Granted Patent B2

US 12,305,148 · App. 15/733,704 · Granted May 20, 2025

Inventors: Frauke Henning (Essen, DE); Jörg Peggau (Essen, DE); Andrea Lohse (Bottrop, DE); Astrid Zündorff (Muelheim an der Ruhr, DE); Sarah Radloff (Bochum, DE); Alexandra Trambitas (Alzenau, DE)

Assignee: Evonik Operations GmbH

C11D3/3742A61Q19/10C08G77/26C08K5/17

Abstract

Claims (147)

1. A siloxane (A) of formula (I):

M 1 a1 M 2 a2 M 3 a3 M 4 a4 D 1 b1 D 2 b2 D 3 b3 T 1 c1 T 4 c4 Q d   Formula (I),

with

M 1 =[R 1 3 SiO 1/2 ];

M 2 =[R 2 R 1 2 SiO 1/2 ];

M 3 =[R 3 R 1 2 SiO 1/2 ];

M 4 =[R 4 R 1 2 SiO 1/2 ];

D 1 =[R 1 2 SiO 2/2 ];

D 2 =[R 1 R 2 SiO 2/2 ];

D 3 =[R 1 R 3 SiO 2/2 ];

T 1 =[R 1 SiO 3/2 ];

T 4 =[R 4 SiO 3/2 ];

Q=[SiO 4/2 ];

a1=0 to 32;

a2=0 to 32;

a3=0 to 32;

a4=0 to 6;

b1=1 to 1000;

b2=0 to 10;

b3=0 to 10;

c1=0 to 10;

c4=0 to 5;

d=0 to 10;

R 1 =each independently identical or different hydrocarbon radicals;

R 2 =R 21 -R 22 ;

R 21 each independently identical or different divalent hydrocarbon radicals having at least one hydroxyl group and optionally further oxygen atoms;

R 22 each independently identical or different radicals of formula (II)

R 3 =R 31 -R 32 ;

R 31 =R 21 ;

R 32 =each independently identical or different radicals of formula (III)

R 4 =each independently identical or different alkoxy groups or acyloxy groups;

R 7 =—NH—;

R 8 =each independently identical or different radicals selected from the group consisting of methyl, ethyl n-propyl, isopropyl, n-butyl, isobutyl, and tert-butyl;

R 9 =each independently identical or different hydrogen and hydrocarbon radicals having 1 to 30 carbon atoms;

R 11 =each independently identical or different hydrocarbon radicals having at least one hydroxyl group and from 1 to 6 carbon atoms;

(A1) m- =each independently identical or different inorganic or organic anions with a charge of m−,

m 1 to 3; and

x=3;

wherein conditions (i) and (ii) are applicable:

a 2+ b 2≥1; and  (i)

a 3+ b 3≥1.  (ii)

2. The siloxane (A) according to claim 1 , wherein in addition, either condition (iii) or condition (iv) is applicable:

a 1= a 4= b 2= b 3= c 1= c 4= d= 0, and  (iii)

a 2= a 3=1; or

b 2= b 3=0,  (iv)

c 1+ c 4+ d≥ 1, and

a 2+ a 3+ a 4≥3.

3. A composition, comprising:

at least one siloxane (A) according to claim 1 .

4. The composition according to claim 3 , wherein the composition additionally comprises:

at least one siloxane selected from the group consisting of siloxane (B) and siloxane (C), wherein:

the siloxane (B) is a siloxane that differs from the siloxane (A) at least in that conditions (v) and (vi) are applicable rather than the conditions (i) to (ii):

a 2= b 2=0, and  (v)

a 3+ b 3≥2; and  (vi)

the siloxane (C) is a siloxane that differs from the siloxane (A) at least in that conditions (vii) and (viii) are applicable rather than conditions (i) and (ii):

a 3= b 3=0, and  (vii)

a 2+ b 2≥2.  (viii)

5. The composition according to claim 4 , wherein

a. a proportion by mass (% by weight) of the at least one siloxane (A) based on the total mass of the siloxanes is from 20% to 70%; and/or

b. a proportion by mass (% by weight) of the siloxane (B) based on the total mass of the siloxanes is from 0% to 15%; and/or

c. a proportion by mass (% by weight) of the siloxane (C) based on the total mass of the siloxanes is from 3% to 80%.

6. The composition according to claim 3 , wherein the composition comprises amide amines, wherein a proportion by mass (% by weight) of the amide amines based on the total mass of the at least one siloxane (A) is less than 1%.

7. A process for preparation of the siloxane (A) according to claim 1 or of a composition comprising the siloxane (A), the process comprising:

reacting at least one epoxy-functional siloxane having at least two epoxy groups with at least one tertiary amine selected from the group consisting of amide amines, and

at least one tertiary amine selected from the group consisting of dialkanolamines,

to form quaternary ammonium groups.

8. The process according to claim 7 , wherein the at least one epoxy-functional siloxane is prepared by hydrosilylation of at least one olefinically unsaturated epoxide with at least one SiH-functional siloxane of formula (V)

M 1 a1 M 5 a5 D 1 b1 D 5 b5 T 1 c1 T 4 c4 Q d   Formula (V),

with

M 5 =[R 1 2 SiHO 1/2 ],

D 5 =[R 1 SiHO 2/2 ],

a5=0 to 32;

b5=0 to 10;

where

M 1 , D 1 , T 1 , T 4 , Q, a1, b1, c1, c4, d, and R 1 are as defined in formula (I).

