EP1290091A2 - Agents de revetement durcissables aux uv, procede de realisation de revetements a partir de ces agents, et leur utilisation - Google Patents
Agents de revetement durcissables aux uv, procede de realisation de revetements a partir de ces agents, et leur utilisationInfo
- Publication number
- EP1290091A2 EP1290091A2 EP01940531A EP01940531A EP1290091A2 EP 1290091 A2 EP1290091 A2 EP 1290091A2 EP 01940531 A EP01940531 A EP 01940531A EP 01940531 A EP01940531 A EP 01940531A EP 1290091 A2 EP1290091 A2 EP 1290091A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- weight
- coating
- radiation
- coating composition
- composition according
- 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- Withdrawn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
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
- B05D7/06—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to wood
- B05D7/08—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to wood using synthetic lacquers or varnishes
-
- 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
- C08F290/08—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 side groups
- C08F290/14—Polymers provided for in subclass C08G
- C08F290/141—Polyesters; Polycarbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/06—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation
- B05D3/061—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation using U.V.
- B05D3/065—After-treatment
- B05D3/067—Curing or cross-linking the coating
Definitions
- Coating agents curable by UV radiation processes for producing coatings from these coating agents and their use
- the invention relates to coating compositions curable by UV radiation, processes for producing coatings from these coating compositions and their use.
- peroxidically curable polyester paints for example paraffin-containing paints based on phthalic anhydride or paraffin-free paints with a glossy surface based on allyl ether.
- the layers were applied using customary paint application methods such as rolling, pouring or spraying.
- the viscosities of these polyester paints are adjusted to a viscosity in the range from about 150 to 250 mPa.s at 21 ° C. so that they are sprayable.
- the polyester lacquers can be applied by compressed air spraying, with the polyester and peroxide components being mixed using the intermixing method and sprayed from a pot. It is also possible to run the two-component spray process, the peroxide component and the polyester component separately to the gun and mix in there in the spray jet.
- the wooden base is used for spray painting by pickling, priming, if necessary patinating and Isolate prepared. After drying, the polyester lacquer layer is sprayed onto the substrate prepared in this way.
- the sprayed polyester paints thixotropize so that they also adhere to vertical surfaces.
- they contain inorganic and / or organic thixotropic agents.
- the individual layers are gelled and UV-cured by UV radiation.
- the intermediate gelation and intermediate curing takes place through the radicals released from the peroxide component by UV radiation and, depending on the setting of the radiation, takes about 10 to 30 minutes for each individual layer.
- the final hardening of the entire layer is carried out by additional radiation with a high-pressure or medium-pressure mercury vapor lamp.
- the shrinking parts that are released into the atmosphere in polyester / styrene systems consist predominantly of monostyrene or of styrene oxide, which is formed from monostyrene during the polymerization. Both substances are volatile organic compounds (VOC), which are undesirable in the sense of VOC regulations. Cyclohexanone, which arises from the cyclohexanone peroxide used for the polymerization, is also undesirable.
- the polyester layer contains more or less volatile constituents, which are also gradually released.
- volatile constituents which are also gradually released.
- these are phthalates and solvent residues.
- the VOC value as a measure of the volatile constituents, is around 1,500 ppm for the above-mentioned gloss coating systems and around 1,700 to 2,200 ppm for polyester coatings containing paraffin.
- UV-curable acrylic lacquer system lends itself.
- radiation-curable acrylate lacquers have been applied by customary lacquer application methods, for example by thin-layer application by means of rollers, the layer thicknesses of the applied layers being 5 to 15 ⁇ m. These thin layers are also applied in several layers, gelled and sometimes even sanded. The intermediate gelling, which is necessary for the adhesion of the next layer, is achieved by UV radiation.
- viscosities of about 300 to 800 mPa.s have been set.
- the object of the invention is to develop a liquid coating composition curable by means of UV light which has good sprayability, good film properties in the end result and a low VOC value.
