EP2217660A1 - Radikalisch vernetzbare polymerisat-zusammensetzungen enthaltend epoxy-funktionelle copolymere - Google Patents
Radikalisch vernetzbare polymerisat-zusammensetzungen enthaltend epoxy-funktionelle copolymereInfo
- Publication number
- EP2217660A1 EP2217660A1 EP08858142A EP08858142A EP2217660A1 EP 2217660 A1 EP2217660 A1 EP 2217660A1 EP 08858142 A EP08858142 A EP 08858142A EP 08858142 A EP08858142 A EP 08858142A EP 2217660 A1 EP2217660 A1 EP 2217660A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- epoxy
- functional
- monomers
- polymer compositions
- radically crosslinkable
- 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.)
- Withdrawn
Links
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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/061—Polyesters; Polycarbonates
-
- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/01—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to unsaturated polyesters
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/08—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds
Definitions
- EP-A 0075765 recommends free-radically crosslinkable polymer compositions for the production of composite components, which contain, as LPA polymers based on vinyl acetate or alkyl acrylates and additionally ethylenically unsaturated fatty acid esters, through which the formation of composite components with as smooth as possible less corrugated surfaces is favored.
- US Pat. No. 4,525,498 discloses radically crosslinkable polymer compositions comprising unsaturated polyester resin, vinyl acetate-based or alkyl acrylate-based LPA and saturated, epoxy group-bearing, low molecular weight compounds by which the shrinkage-reducing effect of the LPA during curing increased the composition and the surface properties of the composite components can be improved.
- a significant increase in the mechanical properties of the composite components did not cause the addition of epoxide group-bearing, low molecular weight compounds. In addition, low molecular weight compounds tend to migrate and are easily released from the composite components.
- epoxy-functional copolymers based on vinyl acetate and one or more monomers b), such as in particular glycidyl methacrylate, and optionally vinyl laurate, acrylic acid or crotonic acid in the abovementioned amounts.
- the epoxy-functional copolymers preferably contain the epoxy-functional monomer units in random distribution, i. the epoxy-functional copolymers are preferably not grafted with epoxy-functional monomers or compounds.
- Suitable reactive monomers are the monomers which are suitable, preferably or particularly preferred, which are also suitable, preferred or particularly preferred for the polymerization for the preparation of the epoxy-functional copolymers.
- Very particularly preferred reactive monomers are styrene, methyl methacrylate, methyl acrylate and butyl acrylate. The most preferred reactive monomer is styrene.
- Suitable polyols preferably have 2 to 20 and more preferably 2 to 10 carbon atoms. Polyols preferably carry 2 to 3, more preferably 2 alcohol groups. Examples of suitable polyols are ethylene glycol, diethylene glycol,
- the unsaturated polyester resins have molecular weights Mw of preferably 500 to 10,000 g / mol, more preferably 500 to 6,000 g / mol, and most preferably 1,000 to 6,000 g / mol.
- Vinyl ester resins are reaction products which are formed by polyadditions or esterification reactions of phenol derivatives and ethylenically unsaturated mono- or dicarboxylic acids or dicarboxylic anhydrides having 3 to 20 carbon atoms, such as, for example, acrylic acids or methacrylic acids.
- Preferred phenol derivatives are bisphenol A and phenol novolac.
- the preparation of the vinyl ester resins is known to the person skilled in the art.
- Suitable initiators are, for example, t-butyl perbenzoate, t-butyl peroxy-2-ethylhexanoate, t-butyl peroxypivalate, t-butyl peroxyneodecanoate, dibenzoyl peroxide, t-amyl peroxypivalate, di (2-ethylhexyl) peroxydicarbonate, 1,1-bis (t-butyl peroxy ) -3, 3, 5-trimethylcyclohexane, di (4-t-butylcyclohexyl) peroxydicarbonate, azobisisobutyronitrile.
- the solutions of the radically crosslinkable polymers in reactive monomer and the epoxy-functional copolymers and optionally the further components such as the initiator, filler, mold release agent or other polymers, low-profile additives or additives are mixed to form a pasty mass, Thereafter, if appropriate, glass fiber is admixed, and then the resulting free-radically crosslinkable polymer compositions are cured using pressure and temperature to form the composite component. For example, reflectors for car headlights are produced with this technology.
- a radically crosslinkable polymer composition in the form of a pasty mass of a solution of free-radically crosslinkable polymers in reactive monomer and the epoxy-functional Copolymer and optionally the other components such as initiator, filler, mold release agents, other polymers, low-profile additives or additives produced and applied to a polyamide film.
