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GB975603A - Improvements in or relating to organosilicon compounds - Google Patents

Improvements in or relating to organosilicon compounds

Info

Publication number
GB975603A
GB975603A GB44117/61A GB4411761A GB975603A GB 975603 A GB975603 A GB 975603A GB 44117/61 A GB44117/61 A GB 44117/61A GB 4411761 A GB4411761 A GB 4411761A GB 975603 A GB975603 A GB 975603A
Authority
GB
United Kingdom
Prior art keywords
oxime
halogeno
siloxane
units
compounds
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.)
Expired
Application number
GB44117/61A
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.)
Dow Silicones Corp
Original Assignee
Dow Corning Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Dow Corning Corp filed Critical Dow Corning Corp
Priority claimed from US222167A external-priority patent/US3189576A/en
Publication of GB975603A publication Critical patent/GB975603A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02Silicon compounds
    • C07F7/08Compounds having one or more C—Si linkages
    • C07F7/0834Compounds having one or more O-Si linkage
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02Silicon compounds
    • C07F7/08Compounds having one or more C—Si linkages
    • C07F7/0834Compounds having one or more O-Si linkage
    • C07F7/0892Compounds with a Si-O-N linkage
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/48Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
    • C08G77/50Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms by carbon linkages

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Silicon Polymers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Paints Or Removers (AREA)

Abstract

The invention comprises silanes of the general formula (X=NO)a SiR14-a, and siloxane copolymers containing the group Si(ON=X), wherein X is R2C= or <FORM:0975603/C3/1> wherein R11 is a divalent hydrocarbon or halogeno substituted hydrocarbon radical, R is a hydrocarbon or halogeno substituted hydrocarbon radical and each may be the same or different, R1 is a hydrocarboxn, halogeno substituted hydrocarbon, cyano alkyl group, or hydrogen atom and may be the same or different, and a is 1, 2, 3, or 4. Specified R and R1 groups include alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl, aralkyl, and alkaryl radicals and these may be substituted by Cl, F, Br or I. Specified R11 groups are: -CH2(CH2)3CH2-, -CH2(CH2)4-CH2-, -C6H4.C6H4-, <FORM:0975603/C3/2> and <FORM:0975603/C3/3> The silanes are prepared by mixing an oxime X=NOH with HalaSiR14-a in the temperature range of 20-100 DEG C. in the presence of acid acceptor. Specified oximes are acetophenone oxime, acetone oxime, benzophenone oxime, 2-butanone oxime, 3-methyl -2- butenone oxime, d-camphor oxime, a -d-carbone oxime, 2-nonaxone oxime, 5-methyl -2- hexanone oxime, 2-pentanone oxime, diisopropylketone oxime, cyclopentanone oxime, cyclohexanone oxime, acrylophenone oxime, 1-acetonaphthone oxime-1-phenyl -2- butanoneoxime, chloro-cyclohexanone oxime, perfluorocyclobutanone oxime, 4-phenyl -2- butanone oxime, 5-isopropyl -2-methyl acetophenone oxime, 12-tricosanone oxime, a -bromo-2, 4, 6-trimethyl-isobutyrophenone oxime, a -bromoacetophenone oxime, anthrone oxime, p-chloro acetophenone oxime and p-a -dibromo acetophenone oxime. The polysiloxane copolymers consist of units <FORM:0975603/C3/4> wherein b is 0, 1, or 2, d is 1, 2, or 3, and b+d<4, with conventional siloxane units. One method of preparation comprises reacting a hydroxy-end-blocked siloxane, having units of the general formula <FORM:0975603/C3/5> wherein c is 0, 1, 2 or 3, with a silane R1bSi(ON=CR2)4-6 wherein b is 0, 1 or 2. An alternative method comprises reaction of a halogeno endblocked siloxane with the oxime. These halogeno end blocked siloxane are prepared by reaction of a halogeno-silane R1bSiZ4-6 where b is as above and Z is halogen, in the presence of a hydrogen halide acceptor, such as pyridine, with a hydroxylated organo silicon compound. Specified hydroxylated organo-silicon compounds are silanediols, silanetriol and hydroxy-end-blocked siloxanes, as above. Halogeno silane and hydroxylated organo-silicon compound must be such that there is at least one R1 radical per silicon in the resulting halogeno-siloxane. The compounds cure in the presence of water vapour to give rubbery or resinous materials. Elevated temperatures or catalysts such as amino compounds or metal carboxylates may be used. They may be modified by presence of fillers, e.g. reinforcing silica fillers with or without organosilyl groups attached to the surface, non-reinforcing fillers such as coarse silicas or metallic oxides, asbestos and glass, graphite and carbon black. Examples describe the preparation of (1) a dimethyl polysiloxane having as end-units (Me2C=NO)2 SiMeO0.5; (3) MeSi(ON=CMe2)3; (5) Si(ON=CMe2)4; (6) (Me2C=NO)3SiO 1/2 ; (7) Me2Si(ON=CMe2)2 (8) Me3SiON=CPh2; (10) MeHSi(ON=CMe2)2; (14) (Me2C=NO)2SiMeO-(SiHMeO)7SiMe-(ON=CM2) 2. Many other examples are given, including vinyl, cyano, chlorine, bromine and fluorine-substituted compounds. Uses; Caulking and coating applications on glass, porcelain, wood, metals, and organic plastics.ALSO:Surfaces such as wood, glass, porcelain, metals and plastics may be coated with a composition comprising a silane of the formula (X=NO)aSiR14-a or a copolymeric siloxane containing units of the formula <FORM:0975603/B1-B2/1> where X is R2C= or <FORM:0975603/B1-B2/2> , wherein R and R11 are respectively monovalent and divalent hydrocarbon or halohydrocarbon radicals, R1 is a hydrocarbon, halohydrocarbon or cyanoalkyl group or a hydrogen atom, a is 1 to 4, b is 0 to 2, d is 1 to 3 and b+d is less than 4 (see Division C3). The compositions may contain other polysiloxanes as well as fillers, e.g. fume and precipitated silicas, silica aerogel, diatomaceous earth, quartz, titania, ferric oxide, zinc oxide, asbestos glass, graphite and carbon black. They may be applied in organic solvents and the compounds cure on exposure to atmospheric moisture; this may be accelerated by amino or carboxylate catalysts.
GB44117/61A 1961-02-27 1961-12-08 Improvements in or relating to organosilicon compounds Expired GB975603A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US9163661A 1961-02-27 1961-02-27
US222167A US3189576A (en) 1962-09-07 1962-09-07 Organosilicon intermediates containing silicon-bonded oxime radicals

