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alpha, alpha-branched alkane carboxylic glycidyl esters compositions and applications

IP.com Disclosure Number: IPCOM000216568D
Publication Date: 2012-Apr-10

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Research Disclosure RD563016: OTHER [+3]

Abstract

We have prepared and evaluated 2,3-epoxypropyl trialkyl substituted acetate (OXI; alpha, alpha-branched alkane carboxylic glycidyl esters) based on branched alkane carboxylic acids, the latter comprising in total 9 or 13 carbon atoms. The alkyl groups substituting the carbon atom in alpha position to the carbonyl group of the carboxylic acids therefore comprise in total 7 or 11 carbon atoms; at least one of the alkyl groups is a methyl group. The isomers of branched alkane carboxylic acid as illustrative example have the structure (R1, R2, R3)-C-COOH where the three R groups are linear or branched alkyl groups having together a total of 7 carbon atoms as depicted in Table 1. For instance, 2,3-epoxypropyl trialkyl substituted acetate (OXI; glycidyl neononanoate; Cardura 9) with isomeric composition as given in Table 2 have been found especially suitable as illustrated in the examples below. Such molecules and their applications have been described in Research Disclosures RD563016, RD573003 and RD573005.

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alpha, alpha-branched alkane carboxylic glycidyl esters compositions and applications

Disclosed anonymously

We have prepared and evaluated 2,3-epoxypropyl trialkyl substituted acetate (OXI; alpha, alpha-branched alkane carboxylic glycidyl esters) based on branched alkane carboxylic acids, the latter comprising in total 9 or 13 carbon atoms. The alkyl groups substituting the carbon atom in alpha position to the carbonyl group of the carboxylic acids therefore comprise in total 7 or 11 carbon atoms; at least one of the alkyl groups is a methyl group. The isomers of branched alkane carboxylic acid as illustrative example have the structure (R1, R2, R3)-C-COOH where the three R groups are linear or branched alkyl groups having together a total of 7 carbon atoms as depicted in Table 1. For instance, 2,3-epoxypropyl trialkyl substituted acetate (OXI; glycidyl neononanoate; Cardura 9) with isomeric composition as given in Table 2 have been found especially suitable as illustrated in the examples below. Such molecules and their applications have been described in Research Disclosures RD563016, RD573003 and RD573005.

Branched alkane carboxylic acids V9XX               

R1

R2

R3

V901

Methyl

Methyl

n-pentyl

V902

Methyl

Methyl

2-pentyl

V903

Methyl

Methyl

2-methyl butyl

V904

Methyl

Methyl

3-methyl butyl

V905

Methyl

Methyl

1,1-dimethyl propyl

V906

Methyl

Methyl

1,2-dimethy propyl

V907

Methyl

Methyl

2,2-dimethyl propyl

V908

Methyl

Methyl

3-pentyl

V909

Methyl

Ethyl

n-butyl

V910 K1

Methyl

Ethyl

s-butyl

V910

K2

Methyl

Ethyl

s-butyl

V911

Methyl

Ethyl

i-butyl

V912

Methyl

Ethyl

t-butyl

V913

Methyl

n-propyl

n-propyl

V914

Methyl

n-propyl

i-propyl

V915

Methyl

i-propyl

i-propyl

V916

Ethyl

Ethyl

n-propyl

V917

Ethyl

Ethyl

i-propyl

Table 1: Structure of branched alkane carboxylic acids V9XX isomers

OXI made from  acid V9XX described in Table 1

A (%)

B (%)

C (%)

D (%)

E (%)

F (%)

V901

6.5

0.1

3.7

0.1

0.1

8.9

V902

0.6

2.55

0.6

2.4

2.65

0.7

V903

1.1

0.7

0.3

1.0

0.4

2.0

V904

0.8

1

0.1

2.2

0.4

1.8

V905

0.2

13.1

0.5

4.1

14.5

0.1

V906

0.4

11.6

0.4

9.6

12.6

0.4

V907

0.2

15.4

0.1

36.4

5.6

0.6

V908

0.1

0

0.1

0.0

0.0

0.1

V909

54.8

2.55

52.8

2.4

2.65

52.8

V910 K1

7.8

0

10.0

0.0

0.0

6.5

V910

K2

7.7

0.6

12.8

0.4

0.7

4.8

V911

2.4

1.2

0.7

2.0

0.8

4.2

V912

0.0

28.3

0.0

22.4

33.5

0.0

V913

6.8

0.1

6.4

0.1

0.1

6.5

V914

4.5

0

3.8

0.0

0.0

5.7

V915

0.6

22.3

0.6

16.8

25.3

0.4

V916

4.4

0.1

5.2

0.1

0.1

3.8

V917

1.1

0.4

2.1

0.1

0.4

0.5

Table 2: Composition of OXI

Chemicals used for below examples

-       GE9S: OXI of composition A (see table 2)

-       GE9H: OXI of composition B (see table 2)

-       OXI of composition C (see table 2)

-       OXI of composition D (see table 2)

-       OXI of composition E (see table 2)

-       OXI of composition F (see table 2)

-       GE5: glycidyl ester of pivalic acid obtained by reaction of the acid with epichlorhydrin.

-       Thinner: A: is a mixture of Xylene 50wt%, Toluene 30wt%, ShellsolA 10wt%, 2-Ethoxyethylacetate 10wt%. Thinner B: is butyl acetate

-       Curing agents, HDI: 1,6-hexamethy...