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WO1986005797A1 - Composition d'etancheisation a silicones vulcanisables a temperature ambiante, a un seul composant et autoadherente, dont l'adjuvant d'adhesion est un silane alcoxyle-oxime a remplacement par le glycidoxyalcyle - Google Patents

Composition d'etancheisation a silicones vulcanisables a temperature ambiante, a un seul composant et autoadherente, dont l'adjuvant d'adhesion est un silane alcoxyle-oxime a remplacement par le glycidoxyalcyle Download PDF

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Publication number
WO1986005797A1
WO1986005797A1 PCT/US1986/000692 US8600692W WO8605797A1 WO 1986005797 A1 WO1986005797 A1 WO 1986005797A1 US 8600692 W US8600692 W US 8600692W WO 8605797 A1 WO8605797 A1 WO 8605797A1
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Prior art keywords
carbon atoms
percent
adhesion promoter
hydrocarbyl
methyl
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Ceased
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PCT/US1986/000692
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English (en)
Inventor
M. Dale Beers
James E. Thompson
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Henkel Loctite Corp
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Henkel Loctite Corp
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Application filed by Henkel Loctite Corp filed Critical Henkel Loctite Corp
Priority to JP61502171A priority Critical patent/JPH0645783B2/ja
Publication of WO1986005797A1 publication Critical patent/WO1986005797A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • C09K3/1018—Macromolecular compounds having one or more carbon-to-silicon linkages
    • 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
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/544—Silicon-containing compounds containing nitrogen
    • C08K5/5465—Silicon-containing compounds containing nitrogen containing at least one C=N bond
    • 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
    • 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
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl 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
    • C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing 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
    • C08G77/70—Siloxanes defined by use of the MDTQ nomenclature
    • 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
    • C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
    • C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
    • C09K2200/0645—Macromolecular organic compounds, e.g. prepolymers obtained otherwise than by reactions involving carbon-to-carbon unsaturated bonds
    • C09K2200/0647—Polyepoxides

