239000004611 light stabiliser Substances 0.000 description 5
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229920003002 synthetic resin Polymers 0.000 description 5
- 239000000057 synthetic resin Substances 0.000 description 5
- 229920000178 Acrylic resin Polymers 0.000 description 4
- 239000004925 Acrylic resin Substances 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 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 4
- 229920000573 polyethylene Polymers 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- 239000005060 rubber Substances 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- NNWUEBIEOFQMSS-UHFFFAOYSA-N 2-Methylpiperidine Chemical compound CC1CCCCN1 NNWUEBIEOFQMSS-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000002861 polymer material Substances 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- 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 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 2
- UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 description 2
- ISAVYTVYFVQUDY-UHFFFAOYSA-N 4-tert-Octylphenol Chemical class CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 ISAVYTVYFVQUDY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- MBHRHUJRKGNOKX-UHFFFAOYSA-N [(4,6-diamino-1,3,5-triazin-2-yl)amino]methanol Chemical compound NC1=NC(N)=NC(NCO)=N1 MBHRHUJRKGNOKX-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 125000002704 decyl 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])* 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- KZTWONRVIPPDKH-UHFFFAOYSA-N hydroxyethyl piperidine Natural products OCCN1CCCCC1 KZTWONRVIPPDKH-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 230000005389 magnetism Effects 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 239000002530 phenolic antioxidant Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 150000003053 piperidines Chemical class 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229920001897 terpolymer Polymers 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
- 238000005406 washing Methods 0.000 description 2
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- 229920003067 (meth)acrylic acid ester copolymer Polymers 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- FXHRAKUEZPSMLJ-UHFFFAOYSA-N 1-methyl-1,4-diazepane Chemical compound CN1CCCNCC1 FXHRAKUEZPSMLJ-UHFFFAOYSA-N 0.000 description 1
- RNTWMPKPEATMJA-UHFFFAOYSA-N 16-iodohexadecanoic acid Chemical compound OC(=O)CCCCCCCCCCCCCCCI RNTWMPKPEATMJA-UHFFFAOYSA-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
- 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
- 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
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
- SDGKUVSVPIIUCF-UHFFFAOYSA-N 2,6-dimethylpiperidine Chemical compound CC1CCCC(C)N1 SDGKUVSVPIIUCF-UHFFFAOYSA-N 0.000 description 1
- GOWUDHPKGOIDIX-UHFFFAOYSA-N 2-(4-methyl-1-piperazinyl)ethanamine Chemical compound CN1CCN(CCN)CC1 GOWUDHPKGOIDIX-UHFFFAOYSA-N 0.000 description 1
- MXALMAQOPWXPPY-UHFFFAOYSA-N 2-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]prop-2-enoic acid Chemical compound CC(C)(C)C1=CC(CC(=C)C(O)=O)=CC(C(C)(C)C)=C1O MXALMAQOPWXPPY-UHFFFAOYSA-N 0.000 description 1
- DZIKPFGVVYFUGO-UHFFFAOYSA-N 2-[(4-hydroxy-3,5-dimethylphenyl)methyl]-2-sulfanylicosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCC(S)(C(O)=O)CC1=CC(C)=C(O)C(C)=C1 DZIKPFGVVYFUGO-UHFFFAOYSA-N 0.000 description 1
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- WWYDYZMNFQIYPT-UHFFFAOYSA-L 2-phenylpropanedioate Chemical compound [O-]C(=O)C(C([O-])=O)C1=CC=CC=C1 WWYDYZMNFQIYPT-UHFFFAOYSA-L 0.000 description 1
- CJNRGSHEMCMUOE-UHFFFAOYSA-N 2-piperidin-1-ylethanamine Chemical compound NCCN1CCCCC1 CJNRGSHEMCMUOE-UHFFFAOYSA-N 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- OVFNLCOUYWXMMV-UHFFFAOYSA-N 2-tert-butyl-4-[14-(5-tert-butyl-4-hydroxy-2-methylphenyl)-17,17-di(tridecyl)triacontan-14-yl]-5-methylphenol dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(CCCCCCCCCCCCC)(CCC(CCCCCCCCCCCCC)(CCCCCCCCCCCCC)CCCCCCCCCCCCC)C1=CC(C(C)(C)C)=C(O)C=C1C OVFNLCOUYWXMMV-UHFFFAOYSA-N 0.000 description 1
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 1
- NMAGCVWUISAHAP-UHFFFAOYSA-N 3,5-ditert-butyl-2-(2,4-ditert-butylphenyl)-4-hydroxybenzoic acid Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1C1=C(C(O)=O)C=C(C(C)(C)C)C(O)=C1C(C)(C)C NMAGCVWUISAHAP-UHFFFAOYSA-N 0.000 description 1
- YEXOWHQZWLCHHD-UHFFFAOYSA-N 3,5-ditert-butyl-4-hydroxybenzoic acid Chemical compound CC(C)(C)C1=CC(C(O)=O)=CC(C(C)(C)C)=C1O YEXOWHQZWLCHHD-UHFFFAOYSA-N 0.000 description 1
- PZRWFKGUFWPFID-UHFFFAOYSA-N 3,9-dioctadecoxy-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C1OP(OCCCCCCCCCCCCCCCCCC)OCC21COP(OCCCCCCCCCCCCCCCCCC)OC2 PZRWFKGUFWPFID-UHFFFAOYSA-N 0.000 description 1
- YYAYTNPNFKPFNG-UHFFFAOYSA-N 3-(2-methylpiperidin-1-yl)propan-1-amine Chemical compound CC1CCCCN1CCCN YYAYTNPNFKPFNG-UHFFFAOYSA-N 0.000 description 1
- MQSXUKPGWMJYBT-UHFFFAOYSA-N 3-butylphenol Chemical compound CCCCC1=CC=CC(O)=C1 MQSXUKPGWMJYBT-UHFFFAOYSA-N 0.000 description 1
- JEGMWWXJUXDNJN-UHFFFAOYSA-N 3-methylpiperidine Chemical compound CC1CCCNC1 JEGMWWXJUXDNJN-UHFFFAOYSA-N 0.000 description 1
- JMUCXULQKPWSTJ-UHFFFAOYSA-N 3-piperidin-1-ylpropan-1-amine Chemical compound NCCCN1CCCCC1 JMUCXULQKPWSTJ-UHFFFAOYSA-N 0.000 description 1
- KEYGKBHQZBQADZ-UHFFFAOYSA-N 4-[16,16-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)-14-methyl-15,15-di(tridecyl)nonacosan-14-yl]-2-tert-butyl-5-methylphenol dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(CCCCCCCCCCCCC)(C=1C(=CC(O)=C(C=1)C(C)(C)C)C)C(CCCCCCCCCCCCC)(CCCCCCCCCCCCC)C(C)(CCCCCCCCCCCCC)C1=CC(C(C)(C)C)=C(O)C=C1C KEYGKBHQZBQADZ-UHFFFAOYSA-N 0.000 description 1
- ABGXADJDTPFFSZ-UHFFFAOYSA-N 4-benzylpiperidine Chemical compound C=1C=CC=CC=1CC1CCNCC1 ABGXADJDTPFFSZ-UHFFFAOYSA-N 0.000 description 1
- UQUHQKVINDTPNE-UHFFFAOYSA-N 4-methylpiperidin-1-amine Chemical compound CC1CCN(N)CC1 UQUHQKVINDTPNE-UHFFFAOYSA-N 0.000 description 1
- AITRTUFPKXVJCM-UHFFFAOYSA-N 4-octoxy-2,6-diphenylphenol Chemical compound C=1C(OCCCCCCCC)=CC(C=2C=CC=CC=2)=C(O)C=1C1=CC=CC=C1 AITRTUFPKXVJCM-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000004709 Chlorinated polyethylene Substances 0.000 description 1
- IVRFYNSETZKRSJ-UHFFFAOYSA-N ClC=C.N#CC=CC=CC1=CC=CC=C1 Chemical compound ClC=C.N#CC=CC=CC1=CC=CC=C1 IVRFYNSETZKRSJ-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- QLEVNOOJHGPAIJ-UHFFFAOYSA-N N1C(CC(CC1)C)C.CC1NCCC(C1)C Chemical compound N1C(CC(CC1)C)C.CC1NCCC(C1)C QLEVNOOJHGPAIJ-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- QAEPIAHUOVJOOM-UHFFFAOYSA-N OP(O)OP(O)O.C(CCCCCCCC)C1=C(C=CC=C1)C(O)(C(CO)(CO)CO)C1=C(C=CC=C1)CCCCCCCCC Chemical compound OP(O)OP(O)O.C(CCCCCCCC)C1=C(C=CC=C1)C(O)(C(CO)(CO)CO)C1=C(C=CC=C1)CCCCCCCCC QAEPIAHUOVJOOM-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 1
- 229920012485 Plasticized Polyvinyl chloride Polymers 0.000 description 1
- 229930182556 Polyacetal Natural products 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-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
- BEIOEBMXPVYLRY-UHFFFAOYSA-N [4-[4-bis(2,4-ditert-butylphenoxy)phosphanylphenyl]phenyl]-bis(2,4-ditert-butylphenoxy)phosphane Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(C=1C=CC(=CC=1)C=1C=CC(=CC=1)P(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C BEIOEBMXPVYLRY-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 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
