WO2008037468A2 - Silanes dimères et oligomères et leurs produits de réaction avec des organosiloxanes - Google Patents

Silanes dimères et oligomères et leurs produits de réaction avec des organosiloxanes Download PDF

Info

Publication number
WO2008037468A2
WO2008037468A2 PCT/EP2007/008413 EP2007008413W WO2008037468A2 WO 2008037468 A2 WO2008037468 A2 WO 2008037468A2 EP 2007008413 W EP2007008413 W EP 2007008413W WO 2008037468 A2 WO2008037468 A2 WO 2008037468A2
Authority
WO
WIPO (PCT)
Prior art keywords
formula
radical
silanes
silane
radicals
Prior art date
Application number
PCT/EP2007/008413
Other languages
English (en)
Other versions
WO2008037468A3 (fr
Inventor
Harald Chrobaczek
Kenneth Chowdhury
Rule Niederstadt
Andreas Eisele
Sabrina Süss
Günther Tschida
Original Assignee
Huntsman Textile Effects (Germany) Gmbh
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
Priority claimed from EP06020359A external-priority patent/EP1905794A1/fr
Priority claimed from EP07018238A external-priority patent/EP2039717A1/fr
Application filed by Huntsman Textile Effects (Germany) Gmbh filed Critical Huntsman Textile Effects (Germany) Gmbh
Publication of WO2008037468A2 publication Critical patent/WO2008037468A2/fr
Publication of WO2008037468A3 publication Critical patent/WO2008037468A3/fr

Links

Classifications

    • 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
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/44—Block-or graft-polymers containing polysiloxane sequences containing only polysiloxane sequences
    • 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
    • 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
    • C08G77/045—Polysiloxanes containing less than 25 silicon atoms
    • 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
    • C08G77/38—Polysiloxanes modified by chemical after-treatment

