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    Bonding thermoplastic resins to inorganic materials
    21.
    发明授权
    Bonding thermoplastic resins to inorganic materials 失效
    将热塑性树脂粘合到无机材料上

    公开(公告)号：US3306800A

    公开(公告)日：1967-02-28

    申请号：US36292364

    申请日：1964-04-27

    Applicant: DOW CORNING

    Inventor： PLUEDDEMANN EDWIN P

    IPC: A61K6/00 ,  B32B15/08 ,  B32B27/00 ,  C03C17/32 ,  C08F8/42 ,  C08G77/00 ,  C08J5/12 ,  C09D201/02 ,  C09J157/00

    CPC classification number: B32B27/00 ,  B32B15/08 ,  C03C17/32 ,  C08F8/42 ,  C08G77/00 ,  C08J5/124 ,  C09D201/02 ,  C09J157/00

    Abstract: 1,084,071. Artificial teeth. DOW CORNING CORPORATION. Feb. 11, 1965 [April 27, 1964], No. 6029/65. Heading A5R. [Also in Divisions B2, B5 and C3] Thermoplastic resins (including thermoplastic cellulose derivatives) are bonded to siliceous materials, such as glass sheets or fabrics, asbestos, ceramics, or silicone elastomers, or to metals such as aluminium or steel, or metal oxides, by bringing the components together after having rendered the surface of one of them plastic, as by heating or applying a solvent, and after applying to one component a polymeric organo-silicon material having per molecule at least one silyl group at least one silicon atom being attached to oxygen, a hydrolysable group, a hydroxyl group or a hydrocarbon or halohydrocarbon radical of less than 10C atoms, the polymer having a molecular weight of at least 2000, preferably 10-20000, and containing at least three siliconbonded non-halogen hydrolysable or hydroxyl groups per molecule, the polymeric material being a graft polymer of the organo-silicon group with the, or a, thermoplastic resin or polyurethane, and being applied as such, or in a volatile solvent, or in aqueous solution or emulsion. The themoplastic component may be applied as a preformed layer, as an impregnant for a fabric layer or in solution as a coating. In a modification the polymeric organo-silicon material, in solution together with the thermoplastic resin, may be admixed with the siliceous component, e.g. chopped glass fibre, to form a moulding composition Examples of thermoplastic resins usable are polythene, polypropylene, polybutylene, polyisobutylene, polystyrene, p.v.c., polyvinylidene, chloride, P.T.F.E., polytrifluoropropene, polyvinyl acetate or acrylonitrile, polyacrylates and methacrylates, polyethyleneterephthalate, poly- 1,4-butane diol isophthalate, polyamides, polycarbonates, and polyformaldehyde; cellulose acetate and ethyl cellulose are included. The silicon-bonded hydrolysable groups in the polymeric organo-silicon material may be any groups replaceable by water to form Si-OH groups, e.g. alkoxy, acyloxy, or cyano or isocyano groups. Reference is made to the bonding by the method of the invention, of porcelain teeth to thermoplastic dentures and of a liner of room temperature-vulcanizing silicon elastomer to the surface of such dentures.

    Alkoxyalkarylalkylsilanes and condensates thereof
    24.
    发明授权
    Alkoxyalkarylalkylsilanes and condensates thereof 失效
    烷氧基烷基硅氧烷及其混合物

