EP3589698A1 - Procédé pour produire des substances pouvant être réticulées pour obtenir des élastomères - Google Patents

Procédé pour produire des substances pouvant être réticulées pour obtenir des élastomères

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Publication number
EP3589698A1
EP3589698A1 EP17708724.4A EP17708724A EP3589698A1 EP 3589698 A1 EP3589698 A1 EP 3589698A1 EP 17708724 A EP17708724 A EP 17708724A EP 3589698 A1 EP3589698 A1 EP 3589698A1
Authority
EP
European Patent Office
Prior art keywords
optionally
radical
weight
hydrocarbon radical
added
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP17708724.4A
Other languages
German (de)
English (en)
Inventor
Torsten Sixt
Franz Neuhauser
Josef SCHNITZINGER
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wacker Chemie AG
Original Assignee
Wacker Chemie AG
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 Wacker Chemie AG filed Critical Wacker Chemie AG
Publication of EP3589698A1 publication Critical patent/EP3589698A1/fr
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Classifications

    • 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
    • C08K5/541—Silicon-containing compounds containing oxygen
    • C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
    • C08K5/5419—Silicon-containing compounds containing oxygen containing at least one Si—O bond containing at least one Si—C 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
    • C08G77/06—Preparatory processes
    • C08G77/08—Preparatory processes characterised by the catalysts used
    • 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 hydroxy 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
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/544—Silicon-containing compounds containing nitrogen
    • 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
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure

Definitions

  • the invention relates to a process for the preparation of elastomers crosslinkable compositions based on
  • Organosilicon compounds in particular neutral-crosslinking compositions based on organosilicon compounds, in which essentially only alcohols are eliminated during the crosslinking.
  • RTV-1 One-component silicone rubber compounds
  • RTV-1 mixtures are polydiorganosiloxanes which are terminated either by OH groups or by silyl groups which carry hydrolyzable groups. These products are storage stable under the exclusion of moisture, polymerize under the influence of water or humidity. Depending on
  • Oxime-crosslinking compounds which act as a cleavage product instead of
  • 2-Butanone oxime other oximes such as 2-propanone oxime or 2-pentanone oxime split off, are usually listed only in individual regions in the chemical registers and can therefore be used only with considerable restrictions as a substitute. In addition, significantly higher market prices are what the
  • Alkoxy-crosslinking RTV-1 compositions are described in many places, but all of these formulations employ organopolysiloxanes endblocked as base polymers with alkoxy groups which must first be provided in a separate functionalization step, the so-called "end-capping", the catalyst generally having to be deactivated thereafter. Examples thereof are described in US 5,055,502 A (catalysis with zinc betadiketonates), US 5,079,324 A (LiOH catalysis), US 5,728,794 A (phosphoric acid partial ester catalysis) and US 3,504,051 A (catalysis with sodium acetate). Thus, a simple production process in a "one-step process" is not possible.
  • Oxi-compounds do not fulfill the requirement for freedom from decla- ration according to hazardous substances legislation, since they exceed the concentration of 1% by weight of free oxime immediately or in the course of storage. Oximes are considered hazardous to health
  • 2-butanone oxime is classified as carcinogenic.
  • oxime compounds are technically easy to prepare, but have a potential hazard or Oximmassen with less critical Oximvernetzern are incomplete
  • EP 1 700 885 A1 and EP 98 369 A2 describe the use of special silanes, the alkoxy and oximo groups on the same
  • EP 1 788 018 A1 and EP 1 705 222 A1 describe oximosilanes which carry 2-propanone oximo groups instead of 2-butanone oximo groups. This prevents the release of 2-butanone oxime but releases a similar amount of another oxime. The amount of free oxime in the compound is thus not significantly reduced. Such silanes are also expensive and also due to the sometimes missing registration status only with great restrictions available.
  • No. 8,618,235 B2 describes compounds of oximosilane-terminated polymers in which alkoxysilane is introduced as a scavenger. The release of the oximosilane in the endblocking and compounding can not be prevented thereby and
  • Oximosilan- crosslinker per 100 parts of polymer easily exceeds the critical mark of 1% of free silane over the storage time. Thus, such products must also be marked as hazardous.
  • Alkoxysilanes is greater, the higher the required
  • the object of the invention is therefore to overcome these disadvantages of the prior art and to provide neutral-crosslinking silicone compositions which have good storage stability, wherein the limit concentrations of free oximes for the classification as hazardous material is reliably not exceeded in the masses over the storage time, and which can be obtained without the separate preparation of functionalized polymers.
  • the invention relates to a process for the preparation of elastomers crosslinkable compositions, characterized in that
  • R is a monovalent hydrocarbon radical having 1 to 18 carbon atoms, preferably a methyl or vinyl radical
  • R 1 is the same or different and a monovalent
  • Hydrocarbon radical having 1 to 8 carbon atoms, preferably a methyl or ethyl radical, and (3) organosilicon compounds having at least one over
  • Carbon-bonded, basic nitrogen-containing radical preferably aminosilanes
  • R 2 is a monovalent hydrocarbon radical having 1 to 18 carbon atoms, preferably a methyl or vinyl radical, and
  • R 3 is the same or different and a monovalent
  • Partial hydrolysates and optionally further
  • radicals R are alkyl radicals, such as the methyl, ethyl, n-propyl, iso-propyl, 1-n-butyl, 2-n-butyl, iso-butyl, tert. Butyl, n-pentyl, iso-pentyl, neo-pentyl, tert. -
  • Cycloheptyl and methylcyclohexyl radicals are cyclohexyl radicals; Alkenyl radicals, such as the vinyl, 5-hexenyl, cyclohexenyl, 1-propenyl, allyl,
  • Alkynyl radicals such as the ethynyl, propargyl and 1-propynyl radicals
  • Aryl radicals such as the phenyl, naphthyl, anthryl and phenanthryl radicals
  • Alkaryl radicals such as o-, m-, p-tolyl radicals, xylyl radicals and ethylphenyl radicals
  • aralkyl radicals such as the benzyl radical, the ⁇ - and the ⁇ -phenylethyl radical.
  • radicals R 1 are alkyl radicals having 1 to 8 C atoms.
  • radicals R 2 are alkyl and alkenyl radicals having 1 to 18 carbon atoms.
  • radicals R 3 are alkyl radicals having 1 to 5 C atoms.
  • the polyorganosiloxane (1) is preferably first initially charged and homogenized with plasticizer (8) in a first step, in addition to the alkoxysilane (2) and the organosilicon compound (3).
  • component (3) can be carried out together with component (2) or after addition of (2).
  • the mixture is homogenized, preferably at the pressure of the environment, such as at the pressure of 900 to 1100 hPa, optionally at reduced pressure, such as at a pressure of 50 to 300 hPa.
  • a second step is in the inventive
  • ketoximosilane (4) was added and mixed.
  • the mixture is homogenized, preferably at the pressure of
  • a third step it is preferable to add to the reaction mixture from the second step further alkoxysilanes (2) of the formula (I) and / or their partial hydrolysates and further organosilicon compounds (3).
  • Steps 2 and 3 can also be done together.
  • alkoxysilanes (2) and / or their partial hydrolysates are preferably used in a total amount of 1 to 25 parts by weight, preferably 2 to 15 parts by weight, based on 100 parts by weight of organopolysiloxane (1),
  • Alkoxysilanes (2) and / or their Generalhydrolysate preferably in an amount of 1 to 5 parts by weight, based on 100 parts by weight of organopolysiloxane (1) used.
  • organosilicon compounds (3) are preferably used in a total amount of from 0.25 to 10 parts by weight, preferably from 1 to 7.5 parts by weight, in each case based on 100 parts by weight of the organopolysiloxanes (1),
  • Organosilicon compounds (3) preferably in amounts of 0.1 to 1 parts by weight, based on 100 parts by weight
  • Condensation catalysts preferably tin catalysts, optionally
  • the process according to the invention preferably takes place
  • the preparation is preferably carried out at temperatures between 10 and 80 ° C, more preferably between 20 and 60 ° C, and at pressures between 50 to 2000 hPa
  • Atmospheres more preferably between 100 to 1500 hPa atmospheres.
  • Component (1) is preferably substantially linear, hydroxyl-terminated organopolysiloxanes, more preferably those of the formula
  • n is an integer from 500 to 2000, preferably from 600 to 1700, preferably from 600 to 1300, is.
  • organopolysiloxane (1) or a mixture of at least two kinds of organopolysiloxanes (1) can be used.
  • radicals R apply in their entirety to radicals R 4 .
  • the radical R 4 is preferably alkyl groups having 1 to 6 carbon atoms, more preferably the methyl radical.
  • the organopolysiloxanes (1) are preferably a, ⁇ -dihydroxydialkylpolysiloxanes, more preferably a, ⁇ -dihydroxypolydimethylsiloxanes.
  • organopolysiloxanes (1) are examples of organopolysiloxanes (1).
  • n is an integer of 500 to 2000, preferably 600 to 1700, more preferably 600 to 1300, and y represents such an integer that y / x is preferably 0.01 to 0.1.
  • the organopolysiloxanes (1) used according to the invention have a viscosity of preferably 10,000 to 700,000 mPa. s, preferably from 20,000 to 400,000 mPa.s, more preferably from 50,000 to 200,000 mPa. , each at 25 ° C.
  • the organopolysiloxanes (1) are N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)
  • Silicon chemistry commonly used methods are produced.
  • alkoxysilanes (2) used according to the invention are organyltrialkoxysilanes, such as methyltrimethoxysilane, ethyltrimethoxysilane, n-propyltrimethoxysilane, vinyltrimethoxysilane, methyltriethoxysilane, ethyltriethoxysilane, n-propyltriethoxysilane and vinyltriethoxysilane, and the partial hydrolysates of the abovementioned silanes with a maximum of 10 silicon atoms.
  • organyltrialkoxysilanes such as methyltrimethoxysilane, ethyltrimethoxysilane, n-propyltrimethoxysilane, vinyltrimethoxysilane, methyltriethoxysilane, ethyltriethoxysilane, n-propyltriethoxysilane and vinyltriethoxysilane
  • silanes (2) used according to the invention are preferably methyltrimethoxysilane and vinyltrimethoxysilane.
  • Component (3) is preferably organosiloxanes or organosilanes having at least one radical bonded via carbon to silicon, basic nitrogen-containing radical, with aminosilanes being preferred.
  • A is a radical of the formula -R 6 - (NR 7 -R 8 -) X NR 7 2 ,
  • R 5 is the same or different and a monovalent
  • Hydrocarbon radical having 1 to 8 C atoms, preferably a methyl or ethyl radical
  • R s is a divalent hydrocarbon radical having 1 to 8 C atoms
  • R 7 is identical or different and is a hydrogen atom or a monovalent hydrocarbon radical having 1 to 8 C atoms, preferably a hydrogen atom,