Definitions

  • the invention relates to dimeric or oligomeric silanes or mixtures thereof and to the reaction products of these silanes with organosiloxanes. It further relates to the use of the polyorganosiloxanes obtained in this reaction for the coating of fabrics.
  • Polysiloxanes which contain acrylate groups are known, e.g. from DE-A 102 19 734, EP-A 564 253, US-A 4 528 081 and EP-A 373 659 and US 6 211 322 B1. Furthermore, it is evident from the abovementioned literature that it is known to cure silicon compounds which contain acrylate units by free-radical polymerization. This free-radical polymerization can take place, for example, by UV irradiation.
  • polyorganosiloxanes with functional groups e.g. acrylate groups
  • side chains can be prepared by condensation or equilibration reactions.
  • polyorganosiloxanes are reacted with monomeric silanes carrying reactive groups, where, in the case of condensation reactions, polysiloxanes with terminal OH groups are used as starting compounds.
  • the polyorganosiloxanes with reactive groups in side chains known from the prior art contain the side chains in random distribution.
  • the reactivity of such polysiloxanes e.g. with regard to their rapid curability or with regard to the oil repellent effects that can be achieved therewith, is not satisfactory in all cases.
  • the object of the present invention was to provide silanes from which, following reaction with polyorganosiloxanes, polymers can be obtained which have increased reactivity, e.g. in curing processes, or which are suitable for improving certain effects, e.g. the oil repellent effect of fiber materials treated with these polymers.
  • the object was achieved by dimeric and/or oligomeric silanes preparable by reaction of a silane of the formula (I) or of a mixture of such silanes, with water, or of a mixture of a silane of the formula (I) and a compound of the formula (Ia), with water,
  • OH O-R or preferably -CH(CH 3 ) 2 where 0.5 to 1.5 mol of water are used per mole of silane or silane mixture, to give a dimeric and/or oligomeric product which contains 2 to 200, in particular 2 to 50, particularly preferably 2 to 15, silicon atoms in the molecule or to give a mixture of such dimeric or oligomeric products, where optionally in a first step firstly two identical or different silanes of the formula (I) are reacted together to give a dimer or oligomer and then this dimer or oligomer is further reacted with water under the abovementioned conditions, where all of the radicals R present, independently of one another, are the phenyl radical or a branched or unbranched alky!
  • R 1 is R or OR or where R 2 is the vinyl radical or a linear or branched alkyl radical having 1 to 18 carbon atoms, which may be substituted by one or more, optionally quaternized, amino groups, amido groups, mercapto groups, epoxy groups, phosphono groups, hydroxy groups or fluorine atoms, or where R 2 is a radical of the formula (II), of the formula (III) or of the formula (IV),
  • R 9 R 3 in which R 8 is H or CH 3 or C 2 H 5 or -CH 2 CH 2 -OH and R 9 is H or -COOR 8 - R- NH-CH 2 CH 2 -NH-CH-CH-COOR 8 (X)
  • R 4 is a divalent linear or branched hydrocarbon radical having 1 to 4 carbon atoms
  • R 3 is in each case H or CH 3 ,
  • R 14 is H or a linear or branched alky! radical having 1 to 18 carbon atoms or is a radical of the formula (XIX), in which the individual units -(CH 2 -CH 2 -O)- and -(CHR 3 -CHR 3 -O)- may be distributed arbitrarily over the chain, in which k and I are in each case a number in the range from 1 to 22 and the sum k+l is in the range from 3 to 25, in which f is 0 or 1 , all of the radicals R 16 , independently of one another, are H or
  • R R 3 can be distributed arbitrarily over the chain, where R 12 is H or C 2 H 5 and where R 17 is R or -R 4 -NH 2 or
  • R 13 R 13 OH in which R 13 is H or — CH(CH 3 ) 2 or -CH 2 -CH(CH 3 ) 2 ,
  • d is a number from 1 to 6, or is a radical of one of the formulae (XXV) to (XXXI),
  • dimeric/oligomeric silanes according to the invention are suitable for the treatment of fabrics, such as, for example, wovens.
  • reaction of the dimeric or oligomeric silanes according to the invention or of mixtures of these silanes with organosiloxanes of the formula (VIII) leads to novel polyorganosiloxanes in which the reactive groups originating from the silanes in side chains are present in block form, whereas products from the prior art have the reactive side chains in statistical distribution.
  • these novel polyorganosiloxanes can on the one hand have excellent reactivity, in particular in curing processes, and on the other hand can bring about improved effects of fiber materials treated therewith, such as, for example, increased oil repellent effect.
  • Advantages result particularly when the functional groups (R 2 ) present in the silanes contain acrylate radicals, see, for example, formulae (III), (IV), (V) and (XVI). These acrylate radicals are then also present in the products obtained following reaction with organosiloxanes and can cure and/or polymerize, e.g. through UV radiation. This makes the novel polysiloxanes highly suited for coating processes, e.g. coating fabrics.
  • Glass-fiber fabric can also be treated with these novel polysiloxanes.
  • glass-fiber fabric can also be treated with dimeric/oligomeric silanes according to the invention and then be cured, or condensed with the elimination of alcohol.
