US20090062471A1 - Crosslinkable materials based on organosilicon compounds - Google Patents

Crosslinkable materials based on organosilicon compounds Download PDF

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US20090062471A1
US20090062471A1 US12/203,172 US20317208A US2009062471A1 US 20090062471 A1 US20090062471 A1 US 20090062471A1 US 20317208 A US20317208 A US 20317208A US 2009062471 A1 US2009062471 A1 US 2009062471A1
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radical
groups
optionally substituted
radicals
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Marko Prasse
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Wacker Chemie AG
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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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/336—Polymers modified by chemical after-treatment with organic compounds containing silicon
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/12—Organo silicon halides
    • C07F7/16—Preparation thereof from silicon and halogenated hydrocarbons direct synthesis
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
    • C08G65/33303—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group
    • C08G65/33306—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group acyclic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/02—Polyalkylene oxides
    • 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
    • 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
    • C08K5/04—Oxygen-containing compounds
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • 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
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • 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
    • 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
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C08L101/02—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • C08L101/10—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing hydrolysable silane groups

Definitions

  • the invention relates to materials which are based on organosilicon compounds, are storable with exclusion of water and are crosslinkable to elastomers on ingress of water at room temperature, which comprise organic acids and basic nitrogen or basic phosphorus, to processes for preparation thereof, and to moldings produced therefrom.
  • One-component sealants which are storable with exclusion of water and vulcanize to elastomers on ingress of water at room temperature are known. These moisture curable products are used in large amounts, for example, in the construction industry. These mixtures are based on polymers which are terminated by silyl groups which bear reactive substituents such as OH groups or hydrolyzable groups, for example alkoxy groups. Typically, such materials comprise curing catalysts, especially tin compounds. The labeling requirements for dibutyltin compounds are becoming much more severe, which is causing a demand for replacement of tin compounds in general.
  • EP-B 538 881 describes materials which comprise organic acids and amines as curing catalysts.
  • EP-B 1 529 071 describes materials which comprise silyl radicals attached to the polymer matrix via N—C bonds.
  • EP-A 1 550 700, EP-A 1 624 027 and EP-A 1 659 155 describe materials which comprise organic acids and amines as curing catalysts. However, the reactivity of these materials is not particularly high.
  • EP-A 1 734 079 describes materials which comprise organic acids and amines as curing catalysts. However, a significant molar excess of basic nitrogen-containing compounds in relation to the organic acid is employed, in order to catalyze the relatively unreactive gamma-propylsilyl groups at the polymer ends.
  • WO-A 2007085620 and WO-A 200785605 describe materials which comprise organic anhydrides and amines as curing catalysts. However, the amino groups here are also in a molar excess, and tin catalysts are added.
  • An object of the invention is to provide moisture curable compositions which do not require a tin catalyst, yet which exhibit rapid crosslinking, particularly under ambient conditions.
  • crosslinkable materials comprising (A) at least one compound of the formula
  • the compounds (A) of the formula (I) have a molecular weight of from 2000 g/mol to 100,000 g/mol, more preferably from 5000 g/mol to 50,000 g/mol, in each case specified as the number average molecular weight.
  • the mixture of components (B), (C) and (D) has a pH of less than or equal to 7, more preferably from 4 to 7, and especially from 5 to 7.
  • the R radicals are optionally substituted, monovalent hydrocarbon radicals having from 1 to 18 carbon atoms, more preferably alkyl radicals, the vinyl radical, the 3,3,3-trifluoroprop-1-yl radical and the phenyl radical, especially the methyl radical.
  • R radicals are alkyl radicals such as the methyl, ethyl, n-propyl, isopropyl, 1-n-butyl, 2-n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl radical; 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 isooctyl 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-oct
  • substituted R radicals are haloalkyl radicals, such as the 3,3,3-trifluoro-n-propyl radical, the 2,2,2,2′,2′,2′-hexafluoroisopropyl radical and the heptafluoroisopropyl radical, haloaryl radicals such as the o-, m- and p-chlorophenyl radical, and the 2-methoxyethyl radical, the 2-methoxypropyl radical and the 2-(2-methoxyethoxy)ethyl radical.
  • haloalkyl radicals such as the 3,3,3-trifluoro-n-propyl radical, the 2,2,2,2′,2′,2′-hexafluoroisopropyl radical and the heptafluoroisopropyl radical
  • haloaryl radicals such as the o-, m- and p-chlorophenyl radical
  • 2-methoxyethyl radical the 2-methoxy
  • R 1 radicals are a hydrogen atom, the radicals specified for R, and organic polymer radicals, for example those which, as the polymer chain, contain polyoxyalkylene moieties such as polyoxyethylene, polyoxypropylene, polyoxybutylene, polyoxytetramethylene, polyoxyethylene-polyoxypropylene copolymer and polyoxypropylene-polyoxybutylene copolymer; hydrocarbon polymers such as polyisobutylene and copolymers of polyisobutylene with isoprene; polychloroprenes; polyisoprene; polyurethanes; polyesters; polyamides; polyacrylates; polymethacrylates; vinyl polymers; and polycarbonates.
  • the R 1 radical is a hydrogen atom or a hydrocarbon radical having from 1 to 20 carbon atoms, especially a hydrogen atom.
  • the A radicals may be an organic polymer radical, or else the X radicals described below.
  • the R 1 radical is preferably a hydrogen atom or a hydrocarbon radical having from 1 to 20 carbon atoms.
  • at least one R 1 radical is an organic polymer radical.
  • the A radicals are preferably organic polymer radicals which, as the polymer chain, contain polyoxyalkylenes such as polyoxyethylene, polyoxypropylene, polyoxybutylene, polyoxytetramethylene, polyoxyethylene-polyoxypropylene copolymer and polyoxypropylene-polyoxybutylene copolymer; hydrocarbon polymers such as polyisobutylene and copolymers of polyisobutylene with isoprene; polychloroprenes; polyisoprene; polyurethanes; polyesters; polyamides; polyacrylates; polymeth-acrylates; vinyl polymers; and polycarbonates, and are preferably bonded via —O—C( ⁇ O)—NH—, —NH—C( ⁇ O)O—, —NH—C( ⁇ O)—NH—, —NH—C( ⁇ O)—, —C( ⁇ O)—NH—, —C( ⁇ O)—O—, —O—C( ⁇ O)—, —
  • R′′ may be the same or different and is a hydrogen atom or is as defined for R.
