WO2012099305A1 - Composition liquide de revêtement de caoutchouc silicone et coussin gonflable de sécurité présentant un film durci de celle-ci - Google Patents

Composition liquide de revêtement de caoutchouc silicone et coussin gonflable de sécurité présentant un film durci de celle-ci Download PDF

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Publication number
WO2012099305A1
WO2012099305A1 PCT/KR2011/005228 KR2011005228W WO2012099305A1 WO 2012099305 A1 WO2012099305 A1 WO 2012099305A1 KR 2011005228 W KR2011005228 W KR 2011005228W WO 2012099305 A1 WO2012099305 A1 WO 2012099305A1
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WO
WIPO (PCT)
Prior art keywords
silicone rubber
coating composition
liquid silicone
composition according
weight
Prior art date
Application number
PCT/KR2011/005228
Other languages
English (en)
Inventor
Ye Jin HONG
Sang Bok Lee
Keun Mook Choi
Original Assignee
Kcc Corporation
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 Kcc Corporation filed Critical Kcc Corporation
Publication of WO2012099305A1 publication Critical patent/WO2012099305A1/fr

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B60—VEHICLES IN GENERAL
    • B60R—VEHICLES, VEHICLE FITTINGS, OR VEHICLE PARTS, NOT OTHERWISE PROVIDED FOR
    • B60R21/00—Arrangements or fittings on vehicles for protecting or preventing injuries to occupants or pedestrians in case of accidents or other traffic risks
    • B60R21/02—Occupant safety arrangements or fittings, e.g. crash pads
    • B60R21/16—Inflatable occupant restraints or confinements designed to inflate upon impact or impending impact, e.g. air bags
    • B60R21/20—Arrangements for storing inflatable members in their non-use or deflated condition; Arrangement or mounting of air bag modules or components
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B60—VEHICLES IN GENERAL
    • B60R—VEHICLES, VEHICLE FITTINGS, OR VEHICLE PARTS, NOT OTHERWISE PROVIDED FOR
    • B60R21/00—Arrangements or fittings on vehicles for protecting or preventing injuries to occupants or pedestrians in case of accidents or other traffic risks
    • B60R21/02—Occupant safety arrangements or fittings, e.g. crash pads
    • B60R21/16—Inflatable occupant restraints or confinements designed to inflate upon impact or impending impact, e.g. air bags
    • B60R21/23—Inflatable members
    • B60R21/235—Inflatable members characterised by their material
    • 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/61—Additives non-macromolecular inorganic
    • 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
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C08K3/36—Silica