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 150000008360 acrylonitriles Chemical class 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
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- 239000011230 binding agent Substances 0.000 description 1
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- SXXILWLQSQDLDL-UHFFFAOYSA-N bis(8-methylnonyl) phenyl phosphite Chemical compound CC(C)CCCCCCCOP(OCCCCCCCC(C)C)OC1=CC=CC=C1 SXXILWLQSQDLDL-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 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
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- IEJNAGSUKYCWCR-UHFFFAOYSA-N chloroethene;1,1-dichloroethene;ethenyl acetate Chemical compound ClC=C.ClC(Cl)=C.CC(=O)OC=C IEJNAGSUKYCWCR-UHFFFAOYSA-N 0.000 description 1
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- KRGNPJFAKZHQPS-UHFFFAOYSA-N chloroethene;ethene Chemical group C=C.ClC=C KRGNPJFAKZHQPS-UHFFFAOYSA-N 0.000 description 1
- SQNNHEYXAJPPKH-UHFFFAOYSA-N chloroethene;prop-2-enoic acid Chemical compound ClC=C.OC(=O)C=C SQNNHEYXAJPPKH-UHFFFAOYSA-N 0.000 description 1
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- 238000000576 coating method Methods 0.000 description 1
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- 229940125782 compound 2 Drugs 0.000 description 1
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- 238000005336 cracking Methods 0.000 description 1
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- 150000007973 cyanuric acids Chemical class 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
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 150000004985 diamines 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
- 238000002845 discoloration Methods 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 239000004794 expanded polystyrene Substances 0.000 description 1
- 239000000835 fiber Substances 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
- 235000011187 glycerol Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 229920003049 isoprene rubber Polymers 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- CXQTTWVBUDFUNO-UHFFFAOYSA-N methyl piperidine-2-carboxylate Chemical compound COC(=O)C1CCCCN1 CXQTTWVBUDFUNO-UHFFFAOYSA-N 0.000 description 1
- RZVWBASHHLFBJF-UHFFFAOYSA-N methyl piperidine-4-carboxylate Chemical compound COC(=O)C1CCNCC1 RZVWBASHHLFBJF-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HMBACZSMXMWPHQ-UHFFFAOYSA-N n'-(3-tert-butylphenyl)-n-ethoxy-n-ethyl-n'-phenyloxamide Chemical compound C=1C=CC(C(C)(C)C)=CC=1N(C(=O)C(=O)N(CC)OCC)C1=CC=CC=C1 HMBACZSMXMWPHQ-UHFFFAOYSA-N 0.000 description 1
- UKJARPDLRWBRAX-UHFFFAOYSA-N n,n'-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine Chemical compound C1C(C)(C)NC(C)(C)CC1NCCCCCCNC1CC(C)(C)NC(C)(C)C1 UKJARPDLRWBRAX-UHFFFAOYSA-N 0.000 description 1
- FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical class C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 description 1
- IGCVAKMLNISJHR-UHFFFAOYSA-N n-methylpiperidin-1-amine Chemical compound CNN1CCCCC1 IGCVAKMLNISJHR-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002816 nickel compounds Chemical class 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- JLXPQFBAFJZAQZ-UHFFFAOYSA-N o-[3-hydroxy-2,2-bis(hydroxymethyl)propyl] 2,2,3-tridodecylpentadecanethioate Chemical compound CCCCCCCCCCCCC(CCCCCCCCCCCC)C(CCCCCCCCCCCC)(CCCCCCCCCCCC)C(=S)OCC(CO)(CO)CO JLXPQFBAFJZAQZ-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
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 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
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 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
- 210000004417 patella Anatomy 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229960000969 phenyl salicylate Drugs 0.000 description 1
- 125000000286 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
- LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 description 1
- VUNPWIPIOOMCPT-UHFFFAOYSA-N piperidin-3-ylmethanol Chemical compound OCC1CCCNC1 VUNPWIPIOOMCPT-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) 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
- 229920005671 poly(vinyl chloride-propylene) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920006324 polyoxymethylene 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
- 229920002620 polyvinyl fluoride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000010454 slate Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 150000003606 tin compounds Chemical class 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
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、特に耐光性の改善された安定化高分子材料組
成物、詳しくは、2.2,6.6−チトラメチルピペリ
ジル基を有するシアヌレート誘導体を含有させてなる、
特に耐光性の改善された安定化高分子材料組成物に関す
る。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention particularly relates to a stabilized polymeric material composition with improved light resistance, specifically a composition having a 2,2,6,6-titramethylpiperidyl group. containing a cyanurate derivative,
In particular, it relates to stabilized polymeric material compositions with improved light resistance.
〔従来の技術及び発明が解決しようとする問題点〕ポリ
エチレン、ポリプロピレン、ポリ塩化ビニル等の合成樹
脂は一般に光の効果に対して敏感であり、その作用によ
り劣化し、変色或いは機械的強度の低下等を引き起こし
、長期の使用に耐えないことが知られている。[Prior art and problems to be solved by the invention] Synthetic resins such as polyethylene, polypropylene, and polyvinyl chloride are generally sensitive to the effects of light, and deteriorate due to the effects of light, resulting in discoloration or a decrease in mechanical strength. It is known that it causes such problems and cannot withstand long-term use.
そこで、この光による合成樹脂の劣化を防止するために
、従来種々の安定剤が用いられてきたが、従来用いられ
てきた光安定剤はその安定化効果がまだ不十分であり、
また安定剤自体が熱或いは酸化に対して不安定であった
り、水等の溶剤によって樹脂から抽出され易いものが多
く、さらに樹脂に着色を与えるものが多い等の欠点を持
っており、長期にわたって合成樹脂を安定化することが
できなかった。Therefore, in order to prevent the deterioration of synthetic resins due to this light, various stabilizers have been used in the past, but the stabilizing effect of the conventionally used light stabilizers is still insufficient.
In addition, many stabilizers themselves are unstable to heat or oxidation, are easily extracted from the resin by solvents such as water, and many also color the resin, making them difficult to maintain over a long period of time. It was not possible to stabilize the synthetic resin.
これら従来用いられてきた光安定剤の中でもピペリジン
系の化合物はそれ自体が非着色性であり、近年特に注目
されている。Among these conventionally used light stabilizers, piperidine compounds are themselves non-coloring and have attracted particular attention in recent years.
しかしながら、従来知られているピペリジン系の化合物
は光安定化能が不十分であり、また、水によって樹脂か
ら容易に抽出されてしまうという欠点もあった。However, conventionally known piperidine-based compounds have insufficient photostabilizing ability and also have the disadvantage that they are easily extracted from the resin by water.
また、これらのピペリジン系の化合物は化合物自体の耐
熱性が不十分であり、合成樹脂を高温で加工する際など
に、分解あるいは揮敗し、その効果を失う場合も多かっ
た。In addition, these piperidine-based compounds themselves have insufficient heat resistance, and when processing synthetic resins at high temperatures, they often decompose or volatilize and lose their effectiveness.
これらのピペリジン系化合物のうち、トリアジン環を含
存する化合物は比較的化合物自体の耐熱性が良好であり
、また、原料として安価な塩化ソアヌルを用いることが
でき、反応も容易である等の利点を有している。Among these piperidine-based compounds, compounds containing a triazine ring have the advantage that the compound itself has relatively good heat resistance, can use inexpensive soarnuric chloride as a raw material, and is easy to react. have.
