JPH0739382B2 - マクロモノマーフルオルアルキル基を有する（メタ）アクリル酸エステルおよびその製法 - Google Patents
マクロモノマーフルオルアルキル基を有する（メタ）アクリル酸エステルおよびその製法Info
- Publication number
- JPH0739382B2 JPH0739382B2 JP1319069A JP31906989A JPH0739382B2 JP H0739382 B2 JPH0739382 B2 JP H0739382B2 JP 1319069 A JP1319069 A JP 1319069A JP 31906989 A JP31906989 A JP 31906989A JP H0739382 B2 JPH0739382 B2 JP H0739382B2
- Authority
- JP
- Japan
- Prior art keywords
- meth
- acrylic acid
- acid ester
- units
- value
- 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 - Lifetime
Links
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title claims description 11
- 125000003709 fluoroalkyl group Chemical group 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 17
- -1 acrylic ester Chemical class 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 7
- 239000000178 monomer Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 125000006353 oxyethylene group Chemical group 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000012966 redox initiator Substances 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
- GGSQMKDPESKTMD-UHFFFAOYSA-N (1,1,1,3,3,3-hexafluoro-2-phenylpropan-2-yl) prop-2-enoate Chemical compound C=CC(=O)OC(C(F)(F)F)(C(F)(F)F)C1=CC=CC=C1 GGSQMKDPESKTMD-UHFFFAOYSA-N 0.000 description 1
- UGVKSFUTKAXDFO-UHFFFAOYSA-N (1,2,2,2-tetrafluoro-1-phenylethyl)benzene Chemical class C=1C=CC=CC=1C(F)(C(F)(F)F)C1=CC=CC=C1 UGVKSFUTKAXDFO-UHFFFAOYSA-N 0.000 description 1
- JDIJDQNYSUHWJJ-UHFFFAOYSA-N 1,1,1,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-henicosafluorodecan-2-ol Chemical compound FC(F)(F)C(F)(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JDIJDQNYSUHWJJ-UHFFFAOYSA-N 0.000 description 1
- HSOOIVBINKDISP-UHFFFAOYSA-N 1-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(CCC)OC(=O)C(C)=C HSOOIVBINKDISP-UHFFFAOYSA-N 0.000 description 1
- RSVZYSKAPMBSMY-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)C(F)F RSVZYSKAPMBSMY-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- JUVSRZCUMWZBFK-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)-4-methylanilino]ethanol Chemical compound CC1=CC=C(N(CCO)CCO)C=C1 JUVSRZCUMWZBFK-UHFFFAOYSA-N 0.000 description 1
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
- KRLZEJYMWDKCNW-UHFFFAOYSA-N [3,3,4,4,5,5-hexafluoro-5-(2-methylprop-2-enoyloxy)pentyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC(F)(F)C(F)(F)C(F)(F)OC(=O)C(C)=C KRLZEJYMWDKCNW-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- IIQWTZQWBGDRQG-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate;isocyanic acid Chemical compound N=C=O.CCOC(=O)C(C)=C IIQWTZQWBGDRQG-UHFFFAOYSA-N 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000002241 glass-ceramic Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 238000010327 methods by industry Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/65—Halogen-containing esters of unsaturated acids
- C07C69/653—Acrylic acid esters; Methacrylic acid esters; Haloacrylic acid esters; Halomethacrylic acid esters
-
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/16—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
-
- 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
- C08F20/00—Homopolymers and 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
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F20/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
-
- 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
- C08F20/00—Homopolymers and 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
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