Definitions

  • the present invention relates to a liquid silicone rubber-coating composition and an airbag with cured film thereof. More specifically, the present invention relates to a liquid silicone rubber-coating composition which contains an adhesion-imparting agent comprising 1-allyl-3,5-diglycidylisocyanurate and thus can maintain excellent adhesion property even after long-term exposure to high temperature/high humidity conditions as well as immediately after coating, and an airbag with cured film of the composition formed on fabric.
  • an adhesion-imparting agent comprising 1-allyl-3,5-diglycidylisocyanurate
  • Silicone rubbers generally have good heat resistance, electrical insulation, flame resistance and restoration after compression and deformation, and thus are widely used in various fields. For example, if a substrate fabric comprising a synthetic fiber such as nylon or an inorganic fiber such as a glass fiber is coated with a silicone rubber composition, it provides good thermal properties, storage stability, flexibility and abrasion resistance. Thus, such a silicone rubber composition is in the spotlight as a coating material for various articles including car airbags.
  • airbags comprising a nylon bag coated with silicone rubber have been marketed, and they have been recognized as reliable and used as a new type of airbag replacing conventional airbags. Furthermore, as the latest airbag system, a side-curtain shield airbag has been developed for alleviating the impact to passenger(s) from broadside collisions and for preventing driver from being catapulted out of the car during lateral turning.
  • silicone rubber-coating compositions for an airbag comprising as an adhesion-imparting ingredient, organosilane compound having epoxy group or isocyanate group are suggested in Japanese Laid-open Patent Publication Nos. (Hei)5-25435 and (Hei)5-98579, respectively.
  • the airbag using such a composition as a coating material therefor cannot secure it long-term wholesomeness since its long-term exposure to abnormal conditions such as high temperature/high humidity leads to the lowering of adhesion and generation of peeling.
  • the present invention has an object of providing a silicone rubber-coating composition which satisfies the basic properties required for application to an airbag, etc. and can maintain excellent adhesion even under high temperature/high humidity conditions.
  • the present invention provides a liquid silicone rubber-coating composition
  • a liquid silicone rubber-coating composition comprising: (A) polyorganosiloxane containing two or more alkenyl groups per molecule; (B) polyorganohydrogensiloxane containing hydrogen in the side chain of the molecule; (C) reinforcing silica; (D) catalyst for addition reaction; and (E) adhesion-imparting agent comprising 1-allyl-3,5-diglycidylisocyanurate.
  • the other aspect of the present invention provides an airbag having a cured film of the liquid silicone rubber-coating composition formed on airbag fabric.
  • the liquid silicone rubber-coating composition of the present invention can maintain excellent adhesion property even after long-term exposure to high temperature/high humidity conditions as well as immediately after coating, has good mechanical properties and low viscosity for easy coating and can secure the required function such as air-leak prevention even by a small amount of coating thereof.
  • Such liquid silicone rubber-coating composition of the present invention can be usefully applied for coating the substrate fabric of synthetic fibers, inorganic fibers, etc. ⁇ in particular, for an airbag.
  • liquid silicone rubber-coating composition of the present invention is explained in detail according to each constitutional component below.
  • Polyorganosiloxane (also referred to as “component (A)”) comprised in the composition of the present invention is the main raw material (base polymer) of the addition-curable-type liquid silicone rubber-coating composition. It contains two or more alkenyl groups (concretely, alkenyl groups bound to Si) per molecule in order for the composition of the present invention to be formed into cured silicone rubber film.
  • the curing of the composition proceeds by the crosslinking reaction of said polyorganosiloxane and polyorganohydrogensiloxane as explained below.
  • the polyorganosiloxane may be a linear polyorganosiloxane represented by the following formula 1:
  • the polyorganosiloxane contains alkenyl groups such as vinyl group, allyl group, butenyl group, pentenyl group, hexenyl group, heptenyl group, etc., and vinyl group is particularly preferred.
  • Alkenyl groups may be contained in both terminus and/or side chain of the polyorganosiloxane molecule. Alkenyl groups are contained preferably in a ratio of 0.001 ⁇ 5 mmol per gram of polyorganosiloxane, and more preferably in a ratio of 0.01 ⁇ 3 mmol/g. If the content is less than 0.001 mmol/g, the composition may not be coated smoothly. If the content is greater than 5 mmol/g, there may be a problem of lowered mechanical properties (strength, etc.) of the silicone rubber film.
  • the viscosity of the polyorganosiloxane is preferably 100 ⁇ 150,000 mPa ⁇ s at 25°C. If the viscosity is less than 100 mPa ⁇ s, the mechanical properties (strength, etc.) of the silicone rubber film may be lowered. If the viscosity is greater than 150,000 mPa ⁇ s, the composition may not be coated smoothly.
