EP1694773A2 - Produits reticulables a base de composes organosilicium - Google Patents

Produits reticulables a base de composes organosilicium

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Publication number
EP1694773A2
EP1694773A2 EP04803981A EP04803981A EP1694773A2 EP 1694773 A2 EP1694773 A2 EP 1694773A2 EP 04803981 A EP04803981 A EP 04803981A EP 04803981 A EP04803981 A EP 04803981A EP 1694773 A2 EP1694773 A2 EP 1694773A2
Authority
EP
European Patent Office
Prior art keywords
radical
optionally
radicals
organosilicon compounds
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP04803981A
Other languages
German (de)
English (en)
Inventor
Uwe Scheim
Christian Ochs
Gabriele Dineiger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wacker Chemie AG
Original Assignee
Wacker Chemie AG
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Filing date
Publication date
Application filed by Wacker Chemie AG filed Critical Wacker Chemie AG
Publication of EP1694773A2 publication Critical patent/EP1694773A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • C08G77/04—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
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/452—Block-or graft-polymers containing polysiloxane sequences containing nitrogen-containing sequences
    • 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
    • C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/34—Filling pastes
    • 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
    • C08G77/22—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
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
    • C08L2666/66—Substances characterised by their function in the composition

Definitions

  • the invention relates to crosslinkable compositions based on organosilicon compounds with biostatic properties and to a process for their production and their use.
  • One-component sealing compounds which are storable with the exclusion of water and which vulcanize to elastomers when water is admitted at room temperature are known. These products are used in large quantities, for example in the construction industry. Especially in environments with high air humidity, such as in bathrooms, kitchens, but also tropical regions, for example, the surface of the sealants easily forms an overgrowth with organisms such as fungi or algae. In order to prevent this, biocides such as fungicides have been added to the sealants to prevent fouling.
  • fungicides used in sealing compounds are methylbenzimidazol-2-ylcarbamate (carbendazim), 10, 10'-oxy-bisphenoxarsin, 2- (4-thiazolyl) -benzimidazole, N-octyl-4-isothiazolin-3-one, 4 , 5-dichloro-2-n-octyl-4-isothiazolin-3-one, diiodomethyl-p-tolylsulfone (Amical, cf. e.g. EP 34 877 A), triazolyl compounds such as tebuconazole in combination with silver-containing zeolites (cf.
  • the invention relates to crosslinkable compositions based on organosilicon compounds, characterized in that they contain organosilicon compounds with quaternary ammonium groups.
  • the crosslinkable compositions are preferably crosslinkable compositions by means of a condensation reaction.
  • condensation reaction is also intended to include a possibly preceding hydrolysis step.
  • compositions according to the invention are particularly preferably those comprising (A) organosilicon compound having at least two condensable groups, (B) organosilicon compound having at least one unit of the formula -SiR 2 2 -R 4 -N + R 3 2 -R 4 -SiR 2 2 - • X " (II),
  • R 2 can be the same or different and has a meaning given for R below
  • R 3 can be the same or different and represents a monovalent, optionally substituted hydrocarbon radical or can be part of a bridging alkylene radical
  • X- represents an organic or inorganic anion
  • R 4 represents a divalent, optionally substituted carbonic acid residue which can be interrupted by heteroatoms, and optionally
  • (C) crosslinker (C) crosslinker.
  • condensable radicals should also be understood to mean those radicals which also include a possibly preceding hydrolysis step.
  • the condensable groups which the organosilicon compounds used which are involved in the crosslinking reaction can have can be any groups, such as hydroxyl, acetoxy, oximato and organyloxy groups, in particular alkoxy radicals, such as ethoxy radicals, alkoxyethoxy radicals and methoxy radicals.
