WO2021002163A1 - Composition d'organopolysiloxane, composition comprenant ledit composé, et procédé de préparation associé - Google Patents

Composition d'organopolysiloxane, composition comprenant ledit composé, et procédé de préparation associé Download PDF

Info

Publication number
WO2021002163A1
WO2021002163A1 PCT/JP2020/022790 JP2020022790W WO2021002163A1 WO 2021002163 A1 WO2021002163 A1 WO 2021002163A1 JP 2020022790 W JP2020022790 W JP 2020022790W WO 2021002163 A1 WO2021002163 A1 WO 2021002163A1
Authority
WO
WIPO (PCT)
Prior art keywords
substituted
group
unsubstituted
carbon atoms
general formula
Prior art date
Application number
PCT/JP2020/022790
Other languages
English (en)
Japanese (ja)
Inventor
優大 今坂
大樹 片山
坂本 隆文
Original Assignee
信越化学工業株式会社
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 信越化学工業株式会社 filed Critical 信越化学工業株式会社
Priority to JP2021529937A priority Critical patent/JP7279790B2/ja
Publication of WO2021002163A1 publication Critical patent/WO2021002163A1/fr

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02Silicon compounds
    • C07F7/08Compounds having one or more C—Si linkages
    • C07F7/18Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00Compositions 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
    • C08L83/04Polysiloxanes
    • C08L83/06Polysiloxanes containing silicon bound to oxygen-containing groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00Compositions 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
    • C08L83/04Polysiloxanes
    • C08L83/08Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING 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
    • C09D183/00Coating 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
    • C09D183/04Polysiloxanes
    • C09D183/08Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J183/00Adhesives 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; Adhesives based on derivatives of such polymers
    • C09J183/04Polysiloxanes
    • C09J183/08Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00Materials not provided for elsewhere
    • C09K3/10Materials in mouldable or extrudable form for sealing or packing joints or covers