- liquid coating agent which can be hardened by UV radiation and which contains the following constituents:
- a thixotropic agent 0.1-5% by weight of a thixotropic agent
- the invention further relates to a method for producing a coating on a prefabricated wooden surface, in which the coating agent is applied by hot spraying at 35 to 80 ° C in several layers with a layer thickness of 50 to 800 microns and applied in each layer by UV radiation.
- the painted, hardened wooden component can be milled, sanded, polished and light-resistant, chemical-resistant and moisture-resistant.
- moisture resistance As far as moisture resistance is concerned, a 500h condensation storage (at 40 ° C and 95% relative humidity) is required.
- the coating agent according to the invention is low in emissions, ie has a low VOC value of ⁇ 100 ppm.
- the invention relates to coating compositions curable by UV light, which use acrylic resins as coating raw materials.
- the importance of the invention is based in particular in the fact that solvent-free and low-emission paints are used which lead to a variety of desired properties.
- the coating composition contains about 5 to 80% by weight, preferably about 10 to 60% by weight, of polyfunctional crosslinkable acrylates or methacrylates.
- Starting materials are, depending on the structural structure, polyether, polyester, epoxy, urethane, melamine, silicone acrylates and / or methacrylates and acrylated and / or methacrylated polyacrylates.
- the materials include all molecular weight ranges between monomers, oligomers and polymers and may contain other functional groups in addition to the acrylate group.
- the molecular weights are in a range from about 500 to 6,000, the composition being selected so that application by spraying is ensured and enough low molecular weight components are present so that a total viscosity of 150 to 250 mPa.s at 21 ° C results. On the other hand, to ensure good film properties of the end product, high-molecular components must also be present.
- the coating composition contains about 5 to 75% by weight of a reactive diluent.
- the reactive diluents are monomers or also low-viscosity oligomers that replace volatile organic solvents. They have molecular weights in the range from about 50 to 500.
- the reactive diluents which contain radical-polymerizable radicals, are selected from the group of acrylic esters of simple alcohols, hexanediol diacrylate, hydroxymethylethylacrylate, hydroxypropyl acrylate, polyethylene glycol diacrylate, trimethylolpropane triacrylate, dipropylene glycol diacrylate or mixtures of the same, tripropylene glycol.
- Styrene-free unsaturated acrylate and polyester acrylate resins are available, for example, from BASF under the trade names Laromer® and Sartomer®.
- a thixotropic agent based on silicon dioxide is added to adjust the thixotropy of the coating agent.
- fumed silica is preferred in an amount of 0.5 to 1.5% by weight.
- the thixotropic agent is combined with the resins or resin components of Van der Waals bonds, which bring about a reduction in viscosity under the action of mechanical forces during processing. After the mechanical stress has ceased, the thixotropy is reset, thereby preventing vertical surfaces from running off.
- photoinitiators which are added in an amount of about 0.01 to 10% by weight, preferably 1 to 3% by weight. These are compounds which, under the action of high-energy radiation, form start radicals which trigger the polymerization of the coating composition.
- UV initiators which can be used in the context of the present invention are, for example, benzoin ether, benzil dimethyl ketal, diethoxyacetophenone, hydroxy ketones, aminoketones, benzophenones, a mixture of benzophenone and 1-hydroxy-cyclohexyl-phenyl ketone (trade name Irgacure® from Ciba Specialty Chemicals, Basel), 2-hydroxy 2-methyl-1-phenyl-propan-1-one (trade name Darocur® from Ciba Specialty Chemicals, Basel), monoacylphosphine oxides and bisacylphosphine oxides, or mixtures thereof (trade name Lucirin® from BASF).
- benzoin ether benzil dimethyl ketal
- diethoxyacetophenone hydroxy ketones
- aminoketones benzophenones
- benzophenones a mixture of benzophenone and 1-hydroxy-cyclohexyl-phenyl ketone
- additives are also added to the coating agent.
- additives to increase the scratch resistance, heat resistance and light fastness. They can optionally be contained in amounts of approximately 0 to 20% by weight.
- surface-active substances are added in concentrations of 0.0001 to 2% by weight, for example organic silicone compounds of the polymethylsiloxane type (trade name Baysilone® from Bayer).
