Heterocyclic amphoteric compounds

Patent metadata

Field	Value
Publication number	US-2016107994-A1
Application number	US-201414518517-A
Country	US
Kind code	A1
Filing date	Oct 20, 2014
Priority date	Oct 20, 2014
Publication date	Apr 21, 2016
Grant date	—

Abstract

Disclosed are a variety of amphoteric compounds having a heterocyclic quaternary nitrogen group. The heterocycle includes pyridines, piperidines, and pyrrolidines, and is linked to the hydrophobe via either an amide or an ester linkage. These heterocyclic amphoteric compounds can be advantageously prepared in high yield and purity by a two-step chemoenzymatic process, and have excellent surfactant properties.

First claim

We claim:

1 . A compound having the formula 1:

wherein
R is a C 3 -C 23 hydrocarbyl group;
R 1 is a C 1 -C 8 hydrocarbyl group;
HETN is a heterocyclic group selected from piperidine, pyridine, pyrollidine, quinoline, tetrahydroquinoline, indole, indoline, octahydroindole, acridine, octahydroacridine, and tetradecahydroacridine;
X is O or NH;
n is 0 or 1; and
m is 0 or 1 and is chosen to afford a quaternary heterocyclic nitrogen.

2 . The compound according to claim 1 , wherein the hydrocarbyl group of R is unsubstituted.

3 . The compound according to claim 1 , wherein the hydrocarbyl group of R is substituted with one to five substituents selected from the group consisting of C 1 -C 6 alkoxy, C 1 -C 6 carboxyl, C 1 -C 15 aminocarbonyl, C 1 -C 15 amido, cyano, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkanoyloxy, hydroxy, aryl, heteroaryl, thioether, C 2 -C 10 dialkylamino, C 3 -C 15 trialkylammonium, chlorine, and bromine.

4 . The compound according to claim 2 , wherein the hydrocarbyl group of R is straight-chain or branched.

5 . The compound according to claim 3 , wherein the hydrocarbyl group of R is straight-chain or branched.

6 . The compound according to claim 2 , wherein the hydrocarbyl group of R is mono-unsaturated or poly-unsaturated.

7 . The compound according to claim 3 , wherein the hydrocarbyl group of R is mono-unsaturated or poly-unsaturated.

8 . The compound according to claim 1 , wherein R is an unsubstituted C 3 -C 8 cycloalkyl group.

9 . The compound according to claim 1 , wherein R is a C 3 -C 8 cycloalkyl group substituted with one to five substituents selected from the group consisting of C 1 -C 6 alkoxy, C 1 -C 6 carboxyl, C 1 -C 15 aminocarbonyl, C 1 -C 15 amido, cyano, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkanoyloxy, hydroxy, aryl, heteroaryl, thioether, C 2 -C 10 dialkylamino, C 3 -C 15 trialkylammonium, chlorine, and bromine.

10 . The compound according to claim 1 , wherein the hydrocarbyl group of R 1 is unsubstituted.

11 . The compound according to claim 1 , wherein the hydrocarbyl group of R 1 is substituted with one to three substituents selected from the group consisting of C 1 -C 6 alkoxy, C 1 -C 6 carboxyl, C 1 -C 15 aminocarbonyl, C 1 -C 15 amido, cyano, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkanoyloxy, hydroxy, aryl, heteroaryl, thioether, C 2 -C 10 dialkylamino, C 3 -C 15 trialkylammonium, chlorine, and bromine.

12 . The compound according to claim 10 , wherein the hydrocarbyl group of R 1 is straight-chain or branched.

13 . The compound according to claim 11 , wherein the hydrocarbyl group of R 1 is straight-chain or branched.

14 . The compound according to claim 10 , wherein the hydrocarbyl group of R 1 is C 1 -C 6 alkyl or alkenyl.

15 . The compound according to claim 11 , wherein the hydrocarbyl group of R 1 is C 1 -C 6 alkyl or alkenyl.

16 . The compound according to claim 1 , wherein R 1 is an unsubstituted C 3 -C 8 cycloalkyl group.

17 . The compound according to claim 1 , wherein R 1 is a C 3 -C 8 cycloalkyl group substituted with one to three substituents selected from the group consisting of C 1 -C 6 alkoxy, C 1 -C 6 carboxyl, C 1 -C 15 aminocarbonyl, C 1 -C 15 amido, cyano, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkanoyloxy, hydroxy, aryl, heteroaryl, thioether, C 2 -C 10 dialkylamino, C 3 -C 15 trialkylammonium, chlorine, and bromine.

