WO2022233411A1 - Mélanges contenant un composé fonctionnalisé par silirane et un polymère - Google Patents

Mélanges contenant un composé fonctionnalisé par silirane et un polymère Download PDF

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Publication number
WO2022233411A1
WO2022233411A1 PCT/EP2021/061920 EP2021061920W WO2022233411A1 WO 2022233411 A1 WO2022233411 A1 WO 2022233411A1 EP 2021061920 W EP2021061920 W EP 2021061920W WO 2022233411 A1 WO2022233411 A1 WO 2022233411A1
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Prior art keywords
radical
group
silirane
independently
hydrogen
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PCT/EP2021/061920
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German (de)
English (en)
Inventor
Maximilian MOXTER
Richard Weidner
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Wacker Chemie Ag
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Priority to PCT/EP2021/061920 priority Critical patent/WO2022233411A1/fr
Publication of WO2022233411A1 publication Critical patent/WO2022233411A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/549—Silicon-containing compounds containing silicon in a ring
    • 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 System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C07F7/0838—Compounds with one or more Si-O-Si sequences
    • 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 System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
    • 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
    • C09D183/00—Coating compositions based on 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; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • 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
    • C08G77/12—Polysiloxanes containing silicon bound to hydrogen
    • 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

Definitions

  • the present invention describes mixtures containing, as adhesion promoter, at least one silirane-functionalized compound from a substrate to which at least two silirane groups of the formula (I) are covalently bonded, and at least one polymer. Also included are moldings containing at least one mixture according to the invention and a slightly polar to non-polar substrate, as well as a method for curing the mixtures and the use of the mixtures.
  • Silicones also called poly(organo)siloxanes or siloxanes for short
  • silicones can be used in a variety of ways due to their chemical and physical properties. Unlike carbon-based plastics, the van der Waals forces between siloxane polymer chains are weak, which is why high molecular weight siloxane polymers are still flowable.
  • the polymer components In order to obtain dimensionally stable, rubber-elastic silicones, the polymer components have to be crosslinked with one another.
  • addition crosslinking condensation crosslinking and free-radical crosslinking.
  • vinyl-functionalized polyorganosiloxanes react with hydridosiloxanes (hydrosilylation).
  • condensation crosslinking terminal Si-OH or Si-OR groups with typically multifunctional siloxane building blocks (containing, for example, Si-O-CH 3 , Si-OC 2 H 5 , Si-O-COCH 3 ) are cured by atmospheric moisture and in the presence a metal-based catalyst (e.g. based on tin) reacted.
  • a metal-based catalyst e.g. based on tin
  • condensation-curing systems can be handled as one-component systems.
  • Radical crosslinking uses organic peroxides, for example, which decompose into highly reactive radicals as a result of thermal or photolysis and link functional polyorganosiloxanes (eg vinyl-methyl-siloxanes) with one another in a free-radical manner.
  • organic peroxides for example, which decompose into highly reactive radicals as a result of thermal or photolysis and link functional polyorganosiloxanes (eg vinyl-methyl-siloxanes) with one another in a free-radical manner.
  • polyorganosiloxanes can be applied to solid surfaces, for example textiles, paper and plastics, to render the surfaces water-repellent, non-stick or to impart lubricity.
  • the polyorganosiloxanes most commonly used for these purposes are functional polymethylsiloxanes or blends with methylhydrogenpolysiloxanes. While the polyorganosiloxanes provide the desired surface properties, they often lack adequate durability. For example, they can be removed by washing or by contact with organic solvents.
  • silicones show only limited adhesion to plastic substrates such as polyolefins (eg polyethylene (PE) and polypropylene (PP)), polyethylene terephthalate (PET) or polycarbonate (PC), which is due to the non-polar nature of the plastics.
  • PET polyethylene terephthalate
  • PC polycarbonate
  • Adhesion to plastic substrates can currently only be achieved by complex manipulations of the substrate, for example by pretreatment with solvents, a multi-stage oxygen plasma treatment and/or by applying a priming can be achieved (U. Stschreib, Vacuum in Research and Practice 2015, 27, 16-21).
  • PCT/EP2019/083744 describes silirane-functionalized compounds as thermally and photochemically activatable crosslinkers for the catalyst-free production of elastomeric silicones.
  • This technology represents a sustainable alternative to established crosslinking technologies such as addition or condensation crosslinking, which require the use of platinum, titanium or tin-based catalysts.
  • silirane-containing substrates are used as storage-stable silylene sources that can be activated in a controlled manner.
  • the three-membered silacyclopropane structure motive is under high ring strain and can be thermally converted from 140°C into an intermediate silylene derivative, which reacts with other functional silicone components of the mixtures to form an elastomeric network (see Scheme 1).
  • Scheme 1 Siliranes can be cleaved by thermolysis or photolysis to give an olefin and a silylene.
  • PCT/EP2019/083737 describes silirane-functionalized compounds for the production of elastomeric silicones by nucleophilic ring-opening polymerization.
  • the silirane-containing compounds are potential sources of silylene, the reactive silicon center upon activation is siloxane skeleton is separated, neither crosslinking nor an adhesion-promoting effect can be achieved.
