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WO2011147965A1 - Composition de silicone durcisable à deux composants - Google Patents

Composition de silicone durcisable à deux composants Download PDF

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Publication number
WO2011147965A1
WO2011147965A1 PCT/EP2011/058728 EP2011058728W WO2011147965A1 WO 2011147965 A1 WO2011147965 A1 WO 2011147965A1 EP 2011058728 W EP2011058728 W EP 2011058728W WO 2011147965 A1 WO2011147965 A1 WO 2011147965A1
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WIPO (PCT)
Prior art keywords
group
organopolysiloxane
carbon
component
carbon atoms
Prior art date
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Ceased
Application number
PCT/EP2011/058728
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English (en)
Inventor
Giorgio Zaffaroni
Antonio Belletti
Sebastien Lanau
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Publication of WO2011147965A1 publication Critical patent/WO2011147965A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups

Definitions

  • the present invention lies in the field of two-component curable compositions as commonly used e. g. in adhesives, sealants and/or coatings.
  • the present invention relates to two-component silicone-based Michael-type-curable compositions with improved mechanical properties and furthermore to their manufacture and use.
  • EP 0 267 004 A2 discloses a curable composition based on an amine-functional organopolysiloxane and an acryl- functional organopolysiloxane.
  • the composition may be utilized in various applications like sealants, caulks, encapsulants and adhesives.
  • EP 0 780 422 A2 discloses an aqueous silicone emulsion which crosslinks by a Michael addition reaction and yields a cured composition upon removal of water, the silicone emulsion comprising the product formed by mixing an organosiloxane polymer, containing at least two acceptor groups per molecule; water; a surfactant and an effective amount of a crosslinker, containing sufficient reactive hydrogens of a Michael donor per molecule or a precursor thereto.
  • WO 98/23691 A1 is a curable coating composition having a binder comprising a polymer (A) containing at least one primary or secondary amine group, a polymer (B) containing at least one ethylenically unsaturated double bond activated by an adjacent electron-withdrawing group, and a polymer (C) containing at least two silicon-bonded alkoxy groups.
  • A polymer containing at least one primary or secondary amine group
  • B containing at least one ethylenically unsaturated double bond activated by an adjacent electron-withdrawing group
  • C polymer containing at least two silicon-bonded alkoxy groups.
  • Either (A) or (B) contains at least one silicon-bonded alkoxy group in its molecule.
  • the coating is capable of curing at ambient temperature and humidity both by hydrolysis and condensation of the Si-O-C bonds of the polyorganosiloxane (C) and of the aminoalkyl silane (A) and by Michael-type addition reaction of the amine group of the aminoalkyl silane (A) with the activated ethylenically unsaturated double bonds of (B).
  • 2005/0171318 A1 which describes a curable composition including a silane compound having an epoxy group and at least one silane compound having an amino group, a mercapto group or an acid anhydride group. At least a part of at least one of the silane compounds includes a condensate.
  • the composition is described to have excellent heat resistance with a small change in storage modulus due to temperatures.
  • curable compositions based on organopolysiloxanes exhibit increased mechanical, in particular elastic properties and allow for filler concentrations being not achievable with conventional systems without significant influence on viscosity if the curing can proceed via Michael-type reactions and if, in a preceding step, aminosilanes having hydrolysable groups at the silicium-atom are reacted with organopolysiloxanes having reactive amino groups and water.
  • the subject matter of the present invention is a two-component curable composition which comprises a component A, at least comprising a product obtainable by reacting
  • R 1 denotes a hydrogen atom or a hydrocarbon residue having 1 to 20 carbon atoms
  • R 2 denotes a divalent organic group having 1 to 20 carbon atoms
  • X, Y, Z mutually independently, denote a hydrocarbon residue having 1 to 20 carbon atoms, a hydroxyl group or a hydrolysable group, provided that at least two of the substituents X, Y and Z denote a hydroxyl group or a hydrolysable group
  • the curable compositions according to the present invention exhibit particularly advantageous properties, in particular increased elongation and tensile strength of the cured material, low viscosity despite high filler contents and optimized thixotropy in the pre-cured state.
  • curable composition is understood to be a substance, or a mixture of multiple substances, that can be converted from a soft state into a harder state by means of physical or chemical actions.
