Ether-amide compounds and uses thereof
View Patent ↗Novel ether-amide compounds are described. Uses of the compounds, in particular as solvents, for example in phytosanitary formulations are also described.
1. A method of using a compound as a solvent, a co-solvent, a crystallization inhibitor, or a plasticizer, wherein the method comprises using a compound of formula (I):
R a R b C(OR 1 )—CONR 2 R 3 (I)
wherein
R a and R b , either identical or different, are groups selected from hydrogen and a linear or branched C 1 -C 6 alkyl groups,
R 1 is a group R′ 1 or -(AO) n R′ 1 , wherein
R′ 1 is a group selected from hydrocarbon groups comprising an average number of carbon atoms, ranging from 1 to 15, optionally substituted, selected from saturated or unsaturated, linear or branched, acyclic aliphatic groups, saturated, unsaturated or aromatic, monocyclic or polycyclic, carbocyclic or heterocyclic groups and the linkings of said groups,
AO, either identical or different, represents a group of formula —CH 2 —CH 2 —O—, —CHMe-CH 2 —O—, or —CH 2 —CHMe-O—,
n is an average number greater than or equal to 0,
R 2 and R 3 , either identical or different, are hydrocarbon groups comprising an average number of carbon atoms, ranging from 1 to 15, optionally substituted, selected from saturated or unsaturated, linear or branched, acyclic aliphatic groups, saturated, unsaturated or aromatic, monocyclic or polycyclic, carbocyclic or heterocyclic groups and the linkings of said groups, and
R 2 and R 3 can optionally form together a cycle, comprising a nitrogen atom to which they are bound, optionally substituted and/or optionally comprising an additional heteroatom,
with the proviso that if R a =R b =H, the compound of formula (I) is used in a phytosanitary formulation.
2. A method of using a compound as a solvent, a co-solvent, a crystallization inhibitor, or a plasticizer, wherein the method comprises using a compound of formula (I):
R a R b C(OR 1 )—CONR 2 R 3 (I)
wherein
R a is a linear or branched C 1 -C 6 alkyl group,
R b is H or a linear or branched C 1 -C 6 alkyl group,
R 1 is a group R′ 1 or -(AO) n R′ 1 , wherein
R′ 1 is a group selected from hydrocarbon groups comprising an average number of carbon atoms, ranging from 1 to 15, optionally substituted, selected from saturated or unsaturated, linear or branched, acyclic aliphatic groups, saturated, unsaturated or aromatic, monocyclic or polycyclic, carbocyclic or heterocyclic groups and the linkings of said groups,
AO, either identical or different, represents a group of formula —CH 2 —CH 2 —O—, —CHMe-CH 2 —O—, or —CH 2 —CHMe-O—
n is an average number are greater than or equal to 0,
R 2 and R 3 , either identical or different, are hydrocarbon groups comprising an average number of carbon atoms, ranging from 1 to 15, optionally substituted, selected from saturated or unsaturated, linear or branched, acyclic aliphatic groups, saturated, unsaturated or aromatic, monocyclic or polycyclic, carbocyclic or heterocyclic groups and the linkings of said groups, and
R 2 and R 3 can optionally form together a cycle, comprising a nitrogen atom to which they are bound, optionally substituted and/or optionally comprising an additional heteroatom.
3. A method of using a compound as a solvent, a co-solvent, a crystallization inhibitor, or a plasticizer in a phytosanitary formulation, wherein the method comprises using a compound of formula (I-1):
R 1 O—H 2 C—CONR 2 R 3 (I-1)
wherein
R 1 is a group R′ 1 or -(AO) n R′ 1 , wherein
R′ 1 is a group selected from hydrocarbon groups comprising an average number of carbon atoms, ranging from 1 to 15, optionally substituted, selected from saturated or unsaturated, linear or branched, acyclic aliphatic groups, saturated, unsaturated or aromatic, monocyclic or polycyclic, carbocyclic or heterocyclic groups and the linkings of said groups,
AO, either identical or different, represents a group of formula —CH 2 —CH 2 —O—, —CHMe-CH 2 —O—, or —CH 2 —CHMe-O—
n is an average number greater than or equal to 0,
R 2 and R 3 , either identical or different, are hydrocarbon groups comprising an average number of carbon atoms, ranging from 1 to 15, optionally substituted, selected from saturated or unsaturated, linear or branched, acyclic aliphatic groups, saturated, unsaturated or aromatic, monocyclic or polycyclic, carbocyclic or heterocyclic groups and the linkings of said groups, and
R 2 and R 3 can optionally form together a cycle, comprising a nitrogen atom to which they are bound, optionally substituted and/or optionally comprising an additional heteroatom.
4. The method as defined by claim 1 , wherein the total number of carbon atoms, excluding groups R 1 , R 2 and R 3 is 2, 3, 4, 5, 6, 7 or 8.
