JPS6411224B2 - - Google Patents
Info
- Publication number
- JPS6411224B2 JPS6411224B2 JP5130885A JP5130885A JPS6411224B2 JP S6411224 B2 JPS6411224 B2 JP S6411224B2 JP 5130885 A JP5130885 A JP 5130885A JP 5130885 A JP5130885 A JP 5130885A JP S6411224 B2 JPS6411224 B2 JP S6411224B2
- Authority
- JP
- Japan
- Prior art keywords
- maleate
- bis
- dibutyltin
- dioctyltin
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 139
- -1 maleate compound Chemical class 0.000 claims description 80
- 229920000642 polymer Polymers 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 12
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical class OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 230000000087 stabilizing effect Effects 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 97
- 229920005989 resin Polymers 0.000 description 34
- 239000011347 resin Substances 0.000 description 34
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 22
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 22
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 21
- PWEVMPIIOJUPRI-UHFFFAOYSA-N dimethyltin Chemical compound C[Sn]C PWEVMPIIOJUPRI-UHFFFAOYSA-N 0.000 description 20
- HGQSXVKHVMGQRG-UHFFFAOYSA-N dioctyltin Chemical compound CCCCCCCC[Sn]CCCCCCCC HGQSXVKHVMGQRG-UHFFFAOYSA-N 0.000 description 19
- 238000012360 testing method Methods 0.000 description 19
- FDNBQVCBHKEDOJ-FPLPWBNLSA-N (z)-4-(6-methylheptoxy)-4-oxobut-2-enoic acid Chemical compound CC(C)CCCCCOC(=O)\C=C/C(O)=O FDNBQVCBHKEDOJ-FPLPWBNLSA-N 0.000 description 11
- 229910052736 halogen Inorganic materials 0.000 description 11
- 150000002367 halogens Chemical class 0.000 description 11
- 230000000694 effects Effects 0.000 description 8
- 239000003381 stabilizer Substances 0.000 description 8
- OZDOQMMXEACZAA-NRFIWDAESA-L (z)-4-butoxy-4-oxobut-2-enoate;dibutyltin(2+) Chemical compound CCCCOC(=O)\C=C/C(=O)O[Sn](CCCC)(CCCC)OC(=O)\C=C/C(=O)OCCCC OZDOQMMXEACZAA-NRFIWDAESA-L 0.000 description 6
- GKOTWPKLOWTGAG-NRFIWDAESA-L (z)-4-butoxy-4-oxobut-2-enoate;dioctyltin(2+) Chemical compound CCCCOC(=O)\C=C/C(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)\C=C/C(=O)OCCCC GKOTWPKLOWTGAG-NRFIWDAESA-L 0.000 description 6
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 6
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 5
- WNDWDJLPMLWBHW-UDVCPWNYSA-L dibutyltin(2+);(z)-4-methoxy-4-oxobut-2-enoate Chemical compound COC(=O)\C=C/C(=O)O[Sn](CCCC)(CCCC)OC(=O)\C=C/C(=O)OC WNDWDJLPMLWBHW-UDVCPWNYSA-L 0.000 description 5
- TUALPPJDVFLVNQ-KUAKSMGGSA-L dibutyltin(2+);(z)-4-oxo-4-phenylmethoxybut-2-enoate Chemical compound C=1C=CC=CC=1COC(=O)\C=C/C(=O)O[Sn](CCCC)(CCCC)OC(=O)\C=C/C(=O)OCC1=CC=CC=C1 TUALPPJDVFLVNQ-KUAKSMGGSA-L 0.000 description 5
- 125000001117 oleyl 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])=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 5
- 230000006641 stabilisation Effects 0.000 description 5
- 238000011105 stabilization Methods 0.000 description 5
- KRKQRRUGEKWXIV-KUAKSMGGSA-L 1-O-cyclohexyl 4-O-[[(Z)-4-cyclohexyloxy-4-oxobut-2-enoyl]oxy-dioctylstannyl] (Z)-but-2-enedioate Chemical compound [Sn++].[CH2]CCCCCCC.[CH2]CCCCCCC.[O-]C(=O)\C=C/C(=O)OC1CCCCC1.[O-]C(=O)\C=C/C(=O)OC1CCCCC1 KRKQRRUGEKWXIV-KUAKSMGGSA-L 0.000 description 4
- NJMGRJLQRLFQQX-HYXAFXHYSA-N 2-isopropylmaleic acid Chemical compound CC(C)C(\C(O)=O)=C\C(O)=O NJMGRJLQRLFQQX-HYXAFXHYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- UTOVMEACOLCUCK-PLNGDYQASA-N butyl maleate Chemical compound CCCCOC(=O)\C=C/C(O)=O UTOVMEACOLCUCK-PLNGDYQASA-N 0.000 description 4
- NBZNVCBJBGDRJI-KKUWAICFSA-L dibutyltin(2+);(z)-4-(2-ethylhexoxy)-4-oxobut-2-enoate Chemical compound CCCCC(CC)COC(=O)\C=C/C(=O)O[Sn](CCCC)(CCCC)OC(=O)\C=C/C(=O)OCC(CC)CCCC NBZNVCBJBGDRJI-KKUWAICFSA-L 0.000 description 4
- JNKCYBSAZHJNIZ-LHJYRGMRSA-L dibutyltin(2+);(z)-4-oxo-4-tridecoxybut-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)\C=C/C(=O)O[Sn](CCCC)(CCCC)OC(=O)\C=C/C(=O)OCCCCCCCCCCCCC JNKCYBSAZHJNIZ-LHJYRGMRSA-L 0.000 description 4
- 229940097413 isopropyl maleate Drugs 0.000 description 4
- 150000002688 maleic acid derivatives Chemical class 0.000 description 4
- QKUGKZFASYQCGO-SREVYHEPSA-N (z)-4-oxo-4-phenylmethoxybut-2-enoic acid Chemical compound OC(=O)\C=C/C(=O)OCC1=CC=CC=C1 QKUGKZFASYQCGO-SREVYHEPSA-N 0.000 description 3
- ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 0.000 description 3
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 3
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 3
