Patent GB-1039931-A (GB)
Title: Composite article and method of making same and coupling agents
IPC: C07F7/18
Filed: 1963-01-23
Abstract: Silanes for surface treatment of inorganic solids are obtained by reaction of an a ,b -olefinically unsaturated carboxylic acid with an amino-aliphatic silane having all N atoms spaced from Si by at least 3 carbon atoms in a chain linked directly to silicon by a C-Si bond, and having at least one hydroxyl-reactive group attached to silicon. Suitable reaction products listed are <FORM:1039931/C3/1> <FORM:1039931/C3/2> <FORM:1039931/C3/3> <FORM:1039931/C3/4> <FORM:1039931/C3/5> <FORM:1039931/C3/6> <FORM:1039931/C3/7> where n is 1-3, Y is H or CH2=CR1-CO-, R1 is H or an alkyl group, -O is a hydroxy, alkoxy, aryloxy or acetoxy group.  In general, compounds produced by reacting acrylochloride or anhydride or an alkyl-acrylochloride or anhydride with a silane containing 1-3 H2N-CaH2a- or H2N-CbH2b-NH-CaH2- a groups attached t silicon are suitable, where a is 3-12 and b is 1-10. Partial hydrolyzates of the silanes may also be used.  In Examples 1-3 the silanes <FORM:1039931/C3/8> <FORM:1039931/C3/9> <FORM:1039931/C3/10> are prepared from the corresponding acid chlorides and aminosilanes. Other suitable acid aminosilanes.  Other suitable acid components are cinnamic acid chloride and linoleic acid chloride and the chlorides or anhydrides of a ,b -unsaturated dicarboxylic acids, e.g. maleic acid, while the amino-silane may contain 1 or 2 alkyl or aryl groups in addition to the -OR and the aminoalkyl group attached to Si, to give compounds such as <FORM:1039931/C3/11>ALSO:Glass fabrics and other inorganic solids suitable for reinforcing rubbers and resins vulcanized or polymerized in situ and normally containing hydroxyl groups are modified by having bonded thereto olefinically unsaturated residues by reaction of such hydroxyl groups with a reaction product of an a , b -olefinically unsaturated carboxylic acid and an amino-aliphatic silane having all nitrogen atoms spaced from silicon by a chain of at least three carbon atoms, the chain being attached to silicon by a C-Sibond, and having at least one hydroxy-reactive group attached to silicon.  (see Division C3).  The treated solid has attached to its surface through siloxy groups, olefinic groups joined via amide groups to the silicon. The olefinic groups will form bonds with polymers formed in situ from a liquid olefinically unsaturated monomer, and any nitrogen atoms having a hydrogen atom attached will form bonds with polymers from liquid curable epoxy-, phenolic-, melamine- or unsaturated polyester resins. The solid may be wetted by a solution of the amido-silane product in an organic solvent or in aqueous emulsion, dried, then heated e.g. to 100-250 DEG C.  In Example 4 glass cloth is dipped in an either/toluene solution of a silane <FORM:1039931/B1-B2/1> , then drained and heated at 175 DEG C., then used, with synthetic resins, to form laminatesALSO:Glass fibres (including glass cloth) suitable for reinforcing rubbers and resins vulcanized or polymerized in situ are treated with a reaction product of an a , b -olefinically unsaturated carboxylic acid and an amino-aliphatic silane having all N atoms spaced from silicon by at least 3 C atoms, and having at least one group attached to silicon which will react with hydroxy groups on the inorganic solid surface. The solid may be wetted by a solution of the amido-silane product in an organic solvent or in aqueous emulsion, then dried and heated.  In Example 4 glass cloth is dipped in an ether/toluene solution of a silane <FORM:1039931/D1-D2/1> , then drained and heated at 175 DEG C.