Method of bonding a urethane adhesive to non-porous substrates

• US 5,468,317 A
• Filed: 02/24/1995
• Issued: 11/21/1995
• Est. Priority Date: 06/03/1993
• Status: Expired due to Fees

• Current Assignee: Essex Specialty Products Incorporated
• Original Assignee: The Dow Chemical Company (Dow, Inc.)
• Inventors: Hsieh, Harry W.
• Primary Examiner(s): Marquis, Melvyn I.
• Assistant Examiner(s): MOORE, MARGARET G
• Application Number:
  US08/395,243
• Time in Patent Office: 270 Days
• Field of Search: 156/108, 156/329, 156/330, 156/331.4, 156/331.7, 523/414, 523/421, 524/536
• US Class Current: 156/108
• CPC Class Codes: C08L 2666/02 Organic macromolecular compounds, natural resins, waxes or and bituminous materials
• CPC Class Codes: C08L 2666/44 Silicon-containing compounds
• CPC Class Codes: C09D 133/06 of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
• CPC Class Codes: C09D 183/08 containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
• CPC Class Codes: C09D 183/14 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms C09D183/10 takes precedence

Abstract

Described herein is a primer composition which comprises a solution or dispersion of: (a) about 2 percent to about 30 percent by weight of a film-forming resin; (b) about 2 percent to about 80 percent by weight of a reaction product of an epoxy silane and an amino silane, wherein the amino silane contains at least two amine groups per molecule, which is prepared by (1) contacting an amino silane and epoxy silane in amounts such that the molar ratio of epoxy silane to amino silane in the reaction mixture is less than about 1.8:1.0 and then (2) adding additional epoxy silane to the reaction mixture so that the molar ratio of epoxy silane to amino silane is at least about 2:1 in a volatile solvent. Described herein is also a method of bonding a vehicle window to a vehicle window flange using the primer composition and a urethane adhesive. It has been discovered that the primer of the invention enhances the bonding of a non-porous substrate, such as glass, to a second substrate, particularly when used in conjunction with a "fast cure" adhesive comprised of an isocyanate-functional prepolymer and dimorpholinodiethyl ether. In addition, such primers are more easily prepared than primers which require the use of a silane "cook" comprising a reaction product of a polyisocyanate and one or more silane-containing compounds.

Claims

1. A process for the bonding of a vehicle window to a vehicle window flange which consists essentially of the steps of:

(A) applying along the periphery of one side of the window a primer composition which comprises a solution or dispersion of;

(1) about 2 percent to about 30 percent by weight, based on the weight of the composition, of a film-forming resin;

(2) about 2 percent to about 80 percent by weight, based on the weight of the composition, of a reaction product of an epoxy silane and an amino silane, wherein the amino silane contains at least two amine groups per molecule, which is prepared by (a) contacting neat an amino silane and epoxy silane in amounts such that the molar ratio of epoxy silane to amino silane is less than about 1.8;

1; and

then (b) adding additional epoxy silane so that the molar ratio of epoxy silane to amino silane is at least about 2;

1; and

(3) at least about 5 percent by weight, based on the weight of the composition, of a volatile organic solvent;

with the proviso that the reaction product of a polyisocyanate and a compound containing at least one silane group and at least one isocyanate reactive group is not present;

(B) superimposing on the primer composition a bead of a moisture-curable urethane adhesive comprising an isocyanate-functional prepolymer and dimorpholinodiethyl ether; and

(C) installing the window by contacting the adhesive with the vehicle window flange and allowing the adhesive and primer composition to cure.

2. The process of claim 1 wherein the primer composition is prepared such that step (b) is conducted neat or in the presence of an organic solvent, wherein such solvent is present in an amount, based on the weight of the reaction mixture, of less than about 90 percent.

3. The process of claim 1 wherein the film-forming resin of the primer composition is a polyacrylate resin or an epoxy resin.

4. The process of claim 1 wherein the epoxy silane in the primer composition is γ

-glycidoxypropyldimethylethoxy silane, γ

-glycidoxypropylmethyldiethoxy silane, γ

-glycidoxypropyltrimethoxy silane, β

-(3,4-epoxycyclohexyl)ethylmethyltrimethoxy silane, or β

-(3,4-epoxycyclohexyl)ethylmethyldimethoxy silane.

5. The process of claim 4 wherein the epoxy silane of the primer composition is γ

-glycidoxypropyltrimethoxy silane.

6. The process of claim 1 wherein the amino silane of the primer composition is N-(β

-aminoethyl)aminomethyltrimethoxy silane, N-(β

-aminoethyl)-γ

-aminopropyltriethoxy silane, or trimethoxysilylpropyldiethylene triamine.

7. The process of claim 3 wherein the amino silane of the primer composition is N-β

-(aminoethyl)-γ

-aminopropyltrimethoxy silane.