  • Polyorganohydrogensiloxane (also referred to as “component (B)”) comprised in the composition of the present invention performs the role of a crosslinking agent and contains hydrogen (concretely, hydrogen bound to Si) in the side chain of the molecule.
  • the curing of the composition proceeds by the crosslinking reaction of polyorganosiloxane and polyorganohydrogensiloxane.
  • the polyorganohydrogensiloxane may be represented by the following formula 2:
  • each of R 2 independently represents a saturated aliphatic hydrocarbyl group or aromatic hydrocarbyl group ⁇ for example, methyl, ethyl, butyl, phenyl, etc. (preferably, methyl); and each of m and n independently denotes an integer of 10 ⁇ 100.
  • Hydrogen is contained in the side chain of the molecule preferably in a ratio of 0.1 ⁇ 20 mmol per gram of polyorganohydrogensiloxane. If the content is less than 0.1 mmol/g, the strength of the silicone rubber film may be lowered. If the content is greater than 20 mmol/g, the heat resistance of the silicone rubber film may be lowered.
  • the amount of polyorganohydrogensiloxane in the present composition is preferably 1 ⁇ 30 parts by weight and more preferably 2 ⁇ 25 parts by weight, based on 100 parts by weight of polyorganosiloxane. If the amount is less than 1 part by weight, the composition may not be cured, or the crosslinking density may become lowered. If the amount is greater than 30 parts by weight, foaming by dehydration reaction may occur, or there may be a problem in releasing property.
  • Reinforcing silica (also referred to as “component (C)”) comprised in the composition of the present invention is an ingredient added to improve the strength of the silicone rubber.
  • any silica containing SiO 2 as the main ingredient may be used as the reinforcing silica without special limitation.
  • fumed silica, precipitated silica, diatomite, pulverized quartz, molten quartz or the like is used alone or in a combination of two or more thereof.
  • the above materials may be used without modification as the reinforcing silica, if they are surface-treated with hexamethyldisilazane, octamethylcyclotetrasiloxane or the like during the process and then used, the dispersibility and storage stability may be further improved.
  • the reinforcing silica has a preferable average particle diameter of 20 ⁇ m or less, more preferably 10 ⁇ m or less, and still more preferably 7 ⁇ m or less. If the average particle diameter is greater than 20 ⁇ m, the strength of the silicone rubber may not be improved sufficiently and in some cases, the strength may even be lowered. For the same reason, as the reinforcing silica (for example, fumed silica or precipitated silica), it is advantageous to use those having a primary particle diameter of sufficiently less than 5 ⁇ m (usually about 0.001 ⁇ 1 ⁇ m) and a specific surface area by BET method of 50 m2/g or greater, preferably 50 ⁇ 400 m2/g, and more preferably 100 ⁇ 350 m2/g.
  • the amount of reinforcing silica in the present composition is preferably 10 ⁇ 50 parts by weight and more preferably 15 ⁇ 35 parts by weight, based on 100 parts by weight of polyorganosiloxane. If the amount is less than 10 parts by weight, it may be difficult to obtain sufficient mechanical strength. If the amount is greater than 50 parts by weight, the viscosity may be too high and thus the processability may be lowered.
  • the catalyst for addition reaction (also referred to as “component (D)”) comprised in the composition of the present invention is an ingredient to promote the addition reaction of components (A) and (B).
  • any catalysts capable of promoting addition reaction of components (A) and (B) such as platinum catalyst, rhodium catalyst, palladium catalyst or the like may be used without special limitation.
  • Platinum compound is preferably used.
  • platinum in the platinum compound acts as a catalyst to crosslink polyorganosiloxane containing alkenyl group (for example, vinyl group) and polyorganohydrogensiloxane.
  • the reactivity and compatibility with a silicone polymer may be improved by using a platinum compound that forms a complex with a vinylsiloxane of low molecular weight and has the oxidation number of 0.
  • Examples of ligand forming a complex with platinum in the platinum compound may include divinyltetramethylsiloxane, tetramethyltertavinyl tetracyclosiloxane and the like, but it is not limited by them.
  • the content of platinum in the platinum compound is preferably 0.5 ⁇ 15% by weight.
  • the amount of catalyst for addition reaction in the present composition is preferably 0.01 ⁇ 1 part by weight and more preferably 0.1 ⁇ 0.5 part by weight, based on 100 parts by weight of polyorganosiloxane. If the amount is less than 0.01 part by weight, the addition reaction of the composition may become significantly slow, or the curing itself may not even occur. If the amount is greater than 1 part by weight, the addition reaction may become faster and thus pot life may become shorter, by which the workability may be lowered.
  • the adhesion-imparting agent (also referred to as “component (E)”) comprised in the composition of the present invention is an ingredient meant to increase the adhesion between the silicone rubber and the woven or non-woven fabric substrate such as an airbag fabric.
  • the present invention uses an adhesion-imparting agent comprising 1-allyl-3,5-diglycidylisocyanurate and not containing silicon. Accordingly, it is possible to provide a silicone rubber film which can maintain excellent adhesion property even upon exposure to high temperature/high humidity conditions as well as immediately after coating.