- 229920006385 Geon Polymers 0.000 description 3
- MHQJUHSHQGQVTM-HNENSFHCSA-N Octadecyl fumarate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)\C=C/C(O)=O MHQJUHSHQGQVTM-HNENSFHCSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- BTSHKFIHOPUJCA-NRFIWDAESA-L (Z)-4-butoxy-4-oxobut-2-enoate dimethyltin(2+) Chemical compound C[Sn+2]C.CCCCOC(=O)\C=C/C([O-])=O.CCCCOC(=O)\C=C/C([O-])=O BTSHKFIHOPUJCA-NRFIWDAESA-L 0.000 description 2
- IQBLWPLYPNOTJC-FPLPWBNLSA-N (z)-4-(2-ethylhexoxy)-4-oxobut-2-enoic acid Chemical compound CCCCC(CC)COC(=O)\C=C/C(O)=O IQBLWPLYPNOTJC-FPLPWBNLSA-N 0.000 description 2
- WBYOSZYSBZQGDJ-KUAKSMGGSA-L (z)-4-cyclohexyloxy-4-oxobut-2-enoate;dibutyltin(2+) Chemical compound C1CCCCC1OC(=O)\C=C/C(=O)O[Sn](CCCC)(CCCC)OC(=O)\C=C/C(=O)OC1CCCCC1 WBYOSZYSBZQGDJ-KUAKSMGGSA-L 0.000 description 2
- ZMQWRASVUXJXGM-SREVYHEPSA-N (z)-4-cyclohexyloxy-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C/C(=O)OC1CCCCC1 ZMQWRASVUXJXGM-SREVYHEPSA-N 0.000 description 2
- IIPCXIGUIPAGQB-SEYXRHQNSA-N (z)-4-dodecoxy-4-oxobut-2-enoic acid Chemical compound CCCCCCCCCCCCOC(=O)\C=C/C(O)=O IIPCXIGUIPAGQB-SEYXRHQNSA-N 0.000 description 2
- RNERBJNDXXEXTK-SREVYHEPSA-N (z)-4-hexoxy-4-oxobut-2-enoic acid Chemical compound CCCCCCOC(=O)\C=C/C(O)=O RNERBJNDXXEXTK-SREVYHEPSA-N 0.000 description 2
- VTWGIDKXXZRLGH-HJWRWDBZSA-N (z)-4-octoxy-4-oxobut-2-enoic acid Chemical compound CCCCCCCCOC(=O)\C=C/C(O)=O VTWGIDKXXZRLGH-HJWRWDBZSA-N 0.000 description 2
- FGACNJFGXDUISO-YPKPFQOOSA-N (z)-4-oxo-4-tridecoxybut-2-enoic acid Chemical compound CCCCCCCCCCCCCOC(=O)\C=C/C(O)=O FGACNJFGXDUISO-YPKPFQOOSA-N 0.000 description 2
- NUSQJGCEUADMON-QQUZTSPOSA-J 1-o-benzyl 4-o-[[(z)-4-[dioctyl-[(z)-4-oxo-4-phenylmethoxybut-2-enoyl]oxystannyl]oxy-4-oxobut-2-enoyl]oxy-dioctylstannyl] (z)-but-2-enedioate Chemical compound C=1C=CC=CC=1COC(=O)\C=C/C(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)\C=C/C(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)\C=C/C(=O)OCC1=CC=CC=C1 NUSQJGCEUADMON-QQUZTSPOSA-J 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- YXNWKYMLMYBZSA-UHFFFAOYSA-N 2-dodecylsulfanylpropanoic acid Chemical compound CCCCCCCCCCCCSC(C)C(O)=O YXNWKYMLMYBZSA-UHFFFAOYSA-N 0.000 description 2
- KZYNPINQSVKGQR-UHFFFAOYSA-N 2-octadecylsulfanylpropanoic acid Chemical compound CCCCCCCCCCCCCCCCCCSC(C)C(O)=O KZYNPINQSVKGQR-UHFFFAOYSA-N 0.000 description 2
- LUHRVCWDUSUHMP-FTHVFMQUSA-L 4-o-[[(e)-4-(2-ethylhexoxy)-4-oxobut-2-enoyl]oxy-dioctylstannyl] 1-o-(2-ethylhexyl) (e)-but-2-enedioate Chemical compound CCCCC(CC)COC(=O)/C=C/C(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)\C=C\C(=O)OCC(CC)CCCC LUHRVCWDUSUHMP-FTHVFMQUSA-L 0.000 description 2
- XITDVRBPGQGVFK-FTHVFMQUSA-L 4-o-[[(e)-4-(6-methylheptoxy)-4-oxobut-2-enoyl]oxy-dioctylstannyl] 1-o-(6-methylheptyl) (e)-but-2-enedioate Chemical compound CC(C)CCCCCOC(=O)/C=C/C(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)\C=C\C(=O)OCCCCCC(C)C XITDVRBPGQGVFK-FTHVFMQUSA-L 0.000 description 2
- CHOXPWSDXIXQDY-YPKQJYFLSA-L 4-o-[[(z)-4-octadecoxy-4-oxobut-2-enoyl]oxy-dioctylstannyl] 1-o-octadecyl (z)-but-2-enedioate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)\C=C/C(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)\C=C/C(=O)OCCCCCCCCCCCCCCCCCC CHOXPWSDXIXQDY-YPKQJYFLSA-L 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- HBGIPOWCFUJKKH-KUAKSMGGSA-L C(\C=C/C(=O)[O-])(=O)OCC1=CC=CC=C1.C[Sn+2]C.C(C1=CC=CC=C1)OC(\C=C/C(=O)[O-])=O Chemical compound C(\C=C/C(=O)[O-])(=O)OCC1=CC=CC=C1.C[Sn+2]C.C(C1=CC=CC=C1)OC(\C=C/C(=O)[O-])=O HBGIPOWCFUJKKH-KUAKSMGGSA-L 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- IVBIJGUAZAPDDJ-LHJYRGMRSA-L [Sn++].[CH2]CCCCCCC.[CH2]CCCCCCC.CCCCCCCCCCCCCOC(=O)\C=C/C([O-])=O.CCCCCCCCCCCCCOC(=O)\C=C/C([O-])=O Chemical compound [Sn++].[CH2]CCCCCCC.[CH2]CCCCCCC.CCCCCCCCCCCCCOC(=O)\C=C/C([O-])=O.CCCCCCCCCCCCCOC(=O)\C=C/C([O-])=O IVBIJGUAZAPDDJ-LHJYRGMRSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- PZGVVCOOWYSSGB-UHFFFAOYSA-L but-2-enedioate;dioctyltin(2+) Chemical compound CCCCCCCC[Sn]1(CCCCCCCC)OC(=O)C=CC(=O)O1 PZGVVCOOWYSSGB-UHFFFAOYSA-L 0.000 description 2
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 2
- 229920006026 co-polymeric resin Polymers 0.000 description 2
- VLQWDCKTDZZUSU-KKUWAICFSA-L dibutyltin(2+);(z)-4-(6-methylheptoxy)-4-oxobut-2-enoate Chemical compound CC(C)CCCCCOC(=O)\C=C/C(=O)O[Sn](CCCC)(CCCC)OC(=O)\C=C/C(=O)OCCCCCC(C)C VLQWDCKTDZZUSU-KKUWAICFSA-L 0.000 description 2