  • the organosilicon compounds (B) used according to the invention can be any organosilicon compounds with at least one radical of the formula (II), which are both pure siloxanes, ie ⁇ Si-O-Si ⁇ structures, and silcarbanes, thus ⁇ Si-R'-Si ⁇ structures with R 'can be a divalent, optionally substituted or interrupted by hetero-hydrocarbon radical or any copolymers containing organosilicon groups.
  • formula (II) are both pure siloxanes, ie ⁇ Si-O-Si ⁇ structures, and silcarbanes, thus ⁇ Si-R'-Si ⁇ structures with R 'can be a divalent, optionally substituted or interrupted by hetero-hydrocarbon radical or any copolymers containing organosilicon groups.
  • the organosilicon compounds (A) used according to the invention can be all organosilicon compounds with at least two condensable groups which have also been used to date in compositions which can be crosslinked by the condensation reaction. These can be both pure siloxanes, ie ⁇ Si-O-Si ⁇ structures, and silcarbanes, i.e. ⁇ Si-R '' - Si ⁇ structures with R '' equal to a divalent, optionally substituted or with heteroatoms interrupted hydrocarbon radical or any copolymers having organosilicon groups.
  • the organosilicon compounds (A) used according to the invention are preferably those containing units of the formula
  • R can be the same or different and means optionally substituted hydrocarbon radicals which can be interrupted by oxygen atoms,
  • R 1 can be the same or different and means hydrogen atom or monovalent, optionally substituted hydrocarbon radicals which can be interrupted by oxygen atoms
  • Y can be the same or different and halogen atom, pseudohalogen radical, Si-N-bonded amine radicals, amide radicals, Oxime radicals, amine oxy radicals and acyloxy radicals means, a is 0, 1, 2 or 3, preferably 1 or 2, b is 0, 1, 2 or 3, preferably 0, 1 or 2, particularly preferably 0, and c is 0, 1, 2 or 3, preferably 0 or 1, particularly preferably 0, with the proviso that the sum of a + b + c is less than or equal to 4 and at least two condensable radicals (OR 1 ) are present per molecule.
  • the sum a + b + c is preferably less than or equal to 3.
  • the radical R is preferably monovalent hydrocarbon radicals having 1 to 18 carbon atoms, which may optionally contain halogen atoms, amino groups, ether groups, ester groups, epoxy groups, mercapto groups, cyano groups or (poly) glycol residues are substituted, the latter being composed of oxyethylene and / or oxypropylene units, particularly preferably alkyl radicals having 1 to 12 carbon atoms, in particular the methyl radical.
  • the radical R can also be divalent radicals which, for example, connect two silyl groups to one another.
  • radicals R are alkyl radicals, such as the methyl, ethyl, n-propyl, iso-propyl, 1-n-butyl, 2-n-butyl, iso-butyl, tert. Butyl, n-pentyl, iso-pentyl, neo-pentyl, tert-pentyl radical; Hexyl radicals, such as the n-hexyl radical; Heptyl residues, such as the n-heptyl residue; 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
  • substituted radicals R are methoxyethyl, ethoxyethyl and the ethoxyethoxyethyl radical.
  • divalent radicals R are polyisobutylene diyl radicals and propanediyl-terminated polypropylene glycol radicals.
  • radicals R 1 are the monovalent radicals indicated for R.
  • the radical R 1 is preferably a hydrogen atom or alkyl radicals having 1 to 12 carbon atoms, particularly preferably a hydrogen atom, methyl or ethyl radical, in particular a hydrogen atom.
  • radical Y examples are acetoxy, dirnethylamino, cyclohexylamino and methylethylketoximo radical, the acetoxy radical being preferred.
  • organosilicon compounds (A) used according to the invention are particularly preferably those of the formula
  • R and R 1 have one of the meanings given above, e is 30 to 3000 and f is 1 or 2.
  • f is 2 if R 1 is hydrogen and f is 1 if R 1 is hydrogen.