  • Those physical or chemical actions can consist, for example, in the delivery of energy in the form of heat, light, or other electromagnetic radiation, but also in simply bringing about contact with atmospheric moisture, water, or a reactive component.
  • organopolysiloxane is understood to be a synthetic polymeric compound, in which silicium- atoms are linked via oxygen-atoms to form a chain or a three-dimensional network and wherein the remaining valencies are saturated by substituted or non-substituted hydrocarbon residues. "Substituted” means in the context of the present invention that a hydrogen atom is replaced by another atom being different from hydrogen or by a functional group.
  • a “polymer” is understood to be a compound that exhibits at least ten repetitive units.
  • a “primary amino group” is understood to be a group -NH 2 being bonded to any substituent except hydrogen.
  • a “secondary amino group” is understood to be a group of the type -NHR' being bonded to any substituent except hydrogen and with R' being any substituted or non- substituted hydrocarbon group.
  • the term “reacting” means that the respective components are mixed in such a way that they are allowed to react chemically. However, “reacting” does not necessarily mean that all compounds will be converted and will chemically contribute to the formation of a new reaction product. Thus, according to the present invention it is possible that if e. g. an organopolysiloxane A1 , a silane of the formula (I) and water are “reacted” only the silane of the formula (I) and water will form a reaction product, whereas organopolysiloxane A1 remains in the mixture unconverted.
  • an "unsaturated carbon-carbon-bond, wherein at least one electron withdrawing group (EWG) is directly attached to said unsaturated carbon-carbon-bond” is understood to be a carbon-carbon- double or triple bond, one carbon atom of which is directly bonded to a substituent which effects a shift of electron density directed to itself in such a way that the carbon-carbon-double bond is activated to react with a nucleophile under formation of a new o-bond, said activation being stronger than the activation provided by a hydrogen atom instead.
  • the unsaturated carbon-carbon-bond wherein at least one electron withdrawing group (EWG) is directly attached to said unsaturated carbon-carbon-bond is regarded as a Michael-acceptor. Therefore, the unsaturated carbon-carbon-bond is not understood to be part of any aromatic system.
  • EWG electron withdrawing group
  • the unsaturated carbon-carbon-bond, wherein at least one electron withdrawing group (EWG) is directly attached to said unsaturated carbon-carbon-bond is a structural element of the following formula (II)
  • organopolysiloxanes of the present invention - organopolysiloxanes A1 , A2 (described below) as well as organopolysiloxanes B1 - preferably comprise D-units of the structure Si0 2/2 R'R", wherein R' and R" are, mutually independent, hydrocarbon residues having 1 to 20 carbon atoms. More preferably, R' and R" denote, mutually independently, linear alkyl residues having 1 to 4 carbon atoms, still more preferably methyl or ethyl residues. Most preferably, both R' and R" are methyl groups.
  • the organopolysiloxanes of the present invention preferably comprise dimethylsiloxane-repetitive units.
  • At least 80 %, still more preferably at least 90 % and most preferably at least 98 % of the repetitive units of the polysiloxane backbone of the organopolysiloxanes according to the present invention are Si0 2/2 Me 2 units.
  • the at least one organopolysiloxane A1 containing at least one primary and/or secondary amino group preferably has a weight average molecular weight of from 500 g/mol to 15.000 g/mol, more preferably of from 1.500 g/mol to 12.000 g/mol, particularly preferably of from 2.000 to 10.000 g/mol and most preferably of from 2.500 to 5.000 g/mol.
  • weight average molecular weights are determined by GPC (gel permeation chromatography), carried out with THF as eluent (1 ml/min) at room temperature; calibration with polystyrene standard; columns: MIXC, 5UM, 300 X 7.5MM - 2 columns in series, injection volume: 50 ⁇ .
  • GPC gel permeation chromatography
  • component A further comprises at least one organopolysiloxane A2 containing at least one primary and/or secondary amino group, the weight average molecular weight of organopolysiloxane A2 being at least by 10.000 g/mol higher than that of organopolysiloxane A1.
  • organopolysiloxane A2 containing at least one primary and/or secondary amino group, the weight average molecular weight of organopolysiloxane A2 being at least by 10.000 g/mol higher than that of organopolysiloxane A1.