Definitions

  • the present invention relates to an organopolysiloxane compound and a method for producing the same, and more specifically, as a silicon-containing group (hereinafter, also referred to as “reactive silicon-containing group”) that can be increased in molecular weight by forming a siloxane bond.
  • the present invention relates to a bifunctional organopolysiloxane compound having one monoorganooxy group such as a monoalkoxy group bonded to a silicon atom at the end of each molecular chain (that is, two in the molecule) and a method for producing the same.
  • the reactive silicon-containing group particularly the hydrolyzable silyl group
  • the polymer having this reactive silicon-containing group is in the presence of water or moisture. It can be used for a curable composition that is cross-linked and cured.
  • silicone polymers those having a silicon-containing structure (particularly preferably a linear, organopolysiloxane structure) in the main chain are generally known as silicone polymers.
  • a room temperature curable (RTV) organopolysiloxane composition using these as a main agent (base polymer) is liquid at room temperature (23 ° C ⁇ 10 ° C) and becomes a rubber elastic body (elastomer) by curing (crosslinking reaction). It has characteristics and is widely used in coating agents, adhesives, building sealants, etc. by utilizing these characteristics.
  • a silane coupling agent In these room temperature curable (RTV) resin compositions, a silane coupling agent, a partially hydrolyzed condensate thereof, or the like is used as a cross-linking agent and a stabilizer.
  • a bifunctional silane coupling agent having two hydrolyzable groups in the molecule is called a chain length extender among cross-linking agents, and by extending the chain length of a silicone polymer, it can be used as a sealant or an RTV rubber cured product. Gives moderate elongation.
  • RTV room temperature curable organopolysiloxane compositions
  • the de-alcohol type which releases alcohol and cures by condensation reaction during cross-linking, has no unpleasant odor and does not corrode metals, so it is suitable for sealing, bonding, and coating of electrical and electronic equipment.
  • the de-alcohol type has lower reactivity with water (moisture) in the air than other conventionally known hardening types such as deacetone type, deoxime type, and deamination type. Due to the slow curing rate, no organopolysiloxane compound was an industrially viable dealcohol-type room temperature curable (RTV) composition chain length extender.
  • RTV room temperature curable
  • the present invention provides an organopolysiloxane compound that serves as a chain length extender for an industrially practical dealcohol-type room temperature curable (RTV) composition that rapidly rubberizes and exhibits rubber elasticity. With the goal.
  • RTV room temperature curable
  • organooxy groups such as an alkoxy group bonded to a silicon atom at the end of the molecular chain represented by the following general formula (1) in each molecular chain.
  • a methylene group having one terminal that is, two mono (organooxy) silyl groups in the molecule
  • the present invention has been completed by finding that a bifunctional organopolysiloxane compound having a specific molecular structure having (that is, an ⁇ -amino group and / or an ⁇ -amine residue) is useful for solving the above-mentioned problems. did.
  • the present invention relates to the following organopolysiloxane compound, a composition containing the compound, a coating agent composed of the composition, an adhesive and a sealing agent, an article having a cured product of the composition, a method for producing the compound, and the like.
  • I will provide a.
  • R 1 , R 2 and R 3 are unsubstituted or substituted alkyl groups having 1 to 10 carbon atoms or unsubstituted or substituted aryl groups having 6 to 10 carbon atoms independently of each other.
  • n is an integer from 0 to 10
  • X is an unsubstituted or substituted amino group.
  • a method for producing an organopolysiloxane compound represented by the following general formula (1)' which comprises a step of subjecting an organosilane compound represented by the following general formula (2) to a condensation reaction in the presence of a catalyst to dimerize the compound.
  • R 2 and R 3 are unsubstituted or substituted alkyl groups having 1 to 10 carbon atoms, or unsubstituted or substituted aryl groups having 6 to 10 carbon atoms, and X is non-substituted or substituted. Substituted or substituted amino group.)
