WO2000047588A1 - Esters d'aminosilane - Google Patents

Esters d'aminosilane Download PDF

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Publication number
WO2000047588A1
WO2000047588A1 PCT/EP2000/000721 EP0000721W WO0047588A1 WO 2000047588 A1 WO2000047588 A1 WO 2000047588A1 EP 0000721 W EP0000721 W EP 0000721W WO 0047588 A1 WO0047588 A1 WO 0047588A1
Authority
WO
WIPO (PCT)
Prior art keywords
esters
carbon atoms
aminosilane
polyols
formula
Prior art date
Application number
PCT/EP2000/000721
Other languages
German (de)
English (en)
Inventor
Patrick Tintillier
Laurence Druene
Martine Gasecki
Original Assignee
Cognis Deutschland 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
Priority claimed from DE19907893A external-priority patent/DE19907893C1/de
Application filed by Cognis Deutschland Gmbh filed Critical Cognis Deutschland Gmbh
Priority to EP00910628A priority Critical patent/EP1153028A1/fr
Publication of WO2000047588A1 publication Critical patent/WO2000047588A1/fr

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
    • C—CHEMISTRY; METALLURGY
    • C03—GLASS; MINERAL OR SLAG WOOL
    • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
    • C03C17/28—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material
    • C03C17/30—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material with silicon-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • 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
    • C08F30/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
    • C08F30/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
    • C08F30/08—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon

Definitions

  • the invention is in the field of photopolymerization and relates to new unsaturated aminosilane esters, a process for their preparation, a process for coating glass using the new esters and their use as photomers.
  • Esters of unsaturated carboxylic acids can polymerize in the presence of suitable starters and under the action of light (photopolymerization). This process is widely used in industry to coat hard surfaces.
  • a special area of application is the finishing of glass with the aim of giving the surface a milky, opaque appearance.
  • the known acrylic acid esters are usually mixed with silicates and then photopolymerized.
  • the disadvantage here is that the coating does not adhere very firmly and, particularly if the film has cracks, easily peels off again.
  • the object of the present invention was to provide new photomers which adhere better to the glass surface and thus overcome the disadvantages of the prior art.
  • the invention relates to new aminosilane esters which are obtained by reacting alk-oxylated polyols with unsaturated carboxylic acids of the formula (I), if appropriate
  • R 1 represents hydrogen or alkyl radicals having 1 to 4 carbon atoms
  • R 2 represents hydrogen or methyl
  • n represents 0 or numbers from 1 to 4
  • the resulting esters are then condensed with aminosilanes of the formula (II), OR 3
  • R 3 , R 4 and R 5 independently of one another represent alkyl and / or hydroxyalkyl radicals having 1 to 4 carbon atoms, and m represents numbers from 1 to 3.
  • the aminosilane esters resulting from the Michael reaction between the unsaturated carboxylic acid esters and the aminosilanes with the hydroxyl groups present on the glass surface enter into a covalent bond with the elimination of alcohol and thus adhere firmly.
  • the aminosilane esters are crosslinked via the double bonds contained in the molecule, which form a film on the glass surface that does not detach even if there is mechanical damage or cracking.
  • the invention further relates to a process for the preparation of aminosilane esters, in which optionally alkoxylated polyols are reacted with unsaturated carboxylic acids of the formula (I),
  • R 1 CH C- (CH 2 ) nCOOH (I)
  • R 1 represents hydrogen or alkyl radicals having 1 to 4 carbon atoms
  • R 2 represents hydrogen or methyl
  • n represents 0 or numbers from 1 to 4
  • the resulting esters are then condensed with aminosilanes of the formula (II)
  • R 3 , R 4 and R 5 independently of one another represent alkyl and / or hydroxyalkyl radicals having 1 to 4 carbon atoms, and m represents numbers from 1 to 3.
  • Polyols which are suitable for the purposes of the invention preferably have 2 to 15 carbon atoms and two to 6 hydroxyl groups. Typical examples are
  • Alkylene glycols such as, for example, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, butylene glycol, hexylene glycol and polyethylene glycols with an average molecular weight of 100 to 1,000 daltons;
  • Methyl compounds such as, in particular, trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol, dipentaerythritol and neopentylglycol;
  • Lower alkyl glucosides in particular those with 1 to 8 carbons in the alkyl radical, such as methyl and butyl glucoside;
  • Sugar alcohols with 5 to 12 carbon atoms such as sorbitol or mannitol,
  • Aminosugars such as glucamine
  • hydrophilized polyols are used which are present as adducts of on average 1 to 10 and preferably 3 to 8 moles of ethylene and / or propylene oxide.
  • the adducts of 3 to 5 moles of ethylene or propylene oxide with glycerol or neopentyl glycol are particularly preferred.
  • the optionally alkoxylated polyols are esterified with acrylic acid, methacrylic acid or mixtures thereof. Because of the higher reactivity in photopolymerization, acrylic acid is preferably used. It is advisable to use the polyols and the carboxylic acids in a molar ratio of 1: 0.5 to 1: 1.5, based on the hydroxyl groups available in the polyol. If polyols with two hydroxyl groups are used, the conditions for the esterification, in particular the use ratio, will be chosen for reasons of application technology so that predominantly diesters are formed.
  • Aminosilanes are known substances which are available, for example, from Witco under the name Silquest® Silan A 1100 or A 1120. 3-aminopropyltrimethoxysilane is preferably used.
  • the polyol esters and the aminosilanes are preferably used in a molar ratio of 1: 2 to 2: 1. In particular that is Select ratio so that a sufficient number of double bonds remain in the resulting aminosilane ester so that photopolymerization can take place.
  • the new aminosilane esters contain double bonds which are amenable to photopolymerization. Another object of the invention therefore relates to the use of the esters as photomers. A final object of the invention is finally directed to a process for coating or matting, in which the new aminosilane esters are first applied to the glass surfaces, the layer thickness preferably being 1 to 10 and preferably 5 to 8 ⁇ m, and then the film in the presence developed by known photoinitiators by irradiation with light of a suitable wavelength and intensity, ie polymerized.
  • NPGPODA neopentyl glycol propoxylated di
  • Example 2 Analogously to Example 1, 79.1 g NPGPODA were reacted with 25.1 g 3-APTS.
  • GPTA glycerol propoxylated triacrylate
  • GPTA glycerol propoxylated triacrylate
  • Phln photoinitiator (irgacure 1173, Ciba-Geigy)