トリアジン環を含をするピペリジン化合物としては特開
昭49−21389号、特開昭52−71486号、特
開昭52−73886号、特開昭53−9782号、特
開昭53−67749号、特開昭54−106483号
、特開昭54−126249号、特開昭55−9818
0号、特開昭55−102637号、特開昭55−10
4279号、特開昭56−4639号、特開昭56−3
0974号及び特開昭58−18378号の各公報に種
々の化合物が提案されている。Examples of piperidine compounds containing a triazine ring include JP-A-49-21389, JP-A-52-71486, JP-A-52-73886, JP-A-53-9782, JP-A-53-67749, JP-A-54-106483, JP-A-54-126249, JP-A-55-9818
No. 0, JP-A-55-102637, JP-A-55-10
No. 4279, JP-A-56-4639, JP-A-56-3
Various compounds have been proposed in JP-A-0974 and JP-A-58-18378.
これら公報記載の化合物において、特開昭52−714
86号公報に記載された化合物に代表される、ジアミン
又はグリコールで2個以上のトリアジン環を縮合させた
化合物が耐熱性、耐抽出性等が比較的優れている。In the compounds described in these publications, JP-A-52-714
Compounds in which two or more triazine rings are condensed with diamine or glycol, such as the compound described in Japanese Patent No. 86, are relatively excellent in heat resistance, extraction resistance, and the like.
しかしながら、これらの化合物でも、その耐熱性、耐抽
出性及び光安定化能は未だ満足し得るものではなく、さ
らに優れた光安定剤の開発が要望されていた。However, even with these compounds, their heat resistance, extraction resistance, and photostabilizing ability are still unsatisfactory, and there has been a demand for the development of even better photostabilizers.
本発明者等は、かかる現状に鑑み、鋭意検討を重ねた結
果、特定の複素環式アミンを置換基として有する次の一
般式(I)で表される化合物が耐熱性、耐抽出性及び光
安定化能に優れ、高分子材料用の安定剤として極めて有
用であることを知見した。In view of the current situation, the present inventors have conducted intensive studies and found that a compound represented by the following general formula (I) having a specific heterocyclic amine as a substituent has excellent heat resistance, extraction resistance, and light resistance. It was found that it has excellent stabilizing ability and is extremely useful as a stabilizer for polymeric materials.
(式中、Aは塩素原子、Xで表される基又はを示し、R
1は水素原子、アルキル基又はアシル基を示す、R2は
炭素原子数2〜20のアルキレに4
R1はそれぞれ水素原子、メチル基、ベンジル基、−C
、!1、、−011又は−COOR,を示し、mは1〜
3を示し、R1はアルキル基を示す、Rhは結合手又は
炭素原子数1〜6のアルキレン基を示を示し、Y2はY
lで表される基又は−〇−を示し、pはO〜2を示す。(In the formula, A represents a chlorine atom, a group represented by X, or R
1 represents a hydrogen atom, an alkyl group or an acyl group, R2 represents an alkylene group having 2 to 20 carbon atoms, 4 R1 represents a hydrogen atom, a methyl group, a benzyl group, -C
,! 1, -011 or -COOR, m is 1 to
3, R1 represents an alkyl group, Rh represents a bond or an alkylene group having 1 to 6 carbon atoms, Y2 represents Y
It represents a group represented by l or -〇-, and p represents O~2.
nは2〜30を示す。)本発明は、上記知見に基づきな
されたもので、高分子材$4100重量部に、上記一般
式(+)で表される化合物0.001〜5重量部を添加
してなる、安定化高分子材料組成物を堤供するものであ
る。n represents 2 to 30. ) The present invention was made based on the above findings, and is a stabilized polymer prepared by adding 0.001 to 5 parts by weight of the compound represented by the general formula (+) to $4,100 parts by weight of a polymer material. The present invention provides a molecular material composition.
以下、本発明の高分子材料組成物について詳述する。The polymer material composition of the present invention will be explained in detail below.
本発明で用いられる前記一般式(I)で表される化合物
において、R1で表されるアルキル基としては、例えば
、メチル、エチル、プロピル、イソプロピル、ブチル、
アミル、ヘキシル、ヘプチル、オクチル、2−エチルヘ
キシル、ノニル、デシル、ドデシル、オクタデシル、ベ
ンジル、フェニルエチル、2−ヒドロキシエチル、2−
ヒドロキシプロピル、2−ヒドロキシブチル、2.3−
エポキシプロピル等があげられ、アシル暴としては、例
えば、アセチル、プロピオニル、ブチロイル、アクリロ
イル、メタクリロイル、オクタノイル、ヘンジイル等が
あげられる。In the compound represented by the general formula (I) used in the present invention, examples of the alkyl group represented by R1 include methyl, ethyl, propyl, isopropyl, butyl,
Amyl, hexyl, heptyl, octyl, 2-ethylhexyl, nonyl, decyl, dodecyl, octadecyl, benzyl, phenylethyl, 2-hydroxyethyl, 2-
Hydroxypropyl, 2-hydroxybutyl, 2.3-
Examples of the acyl group include epoxypropyl, and examples of the acyl group include acetyl, propionyl, butyroyl, acryloyl, methacryloyl, octanoyl, and hendiyl.
また、R1で表されるアルキル基としては、例えば、メ
チル、エチル、プロピル、イソプロピル、ブチル、イソ
ブチル、第2ブチル、ヘキシル、シクロヘキシル、オク
チル、イソオクチル、2−エチルヘキシル、第3オクチ
ル、デシル、ドデシル、テトラデシル、オクタデシル等
があげられる。Further, examples of the alkyl group represented by R1 include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, hexyl, cyclohexyl, octyl, isooctyl, 2-ethylhexyl, tertiary octyl, decyl, dodecyl, Examples include tetradecyl and octadecyl.
本発明の前記一般式(I)で表される化合物は、例えば
、塩化シアヌルとアルキレンビス(テトラメチルピペリ
ジルアミン)とを反応させた後、これとH−X(Xは前
記一般式(I)で表される化合物におけるXと同じもの
を示す、〕で表される特定の複素環式アミン化合物を反
応させる方法、又は塩化シアヌルとH−Xとを反応させ
た後、これとアルキレンビス(テトラメチルピペリジル
アミン)を反応させる方法によって製造することができ
る。The compound represented by the general formula (I) of the present invention can be obtained by, for example, reacting cyanuric chloride with alkylene bis(tetramethylpiperidylamine), and then reacting this with H-X (X is the compound represented by the general formula (I)). A method of reacting a specific heterocyclic amine compound represented by ], which is the same as X in the compound represented by It can be produced by a method of reacting methylpiperidylamine).
前記一般式(I)で表される化合物を製造するのに用い
られるH−Xで表される複素環式アミン化合物としては
、例えば、ピロリジン、ピペリジン、2−ピペコリン(
2−メチルピペリジン)、3−−ピペコリン、4−ピペ
コリン、4−ベンジルピペリジン、2.4−ルペチジン
(2,4−ジメチルピペリジン)、2.6−ルペチジン
、3.5−ルペチジン、3−ヒドロキシメチルピペリジ
ン、2−ヒドロキシエチルピペリジン、ピペコリン酸メ
チル、イソニペコチン酸メチル、イソニペコチン酸エチ
ル、N−メチルピペラジン、N−カルベトキシピペラジ
ン、N−メチルホモピペラジン、N−アミノピペリジン
、N−アミノ−4−メチルピペリジン、N−メチル−N
′ −アミノピペリジ7、N−(3−アミノプロピル)
ピペリジン、N−(3゛ −アミノプロピル)−2−メ
チルピペリジン、N−(3’ −アミノプロピル)−
4−メチルピペリジン、N−(2−アミノエチル)ピペ
リジン、N−(2’ −アミノエチル)−4−メチル
ピペラジン、N−(3−アミノプロピル)モルホリン等
があげられる。Examples of the heterocyclic amine compound represented by H-X used to produce the compound represented by the general formula (I) include pyrrolidine, piperidine, and 2-pipecoline (
2-methylpiperidine), 3-pipecoline, 4-pipecoline, 4-benzylpiperidine, 2,4-lupetidine (2,4-dimethylpiperidine), 2,6-lupetidine, 3.5-lupetidine, 3-hydroxymethyl Piperidine, 2-hydroxyethylpiperidine, methyl pipecolate, methyl isonipecotate, ethyl isonipecolate, N-methylpiperazine, N-carbethoxypiperazine, N-methylhomopiperazine, N-aminopiperidine, N-amino-4-methylpiperidine , N-methyl-N
' -aminopiperidi7,N-(3-aminopropyl)
Piperidine, N-(3'-aminopropyl)-2-methylpiperidine, N-(3'-aminopropyl)-
Examples include 4-methylpiperidine, N-(2-aminoethyl)piperidine, N-(2'-aminoethyl)-4-methylpiperazine, and N-(3-aminopropyl)morpholine.