- IPEIQLRNAOQYPJ-NUJFUEHTSA-L dibutyltin(2+);(z)-4-dodecoxy-4-oxobut-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)\C=C/C(=O)O[Sn](CCCC)(CCCC)OC(=O)\C=C/C(=O)OCCCCCCCCCCCC IPEIQLRNAOQYPJ-NUJFUEHTSA-L 0.000 description 2
- OSGZEAQLLRZGHT-VGKOASNMSA-L dibutyltin(2+);(z)-4-ethoxy-4-oxobut-2-enoate Chemical compound CCOC(=O)\C=C/C(=O)O[Sn](CCCC)(CCCC)OC(=O)\C=C/C(=O)OCC OSGZEAQLLRZGHT-VGKOASNMSA-L 0.000 description 2
- WHWTUCZRUDXTMZ-YPKQJYFLSA-L dibutyltin(2+);(z)-4-octadecoxy-4-oxobut-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)\C=C/C(=O)O[Sn](CCCC)(CCCC)OC(=O)\C=C/C(=O)OCCCCCCCCCCCCCCCCCC WHWTUCZRUDXTMZ-YPKQJYFLSA-L 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- NHDGUEXYQMLBDM-KUAKSMGGSA-L dioctyltin(2+) (Z)-4-oxo-4-phenylmethoxybut-2-enoate Chemical compound [O-]C(=O)\C=C/C(=O)OCC1=CC=CC=C1.[O-]C(=O)\C=C/C(=O)OCC1=CC=CC=C1.CCCCCCCC[Sn+2]CCCCCCCC NHDGUEXYQMLBDM-KUAKSMGGSA-L 0.000 description 2
- LUHRVCWDUSUHMP-KKUWAICFSA-L dioctyltin(2+);(z)-4-(2-ethylhexoxy)-4-oxobut-2-enoate Chemical compound CCCCC(CC)COC(=O)\C=C/C([O-])=O.CCCCC(CC)COC(=O)\C=C/C([O-])=O.CCCCCCCC[Sn+2]CCCCCCCC LUHRVCWDUSUHMP-KKUWAICFSA-L 0.000 description 2
- DSTWFRCNXMNXTR-WAYWQWQTSA-N dipropyl (z)-but-2-enedioate Chemical compound CCCOC(=O)\C=C/C(=O)OCCC DSTWFRCNXMNXTR-WAYWQWQTSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- VTWCVXKFWPSSNK-PLNGDYQASA-N (z)-4-(4-methoxybutoxy)-4-oxobut-2-enoic acid Chemical compound COCCCCOC(=O)\C=C/C(O)=O VTWCVXKFWPSSNK-PLNGDYQASA-N 0.000 description 1
- VPTNWGPGDXUKCY-KHPPLWFESA-N (z)-4-decoxy-4-oxobut-2-enoic acid Chemical compound CCCCCCCCCCOC(=O)\C=C/C(O)=O VPTNWGPGDXUKCY-KHPPLWFESA-N 0.000 description 1
- PKZGKWFUCLURJO-GRHBHMESSA-L (z)-but-2-enedioate;dimethyltin(2+) Chemical compound C[Sn+2]C.[O-]C(=O)\C=C/C([O-])=O PKZGKWFUCLURJO-GRHBHMESSA-L 0.000 description 1
- ZOCXRPUOFGZFCC-OGUYYKQXSA-J 1-O-benzyl 4-O-[dibutyl-[(Z)-4-[dibutyl-[(Z)-4-oxo-4-phenylmethoxybut-2-enoyl]oxystannyl]oxy-4-oxobut-2-enoyl]oxystannyl] (Z)-but-2-enedioate Chemical compound C=1C=CC=CC=1COC(=O)\C=C/C(=O)O[Sn](CCCC)(CCCC)OC(=O)\C=C/C(=O)O[Sn](CCCC)(CCCC)OC(=O)\C=C/C(=O)OCC1=CC=CC=C1 ZOCXRPUOFGZFCC-OGUYYKQXSA-J 0.000 description 1
- PCPYTNCQOSFKGG-UHFFFAOYSA-N 1-chlorobuta-1,3-diene Chemical compound ClC=CC=C PCPYTNCQOSFKGG-UHFFFAOYSA-N 0.000 description 1
- WPMZBGWYNQCTRW-YFQJWWFYSA-L 1-o-decyl 4-o-[dibutyl-[(z)-4-decoxy-4-oxobut-2-enoyl]oxystannyl] (z)-but-2-enedioate Chemical compound CCCCCCCCCCOC(=O)\C=C/C(=O)O[Sn](CCCC)(CCCC)OC(=O)\C=C/C(=O)OCCCCCCCCCC WPMZBGWYNQCTRW-YFQJWWFYSA-L 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
- RSWONZHBQRAOHE-UHFFFAOYSA-N 2-(2-methylphenyl)sulfanylpropanoic acid Chemical compound OC(=O)C(C)SC1=CC=CC=C1C RSWONZHBQRAOHE-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
- QZQJNDLCXSAWEN-UHFFFAOYSA-N 2-(4-methylphenyl)sulfanylpropanoic acid Chemical compound OC(=O)C(C)SC1=CC=C(C)C=C1 QZQJNDLCXSAWEN-UHFFFAOYSA-N 0.000 description 1
- YBSYBIUFIDWBQM-UHFFFAOYSA-N 2-(4-tert-butylphenyl)sulfanylpropanoic acid Chemical compound OC(=O)C(C)SC1=CC=C(C(C)(C)C)C=C1 YBSYBIUFIDWBQM-UHFFFAOYSA-N 0.000 description 1
- LYJMGMQFWYEYMB-UHFFFAOYSA-N 2-(6-methylheptylsulfanyl)propanoic acid Chemical compound CC(C)CCCCCSC(C)C(O)=O LYJMGMQFWYEYMB-UHFFFAOYSA-N 0.000 description 1
- QKHQITUHYKZKJI-UHFFFAOYSA-N 2-benzylsulfanylpropanoic acid Chemical compound OC(=O)C(C)SCC1=CC=CC=C1 QKHQITUHYKZKJI-UHFFFAOYSA-N 0.000 description 1
- VVXUMDXOTNQMQQ-UHFFFAOYSA-N 2-butylsulfanylpropanoic acid Chemical compound CCCCSC(C)C(O)=O VVXUMDXOTNQMQQ-UHFFFAOYSA-N 0.000 description 1
- ISRGONDNXBCDBM-UHFFFAOYSA-N 2-chlorostyrene Chemical compound ClC1=CC=CC=C1C=C ISRGONDNXBCDBM-UHFFFAOYSA-N 0.000 description 1
- LPSIMNDDAHCFHT-UHFFFAOYSA-N 2-cyclohexylsulfanylpropanoic acid Chemical compound OC(=O)C(C)SC1CCCCC1 LPSIMNDDAHCFHT-UHFFFAOYSA-N 0.000 description 1
- CXPPEHVKYJDIMC-UHFFFAOYSA-N 2-decylsulfanylpropanoic acid Chemical compound CCCCCCCCCCSC(C)C(O)=O CXPPEHVKYJDIMC-UHFFFAOYSA-N 0.000 description 1
- QSPCCDNHTPQDKL-UHFFFAOYSA-N 2-ethylsulfanylpropanoic acid Chemical compound CCSC(C)C(O)=O QSPCCDNHTPQDKL-UHFFFAOYSA-N 0.000 description 1
- VNPVINZCQMXQPS-UHFFFAOYSA-N 2-hexadecylsulfanylpropanoic acid Chemical compound CCCCCCCCCCCCCCCCSC(C)C(O)=O VNPVINZCQMXQPS-UHFFFAOYSA-N 0.000 description 1
- VZDIVASYBDRTTN-UHFFFAOYSA-N 2-hexylsulfanylpropanoic acid Chemical compound CCCCCCSC(C)C(O)=O VZDIVASYBDRTTN-UHFFFAOYSA-N 0.000 description 1
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 1
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- CTZWBKHVGXKFLI-KUAKSMGGSA-L dibutyltin(2+);(z)-4-hexoxy-4-oxobut-2-enoate Chemical compound CCCC[Sn+2]CCCC.CCCCCCOC(=O)\C=C/C([O-])=O.CCCCCCOC(=O)\C=C/C([O-])=O CTZWBKHVGXKFLI-KUAKSMGGSA-L 0.000 description 1
