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EP2052000A1 - Résine pour vernis résistant aux milieux - Google Patents

Résine pour vernis résistant aux milieux

Info

Publication number
EP2052000A1
EP2052000A1 EP07728845A EP07728845A EP2052000A1 EP 2052000 A1 EP2052000 A1 EP 2052000A1 EP 07728845 A EP07728845 A EP 07728845A EP 07728845 A EP07728845 A EP 07728845A EP 2052000 A1 EP2052000 A1 EP 2052000A1
Authority
EP
European Patent Office
Prior art keywords
acrylate
meth
isocyanates
hydroxyethyl methacrylate
glycerol mono
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Withdrawn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
EP07728845A
Other languages
German (de)
English (en)
Inventor
Marianne Omeis
Stefan Schrage
Martina Ebert
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.)
Roehm GmbH Darmstadt
Original Assignee
Evonik Roehm 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 Roehm GmbH filed Critical Evonik Roehm GmbH
Publication of EP2052000A1 publication Critical patent/EP2052000A1/fr
Withdrawn legal-status Critical Current

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
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups

Definitions

  • the invention relates to compositions of glycerol mono (meth) acrylate and hydroxyethyl methacrylate, which are polymerized and then crosslinked with isocyanates, a process for their preparation and their use as coating resins with particular media resistance.
  • Glycerol mono (meth) acrylate is a widely used functional comonomer in adhesives, paints and optical materials. Various production methods for glycerol mono (meth) acrylate are known.
  • Glycerol mono (meth) acrylate can be prepared by the transesterification of methyl (meth) acrylate or the esterification of (meth) acrylic acid with glycerol.
  • the result is a product mixture of mono-, di- and trifunctionalized alcohol, which can be separated due to the good solubility of water products only with great effort.
  • the synthetic route is selected via a protected alcohol, the ketalized glycerol or the related glycidol or the corresponding (meth) acrylate to obtain the monoester.
  • the coating of materials to improve the surfaces and change the properties is a wide range of tasks.
  • curable coatings of aromatic tri- or tetracarboxylic acids and dihydroxyalkyl (meth) acrylates are described. These coatings are cured by means of radiation or heat and have good mechanical and optical properties. In particular, the adhesion to plastic surfaces is improved.
  • WO2000 / 23521 claims unsaturated polyester resins with reduced monomer content which are used in gelcoats, coatings or laminates. These materials should be processable with conventional equipment and have mechanical strength.
  • the object of the invention was to produce compositions based on glycerol mono (meth) acrylate, which have a particular media resistance.
  • compositions of glycerol mono (meth) acrylate and hydroxyethyl methacrylate which is radically polymerized and then with
  • Isocyanates are crosslinked.
  • radical polymerization also other comonomers can be used.
  • the notation (meth) acrylate as used herein means both methacrylate, e.g.
  • compositions of the invention have coating resins with excellent media resistance.
  • the invention also provides a process for the preparation of the composition according to the invention.
  • the method is characterized in that glycerol mono (meth) acrylate and hydroxyethyl methacrylate in the appropriate Solvents are polymerized at a temperature of 100-150 0 C and with the addition of initiators and then crosslinked with isocyanates.
  • the isocyanates used are preferably di- and polyfunctional aliphatic and also aromatic representatives.
  • a typical representative of the aliphatic isocyanate is the trimer of hexamethylene diisocyanate (trade name Desmodur N3300, Bayer AG).
  • Organotin compounds are preferably used for catalysis and an NCO / OH ratio preferably adjusted from 42/58.
  • the basis for calculation is the OH number of the resin.
  • Another advantage of the method according to the invention is that the viscosities of the resulting coating resins are below 20,000 mPas at 23 ° C, so that in the subsequent formulation of the clearcoats are therefore no restrictions to be expected.
  • composition of glycerol mono (meth) acrylate and hydroxyethyl methacrylate which are polymerized together and then crosslinked with isocyanates, find application in paint formulations.
  • n-butyl acetate In a 1 liter flask with reflux condenser 100.02 g of n-butyl acetate are initially charged and heated. The polymerization is carried out under a nitrogen atmosphere. 30.66 g of tert-butyl peroxy-2-ethylhexanoate, 78.93 g of isobornyl methacrylate, 157.85 g of n-butyl acrylate, 91.8 g of glycerol monomethacrylate, 71.84 g of hydroxyethyl methacrylate, 11.84 g of methacrylic acid and 7.38 g of mercaptoethanol premixed .; this monomer mixture is added to the bottom over 4 hours.
  • Films having a thickness of 30 +/- 5 ⁇ m were produced.
  • the crosslinked polymer films are treated for 15 minutes with the various media. For this purpose, a soaked cotton cloth is pressed onto the surface. After drying (24 hours at 23 ° C) the pendulum hardness is measured (pendulum hardness according to König, DIN EN ISO 1522).
  • IBMA iso-bornyl methacrylate, nBA n-butyl acrylate, GMMA glycerol monomethacrylate, HEMA hydroxyethyl methacrylate, GMAA methacrylic acid, MEK methyl ethyl ketone
  • a high value of the pendulum hardness stands for a high hardness of the resulting paint film.
  • the glycerol monomethacrylate samples have significantly improved media resistance to the polymer film which does not contain GMMA.
  • the molar ratio of GMMA / HEMA 1/1 shows the best properties.