9. The process according to claim 7 , wherein the at least one epoxy-functional siloxane is a siloxane of the formula (VI)

M 1 a1 M 6 a5 D 1 b1 D 6 b5 T 1 c1 T 4 c4 Q d   Formula (VI),

with

M 6 =[R 13 R 1 2 SiO 1/2 ],

D 6 =[R 13 R 1 SiO 2/2 ],

a5=0 to 32,

b5=0 to 10,

R 13 =each independently identical or different organic epoxy radicals

wherein

M 1 , D 1 , T 1 , T 4 , Q, a1, b1, c1, c4, d, and R 1 are as defined in formula (I).

10. The process according to claim 7 , wherein a residual content of the at least one tertiary amine selected from the group consisting of amide amines after the reaction, as a proportion by mass (% by weight) based on the total mass of the composition, is less than 1%.

11. The process according to claim 7 , wherein the at least one tertiary amine selected from the group consisting of amide amines is a tertiary amine of formula (VII)

wherein R 8 , R 7 , R 9 , and x are as defined in formula (II).

12. The process according to claim 7 , wherein the at least one tertiary amine selected from the group consisting of dialkanolamines is a tertiary amine of formula (VIII)

wherein R 8 and R 11 are as defined in formula (III).

13. A composition obtainable by the process according to claim 7 .

14. A composition, comprising:

water, and

at least one siloxane (A) according to claim 1 or a composition comprising the at least one siloxane (A).

15. A method, comprising:

a) treating two-dimensional structures;

b) producing cleaning and care formulations for household and for industrial purposes;

c) producing cosmetic, pharmaceutical, and dermatological compositions; and/or

d) cleaning hard surfaces,

with the siloxane (A) according to claim 1 .

16. The siloxane (A) according to claim 1 , wherein

a1=0 to 12;

a2=1 to 3;

a3=1 to 2;

a4=0;

b1=10 to 400;

b2=0;

b3=0,

c1=0 to 4;

c4=0;

d=0 to 4;

R 1 =alkyl radicals having 1 to 30 carbon atoms or aromatic hydrocarbon radicals having 6 to 30 carbon atoms, wherein the alkyl radicals are linear, branched, saturated, or unsaturated;

R 21 =each independently identical or different divalent radicals selected from the group consisting of

R 4 =each independently identical or different groups, selected from the group consisting of acetoxy groups, methoxy groups, ethoxy groups, n-propoxy groups, isopropoxy groups, n-butoxy groups, tert-butoxy groups, and alkoxy groups derived from glycol radicals;

R 5 =each independently identical or different radicals selected from the group consisting of hydrogen and hydrocarbon radicals;

R 6 =each independently identical or different divalent hydrocarbon radicals optionally containing ether groups;

R 7 =—NH—;

R 8 =each independently identical or different radicals selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and tert-butyl;

R 9 =each independently identical or different hydrocarbon radicals having 1 to 30 carbon atoms;

R 11 =each independently identical or different radicals selected from the group consisting of alkyl radicals having at least one hydroxyl group and 1 to 6 carbon atoms;

m=1;

x=3; and

y=2 to 18.

17. The Siloxane (A) according to claim 16 , wherein

R 1 =methyl, ethyl, propyl, or phenyl;

R 21 =each independently identical or different divalent radicals selected from the group consisting of

R 5 =each independently identical or different radicals selected from the group consisting of alkyl radicals having 1 to 6 carbon atoms, wherein the alkyl radicals are linear, branched, saturated, or unsaturated;

R 6 =each independently identical or different divalent hydrocarbon radicals optionally containing ether groups, having 1 to 6 carbon atoms;

R 8 =each independently identical or different radicals selected from the group consisting of methyl, ethyl, n-propyl, and isopropyl;

R 9 =each independently identical or different hydrocarbon radicals having 1 to 30 carbon atoms;

R 11 =2-hydroxyethyl and/or 2-hydroxypropyl;

m=1;

y=3,

wherein for R 4 , the glycol radicals, if present, are selected from the group consisting of propylene glycol, dipropylene glycol, tripropylene glycol, hexylene glycol, pentylene glycol, and butyldiglycol.

18. The siloxane (A) according to claim 2 , wherein for condition (iv), a2≥2, a3≥1, and a4=0.

19. The composition according to claim 4 , wherein the siloxane (B) is a siloxane that differs from the siloxane (A) precisely in that the conditions (v) and (vi) are applicable rather than the conditions (i) to (ii), and wherein the siloxane (C) is a siloxane that differs from the siloxane (A) precisely in that the conditions (vii) and (viii) are applicable rather than the conditions (i) and (ii).

20. The composition according to claim 5 , wherein

a. the proportion by mass (% by weight) of the at least one siloxane (A) based on the total mass of the siloxanes is from 30% to 50%;

and/or

b. the proportion by mass (% by weight) of the at least one siloxane (B) based on the total mass of the siloxanes is from 1% to 10%;

and/or

c. the proportion by mass (% by weight) of the at least one siloxane (C) based on the total mass of the siloxanes is from 10% to 50%.

21. The composition of claim 3 , wherein the composition has a content of greater than 0% and less than 3% by weight of one or more dialkanolamines and greater than 0% and less than 1% by weight of one or more amide amines that are tertiary amines.

22. The composition of claim 3 , wherein the composition does not have a phase separation.

23. The siloxane (A) according to claim 1 , obtained by reaction of compounds comprising at least one amide amine and at least one dialkanolamine,

wherein the at least one amide amine is at least one selected from the group consisting of 3-N,N-dimethylaminopropylcocoamide, 3-N,N-dimethylaminopropylstearamide, and 3-N,N-dimethylaminopropylpalmitamide; and

wherein the at least one dialkanolamine is at least one selected from the group consisting of N-methyldiethanolamine and N-methyldiisopropanolamine.

Priority Claims (1)

Continuity (1)

References Cited (47)