  • the A radicals are polyoxyalkylene or polyacrylate radicals, especially polyoxyalkylene radicals which are bonded via —O—C( ⁇ O)—NH—, —C( ⁇ O)—O—, —O—C( ⁇ O)—O—, —O—, —O—CH 2 —C(OH)H—CH 2 —NR′′—, —O—CH 2 —C(OH)H—CH 2 —S—, —O—CH 2 —C(OH)H—CH 2 —C( ⁇ O)— and —O—CH 2 —C(OH)H—CH 2 —O—to the —[CR 1 2 —SiR a (OR 2 ) 3 ⁇ a ] group, where R′′ may be the same or different and is a hydrogen atom or is as defined for R.
  • a radical is a polyoxyalkylene radical A1
  • these preferably comprise repeat units of the formula
  • R 7 radicals are —CH 2 —, —CH 2 —CH 2 —, —CH 2 —CH(CH 3 )—, CH 2 —CH 2 —CH 2 —, —CH 2 —CH(—CH 2 —CH 3 )—, —CH(CH 3 )—CH(CH 3 )—, —CH 2 —CH 2 —CH 2 —CH 2 — and —CH 2 —C(CH 3 ) 2 —.
  • the R 7 radical is a divalent, optionally substituted hydrocarbon radical having from 1 to 4 carbon atoms, more preferably a divalent hydrocarbon radical having from 1 to 4 carbon atoms, yet more preferably —CH 2 —CH 2 — and CH 2 —CH(CH 3 )—, and especially —CH 2 —CH(CH 3 —.
  • a radical is a polyacrylate radical A2
  • Examples of the repeat unit of the formula (VI) are: —CH 2 —C(CH 3 )(COOCH 3 )—, —CH 2 —C(CH 3 )(COOCH 2 CH 3 )—, —CH 2 —C(CH 3 )(COOCH 2 CH 2 CH 3 )—, —CH 2 —C(CH 3 )(COOCH 2 CH 2 CH 2 CH 3 )—, —CH 2 —C(CH 3 )(COOCH(CH 3 ) 2 )—, —CH 2 —C(H)(COOCH 2 CH(CH 3 ) 2 )—, —CH 2 —C(H)(COOC(CH 3 ) 3 )—, —CH 2 —C(CH 3 )(COO(CH 2 ) 4 CH 3 )—, —CH 2 —C(CH 3 )(COO(CH 2 ) 4 CH 3 )—, —CH 2 —C(CH 3 )(COO(
  • Particularly preferred repeat units of the formula (VI) are —CH 2 —C(CH 3 )(COOCH 3 )—, —CH 2 —C(CH 3 )(COOCH 2 CH 3 )—, —CH 2 —C(CH 3 )(COOCH 2 CH 2 CH 3 )—, —CH 2 —C(CH 3 )(COOCH 2 CH 2 CH 2 CH 3 )—, —CH 2 —C(CH 3 )(COOCH(CH 3 ) 2 )—, —CH 2 —C(H)(COOCH 2 CH(CH 3 ) 2 )—, —CH 2 —C(H)(COOC(CH 3 ) 3 )—, —CH 2 —C(CH 3 )(COO(CH 2 ) 4 CH 3 )—, —CH 2 —C(CH 3 )(COO(CH 2 ) 4 CH 3 )—, —CH 2 —C(CH 3 )(COO(CH
  • the A radicals more preferably the polyoxyalkylene radicals A1, contain units of the formula
  • R 2 radical examples are the examples specified for the R radical.
  • the R 2 radicals are alkyl radicals having from 1 to 12 carbon atoms, more preferably alkyl radicals having from 1 to 4 carbon atoms, especially the methyl and ethyl radicals.
  • component (A) examples are organic polymers comprising organyloxysilylmethyl groups, such as polyacrylates, vinyl polymers, polyurethanes and polyglycols, which may be linear or branched.
  • These polymers can be prepared by known methods, such as addition reactions, for example hydrosilylation, Michael addition, Diels-Alder addition, the addition of isocyanate onto epoxides or onto reactive groups comprising active hydrogen such as amines, amides, hydroxyl or mercapto groups, the addition of epoxides onto reactive groups comprising active hydrogen such as amines, carbonyl groups, phenols or mercapto groups, and the addition of aziridines onto carbonyl groups or the copolymerization of vinylsilanes with monomers comprising an organic double bond or the grafting of vinylsilanes onto vinyl polymers.
  • the preparation methods can optionally be combined with one another.
  • the component (A) used may also be a copolymer formed from siloxane blocks and organic polymers, as described, for example, in U.S. Pat. No. 7,060,760 (EP-B1 1 370 602), which is incorporated herein by reference for this purpose.
  • the polymers (A) used in accordance with the invention may be either homopolymers or copolymers, each of which may be linear or branched.
  • Component (A) may have the —[CR 1 2 —SiR a (OR 2 ) 3 ⁇ a ] groups at any positions in the polymer, for instance at pendant and/or terminal positions.
  • component (A) used in accordance with the invention are those of the formula (I) in which A is defined as X and at least one R 1 radical is a polymeric organic radical, for example a polyacrylate, vinyl polymer, polyurethane, or polyglycol, which may be linear or branched, but such are not preferred.
  • R 1 radical is a polymeric organic radical, for example a polyacrylate, vinyl polymer, polyurethane, or polyglycol, which may be linear or branched, but such are not preferred.
  • Component (A) used in accordance with the invention preferably has a viscosity of from 100 to 1,000,000 mPas, more preferably from 1000 to 350,000 mPas, in each case at 25° C.
  • Components (A) are commercial products or are preparable by methods common in chemistry.