  • R 8 is a divalent hydrocarbon radical having 1 to 18 C atoms, preferably 2 C atoms, and
  • x is 0, 1, 2 or 3, preferably 0 or 1.
  • Component (4) is ketoximosilanes of the formula
  • R 2 is a monovalent hydrocarbon radical having 1 to 18 carbon atoms, preferably a methyl or vinyl radical, and
  • R 3 is the same or different and a monovalent
  • Hydrocarbon radical having 1 to 5 carbon atoms
  • Isopropyl radical means.
  • ketoximosilanes (4) of the formula (II) and / or their partial hydrolysates are used in amounts of at most 1% by weight, based on the total weight of the compositions. Preferably, they are used in amounts of at least 0.25 wt .-%, based on the total weight of the masses.
  • the amount of oxime liberated upon storage in the compositions is
  • condensation catalysts (5) For preparing the crosslinkable compositions according to the invention, preference is given to condensation catalysts (5)
  • crosslinking masses could exist.
  • condensation catalysts (5) are organic compounds of calcium, strontium, barium, copper, silver, tin, zinc, zirconium, titanium, bismuth, lead, iron and aluminum.
  • Preferred among these condensation catalysts are alkyl titanates, alkylzirconates, zinc carboxylates, titanium chelates and organic tin compounds such as di-n-butyltin diacetate, di-n-butyltin dilaurate, di-n-octyltin diacetate, di-n-octyltin dilaurate, dibutyltin oxide, dioctyltin oxide and reaction products of at least two molecules per molecule
  • condensation catalysts (5) are basic organic compounds such as
  • the catalysts (5) are
  • organic dialkyltin carboxylates or their reaction products with alkoxysilanes e.g. Dioctyltin dilaurate, alkyl titanates, alkyl zirconates, titanium chelates such as diisobutoxy bis
  • monovalent hydrocarbon radicals as hydrolyzable silane or its oligomer with diorganotin diacylate or diorganotin oxide.
  • catalysts (5) are used in the process according to the invention, these are amounts of preferably 0.0001 to 2% by weight, preferably 0.001 to 1.5% by weight, in each case based on the total weight of the composition of the invention.
  • fillers (6) are non-reinforcing
  • Fillers ie fillers with a BET surface area of up to 50 m 2 / g, such as quartz, diatomaceous earth, calcium silicate, zirconium silicate, zeolites, metal oxide powder, such as aluminum, titanium, iron or zinc oxides or their mixed oxides, barium sulfate , Calcium carbonate, gypsum, talc, kaolin, silicon nitride,
  • Silicon-aluminum mixed oxides of large BET surface area Silicon-aluminum mixed oxides of large BET surface area
  • fillers such as asbestos and plastic fibers.
  • the fillers mentioned may be rendered hydrophobic, for example by treatment with organosilanes or siloxanes or by etherification of hydroxyl groups to alkoxy groups. If fillers (6) are used, they are
  • compositions according to the invention contain fillers (6), these are amounts of preferably 5 to 200 parts by weight, preferably 8 to 150 parts by weight, based in each case on 100 parts by weight of component (1).
  • the compositions of the invention preferably contain fillers (6).
  • fillers (6) are preferably added to the reaction mixture from the second or, if a third step is conducted, to the reaction mixture from the third step, and then tin catalysts (5), optionally
  • Adhesion promoter (7), optionally stabilizers (9) and optionally additives (10) are added and mixed together.
  • adhesion promoter (7) before the addition of
  • the adhesion promoter (7) optionally used in the compositions according to the invention may be silanes and organopolysiloxanes having functional groups, for example those containing amino, glycidoxypropyl, ureidopropyl, carbamato or methacryloxypropyl radicals.
  • adhesion promoters (7) are epoxysilanes, such as
  • Glycidoxypropyltrimethoxysilanes glycidoxypropylmethyldimethoxysilane, glycidoxypropyltriethoxysilane or
  • compositions of the invention preferably contain adhesion promoter (7).
  • the plasticizer (8) which may be used is preferably silicone oils which are resistant to component (1).
  • viscosities between 5 and 10,000 mPas at 25 ° C or hydrocarbon mixtures with viscosities between 1 and 20 mPas at 40 ° C, more preferably with
  • plasticizers (8) are used in the process according to the invention, these are amounts of preferably 5 to 100 parts by weight, more preferably 15 to 70
  • plasticizers are preferred.
  • plasticizers are in the first
  • crosslinkable masses optionally used stabilizers
  • compositions according to the invention are acid phosphoric acid esters, phosphonic acids and acid phosphonic acid esters. If the compositions according to the invention contain stabilizers (9), they are amounts of preferably 0.01 to 1 part by weight, based on 100 parts by weight of component (1). The compositions of the invention preferably contain stabilizers (9).
