EP1791892A1 - Organopolysiloxanes presentant de l'azote et leur utilisation dans des matieres reticulables - Google Patents

Organopolysiloxanes presentant de l'azote et leur utilisation dans des matieres reticulables

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Publication number
EP1791892A1
EP1791892A1 EP05788590A EP05788590A EP1791892A1 EP 1791892 A1 EP1791892 A1 EP 1791892A1 EP 05788590 A EP05788590 A EP 05788590A EP 05788590 A EP05788590 A EP 05788590A EP 1791892 A1 EP1791892 A1 EP 1791892A1
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EP
European Patent Office
Prior art keywords
formula
units
different
sir
optionally
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.)
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Application number
EP05788590A
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German (de)
English (en)
Inventor
Uwe Scheim
Ernst Selbertinger
Wolfgang Ziche
Christian Ochs
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Wacker Chemie AG
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Wacker Chemie AG
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Publication of EP1791892A1 publication Critical patent/EP1791892A1/fr
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    • 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
    • C08G77/48—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
    • C08G77/54—Nitrogen-containing linkages
    • 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
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
    • 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
    • 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
    • C08L83/14—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms

Definitions

  • the invention relates to nitrogen-containing organopolysiloxanes, their preparation and their use in crosslinkable compositions.
  • Nitrogen-containing organopolysiloxanes are already known.
  • US-A 2,567,131 there are e.g. describe cyclic and linear oligomers and polymers which consist exclusively of Si-C-N-C-Si-O repeat units.
  • the invention relates to organopolysiloxanes containing at least one unit (a) selected from units (a1) of the formula
  • R may be identical or different and represents a monovalent, SiC-bonded, optionally substituted hydrocarbon radical
  • Each R 1 may be the same or different and is a monovalent organic radical or a hydrogen atom
  • each R 2 may be the same or different and is a monovalent organic radical or a hydrogen atom
  • Each R 3 may be the same or different and is a monovalent organic radical or hydrogen atom
  • R 4 may be identical or different and is hydrogen or monovalent, optionally substituted hydrocarbon radicals,
  • R 5 may be identical or different and represents monohydric hydrolyzable organic radicals bound via oxygen atom or nitrogen atom on silicon atom, n is 2 or 3, a is an integer from 1 to 6, preferably 1 to 3, particularly preferably 1, b is an integer from 1 to ⁇ , preferably 1 to 3, particularly preferably 1, is and
  • X ⁇ may be identical or different and represents an organic or inorganic anion, with the proviso that with organopolysiloxanes which contain no unit of the formula (VIII), in addition at least one unit of the formula (II) is present and in Organopolysiloxa ⁇ NEN, which contain no unit of formula (I), additionally at least one unit selected from units of the formula (III) and the formula (IV) is present.
  • organopolysiloxanes is intended to encompass both polymeric, oligomeric and dimeric siloxanes.
  • radicals R are alkyl radicals, such as the methyl, ethyl, n-propyl, iso-propyl, n-butyl, s-butyl, isobutyl, tert-butyl, n-pentyl iso-pentyl, neo-pentyl, tert-pentyl; Hexyl radicals, such as the n-hexyl radical; Heptyl radicals, such as the n-heptyl radical; Octyl radicals, such as the n-octyl radical and iso-octyl radicals, such as the 2, 2, 4-trimethylpentyl radical; Nonyl radicals, such as the n-nonyl radical; Decyl radicals, such as the n-decyl radical; Dodecyl radicals, such as the n-dodecyl radical; Octadecyl radicals, such as the n-d
  • substituted radicals R are methoxyethyl, ethoxyethyl, (2-ethoxy) ethoxyethyl, 3-chloropropyl, 2-chloroethyl, chloromethyl and the 3, 3, 3-trifluoropropyl.
  • Radicals R are preferably hydrocarbon radicals having 1 to 12 carbon atoms which are optionally substituted by halogen atoms, amino groups, ether groups, ester groups, epoxy groups, mercapto groups, cyano groups or (poly) glycol radicals, the latter being selected from oxyethylene and / or or oxypropylene units are constructed, more preferably alkyl radicals having 1 to 6 carbon atoms, in particular the methyl radical.
