IP Library Granted Patent US 9,145,362
Granted Patent B2
US 9,145,362 · App. 13/381,718 · Granted Sep 29, 2015

Solvent composition based on an oxide of an organic sulfide with masked odour

Inventors: Paul-Guillaume Schmitt (Lescar, FR); Bernard Monguillon (Mourenx, FR); Mélanie Vauthrin (Denguin, FR)
Assignee: ARKEMA FRANCE
C07C315/06C07C317/00C07C317/02C07C319/26
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Quick Facts
Patent No.
US 9,145,362
App. No.
13/381,718
Granted
Sep 29, 2015
Kind
B2
Abstract

The invention relates to solvent compositions predominantly comprising at least one oxide of an organic sulfide, more particularly dimethyl sulfoxide, to which is added at least one odour-masking agent comprising at least one compound selected from monoesters, diesters or triesters, alcohols, ketones, aldehydes and terpenes.

Claims (94)

1. A solvent composition comprising:

a) at least 50% by weight of at least one oxide of an organic sulfide of general formula (1):

in which

X and Y, which may be identical or different, are chosen, independently of each other, from oxygen, sulfur, —SO—, —SO 2 —, —NH—and —NR″—;

a and b, which may be identical or different, represent, independently of each other, 0 or 1; n is equal to 1 or 2;

R, R′ and R″, which may be identical or different, are chosen, independently of each other, from a linear or branched alkyl radical containing from 1 to 12 carbon atoms, a linear or branched alkenyl radical containing from 2 to 12 carbon atoms, and an aryl radical containing from 6 to 10 carbon atoms; R, R′ and R″ possibly being substituted with radicals chosen from alkyl, alkenyl, aryl and halogen, and possibly containing one or more heteroatoms chosen from O, S, N, P and Si; R and R′ also possibly forming, together with the atoms that bear them, a hydrocarbon-based cyclic structure optionally containing one or more heteroatoms chosen from O, S and N, said cyclic structure comprising in total 5, 6, 7, 8 or 9 ring members; and

b) from 10 ppm to 2%, by weight relative to the total weight of the composition, of at least one odor-masking agent comprising at least one compound chosen from monoesters, diesters andor triesters, alcohols, aldehydes, ketones, and terpenes, wherein the aldehydes and ketones are of formula R a —CO—R b , in which R a represents a linear or branched hydrocarbon-based chain comprising from 1 to 6 carbon atoms, optionally comprising one or more unsaturation(s) in the form of double bonds, and R b represents a hydrogen atom, a cyclic hydrocarbon-based chain or a linear or branched hydrocarbon-based chain optionally substituted with a cyclic structure, R b comprising from 6 to 12 carbon atoms, optionally comprising one or more unsaturation(s) in the form of double bonds and being optionally substituted with one or more hydroxyl groups.

2. The composition as claimed in claim 1 , wherein the content of the odor-masking agent(s) b) is between 0.001% and 0.2% by weight relative to the total weight of the composition.

3. The composition as claimed in claim 1 , wherein a represents 0, —(Y) b —represents —(S) x —, in which x represents 0 or 1, and R and R′ are identical and chosen, independently of each other, from a linear or branched alkyl radical comprising from 1 to 12 carbon atoms, a linear or branched alkenyl radical comprising from 2 to 12 carbon atoms, and an aryl radical.

4. The composition as claimed in claim 1 , wherein component a) of the composition according to the present invention:

corresponds to formula (1′):

in which R is chosen from a linear or branched alkyl radical containing from 1 to 4 carbon atoms, a linear or branched alkenyl radical containing from 2 to 4 carbon atoms, and an aryl radical, n is equal to 1 or 2; x represents 0 or 1; Rs is chosen from a linear or branched alkyl radical containing from 1 to 4 carbon atoms, a linear or branched alkenylene radical containing from 2 to 4 carbon atoms, and an aryl radical;

corresponds to formula (1):

in which R and R′, which may be identical or different, are chosen from a linear or branched alkyl radical containing from 1 to 4 carbon atoms, a linear or branched alkenyl radical containing from 1 to 4 carbon atoms, and a phenyl radical; n is equal to 1 or 2; and x is equal to 0; or

is DSMO.

5. The composition as claimed in claim 1 , wherein the odor-masking agent b) comprises one or more compounds chosen from:

b1) monoesters;

b2) diesters and/or triesters;

b3) alcohols, comprising from 1 to 30 carbon atoms, said carbon atoms forming a linear or branched chain optionally comprising one or more unsaturation(s) in the form of double bonds, and optionally comprising a 5- or 6-membered cyclic structure, which is saturated or partially or totally unsaturated;

b4) aldehydes and ketones of formula R a —CO—R b , in which R a represents a linear or branched hydrocarbon-based chain comprising from 1 to 6 carbon atoms, optionally comprising one or more unsaturation(s) in the form of double bonds, and R b represents a hydrogen atom, a cyclic hydrocarbon-based chain or a linear or branched hydrocarbon-based chain optionally substituted with a cyclic structure, R b comprising from 6 to 12 carbon atoms, optionally comprising one or more unsaturation(s) in the form of double bonds and being optionally substituted with one or more hydroxyl groups; and

b5) terpenes.

