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CA2136491C - Aqueous dispersions of organopolysiloxanes - Google Patents

Aqueous dispersions of organopolysiloxanes

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Publication number
CA2136491C
CA2136491C CA002136491A CA2136491A CA2136491C CA 2136491 C CA2136491 C CA 2136491C CA 002136491 A CA002136491 A CA 002136491A CA 2136491 A CA2136491 A CA 2136491A CA 2136491 C CA2136491 C CA 2136491C
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organopolysiloxane
groups
radical
weight
aqueous dispersion
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CA2136491A1 (en
Inventor
Stefan Oberneder
Rudolf Braun
Karl Braunsperger
Alfred Heinrich
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Wacker Chemie AG
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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
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/544—Silicon-containing compounds containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on 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; Coating compositions based on derivatives of such polymers
    • C09D183/04—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
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
    • 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
    • C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
    • 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
    • C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing groups
    • 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
    • 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
    • C08G77/28—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen sulfur-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
    • 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
    • C08K2201/00—Specific properties of additives
    • C08K2201/019—Specific properties of additives the composition being defined by the absence of a certain additive

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  • Health & Medical Sciences (AREA)
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  • Polymers & Plastics (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Silicon Polymers (AREA)
  • Paints Or Removers (AREA)
  • Colloid Chemistry (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Paper (AREA)

Abstract

Aqueous dispersions of organopolysiloxanes which are free from organic transition metal compounds and organic compounds of metals of main group III, IV and V and can be prepared using the starting substances (A) organopolysiloxane containing groups which can undergo condensation, (B) organopolysiloxane resin having a molecular weight of not more than 20,000 and (C) compound containing basic nitrogen.

Description

21~S4~1 - Docket: WA 9345-S
Paper No. l AQUEOUS DISPERSIONS OF ORGANOPOLYSILOXANES

s Field of Invention The present invention relates to aqueous dispersions of organopolysiloxanes which can be converted into elastomers after removal of water, processes for their preparation and their use as sealing and coating substances.
Backqround of Invention Environmental protection measures are increasingly forcing the avoidance of organic solvents in chemical formulations.
Aqueous systems are accordingly being used more and more.
Aqueous dispersions of organopolysiloxanes are known in many instances. The fundamental build-up of such dispersions, which vulcanize at room temperature to give elastomers, is composed of a linear polymer, a crosslinker component and a crosslinking cata-lyst. In general, an aqueous emulsion of polydiorganosiloxanes, the end groups of which contain groups which can undergo conden-sation, is initially introduced into the reaction vessel. These high molecular weight polysiloxanes are either emulsified directly or usually prepared in emulsion by polymerization, condensation and equilibration from linear or cyclic low molecular weight polysiloxanes by conventional processes. The polymer emulsion is then mixed with a crosslinker component and condensation catalyst, in bulk or as an emulsion, as well as further constituents, such as fillers, adhesion promoters and the like, the catalyst almost exclusively being torgano)metallic compounds.
The ~organo)metallic catalysts employed have the disadvantage that they impair the storage stability of the non-vulcanized 4 9 ~
compositions and also the stability of the vulcanized elastomers ~- and they are toxicologically unacceptable. The very involved, time-consuming and cost-intensive preparation of the aqueous emul-sions also is a disadvantage of a large number of the developments to date. These problems result from an emulsion polymerization, condensation or equilibration of the polydiorganosiloxanes to be employed, which requires a reaction time and must precede the preparation of the end product by admixing of the other consti-tuents. Another disadvantage of most of the aqueous emulsions known to date lies in the low solids content. However, a high solids content is a prerequisite for a low or infinitesimal shrinkage during vulcanization, which is desirable for most fields of use.

~5 German application P 42 17 561.5 (Wacker-Chemie GmbH) published December 2, 1993 describes aqueous dispersions of organopolysi-loxanes comprising organopolysiloxane which can undergo condensa-tion, silicone resin, polyvinyl alcohol, (organo)metallic catalyst and amino-functional substances, with which transparent vulcani-zates are obtained.
U.S. 5,045,231 (Wacker-Chemie GmbH; issued on September 3, 1991) and corresponding DE-A 39 32 025 further claim aqueous dis-persions of organopolysiloxanes comprising organopolysiloxanes which can undergo condensation, (organo)metallic catalysts, organopolysiloxane resins and diorganosilanolates, in which the solids content of the dispersions can be up to 90%.
DE-B 1037707 (Dow Corning; published on August 28, 1958) discloses a process for the preparation of emulsions of high molecular weight organopolysiloxanes starting from an emulsion of low molecular weight siloxanes. The desired molecular size is :-'A 2 2136~9~
achieved with the aid of strongly acid or alkaline catalysts.
These emulsions do not lead to elastomers.
U.S. 5,004,771 (Rhône Poulenc; issued on April 2, 1990) and corresponding EP-A 365 439, disclose acid condensation of a poly-diorganosiloxane blocked with OH end groups carried out in aqueous emulsion. After neutralization of the polymer emulsion, the other constituents, such as methylsiliconate solution and non-silicatic filler, but not compounds which contain basic nitrogen, are added.
However, the emulsions described, which have a solids content of less than 90%, do not result in elastomers.
Summary of Invention The present invention relates to aqueous dispersions of organopolysiloxanes which are free from organic transition metal compounds and organic compounds of metals of main group III, IV
and V and can be prepared using the starting substances (A) organopolysiloxane containing groups which can undergo con-densation, (B) organopolysiloxane resin having a molecular weight of not more than 20,000 and (C) compounds containing basic nitrogen.
Metals of main group III, IV and V of the Periodic Table are to include aluminum, gallium, indium, thallium, germanium, tin, lead, antimony and bismuth.
In the present invention, the term "which can undergo conden-sation" is also to include any preceding hydrolysis.
The organopolysiloxanes (A) containing groups which can undergo condensation and are employed according to the invention are preferably those of the formula HO-[SiRl2o]n-H (I), in which 2i36~1 1 is identical or different SiC-bonded hydrocarbon radicals having 1 to 18 carbon atoms, which are optionally substituted by halogen atoms, amino groups, ether groups, ester groups, epoxide groups, mercapto groups, cyano groups or (poly)glycol radicals, the latter being built up from oxyethylene and/or oxypropylene units, and n is an integer of at least 30.
Examples of hydrocarbon radicals R1 are alkyl radicals, such as the methyl, ethyl, n-propyl, isopropyl, 1-n-butyl, 2-n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl and 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 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-octadecyl radical; alkenyl radicals, such as the vinyl and the allyl radical: cycloalkyl radicals, such as cyclopentyl, cyclohexyl and cycloheptyl radicals and methylcyclohexyl radicals;
aryl radicals, such as the phenyl, naphthyl, anthryl and phen-anthryl radical; alkaryl radicals, such as o-, m- and p-tolyl radicals, xylyl radicals and ethylphenyl radicals; and aralkyl radicals, such as the benzyl radical and the ~- and , ~-phenyl-ethyl radical.
Examples of substituted hydrocarbon radicals R1 are halo-genated radicals, such as the 3-chloropropyl radical, the 3,3,3-trifluoropropyl radical, chlorophenyl radicals and hexafluoro-propyl radicals, such as the 1-trifluoromethyl-2,2,2-trifluoro-ethyl radical; the 2-(perfluorohexyl)ethyl radical, the 1,1,2,2-tetrafluoroethyloxypropyl radical, the 1-trifluoromethyl-2,2,2-213~491 ~ ~ trifluoroethyloxypropyl radical, the perfluoroisopropyloxyethyl radical and the perfluoroisopropyloxypropyl radical; radicals substituted by amino groups, such as the N-(2-aminoethyl)-3-amino-propyl radical, the 3-aminopropyl radical and the 3-(cyclohexyl-amino)propyl radical; radicals with ether functional groups, such as the 3-methoxypropyl radical and the 3-ethoxypropyl radical;
radicals with cyano functional groups, such as the 2-cyanoethyl radical; radicals with ester functional groups, such as the meth-acryloxypropyl radical; radicals with epoxide functional groups, such as the glycidoxypropyl radical, and radicals with sulfur functional groups, such as the 3-mercaptopropyl radical.
Preferred radicals Rl are hydrocarbon radicals having 1 to 10 carbon atoms, more preferably at least 80%, in particular at least 90%, of the radicals R1 being methyl radicals.
The average value for the number n in formula (I) is prefera-bly chosen such that the organopolysiloxane of formula (I) has a viscosity of more than 30 mm2/s, more preferably of more than 10,000 mm2/s, in particular of about 80,000 mm2/s, measured at a temperature of 25~C.
Although not shown in formula (I), up to 10 mole percent of the diorganosiloxane units can be replaced by other siloxane units, which are usually present, however, only as impurities which are more or less unavoidable, such as R13SiOl/2, RlSio3/2 and sio4/2 units, in which Rl has the meaning given above for this radical.
The polydiorganosiloxanes according to formula (I) can be prepared by processes known to experts, for example by polymeriza-tion or condensation of low molecular weight cyclic or linear organopolysiloxanes blocked with hydroxyl and/or alkoxy end groups.

