EP1902112A1 - Matieres adhesives ou d'etancheite a reticulation silane, procede de production et utilisation associes - Google Patents

Matieres adhesives ou d'etancheite a reticulation silane, procede de production et utilisation associes

Info

Publication number
EP1902112A1
EP1902112A1 EP06707071A EP06707071A EP1902112A1 EP 1902112 A1 EP1902112 A1 EP 1902112A1 EP 06707071 A EP06707071 A EP 06707071A EP 06707071 A EP06707071 A EP 06707071A EP 1902112 A1 EP1902112 A1 EP 1902112A1
Authority
EP
European Patent Office
Prior art keywords
adhesive
polymer
radical
atoms
sealant compositions
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Withdrawn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
EP06707071A
Other languages
German (de)
English (en)
Inventor
Thomas Bachon
Jennifer Schmidt
Thomas Tamcke
Nicole Ditges
Patrick Gawlik
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.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP1902112A1 publication Critical patent/EP1902112A1/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Withdrawn legal-status Critical Current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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4825—Polyethers containing two hydroxy groups
    • 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
    • C08G18/71—Monoisocyanates or monoisothiocyanates
    • C08G18/718—Monoisocyanates or monoisothiocyanates containing silicon
    • 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
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • 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
    • C08G2190/00—Compositions for sealing or packing joints
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
    • Y10T428/31609—Particulate metal or metal compound-containing
    • Y10T428/31612—As silicone, silane or siloxane
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31652—Of asbestos
    • Y10T428/31663—As siloxane, silicone or silane

