EP0000929B1 - Compositions à base de polysiloxanes convertibles en élastomères par réticulation - Google Patents

Compositions à base de polysiloxanes convertibles en élastomères par réticulation Download PDF

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EP0000929B1
EP0000929B1 EP78100691A EP78100691A EP0000929B1 EP 0000929 B1 EP0000929 B1 EP 0000929B1 EP 78100691 A EP78100691 A EP 78100691A EP 78100691 A EP78100691 A EP 78100691A EP 0000929 B1 EP0000929 B1 EP 0000929B1
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denotes
radicals
silicon
bonded
formula
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EP0000929A1 (fr
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Erhard Dr. Bosch
Karl Braunsperger
August Dr. Schiller
Eckhart Dr. Louis
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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
    • C08G77/04—Polysiloxanes
    • C08G77/045—Polysiloxanes containing less than 25 silicon atoms
    • 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
    • C08G77/26—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
    • C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S528/00—Synthetic resins or natural rubbers -- part of the class 520 series
    • Y10S528/901—Room temperature curable silicon-containing polymer
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
    • Y10T428/31609—Particulate metal or metal compound-containing
    • Y10T428/31612—As silicone, silane or siloxane
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31652—Of asbestos
    • Y10T428/31663—As siloxane, silicone or silane
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31678—Of metal