  • R 1 , R 2 and R 3 are independently unsubstituted or substituted alkyl groups having 1 to 10 carbon atoms, or unsubstituted or substituted aryl groups having 6 to 10 carbon atoms.
  • X is an unsubstituted or substituted amino group.
  • Silanol group-blocking diorganopolysiloxane at both ends of the molecular chain represented by the following general formula (3) and an organosilane compound represented by the following general formula (2) are subjected to a condensation reaction to block silanol groups at both ends of the molecular chain.
  • a method for producing an organopolysiloxane compound represented by the following general formula (1)'' which comprises a step of sealing both ends of the molecular chain of the siloxane with a residue of the organosilane compound represented by the following general formula (2).
  • R 1 is an alkyl group having 1 to 10 carbon atoms unsubstituted or substituted independently of each other, or an aryl group having 6 to 10 carbon atoms substituted or substituted, and n is an integer of 1 to 10. .
  • R 2 and R 3 are unsubstituted or substituted alkyl groups having 1 to 10 carbon atoms, or unsubstituted or substituted aryl groups having 6 to 10 carbon atoms, and X is non-substituted or substituted.
  • R 1 , R 2 and R 3 are independently unsubstituted or substituted alkyl groups having 1 to 10 carbon atoms, or unsubstituted or substituted aryl groups having 6 to 10 carbon atoms.
  • n is an integer from 1 to 10
  • X is an unsubstituted or substituted amino group.
  • the organopolysiloxane compound of the present invention has excellent reactivity even in a dealcohol type condensation reaction. Further, a room temperature curable (RTV) organopolysiloxane composition containing such an organopolysiloxane compound as a chain length extender quickly rubberizes due to humidity in the air even at room temperature and exhibits rubber elasticity. It can be suitably used for applications such as adhesives and sealants.
  • RTV room temperature curable
  • the organopolysiloxane compound according to the present invention has one organooxy group bonded to a silicon atom at the end of the molecular chain represented by the following general formula (1) (one at the end of each molecular chain (1). That is, a methylene group (that is, ⁇ -amino) having a mono (organooxy) silyl group (two in the molecule) and substituted with an amino group and / or an amine residue on each silicon atom at the end of the molecular chain. It is a bifunctional organopolysiloxane compound having a specific molecular structure and having a group and / or an ⁇ -amine residue).
  • R 1 , R 2 and R 3 independently represent an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted or substituted aryl group having 6 to 10 carbon atoms.
  • the alkyl group having 1 to 10 carbon atoms may be linear, cyclic or branched, and specific examples thereof include methyl, ethyl and n-propyl.
  • Alkyl groups Cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, isobornyl groups and the like can be mentioned.
  • aryl group having 6 to 10 carbon atoms include phenyl, tolyl, xsilyl, ⁇ -naphthyl, ⁇ -naphthyl group and the like.
  • a part or all of the hydrogen atoms of these groups may be substituted with halogen atoms such as alkyl groups, aryl groups, F, Cl and Br, cyano groups and the like, and among these, R 1 , R As 2 and R 3 , a methyl group, an ethyl group, and a phenyl group are preferable, and a methyl group is more preferable from the viewpoints of reactivity, availability, productivity, and cost.
  • X is an unsubstituted or substituted amino group, preferably a secondary or tertiary amino group (for example, a monoorgano-substituted amino group or a diorgano-substituted amino group), and a tertiary amino group (for example,).
  • Diorgano-substituted amino group is more preferable, and specific examples thereof include methylamino group, dimethylamino group, ethylamino group, diethylamino group, propylamino group, isopropylamino group, dipropylamino group, diisopropylamino group and butylamino.
  • those having a small number of carbon atoms such as a dimethylamino group, a diethylamino group, a pyrrolidine residue, and a piperazine residue and which are easily reacted during synthesis are preferable.
  • n represents an integer of 0 to 10.
  • n represents an integer of 0 to 3.
  • Integers are preferred.