Definitions

  • Silane-crosslinking adhesives or sealants process for their preparation and their use
  • the present invention relates to silane-crosslinking adhesive or sealant compositions comprising a) at least one polymer of the general formula (I)
  • R 1 is an alkyl radical having 1 to 8 C atoms
  • R 2 is an alkyl or alkoxy radical having 1 to 8 C atoms
  • A is a carboxy, carbamate, carbonate radical , Ureido, urethane or sulfonate bond or an oxygen atom
  • adhesion promoters adhesion promoters, drying agents and / or reactive diluents.
  • Silane-crosslinking adhesives and sealants contain alkoxysilane-terminated polymers as binders.
  • Polymer systems that have reactive alkoxysilyl groups have long been known. In the presence of atmospheric moisture, these alkoxysilane-terminated polymers are capable, even at room temperature, of condensing one another with elimination of the alkoxy groups.
  • mainly long-chain polymers thermoplastics
  • relatively wide-meshed three-dimensional networks elastomers
  • highly crosslinked systems thermosets
  • the polymers typically have an organic backbone bearing alkoxysilane groups at the ends.
  • the organic skeleton may be, for example, polyurethanes, polyesters, polyethers, etc.
  • a one-component reactive system composition which contains an alkoxysilane-terminated polyurethane, a curing catalyst and optionally conventional additives.
  • WO 99/48942 A1 discloses alkoxysilane-terminated polyurethanes and corresponding polyurethane-containing preparations which, in addition to the alkoxysilated polyurethanes, may contain solvents, catalysts, plasticizers, reactive diluents, fillers and the like.
  • the polymeric backbone may also contain organosiloxane in addition to organic components, as described in WO 96/34030 A1.
  • the alkoxysilane end group-containing polymers used in the prior art generally contain methoxysilane end groups. These binders are often used as a replacement for NCO-terminated polyurethanes and have significant toxicological advantages for the processor due to the isocyanate-free. However, a disadvantage is the elimination of small amounts of methanol during curing.
  • the currently customary silane-terminated polymers generally contain dimethoxymethylsilyl or trimethoxysilyl end groups. Replacement of the methoxy groups with ethoxy groups reduces the reactivity of the polymers to such an extent that the curing rate of the adhesives is no longer acceptable.
  • the present invention therefore provides adhesives or sealants of the type mentioned, which are characterized in that the adhesion promoters, desiccants and / or reactive diluents containing ⁇ -silanes ethoxy groups of the general formula (II)
  • R 3 is an organic radical connected via a heteroatom to the methylene group and R 4 is an alkyl radical having 1 to 8 C atoms or an ethoxy radical.
  • the radical R 3 in the general formula (II) is advantageously a methacryloxy or carbamate radical, an amino group or an alkoxy radical.
  • the polymeric backbone R is a mono- to tetravalent, preferably a di- or trivalent, hydrocarbon radical which may contain heteroatoms and / or organosiloxane groups.
  • Examples of the polymeric backbone are alkyd resins, oil-modified alkyd resins, unsaturated polyesters, natural oils, e.g. As linseed oil, tung oil, soybean oil, as well as epoxies, polyamides, thermoplastic polyesters such.
  • polyethylene terephthalate and polybutylene terephthalate polycarbonates, polyethylenes, polybutylenes, polystyrenes, polypropylenes, Ethylenpropylenco- and terpolymers, acrylates, for. B. homopolymers and copolymers of acrylic acid, acrylates, methacrylates, acrylamides, their salts and the like, phenolic resins, Polyoxymethylenhomo- and copolymers, polyurethanes, polysulfones, polysulfide rubbers, nitrocellulose, vinyl butyrates, vinyl polymers, eg.
  • ethyl cellulose, CeIIu loseacetate and butyrates, rayon, shellac, waxes, Ethylencoplymere such.
  • Ethylene acrylate copolymers organic rubbers, silicone resins and the like.
  • Other examples include polyethers such as polyethylene oxide, polypropylene oxide and polytetrahydrofuran.
  • polyethers, polyesters and polyurethanes are particularly preferred.
  • adhesion promoters, desiccants and / or reactive diluents ⁇ -silanes are selected from the group consisting of ⁇ -amino, ⁇ -methacrylic, ⁇ -carbamatosilanes and ⁇ -alkoxysilanes.
  • Suitable examples are N-cyclohexylaminomethylmethyldiethoxysilane, N-cyclohexylaminomethyltriethoxysilane, N-phenylaminomethyltriethoxysilane, (methacryloxymethyl) methyldiethoxysilane and methacryloxymethyltriethoxysilane, N- (triethoxysilylmethyl) -O-methyl-carbamate and N- (methyldiethoxysilylmethyl) -O-methyl-carbamate.
  • the adhesives and sealants in addition to the polymer and the ⁇ -silane as a further component fillers.
  • Suitable fillers are for. As chalk or lime, precipitated and / or fumed silica, zeolites, bentonites, ground minerals and other familiar to the expert inorganic fillers.
  • organic fillers can also be used, in particular fiber short cuts and the like.
  • fillers are preferred which impart thixotropy to the adhesive or sealant compositions, e.g. B. swellable plastics such as PVC.
  • the adhesives and sealants in addition to the polymer and the ⁇ -silane and the fillers contain other conventional additives such as plasticizers, solvents, UV stabilizers, antioxidants, catalysts, desiccants, reactive diluents and adhesion promoters.
  • the adhesive or sealant compositions according to the invention advantageously contain 5 to 90, preferably 10 to 70 parts by weight, more preferably 15 to 50 parts by weight of polymer a) and 0.1 to 10 parts by weight of ⁇ -silane.
  • the invention also relates to a process for preparing the silane-crosslinking adhesive or sealant compositions, which is characterized in that the polymer a), the ⁇ -silanes b) and optionally fillers are mixed together.
  • the polymer a), the ⁇ -silanes b) and optionally fillers are mixed together.
  • the invention further relates to the use of the adhesive compositions according to the invention for bonding wood, plastics, metals, mirrors, glass, ceramics, mineral substrates, leather, textiles, paper, cardboard and rubber, wherein the materials can be bonded to each other with themselves or with each other ,
  • the invention also relates to the use of the adhesive composition of the invention as a reactive postcrosslinking pressure-sensitive adhesive.
  • the invention relates to the use of the sealant compositions of the invention as a sealant mass.
  • the compositions of the invention can also be used as a surface coating agent, as a water vapor barrier, as a dowel, perforated or cracked filler and for the production of molded parts.
  • Polymer 1 ( ⁇ -triethoxysilyl-terminated polypropylene glycol):
  • Polymer 2 ( ⁇ -trimethoxysilyl-terminated polypropylene glycol):
  • Kaneka MS Polymer S 303 H 1 a dimethoxymethylsilyl-terminated polymer from Kaneka, was used as polymer 4.
  • AMMO aminopropyltrimethoxysilane
  • AMEO aminopropyltriethoxysilane
  • DBTL dibutyltin dilaurate
  • DBTAc dibutyltin acetonate
  • An adhesive formulation based on ⁇ -methoxysilyl-terminated polypropylene glycol and methoxysilanes has good properties, but it does split off> 2% of methanol (Comparison 3).
  • An adhesive formulation based on ⁇ -methoxysilyl-terminated polypropylene glycol and ethoxysilanes has good properties, eliminating ⁇ 0.3% of methanol (Examples 1 and 3).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Sealing Material Composition (AREA)