Publications (1)

Publication Number Publication Date
GB975603A true GB975603A (en) 1964-11-18

Family

ID=26784174

Family Applications (2)

Application Number Title Priority Date Filing Date
GB44117/61A Expired GB975603A (en) 1961-02-27 1961-12-08 Improvements in or relating to organosilicon compounds
GB33886/63A Expired GB1000421A (en) 1961-02-27 1963-08-27 Silicone intermediates and silicones

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB33886/63A Expired GB1000421A (en) 1961-02-27 1963-08-27 Silicone intermediates and silicones

Country Status (1)

Country Link
GB (2) GB975603A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4546017A (en) * 1984-01-14 1985-10-08 Dow Corning Limted Organopolysiloxane composition curable to an elastomer and use thereof
US4766231A (en) * 1986-12-06 1988-08-23 Dynamit Nobel Ag Process for the preparation of ketoximosilanes
EP3527771A1 (en) 2014-07-28 2019-08-21 Dow Silicones Corporation Panelized shadow box

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4546017A (en) * 1984-01-14 1985-10-08 Dow Corning Limted Organopolysiloxane composition curable to an elastomer and use thereof
US4766231A (en) * 1986-12-06 1988-08-23 Dynamit Nobel Ag Process for the preparation of ketoximosilanes
EP3527771A1 (en) 2014-07-28 2019-08-21 Dow Silicones Corporation Panelized shadow box

Also Published As

Publication number Publication date
GB1000421A (en) 1965-08-04

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