  • the application of the dimeric/oligomeric silanes according to the invention or of the novel polysiloxanes according to the invention to the fabrics or to the glass-fiber fabric can take place by known methods, e.g. by coating or padding (bath impregnation).
  • the starting substances used for the preparation of silanes according to the invention are silanes of the formula (I) OR
  • silane or silane mixture is reacted with water in quantitative ratios such that 0.5 to 1.5 mol of water are used per mole of silane. If a mixture of silanes/formula (I) is used, then of course the number of moles of the individual silanes present in the mixture are to be added together in order to calculate the required amount of water.
  • the described reaction of the silanes of the formula (I) with water leads to a dimeric or oligomeric product or a mixture of such products.
  • This comprises on average 2 to 200, in particular 2 to 50 and particularly preferably 2 to 15, silicon atoms in the molecule.
  • the product that forms is a mixture which contains dimeric and oligomeric silanes.
  • These dimeric or oligomeric silanes are formed in the reaction of the silanes of the formula (I) with water by 2 OR groups of two different silane molecules reacting in the presence of water with the elimination of ROH to give compounds which have Si-O-Si bonds.
  • the number of silicon atoms which the resulting mixture contains on average per molecule, and also the relative quantitative ratio of dimer to oligomer can be controlled in a manner known to the chemist through the reaction conditions, thus, for example, through the ratio of the amount of silanes used to the amount of water.
  • the silanes of the formula (I) used are preferably compounds which are liquid at room temperature. If silanes of solid consistency are to be used, it is advisable to use a solvent which does not react with water under the conditions of the reaction of the silanes. Examples of solvents are low molecular weight dialkyl ketones.
  • the reaction of the silanes of the formula (I) with water takes place preferably at a temperature which is 5-10 0 C higher than the boiling point of the alcohols ROH resulting from the silanes, and during the reaction, the alcohol ROH resulting from silane and water is preferably distilled off directly, optionally under reduced pressure. It may be advantageous to add a catalyst for the reaction of silane with water. Suitable catalysts are described below.
  • the silanes of the formula (I) contain two or three OR groups bonded to an Si atom. If the radical R 1 in formula (I) is OR, 3 OR groups are present. From silanes with 2 or 3 OR groups, it is possible, following dimerization/oligomerization and subsequent further reaction with ⁇ , ⁇ - dihydroxydialkylpolysiloxanes, which is described below, to obtain polysiloxanes which contain two or more adjacent reactive groups in block form. These reactive groups originate from the radicals R 2 of the silanes of the formula (I).
  • radicals R present are the unsubstituted phenyl radical or an alkyl radical having 1 to 18 carbon atoms.
  • each radical R is preferably the methyl radical or the ethyl radical.
  • the radical R 1 is either a radical R of the specified meaning or is a radical
  • linear or branched alkyl radical having 1 to 18 carbon atoms which can be substituted by one or more amino groups, amido groups, mercapto groups, epoxy groups or fluorine atoms.
  • amino groups amido groups, mercapto groups, epoxy groups or fluorine atoms.
  • substitution by amino groups the latter may be present in free and/or quaternized form.
  • R 3 is hydrogen or the methyl group
  • R 4 is a divalent linear or branched hydrocarbon radical having 1 to 4 carbon atoms
  • R 5 is hydrogen or
  • R 8 is hydrogen or -CH 3 or -CH 2 -CH 3 Or -CH 2 CH 2 -OH, R 9 is hydrogen or -COOR 8 , p is the value 0, 1 or 2 R 2 can furthermore be a radical of one of the formulae (Xl), (XIa) or (XII) to (XX) or of the formula (XVIIIa) or (XXa) or (XXb) or (XXc),
  • A is a direct bond or a divalent radical of the formula
  • R 3 R 3 can be distributed arbitrarily over the chain, where R 12 is H or C 2 H 5 and where R 17 is R or is -R 4 -NH 2 or is
  • RF is a perfluoroalkyl radical having 5 to 23 carbon atoms.
  • R 3 is hydrogen or the methyl group
  • R 4 is a divalent linear or branched hydrocarbon radical having 1 to 4 carbon atoms
  • R 14 is hydrogen or a linear or branched alky! radical having 1 to 16 carbon atoms or a radical of the formula (XIX),
  • R 10 is a divalent radical of one of the formulae (XXI) to (XXIVa),
  • R" is H or — CH(CH 3 ) 2 or is -CH 2 -CH(CH 3 ) 2 ,
  • d is a number from 1 to 6, or is a radical of one of the formulae (XXV) to (XXXI),
  • z is in each case a number from 8 to 500, preferably from 8 to 20.
  • silanes or silane mixtures of the formula (I) which contain at least one silane of the formula (I) in which R 2 is a radical of the formula (V)
  • organosiloxanes are silanes of the formula (I) in which all of the radicals R, independently of one another, are CH 3 or -CH 2 -CH 3 and the radical R 2 is a radical of the formula (V).
  • the silanes of the formula (I) are commercially available products or can be prepared by methods which are known to the chemist. Possible syntheses are the reaction of a silane which contains an Si-H bond and 2 or 3 chlorine atoms bonded to Si with allyl compounds, e.g. with allyl chloride and subsequent further reaction with ammonia or an amine (where the terminal chlorine atom of the original allyl group is substituted by the corresponding nitrogen-containing radical), and subsequent substitution of the chlorine atoms bonded to Si by OR by means of reaction with alcohol.