213~4~1.

~ The organopolysiloxane (A) containing groups which can under--go condensation which is employed according to the invention can be a single type or a mixture of at least two types of such organopolysiloxanes containing groups which can undergo condensa-tion.
The organopolysiloxane resin (B) having a molecular weight of not more than 20,000 which is employed according to the invention is preferably one comprising units of the formula (R0)eR2asio4_a_e (II), in which R2 is identical or different and has one of the meanings given for Rl, R is identical or different and is a hydrogen atom or alkyl radical having 1 to 6 carbon atoms, a is 0, l, 2 or 3 and e is 0, 1, 2 or 3, with the proviso that the sum of a and e is less than or equal to 3 and a and e are on average greater than 0.
The average value of a is preferably a number between 0.5 and 1.95, in particular between 0.8 and 1.8.
The average value of e is preferably a number between 0.01 and 1, in particular between 0.01 and 0.5.
Although not expressed by formula (II), the organopolysilox-ane resin can contain up to 10% by weight of Si-bonded chlorine atoms resulting from its preparation.
Examples of the radical R2 are the examples for hydrocarbon radicals given for Rl, methyl, ethyl, vinyl and phenyl radicals being preferred and methyl radicals being more preferred.

2136~
_ Preferred radicals R are the hydrogen atom and alkyl groups having 1 to 4 carbon atoms, the hydrogen atom and methyl and ethyl radicals being more preferred.
The organopolysiloxane resin (B) employed according to the S invention has a molecular weight of preferably not more than lO,Ooo, more preferably not more than 4,000.
The organopolysiloxane resin (B) employed according to the invention can be prepared by processes which are known, for exam-ple, by condensation of low molecular weight organopolysiloxane resins in dlspersion, it being possible for the low molecular weight organopolysiloxane resins to be prepared by solvolysis and condensation of a solution of the corresponding silanes with Si-bonded chlorine atoms in a water-immiscible solvent by means of an alcohol/water mixture.
Instead of the organopolysiloxane resin employed according to the invention as component (B), it is also possible to employ an organosilane containing groups which can undergo condensation and/or partial hydrolyzates thereof, although this is not a sub-ject of the present invention.
Examples of such organosilanes are all the organosilanes which have been employed previously in organopolysiloxane compo-sitions which crosslink by condensation, for example, alkoxy-, acetoxy- and oximosilanes.
To prepare the aqueous dispérsions of organopolysiloxanes, according to the invention the organopolysiloxane resin (B) is employed in amounts of preferably 0.1 to 100 parts by weight, more preferably O.S to 35 parts by weight, in particular 2 to 20 parts by weight, per 100 parts by weight of organopolysiloxane (A) con-taining groups which can undergo condensation.

21364~i ._ The organopolysiloxane resin (B) employed according to the ~,_ invention can be a single type or a mixture of such organopoly-siloxane resins.
The compounds (C) containing basic nitrogen which are employed according to the invention are preferably those chosen from the group consisting of compounds of the formula NR33 (III), in which R3 is identical or different and is a hydrogen atom or hydrocar-bon radicals, which are optionally substituted by hydroxyl groups, halogen atoms, amino groups, ether groups, ester groups, epoxide groups, mercapto groups, cyano groups or (poly)glycol radicals, the latter being built up from oxy-ethylene and/or oxypropylene units, with the proviso that in formula (III) not more than two R3 are hydrogen atoms, aliphatic cyclic amines, for example, piperidine and - morpholine, and organosilicon compounds having at least one organic radical containing basic nitrogen, comprising units of the formula R4bYCsi(OR5)dO4-b-c-d (IV), in which R4 is identical or different and is a monovalent, SiC-bonded organic radical which is free from basic nitrogen, R5 is identical or different and is a hydrogen atom, an alkyl radical, an alkali metal cation, or an ammonium or phospho-nium group, Y is identical or different and is a monovalent, SiC-bonded radical containing basic nitrogen, 21364~1 b is 0, 1, 2 or 3, c is 0, 1, 2, 3 or 4 and d is 0, 1, 2 or 3, with the proviso that the sum of b, c and d is less than or equal s to 4 and at least one radical Y is present per molecule.
The optionally substituted hydrocarbon radicals R3 are pref-erably those having 1 to 18 carbon atoms.
The radical R4 is preferably a hydrocarbon radical having 1 to 18 carbon atoms, the methyl, ethyl and propyl radical being more preferred, in particular the methyl radical.
Examples of the radical R3 and R4 are independent of each other the examples for hydrocarbon radicals given for R1.
The radical R5 is preferably a hydrogen atom, methyl or ethyl radical or alkali metal cation, the hydrogen atom, methyl or ethyl radical or sodium and potassium cation being more preferred.
Examples of the radical RS are the hydrocarbon radicals given for radical R, the alkali metal cations, such as those of lithium, sodium, potassium, rubidium and cesium, and radicals of the formula +NR64 (V) or +PR64 (VI), in which R6 is identical or different and is a hydrocarbon radical having 1 to 6 carbon atoms.
The radicals Y are preferably those of the formula R72NR8- (VII), in which R7 is identical or different and is hydrogen or alkyl, cyclo-alkyl or aminoalkyl radicals and R8 is a divalent hydrocarbon radical.

