IP Library Granted Patent US 8,580,712
Granted Patent B2
US 8,580,712 · App. 12/520,425 · Granted Nov 12, 2013

Bis(dialkylamide) compounds and diverse applications thereof

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Quick Facts
Patent No.
US 8,580,712
App. No.
12/520,425
Granted
Nov 12, 2013
Kind
B2
Abstract

Novel bis(dialkylamide) compounds having the formula: R 2 R 3 NOC—R 1a —CONR 4 R 5 are particularly useful solvents, for example in plant-protection formulations.

Claims (78)

1. A composition comprising at least 10% by weight of a bis(dialkylamide) compound of the formula:

R 2 R 3 NOC—R 1a —CONR 4 R 5   (Ia)

wherein:

R 2 , R 3 , R 4 and R 5 , which are identical or different, are each a linear or branched or cyclic C 1 -C 6 alkyl radical or a phenyl radical, and

R 1a is a divalent group of the formula:

—CH 2 —CH 2 —(CHR 6 ) x —

wherein:

x is an integer greater than 0, and

R 6 is a C 1 -C 6 alkyl group,

wherein said composition is formulated as a plant protection formulation, a cleaning formulation, a stripping formulation, a degreasing formulation, a lubricating or textile formulation, a coating formulation, a pigment or ink formulation or a plastic formulation.

2. The composition as defined by claim 1 , comprising an amidation or transamidation product.

3. The composition as defined by claim 1 , further comprising a compound having the following formula (Ib):

R 2 R 3 NOC—R 1b —CONR 4 R 5   (Ib)

wherein:

R 2 , R 3 , R 4 and R 5 , which may be identical or different, are each a linear or branched or cyclic C 1 -C 6 alkyl radical or a phenyl radical, and

R 1b is a divalent radical of formula (IIb):

—CH 2 —(CHR 7 ) z—(CHR 6 ) x —(CHR 7 ) y —  (IIb)

wherein:

x is an integer greater than 0,

y is a mean integer greater than or equal to 0,

z is a mean integer greater than or equal to 0,

R 6 is a C 1 -C 6 alkyl radical, and

R 7 is a hydrogen atom or a C 1 -C 6 alkyl radical.

4. The composition as defined by claim 3 , wherein, in the R 1b radical:

x =1,

y =z =0,

R 6 =ethyl.

5. The composition as defined by claim 1 , comprising a product of the amidation or transamidation of a mixture of methylglutaric acid and ethylsuccinic acid, or of a diester of this mixture.

6. The composition as defined by claim 3 , which comprises:

from 70% to 95% by weight of the compound of formula (la),

from 5% to 30% by weight of a compound of formula (lb), and

optionally, at most 15% by weight of another compound.

7. A process for the preparation of a bis(dialkylamide) compound of the formula:

R 2 R 3 NOC—R 1a —CONR 4 R 5   (Ia)

wherein:

R 2 , R 3 , R 4 and R 5 , which are identical or different, are each a linear or branched or cyclic C 1 -C 6 alkyl radical or a phenyl radical, and

R 1a is a divalent group of the formula:

—CH 2 —CH 2 —(CHR 6 ) x —

wherein:

x is an integer greater than 0, and

R 6 is a C 1 -C 6 alkyl group,

said process comprising a stage of amidation or transamidation by a compound of formula R 2 R 3 NR and/or HNR 4 R 5 of a compound of following formula (l′a):

R 8 OOC—R 1a —COOR 8   (I′a)

the compound of formula (l′a) optionally being in admixture with a compound of following formula (lb):

R 8 OOC—R 1b —COOR 8   (I′b)

wherein:

R 8 is a hydrogen atom or a C 1 -C 6 alkyl radical, and

R 1a is a divalent radical of the formula:

—CH 2 —CH 2 —(CHR 6 ) x —

wherein:

x is an integer greater than 0,

R 6 is a C 1 -C 6 alkyl radical, and

R 1b is a divalent radical of formula (IIb):

—CH 2 —(CHR 7 ) z —(CHR 6 ) x —(CHR 7 ) y —  (IIb)

wherein:

x is an integer greater than 0,

y is a mean integer greater than or equal to 0,

z is a mean integer greater than or equal to 0,

R 6 is a C 1 -C 6 alkyl radical, and

R 7 is a hydrogen atom or a C 1 -C 6 alkyl radical.

8. The composition of claim 1 , wherein the bis(dialkylamide) compound in said composition is coalescence agent, a solvent, a cosolvent and/or a crystallization inhibitor.

9. The composition as defined by claim 1 , wherein said composition comprises at least 50% by weight of said bis(dialkylamide) compound.

10. The composition as defined by claim 1 , wherein, in formula (Ia), R 2 , R 3 , R 4 and R 5 , which are identical or different, are selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-pentyl, amyl, isoamyl, hexyl and cyclohexyl groups.

11. The composition as defined by claim 1 , wherein, in the group R 1a :

x =1,

y =z =0, and

R 6 =methyl.

12. The composition as defined by claim 1 , wherein, in formula (Ia), the R 2 , R 3 , R 4 and R 5 groups, which are identical or different, are linear C1-C4 alkyl groups.

13. A plant-protection formulation comprising an active plant protection agent, an emulsifier and at least one compound of the formula:

R 2 R 3 NOC—R 1a —CONR 4 R 5   (Ia)

wherein:

R 2 , R 3 , R 4 and R 5 , which are identical or different, are each a linear or branched or cyclic C 1 -C 6 alkyl radical or a phenyl radical, and R 1a is a divalent group of the formula:

—CH 2 —CH 2 —(CHR 6 ) x —

wherein:

x is an integer greater than 0, and

R 6 is a C 1 —C 6 alkyl group,

wherein said plant-protection formulation is in the form of an emulsifiable concentrate, a concentrated emulsion, a microemulsion, a wettable-powder or a water-dispersible granule.

14. A composition comprising the plant-protection formulation of claim 13 , wherein said plant-protection formulation is diluted with water.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 26, 2024
From: RHODIA OPERATIONS
To: SPECIALTY OPERATIONS FRANCE
Reel/Frame 066374/0642 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 7, 2023
From: RHODIA OPERATIONS
To: SPECIALTY OPERATIONS FRANCE
Reel/Frame 065488/0365 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 28, 2009
From: MAS, JEAN-MANUEL; BRAMATI, VALERIO; GUGLIERI, MASSIMO; LOURENCO, WAGNER CELIO FERRAZ
To: RHODIA OPERATIONS
Reel/Frame 023705/0936 →