Abstract

L'invention concerne des matières adhésives ou d'étanchéité à réticulation silane contenant a) au moins un polymère de formule (I), dans laquelle R est un groupe hydrocarbure monovalent à quadrivalent, R<SUP>1</SUP> signifie un groupe alkyle doté de 1 à 8 atomes C, R<SUP>2</SUP> représente un groupe alkyle ou alcoxy doté de 1 à 8 atomes C, A désigne une liaison carboxy, carbamate, carbonate, ureido, uréthane ou sulfonate ou bien un atome d'oxygène, x = 1 à 8 et n = 1 à 4, et b) des agents adhésifs, des agents désydratants et/ou des diluants réactifs. Les agents adhésifs, les agents désydratants et/ou les diluants réactifs sont des silanes a contenant des groupes éthoxy de formule (II), dans laquelle R<SUP>3</SUP> est un reste organique lié au groupe méthylène par un hétéroatome et R<SUP>4</SUP> désigne un reste alkyle doté de 1 à 8 atomes C ou bien un reste éthoxy. La présente invention porte également sur un procédé pour produire ces matières adhésives ou d'étanchéité ainsi que sur leur utilisation.
EP06707071A 2005-06-23 2006-02-18 Matieres adhesives ou d'etancheite a reticulation silane, procede de production et utilisation associes Withdrawn EP1902112A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE200510029282 DE102005029282A1 (de) 2005-06-23 2005-06-23 Silanvernetzende Kleb- und Dichtstoffmassen, Verfahren zu ihrer Herstellung und ihre Verwendung
PCT/EP2006/001486 WO2006136211A1 (fr) 2005-06-23 2006-02-18 Matieres adhesives ou d'etancheite a reticulation silane, procede de production et utilisation associes

Publications (1)

Publication Number Publication Date
EP1902112A1 true EP1902112A1 (fr) 2008-03-26

Family

ID=36253851

Family Applications (1)

Application Number Title Priority Date Filing Date
EP06707071A Withdrawn EP1902112A1 (fr) 2005-06-23 2006-02-18 Matieres adhesives ou d'etancheite a reticulation silane, procede de production et utilisation associes

Country Status (7)

Country Link
US (1) US20100055474A1 (fr)
EP (1) EP1902112A1 (fr)
JP (1) JP2008546879A (fr)
CN (1) CN101203580B (fr)
DE (1) DE102005029282A1 (fr)
MX (1) MX2007016276A (fr)
WO (1) WO2006136211A1 (fr)