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Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Description
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The present invention relates to a method for stabilizing a polymer obtained by blending a halogen-containing resin with a styrene resin. [Industrial Field of Application] The method of the present invention can be widely used in the field of molding polymers blended with styrenic resins for the purpose of improving the impact properties of halogen-containing resins. [Prior Art] Generally, halogen-containing resins have poor impact resistance, and styrene-based resins are blended as a reinforcing agent to improve impact resistance. However, although products molded using the blended polymer have improved impact strength, they have the disadvantage of poor thermal stability and weather resistance. Generally, in this field, an organotin maleate compound is added in combination to improve weather resistance, and an organotin sulfur-containing compound is added in order to further improve thermal stability to stabilize the blended polymer. The current situation is that [Problems to be Solved by the Invention] Although the organotin-sulfur-containing compound used to stabilize the above-mentioned blend polymer has an excellent thermal stabilizing effect, it has poor weather resistance. It is not often used in fields that require it, and is stabilized and molded only with organotin maleate compounds, which have excellent weather resistance, but as a result, the thermal stabilization effect is insufficient, so it is necessary to maintain weather resistance The development of a stabilizer with excellent thermal stabilization effects has been awaited. [Means for Solving the Problem] From this perspective, the present inventors have developed a blend polymer consisting of a halogen-containing resin and a styrene resin that takes advantage of the weather resistance of the organotin maleate compound and also has a thermal stabilizing effect. As a result of intensive research into stabilizers with
With respect to 100 parts by weight, (a) 0.1 to 10 parts by weight of an organotin maleate compound, (b) General formula (1) (In the formula, R is an alkyl group, a cycloalkyl group,
It represents an alkenyl group, an aralkyl group, a phenyl group, or an alkyl-substituted phenyl group, and R 1 and R 2 each represent a hydrogen atom, a methyl group, an ethyl group, or a phenyl group. ) 0.005 substituted mercaptopropionic acid
It has been found that by adding ~1 part by weight in combination, the thermal stability of the blended polymer is significantly improved due to the mutual effect, there is no decrease in weather resistance, and plate-out during molding can be prevented. Completed the invention. Examples of the halogen-containing resin used in the present invention include commonly used halogen-containing resins, such as vinyl chloride resin, vinyl bromide resin, vinylidene chloride resin, chlorinated ethylene resin, and chlorinated propylene resin. , post-chlorinated vinyl chloride resin, vinyl chloride-vinyl acetate copolymer resin, vinyl chloride-ethylene copolymer resin, vinyl chloride-propylene copolymer resin, vinyl chloride-styrene copolymer resin, vinyl chloride-vinylidene chloride copolymer resin, Examples include vinyl chloride-ethylene-vinyl acetate copolymer resin. In the present invention, the styrene resin to be blended with the halogen-containing resin includes styrene and vinyl aromatic compounds such as α-substituted styrene such as α-methylstyrene, vinyltoluene, and nuclear-substituted styrene such as o-chlorostyrene. and other monomers copolymerizable with it, such as acrylonitrile, vinyl compounds such as acrylic acid and methacrylic acid and their esters, vinyl heterocyclic compounds such as vinylpyridine and vinylcarbazole, butadiene, 1 -Chlorbutadiene,
Examples include copolymers with monomers such as conjugated diene compounds such as 2-chlorobutadiene and isoprene, such as acrylonitrile-butadiene-styrene copolymers, acrylic ester-butadiene-styrene copolymers, and methacrylic acid. Examples include ester-butadiene-styrene copolymers and blends of these resins. In the present invention, the blend ratio of the halogen-containing resin and the styrene-based resin varies depending on the purpose of the molded product, and the blend ratio varies depending on the purpose, but in general, the blend ratio of the halogen-containing resin and the styrene resin is 100%
