Polyether derivatives, uses, and methods of making the same

Patent metadata

Field	Value
Publication number	US-10844169-B2
Application number	US-202016779232-A
Country	US
Kind code	B2
Filing date	Jan 31, 2020
Priority date	Jul 31, 2017
Publication date	Nov 24, 2020
Grant date	Nov 24, 2020

Abstract

The invention contemplates certain polyethers, polyether derivatives, and methods of making and using those same polymers. For example, the starting materials can, e.g., citronellol, prenol, isocitronellol and isoprenol.

First claim

The invention claimed is:

1. A compound according to Formula I:

or a salt thereof, wherein,
R 1 is optionally substituted C 1 -C 12 alkyl;
R 2 is C 1-2 alkyl, or C(O)—C 1-6 alkyl; and
n is an integer between 0 and 20.

2. The compound according to claim 1 , wherein R 1 is unsubstituted linear C 1 -C 12 alkyl or unsubstituted branched C 3 -C 12 alkyl.

3. The compound according to claim 1 , wherein R 1 is unsubstituted branched or unsubstituted linear C 6 alkyl.

4. The compound according to claim 3 , wherein R 1 is CH 2 CH 2 CH(CH 3 )CH 2 CH 2 .

5. The compound according to claim 1 , wherein R 2 is C 1-20 alkyl.

6. The compound according to claim 1 , wherein R 2 is C(O)—C 1-6 alkyl.

7. The compound according to claim 6 , wherein R 2 is selected from the group consisting of C(O)—C 1-5 alkyl, C(O)—C 1-4 alkyl, C(O)—C 1-3 alkyl and C(O)—C 1-2 alkyl.

8. The compound according to claim 1 , wherein n is 0, 1, 2, or 3.

9. The compound according to claim 1 , wherein R 1 is CH 2 CH 2 CH(CH 3 )CH 2 CH 2 , n is 1-3 and R 2 is C(O)—C 1-6 alkyl and said C 1-6 alkyl is selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, or n-hexyl.

10. A composition comprising the compound according to claim 1 or any salts thereof, or any mixtures thereof, in combination with at least one suitable solvent, carrier, or excipient.

11. The composition according to claim 10 which is a fragrance composition, or a perfume composition, or a soap composition, or an insect repellant composition, or an insecticide composition, or a detergent composition, or a household cleaning agent composition, or an air freshener composition, or a room spray composition, or a pomander composition, or a candle composition, or a cosmetic composition, or a toilet water composition, or a pre-shave or after-shave lotion composition, or a talcum-powder composition, or a hair-care product composition, or a body deodorant composition, or an antiperspirant composition, or a shampoo composition, or a pet litter composition, or a topically applied skin care composition, or a paint or coating composition, or a lubricant composition, or a plastic composition, or a defoamer composition, or a hydraulic fluid composition, or an antimicrobial composition.

12. The composition according to claim 10 , which is a fragrance composition, insect repellent composition, candle composition, or cosmetic composition.

13. A method of making a compound according to claim 1 , or a salt thereof, wherein the method comprises the steps of
(1) introducing into a reactor a compound of Formula A:

wherein, R 1 is optionally substituted C 1 -C 12 alkyl; and

(2) exposing said compound to a solid ion-exchange resin, thereby causing the polymerization of the compound of Formula A to yield the compound of Formula I, wherein R 2 is H; and
(3) isolating and/or purifying said compound, wherein n is from 0-5; and
(4) reacting the compound of Formula I, wherein R 2 is H, with a suitable reagent to convert R 2 to C(O)—C 1-6 alkyl.

14. The method according to claim 13 , wherein the C(O)—C 1-6 alkyl is methyl or ethyl.

15. The compound according to claim 1 , wherein R 1 is CH 2 CH 2 CH(CH 3 )CH 2 CH 2 , n is 1-3 and R 2 is C(O)—C 1-6 alkyl and said C 1-6 alkyl is methyl.

16. The compound according to claim 1 , wherein R 1 is CH 2 CH 2 CH(CH 3 )CH 2 CH 2 , n is 1-3 and R 2 is C(O)—C 1-6 alkyl and said C 1-6 alkyl is ethyl.

17. The compound according to claim 1 , wherein R 1 is CH 2 CH 2 CH(CH 3 )CH 2 CH 2 , n is 1-3 and R 2 is C(O)—C 1-6 alkyl and said C 1-6 alkyl is propyl.

18. The compound according to claim 1 , wherein R 1 is CH 2 CH 2 CH(CH 3 )CH 2 CH 2 , n is 0, 1 or 2, and R 2 is C(O)—C 1-6 alkyl.

19. The compound according to claim 1 , wherein R 1 is CH 2 CH 2 CH(CH 3 )CH 2 CH 2 , n is 0, 1 or 2, and R 2 is C(O)—C 1-6 alkyl and said C 1-6 alkyl is methyl, ethyl or propyl.

20. The compound according to claim 1 , wherein R 1 is CH 2 CH 2 CH(CH 3 )CH 2 CH 2 , n is 0, 1 or 2, and R 2 is C(O)—C 1-6 alkyl and said C 1-6 alkyl is methyl.

21. A compound of the formula:

wherein R 2 is H, C 1-20 alkyl, aryl, aryl C 1-2 alkyl, optionally unsaturated alkyl esters, or optionally substituted aryl esters; and n is an integer between 0 and 20.

22. The compound according to claim 21 , wherein n is 0, 1, 2, or 3.

23. A composition comprising the compound according to claim 21 or any salts thereof, or any mixtures thereof, in combination with at least one suitable solvent, carrier, or excipient.

24. A compound according to Formula II:

or a salt thereof, wherein,
R 1 is optionally substituted C 1 -C 12 alkyl;
n1 and n2 are each independently an integer between 0 and 20; and
X is a diacyl moiety of the formula —C(O)—R 3 —C(O)—, wherein R 3 is optionally substituted C 1-22 alkyl, optionally substituted C 2-22 alkenyl or optionally substituted aryl.

25. The compound according to claim 24 , wherein R 1 is CH 2 CH 2 CH(CH 3 )CH 2 CH 2 .

26. The compound according to claim 25 , wherein R 3 is unsubstituted C 1-10 alkyl or wherein R 3 is unsubstituted C 1-6 alkyl.

27. The compound according to claim 25 , wherein n1 and/or n2 are each independently 0, 1, 2 or 3.

28. A composition comprising the compound according to claim 24 or any salts thereof, or any mixtures thereof, in combination with at least one suitable solvent, carrier, or excipient.

29. A method of making an ester Compound 1A, according to Formula I:

wherein, R 1 is optionally substituted C 1 -C 12 alkyl; and wherein R 2 is (C═O)C 1-4 alkyl, and n is an integer between 0 and 20;
wherein the method comprises reacting the alcohol Compound 1 of Formula I, wherein R 2 is H, with an alkyl anhydride of the formula R 2 O(C═O)OR 2 , wherein R 2 is (C═O)C 1-4 alkyl, and wherein the reaction is conducted under continuous flow conditions in the absence of a base or catalyst.

Assignees

• P2 Science Inc

Inventors

• Foley Patrick
• Yang Yonghua
• Salam Tania

Classifications

• C08G65/34

  from hydroxy compounds or their metallic derivatives {(C08G65/26 takes precedence)} · CPC title

• C08G65/00 Primary

  Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule · CPC title

• C08G65/002 Primary

  from unsaturated compounds (unsaturated oxiranes C08G65/14) · CPC title

• C08G2650/38

  containing oxygen in addition to the ether group · CPC title