  • radicals R 1 are the examples given for radical R and hydrogen atom.
  • Radical R 1 is preferably hydrogen and optionally substituted hydrocarbon radicals, more preferably hydrogen and alkyl radicals having from 1 to 6 carbon atoms, in particular hydrogen.
  • radicals R 2 are the examples given for radical R and hydrogen atom.
  • Radical R 2 is preferably hydrogen atom and optionally substituted hydrocarbon radicals, more preferably hydrogen atom and alkyl radicals having 1 to 6 carbon atoms, in particular hydrogen atom.
  • radicals R 3 are the examples given for radical R and also the hydrogen atom.
  • the radical R 3 is preferably unsubstituted hydrocarbon radicals, particularly preferably alkyl radicals. radicals having from 1 to 20 carbon atoms, in particular the methyl radical.
  • radicals R 4 are the examples given for radical R.
  • Radical R 4 is preferably hydrogen atom and also alkyl radicals having 1 to 6 carbon atoms, hydrogen atom, methyl or ethyl radical being particularly preferred, in particular hydrogen atom.
  • radicals R 5 are all known cash hydrolyzable radicals such as hydrogen radicals bound to silicon atom via oxygen atom or nitrogen atom, optionally substituted hydrocarbons.
  • the radical R 5 is preferably alkoxy radicals, such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, tert-butoxy and 2-methoxyethoxy radical, acyloxy radicals, such as the acetoxy radical, amino radicals, such as methylamino, dimethylamino, ethylamino, diethylamino and cyclohexylamino radicals, amido radicals, such as N-methylacetamido and benzamido radicals, aminooxy radicals, such as diethylaminoxy radical, oxime radicals, such as Metylethylketoximo- and Methylisobutylketoximorest, and Enoxyreste, such as the 2-propenoxy, particularly preferably the methoxy, ethoxy, acetoxy, Methylethylketoximo-, Methylis
  • anion X " are organic anions, such as carboxylate ions, enolations and sulfonate ions, and also inorganic anions, such as halide ions, such as fluoride ions, chloride ions, bromide ions and iodide ions, and sulfate ions.
  • Anion X " is preferably carboxyl ions, sulfonations and halide ions, more preferably chlorides and acetate ions.
  • n is equal to 2.
  • the siloxanes of the invention are preferably liquid and have a viscosity of preferably 10 2 mPas to 10 8 mPas at 25 ° C.
  • the nitrogen-containing organopolysiloxanes according to the invention are preferably those which have no units of the formula (VIII) (siloxanes of type A), such as siloxanes, the units of the formulas (I) and (II) and if appropriate, units of the formulas (III) to (VI) or those containing units of the formula (VIII) (siloxanes type B), such as siloxanes, the units of the formula (VIII) and, where appropriate, units of the formulas ( I) to (VI), wherein in the case of type B siloxanes which do not contain a unit of the formula (I), at least one unit of the formula (III) and / or of the formula (IV) is present.
  • siloxanes of type A such as siloxanes, the units of the formulas (I) and (II) and if appropriate, units of the formulas (III) to (VI) or those containing units of the formula (VIII) (siloxanes type B), such as silox
  • siloxanes of the type A according to the invention are preferably those of the formula
  • E may be the same or different and is as defined for R 4 or a radical meanings (R 5) n n -SiR3- - means may be the same or different and o is 0 or an integer from 1 to 3000, preferably 10 to 2000 , q is 0 or an integer from 1 to 3000, preferably 10 to 2000, p may be the same or different and is an integer from 1 to 20, preferably 1 to 5, particularly preferably 1, and r is one integer from 1 to 20's as well
  • R, R 1 , R 2 and n have the meaning given above, with the proviso that the sum o + q is greater than or equal to 1, preferably 10 to 2000.
  • the siloxanes of the invention have the type A has a viscosity of preferably 10 5 to 10 8 mPas at 25 0 C.
