DE102008001431A1 - Schneller lichthärtbarer Polymerisationsklebstoff auf MMA Basis mit verbesserten Materialeigenschaften - Google Patents
Schneller lichthärtbarer Polymerisationsklebstoff auf MMA Basis mit verbesserten Materialeigenschaften Download PDFInfo
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- DE102008001431A1 DE102008001431A1 DE102008001431A DE102008001431A DE102008001431A1 DE 102008001431 A1 DE102008001431 A1 DE 102008001431A1 DE 102008001431 A DE102008001431 A DE 102008001431A DE 102008001431 A DE102008001431 A DE 102008001431A DE 102008001431 A1 DE102008001431 A1 DE 102008001431A1
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- curing polymerization
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- ZWWQICJTBOCQLA-UHFFFAOYSA-N o-propan-2-yl (propan-2-yloxycarbothioyldisulfanyl)methanethioate Chemical compound CC(C)OC(=S)SSC(=S)OC(C)C ZWWQICJTBOCQLA-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 238000005199 ultracentrifugation Methods 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/10—Homopolymers or copolymers of methacrylic acid esters
- C09J133/12—Homopolymers or copolymers of methyl methacrylate
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- 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
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2312/00—Crosslinking
- C08L2312/06—Crosslinking by radiation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102008001431A DE102008001431A1 (de) | 2008-04-28 | 2008-04-28 | Schneller lichthärtbarer Polymerisationsklebstoff auf MMA Basis mit verbesserten Materialeigenschaften |
PCT/EP2009/052242 WO2009132872A1 (fr) | 2008-04-28 | 2009-02-26 | Adhésif à polymérisation photodurcissable rapide à base de mma présentant des propriétés de matériau améliorées |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102008001431A DE102008001431A1 (de) | 2008-04-28 | 2008-04-28 | Schneller lichthärtbarer Polymerisationsklebstoff auf MMA Basis mit verbesserten Materialeigenschaften |
Publications (1)
Publication Number | Publication Date |
---|---|
DE102008001431A1 true DE102008001431A1 (de) | 2009-10-29 |
Family
ID=40600159
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE102008001431A Withdrawn DE102008001431A1 (de) | 2008-04-28 | 2008-04-28 | Schneller lichthärtbarer Polymerisationsklebstoff auf MMA Basis mit verbesserten Materialeigenschaften |
Country Status (2)
Country | Link |
---|---|
DE (1) | DE102008001431A1 (fr) |
WO (1) | WO2009132872A1 (fr) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102012212429A1 (de) | 2012-07-16 | 2014-01-16 | Voco Gmbh | Dentalhandgerät, Verfahren und Verwendung desselben zum Aushärten lichthärtbaren Materials |
WO2018188716A1 (fr) | 2017-03-05 | 2018-10-18 | Entex Rust & Mitschke Gmbh | Dégazage lors de l'extrusion de matières, en particulier de matières plastiques |
DE102018001412A1 (de) | 2017-12-11 | 2019-06-13 | Entex Rust & Mitschke Gmbh | Entgasen beim Extrudieren von Stoffen, vorzugsweise von Kunststoffen |
Citations (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3616367A (en) | 1968-11-25 | 1971-10-26 | Du Pont | Photopolymerizable acrylic compositions containing rearrangeable ultraviolet stabilizer precursors |
DE2909993A1 (de) | 1979-03-14 | 1980-10-02 | Basf Ag | Lichthaertbare form-, traenk- und ueberzugsmassen |
EP0113924A2 (fr) | 1983-01-10 | 1984-07-25 | Röhm Gmbh | Agent de modification de la résistance à l'impact |
DE3619792A1 (de) | 1986-06-18 | 1987-12-23 | Basf Ag | Photopolymerisierbare aufzeichnungsmaterialien sowie photoresistschichten und flachdruckplatten auf basis dieser aufzeichnungsmaterialien |
GB2216136A (en) | 1988-03-29 | 1989-10-04 | Kendall & Co | Novel processes for bonding polycarbonate substrates and adhesive compositions useful therein |
DE3842796A1 (de) | 1988-12-20 | 1990-06-21 | Roehm Gmbh | Klare schlagzaehe acrylat-formmasse |
DE4000171A1 (de) | 1990-01-05 | 1991-07-11 | Roehm Gmbh | Lichthaertbares klebmittel fuer formkoerper aus acrylkunststoff und klebverfahren |
