Esteramide solvents/coalescing agents in phytosanitary, cleaning, degreasing, stripping, lubricating, coating, and pigment/ink compositions

1. A composition comprising at least one esteramide compound having the formula (I) below:

R 1 OOC-A-CONR 2 R 3   (I)

in which:

R 1 is a radical selected from among saturated or unsaturated, linear or branched, optionally cyclic, optionally aromatic hydrocarbon-based radicals having an average number of carbon atoms ranging from 1 to 36;

R 2 and R 3 , which may be identical or different, are each radicals selected from among saturated or unsaturated, linear or branched, optionally cyclic, optionally aromatic, optionally substituted hydrocarbon-based radicals having an average number of carbon atoms ranging from 1 to 36, with the proviso that R 2 and R 3 may optionally together form a ring member that is optionally substituted and/or that optionally contains a heteroatom; and

A is a branched divalent alkyl radical having an average number of carbon atoms ranging from 2 to 12,

wherein said composition is formulated as a phytosanitary cleaning, degreasing, stripping, lubricating, coating, or pigment/ink composition and where said at least one esteramide compound having the formula (I) solubilizes and/or coalesces other ingredients in said composition.

2. The composition as defined by claim 1 , where in formula (I), R 2 and R 3 are ethyl radicals.

3. The composition as defined by claim 1 , where in formula (I), R 1 , R 2 and R 3 , which may be identical or different, are each radicals selected from among C 1 -C 12 alkyl, aryl, alkaryl or arylalkyl radicals or the phenyl radical, R 2 and/or R 3 optionally being substituted.

4. The composition as defined by claim 1 , where in formula (I), R 1 is selected from among methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, n-pentyl, isopentyl, isoamyl, n-hexyl, cyclohexyl, 2-ethylbutyl, n-octyl, isooctyl, 2-ethylhexyl, and tridecyl radicals.

5. The composition as defined by claim 1 , where in formula (I), R 2 and R 3 , which may be identical or different, are each selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-pentyl, amyl, isoamyl, hexyl, cyclohexyl, hydroxyethyl, morpholine, piperazine and piperidine groups.

6. The composition as defined by claim 1 , where in formula (I), A is a divalent branched alkylene radical having one of the following formulae (IIa), (IIb), (IIc), (IIIa) and (IIIb), or a mixture of at least two radicals selected from the radicals of formulae (IIa), (IIb) and (IIc) or from the radicals of formulae (IIIa) and (IIIb), or a mixture of at least two radicals, one selected from the groups of formulae (IIa), (IIb) and (IIc) and the others selected from the radicals of formulae (IIIa) and (IIIb):

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

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

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

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

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

wherein:

x is an integer greater than 0;

y is an average integer greater than or equal to 0;

z is an average integer greater than or equal to 0;

the radicals R 6 , which may be identical or different, are each a C 1 -C 6 alkyl radical; and

the radicals R 7 , which may be identical or different, are each a hydrogen atom or a C 1 -C 6 alkyl radical.

7. The composition as defined by claim 6 , wherein the formula (IIa) and/or in the formula (IIb) x=1; y=z=0; R 6 =methyl; and/or in the formula (IIIa) and/or in the formula (IIIb) x=1; y=z=0; R 6 =ethyl.

8. The composition as defined by claim 6 , wherein said at least one esteramide compound is selected from the group consisting of following compounds, and mixtures thereof:

MeOOC-A MG -CONMe 2 ;

MeOOC-A ES -CONMe 2 ;

PeOOC-A MG -CONMe 2 ;

PeOOC-A ES -CONMe 2 ;

CycloOOC-A MG -CONMe 2 ;

CycloOOC-A ES -CONMe 2 ;

EhOOC-A MG -CONMe 2 ;

EhOOC-A ES -CONMe 2 ;

PeOOC-A MG -CONEt 2 ;

PeOOC-A ES -CONEt 2 ;

CycloOOC-A MG -CONEt 2 ;

CycloOC-A ES -CONEt 2 ;

BuOOC-A MG -CONEt 2 ;

BuOC-A ES -CONEt 2 ;

BuOOC-A MG -CONMe 2 ;

BuOOC-A ES -CONMe 2 ;

EtBuOOC-A MG -CONMe 2 ; and

EtBuOOC-A ES -CONMe 2 ;

wherein:

A MG is an MG a radical of formula —CH(CH 3 )—CH 2 —CH 2 —, or MG b radical of formula —CH 2 —CH 2 —CH(CH 3 )— or a mixture of MG a and MG b radicals;

A ES is an ES a radical of formula —CH(C 2 H 5 )—CH 2 —, or ES b radical of formula —CH 2 —CH(C 2 H 5 )— or a mixture of ES a and ES b radicals;

Pe is a pentyl radical;

Cyclo is a cyclohexyl radical;

Eh is a 2-ethylhexyl radical;

Bu is a butyl radical; and

EtBu is an ethylbutyl radical.