- Stabilizers or inhibitors which intercept potential start radicals.
- the amounts used are of the order of about 0 to 20% by weight, preferably from 0 to 8% by weight.
- Stabilizers or inhibitors which can be used in the context of the present invention can include hydroquinone, hydroquinone monomethyl ether, p-benzoquinone, p-tertiary-butylcatechol, phenothiazine, 2,6-di-tertiary-butylhydroxytoluene, sterically hindered amines and benzotriazole (trade name Tinuvin® from Ciba Specialty Chemicals , Basel).
- the coating agent of the present invention is a material that has no short-life pot life.
- the polymerisation is only triggered by the action of UV radiation by UV initiators.
- the consequence of this is that sprayed material, which for example reaches the conveyor belt, is recyclable and can be recycled by appropriate devices.
- the functionality of the reactive diluents and thus their crosslinking action is, in addition to the viscosity, the dilution action and volatility, an important selection criterion when using the same. If stabilizers remain in the product during manufacture, the paint properties must not be impaired. At most UV initiators are emitted from the product.
- reaction conditions with regard to temperature, mixing etc., as well as the stabilizer and UV initiator system, must be carefully coordinated. Temperatures of the reaction system of about 110 to 130 ° C should not be exceeded.
- a coating batch is made by simply mixing the components below with heating (to about 40 ° C) to ensure the dissolution of these components.
- the mixture has a viscosity of about 550 mPa.s (measured at 21 ° C). 60 parts by weight of epoxy acrylate, MW: 2,500;
- UV initiator consisting of a mixture of monoacylphosphine oxide and bisacylphosphine oxide
- Example 1 The components of Example 1 are used, with the exception that a mixture of 20 parts by weight of hexanediol diacrylate and 15 parts by weight of tripropylene glycol diacrylate is used instead of the reactive diluent. Instead of the UV initiator, 1 part by weight of a mixture of benzophenone and 1-hydroxycyclohexylphenyl ketone is used.
- the coating batch is prepared as indicated in Example 1. The mixture has a viscosity of about 600 mPa.s (measured at 21 ° C).
- Example 1 The components of Example 1 are used, with the exception that 35 parts by weight of a mixture of hydroxymethyl ethyl acrylate and hydroxypropyl acrylate are used instead of the reactive diluent.
- UV initiator is 2-hydroxy-2-methyl-1-phenylpropan-1-one (Darocur®).
- Example 4 The coating batch is prepared as indicated in Example 1. The mixture has a viscosity of about 580 mPa.s (measured at 21 ° C).
- Example 4 The coating batch is prepared as indicated in Example 1. The mixture has a viscosity of about 580 mPa.s (measured at 21 ° C).
- Example 1 The components of Example 1 are used, with the exception that 20 parts by weight of polyester acrylate (Laromer®), MW: 2,100, are used instead of the reactive diluent.
- Polyester acrylate Laromer®
- suitable application methods for the coating compositions of the invention are also pouring, flooding, dipping or rolling. According to the invention, preference is given to a hot spraying process at a paint temperature of approximately 35 to 60 ° C.
- the total number of paint jobs is 4 to 8 jobs. 50 to 500 g / m 2 , preferably 150 to 250 g / m 2, are sprayed on per application.
- the polymerization is carried out by means of UV radiation. It can advantageously also be carried out in an inert gas atmosphere, for example under nitrogen gas, to exclude the polymerization-inhibiting atmospheric oxygen. Since various additives are considered hazardous substances, for example there are risks of skin contact, it is advantageous to apply the layers of paint in a closed chamber.
- the UV irradiation time required for gelling and / or curing depends on the temperature and the chemical composition of the coating agent, on the type and power of the UV source, on its distance from the coating agent and on any inert gas atmosphere that may be present. Guideline values for the radiation duration are a few seconds to a few minutes.
- the UV radiation source should emit radiation in the range from about 150 to 600 nm, preferably from 200 to 400 nm wavelength.
