Patent GB-990714-A (GB)
Title: Nitrogen-containing organosilicon compounds and their preparation
IPC: C07F7/18
Filed: 1963-05-09
Abstract: The invention comprises compounds of the general formula (R1O)3- bR11bSiRZ, wherein Z is (I) -C(OR1)NH = +2X-, or (II) <FORM:0990714/C3/1> or (III) <FORM:0990714/C3/2> or (IV) <FORM:0990714/C3/3> or <FORM:0990714/C3/4> where Y is hydrogen or a monovalent saturated hydrocarbon radical, R1 is a monovalent hydrocarbon radical containing no aliphatic unsaturation, R11 is a monovalent saturated hydrocarbon radical, or a trifluoropropyl or chlorophenyl radical, R is a divalent saturated aliphatic hydrocarbon radical having at least 2 carbon atoms between Si and Z, X is chlorine, bromine or iodine, and b is 0, 1, 2 or 3.  Preferred values are:  Y-hydrogen, R1-alkyl group of 1-4 C atoms, R11-alkyl radical, R- -CH2CH2-or -CH2CH2CH2-.  The compounds (I) are prepared by treating compounds X3- bR11bSiRCN, or (R1O)3- bR11bSiRCN and HX, with an alcohol R1OH.  The 2-imidazolinyl-2 compounds (II) are prepared by heating compounds (I) with a diamine H2NCY2CY2NH2.  The 1-imidazolinyl-2 (III) and 4- or 5-imidazolinyl-2 (IV) compounds are prepared by heating compounds <FORM:0990714/C3/5> and <FORM:0990714/C3/6> respectively with an orthoester YC(OZ1)3, where Z1 is a monovalent hydrocarbon group, preferably a 1 to 4 carbon-containing alkyl group.  Salts of compounds (II), (III) and (IV), of formula (R1O)3- bR11bSiRZ.HW, where HW is a hydrogen halide or an alkyl or phenyl carboxylic acid, are prepared by heating the compounds with the acid HW or its ammonium salt.  Siloxanes may be prepared from these salts, when b is 0, 1 or 2, by conventional procedures, and from these in turn may be prepared siloxanes of unit <FORM:0990714/C3/7> by neutralizing with e.g. an amine.  Copolymers containing either type of siloxane unit may be prepared by heating homopolymers together, or by treating a conventional siloxane with an alkoxy silane of this invention.  Examples describe the preparation of compounds of types (I), (II), (III) and (IV), and the preparation of salts, siloxanes, and copolysiloxanes from types (II) and (III). Uses:  (all imidazoline compounds)-emulsifying agents; (imidazoline salts)-antistatic coating agents (see Divisions B2 and D1). Specification 858,445 is referred to.ALSO:Antistatic finishes for sheet materials, e.g. cellulose esters and other materials used for making photographic film, and phonographic records made of vinyl resins, are provided by salts of imidazolinylalky-alkoxy-silanes and -siloxanes, and copolymers containing units of the latter, preferably applied as aqueous dispersions.  The compounds are of general formula (R1O)3-bR11bSiRZ,HW or contain siloxane units O3-b/2R11bSiRZ,HW, where R1 is a hydrocarbon group not aliphatically unsaturated, R11 is a saturated hydrocarbon or trifluoropropyl or chlorophenyl group, R is a saturated hydrocarbon group having at least 2 carbon atoms between Si and Z, Z is a 1-, 2-, 4-, or 5-imidazolinyl-2 group, HW is hydrogen halide or an alkyl or phenyl carboxylic acid, and b is 0, 1 or 2, and in the silanes may be 3 (see Division C3).  The dispersions may be applied by immersing the article or material, or by spraying, padding or brushing.  The coating is cured by subjection briefly to heat, e.g. a temperature of 65-150  DEG C., and may amount to from 0,2-10% of the dry weight of the uncoated article.  Specification 858,445 is referred to.ALSO:Antistatic finishes for fibres or fabrics comprising e.g silk, nylon, wool, viscose rayon, polyesters, cellulose acetate or cellulose ester rayons, or vinyl resins, are provided by salts of imidazolinylalkyl-alkoxy-silanes or siloxanes or copolysiloxanes containing units derived therefrom.  The salts are of general formula (R1O)3-bR11b Si RZ , HW or contain units <FORM:0990714/D1-D2/1> where R1 is a hydrocarbon group not aliphatically unsaturated, R11 is a saturated hydrocarbon or trifluoropropyl or chlorophenyl group, R is a saturated divalent hydrocarbon group having at least 2 carbon atoms between Si and Z, Z is 1-, 2-, 4- or 5- imidazolinyl-2 group, HW is a hydrogen halide or an alkyl- or phenyl-carboxylic acid, and b is 0, 1, or 2, and in the silanes may be 3 (see Division C3).  The compounds are best applied as aqueous dispersions.  Specification 858,445 is referred to.