  • components (B1) are those selected from the group consisting of compounds (B11) of the formula
  • R 11 may be the same or different and is a hydrogen atom or a hydrocarbon radical optionally substituted by hydroxyl groups, halogen atoms, amino groups, ether groups, ester groups, epoxy groups, mercapto groups, cyano groups or (poly)glycol radicals, where the latter are formed from oxyethylene and/or oxypropylene units, with the proviso that in formula (VIII) at most two R 11 are defined as a hydrogen atom, and aliphatic cyclic amines, for example piperidine and morpholine, organosilicon compounds (B12) having at least one organic radical comprising basic nitrogen, comprising units of the formula
  • R 14 may be the same or different and is a hydrogen atom or a hydrocarbon radical optionally substituted by hydroxyl groups, halogen atoms, amino groups, ether groups, ester groups, epoxy groups, mercapto groups, imine groups, imide groups or (poly)glycol radicals, where the latter are formed from oxyethylene and/or oxypropylene units, and
  • R 11 radicals are the examples of optionally substituted hydrocarbon radicals specified for R, and also aminoalkyl radicals such as the 3-aminopropyl radical, the 2-aminopropyl radical, the 6-aminohexyl radical, the 2-aminoethyl radical, the 2-, 3- and 4-aminocyclohexyl radicals, the N-butyl-2-aminoethyl radical and the N,N-dimethyl-2-aminoethyl radical, hydroxyalkyl radicals such as the 2-hydroxyethyl radical, and also radicals in which two substituents may be joined to form a ring which may also contain other elements instead of the carbon atoms, such as the —CH 2 —CH 2 —O—CH 2 —CH 2 —, CH 2 —CH 2 —NH—CH 2 —CH 2 —, —CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —, —CH 2 —CH
  • Examples of compounds (B11) are CH 3 CH 2 (CH 3 )CHNH 2 , cyclo-C 6 H 11 NH 2 , (CH 3 CH 2 ) 2 N(CH 2 ) 3 NH 2 , (CH 3 (CH 2 ) 3 ) 2 N(CH 2 ) 3 NH 2 , CH 3 CH 2 CH 2 CH 2 NH 2 , CH 3 (CH 2 ) 7 NH 2 , (CH 3 ) 2 CH(CH 2 ) 5 NH 2 , (CH 3 CH 2 (CH 3 )CH) 2 NH, (cyclo-C 6 H 11 ) 2 NH, (CH 3 CH 2 CH 2 CH 2 ) 2 NH, (CH 3 (CH 2 ) 7 ) 2 NH, ((CH 3 ) 2 CH(CH 2 ) 5 ) 2 NH, (CH 3 CH 2 CH 2 CH 2 ) 3 N, (CH 3 (CH 2 ) 7 ) 3 N, ((CH 3 ) 2 CH(CH 2 ) 5 ) 3 N, cyclic
  • the R 11 radicals are preferably hydrocarbon radicals having from 1 to 18 carbon atoms or aminoalkyl radicals having from 1 to 18 carbon atoms, particular preference being given to the methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, 2-ethylhexyl, cyclohexyl, 1-methylheptyl, and n-octyl radicals, the 3-aminopropyl, the 2-aminopropyl, 6-aminohexyl, 2-aminoethyl, N,N-dimethyl-2-aminoethyl and N,N-dibutyl-2-aminoethyl radicals, and also the —CH 2 —CH 2 —O—CH 2 —CH 2 —, —CH 2 —CH 2 —NH—CH 2 —CH 2 —, —CH 2 —CH 2 —CH 2
  • R 12 radicals are the examples of optionally substituted hydrocarbon radicals specified for R.
  • the R 12 radicals are preferably hydrocarbon radicals having from 1 to 18 carbon atoms, particular preference being given to the methyl, ethyl and n-propyl radicals, especially the methyl radical.
  • R 13 examples of optionally substituted hydrocarbon radicals R 13 are the examples specified for the R 2 radical.
  • the R 13 radicals are preferably hydrogen or optionally nitrogen- or oxygen-substituted hydrocarbon radicals having from 1 to 18 carbon atoms, more preferably hydrogen or hydrocarbon radicals having from 1 to 3 carbon atoms, especially hydrogen, or the methyl and ethyl radicals.
  • D radicals are radicals of the formulae H 2 N(CH 2 ) 2 —, H 2 N(CH 2 ) 3 —, H 2 N(CH 2 ) 2 NH(CH 2 ) 2 —, H 2 N(CH 2 ) 2 NH(CH 2 ) 3 —, H 2 N(CH 2 ) 2 NH(CH 2 ) 2 NH(CH 2 ) 3 —, H 3 CNH(CH 2 ) 3 —, C 2 H 5 NH(CH 2 ) 3 —, H 3 CNH(CH 2 ) 2 —, C 2 H 5 NH(CH 2 ) 2 —, H 2 N(CH 2 ) 4 —, H 2 N(CH 2 ) 5 —, H(NHCH 2 CH 2 ) 3 —, C 4 H 9 NH(CH 2 ) 2 NH(CH 2 ) 2 —, Cyclo-C 6 H 11 NH(CH 2 ) 3 —, cyclo-C 6 H 11 NH(CH 2 ) 2 —
  • the D radical is preferably H 2 N(CH 2 ) 3 —, H 2 N(CH 2 ) 2 NH(CH 2 ) 3 —, H 3 CNH(CH 2 ) 3 —, C 2 H 5 NH(CH 2 ) 3 —, cyclo-C 6 H 11 NH—, CH 3 CH 2 CH(CH 3 )NH— and cyclo-C 6 H 11 NH(CH 2 ) 3 radical, particular preference being given to H 2 N(CH 2 ) 3 —, H 2 N(CH 2 ) 2 NH(CH 2 ) 3 — and cyclo-C 6 H 11 NH(CH 2 ) 3 radicals.
  • organosilicon compounds containing units of the formula (IX) are silanes
  • k is preferably 0, 1 or 2, more preferably 0 or 1
  • 1 is preferably 1 or 2
  • m is preferably 1, 2 or 3, more preferably 2 or 3, with the proviso that the sum of k+l+m is 4.
  • silanes of the formula (IX) optionally used in accordance with the invention are H 2 N(CH 2 ) 3 —Si(OCH 3 ) 3 , H 2 N(CH 2 ) 3 —Si(OC 2 H 5 ) 3 , H 2 N(CH 2 ) 3 —Si(OCH 3 ) 2 CH 3 , H 2 N(CH 2 ) 3 —Si(OC 2 H 5 ) 2 CH 3 , H 2 N(CH 2 ) 2 NH(CH 2 ) 3 —Si(OCH 3 ) 3 , H 2 N(CH 2 ) 2 NH(CH 2 ) 3 —Si(OC 2 H 5 ) 3 , H 2 N(CH 2 ) 2 NH(CH 2 ) 3 —Si(OCH 3 ) 2 CH 3 , H 2 N(CH 2 ) 2 NH(CH 2 ) 3 —Si(OCH 3 ) 2 CH 3 , H 2 N(CH 2 ) 2 NH(CH 2
  • the average value of k is preferably between 0.5 and 2.5, more preferably between 1.4 and 2.0
  • the average value of 1 is preferably between 0.01 and 1.0, more preferably between 0.01 and 0.6
  • the average value of m is preferably between 0 and 2.0, more preferably between 0 and 0.2, with the proviso that the sum of k, l and m is less then or equal to 3.