- the radiated energy is in a range from about 5 to 2,000 mJ / cm 2 .
- Guide values for the distance between the UV source and the lacquer layer are in the range of approximately 20 to 1,000 mm.
- the four coating agents described above are used in a coating process as described below.
- An interior fine wood veneer for motor vehicles is chosen as the substrate.
- the wood is cemented with a spatula and hardener and hardened for about 2 hours at 20 to 28 ° C at 50 to 60% relative humidity.
- the wood substrate is then pickled by spraying a dye solution and dried under the conditions specified for the kitten for 4 hours and cooled back to room temperature.
- a two-component polyurethane system is sprayed on for priming.
- the application quantity is 20 to 40 g / m 2 , depending on the part and type of wood, with 1 or 2 applications and ventilation between the applications.
- Hardening 3 to 16h at 20 to 23 ° C at 50 to 60% relative humidity.
- a colorless insulating base two-component polyurethane system
- hardener 3 to 16h at 20 to 23 ° C at 50 to 60% relative humidity.
- Post-curing is carried out at 50 ° C for 16 hours.
- VOC determination is carried out according to the applicable standards using two methods:
- GC-MS gas chromatography mass spectrometry
- VOC values of around 1,500 ppm were measured up to 90 ° C in so-called polyester gloss coating systems and VOC values of around 1,700 to 2,200 ppm in polyester coatings containing paraffin.
- VOC values of approximately 40 to 60 ppm are measured in the above exemplary embodiments according to the invention.
- the invention relates to acrylate-based coating compositions which are curable by UV radiation and which are suitable for coating wooden components.
- the coating composition contains 5 to 80% by weight of acrylic resins; 5 to 75% by weight of a reactive diluent; 0.1 to 5% by weight of a thixotropic agent; 0.1 to 10% by weight of a photoinitiator and 0.05 to 20% by weight of additives.
- the process for the production of coatings is also protected. In this 4 to 8 layers applied to pre-assembled wooden parts in a hot spraying process and hardened using UV radiation.
Abstract
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10027670 | 2000-06-03 | ||
DE10027670A DE10027670A1 (de) | 2000-06-03 | 2000-06-03 | Durch UV-Strahlung härtbare Beschichtungsmittel, Verfahren zur Herstellung von Überzügen aus diesen Beschichtungsmitteln und deren Verwendung |
PCT/EP2001/006037 WO2001094478A2 (fr) | 2000-06-03 | 2001-05-26 | Agents de revetement durcissables aux uv, procede de realisation de revetements a partir de ces agents, et leur utilisation |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1290091A2 true EP1290091A2 (fr) | 2003-03-12 |
Family
ID=7644670
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP01940531A Withdrawn EP1290091A2 (fr) | 2000-06-03 | 2001-05-26 | Agents de revetement durcissables aux uv, procede de realisation de revetements a partir de ces agents, et leur utilisation |
Country Status (5)
Country | Link |
---|---|
US (1) | US20030176527A1 (fr) |
EP (1) | EP1290091A2 (fr) |
AU (1) | AU2001274072A1 (fr) |
DE (1) | DE10027670A1 (fr) |
WO (1) | WO2001094478A2 (fr) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102051115A (zh) * | 2010-12-14 | 2011-05-11 | 惠州市凯辉化工有限公司 | 一种紫外光固化色漆及其制备方法 |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1485436B1 (fr) * | 2002-03-08 | 2007-07-04 | Valspar Sourcing, Inc. | Revetements a faible teneur en compose organique volatil |