6. The composition as claimed in claim 5 , wherein b1) is chosen from esters of saturated or unsaturated C 2 -C 20 acids, and also mixtures thereof.

7. The composition as claimed in claim 5 , wherein b2) is chosen from ortho-phthalates, citrates, and malonates.

8. The composition as claimed in claim 5 , wherein b3) is chosen from menthol, neomenthol, phenylethyl alcohol, benzyl alcohol, citronellol, dihydromyrcenol, dihydroterpineol, dimetol, ethyllinalool, geraniol, linalool, tetrahydrolinalool, tetrahydromyrcenol, nerol, and also mixtures of two or more thereof.

9. The composition as claimed in claim 5 , wherein b4) is chosen from propionaldehyde, butyraldehyde, valeraldehyde, capraldehyde, benzaldehyde, geranial, neral, citronellal and, in general, aldehydes containing hydrocarbon-based groups comprising one or more unsaturations of olefinic type, menthone, isomenthone, 1,8-cineole, ascaridole, flavonone, damascones, damascenones, ionones, irisones, methylionones, frambinone, and also mixtures of two or more thereof in all proportions.

10. The composition as claimed in claim 5 , wherein b5) is chosen from terpinenes, myrcene, limonene, terpinolene, pinenes, sabinene, camphene, mixtures of two or more thereof, and also terpene-based essences.

11. The composition as claimed in claim 5 , wherein the odor-masking agent is chosen from odor-masking agents comprising:

at least one component b1);

at least one component b1) and at least one component b2);

at least one component b1) and at least one component b3);

at least one component b1) and at least one component b4);

at least one component b1) and at least one component b5);

at least one component b1), at least one component b2) and at least one component b3);

at least one component b 1), at least one component b2) and at least one component b4);

at least one component b1), at least one component b2) and at least one component b5);

at least one component b1), at least one component b3) and at least one component b4);

at least one component b1), at least one component b3) and at least one component b5);

at least one component b1), at least one component b2), at least one component b3) and at least one component b4);

at least one component b1), at least one component b2), at least one component b3) and at least one component b5);

at least one component b1), at least one component b2), at least one component b3), at least one component b4) and at least one component b5);

at least one component b2);

at least one component b2) and at least one component b3);

at least one component b2) and at least one component b4);

at least one component b2) and at least one component b5);

at least one component b2), at least one component b3) and at least one component b4);

at least one component b2), at least one component b3) and at least one component b5);

at least one component b2), at least one component b4) and at least one component b5);

at least one component b2), at least one component b3), at least one component b4) and at least one component b5);

at least one component b3);

at least one component b3) and at least one component b4);

at least one component b3) and at least one component b5);

at least one component b3), at least one component b4) and at least one component b5);

at least one component b4);

at least one component b4) and at least one component b5); and

at least one component b5).

12. The composition as claimed in claim 5 , wherein the odor-masking agent comprises from 1% to 40% by weight of at least one monoester b 1) relative to the total weight of composition b).

13. The composition as claimed in claim 5 , wherein the odor-masking agent comprises from 10% to 70% by weight of at least one diester and/or triester b2) relative to the total weight of composition b).

14. The composition as claimed in claim 5 , wherein the odor-masking agent comprises from 1% to 30% by weight of at least one alcohol b3) relative to the total weight of composition b).

15. The composition as claimed in claim 5 , wherein the odor-masking agent comprises from 0.5% to 20% by weight of at least one aldehyde and/or ketone b4) relative to the total weight of composition b).

16. The composition as claimed in claim 5 , wherein the odor-masking agent comprises up to 20% by weight of at least one terpene indicated in b5) relative to the total weight of composition b).

17. The composition as claimed in claim 1 , wherein the odor-masking agent comprises:

b 1) from 1% to 40% by weight of at least one monoester;

b2) from 10% to 70% by weight of at least one diester and/or triester;

b3) from 1% to 30% of at least one alcohol;

b4) from 0.5% to 20% of at least one aldehyde and/or ketone of formula R a —CO—R b , in which R a represents a linear or branched hydrocarbon-based chain comprising from 1 to 6 carbon atoms, optionally comprising one or more unsaturation(s) in the form of double bonds, and le represents a cyclic hydrocarbon-based chain or a linear or branched hydrocarbon-based chain optionally substituted with a cyclic structure, le comprising from 6 to 12 carbon atoms, optionally comprising one or more unsaturation(s) in the form of double bonds and being optionally substituted with one or more hydroxyl groups; and

b5) optionally up to 20% of at least one terpene.