  • siloxane containing units of the formula (IX) used optionally in accordance with the invention are H 2 N(CH 2 ) 3 —Si(OCH 3 ) 2 —O—Si(CH 3 )(OCH 3 ) 2 , H 2 N(CH 2 ) 3 —Si(OC 2 H5) 2 -O—Si(CH 3 )(OCH 3 ) 2 , H 2 N(CH 2 ) 3 —Si(OC 2 H5) 2 -O—Si(CH 3 )(OC 2 H5) 2 , H 2 N(CH 2 ) 3 —Si(OCH 3 )(CH 3 )—O—Si(CH 3 )(OCH 3 ) 2 , H 2 N(CH 2 ) 3 —Si(OCH 3 )(CH 3 )—O—Si(OCH 3 ) 3 , H 2 N(CH 2 ) 3 —Si(OCH 3 )(CH 3 )—O—Si(OCH
  • R 14 radical examples of optionally substituted hydrocarbon radicals specified for R, the hydrogen atom, and amino imide radicals, such as the amino imide radical and the N,N-dimethylamino imide radical.
  • the R 14 radicals are preferably hydrogen, hydrocarbon radicals having from 1 to 18 carbon atoms, or amino imide radicals having from 1 to 18 carbon atoms, particular preference being given to a hydrogen atom, the methyl, isopropyl, phenyl, ortho-tolyl, amino imide and the N,N-dimethylamino imide radical, especially hydrogen and the methyl and phenyl radicals.
  • R 15 radicals are hydrogen and the examples of optionally substituted hydrocarbon radicals specified for R.
  • the R 15 radicals are preferably hydrogen or optionally substituted hydrocarbon radicals having from 1 to 18 carbon atoms, particular preference being given to hydrogen, the cyano radical, the 3-(trimethoxysilylpropyloxy)-2-hydroxypropyl radical and the trimethoxysilylpropyl radical, especially hydrogen.
  • Examples of compounds (B13) are 1,3-diphenylguanidine, 1,3-di-o-tolylguanidine, 1,3-diisopropylguanidine, 1,3-dimethylguanidine, dicyandiamide, 1,1,3,3-tetramethylguanidine, (1,1,3,3-tetramethylguanidyl)propyltrimethoxysilane, [(1,1,3,3-tetramethyl-guanidyl)propyl]methyldimethoxysilane, 1-o-tolyl-biguanidine or 1,1,5,5-tetramethyl-biguanidine.
  • Component (B1) is preferably H 2 N(CH 2 ) 3 —Si(OCH 3 ) 3 , H 2 N(CH 2 ) 3 —Si(OC 2 H 5 ) 3 , H 2 N(CH 2 ) 3 —Si(OCH 3 ) 2 CH 3 , N 2 N(CH 2 ) 3 —Si(OC 2 H 5 ) 2 CH 3 , H 2 N(CH 2 ) 2 NH(CH 2 ) 3 —Si(OCH 3 ) 3 , H 2 N(CH 2 ) 2 NH(CH 2 ) 3 —Si(OC 2 H 5 ) 3 , H 2 N(CH 2 ) 2 NH(CH 2 ) 3 —Si(OCH 3 ) 2 CH 3 , (CH 3 ) 2 Si(NHCH(CH 3 )CH 2 CH 3 ) 2 , H 2 N(CH 2 ) 3 —Si(OCH 3 ) 2 —(O—Si(CH 3 ) 2 )
  • the compounds (B2) comprising basic phosphorus are preferably those of the formula
  • R 16 are the radicals specified above for the R radical.
  • the R 16 radicals are preferably optionally substituted hydrocarbon radicals having from 1 to 20 carbon atoms, more preferably hydrocarbon radicals having from 1 to 16 carbon atoms, especially hydrocarbon radicals having from 1 to 8 carbon atoms.
  • R 17 radicals are the examples of hydrocarbon radicals specified for the R radical, which may be substituted by halogen atoms, amino groups, ether groups, ester groups, epoxy groups, mercapto groups, cyano groups, (poly)glycol radicals, C(O)O ⁇ , P(O)(R 23 )O ⁇ , —P(O)(OR 23 )O ⁇ , —C(O)OH, —C(O)OR 23 , —P(O)(R 23 )OH or —P(O)(OR 23 )OH groups and/or which may be interrupted by oxygen atoms, where R 23 in each case may be the same or different and is as defined for R 16 , for example the 4-(carboxylic acid)cyclohexyl, cyclohexyl-4-carbonate, O-ethyl-cyclohexyl-4-carbonate, 11-(carboxylic acid)undecyl, 11-undecanoate
  • the R 17 radicals are preferably hydrocarbon radicals optionally substituted by halogen atoms, amino groups, ether groups, ester groups, epoxy groups, mercapto groups, cyano groups, (poly)glycol radicals, —C(O)O—, —P(O)(R 23 )O ⁇ , —P(O)(OR 23 )O ⁇ , —C(O)OH, —C(O)OR 23 , —P(O)(R 23 )OH or —P(O)(OR 23 )OH groups having from 1 to 50 carbon atoms, which may be interrupted by oxygen atoms, more preferably hydrocarbon radicals having from 1 to 30 carbon atoms, especially hydrocarbon radicals having from 1 to 20 carbon atoms, where R 23 in each case may be the same or different and is as defined for R 16 .
  • R 19 radical examples are the examples specified for the R 17 radical.
  • the R 19 radicals are preferably hydrocarbon radicals which have from 1 to 50 carbon atoms, may be interrupted by oxygen atoms, and are optionally substituted by halogen atoms, amino groups, ether groups, ester groups, epoxy groups, mercapto groups, cyano groups, (poly)glycol radicals, —C(O)O ⁇ , —P(O)(R 23 )O ⁇ , —P(O)(OR 23 )O ⁇ , —C(O)OH, —(O)OR 23 , —P(O)(R 23 )OH or —P(O)(OR 23 )OH groups, more preferably hydrocarbon radicals which have from 1 to 50 carbon atoms and may be interrupted by oxygen atoms and/or which may be substituted by the —C(O)OR 23 , —C(O)O— or —C(O)OH group, especially hydrocarbon radicals which
  • R 18 radicals are hydrogen, the examples specified for the R 16 , radical and the lauryldiethyleneglycolate-ethyl, 4-nonylphenylpentaethyleneglycolateethyl, oleyletherhexaethyleneglycolateethyl and the 4-tert-butylphenyletheroligoethyleneglycolateethyl radicals.