  • JP 63048674 A2 describes a method for coating metallic or ceramic surfaces with hexamethyldisilazane with reference to a silylene reaction. In terms of content, however, the silylation of OH groups on the substrate surface is carried out with hexamethyldisilazane. Reaction conditions which lead to the release of silylenes are not mentioned.
  • the object of the invention was to improve the adhesion of silicones to plastic surfaces without having to subject the plastic surface to an expensive pretreatment.
  • R 2 , R 3 , R 4 , R 5 are independently selected from the group consisting of hydrogen, halogen and C 1 -C 20 hydrocarbon radical, where R 2 and R 4 can be part of a cyclic radical; b) at least one natural or synthetic polymer selected from the group consisting of bl) addition-crosslinking silicone compositions, b2) condensation-crosslinking silicone compositions, b3) hybrid materials/silyl-terminated polymers (STP) and b4) inorganic polymers and organic polymers and combinations of bl to b4.
  • silane-containing compounds as adhesion promoters for existing silicone products or as a component of self-adhesive crosslinkable silicone (hybrid) compositions for plastics with little or no polarity is not known to date.
  • addition-crosslinking silicone masses generally designates hydrosilylatable mixtures containing hydridopolysiloxanes, alkenyl-containing polyorganosiloxanes and fillers (eg silicas). These mixtures can only be crosslinked thermally or photochemically to form elastomeric silicones in the presence of catalysts (eg the platinum-based Karstedt catalyst) and inhibitors. Such mixtures are, for example, in EP 0651 019 A1 or EP 0 444 960 A2.
  • the addition-crosslinking silicone compositions therefore contain metal catalysts.
  • the condensation-crosslinking silicone masses contain metal catalysts.
  • hybrid materials / STP are generally reactive silane-terminated organic polymers (e.g.
  • Polyether which are used, for example, as adhesives, sealants and coating materials. Such materials are described by way of example in WO 2017/137281 A1.
  • inorganic polymers are generally natural and synthetic inorganic polymers (e.g. silicic acids, silicate structures, polysilanes and polysiloxanes).
  • organic polymers are generally natural and synthetic organic polymers suitable for producing molded articles, coatings or laminates. Examples of such polymers can be found in US 5,792,812; US 2007/0141250 A1 and US 4,686,124.
  • the silirane-functionalized compounds thus act as adhesion promoters between the inert polymer carrier body and the applied crosslinkable siloxane mixture
  • the mixture is therefore, with particular advantage, a self-adhesive mixture for the coating of, in particular, chemically inert materials.
  • the silirane functionalized compounds are stable
  • Scheme 2 Top: The Si atoms of the silirane-functionalized compound are bridged through a structural backbone, resulting in a crosslinkable reactive bis-silylene species upon activation. Bottom: The silirane groups are not bridged via the Si atoms, resulting in non-crosslinking cleavage products upon activation.
  • the substrate of the silirane-functionalized compound is preferably selected from the group consisting of silanes, organosilicon compounds, hydrocarbons, silicic acids, carbon-based oligomers and polymers.
  • the substrate of the silirane-functionalized compound is particularly preferably selected from the group consisting of siloxanes, precipitated silica, pyrogenic silica, polyolefins, acrylates, polyacrylates, polyvinyl acetates, polyurethanes and polyethers made from propylene oxide and/or ethylene oxide units
  • the substrate is organosilicon compounds of the general formula
  • R x is independently selected from the group consisting of hydrogen, halogen, an unsubstituted or substituted C 1 -C 20 hydrocarbyl radical and an unsubstituted or substituted C 1 -C 20 hydrocarbyloxy radical.
  • the indices a, b, b′, c, c′, c′′, d, d′, d′′, d′′′′ indicate the number of the respective siloxane unit in the compound and are independently zero or an integer from 1 to 10,000, provided that the sum of a, b, b', c, c', c'', d, d', d'', d''' is at least 2 and at least one of the indices b', c', d'> 2 or at least one of the indices c'', d'' or d , '' is not equal to zero.
  • the radical R' is the silirane group of the formula (I).
  • the radical R a in the formula (I) is preferably a C 1 -C 3 - alkylene radical, particularly preferably an ethylene radical.
  • R 1 is preferably a C 1 -C 6 hydrocarbyl radical or amine radical -N(SiR a R b R c ) 2 , where R a , R b , R c are independently a C 1 -C 6 hydrocarbyl radical.
  • R 1 is particularly preferably a C 1 -C 6 -alkyl radical or -N(SiMe 3 ) 2 .
  • the indices a, b, b', c, c', c'', d, d'' and d''' are preferably zero and the index d' has the value 2, where in formula (I) the index n is 1, R a is a C 1 -C 3 alkylene group and R 1 is a C 1 -C 6 hydrocarbyl group or an amine group -N(SiR a R b R c ) 2 wherein R a ,R b ,R c are independently C 1 -C 6 hydrocarbon radicals.
  • the radicals R 2 , R 3 , R 4 , R 5 are, independently of one another, hydrogen or a C 1 -C 6 -alkyl radical, where R 2 and R 4 can also be part of a cyclic radical.
  • the indices a, b, b', c, c', c'', d, d'' and d''' are particularly preferably zero and the index d' has the value 2, where in formula (I) the Index n is 1, R a is an ethylene radical and R 1 is a C 1 -C 6 alkyl radical or -N(SiMe 3 ) 2 .
  • the radicals R 2 , R 3 , R 4 , R 5 are, independently of one another, hydrogen or a C 1 -C 6 - alkyl radical, where R 2 and R 4 can also be part of a cyclic radical.
  • the radical R x in the formula (II) is preferably selected independently from the group consisting of methyl, ethyl,
  • the silirane-functionalized compound is particularly preferably selected from the group with SV1, SV2 and SV3, where SV1, SV2 and SV3 have the following structures:
  • the proportion of the silirane-functionalized compound in the mixture is preferably 0.5 to 10% by weight, particularly preferably 0.5 to 5% by weight, in particular 0.5 to 2% by weight.