    公开(公告)号：US3427339A

    公开(公告)日：1969-02-11

    申请号：US3427339D

    申请日：1966-02-01

    Applicant: DOW CORNING

    Inventor： PLUEDDEMANN EDWIN P

    IPC: C07F7/08 ,  C07F7/12 ,  C07F7/18 ,  C08G77/14 ,  C08G31/09

    CPC classification number: C07F7/182 ,  C07F7/0834 ,  C07F7/12 ,  C08G77/14

    Abstract: 1,180,601. Alkoxyalkylarylsilanes and siloxanes. DOW CORNING CORP. 10 Jan., 1967 [1 Feb., 1966(2)], No. 1325/67. Headings C3S and C3T. The invention comprises silanes of the general formula XnR 1 3-n SiQ m ArCH 2 OR and condensates thereof which are polymers of the average general formula, where R is a lower alkyl radical with 1-4 C atoms, Q is an alkylene radical, Ar is a divalent arylene radical or a divalent aryl ether radical, X is a hydroxyl radical or a hydrolysable atom or radical, R 1 is a monovalent hydrocarbon radical with not more than 18 C atoms, n is 1 to 3, m is 0 or 1, a has an average value of 1 to 3; b an average value of 0 to 2; (a + b) is from 1 to 3. The silanes of the invention may be prepared by three methods: (1) Reacting a silane of the general formula with RONa in a solvent such as methanol; (2) reacting a silane of the general formula X n R 1 3-n SiCl with a Grignard reagent prepared from ROCH 2 ArQ m ,Br; and (3) reacting X n R 1 3-n SiH with ROCH 2 ArQ 1 in the presence of chloroplatinic acid, where Q 1 is a monovalent aliphatic hydrocarbon radical which contains one unsaturated group. Preferably the silane comprises R 1 = Me, R = Me, X = OMe or Cl, Ar = C 6 H 4 , n = 3 and Q = -CH 2 -CH 2 -, e.g. CH 3 OCH 2 C 6 H 4 CH 2 CH 2 Si(OCH 3 ) 3 , which is prepared from ClCH 2 (CH 4 CH 2 CH 2 Si(OCH 3 ) 3 and NaOMe (method 1) in one of the examples. A silane CH 8 OCH 2 C 6 H 4 Si(OCH 3 ) 3 , having the further preferred characteristics n = 3, X = Cl or OMe, m = 0, Ar = C 6 H 4 , R = Me, is prepared by method 1 from the corresponding bromide and NaOMe and is hydrolysed to a siloxane of the unit formula The condensates are prepared by conventional hydrolysis of the silanes.

    Polymercaptoorgano and polyhydroxyorgano silanes and siloxanes
    25.
    发明授权
    Polymercaptoorgano and polyhydroxyorgano silanes and siloxanes 失效
    聚合物有机和聚羟基有机硅烷和硅氧烷

    公开(公告)号：US3388144A

    公开(公告)日：1968-06-11

    申请号：US47231065

    申请日：1965-07-15

    Applicant: DOW CORNING

    Inventor： MUSOLF MARTIN C ,  PLUEDDEMANN EDWIN P

    IPC: C07F7/18 ,  C08G18/10 ,  C08G77/392 ,  C09D175/04

    CPC classification number: C09D175/04 ,  C07F7/182 ,  C08G18/10 ,  C08G77/392 ,  C08G18/3893 ,  C08G18/38

    Abstract: 1,154,693. Hydroxy α mercapto silanes and siloxanes. DOW CORNING CORP. 21 June, 1966 [15 July, 1965], No. 27643/66. Headings C3S and C3T. Novel silanes have the general formula (RO) 4-xa (R 11 ) a Si[R 1 (QH) y ] x , wherein Q is oxygen or sulphur and R is a monovalent hydrocarbon radical free from aliphatic nnsaturation, and siloxanes. The general formula wherein in both silanes and siloxanes R 1 is a hydrocarbon, hydrocarbon ether, hydrocarbon ester, hydrocarbon thioether or hydrocarbon thioester radical, R 1 being attached to the silicon atom via a silicon-carbon bond, R 11 is a monovalent hydrocarbon radical free from aliphatic unsaturation, a is 0, 1 or 2, x is 1 or 2, y is 2 or 3 and the sum of x + a is 1, 2 or 3. The silanes and siloxanes are prepared when Q is sulphur by reacting a silane or siloxane containing one or two unsaturated groups per silicon atom with a polymercapto carbon compound in the presence of a catalyst, and the silanes when Q is oxygen are prepared by reaction of a silane containing one or two silicon-bonded hydrogen atoms per silicon atom with a polyhydroxylated carbon compound containing an unsaturated group in the presence of a platinum catalyst. In the examples the silanes (HOCH 2 ) 2 (C 2 H 5 )CCH 2 O(CH 2 ) 3 Si(OCH 3 ) 3 , (HOCH 2 ) 2 (C 2 H 5 )C(CH 2 ) 3 Si(OCH 3 ) 3 , CH 2 (OH)CH(OH)CH 2 SCH 2 CH 2 Si(OCH 3 ) 3 , (HOCH 2 ) 2 (C 2 H 5 )CCH 2 O(CH 2 ) 3 S(CH 2 ) 2 Si(OCH 3 ) and (CH 3 O) 3 Si(CH 2 ) 2 SCH 2 CO.OCH 2 (CH 2 O.CO. CH 2 SH) 2 (C 7 H 5 ) are prepared. The silanes may be used as primers or coupling agents for melamine, phenolic, urea and formaldehyde resins and for urethanes. The silanes and siloxanes may be used in the preparation of polyurethane rubbers.