  • An amino group is introduced at the position, and a bifunctional ⁇ -amino group-containing hydrolyzable organosilane compound having two organooxy groups such as an alkoxysilyl group in the molecule is subjected to a condensation reaction in the presence of a catalyst such as a hydrochloric acid catalyst. It can be obtained by quantifying it.
  • the organosilane compound represented by the above general formula (2) are subjected to a condensation reaction to form both ends of the molecular chain of the silanol group-blocking diorganopolysiloxane represented by the above general formula (2). It can be obtained by sealing with a residue of the silane compound.
  • a catalyst is used as necessary. May be good.
  • R 1 is an alkyl group having 1 to 10 carbon atoms unsubstituted or substituted independently of each other, or an aryl group having 6 to 10 carbon atoms substituted or substituted, and n is an integer of 1 to 10. .
  • the bifunctional organopolysiloxane compound of the present invention is mainly composed of a linear diorganopolysiloxane having both ends of the molecular chain sealed with a silanol group or a hydrolyzable silyl group.
  • base polymer particularly a dealcohol type room temperature curable (RTV) organopolysiloxane composition
  • RTV room temperature curable
  • the room temperature curable (RTV) organopolysiloxane composition containing the bifunctional organopolysiloxane compound rapidly condenses with moisture in the atmosphere even at room temperature to have rubber elasticity and excellent extensibility.
  • An elastic body elastomer
  • the composition of the present invention can be suitably used for applications such as coating agents, adhesives, and sealing agents.
  • Articles using the coating agent, adhesive and sealing agent of the present invention include epoxy resin, phenol resin, polyimide resin, polycarbonate resin such as polycarbonate and polycarbonate blend, acrylic resin such as poly (methyl methacrylate), and poly (poly).
  • Ethylene terephthalate poly (butylene terephthalate), polyester resins such as unsaturated polyester resins, polyamide resins, acrylonitrile-styrene copolymer resins, styrene-acrylonitrile-butadiene copolymer resins, polyvinyl chloride resins, polystyrene resins, polystyrene Organic resin base material such as blend of polyphenylene ether, cellulose acetate butyrate, polyethylene resin; metal base material such as iron plate, copper plate, steel plate; paint coated surface; glass; ceramic; concrete; slate plate; textile; wood, stone, tile , (Hollow) Inorganic fillers such as silica, titania, zirconia, alumina; glass cloth including glass fiber, glass fiber products such as glass tape, glass mat, glass paper, etc., and the material and shape of the base material Is not particularly limited.
  • polyester resins such as unsaturated polyester resins, polyamide resins, acryl
  • the organopolysiloxane used as the main agent (base polymer) here has a hydroxyl group (silanol group) or a hydrolyzable silyl group bonded to one silicon atom (two in the molecule) at each end of the molecular chain. It is a thing.
  • the molecular terminal group represented by the following general formula (4) or (5) is a hydroxyl group (diorganohydrosilyl group) or a hydrolyzable group (hydrolyzable group-containing tri).
  • a linear diorganopolysiloxane sealed with an organosilyl group) is used.
  • R 1 is the same as above, X'is an oxygen atom or a divalent hydrocarbon group having 1 to 8 carbon atoms, Y is a hydrolyzable group, and b is 0 or 1.
  • m is an integer in which the viscosity of this diorganopolysiloxane at 25 ° C. is 100 to 1,000,000 mPa ⁇ s, and is usually 30 to 2,000, preferably 50 to 1,200, and more preferably 100 to 800. It is an integer of degree.
  • the viscosity can be measured with a rotational viscometer (for example, BL type, BH type, BS type, cone plate type, rheometer).
  • the number of repetitions (m) or the degree of polymerization of the bifunctional diorganosiloxane unit ((R 1 ) 2 SiO 2/2 ) constituting the main chain of diorganopolysiloxane is determined by gel using, for example, toluene or the like as a developing solvent. It can be determined as a polystyrene-equivalent number average degree of polymerization (or number average molecular weight) or the like in permeation chromatography (GPC) analysis.
  • Y is a hydrolyzable group, for example, an alkoxy group such as a methoxy group, an ethoxy group or a propoxy group; an alkoxyalkoxy group such as a methoxyethoxy group, an ethoxyethoxy group or a methoxypropoxy group; an acetoxy group.
  • Octanoyloxy group benzoyloxy group and other acyloxy groups