  • optionally used additives (10) are fungicides, dyes, pigments, heat stabilizers,
  • Antioxidants organic solvents, electrical property modifiers such as conductive carbon black, flame retardants and light stabilizers.
  • inventive mass additives (10) contain amounts of preferably 0.01 to 30
  • compositions of the invention preferably contain additives (10).
  • the inventive preparation of the crosslinkable compositions and their storage is preferably carried out under substantially anhydrous conditions, so that the masses can not cure prematurely.
  • the inventive method is under
  • Inert gas atmosphere particularly preferably under nitrogen, carried out.
  • the normal water content of the air is sufficient.
  • compositions according to the invention are preferably added
  • the crosslinking can, if desired, also at higher or lower temperatures than room temperature and / or by means of the normal water content of the air
  • compositions prepared according to the invention can be used for all
  • Uses can be used, for which can be used when accessing water at room temperature to elastomer crosslinking compositions.
  • compositions prepared according to the invention are thus excellently suitable, for example, as sealing compounds for joints, including vertically extending joints, and similar voids of e.g. 10 to 40 mm clear width, e.g. from
  • Adhesives or sealants e.g. in window construction or in the production of aquariums or showcases, as well as for
  • Components or used as a protective coating are Components or used as a protective coating.
  • the viscosity data are based on the measurement according to DIN 53019 at 25 ° C.
  • the mechanical properties of the elastomers are determined in each case according to the following standardized tests:
  • the determination of the oxime content of the crosslinkable composition is carried out by gas chromatography (GC).
  • sample bags are tempered for 10 minutes at 90 ° C, then a sample is drawn from the gas phase over the crosslinkable mass and injected into the injector.
  • the carrier gas used for the gas chromatography is hydrogen with a volume flow of 78 ml / min and a split ratio of 1: 150, the detection is carried out by means of FID.
  • the injector temperature is 250 ° C.
  • the temperature profile starts with 110 ° C at a heating rate of 40 ° C / min to the end point 250 ° C.
  • the column material is a 10 m silica column CP-Sil 19 CB with 0.1 mm inner diameter and 0.2 ⁇ coating thickness.
  • Viscosity of 80 000 mPa.s and 115 g of a trimethylsilyl-endblocked polydimethylsiloxane having a viscosity of 100 mPa.s were homogenized in a planetary mixer and with 18g of methyltris (methylethylketoximo) silane and 6 g
  • Viscosity of 80,000 mPa.s and 115 g of a trimethylsilyl-endblocked polydimethylsiloxane having a viscosity of 100 mPa.s were homogenized in a planetary mixer and mixed with 14 g of vinyltrimethoxysilane and 2 g of 3- (2-aminoethyl) aminopropyltrimethoxysilane for 5 minutes , Subsequently, another 4 g of 3- (2-aminoethyl) aminopropyltrimethoxysilane
  • Viscosity of 80,000 mPa.s and 115 g of a trimethylsilyl-endblocked polydimethylsiloxane having a viscosity of 100 mPa.s were homogenized in a planetary mixer and mixed with 8.7 g of vinyltrimethoxysilane and 1.3 g of 3- (2-aminoethyl) aminopropyltrimethoxysilane ,
  • a second step after stirring for 8 minutes, 5 g of vinyltris (methyl ethyl ketoximo) silane were added and mixed for a further 2 minutes.
  • Dibutyltin diacetate mixed under vacuum. The product was bottled for storage in moisture-proof containers.
  • the compound obtained in each case according to Examples 1-4 and Comparative Examples 1 and 2 is packed in moisture-tight containers and the compounds are each allowed to crosslink fresh after preparation and also left to crosslink after storage at 14d / 70 ° C.
  • the compound obtained in each case in a 2 mm thick is packed in moisture-tight containers and the compounds are each allowed to crosslink fresh after preparation and also left to crosslink after storage at 14d / 70 ° C.
  • Table 1 Determination of the oxime content and the skin formation time fresh after preparation and after storage
  • Comparative Example 2 shows initially not stable consistency after production, but this changes after a short storage time at room temperature.
  • Examples 1-4 according to the invention show good and very stable paste properties as well as good mechanical properties
  • Examples 1-4 have a content of free oxime of only 0.3 to 0.5% and thus well below 1% and are therefore not classified as hazardous.
  • the oxime masses according to Comparative Experiment 1 have a content of free oxime of 1.7%, ie significantly higher than 1% and are therefore classified as hazardous.