21364~1 The examples of alkyl and cycloalkyl radicals R1 also apply in their full scope to alkyl and cycloalkyl radicals R7.
Preferably, at least one hydrogen atom is bonded to each nitrogen atom in the radicals of formula (VII).
The radical R8 is preferably a divalent hydrocarbon radical having 1 to 10 carbon atoms, more preferably 1 to 4 car~on atoms, in particular the n-propylene radical.
Examples of the radical R8 are the methylene, ethylene, propylene, butylene, cyclohexylene, octadecylene, phenylene and butenylene radical.
Examples of radicals Y are ~2N(cH2)3 H2N(C~2)2NH(C~2)2-~
H2N(CH2)2NH(Ca2)3-H2N(C~2)2-~
H3CN~(CH2)3-~
C2H5NH(Ca2)3-r H?CNH(CH2)2-~
C2~I5NH ( C~2 ~ 2-H2N(C~2) 4-~
H2N(C~2) s~~
H(NHCH2C~2)3-~
C4H,N~(CH2)2NH(C~)2-cyclo-CsH.lNH(CH,) 3 -, cyclo-Cs~,,,,NH ( C~2 ) 2- /
(c~)2N(c~2)3 (C~.)2N(C~2)2-~
(C2~s)2N(cH2)3- and (C2~5)2N(C~2)i--Y is preferably H2N(CH2)3-, H2N(cH2)2NH(cH2)3-l H3CNH(CH2)3_ C2H5NH(CH2)3- and cyclo-C6H11NH(CH2)3- where H2N(CH2)2NH(CH2)3-and cyclo-C6Hl1NH(CH2)3- being more preferred.
If the organosilicon compounds consisting of units of formula (IV) are silanes, 21364~
~~ b is preferably O, 1 or 2, more preferably O or l, c is preferably 1 or 2, more preferably 1, and d is preferably 1, 2 or 3, more preferably 2 or 3, with the proviso that the sum of b, d and d is 4.
Examples of the silanes of formula (IV) according to the invention are H2N(CH2)3-Si(OcH3)3 H2N(CH2)3-Si(Oc2H5)3 E2N ( C~2 ) 3-Si ( OC}Il ) 2Cgl E~2N( CH2 ) 3-Si ( ~C2~ ) 2cg~
H2N(C~I2) 3-Si(o~) 3_S~ON)~
H2N ( cg2 ) 3-Si ( OH) 2-y ( OM! yC~5~
H2N(CH2)2NH(Cg2) 3-Si(OCg3) 3 H2N(CH2)2N~I(cg2)3-Si(oc~g~)3 H2N ( CH2 ) 2N~ ( CH2 ) 3-Si ( ~C~ ) 2cg3 H2N ( CH2 ) 2NH ( C~2 ) 3-si ( OC2gs ) 2C~3 ~2N(C~2),N~(C~2)3-Si(O~) 3_~(0M)~
H2N ( CH2 ) 2NH ( Cg~ ) 3-Si ( OH ) 2-y ( OM~ yC~3 CyC10-C5~llNH ( C~2 ) 3-Ci ( OC~ ) 3 cyclo-C6HllNH ( cg2 ) 3-si ( 0C2E~ ) 3 CyClO-C5gllN~ ( CH2 ) 3-Si ( OC~ C~I3 cyclo-C6gllNH ( cg2 ) 3-~ii ( ~C2~ ) 2CH3 cyclo-C6HllNH(CH2) 3 - 5 i ( ~~ ~ 3.S ~OM)s and CyClO-C6~llNH(Cg2) 3-Si( OH)~y(OM) yC~I3 where H2N(cg2)2N~(c~2) 3-Si(ocg7) 3 H2N ( C~2 ) 2N~I ( C~12 ) ,-Si ( OC. 5 ) 3 EI2N ( CH2 ) 2NH ( C~2 ) 3-Si ( 0C~3 ) 2 H2N(C~2)~NH ( C~2 ) 3-Si ( 0c2g~ ) 2cg3 H2N(CH2)2NH(CH2)3-Si(OH)3-xtoK)x H2N(CH2)2NH(cH2)3-si(oH)2-y(oK)ycH3 cyclo-CsH~lNH(cg2) 3-_ i ( OCg- ) 3 cycio-Cs~l~NH ( C~. ) 3-Si ( OC2~. ) 3 CyClO-C5HllNH ( cg2 ) 3-'~i ( 0Cg3 ) 2cg3 cyclo-CSHllN~ ( Cg. ) 3-S i ( ~C2~ ) 2C~3 cyclo-c6HllNH(cH2)3-si(oH)3-x(oK)x and 2136~91 cyclo-C6HllNH(CH2)3-Si(OH)2_y(0K)yCH3 are preferred and _ ~2N ( C~2 ) 2N~ ( C~2 ) 3-Si ( OC~3 ) 3 ~2N ( C~2 ) 2~ ( C~2 ) 3-Si(OC~3)2CH3 cyclo-C6H~lNE(C~2)3-Si(OCH3)3 cyclo-C5~llN~(C~.)3-Si(OCE3)2C~3 H2N(cH2)2NH(cH2)3si(oH)3-x(oK)x and H2N(cH2)2NH(cH2)3-si(OH)2-y(OK)yCH3 are particularly preferred, where x is 0, 1, 2 or 3, y is 0, 1 or 2 and M is the cation of sodium or potassium.
Silanes of formula (IV) are commercially available products and can be prepared by processes customary in silicon chemistry.
If the organosilicon compound consisting of units of formula (IV) is an organopolysiloxane, the average value of b is prefera-bly between 0.5 and 2.5, more preferably between 1.4 and 2.0, the average value of c is preferably between 0.01 and 1.0, more pref-erably between 0.01 and 0.6, and the average value of d is prefer-ably between o and 2.0, more preferably between O and 0.2, with the proviso that the sum of b, c and d is less than or equal to 3.
The organopolysiloxanes consisting of units of formula (IV) employed according to the invention have a viscosity at 25~C of preferably 5 to 105 mm2/s, more preferably 10 to 104 mm2/s.
Examples of the organopolysiloxanes consisting of units of formula (IV) are H2N(CH2)2NH(fH2)3 (cH3)3sio[(cH3)2sio]k[cH3sio]msi(cH3)3 (IVa) and cyclo-C6H11NH(lCH2)3 (cH3)3sio[(cH3)2sio]k[cH3sio]msi(cH3)3 (IVb) in which the ratio of k to m is between 2:3 and 9:1 and the sum of k and m is between 10 and 1000, and H2N(CH2)2NH(fH2)3 [(CH3)2SiO]O[Sio3/2]p[(cH3)3siol/2]r (IVc) 213~191 i- and cyclo-C6Hl1NH(CH2)3 t(CH3)2SiO]O[SiO3/2]p[(CH3)3SiOl/2]r (IVd), in which the sum of o+p+r is between lO and lOO0, the ratio of o:(o+p+r) is between 0 and 0.9, in particular between 0.2 and 0.7, the ratio of p:(o+p+r) is between 0.05 and 0.6, in particular between 0.1 and 0.5, and the ratio of r:(o+p+r) is between 0.05 and 0.75, in particular between 0.2 and 0.6 Organopolysiloxanes consisting of units of formula (IV) are commercially available products and can be prepared by processes customary in silicon chemistry.
Examples of amines of formula (III) are cyclohexylamine, triethylamine, dodecylamine, diethyl-n-propylamine, cyclohexyl-methylamine, 2-aminoethanol, 2-amino-n-propanol, 2-amino-2-methyl-1-propanol, 2-dimethylamino-2-methyl-1-propanol, N,N-diethyl-ethanolamine, ethylenediamine, coconut fatty amine, coconut fatty methylamine, N,N-dimethylethanolamine and aniline.
organosilicon compounds having at least one organic radical containing basic nitrogen consisting of units of formula (IV), in particular potassium N-(2-aminoethyl)-3-aminopropylmethylsilano-late and sodium N-(2-aminoethyl)-3-aminopropylmethylsilanolate, are preferably employed as component (C).
The compound (C) containing basic nitrogen which is employed according to the invention can bè a single type or a mixture of at least two types of such compounds.
To prepare the aqueous dispersions of organopolysiloxanes, according to the invention component (C) is employed in an amount such that the content of basic nitrogen is preferably 0.01 to 5 parts by weight, more preferably 0.01 to 1 part by weight, in particular 0.04 to 0.5 part by weight, per 100 parts by weight of 2136~1 '~ organopolysiloxane (A) containing groups which can undergo conden-_ sation.
The aqueous dispersions of organopolysiloxanes according to the invention are in general stabilized by emulsifiers (D).
Cationic, anionic, ampholytic and nonionic emulsifiers can be used. These emulsifiers and their metering are sufficiently known in the art. One type of emulsifier, for example an anionic emul-sifier, or mixtures of at least two types of emulsifiers, for example a mixture of at least one anionic with at least one non-ionic emulsifier, can be used.
The emulsifiers (D) can be added to the mixture to be dis-persed or to be stabilized as a dispersion, and they can also be formed from a precursor, for example the corresponding acid or base or a salt of the actual emulsifier, by chemical reaction(s) in the mixture to be dispersed or to be stabilized as a disper-sion.
The anionic emulsifiers are preferably the salts of the surface-active sulfonic acids used in the emulsion polymerization to form the organopolysiloxane (A) containing groups which can undergo condensation, according to U.S. 3,294,725 (D.E. Findley, Dow Corning Corp.; issued on December 27, 1966), where the surface-active sulfonic acids and salts thereof are mentioned.
The alkali metal or ammonium salts of the sulfonic acids are preferred, in particular the natrium salts.
Examples which may be mentioned of the sulfonic acids are aliphatically substituted benzenesulfonic acids, aliphatically substituted naphthalenesulfonic acids, aliphatic sulfonic acids, silylalkylsulfonic acids and aliphatically substituted diphenyl-ether-sulfonic acids.

