# US 8,785,544 B2 · Primer composition and laminate using the same

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- Number: US 8,785,544 B2
- Document ID: US8785544B2
- Status: Granted
- Kind: B2
- Application number: 13/221,712
- Filed: 2011-08-30
- Published: 2012-03-15
- Granted: 2014-07-22
- Earliest claimed: 2010-09-13
- Assignees: The Yokohama Rubber Co., Ltd.
- Applicants: Akihiro Miyata
- Inventors: Akihiro Miyata
- Web page: https://patentgrep.com/patent/US8785544B2

## CPC

- C03C 17/30: with silicon-containing compounds
- B32B 7/12: using interposed adhesives or interposed materials with bonding properties
- C03C 17/322: {Polyurethanes or polyisocyanates}
- C08G 18/289: {containing silicon}
- C08G 18/73: acyclic
- C08G 18/7621: {being toluene diisocyanate including isomer mixtures}
- C08L 75/06: from polyesters
- B32B 2255/26: Polymeric coating
- B32B 2419/00: Buildings or parts thereof
- B32B 2605/00: Vehicles
- C08G 2190/00: Compositions for sealing or packing joints
- C08K 3/04: Carbon
- C08K 5/544: containing nitrogen
- Y10T 428/31551: Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T 428/31598: Next to silicon-containing [silicone, cement, etc.] layer
- Y10T 428/31601: Quartz or glass
- C03C: CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- 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
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

A primer composition is provided that includes a reactant having an alkoxysilyl group, the reactant being obtained by reacting a polyisocyanate (I), an isocyanate group, and an alkoxysilane having a reactable functional group; a polyisocyanate (II); a polyurethane compound; a (meth) acrylic resin; and a solvent. In the primer composition, a molecular weight of the (meth) acrylic resin is from 15,000 to 150,000 and a weight ratio [(meth) acrylic resin/polyurethane compound] of the (meth) acrylic resin to the polyurethane compound is from 90/10 to 10/90. Additionally, a laminate is provided that includes an inorganic material and a primer layer obtained from the primer composition.

## Claims

### Claim 1

A primer composition comprising:
a reactant having an alkoxysilyl group, the reactant being obtained by reacting a polyisocyanate (I) and an alkoxysilane having a functional group that is reactable with an isocyanate group;
a polyisocyanate (II);
a polyurethane compound;
a (meth) acrylic resin; and
a solvent; wherein
a molecular weight of the (meth) acrylic resin is from 15,000 to 150,000, and
a weight ratio of the (meth) acrylic resin to the polyurethane compound is from 90/10 to 10/90.

### Claim 2 (depends on 1)

The primer composition according to claim 1, wherein the (meth) acrylic resin is one or two or more of a polymer obtained from a methyl methacrylate homopolymer; a methyl acrylate homopolymer; and a copolymer of at least two selected from the group consisting of methyl acrylate, methyl methacrylate, butyl acrylate, and butyl methacrylate.

### Claim 3 (depends on 1)

The primer composition according to claim 1, wherein a content of the reactant is from 10 to 400 parts by mass per a total 100 parts by mass of the polyurethane compound and the (meth) acrylic resin.

### Claim 4 (depends on 1)

The primer composition according to claim 1, wherein a content of the polyisocyanate (II) is from 30 to 300 parts by mass per the total 100 parts by mass of the polyurethane compound and the (meth) acrylic resin.

### Claim 5 (depends on 1)

The primer composition according to claim 1, wherein a content ratio of the reactant to the polyisocyanate (II) is from 10/90 to 90/10.

### Claim 6 (depends on 1)

The primer composition according to claim 1, further comprising a carbon black.

### Claim 7 (depends on 6)

The primer composition according to claim 6, wherein a content of the carbon black is from 3 to 100 parts by mass per a total 100 parts by mass of a solid content of the reactant, the polyisocyanate (II), the polyurethane compound, and the (meth) acrylic resin.

### Claim 8 (depends on 1)

The primer composition according to claim 1, wherein the solvent comprises ethyl acetate or methyl ethyl ketone (MEK), and wherein the reactant comprises an isocyanate group and is obtained by mixing the polyisocyanate (I) and the alkoxysilane in the solvent and agitating under conditions from room temperature to about 40 ° C.

### Claim 9 (depends on 1)

The primer composition according to claim 1, wherein the reactant is expressed by Formula (I):
where R1 is a residue of the polyisocyanate (I) from which an isocyanate group has been removed; Y is a group formed from a functional group that is reactable with an isocyanate group and the isocyanate group; R4 is an organic group or a single bond; R2 is an alkoxy group; R3 is a hydrocarbon group; m is an integer from 1 to 4; n is an integer from 1 to 3; and x is an integer from 0 to 3.

### Claim 10 (depends on 9)

The primer composition according to claim 9, wherein:
the organic group R4 has from 1 to 8 carbon atoms and includes one or more groups selected from methylene groups, ethylene groups, trimethylene groups, tetramethylene groups, pentamethylene groups, hexamethylene groups, heptyl groups, and octyl groups;
the hydrocarbon group R3 includes one or more groups selected from selected from methyl groups, ethyl groups, phenyl groups, and combinations thereof;
m is an integer from 1 to 3;
n is an integer from 2 to 3; and
x is an integer from 0 to 2.

### Claim 11 (depends on 1)

The primer composition according to claim 1, wherein the reactant is obtained by reacting an adduct body formed from 1,1,1-trimethylolpropane (TMP) and tolylene diisocyanate (TDI) and/or an isocyanurate body obtained from HDI and TDI with N-phenyl-γ-aminopropyltrimethoxysilane and/or 3-mercaptopropyltrimethoxysilane.

### Claim 12 (depends on 1)

The primer composition according to claim 1, wherein the reactant comprises a combination of a plurality of reactants including: a compound (III) having one or more isocyanate groups, from 1 to 3 alkoxysilyl groups, and at least one selected from the group consisting of a thiourethane bond, a urea bond, an adduct body skeleton, and a triisocyanurate skeleton; and a compound (IV) having 4 or more alkoxysilyl groups and at least one selected from the group consisting of a thiourethane bond, a urea bond, an adduct body skeleton, and a triisocyanurate skeleton.

### Claim 13 (depends on 12)

The primer composition according to claim 12, wherein a mass ratio of the compound (III) to the compound (IV) is from 10:1 to 1:10.

### Claim 14 (depends on 1)

The primer composition according to claim 1, wherein the polyisocyanate (II) is an adduct body of 1,1,1-trimethylolpropane (TMP) and hexamethylene diisocyanate (HDI) or tolylene diisocyanate (TDI), or an isocyanurate body obtained from HDI and/or TDI.

### Claim 15 (depends on 1)

The primer composition according to claim 1, wherein the molecular weight of the (meth) acrylic resin is from 50,000 to 150,000 and the weight ratio of the (meth) acrylic resin to the polyurethane compound is from 70/30 to 30/70.

### Claim 16 (depends on 1)

The primer composition according to claim 1, further comprising a carbon black, and wherein:
a content of the reactant is from 20 to 300 parts by mass per a total 100 parts by mass of the polyurethane compound and the (meth) acrylic resin;
a content of the polyisocyanate (II) is from 40 to 250 parts by mass per the total 100 parts by mass of the polyurethane compound and the (meth) acrylic resin;
a weight ratio (II) of the reactant to the polyisocyanate (II) is from 20/80 to 80/20; and
a content of the carbon black is from 5 to 80 parts by mass per 100 parts by mass of a solid content of the primer composition excluding the carbon black.