- C08F20/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/288—Compounds containing at least one heteroatom other than oxygen or nitrogen
- C08G18/2885—Compounds containing at least one heteroatom other than oxygen or nitrogen containing halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/81—Unsaturated isocyanates or isothiocyanates
- C08G18/8108—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group
- C08G18/8116—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group esters of acrylic or alkylacrylic acid having only one isocyanate or isothiocyanate group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Epidemiology (AREA)
- Plastic & Reconstructive Surgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dental Preparations (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3841617.4 | 1988-12-10 | ||
| DE3844619A DE3844619A1 (de) | 1988-12-10 | 1988-12-10 | Verwendung von perfluoroalkylgruppen aufweisenden (meth-)acrylsaeureestern in der dentaltechnik |
| DE3841617A DE3841617C1 (enExample) | 1988-12-10 | 1988-12-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02202866A JPH02202866A (ja) | 1990-08-10 |
| JPH0739382B2 true JPH0739382B2 (ja) | 1995-05-01 |
Family
ID=25874996
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1319069A Expired - Lifetime JPH0739382B2 (ja) | 1988-12-10 | 1989-12-11 | マクロモノマーフルオルアルキル基を有する（メタ）アクリル酸エステルおよびその製法 |
| JP1319070A Expired - Lifetime JPH0791172B2 (ja) | 1988-12-10 | 1989-12-11 | 歯科材料を調製するための硬化性モノマー混合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1319070A Expired - Lifetime JPH0791172B2 (ja) | 1988-12-10 | 1989-12-11 | 歯科材料を調製するための硬化性モノマー混合物 |
Country Status (5)
| Country | Link |
|---|---|
| EP (2) | EP0373384B1 (enExample) |
| JP (2) | JPH0739382B2 (enExample) |
| DE (3) | DE3841617C1 (enExample) |
| ES (2) | ES2052867T3 (enExample) |
| GR (2) | GR3006881T3 (enExample) |
Families Citing this family (73)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1270818B (it) * | 1993-04-28 | 1997-05-13 | Ausimont Spa | Coatings a base di perfluoropolieteri contenenti gruppi acrilici |
| US5662887A (en) * | 1994-12-01 | 1997-09-02 | Minnesota Mining And Manufacturing Company | Fluorocarbon containing coatings, compositions and methods of use |
| DE4445266A1 (de) * | 1994-12-19 | 1996-06-20 | Thera Ges Fuer Patente | Fluoridabgebende Composite-Massen |
| FR2749170B1 (fr) * | 1996-05-30 | 1998-08-21 | Bellesort Stephane | Protheses dentaires modifiees en surface et procede d'obtention |
| JP2002537422A (ja) | 1999-02-18 | 2002-11-05 | ノバルティス アクチエンゲゼルシャフト | 新しい生体材料 |
| DE60005423T2 (de) | 1999-03-03 | 2004-07-22 | KURARAY CO., LTD, Kurashiki | Unterfütterungsmaterial für Zahnprothesen |
| JP2003502493A (ja) * | 1999-06-22 | 2003-01-21 | ノバルティス アクチエンゲゼルシャフト | 成形物の製造方法 |
| US7134875B2 (en) | 2002-06-28 | 2006-11-14 | 3M Innovative Properties Company | Processes for forming dental materials and device |
| US6773261B2 (en) | 2002-06-28 | 2004-08-10 | 3M Innovative Properties Company | Processes for forming dental materials |
| US20040206932A1 (en) | 2002-12-30 | 2004-10-21 | Abuelyaman Ahmed S. | Compositions including polymerizable bisphosphonic acids and methods |
| US7449499B2 (en) | 2003-08-12 | 2008-11-11 | 3M Innovative Properties Company | Self-etching dental compositions and methods |
| US7030169B2 (en) | 2003-09-26 | 2006-04-18 | 3M Innovative Properties Company | Arylsulfinate salts in initiator systems for polymeric reactions |