Definitions

  • the present invention relates to a glycidoxyalkyl substituted alkoxy-oxime silane as an adhesion promoter, which can be used in a silicone sealant.
  • U.S. Patent No. 4,356,116 to Beers relates to a low volatile room temperaure vulcanizable silicone rubber composition, containing various components including a silanol polymer, a crosslinking agent, and a filler.
  • U.S. Patent No. 4,100,129 to Beers also relates to adhesion promoter compositions curable in the presence of moisture.
  • U.S. Patent No. 4,395,526 to White et al relates to a stable, substantially acid-free, one-component curable polyalk oxy-terminated organosiloxane composition having a condensation catalyst, such as a tin compound.
  • the material in this patent also serves as an adhesion promoter.
  • acetoxy curing room temperature vulcanizable silicones include Ceyzeriat, U.S. Patent No. 3,133,891, Brunner, 3,035,016, and Beers, 3,382,205. More specifically, the Beers' patent relates to or ⁇ anopolysiloxane composition comprising a mixture of organetriacyloxysilane and a base mixture containing organosiloxane having chemically combined organsiloxy units.
  • U.S. Patent No. 3,541,044 to Beers relates to a substantially anhydrous organopolysiloxane composition curable to the elastomeric state upon exposure to moisture.
  • Another patent by Beers namely U.S. Patent No. 3,837,878 relates to a two-component room temperature vulcanizable silicone rubber composition suitable for molding applications whereas Patent No. 3,837,878 also to Beers relates to a process for treating silicone fillers.
  • U.S. Patent No. 3,776,933 to Toporcerer relates to chain extenders with regard to RTV systems.
  • an adhesion promoter comprising a glycidoxyalkyl substituted mixed alkoxy-oxime silane- type compound.
  • the inventive adhesion promoter is a compound having the formula:
  • R 1 is a hydrocarbyl, or a halohydrocarbyl having from
  • R 2 is a divalent hydrocarbyl, or a halohydrocarbyl having from 1 to 10 carbon atoms
  • R 3 is a hydrocarbyl, a halohydrocarbyl, or a carboxyalkyl having from 1 to 10 carbon atoms
  • m is from 0 to 3
  • R 4 and R 5 can independently be a hydrocarbyl, halohydrocarbyl or carboxyalkyl having from 1 to 10 carbon atoms
  • x is 0 ro 3
  • R 6 is hydrocarbyl, a halohydrocarbyl, or a carboxyalkyl having from 1 to 10 carbon atoms
  • p is 0 - 2
  • the R 7 groups are indepently hydrogen, hydrocarbyl, halohydrocarbyl, or carboxyalkyl having from 1 to
  • the adhesion promoter of the present invention can be utilized in silicone sealants.
  • the sealant sealant composition exhibits very good auto-adhering adhesion even on oil contaminated metal such as aluminum and steel surfaces as encountered in the auto industry. Additionally, such compositions have excellent oil resistance properties, even at high temperatures for example, 300°F, and are particularly useful as silicone formed-in-place gasketing.
  • an auto adhering one-component RTV silicone sealant is prepared utilizing a glycidoxyalkyl adhesion substituted mixed alkoxy-oxime silane.
  • the adhesion promoter can be presented by the following formula.
  • R 1 is a hydrocarbyl having from 1 to 10 carbon atoms.
  • hydrocarbyl it is meant that the hydrocarbon group is an aliphatic or cycloaliphatic group such as an alkyl, an alkenyl, an acetylene group or cycloalkyl, etc. with alkyl being preferred, or an aromatic group including aliphatic substituted aromatic or an aromatic substituted aliphatic.
  • This definition of hydrocarbyl is applicable not only with regard to R 1 but also with regard to R 2 through R 8 groups with the exception that R 3 does not contain aromatic groups.
  • R 1 can also be a halohydrocarbyl having from 1 to 10 carbon atoms.
  • R 2 can be a hydrocarbyl group, or a halohydrocarbyl having from 1 to 10 carbon atoms.
  • An alkylene group is desired, preferably a 3-8 carbon alkylene group.
  • the R 3 group can be a hydrocarbyl group, a halohydrocarbyl group or a carboxyalkyl group having from 1 to 10 carbon atoms .
  • an alkyl group is preferred with methyl being highly preferred.
  • the number of "OR “ groups or “m” is from 0 to 3, desirably 1 to 2 with 1 being preferred.
  • R 4 and R 5 can be the same or different and include a hydrocarbyl, a halohydrocarbyl, or a carboxyalkyl, all having from 1 to 10 carbon atoms.
  • alkyl groups are desired with methyl or ethyl being highly preferred.
  • the number of oxime groups on the silicon atom, that is "x" is generally from 0 to 3, desirably 1 to 3, with 2 being preferred.
  • R 6 is a hydrocarbyl, a halohydrocarbyl, or a carboxyalkyl having from 1 to 10 carbon atoms.
  • the number of such R 6 groups, that is "p" can be 0 co 2, preferably 0.
  • R 7 can be hy ⁇ rogen, hydrocarbyl, halohydrocarbyl, or carboxyalkyl having from 1 to 10 carbon atoms with methyl being desirable, Preferrably, however, both R 7 groups are H.
  • Examples of specific adhesion promoters according to the present invention include the following compounds:
  • the adhesion promoter of the present invention having the above formulation is prepared in the manner as set forth below involving reaction of a glyciloxy silane compound with an oxime compound.
  • the oxime crosslinking units are grafted onto the glycidoxyalkyl silane by carrying out the reaction at a temperature from about 45°C. to about 150°C, preferably from about 50°C to abotit 120°C.
  • the type of oxime compounds utilized are generally of the type set forth in formulae A and B below or mixtures thereof. As should be apparent from the reaction set forth above, a large variety of different compounds can be made according to the present invention.