  • the weight average molecular weight of the organopolysiloxane A2 is preferably from 12.000 g/mol to 60.000 g/mol, more preferably from 15.000 g/mol to 55.000 g/mol, particularly preferably from 18.000 g/mol to 50.000 g/mol and most preferably from 22.000 to 47.000 g/mol.
  • component A comprises at least two organopolysiloxanes A2 each containing at least one primary and/or secondary amino group, the weight average molecular weight of each of the organopolysiloxanes A2 being at least by 10.000 g/mol higher than that of organopolysiloxane A1.
  • At least one of the organopolysiloxanes A1 and A2 contains at least one primary amino group (-NH 2 ).
  • the amino functions of polyorganosiloxanes A1 and A2 can be provided by grafting aminoalkyl groups onto the polyorganosiloxanes.
  • Preferred aminoalkyl groups bonded to the organopolysiloxanes comprise monoaminoalkyl groups of the structure - R 3 -NH 2 , R 3 being an alkylene residue having 1 to 8, preferably 1 to 5 and most preferably 1 to 3 carbon atoms.
  • aminoalkyl groups comprise aminomethyl groups -CH 2 -NH 2 , aminoethyl groups -(CH 2 ) 2 -NH 2 and aminopropyl groups -(CH 2 ) 2 -NH 2 .
  • (N- aminoalkyl)-aminoalkyl groups of the structure -R 4 -NH-R 5 -NH 2 are preferred, wherein R 4 and R 5 , mutually independently, denote alkylene residues having 1 to 8, preferably 1 to 5 and most preferably 1 to 3 carbon atoms.
  • polyorganosiloxanes A1 and A2 each contain at least one aminopropyl group and/or at least one (N-aminoethyl)-aminopropyl group.
  • the number of primary amino groups per molecule of organopolysiloxanes A1 preferably is 1 to 9 and more preferably 2 to 8.
  • the number of primary amino groups per molecule of organopolysiloxanes A1 and A2 preferably is 1 to 9 and more preferably 2 to 8. According to the invention, it is possible, that the number of primary amino groups per molecule of organopolysiloxanes A1 and A2 differs within the various amino-functionalized
  • organopolysiloxanes used. Due to grafting as the preferred method to functionalize the organopolysiloxanes with amino groups, the amino functions are preferably distributed statistically over the organopolysiloxane molecules.
  • the amount by weight of organopolysiloxane(s) A1 is preferably 3 wt% to 30 wt%, more preferably 5 wt% to 25 wt% and most preferably 6 wt% to 23 wt%.
  • the amount by weight of organpolysiloxane(s) A2, based on the total weight of component A, is preferably 40 wt% to 90 wt%, more preferably 50 wt% to 80 wt% and most preferably 55 wt% to 75 wt%.
  • the viscosity of any organopolysiloxane(s) A1 present in component A preferably is 1 to 200 mPas, more preferably 20 to 80 mPas.
  • the viscosity of any organopolysiloxane(s) A2 present in component A preferably is 500 to 8000 mPas, more preferably 1000 to 5000 mPas. In the context of the present invention, viscosities are measured by means of a TA INSTRUMENT, cone 2°, shear rate 201/s, at 25°C.
  • Component A of the two-component curable composition according to the invention at least comprises a product obtainable by reacting at least one organopolysiloxane A1 with at least one silane of the formula (I)
  • R 1 in formula (I) denotes a hydrogen atom or a hydrocarbon residue having 1 to 20, preferably 1 to 6 and more preferably 1 to 3 carbon atoms. Most preferably, however, R 1 denotes a hydrogen atom.
  • R 2 denotes a divalent organic group having 1 to 20, preferably 1 to 8 and more preferably 1 to 3 carbon atoms. Generally, the divalent organic group can comprise any heteroatoms, e. g. nitrogen and/or oxygen atoms.
  • R 2 denotes a divalent hydrocarbon group having 1 to 10, preferably 1 to 6 and more preferably 1 to 4 carbon atoms, e. g. a methylene, ethylene or n-propylene group. Most preferably, R 2 denotes a n-propylene group.
  • R 1 denotes a hydrogen atom and R 2 denotes a methylene, ethylene or n-propylene group.
  • hydrolysable group is understood to be any group that can be converted into an OH-Group by chemical reaction with water, e. g. an alkoxy group or an acetoxy group.
  • Preferred alkoxy groups are methoxy and ethoxy groups.
  • X, Y and Z each denote a methoxy group.
