# US 9,751,982 B2 · Polyether polyol resins compositions

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- Number: US 9,751,982 B2
- Document ID: US9751982B2
- Status: Granted
- Kind: B2
- Application number: 14/352,247
- Filed: 2012-10-16
- Published: 2014-08-14
- Granted: 2017-09-05
- Earliest claimed: 2011-10-19
- Assignees: Hexion Inc.
- Applicants: Momentive Specialty Chemicals Research Beigium S.A.; Momentive Specialty Chemicals Inc.
- Inventors: Denis Heymans; Christophe Steinbrecher; Cédric Le Fevere De Ten Hove
- Web page: https://patentgrep.com/patent/US9751982B2

## CPC

- C08G 65/22: Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
- C08G 63/664: derived from hydroxy carboxylic acids
- C08G 65/14: Unsaturated oxiranes
- C08G 65/2609: {containing aliphatic hydroxyl groups}
- C08G 65/3322: {acyclic}
- C09D 7/65: macromolecular (C09D7/41-C09D7/48 take precedence)
- C09D 171/00: Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain (based on polyacetals C09D159/00; based on epoxy resins C09D163/00; based on polythioether-ethers C09D181/02; based on polyethersulfones C09D181/06); Coating compositions based on derivatives of such polymers
- C09D 171/02: Polyalkylene oxides
- Y10T 428/31504: Composite [nonstructural laminate]
- Y10T 428/31678: Of metal
- 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)
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

The invention relates to compositions of polyether polyol resins (hydroxyfunctional oligo or poly ether) comprising a mixture of α,α-branched alkane carboxylic glycidyl esters derived from butene oligomers characterized in that the sum of the concentration of the blocked and of the highly branched isomers is maximum 55%, preferably below 40%, and most preferably below 30% weight on total composition.

## Claims

### Claim 1

A process to prepare a composition of polyether polyol resin comprising reacting at least one polyol having at least three hydroxyl groups and a composition of α,α-branched alkane carboxylic glycidyl esters from butene oligomers, comprising a glycidyl ester mixture of neo-acids derived from a dimer or trimer of butene having both blocked isomers and highly branched isomers wherein a sum of a concentration of blocked isomers and the concentration of highly branched isomers is a maximum of 55 wt % based on the weight of the composition of α,α-branched alkane carboxylic glycidyl esters, wherein the highly branched isomers are isomers of neo-acids having at least 5 methyl groups.

### Claim 2 (depends on 1)

The process of claim 1, wherein the composition of α,α-branched alkane carboxylic glycidyl esters is based on a neononanoic acid mixture wherein the sum of the concentration of the blocked and of the highly branched isomers is a maximum of 55 wt % based on the total weight of the composition.

### Claim 3 (depends on 2)

The process of claim 2 wherein the composition of α,α-branched alkane carboxylic glycidyl esters comprises 2,2-dimethyl heptanoic acid glycidyl ester, or 2-methyl 2-ethyl hexanoic acid glycidyl ester or 2-methyl 2-ethyl 3-methyl pentanoic acid glycidyl esters.

### Claim 4 (depends on 2)

The process of claim 2 wherein the composition of α,α-branched alkane carboxylic glycidyl esters comprises 2-methyl 2-ethyl 3-methyl pentanoic acid glycidyl ester stereoisomers in an amount below 40 wt % based on the total weight of the composition.

### Claim 5 (depends on 4)

The process of claim 4 wherein the mixture of α,α-branched alkane carboxylic glycidyl esters comprises 2-methyl 2-ethyl 3-methyl pentanoic acid glycidyl ester stereoisomers in an amount below 30 wt % based on the total weight of the composition.

### Claim 6 (depends on 4)

The process of claim 4 wherein the mixture of α,α-branched alkane carboxylic glycidyl esters comprises 2-methyl 2-ethyl 3-methyl pentanoic acid glycidyl ester stereoisomers in an amount below or equal to 25 wt % based on the total weight of the composition.

### Claim 7 (depends on 2)

The process of claim 2 wherein the composition of α,α-branched alkane carboxylic glycidyl esters comprises 2-methyl 2-ethyl hexanoic acid glycidyl ester in an amount above 10 wt % based on the total weight of the composition.