  • organosilicon compounds (A) are (MeO) 2 MeSiO [SiMe 2 0] 200 _ 2000 SiMe (OMe) 2 ,
  • the organosilicon compounds (A) used according to the invention have a viscosity of preferably 100 to 10 6 Pas, particularly preferably 10 3 to 350 000 mPas, in each case at 25 ° C.
  • organosilicon compounds (A) are commercially available products or can be prepared by methods customary in silicon chemistry.
  • radicals R 2 are the one-valent examples given for radical R.
  • the radical R 2 is preferably hydrocarbon radicals having 1 to 18 carbon atoms, which are optionally substituted by halogen atoms, amino groups, ether groups, ester groups, epoxy groups, mercapto groups, cyano groups or (poly) glycol radicals, the latter consisting of oxyethylene and / or oxypropyl radicals units are built up, particularly preferably around alkyl radicals with 1 to 12 carbon atoms, in particular around the methyl radical.
  • radicals R 3 are the monovalent examples given for radical R as well as divalent optionally substituted hydrocarbon radicals having 1 to 30 carbon atoms.
  • the radical R 3 is preferably hydrocarbon radicals having 1 to 8 carbon atoms, particularly preferably alkyl radicals having 1 to 6 carbon atoms and benzyl radicals.
  • the radical R 3 can also be a divalent radical derived therefrom, so that for example two radicals R 3 form a ring with the nitrogen atom.
  • anion X examples include organic anions, such as carboxylate ions, enolate ions and sulfonate ions, as well as inorganic anionic such as halide ions such as fluoride ions, chloride ions, bromide ions and iodide ions, and sulfate ions.
  • organic anions such as carboxylate ions, enolate ions and sulfonate ions
  • inorganic anionic such as halide ions such as fluoride ions, chloride ions, bromide ions and iodide ions, and sulfate ions.
  • Anion X ′′ is preferably carboxylate ion and halide ion, particularly preferably chloride ion and acetate ion.
  • radical R 4 are divalent linear, cyclic or branched, saturated or unsaturated hydrocarbon radicals which are interrupted once or several times by oxygen atoms, like all alkylene radicals, arylene radicals,
  • the radical R 4 is preferably alkylene radicals and - (CH 2 ) 3 OCH 2 -CH (OH) -CH 2 - and - (CH 2 ) 3 OCH 2 -CH [-CH 2 (OH)] -, particularly preferably around - (CH 2 ) 3 OCH 2 -CH (OH) -CH 2 - and - (CH 2 ) 3 OCH 2 -CH [-CH 2 (OH)] -.
  • the organosilicon compounds (B) used according to the invention are preferably those of the formula
  • D 1 represents a hydrogen atom, hydroxyl radical, halide radical, a radical -NR * 2 or a monovalent organic radical, where R * can be the same or different and represents a hydrogen atom or a monovalent, optionally substituted hydrocarbon radical and the radical -NR * 2 also as ammonium - salt may be present, and
  • D 2 is a group of the formula - (OSiR 2 2 ) g -R 4 k -D 1 means with R 2 , R 3 , D 1 , X ⁇ and R 4 equal to one of the meanings given above, the two radicals D 1 in each polymer molecule of formula (III) may be the same or different, and d is an integer from 1 to 200, h is 0 or 1, k is 0 or 1, g is a number from 0 to 1000 and n is an integer Number is from 1 to 50.
  • Examples of D 1 equal to halide are -Cl and -Br and for -NR * 2 the -N (CH 3 ) 2 -rest.
  • the organosilicon compounds (B) used according to the invention are particularly preferably polymers of the formula (III) where R 4 is alkylene radicals having at least 4 carbon atoms and at least one hydroxyl group, - (CH 2 ) 3 OCH 2 -CH (OH) - CH 2 - and - (CH 2 ) 3 OCH 2 -CH [-CH 2 (OH)] -, particularly preferably around - (CH 2 ) 3 OCH 2 -CH (OH) -CH 2 - and - (CH 2 ) 3 OCH 2 -CH [-CH 2 (OH)] -.