18. The composition as claimed in claim 17 , wherein the odor-masking agent comprises:

from 5% to 30% by weight of at least one monoester b1), chosen from isoamyl acetate, ethyl 2-methylbutyrate, isoamyl butyrate, phenylethyl acetate, ethyl caproate, benzyl acetate and hexyl acetate, and mixtures thereof;

from 20% to 60% by weight of at least one diester and/or triester b2) chosen from ortho-phthalates; citrates; malonates, and mixtures thereof;

from 5% to 25% of at least one alcohol, as described previously in b3);

from 1% to 10% of at least one ketone, as described previously in b4); and

from 1% to 10% of at least one terpene referenced above in b5).

19. The composition as claimed in claim 1 , comprising:

a) from 50% to 95% by weight of at least one oxide of an organic sulfide of general formula (1);

b) from 10 ppm to 2%, relative to the total weight of the composition, of at least one odor-masking agent b); and

c) from 5% to 50% by weight of at least one cosolvent.

20. The composition as claimed in claim 19 , wherein the cosolvent is chosen from compounds that are at least partially or totally soluble in oxides of organic sulfides a).

21. The composition as claimed in claim 19 , comprising:

a) about 80% by weight of DMSO;

b) from 10 ppm to 2%, relative to the total weight of the composition, of masking agent comprising:

from 5% to 30% by weight of at least one monoester b1), chosen from isoamyl acetate, ethyl 2-methylbutyrate, isoamyl butyrate, phenylethyl acetate, ethyl caproate, benzyl acetate and hexyl acetate, and mixtures thereof;

from 20% to 60% by weight of at least one diester and/or triester b2) chosen from ortho-phthalates; malonates, and mixtures thereof;

from 5% to 25% of at least one alcohol, as described previously in b3);

from 1% to 10% of at least one ketone, as described previously in b4); and

from 1% to 10% of at least one terpene referenced above in b5); and

c) about 20% by weight of glycerol.

22. The composition of claim 2 , wherein the content of the odor-masking agent(s) b) is between 100 ppm and 1000 ppm.

23. The composition of claim 20 , wherein the cosolvent is chosen from carbonates, esters, ketones, amines, amides, and alcohols.

24. The composition of claim 20 , wherein the cosolvent is chosen from saturated alcohols comprising from 1 to 10 carbon atoms.

25. The composition of claim 20 , wherein the cosolvent is chosen from methanol, ethanol, propanol, butanol, pentanol, ethylene glycol, propylene glycol, and glycerol (1,2,3-propanetriol).

26. The composition of claim 1 , wherein the at least one oxide of an organic sulfide of general formula (1) is present in the composition in an amount of at least 70% by weight.

27. The composition of claim 1 , wherein the at least one oxide of an organic sulfide of general formula (1) is present in the composition in an amount of at least 80% by weight.

28. The composition of claim 6 , wherein b 1) is selected from the group consisting of acetates, propionates, butyrates, methylbutyrates, pentanoates, hexanoates, heptanoates, caproates, oleates, and linoleates or linolenates of ethyl, propyl, butyl, pentyl, 2-methylbutyl, isoamyl, hexyl, benzyl, phenylethyl, menthyl, and carvyl.

29. The composition of claim 5 , wherein the alcohols are monoalcohols.

Assignments (6)
SECURITY INTEREST Recorded Mar 30, 2021
From: GAYLORD CHEMICAL COMPANY, L.L.C.
To: OWL ROCK CAPITAL CORPORATION
Reel/Frame 055762/0584 →
RELEASE OF SECURITY INTEREST Recorded Mar 30, 2021
From: TWIN BROOK CAPITAL PARTNERS, LLC, AS AGENT
To: GAYLORD CHEMICAL COMPANY, L.L.C.
Reel/Frame 055773/0723 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 30, 2020
From: ARKEMA FRANCE
To: GAYLORD CHEMICAL COMPANY LLC
Reel/Frame 054203/0021 →
SECURITY INTEREST Recorded Sep 15, 2020
From: GAYLORD CHEMICAL COMPANY, LLC, AS GRANTOR
To: TWIN BROOK CAPITAL PARTNERS, LLC, AS GRANTEE
Reel/Frame 053773/0009 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 15, 2020
From: ARKEMA FRANCE
To: GAYLORD CHEMICAL COMPANY, LLC
Reel/Frame 053778/0432 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 26, 2012
From: SCHMITT, PAUL-GUILLAUME; MONGUILLON, BERNARD; VAUTHRIN, MELANIE
To: ARKEMA FRANCE
Reel/Frame 027600/0338 →
Priority Claims (2)
FR 09 55398 · Jul 31, 2009 · national
FR 10 50157 · Jan 12, 2010 · national
Continuity (2)
Provisional Application 61234680 · Aug 18, 2009
Related Publication 20120132858A1 · May 31, 2012