  • a further aspect of the invention relates to moldings comprising at least one of the mixtures according to the invention and a slightly polar to non-polar carrier material.
  • the molding is preferably selected from the group consisting of extrusion or injection molding, single or multi-layer laminates (e.g. produced by spin coating, calendering or dipping processes), encapsulated moldings (e.g. produced in electrocasting by filling, dipping or plasticizing), adhesive or sealable shaped bodies (reactive adhesives) and transitions between identical or different shaped bodies of the same or different carrier materials.
  • the latter means in particular jointing compounds for bonding several dissimilar materials.
  • the shaped body can contain the carrier material in the form of a coating.
  • the shaped body can consist of the carrier material to which the mixture is applied.
  • the carrier material preferably comprises at least one synthetic hydrocarbon polymer selected from the Group with polyolefins made from mono- or polyenes, polyhaloolefin, polyether, polyvinyl chloride, polyvinylidene difluoride, polytetrafluoroethene, polycarbonate, polyester and copolymers thereof. Furthermore, the carrier material can consist of or comprise polymer blends of the hydrocarbon polymers mentioned.
  • the copolymers can be, for example, ethylene propylene diene monomer rubber (EPDM) or acrylonitrile butadiene styrene (ABS).
  • EPDM ethylene propylene diene monomer rubber
  • ABS acrylonitrile butadiene styrene
  • a further aspect of the invention relates to a method for curing the mixture according to the invention by thermal and/or photochemical activation.
  • the mixture is brought into contact with a slightly polar to non-polar carrier material as described above.
  • thermal activation requires a temperature above the decomposition temperature of the silirane compound.
  • the wavelength required for photochemical activation is in the UV range.
  • the reactivity of the siliranes is identical for both activation methods.
  • the activated silirane-functionalized compounds can react with a variety of functional groups due to their high reactivity. Possible reaction partners are, for example, Si-H, Si-OR, Si-OH, C-OH, CH, -NH 2 and vinyl. This covers all typical functional groups of silicones as well as slightly polar to non-polar carrier materials. Curing can take place by means of a one-stage or multi-stage thermal activation in a temperature range from 0 to 200°C, preferably from 10 to 180°C, particularly preferably from 15 to 160°C.
  • Curing preferably takes place by means of a two-stage thermal activation, comprising the following steps: a) setting a temperature T1 in a temperature range from 0 to 140° C. and b) setting a temperature T2 in a temperature range from 120 to 180° C., with the following that T1 ⁇ T2.
  • the mixture to be cured is preferably a component of the molding according to the invention.
  • the process is therefore preferably used in a shaped body according to the invention, with adhesion being promoted between the carrier material and the mixture component b).
  • Another object of the invention is the use of the silirane-functionalized compound according to a) of the mixture according to the invention as an adhesion promoter, in particular as an adhesion promoter between a slightly polar to non-polar carrier material as described above and a polymer according to b) of the mixture according to the invention .
  • Also covered by the invention is the use of the mixture of the invention as a self-adhesive coating material for low-polarity to non-polar carrier materials as described above.
  • the XPS analysis was carried out with a KRATOS Axis Supra spectrometer. The spectra were recorded at a pressure of ⁇ 3*10 -8 Torr with a focused scan using a monochromatic Al-K ⁇ source. The penetration energy in the hybrid lens mode with charge neutralization was 15 eV and the spot size was 800 x 300 ⁇ m. The data were analyzed with the program CasaXPS (version 2.3.15). The signals were integrated using the Shirley background subtraction method. The elemental proportions were quantified using CASA XPS and IMFP data from the NIST database. Sensitivity factors were calculated using published ionization crossing (Scofield, J.
  • Hönel (illuminance: max. 250 mW/cm 2 ) is used.
  • ELASTOSIL® RT604 A/B (from Wacker Chemie AG): Room-temperature-curing silicone rubber (RTV-2).
  • Adhesion promoter SV3 The silirane-functionalized compound SV3 was synthesized as described in PCT/EP2019/083744. 1. Coating of polypropylene with SV3
  • Polypropylene was provided as a square plate with a side length of 2 cm and cleaned three times with isopropanol in an ultrasonic bath for 20 minutes.
  • the coating was carried out by spin-coating n-hexane solutions (concentration 13% by weight) of Siliran SV3. Layer thicknesses of approx. 1/100 mm were obtained.
  • the reaction crosslinking/curing was triggered either by UV-C treatment (at least 15 min at approx. 4-5 raW/cm 2 ) or by heat treatment (1 h at 140°C). Each sample was then extracted three times with THF/diethyl ether and dried in a gas stream.
  • mixtures A and B are mixed in a mass ratio of 1:1 (e.g. with a "DAC-150.1" speed mixer from Hausschild).
  • a) 1, 5 and 10% by weight are used for the additives.
  • of the silirane-functionalized siloxane SV3 was added and mixed with the ELASTOSIL® by hand or using a speed mixer
  • Polypropylene specimens were primed with a 10% by weight solution of SV3 in pentane, which evaporates rapidly at room temperature
  • the amounts used and all of the crosslinking conditions can be found in Table 2. The adhesion of the crosslinked silicone coating to the specimens was evaluated via the detachment stability of the coating.
  • Peel stability was tested by peeling off the crosslinked silicone coating. If, like the reference, it could be released in one piece without tearing, there was no improvement in adhesion. If the material tore because it stuck particularly firmly to the carrier material and had to be removed piecemeal, the adhesion was rated as better than the reference.

