JPH0562125B2 - - Google Patents
Info
- Publication number
- JPH0562125B2 JPH0562125B2 JP23883383A JP23883383A JPH0562125B2 JP H0562125 B2 JPH0562125 B2 JP H0562125B2 JP 23883383 A JP23883383 A JP 23883383A JP 23883383 A JP23883383 A JP 23883383A JP H0562125 B2 JPH0562125 B2 JP H0562125B2
- Authority
- JP
- Japan
- Prior art keywords
- macromonomer
- parts
- mercaptopropionic acid
- 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 - Fee Related
Links
- 239000000178 monomer Substances 0.000 claims description 19
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 8
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- 239000012986 chain transfer agent Substances 0.000 claims description 5
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 18
- 239000000243 solution Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229920000578 graft copolymer Polymers 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 6
- 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 5
- 238000004040 coloring Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical group CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- 238000010526 radical polymerization reaction Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000004042 decolorization Methods 0.000 description 3
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 3
- 238000009776 industrial production Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 231100000676 disease causative agent Toxicity 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 150000004714 phosphonium salts Chemical group 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- -1 alkyl methacrylates Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- IKWKJIWDLVYZIY-UHFFFAOYSA-M butyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCC)C1=CC=CC=C1 IKWKJIWDLVYZIY-UHFFFAOYSA-M 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23883383A JPS60133007A (ja) | 1983-12-20 | 1983-12-20 | マクロモノマ−の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23883383A JPS60133007A (ja) | 1983-12-20 | 1983-12-20 | マクロモノマ−の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60133007A JPS60133007A (ja) | 1985-07-16 |
| JPH0562125B2 true JPH0562125B2 (enrdf_load_stackoverflow) | 1993-09-07 |
Family
ID=17035947
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP23883383A Granted JPS60133007A (ja) | 1983-12-20 | 1983-12-20 | マクロモノマ−の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60133007A (enrdf_load_stackoverflow) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62212415A (ja) * | 1986-03-13 | 1987-09-18 | Toagosei Chem Ind Co Ltd | オリゴマ−の製造法 |
| JPH01178512A (ja) * | 1987-12-29 | 1989-07-14 | Nitto Denko Corp | アクリル酸系マクロモノマ及びその製造方法 |
| JPH01245001A (ja) * | 1988-03-28 | 1989-09-29 | Toagosei Chem Ind Co Ltd | マクロモノマーおよびグラフトポリマーの製造方法 |
| JP2780722B2 (ja) * | 1989-10-02 | 1998-07-30 | 三井化学株式会社 | アクリル系共重合体、その製法およびその用途 |
| US5618898A (en) * | 1992-02-10 | 1997-04-08 | Toagosei Chemical Industry Co., Ltd. | Weather-resistant solvent-based coating obtained by polymerization with thioether bond converted to sulfone bond |
| JP3906493B2 (ja) * | 1996-05-29 | 2007-04-18 | 東亞合成株式会社 | マクロモノマー分散液の製造方法 |
| FR2750321B1 (fr) * | 1996-06-28 | 1998-07-31 | Oreal | Utilisation en cosmetique de copolymeres a squelette flexible, greffes par des macromonomeres hydrophobes et rigides ; compositions mises en oeuvre |
| US6388026B1 (en) | 1997-08-05 | 2002-05-14 | S. C. Johnson Commercial Markets, Inc. | Process for the preparation of macromers |
| JP4878411B2 (ja) * | 2000-09-26 | 2012-02-15 | 綜研化学株式会社 | 分子末端に重合性不飽和基を有するアクリル系重合体 |
| TWI403838B (zh) | 2007-04-11 | 2013-08-01 | Lg Chemical Ltd | 包含由做為鹼溶性樹脂之大分子單體所製備之聚合物之光感樹脂組成物 |
| JP5347115B2 (ja) | 2007-04-24 | 2013-11-20 | 綜研化学株式会社 | 粘着剤の製造方法 |
| JP5888228B2 (ja) | 2011-01-06 | 2016-03-16 | 三菱レイヨン株式会社 | ポリフッ化ビニリデン用改質剤、電池用バインダー樹脂組成物、二次電池用電極及び電池 |
| WO2014098141A1 (ja) | 2012-12-18 | 2014-06-26 | 三菱レイヨン株式会社 | ポリマー及びその製造方法、成形材料並びに成形体 |
| EP2937134A4 (en) | 2012-12-20 | 2016-01-13 | Mitsubishi Rayon Co | POLYMERIC COMPOSITION AND POROUS MEMBRANE |
| JP5858154B2 (ja) | 2013-03-15 | 2016-02-10 | 三菱レイヨン株式会社 | 多孔質膜用樹脂組成物、製膜原液、多孔質膜の製造方法、中空糸膜用多孔質膜の製造方法、水処理装置用多孔質膜の製造方法、電解質支持体用多孔質膜の製造方法、及びセパレーター用多孔質膜の製造方法 |
| JP6413767B2 (ja) | 2013-10-16 | 2018-10-31 | 三菱ケミカル株式会社 | 重合体及びその製造方法、並びに成形体 |
| JP6868979B2 (ja) * | 2016-07-06 | 2021-05-12 | 株式会社日本触媒 | アクリル酸エステル重合体およびその製造方法 |
| JP6690780B2 (ja) | 2017-03-27 | 2020-04-28 | 三菱ケミカル株式会社 | 多孔質膜、膜モジュール、水処理装置、及び多孔質膜の製造方法 |
| JP7099467B2 (ja) | 2017-09-25 | 2022-07-12 | 三菱ケミカル株式会社 | 中空糸膜 |
| WO2019103102A1 (ja) | 2017-11-24 | 2019-05-31 | 三菱ケミカル株式会社 | ブロック共重合体組成物及びその製造方法 |
| KR20220159357A (ko) | 2020-03-25 | 2022-12-02 | 미쯔비시 케미컬 주식회사 | 중합체 조성물, 윤활유 첨가제, 점도 지수 향상제, 윤활유 조성물, 중합체 조성물의 제조 방법, 및 매크로 모노머의 제조 방법 |
| CN115210279A (zh) | 2020-03-26 | 2022-10-18 | 三菱化学株式会社 | 共聚物、树脂组合物、成型体、膜状成型体以及共聚物的制造方法 |
| JP7472001B2 (ja) | 2020-11-13 | 2024-04-22 | 日産自動車株式会社 | 複層塗膜形成方法 |
| JPWO2022114157A1 (enrdf_load_stackoverflow) | 2020-11-30 | 2022-06-02 | ||
| JPWO2023068375A1 (enrdf_load_stackoverflow) | 2021-10-22 | 2023-04-27 | ||
| JP2023086718A (ja) | 2021-12-10 | 2023-06-22 | 三菱ケミカル株式会社 | 硬化性組成物、成形体、シリコーンハイドロゲル及びその製造方法、マクロモノマー |
| CN119816532A (zh) | 2022-09-09 | 2025-04-11 | 三菱化学株式会社 | 聚合物、润滑油用减磨剂和润滑油组合物 |
| JP7663156B2 (ja) | 2022-09-09 | 2025-04-16 | 三菱ケミカル株式会社 | 重合体、潤滑油用摩擦低減剤、および潤滑油組成物 |
| TW202440693A (zh) | 2022-12-27 | 2024-10-16 | 日商三菱化學股份有限公司 | 硬化性組合物、成形體、聚矽氧水凝膠及其製造方法 |
-
1983
- 1983-12-20 JP JP23883383A patent/JPS60133007A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60133007A (ja) | 1985-07-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |