# US 9,040,622 B2 · Solvent-based primer solution based on silylated polyurethane (SPUR) chemistry for polycarbonate substrates

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- Number: US 9,040,622 B2
- Document ID: US9040622B2
- Status: Granted
- Kind: B2
- Application number: 13/463,535
- Filed: 2012-05-03
- Published: 2013-11-07
- Granted: 2015-05-26
- Earliest claimed: 2012-05-03
- Assignees: PPG Industries Ohio, Inc.
- Applicants: Razmik Boghossian
- Inventors: Razmik Boghossian
- Web page: https://patentgrep.com/patent/US9040622B2

## CPC

- C08K 5/05: Alcohols; Metal alcoholates
- B32B 15/02: {Layer formed of wires, e.g. mesh}
- B32B 15/08: of synthetic resin
- B32B 27/08: of synthetic resin
- B32B 27/365: {comprising polycarbonates}
- B32B 27/40: comprising polyurethanes
- C08G 18/44: Polycarbonates
- C08G 18/755: {and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate}
- C08G 18/7843: {containing urethane groups}
- C08K 5/101: of monocarboxylic acids
- C09D 175/12: from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group
- C09J 175/04: Polyurethanes
- B32B 2255/10: on synthetic resin layer or on natural or synthetic rubber layer
- B32B 2255/26: Polymeric coating
- B32B 2605/18: Aircraft
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- B32B: LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H)

## Abstract

A primer solution for enhanced adhesion to a rigid substrate for aviation and aerospace applications includes an aminosilane-capped polyurethane prepolymer and a first solvent. The first solvent reacts with or modifies the surface of the rigid substrate, enabling the primer solution including the aminosilane-capped polyurethane prepolymer to become a part of the surface of the rigid substrate.

## Claims

### Claim 1

A primer solution for use on a rigid substrate, the primer solution comprising:
a first solvent capable of reacting with or modifying a surface of the rigid substrate;
a second solvent having a boiling point greater than 100° C., and
an aminosilane-capped polyurethane prepolymer represented by Chemical Formula 1a or Chemical Formula 1b:
wherein each of R1, R1′ R2, R3 and R4 comprises an aliphatic hydrocarbon, R5 comprises a polyhydroxy linkage, R6 comprises an aliphatic or cycloaliphatic hydrocarbon group, and x is an integer between 1 and 5.

### Claim 2 (depends on 1)

The primer solution according to claim 1, wherein the second solvent comprises diacetone alcohol.

### Claim 3 (depends on 1)

The primer solution according to claim 1, wherein the first solvent is present in an amount of 0.5% to 5% by weight based on the total weight of the primer solution.

### Claim 4 (depends on 1)

The primer solution according to claim 1, wherein the first solvent is present in an amount of 1.2% to 1.8% by weight based on the total weight of the primer solution.

### Claim 5 (depends on 1)

The primer solution according to claim 1, wherein the first solvent comprises butyl acetate.

### Claim 6 (depends on 1)

The primer solution according to claim 1, further comprising a low molecular weight alcohol.

### Claim 7 (depends on 6)

The primer solution according to claim 6, wherein the low molecular weight alcohol comprises methanol, ethanol and/or isopropyl alcohol.

### Claim 8 (depends on 1)

The primer solution according to claim 1, wherein R6 comprises an aliphatic hydrocarbon group.

### Claim 9 (depends on 8)

The primer solution according to claim 8, wherein the aliphatic hydrocarbon group comprises isophorone.

### Claim 10 (depends on 1)

The primer solution according to claim 1, wherein R5 comprises a polycarbonate group.

### Claim 11 (depends on 1)

The primer solution according to claim 1, wherein R1 and R3 each comprise a propyl group, and R2 and R4 each comprise a methyl group.

### Claim 12 (depends on 1)

The primer solution according to claim 1, further comprising a catalyst.

### Claim 13 (depends on 12)

The primer solution according to claim 12, wherein the catalyst comprises dibutyl tin diacetate, dibutyl tin dioctate and/or dibutyl tin dilaurate.