以下に本発明で用いられる前記一般式<1)で表される
化合物の合成例を示し、本発明をさらに詳細に説明する
が、本発明は以下の合成例によって制限を受けるもので
はない。Hereinafter, the present invention will be explained in more detail by showing synthesis examples of the compound represented by the general formula <1) used in the present invention, but the present invention is not limited by the following synthesis examples.
合成例1
塩化シアヌル9.2 g (・0.05モル)、2−メ
チルピペリジン5、Og(0,05モル)、水酸化ナト
リウム2.0g及びキシレン100M1をとり80℃で
8時間攪拌した。ここに1.6−ビス(2,2゜6.6
−テトラメチル−4−ピペリジルアミノ)ヘキサン21
.7g(Q。055モル)及び水酸化ナトリウム4.4
gを加え、還流下15時間攪拌した。Synthesis Example 1 9.2 g (0.05 mol) of cyanuric chloride, 5.0 g (0.05 mol) of 2-methylpiperidine, 2.0 g of sodium hydroxide, and 100 M1 of xylene were taken and stirred at 80° C. for 8 hours. Here 1.6-bis (2,2゜6.6
-tetramethyl-4-piperidylamino)hexane 21
.. 7g (Q. 055 mol) and sodium hydroxide 4.4
g was added thereto, and the mixture was stirred under reflux for 15 hours.
水洗、乾燥後脱溶媒して分子量約3500の淡黄色固体
の生成物〔下記式で表される化合物11hl(N =
18..9%、Cl−0,15%)〕を得た。After washing with water and drying, the solvent was removed to produce a pale yellow solid product with a molecular weight of about 3500 [Compound 11hl (N =
18. .. 9%, Cl-0.15%)] was obtained.
合成例2
塩化シアヌル9.2g(0,05モル)、1.6−ビス
(2,2,6,6−テトラメチル−4−ピペリジルアミ
ノ)ヘキサン21.7 g (0,055モル)、水酸
化ナトリウム4.4g及びキシレン100−をとり80
℃で8時間攪拌した。ここにN−(3−アミノプロピル
)モルホリン7.2g(0,05モル)及び水酸化ナト
リウム2.0gを加え、還流下15時間攪拌した。Synthesis Example 2 Cyanuric chloride 9.2 g (0.05 mol), 1,6-bis(2,2,6,6-tetramethyl-4-piperidylamino)hexane 21.7 g (0,055 mol), water Take 4.4 g of sodium oxide and 100 - of xylene and 80
The mixture was stirred at ℃ for 8 hours. 7.2 g (0.05 mol) of N-(3-aminopropyl)morpholine and 2.0 g of sodium hydroxide were added thereto, and the mixture was stirred under reflux for 15 hours.
水洗、乾燥後脱溶媒して分子量約2000の淡黄色固体
の生成物〔下記式で表される化合物−2(N=19.3
%、Cl−0,18%)〕を得た。After washing with water and drying, the solvent was removed to obtain a pale yellow solid product with a molecular weight of about 2000 [Compound-2 represented by the following formula (N=19.3
%, Cl-0.18%)] was obtained.
合成例3〜12
合成例1又は2と同様にして下記式で表される化合動磁
3〜12を合成した。尚、下記式において、(HDA)
、(ODA) 、(UDA)、0’IHDA) 、及
び(八HD^)はそれぞれ次の通りである。Synthesis Examples 3 to 12 Compound dynamic magnets 3 to 12 represented by the following formulas were synthesized in the same manner as in Synthesis Example 1 or 2. In addition, in the following formula, (HDA)
, (ODA), (UDA), 0'IHDA), and (8HD^) are as follows, respectively.
II H HH HlI C113Cl13 O=COコC an、 co。II H HH HlI C113Cl13 O=COCOC an, co.
化合動磁3
化合動磁7
化合物隘8
化合物階IO
化合物−11
化合物階12
本発明は、前記一般式(+)で表される化合物を高分子
材料に添加して特にその耐光性を改善するものであり、
その添加量は、通常、高分子材料100ffi積部に対
し0.001〜5重量部、好ましくは0.01〜3重量
部である。Compound dynamic magnetism 3 Compound dynamic magnetism 7 Compound level 8 Compound level IO Compound-11 Compound level 12 The present invention adds a compound represented by the general formula (+) to a polymeric material to particularly improve its light resistance. It is a thing,
The amount added is usually 0.001 to 5 parts by weight, preferably 0.01 to 3 parts by weight per 100 ffi parts of the polymeric material.
本発明における安定性改善の対象となる高分子材料とし
ては、例えば、ポリエチレン、ポリプロピレン、ポリブ
テン、ポリ−3−メチルブテン等のα−オレフィン重合
体又はエチレン−酢酸ビニル共重合体、エチレン−プロ
ピレン共重合体等のポリオレフィン及びこれらの共重合
体、ポリ塩化ビニル、ポリ臭化ビニル、ポリフッ化ビニ
ル、ポリ塩化ビニリデン、塩素化ポリエチレン、塩素化
ポリプロピレン、ポリフッソ化ビニルデン、臭素化ポリ
エチレン、塩化ゴム、塩化ビニル−酢酸ビニル共重合体
、塩化ビニル−エチレン共重合体、塩化ビニル−プロピ
レン共重合体、塩化ビニル−スチレン共重合体、塩化ビ
ニル−イソブチレン共重合体、塩化ビニル−塩化ビニリ
デン共重合体、塩化ビニル−スチレン−無水マレイン酸
三元共重合体、塩化ビニル−スチレン−アクリロニトリ
ル共重合体、塩化ビニル−ブタジェン共重合体、塩化ビ
ニル−イソプレン共重合体、塩化ビニル−塩素化プロピ
レン共重合体、塩化ビニル−塩化ビニリデン−酢酸ビニ
ル三元共重合体、塩化ビニル−アクリル酸エステル共重
合体、塩化ビニル−マレイン酸エステル共重合体、塩化
ビニル−メタクリル酸エステル共重合体、塩化ビニル−
アクリロニトリル共重合体、内部可塑化ポリ塩化ビニル
等の含ハロゲン合成樹脂、石油樹脂、クマロン樹脂、ポ
リスチレン、ポリ酢酸ビニル、アクリル樹脂、スチレン
と他の単量体(例えば無水マレイン酸、ブタジェン、ア
クリロニトリル等)との共重合体、アクリロニトリル−
ブタジェン−スチレン共重合体、アクリル酸エステル−
ブタジェン−スチレン共重合体、メタクリル酸エステル
−ブタジェン−スチレン共重合体、ポリメチルメタクリ
レート等のメタクリレート樹脂、ポリビニルアルコール
、ポリビニルホルマール、ポリビニルブチラール、直鎖
ポリエステル、ポリフェニレンオキンド、ポリアミド、
ポリカーボネート、ポリアセタール、ポリウレタン、繊
維素系樹脂、或いはフェノール樹脂、ユリア樹脂、メラ
ミン樹脂、エポキシ樹脂、不飽和ポリエステル樹脂、シ
リコーン樹脂等をあげることができる。更に、イソプレ
ンゴム、ブタジェンゴム、アクリロニトリル−ブタジェ
ン共重合ゴム、スチレン−ブタジェン共重合ゴム等のゴ
ム類やこれらの樹脂のブレンド品であってもよい。Examples of polymeric materials whose stability is to be improved in the present invention include α-olefin polymers such as polyethylene, polypropylene, polybutene, and poly-3-methylbutene, ethylene-vinyl acetate copolymers, and ethylene-propylene copolymers. Polyolefins such as polymers and their copolymers, polyvinyl chloride, polyvinyl bromide, polyvinyl fluoride, polyvinylidene chloride, chlorinated polyethylene, chlorinated polypropylene, polyvinyldene fluoride, brominated polyethylene, chlorinated rubber, vinyl chloride Vinyl acetate copolymer, vinyl chloride-ethylene copolymer, vinyl chloride-propylene copolymer, vinyl chloride-styrene copolymer, vinyl chloride-isobutylene copolymer, vinyl chloride-vinylidene chloride copolymer, vinyl chloride- Styrene-maleic anhydride terpolymer, vinyl chloride-styrene-acrylonitrile copolymer, vinyl chloride-butadiene copolymer, vinyl chloride-isoprene copolymer, vinyl chloride-chlorinated propylene copolymer, vinyl chloride- Vinylidene chloride-vinyl acetate terpolymer, vinyl chloride-acrylic acid ester copolymer, vinyl chloride-maleic acid ester copolymer, vinyl chloride-methacrylic acid ester copolymer, vinyl chloride-
Acrylonitrile copolymers, halogen-containing synthetic resins such as internally plasticized polyvinyl chloride, petroleum resins, coumaron resins, polystyrene, polyvinyl acetate, acrylic resins, styrene and other monomers (e.g. maleic anhydride, butadiene, acrylonitrile, etc.) ) copolymer with acrylonitrile-
Butadiene-styrene copolymer, acrylic ester-
Butadiene-styrene copolymer, methacrylic acid ester-butadiene-styrene copolymer, methacrylate resin such as polymethyl methacrylate, polyvinyl alcohol, polyvinyl formal, polyvinyl butyral, linear polyester, polyphenylene oxide, polyamide,
Examples include polycarbonate, polyacetal, polyurethane, cellulose resin, phenol resin, urea resin, melamine resin, epoxy resin, unsaturated polyester resin, and silicone resin. Furthermore, rubbers such as isoprene rubber, butadiene rubber, acrylonitrile-butadiene copolymer rubber, styrene-butadiene copolymer rubber, and blends of these resins may also be used.
