Polymeric amphoteric surfactant compound

Patent metadata

Field	Value
Publication number	US-12473322-B2
Application number	US-202117915843-A
Country	US
Kind code	B2
Filing date	Mar 31, 2021
Priority date	Apr 1, 2020
Publication date	Nov 18, 2025
Grant date	Nov 18, 2025

Abstract

Disclosed herein is a polymeric amphoteric surfactant compound of formula (I).

First claim

The invention claimed is:

1 . A polymeric amphoteric surfactant compound having chemical formula I:

wherein:
R 1 represents a C 8 to C 22 alkyl group, a —((CH 2 ) 2 O) o —R 5 group, a —((CH(CH 3 )CH 2 ) p O)—R 6 group, a —((CH 2 ) 2 O) q —((CH(CH 3 )CH 2 ) r O)—R 7 group, or a —((CH(CH 3 )CH 2 ) q′ O)—((CH 2 ) 2 O) r′ —R 8 group;
o and p each independently represent a number from 2 to 8;
q, q′, r and r′ each independently represent a number from 1 to 5;
L 1 to L 3 each independently represent a C 1 to C 3 alkyl group;
R 2 and R 3 each independently represent a C 1 to C 3 alkyl group;
R 4 represents OH or a C 1 to C 3 alkyl group;
R 5 to R 8 each independently represent a C 8 to C 22 alkyl group;
n represents a number from 1 to 5 and m represents a number from 0 to 4, where the sum of n+m is from 1 to 5, provided that n is at least 1.

2 . The polymeric amphoteric surfactant compound according to claim 1 , wherein R 1 represents a C 8 to C 16 alkyl group.

3 . The polymeric amphoteric surfactant compound according to claim 2 , wherein R 1 represents a C 8 , C 10 , C 12 , C 14 or C 16 alkyl group.

4 . The polymeric amphoteric surfactant compound according to claim 3 , wherein R 1 represents a C 8 , C 10 or C 12 alkyl group.

5 . The polymeric amphoteric surfactant compound according to claim 1 , wherein R 1 represents a —((CH 2 ) 2 O) o —R 5 group, a —((CH(CH 3 )CH 2 ) p O)—R 6 group, a —((CH 2 ) 2 O) q —((CH(CH 3 )CH 2 ) r O)—R 7 group, or a —((CH(CH 3 )CH 2 ) q′ O)—((CH 2 ) 2 O) r′ —R 8 group.

6 . The polymeric amphoteric surfactant compound according to claim 5 , wherein:
o and p each independently represent a number from 3 to 5; and q, q′, r and r′ each independently represent a number from 1 to 3.

7 . The polymeric amphoteric surfactant compound according to claim 5 , wherein R 1 represents a —((CH 2 ) 2 O) o —R 5 group or a —((CH(CH 3 ) CH 2 ) p O)—R 6 group.

8 . The polymeric amphoteric surfactant compound according to claim 1 , wherein R 2 and R 3 are methyl.

9 . The polymeric amphoteric surfactant compound according to claim 1 , wherein:
R 4 represents OH; and/or R 5 to R 8 each independently represent a C 8 to C 16 alkyl group.

10 . The polymeric amphoteric surfactant compound according to claim 1 , wherein:
L 1 represents CH 2 ; and/or L 2 represents (CH 2 ) 3 ; and/or L 3 represents CH 2 .

11 . A polymeric amphoteric surfactant formulation comprising one or more compounds of formula I as defined in claim 1 , wherein:
(a) when R 1 is a C 8 to C 22 alkyl group, then the formulation is formed of compounds of formula I having the same R 1 group or is formed from a mixture of compounds of formula I having different R 1 groups; (b) when R 1 is a —((CH 2 ) 2 O) o —R 5 group, a —((CH(CH 3 ) CH 2 ) p O)—R 6 group, a —((CH 2 ) 2 O) q —((CH(CH 3 )CH 2 ) r O)—R 7 group, or a —((CH(CH 3 )CH 2 ) q′ O)—((CH 2 ) 2 O) r′ —R 8 group, then the formulation is formed of compounds of formula I having the same R 1 group.