  • component A preferably comprises a composition obtainable by reacting at least one organopolysiloxane A1 , at least one silane of the formula (I) and a molar amount of water equaling 0.5 to 3 times the molar amount of hydrolysable groups contained in the silane(s) of formula (I).
  • the molar amount of water equals 0.6 to 2 times, e. g. 0.7 to 1 .5 times and most preferably 0.8 to 1 .3 times the molar amount of hydrolysable groups contained in the silane(s) of the formula
  • the two-component curable composition according to the present invention furthermore comprises a component B which comprises at least one organopolysiloxane B1 containing at least one unsaturated carbon-carbon-bond, wherein at least one electron withdrawing group (EWG) is directly attached to said unsaturated carbon-carbon-bond.
  • a component B which comprises at least one organopolysiloxane B1 containing at least one unsaturated carbon-carbon-bond, wherein at least one electron withdrawing group (EWG) is directly attached to said unsaturated carbon-carbon-bond.
  • EWG electron withdrawing group
  • component B preferably comprises at least one organopolysiloxane B1 containing at least one acrylate, methacrylate and/or acrylamide group, the acrylate and methacrylate groups being understood to be embedded in ester structures of acrylic or (meth)acrylic acid.
  • the term "(meth)acrylate” is understood to comprise “methacrylate” and "acrylate”.
  • -O-C(O)- preferably denotes a -O-C(O)- or a -NH-C(O)- group, the -O-C(O)- group being more preferred.
  • the weight average molecular weight of at least one of organopolysiloxanes B1 is 5.000 g/mol to 30.000 g/mol, more preferably 8.000 g/mol to 26.000 g/mol, e. g. 1 1.000 g/mol to 23.000 g/mol and most preferably 14.000 g/mol to 20.000 g/mol. It has been found that organopolysiloxanes B1 having such molecular weights are highly reactive towards
  • organopolysiloxanes A1 and/or A2 and therefore allow for curable compositions exhibiting good curing properties.
  • the number of unsaturated carbon-carbon-bonds, wherein at least one electron withdrawing group (EWG) is directly attached to said unsaturated carbon-carbon-bond, per molecule of organopolysiloxane(s) B1 is preferably 1 to 3 and more preferably 2.
  • the unsaturated carbon- carbon-bonds, wherein at least one electron withdrawing group (EWG) is directly attached to said unsaturated carbon-carbon-bond are preferably located at the termini of the organopolysiloxane chains and particularly preferably comprise a terminal CH 2 -unit.
  • the unsaturated carbon-carbon-bonds, wherein at least one electron withdrawing group (EWG) is directly attached to said unsaturated carbon-carbon-bond are incorporated into a structure as given by the following formula (III):
  • R 7 denotes an organopolysiloxane residue and R 6 denotes a divalent organic group having 1 to 20, preferably 1 to 10, e. g. 1 to 6 and most preferably 1 to 3 carbon atoms.
  • the viscosity of any organopolysiloxane(s) B1 present in component B is preferably 80 mPas to 5000 mPas, more preferably 100 mPas to 3000 mPas.
  • Both component A and component B of the curable composition according to the invention may contain one or more fillers.
  • the amount of filler, based on the total weight of component A is preferably 3 wt% to 25 wt%, more preferably 4 wt% to 20 wt%, e. g. 5 wt% to 17 wt% and most preferably 6 wt% to 14 wt%.
  • the amount of filler, based on the total weight of component B is preferably 5 wt% to 30 wt%, more preferably 8 wt% to 25 wt%, e. g. 10 wt% to 20 wt% and most preferably 12 wt% to 17 wt%.
  • the filler is variable and can be adapted to the required properties of the formulation.
  • the filler comprise calcium carbonate, lime powder, precipitated and/or pyrogenic silicic acid, zeolites, bentonites, magnesium carbonate, diatomite, aluminia, clay, talc, titanium dioxide, iron oxide, zinc oxide, modified silica, quartz, cristoballite, flint, mica, glass powder and other mineral ground substances.
  • both component A and component B contain treated silica.
  • “Modified silica” is understood to be silicic acid, the surface of which has been treated chemically.
  • Such treatment may consist in reacting hydroxyl groups being present in the surface with organic chlorosilanes, resulting in an increased hydrophobicity.