2136~1 Furthermore, alkali metal sulforicinoleates, sulfonated glycerol esters of fatty acids, salts of sulfonated monovalent alcohol esters, amides of aminosulfonic acids, such as the sodium salt of oleylmethyltauride, alkali metal salts of sulfonated aromatic hydrocarbons, such as sodium ~-naphthalene-monosulfonate, and condensation products of naphthalenesulfonic acids with form-aldehyde and sulfates, such as ammonium lauryl sulfate, triethanolamine lauryl sulfate and sodium lauryl ether-sulfate, can also be used as anionic emulsifying agents.
Nonionic emulsifiers are preferably used in addition to anionic emulsifier. Examples of such nonionic emulsifiers are saponins, addition products of fatty acids with ethylene oxide, such as dodecanoic acid esters with tetraethylene oxide, addition products of ethylene oxide with sorbitan trioleate, addition products of phenolic compounds having side chains with ethylene oxide, such as addition products of ethylene oxide with isodo-decylphenol, and imine derivatives, such as polymerized ethyl-eneimine, and addition products of alcohols with ethylene oxide, such as polyethylene glycol (10)-isotridecyl ether.
Examples of cationic emulsifiers are salts of fatty amines, quaternary ammonium compounds and quaternary compounds of pyri-dine, morpholine and imidazoline.
Examples of ampholytic emulsifiers are long-chain substituted amino acids, such as N-alkyldi(aminoethyl)-glycine, N-alkyl-2-aminopropionate, and betaines, such as (3-acylaminopropyl)di-methylglycine and alkylimidazolium betaine.
Water-soluble polymers which are described as being suitable for stabilizing dispersions, for example, polyvinyl alcohols, polyvinylpyrrolidones, polyvinyl sulfates, polyacrylates, poly-acrylamides and malonic acid/styrene copolymers, or else poly-~136 l9~.
saccharides, can also be employed as emulsifiers for the prepara-tion of dispersionsaccording to the invention.
If an emulsifier (D) is employed, preferred emulsifiers are anionic emulsifiers, nonionic emulsifiers and mixtures thereof, more preferably alkali metal salts of organosulfonic acids, organopolyglycol ethers and polyvinyl alcohols.
An emulsifier (D) is preferably employed for the preparation of the aqueous dispersions of organopolysiloxanes according to the invention.
The amount of emulsifier which is advantàgeous for stabili-zing the aqueous dispersions of organopolysiloxanes according to the invention depends greatly on the composition of the particular dispersion. In general, 0.5 to 10 parts by weight of emulsi-fier(s) are sufficient per 100 parts by weight of organopolysilox-ane (A) containing groups which can undergo condensation.
The aqueous dispersions of organopolysiloxanes according to the invention can also contain fillers (E).
Examples of fillers (E) are nonreinforcing fillers, or fillers having a BET surface area of up to 50 m2/g, such as quartz, diatomaceous earth, calcium silicate, zirconium silicate and zeolites, metal oxide powders, such as aluminum, titanium, iron or zinc oxides and mixed oxides thereof, barium sulfate, cal-cium carbonate, gypsum, silicon nitride, silicon carbide, boron nitride and powders of glass and plastics; reinforcing fillers, having a BET surface area of more than 50 m2/g, such as pyrogeni-cally prepared silicic acid, precipitated silicic acid, carbon black, such as furnace black and acetylene black, and silicon/
aluminum mixed oxides of high BET surface area; and fibrous fillers, such as asbestos and fibres of plastic. The fillers mentioned can be rendered hydrophobic, for example by treatment 213~91 with organosilanes or organosiloxanes or by etherification of hydroxyl groups to alkoxy groups.
If fillers (E) are employed, the amounts are preferably 0.1 to 200 parts by weight, more preferably 0.5 to 100 parts by weight, per 100 parts by weight of organopolysiloxane (A) con-taining groups which can undergo condensation. The amount of filler (E) employed can be varied within wide limits and depends especially on the particular intended use of the dispersions according to the invention.
The aqueous dispersions of organopolysiloxanes according to the invention can also contain additives (F), preferably chosen from the group consisting of adhesion promoters, plasticizers, foam prevention agents, thixotropic and dispersing agents, pig-ments, soluble dyestuffs, fungicides, odoriferous substances and organic solvents which are inert with respect to the dispersions.
Examples of adhesion promoters, may be added to improve the adhesion of the elastomeric products, obtained from the aqueous dispersions according to the invention after removal of their solvent contents, to the substrate to which the dispersions according to the invention have been applied, are silanes contain-ing amino functional groups, such as N-(2-aminoethyl)-3-amino-propyltrialkoxysilanes, in which the alkoxy radical is a methoxy, ethoxy, n-propoxy or isopropoxy radical.
Examples of plasticizers are dimethylpolysiloxanes which are liquid at room temperature and blocked by trimethylsiloxy end groups and have a viscosity of at least 10 mm2/s.
Examples of organic solvents which are inert with respect to the dispersions are hydrocarbons, such as petroleum ether having various boiling ranges, n-pentane, n-hexane, a hexane isomer mixture, toluene and xylene.