また、過酸化物或いは放射線等によって架橋させた架橋
ポリエチレン等の架橋重合体及び発泡剤によって発泡さ
せた発泡ポリスチレン等の発泡重合体も包含される。Also included are crosslinked polymers such as crosslinked polyethylene crosslinked with peroxide or radiation, and foamed polymers such as expanded polystyrene foamed with a foaming agent.
本発明の組成物に更にフェノール系の抗酸化剤を添加す
ることによってその酸化安定性を一層改善することがで
きる。このフェノール系抗酸化剤としでは、例えば、2
,6−ジー第3ブチル−p−クレゾール、2.6−ジフ
ェニル−4−オクトキシフェノール、ステアリル−(3
,5−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
−ジー第3ブチルフエニル)プロピオネート、ジステア
リル−3,5−ジー第3ブチル−4−ヒドロキシベンジ
ルホスホネート、2.4.6−)リス(3’ 、5’
−ジー第3ブチル−4−ヒドロキシヘンシルチオ)1.
3,5.−)リアジン、ジステアリル(4−ヒドロキシ
−3−メチル−5=第3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−第3ブチル
フエノール)、4.4’−メチレンビス(2,6−ジー
第3ブチルフエノール)、2,2°−メチレンビス(6
−(I−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−第3ブチルフ
エニル)ブチリックアシドコグリコールエステル、4.
4゛−ブチリデンビス(6−第3ブチル−m−クレゾー
ル)、2.2’−エチリデンビス(4,6−ジー第3ブ
チルフエノール)、2.2°−エチリデンビス(4−第
2ブチル−6−第3ブチルフエノール)、1.1゜3−
トリス (2−メチル−4−ヒドロキシ−5−第3ブチ
ルフエニル)ブタン、ビス〔2−第3ブチル−4−メチ
ル−6−(2−ヒドロキソ−3−第3ブチル−5−メチ
ルベンジル)フェニル]テレフタレート、1,3.5−
1−リス(2,6−シメチルー3−ヒドロキシ−4−第
3ブチル)ヘンシルイソシアヌレート、1.3.5−)
リス(3゜5−ジー第3ブチル−4−ヒドロキンヘンシ
ル)−2,4,6−)リメチルヘンゼン、テトラキス〔
メチレン−3−(3,5−ジー第3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−
トリス(3,5−ジー第3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−ジー第3ブチル−4−ヒドロキシフェニル)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−ジー第3
ブチル)フェノキシ−1,3,5−4リアジン、4゜4
゛−チオヒ=ス(6−第3ブチル−m−クレゾール)等
があげられる。By further adding a phenolic antioxidant to the composition of the present invention, its oxidative stability can be further improved. As this phenolic antioxidant, for example, 2
, 6-di-tert-butyl-p-cresol, 2,6-diphenyl-4-octoxyphenol, stearyl-(3
, 5-di-methyl-4-hydroxybenzyl)thioglycolate, stearyl-β-(4-hydroxy-3,5
-di-tert-butyl phenyl)propionate, distearyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate, 2.4.6-)lis(3',5'
-tert-butyl-4-hydroxyhensylthio)1.
3,5. -) riazine, distearyl (4-hydroxy-3-methyl-5=tert-butyl)benzylmalonate,
2.2'-methylenebis(4-methyl-6-tert-butylphenol), 4.4'-methylenebis(2,6-di-tert-butylphenol), 2,2°-methylenebis(6-tert-butylphenol)
-(I-methylcyclohexyl)p-cresol], bis[3,5-bis(4-hydroxy-3-tert-butylphenyl)butyric acidocoglycol ester, 4.
4'-Butylidenebis (6-tert-butyl-m-cresol), 2.2'-ethylidenebis (4,6-di-tert-butylphenol), 2.2'-ethylidenebis (4-tert-butyl-6 -tertiary butylphenol), 1.1°3-
Tris (2-methyl-4-hydroxy-5-tert-butylphenyl)butane, bis[2-tert-butyl-4-methyl-6-(2-hydroxo-3-tert-butyl-5-methylbenzyl)phenyl] Terephthalate, 1,3.5-
1-Lis(2,6-dimethyl-3-hydroxy-4-tert-butyl)hensyl isocyanurate, 1.3.5-)
Lis(3゜5-di-tert-butyl-4-hydroquinhensyl)-2,4,6-)limethylhenzene, tetrakis[
Methylene-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate comethane, 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-1,3,5-4 riazine, 4゜4
Examples include ゛-thiohy-su(6-tert-butyl-m-cresol).
本発明の組成物に更に硫黄系の抗酸化剤を加えてその酸
化安定性の改善をはかることもできる。It is also possible to further add a sulfur-based antioxidant to the composition of the present invention to improve its oxidative stability.
この硫黄系抗酸化剤としては、例えば、ジラウリル−、
シミリスチル−、ジステアリル−等のジアルキルチオジ
プロピオネート及びブチル−、オクチル−、ラウリル−
、ステアリル−等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
スヒドロキシエチルイソシアヌレート)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)があげられる。Examples of the sulfur-based antioxidant include dilauryl,
Dialkyl thiodipropionates such as similystyl, distearyl, and butyl, octyl, lauryl
, alkylthiopropionic acid polyhydric alcohols such as stearyl (e.g. glycerin, trimethylolethane,
trimethylolpropane, pentaerythritol, trishydroxyethyl isocyanurate) (for example, pentaerythritol tetralaurylthiopropionate).