  • Examples of the type B siloxanes according to the invention are HO [(SiMe 2 O) 30-1000 (SiMe 2 CH 2 Me 2 N + Cl-CH 2 SiMe 2 O) x _ 2 ] 1-5 (SiMe 2 O) 30 1000H,
  • the siloxanes of the type B according to the invention are preferably essentially linear siloxanes, particularly preferably essentially linear siloxanes comprising at least one unit of the formula (VIII), at least one unit of the formula (III) and optionally units of the formulas (II), (IV), (V) and (VI), particularly those of the formula HO [(SiMe 2 O) 0-30 (SiMe 2 CH 2 (H 3 C) 2 N + Cl ⁇ CH 2 SiMe 2 0) 1-2] 1-20 (SiMe 2 O) 0-30H, where Me is equal to methyl radical.
  • the type B siloxanes of the invention have a viscosity of preferably from 10 2 to 5-10 7 mPas at 25 ° C.
  • the organopolysiloxanes according to the invention have the advantage that they can be used for the preparation of crosslinkable compositions, in particular of particularly low-modulus RTVl compositions, without it being necessary to prepare very highly viscous polymers separately.
  • the organopolysiloxanes of the type B according to the invention have the advantage that they allow formulations having permanent biostatic properties.
  • the nitrogen-containing organopolysiloxanes according to the invention can now be prepared by any method known per se in silicon chemistry, for example by hydrolysis and condensation of organosilicon compounds.
  • siloxanes according to the invention are preferably prepared by reacting OH-terminated polydiorganosiloxanes with organosilicon compounds of the formulas
  • R, R 1 , R 2 , R 3 , R 4 , R 5 , X, a, b and n have one of the meanings given above.
  • the siloxanes of the type A according to the invention are preferably prepared by reacting OH-terminated polydiorganosiloxanes with silanes of the formula (IX) and, if appropriate, (XI).
  • the siloxanes of the type B according to the invention can be prepared by reacting OH-terminated polydiorganosiloxanes with silanes of the formula (X) and, if appropriate, (XI) and, if appropriate, (XII).
  • siloxanes of the type B according to the invention are preferably prepared by reacting OH-terminated polydiorganosiloxanes with silanes of the formula (IX) and, if appropriate, (XI) and then quaternizing the basic nitrogen.
  • the inventive method is Trains t at temperatures of Credit ⁇ 0 to 100 0 C, particularly preferably 20 to 80 0 C, and Cards ⁇ Trains t at a pressure of the surrounding atmosphere, at about 900 to 1100 hPa.
  • the inventive method can also be carried out at higher or lower pressures.
  • the molar ratio of the OH groups in the OH-terminated polydiorganosiloxanes used to the organosilicon compounds of the formula (IX) is preferably 40: 1 to 1:10. At a molar ratio of between 40: 1 and greater than 4: 1, such OH excess is mathematically present that only a portion of the OH-terminated polydiorganosiloxane used with the organosilicon compound of the formula (IX) becomes siloxanes of the type A Rea ⁇ can ferment while leaving a portion of the OH-terminated polydiorganosiloxane used unreacted.
  • the molar ratio of the OH groups in the OH-terminated polydiorganosiloxanes used to the silane of the formula (XI) is preferably 1: 1 to 1: 100, more preferably 1:10 to 1:50.
  • the reaction according to the invention of the OH-terminated polydiorganosiloxane used with the organosilicon compound of the formula (IX) and optionally other organosilicon compounds can be carried out both in substance and in solvents. Suitable solvents are those which do not interfere with the reaction of the components.
  • optionally used solvents are trimethylsilyl-terminated polydimethylsiloxanes, such as those having a viscosity of from 5 to 1000 mPas at 25 ° C., and hydrocarbons having from about 16 to 30 carbon atoms.
  • the process according to the invention is preferably carried out in the absence of solvents, unless they are chosen so that they do not have to be removed after the reaction has taken place.
  • the reaction according to the invention of the OH-terminated polydiorganosiloxane used with the organosilicon compound of the formula (IX) and, if appropriate, further organosilicon compounds generally requires no catalyst, which is very advantageous.
  • the use of a catalyst may be advantageous, in particular when silanes of the formula (XI) where R 5 is organo-yxxy.
  • end-capping has been previously described in numerous ways.
