Polyether derivatives, uses, and methods of making the same

Patent metadata

Field	Value
Publication number	US-2021024691-A1
Application number	US-202017069696-A
Country	US
Kind code	A1
Filing date	Oct 13, 2020
Priority date	Jul 31, 2017
Publication date	Jan 28, 2021
Grant date	—

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

1 . A compound according to Formula Y:

wherein the dashed bonds (A, B and C) represent optional bonds, and wherein R 1 is optionally substituted Ci-C12 alkyl; R 2 is H, Ci-2oalkyl, aryl, aryl-Ci-2 alkyl, optionally unsaturated alkyl esters or aryl esters, or R 2 is a moiety:

wherein X is a diacyl moiety of formula —C(0)-R 3 —C(0)-, wherein R 3 is optionally substituted Ci-22 alkyl, optionally substituted C2-22 alkenyl or optionally substituted aryl;
and wherein n is an integer between 0 and 20;
provided that if the intramolecular bridging bond A is present then dashed bonds B and C are absent and substituted R 2 is absent

2 . The compound according to claim 1 , wherein the compound according to Formula Y is an ether compound according to Formula I

or a salt thereof, wherein,
R 1 is optionally substituted Ci-C12 alkyl (e.g., C1-C12 alkyl optionally further substituted with Ci-C12 alkyl or aryl);
R 2 is H, Ci-2oalkyl (e.g., lower alkyl (e.g., Ci-6 alkyl), or Ci-12 alkyl), aryl (e.g., phenyl), arylCi-2 alkyl (e.g., benzyl), optionally unsaturated alkyl esters (e.g., C(O)—Ci-20 alkyl), or optionally substituted aryl esters (e.g., C(O)-aryl);
n is an integer between 0 and 20.

3 . The compound according to claim 2 , wherein R 1 is unsubstituted linear C1-C12 alkyl or unsubstituted branched C3-C12 alkyl

4 . The compound according to claim 2 or 3 , wherein R 1 is unsubstituted branched or linear C 6 alkyl.

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

6 . The compound according to any of claims 2 - 5 , wherein R 2 is alkyl (e.g., lower alkyl (e.g., Ci-6), or Ci-12).

7 . The compound according to any of claims 2 - 5 , wherein R 2 is an optionally unsaturated alkyl ester (e.g., C(0)-Ci-2o alkyl, or C(0)-O— 6 alkyl).

8 . The compound according to claim 7 , wherein R 2 is C(0)-Ci-6 alkyl, optionally wherein R 2 is C(0)-Ci-5 alkyl, C(0)-Ci- 4 alkyl, C(0)-Ci- 3 alkyl or C(0)-Ci_ 2 alkyl.

9 . The compound according to any of claims 2 - 8 , wherein n is greater than 1 (e.g., between 2 and 20).

10 . The compound according to any of claims 2 - 9 , wherein R 1 is CH 2 CH 2 CHiCH 3 )CH 2 CH 2 , n is 1-3 (e.g. 1-2) and R 2 is C(0)-Ci-6 alkyl and said Ci-6 alkyl is selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, or n-hexyl.

11 . The compound according to claim 2 , wherein the compound is:

wherein R 2 and n are as defined in claim 2 .

12 . The compound according to claim 1 , wherein the compound according to Formula Y is an ether or polyether diester compound according to Formula II:

or a salt thereof, wherein,
R 1 is optionally substituted Ci-C12 alkyl (e.g., C1-C12 alkyl optionally further substituted with Ci-C12 alkyl or aryl);
n1 and n2 are each independently an integer between 0 and 20; and
X is a diacyl moiety of the formula —C(0)-R 3 —C(0)-, wherein R 3 is optionally substituted Ci-22 alkyl, optionally substituted C2-22 alkenyl or optionally substituted aryl.

13 . The compound according to claim 12 , wherein R 1 is unsubstituted linear C1-C12 alkyl or branched C3-C12 alkyl.

14 . The compound according to claim 13 , wherein R 1 is CH 2 CH2CH(CH3)CH 2 CH2.

15 . The compound according to claim 13 or 14 , wherein R 3 is unsubstituted Ci-10 alkyl, e.g., linear unsubstituted Ci-10 alkyl or branched unsubstituted Ci-10 alkyl, or wherein R 3 is unsubstituted Ci-6 alkyl, e.g., linear unsubstituted Ci-6 alkyl or branched unsubstituted Ci- 6 alkyl.

16 . The compound according to claim 13 , wherein R 3 is unsubstituted C2-22 alkenyl, e.g., linear unsubstituted C2-22 alkenyl or branched unsubstituted C2-22 alkenyl, optionally wherein any of said alkenyl are mono-unsaturated.

17 . The compound according to claim 13 , wherein R 3 is aryl, e.g., substituted or unsubstituted phenyl.

18 . The compound according to any of claims 13 - 17 , wherein n1 and/or n2 is greater than 1 (e.g., between 2 and 20).

19 . The compound according to claim 1 , wherein the compound according to Formula Y is a compound according to Formula III:

or a salt thereof, wherein,
R 1 is optionally substituted Ci-C12 alkyl (e.g., C1-C12 alkyl optionally further substituted with Ci-C12 alkyl or aryl); and
n is an integer between 0 and 20.

20 . The compound according to claim 19 , wherein R 1 is unsubstituted linear C1-C12 alkyl or branched C3-C12 alkyl, e.g., wherein R 1 is CH2CH 2 CH(CH3)CH 2 CH2.

21 . The compound according to claim 19 or 20 , wherein n is 0 to 5, e.g., wherein n is 0, 1, 2 or 3.

22 . A composition comprising the compound according to any of claim 1 - 21 or any salts thereof, or any mixtures thereof, in combination with at least one suitable solvent, carrier, or excipient.

23 . The composition according to claim 22 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.

24 . The composition according to claim 22 , which is a fragrance composition, insect repellent composition, candle composition, or cosmetic composition.

25 . A method of making a compound according to claim 2 , wherein R 2 is H, 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 Ci-C12 alkyl (e.g., C1-C12 alkyl optionally further substituted with Ci-C12 alkyl or aryl); 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 according to claim 2 , wherein R 2 is H; and
(3) isolating and/or purifying (e.g., by distillation) said compound, e.g., a group of related Compounds 1 wherein n varies within a range, e.g., wherein n is from 0-5, or from 5-10, or from 10

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

• C08G2650/38

  containing oxygen in addition to the ether group · CPC title

• C08G65/002 Primary

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