  • vinyloxy group allyloxy group, propenyloxy group, isopropenyloxy group, 1-ethyl-2-methylvinyloxy group and other alkoxy group
  • dimethylketooxime group Ketooxime groups such as methylethylketooxime group and diethylketooxime group
  • amino groups such as dimethylamino group, diethylamino group, butylamino group and cyclohexylamino group
  • aminoxy groups such as dimethylaminoxy group and diethylaminoxy group
  • N-methylacetamide group N-ethylacetamide group, N-methylbenzamide group and other amide groups and the like.
  • a methoxy group, an ethoxy group and a propoxy group are preferable.
  • organopolysiloxane used as the main agent (base polymer) include the following diorganopolysiloxane. (In the formula, R 1 , Y, b, m are the same as above.)
  • organopolysiloxanes can be used individually by 1 type, or can be used in combination of 2 or more types having different structures and molecular weights.
  • the prepared composition is rubberized in a short time and exhibits rubber elasticity.
  • the bifunctional organopolysiloxane compound represented by the above general formula (1) is preferably contained in an amount of 0.1 to 10% by mass, more preferably 0.2 to 6% by mass. It is preferably contained in an amount of 0.4 to 4% by mass, more preferably.
  • the bifunctional organopolysiloxane compound may be used alone or in combination of two or more.
  • the bifunctional organopolysiloxane compound has 0. 0 parts by mass of a linear diorganopolysiloxane having both ends of the molecular chain sealed with a silanol group or a hydrolyzable silyl group. It is preferably contained in an amount of 05 to 5 parts by mass, more preferably 0.1 to 3 parts by mass, and even more preferably 0.2 to 2 parts by mass.
  • a cross-linking agent may be used as an arbitrary additive as long as the effect of the present invention is not impaired.
  • Organic silicon compounds other than the bifunctional organopolysiloxane compound of the present invention can also be used as the cross-linking agent, and specifically, methyltrimethoxysilane, dimethyldimethoxysilane, vinyltrimethoxysilane, phenyltrimethoxysilane, and methyltri.
  • Ekoxysilanes such as ethoxysilane and ⁇ - (dimethoxymethylsilyl) propionic acid 2-ethylhexyl; isopropenoxy such as methyltriisopropenoxysilane, ethyltriisopropenoxysilane, vinyltriisopropenoxysilane, and phenyltriisopropenoxysilane Group-containing silanes; acetoxysilanes such as methyltriacetoxysilanes, ethyltriacetoxysilanes, vinyltriacetoxysilanes; and partial hydrolysis condensates of these silanes. These can be used alone or in combination of two or more.
  • the blending amount of the cross-linking agent is 0 to 30% by mass in the composition, preferably 0.1 to 20% by mass, and more preferably 0.5 to 15% by mass.
  • the curing catalyst is not particularly limited as long as it is a curing catalyst used for curing a general moisture condensation curing type composition, and specific examples thereof include alkyl tin compounds such as dibutyltin oxide and dioctyltin oxide.
  • Alkyltin ester compounds such as dibutyltin diacetate, dibutyltin dilaurate, dioctyltin dilaurate, dibutyltin dioctate, dioctyltin dioctate, dioctyltin diversateate; tetraisopropoxytitanium, tetran-butoxytitanium, tetrakis (2-ethylhexoxy) titanium.
  • Titanium esters such as dipropoxybis (acetylacetonato) titanium, titanium diisopropoxybis (ethylacetoacetate), titanium isopropoxyoctylene glycol, and titanium chelate compounds and their partial hydrolyzates; zinc naphthenate, Zinc stearate, zinc-2-ethyloctate, iron-2-ethylhexoate, cobalt-2-ethylhexoate, manganese-2-ethylhexoate, cobalt naphthenate, aluminum trihydroxylate, aluminum alcoholate , Aluminum acylate, salt of aluminum acylate, organosiloxy compound, aluminum chelate compound and other organic metal compounds; 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropylmethyldimethoxysilane, 3- Aminopropylmethyldiethoxysilane, N- ⁇ (aminoethyl) ⁇ -
  • dioctyltin dilaurate dioctyltin diversate, tetraisopropoxytitanium, tetran-butoxytitanium, titanium diisopropoxybis (ethylacetoacetate), 3-aminopropyltrimethoxysilane, because they are more reactive.
  • N- ⁇ (aminoethyl) ⁇ -aminopropyltrimethoxysilane, bis [3- (trimethoxysilyl) propyl] amine, N, N'-bis [3- (trimethoxysilyl) propyl] ethane-1,2- Diamine and tetramethylguanidylpropyltrimethoxysilane are preferable, and dioctyltin dilaurate, dioctyltin diversate, 3-aminopropyltrimethoxysilane, and tetramethylguanidylpropyltrimethoxysilane are more preferable from the viewpoint of curability of the composition.