18 . The compound according to claim 1 , wherein
R is selected from the group consisting of C 5 -C 19 alkyl, C 5 -C 17 alkenyl, C 5 -C 17 dienyl, and C 3 -C 8 cycloalkyl; R 1 is a C 1 -C 6 alkyl group; and HETN is selected from the group consisting of piperidine, pyridine, and pyrollidine.

19 . The compound according to claim 1 , wherein
RCO— is octanoyl, decanoyl, lauroyl, myristoyl, or a C 6 to C 20 acyl radical derived from coconut oil, hydrogenated coconut oil, or hydrogenated and/or fractionated coconut oil fatty acids; R 1 is methyl; HETN is a 3-piperidine group or a 4-piperidine group; and m is 1.

20 . The compound according to claim 19 , wherein RCO— is lauroyl.

21 . The compound according to claim 1 , wherein
RCO— is octanoyl, decanoyl, lauroyl, myristoyl, or a C 6 to C 20 acyl radical derived from coconut oil, hydrogenated coconut oil, or hydrogenated and/or fractionated coconut oil fatty acids; HETN is a 3-pyridine group or a 4-pyridine group; and m is 0.

22 : The compound according to claim 21 , wherein RCO— is lauroyl.

23 . The compound according to claim 1 , wherein the compound is selected from the group consisting of (4-cocoyloxy-1-methylpiperidinium-1-yl)acetate, (3-cocoyloxymethyl-1-methylpiperidinium-1-yl)acetate, (4-cocoyloxymethyl-1-methylpiperidinium-1yl)acetate, (4-lauroyloxy-1-methylpiperidinium-1-yl)acetate, (3-lauroyloxymethyl-1-methylpiperidinium-1-yl)acetate, 4-(lauroyloxymethylpyridinium-1-yl)acetate, 4-(lauramidomethylpyridinium-1-yl)acetate, and (4-lauramido-1-methylpiperidinium-1-yl)acetate.

24 . A mixture comprising at least two compounds having the formula 1:

wherein
R is a C 3 -C 23 hydrocarbyl group;
R 1 is a C 1 -C 8 hydrocarbyl group;
HETN is a heterocyclic group selected from piperidine, pyridine, pyrollidine, quinoline, tetrahydroquinoline, indole, indoline, octahydroindole, acridine, octahydroacridine, and tetradecahydroacridine;
X is O or NH;
n is 0 or 1; and
m is 0 or 1 and is chosen to afford a quaternary heterocyclic nitrogen, and

wherein the at least two compounds have at least one different R substituent.

25 . The mixture according to claim 24 , wherein
RCO— is selected from octanoyl, decanoyl, lauroyl, myristoyl, and a C 6 to C 20 acyl radical derived from coconut oil, hydrogenated coconut oil, or hydrogenated and/or fractionated coconut oil fatty acids; R 1 is methyl; HETN is a 3-piperidine group or a 4-piperidine group; and m is 1.

26 . The mixture according to claim 25 , wherein the at least two compounds have different R substituents selected from C 6 to C 20 acyl radicals derived from coconut oil, hydrogenated coconut oil, or hydrogenated and/or fractionated coconut oil fatty acids.

27 . The mixture according to claim 25 , wherein RCO— in one compound is lauroyl and RCO— in another compound is myristoyl.

28 . The mixture according to claim 25 , wherein RCO— in one compound is octanoyl and RCO— in another compound is decanoyl.

29 . The mixture according to claim 24 , wherein
RCO— is selected from octanoyl, decanoyl, lauroyl, myristoyl, and a C 6 to C 20 acyl radical derived from coconut oil, hydrogenated coconut oil, or hydrogenated and/or fractionated coconut oil fatty acids; HETN is a 3-pyridine group or a 4-pyridine group; and m is 0.

30 . The mixture according to claim 29 , wherein the at least two compounds have different R substituents selected from C 6 to C 20 acyl radicals derived from coconut oil, hydrogenated coconut oil, or hydrogenated and/or fractionated coconut oil fatty acids.

31 . The mixture according to claim 29 , wherein RCO— in one compound is lauroyl and R

Assignees

• Eastman Chem Co

Inventors

• Boaz Neil Warren
• Boone Matthew Allen

Classifications

• A61Q19/00

  Preparations for care of the skin · CPC title

• C07D213/75

  Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates · CPC title

• C07D211/58

  attached in position 4 · CPC title

• C07D213/30

  Oxygen atoms · CPC title

• C07D211/22

  by oxygen atoms · CPC title