JPS6143363B2 - - Google Patents
Info
- Publication number
- JPS6143363B2 JPS6143363B2 JP23369582A JP23369582A JPS6143363B2 JP S6143363 B2 JPS6143363 B2 JP S6143363B2 JP 23369582 A JP23369582 A JP 23369582A JP 23369582 A JP23369582 A JP 23369582A JP S6143363 B2 JPS6143363 B2 JP S6143363B2
- Authority
- JP
- Japan
- Prior art keywords
- fluorine
- containing monomer
- molecular weight
- telomer
- acid chloride
- 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
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 25
- 239000011737 fluorine Substances 0.000 claims abstract description 25
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000000178 monomer Substances 0.000 claims abstract description 16
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000005886 esterification reaction Methods 0.000 abstract description 3
- 230000032050 esterification Effects 0.000 abstract description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 abstract 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-AKLPVKDBSA-N carbane Chemical compound [15CH4] VNWKTOKETHGBQD-AKLPVKDBSA-N 0.000 description 2
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 2
- 239000012567 medical material Substances 0.000 description 2
- 239000011505 plaster Substances 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002788 crimping Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 150000002221 fluorine Chemical class 0.000 description 1
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- YPVDWEHVCUBACK-UHFFFAOYSA-N propoxycarbonyloxy propyl carbonate Chemical compound CCCOC(=O)OOC(=O)OCCC YPVDWEHVCUBACK-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000003797 telogen phase Effects 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- -1 trifluoroethylene, tetrafluoroethylene, chlorotrifluoroethylene, hexafluoropropylene Chemical group 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
- A61K6/887—Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/14—Esterification
-
- 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
- C08F2810/00—Chemical modification of a polymer
- C08F2810/30—Chemical modification of a polymer leading to the formation or introduction of aliphatic or alicyclic unsaturated groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Plastic & Reconstructive Surgery (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Dental Preparations (AREA)
- Polymerisation Methods In General (AREA)
- Dental Prosthetics (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57233695A JPS59117503A (ja) | 1982-12-24 | 1982-12-24 | 新規な含フツ素単量体の製造法 |
| GB08334072A GB2132209B (en) | 1982-12-24 | 1983-12-21 | Fluorine-containing macromonomer |
| FR8320713A FR2538383B1 (fr) | 1982-12-24 | 1983-12-23 | Nouveau monomere fluore et procede pour sa preparation |
| DE3346871A DE3346871C2 (de) | 1982-12-24 | 1983-12-23 | Fluorhaltige Monomere und Verfahren zu deren Herstellung |
| US06/694,665 US4580981A (en) | 1982-12-24 | 1985-01-24 | Fluorine-containing monomer and process for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57233695A JPS59117503A (ja) | 1982-12-24 | 1982-12-24 | 新規な含フツ素単量体の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59117503A JPS59117503A (ja) | 1984-07-06 |
| JPS6143363B2 true JPS6143363B2 (en]) | 1986-09-27 |
Family
ID=16959094
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57233695A Granted JPS59117503A (ja) | 1982-12-24 | 1982-12-24 | 新規な含フツ素単量体の製造法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4580981A (en]) |
| JP (1) | JPS59117503A (en]) |
| DE (1) | DE3346871C2 (en]) |
| FR (1) | FR2538383B1 (en]) |
| GB (1) | GB2132209B (en]) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01118068U (en]) * | 1988-01-30 | 1989-08-09 | ||
| JPH02115874U (en]) * | 1989-03-02 | 1990-09-17 |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60146810A (ja) * | 1984-01-05 | 1985-08-02 | Kureha Chem Ind Co Ltd | 軟質義歯床裏装材料 |
| JPH0319368Y2 (en]) * | 1986-11-05 | 1991-04-24 | ||
| JPH01100108A (ja) * | 1987-10-09 | 1989-04-18 | Kureha Chem Ind Co Ltd | ポイント型歯科用根管充填材料 |
| US5328362A (en) * | 1992-03-11 | 1994-07-12 | Watson Sherman L | Soft resilient interocclusal dental appliance, method of forming same and composition for same |
| US6166156A (en) * | 1998-11-12 | 2000-12-26 | Wu; Chengjiu | Method for making photocurable halofluorinated acrylates |
| FR2810668B1 (fr) * | 2000-06-23 | 2003-09-19 | Commissariat Energie Atomique | Procede de preparation de polymeres fluores telecheliques et polymeres ainsi prepares |
| US7176265B2 (en) * | 2002-11-22 | 2007-02-13 | E. I. Du Pont De Nemours And Company | Directly polymerized low molecular weight granular polytetrafluoroethylene |
| EP1607986B1 (en) | 2003-03-26 | 2011-07-27 | Daikin Industries, Limited | Method for forming ferroelectric thin film |
| JP3867709B2 (ja) | 2003-03-26 | 2007-01-10 | ダイキン工業株式会社 | 薄膜の形成方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3073795A (en) * | 1959-09-25 | 1963-01-15 | Joseph E Veverka | Dental liner comprising polymethyl methacrylate, talc and methyl methacrylate |
| US3457247A (en) * | 1965-02-12 | 1969-07-22 | Daikin Ind Ltd | Fluorocarbon compounds and polymers thereof |
| BE622421A (en]) * | 1967-02-23 | 1900-01-01 | ||
| US3647887A (en) * | 1967-04-25 | 1972-03-07 | Allied Chem | Aryl-substituted polyfluoroalkoxyalkanes |
| US3523133A (en) * | 1967-11-22 | 1970-08-04 | Pennwalt Corp | Preparation of fluorinated esters |
| US3547861A (en) * | 1968-04-12 | 1970-12-15 | Allied Chem | Novel fluorinated acrylates and polyacrylates |
| US3864318A (en) * | 1970-01-24 | 1975-02-04 | Monteratini Edison S P A | Acrylic and methacrylic monomers, polymers and copolymers |
| DE2350571A1 (de) * | 1972-10-18 | 1974-05-02 | Ciba Geigy Ag | Verfahren zu ihrer herstellung und verwendung von neuer carbonsaeureperfluoralkylester |
-
1982
- 1982-12-24 JP JP57233695A patent/JPS59117503A/ja active Granted
-
1983
- 1983-12-21 GB GB08334072A patent/GB2132209B/en not_active Expired
- 1983-12-23 FR FR8320713A patent/FR2538383B1/fr not_active Expired
- 1983-12-23 DE DE3346871A patent/DE3346871C2/de not_active Expired
-
1985
- 1985-01-24 US US06/694,665 patent/US4580981A/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01118068U (en]) * | 1988-01-30 | 1989-08-09 | ||
| JPH02115874U (en]) * | 1989-03-02 | 1990-09-17 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2538383A1 (fr) | 1984-06-29 |
| DE3346871A1 (de) | 1985-07-18 |
| JPS59117503A (ja) | 1984-07-06 |
| GB2132209B (en) | 1986-06-18 |
| FR2538383B1 (fr) | 1988-11-04 |
| DE3346871C2 (de) | 1986-07-03 |
| GB2132209A (en) | 1984-07-04 |
| US4580981A (en) | 1986-04-08 |
| GB8334072D0 (en) | 1984-02-01 |
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