9. The composition as defined by claim 1 , wherein said at least one esteramide compound is different from the following compounds:

MeOOC—CHEt-CH 2 —CONMe 2 ; and

MeOOC—CH 2 —CH(CH 3 )—CH 2 —CONMe 2 .

10. The composition as defined by claim 1 , wherein said at least one esteramide compound is different from the following compounds thereof:

MeOOC—CHEt-CH 2 —CONMe 2 ;

MeOOC—CH 2 —CH(CH 3 )—CH 2 —CONMe 2 ;

PhOOC—CH(CH 3 )—CH 2 —CONEt 2 ;

EtOOC—CH(CH 3 )—CH 2 —CONEt 2 ;

MeOOC—CH(CH 3 )—CH 2 —CONEt 2 ;

Me-CH(OMe)-OOC—CH(CH 3 )—CH 2 —CONEt 2 ;

Cyclohexyl-OOC—CH(CH 3 )—CH 2 —CONEt 2 :

Ph-CH 2 OOC—CH(CH 3 )—CH 2 —CONEt 2 ;

p-cresyl-OOC—CH(CH 3 )—CH 2 —CONEt 2 ;

EtOOC—CHEt-CH 2 —CONEt 2 ;

EtOOC—CH(CH 3 )—CH 2 —CH 2 —CONEt 2 ;

EtOOC—CH 2 —CH 2 —CH 2 —CH 2 —CONEt 2 ; and

MeOOC—CH 2 —CH(CH 3 )—CH 2 —CONH(n-butyl).

11. The composition as defined by claim 1 , wherein said at least one esteramide compound has a melting point that is less than or equal to 20° C.

12. At least one esteramide compound having the formula (I) below:

R 1 OOC-A-CONR 2 R 3   (I)

wherein:

R 1 is a radical selected from among saturated or unsaturated, linear or branched, optionally cyclic, optionally aromatic hydrocarbon-based radicals having an average number of carbon atoms ranging from 1 to 36;

R 2 and R 3 , which may be identical or different, are each radicals selected from among saturated or unsaturated, linear or branched, optionally cyclic, optionally aromatic, optionally substituted hydrocarbon-based radicals having an average number of carbon atoms ranging from 1 to 36, with the proviso that R 2 and R 3 may optionally together form a ring member, that is optionally substituted and/or that optionally contains a heteroatom; and

A is a branched divalent alkyl radical having an average number of carbon atoms ranging from 2 to 12, other than the following compounds:

MeOOC—CHEt-CH 2 —CONMe 2 ;

MeOOC—CH 2 —CH(CH 3 )—CH 2 —CONMe 2 ;

PhOOC—CH(CH 3 )—CH 2 —CON Et 2 ;

EtOOC—CH(CH 3 )—CH 2 —CONEt 2 ;

MeOOC—CH(CH 3 )—CH 2 —CONEt 2 ;

Me-CH(OMe)-OOC—CH(CH 3 )—CH 2 —CONEt 2 ;

Cyclohexyl-OOC—CH(CH 3 )—CH 2 —CONEt 2 ;

Ph-CH 2 OOC—CH(CH 3 )—CH 2 —CONEt 2 ;

p-cresyl-OOC—CH(CH 3 )—CH 2 —CONEt 2 ;

EtOOC—CHEt-CH 2 —CONEt 2 ,

EtOOC—CH(CH 3 )—CH 2 —CH 2 —CONEt 2 ;

MeOOC—CH 2 —CH(CH 3 )—CH 2 —CONH(n-butyl).

13. A process for preparing an esteramide compound as defined in claim 12 , comprising reacting an anhydride of formula (I′) with an alcohol of formula R 1 —OH and/or an amine of formula HNR 2 R 3 :

14. The process as defined by claim 13 , wherein the anhydride is prepared during a prior step a) of cyclization of a diacid of formula HOOC-A-COOH.