Definitions

  • constituent (3) is at least one silane, that is to say a monomeric silicon compound, this silane, in addition to at least one amino group bonded to silicon via carbon, at least one monovalent hydrocarbon radical which is bonded to silicon via oxygen and is optionally substituted by an amino or alkoxy group contains.
  • the compositions according to the invention have the particular advantage that they crosslink completely even in thicker layers.
  • the compositions according to the invention are completely crosslinked in thicker layers even if they do not contain any condensation catalysts, such as dibutyltin dilaurate.
  • the invention relates to the exclusion of water-storable masses of (1) diorganopolysiloxane having end groups capable of condensation when water is admitted at room temperature, (2) a total of at least three amino groups bonded to silicon via nitrogen and / or oxime groups bonded to silicon via oxygen per molecule of silicon compound and at least one (3) organosilicon compound with at least one amino group bonded to silicon via carbon as at least one further constituent, characterized in that at least part of organosilicon compound (3) contains at least one siloxane oxygen atom and in amounts of 0.1 to 20 percent by weight, based on the total weight of the mass, is included.
  • compositions according to the invention can be prepared from the same diorganopolysiloxanes (1) which have end groups capable of condensation and from which the hitherto known compositions of diorganopolysiloxane which have condensable end groups and which crosslink under the exclusion of water and which adhere to water when exposed to water at room temperature, and a total of at least three amino groups bonded to silicon via nitrogen and / or oxime groups bonded to silicon via oxygen could be prepared per silicon compound having a molecule.
  • the diorganopolysiloxanes (1) which are mostly used for the production of such compositions and which are also preferably used in the context of the invention have diorganopolysiloxanes (1) by the general formula are reproduced.
  • R 3 means identical or different, monovalent, optionally substituted and / or polymeric hydrocarbon radicals and x is an integer with a value of at least 10.
  • siloxane units in addition to the diorganosiloxane units (SiR30).
  • examples of such other siloxane units, which are usually only present as impurities, are those of the formulas R 3 SiO 3/2 , R 3 3 SiO 1/2 and Si0 4 , z , where R 3 has the meaning given above for each.
  • the amount of such siloxane units as diorganosiloxane units is preferably at most 10 mol percent, in particular at most 1 mol percent, in each case based on the weight of the diorganopolysiloxanes (1).
  • the hydroxyl groups in the above-mentioned diorganopolysiloxane group having condensable end groups can, if desired, be completely or partially replaced by condensable groups other than Si-bonded hydroxyl groups.
  • Examples of such other groups capable of condensation are connected in particular via nitrogen to silicon bonded amino groups, as will be explained in more detail below, through oxygen to silicon-bonded oxime groups, as will also be discussed in more detail below, alkoxy groups having 1 to 5 carbon atoms and Alkoxyalkylenoxy phenomenon 1 to 5 carbon atoms, like the rest of the formula CH 3 0CH Z CH z O-.
  • hydrocarbon radicals R 3 are alkyl radicals, such as the methyl, ethyl, n-propyl and isopropyl radical and octadecyl radicals; Alkenyl groups such as the vinyl and allyl groups; cycloaliphatic hydrocarbon radicals, such as the cyclopentyl and cyclohexyl radical and methylcyclohexyl and cyclohexenyl radicals; Aryl groups such as phenyl groups and xenyl groups; Aralkyl radicals, such as the benzyl, beta-phenylethyl and beta-phenylpropyl radicals; and alkaryl radicals, such as tolyl radicals.
  • alkyl radicals such as the methyl, ethyl, n-propyl and isopropyl radical and octadecyl radicals
  • Alkenyl groups such as the vinyl and allyl groups
  • Substituted hydrocarbon radicals R 3 are haloaryl radicals, such as chlorophenyl and bromophenyl radicals; and cyanalkyl radicals, such as the beta-cyanoethyl radical, are preferred.
  • substituted polymeric and unsubstituted polymeric hydrocarbon radicals R 3 where such polymeric hydrocarbon radicals can also be referred to as modifying hydrocarbon radicals are, in particular, those which, when polymerizable compounds are polymerized by means of free radicals in the presence of diorganopolysiloxanes of the general formula where x has the meaning given above and R is the same or different, monovalent, optionally substituted hydrocarbon radicals are formed.
