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    13.
    发明专利
    未知

    公开(公告)号：DE1720860A1

    公开(公告)日：1971-07-22

    申请号：DE1720860

    申请日：1967-08-24

    Applicant: GEN ELECTRIC

    Inventor： STUART HAY ALLAN

    IPC: C08G65/44 ,  C08G23/18

    Abstract: 1,178,555. Polyphenylene ethers. GENERAL ELECTRIC CO. 25 April, 1967 [14 Nov.. 1966]. No. 19106/67. Heading C3R. Poly - (2,6 - diaryl - 1,4 - phenylene ether) is obtained by reacting oxygen with a 2,6-diarylphenol, wherein one aryl substituent is phenyl and the other is phenyl, alkyl-substituted phenyl, biphenylyl, terphenylyl or naphthyl, the catalyst being an amine-basic cupric salt complex having a nitrogen-to-copper ratio not greater than 5 to 1, the amine being n-butylamine, di-n-butylamine, tri-n-butylamine, cyclohexylamine, p-menthane-1,8-diamine or an amine of formula where R is hydrogen or methyl and n is 1 or 2, the reaction being carried out at 50‹ to 130‹ C. in a solvent in which the phenol and the complex are dissolved and the water formed in the reaction is removed as fast as it is formed. The complex may be prepared from either a cupric salt or a cuprous salt which can be converted to the cupric state by the oxygen. The water may be removed by distillation, e.g. as an azeotrope, or by using a solid drying agent. In examples, polymers are obtained from 2,6-diphenylphenol, 2 - phenyl - 6 - (4 - t - butylphenyl) phenol, 2 - phenyl - 6 - (4 - methylphenyl) phenol, 2 - phenyl - 6 - (x - naphthyl) phenol, 2 - phenyl - 6 - (o - biphenylyl) phenol, 2 - phenyl - 6 - (2,3 - diphenylphenyl) phenol and 2 - phenyl - 6 - (2 - methylphenyl) phenol; the amine complexes are prepared from cuprous bromide and cuprous chloride and from N,N,N 1 ,N 1 - tetramethyl - 1,3 - butanediamine, N,N,N 1 ,N 1 - tetramethylethylenediamine, N,N 1 - dimethyl - 1,3 - propanediamine, di - n - butylamine, n-butylamine, cyclohexylamine, pmenthane - 1,8 - diamine and N,N,N 1 - tetramethyl - 1-2 - propanediamine.

    16.
    发明专利
    未知

    公开(公告)号：DE1595726A1

    公开(公告)日：1970-02-12

    申请号：DE1595726

    申请日：1966-02-11

    Applicant: GEN ELECTRIC

    Inventor： STUART HAY ALLAN

    IPC: C07F1/02 ,  C07F3/10 ,  C07F7/08 ,  C07F9/74 ,  C08G77/60 ,  C08G79/00 ,  C08G79/06 ,  C08F35/04

    Abstract: The invention comprises compounds containing both (a) divalent units M and (b) -C­C-R1-C­C-units, the two valencies of the M unit are connected directly to said acetylenic units and the remaining valency of each of said acetylenic unit is connected to H, an M unit or an acetylenic unit, where M is S, Se, Te, RP, Hg, T1R, GeR2, SnR2, PbR2, AsR, SbR, BiR, Ni(M1R3)2, Pd(M1R3)2, Pt(M1R3)2; M1 is P, As or Sb; R is a hydrocarbon radical and R1 is a divalent hydrocarbon radical. These compounds may have the formula where n is an integer. Specific types of compounds disclosed have:- (i) M as Hg and R1 may be phenylene, ethylene -C3H6- or -C4H8. (ii) M as C6H5As where R1 may be phenylene. These compounds may be made by treating the alkali metallo derivative of a diethynyl hydrocarbon with a dihalogen compound. In an example LiC6H5 is formed from Li and C6H5Br, the lithium compound is treated with p-diethynylbenzene to give the dilithio derivative and the derivative treated with HgCl2 to give a precipitate of a phenylene ethynyl mercury compound. Alternatively the mercury compounds may be prepared by direct reaction between a mercury halide and diethynyl hydrocarbon, in an embodiment HgCl2 is treated with eicosatebayne in alkaline KI solution to give the required compound. Compounds corresponding to the formula above may be condensed to form polymers by treating them in solution with an amine-cuprous or basic cupric salt complex as an oxygen carrying intermediate, the amine nitrogen atom being free of directly bonded aryl substituents (see Division C3).ALSO:The invention comprises compounds containing both (a) SiR2 units and (b) -C­C-R1-­C-units, the two valencies of the SiR2 unit being connected directly to said acetylenic units and the remaining valency of each of said acetylenic units being connected to H, R being a hydrocarbon radical and R1 being a divalent hydrocarbon radical. The preferred compounds have the formula where M=R2Si. In specific examples the compounds disclosed have R as phenyl, ethyl or methyl and R1 as phenylene. These compounds are prepared by treating the alkali metalloderivative of a diethynyl hydrocarbon with a dihalogen silicon compound. In specific examples the dilithioderivative of a diethynylbenzene is treated with a dichloro silane to give the desired product. The invention further comprises polymers of formula wherein M is Hg, TlR, SiR2, GeR2, SnR2, PbR2, PR, AsR, SbR, BiR, S, Se, Te, Ni(M1R3)2, Pd(M1R3)2, Pt(M1R3)2; where M1 is P, As or Sb; R is a hydrocarbon radical and R1 is a divalent hydrocarbon radical, and n and m are integers. These polymers may be made by the self-condensation of a compound according to the first formula by treating a solution of them with an amine-cuprous or basic cupric salt complex as an oxygen carrying intermediate, the amine nitrogen atom being free of directly bonded aryl substituents. Numerous lists of suitable copper salts and amines are given together with passages explaining their oxygen carrying ability. In specific examples organomercury polymers having 6, 9 and 10 repeating units are illustrated. A compound made from eicosatetrayne and mercuric chloride is further polymerized using a cuprous chloride/pyridine solution. Organo-arsenic polymers are made from the reaction product of the dilithioderivative of a diethynyl benzene with phenyl di-iodoasine, by taking this product and treating it with copper salt/pyridine complex. Organo-silicon polymers are made by treating compounds having the first formula above with a solution of cuprous chloride or basic cupric chloride in pyridine.