KR100703856B1 (ko) | 2005-10-10 | 2007-04-06 | 에스에스씨피 주식회사 | 하이솔리드 자외선 경화형 도료 조성물 |
DE102006012274A1 (de) * | 2006-03-15 | 2007-09-20 | Votteler Lackfabrik Gmbh & Co. Kg | Lack zur Oberflächenbeschichtung von Formteilen |
US20080050559A1 (en) * | 2006-08-25 | 2008-02-28 | Building Materials Investment Corporation | UV-cured coating for roofing materials |
DE102006061379A1 (de) | 2006-12-23 | 2008-06-26 | Evonik Degussa Gmbh | Kieselsäurehaltige strahlenhärtbare Formulierungen mit erhöhtem Korrosionsschutz auf Metalluntergründen |
US8796348B2 (en) * | 2007-09-26 | 2014-08-05 | Henkel Ag & Co. Kgaa | UV curable coating composition |
US7618687B2 (en) * | 2007-10-17 | 2009-11-17 | Ppg Industries Ohio, Inc. | Method for coating substrates |
DE102008010346B4 (de) * | 2008-02-14 | 2019-05-09 | Karl Wörwag Lack- Und Farbenfabrik Gmbh & Co. Kg | UV-härtbare Zusammensetzung, ihre Verwendung als Beschichtungsmittel und Verfahren zur Lackierung von Fahrzeugachsen |
US8298675B2 (en) * | 2009-07-17 | 2012-10-30 | Honda Motor Co., Ltd. | Low gloss wood for interior trim |
CN104893411A (zh) | 2009-12-17 | 2015-09-09 | 帝斯曼知识产权资产管理有限公司 | 聚合物组合物 |
CN102031055B (zh) * | 2010-12-15 | 2013-01-09 | 东莞大宝化工制品有限公司 | 一种不含挥发性有机溶剂的uv喷涂面漆 |
DE102019113331A1 (de) * | 2019-05-20 | 2020-11-26 | Brillux Gmbh & Co. Kg | Verfahren zum Beschichten einer Oberfläche |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3657001A (en) * | 1970-12-22 | 1972-04-18 | Du Pont | Process for hot spraying a thermosetting acrylic enamel modified with cellulose acetate butyrate |
US4504374A (en) * | 1983-03-09 | 1985-03-12 | Desoto, Inc. | Ultraviolet cured coating method to provide stone chip resistance |
DE3616434A1 (de) * | 1986-05-15 | 1987-11-19 | Bayer Ag | Verfahren zur grundierung von holz |
US5773487A (en) * | 1991-05-15 | 1998-06-30 | Uv Coatings, Inc. | Finishing composition which is curable by UV light and method of using same |
WO1992020719A1 (fr) * | 1991-05-15 | 1992-11-26 | Sokol Andrew A | Composition de finition polymerisable par la lumiere ultraviolette, et procede d'utilisation de ladite composition |
WO1997045458A1 (fr) * | 1995-09-26 | 1997-12-04 | Uv Coatings Limited | Composition de finition durcissable a la lumiere ultraviolette et son procede d'utilisation |
DE19826715A1 (de) * | 1997-07-21 | 1999-01-28 | Basf Ag | Strahlungshärtbare Verbindungen auf Basis von 2,4-Diethyloctandiol |
-
2000
- 2000-06-03 DE DE10027670A patent/DE10027670A1/de not_active Ceased
-
2001
- 2001-05-26 AU AU2001274072A patent/AU2001274072A1/en not_active Abandoned
- 2001-05-26 WO PCT/EP2001/006037 patent/WO2001094478A2/fr active Application Filing
- 2001-05-26 EP EP01940531A patent/EP1290091A2/fr not_active Withdrawn
- 2001-05-26 US US10/297,140 patent/US20030176527A1/en not_active Abandoned
Non-Patent Citations (1)
Title |
---|
See references of WO0194478A2 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102051115A (zh) * | 2010-12-14 | 2011-05-11 | 惠州市凯辉化工有限公司 | 一种紫外光固化色漆及其制备方法 |
CN102051115B (zh) * | 2010-12-14 | 2013-03-20 | 惠州市凯辉化工有限公司 | 一种紫外光固化色漆及其制备方法 |
Also Published As
Publication number | Publication date |
---|---|
AU2001274072A1 (en) | 2001-12-17 |
US20030176527A1 (en) | 2003-09-18 |
DE10027670A1 (de) | 2001-12-13 |
WO2001094478A2 (fr) | 2001-12-13 |
WO2001094478A3 (fr) | 2002-07-18 |
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