  • an organic tin salt catalyst is generally utilized.
  • the amount of tin catalyst is generally from about 0.01 to about 0.5 percent by weight and preferably from about 0.02 to about 0.2 by weight based upon the total amount of said silicone sealant compound .
  • Such tin catalysts are generally well known to the art, such as those set forth in U.S. Patent Nos. 4,356,116 and 4,395,526 hereby fully incorporated by reference.
  • tin catalysts examples include dibutyltindilaurate, dibutyltindiacetate, tin octoate, dimethyltindibutyrate, triethyltintartrate, tin oleate, dibutyltinoxide and dimethyltin bisneodecanoate.
  • the adhesion promoter as discussed above forms a part of a silicone composition containing various components thereof such as a base polymer, a plasticizer, a thixotropic agent, and the like.
  • a base polymer it is a silanol terminated diorganopolysiloxane polymer.
  • This linear polymer may be devolatilized in a manner such as set forth in U.S. Patent No. 4,356,116 and generally has a viscosity of from about 2,000 to about 250,000 centipoise and preferably from about 10,000 to about 120,000 centipoise.
  • the polymer has the formula
  • n is from about 300 to about 1,000, where R 1 ana R 2 can be the same or different, where R 1 and R 2 is an alkyl group having from 1 to 8 carbon atoms with methyl being preferred, a cycloalkyl group having from 4 to 7 carbon atoms such as cyclohexyl, an alkenyl group having from 2 to 8 carbon atoms such as allyl with vinyl being preferred, an aryl or an alkyl substituted aryl group having from 6 to 14 carbon atoms such as phenyl, methylphenyl, or a fluoroalkyl group having from 1 to 8 carbon atoms with
  • the amount of the linear polymer generally ranges from about 25 to about 90 percent by weight and preferably from 30 to about 60 percent by weight based upon the total weight of the low modulus RTV silicone composition.
  • Such polymers are commercially available and are manufactured by
  • the silanol terminated silicone polymer also is reacted with an oxime compound having the formulation set forth in formula A wherein the oxime compound is grafted onto the polymer .
  • Simple types of oxime compounds which can be utilized in the present invention is set forth in formulations A and/or B wherein on a molar basis, from 0.0 or 0.05 moles to about 0.4 moles of the formula A oxime is utilized and preferably from about 0.1 to about 0.2 moles of the formulation A oxime compound per 1 mole of said Formula "A" and “B” compounds.
  • the amount of the Formula "B” compound is the difference, that is from 0.6 to 0.95 and preferably from 0.8 to 0.9 moles per 1 mole of said Formula "A" and said "B” compounds.
  • R 4 and R 5 are as set forth above.
  • "x" is the same as set forth above, that is from 0 to 3 with 2 being preferred. It is to be understood that when one of the oxime types has “x" as zero, the remaining type or formula must be more than 2, R 9 can be an alkyl having from 1 to 8 carbon atoms with methyl being preferred, an alkenyl group having from 2 to 8 carbon atoms with vinyl being preferred, a haloalkyl having from 1 to 6 carbon atoms, a trifluoroalkyl having from 1 to 8 carbon atoms, or a haloalkenyl having from 2 to 8 carbon atoms.
  • R 8 can be a hydrocarbyl, a halohydrocarbyl, or a carboxyalkyl having from 1 to 10 carbon atoms. Preferably R 8 is methyl or ethyl.
  • an oxime compound when utilized as set forth in Formulas A or B wherein R 4 is methyl, R 5 is ethyl, R 9 is methyl or vinyl and R 8 is methoxy, with x being 2, an unexpected synergistic result is obtained with regard to adhesion.
  • An enhancement of adhesion results. The enhancement is maximized when R 9 is vinyl.
  • Preparation of an oxime type compound as set forth in Formula A is generally well known to the art and literature, as for example U.S. Patent No. 3,189,576 which is hereby fully incorporated by reference as to the manner and method of preparing such oxime compounds.
  • an excess of the crosslinker containing the oxime group to the silanol in the base polymer, set forth below, is utilized at a ratio of from about 1.2 to about 4.0 with from about 2.0 to about 3.0 being preferred molar ratio of crosslinker to silanol groups.
  • the plasticizer utilized along with the linear base polymer in the sealant composition is a devolatilized triorganosiloxy terminated diorganopolysiloxane fluid existing in an amount of from 0 or 1 to about 40 percent by weight and desirably from 5 to about 25 percent by weight based upon the total weight of the siloxane sealant composition.
  • the plasticizer lowers the durometer and modulus of the cured rubber and lowers the viscosity of the overall system or composition.
  • the viscosity of the plasticizer should not be too low inasmuch as it will tend to bleed out of the composition. Accordingly, the viscosity generally ranges from about 50 to about 100,000 centipoise and preferably from about 500 to about 10,000 centipoise.
  • the plasticizer is a diorganopolysiloxane polymer terminated with monofunctional, triorgano siloxy end groups.
  • the organo compounds within the repeating units are the same as R 1 and R 2 set forth herein above with regard to the base polymer. However, it may contain trace quantities of trifunctional monoorganosiloxy units originating from impurities in the starting materials.
  • the siloxy units contain an alkyl group having from 1 to 8 carbon atoms with methyl being preferred.
  • the number of repeating units in the plasticizer is generally from about 20 to about 900.