EP0465049A2 (fr) | 1990-07-03 | 1992-01-08 | Rohm And Haas Company | Matières plastiques claires résistant aux chocs |
EP0522351A1 (fr) | 1991-06-29 | 1993-01-13 | Röhm Gmbh | Agent pour la modification de la résistance à l'impact |
EP0528196A1 (fr) | 1991-08-03 | 1993-02-24 | Röhm Gmbh | Feuille mate de polyméthacrylate |
DE4142681A1 (de) * | 1991-12-21 | 1993-07-01 | Roehm Gmbh | Lichthaertbarer polymerisationskleber auf methylmethacrylat-basis |
EP0683028A1 (fr) | 1994-05-19 | 1995-11-22 | Röhm GmbH | Procédé de déshydratation de résine aqueuse dans une extrudeuse à deux vis |
DE10212458A1 (de) * | 2002-03-20 | 2003-10-02 | Roehm Gmbh | Hagelbeständiges Verbund-Acrylglas und Verfahren zu seiner Herstellung |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3724838A1 (de) * | 1987-07-27 | 1989-02-09 | Henkel Kgaa | Verwendung von lichtinduziert vernetzbaren monomer-zusammensetzungen als dunkelhaertende klebstoffe |
-
2008
- 2008-04-28 DE DE102008001431A patent/DE102008001431A1/de not_active Withdrawn
-
2009
- 2009-02-26 WO PCT/EP2009/052242 patent/WO2009132872A1/fr active Application Filing
Patent Citations (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3616367A (en) | 1968-11-25 | 1971-10-26 | Du Pont | Photopolymerizable acrylic compositions containing rearrangeable ultraviolet stabilizer precursors |
DE2909993A1 (de) | 1979-03-14 | 1980-10-02 | Basf Ag | Lichthaertbare form-, traenk- und ueberzugsmassen |
EP0113924A2 (fr) | 1983-01-10 | 1984-07-25 | Röhm Gmbh | Agent de modification de la résistance à l'impact |
US4513118A (en) | 1983-01-10 | 1985-04-23 | Rohm Gmbh | Emulsion polymers for modifying impact strength |
DE3619792A1 (de) | 1986-06-18 | 1987-12-23 | Basf Ag | Photopolymerisierbare aufzeichnungsmaterialien sowie photoresistschichten und flachdruckplatten auf basis dieser aufzeichnungsmaterialien |
GB2216136A (en) | 1988-03-29 | 1989-10-04 | Kendall & Co | Novel processes for bonding polycarbonate substrates and adhesive compositions useful therein |
DE3842796A1 (de) | 1988-12-20 | 1990-06-21 | Roehm Gmbh | Klare schlagzaehe acrylat-formmasse |
DE4000171A1 (de) | 1990-01-05 | 1991-07-11 | Roehm Gmbh | Lichthaertbares klebmittel fuer formkoerper aus acrylkunststoff und klebverfahren |
EP0465049A2 (fr) | 1990-07-03 | 1992-01-08 | Rohm And Haas Company | Matières plastiques claires résistant aux chocs |
EP0522351A1 (fr) | 1991-06-29 | 1993-01-13 | Röhm Gmbh | Agent pour la modification de la résistance à l'impact |
EP0528196A1 (fr) | 1991-08-03 | 1993-02-24 | Röhm Gmbh | Feuille mate de polyméthacrylate |
DE4142681A1 (de) * | 1991-12-21 | 1993-07-01 | Roehm Gmbh | Lichthaertbarer polymerisationskleber auf methylmethacrylat-basis |
EP0683028A1 (fr) | 1994-05-19 | 1995-11-22 | Röhm GmbH | Procédé de déshydratation de résine aqueuse dans une extrudeuse à deux vis |
DE10212458A1 (de) * | 2002-03-20 | 2003-10-02 | Roehm Gmbh | Hagelbeständiges Verbund-Acrylglas und Verfahren zu seiner Herstellung |
Non-Patent Citations (6)
Title |
---|
DIN 53 727 bzw. 51 562, Teil 1 |
DIN 53283 |
DIN EN 1465 |
ISO 306-650 |
Polym. Paint Colour J., 175 (4150), 636-8, 640 (1985) |
siehe z. B. H. F. Mark et al., Encyclopedia of Polymer Science and Engineering, 2nd. Edition, Vol. 10, Seiten 1 ff., J. Wiley, 1989 |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102012212429A1 (de) | 2012-07-16 | 2014-01-16 | Voco Gmbh | Dentalhandgerät, Verfahren und Verwendung desselben zum Aushärten lichthärtbaren Materials |
WO2018188716A1 (fr) | 2017-03-05 | 2018-10-18 | Entex Rust & Mitschke Gmbh | Dégazage lors de l'extrusion de matières, en particulier de matières plastiques |
US11613060B2 (en) | 2017-03-05 | 2023-03-28 | Entex Rust & Mitschke Gmbh | Planetary roller extruder with a degassing section |
DE102018001412A1 (de) | 2017-12-11 | 2019-06-13 | Entex Rust & Mitschke Gmbh | Entgasen beim Extrudieren von Stoffen, vorzugsweise von Kunststoffen |
Also Published As
Publication number | Publication date |
---|---|
WO2009132872A1 (fr) | 2009-11-05 |
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