EP4103634A1 - Polymère ramifié contenant un groupe silane - Google Patents

Polymère ramifié contenant un groupe silane

Info

Publication number
EP4103634A1
EP4103634A1 EP21703266.3A EP21703266A EP4103634A1 EP 4103634 A1 EP4103634 A1 EP 4103634A1 EP 21703266 A EP21703266 A EP 21703266A EP 4103634 A1 EP4103634 A1 EP 4103634A1
Authority
EP
European Patent Office
Prior art keywords
groups
polymer
silane
group
range
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.)
Pending
Application number
EP21703266.3A
Other languages
German (de)
English (en)
Inventor
Andreas Kramer
Marcel Oertli
Ursula Stadelmann
Sven Reimann
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.)
Sika Technology AG
Original Assignee
Sika Technology AG
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 Sika Technology AG filed Critical Sika Technology AG
Publication of EP4103634A1 publication Critical patent/EP4103634A1/fr
Pending 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
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/288—Compounds containing at least one heteroatom other than oxygen or nitrogen
    • C08G18/289—Compounds containing at least one heteroatom other than oxygen or nitrogen containing silicon
    • 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
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • 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
    • C08G18/28—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
    • C08G18/4833—Polyethers containing oxyethylene units
    • C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
    • C08G18/4841—Polyethers containing oxyethylene units and other oxyalkylene units containing oxyethylene end 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
    • C08G18/72—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
    • C08G18/70—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
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
    • C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
    • 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
    • C09D175/08—Polyurethanes from polyethers
    • 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
    • C09J175/08—Polyurethanes from polyethers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • C09K3/1006—Materials in mouldable or extrudable form for sealing or packing joints or covers characterised by the chemical nature of one of its constituents
    • C09K3/1021—Polyurethanes or derivatives thereof

Definitions

  • Combinations of different catalysts in particular combinations of at least one metal catalyst and at least one nitrogen-containing compound, are also suitable.
  • this further polymer containing silane groups is linear. It preferably has an average of 1.7 to 2, particularly preferably 1.8 to 2, in particular 1.9 to 2, silane groups per molecule.
  • the weight ratio between the branched polymer containing silane groups according to the invention and the further polymer containing silane groups is preferably in the range from 10/90 to 70/30, in particular 15/85 to 60/40.
  • the curable composition can be in the form of a one-component or in the form of a two-component composition.
  • “One-component” is a composition in which all components of the composition are stored mixed in the same container and which can be hardened with moisture.
  • Curing is also preferably carried out at ambient temperature.
  • Polymer T-3 725.0 g ethylene oxide-terminated polyoxypropylene triol (OH number 28 mg KOH / g,
  • the volatile constituents in particular a large part of the monomeric 4,4'-diphenylmethane diisocyanate, were then des- Tillatively removed (jacket temperature 180 ° C, pressure 0.1 to 0.005 mbar, condensation temperature 47 ° C).
  • the polymer thus obtained had an NCO content of 1.7% by weight, a viscosity of 19 Pa s at 20 ° C. and a monomeric 4,4'-diphenylmethane diisocyanate content of 0.04% by weight.
  • compositions were tested as follows:

Landscapes

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

Abstract

L'invention concerne un polymère ramifié contenant un groupe silane ayant en moyenne au moins 2,1 groupes silane par molécule, à partir de la réaction (i) d'un polymère contenant un groupe isocyanate ayant une teneur en NCO dans la plage de 0,7 à 4 % en poids, obtenu à partir de la réaction d'au moins un diisocyanate monomère avec au moins un polyol de polyéther dans un rapport molaire NCO:OH d'au moins 1,5:1, avec (ii) au moins un amino-, mercapto- ou hydroxysilane, dans un rapport stœchiométrique d'au moins un amino-, mercapto- ou hydroxysilane par équivalent molaire de groupes isocyanate. Le polymère contenant un groupe silane est stable au stockage, liquide à température ambiante et facile à manipuler, et permet des compositions durcissables caractérisées par une excellente aptitude au façonnage, un durcissement rapide, une résistance élevée avec une ductilité élevée et une stabilité thermique étonnamment bonne. Le polymère est particulièrement adapté en tant que composant de produits d'étanchéité durcissant à l'humidité, d'adhésifs ou de revêtements qui contiennent en particulier un polymère contenant un groupe silane, en particulier linéaire.
EP21703266.3A 2020-02-10 2021-02-03 Polymère ramifié contenant un groupe silane Pending EP4103634A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP20156461 2020-02-10
PCT/EP2021/052560 WO2021160493A1 (fr) 2020-02-10 2021-02-03 Polymère ramifié contenant un groupe silane

Publications (1)

Publication Number Publication Date
EP4103634A1 true EP4103634A1 (fr) 2022-12-21

Family

ID=69570575

Family Applications (1)

Application Number Title Priority Date Filing Date
EP21703266.3A Pending EP4103634A1 (fr) 2020-02-10 2021-02-03 Polymère ramifié contenant un groupe silane

Country Status (7)

Country Link
US (1) US20230054396A1 (fr)
EP (1) EP4103634A1 (fr)
JP (1) JP2023513877A (fr)
KR (1) KR20220139865A (fr)
CN (1) CN115066447A (fr)
BR (1) BR112022014200A2 (fr)
WO (1) WO2021160493A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116355573B (zh) * 2023-02-27 2023-12-01 广东德聚技术股份有限公司 一种多粘接功能的硅烷改性聚醚密封胶及其制备方法

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19849817A1 (de) 1998-10-29 2000-05-04 Bayer Ag Alkoxysilan-Endgruppen aufweisende Polyurethanprepolymere, ein Verfahren zu ihrer Herstellung sowie ihre Verwendung zur Herstellung von Dichtstoffen
DE10353663A1 (de) * 2003-11-17 2005-06-16 Henkel Kgaa Polyurethanzusammensetzungen mit NCO- und Silylreaktivität
DE102011077200A1 (de) 2011-06-08 2012-12-13 Bayer Materialscience Aktiengesellschaft Klebstoffe
JP6181745B2 (ja) * 2012-05-23 2017-08-16 シーカ テクノロジー アクチェンゲゼルシャフト シラン基含有ポリマー
EP2805985A1 (fr) * 2013-05-22 2014-11-26 Sika Technology AG Hydroxysilane et polymère contenant des groupes silanes
EP2832757A1 (fr) * 2013-07-30 2015-02-04 Sika Technology AG Polymère contenant des groupes de silanes
US9982173B2 (en) * 2014-03-11 2018-05-29 Sika Technology Ag Polyurethane hot-melt adhesive having a low content of diisocyanate monomers and good cross-linking speed
EP3023428A1 (fr) * 2014-11-24 2016-05-25 Sika Technology AG Polymère contenant des groupes de silanes
DK3224295T3 (en) * 2014-11-24 2019-01-28 Sika Tech Ag COMPOSITION CONTAINING QUICK CURRENT SILANE GROUPS.

Also Published As

Publication number Publication date
JP2023513877A (ja) 2023-04-04
US20230054396A1 (en) 2023-02-23
BR112022014200A2 (pt) 2022-10-04
KR20220139865A (ko) 2022-10-17
WO2021160493A1 (fr) 2021-08-19
CN115066447A (zh) 2022-09-16

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