2136~91 Examples of thixotropic agents are carboxymethylcellulose and polyvinyl alcohol.
Examples of dispersing agents are polyacrylic acid salts and polyphosphates.
The thixotropic and dispersing agents mentioned in some cases also have emulsifying properties, so that they can be used as emulsifiers.
From each of the groups of substances mentioned above as possible components for the aqueous dispersions according to the invention, it is possible to use one substance of this group as a component or a mixture of at least two different substances of this group.
The aqueous dispersions of organopolysiloxanes according to the invention preferably have a pH from 5 to 13, more preferably from 6 to 11.
Solids contents of up to 95% by weight can be achieved in the aqueous dispersions of organopolysiloxanes according to the inven-tion. Lower solids contents are of course possible. A solids content of more than 90% can be achieved even in aqueous silicone dispersions according to the invention which contain no fillers.
The solids content here is to be understood as meaning the weight content of all the constituents of the dispersion apart from water and, if used, organic solvent with respect to the total weight of the dispersion.
The aqueous dispersions of organopolysiloxanes according to the invention can be dimensionally stable or free-flowing, depend-ing on their use.
The organosiloxane dispersions according to the invention are preferably those which are prepared using components (A), (B), (C), (D), water and optionally (E) and (F). Other substances are preferably not employed.

2136~91 "- The aqueous dispersions according to the invention can in ._ principle be prepared by any desired processes which are known to date.
Process 1 which comprises mixing all the constituents of the dispersion apart from the filler (E) with one another and dis-persing them together results as a considerably simplified and therefore economic preparation procedure from the combination according to the invention of the aqueous dispersions of organo-polysiloxanes. Thereafter, optionally, the filler (E) can be incorporated immediately into the dispersion.
In process 2, all the constituents of the dispersion, apart from component (C) and filler (E), are mixed with one another and dispersed together. Thereafter, component (C) and optionally, filler (E) are incorporated into the dispersion.
The dispersions according to the invention are preferably prepared by process 2.
The emulsification or dispersion operation can be carried out in customary mixing apparatuses which are suitable for the prepa-ration of emulsions and dispersions, for example, high-speed stator-rotor stirred apparatuses according to Prof. P. Willems, known by the registered trade mark "Ultra-Turrax". In this con-text, reference may also be made to Ullmanns Encyklopadie der Technischen Chemie (Ullmann's Encyclopedia of Industrial Chemis-try), Urban & Schwarzenberg, Munich, Berlin, 3rd ed. vol. 1, page 720 et seq.
The dispersion according to the invention can of cour~e also be prepared in another manner. However, it has been found that the procedure is critical and not all types of preparation give dispersions which lead to elastomers after removal of water.

2136~91 The processes according to the invention disclosed herein have the advantage that they are very easy to carry out and aqueous dispersions having very high solids contents can be pre-pared.
The processes according to the invention furthermore have the advantage that the individual constituents of the aqueous disper-sion of organopolysiloxanes can be employed without pretreatments, in particular the condensation of the polyorganosiloxane component before emulsification which is often described and the condensa-tion of the silicone resin component are omitted.
The processes according to the invention thus have the advantage that the aqueous dispersions can be prepared in a single working operation without having to allow for maturing times during the preparation, which would make the preparation process complicated and slow it down.
The process according to the invention can be carried out discontinuously or continuously.
The aqueous dispersions according to the invention have the advantage that they are free from organic transition metal comp-ounds and organic compounds of metals of main group III, IV and V, by which among other things a high stability is caused. The aqueous dispersions according to the invention are preferably storage-stable over a period of at least several years at room temperature and atmospheric pressure.
The aqueous dispersions of organopolysiloxanes according to the invention can be employed for all purposes for which aqueous dispersions of organopolysiloxanes have previously been used.
They can be used, for example, as sealing compositions, paints and coating systems and as electrically insulating or conductive, hydrophobic nonstick coating systems, or as a base or additives for such systems.

2136'1~1 '~ The aqueous dispersions of organopolysiloxanes according to the invention cure even at room temperature within a short time after evaporation of the solvent content, that is of the water and optionally organic solvent, to give elastomers.
The aqueous dispersions according to the invention, in parti-cular those which have been prepared using polyvinyl alcohols, have the advantage that they cure in thin layers to give trans-parent elastomers.
The aqueous dispersions according to the invention have the further advantage that they form firmly adhering coatings on many substrates, such as paper, textiles, mineral building materials, plastics, wood and many other substrates. Coating can be carried out by brushing, rolling, dipping or spraying.
A preferred application is as sealing compositions and coat-ing materials. Examples which may be mentioned are joint sealing compositions for facades and buildings and window glazing, as well as the use as sealing compositions in the sanitary sector. Exam-ples of coatings are, inter alia, facade coatings and impregna-tions, elastic masonry paints and textile and fabric coatings.
In the examples described below, all the parts and percentage data relate to the weight, unless stated otherwise. Furthermore, all the viscosity data are based on a temperature of 25~C. Unless stated otherwise, the following examples are carried out under the pressure of the surrounding atmosphere, that is about 1000 hPa, and at room temperature of about 22~C, or a temperature which is established when the reactants are brought together at room tem-perature without additional heating or cooling.
The amine number corresponds numerically to the value which indicates the consumption in ml of 1 N HCl on neutralization of 1 g of organosilicon compound containing amino functional groups.

