WO2004056930A1 - Uv-curable epoxy acrylates - Google Patents
Uv-curable epoxy acrylates Download PDFInfo
- Publication number
- WO2004056930A1 WO2004056930A1 PCT/EP2003/051057 EP0351057W WO2004056930A1 WO 2004056930 A1 WO2004056930 A1 WO 2004056930A1 EP 0351057 W EP0351057 W EP 0351057W WO 2004056930 A1 WO2004056930 A1 WO 2004056930A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- epoxy acrylate
- mixture
- epoxy
- weight
- formula
- Prior art date
Links
- 0 C=CC(OCC(COC*(CC1)CC2C1C1(COCC(COC(C=C)=O)O)CC2CC1)O)=O Chemical compound C=CC(OCC(COC*(CC1)CC2C1C1(COCC(COC(C=C)=O)O)CC2CC1)O)=O 0.000 description 1
- WNVVROQZLZADJY-UHFFFAOYSA-N C=CC(OCC(COC1CCC(CC(CC2)CCC2OCC(COC(C=C)=O)O)CC1)O)=O Chemical compound C=CC(OCC(COC1CCC(CC(CC2)CCC2OCC(COC(C=C)=O)O)CC1)O)=O WNVVROQZLZADJY-UHFFFAOYSA-N 0.000 description 1
- RHYFWDXPRUVTNO-UHFFFAOYSA-N CC(C)(C(CC1)CCC1OCC(COC(C=C)=O)O)C(CC1)CCC1OCC(COC(C=C)=O)O Chemical compound CC(C)(C(CC1)CCC1OCC(COC(C=C)=O)O)C(CC1)CCC1OCC(COC(C=C)=O)O RHYFWDXPRUVTNO-UHFFFAOYSA-N 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
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
- C09J163/10—Epoxy resins modified by unsaturated compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/60—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members
- C07C2603/66—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing five-membered rings
- C07C2603/68—Dicyclopentadienes; Hydrogenated dicyclopentadienes
Definitions
- the present invention relates to novel epoxy acrylates and epoxy acrylate mixtures, to a process for the preparation and to the use of the epoxy acrylates of the invention in coating materials or adhesives with high UV stability, and also to coating compositions and adhesive compositions.
- Epoxy acrylates are compounds prepared by reacting epoxides, either glycidyl ethers or cyclohexene oxides, with acrylic acid, that is producing hydroxyacrylates.
- the aromatic, industrially widespread BPA-DGE e.g Araldit® GY240
- epoxyphenol novolaks e.g. Araldit® EPN 1179
- BPA-DGE e.g Araldit® GY240
- epoxyphenol novolaks e.g. Araldit® EPN 1179
- Viscosities of about 500-1000 Pas (25°C) in the undiluted state.
- a low-viscosity such as HDDA, TMPTA, TPGDA, and other monomers known to the person skilled in the art. Radiation-induced free-radical curing of such products produces films having good mechanical properties.
- Typical surface hardnesses (Persoz hardness) of such termed termed "Persoz hardness) of such termed "Persoz hardness" homopolymers are 300-330 seconds. However, these high hardnesses are accompanied by Erichsen indentation values of ⁇ 1 mm. Use is made generally of aromatic epoxy acrylates when scratch resistance and chemical resistance are priorities. Aromatic compounds are unsuitable in films exposed to weathering. In artificial weathering in a Weather-O-meter, for example, severe loss of gloss and yellowing are observed within 100 hours.
- Epoxy acrylates made from linear aliphatic alcohols are also known. Commercially available examples include butanediol diglycidyl diacrylate and hexanediol diglycidyl diacrylate. They are notable for a low viscosity (about 1 Pa*s, 25°C) and solubility in water. Homopolymers, however, have weak mechanical properties. Neat resin Persoz hardnesses of around 50 seconds are commonplace. The known epoxy acrylates, however, are not entirely satisfactory, particularly when not only outstanding mechanical properties but also high UV stabilities are required. In many cases the known epoxy acrylates also have a considerable odour.
- an epoxy acrylate mixture comprising A and B or an epoxy acrylate mixture which in addition to the compound of the formula A or B comprises at least one compound of the formula
- the epoxy acrylate mixtures according to the invention contain as epoxy acrylates at least 30% by weight, more preferably, at least 50% by weight, of compound A and/or B.
- compositions which have a solids content of 100%, are odourless, and have good mechanical properties and high UV stabilities.
- the compositions of the invention display the stated advantages when irradiated even with a low UV dose and are also suitable, when using corresponding monomers containing acceptor groups (such as NCO or COOR, for example), for the process known as dual cure, where an additional thermal cure is accomplished.