  • Examples of the organosilicon compounds (B) used according to the invention are
  • D 1 Cl
  • D 2 -OSi (CH 3 ) 2 (CH 2 ) 3 OCH 2 CH (OH) CH 2 -N (CH 3 ) 2 and n approx. 20,
  • D 1 (CH 3 ) 2 N-
  • D 2 - (OSi (CH 3 ) 2 ) g (CH 2 ) 3 OCH 2 CH (OH) CH 2 -N (CH 3 ) 2
  • n approx. 20
  • the organosilicon compounds (B) used according to the invention have a viscosity of preferably 10 4 to 10 8 mPas, particularly preferably 10 5 to 5 * 10 7 mPas, in each case at 25 ° C.
  • organosilicon compounds (B) used according to the invention are commercially available products or can be prepared by known processes, for example by reacting the corresponding epoxy-functional silanes and / or siloxanes with dialkylammonium salts such as, for example, dimethylammonium chloride or by reacting the corresponding amino compounds with alkyl halides.
  • crosslinking agents (C) optionally used in the compositions according to the invention can be any, previously known crosslinking agents with at least three condensable radicals, such as, for example, silanes or siloxanes with at least three organyloxy groups.
  • crosslinking agents (C) optionally used in the compositions according to the invention are preferably organosilicon compounds of the formula
  • R 5 can be the same or different and means monovalent, optionally substituted hydrocarbon radicals which can be interrupted by oxygen atoms, R 5 can be the same or different and has the meaning given above for R 1 ,
  • Z can be the same or different and has a meaning given for Y, k is 0, 1, 2, 3 or 4, preferably 2 or 3, particularly preferably 3, and
  • the partial hydrolyzates can be partial homohydrolysates, i.e. Partial hydrolyzates of some kind of organosilicon compound of formula (V) as well as partial hydrolyzates, i.e. Partial hydrolysates of at least two different types of organosilicon compounds of the formula (V).
  • crosslinking agents (C) used in the compositions according to the invention are partial hydrolysates of organosilicon compounds of the formula (V), preference is given to those having up to 6 silicon atoms.
  • radical R 5 examples are the examples mentioned above for radical R 1 .
  • the radical R 6 is preferably a hydrogen atom and alkyl radicals, particularly preferably a hydrogen atom and alkyl radicals having 1 to 4 carbon atoms, in particular a hydrogen atom, the methyl and the ethyl radical.
  • radical R 5 are the monovalent examples mentioned above for radical R, hydrocarbon radicals having 1 to 12 carbon atoms being preferred and the methyl and vinyl radicals being particularly preferred.
  • Z are the examples given for Y, preference being given to acetooxy radicals and methylethylketoximo radicals.
  • crosslinking agents (C) optionally used in the compositions according to the invention are particularly preferably tetramethoxysilane, tetraethoxysilane, tetrapropoxysilane, tetrabutoxysilane, methyltrimethoxysilane, methyltriethoxysilane, vinyltrimethoxysilane, vinyltriethoxysimylililililtrilyltrimyloxysilane, phenyltriethoxysimylilililililililililililililililtrilyltrimethoxysilane, phenyltriethoxysimylilililililililililililtrilyltrimethoxysilane, phenyltriethoxysimylilililililililililtrilyltrimethoxysilane, phenyltriethoxysimyliloxililililtrilyltriloxysilane, phenyltri
  • crosslinking agents (C) optionally used in the compositions according to the invention are commercially available products or can be prepared by processes known in silicon chemistry.
  • compositions according to the invention contain crosslinking agents (C), the amounts are preferably 0.01 to 20 parts by weight, particularly preferably 0.5 to 10 parts by weight, in particular 1.0 to 5.0 parts by weight, in each case based on 100 parts by weight of organopolysiloxane ( A).
  • compositions according to the invention can now contain all other substances which have also been used in compositions which can be crosslinked by the condensation reaction, such as, for example, gates (D), plasticizers (E), fillers (F), adhesion promoters (G) and additives (H).