    17.
    发明专利
    未知

    公开(公告)号：DE1900680A1

    公开(公告)日：1969-07-31

    申请号：DE1900680

    申请日：1969-01-08

    Applicant: GEN ELECTRIC

    Inventor： STUART HAY ALLAN ,  BECKER HANS-DIETER

    IPC: C07C37/07 ,  C07C37/11 ,  C07C39/15 ,  C07C39/12

    Abstract: 1,193,526. O,O 1 -Biphenols. 1 Oct., 1968 [12 Jan., 1968], No. 46548/68. Heading C2C. 4,4 1 ,6,6 1 - Tetra - substituted - 0,0 1 - biphenols are obtained by reacting in the liquid phase a phenol of formula with a spiro quinol ether of the formula where R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are tert. alkyl groups having from 4 to 8 carbon atoms. Dealkylated biphenols may be obtained by treatment with an alkylation catalyst under atmospheric or subatmospheric pressure, high temperature and removal of the olefin from the reaction mixture. Basic catalysts may be used to remove the alkyl groups in o position to the OH groups first, further heating or the use of an acidic catalyst is required to remove the alkyl groups in p-positions to the OH groups. Examples are given which illustrate these processes. The spiro quinol ether of the above formula may be obtained by oxidatively coupling a di- (tert-alkyl)-phenol or a portion of the biphenol product. Examples are given where 3,3 1 ,5,5 1 - tetra - tert - butyl - spiro - (3,5 - cyclohexadiene - 1 ,8 1 [7]oxabicyclo[4,2,0]octa[1,3,5]tri ene)-2-one is prepared.

    18.
    发明专利
    未知

    公开(公告)号：DE1801230A1

    公开(公告)日：1969-04-30

    申请号：DE1801230

    申请日：1968-10-04

    Applicant: GEN ELECTRIC

    Inventor： EARL BOSTICK EDGAR ,  STUART HAY ALLAN ,  JOHN CHALK ALAN

    IPC: C08F283/06 ,  C08F283/08

    Abstract: 1,241,683. Grafted poly(1,4-phenylene ethers). GENERAL ELECTRIC CO. 2 Oct., 1968 [5 Oct., 1967], No. 46868/68. Headings C3G, C3R and C3T. A graft copolymer comprises a poly (1,4- phenylene ether) backbone having grafted on to it a polymer of an anionically polymerizable monomer. Specified monomers are 1-alkenes having 2 to 8 carbon atoms, monomers of formula where R is hydrogen, C 1 to C 8 -alkyl or chlorine, X is chlorine, -CN or -COOR 1 , where R 1 is hydrogen, C 1 to C 8 -alkyl or phenyl, cyclic organosil oxanes, alkyl or aryl isocyanates having up to 18 carbon atoms in the alkyl or aryl group and 1,2-epoxyalkanes having 2 to 8 carbon atoms. The poly- (1,4-phenylene ether) is metalated by reaction with an alkyl or aryl alkali metal compound before being grafted. Examples are given in which poly(2,6-dimethyl1-1,4-phenylene ether) is metalated with butyl lithium prior to being grafted with styrene, acrylonitrile, isoprene or methyl methacrylate. In other examples, the lithiated polyether is reacted with (a) tetramethylethylene diamine before being grafted with styrene, (b) 1,1-diphenyl ethylene before being grafted with methyl methacrylate or (c) titanium tetrachloride before being grafted with ethylene. The polyether is metalated in Example II with the potassium dianion of α-methylstyrene dimer and grafted with styrene. In Examples 7, 12 and 13, the lithiated polyether is grafted with hexamethylcyclotrisiloxane, the graft reaction is terminated by addition of dimethyl sulphate or trimethylchlorosilane and the graft polymer of Example 13 is mixed with pyridine, lauric acid or trichloracetic acid and heated. The lithiated polyether is reacted in Example 8 with tetramethylethylene diamine and grafted with phenyl isocyanate, using methyl iodide as terminator. In Example 18, the polyether is metalated with a Na, K or Li alkyl and grafted with ethylene oxide. Poly- (2 - methyl - 6 - phenyl - 1,4 - phenylene ether) is metalated in Example 14 with butyl lithium prior to being grafted with styrene, or reacted with 1,1-diphenylethylene and grafted with methyl methacrylate. In Examples 15 and 16, poly(2,6-diphenyl-1,4-phenylene ether) is similarly metalated and grafted with styrene or methyl methacrylate.

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