~ ~ 3~4~ ~
The elastomer properties are determined in accordance with ~~ the following standardized tests:
Tear strength : DIN 53504-85S1 Elongation at break : DIN 53504-85S1 Modulus : DIN 53504-85Sl Shore A : DIN 53505-87 Tear propagation resistance : ASTM D624B-73 Example 1 (I) Preparation of an aqueous solution of potassium N-(2-amino-ethyl)-3-aminopropylmethylsilanolate 103 g of N-(2-aminoethyl)-3-aminopropylmethyldimethoxy-silane (commercially obtainable under the name "SilanTM GF 95"
from Wacker-Chemie GmbH, Munich) are metered into a solution of 63.7 g of potassium hydroxide (88% strength in water) in 200 g of water, while stirring vigorously. First methanol and then about 70 g of water are distilled off from the mixture by heating. The mixture is then topped up to a total weight of 317 g by addition of water to give a 40% strength potassium N-(2-aminoethyl)-3-aminopropylmethylsilanolate solution.
323 g of ~,~-dihydroxypolydimethylsiloxane having a visco-sity of 80,000 mm2/s, 16 g of organopolysiloxane resin of the average formula [(CH3)2Siol/2]1.1[Sio2] having an average molecular weight of 2000 and an average ethoxy content of 2.1~ by weight, based on the resin molecule, and 17 g of organopolysiloxane resin of the average formula [(CH3)2siO]o.2[(cH3)sio3/2]o.g having an average molecular weight of 3000 and an average ethoxy content of 2.6% by weight, based on the resin molecule, are mixed together with 30 g of a 75% strength aqueous sodium dodecylbenzenesulfonate ~ 22 solution (commercially obtainable under the name MarlonTM A
375" from Huls) and 50 g of water and the mixture is con-verted into an emulsion with the aid of an Ultra-Turrax mixer. After 4 g of the aqueous solution of potassium N-(2-aminoethyl)-3-aminopropylmethylsilanolate described under (I) and 219 g of precipitated chalk have been added, a creamy-soft, smooth, permanently homogeneous dimensionally stable composition having a solids content of 91% and a pH of 10.5 is obtained and is introduced into cartridges under air-tight conditions. The properties of the dispersion stored in this way are unchanged over a period of more than 1 year.
Films 2 mm thick are produced from the resulting disper-sion of organopolysiloxanes by applying the aqueous disper-sion to a surface of polytetrafluoroethylene (PTFE) and allowing the water to evaporate at room temperature. Two weeks after the application, dry, elastic films are formed, and these are investigated for their elastomer properties.
Data on the elastomer properties are to be found in Table 1.
Example 2 The procedure described in Example 1 is repeated, with the modification that instead of 30 g of a 75% strength aqueous sodium dodecylbenzenesulfonate solution, 28 g of an 80%
strength aqueous solution of polyethylene glycol 10-isotri-decyl ether (commercially obtainable under the name Arylpon TM
IT 10" from Grunau) are employed. After 219 g of precipi-tated chalk have been added, a creamy-white, smooth, perma-nently homogeneous dimensionally stable composition having a solids content of 91% and a pH of 10.0 is obtained and is introduced into cartridges under air-tight conditions. The properties of this dispersion stored in this way are A

23 ~

unchanged over a period of more than 1 year. Data on the -~ elastomer properties are to be found in Table 1.
Example 3 The procedure described in Example 1 is repeated, with the modification that instead of 30 g of a 75% strength aqueous sodium dodecylbenzenesulfonate solution, 30 g of a mixture of a 75% strength aqueous sodium dodecylbenzenesulfonate solu-tion and an 80% strength aqueous solution of polyethylene glycol 10-isotridecyl ether (commercially obtainable under the name "Arlypon IT 10" from Grunau) are employed. After 219 g of precipitated chalk have been added, a creamy-white, smooth, permanently homogeneous dimensionally stable composition having a solids content of 91% and a pH of 10.0 is obtained and is introduced into cartridges under air-tight conditions. The properties of this dispersion stored in this way are unchanged over a period of more than 1 year. Data on the elastomer properties are to be found in Table l.
Example 4 The procedure described in Example 1 is repeated, with the modification that instead of 30 g of a 75% strength aqueous sodium dodecylbenzenesulfonate solution, 30 g of an 80%
strength aqueous solution of polyethylene glycol (18)-phenol (commercially obtainable under the name Sapogenat TM T-180"
from Hoechst) are employed in a ratio of 1:3. After 219 g of precipitated chalk have been added, a creamy-soft, smooth, permanently homogeneous dimensionally stable composition having a solids content of 91% and a pH of 10.0 is obtained and is introduced into cartridges under air-tight conditions.
The properties of this dispersion stored in this way are 4 ~ ~ C
unchanged over a period of more than 1 year. Data on the '~- elastomer properties are to be found in Table 1.
Example 5 200 g of ~ dihydroxypolydimethylsiloxane having a visco-sity of 80,000 mm2/s, 12 g of organopolysiloxane resin with the average formula [(CH3)2Siol/2]l.l[Sio2] having an average molecular weight of 2000 and an average ethoxy content of 2.1% by weight, based on the resin molecule, 6 g of organo-polysiloxane resin with the average formula [(CH3)2siO]o.2[(cH3)sio3/2]o.g having an average molecular weight of 3000 and an average ethoxy content of 2.6% by weight, based on the resin molecule, and 10 g of polydi-methylsiloxane with 3-(2-aminoethylamino)propyl functional groups having a viscosity of 1000 mm2/s and an amine number of 0.3 (commercially obtainable under the name "Finish W RTM
1300" from Wacker-Chemie GmbH) are mixed together with 50 g of a 10% strength aqueous solution of a polyvinyl alcohol having a molecular weight of 85,000 and a hydrolysis number of 240 (commercially obtainable under the name Polyviol WTM
30/240" from Wacker-Chemie GmbH) and the mixture is converted into an emulsion with the aid of an Ultra-Turrax mixer.
After 2 g of the aqueous solution of potassium N-(2-amino-ethyl)-3-aminopropylmethylsilanolate described in Example 1 under (I)) have been added, a white, creamy-soft, smooth, permanently homogeneous dimensionally stable composition having a solids content of 84% and a pH of 8.0 is obtained and is introduced into cartridges under air-tight conditions.
The properties of this dispersion stored in this way are unchanged over a period of more than 1 year. The vulcanized product is transparent.