  • Possible syntheses are the reaction of a silane which contains an Si-H bond and 2 or 3 chlorine atoms bonded to Si with allyl compounds, e.g. with allyl chloride and subsequent further reaction with ammonia or an amine (where the terminal chlorine atom of the original allyl group is substituted by the corresponding nitrogen-containing radical), and subsequent substitution of the chlorine atoms bonded to Si by OR by means of reaction with alcohol.
  • Silanes of the formula (I) in which the radical R 2 is a radical of the formula (V) can be prepared through reaction of (RO) 2 Si(R 1 )- R 4 — Cl with
  • silanes can be obtained from ABCR, Germany.
  • Silanes of the formula (I) in which the radical R 2 is a radical of the formula (Vl) can be obtained through reaction of (CI) 2 Si(R)-H with
  • Silanes of the formula (I) in which the radical R 2 is a radical of the formula (111) or of the formula (IV) can be obtained by addition of a lactone, e.g. ⁇ -butyrolactone, onto an aminoalkyi- dialkoxysilane and subsequent reaction with (meth)acrylic acid or derivatives thereof.
  • a lactone e.g. ⁇ -butyrolactone
  • Silanes of the formula (I) in which the radical R 2 is a radical of the formula (VII) can be prepared through addition of (meth)acrylic acid esters onto aminoalkyldialkoxysilane.
  • Silanes of the formula (I) used are preferably silanes in which the radical R 2 contains acrylate units or methacrylate units.
  • Such silanes are commercially available, e.g. from ABCR GmbH & Co., Düsseldorf, Germany. Furthermore, such silanes can be prepared in accordance with the teaching of DE-A 102 19 734.
  • Silanes in which the radical R 10 is a radical of one of the formulae (XVII), (XVIII) or (XX) can be obtained by reacting corresponding epoxides with corresponding amines.
  • Silanes of the formula (I) in which the radical R 2 contains acrylate units or methacrylate units are commercially available, e.g. from ABCR GmbH & Co., Düsseldorf, Germany. Furthermore, such silanes, e.g. of the formula (XVI), can be prepared by reacting
  • a catalyst or a mixture of catalysts is optionally co-used.
  • Suitable catalysts are basic or acidic catalysts, such as, for example, potassium hydroxide or mineral acids or catalysts which are specified below for the reaction of the silanes according to the invention with organosiloxane of the formula (VIlI).
  • the reaction of the silanes of the formula (I) or of the mixtures of such silanes with water can be carried out in the normal case at room temperature. However, if appropriate, it is also possible to work at a somewhat elevated temperature, preferably at a temperature which is somewhat higher than the boiling point of the alcohol ROH to be eliminated.
  • the reaction time can be a few minutes to several days depending on the type and amount of the starting compounds.
  • processing can be without use of an additional solvent.
  • Dimeric or oiigomeric silanes according to the invention can be used for the modification of carbon nanotubes or for the treatment of sheet materials made of polypropylene fibers or for the modification of epoxy resins.
  • Dimeric or oiigomeric silanes according to the invention or mixtures thereof are particularly well suited for the preparation of new types of polyorganosiloxanes.
  • These new types of polyorganosiloxanes are particularly well suited for the treatment or coating of fabrics and can be prepared through reaction of a dimeric and/or oiigomeric silane according to claim 1 or 2 or of a mixture of such silanes with an organosiloxane of the formula (VIII)
  • R 6 is a radical R of the specified meaning or is a radical of the formula (IX)
  • polyorganosiloxanes although for low values of x, they are oligoorganosiloxanes.
  • x is a number from 0 to 1500, preferably 10 to 1500, and y is a number from 0 to 500, also in the formulae (VIII) and (IX), all of the radicals R 7 present are R or OH or are a group OR, where R has the abovementioned meaning, where the organosiloxane of the formula (VIII) preferably contains at least one radical R 7 which is a hydroxy group.
  • the polyorganosiloxane and the dimeric or oiigomeric silane are preferably used in quantitative ratios such that 0.001 to 5 silicon atoms of the dimeric or oiigomeric silane are used per silicon atom of the polyorganosiloxane.
  • the polyorganosiloxanes of the formula (VII!) used for this reaction contain at least two radicals R 7 at the ends of the polysiloxane chain.
  • Each radical R 7 is a radical R of the abovementioned meaning or is a hydroxy group or a group -OR, where R has the abovementioned meaning.
  • At least one of the radicals R 7 present is an OH group.
  • the polyorganosiloxanes used for the reaction can also, although this is not expressed in formula (VIII), contain further functional groups in side chains, e.g. amino groups.
  • one or more of the radicals R 6 present are a radical with such a functional group.
  • further organosiloxanes can be co-used, e.g. low molecular weight oligodialkylsiloxanes.
  • a polyorganosiloxane of the formula (VIII) is used in which two of the radicals R 7 present are in each case an OH group, and that the reaction is carried out at a temperature in the range from 80 to 120 0 C.