  • catalysts (D) are the previously known titanium compounds and organic tin compounds, such as di-n-butyltin dilaurate and di-n-butyltin diacetate, di-n-butyltin oxide, dioctyltin diacetate, dioctyltin dilaurate, dioctyltin oxide and reaction products of these compounds with alkoxoxysilanesilane such as tetraoxysilanes , with di-n-butyltin diacetate and dibutyltin oxide in tetraethylsilicate hydrolyzate being preferred and di-n-butyltin oxide in tetraethylsilicate hydrolyzate being particularly preferred.
  • organic tin compounds such as di-n-butyltin dilaurate and di-n-butyltin diacetate, di-n-butyltin oxide, dioctyltin diacetate
  • compositions according to the invention contain catalyst (D), they are amounts of preferably 0.01 to 3 parts by weight, preferably 0.05 to 2 parts by weight, in each case based on 100 parts by weight of component (A).
  • plasticizers (E) are dimethylpolysiloxanes which are liquid at room temperature and are endblocked by trimethylsiloxy groups, in particular with viscosities at 25 ° C. in the range between 50 and 1000 mPas, and high-boiling hydrocarbons, such as paraffin oils or mineral oils consisting of naphthenic and paraffinic Units.
  • compositions according to the invention contain plasticizers (E) in amounts of preferably 0 to 300 parts by weight, particularly preferably 10 to 200 parts by weight, in particular 20 to 100 parts by weight, in each case based on 100 parts by weight of organopolysiloxane (A).
  • fillers (F) are non-reinforcing fillers, ie 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, titanium, iron - or Zinc oxides or their mixed oxides, barium sulfate, calcium carbonate, gypsum, silicon nitride, silicon carbide, boron nitride, glass and plastic powder, such as polyacrylonitrile powder; reinforcing fillers, ie fillers with a BET surface area of more than 50 m 2 / g, such as pyrogenically prepared silica, precipitated silica, precipitated chalk, carbon black, such as furnace black and acetylene black and silicon-aluminum mixed oxides having a large BET surface area; fibrous fillers such as asbestos and plastic fibers.
  • BET surface area such as quartz, diatomaceous
  • fillers mentioned can be rendered hydrophobic, for example by treatment with organosilanes or organosiloxanes or with stearic acid or by etherification of hydroxyl groups to alkoxy groups. If fillers (E) are used, they are preferably hydrophilic fumed silica and precipitated or ground calcium carbonate.
  • compositions according to the invention contain fillers (F) in amounts of preferably 0 to 300 parts by weight, particularly preferably 1 to 200 parts by weight, in particular 5 to 200 parts by weight, in each case based on 100 parts by weight of organopolysiloxane (A).
  • adhesion promoters (G) used in the compositions according to the invention are silanes and organopolysiloxanes with functional groups, such as, for example, those with glycidoxypropyl or methacryloxypropyl radicals and tetraalkoxysilanes.
  • compositions according to the invention contain adhesion promoters (G) in amounts of preferably 0 to 50 parts by weight, particularly preferably 1 to 20 parts by weight, in particular 1 to 10 parts by weight parts by weight, each based on 100 parts by weight of organopolysiloxane (A).
  • additives (H) are pigments, dyes, fragrances, oxidation inhibitors, agents for influencing the electrical properties, such as conductive carbon black, flame retardants, light stabilizers and agents for prolonging the skin formation time, such as silanes with a SiC-bound mer - captoalkyl radical, cell-producing agents, for example Azodicarbonamide, heat stabilizers and thixotropic agents, such as, for example, phosphoric acid esters, and organic solvents, such as alkylates.
