EP1902109A1 - Procede de production de formulations radiodurcissables assurant une protection accrue contre la corrosion sur des supports metalliques et ces formulations - Google Patents

Procede de production de formulations radiodurcissables assurant une protection accrue contre la corrosion sur des supports metalliques et ces formulations

Info

Publication number
EP1902109A1
EP1902109A1 EP06763139A EP06763139A EP1902109A1 EP 1902109 A1 EP1902109 A1 EP 1902109A1 EP 06763139 A EP06763139 A EP 06763139A EP 06763139 A EP06763139 A EP 06763139A EP 1902109 A1 EP1902109 A1 EP 1902109A1
Authority
EP
European Patent Office
Prior art keywords
radiation
curable
formulation according
glycol
curable formulation
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Withdrawn
Application number
EP06763139A
Other languages
German (de)
English (en)
Inventor
Emmanouil Spyrou
Marion Ebbing-Ewald
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Evonik Operations GmbH
Original Assignee
Evonik Degussa GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Evonik Degussa GmbH filed Critical Evonik Degussa GmbH
Publication of EP1902109A1 publication Critical patent/EP1902109A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
    • C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
    • 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
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/671—Unsaturated compounds having only one group containing active hydrogen
    • C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
    • 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
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • C09D175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds

Definitions

  • the invention relates to radiation-curable formulations containing phosphoric acid-containing adhesion promoters and in the cured state to a particular extent provide corrosion protection for metallic substrates and a process for their preparation.
  • Ethylenically unsaturated prepolymers are z.
  • PKT Oldring ed.
  • SITA Technology Vol. II. SITA Technology, London 1991, for example, based on epoxy acrylates (pages 31-68 Urethane acrylates (pages 73 to 123) and melamine acrylates (pages 208 to 214).
  • Such formulations are also frequently mentioned in the patent literature, examples being JP 62110779 and EP 947 565.
  • the coating of metallic substrates is a particular problem for radiation-curable formulations, as it may lead to loss of adhesion due to shrinkage processes. Therefore, phosphoric acid-containing adhesion promoters are often used for such substrates. Examples are US-5, 128,387 (coating of beer cans) and JP2001172554 (coating of various doses).
  • the present invention is a radiation-curable formulation consisting of
  • F optionally other additives, obtained by first tempering for 30 minutes to 48 hours at a temperature of 40 to 100 ° C prior to application and curing.
  • Urethanpolyesteracrylate a A special position among the radiation-curable resins and particularly suitable according to the invention, take Urethanpolyesteracrylate a, since they have particularly good properties in terms of mechanics and weather stability. Urethane polyester acrylates are described, for. In US 5719227.
  • Urethane polyester acrylates which are particularly suitable consist of a hydroxyl-containing polyester to which urethane groups and acrylate groups are bonded by reaction with polyisocyanates and acrylate-containing alcohols.
  • Urethane polyester acrylates are prepared from hydroxyl-containing polyesters by reaction with polyisocyanates and a compound which simultaneously contains at least one alcohol group and contains at least one polymerizable acrylate group prepared. They also have urethane groups such as terminal acrylate groups.
  • Hydroxyl-containing polyesters are prepared by polycondensation of suitable dicarboxylic acids and diols. The condensation is carried out in a manner known per se in an inert gas atmosphere at temperatures of 100 to 260 ° C, preferably 130 to 220 ° C, are recovered in the melt or in azeotropic procedure, as it is z.
  • in methods of organic chemistry Houben-Weyl; Vol. 14/2, pages 1 to 5, 21 to 23, 40 to 44, Georg Thieme Verlag, Stuttgart, 1963, or by C.R. Martens, Alkyd Resins, pages 51 to 59, Reinhold Plastics Appl. Series, Reinhold Publishing Comp., New York, 1961.