  • Examples of polymerizable compounds which can be used in such a polymerization carried out in the presence of diorganopolysiloxane are vinyl acetate, ethylene, styrene, acrylic acid, methacrylic acid, acrylic acid esters such as n-butyl acrylate, methacrylic acid esters such as n-butyl methacrylate, acrylonitrile and methacrylonitrile, and Mixtures of at least two of the monomers mentioned, such as mixtures of vinyl acetate and ethylene.
  • At least 50% of the number of SiC-bonded residues in diorganopolysiloxane (1) and thus the residues R 3 in the formulas given above are preferably methyl residues.
  • the diorganopolysiloxanes (1) which have condensable end groups can be homopolymers or copolymers. Mixtures of different diorganopolysiloxanes with condensable end groups can be used.
  • the viscosity of the diorganopolysiloxanes having condensable end groups is advantageously 100 to 500,000 mPa.s at 25 ° C.
  • a total of at least three amino groups bonded to silicon via nitrogen and / or oxime groups bonded via silicon to oxygen per molecule can also contain the same silicon compounds with a total of at least three amino groups bonded to silicon via nitrogen and / or Oxime groups bonded to silicon via oxygen are used per molecule, which have also been used hitherto for the preparation of compositions which can be stored in the absence of water and which crosslink to form elastomers when water is admitted at room temperature by mixing such a silicon compound with diorganopolysiloxane having condensable end groups.
  • silicon compounds (2) which can be used in the context of the invention are thus aminosilanes of the general formula wherein R has the meaning given above for it, R 1 is hydrogen or a monovalent, optionally substituted hydrocarbon radical and a is 0 or 1, and their partial hydrolysates containing at most 10 silicon atoms per molecule.
  • substituted and unsubstituted hydrocarbon radicals R also apply in full to the substituted and unsubstituted hydrocarbon radicals R 1 .
  • Further examples of hydrocarbon radicals R 1 are the n-butyl, sec-butyl and the tert-butyl radical.
  • Preferred radicals R 1 are the sec-butyl and the cyclohexyl radical.
  • examples of silicon compounds (2) are also silanes of the general formula wherein R, R 'and X each have the meaning given above and c is on average at least 0.1, preferably at least 0.5 and at most 2.9, the sum of a + c being at most 3.
  • silicon compounds (2) are methyltris (n-butylamino) silane, methyltris (sec.butylamino) silane, methyltris (cyclohexylamino) silane, methyltris (methylethylketoxirn) silane, methylbis (methylethylketoxime) -cyclohexylaminosilane and methyltris (acetone oxime) -silane.
  • Mixtures of different silicon compounds (2) e.g. a mixture of 1 mol of methyl tris (cyclohexylamino) silane and 2 mol of methyl tris (methyl ethyl ketoxime) silane can be used.
  • the total of at least three amino groups per molecule bonded to silicon via nitrogen and / or oxime groups bonded to silicon via oxygen (2) is preferably used in amounts such that there are a total of at least three amino groups bonded to silicon via nitrogen and / or oxime groups bonded to silicon via oxygen per end group capable of condensation in the diorganopolysiloxane (1).
  • 0.2 to 15 percent by weight, usually 1 to 8 percent by weight, based in each case on the total weight of the particular mass, of silicon compound (2) is used.
  • organosilicon compound (3) with at least one amino group bonded to silicon via carbon and at least one siloxane oxygen atom it is also possible, for example, to use compounds of the general formula where R and a each have the meaning given above, are used. Particularly because of the easy accessibility, organosilicon compounds (3) are those of the general formula prefers.
  • R has the meaning given above for it, A means identical or different radicals of the formula where R 1 and a each have the meaning given above, Q is oxygen or the grouping -NR 'and p is an integer from 1 to 10, Y are identical or different radicals of the formula where A, R and a each have the meaning given above, R I is hydrogen or the same or different monovalent hydrocarbon radicals which are optionally interrupted by at least one ether oxygen atom, b O, 1, 2 or 3 and the sum of a + b is at most 3, m means 0 or an integer from 1 to 2,000 and n O or an integer from 1 to 1,000, with the proviso that at least one radical A is present per organopolysiloxane (3).
  • R is also preferably the methyl radical in the organosilicon compound (3).
  • radicals A are those of the following formulas:
  • R 1 in group A preferably denotes hydrogen. However, R 1 does not always have to be hydrogen, as is the case with the grouping is illustrated. As can also be seen from the above formulas, the values p in one and the same grouping A and thus also in different groupings A can be the same or different.