    Silylalkyl phenols
    26.
    发明授权
    Silylalkyl phenols 失效
    甲硅烷基酚

    公开(公告)号：US3328450A

    公开(公告)日：1967-06-27

    申请号：US25024763

    申请日：1963-01-09

    Applicant: DOW CORNING

    Inventor： PLUEDDEMANN EDWIN P

    IPC: C07F7/02 ,  C07F7/08 ,  C07F7/10 ,  C07F7/12 ,  C07F7/18 ,  C08G77/00 ,  C08G77/14 ,  C09D161/06

    CPC classification number: C08G77/14 ,  C07F7/025 ,  C07F7/0818 ,  C07F7/0836 ,  C07F7/0852 ,  C07F7/10 ,  C07F7/12 ,  C07F7/1836 ,  C07F7/1844 ,  C07F7/1852 ,  C07F7/1868 ,  C07F7/1896 ,  C08G77/00 ,  C09D161/06 ,  C08L2666/44

    Abstract: The invention comprises organo-silicon compounds of general formulae (1) and (2) and (3) siloxanes of the unit general formula wherein each Y is a hydrolysable substituent, R is a monovalent hydrocarbon or halohydrocarbon radical free from aliphatic unsaturation, R1 is an alkylene radical, there being at least two carbon atoms between the benzenoid nucleus and the silicon atom, each X is a halogen atom or an alkyl, alkoxy, haloalkyl or haloalkoxy radical, each Z is a hydrogen atom or a triorganosilyl or diorganosilyl radical, the latter being present only when p is 2 and the OZ radicals are on adjacent carbon radicals of the benzenoid ring, each Z radical thereof being onehalf a diorgano-silyl radical, m is 0 to 3, n 0 to 3 in (1) and (3) and 0 to 2 in (2), p is 1 to 3, r has an average value of 0.001 to 1 inclusive, and n + r is no greater than 3. Suitable R radicals are alkyl, cycloalkyl, aryl, alkaryl, aralkyl and their halogenated derivatives. Suitable R1 radicals, which may be linear or branched, are ethylene, propylene, decylene and octadecylene. Specified Y radicals are halogen, cyanide, isocyanate, thiocyanate, amino, hydroxyamino, metalloxy, trichloromethyl, b -chloroethyl, alkoxy, acyloxy and oxime. Compounds (1) are prepared by heating an alkenyl phenol of general formula (4) where A is an alkenyl radical (e.g. vinyl, allyl, methallyl, propyl, octenyl and octadecenyl), with a silane (Y)3- nSi(R)nH at 50 DEG to 150 DEG C. in the presence of a platinum catalyst or an organic peroxide. Compounds (1) wherein Z is a silyl radical may be hydrolysed to the corresponding phenol by exposure to water. Compounds (1) may be further hydrolysed to compounds and their partial siloxane condensation products. Compounds (2) are prepared by intramolecular reaction in compound (1) between an -OZ group (wherein Z is H) and a Y radical eliminating HY, wherein Y is preferably halogen. Reaction is effected by heating, optionally in the presence of a hydrogen halide acceptor. Siloxanes (3) are prepared either by hydrolysis of compounds (1) or (2) either with or without compounds of the formula Siloxanes (3) are also prepared by reacting phenols or triorganosilyl blocked phenols of formula (4) with siloxanes of the unit formula Many examples are given. The disiloxane products (II) of Examples (4) and (5) may be reacted with diphenylcarbonate forming polycarbonate resins. Uses.-Curing agents and accelerators in epoxy resins, softeners in phenolic varnishes and coating resins, finishing agents on glass, glass cloth, silica, sand, mouldings, laminates, shell moulding, sand consolidation, sizes, cosmetics and antiseptics.ALSO:Silica and sand may be coated with silyl phenolic compounds (see Division C3). In Example (2) a 65% aqueous ethanol solution of the compound is used for sizing silicaeous surfaces.ALSO:Glass-cloth is coated with silyl-phenolic compounds (see Division C3). In Example (8) an aqueous methanol solution of the compound is used.ALSO:The disiloxanes dissolved in 60 per cent aqueous ethanol are suitable for cosmetic and antiseptic applications, (see Example 5).

    Vinyl sulfide organosilicon compounds
    27.
    发明授权
    Vinyl sulfide organosilicon compounds 失效
    乙烯硫醚有机硅化合物

    公开(公告)号：US3186965A

    公开(公告)日：1965-06-01

    申请号：US17640562

    申请日：1962-02-28

    Applicant: DOW CORNING

    Inventor： PLUEDDEMANN EDWIN P

    IPC: C03C17/30 ,  C03C25/40 ,  C07F7/08 ,  C07F7/18 ,  C08G77/00 ,  C08G77/28 ,  C08G77/392

    CPC classification number: C07F7/1836 ,  C03C17/30 ,  C03C25/40 ,  C07F7/0834 ,  C07F7/0856 ,  C07F7/182 ,  C08G77/00 ,  C08G77/28 ,  C08G77/392 ,  Y10T428/31612 ,  Y10T428/31652