  • the preferred carboxylic acids for the preparation of polyesters may be aliphatic, cycloaliphatic, aromatic and / or heterocyclic in nature and optionally substituted by halogen atoms and / or unsaturated. Examples which may be mentioned are: succinic, adipic, cork, azelaic, sebacic, phthalic, terephthalic, isophthalic, trimellitic, pyromellitic, tetrahydrophthalic, hexahydrophthalic, hexahydroterephthalic, di- and tetrachlorophthalic, Endomethylenetetrahydrophthalic, glutaric, 1,4-cyclohexanedicarboxylic acid or - if available - their anhydrides or esters. Particularly suitable are isophthalic acid, terephthalic acid, hexahydroterephthalic acid and 1-cyclohexanedicarboxylic acid.
  • polyols come z.
  • B monoethylene glycol, 1,2- and 1,3-propylene glycol, 1,4- and 2,3-butylene glycol, di-ß-hydroxyethylbutandiol, 1,5-pentanediol, 1,6-hexanediol, 1,8-octanediol, Decane diol, dodecane diol, neopentyl glycol, cyclohexane diol, 3 (4), 8 (9) bis (hydroxymethyl) tricyclo [5.2.1.0 2 ' 6 ] decane (dicidol), bis (1,4-hydroxymethyl) cyclohexane, 2 , 2-bis- (4-hydroxycyclohexyl) -propane, 2,2-bis [4- ( ⁇ -hydroxyethoxy) -phenyl] -propane, 2-methyl-1,3-propanediol, 2-methyl-pentanediol-1
  • polyesters Preference is given to monoethylene glycol, neopentyl glycol, dicidol, cyclohexanedimethanol, trimethylolpropane and glycerol.
  • polyesters have an OH number of 15 to 750 mg KOH / g. It is also possible to use mixtures of polyesters.
  • polyisocyanates diisocyanates of aliphatic, (cyclo) aliphatic or cycloaliphatic structure.
  • Representative examples of the polyisocyanates are 2-methylpentamethylene-1,5-diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene-1,6-diisocyanate, in particular the 2,2,4- and 2,4,4-isomers, and technical mixtures of both isomers, 4, 4'-methylene bis (cyclohexyl isocyanate), norbornane diisocyanate, and 3,3,5-trimethyl-1-isocyanato-3-isocyanatomethylcyclohexane (IPDI).
  • IPDI 3,3,5-trimethyl-1-isocyanato-3-isocyanatomethylcyclohexane
  • polyisocyanates which are obtainable by reacting polyisocyanates with themselves via isocyanate groups, such as isocyanurates, which are formed by reaction of three isocyanate groups.
  • the polyisocyanates may also contain biuret or allophanate groups. Particularly suitable is IPDI.
  • hydroxyethyl acrylate hydroxypropyl acrylate, hydroxybutyl acrylate and glycerol diacrylate in question.
  • HSA hydroxyethyl acrylate
  • the polyisocyanate is initially charged, treated with DBTL as catalyst and IONOL CP (Shell) as a polymerization inhibitor and in an NCO: OH ratio of 2.5 to 1, 5: 1 of the polyester added.
  • the acrylate-containing component for. B. hydroxyethyl acrylate in the ratio residual NCO: OH from 1.0 to 1.1: 1 and the reaction at 40 to 120 ° C completed, so that an NCO content is reached below 0.1%.
  • a pre-reaction of a polyisocyanate eg. As IPDI, with the acrylate component and the addition of this NCO-containing precursor to the hydroxyl-containing polyester.
  • the amount of A) in the formulation varies from 5 to 95% by weight, preferably from 10 to 70% by weight.
  • Radiation-curable reactive diluents B) and their preparation are z. As described in "Radiation Curing in Polymer Science & Technology, Vol I: Fundamentals and Methods" by J 1 P. Fouassier, JF Rabek, Elsevier Applied Science, London and New York, 1993, Chapter 5, pp. 237-240 These are generally acrylate or methacrylate-containing substances which are liquid at room temperature and thus capable of lowering the overall viscosity of the formulation.
  • Adhesion promoter C) for radiation-curable formulations for metallic substrates generally consist of reaction products (eg esters) of phosphoric acid and alcohol-functionalized acrylates. While the free phosphoric acid groups are responsible for direct adhesion to the metal, the acrylate groups provide a bond with the coating matrix. Such products are also described in WO 01/98413, in JP 08231564, and in JP 06313127.
  • Typical commercial products are EBECRYL 169 and 170 from UCB, ALDITOL VxI 6219 from VIANOVA, CD 9050 and CD 9052 from Sartomer, SIPOMER PAM-100, SIPOMER PAM-200 and SIPOMER PAM-300 from Rhodia and GENORAD 40 from Rahn.