15. The process as defined by claim 13 , comprising one of the following reaction sequences 1) or 2):

Sequence 1):

Step 1b) the anhydride of formula (I′) is reacted with an alcohol of formula R 1 —OH, so as to obtain an ester acid compound of formula (I″):

R 1 —OOC-A-COOH  (I″);

Step 1c) the compound of formula (I″) is converted to a compound of formula (I) using an amine of formula HNR 2 R 3 ;

Sequence 2):

Step 2b) the anhydride of formula (I′) is reacted with an amine of formula HNR 2 R 3 to obtain an amide acid compound of formula (II″):

HOOC-A-CONR 2 R 3   (II″);

Step 2c) the compound of formula (II″) is converted to a compound of formula (I) using an alcohol of formula R 1 —OH.

16. The process as defined by claim 15 , wherein step 1c) comprises the following steps:

1c1) the compound of formula (I″) is converted to an acyl chloride of formula (I′″) below:

R 1 —OOC-A-COCl  (I′″);

1c2) the compound of formula (III′″) is reacted with the amine of formula NR 3 R 4 to obtain the compound of formula (I).

17. The process as defined by claim 15 , wherein step 2c) is carried out in the presence of thionyl chloride.

18. A process for preparing an esteramide compound as defined in claim 12 , comprising reacting as diester of formula R 1 OOC-A-COOR 1 with an amine of formula HNR 2 R 3 , then optionally a reaction with an alcohol of formula R 1′ —OH, wherein R 1′ is a radical selected from among the R 1 radicals, but different from the R 1 radical of the diester.

19. At lease one esteramide compound as defined by claim 12 , wherein R 1 , R 2 and R 3 , which may be identical or different, are radicals selected from among C 1 -C 12 alkyl, aryl, alkaryl or arylalkyl radicals or the phenyl radical, R 2 and/or R 3 optionally being substituted.

20. At least one esteramide compound as defined by claim 12 , wherein R 1 is selected from among methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, n-pentyl, isopentyl, isoamyl, n-hexyl, cyclohexyl, 2-ethylbutyl, n-octyl, isooctyl, 2-ethylhexyl, and tridecyl radicals.

21. At least one esteramide compound as defined by claim 12 , wherein R 2 and R 3 , which may be identical or different, are each selected from among methyl, ethyl, propyl (n-propyl), isopropyl, n-butyl, isobutyl, n-pentyl, amyl, isoamyl, hexyl, cyclohexyl, hydroxyethyl, morpholine, piperazine and piperidine radicals.

22. At least one esteramide compound as defined by claim 12 , wherein A is a divalent branched alkylene radical having one of the following formulae (IIa), (IIb), (IIc), (IIIa) and (IIIb), or a mixture of at least two radicals selected from among the radicals of formulae (IIa), (IIb) and (IIc) or from the radicals of formulae (IIIa) and (IIIb), or a mixture of at least two radicals, one selected from the radicals of formulae (IIa), (IIb) and (IIc) and the others selected from the radicals of formulae (IIIa) and (IIIb):

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

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

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

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

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

wherein:

x is an integer greater than 0;

y is an average integer greater than or equal to 0;

z is an average integer greater than or equal to 0;

the radicals R 6 , which may be identical or different, are each a C 1 -C 6 alkyl radical; and

the radicals R 7 , which may be identical or different, are each a hydrogen atom or a C 1 -C 6 alkyl radical.

23. At least one esteramide compound as defined by claim 22 , wherein formula (IIa) and/or in the formula (IIb) x=1; y=z=0; R 6 =methyl; and/or in the formula (IIIa) and/or in the formula (IIIb) x=1; y=z=0; R 6 =ethyl.

24. At least one esteramide compound as defined by claim 22 , selected from among the following compounds, and mixtures thereof:

MeOOC-A MG -CONMe 2 ;

MeOOC-A ES -CONMe 2 ;

PeOOC-A MG -CONMe 2 ;

PeOOC-A ES -CONMe 2 ;

CycloOOC-A MG -CONMe 2 ;

CycloOC-A ES -CONMe 2 ;

EhOOC-A MG -CONMe 2 ;

EhOOC-A ES -CONMe 2 ;

PeOOC-A MG -CONEt 2 ;

PeOOC-A ES -CONEt 2 ;

CycloOOC-A MG -CONEt 2 ;