  • catalysts which may be used in the process according to the invention are Bronsted or Lewis acids or bases such as zinc acetylacetonate, titanium chelates, acidic phosphoric esters, amines, oximes, acetic acid, formic acid, ammonium salts such as dibutylammonium formate, lithium hydroxide, fluorides and many others ,
  • the silanes used in the process according to the invention are commercially available products or can be prepared by methods customary in organosilicon chemistry.
  • the method according to the invention has the advantage that it is easy to perform and can be carried out immediately prior to the further use of the nitrogen-containing siloxanes in the 'particular for further processing containers.
  • organopolysiloxanes according to the invention can now be used for all purposes for which organopolysiloxanes could hitherto also be used.
  • they are suitable for the preparation of crosslinkable compositions.
  • organopolysiloxanes (i) tend at least one unit (a) selected from units (al) of the formula
  • Each R may be the same or different and represents a monovalent, SiC-bonded, optionally substituted hydrocarbon radical,
  • Each R 1 may be the same or different and is monovalent or ⁇ ganische radicals or hydrogen atom,
  • Each R 2 may be the same or different and is monovalent or ⁇ ganische radicals or hydrogen atom
  • R 3 may each be the same or different and is monovalent or ⁇ ganische radicals or hydrogen atom
  • R 4 may be identical or different and is hydrogen or monovalent, optionally substituted hydrocarbon radicals, each R 5 may be the same or different and is monohydric O over oxygen atom or nitrogen atom bound to silicon atom hydrolyzable organic radicals, n is 2 or 3, a an integer from 1 to 6, preferably 1 to 3, particularly preferably 1, is, b is an integer from 1 to 6, preferably 1 to 3, particularly preferably 1, and
  • X - may be the same or different and represents an organic or inorganic anion.
  • crosslinkable compositions according to the invention are preferably compositions crosslinkable by condensation reaction.
  • crosslinkable compositions comprising (i) organopolysiloxanes having nitrogen, optionally (ii) crosslinking agents, possibly
  • crosslinkable compositions according to the invention are preferably one-component compositions.
  • the components used in each case can be mixed with one another in any desired and hitherto known manner. This mixing is preferably carried out at room temperature or at a temperature which occurs when the components are added together at room temperature without additional heating or cooling, and the pressure of the surrounding atmosphere, ie about 900 to 1100 hPa. If desired, this can be However, mixing also occurs at higher or lower pressures, for example at low pressures to avoid gas inclusions.
  • compositions according to the invention and their storage are preferably carried out under essentially anhydrous conditions in order to avoid premature reaction of the compositions.
  • crosslinkers (ii) it is possible to use all crosslinkers which have hitherto been used in compositions which can be crosslinked by condensation.
  • crosslinker (ii) organyloxysilanes and also their partial hydrolysates, such as, for example, tetraethoxysilane, tetraisopropoxysilane, tetra-n-propoxysilane, methyltrimethoxysilane, methyltriethoxysilane, n-butyltrimethoxysilane, n-octyltrimethoxysilane, i-octyltrimethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane , Methyltriacetoxysilane, ethyltriacetoxysilane, so ⁇ as methyl and Vinylketoximosilane and their Generalhydrolysa ⁇ te, with methyl and vinyltrimeth
  • crosslinkable compositions according to the invention contain crosslinkers (ii), these are amounts of preferably 0.05 to 10 parts by weight, more preferably 0.2 to 5 parts by weight, based in each case on 100 parts by weight of crosslinkable composition.
  • catalysts (iii) it is possible to use all condensation catalysts known to the person skilled in the art.
  • condensation catalysts (iii) are butyl titanates and organic tin compounds, such as di-n-butyltin dilaurate and di-n-butyltin diacetate, and also reaction products thereof with the alkoxysilanes called crosslinkers or adhesion promoters, dialkyltin oxide solutions in the crosslinking agent or Adhesion promoters mentioned alkoxysilanes, with di-n-butyltin dilaurate and dibutyltin oxide in tetraethoxysilane hydrolyzate preferred and dibutyltin oxide in tetraethoxysilane hydrolyzate is particularly preferred.
  • organic tin compounds such as di-n-butyltin dilaurate and di-n-butyltin diacetate
  • crosslinkable compositions according to the invention comprise catalyst (ii), these are amounts of preferably 0.01 to 3 parts by weight, preferably 0.05 to 2 parts by weight, in each case based on 100 parts by weight of crosslinkable composition.