  • the amount of B) in the formulation is 0.1 to 10% by weight.
  • Photoinitiators D) and their preparation are described, for example, in “Radiation Curing in Polymer Science & Technology, VoI II: Photoinitiating Systems” by JP Fouassier, JF Rabek, Elsevier Applied Science, London and New York, 1993.
  • a manufacturer of photoinitiators is, for example CIBA and may be contained in amounts of from 0.2 to 10% by weight.
  • Suitable pigments E) in radiation-curable formulations are described, for. In “Radiation Curing in Polymer Science & Technology, Vol IV: Practical Aspects and Application” by JP Fouassier, JF Rabek, Elsevier Applied Science, London and New York, 1993, Chapter 5, pp.
  • anticorrosive pigments can be found, for example, in Pigment + Filler Tables, O. Lückert, Vincentz Verlag Hannover, 6th edition 2002. Examples include: SHIELDEX C 303 (Grace Davison) and HALOX Coü X 100, HALOX Coü X 200 and HALOX CW 491 (Erbslöh), HEUCOSPHOS SAPP (Heubach), K-White TC 720 (Tayca) and HOMBICOR (Sachtleben). Of course, simple inorganic salts such as zinc phosphate are also suitable.
  • Aggregates F) for radiation-curable formulations are available in various compositions and for various purposes, eg. B. leveling agents, matting agents, degassing agents and others.
  • the invention also provides a process for the production of radiation-curable
  • Formulations with increased corrosion protection on metal substrates characterized in that a mixture consisting of A) radiation-curable resins,
  • E) optional pigments, F) optional other additives, is obtained by the fact that this is first annealed before application and curing for 30 minutes to 48 hours at a temperature of 40 to 100 ° C.
  • feedstocks are intimately mixed in a suitable mixing unit (eg stirred tank, dispermat, static mixer, extruder or flow tube).
  • a suitable mixing unit eg stirred tank, dispermat, static mixer, extruder or flow tube.
  • the mixture temperature may be from room temperature (20 ° C) to 140 ° C, but usually does not exceed 80 ° C and is preferably 20 to 60 ° C.
  • Annealing can be carried out either in the overall formulation or else in constituents of this formulation in which the phosphoric acid-containing adhesion promoter must be present. Annealing involves storage for 30 minutes to 48 hours at a temperature of 40 to 100 ° C. Preference is given to 2 to 8 hours at 40 to 60 ° C. Particularly preferred are 4 to 8 hours at 40 to 50 ° C.
  • the mixture is still ground and sieved prior to application, as is usual with powder coatings.
  • the application can be carried out by application techniques known in paint technology, for. As doctoring, rolling, spraying or spraying.
  • a metallic substrate is particularly suitable steel, with all the different pre-treatment methods, but also aluminum and other alloys, which are provided for corrosion protection reasons with a coating.
  • the curing takes place in the presence of photoinitiators under a UV lamp or in the absence of photoinitiators under electron beams.
  • the properties of the cured coatings are almost identical regardless of the curing method.
  • UV curing and UV lamps are z. As described in "Radiation Curing in Polymer Science & Technology, Vol I: Fundamentals and Methods" by JP Fouassier, JF Rabek, Elsevier Applied Science, London and New York, 1993, Chapter 8, pages 453 to 503.
  • Electron beam hardening and hardener are z. As described in "Radiation Curing in Polymer Science & Technology, Vol I: Fundamentals and Methods" by JP Fouassier, JF Rabek, Elsevier Applied Science, London and New York, 1993, Chapter 4, pages 193 to 225, and in Chapter 9, Pages 503 to 555.
  • the urethane acrylate (BAB) was well mixed with the other formulation ingredients.
  • pigmented systems was additionally dispersed in Dispermaten 20 minutes at 9000 U / min. Thereafter, in the experiments of the invention, the
  • the ready-to-use formulation was knife-coated onto steel sheets (Q-panel, R 36) (40 ⁇ m layer thickness) and subsequently under a UV lamp (UV, minicure, mercury-vapor lamp, 80 W / cm, Technigraf) or an electron beam hardener (ESH, Energy Sciences) cured.
  • a UV lamp UV, minicure, mercury-vapor lamp, 80 W / cm, Technigraf
  • ESH electron beam hardener