  • the plasticizer is devolatilized in accordance with any conventional manner or process, well known to the art. A specific example of devolatilization is seth forth in U.S. Patent No. 4,356,116 which is hereby fully incorporated by reference.
  • a thixotropic agent is added to the overall composition.
  • This agent which also adds physical strength to the system desirably is a treated or an untreated silica filler with a treated fumed silica filler being preferred.
  • Treated or untreated silica fillers are well known to the art and generally any such conventional filler can be utilized. Examples cf specific silica fillers are are noted in U.S. Patent No. 3,837,878 whuich is hereby full incorporated by reference. Additionally, treated silica as set forth in Lucas U,.S. Patent No. 2,938,009, Lichtenwalner U.S. Patent No. 3,004,859, and Smith U.S. Patent No. 3,635,743, all hereby full incorporated by reference, can be utilized. Typically, the silica filler has a very high surface area such as about 200M 2 /gram.
  • thermal aging additive can be utilized.
  • This optional component functions to reduce oxidation and thermal rearrangement of polymers at elevated temperatures.
  • These antioxidants may include materials like cerium neodecanoate, rare earth octoates and iron octoates.
  • Representative samples can also usually include thermal aging additives such as carbon black, iron oxide powder, and titanium dioxide. Naturally, other pigments can be utilized.
  • Another optional ingredient is an inert non-reinforcing filler such as ground quartz, calcium carbonate, talc, clay, various silicate compounds and other materials well known in the art.
  • the amount utilized is from about 5% to about 60% by weight bases upon the total weight of the sealant composition.
  • the sealants of the present invention containing the adhesion promoter therein exhibits numerous improved and desirous properties.
  • a silicone resin primer is no longer needed to obtain good adhesion, but rather a silicone sealant of the present invention can be directly applied to a metallic or other surface.
  • the sealant composition of the present invention has good adhesion to various substrates such as steel, iron, aluminum, acrylic plastics and paints, polycarbonate, polyester, ABS, glass, ceramics, brick, concrete and the like.
  • the silicone sealants of the present invention have low odor characteristics as opposed to the sometime nauseating odor of prior art sealants and are generally non-corrosive with regard to iron or aluminum substrates.
  • the silicone sealants of the present invention can be utilized as in-place gasketing sealants due to their good thermal resistance at high temperatures as for example from about 250°F to about 500°F and still maintain good flexibility at low temperatures, that is about 85°F.
  • Particular uses include RTV silicone adhesives, bathtub caulking compounds, masonry joint materials, as a plastic adhesive, and the like.
  • the silicone sealants are particularly suitable for usage in various internal combustion engine for various gasket applications such as oil pan gaskets, valve cover gaskets, water seals, intake seals, and the like.
  • the preparation and incorporation of the aforementioned silane adhesion promoter can be accomplished according to one of two modes.
  • first mode there is a reaction product of various oxime type products and thus the exact end product or type is not known.
  • second mode a specific oxime product is produced.
  • the silicone sealant compound is then prepared by charging the various ingredients into a mixer under dry conditions as through the use of dry nitrogen to prevent hydrolysis of the oxime crosslinking compound.
  • the polymer is added first with the plasticizer.
  • the oxime crosslinker and adhesion promoter composition is then added followed by the fumed silica, as well as any thermal stabilizing agent.
  • the treated calcium carbonate filler is then added.
  • the composition is mixed under high speed or agitation as well as under a vacuum for several minutes or even hours to remove the entrapped nitrogen bubbles.
  • the resulting paste formed can be placed or extruded into a desirable container and the like.
  • This composition was prepared by charging the ingredients into the mixing can of a vertical laboratory change can mixer which had been flushed with dry nitrogen to prevent the hydrolysis of the oxime crosslinker.
  • peel adhesion of this sealant to Alclad aluminum after curing for 14 days was 8 to 10 pounds per linear inch with 100% cohesive failure versus 0 to 2 pounds per linear inch with 100% adhesive failure for a sealant without (8) and also for a sealant with (8) but excluding in the preparation of said sealant the step of heating at 50°C for 16 hours the mixture of (6), (7) and (8).
  • a glycidoxyalkyl trialkoxysilane is heated with a sufficient amount of a ketoxime compound such as methyl ethylketoxime to cause a partial substitution of the ketoxime on the silicon atom by displacing the alkoxy moiety.
  • the sealant is prepared as described for the first mode of preparation.
  • This composition was prepared as in Example 1.
  • the ingredients were added in the order: (1), (2), (3), (4), (5), (6), (7), and (8), then mixed at high speed under vacuum for approximately two hours and afterward the resulting paste was transferred to a pressure Semco mixer and extruded into six ounce polyethylene cartridges.
  • the peel adhesion of this sealant to Aiclad aluminum after curing for four weeks was 13 pli (lbs. per linear inch) with 100% cohesive failure.

