Organic oligomers of acylglycerol

Patent metadata

Field	Value
Publication number	US-9957222-B2
Application number	US-201414774570-A
Country	US
Kind code	B2
Filing date	Mar 12, 2014
Priority date	Mar 14, 2013
Publication date	May 1, 2018
Grant date	May 1, 2018

Abstract

Organic oligomers of acylglycerol having general formula (I): Formula (I), in which M1 and Q1 are organic groups; G11 is a hydroxylpropyl group; G12 and G13 are α/α′-acylglycerols; n is a natural integer from the range [0; 8]; m is a natural integer from the range [0; 4]; and p is a natural integer from the range [0; 3].

First claim

The invention claimed is:

1. An acylated organic glycerol oligomer of general formula (I):

wherein:
M 1 is an organic group selected from formulae (I A ), (I B ), (I C ), and (I D ):

wherein
R is a hydrocarbon group, a saturated hydrocarbon group, an unsaturated hydrocarbon group or a branched hydrocarbon group, having from 1 to 21 carbon atoms;
G 11 is selected from the of hydroxylated propyl groups of formulae (II A ) and (II B ):

G 12 and G 13 are α/α′-hydroxyacylated propyl groups of formula (III):

and
Q 1 is chosen from the group formed of hydrogen and organic groups formed of at least two atoms bonded by covalent bonds and belonging to the group formed of carbon (C), hydrogen (H) and oxygen (O);
n is a natural integer less than 9 such that if n=0, then M 1 is of formula (I C ) or (I D ); and
m is a non-zero integer less than 5; and
p is an integer less than 4.

2. The oligomer as claimed in claim 1 , wherein Q 1 is selected from the group consisting of:
hydrogen (H),
hydroxylated propyl groups of formula (III A ):

hydroxylated propyl groups of formula (III B ):

and
groups of formulae (I A ), (I B ), (I C ) and (I D ).

3. An acylated organic glycerol oligomer of formula (IV):

wherein
R is a hydrocarbon group, a saturated hydrocarbon group, an unsaturated hydrocarbon group or a branched hydrocarbon group, having from 1 to 21 carbon atoms; and
a is a non-zero integer less than 9.

4. An acylated organic glycerol oligomer of formula (V):

wherein
R is a hydrocarbon group, a saturated hydrocarbon group, an unsaturated hydrocarbon group or a branched hydrocarbon group, having from 1 to 21 carbon atoms; and
a is a non-zero integer less than 9.

5. An acylated organic glycerol oligomer of formula (VI):

wherein
R is a hydrocarbon group, a saturated hydrocarbon group, an unsaturated hydrocarbon group or a branched hydrocarbon group, having from 1 to 21 carbon atoms; and
a is a non-zero integer less than 4.

6. The oligomer claim 1 , having the formula (VII):

wherein b is a non-zero integer less than 5.

7. The oligomer of claim 1 , having the formula (VIII):

wherein b is a non-zero integer less than 5.

8. The oligomer of claim 1 , having the formula (IX):

wherein b is a non-zero integer less than 5.

9. The oligomer of claim 1 , having the formula (X):

wherein b is a non-zero integer less than 5.

10. The oligomer of claim 1 , having the formula (XI):

wherein b is a non-zero integer less than 5.

11. The oligomer of claim 1 , having the formula (XII):

wherein b is a non-zero integer less than 5.

12. The oligomer of claim 1 , having the formula (XIII):

wherein b is a non-zero integer less than 5.

13. The oligomer of claim 1 , having the formula (XIV):

wherein b is a non-zero integer less than 5.

14. The oligomer of claim 1 , wherein R is a hydrocarbon group selected from the group consisting of:
saturated hydrocarbon groups of the general formula —C q H 2q+1 wherein q is an integer from 1 to 21; and
unsaturated hydrocarbon groups, monounsaturated hydrocarbon groups of the general formula —C s H 2s-1 wherein s is an integer from 1 to 21, and polyunsaturated hydrocarbon groups.

15. The oligomer of claim 1 , wherein R is a hydrocarbon group selected from the group consisting of methyl (—CH 3 ), ethyl (—CH 2 —CH 3 ), n-propyl (—CH 2 —CH 2 —CH 3 ), iso-propyl (—CH(CH 3 ) 2 ), n-butyl (—CH 2 —CH 2 —CH 2 —CH 3 ), iso-butyl (—CH 2 —CH(CH 3 ) 2 ), tert-butyl (—C(CH 3 ) 3 ), n-pentyl (—CH 2 —(CH 2 ) 3 —CH 3 ), hexyl (—(CH 2 ) 5 —CH 3 ) octyl (—(CH 2 ) 7 —CH 3 ) undecyl (—(CH 2 ) 10 —CH 3 ), pentadecyl (—(CH 2 ) 14 —CH 3 ) heptadecyl (—(CH 2 ) 16 —CH 3 ), 9-ene-decyl (—CH═CH—(CH 2 ) 7 —CH 3 ) and 9-ene-heptadecyl (—(CH 2 ) 7 —CH═CH—(CH 2 ) 7 —CH 3 ).

16. A liquid organic composition comprising at least one acylated organic glycerol oligomer of claim 1 .

17. The composition of claim 16 , comprising a plurality of said acylated organic glycerol oligomers.

18. The oligomer of claim 2 , wherein R is a hydrocarbon group selected from the group consisting of methyl (—CH 3 ), ethyl (—CH 2 —CH 3 ), n-propyl (—CH 2 —CH 2 —CH 3 ), iso-propyl (—CH(CH 3 ) 2 ), n-butyl (—CH 2 —CH 2 —CH 2 —CH 3 ), iso-butyl (—CH 2 —CH(CH 3 ) 2 ), tert-butyl (—C(CH 3 ) 3 ), n-pentyl (—CH 2 —(CH 2 ) 3 —CH 3 ), hexyl (—(CH 2 ) 5 —CH 3 ), octyl (—(CH 2 ) 7 —CH 3 ), undecyl (—(CH 2 ) 10 —CH 3 ), pentadecyl (—(CH 2 ) 14 —CH 3 ), heptadecyl (—(CH 2 ) 16 —CH 3 ), 9-ene-decyl (—CH═CH—(CH 2 ) 7 —CH 3 ) and 9-ene-heptadecyl (—(CH 2 ) 7 —CH═CH—(CH 2 ) 7 —CH 3 ).

19. The oligomer of claim 2 , having the following general formula (VII):

wherein b is a non-zero integer less than 5.

Assignees

• Agronutrition
• Inst Nat Polytechnique Toulouse
• Agronomique Inst Nat Rech

Inventors

• Mouloungui Zephirin
• Abdel Baki Zaher
• Valentin Romain
• Zebib Bachar

Classifications

• C08G64/42

  Chemical after-treatment · CPC title

• C08G64/0216 Primary

  containing a chain-terminating or -crosslinking agent · CPC title

• C07C69/708 Primary

  Ethers · CPC title

• C07C59/305

  containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups · CPC title

• C08G64/02 Primary

  Aliphatic polycarbonates · CPC title