  • radicals A are those of the general formula where Q has the meaning given above, preferred.
  • the radicals R 2 preferably have 1 to 18 carbon atoms, but the methyl and ethyl radicals are particularly preferred.
  • the most important example of a hydrocarbon radical R 2 interrupted by an ether oxygen atom is the methoxyethylene radical.
  • M is preferably an integer from 3 to 1,000. It is further preferred that in the compounds of the general formula Y (OSiR 2 ) m (OSiAR) n OY at most 100 units of the formula R z SiO there are a for each grouping.
  • organosilicon compounds (3) of the preferred type are those of the general formula where R, A and n each have the meaning given above and m 'is an integer with a value of at least 3.
  • the preparation of such organopolysiloxanes is known, for example from FR-PS 11 84 097, published: July 16, 1959, applicant: Union Carbide Corporation, and FR-PS 12 97 045, published by "Bulletin founded de la Propriete industrial" No. 25 1962, applicant: Union Carbide Corporation.
  • organosilicon compounds (3) of the preferred type are those of the general formula where R, R 2 , A, m 'and n each have the meaning given above.
  • organopolysiloxanes can, for example, by reacting at least one compound of the general formula where A, R and R 2 each have the meaning given above, with at least one organopolysiloxane of the general formula where R and m 'each have the meaning given above, optionally in the presence of a condensation catalyst, such as sodium hydroxide or dibutyltin dilaurate, with elimination of a compound of the general formula getting produced.
  • a condensation catalyst such as sodium hydroxide or dibutyltin dilaurate
  • organosilicon compounds (3) of the preferred type are also those of the general formula wherein R, R 2 , A, b, m 'and n each have the meaning given above, with the proviso that there is at least one group A per molecule.
  • the preparation of such organopolysiloxanes is also known, for example from DE-OS 23 39 761, published February 21, 1974, applicant: Stauffer Chemical Co., and FR-PS 12 94 235, published by "Bulletin founded de la Propriete industrial no. 21 of 1962, applicant: Dow Corning Corporation.
  • siloxane units SiR 2 O and SiARO can also be present within or along the siloxane chains of the formulas given above for organosilicon compounds (3).
  • examples of such other siloxane units are those of the formulas RSi0 3 , 2 , R 3 SiO 1/2 and Si0 "2, where R in each case has the meaning given above.
  • the amounts of such siloxane units as diorganosiloxane units are also in the organosilicon compounds (3 ) preferably at most 10 mole percent.
  • the organosilicon compounds (3) are used in amounts of 0.1 to 20 percent by weight, in particular 0.1 to 5 percent by weight, in each case based on the total weight of the composition.
  • At least one siloxane oxygen atom can also be used in the preparation of the compositions according to the invention which have also been used up to now in the preparation of compositions from the silicon compounds (1) and (2) which can be stored in the absence of water and which crosslink to form elastomers when water enters at room temperature could.
  • Examples of such additionally usable substances are reinforced fillers, non-reinforcing fillers, pigments, soluble dyes, fragrances, organopolysiloxane resins, including those made from (CH 3 ) 3 SiO 1/2 and SiO 4/2 units, organic resins, such as polyvinyl chloride powder, corrosion inhibitors , Oxidation inhibitors, heat stabilizers, solvents, other agents for improving the adhesion of the elastomers produced from the compositions to the substrates on which the elastomers were produced, such as the compound of the formula CH 3 Si [O (CH 2 ) 2 NH 2 ] 2 ( CH 2 ) 3 O (CH 2 ) 2 NH 2 , condensation catalysts, such as tin salts or organotin salts of carboxylic acids, for example dibutyltin dilaurate or aliphatic basic nitrogen compounds, for example 3-ethoxypropylamine-1 or n-hexylamine, plasticizers, such as dimethylpolys
  • reinforcing fillers that is to say fillers with a surface area of at least 50 m 2 / g
  • fillers with a surface area of at least 50 m 2 / g are, in particular, pyrogenically produced silicon dioxide, silica hydrogels dehydrated while maintaining the structure and other types of precipitated silicon dioxide with a surface area of at least 50 ml / g.
  • other fillers with a surface area of at least 50 m 2 / g can be used instead of the named types of silicon dioxide or together with these types of silicon dioxide.
  • examples of such other fillers are metal oxides, such as titanium dioxide, ferric oxide, aluminum oxide and zinc oxide, provided that they each have a surface area of at least 50 m 2 / g.
