Zwitterionic imidazolinium surfactant and use in the manufacture of absorbent paper

Patent metadata

Field	Value
Publication number	US-10697123-B2
Application number	US-201815865353-A
Country	US
Kind code	B2
Filing date	Jan 9, 2018
Priority date	Jan 17, 2017
Publication date	Jun 30, 2020
Grant date	Jun 30, 2020

Abstract

Zwitterionic surfactant compounds and their use in connection with absorbent paper manufacture in debonder and softener formulations. An exemplary surfactant is an imidazolinium compound of formula:

wherein X is SO 3 , R 1 is a hydrocarbyl spacer group having a chain length of from 2-6 carbon atoms, R 2 is a hydrocarbyl group having from 8 to 22 carbon atoms; and R 3 is an alkenylamidoalkyl moiety having from 8 to 30 carbon atoms.

First claim

What is claimed is:

1. A zwitterionic surfactant compound useful for debonder and softener compositions utilized in absorbent paper manufacture, said compound having the formula I:

wherein:
R 1 is an alkylene group of the formula (—CH 2 —) n wherein n is an integer from 2 to 6;
R 2 is a straight or branched saturated or unsaturated hydrocarbon moiety having from 3 to 30 carbon atoms wherein said R 2 :
(i) is unsubstituted or optionally substituted with one or more groups which are the same or different and are independently selected from the group consisting of halogen, cyano, alkyl, cycloalkyl, —OH, O(C 1 —C 6 ) alkyl, —CO 2 H, —C(═O)(C 1 —C 6 ) alkyl, —C(═O)O(C 1 —C 6 ) alkyl, —N[(C 1 —C 6 ) alkyl] 2 , —NH—C(O)(C 1 —C 6 ) alkyl, —C(O)NH 2 , —C(O)—NH(C 1 —C 6 ) alkyl, and —NH(C 1 —C 6 ) alkyl, and/or
(ii) optionally have interposed within said hydrocarbon moiety one or more groups which are the same or different and are independently selected from the group consisting of —NH—C(O)—, —C(O)—NH—, —O—, —SO 2 — and —C(═O)—;

R 3 is a straight or branched saturated or unsaturated hydrocarbon moiety having from 3 to 30 carbon atoms wherein said R 3 :
(i) is unsubstituted or optionally substituted with one or more groups which are the same or different and are independently selected from the group consisting of halogen, cyano, alkyl, cycloalkyl, —OH, O(C 1 —C 6 ) alkyl, —CO 2 H, —C(═O)(C 1 —C 6 ) alkyl, —C(═O)O(C 1 —C 6 ) alkyl, —N [(C 1 —C 6 ) alkyl] 2 , —NH—C(O)(C 1 —C 6 ) alkyl, —C(O)NH 2 , —C(O)—NH(C 1 —C 6 ) alkyl, and —NH(C 1 —C 6 ) alkyl, and/or
(ii) optionally have interposed within said hydrocarbon moiety one or more groups which are the same or different and are independently selected from the group consisting of —NH—C(O)—, —C(O)—NH—, —O—, —SO 2 — and —C(═O)—;

wherein at least one of R 2 or R 3 or has from 8 to 30 carbon atoms;
X is SO 3 ; and
p is 1 or 2.

2. The zwitterionic surfactant compound of claim 1 , wherein R 2 and R 3 have from 8 to 30 carbon atoms.

3. The zwitterionic surfactant compound of claim 1 , wherein said compound of formula I is an imidazolinium compound of formula II:

4. The zwitterionic surfactant compound of claim 3 , wherein:
R 1 is as defined above;
R 2 is a hydrocarbyl group having from 8 to 22 carbon atoms; and
R 3 is an alkenylamidoalkyl moiety having from 8 to 22 carbon atoms.

5. The zwitterionic surfactant compound according to claim 4 , wherein R 1 is an alkylene group of the formula (—CH 2 —) n wherein n is 3 or 4.

6. The zwitterionic surfactant compound according to claim 4 , wherein R 2 is an alkenyl substituent with from 10 to 20 carbon atoms.

7. The zwitterionic surfactant compound according to claim 4 , wherein R 3 is an alkenylamidoalkyl moiety of the formula:
(—CH 2 —) m —NH—CO—R 4

wherein R 4 is an alkenyl group and m is an integer from 2 to 10.

8. The zwitterionic surfactant compound according to claim 7 , wherein R 4 is an alkenyl substituent having from 10-20 carbon atoms.

9. A debonder composition for absorbent paper manufacture comprising a zwitterionic imidazolinium surfactant of claim 1 in admixture with a nonionic surfactant.

10. The debonder composition according to claim 9 , wherein the debonder composition comprises from 5 to 45 wt. % of zwitterionic imidazolinium surfactant and from 65 to 95 wt. percent of nonionic surfactant.

11. The debonder composition according to claim 10 , wherein the debonder composition comprises from 10 to 20 wt. % of zwitterionic imidazolinium surfactant and from 80 to 90 wt. % of nonionic surfactant.

12. The debonder composition according to claim 9 , wherein the debonder composition comprises a nonionic surfactant selected from alkoxylated fatty acids and alkoxylated fatty alcohols.

13. The debonder composition according to claim 12 , wherein the debonder composition comprises a mixture of mono- and diesters of one or more fatty acids.

14. The debonder composition according to claim 13 , wherein the mixture of mono- and diesters of the fatty acid(s) are a mixture of PEG monoesters and PEG diesters having a PEG chain molecular weight in the range of 200 to 800.

15. (Original; withdrawn) A method of making absorbent sheet comprising:
(a) preparing an aqueous furnish of papermaking fibers;
(b) incorporating a debonder composition into the aqueous furnish comprising a zwitterionic imidazolinium surfactant of claim 1 ;
(c) incorporating a cationic wet strength resin into the aqueous furnish; and
(d) forming the papermaking furnish into absorbent sheet.

16. The method of making absorbent sheet according to claim 15 , wherein the debonder composition is incorporated into the aqueous furnish prior to incorporating the cationic wet strength resin into the aqueous furnish.

17. The method of making absorbent sheet according to claim 15 , wherein the cationic wet strength resin is incorporated into the aqueous furnish prior to incorporating the debonder composition into the aqueous furnish.

18. The method according to claim 15 , wherein the cationic wet strength resin is incorporated into the aqueous furnish at a level of from 5 to 25 lbs/ton of papermaking fiber.

19. The method according to claim 15 , wherein the debonder composition is incorporated into the aqueous furnish at a level of from 1 to 16 lbs debonder composition per ton of papermaking fiber.

20. The method according to claim 19 , wherein the debonder composition comprises a zwitterionic imidazolinium surfactant in admixture with a nonionic surfactant.

Assignees

• Gpcp Ip Holdings Llc

Inventors

• Chen Yu
• Hammes Brian S

Classifications

• D21H17/72

  of organic material · CPC title

• D21H21/22

  Agents rendering paper porous, absorbent or bulky · CPC title

• D21H21/24 Primary

  Surfactants · CPC title

• D21H21/20

  Wet strength agents · CPC title

• C07D233/16

  Radicals substituted by nitrogen atoms · CPC title