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(12) Patent Application Publication (10) Pub. No.: US 2004/0122198 A1 Ziche Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2004/0122198 A1 Ziche Et Al US 2004O122198A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2004/0122198 A1 Ziche et al. (43) Pub. Date: Jun. 24, 2004 (54) CROSSLINKABLE COMPOUNDS ON THE Publication Classification BASIS OF ORGANOSLC COMPOUNDS (51) Int. Cl." ..................................................... C08G 77/06 (76) Inventors: Wolfgang Ziche, Diera (DE); Uwe (52) U.S. Cl. ................................................................ 528/17 Scheim, Coswig (DE) Correspondence Address: (57) ABSTRACT BROOKS KUSHMAN PC. 1000 TOWN CENTER The invention relates to compounds on the basis of organo TWENTY-SECOND FLOOR Silic compounds, which can be crosslinked at room tem SOUTHFIELD, MI 48.075 (US) perature, So-called RTV-1 compounds, and which are char acterized by containing as the catalyst at least one (21) Appl. No.: 10/476,827 organozinc compound (C) that contains moieties of the PCT Fed: Aug. 14, 2002 general formula (I): R.R.(XR). SnX2, and com (22) pounds (D) that contain basic nitrogen, wherein R' is the (86) PCT No.: PCT/EP02/09143 same or different and represents -OS(=O).R, and R, X, R. R., a, b and c are defined as in claim 1, with the proviso (30) Foreign Application Priority Data that the organozinc compound comprises at least one R' group. The invention further relates to a method for produc Aug. 23, 2001 (DE)..................................... 101 41237.1 ing the inventive compounds. US 2004/O122198 A1 Jun. 24, 2004 CROSSLINKABLE COMPOUNDS ON THE BASIS sulfonic acids, for stabilizing RTV-1 acetoxy materials if the OF ORGANOSLC COMPOUNDS polymers contained have been prepared by anionic poly 0001. The invention relates in particular to materials merization of cyclic compounds and, for example, phospho Vulcanizable at room temperature and based on organosili ric acid was used for neutralizing the basic polymerization con compounds, e.g. So-called RTV-1 materials, using Spe catalysts and the materials thus contain, for example, alkali cial tin catalysts, and a process for the preparation of Such metal phosphates. materials. 0011. The use of reaction products of sulfonic acids with 0002 The use of dialkyltin (IV) compounds as conden amines or basic fillers in filled RTV systems is known, in sation catalysts in RTV-1 and RTV-2 silicon rubbers is order to facilitate the dispersing of the fillers and to obtain generally known. In RTV-1 alkoxy materials, however, these an elastomer having a low modulus. In this context, refer tin compounds have the disadvantage that you also catalyze ence may be made, for example, to U.S. Pat. No. 5,073,586 the undesired cleavage of the Siloxane chains by alcohol and U.S. Pat. No. 5,118,738. radicals (“equilibration”), Vulcanizable terminal alkoxy 0012 Finally, U.S. Pat. No. 5,425,947 states that RTV groups of the polysiloxane chain no longer being formed and materials which contain carboxylic anhydride-containing hence Sufficient Vulcanization of the material no longer polymers as rheological additives may contain Sulfonic acids being possible; i.e. with use in the intended manner, no as a further modulus-reducing additive. Stable Vulcanized products or no Sufficiently stable Vulca nized products being obtained. The shelf life, Stated as a 0013 The invention relates to Vulcanizable materials period in which the RTV-1 material can be stored without based on organosilicon compounds with at least two hydro markedly reducing its properties, is dramatically reduced by ly Zable groups, characterized in that at least one organotin the equilibration. compound (c) containing units of the formula 0003) The methods of choice for extending the shelf life RaR' (XR). SnX4ae. (I) consist to date in 0014) and 0004 replacement of the tin catalyst by a titanium 0015 compounds (D) containing basic nitrogen catalyst. The disadvantage here is the yellow colora 0016 are contained as a catalyst, where tion of the materials, with the result that only opaque, but not translucent, materials are possible. 0017 R may be identical or different and is a monova lent, optionally substituted hydrocarbon radical which 0005 Reduction of the amount of the tin catalyst. can be interrupted by oxygen atoms, 0006 Use of less aggressive tin catalysts, for 0018 X may be identical or different and is -O- or example tin-chelate catalysts. An excess of chelate compound, Such as, for example, acetylacetonate, is -S-, necessary; however, this is Volatile, toxicologically 0019 R' may be identical or different and has the unacceptable and hazardous to health. meaning of -OS(=O).R., 0007 Addition of alcohol scavengers which, owing 0020 R may be identical or different and is an amine to their high reactivity, react with alcohols. This radical bonded via nitrogen, a monovalent, optionally addition is, however, expensive and in general has an Substituted hydrocarbon radical which may be inter adverse effect on the adhesion behavior. rupted