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  • 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)
  • Sealing Material Composition (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

Produit d'étanchéisation à silicones vulcanisables à la température ambiante, à un seul composant et autoadhérente, dans lequel on utilise comme adjuvant d'adhésion un silane alcoxyle-oxime mélangé à remplacement par le glycidoxyalcyle. Le produit adhère à une gamme de substrats y compris au verre, au métal et aux céramiques; il ne requiert pas l'application au substrat d'une couche primaire; il possède une faible odeur et ne corrode pas les substrats ferreux. Le produit est utile comme matériau de joint d'étanchéité pour formage sur place, comme par exemple pour un moteur à combustion interne. Il possède une bonne résistance à l'huile en tant que matériau de joint aux silicones vulcanisables à température ambiante.
PCT/US1986/000692 1985-04-04 1986-04-04 Composition d'etancheisation a silicones vulcanisables a temperature ambiante, a un seul composant et autoadherente, dont l'adjuvant d'adhesion est un silane alcoxyle-oxime a remplacement par le glycidoxyalcyle Ceased WO1986005797A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP61502171A JPH0645783B2 (ja) 1985-04-04 1986-04-04 グリシドキシアルキル置換アルコキシオキシムシランを定着剤として利用する自粘着一成分自然加硫シリコ−ンシ−ラント組成物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US719,753 1976-09-02
US71975385A 1985-04-04 1985-04-04

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WO1986005797A1 true WO1986005797A1 (fr) 1986-10-09

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0273705A3 (en) * 1987-01-02 1989-04-26 Dow Corning Corporation Curable silicone composition for corrosion protection
CN116179145A (zh) * 2022-12-28 2023-05-30 广州市白云化工实业有限公司 一种抗高温蠕变的单组分缩合型室温硫化硅橡胶及其制备方法

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7604931B2 (ja) * 2021-02-12 2024-12-24 信越化学工業株式会社 室温硬化性オルガノポリシロキサン組成物の製造方法及び室温硬化性オルガノポリシロキサン組成物、接着剤、シーリング材並びに物品

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JPS5490348A (en) * 1977-12-28 1979-07-18 Toshiba Silicone Room temperature setting polysiloxane
BE881499A (fr) * 1980-01-14 1980-08-01 Toray Silicone Co Compositions de resine de silicone durcissant a la temperature ambiante et articles revetus d'un film durci de ces compositions
US4371682A (en) * 1980-06-17 1983-02-01 Toshiba Silicones, Ltd. Room temperature curable polyorganosiloxane composition and method
EP0157580A2 (fr) * 1984-03-27 1985-10-09 Loctite Corporation Composition d'étanchéité résistant à l'huile, avec module bas, à base de silicone

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JPS5443868A (en) * 1977-09-14 1979-04-06 Nippon Steel Corp Removing method for nox in exhaust gas
JPS58142935A (ja) * 1982-02-19 1983-08-25 Toray Silicone Co Ltd プライマ−組成物

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JPS5490348A (en) * 1977-12-28 1979-07-18 Toshiba Silicone Room temperature setting polysiloxane
BE881499A (fr) * 1980-01-14 1980-08-01 Toray Silicone Co Compositions de resine de silicone durcissant a la temperature ambiante et articles revetus d'un film durci de ces compositions
US4371682A (en) * 1980-06-17 1983-02-01 Toshiba Silicones, Ltd. Room temperature curable polyorganosiloxane composition and method
EP0157580A2 (fr) * 1984-03-27 1985-10-09 Loctite Corporation Composition d'étanchéité résistant à l'huile, avec module bas, à base de silicone

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CHEMICAL ABSTRACTS, Vol. 92, January 1980 (Columbus, Ohio, US) see page 56, Abstract No. 7696q, & JP,A,54 090 348 (Toshiba Silicone Co., Ltd.) 18 July 1979 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0273705A3 (en) * 1987-01-02 1989-04-26 Dow Corning Corporation Curable silicone composition for corrosion protection
CN116179145A (zh) * 2022-12-28 2023-05-30 广州市白云化工实业有限公司 一种抗高温蠕变的单组分缩合型室温硫化硅橡胶及其制备方法

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JPS62502410A (ja) 1987-09-17
EP0216910A1 (fr) 1987-04-08
JPH0645783B2 (ja) 1994-06-15

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