  • 1-allyl-3,5-diglycidylisocyanurate comprised in the adhesion-imparting agent may be represented by the following formula 3 and structural formula 1, which is obtainable ⁇ for example, as the trade name of MA-DGIC (Shikoku Co. Ltd., Japan).
  • 1-allyl-3,5-diglycidylisocyanurate may be used alone or in combination with another adhesion-imparting component (organosilane compound, organotitanium compound, etc.) conventionally added for silicone rubber.
  • the amount of adhesion-imparting agent in the present composition is preferably 0.01 ⁇ 0.5 part by weight, based on 100 parts by weight of polyorganosiloxane. If the amount is less than 0.01 part by weight, the effect of improving adhesion from its addition may not be expected. If the amount is greater than 0.5 part by weight, excessive increase of viscosity and lowering of storage stability may result.
  • composition of the present invention may further comprise a curing retarder (also referred to as “component (F)”). If a curing retarder is added to the addition-curable type liquid silicone rubber-coating composition together with the catalyst for addition reaction, the curing rate can be controlled smoothly. By properly adjusting the ratio of the catalyst for addition reaction and curing retarder, the workability required for specific application may be secured.
  • a curing retarder also referred to as “component (F)
  • compounds having a double bond including alkenyl or a triple bond such as 1-ethynyl-1-cyclohexanol, 1,1,3,3-tetramethyl-1,3-divinyldisilazane, 2,4,6,8-tetramethyl-2,4,6,8-tetravinylcyclotetrasiloxane, 2-methyl-3-butyn-2-ol, etc. may be used, but it is not limited by them.
  • the preferable amount of curing retarder in the present composition is 0.02 ⁇ 0.5 part by weight, based on 100 parts by weight of polyorganosiloxane. If the amount is less than 0.02 part by weight, there may be a problem due to an overly high curing rate. If the amount is greater than 0.5 part by weight, the curing itself may not occur.
  • composition of the present invention may further comprise additive(s) generally used for silicone rubber.
  • inorganic filler for improving strength and heat resistance such as fumed titanium dioxide, crystalline silica, calcium silicate, titanium dioxide, ferric oxide and carbon black
  • wetter for improving dispersibility including low molecular weight organosilane compound such as diorganopolysiloxane having terminal hydroxy group, diphenylsilanediol, hexaorganopolysiloxane and organoalkoxysilane
  • heat-resistance promoter including metal oxide such as iron oxide, cerium oxide, zinc oxide and titanium oxide, cerium silanolate and cerium fatty acid salt
  • flame-resistance imparting agent including platinum compound such as complexes of platinum tetrachloride, hydrogen hexachloroplatinate and hydrogen hexachloroplatinate hexahydrate with olefin or divinyldimethylpolysiloxane, alcohol
  • the method for preparing the present liquid silicone rubber-coating composition from the above components is not particularly limited, and the present composition may be prepared by using a conventional method in this field of art.
  • components (A) and (C) may be mixed by using a rubber kneader to prepare a base compounding, and components (B), (D) and (E) and optionally (F) if needed, and other additives may then be added thereto and mixed to prepare the present composition.
  • composition of the present invention comprises polyorganosiloxane, polyorganohydrogensiloxane and reinforcing silica in an appropriate amount, and thus can form silicone rubber film having excellent mechanical properties and can be coated easily on an airbag fabric, etc. since the viscosity is usually 80 Pa ⁇ s or less.
  • the other aspect of the present invention provides an airbag characterized in having a cured film of the present liquid silicone rubber-coating composition formed on an airbag fabric.
  • the liquid silicone rubber-coating composition of the present invention may be usefully applied for coating a substrate fabric of synthetic fibers, inorganic fibers, etc., in particular, for coating an airbag installed in vehicles or the like.
  • the composition may be coated and cured by a conventional method in this field of art to form cured film on an airbag fabric.
  • the coating amount of the composition may be adjusted properly according to the kind, use and structure of the airbag, and the curing of the composition is generally conducted at 80 ⁇ 250°C for 30 seconds ⁇ 10 minutes.
  • composition of the present invention comprises the adhesion-imparting agent containing 1-allyl-3,5-diglycidylisocyanurate as the main ingredient, its excellent adhesion property can be maintained even after long-term exposure to high temperature/high humidity conditions as well as immediately after coating.
  • liquid silicone rubber-coating compositions prepared in the Examples and Comparative Examples were cured in a press at 170°C for 10 minutes to prepare rubber sheet samples with a thickness of 2 mm.
  • the prepared samples were tested for various mechanical properties by the below methods, the results of which are provided in the following Table 1.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Mechanical Engineering (AREA)
  • Air Bags (AREA)
  • Paints Or Removers (AREA)

