JPH0254364B2 - - Google Patents
Info
- Publication number
- JPH0254364B2 JPH0254364B2 JP9507183A JP9507183A JPH0254364B2 JP H0254364 B2 JPH0254364 B2 JP H0254364B2 JP 9507183 A JP9507183 A JP 9507183A JP 9507183 A JP9507183 A JP 9507183A JP H0254364 B2 JPH0254364 B2 JP H0254364B2
- Authority
- JP
- Japan
- Prior art keywords
- temperature
- maleic anhydride
- styrene
- polymerization
- 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.)
- Expired
Links
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 53
- 238000006116 polymerization reaction Methods 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 36
- 229920001577 copolymer Polymers 0.000 claims description 31
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 31
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 23
- 239000000178 monomer Substances 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000007870 radical polymerization initiator Substances 0.000 claims description 7
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 239000011347 resin Substances 0.000 description 17
- 229920005989 resin Polymers 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000000704 physical effect Effects 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 239000003505 polymerization initiator Substances 0.000 description 8
- 238000002156 mixing Methods 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 238000007872 degassing Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 230000007423 decrease Effects 0.000 description 5
- 238000002845 discoloration Methods 0.000 description 5
- GEJJECIDFXFUMI-UHFFFAOYSA-N dodecanethioic s-acid Chemical compound CCCCCCCCCCCC(S)=O GEJJECIDFXFUMI-UHFFFAOYSA-N 0.000 description 5
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 239000000113 methacrylic resin Substances 0.000 description 4
- 239000008188 pellet Substances 0.000 description 4
- 229920001897 terpolymer Polymers 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- -1 K 11 /K 13 = 0.5 Chemical compound 0.000 description 3
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000001746 injection moulding Methods 0.000 description 3
- OXOBLVKOVYDHQV-UHFFFAOYSA-N methyl 2-methylprop-2-enoate 3-(2-phenylethenyl)furan-2,5-dione Chemical compound COC(=O)C(C)=C.O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 OXOBLVKOVYDHQV-UHFFFAOYSA-N 0.000 description 3
- 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
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 238000012662 bulk polymerization Methods 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CUYHZUQBWIJJCT-UHFFFAOYSA-N 1-[(1-cyanocyclopentyl)diazenyl]cyclopentane-1-carbonitrile Chemical compound C1CCCC1(C#N)N=NC1(C#N)CCCC1 CUYHZUQBWIJJCT-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical group C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- ZYUVGYBAPZYKSA-UHFFFAOYSA-N 5-(3-hydroxybutan-2-yl)-4-methylbenzene-1,3-diol Chemical compound CC(O)C(C)C1=CC(O)=CC(O)=C1C ZYUVGYBAPZYKSA-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical class CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 1
- JWKNCJFGBOQAQL-UHFFFAOYSA-N butyl dodecaneperoxoate Chemical group CCCCCCCCCCCC(=O)OOCCCC JWKNCJFGBOQAQL-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical group CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- NWADXBLMWHFGGU-UHFFFAOYSA-N dodecanoic anhydride Chemical compound CCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCC NWADXBLMWHFGGU-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical class CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])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
- 239000000314 lubricant Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- KOPQZJAYZFAPBC-UHFFFAOYSA-N propanoyl propaneperoxoate Chemical compound CCC(=O)OOC(=O)CC KOPQZJAYZFAPBC-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000005341 toughened glass Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9507183A JPS59221315A (ja) | 1983-05-31 | 1983-05-31 | メタクリル共重合体の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9507183A JPS59221315A (ja) | 1983-05-31 | 1983-05-31 | メタクリル共重合体の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59221315A JPS59221315A (ja) | 1984-12-12 |