Landscapes

  • Chemical & Material Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne des compositions de mono(méth)acrylate de glycérine et de méthacrylate d'hydroxyéthyle, également avec addition d'autres monomères, qui sont polymérisées de manière radicalaire et ensuite réticulées avec des isocyanates, un procédé pour leur préparation, ainsi que leur utilisation comme résine pour vernis présentant une résistance particulière aux milieux.
EP07728845A 2006-08-18 2007-05-07 Résine pour vernis résistant aux milieux Withdrawn EP2052000A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102006038714A DE102006038714A1 (de) 2006-08-18 2006-08-18 Medienbeständige Lackharze
PCT/EP2007/054392 WO2008019895A1 (fr) 2006-08-18 2007-05-07 Résine pour vernis résistant aux milieux

Publications (1)

Publication Number Publication Date
EP2052000A1 true EP2052000A1 (fr) 2009-04-29

Family

ID=38229383

Family Applications (1)

Application Number Title Priority Date Filing Date
EP07728845A Withdrawn EP2052000A1 (fr) 2006-08-18 2007-05-07 Résine pour vernis résistant aux milieux

Country Status (6)

Country Link
US (1) US20090318648A1 (fr)
EP (1) EP2052000A1 (fr)
CN (1) CN101479303A (fr)
DE (1) DE102006038714A1 (fr)
TW (1) TW200815486A (fr)
WO (1) WO2008019895A1 (fr)

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3376567B2 (ja) * 1994-01-26 2003-02-10 関西ペイント株式会社 ２液型水性被覆用組成物
US5722424A (en) * 1995-09-29 1998-03-03 Target Therapeutics, Inc. Multi-coating stainless steel guidewire
JP4351519B2 (ja) * 2003-11-26 2009-10-28 東洋インキ製造株式会社 感光性組成物およびカラーフィルタ
DE102005004639A1 (de) * 2005-02-01 2006-08-03 Ashland-Südchemie-Kernfest GmbH Modifiziertes Poly(meth)acrylat mit reaktiven ethylenischen Gruppen und dessen Verwendung
DE102005010109A1 (de) * 2005-03-02 2006-09-07 Basf Ag Modifizierte Polyolefinwachse

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2008019895A1 *

Also Published As

Publication number Publication date
DE102006038714A1 (de) 2008-02-21
WO2008019895A1 (fr) 2008-02-21
TW200815486A (en) 2008-04-01
US20090318648A1 (en) 2009-12-24
CN101479303A (zh) 2009-07-08

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