  • the R 18 radicals are preferably hydrogen or optionally substituted hydrocarbon radicals which have from 1 to 50 carbon atoms and may be interrupted by oxygen atoms, more preferably a hydrogen atom, hydrocarbon radicals having from 1 to 20 carbon atoms or hydrocarbon radicals having from 1 to 40 carbon atoms, which may be interrupted by oxygen atoms, especially hydrogen or hydrocarbon radicals having from 1 to 16 carbon atoms.
  • s is 1 or 2; more preferably, s is 1.
  • the anions Z are preferably acylate groups having from 4 to 31 carbon atoms, phosphate groups having from 4 to 30 carbon atoms, hydrogenphosphate groups having from 2 to 15 carbon atoms, phosphonate groups having from 2 to 15 carbon atoms, hydrogenphosphonate groups having from 2 to 15 carbon atoms or phosphinate groups having from 4 to 30 carbon atoms.
  • the anions Z are more preferably acylate groups having from 6 to 25 carbon atoms, phosphate groups having from 6 to 20 carbon atoms, hydrogenphosphate groups having from 4 to 10 carbon atoms, phosphonate groups having from 2 to 12 carbon atoms, hydrogenphosphonate groups having from 2 to 12 carbon atoms, and phosphinate groups having from 6 to 24 carbon atoms.
  • the anions Z are acylate groups having from 2 to 25 carbon atoms, phosphonate groups having from 2 to 10 carbon atoms, hydrogenphosphonate groups having from 2 to 10 carbon atoms, or phosphinate groups having from 8 to 20 carbon atoms. Most preferably, the anions Z are acylate groups or phosphinate groups.
  • Examples of compounds (B2) are tetra-n-butylphosphonium bis(2,4,4-trimethylpentyl)phosphinate, tri-n-butylmethylphosphonium bis(2,4,4-trimethylpentyl)phosphinate, tri-n-hexyltetradecylphosphonium bis(2,4,4-trimethylpentyl)phosphinate, tetra-n-butylphosphonium octylhydrogenphosphonate, bis(tetra-n-butylphosphonium)octylphosphonate, tetra-n-butylphosphonium vinylhydrogenphosphonate, bis(tetra-n-butylphosphonium)vinylphosphonate, tetra-n-butylphosphonium laurylhydrogenphosphonate, bis(tetra-n-butylphosphonium)laurylphosphonate, tri-n-butylmethylphosphonium octyl
  • Compound (B2) is preferably tetra-n-butylphosphonium bis(2,4,4-trimethylpentyl)phosphinate, tri-n-butylmethylphosphonium bis(2,4,4-trimethylpentyl)phosphinate, tetra-n-butylphosphonium octylhydrogenphosphonate, bis(tetra-n-butylphosphonium)octylphosphonate, tetra-n-butylphosphonium vinylhydrogenphosphonate, bis(tetra-n-butylphosphonium)vinylphosphonate, tetra-n-butylphosphonium laurylhydrogenphosphonate, bis(tetra-n-butylphosphonium)laurylphosphonate, tri-n-butylmethylphosphonium octylhydrogenphosphonate, bis(tri-n-butylmethylphosphonium)octylphosphonate, tetra-
  • Components (B2) used in accordance with the invention are commercial products or are preparable by methods common in chemistry.
  • the inventive materials preferably contain component (B) in amounts of from 0.001 to 10 parts by weight, more preferably from 0.01 to 5 parts by weight, and especially from 0.05 to 2 parts by weight, based in each case on 100 parts by weight of component (A).
  • the phosphorus acid (C1) is preferably are of the formula (III) where r is 1 or 2.
  • Examples of the phosphorus acids (C1) used in accordance with the invention are mono- and diesters of phosphoric acid, such as n-octyl phosphate, (2-ethylhexyl)phosphate, di-n-octyl phosphate, di-n-butyl phosphate, bis(2-ethylhexyl)phosphate, diisooctyl phosphate, dihexadecyl phosphate; phosphonic acids and monoesters of phosphonic acid, such as n-octylphosphonic acid, monoethyloctylphosphonate, (2,4,4-trimethylpentyl)-phosphonic acid, dodecylphosphonic acid; and also phosphinic acids, such as bis(2-ethylhexyl)phosphinic acid, bis(2,4,4-trimethylpenty
  • the carboxylic acid (C2) is preferably a compound having a melting point at 1000 hPa of below 100° C., more preferably a compound having a melting point at 1000 hPa of below 100° C. and a molar mass of more than 80 g/mol, especially compounds having a melting point at 1000 hPa of below 80° C. and a molar mass of more than 120 to 1200 g/mol.
  • carboxylic acids (C2) used in accordance with the invention are saturated carboxylic acids, such as octanoic acid, neodecanoic acid, 2-ethylhexanoic acid, 4-cyclohexylbutanoic acid, dodecanoic acid, palmitic acid and stearic acid; unsaturated carboxylic acids, such as oleic acid, linoleic acid, linolenic acid; aromatic carboxylic acids, such as benzoic acid; hydroxycarboxylic acids and the ethers thereof, such as glycolic acid ethers, ricinoleic acid, salicylic acid, glycolic acid ethoxylate lauryl ether with average molar masses from 360 g/mol to 1000 g/mol, glycolic acid ethoxylate 4-tert-butylphenyl ether with average molar masses from 360 g/mol to 1000 g/mol, glycolic acid ethoxylate nonylphenyl
  • the inventive materials preferably comprise component (C) in amounts of from 0.1 to 20 parts by weight, more preferably from 0.5 to 15 parts by weight, and especially from 1.0 to 10 parts by weight, based in each case on 100 parts by weight of component (A).
  • component (C) used in accordance with the invention are commercially available products or are preparable by methods common in chemistry.
  • the X radicals are preferably R 3 R 4 N—, R 5 O—, R 5 ′S—, (R 5 ′′O) 2 P( ⁇ O)—, O ⁇ C ⁇ N—, R 6 C( ⁇ O)—, or R 6 ′O—C( ⁇ O)— radicals, where R 3 and R 4 are each independently a hydrogen atom or monovalent, optionally substituted hydrocarbon radical, where the R 3 R 4 N— moiety may also be joined to form a ring which may also contain other elements instead of the carbon atoms, R 5 is as defined for the R radical or is a CH 3 (C ⁇ CH 2 )—(C ⁇ O)— or CH 3 —O—(C ⁇ O)— radical, R 5 ′, R 5 ′′, R 6 and R 6 ′ may each independently be the same or different and may be as defined for the R radical.
