Method for adhering cured silicones to low energy plastics and composite prepared by the method
AssigneeDow Silicones Corporation
InventorBizhong Zhu
Life of this patent
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Abstract
A primer is useful for adhering cured silicones to low energy plastic substrates. The primer is prepared from starting materials including a) an organoboron compound capable of forming a free radical generating species, and at least one of b) an organosilicon compound having, per molecule, at least one free radical reactive group and at least one other reactive group, and/or c) an organoborane liberating compound capable of reacting with starting material a) to liberate the free radical generating species. The method for forming the primer may further include use of d) an organic solvent, and e) a free radical polymerizable monomer, oligomer, macromonomer, or polymer.
Claims22
A method for adhering a cured silicone to a substrate, where the method comprises:
- 1) applying a primer composition to a surface of a substrate, where the primer composition comprises
- a) an organoboron compound capable of forming a free radical generating species, and
- 2) contacting a curable silicone composition with the surface of the substrate, where the primer composition and/or the curable silicone composition further comprise at least one of
- b) an organosilicon compound having, per molecule, at least one free radical reactive group and at least one other reactive group, and/or
- c) an organoborane liberating compound capable of reacting with starting material a) to liberate the free radical generating species, with the proviso that starting material c) is used in the method when either starting material b) is absent or starting material b) does not contain a group capable of reacting with starting material a) to liberate the free radical generating species.
The method of any one of the preceding claims, where a) the organoboron compound is selected from the group consisting of:
- i) an organoborane-organonitrogen compound complex, ii) an organoborate containing at least one B—C bond, and iii) both i) the organoborane-organonitrogen compound complex and ii) the organoborate containing at least one B—C bond.
The method of any one of the preceding claims, where starting material b), the organosilicon compound having, per molecule, at least one hydrolyzable group and at least one free radical reactive group, is present and starting material b) is a silane of formula R1mRnSiX(4-m-n), where each R is independently a monovalent hydrocarbon group of 1 to 18 carbon atoms, each R1 is a methacryl-functional alkyl group or an acryl-functional alkyl group, each X independently represents a hydrolyzable group selected from an acetamido group, an acyloxy group such as acetoxy, an alkoxy group, an amido group, an amino group, an aminoxy group, an oximo group, a ketoximo group, and a methylacetamido group, subscript m is 1 to 2, subscript n is 0 to 2, and a quantity (m+n) is 2 to 3.
The method of any one of the preceding claims, where starting material c) the organoborane liberating compound is present, and starting material c) is selected from the group consisting of:
- i) an acid, ii) an aldehyde, iii) an isocyanate, iv) an epoxide, v) an acid chloride, vi) an anhydride, vii) an acyloxysilane, viii) an acyloxysiloxane, ix) a halosilane, x) a halosiloxane, xi) a carboxylic acid functional silane, xii) a carboxylic acid functional siloxane, xiii) an anhydride functional silane, xiv) an anhydride functional siloxane, xv) an epoxy functional silane, xvi) an epoxy functional siloxane, xvii) a sulphonyl chloride, and a combination of two or more of i), ii), iii), iv), v), vi), vii), viii), ix), x), xi), xii), xiii), xiv), xv), xvi), and xvii).
A primer composition comprising:
- a) a tri-n-butyl borane-3-methoxypropyl amine complex,
- b) a (meth)acryloxyalkyl, trialkoxysilane
- c) an acid capable of reacting with starting material a) to liberate the free radical generating species,
- d) an organic solvent;
- and
- e) methyl(meth)acrylate.
Dependencies are inferred from the claim text.