  • one or more of the radicals R 7 present is an OH group
  • condensation reactions between these OH groups and OR groups of the dimeric or oligomeric silane can take place with elimination of alcohol ROH.
  • the reaction of the silanes of the formula (I) with polysiloxanes of the formula (VIII) is carried out such that a condensation takes place.
  • Suitable catalysts are, if appropriate, Lewis acids or dilute mineral acids.
  • basic catalysts such as alkali metal hydroxides or alkoxides, or the catalysts specified below.
  • polyorganosiloxanes of the formula (VIII) in which two of the radicals R 7 present are in each case an OH group are particularly well suited.
  • the specified polyorganosiloxanes containing hydroxy groups which are referred to below as " ⁇ , ⁇ -dihydroxypolyorganosiloxanes", are thus reacted with dimeric or oligomeric silanes according to the invention.
  • This reaction can, as explained in more detail below, be carried out in such a way that either an equilibration takes place during which structural units of the silanes are incorporated into the chain of the ⁇ , ⁇ -dihydroxypolyorganosiloxane. Or else, and this is preferred, the reaction is carried out in such a way that condensation reactions between terminal OH groups of the polysiloxane and the silanes take place.
  • the second variant namely condensation
  • the specified reactions give polyorganosiloxanes which contain units R 2 originating from the silanes.
  • 2 types of reaction mechanisms are conceivable, namely reaction control which leads to equilibration reactions, or reaction control which leads to condensation reactions. It is preferred to carry out the reaction so that only condensation takes place, but no equilibration.
  • the condensation proceeds at lower temperatures.
  • OR groups of the dimeric or oligomeric silanes react with terminal OH groups of the ⁇ . ⁇ -dihydroxypolysiloxane with the elimination of alcohol ROH and chain extension.
  • the reaction can be carried out as condensation at a temperature in the range from 80 to 105 0 C over 3 to 4 hours, preferably under reduced pressure, e.g. at a pressure in the region of 100 mbar. Details of condensation reactions are known from silicone chemistry. In order that condensation can take place at all, the polysiloxane used must have hydroxy groups on at least two chain ends.
  • the reaction which leads to new types of polyorganosiloxanes according to the invention is preferably carried out with co-use of a catalyst or of a mixture of catalysts, both in the case of the reaction in the form of a condensation and also in the form of an equilibration.
  • Suitable catalysts are known from the silicone literature.
  • acidic catalysts can be used, e.g. Lewis acids or dilute mineral acids; normally, however, basic catalysts are better suited and therefore preferred.
  • Highly suitable basic catalysts are alkali metal hydroxides, such as NaOH, KOH or LiOH and in particular metal alkoxides.
  • alkali metal alkoxides alkali metal alkoxides of the formula M(OR) are particularly well suited. These metal alkoxides can be used, for example, as 20 to 30% strength solution in the parent alcohol.
  • M is Na or K and R is an alkyl radical having 1 to 4 carbon atoms.
  • catalysts are 4-dimethylaminopyridine and bicyclic compounds which contain one or more nitrogen atoms as ring members. Examples are 1 ,5-diazabicyclo[2.2.2.]octane, 1 ,5- diazabicyclo[4.3.0]non-5-ene and 1 ,8-diazabicyclo[5.4.0]undec-7-ene. These catalysts are also suitable for the reaction of the silanes of the formula (I) with water.
  • polyorganosiloxanes according to the invention which can be prepared by reacting the dimeric or oligomeric silanes according to the invention with polyorganosiloxanes of the formula (VIII) can be used well inter alia for the treatment of fabrics made of fiber materials.
  • Suitable fiber materials here are wovens, knits or nonwovens made of natural or synthetic fibers, such as, for example, made of cotton, polyester, polypropylene or polyamide or mixtures of such fibers, where in the case of polypropylene a plasma pretreatment may be connected upstream.
  • the application can take place, for example, by means of padding processes or spraying. If appropriate, the application takes place in the form of a coating.
  • the new type of polyorganosiloxanes according to the invention are also highly suitable for the methods of curtain coating known to the person skilled in the art. If the radical R 2 present in the silanes of the formula (I) has (meth)acrylate units, the curtain coating can be followed by a curing operation in which the acrylate units are polymerized.
  • the new type of polysiloxanes according to the invention can also be used for the finishing of precursor fibers, e.g. acrylic fibers, in the manufacture of carbon fibers. Furthermore, they can be used for the modification of epoxy resins for highly diverse application purposes.
  • Example 1 (according to the invention): Preparation of a dimeric disilane
  • x had a value of about 2.5.
  • the acrylic acid ester used was a mixture of decyl acrylate and octyl acrylate.
  • Example 5 (according to the invention) 8.5 g of water were added dropwise to 91 g of (C 2 H 5 O) 2 Si(CH3)-CH2CH 2 CH 2 -NH 2 over the course of 30 min. Then, the mixture was heated to 45 0 C and stirred for 2 hours at this temperature.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Silicon Polymers (AREA)