  • R 3 and R 4 radicals are a hydrogen atom and the examples specified above for R.
  • R 5 , R 5 ′, R 5 ′′, R 6 and R 6 ′ radicals are each independently the examples specified above for R.
  • the R 3 radical is preferably a methyl, ethyl, propyl, butyl, hexyl, phenyl, cyclohexyl, 2-aminoethyl, N-(2-aminoethyl)aminoethyl, 6-aminohexyl or octyl radical or a hydrogen atom or the CH 3 —O—(C ⁇ O)— radical.
  • the R 4 radical is a methyl, ethyl, propyl, butyl, hexyl or octyl radical or a hydrogen atom. More preferably, the two R 3 and R 4 radicals are joined to form a ring, which especially also comprises oxygen or nitrogen.
  • Examples of the X radical as R 3 R 4 N in which the R 3 and R 4 radicals are bonded cyclically to one another are piperazine, morpholine or hexahydropyridine radicals bonded via a nitrogen atom, but also aromatic radicals, for example pyrrole radicals.
  • the R 5 radical is the CH 3 (C ⁇ CH 2 )—(C ⁇ O)— radical and the CH 3 —O—(C ⁇ O)— radical.
  • the R 5 ′ radical is a methyl, ethyl, propyl, butyl, hexyl or octyl radical.
  • the R 5 ′′ radical is a methyl, ethyl, propyl, butyl, hexyl or octyl radical.
  • the R 6 radical is a methyl, ethyl, propyl, butyl, hexyl or octyl radical.
  • the R 6 ′radical is a methyl, ethyl, propyl, butyl, hexyl or octyl radical.
  • X radicals are the N-cyclohexylamino, the N-phenylamino, the diethylamino, the N-(2-aminoethyl)amino, the N-(2-aminohexyl)amino, the N—(N′-(2-aminoethyl)2-aminoethyl)amino, the methacryloyloxy, the acetoxy, the isocyanato, the N-morpholino, the N-pyrrolidino, the N-piperidino and the O-methylcarbamato radicals.
  • Particularly preferred X radicals are the N-cyclohexylamino, the diethylamino, the N-(2-aminoethyl)amino, the N-(2-aminohexyl)amino, the methacryloyloxy, the acetoxy, the N-morpholino, the N-pyrrolidino, the N-piperidino and the O-methylcarbamato radical, and even more preferably the N-cyclohexylamino, the diethylamino, the N-(2-aminohexyl)amino, the methacryloyloxy, the acetoxy, the N-morpholino and the O-methylcarbamato radicals.
  • R′ examples of preferred and particularly preferred radicals for R′ are the radicals specified above for the R radical.
  • R 1 ′ are the radicals specified above for the R 1 radical.
  • the R 1 ′ radicals are preferably hydrogen or hydrocarbon radicals having from 1 to 20 carbon atoms, especially hydrogen and the methyl radical.
  • Y radicals are all hydrolyzable radicals useful in condensation curing systems, for example halogen atoms, organyloxy radicals, Si—N-bonded amine radicals, amide radicals, oxime radicals, acyloxy radicals and amineoxy radicals.
  • the Y radicals are preferably organyloxy radicals such as the methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, tert-butoxy and 2-methoxyethoxy radicals; amido radicals such as the N-methylacetamido and benzamido radical; and eneoxy radicals such as the 2-propeneoxy radical, more preferably the methoxy, ethoxy, n-propoxy, i-propoxy, 2-methoxyethoxy, benzamido and 2-propeneoxy radicals, and especially the methoxy or ethoxy radicals.
  • organyloxy radicals such as the methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, tert-butoxy and 2-methoxyethoxy radicals
  • amido radicals such as the N-methylacet
  • the silanes (D) used in accordance with the invention may have a certain proportion of silanol groups, i.e. Y is a hydroxyl group, which is, however, not preferred. These silanol groups form generally through contact with atmospheric humidity which is generally unavoidable in practice during the preparation and storage of the organosilicon compounds of the formula (II).
  • Silanes (D) used in accordance with the invention contain silanol groups in amounts up to not more than 5% by weight, preferably up to not more than 3% by weight, more preferably up to not more than 1.0% by weight.
  • organosilicon compound (D) used in accordance with the invention are H 2 N—CH 2 —Si(OCH 3 ) 3 , H 2 N—CH 2 —Si(OCH 2 CH 3 ) 3 , (CH 3 —(CH 2 ) 3 ) 2 N—CH 2 —Si(OCH 2 CH 3 ) 3 , (H 3 C—CH 2 ) 2 N—CH 2 —Si(OCH 2 CH 3 ) 3 , (CH 3 —(CH 2 ) 3 ) 2 N—CH 2 —Si(OCH 3 ) 3 , (H 3 C—CH 2 ) 2 N—CH 2 —Si(OCH 3 ) 3 , ((CH 3 ) 2 CH) 2 N—CH 2 —Si(OCH 2 CH 3 ) 3 , ((CH 3 ) 2 CH) 2 N—CH 2 —Si(OCH 3 ) 3 , (CH 3 CH 2 (CH 3 )CH) 3 , (CH 3 CH 2 (CH
  • the organosilicon compounds (D) used in accordance with the invention are preferably (CH 3 —(CH 2 ) 3 ) 2 N—CH 2 —Si(OCH 2 CH 3 ) 3 , (H 3 C—CH 2 ) 2 N—CH 2 —Si(OCH 2 CH 3 ) 3 , (CH 3 —(CH 2 ) 3 ) 2 N—CH 2 —Si(OCH 3 ) 3 , (H 3 C—CH 2 ) 2 N—CH 2 —Si(OCH 3 ) 3 , (CH 3 CH 2 (CH 3 )CH) 2 N—CH 2 —Si(OCH 2 CH 3 ) 3 , (CH 3 CH 2 (CH 3 )CH) 2 N—CH 2 —Si(OCH 3 ) 3 , C 6 H 5 (CH 3 )N—CH 2 —Si(OCH 2 CH 3 ) 3 , C 6 H 5 (CH 3 )N—CH 2 —Si(OCH 2 CH 3 )
  • the organosilicon compounds (D) are commercially available products or can be prepared by methods common in silicon chemistry.
