IP Library Granted Patent US 12,240,795
Granted Patent B2
US 12,240,795 · App. 17/288,100 · Granted Mar 4, 2025

Rheological additive based on optionally biosourced 1,5-pentamethylenediamine

Inventors: Carine Fouilliart (Verneuil en Halatte, FR); Virginie Ducastel (Verneuil en Halatte, FR); Vincent Leroy (Verneuil en Halatte, FR); Dmitri Colesnic (Verneuil en Halatte, FR)
Assignee: Arkema France
C07C235/10C08K5/20C09D7/43
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Quick Facts
Patent No.
US 12,240,795
App. No.
17/288,100
Granted
Mar 4, 2025
Kind
B2
Abstract

The present invention relates to a rheology additive, according to which A) said additive consists of: a) at least one symmetrical fatty diamide of formula (I): (AGH)-CONH-(PMDA)-NHCO-(AGH) (I) with: (AGH): hydroxylated fatty acid residue R1CO2H, without —CO2H group, with R1 of C18 to C20 comprising a hydroxyl group, —NHCO— or —CONH—: amide group, —(PMDA): residue without amine groups of 1,5-pentamethylenediamine; or alternatively according to which: B) said additive comprises: a) at least one symmetrical fatty diamide as defined above according to formula (I) and, in addition, b) at least one other symmetrical fatty diamide of formula (II): (AGH)-CONH-(R)-NHCO-(AGH) (II) with (AGH), —NHCO— and —CONH— having the same definition as that above in said formula (I), and (R) being the residue without amine groups of a diamine, other than (PMDA), chosen from a cycloaliphatic, aliphatic or aromatic diamine.

Claims (31)

1. A rheology additive wherein:

said additive comprises:

a) at least one symmetrical fatty acid diamide of formula (I):

(AGH)-CONH-(PMDA)-NHCO-(AGH)  (I),

and, in addition,

b) at least one other symmetrical fatty diamide of formula (II):

(AGH)-CONH-(R)-NHCO-(AGH)  (II)

wherein:

(AGH) is a residue of a hydroxylated fatty acid R 1 CO 2 H, without —CO 2 H group, wherein the hydroxylated fatty acid R 1 CO 2 H is selected from the group consisting of: 12-hydroxystearic acid (12HSA), 9-hydroxystearic acid, 10-hydroxystearic acid and 14-hydroxyeicosanoic acid,

—NHCO— and —CONH— is each an amide group,

(PMDA) is a residue without amine groups of 1,5-pentamethylenediamine, and

(R) is a residue without amine groups of a diamine, other than (PMDA), chosen from the group consisting of a cycloaliphatic, linear aliphatic and aromatic diamine.

2. The rheology additive according to claim 1 , wherein said fatty diamide a) is present at a content by weight, relative to a)+b), ranging from 0.5 to 99.5%.

3. The rheology additive according to claim 1 , wherein said fatty diamide a) is present at a content by weight, relative to a)+b), ranging from 0.5 to 99.5% or 1 to 95% or 5 to 75% or 5 to 50% or 5 to 45% or 7 to 50% or 7 to 45% or 10% to 50% or 10% to 45% or 50 to 95% or 60 to 95% or 70 to 95% or 50 to 90% or 55 to 90% or 60 to 90% or 70 to 90% or 30 to 70% or 35 to 65% or 40 to 60% or 45 to 55%.

4. The rheology additive according to claim 1 , wherein (R) is the residue of a cycloaliphatic diamine chosen from 1,3- or 1,4-diaminecyclohexane, 1,3- or 1,4-bis(aminomethyl)cyclohexane and isophorone diamine.

5. The rheology additive according to claim 1 , wherein (R) is a residue of 1,3-bis(aminomethyl)cyclohexane.

6. The rheology additive according to claim 1 in the form of a micronized powder with a particle size corresponding to a volume mean size ranging from 1 to 15 μm.

7. The rheology additive according to claim 4 , wherein the content by weight of the fatty diamide a), relative to the weight a)+b), is from 5 to 50% or 5 to 45% or 7 to 50% or 7 to 45% or 10 to 50% or 10 to 45% or 50 to 95% or 55 to 95% or 60 to 95% or 70 to 95% or 50 to 90% or 55 to 90% or 60 to 90% or 70 to 90%.

8. The rheology additive according to claim 1 , wherein (R) is the residue of a linear aliphatic diamine chosen from ethylenediamine, diethylenetriamine, 1,3-propylenediamine, 1,4-butylenediamine, and 1,6-hexamethylenediamine.

9. The rheology additive according to claim 8 , wherein (R) is the residue of 1,6-hexamethylenediamine.

10. The rheology additive according to claim 8 , wherein the content by weight of the fatty diamine a), relative to the weight a)+b), ranges from 30 to 70% or 35 to 65% or 40 to 60% or 45 to 55%.

11. The rheology additive according to claim 1 , wherein (R) is the residue of an aromatic diamine chosen from o-, m- and p-phenylenediamine or o-, m- and p-xylenediamine.

12. An organic binder composition, comprising at least one rheology additive as defined according to claim 1 .

13. The organic binder composition according to claim 12 , wherein said organic binder composition is a coating composition, adhesive-bonding agent or adhesive composition, moulding composition, composite, mastic or leaktightness agent composition or cosmetic composition.

14. The organic binder composition according to claim 12 , wherein said organic binder is selected from: epoxy resins, unsaturated and saturated polyesters, vinyl ester, alkyds, silanized resins, polyurethanes, polyester amides, solvented acrylic resins, multifunctional acrylic monomers and/or oligomers, and acrylated acrylic resins with reactive diluent or inert resins diluted in a reactive or non-reactive solvent.

15. The rheology additive according to claim 2 , wherein said fatty diamide a) is present at a content by weight, relative to a)+b), ranging from 5 to 75%.

16. The rheology additive according to claim 15 , wherein said fatty diamide a) is present at a content by weight, relative to a)+b), ranging from 7 to 45%.

17. The rheology additive according to claim 4 , wherein the content by weight of the fatty diamide a), relative to the weight a)+b), is from 5 to 50%.

18. The rheology additive according to claim 4 , wherein the content by weight of the fatty diamide a), relative to the weight a)+b), is from 50 to 95%.

19. The rheology additive according to claim 8 , wherein the content by weight of the fatty diamine a), relative to the weight a)+b), ranges from 30 to 70%.

20. The rheology additive according to claim 19 , wherein the content by weight of the fatty diamine a), relative to the weight a)+b), ranges from 40 to 60%.

Assignments (2)
CHANGE OF ADDRESS Recorded Jul 4, 2025
From: ARKEMA FRANCE
To: ARKEMA FRANCE
Reel/Frame 071814/0739 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 15, 2022
From: FOUILLIART, CARINE; DUCASTEL, VIRGINIE; LEROY, VINCENT; COLESNIC, DMITRI
To: ARKEMA FRANCE
Reel/Frame 059009/0805 →
Priority Claims (1)
FR 18.59908 · Oct 26, 2018 · national
Continuity (1)
Related Publication 20210380527A1 · Dec 9, 2021
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