Abstract

La présente invention concerne une composition liquide de revêtement de caoutchouc silicone et un coussin gonflable de sécurité pourvu d'un film durci de celle-ci. Plus précisément, la présente invention concerne une composition liquide de revêtement de caoutchouc silicone qui contient un agent conférant de l'adhérence, celui-ci comportant de l'isocyanurate de 1-allyle et de -3,5-diglycidyle, et qui permet ainsi de conserver une excellente propriété d'adhérence même après une exposition de longue durée à des conditions de haute température/d'humidité élevée, ainsi que juste après l'application en revêtement. L'invention concerne également un coussin gonflable de sécurité pourvu d'un film durci de la composition formé sur du tissu.
PCT/KR2011/005228 2011-01-20 2011-07-15 Composition liquide de revêtement de caoutchouc silicone et coussin gonflable de sécurité présentant un film durci de celle-ci WO2012099305A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020110005817A KR101244640B1 (ko) 2011-01-20 2011-01-20 액상 실리콘 고무 코팅 조성물 및 그의 경화 피막이 형성된 에어백
KR10-2011-0005817 2011-01-20

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015110694A (ja) * 2013-12-06 2015-06-18 サンユレック株式会社 シリコーン樹脂組成物
JP2021181522A (ja) * 2020-05-18 2021-11-25 信越化学工業株式会社 液状シリコーンゴムコーティング剤組成物
US11530333B2 (en) 2016-12-26 2022-12-20 Akzo Nobel Coatings International B.V. Coating composition system, the preparation method, and the use thereof

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102360587B1 (ko) * 2020-01-29 2022-02-09 김철신 자기점착형 투명 키보드 덮개

Citations (4)

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Publication number Priority date Publication date Assignee Title
JP2001287610A (ja) * 2000-04-07 2001-10-16 Asahi Kasei Corp エアバッグ用コーティング組成物およびエアバッグ
JP2002138249A (ja) * 2000-11-01 2002-05-14 Dow Corning Toray Silicone Co Ltd 液状シリコーンゴムコーティング剤組成物
JP2006137800A (ja) * 2004-11-10 2006-06-01 Shin Etsu Chem Co Ltd 固体高分子型燃料電池用付加反応硬化型シリコーンゴム接着剤組成物およびそれを使用する固体高分子型燃料電池
US20070166555A1 (en) * 2006-01-13 2007-07-19 Shin -Etsu Chemical Co., Ltd. Liquid silicone rubber coating composition, curtain airbag and making method

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001287610A (ja) * 2000-04-07 2001-10-16 Asahi Kasei Corp エアバッグ用コーティング組成物およびエアバッグ
JP2002138249A (ja) * 2000-11-01 2002-05-14 Dow Corning Toray Silicone Co Ltd 液状シリコーンゴムコーティング剤組成物
JP2006137800A (ja) * 2004-11-10 2006-06-01 Shin Etsu Chem Co Ltd 固体高分子型燃料電池用付加反応硬化型シリコーンゴム接着剤組成物およびそれを使用する固体高分子型燃料電池
US20070166555A1 (en) * 2006-01-13 2007-07-19 Shin -Etsu Chemical Co., Ltd. Liquid silicone rubber coating composition, curtain airbag and making method

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015110694A (ja) * 2013-12-06 2015-06-18 サンユレック株式会社 シリコーン樹脂組成物
US11530333B2 (en) 2016-12-26 2022-12-20 Akzo Nobel Coatings International B.V. Coating composition system, the preparation method, and the use thereof
JP2021181522A (ja) * 2020-05-18 2021-11-25 信越化学工業株式会社 液状シリコーンゴムコーティング剤組成物
JP7353235B2 (ja) 2020-05-18 2023-09-29 信越化学工業株式会社 液状シリコーンゴムコーティング剤組成物

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KR20120084451A (ko) 2012-07-30

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