  • non-reinforcing fillers that is to say fillers with a surface area of less than 50 ml / g
  • quartz powder diatomaceous earth, pebble chalk, Neuburg chalk, calcium silicate, zirconium silicate, calcium carbonate, for example in the form of ground chalk, and calcined aluminum silicate and powdered sodium aluminum silicate with molecular sieve properties.
  • the reinforcing and the non-reinforcing fillers can be made hydrophobic, for example by treatment with trimethylethoxysilane or stearic acid. If desired, such treatment may have been carried out, for example, in a ball mill.
  • Fibrous fillers such as asbestos and glass fibers, in particular those with an average length of at most 0.5 mm, and / or organic fibers can also be used.
  • compositions according to the invention all constituents of the particular composition can be mixed together in any order. This mixing is expediently carried out at room temperature and with the exclusion of water. If desired, this mixing can also take place at higher temperatures, e.g. at a temperature in the range of 35 ° C to 150 ° C.
  • the normal water content of the air is sufficient for the crosslinking of the compositions according to the invention. If desired, however, the crosslinking can also be carried out at temperatures higher than room temperature or lower temperatures than room temperature, e.g. at 5 ° to 10 ° C, and / or by means of concentrations of water exceeding the normal water content of the air.
  • compositions according to the invention adhere to these substrates very good even without the use of the usual primers.
  • substrates such as glass, porcelain, earthenware, mortar, aluminum, brass, stainless steel, galvanized sheet metal, wood, paper or plastics, such as polyvinyl chloride, polyester, polystyrene or polymethyl methacrylate, adhere to these substrates very good even without the use of the usual primers.
  • the compositions according to the invention are therefore not only suitable for sealing joints, including vertically running joints, and similar empty spaces with clear widths of, for example 1 mm to 50 mm, for example of land, water or aircraft as well as of buildings, including those made of lightweight building blocks or prefabricated components.
  • compositions of the invention are also excellent as adhesives or putties, as well as for producing electrical conductor insulations and for producing coatings on a wide variety of substrates, such as the adhesive-repellent finishing of paper and other coatings, such as those of metals, artificial and natural stones or non-woven textiles.
  • Example 2 The procedure described in Example 1 is repeated with the modification that 2 parts of an organosilicon compound are used as the organosilicon compound with amino groups bonded to silicon via carbon and siloxane oxygen atoms, which are obtained by reaction of the silane of the formula with a dimethylpolysiloxane each having an Si-bonded hydroxyl group in the terminal units, the amount of Si-bonded hydroxyl groups being 3.7%.
  • this organosilicon compound consisted of 0.6 mol percent Si-bonded C 2 H 5 O groups, 95.4% dimethylsiloxane units and 4 mol percent groupings of the formula
  • Example 1 The procedure described in Example 1 is repeated with the modification that no organosilicon compound with amino groups bonded to silicon via carbon and siloxane oxygen atoms is used.
  • Example 3 The procedure described in Example 3 is repeated with the modification that no organosilicon compound with amino groups bonded to silicon via carbon and siloxane oxygen atoms is used.
  • the masses prepared according to Examples 1 to 3 and also the masses prepared according to Comparative Experiment V 1 and V 2 can be stored in the absence of water and cure to give elastomers under the action of the water vapor contained in the air.
  • Example 3 The procedure described in Example 3 is repeated with the modification that 2 parts of the silane of the formula instead of the 2 parts of the organosilicon compound described in Example 1 with amino groups bonded to silicon via carbon and siloxane oxygen atoms.
  • the mass produced in this way can be stored in the absence of water. However, under the influence of the water vapor contained in the air, the mass only forms a skin on the surface and does not harden into an elastomer.
  • compositions according to the invention would cure even in the absence of a condensation catalyst, because the organosilicon compounds (3) used according to the invention, the organosilicon compounds used according to DE-OS 19 64 502 with an amino group bonded via carbon to silicon, essentially only by the additional Distinguish the presence of siloxane oxygen.