  • the inventive materials preferably contain organosilicon compound (D) in amounts of from 0.01 to 20 parts by weight, more preferably from 0.5 to 10 parts by weight, and especially from 1.0 to 5.0 parts by weight, based in each case on 100 parts by weight of component (A).
  • inventive materials may comprise all further substances which have also been used to date in crosslinkable materials, for example further crosslinkers (E), plasticizers (F), fillers (G), adhesion promoters (H) and additives (I), where (E), (F) and (H) are different than components (A) to (D).
  • crosslinkable materials for example further crosslinkers (E), plasticizers (F), fillers (G), adhesion promoters (H) and additives (I), where (E), (F) and (H) are different than components (A) to (D).
  • crosslinkers (E) which may be used in the inventive materials may be any crosslinkers known to date having at least two condensable radicals, for example silanes having at least two organyloxy groups which are different than component (B12) and component (D).
  • the crosslinkers (E) which may be used in the inventive materials are silane crosslinkers, such as tetramethoxysilane, tetraethoxysilane, tetrapropoxysilane, tetrabutoxysilane, methyltrimethoxysilane, dimethyldimethoxysilane, methyltriethoxysilane, methylvinyldimethoxysilane, vinyltrimethoxysilane, butyltrimethoxysilane, vinyltriethoxysilane, phenyltrimethoxysilane, diphenyldimethoxysilane, phenyltriethoxysilane, 3-cyanopropyltrimethoxysilane, 3-cyanopropyltriethoxysilane, 3-(glycidoxy)propyltriethoxysilane, 1,2-bis(trimethoxysilyl)ethane, 1,2-bis(triethoxysilyl)ethanethanethan
  • crosslinkers (E) which may be used in the inventive materials are commercially available products or can be prepared by processes known in silicon chemistry. If the inventive materials comprise crosslinkers (E), the amounts are preferably from 0.1 to 10 parts by weight, more preferably from 0.5 to 3 parts by weight, based in each case on 100 parts by weight of component (A). The inventive materials preferably do not comprise any additional crosslinker (E).
  • plasticizers (F) are room temperature liquid dimethylpolysiloxanes end-capped by trimethylsiloxy groups, especially those having viscosities at 25° C. in the range between 50 and 1000 mPas, and also high-boiling hydrocarbons, for example paraffin oils, dialkylbenzenes, dialkylnaphthalenes or mineral oils consisting of naphthenic and paraffinic units, polyglycols, especially polypropylene glycols, which may optionally be substituted, high-boiling esters, for example phthalates, citric esters or diesters of dicarboxylic acids, liquid polyesters, polyacrylates or polymethacrylates, and also alkylsulfonic esters.
  • high-boiling hydrocarbons for example paraffin oils, dialkylbenzenes, dialkylnaphthalenes or mineral oils consisting of naphthenic and paraffinic units
  • polyglycols especially polypropylene glycols, which may optional
  • the amounts are preferably from 1 to 300 parts by weight, more preferably from 10 to 200 parts by weight, and especially from 20 to 100 parts by weight, based in each case on 100 parts by weight of constituent (A).
  • the inventive materials preferably comprise plasticizers (F).
  • fillers (G) are nonreinforcing fillers, i.e. 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 powders, such as aluminum oxides, titanium oxides, iron oxides or zinc oxides or mixed oxides thereof, barium sulfate, calcium carbonate, gypsum, silicon nitride, silicon carbide, boron nitride, glass and polymer powders, such as polyacrylonitrile powder; reinforcing fillers, i.e.
  • nonreinforcing fillers i.e. 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 powders, such as aluminum oxides, titanium oxides, iron oxides or zinc oxides or mixed oxides thereof, barium sul
  • fillers with a BET surface area of more than 50 m2/g such as fumed silica, precipitated silica, precipitated chalk, carbon black such as furnace black and acetylene black, and silicon-aluminum mixed oxides of high BET surface area; hollow spherical fillers, such as ceramic microspheres, for example those obtainable under the trade name ZeeospheresTM, elastic polymer spheres, for example those obtainable under the trade name EXPANCEL®, or glass spheres; fibrous fillers, such as asbestos and polymer fibers.
  • fillers mentioned may be hydrophobized, for example by treatment with organosilanes or -siloxanes or with stearic acid, or by etherification of hydroxyl groups to alkoxy groups. If fillers (G) are used, they are preferably hydrophobic fumed silica and precipitated or ground calcium carbonate.
  • the amounts are preferably from 1 to 300 parts by weight, more preferably from 1 to 200 parts by weight, and especially from 5 to 200 parts by weight, based in each case on 100 parts by weight of constituent (A).
  • the inventive materials preferably comprise fillers (G).
  • adhesion promoters (H) used in the inventive materials are silanes and organopolysiloxanes with functional groups, for example those with glycidoxypropyl, amino or methacryloyloxypropyl radicals, and also tetraalkoxysilanes and siloxanes containing T or Q groups, which may optionally comprise alkoxy groups. If, however, another component, for instance component (A), (B12), (D) or crosslinker (E), has the functional groups mentioned, it is possible to dispense with addition of adhesion promoters. If the inventive materials comprise adhesion promoters (H), the amounts are preferably from 0. 1 to 50 parts by weight, more preferably from 0.5 to 20 parts by weight, and especially from 1 to 10 parts by weight, based in each case on 100 parts by weight of constituent (A). The inventive materials preferably comprise adhesion promoters (H).
  • additives (I) are pigments, dyes, odorants, oxidation inhibitors such as sterically hindered phenols, e.g. 2,6-di-tert-butyl-4-methylphenol (BHT), 4,6-(dodecylthiomethyl)-o-cresol, pentaerythrityl tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate or C 7 -C 9 -branched alkyl [3-(3,5-di-tert-butyl-4-hydroxyphenyl)]propionate or vitamin E, fungicides, for example isothiazolinones, especially n-2-octyl-2H-isothiazolin-3-one, n-butyl-1,2-benzisothiazolin-3-one or 4,5-dichloro-2-octyl-3 (2H)-isothiazolin-3-one, 3-i
  • benzotriazole derivatives for example 2-(2H-benzotriazol-2-yl)-4,6-bis(1-methyl-1-phenylethyl)phenol, 2,4-di-tert-butyl-6-(5-chlorobenzotriazol-2-yl)phenol, 2-(2H-benzotriazol-2-yl)-4,6-di-tert-pentylphenol, 2-(2H-benzotriazol-2-yl)-4-methyl-6-dodecylphenol, 2-(2H-benzotriazol-2-yl)-4-alkyl-PEG-6-t-butylphenol, nanometal oxides, for example of titanium or zinc, cyanoacrylates, e.g.
