Ester resin compositions

Patent metadata

Field	Value
Publication number	US-8952191-B2
Application number	US-201213680200-A
Country	US
Kind code	B2
Filing date	Nov 19, 2012
Priority date	Nov 19, 2012
Publication date	Feb 10, 2015
Grant date	Feb 10, 2015

Abstract

A composition including one or more ester resins useful for various applications is disclosed. For example, the composition including one or more ester resins may function as a component that is incorporated into an ink composition.

First claim

What is claimed is:

1. An ester composition comprising at least one ester compound represented by:

where R 1 is:
an alkylene group having the structure —(CH2)p- in which p is an integer in a range of from about 2 to about 12, each of R 2 -R 25 are independently selected from the group consisting of hydrogen, alkyl groups, arylalkyl groups, alkylaryl groups, and heterocyclic groups; and wherein x is an integer of one or more.

2. The composition of claim 1 , wherein one or more of the R 2 -R 25 groups are a methyl group and one or more of the R 2 -R 25 groups are hydrogen.

3. The composition of claim 1 , wherein x is an integer from 1 to about 20.

4. The composition of claim 1 , further comprising at least one ester compound represented by

or a mixture of one or more compounds of General Formulas III and/or IV;
where R 1 is:
a) an alkylene group, including substituted and unsubstituted alkylene groups, wherein hetero atoms either may or may not be present in the alkylene group;
b) an arylene group, including substituted and unsubstituted arylene groups, wherein hetero atoms either may or may not be present in the arylene group;
c) an arylalkylene group, including substituted and unsubstituted arylalkylene groups, wherein hetero atoms either may or may not be present in either or both of the alkyl portion and the aryl portion of the arylalkylene group; or
d) an alkylarylene group, including substituted and unsubstituted alkylarylene groups, wherein hetero atoms either may or may not be present in either or both of the alkyl portion and the aryl portion of the alkylarylene group.

5. The composition of claim 4 , wherein the composition has at least 80 percent by weight bio-renewable content, or R 1 is derived from a bio-renewable compound.

6. The composition of claim 5 , wherein the bio-renewable compound is one or more member selected from the group consisting of succinic acid, tartaric acid, malic acid and itaconic acid.

7. The composition of claim 4 where the ester composition includes a mixture of a diester and a monoester, the mixture selected from the group consisting of:

8. The composition of claim 4 , wherein the ester of General Formula IV is present in the composition in an amount in the range of from about 5% to about 50% by weight of the composition.

9. The composition of claim 4 , wherein the ester of General Formula III is present in the composition in an amount in the range of from about 50% to about 95% by weight of the composition.

10. A method for forming the composition of claim 4 , comprising:
melting a carboxylic acid and Abitol E alcohol under an inert atmosphere in the presence of a catalyst, reacting the molten carboxylic acid and Abitol E at an elevated temperature of about 110° C. to about 230° C. under an inert atmosphere, optionally in the presence of a solvent, to form at least one ester compound, and
cooling and isolating the at least one ester compound; wherein the at least one ester compound comprises one or more compound represented by General Formulas I-IV.

11. The method according to claim 10 , wherein reacting the molten carboxylic acid and Abitol E to form at least one ester compound includes removing water.

12. The method according to claim 10 , wherein the reaction to form the at least one ester compound occurs in a solvent selected from the group consisting of toluene, xylenes, and mesitylene.

13. The method according to claim 10 , wherein the catalyst is selected from the group consisting of tetraalkyl titanates, dialkyltin oxides, dibutyltin oxide, dibutyl oxostarmane, tetraalkyltin oxide compounds, dibutyltin dilaurate, dialkylstannoic acid compounds, butylstannoic acid, aluminum alkoxides, alkyl zinc, dialkyl zinc, zinc oxide, stannous oxide, titanium oxide, p-toluenesulfonic acid, sulphuric acid, phosphoric acid, methane sulfonic acid and mixtures thereof.

14. The method according to claim 10 , wherein the catalyst is present in an amount in a range of from about 0.005% to about 5% by weight based on the starting carboxylic acid.

15. The method according to claim 10 , wherein the reaction to form the at least one ester compound is about 99% complete in less than about 15 hours.

16. The ester composition of claim 1 , further comprising in a mixture at least one ester compound represented by:

where R 1 of Formula II is:
a) an alkylene group, including substituted and unsubstituted alkylene groups, wherein hetero atoms selected from the group consisting of oxygen, nitrogen, silicon, phosphorus, fluorine, chorine, bromine and iodide, either may or may not be present in the alkylene group;
b) an arylene group, including substituted and unsubstituted arylene groups, wherein hetero atoms either may or may not be present in the arylene group;
c) an arylalkylene group, including substituted and unsubstituted arylalkylene groups, wherein hetero atoms either may or may not be present in either or both of the alkyl portion and the aryl portion of the arylalkylene group; or
d) an alkylarylene group, including substituted and unsubstituted alkylarylene groups, wherein hetero atoms either may or may not be present in either or both of the alkyl portion and the aryl portion of the alkylarylene group;
two or more substituents can be joined together to form a ring; and
each of R 2 -R 13 are independently selected from the group consisting of hydrogen, alkyl groups, arylalkyl groups, alkylaryl groups, and heterocyclic groups; and wherein x is an integer of one or more.

17. The composition of claim 16 , wherein R 1 of Formula II is an alkylene group having the structure —(CH 2 )p- in which p is an integer in a range of from about 2 to about 12.

18. The composition of claim 16 , wherein the amount of at least one ester compound represented by General Formula I is in the range of from about 50% to about 95% by weight of the composition.

19. The composition of claim 16 , wherein the amount of at least one ester compound represented by General Formula II is in the range of from about 5% to about 50% by weight of the composition.

20. The composition of claim 16 , wherein x of Formula II is an integer from 1 to 20.

Assignees

• Xerox Corp

Inventors

• Goredema Adela
• Carlini Rina
• Belelie Jennifer L
• Chopra Naveen
• Morimitsu Kentaro

Classifications

• C07C69/40

  Succinic acid esters · CPC title

• C07C69/533

  Monocarboxylic acid esters having only one carbon-to-carbon double bond · CPC title

• C07C69/675

  of saturated hydroxy-carboxylic acids · CPC title

• C07C69/70 Primary

  Tartaric acid esters · CPC title

• C09D11/34

  Hot-melt inks · CPC title