  • additives (H) are pigments, dyes, fragrances, oxidation inhibitors, agents for influencing the electrical properties, such as conductive carbon black, flame retardants, light stabilizers and agents for prolonging the skin formation time, such as silanes with a SiC-bound mer - captoalkyl radical, cell-producing agents, for example Azodicarbonamide, heat stabilizers and thixotropic agents, such as, for example, phosphoric acid esters, and organic solvents, such as al
  • compositions according to the invention contain additives (H) in amounts of preferably 0 to 100 parts by weight, particularly preferably 0 to 30 parts by weight, in particular 0 to 10 parts by weight, in each case based on 100 parts by weight of organopolysiloxane (A).
  • compositions according to the invention are particularly preferably those which consist of
  • (D) catalyst optionally (E) plasticizer, optionally (F) fillers, optionally (G) adhesion promoters and optionally (H) additives.
  • compositions according to the invention all of the constituents can be mixed with one another in any order. This mixing can take place at room temperature and the pressure of the surrounding atmosphere, ie about 900 to 1100 hPa. If desired, this mixing can also take place at higher temperatures, e.g. at temperatures in the range of 35 ° C to 135 ° C.
  • compositions according to the invention can each be a type of such constituent or a mixture of at least two different types of such constituents.
  • compositions according to the invention are preferably crosslinked at room temperature. If desired, it can also be used at temperatures higher or lower than room temperature, e.g. at -5 ° to 15 ° C or at 30 ° to 50 ° C and / or by means of concentrations of water exceeding the normal water content of the air.
  • the crosslinking is preferably carried out at a pressure of 100 to 1100 hPa, in particular at the pressure of the surrounding atmosphere.
  • the present invention furthermore relates to moldings produced by crosslinking the compositions according to the invention.
  • the compositions according to the invention can be used for all purposes for which compositions which can be stored with the exclusion of water and which crosslink to form elastomers when water is admitted at room temperature can be used.
  • compositions of the invention are therefore extremely suitable, for example, as sealing compounds for joints, including vertical joints, and similar empty spaces, e.g. 10 to 40 mm clear width, e.g. of buildings, land, water and aircraft, or as adhesives or cementing compounds, e.g. in window construction or in the production of aquariums or showcases, as well as e.g. for the production of protective coatings, including those surfaces which are exposed to the constant action of fresh or sea water, or coatings which prevent sliding, or of rubber-elastic molded articles, and for the insulation of electrical or electronic devices.
  • sealing compounds for joints including vertical joints, and similar empty spaces, e.g. 10 to 40 mm clear width, e.g. of buildings, land, water and aircraft, or as adhesives or cementing compounds, e.g. in window construction or in the production of aquariums or showcases, as well as e.g. for the production of protective coatings, including those surfaces which are exposed to the constant action of fresh or sea water, or coatings which prevent sliding, or of
  • compositions of the invention have the advantage that they are easy to manufacture and have a biocidal action over a long period of time.
  • compositions according to the invention have the advantage that the tendency to discolour both the not yet cured composition and the cured molded articles is extremely low due to the biocidal treatment.
  • crosslinkable compositions according to the invention have the advantage that they are distinguished by a very high storage stability and a high crosslinking rate.
  • Test specimens according to DIN EN ISO 846 are produced from the vulcanizate plates thus produced and tested according to method B as described in the standard. The results are shown in Table 1.
  • Test specimens are produced from the mass obtained in this way as described in Example 1 and tested in accordance with DIN EN ISO 846. The results are shown in Table 1.
  • Example 1 The procedure described in Example 1 is repeated with the modification that twice the amount of the polyquaternary polysiloxane has been used.
  • Test specimens are produced from the mass obtained in this way as described in Example 1 and tested in accordance with DIN EN ISO 846. The results are shown in Table 1.