The amount of styrene resin added is 3 to 3 parts by weight.
It is 100 parts by weight. The organotin maleate compounds used in the present invention include commonly used compounds,
For example, preferably general formulas (2) and (3) [In formulas (2) and (3), R 3 is an alkyl group, an alkenyl group,
Aralkyl group or alkoxyalkyl group, R 4
is an alkyl group having 1 to 12 carbon atoms, A is oxygen or a group represented by -OOCCH=CHCOO-, k is 0 or 1, and l is an integer of 1 to 10. ] and the like. Examples of the organotin maleate compounds represented by the above general formula (2) include the following. Dimethyltin bis(methyl maleate), dimethyltin bis(ethyl maleate), dimethyltin bis(isopropyl maleate), dimethyltin bis(butyl maleate), dimethyltin bis(hexyl maleate), dimethyltin bis(octyl) dimethyltin bis(isooctyl maleate), dimethyltin bis(2-ethylhexyl maleate),
Dimethyltin bis(decyl maleate), dimethyltin bis(dodecyl maleate), dimethyltin bis(tridecyl maleate), dimethyltin bis(octadecyl maleate), dimethyltin bis(oleyl maleate), dimethyltin bis(benzyl maleate) ate), dimethyltin bis(cyclohexyl maleate), dimethyltin bis(methoxybutyl maleate), dibutyltin bis(methyl maleate),
Dibutyltin bis(ethyl maleate), dibutyltin bis(propyl maleate), dibutyltin bis(isopropyl maleate), dibutyltin bis(butyl maleate), dibutyltin bis(amyl maleate), dibutyltin bis(hexyl maleate) ), dibutyltin bis(heptyl maleate), dibutyltin bis(octyl maleate), dibutyltin bis(isooctyl maleate), dibutyltin bis(2-ethylhexyl maleate), dibutyltin bis(nonyl maleate), dibutyltin Bis(decyl maleate), dibutyltin bis(dodecyl maleate), dibutyltin bis(tridecyl maleate), dibutyltin bis(octadecyl maleate), dibutyltin bis(allyl maleate), dibutyltin bis(oleyl maleate) , dibutyltin bis(benzyl maleate), dibutyltin bis(cyclohexyl maleate), dibutyltin bis(methoxybutyl maleate), dioctyltin bis(ethyl maleate), dioctyltin bis(propyl maleate), dioctyltin bis(propyl maleate) (isopropyl maleate), dioctyltin bis(butyl maleate), dioctyltin bis(hexyl maleate), dioctyltin bis(octyl maleate),
Dioctyltin bis(isooctyl maleate),
Dioctyltin bis(2-ethylhexyl maleate), dioctyltin bis(decyl maleate), dioctyltin bis(dodecyl maleate), dioctyltin bis(tridecyl maleate), dioctyltin bis(octadecyl maleate), dioctyltin bis( oleyl maleate), dioctyltin bis(benzyl maleate), dioctyltin bis(cyclohexyl maleate), dioctyltin bis(methoxybutyl maleate), dilauryltin bis(ethyl maleate), dilauryltin bis(isopropyl maleate) , dilauryltin bis(butyl maleate), dilauryltin bis(hexyl maleate), dilauryltin bis(octyl maleate), dilauryltin bis(isooctyl maleate), dilauryltin bis(2-ethylhexyl maleate, dilauryltin Bis(decyl maleate), dilauryltin bis(dodecyl maleate),
Dilauryltin bis (tridecyl maleate), dilauryltin bis (octadecyl maleate), dilauryltin bis (oleyl maleate), dilauryltin bis (benzyl maleate), dilauryltin bis (cyclohexyl maleate), dilauryltin bis (cyclohexyl maleate) methoxybutyl maleate), bis(dimethyltin methyl maleate) maleate, bis(dimethyltin ethyl maleate) maleate,
Bis(dimethyltin isopropyl maleate) maleate, bis(dimethyltin butyl maleate) maleate, bis(dimethyltin hexyl maleate) maleate, bis(dimethyltin octyl maleate) maleate, bis(dimethyltin isooctyl maleate) maleate , bis(dimethyltin 2-ethylhexyl maleate) maleate, bis(dimethyltin decyl maleate) maleate,
Bis(dimethyltin dodecyl maleate) maleate, bis(dimethyltin tridecyl maleate) maleate, bis(dimethyltin octadecyl maleate) maleate, bis(dimethyltin oleyl maleate) maleate, bis(dimethyltin benzyl maleate) maleate , bis(dimethyltin cyclohexyl maleate) maleate, bis(dimethyltin methoxybutyl maleate) maleate, bis(dibutyltin methyl maleate) maleate, bis(dibutyltin ethyl maleate) maleate, bis(dibutyltin propyl maleate)
Maleate, bis(dibutyltin isopropyl maleate) maleate, bis(dibutyltin butyl maleate) maleate, bis(dibutyltin amyl maleate) maleate, bis(dibutyltin hexyl maleate) maleate, bis(dibutyltin heptyl maleate) maleate, Bis(dibutyltin octyl maleate) maleate, bis(dibutyltin isooctyl maleate) maleate,