  • fillers (iv) all fillers can be used, which have also been used in crosslinkable compositions.
  • fillers are reinforcing fillers, ie fillers having a BET surface area of at least 30 m 2 / g, such as, for example, carbon blacks, fumed silica, precipitated silica and silicon-aluminum mixed oxides, where the fillers mentioned may be hydrophobic , as well as non-reinforcing fillers, ie fillers having a BET surface area of less than 30 ru 2 / g, such as, for example, powders of quartz, cristobalite, diatomaceous earth, calcium silicate, zirconium silicate, montmorillonites, such as benzonites, zeolites, including molecular sieves, such as Natri ⁇ umumuminiumsilikat, metal oxides such as aluminum or zinc oxide or their mixed oxides, metal hydroxides such as aluminum hydroxide, barium sulfate, calcium carbonate, gypsum, silicon nitride, silicon carbide, boron nitride,
  • Filler (iv) is preferably pyrogenic silica or calcium carbonate or mixtures thereof, pyrogenic silica having a BET surface area of 150 m 2 / g and calcium carbonate having BET surface areas of from 1 to 40 m 2 / g are particularly preferred.
  • compositions according to the invention comprise fillers (iv), these are amounts of preferably 1 to 50 parts by weight, preferably 2 to 30 parts by weight, in each case based on 100 parts by weight of crosslinkable composition.
  • adhesion promoter (s) optionally used it is possible to use all adhesion promoters which have hitherto been used in compositions crosslinkable by condensation.
  • adhesion promoters (v) are silanes with hydrolyzable groups and SiC-bonded vinyl, acryloxy, methacryloxy, epoxy, acid anhydride, acid, ester or ether groups and their partial and mixed hydrolyzate.
  • Preferred adhesion promoters (v) used are 3-aminopropyltriethoxysilane, 3- (2-aminoethyl) aminopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane and 3- (2-aminoethyl) aminopropyltriethoxysilane, with 3-aminopropyltriethoxysilane being particularly preferred.
  • compositions according to the invention contain adhesion promoters (v), these are amounts of preferably 0.01 to 5 parts by weight, preferably 0.5 to 4 parts by weight, in each case based on 100 parts by weight of crosslinkable composition.
  • plasticizers such as trimethylsilyl-terminated polydimethylsiloxanes and hydrocarbons having about 16 to 30 carbon atoms
  • stabilizers such as 2-ethylhexyl phosphate, octylphosphonic acid, polyethers, antioxidants, flame retardants, such as phosphoric acid esters, light stabilizers and Pigments, such as titanium dioxide, iron oxides.
  • the optionally used further substances (vi) are preferably plasticizers, such as trimethylsilyl-terminated polydimethylsiloxanes and hydrocarbons having about 16 to 30 carbon atoms, stabilizers, such as 2-ethylhexyl phosphate, octylphosphonic acid, polyethers, flame retardants, such as phosphoric acid esters and pigments, such as titanium dioxide, iron oxides, wherein plasticizers and stabilizers are particularly preferred.
  • plasticizers such as trimethylsilyl-terminated polydimethylsiloxanes and hydrocarbons having about 16 to 30 carbon atoms
  • stabilizers such as 2-ethylhexyl phosphate, octylphosphonic acid, polyethers
  • flame retardants such as phosphoric acid esters and pigments, such as titanium dioxide, iron oxides, wherein plasticizers and stabilizers are particularly preferred.
  • component (vi) amounts of preferably 0.01 to 30 parts by weight, especially preferred kart 0.05 to 25 parts by weight, in each case based on 100 parts by weight crosslinkable mass.
  • crosslinkable compositions according to the invention can contain crosslinkable polymers (vii), such as organopolysiloxanes having reactive end groups.
  • crosslinkable siloxanes are ⁇ , ⁇ -dihydroxypolydimethylsiloxanes and ⁇ , ⁇ -bis (dimethoxymethylsilyl) -terminated polydimethylsiloxanes.
