Cycloaliphatic and aliphatic diamine-based fatty acid diamides used as organogelators

Patent metadata

Field	Value
Publication number	US-10029978-B2
Application number	US-201414906312-A
Country	US
Kind code	B2
Filing date	Jul 18, 2014
Priority date	Jul 25, 2013
Publication date	Jul 24, 2018
Grant date	Jul 24, 2018

Abstract

The invention also covers the use of this diamide as an organogelling agent, in particular as a rheology additive, for coating, glue, adhesive or cosmetic, stripping, molding, mastic or sealing compositions.

First claim

The invention claimed is:

1. Fatty acid diamide consisting of a product which is mixture of diamides, the product obtained from a reaction mixture comprising:
a) at least one cycloaliphatic diamine comprising a ring of 6 carbon atoms,
b) a fatty hydroxy acid chosen from the group consisting of 12-hydroxystearic acid (12-HSA), 9 hydroxystearic acid (9-HSA), 10-hydroxystearic acid (10-HSA), 14-hydroxyeicosanoic acid (14-HEA) and binary, ternary, and quaternary mixtures thereof,
c) at least a second diamine selected from the group consisting of linear primary aliphatic C2 to C12 diamines,
d) optionally, at least one monoacid selected from the group consisting of saturated and non-hydroxylated linear C6 to C18 carboxylic acids,
e) optionally, at least a third primary diamine different from selected from the group consisting of linear aliphatic C2 to C12 diamines,
f) at least one aromatic diamine chosen from the group consisting of xylylenediamines, said aromatic diamine optionally being partially or totally replaced with a cycloaliphatic diamine as defined in point a);
said fatty acid diamine having a molar percentage of a/(a+f) of at least 50% and up to 100% and having a molar percentage of (a+f)/(a+c+e+f) from 30% to 80%.

2. The fatty acid diamide of claim 1 , having a molar percentage of a/(a+f) of at least 50% up to 100%, and having a molar percentage of (a+f)/(a+c+e+f) from 30% to 65%.

3. The fatty acid diamide of claim 1 wherein said cycloaliphatic diamine a), is in the presence of xylylenediamines f), and in that said diamine a) represents from 50 mol % to 99 mol % of the total number of moles of diamines a)+xylylenediamine f).

4. The fatty acid diamide of claim 1 wherein said diamine f) is absent, with a mole ratio a/(a+f) of 100%, said cycloaliphatic diamine a) being 1,4-BAC or 1,3-BAC.

5. The fatty acid diamide of claim 1 comprising:
i) a diamide consisting of the product of reaction of 1 mol of said diamine a) with 2 mol of said hydroxy acid b) as defined according to claim 1 , and
ii) a diamide consisting of the product of reaction of 1 mol of diamine c) with 2 mol of hydroxy acid b) as defined according to claim 1 and
iii) a diamide consisting of the product of reaction of 1 mol of diamine according to e) and of 2 mol of hydroxy acid b) as defined according to claim 1 .

6. The fatty acid diamide of claim 1 comprising at least 2 different reaction products as derived from the reaction between said diamines a), c) and e) and optionally the xylylenediamines f) and the monoacids b) and optionally d).

7. The fatty acid diamide of claim 1 wherein said monoacid d) is present in a proportion such that the mole ratio d/(b+d) is less than 0.5.

8. The fatty acid diamide of claim 1 in the form of a micronized powder having a mean size by volume of less than 20μ.

9. A method of gelling an organic solvent medium, said method comprising the step of adding the fatty acid diamide of claim 1 to the organic solvent medium.

10. Organogelling agent comprising at least one diamide of claim 1 .

11. Organic binder composition comprising a rheology additive that is at least one diamide according to claim 1 .

12. The organic binder composition of claim 11 , wherein said binder is selected from the group consisting of: epoxy resins, unsaturated polyesters, vinyl esters, alkyds, silane resins, polyurethanes, polyester amides, solvent-based acrylic resins, acrylic monomers and oligomers, chlorinated elastomers, non-chlorinated elastomers, and chlorinated polymers other than chlorinated elastomers.

13. The fatty acid diamide of claim 1 , wherein said cycloaliphatic diamine a) comprises, including said ring, from 6 to 18 carbon atoms, and is chosen from the group consisting of: 1,3-bis(aminomethyl)cyclohexane (1,3-BAC), 1,4-bis(aminomethyl)cyclohexane (1,4-BAC), 1,2-bis(aminomethyl)cyclohexane (1,2-BAC) and isomer mixtures thereof, decahydronaphthalenediamines, and isophoronediamines.

14. The fatty acid diamide of claim 1 , wherein said cycloaliphatic diamine a) is chosen from the group consisting of 1,3-bis(aminomethyl)cyclohexane (1,3-BAC), and 1,4-bis(aminomethyl)cyclohexane (1,4-BAC).

15. The fatty acid diamide of claim 1 , wherein said cycloaliphatic diamine a) is chosen from the group consisting of 1,3-bis(aminomethyl)cyclohexane (1,3-BAC), and 1,4-bis(aminomethyl)cyclohexane (1,4-BAC).

16. The fatty acid diamide of claim 1 , wherein said cycloaliphatic diamine a) is 1,3-bis (aminomethyl) cyclohexane (1,3-BAC).

17. The fatty acid diamide of claim 1 , wherein said hydroxy acid b) is chosen from the group consisting of 12-hydroxystearic acid, and a binary or ternary mixture of 12-hydroxystearic acid with hydroxy acid.

18. The fatty acid diamide of claim 1 , wherein said aromatic diamine f) is m-xylylenediamine (m-XDA).

Assignees

• Arkema France

Inventors

• Bernard Michael Y

Classifications

• C08K5/20

  Carboxylic acid amides · CPC title

• C09D5/34

  Filling pastes (materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12) · CPC title

• C09D7/00

  Features of coating compositions, not provided for in group C09D5/00 (driers C09F9/00); Processes for incorporating ingredients in coating compositions · CPC title

• C09D5/04

  Thixotropic paints · CPC title

• C09D163/00

  Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins · CPC title