    Abstract: Siliceous materials in the form of fibres, flakes, or granules, of glass, silica, quartz, asbestos, silicates, mica &c. are sized with vinyl-sulphide-containing silicon compounds. These may be applied in any conventional manner, in solution or alone, as siloxane compounds, or as silanes which hydrolyse to siloxanes in situ. The silanes have the general formula and the siloxanes where R is a group containing C and H atoms, with or without O atoms, only. The oxygen may be present as -OH, -COO-, or -O-. A is methyl or hydrogen, Y is a monovalent hydrocarbon or halohydrocarbon radical, X is halogen, or R1O(CH2CH2O)n or R1COO (CH2CH2O)n where R1 is an alkyl group of fewer than 5 C atoms, and n is 0, 1 or 2, and a or b are each 1, 2, or 3, and total 2, 3, or 4 (see Division C3).ALSO:The invention comprises compounds of the formula (I) [Yy(X3-y)Si-CH2CHA]a-R-[S-CH=CH2]b wherein X is a halogen or is of formula R1(OCH2CH2)nO-, where n is 0, 1 or 2, and R1 is an aliphatic radical of less than five carbon atoms, or is R11CO-, where R11 is an aliphatic radical of less than five carbon atoms; R is attached to sulphur by a carbon-sulphur bond, and contains carbon and hydrogen or oxygen atoms only, the latter being in hydroxyl, ether or carboxyl groups only, and no carbon having more than one ether group attached; A is a hydrogen atom or methyl group; Y is a monovalent hydrocarbon or halohydrocarbon radical, lacking aliphatic unsaturation; y is 0, 1 or 2; and a and b are each 1, 2 or 3, and total 2, 3, or 4. The invention also comprises siloxanes containing units of the general formula (II) [O 3-y/2 (Yy)Si-CH2CHA]a-R-[S-CH=CH2]b the remaining units being of formula ZcSiO 4-c,/2 where Z is a monovalent hydrocarbon or halohydrocarbon radical, and c is 0, 1, 2, or 3. Preferred forms of compounds (I) are (R111O)3Si-CH2CHA-R1111-S-CH=CH2 where R111 is an alkyl group of less than three carbon atoms, and R1111 contains less than eight atoms of carbon and oxygen together, and preferred forms of (II) are the corresponding hydrolysates O3/2Si-CH2CHA-R1111-S-CH= CH2. The compounds (I) may be prepared in three ways: (a) by reaction of a silane Yy(X3-y)SiH with a compound CH2=CHC .... S-CH=CH2 in the presence of a catalyst, e.g. chlorplatinic acid or platinum/charcoal, the silane adding preferentially to the vinyl group not attached directly to sulphur; (b) by reaction of an epoxy silane with alcohols or acids terminated -S-CH=CH2. Amine catalysts are suitable. X should not be sensitive to hydroxyl groups; or (c) by reaction of an epoxy silane as in (b) and an epoxy vinyl sulphide with a di-, tri-, or tetra-hydroxy alcohol. The siloxanes (II) are prepared (d) from the compounds (I) by hydrolysis, or by co-hydrolyzing them with other silanes ZcSiX4-c or (e) from siloxanes containing Si-H bonds or epoxy groups, in the manner of (a), (b) and (c) above. The compounds may be copolymerized with vinylic and acrylic resins e.g. styrene, methyl methacrylate, butyl acrylate, vinyl chloride, vinylidene dichloride, acrylonitrile and allyl cyanurate, or with unsaturated polyester resins e.g. copolymers of maleic acid with ethylene glycol, butadiene, mixtures of butadiene and styrene, and chloroprene. The Examples 1-11 describe the preparation, according to method (a) of (CH3O)3SiCH2CH2CH2O-CH2 CH2SCH =CH2, and compounds having (CH3O)3Siattached to -(CH2)3SCH=CH2, -(CH2)4SCH =CH2, -(CH2)3OOC.CH2SCH=CH2 