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Paints Or Removers (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)

Abstract

L'invention concerne des formulations radiodurcissables qui comprennent des agents adhésifs contenant de l'acide phosphorique et qui, à l'état durci, assurent une protection accrue contre la corrosion sur des substrats métalliques. L'invention concerne également un procédé de production de ces formulations.
EP06763139A 2005-07-05 2006-05-12 Procede de production de formulations radiodurcissables assurant une protection accrue contre la corrosion sur des supports metalliques et ces formulations Withdrawn EP1902109A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005031271A DE102005031271A1 (de) 2005-07-05 2005-07-05 Verfahren zur Herstellung von strahlenhärtbaren Formulierungen mit erhöhtem Korrosionsschutz auf Metalluntergründen und solche Formulierungen
PCT/EP2006/062286 WO2007003462A1 (fr) 2005-07-05 2006-05-12 Procede de production de formulations radiodurcissables assurant une protection accrue contre la corrosion sur des supports metalliques et ces formulations

Publications (1)

Publication Number Publication Date
EP1902109A1 true EP1902109A1 (fr) 2008-03-26

Family

ID=36636152

Family Applications (1)

Application Number Title Priority Date Filing Date
EP06763139A Withdrawn EP1902109A1 (fr) 2005-07-05 2006-05-12 Procede de production de formulations radiodurcissables assurant une protection accrue contre la corrosion sur des supports metalliques et ces formulations

Country Status (11)

Country Link
US (1) US8222312B2 (fr)
EP (1) EP1902109A1 (fr)
JP (1) JP2009500480A (fr)
CN (1) CN1896162B (fr)
AU (1) AU2006265229B2 (fr)
BR (1) BRPI0612592A2 (fr)
CA (1) CA2614136A1 (fr)
DE (1) DE102005031271A1 (fr)
MX (1) MX2007015938A (fr)
WO (1) WO2007003462A1 (fr)
ZA (1) ZA200800065B (fr)

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DE102006003956A1 (de) * 2006-01-26 2007-08-02 Degussa Gmbh Korrossionsschutzschicht auf Metalloberflächen
KR101029340B1 (ko) 2006-03-31 2011-04-13 후지쿠라 가세이 가부시키가이샤 금속기재용 하드 코트 도료 조성물
DE102006045041A1 (de) * 2006-09-25 2008-03-27 Evonik Degussa Gmbh Strahlenhärtbare Formulierung, die zu flexiblen Beschichtungen mit erhöhtem Korrosionsschutz auf Metalluntergründen führt
DE102006061380A1 (de) * 2006-12-23 2008-06-26 Evonik Degussa Gmbh Kieselsäure und Dispergiermittelhaltige strahlenhärtbare Formulierungen mit erhöhtem Korrosionsschutz auf Metalluntergründen
WO2009001818A1 (fr) 2007-06-26 2008-12-31 Fujikura Kasei Co., Ltd. Composition de revêtement pour film mince métallique et film de revêtement composite brillant obtenu à partir de la composition de revêtement
DE102007038313A1 (de) * 2007-08-14 2009-02-19 Evonik Degussa Gmbh Anorganisch-modifizierte Polyesterbindemittelzubereitung, Verfahren zur Herstellung und ihre Verwendung
DE102007038314A1 (de) * 2007-08-14 2009-04-16 Evonik Degussa Gmbh Verfahren zur kontrollierten Hydrolyse und Kondensation von Epoxy-funktionellen Organosilanen sowie deren Condensation mit weiteren organofunktionellen Alkoxysilanen
DE102007040246A1 (de) * 2007-08-25 2009-02-26 Evonik Degussa Gmbh Strahlenhärtbare Formulierungen
DE102008000721A1 (de) * 2008-03-18 2009-09-24 Evonik Degussa Gmbh Strahlenhärtbare Formulierungen
US8329772B2 (en) * 2010-05-20 2012-12-11 E I Du Pont De Nemours And Company UV-curable polymer thick film dielectric compositions with excellent adhesion to ITO
DE102010041247A1 (de) 2010-09-23 2012-03-29 Evonik Degussa Gmbh Verfahren zur Herstellung von lagerstabilen Polyurethan-Prepregs und daraus hergestellte Formkörper aus Polyurethanzusammensetzung in Lösung
DE102011006163A1 (de) 2011-03-25 2012-09-27 Evonik Degussa Gmbh Lagerstabile Polyurethan-Prepregs und daraus hergestellte Formkörper aus Polyurethanzusammensetzung mit flüssigen Harzkomponenten
DE102012219324A1 (de) 2012-10-23 2014-04-24 Evonik Industries Ag Zusammensetzungen umfassend alkoxysilanhaltige Isocyanateund saure Stabilisatoren
CN104559698B (zh) * 2014-12-11 2017-06-06 惠州市长润发涂料有限公司 一种用于静电喷涂的耐黄变uv透明底漆

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Also Published As

Publication number Publication date
CA2614136A1 (fr) 2007-01-11
DE102005031271A1 (de) 2007-01-18
BRPI0612592A2 (pt) 2010-11-23
ZA200800065B (en) 2008-12-31
AU2006265229B2 (en) 2011-09-01
AU2006265229A1 (en) 2007-01-11
CN1896162B (zh) 2013-10-30
US8222312B2 (en) 2012-07-17
CN1896162A (zh) 2007-01-17
US20080200577A1 (en) 2008-08-21
MX2007015938A (es) 2008-03-07
JP2009500480A (ja) 2009-01-08
WO2007003462A1 (fr) 2007-01-11

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