Abstract

L'invention concerne des mélanges contenant a), en tant que promoteur d'adhérence, au moins un composé fonctionnalisé par silirane d'un substrat auquel au moins deux groupes silirane de formule (I) sont liés de manière covalente, n = 0 ou 1, Ra étant un groupe hydrocarbure en C1-C20 divalent et R1 étant sélectionné dans le groupe comprenant (i) un groupe hydrocarbure en C1-C20, (ii) un groupe hydrocarbure-oxy en C1-C20, (iii) un groupe silyle -SiRaRbRc, Ra, Rb, Rc représentant indépendamment les uns des autres un groupe hydrocarbure en C1-C6, (iv) un groupe amine -NRx 2, Rx étant indépendamment les uns des autres sélectionnés dans le groupe comprenant (iv.i) un hydrogène, (iv.ii) un groupe hydrocarbure en C1-C20 et (iv.iii) le groupe silyle -SiRaRbRc, et (v) un groupe imine -N=CR1R2, R1, R2 étant indépendamment l'un de l'autre sélectionnés dans le groupe comprenant (v.i) un hydrogène, (v.ii) un groupe hydrocarbure en C1-C20 et (v.iii) le groupe silyle -SiRaRbRc ; et R2, R3, R4, R5 étant indépendamment les uns des autres sélectionnés dans le groupe comprenant un hydrogène, un halogène et un groupe hydrocarbure en C1-C20, avec R2 et R4 faisant potentiellement partie d'un groupe cyclique ; b) au moins un polymère, sélectionné dans le groupe comprenant des composés de silicone de réticulation par addition, des composés de silicone de réticulation par condensation, des matériaux hybrides/STP, des polymères inorganiques et organiques et des combinaisons correspondantes.
PCT/EP2021/061920 2021-05-05 2021-05-05 Mélanges contenant un composé fonctionnalisé par silirane et un polymère WO2022233411A1 (fr)