~ 25 2136~91 Transparent films 2 mm thick are produced from the resulting dispersion of organopolysiloxanes by applying the aqueous dispersion to a surface of polytetrafluoroethylene (PTFE) and allowing the water to evaporate at room tempera-ture. Two weeks after the application, dry, elastic films are formed, and are investigated for their elastomer proper-ties. Data on the elastomer properties are to be found in Table 1.
Example 6 (II) Preparation of an aqueous solution of potassium N-(2-amino-ethyl)-3-aminopropylsilanolate 111 g of N-(2-aminoethyl)-3-aminopropyltrimethoxysilane (commercially obtainable under the name "Silan GF 91" from Wacker-Chemie GmbH, Munich) are metered into a solution of 95.5 g of potassium hydroxide in 400 g of water, while stir-ring vigorously. First methanol and then about 200 g of water are distilled off from the mixture by heating. The mixture is then topped up to a total weight of 367 g by addi-tion of water to give a 40% strength potassium N-(2-amino-ethyl)-3-aminopropylsilanolate solution.
The procedure described in Example 1 is repeated, with the modification that instead of the 4 g of the aqueous solution of potassium N-(2-aminoethyl?-3-aminopropylmethylsilanolate described under I), 4 g of the aqueous solution of potassium N-(2-aminoethyl)-3-aminopropylsilanolate described above under II) are employed. After 219 g of precipitated chalk have been added, a creamy-soft, smooth, permanently homoge-neous dimensionally stable composition having a solids con-tent of 91% and a pH of 10.5 is obtained and is introduced into cartridges under air-tight conditions. The properties of this dispersion stored in this way are unchanged over a ~ period of more than 1 year. Data on the elastomer properties are to be found in Table I.
Example 7 The procedure described in Example l is repeated, with the modification that instead of 4 g of the aqueous solution of potassium N-(2-aminoethyl)-3-aminopropylmethylsilanolate described under I), 5 g of potassium N-(2-aminoethyl)-3-aminopropyltrimethoxysilane (commercially obtainable under the name "Silan GF 91" from Wacker-Chemie GmbH) are employed.
After 219 g of precipitated chalk have been added, a creamy-soft, smooth, permanently homogeneous dimensionally stable composition having a solids content of 91% and a pH of 9.5 is obtained and is introduced into cartridges under air-tight conditions. The properties of this dispersion stored in this way are unchanged over a period of more than l year. Data on the elastomer properties are to be found in Table 1.
Example 8 The procedure described in Example 1 is repeated, with the modification that instead of the 4 g of the aqueous solution of potassium N-(2-aminoethyl)-3-aminopropylmethylsilanolate described under I), 10 g of polydimethylsiloxane with 3-(cyclohexylamino)propyl functional groups having a viscosi-ty of 200 mm2/s and an amine number of 2.5 (commercially obtainable under the name "Haftvermitt1erTM A MS 61"from Wacker-Chemie GmbH) are employed. After 219 g of precipi-tated chalk have been added, a creamy-soft, smooth, perma-nently homogeneous dimensionally stable composition having a solids content of 91% and a pH of 9.0 is obtained and is introduced into cartridges under air-tight conditions. The 213S4~1 "~, properties of this dispersion stored in this way are ,.,._ unchanged over a period of more than 1 year. Data on the elastomer properties are to be found in Table 1.
Example 9 The procedure described in Example 1 is repeated, with the modification that instead of the 4 g of the aqueous solution of potassium N-(2-aminoethyl)-3-aminopropylmethylsilanolate described under I), 5 g of diethylamine are employed. After 219 g of precipitated chalk have been added, a creamy-soft, smooth, permanently homogeneous dimensionally stable composi-tion having a solids content of 91% and a pH of 9.5 is obtained and is introduced into cartridges under air-tight conditions. The properties of this dispersion stored in this way are unchanged over a period of more than 1 year. Data on the elastomer properties are to be found in Table 1.
Example 10 The procedure described in Example 1 is repeated, with the modification that instead of the 4 g of the aqueous solution of potassium N-(2-aminoethyl)-3-aminopropylmethylsilanolate described under I), 10 g of coconut fatty amine (commercially obtainable under the name "Genamin CC 100 D" from Hoechst) are employed. After 219 g of precipitated chalk have been added, a creamy-soft, smooth, permanently homogeneous dimen-sionally stable composition having a solids content of 91%
and a pH of 10.0 is obtained and is introduced into car-tridges under air-tight conditions. The properties of this dispersion stored in this way are unchanged over a period of more than 1 year. Data on the elastomer properties are to be found in Table l.

2136~9~
Comparison Example 1 ,_ The procedure described in Example 1 is repeated, with the modification that instead of the 4 g of the aqueous solution of potassium N-(2-aminoethyl)-3-aminopropylmethylsilanolate described under I), 4 g of a 42% strength aqueous solution of potassium methyl silanolate (commercially obtainable under the name "BS 15" from Wacker-Chemie GmbH) are employed.
After 219 g of precipitated chalk have been added, a creamy-soft, smooth, dimensionally stable composition having a solids content of 91% and a pH of 10.0 is obtained and is introduced into cartridges under air-tight conditions. The dispersion of organopolysiloxanes prepared in this manner does not vulcanize to an elastomer even after a maturing or storage time of 2 months. After release of the water, an oily, viscous composition results. After storage for three months, the dispersion demixes.
Comparison Example 2 The procedure described in Example 1 is repeated, with the modification that instead of the 4 g of the aqueous solution of potassium N-(2-aminoethyl)-3-aminopropylmethylsilanolate described under I), 4 g of a 30% strength aqueous KOH solu-tion are employed. After 219 g of precipitated chalk have been added, a creamy-soft, smooth, dimensionally stable composition having a solids content of 91% and a pH of 10.5 is obtained and is introduced into cartridges under air-tight conditions. The dispersion of organopolysiloxanes prepared in this manner does not vulcanize to an elastomer even after a maturing or storage time of 2 months. After release of the water, an oily, viscous composition results.

Comparison Example 3 ~- The procedure described in Example 1 is repeated, with the modification that instead of the 4 g of the aqueous solution of potassium N-(2-aminoethyl)-3-aminopropylmethylsilanolate described under I), 4 g of a 30~ strength aqueous benzyltri-ammonium hydroxide solution are employed. After 219 g of precipitated chalk have been added, a creamy-soft, smooth, dimensionally stable composition having a solids content of 90% and a pH of 9.0 is obtained and is introduced into cartridges under air-tight conditions. The dispersion of organopolysiloxanes prepared in this manner does not vulcanize to an elastomer even after a maturing or storage time of 2 months. After release of the water, an oily, viscous composition results.
Comparison Example 4 The procedure described in Example 1 is repeated, with the modification that instead of the 4 g of the aqueous solution of potassium N-(2-aminoethyl)-3-aminopropylmethylsilanolate described under I), 2 g of dodecylbenzenesulfonic acid (commercially obtainable under the name "Marlon AS-SaureTM"
from Huls AG) are employed. After 219 g of precipitated chalk have been added, a creamy-soft, smooth, permanently homogeneous dimensionally stable composition having a solids content of 91% and a pH of 6 is obtained and is introduced into cartridges under air-tight conditions. The dispersion of organopolysiloxanes prepared in this manner does not vulcanize to an elastomer even after a maturing or storage time of 2 months.

. 4 ~ 30 213~4~ ~
, Example 11 The procedure described in Example 1 is repeated, with the modification that instead of the 16 g of [(CH3)3Siol/2]l.l[sio2] silicone resin having an average molecular weight of 2000 and an average ethoxy content of 2.1% by weight, based on the resin molecule, 16 g of [(cH2=CH)(cH3)2Siol/2][sio2] having an average molecular weight of 1300 and an average ethoxy content of 9.9% by weight, based on the resin molecule, are employed. After 219 g of precipitated chalk have been added, a creamy-soft, smooth, permanently homogeneous dimensionally stable composi-tion having a solids content of 91% and a pH of 10.5 is obtained and is introduced into cartridges under air-tight conditions. The properties of this dispersion stored in this way are unchanged over a period of more than 1 year. Data on the elastomer properties are to be found in Table 1.
Example 12 The procedure described in Example 1 is repeated, with the modification that the 16 g of [(CH3)3siOl/2]l.l[sio2] sili-cone resin having an average molecular weight of 2000 and an average ethoxy content of 2.1% by weight, based on the resin molecule, are omitted. After 219 g of precipitated chalk have been added, a creamy-soft, smooth, permanently homoge-neous dimensionally stable composition having a solids con-tent of 91% and a pH of 10.5 is obtained and is introduced into cartridges under air-tight conditions. The properties of this dispersion stored in this way are unchanged over a period of more than 1 year. Data on the elastomer properties are to be found in Table 1.