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Claims (3)

1. Matières se conservant à l'abri de l'eau et se réticulant en présence d'eau, à la température ambiante, en donnant des élastomères, constituées (1) d'un poly-diorganosiloxane à groupes terminaux condensables, (2) d'un composé du silicium contenant au total, par molécule, au moins trois groupes amino reliés au silicium par l'azote et/ou groupes oximes reliés au silicium par l'oxygène, et (3), comme constituant supplémentaire, éventuellement parmi d'autres, au moins un composé organosilicique renfermant au moins un groupe amino relié au silicium par du carbone, matières caractérisées en ce qu'au moins une partie du composé organosilicique (3) contient au moins un atome d'oxygène siloxanique et est contenue en des quantités de 0,1 à 20% en poids par rapport au poids total de la matière.
2. Matières selon la revendication 1, caractérisées en ce qu'elles contiennent, comme composé organosilicique (3), au moins un polyorganosiloxane répondant à la formule générale
Figure imgb0033
dans laquelle les R représentent des radicaux hydrocarbonés monovalents, éventuellement substitués, identiques ou différents, les A représentent des radicaux, identiques ou différents, répondant à la formule:
Figure imgb0034
dans laquelle R1 désigne l'hydrogène ou un radical hydrocarboné monovalent éventuellement substitué, Q représente l'oxygène ou un groupement -NR', a est égal à zéro ou à 1 et p est un nombre entier de 1 à 10, les Y représentent des radicaux identiques ou différents, répondant à la formule:
Figure imgb0035
dans laquelle A, R et a ont les significations indiquées ci-dessus pour ces symboles, les RZ représentent l'hydrogène ou des radicaux hydrocarbonés monovalents, éventuellement interrompus par au moins un atome d'oxygène d'éther, identiques ou différents, b est égal à zéro, à 1, à 2 ou à 3 et la somme a+ b est au plus égale à 3, m est égal à zéro ou désigne un nombre entier de 1 à 2000 et n est égal à zéro ou désigne un nombre entier de 1 à 1000, avec la condition qu'il y ait au moins un radical A par polyorganosiloxane (3).
3. Matières selon la revendication 2, caractérisées en ce que les A représentent des radicaux, identiques ou différents, répondant à la formule:
Figure imgb0036
dans laquelle Q a la signification donnée à la revendication 2 pour ce symbole.
EP78100691A 1977-08-18 1978-08-17 Compositions à base de polysiloxanes convertibles en élastomères par réticulation Expired EP0000929B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2737303 1977-08-18
DE2737303A DE2737303C3 (de) 1977-08-18 1977-08-18 Unter Ausschluß von Wasser lagerfähige, bei Zutritt von Wasser bei Raumtemperatur zu Elastomeren vernetzende Formmassen