  • the component (vii) optionally used in the crosslinkable compositions according to the invention is preferably polydiorganosiloxanes having at least one OH group or a hydrolyzable group at the chain ends, more preferably polydimethylsiloxanes having at least one OH group or a hydrolyzable group at the chain ends, in particular by oc, ⁇ -dihydroxypolydimethylsiloxanes or ⁇ , ⁇ -bis (di-methoxymethylsilyl) terminated polydimethylsiloxanes having a viscosity of 100 to 500,000 mPas.
  • the crosslinkable compositions according to the invention preferably contain component (vii).
  • This component is preferably used for adjusting the processing properties, such as, for example, viscosity, skinning time or pot life.
  • component (vii) are amounts of preferably 1 to 50 parts by weight, more preferably 2 to 25 parts by weight, in each case based on 100 parts by weight of crosslinkable composition.
  • compositions according to the invention may in each case be one type of such constituent as well as a mixture of at least two different types of such constituents.
  • compositions according to the invention contain no further constituents apart from component (i), if appropriate (ii), (iii), (iv), (v), (vi) and (vii).
  • the preparation of the crosslinkable compositions according to the invention is carried out by methods which are known to the person skilled in the art, for example by means of extruders, kneaders, roll mills, dynamic or static mixers.
  • the preparation of the compositions according to the invention can be carried out continuously or batchwise. Preferably, the preparation is carried out continuously.
  • the usual water content of the air is preferably sufficient.
  • the crosslinking of the compositions according to the invention is preferably carried out at room temperature. It can, if desired, also at higher orene ⁇ ren temperatures than room temperature, such as at -5 to 15 ° C or at 30 to 5O 0 C, for example, also by means of the normal water content of the air over increasing concentrations be carried out by water.
  • the crosslinking is carried out at a pressure of 100 to 1100 hPa, in particular at the pressure of the surrounding atmosphere, that is about 900 to 1100 hPa.
  • a further subject of the present invention are molded articles produced by crosslinking of the compositions according to the invention.
  • compositions of the invention have the advantage that they are easy to prepare and easy to handle during processing.
  • compositions of the invention have the advantage that they have a high storage stability.
  • compositions according to the invention, for the preparation of which inventive siloxanes of type A have been used have the advantage that they can be used to produce moldings having a particularly low stress at 100% elongation without having to handle very high-viscosity polymers.
  • compositions according to the invention for the production of which inventive siloxanes of type A have been used, furthermore have the advantage that they can be used to produce moldings having a particularly low stress at 100% elongation without having to handle very high-viscosity masses.
  • compositions according to the invention which have been prepared using silicoxanes of the type B according to the invention, have the advantage that moldings having a particularly low stress at 100% elongation can be produced therefrom, which moreover have permanent biostatic properties, e.g. Over a long period of time, the moldings are prevented from being destroyed by microorganisms.
  • Me is methyl and Vi is vinyl.
  • the crosslinkable mass thus obtained was filled into moisture-tight containers.
  • composition specimens were prepared, in ⁇ which the composition was applied lyethylen than 2 mm thick layer on a backing of polyvinyl and then 7 days at 50% re ⁇ lative humidity and was allowed to crosslink 23 0 C. Subsequently, test specimens of the form S2 measured in accordance with DIN 53504 were punched out of these plates.
  • Example 1 The experiment of Example 1 was repeated, omitting the 0.5 g of bis (methoxydimethylsilylmethyl) amine. Using the thus obtained composition specimens were prepared, in ⁇ which the composition was applied lyethylen than 2 mm thick layer on a backing of polyvinyl and then 7 days at 50% re- lative humidity and was allowed to crosslink 23 0 C. Subsequently, specimens of the form S2 according to DIN 53504 were punched out of these plates.
  • a tin catalyst obtainable by reacting 4 parts of tetraethoxysilane with 2.2 parts of dibutyltin diacetate, added added.
  • the crosslinkable mass thus obtained was filled into moisture-tight containers.
  • composition specimens were prepared, in ⁇ which the composition was applied lyethylen than 2 mm thick layer on a backing of polyvinyl and then 7 days at 50% re- lative humidity and was allowed to crosslink 23 0 C. Subsequently, specimens of the form S2 according to DIN 53504 were punched out of these plates.