CycloOC-A ES -CONEt 2 ;

BuOOC-A MG -CONEt 2 ;

BuOC-A ES -CON Et 2 ;

BuOOC-A MG -CONMe 2 ;

BuOOC-A ES -CONMe 2 ;

EtBuOOC-A MG -CONMe 2 ;

EtBuOOC-A ES -CONMe 2 ;

n-HeOOC-A MG -CONMe 2 ; and

n-HeOOC-A ES -CONMe 2 ;

wherein:

A MG is an MG a radical of formula —CH(CH 3 )—CH 2 —CH 2 —, or MG b radical of formula —CH 2 —CH 2 —CH(CH 3 )— or a mixture of MG a and MG b radicals;

A ES is an ES a radical of formula —CH(C 2 H 5 )—CH 2 —, or ES b radical of formula —CH 2 —CH(C 2 H 5 )— or a mixture of ES a and ES b radicals;

Pe is a pentyl radical;

Cyclo is a cyclohexyl radical;

Eh is a 2-ethylhexyl radical;

Bu is a butyl radical;

EtBu is an ethylbutyl radical; and

n-He is an n-hexyl radical.

25. A composition comprising:

(a) an active substance selected from the group consisting of an insecticide, a herbicide, a fungicide, an acaricide and a rodeticide;

(b) at least one esteramide compound having the formula (I):

R 1 OOC-A-CONR 2 R 3   (I)

in which:

R 1 is a radical selected from among saturated or unsaturated, linear or branched, optionally cyclic, optionally aromatic hydrocarbon-based radicals having an average number of carbon atoms ranging from 1 to 36;

R 2 and R 3 , which may be identical or different, are each radicals selected from among saturated or unsaturated, linear or branched, optionally cyclic, optionally aromatic, optionally substituted hydrocarbon-based radicals having an average number of carbon atoms ranging from 1 to 36, with the proviso that R 2 and R 3 may optionally together form a ring member that is optionally substituted and/or that optionally contains a heteroatom; and

A is a branched divalent alkyl radical having an average number of carbon atoms ranging from 2 to 12,

(c) optionally at least one emulsifier; and

(d) optionally water;

wherein said active substance is solubilized in a solution comprising said at least one esteramide compound of formula (I).

26. The composition of claim 25 , wherein said active substance is insoluble in water.

27. A method of solubilizing an active substance that is insoluble in water, said method comprising dissolving said active substance in at least one esteramide compound having the formula (I):

R 1 OOC-A-CONR 2 R 3   (I)

in which:

R 1 is a radical selected from among saturated or unsaturated, linear or branched, optionally cyclic, optionally aromatic hydrocarbon-based radicals having an average number of carbon atoms ranging from 1 to 36;

R 2 and R 3 , which may be identical or different, are each radicals selected from among saturated or unsaturated, linear or branched, optionally cyclic, optionally aromatic, optionally substituted hydrocarbon-based radicals having an average number of carbon atoms ranging from 1 to 36, with the proviso that R 2 and R 3 may optionally together form a ring member that is optionally substituted and/or that optionally contains a heteroatom; and

A is a branched divalent alkyl radical having an average number of carbon atoms ranging from 2 to 12.

28. A composition comprising a mixture of two or more esteramide compounds having formula (I) below:

R 1 OOC-A-CONR 2 R 3   (I)

in which:

R 1 is a radical selected from among saturated or unsaturated, linear or branched, optionally cyclic, optionally aromatic hydrocarbon-based radicals having an average number of carbon atoms ranging from 1 to 36;

R 2 and R 3 , which may be identical or different, are each radicals selected from among saturated or unsaturated, linear or branched, optionally cyclic, optionally aromatic, optionally substituted hydrocarbon-based radicals having an average number of carbon atoms ranging from 1 to 36, with the proviso that R 2 and R 3 may optionally together form a ring member that is optionally substituted and/or that optionally contains a heteroatom; and

A is a branched divalent alkyl radical having an average number of carbon atoms ranging from 2 to 12.

29. The composition of claim 28 , wherein said mixture of two or more esteramide compounds having formula (I) comprises:

Me 2 NOC—CH 2 —CH(CH 2 —CH 3 )—COOMe,

Me 2 NOC—CH(CH 3 )—CH 2 —CH 2 —COOMe, and

Me 2 NOC—CH 2 —CH 2 —CH(CH 3 )—COOMe.