| US7250452B2 (en) | 2003-09-26 | 2007-07-31 | 3M Innovative Properties Company | Dental compositions and methods with arylsulfinate salts |
| US7026367B2 (en) | 2003-09-26 | 2006-04-11 | 3M Innovative Properties Company | Photoiniators having triarylsulfonium and arylsulfinate ions |
| US7649029B2 (en) | 2004-05-17 | 2010-01-19 | 3M Innovative Properties Company | Dental compositions containing nanozirconia fillers |
| US7156911B2 (en) | 2004-05-17 | 2007-01-02 | 3M Innovative Properties Company | Dental compositions containing nanofillers and related methods |
| US7090722B2 (en) | 2004-05-17 | 2006-08-15 | 3M Innovative Properties Company | Acid-reactive dental fillers, compositions, and methods |
| US7090721B2 (en) | 2004-05-17 | 2006-08-15 | 3M Innovative Properties Company | Use of nanoparticles to adjust refractive index of dental compositions |
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Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL266570A (enExample) * | 1960-07-09 | |||
| CH1753669D (enExample) * | 1968-11-25 | |||
| US3660360A (en) * | 1970-06-24 | 1972-05-02 | Nat Starch Chem Corp | Water- and oil repellency agents |
| US4508916A (en) * | 1979-04-11 | 1985-04-02 | Minnesota Mining And Manufacturing Company | Curable substituted urethane acrylates |
| JPS60146810A (ja) * | 1984-01-05 | 1985-08-02 | Kureha Chem Ind Co Ltd | 軟質義歯床裏装材料 |
| US4616073A (en) * | 1984-08-09 | 1986-10-07 | The United States Of America As Represented By The Department Of Health And Human Services | Hydrophobic dental composites based on a polyfluorinated dental resin |
| US4612356A (en) * | 1984-10-01 | 1986-09-16 | Ciba-Geigy Corporation | Homo- and co- (addition) polymers of di-perfluoroalkyl carbamyl group containing (meth) acrylate monomers |
| JPS61111309A (ja) * | 1984-11-02 | 1986-05-29 | Daikin Ind Ltd | α−フルオロアクリル酸誘導体ポリマ− |
| IT1185520B (it) * | 1985-02-22 | 1987-11-12 | Montefluos Spa | Poliacrilati e poliacrilammidi fluorurati a grado di reticolazione controllato e loro procedimento di preparazione |
| JPH01305052A (ja) * | 1988-06-01 | 1989-12-08 | Nippon Oil & Fats Co Ltd | ポリフルオロアルキルポリオキシアルキレン（メタ）アクリレート |
-
1988
- 1988-12-10 DE DE3841617A patent/DE3841617C1/de not_active Expired - Lifetime
- 1988-12-10 DE DE3844619A patent/DE3844619A1/de not_active Ceased
-
1989
- 1989-11-20 DE DE8989121424T patent/DE58903288D1/de not_active Expired - Fee Related
- 1989-11-20 ES ES89121422T patent/ES2052867T3/es not_active Expired - Lifetime
- 1989-11-20 EP EP89121422A patent/EP0373384B1/de not_active Expired - Lifetime
- 1989-11-20 ES ES89121424T patent/ES2053923T3/es not_active Expired - Lifetime
- 1989-11-20 EP EP89121424A patent/EP0373385B1/de not_active Expired - Lifetime
- 1989-12-11 JP JP1319069A patent/JPH0739382B2/ja not_active Expired - Lifetime
- 1989-12-11 JP JP1319070A patent/JPH0791172B2/ja not_active Expired - Lifetime
-
1993
- 1993-01-26 GR GR920403056T patent/GR3006881T3/el unknown
- 1993-02-11 GR GR920402397T patent/GR3007024T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02202866A (ja) | 1990-08-10 |
| EP0373384B1 (de) | 1992-10-28 |
| GR3006881T3 (enExample) | 1993-06-30 |
| JPH02202850A (ja) | 1990-08-10 |
| DE58903288D1 (de) | 1993-02-25 |
| ES2052867T3 (es) | 1994-07-16 |
| GR3007024T3 (enExample) | 1993-07-30 |
| EP0373384A1 (de) | 1990-06-20 |
| EP0373385B1 (de) | 1993-01-13 |
| EP0373385A1 (de) | 1990-06-20 |
| DE3844619A1 (de) | 1990-07-12 |
| ES2053923T3 (es) | 1994-08-01 |
| JPH0791172B2 (ja) | 1995-10-04 |
| DE3841617C1 (enExample) | 1990-05-10 |
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