Bis(dibutyltin 2-ethylhexyl maleate) maleate, bis(dibutyltin nonyl maleate) maleate, bis(dibutyltin decyl maleate) maleate, bis(dibutyltin dodecyl maleate) maleate, bis(dibutyltin tridecyl maleate) maleate, bis (dibutyltin octadecyl maleate) maleate, bis(dibutyltin allyl maleate) maleate, bis(dibutyltin oleyl maleate) maleate, bis(dibutyltin benzyl maleate) maleate, bis(dibutyltin cyclohexyl maleate) maleate, bis (dibutyltin methoxybutyl maleate) maleate, bis(dioctyltin ethyl maleate) maleate, bis(dioctyltin propyl maleate) maleate, bis(dioctyltin isopropyl maleate) maleate, bis(dioctyltin butyl maleate) maleate, Bis(dioctyltin hexyl maleate) maleate, bis(dioctyltin octyl maleate) maleate, bis(dioctyltin isooctyl maleate) maleate, bis(dioctyltin 2-ethylhexyl maleate) maleate, bis(dioctyltin decyl maleate) maleate , bis(dioctyltin dodecyl maleate) maleate, bis(dioctyltin tridecyl maleate) maleate, bis(dioctyltin octadecyl maleate) maleate, bis(dioctyltin oleyl maleate) maleate, bis(dioctyltin benzyl maleate) maleate,
Bis(dioctyltin cyclohexyl maleate)
Maleate, bis(dioctyltin methoxybutyl maleate) maleate, bis(dilauryltin ethyl maleate) maleate, bis(dilauryltin isopropyl maleate) maleate, bis(dilauryltin butyl maleate) maleate,
Bis(dilauryltin hexyl maleate) maleate, Bis(dilauryltin octyl maleate)
maleate, bis(dilauryltin isooctyl maleate, maleate, bis(dilauryltin 2-
ethylhexyl maleate) maleate, bis(dilauryltindecyl maleate) maleate,
Bis(dilauryltin dodecyl maleate) maleate, Bis(dilauryltin tridecyl maleate) maleate, Bis(dilauryltin octadecyl maleate) maleate, Bis(dilauryltin oleyl maleate) maleate, Bis(dilauryltin benzyl maleate) maleate , bis(dilauryltin cyclohexyl maleate) maleate, bis(dilauryltin methoxybutyl maleate) maleate, bis(dimethyltin thyl maleate) oxide, bis(dimethyltin butyl maleate) oxide, bis(dimethyltin isooctyl maleate) oxide , bis(dimethyltin benzyl maleate) oxide, bis(dibutyltin methyl maleate) oxide, bis(dibutyltin butyl maleate) oxide, bis(dibutyltin isooctyl maleate) oxide, bis(dibutyltin benzyl maleate) Oxide, bis(dioctyltin butyl maleate)
oxide, bis(dioctyltin isooctyl maleate) oxide, bis(dioctyltin benzyl maleate) oxide, bis(dilauryltin butyl maleate) oxide, bis(dilauryltin isooctyl maleate) oxide, bis(dilauryltin benzyl maleate) ate) oxide, and preferred examples include dibutyltin bis(methyl maleate), dibutyltin bis(butyl maleate), dibutyltin bis(isooctyl maleate), dibutyltin bis(2-ethylhexyl maleate), Dibutyltin bis(tridecyl maleate), dibutyltin bis(octadecyl maleate), dibutyltin bis(oleyl maleate), dibutyltin bis(benzyl maleate), dibutyltin bis(cyclohexyl maleate), dioctyltin bis( butyl maleate), dioctyltin bis(isooctyl maleate), dioctyltin bis(2-ethylhexyl maleate), dioctyltin bis(tridecyl maleate), dioctyltin bis(octadecyl maleate, dioctyltin bis(oleyl maleate) ate), dioctyltin bis(benzyl maleate), dioctyltin bis(cyclohexyl maleate), bis(dibutyltin methyl maleate) maleate, bis(dibutyltin butyl maleate) maleate, bis(dibutyltin isooctyl maleate) maleate,
Bis(dibutyltin 2-ethylhexyl maleate) maleate, bis(dibutyltin tridecyl maleate) maleate, bis(dibutyltin octadecyl maleate) maleate, bis(dibutyltin oleyl maleate) maleate, bis(dibutyltin benzyl maleate) ) maleate, bis(dibutyltin cyclohexyl maleate) maleate, bis(dioctyltin butyl maleate) maleate, bis(dioctyltin isooctyl maleate) maleate, bis(dioctyltin 2-ethylhexyl maleate) maleate, bis(dioctyltin tridecyl maleate) maleate,
Bis(dioctyltin octadecyl maleate) maleate, bis(dioctyltin oleyl maleate) maleate, bis(dioctyltin benzyl maleate) maleate, bis(dioctyltin cyclohexyl maleate) maleate, bis(sibutyltin methyl maleate) oxide, Bis(dibutyltin butyl maleate) oxide, bis(dibutyltin benzyl maleate) oxide,
Examples include bis(dioctyltin butyl maleate) oxide and bis(dioctyltin benzyl maleate) oxide. Examples of the organotin maleate compound represented by the general formula (3) include the following. dimethyltin maleate,
These include dibutyltin maleate, dioctyltin maleate, dilauryltin maleate, and polymers thereof, and preferred examples include dibutyltin maleate, dioctyltin maleate, and polymers thereof. In the substituted mercaptopropionic acid represented by the general formula (1) used in the present invention, R in the formula is, for example, a straight or branched alkyl group having 1 to 22 carbon atoms, a cycloalkyl group, an alkenyl group, an aralkyl group, a phenyl group, an alkyl-substituted phenyl group substituted with an alkyl group having 1 to 12 carbon atoms,
R 1 and R 2 are hydrogen atoms, methyl groups, ethyl groups,