  • Organic fillers can also be used, in particular carbon black, graphite, wood fibers, wood flour, sawdust, cellulose, cotton, pulp, wood chips, chopped straw, chaff, ground walnut shells and other chopped fibers.
  • short fibers such as glass fibers, glass filament,
  • polyacrylonitrile, carbon fibers, Kevlar ® -fibers or polyethylene fibers an be used.
  • component A and/or component B may comprise inhibitors, solvents, pigments, dyes, stabilizers, extenders, plasticizers, blowing agents, lubricants, antioxidants, adhesion promoters, light stabilizers, UV absorbers, antifoams, fragrances and fungicides as well as other adjuvants commonly used in the art.
  • a further subject matter of the present invention is a method for manufacturing a two component curable composition, at least comprising the steps of
  • R 1 denotes a hydrogen atom or a hydrocarbon residue having 1 to 20 carbon atoms
  • R 2 denotes a divalent organic group having 1 to 20 carbon atoms
  • X, Y, Z mutually independent, denote a hydrocarbon residue having 1 to 20 carbon atoms, a hydroxyl group or a hydrolysable group, provided that at least two of the substituents X, Y and Z denote a hydroxyl group or a hydrolysable group
  • reaction product according to the present invention is understood in the same manner as the abovementioned term “reacting”. Thus, “reaction product” does not necessarily mean that all compounds being reacted will be in fact converted and will chemically contribute to the formation of a new product. Thus, according to the present invention it is possible that if e. g. an organopolysiloxane A1 , a silane of the formula (I) and water are reacted only the silane of the formula (I) and water will form the "reaction product", whereas organopolysiloxane A1 remains in the mixture unconverted.
  • mixing of components can generally be provided by any suitable means known in the art, e. g. by a mechanical stirrer.
  • component A is provided by mixing at least one organopolysiloxane A1 and at least one silane of the formula (I), to which composition water is dropped under stirring, followed by heating the composition under vacuum, simultaneous continuation of stirring and, if appropriate, adding further substances comprised by component A, for example organopolysiloxane(s) A2, filler and the like.
  • step a) at least comprises the steps of
  • R 1 denotes a hydrogen atom or a hydrocarbon residue having 1 to 20 carbon atoms
  • R 2 denotes a divalent organic group having 1 to 20 carbon atoms
  • X, Y, Z mutually independent, denote a hydrocarbon residue having 1 to 20 carbon atoms, a hydroxyl group or a hydrolysable group, provided that at least two of the substituents X, Y and Z denote a hydroxyl group or a hydrolysable group
  • organopolysiloxane A2 containing at least one primary and/or secondary amino group, the number average molecular weight of organopolysiloxane A2 being at least by 10.000 g/mol higher than that of organopolysiloxane A1.
  • the weight/weight-ratio of all silanes of formula (I) to all organopolysiloxanes A1 is preferably 1 :10 to 1 :1 , more preferably 1 :5 to 1 :1 and most preferably 1 :3 to 1 :1.
  • a further subject matter of the present invention is the use of a two-component curable composition according to the invention or of a two-component curable composition
  • Plasticizer methyl terminated PDMS
  • the synthesis was carried out in a three-necked flask, equipped with a mechanical stirrer and a heating system. Time values are given here for producing about 200 g of component A.
  • a first step water was dropped into a solution of PDMS A1 and aminopropyltrimethoxysilane under vigorous stirring (3 min) at room temperature.
  • a second step the mixture was heated under vacuum and stirring was continued (1 h). This gave rise to the elimination of residual water and of methanol resulting from condensation of aminopropyltrimethoxysilane molecules.
  • all further components were added (further stirring for 1 h).
  • Plasticizer methyl terminated PDMS
  • component B All components of component B were mixed using a mechanical stirrer at room temperature (1 h stirring).
  • Tensile strength and elongation at break were measured using an Instron 4302 dynamometer with a static cell load of 1 kN according to DIN 53504 and ISO 37, respectively (crosshead speed: 500 mm/min).
  • Viscosity was measured using a rheometer from TA Instrument (plate-plate system with 250 ⁇ gap, shear rate 30/s, recorded for 3 min).