本発明の組成物に更にホスファイト等の含リン化合物を
添加することによってその耐光性及び耐熱性を一層改善
することができる。この含リン化合物としては、例えば
、トリオクチルホスファイト、トリラウリルホスファイ
ト、トリデシルホスファイト、オクチル−ジフェニルホ
スファイト、トリス(2,4−ジー第3ブチルフエニル
)ホスファイト、トリフェニルホスファイト、トリス(
ブトキシエチル)ホスファイト、トリス(ノニルフェニ
ル)ホスファイト、ジステアリルペンタエリスリトール
ジホスファイト、テトラ(トリデシル)−1,1,3−
トリス(2−メチル−5−第3ブチル−4−ヒドロキシ
フェニル)ブタンジホスファイト、テトラ(C52〜1
.混合アルキル)−4,4’−イソプロピリデンジフェ
ニルジホスファイト、テトラ (トリデシル)−4,4
’−ブチリデンビス(3−メチル−6−第3ブチルフエ
ノール)ジホスファイト、トリス(3,5−ジー第3ブ
チル−4−ヒドロキシフェニル)ホスファイト、トリス
(モノ・ジ混合ノニルフェニル)ホスファイト、水素化
−4,4゛−イソプロピリデンジフェノールポリホスフ
ァイト、ビス(オクチルフェニル)・ビス〔4,4°−
ブチリデンヒス(3−メチル−6−第3ブチルフエノー
ル)〕 ・1.6−ヘキサンジオールジホスファイト、
フェニル・4,4°−イソプロピリデンジフェノール・
ペンタエリスリトールジホスファイト、ビス(2、4−
シー第3 メチルフェニル)ペンタエリスリトールジホ
スファイト、ビス(2,6−ジー第3ブチル−4−メチ
ルフェニル)ペンタエリスリトールジホスファイト、ト
リス(4,4’−イソプロピリデンビス(2−第3ブチ
ルフエノール)〕ホスファイト、フェニル・ジイソデシ
ルホスファイト、ジ(ノニルフェニル)ペンタエリスリ
トールジホスファイト、トリス(I,3−ジ−ステアロ
イルオキシイソプロピル)ホスファイト、4.4°−イ
ソプロピリデンビス(2−第3ブチルフエノール)・ジ
(ノニルフェニル)ホスファイト、9.10−ジ−ハイ
ドロ−9−オキサ−10−フォスファフェナンスレンー
1O−オキサイド、テトラキス(2,4−ジー第3ブチ
ルフエニル)−4,4’−ビフエニレンジホスホナイト
等があげられる。By further adding a phosphorus-containing compound such as phosphite to the composition of the present invention, its light resistance and heat resistance can be further improved. Examples of the phosphorus-containing compound include 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(C52-1
.. mixed alkyl)-4,4'-isopropylidene diphenyl diphosphite, 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°-
Butylidenehis (3-methyl-6-tert-butylphenol)] ・1,6-hexanediol diphosphite,
Phenyl・4,4°-isopropylidenediphenol・
Pentaerythritol diphosphite, bis(2,4-
Bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite, tris(4,4'-isopropylidene bis(2-tert-butyl) phenol)] phosphite, phenyl diisodecyl phosphite, di(nonylphenyl) pentaerythritol diphosphite, tris(I,3-di-stearoyloxyisopropyl) phosphite, 4.4°-isopropylidene bis(2-st) 3-butylphenol) di(nonylphenyl) phosphite, 9.10-di-hydro-9-oxa-10-phosphaphenanthrene-1O-oxide, tetrakis(2,4-di-tert-butylphenyl)-4 , 4'-biphenylene diphosphonite and the like.
本発明の組成物に他の光安定剤を添加することによって
その耐光性をさらに改善することができる。この光安定
剤としては、例えば、2−ヒドロキシ−4−メトキシヘ
ンシフエノン、2−ヒドロキン−4−n−オクトキシヘ
ンシフエノン、2゜2゛−ジ−ヒドロキシ−4−メトキ
シヘンシフエノン、2.4−ジヒドロキシヘンシフエノ
ン等のヒドロキシベンゾフェノン類、2−(2°−ヒド
ロキシ−3°−t−ブチル−5゛−メチルフェニル)−
5−クロロヘンシトリ7ゾール、2−(2°−ヒドロキ
シ−3゛ 、5°−ジ−t−ブチルフェニル)−5−ク
ロロヘンシトリアゾール、2−(2“−ヒドロキシ−5
゛−メチルフェニル)ベンゾトリアゾール、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等のベンゾトリアゾール類、フェニ
ルサリシレート、p−t−プチルフェニルサリシレート
、2.4−ジ−t−ブチルフェニル−3,5−ジ−t−
ブチル−4−ヒドロキシベンゾエート、ヘキサデシル−
3,5−ジ−t−ブチル−4−ヒドロキシベンゾエート
等のベンゾニー)1.2゜2°−チオビス(4−t−オ
クチルフェノール]Ni塩、(2,2’−チオビス(4
−t−オクチルフェノラート)〕−〕n−ブチルアミン
Ni、 (3゜5−ジ−t−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塩等のニッ
ケル化合物類、α−シ了メノーβ−メチル−β−p−メ
トキシフェニル)アクリル類メチル等の置換アクリロニ
トリル1及びN−2−エチルフェニル−N゛−2−エト
キシ−5−第3ブチルフエニルシユウ酸ジアミド、N−
2−エチルフェニル−N゛−2−エトキシフェニルシュ
ウ酸ジアミド等のシュウ酸ジアニリド類があげられる。By adding other light stabilizers to the compositions of the invention, their lightfastness can be further improved. Examples of the light stabilizer include 2-hydroxy-4-methoxyhensiphenone, 2-hydroquine-4-n-octoxyhensiphenone, 2゜2゛-di-hydroxy-4-methoxyhensiphenone, Hydroxybenzophenones such as 2.4-dihydroxyhensiphenone, 2-(2°-hydroxy-3°-t-butyl-5′-methylphenyl)-
5-chlorohencytriazole, 2-(2'-hydroxy-3', 5'-di-t-butylphenyl)-5-chlorohencytriazole, 2-(2'-hydroxy-5
゛-Methylphenyl)benzotriazole, 2-(2'
-Hydroxy-3゛5''-di-t-amylphenyl)
Benzotriazoles such as benzotriazole, phenyl salicylate, pt-butylphenyl salicylate, 2,4-di-t-butylphenyl-3,5-di-t-
Butyl-4-hydroxybenzoate, hexadecyl-
Benzony such as 3,5-di-t-butyl-4-hydroxybenzoate) 1.2°2°-thiobis(4-t-octylphenol)Ni salt, (2,2'-thiobis(4
-t-octylphenolate)]-]N-butylamine Ni, (3゜5-di-t-butyl-4-hydroxybenzyl)phosphonic acid monoethyl ester Ni salt, etc., nickel compounds, -Methyl-β-p-methoxyphenyl) acrylics Substituted acrylonitrile such as methyl 1 and N-2-ethylphenyl-N-2-ethoxy-5-tert-butylphenyl oxalic acid diamide, N-
Examples include oxalic dianilides such as 2-ethylphenyl-N-2-ethoxyphenyl oxalic diamide.
その他必要に応じて、本発明の組成物には重金属不活性
化剤、造核剤、金属石けん、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、難
燃剤、滑剤、加工助剤等を包含させることができる。In addition, if necessary, the composition of the present invention may contain a heavy metal deactivator, a nucleating agent, a metal soap, an organic tin compound, a plasticizer, an epoxy compound, a pigment, a filler, a blowing agent, an antistatic agent, and a flame retardant. , lubricants, processing aids, and the like.
本発明によって安定化された高分子材料は掻めて多様な
形で、例えば、フィルム、繊維、テープ、シート、各種
成型品として使用でき、また、塗料、ラッカー用結合剤
、接着剤、パテ及び写真材料における基材としても用い
ることができる。The polymeric materials stabilized according to the invention can be used in a wide variety of forms, for example as films, fibers, tapes, sheets, various molded products, and also as paints, binders for lacquers, adhesives, putties, etc. It can also be used as a base material in photographic materials.
次に本発明を実施例によって具体的に説明する。 Next, the present invention will be specifically explained with reference to Examples.
しかしながら、本発明はこれらの実施例によって限定さ
れるものではない。However, the present invention is not limited to these examples.
実施例1
〈配 合〉
ポリプロピレン 100 重量部プロピオネ
ート
安定剤(表−1参照)0.3
上記配合にて厚さ0.3mmのプレスシートを作成し、
このシートについて高圧水銀ランプを用いての耐光性試
験を行った。また、80℃の熱水に15時間浸漬後のシ
ートについても耐光性試験を行った。その結果を表−1
に示す。Example 1 <Blend> Polypropylene 100 parts by weight Propionate stabilizer (see Table-1) 0.3 A press sheet with a thickness of 0.3 mm was created with the above blend,
A light resistance test was conducted on this sheet using a high-pressure mercury lamp. Further, a light resistance test was also conducted on the sheet after being immersed in hot water at 80° C. for 15 hours. Table 1 shows the results.
Shown below.
表−1
実施例2
通常の安定剤は樹脂の高温加工時に揮発、分解等により
その効果が著しく失われることが知られている。Table 1 Example 2 It is known that ordinary stabilizers lose their effectiveness significantly due to volatilization, decomposition, etc. during high-temperature processing of resins.
本実施例では押し出し加工を繰り返し行うことにより高
温加工による影響を確かめた。In this example, the influence of high temperature processing was confirmed by repeatedly performing extrusion processing.
次の配合により樹脂と添加剤をミキサーで5分間混合し
た後、押し出し機でコンバンドを作成した(シリンダ一
温度230℃、240℃、ヘッドダイス温度250℃、
回転数20rpm)。押し出しを5回繰り返し行った後
このコンバンドを用いて試験片を射出成形機で作成した
(シリンダ一温度240℃、ノズル温度250℃、射出
圧475Kg/cd)。After mixing the resin and additives in a mixer for 5 minutes according to the following formulation, a combination was created using an extruder (cylinder temperature 230°C, 240°C, head die temperature 250°C,
Rotation speed: 20 rpm). After extrusion was repeated 5 times, test pieces were made using this combination using an injection molding machine (cylinder temperature 240°C, nozzle temperature 250°C, injection pressure 475 kg/cd).