- glass fiber is sprinkled onto this layer, then optionally a further layer of the pasty mass is applied and finally covered with a further polyamide film.
- This sheet sandwich is then peeled from the film, cut into pieces and pressed using compression and temperature to composite components.
- Composite components made by this technique are used, for example, as tailgates of automobiles.
- GMA glycidyl methacrylate; the indication in Gew. -% refers to the total weight of the copolymer.
- Mw molecular weight M w (weight average) determined by means of SEC "Si ze exclusion chromatography", polystyrene standard, THF; 6O 0 C.
- BF flexural strength: determined according to DIN EN I SO 14125. The flexural strength of the composite components was determined on the basis of the test specimens according to EN ISO 14125. The test results for the various specimens are listed in Table 2.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102007055692A DE102007055692A1 (de) | 2007-12-03 | 2007-12-03 | Radikalisch vernetzbare Polymerisat-Zusammensetzungen enthaltend Epoxy-funktionelle Copolymere |
PCT/EP2008/066531 WO2009071508A1 (de) | 2007-12-03 | 2008-12-01 | Radikalisch vernetzbare polymerisat-zusammensetzungen enthaltend epoxy-funktionelle copolymere |
Publications (1)
Publication Number | Publication Date |
---|---|
EP2217660A1 true EP2217660A1 (de) | 2010-08-18 |
Family
ID=40336469
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP08858142A Withdrawn EP2217660A1 (de) | 2007-12-03 | 2008-12-01 | Radikalisch vernetzbare polymerisat-zusammensetzungen enthaltend epoxy-funktionelle copolymere |
Country Status (6)
Country | Link |
---|---|
US (1) | US20100256287A1 (zh) |
EP (1) | EP2217660A1 (zh) |
CN (1) | CN101883823A (zh) |
CA (1) | CA2704889C (zh) |
DE (1) | DE102007055692A1 (zh) |
WO (1) | WO2009071508A1 (zh) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102008054482A1 (de) * | 2008-12-10 | 2010-06-17 | Wacker Chemie Ag | Pfropfcopolymere und deren Verwendung als Low-Profile-Additive |
CN111154370B (zh) * | 2020-01-15 | 2021-06-08 | 华东理工大学 | 一种抗菌丙烯酸酯涂料及其制备方法与应用 |
CN113930060A (zh) * | 2021-10-25 | 2022-01-14 | 河北多凯复合材料有限公司 | 一种新型高性能防静电阻燃复合材料及其制备方法 |
Family Cites Families (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3437514A (en) * | 1967-08-02 | 1969-04-08 | Ford Motor Co | Radiation crosslinking of alpha-beta unsaturated paint binder resin |
US3574157A (en) * | 1969-02-03 | 1971-04-06 | Fred Markus | Coating composition of epoxy resins,polyester resins,and vinyl monomers |
US3718714A (en) | 1970-09-16 | 1973-02-27 | Union Carbide Corp | Unsaturated polyester compositions |
US3689307A (en) * | 1970-12-21 | 1972-09-05 | Ford Motor Co | Graded rubber-urethane-acrylate paint and painting process |
US4284736A (en) | 1971-01-18 | 1981-08-18 | Union Carbide Corporation | Unsaturated polyester compositions |
DE2441025C3 (de) * | 1973-08-29 | 1978-10-26 | Mitsubishi Rayon Co. Ltd., Tokio | Schwundarm härtbare ungesättigte Polyesterharzgemische und deren Verwendung für Formkörper mit verbesserter Haftfähigkeit für Überzüge |
US4341877A (en) * | 1980-06-04 | 1982-07-27 | Ppg Industries, Inc. | Sizing composition and sized glass fibers and process |
US4525498A (en) | 1980-10-16 | 1985-06-25 | Union Carbide Corporation | Polyester fiber reinforced molding compounds |
CA1196118A (en) | 1981-09-11 | 1985-10-29 | Kenneth E. Atkins | Polyester molding compositions |
US4448941A (en) * | 1981-12-07 | 1984-05-15 | Ford Motor Company | Resin binder for fiber composite materials |
US4473618A (en) * | 1983-05-13 | 1984-09-25 | Owens-Corning Fiberglas Corporation | Chrome-free sizing composition containing titanium acetyl acetonate for glass fiber gun roving |