- novel compounds A and B can be prepared in a conventional manner by reacting the corresponding diglycidyl ethers with acrylic acid, preferably in a near-equinormal ratio of from 1 :0.9 to 1:1.1. Further details and preferences are evident from the examples. Also of advantage is the simultaneous reaction of different glycidyl ethers with acrylic acid, leading directly to a composition of the invention comprising at least one compound A or B and also at least one further compound A to E.
- the present invention provides for the use of the epoxy acrylates of the invention in coating compositions and adhesive compositions.
- the present invention further provides a radiation-curable coating composition based on an epoxy acrylate binder containing from 5 to 90% by weight, preferably from 10 to 80% by weight, of the epoxy acrylate of the invention, based on the total amount of binder.
- the present invention further provides a radiation-curable adhesive composition based on an epoxy acrylate binder containing from 5 to 90% by weight, preferably from 10 to 80% by weight, of the epoxy acrylate of the invention, based on the total amount of binder.
- the radiation-curable compositions of the invention normally include a photoinitiator.
- the photoinitiator content is preferably from 0.1 to 10% by weight and in particular from 1 to 8% by weight, based in each case on the total amount of the epoxy acrylates.
- Suitable photoinitiators are known to the person skilled in the art and some are also available commercially. Use may be made, for example, of the products available commercially under the name Irgacure® from Ciba Spezialitatenchemie.
- Irgacure® from Ciba Spezialitatenchemie.
- initiators for photocationic polymerization which are likewise known to the person skilled in the art.
- Photoinitiators for cationic polymerization generate strong Br ⁇ nsted acids when exposed to UV radiation and thereby initiate the polymerization of the epoxide groups.
- the compositions contain cationic photoinitiators generally in amounts from 0.05 to 3% by weight, based on the epoxy resin component.
- cationic photoinitiators have as their general formula either S + (A 1 A 2 A 3 )Q “ or l + ( A -JQ " , in which A-i, A 2 and A 3 are identical or different aromatic radicals, which may be singly or multiply substituted and can contain heteroatoms, and Q " is an anion such as BF “ , PF 6 “ , AsF 6 “ , SbF 6 “ or SnCI 6 ' , for example.
- compositions of the invention are advantageously cured with actinic radiation, with UV radiation or with electron beams. Where appropriate this can be carried out with or supplemented by actinic radiation from other sources.
- actinic radiation with UV radiation or with electron beams.
- electron beams it is preferred to operate under an inert gas atmosphere. This can be ensured, for example, by supplying carbon dioxide and/or nitrogen directly to the surface of the coating.
- UV radiation curing as well it is possible to operate under inert gas in order to prevent formation of ozone.
- Curing with actinic radiation is carried out using the conventional and known radiation sources and optical auxiliary measures.
- suitable radiation sources are high- pressure or low- pressure mercury vapour lamps, which are described for example in the brochures from Fusion Systems Inc. or Heraeus Holding GmbH. Their arrangement is known in principle and can be adapted to the circumstances of the workpiece and the process parameters. In the case of workpieces of complex shape those regions not accessible to direct radiation (shadow regions), such as cavities, folds and other structural undercuts, can be (partly) cured using pointwise, small-area or all-round sources in conjunction with an automatic movement means for the irradiation of cavities or edges.
- the substrate can be at rest or can be guided past the radiation source at an appropriate speed.
- the UV lamps here are preferably of 100 to 200 W/cm, more preferably from 120 to 190 W/cm and in particular from 140 to 180 W/cm. Irrespective of whether the substrate is moved or is at rest, a radiation dose in the range from 50 to 6,000 mJ/cm 2 , more preferably from 50 to 2,000 mJ/cm 2 , proves to be advantageous.
- compositions of the invention may further comprise the epoxy resins, preferably aliphatic epoxy resins, which are customary in epoxy resin technology.
- epoxy resins include the following:
- Polyglycidyl ethers or poly-( ⁇ -methylglycidyl) ethers obtainable by reacting a compound having at least one, preferably two, free alcoholic hydroxyl groups with epichlorohydrin or ⁇ - methylepichlorohydrin under alkaline conditions or in the presence of an acidic catalyst with subsequent alkali treatment.