Phenyl group, and preferred examples of such compounds are methylmercaptopropionic acid, ethylmercaptopropionic acid, propylmercaptopropionic acid, butylmercaptopropionic acid, hexylmercaptopropionic acid, octylmercaptopropionic acid, 2-ethylhexylmercapto. Propionic acid, isooctylmercaptopropionic acid, decylmercaptopropionic acid, dodecylmercaptopropionic acid, tetradecylmercaptopropionic acid, hexadecylmercaptopropionic acid, octadecylmercaptopropionic acid, oleylmercaptopropionic acid, phenylmercaptopropionic acid, p- Methylphenylmercaptopropionic acid, o-methylphenylmercaptopropionic acid, p-nonylphenylmercaptopropionic acid, p-tert-butylphenylmercaptopropionic acid, benzylmercaptopropionic acid, cyclohexylmercaptopropionic acid, butylmercapto α- Methylpropionic acid, hexylmercapto α-methylpropionic acid, octylmercapto α-methylpropionic acid, 2-ethylhexylmercapto α-methylpropionic acid, isooctylmercapto α-methylpropionic acid, decylmercapto α-methylpropionic acid, dodecylmercapto α -Methylpropionic acid, tridecylmercapto α-methylpropionic acid, tetradecylmercapto α-methylpropionic acid, hexadecylmercapto α-methylpropionic acid, octadecylmercapto α-methylpropionic acid, oleylmercapto α-methylpropionic acid, phenyl Mercapto α-methylpropionic acid, p-methylphenylmercapto α-methylpropionic acid, o-methylphenylmercapto α-methylpropionic acid, p-nonylphenylmercapto α-methylpropionic acid, p-tertiarybutyl phenyl Mercapto α
-Methylpropionic acid, benzylmercapto α-methylpropionic acid, cyclohexylmercapto α-methylpropionic acid, butylmercapto β-methylpropionic acid, octylmercapto β-methylpropionic acid, dodecylmercapto β-methylpropionic acid, tetradecylmercapto β- Methylpropionic acid, hexadecylmercapto β-methylpropionic acid, octadecylmercapto β-methylpropionic acid, dodecylmercapto β-phenylpropionic acid, benzylmercapto β-phenylpropionic acid, dodecylmercapto α-ethylpropionic acid, dodecylmercapto β-phenylpropionic acid Particularly preferred examples include dodecylmercaptopropionic acid, octadecylmercaptopropionic acid, dodecylmercapto α-methylpropionic acid, and octadecylmercapto α-methylpropionic acid. In the present invention, for 100 parts by weight of a blend polymer of a halogen-containing resin and a styrene resin,
If the amount of the organic tin maleate compound added is less than 0.1 part by weight, the thermal stabilizing effect will be small, and if the amount exceeds 10 parts by weight, the expected thermal stabilizing effect will not be observed, and the amount is preferably 0.5 to 5.0 parts by weight. If the added amount of the substituted mercaptopropionic acid represented by the general formula (1) is 0.005 parts by weight or less, no additive effect will be observed, and if the amount exceeds 1 part by weight, the heat stabilizing effect will be caused. The amount is preferably 0.01 to 0.5 parts by weight. The method for adding the stabilizer used in the present invention to the polymer blend of the halogen-containing resin and the styrene resin may be carried out by a conventionally known technique. The mixture may be mixed using a ribbon blender, a Banbury mixer, etc., or an organotin maleate compound and a substituted mercaptopropionic acid represented by the general formula (1) may be mixed in advance and mixed with the blend polymer using the above-mentioned mixer. You can. Further, in addition to these stabilizers, known stabilizers such as dialkyltin fatty acid salts, metal soaps, organic phosphorus compounds, etc. can be used in combination. Furthermore, if necessary, plasticizers, lubricants, antioxidants, pigments, fillers, processing aids, etc. can be added. [Examples and Effects] The present invention will be specifically described below with reference to Examples, but the present invention is not limited thereto. In the examples, parts refer to parts by weight. Example 1 Vinyl chloride resin [Geon 103Ep manufactured by Nippon Zeon Co., Ltd.
-8] 100 parts, 5 parts of methacrylic acid ester-butadiene-styrene copolymer [Kane Ace B-28 manufactured by Kanekabuchi Chemical Co., Ltd.], and 3 parts of di-n-butyltin maleate polymer [Table-1] A compound containing 0.02 part of the stabilizer shown in 1 was kneaded for 5 minutes using an 8-inch test roll adjusted to 170°C to produce a sheet with a thickness of 0.5 mm. Next, create a 3cm x 5cm test piece from this sheet, place this test piece in a gear oven adjusted to 190â, and measure the time (minutes) until the test piece deteriorates (becomes black or blackish brown). did. In addition, 5 test pieces of 5 cm x 5 cm were made from a 0.5 mm sheet, and these 5 test pieces were stacked and heated at 200â and 30Kg/ cm2 .
The color tone was observed when pressed for 20 minutes. In addition, the plate-out property was evaluated by observing the amount of deposits on the roll after kneading with a test roll for 5 minutes.