Abstract

L'invention concerne des silanes dimères et/ou oligomères et leurs produits de réaction avec des organosiloxanes. Les silanes dimères ou oligomères ou leurs mélanges peuvent être préparés par réaction de silanes qui contiennent 2 ou 3 groupes OR avec de l'eau. La poursuite de la réaction de ces silanes diméres et/ou oligomères avec des organosiloxanes conduit à des polysiloxanes ayant des groupes fonctionnels. Les polysiloxanes qui se forment sont appropriés entre autres pour l'enduction de tissus.
PCT/EP2007/008413 2006-09-28 2007-09-27 Silanes dimères et oligomères et leurs produits de réaction avec des organosiloxanes WO2008037468A2 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP06020359.3 2006-09-28
EP06020359A EP1905794A1 (fr) 2006-09-28 2006-09-28 Siloxanes dimériques et oligomériques et leurs produits de réaction avec des organosiloxanes
EP07018238.1 2007-09-18
EP07018238A EP2039717A1 (fr) 2007-09-18 2007-09-18 Silanes dimères et oligomères et leurs produits de transformation à l'aide d'organosiloxanes

Publications (2)

Publication Number Publication Date
WO2008037468A2 true WO2008037468A2 (fr) 2008-04-03
WO2008037468A3 WO2008037468A3 (fr) 2008-06-05

Family

ID=38962649

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2007/008413 WO2008037468A2 (fr) 2006-09-28 2007-09-27 Silanes dimères et oligomères et leurs produits de réaction avec des organosiloxanes

Country Status (1)

Country Link
WO (1) WO2008037468A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111116632A (zh) * 2018-11-01 2020-05-08 中国石油化工股份有限公司 一种钻井液用胺基成膜抑制剂及制备方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5282998A (en) * 1991-06-08 1994-02-01 Huls Aktiengesellschaft Mixtures of linear and cyclic siloxanes or siloxane oligomers and a process for their preparation
US5576408A (en) * 1994-08-25 1996-11-19 Shin-Etsu Chemical Co., Ltd. Process for preparing low molecular weight organosiloxane terminated with silanol group
US6015858A (en) * 1998-09-08 2000-01-18 Dow Corning Corporation Thermoplastic silicone elastomers based on fluorocarbon resin
US6586535B1 (en) * 2000-06-22 2003-07-01 Dow Corning Corporation Coatings containing silicone mist suppressant compositions
US20050282977A1 (en) * 2004-06-17 2005-12-22 Emil Stempel Cross-linked gel and pressure sensitive adhesive blend, and skin-attachable products using the same