### Claim 14

A method of preparing a primer solution for use on a rigid substrate, comprising:
mixing a polyol represented by Chemical Formula 3 with a first solvent capable of activating or modifying a surface of the rigid substrate;
reacting an isocyanate represented by Chemical Formula 4 and the polyol to produce a polyurethane prepolymer represented by Chemical Formula 2;
reacting an aminosilane represented by Chemical Formula 5a or Chemical Formula 5b with the polyurethane prepolymer to produce an amino silane-capped polyurethane prepolymer represented by Chemical Formula 1a or Chemical Formula 1b; and
adding a second solvent to the amino silane-capped polyurethane prepolymer, the second solvent having a boiling point of greater than 100° C.,
wherein each of R1, R1′ R2, R3 and R4 comprises an aliphatic hydrocarbon, R5 comprises a polyhydroxy linkage, R6 comprises an aliphatic or cycloaliphatic hydrocarbon group, and x is an integer between 1 and 5;
wherein R5 comprises a polyhydroxy linkage, R6 comprise an aliphatic or cycloaliphatic hydrocarbon group, and x is an integer between 1 and 5;
(HO)aR5 Chemical Formula 3
wherein R5 comprises a polyhydroxy linkage, and a is 1 or 2;
R6—(N═C═O)b Chemical Formula 4
wherein R6 comprises an aliphatic or cycloaliphatic hydrocarbon, and b is 1 or 2
wherein R1, R1′, R3, R3′ and R3″ each comprise an aliphatic hydrocarbon, and R2 and R4 each comprise an aliphatic hydrocarbon.

### Claim 15 (depends on 14)

The method according to claim 14, wherein the second solvent comprises diacetone alcohol.

### Claim 16 (depends on 14)

The method according to claim 14, wherein the first solvent is added in an amount of 0.5% to 5% by weight based on the total weight of the primer solution.

### Claim 17 (depends on 14)

The method according to claim 14, wherein the first solvent is added in an amount of 1.2% to 1.8% by weight based on the total weight of the primer solution.

### Claim 18 (depends on 14)

The method according to claim 14, wherein the first solvent comprises butyl acetate.

### Claim 19 (depends on 14)

The method according to claim 14, further comprising adding a low molecular weight alcohol to the aminosilane-capped polyurethane prepolymer.

### Claim 20 (depends on 14)

The method according to claim 14, wherein the isocyanate comprises an aliphatic diisocyanate.

### Claim 21 (depends on 20)

The method according to claim 20, wherein the aliphatic diisocyanate comprises isophorone diisocyanate (“IPDI”).

### Claim 22 (depends on 14)

The method according to claim 14, wherein the polyol comprises a polycarbonate diol.

### Claim 23 (depends on 14)

The method according to claim 14, wherein the aminosilane comprises bis-(gamma-Trimethoxysilylpropyl)amine.

### Claim 24 (depends on 14)

The method according to claim 14, wherein the reacting the isocyanate and the polyol further comprises adding a catalyst.

### Claim 25 (depends on 24)

The method according to claim 24, wherein the catalyst comprises dibutyl tin diacetate, dibutyl tin dioctate and/or dibutyl tin dilaurate.

### Claim 26 (depends on 14)

The method according to claim 14, further comprising melting the polyol before mixing the polyol with the first solvent.

### Claim 27 (depends on 1)

An article, comprising:
a substrate; and
the primer solution according to claim 1 on at least a portion of the substrate.

### Claim 28 (depends on 27)

The article according to claim 27, wherein the substrate is rigid.

### Claim 29 (depends on 27)

The article according to claim 27, wherein the substrate is transparent.

### Claim 30 (depends on 27)

The article according to claim 27, wherein the substrate comprises a polymer.

### Claim 31 (depends on 27)

The article according to claim 27, wherein:
the substrate comprises a polymer;
the substrate is rigid; and
the substrate is transparent.

### Claim 32 (depends on 27)

The article according to claim 27, wherein the substrate comprises at least one selected from the group consisting of a polycarbonate, glass, and an acrylic.

### Claim 33 (depends on 27)

The article according to claim 27, wherein the substrate comprises polycarbonate.

### Claim 34 (depends on 27)

A window, comprising the article according to claim 27.

### Claim 35 (depends on 34)

The window according to claim 34, wherein the window is selected from the group consisting of a windshield and a canopy.