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

Abstract

L'invention concerne un procédé pour produire des substances pouvant être réticulées pour obtenir des élastomères, caractérisé en ce qu'il consiste : à produire, au cours d'une première étape, un mélange renfermant (1) des organopolysiloxanes présentant au moins deux groupes hydroxyle, (2) des alcoxysilanes de formule RSi(OR1)3 (I) et/ou leurs hydrolysats partiels, R désignant un groupe hydrocarbure monovalent en C1-C18 et R1 représentant un groupe hydrocarbure monovalent en C1-C8 et (3) des composés organosilicium comprenant au moins un groupe présentant de l'azote basique à liaison SiC ; à ajouter, au cours d'une deuxième étape, au mélange issu de la première étape, (4) des cétoximosilanes de formule R2Si (ON=CR3 2) 3 (II) et/ou leurs hydrolysats partiels, R2 désignant un groupe hydrocarbure monovalent en C1-C18 et R3 représentant un groupe hydrocarbure monovalent en C1-C5, selon des quantités maximales égales à 1% en poids par rapport au poids total de la substance, à condition qu'éventuellement des alcoxysilanes (2) supplémentaires et éventuellement des composés organosilicium (3) supplémentaires soient ajoutés au cours de la deuxième étape ou éventuellement au cours d'une troisième étape suivant la deuxième étape ; puis à ajouter, au mélange réactionnel issu de la deuxième ou éventuellement de la troisième étape, (5) des catalyseurs de condensation, éventuellement (6) des matières de charge, éventuellement (7) des promoteurs d'adhésion, éventuellement (8) des plastifiants, éventuellement (9) des stabilisateurs et éventuellement (10) des additifs et à les mélanger audit mélange réactionnel.
EP17708724.4A 2017-02-28 2017-02-28 Procédé pour produire des substances pouvant être réticulées pour obtenir des élastomères Withdrawn EP3589698A1 (fr)

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PCT/EP2017/054639 WO2018157914A1 (fr) 2017-02-28 2017-02-28 Procédé pour produire des substances pouvant être réticulées pour obtenir des élastomères

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US (1) US11028268B2 (fr)
EP (1) EP3589698A1 (fr)
JP (1) JP2020509101A (fr)
KR (1) KR102256900B1 (fr)
CN (1) CN110402272B (fr)
WO (1) WO2018157914A1 (fr)

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US12043738B2 (en) * 2018-01-03 2024-07-23 Sika Technology Ag Silicone sealant having adjustable flow properties
KR20250022715A (ko) 2022-06-02 2025-02-17 셰브론 필립스 케미컬 컴퍼니 엘피 고다공성 플루오린화 실리카 코팅된 알루미나 활성제-지지체 및 올레핀 중합을 위한 메탈로센 기반 촉매 시스템에서의 이의 용도
JP2024106825A (ja) * 2023-01-27 2024-08-08 旭化成ワッカーシリコーン株式会社 １液硬化型組成物に使用される組成物セット
CN119709106A (zh) * 2024-12-13 2025-03-28 湖北兴瑞硅材料有限公司 低水汽透过率光伏组件用硅酮密封胶及制备方法

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US20200239688A1 (en) 2020-07-30
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CN110402272B (zh) 2021-11-26
US11028268B2 (en) 2021-06-08

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