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5282998A (en) * 1991-06-08 1994-02-01 Huls Aktiengesellschaft Mixtures of linear and cyclic siloxanes or siloxane oligomers and a process for their preparation
US5576408A (en) * 1994-08-25 1996-11-19 Shin-Etsu Chemical Co., Ltd. Process for preparing low molecular weight organosiloxane terminated with silanol group
US6015858A (en) * 1998-09-08 2000-01-18 Dow Corning Corporation Thermoplastic silicone elastomers based on fluorocarbon resin
US6586535B1 (en) * 2000-06-22 2003-07-01 Dow Corning Corporation Coatings containing silicone mist suppressant compositions
US20050282977A1 (en) * 2004-06-17 2005-12-22 Emil Stempel Cross-linked gel and pressure sensitive adhesive blend, and skin-attachable products using the same

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111116632A (zh) * 2018-11-01 2020-05-08 中国石油化工股份有限公司 一种钻井液用胺基成膜抑制剂及制备方法
CN111116632B (zh) * 2018-11-01 2022-11-29 中国石油化工股份有限公司 一种钻井液用胺基成膜抑制剂及制备方法

Also Published As

Publication number Publication date
WO2008037468A3 (fr) 2008-06-05

Similar Documents

Publication Publication Date Title
US9273072B2 (en) Method for producing organosilicon compounds which have amino groups
EP2252621B1 (fr) Silanes et polysiloxanes
CN111133035B (zh) 包含草酰胺基酯基团的硅氧烷的制备方法
US5118777A (en) Polydimethylsiloxane terminated at one end by a branched aminoalkyl group and preparation thereof
EP3594220B1 (fr) Composé silicium organique, et procédé de fabrication de celui-ci
CN107849068B (zh) 用于制备多面体低聚倍半硅氧烷的方法
EP0130731A2 (fr) Siloxanes méthacrylés
JPH0242089A (ja) オルガノシロキサン化合物
EP3594261B1 (fr) Composé silicium organique comprenant un groupe polyoxyalkylène, et procédé de fabrication de celui-ci
US5256754A (en) Hydrogenpolysiloxanes and methods of making
EP1622964A1 (fr) Melanges de siloxane organofonctionnels
JP6214625B2 (ja) 新規の、簡単に製造可能な、ｖｏｃ還元された、環境保護性の（メタ）アクリルアミド官能性シロキサン系、その製造法ならびに前記シロキサン系の使用
EP1856192B1 (fr) Polysiloxanes de groupements acrylatoyles
WO2008037468A2 (fr) Silanes dimères et oligomères et leurs produits de réaction avec des organosiloxanes
EP0484120B1 (fr) Polysiloxanes ayant des atomes d'hydrogène liés à l'atome de silicium et procédé pour leur préparation
US20080312398A1 (en) Enamine Oils and Method for The Production Thereof
JP2015110527A (ja) オキセタン環を有する有機珪素化合物及びその製造方法
CN114539535B (zh) 一种含酰胺基单组份室温固化弹塑性硅树脂及其制备方法
JP2024516976A (ja) ポリマーアルキルシリケートの混合物
WO2019239782A1 (fr) Procédé de production d'organopolysiloxane à fonction éther vinylique, composition polymérisable et produit durci obtenu à partir de celle-ci
KR20040078455A (ko) 알콕시 실란의 공가수분해에 의한 발수성 알콕시 실록산올리고머의 제조방법

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: 07818496

Country of ref document: EP

Kind code of ref document: A2

NENP Non-entry into the national phase in:

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 07818496

Country of ref document: EP

Kind code of ref document: A2