  • Example 4 233 g of dimethylammonium chloride were dissolved in 1700 ml of water. 2238 g of a polysiloxane consisting of (3-glycidoxypropyl) dimethylsiloxy and dimethylsiloxy units with an average of 8 silicon atoms and an epoxy group content of 2.4 mmol / g are added to the solution, and the mixture is heated under reflux with thorough stirring , The reaction mixture was stirred for 6 hours at 105-110 ° C, the reaction mixture changing from colorless cloudy to clear yellow. The solvent was then removed in vacuo at 120 ° C. The reaction product was a dark yellow, highly viscous oil with a viscosity of approx. 6 * 10 6 mPas. The IH-NMR spectroscopic examination confirmed the formation of a polyquaternary polysiloxane with about 30 to 35 repetition units on average according to the formula
  • 35 g of the polyquaternary polysiloxane thus produced 1400 g of an, ⁇ -dihydroxypolydimethylsiloxane with a viscosity of 80,000 mPas, 600 g of a polydimethylsiloxane with -OSi (CH 3 ) 3 end groups and a viscosity of 100 mPas, 90 g
  • Ethyltriacetoxysilane and 190 g of a pyrogenic hydrophilic silica with a specific surface area of 150 m 2 / g were mixed homogeneously in vacuo in a planetary mixer. Then 0.5 g of dibutyltin diacetate was added and homogenized again for 5 minutes.
  • Test specimens are produced from the mass obtained in this way as described in Example 1 and tested in accordance with DIN EN ISO 846. The results are shown in Table 1.

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Abstract

L'invention concerne des produits réticulables à base de composés organosilicium à propriétés biostatiques, ainsi que leur procédé de fabrication et leur utilisation. Les produits réticulables sont caractérisés en ce qu'ils comprennent des composés organosilicium présentant des groupes ammonium quaternaire.
EP04803981A 2003-12-22 2004-12-16 Produits reticulables a base de composes organosilicium Withdrawn EP1694773A2 (fr)

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DE10360469A DE10360469A1 (de) 2003-12-22 2003-12-22 Vernetzbare Massen auf der Basis von Organosiliciumverbindungen
PCT/EP2004/014370 WO2005063872A2 (fr) 2003-12-22 2004-12-16 Produits reticulables a base de composes organosilicium

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EP (1) EP1694773A2 (fr)
JP (1) JP2007515530A (fr)
KR (1) KR100753590B1 (fr)
CN (1) CN1898332A (fr)
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WO (1) WO2005063872A2 (fr)

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US7875149B2 (en) 2005-06-08 2011-01-25 Ppg Industries Ohio, Inc. Aircraft adhesive
WO2007099042A1 (fr) * 2006-02-28 2007-09-07 Ciba Holding Inc. Composés antimicrobiens
DE102006026227A1 (de) * 2006-06-06 2007-12-13 Wacker Chemie Ag Vernetzbare Massen auf der Basis von Organosiliciumverbindungen
DE102006036556A1 (de) 2006-08-04 2008-02-07 Wacker Chemie Ag Vernetzbare Massen auf der Basis von Organosiliciumverbindungen
DE102008042632A1 (de) * 2008-10-06 2010-04-08 Wacker Chemie Ag Vernetzbare Massen auf der Basis von Organosiliciumverbindungen
US8742012B2 (en) * 2010-10-21 2014-06-03 Ppg Industries Ohio, Inc. Thermosetting film-forming compositions that produce atrane-containing cured coatings
DE102015201099A1 (de) * 2015-01-22 2016-07-28 Wacker Chemie Ag Vernetzbare Beschichtungsmassen auf Basis von organyloxysilanterminierten Polymeren
CN109699644A (zh) * 2018-12-28 2019-05-03 东南大学苏州医疗器械研究院 非释放性抗菌材料及其应用

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US20070100110A1 (en) 2007-05-03
DE10360469A1 (de) 2005-07-14
WO2005063872A2 (fr) 2005-07-14
KR100753590B1 (ko) 2007-08-30
KR20060103928A (ko) 2006-10-04
CN1898332A (zh) 2007-01-17
WO2005063872A3 (fr) 2006-02-23
JP2007515530A (ja) 2007-06-14

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