| JPH0254364B2 true JPH0254364B2 (enrdf_load_stackoverflow) | 1990-11-21 |
Family
ID=14127753
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9507183A Granted JPS59221315A (ja) | 1983-05-31 | 1983-05-31 | メタクリル共重合体の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59221315A (enrdf_load_stackoverflow) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4866136A (en) * | 1987-08-12 | 1989-09-12 | Pennwalt Corporation | Process for producing polymer bound hindered amine light stabilizers |
| US5096977A (en) * | 1987-08-12 | 1992-03-17 | Atochem North America, Inc. | Process for preparing polymer bound UV stabilizers |
| US5096974A (en) * | 1987-08-12 | 1992-03-17 | Atochem North America, Inc. | Process for preparing multipurpose polymer bound stabilizers and polymer bound stabilizer produced thereby |
| US4975489A (en) * | 1987-08-12 | 1990-12-04 | Atochem North America, Inc. | Process for preparing polymer bound hindered amine light stabilizers |
| US4857596A (en) * | 1987-08-12 | 1989-08-15 | Pennwalt Corporation | Polymer bound antioxidant stabilizers |
| US4981914A (en) * | 1987-08-12 | 1991-01-01 | Atochem North America, Inc. | Polymer bound UV stabilizers |
| US4857595A (en) * | 1987-08-12 | 1989-08-15 | Pennwalt Corporation | Polymer bound hindered amine light stabilizers |
| US4981915A (en) * | 1987-08-12 | 1991-01-01 | Atochem North America, Inc. | Multipurpose polymer bound stabilizers |
| US4863999A (en) * | 1987-08-12 | 1989-09-05 | Pennwalt Corporation | Multipurpose polymer bound stabilizers |
| US5206378A (en) * | 1987-08-12 | 1993-04-27 | Elf Atochem North America, Inc. | Hydrazido functionalized 2-(2-hydroxyphenyl)-2h-benzotriazoles |
| US4868246A (en) * | 1987-08-12 | 1989-09-19 | Pennwalt Corporation | Polymer bound UV stabilizers |
| US4981917A (en) * | 1987-08-12 | 1991-01-01 | Atochem North America, Inc. | Process for preparing polymer bound antioxidant stabilizers |
| US4956416A (en) * | 1988-08-18 | 1990-09-11 | Atochem North America, Inc. | Amino or hydrazino peroxides, derivatives and their uses |
| US5272219A (en) * | 1988-08-18 | 1993-12-21 | Elf Atochem North America, Inc. | Process for preparing amino or hydrazino peroxides, derivatives and their uses |
| US5220015A (en) * | 1988-11-07 | 1993-06-15 | Elf Atochem North America, Inc. | Flame retardants compounds |
| US5037894A (en) * | 1988-11-07 | 1991-08-06 | Atochem North America, Inc. | Polymer bound flame retardants |
| US5140070A (en) * | 1988-11-07 | 1992-08-18 | Elf Atochem North America, Inc | Compositions comprising polymer bond flame retardants |
| JP2001270905A (ja) | 2000-01-21 | 2001-10-02 | Mitsubishi Rayon Co Ltd | 耐熱性メタクリル共重合体、その製造方法および光学素子 |
| WO2016024553A1 (ja) * | 2014-08-11 | 2016-02-18 | 電気化学工業株式会社 | メタクリル樹脂の耐熱性向上に適した共重合体 |
-
1983
- 1983-05-31 JP JP9507183A patent/JPS59221315A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59221315A (ja) | 1984-12-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0254364B2 (enrdf_load_stackoverflow) | ||
| JPH0251445B2 (enrdf_load_stackoverflow) | ||
| JPS60202128A (ja) | メタクリル系樹脂成形材料およびその製造方法 | |
| TW307772B (enrdf_load_stackoverflow) | ||
| EP0097948B2 (en) | Information recording substrate | |
| JPH0582405B2 (enrdf_load_stackoverflow) | ||
| JPS646214B2 (enrdf_load_stackoverflow) | ||
| JPS58217501A (ja) | 新規共重合体 | |
| KR101432597B1 (ko) | 내열성과 내스크래치성이 우수한 열가소성 수지 조성물 제조방법 | |
| JP3215719B2 (ja) | 重合体組成物 | |
| JPS58455B2 (ja) | 耐溶剤性アクリル樹脂の製造方法 | |
| JP5046446B2 (ja) | 共重合樹脂及びその製造方法 | |
| JPH0240260B2 (enrdf_load_stackoverflow) | ||
| JP3061551B2 (ja) | メタクリル系樹脂の製造方法 | |
| JPH0129220B2 (enrdf_load_stackoverflow) | ||
| JPS6330511A (ja) | メタクリル系樹脂成形材料 | |
| JPS6330510A (ja) | 架橋メタクリル系樹脂用シラツプ組成物 | |
| CN113698527B (zh) | 一种透明阻燃pmma树脂及其制备方法 | |
| JPH0158204B2 (enrdf_load_stackoverflow) | ||
| JPH0582406B2 (enrdf_load_stackoverflow) | ||
| JP2778916B2 (ja) | 光学用素子 | |
| JPH05310853A (ja) | 耐熱性アクリル樹脂の製造方法 | |
| KR101104510B1 (ko) | 내열성 및 투명성이 우수한 스티렌계 공중합체 및 그제조방법 | |
| KR100646602B1 (ko) | 투명 아크릴계 수지용 충격보강제 및 그 제조방법 | |
| JPH1087739A (ja) | 熱安定性に優れたメタクリル系樹脂 |