IP Library Granted Patent US 12,692,367
Granted Patent B2
US 12,692,367 · App. 16/766,019 · Granted Jul 28, 2026

Rheology additives based on di- or tri-amides and mixtures thereof

Inventors: Michael Y. Bernard (Enghien-les-Bains, FR); Dmitri Colesnic (Paris, FR); Laurent Lepinay (Meru, FR); Vincent Leroy (Fitz James, FR); Francois Vettier (Chatou, FR)
Assignee: Arkema France
C08K5/20C07C233/05C09J177/00
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Quick Facts
Patent No.
US 12,692,367
App. No.
16/766,019
Granted
Jul 28, 2026
Kind
B2
Abstract

The invention relates to a fatty amide which is a di- or triamide based on a polyether diamine or triamine which can be used as organogelator and in particular as rheology additive. The invention also relates to a formulation composition using said fatty amide as rheology additive and to its use with this aim in coating, adhesive or PVC plastisol compositions and in particular transparent or non-transparent mastic compositions. said rheology additive has the advantage of not needing a specific activation process before use, in contrast to the other known fatty amide additives based on hydrogenated castor oil derivatives.

Claims (41)

1 . A polyfunctional fatty amide which is a diamide or a triamide or a mixture thereof, wherein said polyfunctional fatty amide is represented by:

A) formula (I):

[(R2'—OCNH-R1-X) n 1—R—(X—R1—NHCO—R2) n — n 1]  (I)

with

n being 2 or 3,

n 1 being equal to 0 or 1,

R1 being a bivalent oligomer chain segment chosen from alkoxylated polyester and polyether,

R being a C 3 -C 10 bivalent or trivalent alkylene,

X being O, NH or N(R3),

R2 being a hydroxylated or non-hydroxylated C 12 -C 52 hydrocarbon chain of a monocarboxylic fatty acid, wherein said R2 are identical or different when n-n1 is >1, wherein at least one R2 is a hydroxylated C 12 -C 52 hydrocarbon chain with a non-terminal hydroxyl group, and wherein the monocarboxylic fatty acid excludes any polyester or oligoester derived from the self-polycondensation of a hydroxylated fatty acid,

R2' being a C 2 to C 10 hydrocarbon chain of a monocarboxylic acid, and

R3 being a C1-C2 alkyl substituent, or by

B) formula (II), wherein said polyfunctional fatty amide is a diamide:

R2CONH-R'—O—[CH2—CH(R4)—O] x —CH2—CH(R4)—NHCOR2′  (II)

with R' being —CH(CH3)—CH2—

R2 and R2′ being defined as in said formula (I), and

each R4 being independently H or methyl

wherein the value of x is such that a number-average molecular weight Mn of the polyfunctional fatty amide, measured by gel permeation chromatography in tetrahydrofuran as polystyrene equivalents, is from 800 to 4000 when n in formula (I) is 2 and from 1,000 to 6,000 when n in formula (I) is 3,

and wherein said polyfunctional fatty amide has a melting temperature ranging from 10°C. to 110°C., as measured after two passes on a differential scanning calorimetry (“DSC”) having a temperature ramp rate of 10°C./min.

2 . The polyfunctional fatty amide according to claim 1 wherein said bivalent oligomer chain segment R1 is a polyether chain segment.

3 . The polyfunctional fatty amide according to claim 1 wherein said bivalent oligomer chain segment R1 is a polyoxypropylene chain segment.

4 . The polyfunctional fatty amide according to claim 1 wherein R1 has a number-average molecular weight (Mn) ranging from 400 to 2000.

5 . The polyfunctional fatty amide according to claim 1 wherein said monocarboxylic fatty acid is a hydroxylated fatty acid selected from 12-hydroxystearic acid (12-HSA), 9-hydroxystearic acid (9-HSA), 10-hydroxystearic acid (10-HSA), a mixture of 9- and 10-hydroxystearic acids, and 14-hydroxyeicosanoic acid (14-HEA).

6 . The polyfunctional fatty amide according to claim 1 wherein said monocarboxylic fatty acid is 12-hydroxystearic acid.

7 . The polyfunctional fatty amide according to claim 1 wherein R2' is a C 2 to C 10 hydrocarbon chain of a monocarboxylic acid selected from the group consisting of: acetic acid, propionic acid, butyric acid, pentanoic (valeric) acid, hexanoic (caproic) acid, heptanoic acid, and octanoic acid.

8 . The polyfunctional fatty amide according to claim 1 wherein said polyfunctional fatty amide is a diamide according to A) or B) or a triamide according to A) with all R2 groups being a hydroxylated C 12 -C 52 hydrocarbon chain of a monocarboxylic fatty acid.

9 . The polyfunctional fatty amide according to claim 1 wherein said polyfunctional fatty amide is a diamide according to A) or B) with one R2 group being a hydroxylated C 12 -C 52 hydrocarbon chain of a monocarboxylic fatty acid.

10 . The polyfunctional fatty amide according to claim 1 wherein said polyfunctional fatty amide is a triamide according to A) with two R2 groups being a hydroxylated C 12 -C 52 hydrocarbon chain of a monocarboxylic fatty acid and one R2 group being a non-hydroxylated C 12 -C 52 hydrocarbon chain of a monocarboxylic fatty acid.

11 . The polyfunctional fatty amide according to claim 1 wherein the polyfunctional fatty amide is a diamide represented by A) according to formula (I).

12 . The polyfunctional fatty amide according to claim 1 wherein the polyfunctional fatty amide is a diamide represented by B) according to formula (II).

13 . A formulation composition of an organic binder comprising:

a) at least one organic binder, and

b) at least one polyfunctional fatty amide as defined according to claim 1 .

14 . The composition according to claim 13 , wherein said at least one organic binder a) is selected from the group consisting of: polysiloxane resins terminated by blocked silane groups, polyether resins terminated by blocked silane groups, polysulfide resins terminated by blocked silane groups, polyurethane prepolymer resins terminated by isocyanate groups, polyvinyl chloride (PVC) plastisols, and epoxy resins carrying epoxy groups.

15 . The composition according to claim 13 further comprising a plasticizer or a reactive diluent as defined below:

c) a plasticizer selected from the group consisting of phthalates, adipates, trimellitates, sebacates, benzoates, citrates, phosphates, epoxides, polyesters, alkylsulfonate esters and non-phthalate substitutes for phthalates, or

d) a reactive diluent selected from epoxidized monomers, and

e) optionally, a hardener for the epoxy or polyurethane resins.

16 . The composition according to claim 13 wherein said polyfunctional fatty amide is a thixotropic agent.

17 . The composition according to claim 15 wherein said organic binder a) is a polysiloxane resin, a polyurethane prepolymer resin or a PVC plastisol.

18 . The composition according to claim 17 , wherein the composition is a transparent or non-transparent mastic formulation composition.