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CA2665495C (fr) * 2006-10-05 2018-02-06 Dow Global Technologies Inc. Composition d'amorce destinee a la liaison du verre
DE102007038030B4 (de) * 2007-08-10 2009-07-09 Henkel Ag & Co. Kgaa Härtbare Zusammensetzungen aus Dimethoxysilanen
US7891636B2 (en) * 2007-08-27 2011-02-22 3M Innovative Properties Company Silicone mold and use thereof
JP5765938B2 (ja) 2007-10-17 2015-08-19 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ 有機金属化合物を主成分とする光潜伏性触媒
DE102008032580A1 (de) * 2008-07-11 2010-01-14 Henkel Ag & Co. Kgaa Härtbare Zusammensetzungen
DE102008038488A1 (de) 2008-08-20 2010-02-25 Henkel Ag & Co. Kgaa Feuchtigkeitshärtende wasserfeste Beschichtung
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DE102009027357A1 (de) * 2009-06-30 2011-01-05 Wacker Chemie Ag Alkoxysilanterminierte Polymere enthaltende Kleb- oder Dichtstoffmassen
CN102497931B (zh) 2009-09-15 2016-03-09 巴斯夫欧洲公司 光潜钛催化剂
ES2720595T3 (es) 2009-09-15 2019-07-23 Basf Se Catalizadores quelantes de titanio fotolatentes
DE102009046190A1 (de) * 2009-10-30 2011-05-05 Henkel Ag & Co. Kgaa Kaschierklebstoff mit Silanvernetzung
DE102010010598A1 (de) 2010-03-08 2011-09-08 Delo Industrie Klebstoffe Gmbh & Co. Kgaa Dual härtende Masse und deren Verwendung
EP2500009A1 (fr) 2011-03-17 2012-09-19 3M Innovative Properties Company Article dentaire en céramique, son procédé de fabrication et son utilisation
DE102011006366A1 (de) 2011-03-29 2012-10-04 Evonik Goldschmidt Gmbh Alkoxysilylhaltige Klebdichtstoffe mit erhöhter Bruchspannung
RU2610090C9 (ru) 2011-04-05 2018-04-26 Басф Се Фотолатентные катализаторы на основе титан-оксо-хелатов
JP5993367B2 (ja) * 2011-04-15 2016-09-14 株式会社カネカ 建築用外装材
JP5974013B2 (ja) * 2011-09-22 2016-08-23 株式会社カネカ 硬化性組成物およびその硬化物
DE102013206883A1 (de) 2013-04-17 2014-10-23 Evonik Industries Ag Alkoxysilylhaltige Klebdichtstoffe mit intrinsisch reduzierter Viskosität
DE102013223444B4 (de) 2013-11-18 2015-06-03 Evonik Industries Ag Verwendung von Guanidinumsetzungsprodukten bei der Herstellung von Polyurethansystemen
DE102013224708A1 (de) 2013-12-03 2015-06-03 Evonik Industries Ag Alkoxysilylhaltige Klebdichtstoffe mit intrinsisch reduzierter Viskosität
CN107207870B (zh) * 2015-01-16 2020-06-23 株式会社钟化 固化性组合物及其固化物
DK3050910T3 (en) 2015-01-28 2017-02-27 Evonik Degussa Gmbh MODIFIED ALCOXYLING PRODUCTS, WHICH HAVE AT LEAST A NON-TERMINAL ALCOXYSILYL GROUP, WITH INCREASED STOCK STABILITY AND IMPROVED EXTENSION, AND THE POLYMES USED THEREOF
EP3202816B1 (fr) 2016-02-04 2018-09-19 Evonik Degussa GmbH Colle d'etancheite contenant des alkoxysilyles et ayant une resistance amelioree a l'allongement d'une dechirure amorcee
WO2018042030A1 (fr) * 2016-09-05 2018-03-08 Merz+Benteli Ag Utilisation d'un prépolymère modifié par un organocarbonate comme produit de départ pour la préparation de polymères alkoxysilane exempts d'isocyanates et d'isothiocyanates
KR20200128062A (ko) * 2018-02-27 2020-11-11 헨켈 아게 운트 코. 카게아아 바이오기반 반응성 가소제 및 이를 함유하는 접착제 및 실란트
CN111849412B (zh) * 2019-04-30 2023-03-21 杭州先创高新材料有限公司 一种固定中等尺寸纳米晶磁芯的有机硅胶粘剂及制备方法
CN112608444B (zh) * 2020-12-04 2023-05-12 浙江皇马科技股份有限公司 一种聚氨酯树脂、ms密封胶及制备方法
CN114854022B (zh) * 2022-04-12 2023-06-16 华南理工大学 一种高折射率含甲基丙烯酰氧基有机硅增粘剂及其制备方法与应用

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Also Published As

Publication number Publication date
CN101203580B (zh) 2011-08-17
MX2007016276A (es) 2008-03-05
JP2008546879A (ja) 2008-12-25
WO2006136211A1 (fr) 2006-12-28
CN101203580A (zh) 2008-06-18
DE102005029282A1 (de) 2006-12-28
US20100055474A1 (en) 2010-03-04

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