- the glycidyl ethers of this type are derived for example from acyclic alcohols, such as ethylene glycol, diethylene glycol or higher poly(oxyethylene) glycols, propane-1,2-diol or poly(oxypropylene) glycols, propane-1,3-diol, butane-1,4-diol, poly(oxytetramethylene) glycols, pentane-1,5-diol, hexane-1,6-diol, hexane-2,4,6-triol, glycerol, C ⁇ 2 - ⁇ OH (Araldit® DY- E) 1,1,1-trimethylolpropane, pentaerythritol, sorbitol, and also from polyepichlorohydrins.
- acyclic alcohols such as ethylene glycol, diethylene glycol or higher poly(oxyethylene) glycols, propane-1,2-diol or poly(oxypropylene
- glycidyl ethers of this type are derived from cycloaliphatic alcohols, such as 1 ,4-cyclohexanedimethanol, bis(4-hydroxycyclohexyl)methane, 2,2-bis(4-hydroxycyclohexyl)- propane or tricyclodecanedimethanol.
- Cycloaliphatic epoxy resins such as bis(2,3-epoxycyclopentyl) ether, 2,3-epoxycyclopentylglycidyl ether, 1 ,2-bis(2,3-epoxycyclopentyloxy)ethane or the corresponding hydrogenated bisphenol A diglycidyl ethers, bisphenol F diglycidyl ethers, or TCD diglycidyl ethers.
- Particularly preferred additional epoxy resins used are aliphatic epoxy resins such as trimethylolpropane triglycidyl ether and also cycloaliphatic epoxy resins such as bis(2,3- epoxycyclopentyl) ether.
- compositions of the invention may of course comprise other components, which may differ according to the field of use of the compositions, and which are known to the person skilled in the particular art field.
- Coating compositions based on the epoxy acrylates may further comprise, for example, additives which are customary in the coatings industry, in the amounts customary for those additives: they include light stabilizers, curing accelerators, dyes, pigments, e.g. titanium dioxide pigment, devolatilizers, or else additional levelling agents.
- additives which are customary in the coatings industry, in the amounts customary for those additives: they include light stabilizers, curing accelerators, dyes, pigments, e.g. titanium dioxide pigment, devolatilizers, or else additional levelling agents.
- Substrates suitable for coating include all surfaces amenable to cooling by actinic radiation. Examples include metals, plastics, wood, ceramic, stone, textile, leather, glass, including glass fibers, glass wool and rock wool, mineral-bound and resin-bound building materials, such as plasterboard panels, cement slabs or roof tiles. Accordingly the coating composition of the invention is suitable for applications such as automotive finishing, and also in particular for the coating of furniture and for industrial coating, including coil coating and container coating.
- primed or unprimed plastics such as, for example, ABS, AMMA, ASA, CA, CAB, EP, UF, CF, MP, MPF, PF, PAN, PA, PE, HDPE, LDPE, LLDPE, UHMWPE, PET, PMMA, PP, PS, SB, PUR, PVC, RF, SAN, PBT, PPE, POM, PUR-RIM, SMC, BMC, PP-EPDM and UP (abbreviations according to DIN 7728T1).
- plastics such as, for example, ABS, AMMA, ASA, CA, CAB, EP, UF, CF, MP, MPF, PF, PAN, PA, PE, HDPE, LDPE, LLDPE, UHMWPE, PET, PMMA, PP, PS, SB, PUR, PVC, RF, SAN, PBT, PPE, POM, PUR-RIM, SMC, BMC, PP-EPDM and UP (abbreviations according to
- Examples 3-5 The table below symbolizes the investigations and the coatings obtained on the epoxy acrylates of the invention.