  • the product (after curing) obtained by the method using aminosilane/water in component A exhibited considerably improved elastic properties - elongation at break was enlarged by about 10 % and tensile strength was enlarged by about 15 %, compared with a formulation obtained by a method in which no aminosilane/water system was used (examples 1 and 2). Furthermore, a component A obtained by a method using aminosilane/water exhibited significantly decreased viscosity and thixotropy which greatly facilitates the application of such component, e. g. when passing the outlet of the package (examples 3 and 4). The use of a component A obtained by a method using aminosilane but no water lead to a product (after curing) which was not even consistent enough to allow for measuring the mechanical properties.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Silicon Polymers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Les propriétés mécaniques d'une composition durcissable doivent être améliorées. On y parvient en proposant une composition durcissable à deux composants comprenant un composant A, comprenant au moins un produit pouvant être obtenu par réaction d'au moins un organopolysiloxane A1 contenant au moins un groupe amino primaire et/ou secondaire, au moins un silane de la formule suivante (I) R1HN-R2-SiXYZ (I) dans laquelle R1 représente un atome d'hydrogène ou un reste hydrocarboné ayant 1 à 20 atomes de carbone, R2 représente un groupe organique divalent ayant 1 à 20 atomes de carbone, X, Y, Z, de façon mutuellement indépendante, représentent un reste hydrocarboné ayant 1 à 20 atomes de carbone, un groupe hydroxyle ou un groupe hydrolysable, à la condition qu'au moins deux des substituants X, Y et Z représentent un groupe hydroxyle ou un groupe hydrolysable, et de l'eau ; un composant B comprenant au moins un organopolysiloxane B1 contenant au moins une liaison carbone-carbone insaturée, dans laquelle au moins un groupe accepteur d'électrons (EWG) est directement attaché à ladite liaison carbone-carbone insaturée. La présente invention concerne également un procédé de fabrication d'une telle composition durcissable et son utilisation comme adhésif, matériau d'étanchéité et/ou revêtement.
PCT/EP2011/058728 2010-05-28 2011-05-27 Composition de silicone durcisable à deux composants Ceased WO2011147965A1 (fr)

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IT000975A ITMI20100975A1 (it) 2010-05-28 2010-05-28 Composto polimerizzabile bicomponente di silicone
ITMI2010A000975 2010-05-28

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110183854A (zh) * 2019-06-03 2019-08-30 浙江新安化工集团股份有限公司 一种腻子型硅橡胶组合物及其制备方法和应用

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0267004A2 (fr) 1986-11-04 1988-05-11 Dow Corning Corporation Composition réticulable à base d'organopolysiloxanes
EP0780422A2 (fr) 1995-12-20 1997-06-25 Dow Corning Corporation Emulsions à base de silicones réticulant par réaction d'addition Michael
WO1998023691A1 (fr) 1996-11-29 1998-06-04 International Coatings Limited Composition de revetement
US6265514B1 (en) * 2000-02-17 2001-07-24 Dow Corning Corporation Poly(siloxane-acrylate) elastomers with oxycarbonylethyleneimino-containing organic group and method of making the same
US6281321B1 (en) * 1997-11-27 2001-08-28 Akzo Nobel N.V. Coating compositions
US20050171318A1 (en) 2004-02-03 2005-08-04 The Yokohama Rubber Co., Ltd. Curable resin composition

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0267004A2 (fr) 1986-11-04 1988-05-11 Dow Corning Corporation Composition réticulable à base d'organopolysiloxanes
EP0780422A2 (fr) 1995-12-20 1997-06-25 Dow Corning Corporation Emulsions à base de silicones réticulant par réaction d'addition Michael
WO1998023691A1 (fr) 1996-11-29 1998-06-04 International Coatings Limited Composition de revetement
US6281321B1 (en) * 1997-11-27 2001-08-28 Akzo Nobel N.V. Coating compositions
US6265514B1 (en) * 2000-02-17 2001-07-24 Dow Corning Corporation Poly(siloxane-acrylate) elastomers with oxycarbonylethyleneimino-containing organic group and method of making the same
US20050171318A1 (en) 2004-02-03 2005-08-04 The Yokohama Rubber Co., Ltd. Curable resin composition

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110183854A (zh) * 2019-06-03 2019-08-30 浙江新安化工集团股份有限公司 一种腻子型硅橡胶组合物及其制备方法和应用
CN110183854B (zh) * 2019-06-03 2020-11-03 浙江新安化工集团股份有限公司 一种腻子型硅橡胶组合物及其制备方法和应用

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