by -S(=O), or a radical -OR" with R' 0008 Dialkyldiacyltin catalysts blocked with Sulfonic having the meaning stated for R, acid are known for polyurethanes, activation being effected 0021) R' may be identical or different and is a hydro via amines. In this context, reference may be made, for gen atom or a monovalent, optionally Substituted example, to U.S. Pat. No. 5,849,864 or WO99/11369, Ash hydrocarbon radical which may be interrupted by oxy land Chemical Company. gen atoms, 0009 Organotin-based RTV-2 curing agents (catalyst/ crosslinking agent compositions) are described in DE-A 195 0022) a is 0, 1, 2 or 3, 27 101 and may also contain organic acids as reaction time 0023) b is 0, 1, 2 or 3, regulators, the reaction time regulators being intended to improve the reactivity of the claimed catalyst/crosslinking 0024 c is 0, 1, 2 or 3, agent compositions. 0025 with the proviso that the sum a+b+c is <4 and the 0.010 The use of Sn-O-SOR-containing compounds, organotin compound has at least one radical R'. which can be prepared, for example, from alkyltin oxides and Sulfonic acids, in, inter alia, condensation-Vulcanizing 0026. The organotin compounds used according to the polymer Systems has been described. In this context, refer invention may be both Stannanes, i.e. compounds of the ence may be made, for example, to U.S. Pat. No. 3,095,434 formula (I) with a+b+c-4, and oligomeric or polymeric tin and U.S. Pat. No. 5,981,685. Not described in the examples compounds, Such as, for example, Stannoxanes, i.e. com is the use of the claimed catalysts with Sn Sulfonate units for pounds containing units of the formula (I) with a+b+cs3. RTV silicone systems. However, alkoxy-RTV-1 systems Preferably, the organotin compounds used according to the with their specific problems with regard to the shelf life and invention are those which consist of units of the formula (I). the necessity of cocatalyzing additives are not described. 0027 Preferably, radical R is a hydrocarbon radical hav EP-A 623 642 describes the addition of acids, including ing 1 to 18 carbon atoms, particularly preferably an alkyl US 2004/O122198 A1 Jun. 24, 2004 radical having 1 to 12 carbon atoms, in particular the n-butyl or Sulfonic acid derivatives. In this context, reference may radical and the n-octyl radical. be made, for example, to F. Thunecke, R. Borsdorf, J. Prakt. 0028. Examples of radicals R are alkyl radicals, such as Chem., 333(1991), 489-494, and A. G. Davies Organotin methyl, ethyl, n-propyl, isopropyl, 1-n-butyl, 2-n-butyl, Chemistry, VCH Verlagsgesellschaft, Weinheim, 1997, Sec isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl and tert tion 11.4. pentyl radicals; hexyl radicals, Such as the n-hexyl radical; 0038. The preparation of the catalysts (C) according to heptyl radicals, Such as the n-heptyl radical; octyl radicals, the invention is also possible in situ by direct addition of the Such as the n-octyl radical and isooctyl radicals, Such as the Starting materials to the other components of the Vulcaniz 2,2,4-trimethylpentyl radical; nonyl radicals, Such as the able materials, which is included in the disclosure of the n-nonyl radical; decyl radicals, Such as the n-decyl radical; present invention but is not preferred. If the catalysts (C) dodecyl radicals, Such as the n-dodecyl radical; octadecyl according to the invention are to be prepared in situ, it is radicals, Such as the n-octadecyl radical, cycloalkyl radicals, preferable if basic components are added only after the in Such as the cyclopentyl, cyclohexyl and cycloheptyl radical Situ reaction of the tin compound and the Sulfonic acid. and methylcyclohexyl radicals, alkenyl radicals, Such as the Vinyl, 1-propenyl and 2-propenyl radical, aryl radicals, Such 0039 The compounds (D) containing basic nitrogen may as the phenyl, naphthyl, anthryl and phenanthryl radical; be amines, nitrogen-containing heterocycles or amino-func alkaryl radicals, Such as o-, m- and p-tolyl radicals, Xylyl tional organosilicon compounds, the last-mentioned being radicals and ethylphenyl radicals, and aralkyl radicals, Such preferred. as the benzyl radical and the the C- and the B-phenylethyl 0040 Examples of amino-functional organosilicon com radical. pounds (D) are silanes containing basic nitrogen, and orga 0029. Examples of Substituted radicals R are methoxy nosiloxanes containing basic nitrogen, Such as, for example, ethyl, ethoxyethyl and the ethoxyethoxyethyl radical. those of the formula (II) in which at least one radical R is a hydrocarbon radical Substituted by amino groups. 0030 X is preferably an oxygen atom. 0041) The organosilicon compounds (D) containing basic 0031) Radical R is preferably an optionally -SOH nitrogen are preferably those of the formula substituted hydrocarbon radical having 1 to 40 carbon atoms, which may be interrupted by -S(=O)-, particu (RO), SiR', (IV), larly preferably an alkyl or aryl radical having 1 to 40 carbon in which atoms, in particular an alkyl-Substituted aryl radical having 0042 7 to 40 carbon atoms.
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