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Geochemistry & Mineralogy (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne de nouveaux esters d'aminosilane. Pour obtenir lesdits esters, on fait réagir des polyols éventuellement alcoxylés avec des acides carboxyliques insaturés de formule (I), dans laquelle R1 représente hydrogène ou des résidus alkyle renfermant 1 à 4 atomes de carbone, R2 représente hydrogène ou méthyle, et n représente O ou un nombre compris entre 1 et 4; puis on condense les esters obtenus avec des aminosilanes de formule (II), dans laquelle R?3, R4 et R5¿ représentent indépendamment des résidus alkyle et/ou hydroxyalkyle renfermant 1 à 4 atomes de carbone, et m est un nombre compris entre 1 et 3. Ces esters peuvent être utilisés comme photomères pour le revêtement des surfaces de verre.
PCT/EP2000/000721 1999-02-09 2000-01-29 Esters d'aminosilane WO2000047588A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP00910628A EP1153028A1 (fr) 1999-02-09 2000-01-29 Esters d'aminosilane

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE19905106.2 1999-02-09
DE19905106 1999-02-09
DE19907893A DE19907893C1 (de) 1999-02-09 1999-02-24 Aminosilanester
DE19907893.9 1999-02-24

Publications (1)

Publication Number Publication Date
WO2000047588A1 true WO2000047588A1 (fr) 2000-08-17

Family

ID=26051730

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2000/000721 WO2000047588A1 (fr) 1999-02-09 2000-01-29 Esters d'aminosilane

Country Status (2)

Country Link
EP (1) EP1153028A1 (fr)
WO (1) WO2000047588A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017191455A1 (fr) * 2016-05-05 2017-11-09 Itaconix (U.K.) Limited Promoteurs d'adhésion

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4122074A (en) * 1977-07-05 1978-10-24 Union Carbide Corporation Polyester aminoalkylalkoxysilanes
EP0149741A1 (fr) * 1983-11-10 1985-07-31 DeSOTO, INC. Composition de revêtement liquide, durcissable par rayons et fibres optiques de verre ainsi recouvertes
EP0230342A2 (fr) * 1986-01-06 1987-07-29 Dow Corning Corporation Composés silicones avec des fonctions acryliques
JPH06107672A (ja) * 1992-09-30 1994-04-19 Three Bond Co Ltd （メタ）アクリル官能性ケイ素化合物の製造及び利用
EP0666290A1 (fr) * 1994-02-08 1995-08-09 Dow Corning Corporation Revêtement résistant à l'abrasion
EP0687713A1 (fr) * 1994-06-13 1995-12-20 Dow Corning Corporation Composition de revêtement durcissable par irradiation et à base d'oligomères
US5739192A (en) * 1996-11-20 1998-04-14 Dow Corning Corporation Polysiloxane copolymers from Michael Adduct reactions

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4122074A (en) * 1977-07-05 1978-10-24 Union Carbide Corporation Polyester aminoalkylalkoxysilanes
EP0149741A1 (fr) * 1983-11-10 1985-07-31 DeSOTO, INC. Composition de revêtement liquide, durcissable par rayons et fibres optiques de verre ainsi recouvertes
EP0230342A2 (fr) * 1986-01-06 1987-07-29 Dow Corning Corporation Composés silicones avec des fonctions acryliques
JPH06107672A (ja) * 1992-09-30 1994-04-19 Three Bond Co Ltd （メタ）アクリル官能性ケイ素化合物の製造及び利用
EP0666290A1 (fr) * 1994-02-08 1995-08-09 Dow Corning Corporation Revêtement résistant à l'abrasion
EP0687713A1 (fr) * 1994-06-13 1995-12-20 Dow Corning Corporation Composition de revêtement durcissable par irradiation et à base d'oligomères
US5739192A (en) * 1996-11-20 1998-04-14 Dow Corning Corporation Polysiloxane copolymers from Michael Adduct reactions

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 018, no. 385 (C - 1227) 20 July 1994 (1994-07-20) *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017191455A1 (fr) * 2016-05-05 2017-11-09 Itaconix (U.K.) Limited Promoteurs d'adhésion

Also Published As

Publication number Publication date
EP1153028A1 (fr) 2001-11-14

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