  • 3-Aminopropyltrimethoxysilane and tetramethylguanidylpropyltrimethoxysilane are more preferable from the viewpoint of curability of the composition, because they do not contain organic tin compounds and have lower toxicity. Guanidylpropyltrimethoxysilane is particularly preferred.
  • the amount of the curing catalyst added is not particularly limited, but is preferably 0.01 to 15% by mass in the composition, preferably 0, in consideration of adjusting the curing rate to an appropriate range to improve workability. .1 to 5% by mass is more preferable.
  • fillers can be used, for example, fine powder silica, fumigant silica, precipitated silica, silica whose surface is hydrophobized with an organic silicon compound, glass beads, glass balloons, and transparent.
  • inorganic fillers such as silica, calcium carbonate, and zeolite are preferable, and aerosol silica and calcium carbonate whose surface is hydrophobized are particularly preferable
  • the blending amount of the filler is preferably 0 to 1,000% by mass, particularly 1 to 1,000% by mass, and particularly preferably 1 to 400% by mass in the composition.
  • thermosetting resin composition of the present invention can be produced by the method shown below.
  • an organopolysiloxane compound represented by the above general formula (1) and a linear diorganopolysiloxane having both ends of the molecular chain sealed with a silanol group or a hydrolyzable silyl group are required at the same time or separately.
  • the mixture may be obtained by mixing with, stirring, dissolving and / or dispersing. Further, depending on the intended use, additives may be added to the mixture and mixed. Each component may be used alone or in combination of two or more.
  • the method for producing the composition is not particularly limited with respect to the apparatus for mixing, stirring and dispersing.
  • a mixing stirrer manufactured by Dalton Corporation, a universal mixing stirrer manufactured by Dalton Corporation, or the like can be used, and these devices may be used in combination as appropriate.
  • Me represents a methyl group
  • the viscosity is a value measured at 25 ° C. by a B-type rotational viscometer.
  • the peak of the target product was confirmed by GC (gas chromatography) measurement, distilled off under reduced pressure with an evaporator and a vacuum pump, and the disappearance of the raw material peak was confirmed by GC measurement to obtain an organopolysiloxane compound 1 having the above structural formula.
  • the organopolysiloxane compound having the above structural formula I got 2.
  • Comparative Reference Example 2 As shown in Table 1, the compositions prepared in Reference Examples 2-1 to 2-3 using the organopolysiloxane compounds 1 to 3 obtained in Examples 1-1 to 1-3 are used in Comparative Reference Example 2. It was found that the thickening rate was much higher than that of the composition prepared in -1, and the reactivity as a chain length extender was good. On the other hand, the composition prepared in Comparative Reference Example 2-1 was hardly thickened, and sufficient reactivity could not be ensured.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Silicon Polymers (AREA)
  • Sealing Material Composition (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne un composé d'organopolysiloxane qui devient un allongeur de chaîne pour une composition vulcanisable à température ambiante (RTV) désalcoolisée qui est rapidement caoutchouté et présente l'élasticité du caoutchouc. Ce composé d'organopolysiloxane est représenté par la formule générale (1), et une composition selon la présente invention contient : ledit composé ; et un diorganopolysiloxane linéaire ayant les deux extrémités d'une chaîne moléculaire scellée avec un groupe silanol ou un groupe silyle hydrolysable. (Dans la formule, R1, R2, et R3 sont chacun indépendamment un groupe alkyle non substitué ou substitué ayant 1 à 10 atomes de carbone, ou un groupe aryle non substitué ou substitué ayant 6 à 10 atomes de carbone ; n est un nombre entier de 0 à 10 ; et X est un groupe amino non substitué ou substitué.)
PCT/JP2020/022790 2019-07-02 2020-06-10 Composition d'organopolysiloxane, composition comprenant ledit composé, et procédé de préparation associé WO2021002163A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2021529937A JP7279790B2 (ja) 2019-07-02 2020-06-10 オルガノポリシロキサン化合物、該化合物を含む組成物及びそれらの製造方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2019-123335 2019-07-02
JP2019123335 2019-07-02