### Claim 8 (depends on 7)

The process of claim 7 wherein the mixture of α,α-branched alkane carboxylic glycidyl esters comprises 2-methyl 2-ethyl hexanoic acid glycidyl ester in an amount above 30 wt % based on the total weight of the composition.

### Claim 9 (depends on 7)

The process of claim 7 wherein the mixture of α,α-branched alkane carboxylic glycidyl esters comprises 2-methyl 2-ethyl hexanoic acid glycidyl ester in an amount above 45 wt % based on the total weight of the composition.

### Claim 10 (depends on 2)

The process of claim 2 wherein the composition of α,α-branched alkane carboxylic glycidyl esters comprises 2,2-dimethyl heptanoic acid glycidyl ester, 2-methyl 2-ethyl hexanoic acid glycidyl ester and 2-methyl 2-ethyl 3-methyl pentanoic acid glycidyl ester stereoisomers in an amount above 40 wt % based on the total weight of the composition.

### Claim 11 (depends on 10)

The process of claim 10 wherein the mixture of α,α-branched alkane carboxylic glycidyl esters comprises 2,2-dimethyl heptanoic acid glycidyl ester, 2-methyl 2-ethyl hexanoic acid glycidyl ester and 2-methyl 2-ethyl 3-methyl pentanoic acid glycidyl ester stereoisomers in an amount above 55 wt % based on the total weight of the composition.

### Claim 12 (depends on 10)

The process of claim 10 wherein the mixture of α,60 -branched alkane carboxylic glycidyl esters comprises 2,2-dimethyl heptanoic acid glycidyl ester, 2-methyl 2-ethyl hexanoic acid glycidyl ester and 2-methyl 2-ethyl 3-methyl pentanoic acid glycidyl ester stereoisomers in an amount above 65 wt % based on the total weight of the composition.

### Claim 13 (depends on 2)

The process of claim 2 wherein the composition of α,α-branched alkane carboxylic glycidyl esters comprises 2,2-dimethyl heptanoic acid glycidyl ester in an amount of 1 to 15 wt %, 2-methyl 2-ethyl hexanoic acid glycidyl ester in an amount of 40 to 70 wt % and 2-methyl 2-ethyl 3-methyl pentanoic acid glycidyl ester stereoisomers in an amount of 8 to 32 wt % based on the total weight of the composition.

### Claim 14 (depends on 2)

The process of claim 2 wherein the composition of α,α-branched alkane carboxylic glycidyl esters comprises 2,2-dimethyl heptanoic acid glycidyl ester in an amount of 2 to 10 wt %, 2-methyl 2-ethyl hexanoic acid glycidyl ester in an amount of 47 to 61 wt % and 2-methyl 2-ethyl 3-methyl pentanoic acid glycidyl ester stereoisomers in an amount of 10 to 25 wt % based on the total weight of the composition.

### Claim 15 (depends on 2)

The process of claim 2 wherein the sum of the concentration of the blocked isomers and of the highly branched isomers is below 40 wt % based on the total weight of the composition.

### Claim 16 (depends on 2)

The process of claim 2 wherein the sum of the concentration of the blocked isomers and of the highly branched isomers is below 30 wt % based on the total weight of the composition.

### Claim 17 (depends on 1)

The process of claim 1 wherein the polyether polyol resin composition has a number average molecular weight (Mn) lower than 4500 Dalton according the polystyrene standard or has an hydroxyl value above 120 mg KOH/g on solids.

### Claim 18 (depends on 1)

The process of claim 1, wherein the sum of the concentration of the blocked isomers and of the highly branched isomers is below 40 wt % based on the total weight of the composition.

### Claim 19 (depends on 1)

The process of claim 1, wherein the sum of the concentration of the blocked isomers and of the highly branched isomers is below 30 wt % based on the weight of the composition.

### Claim 20 (depends on 1)

The process of claim 1 wherein the mixture of α,α-branched alkane carboxylic glycidyl esters is derived from butene oligomers.

### Claim 21 (depends on 1)

A binder composition useful for a coating application with a low VOC and comprising the polyether polyol resin composition from the process of claim 1.

### Claim 22 (depends on 21)

A metal or plastic substrate coated with a coating composition comprising the binder composition of claim 21.

### Claim 23 (depends on 1)

A polyester-ether resin comprising the reaction product of the polyether polyol resin composition from the process of claim 1 and dimethylol propionic acid.