# US 10,118,986 B2 · Corrosion-resistant coatings and methods using polyepdxysilane precursors

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- Number: US 10,118,986 B2
- Document ID: US10118986B2
- Status: Granted
- Kind: B2
- Application number: 14/203,075
- Filed: 2014-03-10
- Published: 2014-09-18
- Granted: 2018-11-06
- Earliest claimed: 2013-03-12
- Assignees: Eastern Michigan University
- Applicants: Eastern Michigan University
- Inventors: Vijaykumar M. Mannari
- Web page: https://patentgrep.com/patent/US10118986B2

## CPC

- C08G 59/14: Polycondensates modified by chemical after-treatment
- C07F 7/18: Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F 7/1804: {Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896)}
- C08G 59/504: {containing an atom other than nitrogen belonging to the amine group, carbon and hydrogen}
- Y10T 428/31515: As intermediate layer
- Y10T 428/31529: Next to metal
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

The disclosure relates to curable polyepoxysilane compounds and compositions, methods related to curing of such compounds via hydrolysis and/or condensation to form coatings on a substrate, and coated articles formed from the curable polyepoxysilane compounds. The polyepoxysilane compounds are silane-functional precursors and can be used as coatings (or pretreatments) on various substrates (e.g., metals such as aluminum) and provide a substantial improvement in corrosion resistance relative to other anti-corrosion coatings. The silane-functional precursors can be prepared by reaction of functional silanes (e.g., amino-functional silanes or other epoxide-reactive functionalized silanes) with epoxide-containing organic or hydrocarbon compounds and oligomers/polymers thereof (e.g., glycidyl-type ethers or other epoxide-/oxirane-functionalized hydrocarbon compounds), for example including hydrocarbons with one or more aromatic hydrocarbon groups (e.g., in an aromatic polyether).

## Claims

### Claim 1

A curable polyepoxysilane compound comprising:
a compound having the formula
R—[—O—R4—CH(OH)—CH2—NA1A2]x; (1)
wherein:
(i) R is selected from the group consisting of linear aliphatic, branched aliphatic, and alicyclic hydrocarbons containing from 8 to 50 carbon atoms when x is 2or from 4 to 50 carbon atoms when x is 3or 4, the hydrocarbons being free from aromatic moieties;
(ii) A1 is represented by —R1—Si(R3)3-yXy;
(iii) A2 is represented by —R2—Si(R3)3-zXz or H or R3;
(iv) X is a hydrolysable group independently selected from the group consisting of alkoxy groups, aryloxy groups, carboxyloxy groups, and halogens;
(v) R1 and R2 are independently selected from the group consisting of hydrocarbons containing from 1 to 20 carbon atoms and heteroatom-substituted hydrocarbons containing from 1 to 20 carbon atoms;
(vi) R3 is independently selected from the group consisting of H, hydrocarbons containing from 1 to 20 carbon atoms, and heteroatom-substituted hydrocarbons containing from 1 to 20 carbon atoms;
(vii) R4 is either (A) absent or (B) selected from the group consisting of hydrocarbons containing from 1 to 20 carbon atoms and heteroatom-substituted hydrocarbons containing from 1 to 20 carbon atoms;
(viii) x is 2, 3, or 4;
(ix) y is 1, 2, or 3;
(x) z is 1, 2, or 3 when A2 is not H or R3; and
(xi) the number of hydrolysable groups X ranges from 9 to 24.

### Claim 2 (depends on 1)

The compound of claim 1, wherein the hydrolysable groups X are alkoxy groups and are further independently selected from the group consisting of methoxy groups, ethoxy groups, propoxy groups, and isopropoxy groups.

### Claim 3 (depends on 1)

The compound of claim 1, wherein:
(i) A1 is represented by —C3H6—Si(OCH3)3 or —C3H6—Si(OC2H5)3;
(ii) A2 is represented by H; and
(iii) R4 is present and is represented by —CH2—.

### Claim 4 (depends on 1)

The compound of claim 1, wherein:
(i) A1 is represented by —C3H6—Si(OCH3)3 or —C3H6—Si(OC2H5)3;
(ii) A2 is represented by —C3H6—Si(OCH3)3 or —C3H6—Si(OC2H5)3; and
(iii) R4 is present and is represented by —CH2—.

### Claim 5 (depends on 1)

A process for curing a curable polyepoxysilane compound, the process comprising:
(a) providing a curable polyepoxysilane compound according to claim 1; and
(b) curing the curable polyepoxysilane compound with water, thereby hydrolyzing and condensing at least some of the hydrolysable silyl groups to form a cured polyepoxysilane compound comprising covalent intermolecular siloxane crosslinks in the cured polyepoxysilane compound.

### Claim 6 (depends on 5)

The process of claim 5, wherein providing the curable polyepoxysilane compound in part (a) comprises providing a mixture comprising: (i) the curable polyepoxysilane compound, (ii) an organic solvent for the curable polyepoxysilane compound, (iii) water, (iv) a catalyst, (v) optionally a corrosion inhibitor; and (vi) optionally a silane crosslinker.

### Claim 7 (depends on 5)

The process of claim 5, further comprising:
(c) applying partially cured polyepoxysilane compound from part (b) to a substrate; and
(d) further curing the partially cured polyepoxysilane compound on the substrate, thereby forming the cured polyepoxysilane compound as a coating on the substrate.

### Claim 8 (depends on 7)

The process of claim 7, wherein the substrate is a metallic substrate and the cured polyepoxysilane compound coating reduces or prevents corrosion of the metallic substrate.

### Claim 9 (depends on 8)

The process of claim 8, wherein the cured polyepoxysilane compound coating is covalently bonded to the metallic substrate via a —SiO—functional group.

### Claim 10 (depends on 8)

The process of claim 8, wherein the metallic substrate comprises aluminum.

### Claim 11 (depends on 7)

The process of claim 7, further comprising:
applying a polymeric primer as a coating on a surface of the cured polyepoxysilane compound opposite the substrate; and
applying a polymeric topcoat as a coating on a surface of the polymeric primer opposite the cured polyepoxysilane compound.

### Claim 12 (depends on 1)

The compound of claim 1, wherein R contains 8to 50carbon atoms when x is 2, 3, or 4.

### Claim 13 (depends on 1)

The compound of claim 1, wherein R is an alicyclic hydrocarbon.