12 . The polymeric amphoteric surfactant compound according to claim 1 , wherein R 1 represents a C 8 to C 12 alkyl group or a C 12 to C 14 alkyl group.

13 . The polymeric amphoteric surfactant compound according to claim 1 , wherein R 1 represents a C 8 to C 14 alkyl group.

14 . A composition comprising:
a polymeric amphoteric surfactant compound according to claim 1 .

15 . A composition comprising:
a polymeric amphoteric surfactant formulation according to claim 11 .

16 . A method of forming a compound according to formula I:

the method comprising the step of reacting a compound for formula II:

with a compound of formula III:

in the presence of a suitable solvent and a suitable base, wherein:
L 1 to L 3 , R 1 to R 4 , n and m are as defined in claim 1 ;
X is a leaving group; and
Y + is a monovalent metal cation.

17 . The method according to claim 16 , wherein the compound of formula II is formed by reaction of a compound of formula IV:

with a compound of formula V:

in the presence of a suitable solvent and a suitable base, wherein:
R 1 represents a C 8 to C 22 alkyl group, a —((CH 2 ) 2 O) o —R 5 group, a —((CH(CH 3 )CH 2 ) p O)—R 6 group, a —((CH 2 ) 2 O) q —((CH(CH 3 )CH 2 ) r O)—R 7 group, or a —((CH(CH 3 )CH 2 ) q′ O)—((CH 2 ) 2 O) r′ —R 8 group;
o and p each independently represent a number from 2 to 8;
q, q′, r and r′ each independently represent a number from 1 to 5;
L 1 and L 2 each independently represent a C 1 to C 3 alkyl group;
R 2 and R 3 each independently represent a C 1 to C 3 alkyl group;
n represents a number from 1 to 5 and m represents a number from 0 to 4, where the sum of n+m is from 1 to 5, provided that n is at least 1; and
R 9 represents H or C 1 to C 3 alkyl.

18 . The method according to claim 17 , wherein the compound of formula IV is formed by reaction of a compound of formula VI:

with a compound of formula VII:

in the presence of a suitable solvent and a suitable base, wherein:
R 1 represents a C 8 to C 22 alkyl group, a —((CH 2 ) 2 O) o —R 5 group, a —((CH(CH 3 )CH 2 ) p O)—R 6 group, a —((CH 2 ) 2 O) q —((CH(CH 3 )CH 2 ) r O)—R 7 group, or a —((CH(CH 3 )CH 2 ) q′ O)—((CH 2 ) 2 O) r′ —R 8 group;
o and p each independently represent a number from 2 to 8;
q, q′, r and r′ each independently represent a number from 1 to 5;
n represents a number from 1 to 5 and m represents a number from 0 to 4, where the sum of n+m is from 1 to 5, provided that n is at least 1;
R 9 represents H or C 1 to C 3 alkyl;
X′ represents a leaving group; and
L 1′ represents a bond or a C 1 to C 2 alkyl group.

19 . The method according to claim 18 , wherein X′ represents Cl, Br or I.

20 . The method according to claim 16 , wherein one or both of the following apply:
X is selected from Cl, Br or I; and Y + is Na + .

Assignees

• Petroliam Nasional Berhad Petronas

Inventors

• Samsodin Normawati
• Shahruddin Sara
• Ismail Nur Liyana
• Sharma Karam Chand Navin
• Leong Jun Xing

Classifications

• C07H15/12

  attached to a nitrogen atom of the saccharide radical · CPC title

• C07H15/04 Primary

  attached to an oxygen atom of the saccharide radical · CPC title

• C07H1/00 Primary

  Processes for the preparation of sugar derivatives · CPC title

• C11D1/008

  Polymeric surface-active agents · CPC title

• C07H15/14 Primary

  attached to a sulfur, selenium or tellurium atom of a saccharide radical · CPC title