JPS58108213A - ２−シアノアクリル酸エステル重合体の製造方法 - Google Patents

２−シアノアクリル酸エステル重合体の製造方法

Info

Publication number: JPS58108213A
Authority: JP; Japan
Prior art keywords: polymerization; polymer; acid ester; molecular weight; cyanoacrylic acid
Prior art date: 1981-12-22
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.): Granted

Application number

JP20624381A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0222762B2 (2

Inventor

Shohei Hattori

正平服部

Kaoru Kimura

馨木村

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Toagosei Co Ltd

Original Assignee

Toagosei Co Ltd

Priority date (The priority date 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 date listed.)

1981-12-22

Filing date

1981-12-22

Publication date

1983-06-28

1981-12-22 Application filed by Toagosei Co Ltd filed Critical Toagosei Co Ltd

1981-12-22 Priority to JP20624381A priority Critical patent/JPS58108213A/ja

1983-06-28 Publication of JPS58108213A publication Critical patent/JPS58108213A/ja

1990-05-21 Publication of JPH0222762B2 publication Critical patent/JPH0222762B2/ja

Status Granted legal-status Critical Current

Links

-1 2-cyanoacrylic acid ester Chemical class 0.000 title claims abstract description 44
229920000642 polymer Polymers 0.000 title claims abstract description 39
239000002904 solvent Substances 0.000 claims abstract description 19
239000003505 polymerization initiator Substances 0.000 claims abstract description 18
230000000379 polymerizing effect Effects 0.000 claims abstract description 4
238000004519 manufacturing process Methods 0.000 claims description 13
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 2
238000006116 polymerization reaction Methods 0.000 abstract description 37
238000009826 distribution Methods 0.000 abstract description 21
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 18
239000000463 material Substances 0.000 abstract description 14
238000010539 anionic addition polymerization reaction Methods 0.000 abstract description 9
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 abstract description 6
239000003112 inhibitor Substances 0.000 abstract description 6
MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 abstract description 4
238000010526 radical polymerization reaction Methods 0.000 abstract description 3
238000000034 method Methods 0.000 description 16
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
230000035945 sensitivity Effects 0.000 description 9
WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 8
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 description 4
230000005855 radiation Effects 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical compound CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 description 3
239000003999 initiator Substances 0.000 description 3
QRWOVIRDHQJFDB-UHFFFAOYSA-N isobutyl cyanoacrylate Chemical compound CC(C)COC(=O)C(=C)C#N QRWOVIRDHQJFDB-UHFFFAOYSA-N 0.000 description 3
MYWWWNVEZBAKHR-UHFFFAOYSA-N methyl 3-(3-methoxy-3-oxopropyl)sulfanylpropanoate Chemical compound COC(=O)CCSCCC(=O)OC MYWWWNVEZBAKHR-UHFFFAOYSA-N 0.000 description 3
239000012046 mixed solvent Substances 0.000 description 3
RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 3
IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical compound OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 description 2
GASDVTHQNCFANM-UHFFFAOYSA-N 3-methylbutyl 2-cyanoprop-2-enoate Chemical compound CC(C)CCOC(=O)C(=C)C#N GASDVTHQNCFANM-UHFFFAOYSA-N 0.000 description 2
229920001651 Cyanoacrylate Polymers 0.000 description 2
GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
125000000304 alkynyl group Chemical group 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
230000007423 decrease Effects 0.000 description 2
XDZLHTBOHLGGCJ-UHFFFAOYSA-N hexyl 2-cyanoprop-2-enoate Chemical compound CCCCCCOC(=O)C(=C)C#N XDZLHTBOHLGGCJ-UHFFFAOYSA-N 0.000 description 2
239000000178 monomer Substances 0.000 description 2
150000003003 phosphines Chemical class 0.000 description 2
229920002120 photoresistant polymer Polymers 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
150000003568 thioethers Chemical class 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
ZBNDUFSAYHVJNN-UHFFFAOYSA-N 2,2,2-trifluoroethyl 2-cyanoprop-2-enoate Chemical compound FC(F)(F)COC(=O)C(=C)C#N ZBNDUFSAYHVJNN-UHFFFAOYSA-N 0.000 description 1
RANXVQXZDJJZOE-UHFFFAOYSA-N 2-chloroethyl 2-cyanoprop-2-enoate Chemical compound ClCCOC(=O)C(=C)C#N RANXVQXZDJJZOE-UHFFFAOYSA-N 0.000 description 1
WXAFTQJQXYGOKV-UHFFFAOYSA-N 2-ethylhexyl 2-cyanoprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(=C)C#N WXAFTQJQXYGOKV-UHFFFAOYSA-N 0.000 description 1
JYTXVMYBYRTJTI-UHFFFAOYSA-N 2-methoxyethyl 2-cyanoprop-2-enoate Chemical compound COCCOC(=O)C(=C)C#N JYTXVMYBYRTJTI-UHFFFAOYSA-N 0.000 description 1
IXKVYKPPJAWZLH-UHFFFAOYSA-N 7-thiabicyclo[4.1.0]hepta-2,4-diene Chemical class C1=CC=CC2SC21 IXKVYKPPJAWZLH-UHFFFAOYSA-N 0.000 description 1
HTIRHQRTDBPHNZ-UHFFFAOYSA-N Dibutyl sulfide Chemical compound CCCCSCCCC HTIRHQRTDBPHNZ-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
238000010669 acid-base reaction Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
VRKSJXIKRFNNFZ-UHFFFAOYSA-N benzyl 2-cyanoprop-2-enoate Chemical compound N#CC(=C)C(=O)OCC1=CC=CC=C1 VRKSJXIKRFNNFZ-UHFFFAOYSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000002019 disulfides Chemical class 0.000 description 1
238000010894 electron beam technology Methods 0.000 description 1
JJJFUHOGVZWXNQ-UHFFFAOYSA-N enbucrilate Chemical compound CCCCOC(=O)C(=C)C#N JJJFUHOGVZWXNQ-UHFFFAOYSA-N 0.000 description 1
229950010048 enbucrilate Drugs 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
VCXUFKFNLUTDAX-UHFFFAOYSA-N ethyl 3-(3-ethoxy-3-oxopropyl)sulfanylpropanoate Chemical compound CCOC(=O)CCSCCC(=O)OCC VCXUFKFNLUTDAX-UHFFFAOYSA-N 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
RPQUGMLCZLGZTG-UHFFFAOYSA-N octyl cyanoacrylate Chemical compound CCCCCCCCOC(=O)C(=C)C#N RPQUGMLCZLGZTG-UHFFFAOYSA-N 0.000 description 1
SXRFXXNXVPFXDU-UHFFFAOYSA-N pentyl 2-cyanoprop-2-enoate Chemical compound CCCCCOC(=O)C(=C)C#N SXRFXXNXVPFXDU-UHFFFAOYSA-N 0.000 description 1
IPDQIHIYQHAUCO-UHFFFAOYSA-N phenyl 2-cyanoprop-2-enoate Chemical compound N#CC(=C)C(=O)OC1=CC=CC=C1 IPDQIHIYQHAUCO-UHFFFAOYSA-N 0.000 description 1
ITCZEZQMUWEPQP-UHFFFAOYSA-N prop-2-enyl 2-cyanoprop-2-enoate Chemical compound C=CCOC(=O)C(=C)C#N ITCZEZQMUWEPQP-UHFFFAOYSA-N 0.000 description 1
UVTYYXOSOUBFIW-UHFFFAOYSA-N prop-2-ynyl 2-cyanoprop-2-enoate Chemical compound N#CC(=C)C(=O)OCC#C UVTYYXOSOUBFIW-UHFFFAOYSA-N 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
ZTYMNUBYYQNBFP-UHFFFAOYSA-N propyl 2-cyanoprop-2-enoate Chemical compound CCCOC(=O)C(=C)C#N ZTYMNUBYYQNBFP-UHFFFAOYSA-N 0.000 description 1
MFJWXQWSVLNYKZ-UHFFFAOYSA-N propyl 3-(3-oxo-3-propoxypropyl)sulfanylpropanoate Chemical compound CCCOC(=O)CCSCCC(=O)OCCC MFJWXQWSVLNYKZ-UHFFFAOYSA-N 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
125000000101 thioether group Chemical group 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
150000004992 toluidines Chemical class 0.000 description 1