得られた試験片を用いて高圧水銀ランプで耐光性試験を
行った。また、押し出し1回のものについても同様に試
験した。その結果を表−2に示す。A light resistance test was conducted using the obtained test piece using a high-pressure mercury lamp. In addition, the same test was conducted for a sample that had been extruded once. The results are shown in Table-2.
く配 合〉
エチレン−プロピレン共重合樹脂100 重量部ステア
リン酸カルシウム 0.2フエニルブロピオ
ネート
ジラウリルチオジプロピオネ−) 0.2安定剤(
表−2参照)0.2
表−2
実施例3
く配 合〉
ポリエチレン 100 重量部Ca−ス
テアレート 1.0ビオネート〕メタン
ジステアリルチオジプロピオネート0.3安定剤(表−
3参照)0.2
上記配合物を混線後プレスして厚さ0.5msのシート
を作成した。このシートを用いてウエザオフ−ター中で
耐光性を測定し、脆化するまでの時間を測定した。その
結果を表−3に示す。Blend> Ethylene-propylene copolymer resin 100 parts by weight Calcium stearate 0.2 Phenylpropionate dilauryl thiodipropione) 0.2 Stabilizer (
(See Table 2) 0.2 Table 2 Example 3 Formulation> Polyethylene 100 parts by weight Ca-stearate 1.0 Bionate] Methanedistearylthiodipropionate 0.3 Stabilizer (Table -
3) 0.2 The above blend was mixed and pressed to form a sheet with a thickness of 0.5 ms. Using this sheet, the light resistance was measured in a weather oven, and the time until it became brittle was measured. The results are shown in Table-3.
表−3
実施例4
〈配 合〉
ABS樹脂 100 重量部4.4゛
−ブチリデンビス(2−第 0.13ブチル−M−
クレゾール)
安定剤(表−4参照)0.3
上記配合物をロール練り後プレスして厚さ3Il111
のシートを作成した。このシートを用いてウエザオメー
ターで800時間照、射後の抗張力残率を測定した。そ
の結果を表−4に示す。Table 3 Example 4 <Formulation> ABS resin 100 parts by weight 4.4'-butylidene bis(2-0.13-butyl-M-
Cresol) Stabilizer (see Table 4) 0.3 The above mixture was kneaded with a roll and then pressed to a thickness of 3Il111.
A sheet was created. This sheet was irradiated for 800 hours using a weatherometer, and the residual tensile strength after irradiation was measured. The results are shown in Table 4.
表−4
実施例5
〈配 合〉
ポリ塩化ビニル 10000重量部ジオ
クチルツクレート 48エポキシ化大豆油
2トリスノニルフエニルホスフアイト
0.2Ca−ステアレート1.0
Zn−ステアレート 0.1安定剤
(表−5参照)0.2
上記配合物を混練ロール上で混練し、厚さ11のシート
を作成した。このシートを用いてウエザオフ−ター中で
の耐光性試験を行った。その結果を表−5に示す。Table 4 Example 5 <Blend> Polyvinyl chloride 10,000 parts by weight Dioctyl slate 48 Epoxidized soybean oil
2-trisnonylphenyl phosphite
0.2 Ca-stearate 1.0 Zn-stearate 0.1 Stabilizer (see Table 5) 0.2 The above blend was kneaded on a kneading roll to create a sheet with a thickness of 11. A light resistance test in a weather offter was conducted using this sheet. The results are shown in Table-5.
表−5
実施例6
〈配 合〉
Ba−ステアレート 0,7Zn−ス
テアレート0.3
2.6−ジー第3ブチル−p−クレゾールO0l安定剤
(表−6参照)0.3
上記配合物を70℃で5分間ロール上で混練し、120
℃で5分間プレスして厚さ0.51のシートを作成した
。このシートを用いてフェードメーターにて50時間照
射後の伸び残率を測定した。その結果を表−6に示す。Table-5 Example 6 <Formulation> Ba-stearate 0,7Zn-stearate 0.3 2.6-di-tert-butyl-p-cresol O0l stabilizer (see Table-6) 0.3 Above formulation was kneaded on a roll for 5 minutes at 70°C, and
A sheet with a thickness of 0.51 was prepared by pressing at ℃ for 5 minutes. Using this sheet, the residual elongation rate after 50 hours of irradiation was measured using a fade meter. The results are shown in Table-6.
表−6
実施例7
本発明の化合物は塗料用の光安定剤としても有用である
。本実施例においては金属顔料を含有するベースコート
及び透明なトップコートからなる二層金属光沢塗料につ
いてその効果をみた。Table 6 Example 7 The compounds of the present invention are also useful as light stabilizers for paints. In this example, the effect of a two-layer metallic luster paint consisting of a base coat containing a metal pigment and a transparent top coat was examined.
a)ベースコート塗料
メタクリル酸メチル100g、アクリル酸n −ブチル
66g1メタクリル酸−2−ヒドロキシエチル30g1
メタクリル酸4g1キシレン80g及びn〜ブタノール
20gをとり、110℃に加熱攪拌しながらアゾビスイ
ソブチロニトリル2g、ドデシルメルカプタン0.5g
、キシレン80g及びn−ブタノール20gからなる溶
液を3時間で滴下した。その後同温度で2時間撹拌し、
樹脂固形分50%のアクリル樹脂溶液を調製した。a) Base coat paint Methyl methacrylate 100g, n-butyl acrylate 66g1 2-hydroxyethyl methacrylate 30g1
Take 4 g of methacrylic acid, 80 g of xylene and 20 g of n-butanol, heat to 110°C and add 2 g of azobisisobutyronitrile and 0.5 g of dodecyl mercaptan while stirring.
, a solution consisting of 80 g of xylene and 20 g of n-butanol was added dropwise over 3 hours. After that, stir at the same temperature for 2 hours,
An acrylic resin solution having a resin solid content of 50% was prepared.
上記アクリル樹脂溶液12重量部、ブトキシ化メチロー
ルメラミン(三片東圧社製;ニーパン203E60;樹
脂固形分60%)2.5重世部、セルロースアセテート
ブチレート樹脂(20%酢酸ブチル溶液)50重量部、
アルミニウム顔料(東洋アルミニウム社製:アルペース
ト1123N)5.5重量部、キシ1210重量部、酢
酸ブチル20重量部及び銅フタロシアニンブルー0.2
重量部をとりベースコート塗料とした。12 parts by weight of the above acrylic resin solution, 2.5 parts by weight of butoxylated methylolmelamine (manufactured by Mikata Toatsu Co., Ltd.; Kneepan 203E60; resin solid content 60%), 50 parts by weight of cellulose acetate butyrate resin (20% butyl acetate solution) Department,
5.5 parts by weight of aluminum pigment (manufactured by Toyo Aluminum Co., Ltd.: Alpaste 1123N), 1210 parts by weight of Xylene, 20 parts by weight of butyl acetate, and 0.2 parts by weight of copper phthalocyanine blue.
The weight part was taken and used as a base coat paint.
b))ツブコート塗料
上記アクリル樹脂溶液48重量部、ブトキシ化メチロー
ルメラミン10重量部、キシレン10重世部、ブチルグ
リコールアセテート4重量部及び安定剤(表−7参照)
0.15重量部(固形分に対し0.5%)をとり、トッ
プコート塗料とした。b)) Tubu coat paint 48 parts by weight of the above acrylic resin solution, 10 parts by weight of butoxylated methylolmelamine, 10 parts by weight of xylene, 4 parts by weight of butyl glycol acetate, and stabilizer (see Table 7)
0.15 parts by weight (0.5% based on solid content) was taken and used as a top coat paint.
ブライマー処理した鋼板にベースコート塗料を乾燥膜厚
が20μになるようにスプレーし、10分間放放置後ッ
プコート塗料を乾燥膜厚が30μになるようにスプレー
した。15分間放置後140℃で30分間焼付し試片と
した。A base coat paint was sprayed on the steel plate treated with the brimer so that the dry film thickness was 20 μm, and after being left for 10 minutes, a top coat paint was sprayed so that the dry film thickness was 30 μm. After leaving it for 15 minutes, it was baked at 140° C. for 30 minutes to obtain a test piece.
上記試片をウエザオメーターに入れ塗膜のワレの発生す
るまでの時間を測定した。その結果を表=7に示す。The above sample was placed in a weatherometer and the time until cracking of the coating film appeared was measured. The results are shown in Table 7.
表−7
〔発明の効果〕
本発明の高分子材料組成物は、高分子材料に、耐熱性、
耐抽出性及び光安定化能に著しく優れた化合物を安定剤
として添加してなるもので、特に耐光性に優れ、且つそ
の優れた耐光性が高温で加工する等しても失われること
がな(、長期にわたって保持されている。Table 7 [Effects of the invention] The polymer material composition of the present invention has heat resistance,
It is made by adding a compound with extremely high extraction resistance and light stabilizing ability as a stabilizer, and has particularly excellent light resistance, and does not lose its excellent light resistance even when processed at high temperatures. (, held for a long time.
Claims (1)
れる化合物0.001〜5重量部を添加してなる、安定
化高分子材料組成物。 ▲数式、化学式、表等があります▼( I ) (式中、Aは塩素原子、Xで表される基又は▲数式、化
学式、表等があります▼を示し、Bは水素原子又は▲数
式、化学式、表等があります▼を示し、Cは塩素原子又
はXで表される基を示す。R_1は▲数式、化学式、表
等があります▼を示し、R_3は水素原子、アルキル基
又はアシル基を示す。R_2は炭素原子数2〜20のア
ルキレン基を示す。Xは▲数式、化学式、表等がありま
す▼又は▲数式、化学式、表等があります▼を示し、R
_4、及びR_5はそれぞれ水素原子、メチル基、ベン
ジル基、−C_mH_2_m−OH又は−COOR_7
を示し、mは1〜3を示し、R_7はアルキル基を示す
。R_6は結合手又は炭素原子数1〜6のアルキレン基
を示す。Y_1は▲数式、化学式、表等があります▼又
は▲数式、化学式、表等があります▼を示し、Y_2は
Y_1で表される基又は−O−を示し、pは0〜2を示
す。nは2〜30を示す。)[Scope of Claim] A stabilized polymeric material composition comprising 0.001 to 5 parts by weight of a compound represented by the following general formula (I) added to 100 parts by weight of a polymeric material. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, A is a chlorine atom, a group represented by There are chemical formulas, tables, etc. ▼, C represents a chlorine atom or a group represented by X. R_1 represents ▲ There are mathematical formulas, tables, etc. R_2 represents an alkylene group having 2 to 20 carbon atoms.
_4 and R_5 are each a hydrogen atom, a methyl group, a benzyl group, -C_mH_2_m-OH or -COOR_7
, m represents 1 to 3, and R_7 represents an alkyl group. R_6 represents a bond or an alkylene group having 1 to 6 carbon atoms. Y_1 represents ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, Y_2 represents the group represented by Y_1 or -O-, and p represents 0 to 2. n represents 2 to 30. )
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2762887A JPS63196654A (en) | 1987-02-09 | 1987-02-09 | Stabilized high-molecular material composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2762887A JPS63196654A (en) | 1987-02-09 | 1987-02-09 | Stabilized high-molecular material composition |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS63196654A true JPS63196654A (en) | 1988-08-15 |
Family
ID=12226222
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2762887A Pending JPS63196654A (en) | 1987-02-09 | 1987-02-09 | Stabilized high-molecular material composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS63196654A (en) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5091450A (en) * | 1990-07-27 | 1992-02-25 | Ciba-Geigy Corporation | Piperidine-triazine compounds containing tetrahydrofuran or tetrahydropyran groups, for use as stabilizers for organic materials |
US5102928A (en) * | 1989-12-28 | 1992-04-07 | Ciba-Geigy Corporation | Piperidine-triazine compounds for use as stabilizers for organic materials |
EP0479724A2 (en) | 1990-10-03 | 1992-04-08 | Ciba-Geigy Ag | Piperidine-triazine compounds for use as stabilisers for organic materials |
US5198546A (en) * | 1989-11-10 | 1993-03-30 | Ciba-Geigy Corporation | Piperidine-triazine compounds for use as stabilizers for organic materials |
US5256787A (en) * | 1990-09-03 | 1993-10-26 | Ciba-Geigy Corporation | Tri-piperdine compounds as stabilizers for organic materials |
US5268401A (en) * | 1990-04-30 | 1993-12-07 | Ciba-Geigy Corporation | Piperidine-triazine compounds for use as stabilizers for organic materials |
US5324834A (en) * | 1990-06-13 | 1994-06-28 | Ciba-Geigy Corporation | Piperidine-triazine co-oligomers for use as stabilizers for organic materials |
US5466803A (en) * | 1993-02-11 | 1995-11-14 | Ciba-Geigy Corporation | Piperidine-triazine compounds suitable for use as stabilizers for organic materials |
WO1999029684A1 (en) * | 1997-12-08 | 1999-06-17 | Cytec Technology Corp. | Morpholino end-capped, hindered amine substituted aminotriazine and their use as light stabilizers |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5662840A (en) * | 1979-10-26 | 1981-05-29 | Sumitomo Chem Co Ltd | Method for improving weathering resistance of polyolefin |
JPS5841876A (en) * | 1981-07-20 | 1983-03-11 | アメリカン・サイアナミド・カンパニ− | Photostabilizer compound |
JPS5898180A (en) * | 1981-12-08 | 1983-06-10 | 三菱電機株式会社 | Selector |
JPS59176278A (en) * | 1983-02-04 | 1984-10-05 | チバ−ガイギ−ソシエテパルアクチオン | Novel piperidinyl-triazine compound useful as stabilizer forsynthetic polymer |
-
1987
- 1987-02-09 JP JP2762887A patent/JPS63196654A/en active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5662840A (en) * | 1979-10-26 | 1981-05-29 | Sumitomo Chem Co Ltd | Method for improving weathering resistance of polyolefin |
JPS5841876A (en) * | 1981-07-20 | 1983-03-11 | アメリカン・サイアナミド・カンパニ− | Photostabilizer compound |
JPS5898180A (en) * | 1981-12-08 | 1983-06-10 | 三菱電機株式会社 | Selector |
JPS59176278A (en) * | 1983-02-04 | 1984-10-05 | チバ−ガイギ−ソシエテパルアクチオン | Novel piperidinyl-triazine compound useful as stabilizer forsynthetic polymer |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5198546A (en) * | 1989-11-10 | 1993-03-30 | Ciba-Geigy Corporation | Piperidine-triazine compounds for use as stabilizers for organic materials |
US5102928A (en) * | 1989-12-28 | 1992-04-07 | Ciba-Geigy Corporation | Piperidine-triazine compounds for use as stabilizers for organic materials |
US5268401A (en) * | 1990-04-30 | 1993-12-07 | Ciba-Geigy Corporation | Piperidine-triazine compounds for use as stabilizers for organic materials |
US5324834A (en) * | 1990-06-13 | 1994-06-28 | Ciba-Geigy Corporation | Piperidine-triazine co-oligomers for use as stabilizers for organic materials |
US5091450A (en) * | 1990-07-27 | 1992-02-25 | Ciba-Geigy Corporation | Piperidine-triazine compounds containing tetrahydrofuran or tetrahydropyran groups, for use as stabilizers for organic materials |
US5256787A (en) * | 1990-09-03 | 1993-10-26 | Ciba-Geigy Corporation | Tri-piperdine compounds as stabilizers for organic materials |
US5187275A (en) * | 1990-10-03 | 1993-02-16 | Ciba-Geigy Corporation | Piperidine-triazine compounds |
EP0479724A2 (en) | 1990-10-03 | 1992-04-08 | Ciba-Geigy Ag | Piperidine-triazine compounds for use as stabilisers for organic materials |
US5336706A (en) * | 1990-10-03 | 1994-08-09 | Ciba-Geigy Corporation | Piperidine-triazine compounds for use as stabilizers for organic materials |
US5466803A (en) * | 1993-02-11 | 1995-11-14 | Ciba-Geigy Corporation | Piperidine-triazine compounds suitable for use as stabilizers for organic materials |
WO1999029684A1 (en) * | 1997-12-08 | 1999-06-17 | Cytec Technology Corp. | Morpholino end-capped, hindered amine substituted aminotriazine and their use as light stabilizers |
US6096886A (en) * | 1997-12-08 | 2000-08-01 | Cytec Technology Corp. | Morpholino end-capped, hindered amine substituted aminotriazine |
AU740074B2 (en) * | 1997-12-08 | 2001-10-25 | Cytec Technology Corp. | Morpholino end-capped, hindered amine substituted aminotriazine and their use as light stabilizers |
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