GB1576741A - Electron sensitive acrylate resin - Google Patents
Electron sensitive acrylate resin Download PDFInfo
- Publication number
- GB1576741A GB1576741A GB21007/77A GB2100777A GB1576741A GB 1576741 A GB1576741 A GB 1576741A GB 21007/77 A GB21007/77 A GB 21007/77A GB 2100777 A GB2100777 A GB 2100777A GB 1576741 A GB1576741 A GB 1576741A
- Authority
- GB
- United Kingdom
- Prior art keywords
- resin
- epithiopropylmethacrylate
- solution
- formula
- alkyl group
- 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
- 239000004925 Acrylic resin Substances 0.000 title description 2
- 239000011347 resin Substances 0.000 claims description 28
- 229920005989 resin Polymers 0.000 claims description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000000178 monomer Substances 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical group [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- 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 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000004377 microelectronic Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000013043 chemical agent Substances 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- -1 potassium ferricyanide Chemical compound 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/38—Esters containing sulfur
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
- Y10S430/111—Polymer of unsaturated acid or ester
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/143—Electron beam
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Polymerisation Methods In General (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7615520A FR2352007A1 (fr) | 1976-05-21 | 1976-05-21 | Resine sensible aux electrons et procede de fabrication de ladite resine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1576741A true GB1576741A (en) | 1980-10-15 |
Family
ID=9173500
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21007/77A Expired GB1576741A (en) | 1976-05-21 | 1977-05-18 | Electron sensitive acrylate resin |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4315067A (enExample) |
| JP (1) | JPS5835527B2 (enExample) |
| DE (1) | DE2722951C2 (enExample) |
| FR (1) | FR2352007A1 (enExample) |
| GB (1) | GB1576741A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4414081A (en) | 1977-03-04 | 1983-11-08 | Thomson - Csf | Family of compounds crosslinkable by photon irradiation |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2441634A1 (fr) * | 1978-11-14 | 1980-06-13 | Thomson Csf | Resine a cycle thietane reticulable par irradiation electronique ou photonique et son utilisation pour la fabrication de composants electroniques et de couches de protection |
| FR2472768A1 (fr) * | 1979-12-27 | 1981-07-03 | Thomson Csf | Composition photopolymerisable comportant un cycle thiirane, procede de revetement d'une fibre optique utilisant une telle composition, et fibre ainsi revetue |
| JPS59146048A (ja) * | 1983-02-09 | 1984-08-21 | Chisso Corp | 電子線又はｘ線に感応性の樹脂 |
| GB2163435B (en) * | 1984-07-11 | 1987-07-22 | Asahi Chemical Ind | Image-forming materials sensitive to high-energy beam |
| FR2630744B1 (fr) * | 1988-04-29 | 1992-04-17 | Thomson Csf | Procede d'obtention d'un materiau polymere utilisable en optique non lineaire et materiau polymere obtenu |
| JP3245324B2 (ja) * | 1995-03-31 | 2002-01-15 | カネボウ株式会社 | 金属接着剤及び接着方法 |
| TWI482814B (zh) * | 2007-03-16 | 2015-05-01 | Mitsubishi Gas Chemical Co | 光學材料用樹脂組成物及由該組成物得到之光學材料 |
| GB2515697B (en) * | 2012-04-26 | 2020-03-04 | Ppg Ind Ohio Inc | Polymerizable compositions containing ethylenically unsaturated monomers having episulfide functional groups and related methods |
| US9279907B2 (en) | 2012-12-05 | 2016-03-08 | Ppg Industries Ohio, Inc. | Epoxide and thioepoxide functional, polymerizable compositions and methods of preparing optical articles therefrom |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3364184A (en) * | 1959-12-04 | 1968-01-16 | Shell Oil Co | Oil - soluble polymeric glycidyl compounds and functional organic compositions containing them |
| US3404158A (en) * | 1964-05-18 | 1968-10-01 | Thiokol Chemical Corp | Thioglycidyl compounds |
| US4130424A (en) * | 1976-08-06 | 1978-12-19 | Bell Telephone Laboratories, Incorporated | Process using radiation curable epoxy containing resist and resultant product |
-
1976
- 1976-05-21 FR FR7615520A patent/FR2352007A1/fr active Granted
-
1977
- 1977-05-18 GB GB21007/77A patent/GB1576741A/en not_active Expired
- 1977-05-20 DE DE2722951A patent/DE2722951C2/de not_active Expired
- 1977-05-21 JP JP52059292A patent/JPS5835527B2/ja not_active Expired
-
1980
- 1980-07-09 US US06/167,036 patent/US4315067A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4414081A (en) | 1977-03-04 | 1983-11-08 | Thomson - Csf | Family of compounds crosslinkable by photon irradiation |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2722951A1 (de) | 1977-12-01 |
| FR2352007A1 (fr) | 1977-12-16 |
| JPS52142793A (en) | 1977-11-28 |
| DE2722951C2 (de) | 1987-05-07 |
| JPS5835527B2 (ja) | 1983-08-03 |
| FR2352007B1 (enExample) | 1979-08-17 |
| US4315067A (en) | 1982-02-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1088737A (en) | High energy radiation curable resist and preparatory process | |
| EP0005551B1 (en) | Article comprising a substrate and an overlying layer of electron beam radiation-sensitive material and process for fabrication thereof | |
| GB1576741A (en) | Electron sensitive acrylate resin | |
| CA1166061A (en) | Method of forming a negative resist pattern by exposing to crosslink a copolymer containing halomethyl or acrylymethyl substituted styrene units | |
| JPS6052845A (ja) | パタ−ン形成材料 | |
| ES8103476A1 (es) | Procedimiento para la produccion de dispositivos en estado solido mediante tecnicas de procesado con plasma | |
| GB1582735A (en) | Positive resist mask formation | |
| GB1580302A (en) | Compounds crosslinkable by photon irradiation | |
| US5192643A (en) | Pattern-forming method and radiation resist for use when working this pattern-forming method | |
| GB1595886A (en) | Electrolithographic process which makes it possible to improve the sensitivity of masking resins and a mask obtained by this kind of process | |
| CA2118753C (en) | Method of forming a micro structure and an x-ray mask | |
| US4965340A (en) | Copolymer from sulfur dioxide and vinyl compound | |
| DE3339267C2 (de) | In Lösungsmitteln lösliche Copolymere, Verfahren zu ihrer Herstellung und ihre Verwendung in gegenüber ionisierender Strahlung empfindlichem Fotolack | |
| US4504646A (en) | Positive type, radiation-sensitive organic polymer materials | |
| JPH0629323B2 (ja) | 二酸化硫黄とビニル化合物から成る多元共重合体 | |
| JPS6120031A (ja) | レジスト材料およびその製造方法 | |
| JPH0734113B2 (ja) | レジスト材料 | |
| JPS62280839A (ja) | レジスト材料およびパタ−ン形成方法 | |
| JPS6125140A (ja) | エネルギ−線感応性高分子レジスト | |
| JPS5975244A (ja) | 放射線感応性有機高分子材料 | |
| JPH0427542B2 (enExample) | ||
| JPS6234908A (ja) | ケイ素とビニル基を含むα−メチルスチレン系重合体とそれを含む組成物とその使用方法 | |
| JPS61151530A (ja) | 電子線レジスト材料組成物 | |
| JPS6091350A (ja) | 電離放射線感応ネガ型レジスト | |
| JPS6347753A (ja) | レジスト材料およびパタ−ン形成方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19950518 |