Landscapes

Polymerization Catalysts (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

JP20624381A 1981-12-22 1981-12-22 ２−シアノアクリル酸エステル重合体の製造方法 Granted JPS58108213A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP20624381A JPS58108213A (ja)	1981-12-22	1981-12-22	２−シアノアクリル酸エステル重合体の製造方法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP20624381A JPS58108213A (ja)	1981-12-22	1981-12-22	２−シアノアクリル酸エステル重合体の製造方法

Publications (2)

Publication Number	Publication Date
JPS58108213A true JPS58108213A (ja)	1983-06-28
JPH0222762B2 JPH0222762B2 (2)	1990-05-21

Family

ID=16520107

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP20624381A Granted JPS58108213A (ja)	1981-12-22	1981-12-22	２−シアノアクリル酸エステル重合体の製造方法

Country Status (1)

Country	Link
JP (1)	JPS58108213A (2)

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4675273A (en) *	1986-02-10	1987-06-23	Loctite (Ireland) Limited	Resists formed by vapor deposition of anionically polymerizable monomer
JPS63271250A (ja) *	1986-12-29	1988-11-09	Toppan Printing Co Ltd	耐ドライエッチング性ポジ型レジスト材料
JPS63271253A (ja) *	1986-12-29	1988-11-09	Toppan Printing Co Ltd	高解像度ポジ型放射線感応性レジスト
JPS63271249A (ja) *	1986-12-29	1988-11-09	Toppan Printing Co Ltd	ポジ型高感度放射線感応性レジスト
JPS63271251A (ja) *	1986-12-29	1988-11-09	Toppan Printing Co Ltd	高感度高解像度放射線感応性レジスト
JPS63271254A (ja) *	1986-12-29	1988-11-09	Toppan Printing Co Ltd	高解像度放射線感応性ポジ型レジスト
JPS63277218A (ja) *	1986-12-29	1988-11-15	Toppan Printing Co Ltd	単分散重合体の製造方法
JPS6433109A (en) *	1986-12-29	1989-02-03	Toppan Printing Co Ltd	Production of alpha-cyanoacrylate polymer
JPH01273039A (ja) *	1988-04-26	1989-10-31	Toppan Printing Co Ltd	ポジ型電子線レジスト
JPH02264955A (ja) *	1989-04-06	1990-10-29	Toppan Printing Co Ltd	ポジ型電子線レジスト
US5187048A (en) *	1989-06-23	1993-02-16	Loctite (Ireland) Limited	Photoresists formed by polymerization of di-unsaturated monomers
WO1994015907A1 (en) *	1993-01-11	1994-07-21	Eurotax Limited	Process for the preparation of esters of 2-cyanoacrylic acid and use of the esters so prepared as adhesives
US5359101A (en) *	1989-11-21	1994-10-25	Loctite Ireland, Ltd.	Anionically polymerizable monomers, polymers thereof and use of such polymers in photoresists
WO1995025753A1 (en) *	1994-03-23	1995-09-28	Kuraray Co., Ltd.	Process for producing polymer terminated with optionally protected functional group
JP2021134283A (ja) *	2020-02-27	2021-09-13	日本ゼオン株式会社	共重合体の製造方法およびポジ型レジスト組成物の製造方法

1981
- 1981-12-22 JP JP20624381A patent/JPS58108213A/ja active Granted

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4675273A (en) *	1986-02-10	1987-06-23	Loctite (Ireland) Limited	Resists formed by vapor deposition of anionically polymerizable monomer
JPS63271250A (ja) *	1986-12-29	1988-11-09	Toppan Printing Co Ltd	耐ドライエッチング性ポジ型レジスト材料
JPS63271253A (ja) *	1986-12-29	1988-11-09	Toppan Printing Co Ltd	高解像度ポジ型放射線感応性レジスト
JPS63271249A (ja) *	1986-12-29	1988-11-09	Toppan Printing Co Ltd	ポジ型高感度放射線感応性レジスト
JPS63271251A (ja) *	1986-12-29	1988-11-09	Toppan Printing Co Ltd	高感度高解像度放射線感応性レジスト
JPS63271254A (ja) *	1986-12-29	1988-11-09	Toppan Printing Co Ltd	高解像度放射線感応性ポジ型レジスト
JPS63277218A (ja) *	1986-12-29	1988-11-15	Toppan Printing Co Ltd	単分散重合体の製造方法
JPS6433109A (en) *	1986-12-29	1989-02-03	Toppan Printing Co Ltd	Production of alpha-cyanoacrylate polymer
JPH01273039A (ja) *	1988-04-26	1989-10-31	Toppan Printing Co Ltd	ポジ型電子線レジスト
JPH02264955A (ja) *	1989-04-06	1990-10-29	Toppan Printing Co Ltd	ポジ型電子線レジスト
US5187048A (en) *	1989-06-23	1993-02-16	Loctite (Ireland) Limited	Photoresists formed by polymerization of di-unsaturated monomers
US5359101A (en) *	1989-11-21	1994-10-25	Loctite Ireland, Ltd.	Anionically polymerizable monomers, polymers thereof and use of such polymers in photoresists
WO1994015907A1 (en) *	1993-01-11	1994-07-21	Eurotax Limited	Process for the preparation of esters of 2-cyanoacrylic acid and use of the esters so prepared as adhesives
WO1995025753A1 (en) *	1994-03-23	1995-09-28	Kuraray Co., Ltd.	Process for producing polymer terminated with optionally protected functional group
US5847061A (en) *	1994-03-23	1998-12-08	Kuraray Co., Ltd.	Process for producing polymers having terminal functional group which may be protected
JP3256544B2 (ja) *	1994-03-23	2002-02-12	株式会社クラレ	末端に保護されていてもよい官能基を有する重合体の製造方法
JP2021134283A (ja) *	2020-02-27	2021-09-13	日本ゼオン株式会社	共重合体の製造方法およびポジ型レジスト組成物の製造方法

Also Published As

Publication number	Publication date
JPH0222762B2 (2)	1990-05-21

Publication	Publication Date	Title
JPS58108213A (ja)	1983-06-28	２−シアノアクリル酸エステル重合体の製造方法
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CA1264394A (en)	1990-01-09	Copolymerisable surfactants, adhesive copolymers thereof and their manufacture
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US3515656A (en)	1970-06-02	Photopolymerization process for hydroxy alkyl acrylates
JPS63277218A (ja)	1988-11-15	単分散重合体の製造方法
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