This was done using A, B, and C below. A: Almost no plate out is observed. B: Slight plate out is observed. C: Significant plate-out is observed. The results are shown in [Table 1]. As can be seen from [Table 1], the combined use of the organotin maleate polymer of the present invention and substituted mercaptopropionic acid improves the thermal stabilization effect and also greatly improves the plate-out property.
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WELâSONâDCåã«å
¥ãå£åïŒé»åïŒè¿ã®æ
éã枬å®ãããçµæããè¡šâïŒãã«ç€ºãããè¡šâ
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å®åå¹æã®çžå°å¹æãé¡èã«è¡šãããææ©é«ãã¬
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ããã[Table] Example 2 Vinyl chloride resin [Geon 103Ep manufactured by Nippon Zeon Co., Ltd.]
-8] 100 parts, acrylonitrile-butadiene-
A mixture of 40 parts of styrene copolymer [Toughflex TFX-410, manufactured by Mitsubishi Monsanto Chemical Co., Ltd.] and the stabilizer shown in [Table 2] was prepared using an 8-inch roll adjusted to 170°C in the same manner as in Example 1. A sheet with a thickness of 0.5 mm was prepared. Next, create a 3cm x 5cm test piece from this sheet, place this test piece in a gear oven adjusted to 190â, and measure the time (minutes) until the test piece deteriorates (becomes black or blackish brown). did. In addition, 5 test pieces of 5 cm x 5 cm were made from a 0.5 mm sheet, and these 5 test pieces were stacked and heated at 200â and 30Kg/ cm2 .
The color tone was observed when pressed for 20 minutes. Weather resistance was evaluated by pressing a 0.5 mm sheet to create a 5 cm x 15 cm test piece, and using a Sunshine Weather Meter manufactured by Suga Test Instruments Co., Ltd.
It was placed in a WEL-SON-DC mold and the time until deterioration (blackening) was measured. The results are shown in [Table 2]. ãtable-
2], it was found that the thermal stabilizing effect of organotin maleate compounds alone is small, and that organotin sulfur-containing compounds have excellent thermal stabilizing effects but poor weather resistance. It can be seen that the combined use of substituted mercaptopropionic acid and substituted mercaptopropionic acid produces a remarkable mutual effect of thermal stabilization, and maintains the weather resistance of the organotin maleate compound.
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ïŒæäœè£œãããã®ïŒæãéãã200âã30Kg/cm2ã§
20åéãã¬ã¹ããæã®è²èª¿ã芳å¯ãããçµæã
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æãåªããããšããããã[Table] Example 3 Vinyl chloride resin [Geon 103Ep manufactured by Nippon Zeon Co., Ltd.
-8] 100 parts, methacrylic acid ester-butadiene-styrene copolymer [BTA manufactured by Kureha Chemical Industry Co., Ltd.
-s] 60 parts, titanium white 1 part, and the stabilizer shown in [Table 3] were added and the mixture was adjusted to 170â 8
A 0.5 mm sheet was produced using an inch roll in the same manner as in Example 1. Next, create a 3cm x 5cm test piece from this sheet, place this test piece in a gear oven adjusted to 190â, and measure the time (minutes) until the test piece deteriorates (becomes black or blackish brown). did. In addition, 5 test pieces of 5 cm x 5 cm were made from a 0.5 mm sheet, and these 5 test pieces were stacked and heated at 200â and 30Kg/ cm2 .
The color tone was observed when pressed for 20 minutes. The results are shown in [Table 3]. It can be seen that the thermal stabilization effect is excellent due to the mutual effect of the organotin maleate compound of the present invention and the substituted mercaptopropionic acid.
Claims (1)
ã¬ã³ãããªããŒ100éééšã«å¯Ÿãã (a) ææ©é«ãã¬ãšãŒãç³»ååç©ã0.1ã10éééš
ãšã (b) äžè¬åŒ ïŒåŒäžãã¯ã¢ã«ãã«åºãã·ã¯ãã¢ã«ãã«åºã
ã¢ã«ã±ãã«åºãã¢ã©ã«ãã«åºãããšãã«åºãã¢
ã«ãã«çœ®æããšãã«åºã瀺ããR1ãR2ã¯ãã
ããæ°ŽçŽ ååãã¡ãã«åºããšãã«åºãŸãã¯ããš
ãã«åºã瀺ããïŒ ã§ç€ºããã眮æã¡ã«ã«ããããããªã³é žã0.005
ãïŒéééšãšã䜵çšæ·»å ããããšãç¹åŸŽãšãã該
ãã¬ã³ãããªããŒã®å®å®åæ³ã[Scope of Claims] 1. (a) 0.1 to 10 parts by weight of an organotin maleate compound, (b) General formula (In the formula, R is an alkyl group, a cycloalkyl group,
It represents an alkenyl group, an aralkyl group, a phenyl group, or an alkyl-substituted phenyl group, and R 1 and R 2 each represent a hydrogen atom, a methyl group, an ethyl group, or a phenyl group. ) 0.005 substituted mercaptopropionic acid
A method for stabilizing the blend polymer, characterized by adding 1 part by weight in combination.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5130885A JPS61209248A (en) | 1985-03-14 | 1985-03-14 | Method of stabilizing synthetic resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5130885A JPS61209248A (en) | 1985-03-14 | 1985-03-14 | Method of stabilizing synthetic resin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61209248A JPS61209248A (en) | 1986-09-17 |
| JPS6411224B2 true JPS6411224B2 (en) | 1989-02-23 |
Family
ID=12883284
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5130885A Granted JPS61209248A (en) | 1985-03-14 | 1985-03-14 | Method of stabilizing synthetic resin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61209248A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0354245A (en) * | 1989-07-21 | 1991-03-08 | Nitto Kasei Co Ltd | Stabilized chlorinated vinyl chloride resin composition |
-
1985
- 1985-03-14 JP JP5130885A patent/JPS61209248A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61209248A (en) | 1986-09-17 |
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