~ 21~5191 _ Example 13 The procedure described in Example 1 is repeated, with the modification that the 17 g of [(CH3)2SiO]o 2[(CH3)SiO2]0 8 silicone resin having an average molecular weight of 3000 and an average ethoxy content of 2.6% by weight, based on the resin molecule, are omitted. After 219 g of precipitated chalk have been added, a creamy-soft, smooth, permanently homogeneous dimensionally stable composition having a solids content of 90% and a pH of 10.5 is obtained and is introduced into cartridges under air-tight conditions. The properties of this dispersion stored in this way are unchanged over a period of more than 1 year. Data on the elastomer prcperties are to be found in Table 1.
Example 14 The procedure described in Example 1 is repeated, with the modification that instead of the 16 g of [(CH3)3Siol/2]l.l[sio2] silicone resin having an average molecular weight of 2000 and an average ethoxy content of 2.1% by weight, based on the resin molecule, and 17 g of [(cH3)2Sio]o.2[(cH3)sio2]o.8 silicone resin having an average molecular weight of 3000 and an average ethoxy content of 2.6% by weight, based on the resin molecule, 15 g of [(CH3)3siOo 5]1 l[(cH3)2sio~o.s[(cH3)siol.s]l.g[sio2] having an average molecular weight of 2500 and an average ethoxy content of 2.3% by weight, based on the resin molecule, are employed. After 219 g of precipitated chalk have been added, a creamy-soft, smooth, permanently homogeneous dimensionally stable composition having a solids content of 91% and a pH of 10.5 is obtained and is introduced into cartridges under air-tight conditions. The properties of this dispersion stored 3~

213S49~
~ in this way are unchanged over a period of more than 1 year.
_ Data on the elastomer properties are to be found in Table 1.
Example 15 The procedure described in Example 1 is repeated, with the modification that instead of the 50 g of water, only 20 g of water are employed. After 219 g of precipitated chalk have been added, a creamy-soft, smooth, permanently homogeneous dimensionally stable composition having a solids content of 95% and a pH of 10.5 is obtained and is introduced into lo cartridges under air-tight conditions. The properties of this dispersion remain unchanged for at least 3 months. Data on the elastomer properties are to be found in Table 1.
The dispersion filled with chalk and also the nonfilled emulsion before addition of the chalk can be diluted with water down to solids contents of 5~ and less. The resulting dispersions, which are storage-stable for at least 6 months, can be used for coatings, for example of facades or fabrics.

Expe. ~ -cl Tear Strength F'-na -~ Modulus' Shore A Tear Propagation (N/mmZ) at break (%) (N/mm2) Hardness Resistance (N/mm) 0.7 1040 0.14 10 5.17 2 0.8 710 0.15 8 4.62 3 1.0 650 0.17 10 4.95 4 1.5 810 0.40 17 7.60 0.8 420 0.37 14 5.36 6 1.1 590 0.42 17 6.32 7 0.8 930 0.21 10 3.98 8 0.8 870 0.19 12 3.75 9 0.9 790 0.26 14 4.70 1.1 620 0.25 15 4.23 I l 1.1 580 0.49 21 6.77 12 0.6 320 0.13 7 3.04 13 0.4 250 0.10 6 2.45 14 1.2 420 0.50 23 4.77 0.9 900 0.23 13 5.56 I Tensile strength at 100% elongation.

Claims (10)

1. An aqueous dispersion of an organopolysiloxane which is free from organic transition metal compounds and organic compounds of metals of main group III, IV and V, comprising (A) an organopolysiloxane containing groups which undergo condensation;
(B) an organopolysiloxane resin having a molecular weight of not more than 20,000 and (C) compounds containing basic nitrogen.
2. An aqueous dispersion of an organopolysiloxane as claimed in claim 1, wherein the organopolysiloxane (A) containing groups which undergo condensation is one of the formula HO-[SiR1 2O]n-H (I), in which R1 is identical or different SiC-bonded hydrocarbon radicals having 1 to 18 carbon atoms, which are optionally substituted by halogen atoms, amino groups, ether groups, ester groups, epoxide groups, mercapto groups, cyano groups or (poly)glycol radicals, the latter being built up from oxyethylene and/or oxypropylene units, and n is an integer of at least 30.
3. An aqueous dispersion of an organopolysiloxane as claimed in claim 1, wherein the organopolysiloxane resin (B) is comprised of units of the formula in which R2 is identical or different and has one of the meanings given for R1, R is identical or different and is a hydrogen atom or alkyl radical having 1 to 6 carbon atoms, a is 0, 1, 2 or 3 and e is 0, 1, 2 or 3, with the proviso that the sum of a and e is less than or equal to 3 and a and e are on average greater than 0.
4. An aqueous dispersion of an organopolysiloxane as claimed in claim 1, wherein the organopolysiloxane resin (B) is employed in an amount of 0.1 to 100 parts by weight per 100 parts by weight of organopolysiloxane (A).
5. An aqueous dispersion of an organopolysiloxane as claimed in claim 1, wherein compound (C) containing basic nitrogen is an organosilicon compound having at least one organic radical containing basic nitrogen, comprising units of the formula in which R4 is identical or different and is a monovalent, organic radical which is free from basic nitrogen, R5 is identical or different and is a hydrogen atom, an alkyl radical, an alkali metal cation, or an ammonium or phosphonium group, Y is identical or different and is a monovalent, SiC-bonded radical containing basic nitrogen, b is 0, 1, 2 or 3, c is 0, 1, 2, 3 or 4 and d is 0, 1, 2 or 3, with the proviso that the sum of b, c and d is less than or equal to 4 and at least one radical Y is present per molecule.
6. An aqueous dispersion of an organopolysiloxane as claimed in claim 1, wherein the compound (C) containing basic nitrogen is present in an amount such that the content of basic nitrogen is 0.01 to 5 parts by weight per 100 parts by weight of organopolysiloxane (A).
7. An aqueous dispersion of an organopolysiloxane as claimed in claim 1, further containing an emulsifier (D) in an amount of 0.5 to 10 parts by weight per 100 parts by weight of organopolysiloxane (A).
8. An aqueous dispersion of an organopolysiloxane as claimed in claim 1, further containing a filler (E) in amounts of 0.1 to 200 parts by weight, per 100 parts by weight of organopolysiloxane (A).
9. A process for the preparation of an aqueous dispersion of an organopolysiloxane as claimed in claim 1, which comprises mixing (A) an organopolysiloxane containing groups which undergo condensation, and (B) an organopolysiloxane resin having a molecular weight of not more than 20,000 .
10. A sealing or coating composition comprised of an aqueous dispersion of an organopolysiloxane prepared by a process as claimed in claim 9.
CA002136491A 1993-11-26 1994-11-23 Aqueous dispersions of organopolysiloxanes Expired - Fee Related CA2136491C (en)

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