  • composition specimens were prepared, in- which the composition was applied lyethylen than 2 mm thick layer on a backing of polyvinyl and then 7 days at 50% re ⁇ lative humidity and was allowed to crosslink 23 0 C. Subsequently, specimens of the form S2 according to DIN 53504 were punched out of these plates.
  • a mixture of a type A siloxane with the formula MeOSiMe 2 CH 2 NHCH 2 SiMe 2 O [(SiMe 2 O) 3 o] was then formed.
  • the crosslinkable mass thus obtained was filled into moisture-tight containers.
  • composition specimens were prepared, in ⁇ which the composition was applied lyethylen than 2 mm thick layer on a backing of polyvinyl and then 7 days at 50% re ⁇ lative humidity and was allowed to crosslink 23 0 C. Subsequently, specimens of the form S2 according to DIN 53504 were punched out of these plates.
  • a mixture of 294 g of an ⁇ , ⁇ -dihydroxypolydimethylsiloxane having a viscosity of 80,000 mPas (available from Wacker Chemie GmbH, Germany under the name "Polymer FD 80 "), 105 g of an ⁇ , ⁇ -bis (trimethylsiloxy) polydimethylsiloxane having a viscosity of 1000 mPas (available from Wacker-Chemie GmbH, Germany under the name” Plasticizer 1000 ”) and 61 g of an aliphatic hydrocarbon mixture (commercially available under the name "Hydroseal G400H” at TotalFinaElf Germany GmbH) was mixed with 0.2 g of bis (methoxy-dimethylsilylmethyl) amine, dissolved in 1.8 g of the above aliphatic hydrocarbon mixture.
  • a mixture of a type A siloxane with the formula HO [(SiMe 2 O) 30-1000 (SiMe 2 CH 2 NHCH 2 SiMe 2 O) x - 2 ] i-5 (SiMe 2 O) was formed here. 3 ooooH.
  • the ⁇ se polymer mixture was then added 20.0 g of E- thyltriacetoxysilan and 1.84 g of di-tert-butyldiacetoxysilan and mixed for 5 minutes.
  • a polymer of the formula (MeCOO) 2 EtSiO [(SiMe 2 O) 30-1000 (SiMe 2 CH 2 NHCH 2 SiMe 2 O) i_ 2 ] 1-5 (SiMe 2 O) 30 was formed from the abovementioned polymer. 1 00 0SiEt (OOCMe) 2 .
  • 42.0 g of fumed silica with a specific surface area of 150 m 2 / g available from Wacker-Chemie GmbH, Germany under the name HDK® V15
  • dibutyltin diacetate were added and homogeneous for 10 minutes mixed.
  • the mixture was mixed at a pressure of about 100 mbar for a further 15 minutes.
  • the crosslinkable composition thus obtained was filled into moisture-tight containers.
  • composition specimens were prepared, in ⁇ which the composition was applied lyethylen than 2 mm thick layer on a backing of polyvinyl and then 7 days at 50% re ⁇ lative humidity and was allowed to crosslink 23 0 C. Subsequently, test specimens of the form S2 measured in accordance with DIN 53504 were punched out of these plates. The test specimens thus prepared were examined with regard to their mechanical values. The results can be found in Table 1.
  • 35 g of the polyquaternary polysiloxane thus prepared 1400 g of a dihydroxypolydimethylsiloxane having a viscosity of 80,000 mPas, 600 g of a polydimethylsiloxane having -OSi (CH 3 ) 3 end groups and a viscosity of 100 mPas, 90 g of ethyltriacetoxysilane and 190 g of a pyrogenic hydrophilic Kie ⁇ selklare with a specific surface area of 150 m 2 / g was in a planetary mixer homogeneously mixed in a vacuum. Subsequently, 0.5 g of dibutyltin diacetate was added and homogenized again for 5 minutes.
  • Test specimens according to DIN EN ISO 846 were prepared from the vulcanizate sheets produced in this way and tested according to Method B as described in the standard. There was no or only slight growth (stage 0 or 1).