US6329475B1 (en) * | 1992-08-12 | 2001-12-11 | The Dow Chemical Company | Curable epoxy vinylester composition having a low peak exotherm during cure |
AU7845594A (en) * | 1993-09-28 | 1995-04-18 | Cambridge Industries, Inc. | Additives to improve surface characteristics of unsaturated polyester molding composition |
US5541253A (en) * | 1994-10-11 | 1996-07-30 | The B. F. Goodrich Company | High solids copolymer dispersion from a latex and its use in sealants |
US5712036A (en) * | 1996-05-08 | 1998-01-27 | N.V. Owens-Corning S.A. | High solubility size compositon for fibers |
US6221425B1 (en) * | 1998-01-30 | 2001-04-24 | Advanced Cardiovascular Systems, Inc. | Lubricious hydrophilic coating for an intracorporeal medical device |
US6348270B1 (en) * | 1999-09-01 | 2002-02-19 | Reichhold Inc. | High performance polyetherester containing laminating resin compositions |
US6803414B2 (en) * | 1999-09-29 | 2004-10-12 | Mitsubishi Fuso Truck And Bus Corporation | Damping resin composition and damping resin article for structure using the resin composition |
DE10054162A1 (de) * | 2000-11-02 | 2002-05-16 | Wacker Polymer Systems Gmbh | Verfahren zur Herstellung von Holzpressplatten |
IT1319683B1 (it) * | 2000-12-06 | 2003-10-23 | Quarella Spa | Composizioni induribili comprendenti un poliestere insaturoepossidato e cariche minerali. |
DE10309857A1 (de) * | 2003-03-06 | 2004-09-23 | Wacker Polymer Systems Gmbh & Co. Kg | Epoxy-modifizierte Vinylchlorid-Vinylester-Copolymer-Festharze |
US7279174B2 (en) * | 2003-05-08 | 2007-10-09 | Advanced Cardiovascular Systems, Inc. | Stent coatings comprising hydrophilic additives |
CN1528622A (zh) * | 2003-10-17 | 2004-09-15 | 江阴协统汽车附件有限公司 | 汽车外装用涂漆间苯型片状模塑料保险杠 |
DE102004051353A1 (de) * | 2004-10-21 | 2006-04-27 | Wacker Polymer Systems Gmbh & Co. Kg | Silan-modifizierte Polyvinylalkohole |
JP5076499B2 (ja) * | 2005-03-28 | 2012-11-21 | 東レ株式会社 | ポリ乳酸発泡体 |
DE102006019686A1 (de) | 2006-04-27 | 2007-10-31 | Wacker Polymer Systems Gmbh & Co. Kg | Verwendung von carboxylfunktionellen Polyvinylacetaten zur Herstellung von BMC-Formteilen |
DE102007055694A1 (de) * | 2007-12-03 | 2009-06-04 | Wacker Chemie Ag | Vernetzbare Vinylester-Copolymerisate und deren Verwendung als Low-Profile-Additive |
-
2007
- 2007-12-03 DE DE102007055692A patent/DE102007055692A1/de not_active Ceased
-
2008
- 2008-12-01 CA CA2704889A patent/CA2704889C/en not_active Expired - Fee Related
- 2008-12-01 EP EP08858142A patent/EP2217660A1/de not_active Withdrawn
- 2008-12-01 WO PCT/EP2008/066531 patent/WO2009071508A1/de active Application Filing
- 2008-12-01 US US12/746,035 patent/US20100256287A1/en not_active Abandoned
- 2008-12-01 CN CN2008801187709A patent/CN101883823A/zh active Pending
Non-Patent Citations (1)
Title |
---|
See references of WO2009071508A1 * |
Also Published As
Publication number | Publication date |
---|---|
US20100256287A1 (en) | 2010-10-07 |
WO2009071508A1 (de) | 2009-06-11 |
CA2704889C (en) | 2012-09-11 |
CN101883823A (zh) | 2010-11-10 |
DE102007055692A1 (de) | 2009-06-04 |
CA2704889A1 (en) | 2009-06-11 |
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Legal Events
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AX | Request for extension of the european patent |
Extension state: AL BA MK RS |
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DAX | Request for extension of the european patent (deleted) | ||
17Q | First examination report despatched |
Effective date: 20110211 |
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Effective date: 20130404 |
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STAA | Information on the status of an ep patent application or granted ep patent |
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18D | Application deemed to be withdrawn |
Effective date: 20130815 |