- the gloss is determined in accordance with ISO 2813 standard.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Paints Or Removers (AREA)
- Epoxy Resins (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE60331168T DE60331168D1 (en) | 2002-12-19 | 2003-12-18 | UV-RAY-HARDENED EPOXY ACRYLATES |
DK03808308.5T DK1572814T3 (en) | 2002-12-19 | 2003-12-18 | UV curable epoxy acrylates |
EP03808308A EP1572814B1 (en) | 2002-12-19 | 2003-12-18 | Uv-curable epoxy acrylates |
US10/537,656 US7087696B2 (en) | 2002-12-19 | 2003-12-18 | Uv-curable epoxy acrylates |
JP2004561511A JP4537209B2 (en) | 2002-12-19 | 2003-12-18 | UV curable epoxy acrylate |
AT03808308T ATE456629T1 (en) | 2002-12-19 | 2003-12-18 | EPOXY ACRYLATES CURED BY UV RADIATION |
AU2003303223A AU2003303223A1 (en) | 2002-12-19 | 2003-12-18 | Uv-curable epoxy acrylates |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH2161/02 | 2002-12-19 | ||
CH21612002 | 2002-12-19 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2004056930A1 true WO2004056930A1 (en) | 2004-07-08 |
Family
ID=32661014
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2003/051057 WO2004056930A1 (en) | 2002-12-19 | 2003-12-18 | Uv-curable epoxy acrylates |
Country Status (11)
Country | Link |
---|---|
US (1) | US7087696B2 (en) |
EP (1) | EP1572814B1 (en) |
JP (1) | JP4537209B2 (en) |
CN (1) | CN1331953C (en) |
AT (1) | ATE456629T1 (en) |
AU (1) | AU2003303223A1 (en) |
DE (1) | DE60331168D1 (en) |
DK (1) | DK1572814T3 (en) |
ES (1) | ES2339658T3 (en) |
TW (1) | TWI275621B (en) |
WO (1) | WO2004056930A1 (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102005021086A1 (en) * | 2005-05-06 | 2006-11-09 | Basf Coatings Ag | Coating material, process for its preparation and its use for the production of adherent, corrosion-inhibiting coatings |
DE102005024381A1 (en) * | 2005-05-27 | 2006-11-30 | Basf Coatings Ag | Coating material, process for its preparation and its use for the production of adhesive, color and / or effect coatings |
WO2009036847A1 (en) | 2007-09-18 | 2009-03-26 | Cook Composites And Polymers Company | Low voc thermosetting composition of polyester acrylic resin for gel coat |
CN101450992B (en) * | 2007-12-07 | 2010-12-22 | 比亚迪股份有限公司 | Polymer and preparation method thereof and conducting resin containing the same |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102005014958A1 (en) * | 2005-03-30 | 2006-10-05 | Sensient Imaging Technologies Gmbh | Covering layer for electrophotographic printing rollers |
KR100643186B1 (en) * | 2006-05-03 | 2006-11-10 | 이승욱 | A lcd window covered with glass sheet and its preparation |
KR101650693B1 (en) | 2010-03-09 | 2016-08-25 | 헨켈 아이피 앤드 홀딩 게엠베하 | Cationic uvcrosslinkable acrylic polymers for pressure sensitive adhesives |
JP2012014053A (en) * | 2010-07-02 | 2012-01-19 | Fujifilm Corp | Photocurable color composition for color filter, color filter, method for manufacturing color filter, and liquid crystal display device |
US8513321B2 (en) | 2010-11-05 | 2013-08-20 | Ppg Industries Ohio, Inc. | Dual cure coating compositions, methods of coating a substrate, and related coated substrates |
CN103087640A (en) | 2011-11-08 | 2013-05-08 | 汉高股份有限公司 | Dual-curing adhesive composition and application thereof and method for bonding substrates |
CN102925033B (en) * | 2012-11-12 | 2015-03-18 | 江苏广信感光新材料股份有限公司 | White ultraviolet light polymerization resin composition, and preparation method and application method thereof |
WO2016089141A1 (en) * | 2014-12-03 | 2016-06-09 | 주식회사 동진쎄미켐 | Photo-curable and thermo-curable binder |
KR20180030845A (en) * | 2015-07-14 | 2018-03-26 | 헨켈 아이피 앤드 홀딩 게엠베하 | Monomers and oligomer resins for one drop fill sealant field |
TR201807994A2 (en) * | 2018-06-05 | 2018-06-21 | Atatuerk Ueniversitesi Bilimsel Arastirma Projeleri Birimi | UV-HARDENING, BIO-ADHESIVE, SUPERAMPHIPHOBIC COATING |
KR102190637B1 (en) * | 2018-11-26 | 2020-12-15 | 주식회사 제일화성 | Epoxy acrylate oligimer and method for manufacturing the same, and photocurable resin composition for 3d printing using the same |
CN113292903A (en) * | 2021-05-21 | 2021-08-24 | 无锡时生高分子科技有限公司 | Solvent-free UV-curing type three-proofing adhesive |