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EP0000929A1 EP0000929A1 (fr) 1979-03-07
EP0000929B1 true EP0000929B1 (fr) 1981-03-18

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EP78100691A Expired EP0000929B1 (fr) 1977-08-18 1978-08-17 Compositions à base de polysiloxanes convertibles en élastomères par réticulation

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US (1) US4191817A (fr)
EP (1) EP0000929B1 (fr)
JP (1) JPS5443261A (fr)
AT (1) AT383608B (fr)
AU (1) AU521250B2 (fr)
BR (1) BR7805201A (fr)
CA (1) CA1124429A (fr)
DE (2) DE2737303C3 (fr)
IT (1) IT1106889B (fr)
NO (1) NO149697C (fr)
SE (1) SE443989B (fr)

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US4420578A (en) * 1980-11-10 1983-12-13 Diversey Corporation Surface treatment of glass containers
DE3133564A1 (de) * 1981-08-25 1983-03-10 Wacker-Chemie GmbH, 8000 München "silikonkautschuk mit verzoegerter hautbildung"
DE3212008A1 (de) * 1982-03-31 1983-10-06 Wacker Chemie Gmbh Unter ausschluss von wasser lagerfaehige, bei zutritt von wasser bei raumtemperatur zu elastomeren vernetzende massen
DE3303649A1 (de) * 1983-02-03 1984-08-09 Wacker-Chemie GmbH, 8000 München Unter ausschluss von wasser lagerfaehige, bei zutritt von wasser bei raumtemperatur zu elastomeren vernetzende massen
US4551516A (en) * 1983-05-17 1985-11-05 Toray Industries, Inc. Coating composition and the use thereof
DE3323911A1 (de) * 1983-07-02 1985-01-03 Bayer Ag, 5090 Leverkusen Bei raumtemperatur zu elastomeren haertende polyorganosiloxanmassen
US4525566A (en) * 1984-03-02 1985-06-25 Dow Corning Corporation Coating method and silicone composition for PSA release coating
US4530882A (en) * 1984-03-02 1985-07-23 Dow Corning Corporation Coating method and silicone composition for PSA release coating
EP0234720B1 (fr) * 1986-01-21 1991-09-18 General Electric Company Compositions à base d'un caoutchouc de polysiloxane
JPS62276090A (ja) * 1986-05-22 1987-11-30 信越化学工業株式会社 合成繊維用処理剤
JPH0830181B2 (ja) 1986-08-25 1996-03-27 東レ・ダウコ−ニング・シリコ−ン株式会社 ガスケツト・パツキング材組成物
US4814230A (en) * 1988-01-28 1989-03-21 Vockler Larry D Silicone-coated opaque glass
DE3808200A1 (de) * 1988-03-11 1989-09-21 Wacker Chemie Gmbh Bei raumtemperatur zu anstrichvertraeglichen bis ueberstreichbaren elastomeren vernetzende organopolysiloxanmassen
US5088179A (en) * 1990-10-12 1992-02-18 Jmk International, Inc. Method of forming a microwaveable container
DE4137698A1 (de) * 1991-11-15 1993-05-19 Wacker Chemie Gmbh Zinnverbindung enthaltende massen als eine der beiden komponenten von bei raumtemperatur zu organopolysiloxanelastomeren vernetzenden zweikomponentensystemen
US5352491A (en) * 1993-06-11 1994-10-04 Dow Corning Corporation Method for coating using molten organosiloxane compositions
US5302671A (en) * 1993-06-11 1994-04-12 Dow Corning Corporation Moisture-curable compositions containing aminoalkoxy-functional silicone
FR2724661B1 (fr) * 1994-09-16 1997-10-24 Rhone Poulenc Chimie Dispersion silicone aqueuse, reticulable en un elastomere adherent, selon un mecanisme reactionnel de condensation
US6471820B1 (en) 1995-01-05 2002-10-29 3M Innovative Properties Moisture-curable silicone composition
DE60115003T2 (de) * 2000-04-04 2006-08-10 Koninklijke Philips Electronics N.V. Ein digital-analog-wandler
DE10156918A1 (de) * 2001-11-21 2003-06-05 Ge Bayer Silicones Gmbh & Co Anstrichverträgliche bis überstreichbare Polyorganosiloxan-Zusammensetzungen
GB0302840D0 (en) * 2003-02-07 2003-03-12 Dow Corning Process for making silicone emulsions
FR2887552B1 (fr) * 2005-06-24 2007-10-12 Rhodia Chimie Sa Utilisation d'une composition organopolysiloxanique vulcanisable des la temperature ambiante pour former un elastomere auto adherent
KR102036627B1 (ko) 2019-04-24 2019-10-25 주식회사 청호엔텍 플랩형 파이프 스컴 스키머

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GB1171848A (en) * 1966-10-20 1969-11-26 Gen Electric Room Temperature Vulcanizing Silicone Compositions
DE1910014C3 (de) * 1969-02-27 1973-11-15 Wacker-Chemie Gmbh, 8000 Muenchen Unter Ausschluß von Wasser lager fähige, nach Zutritt desselben bei Raumtemperatur zu Elastomeren hartende Organopolysiloxanformmassen
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Also Published As

Publication number Publication date
AU3869278A (en) 1980-02-14
US4191817A (en) 1980-03-04
NO149697C (no) 1984-06-06
JPS5525228B2 (fr) 1980-07-04
DE2737303C3 (de) 1980-07-17
CA1124429A (fr) 1982-05-25
SE7808733L (sv) 1979-02-19
DE2737303B2 (de) 1979-10-18
DE2737303A1 (de) 1979-03-01
IT7850743A0 (it) 1978-08-16
DE2860547D1 (en) 1981-04-16
EP0000929A1 (fr) 1979-03-07
AU521250B2 (en) 1982-03-25
NO149697B (no) 1984-02-27
NO782794L (no) 1979-02-20
IT1106889B (it) 1985-11-18
AT383608B (de) 1987-07-27
BR7805201A (pt) 1979-05-02
JPS5443261A (en) 1979-04-05
SE443989B (sv) 1986-03-17
ATA595678A (de) 1986-12-15

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