and -(CH2)2O(CH2)2SCH=CH2, and hydrolysates of these, and of CH3SiCl2(CH2)2C6 H4SCH= CH2, C18H37(CH3)SiF(CH2)2 C6H10SCH= CH2, ClC6H4Si(OC4H9)2C18 H37SCH=CH2, (CH3OCH2CH2O)2Si(C2H4CF3 (CH3)2O CH2C­CCH2SCH=CH2, (CH3-COO)3Si(CH2)3SCH=CH2, [(CH3)2CHO](C6H5)Si(C6H11) (CH2)2CH(CH3) SCH=CH2, (C2H5COO)(C2H5)(pC6H4CF3 Si(CH2)3 OOC-CH2SCH=CH2, [CH3-COO-(CH2)2O(CH2)2O]2Si(2, 4-C6H3Br2) (CH2)4SCH=CH2, and [(CH2)3O (CH2)2O]2 [Cl(CH2)3]Si(CH2)3SCH=CH2, and of materials derived from various Si-H containing siloxanes and CH2=CHCH2SCH=CH2. By method (b) is prepared (CH3O)3Si(CH2)3OCH2CHOH CH2O(CH2)2SCH=CH2, and by method (c) [(CH3O)3Si(CH2)3OCH2CHOHCH2 OCH2]1 or 2 C(CH3)[CH2OCH2CHOHCH2O(CH2)2 SCH = CH2]2 or 1, (CH3O)3Si(CH2) 3OCH2CHOHCH2 OOC CH2COO CH2CHOH CH2SCH=CH2 and [(CH3O)3Si(CH2)3OCH2CHOH CH2 OCH2]1, 2 or 3, C[CH2OCH2CHOH CH2O(CH2)2SCH= CH2]3, 2 or 1. Also prepared are co-hydrolysates of CH3SiCl2(CH2)3O(CH2)2SCH= CH2 with CH2=CH(CH3)SiCl2, C6H5(CH3)Si Cl2, CF2=CF(CH3)SiCl2, CH2=CH CH=CH (C6H5)SiCl2 and ClCH=CHCH2CH2 (CH3) SiCl2, and compounds (CH3COO)2(CH3) SiCH2CH(CH3)COOCH2CHOH CH2O(CH2) 2 SCH=CH2 and (CH3O)2[C6H5(CH3) CHCH2] Si(CH2)3OCH2CHOH CH2O(CH2)2SCH =CH2, Example 12 describes the preparation of a glass cloth laminate from a polyester resin (70 parts of phthalic acid/maleic acid/propylene glycol linear polyester in 30 parts of styrene, plus 0.5 part of benzoyl peroxide in 7 parts styrene). The compounds may also be used for sizing siliceous materials, for which purpose those of formula (R1 1 1O)3Si-CH2CHA-R1 1 1-SCH= CH2 and their hydrolyzates are preferred, and as coating compositions, alone or copolymerized with vinylic, acrylic or unsaturated polyester resins.ALSO:Glass cloth is coated with vinyl sulphide-containing silicon compounds, which may be applied in any conventional manner, in solution or alone, as siloxane compounds or as silanes which hydrolyse to siloxanes in situ. The siloxanes have the general formula and the silanes where R is a group containing CH and O atoms only, the latter as -OH, -COO- or -O-groups, A is H or CH3, Y is a hydrocarbon or halohydrocarbon monovalent radical, X is halogen, or a group R1(O CH2CH2)nO or R1CO(OCH2CH2)nO, where R1 is an alkyl group of less than 5 carbon atoms and n is 0, 1, or 2, and a and b are each 1, 2, or 3, and total 2, 3, or 4 (see Division C3). In Example 12 glass cloth is dipped in solutions of 0,5% of (CH3O)3Si(CH2)3OCH2CHOHCH2O (CH2)2SCH=CH2 in methanol, 0,5% of in 0,1% acetic acid in water, and 0,5% of in a 3 : 1 water/propanol mixture. The treated cloths are treated with an unsaturated polyester resin.

    Preparation of methallylsilanes
    30.
    发明授权
    Preparation of methallylsilanes 失效
    甲基硅烷的制备

    公开(公告)号：US3631085A

    公开(公告)日：1971-12-28

    申请号：US3631085D

    申请日：1970-03-23

    Applicant: DOW CORNING

    Inventor： KRAHNKE ROBERT H ,  MICHAEL KEITH W ,  PLUEDDEMANN EDWIN P

    IPC: C07F7/18 ,  C07F7/08

    CPC classification number: C07F7/0801

    Abstract: THE PREPARATION OF METHALLYLSILANES WHICH INVOLVES CONTACTING (IN AN OPEN SYSTEM) A HYDROGEN-SUBSTITUTED ORGANOSILICON COMPOUND WITH DIISOBUTYLENE, AT A TEMPERATURE OF FROM 400*C, TO 600*C. THE PRESENT METHOD IS LESS DIFFICULT (AND THUS LESS EXPENSIVE) THAN PRIOR ART METHODS AND THE RECOVERED METHALLYLSILANES ARE USEFUL IN THE PRODUCTION OF CERTAIN SYNTHETIC RESINS.

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