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EP0023686A2 (en) * | 1979-08-07 | 1981-02-11 | Bayer Ag | (Meth)acrylic esters of tricyclic decandiols that contain ether groups, process for their preparation and use in the manufacture of adhesive and sealing compositions |
US4844604A (en) * | 1987-11-13 | 1989-07-04 | Desoto, Inc. | Optical fiber bundling material and bundled optical fibers |
WO1999006888A1 (en) * | 1997-07-30 | 1999-02-11 | Dsm N.V. | Radiation curable resin composition |
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JPS6248111A (en) * | 1985-08-27 | 1987-03-02 | Fujitsu Ltd | Frequency modulator |
JPS62232427A (en) * | 1986-04-03 | 1987-10-12 | Nippon Kayaku Co Ltd | Novel epoxy acrylate of methacrylate resin composition and solder resist in composition |
US5277739A (en) * | 1988-08-19 | 1994-01-11 | Bayer Aktiengesellschaft | Process for bonding a material to a collagen-containing material |
JP3217126B2 (en) * | 1992-06-18 | 2001-10-09 | タムラ化研株式会社 | Photosensitive resin composition |
JPH07140652A (en) * | 1993-10-22 | 1995-06-02 | Tamura Kaken Kk | Photosensitive resin composition |
EP0872529B2 (en) * | 1996-11-07 | 2008-07-09 | Asahi Kasei Kabushiki Kaisha | Binder for building structures |
JP2002012814A (en) * | 2000-04-28 | 2002-01-15 | Kansai Paint Co Ltd | Coating material composition |
JP4532724B2 (en) * | 2000-12-08 | 2010-08-25 | 互応化学工業株式会社 | UV curable resin composition, photo solder resist ink, pre-dried film, substrate, printed wiring board and dry film |
-
2003
- 2003-12-17 TW TW092135722A patent/TWI275621B/en not_active IP Right Cessation
- 2003-12-18 JP JP2004561511A patent/JP4537209B2/en not_active Expired - Fee Related
- 2003-12-18 WO PCT/EP2003/051057 patent/WO2004056930A1/en active Application Filing
- 2003-12-18 DK DK03808308.5T patent/DK1572814T3/en active
- 2003-12-18 US US10/537,656 patent/US7087696B2/en not_active Expired - Fee Related
- 2003-12-18 EP EP03808308A patent/EP1572814B1/en not_active Expired - Lifetime
- 2003-12-18 AT AT03808308T patent/ATE456629T1/en active
- 2003-12-18 CN CNB2003801066472A patent/CN1331953C/en not_active Expired - Fee Related
- 2003-12-18 DE DE60331168T patent/DE60331168D1/en not_active Expired - Lifetime
- 2003-12-18 ES ES03808308T patent/ES2339658T3/en not_active Expired - Lifetime
- 2003-12-18 AU AU2003303223A patent/AU2003303223A1/en not_active Abandoned
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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EP0023686A2 (en) * | 1979-08-07 | 1981-02-11 | Bayer Ag | (Meth)acrylic esters of tricyclic decandiols that contain ether groups, process for their preparation and use in the manufacture of adhesive and sealing compositions |
US4844604A (en) * | 1987-11-13 | 1989-07-04 | Desoto, Inc. | Optical fiber bundling material and bundled optical fibers |
WO1999006888A1 (en) * | 1997-07-30 | 1999-02-11 | Dsm N.V. | Radiation curable resin composition |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102005021086A1 (en) * | 2005-05-06 | 2006-11-09 | Basf Coatings Ag | Coating material, process for its preparation and its use for the production of adherent, corrosion-inhibiting coatings |
DE102005024381A1 (en) * | 2005-05-27 | 2006-11-30 | Basf Coatings Ag | Coating material, process for its preparation and its use for the production of adhesive, color and / or effect coatings |
WO2009036847A1 (en) | 2007-09-18 | 2009-03-26 | Cook Composites And Polymers Company | Low voc thermosetting composition of polyester acrylic resin for gel coat |
US8546486B2 (en) | 2007-09-18 | 2013-10-01 | Ccp Composites Us Llc | Low VOC thermosetting polyester acrylic resin for gel coat |
CN101450992B (en) * | 2007-12-07 | 2010-12-22 | 比亚迪股份有限公司 | Polymer and preparation method thereof and conducting resin containing the same |
Also Published As
Publication number | Publication date |
---|---|
JP2006510777A (en) | 2006-03-30 |
DK1572814T3 (en) | 2010-05-17 |
ES2339658T3 (en) | 2010-05-24 |
JP4537209B2 (en) | 2010-09-01 |
AU2003303223A1 (en) | 2004-07-14 |
EP1572814A1 (en) | 2005-09-14 |
DE60331168D1 (en) | 2010-03-18 |
CN1331953C (en) | 2007-08-15 |
CN1729256A (en) | 2006-02-01 |
US7087696B2 (en) | 2006-08-08 |
US20060052628A1 (en) | 2006-03-09 |
TWI275621B (en) | 2007-03-11 |
ATE456629T1 (en) | 2010-02-15 |
EP1572814B1 (en) | 2010-01-27 |
TW200416263A (en) | 2004-09-01 |
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