Abstract

L'invention concerne des organopolysiloxanes présentant de l'azote, qui contiennent au moins une unité (a) sélectionnée parmi des unités (a1) de formule (I) et des unités (a2) de formule (VIII), éventuellement des unités de formule (II), éventuellement des unités de formule (III), éventuellement des unités de formule (IV), éventuellement des unités de formule (V) et éventuellement des unités de formule (VI). Les restes et les indices ont la signification mentionnée dans la revendication 1. L'invention concerne également leur production et leur utilisation dans des matières réticulables.
EP05788590A 2004-09-23 2005-09-14 Organopolysiloxanes presentant de l'azote et leur utilisation dans des matieres reticulables Withdrawn EP1791892A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004046180A DE102004046180A1 (de) 2004-09-23 2004-09-23 Stickstoff aufweisende Organopolysiloxane und deren Verwendung in vernetzbaren Massen
PCT/EP2005/009879 WO2006032396A1 (fr) 2004-09-23 2005-09-14 Organopolysiloxanes presentant de l'azote et leur utilisation dans des matieres reticulables

Publications (1)

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EP1791892A1 true EP1791892A1 (fr) 2007-06-06

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US (1) US20070249782A1 (fr)
EP (1) EP1791892A1 (fr)
JP (1) JP2008513589A (fr)
KR (1) KR20070046190A (fr)
CN (1) CN101027342A (fr)
DE (1) DE102004046180A1 (fr)
WO (1) WO2006032396A1 (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102006016753A1 (de) * 2006-04-10 2007-10-11 Wacker Chemie Ag Vernetzbare Massen auf der Basis von Organosiliciumverbindungen
DE102006026227A1 (de) * 2006-06-06 2007-12-13 Wacker Chemie Ag Vernetzbare Massen auf der Basis von Organosiliciumverbindungen
DE102006036303A1 (de) * 2006-08-03 2008-02-07 Wacker Chemie Ag Kontinuierliches Verfahren zur Herstellung von vernetzbaren Organopolysiloxanmassen
EP2134429B1 (fr) * 2007-04-10 2015-08-26 Bünyamin Sürmeci Agent de rugosification et de maintien de la rugosité de cordages de raquettes de tennis, de badminton et de squash et procédé de fabrication de cet agent
DE102008001867A1 (de) * 2008-05-19 2009-11-26 Wacker Chemie Ag Verfahren zur Herstellung von quartäre Ammoniumgruppen aufweisenden Organopolysiloxanen
DE102009028140A1 (de) * 2009-07-31 2011-02-03 Wacker Chemie Ag Kondensation vernetzende Siliconmassen
DE102009028142A1 (de) * 2009-07-31 2011-02-03 Wacker Chemie Ag Bei Raumtemperatur durch Kondensation vernetzende Siliconmassen
DE102012206489A1 (de) * 2012-04-19 2013-10-24 Wacker Chemie Ag Härterzusammensetzungen für kondensationsvernetzende RTV-2-Systeme
EP3589698A1 (fr) * 2017-02-28 2020-01-08 Wacker Chemie AG Procédé pour produire des substances pouvant être réticulées pour obtenir des élastomères

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BE503146A (fr) * 1950-06-30 1900-01-01
DE902190C (de) * 1950-06-30 1954-01-21 Dow Corning Verfahren zur Herstellung neuer Aminomethylsiloxane
LU84463A1 (fr) * 1982-11-10 1984-06-13 Oreal Polymeres polysiloxanes polyquaternaires
DE3705121A1 (de) * 1987-02-18 1988-09-01 Goldschmidt Ag Th Polyquaternaere polysiloxan-polymere, deren herstellung und verwendung in kosmetischen zubereitungen
DE10139963A1 (de) * 2001-08-14 2003-03-06 Wacker Chemie Gmbh Quaternäre Ammoniumgruppen aufweisende Organopolysiloxane und Verfahren zu deren Herstellung

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Title
See references of WO2006032396A1 *

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DE102004046180A1 (de) 2006-03-30
JP2008513589A (ja) 2008-05-01
WO2006032396A1 (fr) 2006-03-30
US20070249782A1 (en) 2007-10-25
KR20070046190A (ko) 2007-05-02
CN101027342A (zh) 2007-08-29

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