Publications (1)

Publication Number Publication Date
WO2021002163A1 true WO2021002163A1 (fr) 2021-01-07

Family

ID=74100605

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2020/022790 WO2021002163A1 (fr) 2019-07-02 2020-06-10 Composition d'organopolysiloxane, composition comprenant ledit composé, et procédé de préparation associé

Country Status (2)

Country Link
JP (1) JP7279790B2 (fr)
WO (1) WO2021002163A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023272417A1 (fr) * 2021-06-28 2023-01-05 Dow Silicones Corporation Compositions de silicone et leur préparation

Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4005028A (en) * 1975-04-22 1977-01-25 The Procter & Gamble Company Organosilane-containing detergent composition
US4005030A (en) * 1975-04-22 1977-01-25 The Procter & Gamble Company Organosilane-containing anionic detergent composition
JP2004197097A (ja) * 2002-12-19 2004-07-15 Wacker Chemie Gmbh オルガノポリシロキサン組成物、その製造方法、前記組成物から製造された架橋可能な材料、及び前記材料から製造された成形品
JP2012511607A (ja) * 2008-12-11 2012-05-24 ワッカー ケミー アクチエンゲゼルシャフト アルコキシシラン末端ポリマー含有ポリマー混合物
JP2012528823A (ja) * 2009-06-04 2012-11-15 ワッカー ケミー アクチエンゲゼルシャフト アミノオルガノシランの製造方法
WO2015011259A1 (fr) * 2013-07-26 2015-01-29 L'oreal Procédé de traitement capillaire avec au moins un silicone fonctionnalisé avec au moins une unité alcoxysilane, un solvant particulier et moins de 5 % d'eau
WO2015011258A1 (fr) * 2013-07-26 2015-01-29 L'oreal Procédé de traitement capillaire avec au moins un polymère de silicone fonctionnalisé par au mois une unité alcoxysilane et au moins un alcoxysilane spécifique
FR3008887A1 (fr) * 2013-07-26 2015-01-30 Oreal Procede de traitement des cheveux avec au moins un polymere fonctionnalise par au moins un motif alcoxysilane et au moins un polymere cationique
CN105131899A (zh) * 2015-10-15 2015-12-09 成都硅宝科技股份有限公司 高稳定性混凝土硅酮接缝胶及其制备方法
WO2017063419A1 (fr) * 2015-10-15 2017-04-20 成都硅宝科技股份有限公司 Agent d'extension de chaîne d'organosilicone et application
JP2017537186A (ja) * 2014-11-07 2017-12-14 ワッカー ケミー アクチエンゲゼルシャフトWacker Chemie AG 架橋性オルガノポリシロキサン組成物
FR3067603A1 (fr) * 2017-06-15 2018-12-21 L'oreal Composition cosmetique comprenant des polymeres silicones a groupements alcoxy-(aminomethyl)-silyle, des tensioactifs et des acides gras, et procede de traitement cosmetique
CN110256959A (zh) * 2019-05-21 2019-09-20 郝建强 可uv固化有机硅离型剂
CN110922600A (zh) * 2019-10-22 2020-03-27 武汉大学 一类羟烃基有机硅化合物及其制备方法和应用

Patent Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4005028A (en) * 1975-04-22 1977-01-25 The Procter & Gamble Company Organosilane-containing detergent composition
US4005030A (en) * 1975-04-22 1977-01-25 The Procter & Gamble Company Organosilane-containing anionic detergent composition
JP2004197097A (ja) * 2002-12-19 2004-07-15 Wacker Chemie Gmbh オルガノポリシロキサン組成物、その製造方法、前記組成物から製造された架橋可能な材料、及び前記材料から製造された成形品
JP2012511607A (ja) * 2008-12-11 2012-05-24 ワッカー ケミー アクチエンゲゼルシャフト アルコキシシラン末端ポリマー含有ポリマー混合物
JP2012528823A (ja) * 2009-06-04 2012-11-15 ワッカー ケミー アクチエンゲゼルシャフト アミノオルガノシランの製造方法
WO2015011258A1 (fr) * 2013-07-26 2015-01-29 L'oreal Procédé de traitement capillaire avec au moins un polymère de silicone fonctionnalisé par au mois une unité alcoxysilane et au moins un alcoxysilane spécifique
WO2015011259A1 (fr) * 2013-07-26 2015-01-29 L'oreal Procédé de traitement capillaire avec au moins un silicone fonctionnalisé avec au moins une unité alcoxysilane, un solvant particulier et moins de 5 % d'eau
FR3008887A1 (fr) * 2013-07-26 2015-01-30 Oreal Procede de traitement des cheveux avec au moins un polymere fonctionnalise par au moins un motif alcoxysilane et au moins un polymere cationique
JP2017537186A (ja) * 2014-11-07 2017-12-14 ワッカー ケミー アクチエンゲゼルシャフトWacker Chemie AG 架橋性オルガノポリシロキサン組成物
CN105131899A (zh) * 2015-10-15 2015-12-09 成都硅宝科技股份有限公司 高稳定性混凝土硅酮接缝胶及其制备方法
WO2017063419A1 (fr) * 2015-10-15 2017-04-20 成都硅宝科技股份有限公司 Agent d'extension de chaîne d'organosilicone et application
FR3067603A1 (fr) * 2017-06-15 2018-12-21 L'oreal Composition cosmetique comprenant des polymeres silicones a groupements alcoxy-(aminomethyl)-silyle, des tensioactifs et des acides gras, et procede de traitement cosmetique
CN110256959A (zh) * 2019-05-21 2019-09-20 郝建强 可uv固化有机硅离型剂
CN110922600A (zh) * 2019-10-22 2020-03-27 武汉大学 一类羟烃基有机硅化合物及其制备方法和应用