  • HALS sterically hindered amines
  • the amounts are preferably from 0.01 to 100 parts by weight, more preferably from 0.05 to 30 parts by weight, especially from 0.1 to 10 parts by weight, based in each case on 100 parts by weight of constituent (A).
  • the inventive materials preferably comprise additives (I).
  • inventive materials are those preparable using
  • inventive materials apart from components (A) to (I), do not comprise any further constituents.
  • inventive materials are preferably viscous to pasty materials.
  • all constituents can be mixed with one another in any sequence.
  • This mixing can be effected at room temperature and the pressure of the surrounding atmosphere, i.e. from about 900 to 1100 hPa. If desired, this mixing can also be effected at higher temperatures, for example at temperatures in the range from 35 to 135° C.
  • the individual constituents of the inventive materials may each either be one type of such constituents or a mixture of at least two different types of such constituents, and all of the various R, X, Y, etc., can be the same or different.
  • the typical water content of air is sufficient.
  • the crosslinking of the inventive materials is preferably effected at room temperature. It can, if desired, also be carried out at temperatures higher or lower than room temperature, for example at from ⁇ 5° to 15° C. or from 30° to 50° C. and/or by means of concentrations of water exceeding the normal water content of air.
  • the crosslinking is carried out preferably at a pressure of from 100 to 1100 hPa, especially at the pressure of the surrounding atmosphere, i.e. from about 900 to 1100 hPa.
  • the present invention further provides moldings produced by crosslinking the inventive materials.
  • inventive materials can be used for all end uses for which materials which are storable with exclusion of water and crosslink to elastomers on ingress of water at room temperature can be used.
  • inventive materials thus have excellent suitability, for example, as sealants for joints, including vertical joints, and similar cavities having an internal diameter of, for example, from 10 to 40 mm, for example of buildings, land vehicles, watercraft and aircraft, or as adhesives or cementing compositions, for example in window construction or in the production of glass cabinets and, for example, for the production of protective coatings, or coatings preventing sliding, or of elastomeric moldings and for the insulation of electrical or electronic devices.
  • inventive materials have the advantage that they are easy to prepare.
  • inventive condensation-crosslinkable materials have the distinct advantage that they comprise only exceptionally small amounts, if any, of heavy metal compounds and are thus free of labeling requirements and toxicologically safe.
  • inventive materials have the advantage that they do not yellow in the course of storage or in the cured state, that it is thus also possible to produce high-grade transparent products, and the still further advantages that they feature a very high storage stability and that the resilience is adjustable within a wide range.
  • the crosslinkable materials obtained in the examples are applied to PE film in a layer of thickness 2 mm and stored under standard climatic conditions (23° C. and 50% relative atmospheric humidity).
  • standard climatic conditions 23° C. and 50% relative atmospheric humidity.
  • the formation of a skin is checked every 5 min.
  • a dry finger is placed cautiously onto the surface of the sample and pulled upward. When sample remains stuck to the finger, no skin has formed yet. When no sample remains stuck to the finger any longer, a skin has formed and the time is noted.
  • constituents (B), (C) and (D) are mixed in the ratio used and left to stand for one hour, and then a small sample is applied to moistened universal indicator paper (e.g. universal indicator from Merck, Germany, with a measurement range of pH 1-14).
  • moistened universal indicator paper e.g. universal indicator from Merck, Germany, with a measurement range of pH 1-14.
  • the pH is determined after an action time of from 1 to 3 min by comparison with the color scale.
  • Me shall represent a methyl group.
  • a sterically hindered amine principally consisting of bis(1,2,2,6,6-pentamethyl-4-piperidyl)sebacate and methyl 1,2,2,6,6-pentamethyl-4-piperidyl sebacate, as a free-radical scavenger, approx. 35% of a UV absorber of the benzotriazole type, principally consisting of 2-(2H-benzotriazol-2-yl)-4-methyl-6-dodecylphenol and approx.
  • a sterically hindered phenol principally consisting of C7-C9-branched alkyl [3-(3,5-di-tert-butyl-4-hydroxyphenyl)]propionate as an oxidation inhibitor (commercially available under the name Tinuvin® B 75 from Bodo Möller Chemie GmbH, Germany), 0.25 g of tetramethylguanidine (commercially available from Sigma-Aldrich, Germany) and 2.0 g of octanoic acid (commercially available from Sigma-Aldrich, Germany). Finally, the mixture is stirred at absolute pressure approx. 100 mbar for 5 minutes, transferred under airtight conditions and stored. After one day of storage at room temperature, tests 1 to 3 are carried out. The results can be found in table 1.
  • fumed hydrophobic silica having a specific surface area of 200 m 2 /g (commercially available under the name HDK® H18 from Wacker Chemie AG, Kunststoff, Germany) are stirred in and homogenized at an absolute pressure of 100 mbar for 5 min.
  • the mixture is completed by homogeneously mixing in 6.0 g of a liquid stabilizer mixture consisting of approx. 50% of a sterically hindered amine, principally consisting of bis(1,2,2,6,6-pentamethyl-4-piperidyl)sebacate and methyl 1,2,2,6,6-pentamethyl-4-piperidyl sebacate, as a free-radical scavenger, approx.
  • UV absorber of the benzotriazole type principally consisting of 2-(2H-benzotriazol-2-yl)-4-methyl-6-dodecylphenol and approx. 15% of a sterically hindered phenol, principally consisting of C7-C9-branched alkyl[3-(3,5-di-tert-butyl-4-hydroxyphenyl)]propionate as an oxidation inhibitor (commercially available under the name Tinuvin® B 75 from Bodo Möller Chemie GmbH, Germany), 150 g of a polypropylene glycol monohydroxymonobutyl ether having a viscosity at 50° C.

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US20150232777A1 (en) * 2014-02-20 2015-08-20 Ut-Battelle, Llc Ionic liquids containing symmetric quaternary phosphonium cations and phosphorus-containing anions, and their use as lubricant additives

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DE102007041856A1 (de) 2009-03-05
EP2031024B1 (de) 2010-02-24
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US20120004364A1 (en) 2012-01-05
US8399575B2 (en) 2013-03-19
EP2031024A1 (de) 2009-03-04

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