5. The method as defined by claim 2 , wherein:
R a =Me or Et, and
R b =H.
6. The method as defined by claim 1 , wherein R 2 and R 3 , either identical or different, are selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-pentyl, amyl, isoamyl, hexyl, a cyclohexyl group, or in that they form together with the nitrogen atom, a morpholine, pyrrolidine, a piperazine and a piperidine group.
7. The method as defined by claim 1 , wherein R 2 and R 3 are methyl groups.
8. The as defined by claim 1 , wherein R′ 1 is selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, n-pentyl, isopentyl, isoamyl, n-hexyl, cyclohexyl, n-octyl, isooctyl, 2-ethylhexyl, decyl, dodecyl, tridecyl, phenyl, 1-phenylethyl, and benzyl groups.
9. The method as defined by claim 1 , wherein R′ 1 is selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, n-pentyl, isopentyl, isoamyl, n-hexyl, cyclohexyl, n-octyl, isooctyl, 2-ethylhexyl, decyl, dodecyl, tridecyl and 1-phenylethyl groups.
10. The method as defined by claim 1 , wherein the compound has a melting point of less than or equal to 20° C.
11. The method as defined by claim 1 , wherein the compound has one of the following formulae:
wherein Cy represents a cyclohexyl group.
12. The method as defined by claim 1 , wherein the compound is used in a phytosanitary formulation, in a cleaning formulation, in a stripping formulation, in a lubricant formulation, in a coating formulation, in a formulation of pigments or ink, or in a plastic formulation.
13. A compound of the following formula (I):
R a R b C(OR 1 )—CONR 2 R 3 (I)
wherein
R a is a linear or branched C 1 -C 6 alkyl group,
R b is H or a linear or branched C 1 -C 6 alkyl group,
R 1 is a group R′ 1 or -(AO) n R′ 1 , wherein
R′ 1 is a group selected from hydrocarbon groups comprising an average number of carbon atoms, ranging from 1 to 15, optionally substituted, selected from saturated or unsaturated, linear or branched, acyclic aliphatic groups, saturated, unsaturated or aromatic, monocyclic or polycyclic, carbocyclic or heterocyclic groups and the linkings of said groups,
AO, either identical or different, represents a group of formula —CH 2 —CH 2 —O—, —CHMe-CH 2 —O—, or —CH 2 —CHMe-O—
n is an average number greater than or equal to 0,
R 2 and R 3 , either identical or different, are hydrocarbon groups comprising an average number of carbon atoms, ranging from 1 to 15, optionally substituted, selected from saturated or unsaturated, linear or branched, acyclic aliphatic groups, saturated, unsaturated or aromatic, monocyclic or polycyclic, carbocyclic or heterocyclic groups and the linkings of said groups, and
R 2 and R 3 may can optionally form together a cycle, comprising the a nitrogen atom to which they are bound, optionally substituted and/or optionally comprising an additional heteroatom, and
with the following conditions:
if R a =Me and R b =H, then R 1 is a group different from methyl, n-butyl, benzyl or t-butyl groups.
14. The compound as defined by claim 13 , wherein R a is a linear or branched C 1 -C 3 alkyl group, and R b is H or a linear or branched C 1 -C 3 alkyl group.
15. The compound as defined by claim 13 , wherein:
R a =Me, Et, n-Pr or n-Bu, and
R b =H.
16. The compound as defined by claim 13 , wherein R 2 and R 3 are methyl groups.
17. The compound as defined by claim 13 , wherein R′ 1 is selected from the group consisting of ethyl, propyl, isopropyl, n-pentyl, isopentyl, isoamyl, n-hexyl, cyclohexyl, n-octyl, isooctyl, 2-ethylhexyl, decyl, dodecyl, tridecyl and 1-phenylethyl groups.
18. The compound as defined by claim 13 , wherein R 1 is a methyl or ethyl group.
19. The compound as defined by claim 13 , wherein the compound is selected from the group consisting of:
20. The compound as defined by claim 13 , wherein the compound is by itself or in a mixture.
21. The method as defined by claim 1 , wherein R a is a C 1 -C 3 alkyl group.
22. The method as defined by claim 2 , wherein R a is a C 1 -C 3 alkyl group.
23. The method as defined by claim 2 , wherein R b is a C 1 -C 3 alkyl group.
24. The method as defined by claim 2 , wherein n ranges from 0 to 50.
25. The method as defined by claim 10 , wherein the melting point is 5° C.
26. The method as defined by claim 10 , wherein the melting point is 0° C.
27. The compound as defined by claim 13 , wherein R a is a C 1 -C 3 alkyl group.
28. The compound as defined by claim 13 , wherein R b is a C 1 -C 3 alkyl group.