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
ANDRIANOV,K.A. ET AL.: "Methods of synthesis of 1-p- diethoxymethylchloromethylsiloxanes and the reaction of substitution of chlorine in the a-chloromethyl group", ZHURNAL OBSHCHEI KHIMII, vol. 30, 1960, pages 2393 - 2397, ISSN: 0044-460X *
BARYSHOK,V.P. ET AL.: "Interaction of 1,3-dimethyl-1,3-bis(chloromethyl)-1,3- diethoxy-1,3- disiloxane with primary and secondary amines", METALLOORGANICHESKAYA KHIMIYA, vol. 4, no. 5, 1991, pages 1079 - 1082, ISSN: 0235-0114 *
DATABASE REGISTRY 5 August 2020 (2020-08-05), XP055784118, retrieved from CAS Database accession no. 744999-44-8 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023272417A1 (fr) * 2021-06-28 2023-01-05 Dow Silicones Corporation Compositions de silicone et leur préparation

Also Published As

Publication number Publication date
JPWO2021002163A1 (fr) 2021-01-07
JP7279790B2 (ja) 2023-05-23

Similar Documents

Publication Publication Date Title
US9644124B2 (en) Silicon-containing compound having alkoxysilyl-ethylene group at its terminal, room temperature-curable organopolysiloxane composition, and molded product obtained by curing the composition
JP2738235B2 (ja) 紫外線及び湿気硬化性オルガノポリシロキサン組成物、その硬化物及びその製造方法
KR102326223B1 (ko) 실온 경화성 오르가노폴리실록산 조성물 및 해당 실온 경화성 오르가노폴리실록산 조성물의 경화물인 성형물
JP6747507B2 (ja) 室温硬化性組成物、シーリング材並びに物品
JP2018087348A (ja) 室温硬化性組成物、シーリング材及び物品
JP6760223B2 (ja) 室温硬化性オルガノポリシロキサン組成物、およびこれを含有するシール剤、コーティング剤、接着剤、成形物
JP7279790B2 (ja) オルガノポリシロキサン化合物、該化合物を含む組成物及びそれらの製造方法
JP7467891B2 (ja) オルガノポリシロキサンおよびそれを含有するコーティング用組成物
JP7378906B2 (ja) 鎖長延長剤とそれを含む脱アルコール型室温硬化性オルガノポリシロキサン組成物、並びにオルガノポリシロキサン化合物及びその製造方法
JP6402690B2 (ja) オルガノポリシルメチレンシロキサン組成物
JP5177344B2 (ja) 室温硬化性オルガノポリシロキサン組成物
JP6315100B2 (ja) 新規有機チタン化合物、該有機チタン化合物の製造方法、硬化触媒及び室温硬化性オルガノポリシロキサン組成物
JP7315008B2 (ja) 室温硬化性樹脂組成物、コーティング剤、接着剤及びシーリング剤、並びに物品
JP6156211B2 (ja) 室温硬化性オルガノポリシロキサン組成物及び物品
JP7110722B2 (ja) 含フッ素有機ケイ素化合物及びその製造方法、室温硬化性含フッ素ゴム組成物及びその硬化物並びに物品
JPH06212077A (ja) 室温硬化性組成物
JP2012233040A (ja) 室温硬化性オルガノポリシロキサン組成物
JP7523868B2 (ja) 室温硬化性樹脂組成物、コーティング剤、接着剤及びシーリング剤、並びに物品
JP7276245B2 (ja) 室温硬化性オルガノポリシロキサン組成物及び物品
JP6243922B2 (ja) 室温硬化性樹脂組成物
JP3344012B2 (ja) 湿気硬化性オルガノポリシロキサン組成物
JP2529022B2 (ja) 室温硬化性組成物およびその硬化物
JP2711613B2 (ja) 室温硬化性組成物
WO2022030470A1 (fr) Composition de résine durcissable à température ambiante, agent de revêtement, agent adhésif, agent d'étanchéité, et article
US20230220163A1 (en) Organopolysiloxane and a composition comprising the same

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 20835052

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2021529937

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 20835052

Country of ref document: EP

Kind code of ref document: A1