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Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1026520B (de) 1956-01-20 1958-03-20 Wacker Chemie Gmbh Verfahren zum Kalthaerten von Silikonkautschuk bildenden Massen in Schichtstoffen
US3696090A (en) 1970-09-28 1972-10-03 Gen Electric Room temperature vulcanizable silicone rubber composition
US4686124A (en) 1983-12-12 1987-08-11 Sumitomo Bakelite Company Ltd. Thermoplastic resin-silicone rubber composite shaped article
JPS6348674A (ja) 1986-08-19 1988-03-01 Nippon Telegr & Teleph Corp <Ntt> 磁気ヘツドスライダ
EP0444960A2 (fr) 1990-03-02 1991-09-04 Shin-Etsu Chemical Co., Ltd. Compositions d'organopolysiloxane durcissables
EP0651019A1 (fr) 1993-10-27 1995-05-03 Wacker-Chemie GmbH Compositions de siloxane reticulable et revêtements anti-adhésifs
US5792812A (en) 1994-12-26 1998-08-11 Shin-Etsu Chemical Co., Ltd. Thermoplastic resin compoistions for use in integral molding with silicone rubber and integrally molded parts
US20070141250A1 (en) 2005-10-04 2007-06-21 Dow Corning Taiwan, Inc. Liquid Silicone Rubber Composition For Textile Coating
WO2017137281A1 (fr) 2016-02-12 2017-08-17 Wacker Chemie Ag Matières réticulables à base de polymères à terminaison organyloxysilane

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1026520B (de) 1956-01-20 1958-03-20 Wacker Chemie Gmbh Verfahren zum Kalthaerten von Silikonkautschuk bildenden Massen in Schichtstoffen
US3696090A (en) 1970-09-28 1972-10-03 Gen Electric Room temperature vulcanizable silicone rubber composition
US4686124A (en) 1983-12-12 1987-08-11 Sumitomo Bakelite Company Ltd. Thermoplastic resin-silicone rubber composite shaped article
JPS6348674A (ja) 1986-08-19 1988-03-01 Nippon Telegr & Teleph Corp <Ntt> 磁気ヘツドスライダ
EP0444960A2 (fr) 1990-03-02 1991-09-04 Shin-Etsu Chemical Co., Ltd. Compositions d'organopolysiloxane durcissables
EP0651019A1 (fr) 1993-10-27 1995-05-03 Wacker-Chemie GmbH Compositions de siloxane reticulable et revêtements anti-adhésifs
US5792812A (en) 1994-12-26 1998-08-11 Shin-Etsu Chemical Co., Ltd. Thermoplastic resin compoistions for use in integral molding with silicone rubber and integrally molded parts
US20070141250A1 (en) 2005-10-04 2007-06-21 Dow Corning Taiwan, Inc. Liquid Silicone Rubber Composition For Textile Coating
WO2017137281A1 (fr) 2016-02-12 2017-08-17 Wacker Chemie Ag Matières réticulables à base de polymères à terminaison organyloxysilane

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
JOON SOO HAN ET AL: "Reactivity of an Aryl-Substituted Silicon−Silicon Triple Bond: Reactions of a 1,2-Diaryldisilyne with Alkenes", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 132, no. 8, 3 March 2010 (2010-03-03), pages 2546 - 2547, XP055704295, ISSN: 0002-7863, DOI: 10.1021/ja9108566 *
SCOFIELD, J. H. J., J. ELEC. SPEC. REL. PHEN., vol. 8, 1976, pages 129
TAKAHIRO SASAMORI ET AL: "Reaction of a diaryldigermyne with ethylene", CHEMICAL SCIENCE, vol. 6, no. 10, 1 January 2015 (2015-01-01), United Kingdom, pages 5526 - 5530, XP055704254, ISSN: 2041-6520, DOI: 10.1039/C5SC01266J *
U. STÖHR, VAKUUM IN FORSCHUNG UND PRAXIS, vol. 27, 2015, pages 16 - 21

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