Molecules having one hydrophobic group and two identical hydrophilic ionic groups and compositions thereof and methods of preparation thereof
A novel class of compounds is described here. The disclosed novel compounds have one hydrophilic group and two identical hydrophilic ionic groups. The two hydrophilic groups of the disclosed compounds contain or end with a cationic or anionic charged group. The disclosed novel compounds herein can be used as surfactants in an article, product, or composition, or for some other purposes. A method to synthesize the disclosed novel compounds is also described.
1. A compound according to Formula I:
wherein,
X is NH or O;
R 11 is R 1 —Z—(CH 2 ) m —;
R 1 is an unsubstituted or substituted linear or branched C 5 -C 30 alkyl, cyclic alkyl, alkenyl, or alkynyl group;
Z is O;
R 2 is H, CH 3 , or an unsubstituted linear or branched C 2 -C 10 alkyl, alkenyl, or alkynyl group;
m is an integer of 1 to 4;
R 3 is absent, an unsubstituted linear C 1 -C 30 alkylene group, or C(CH 3 ) 2 ;
Y is —NR 4 R 5 R 6(+) , or a salt thereof; and
R 4 and R 5 are independently a C 1 -C 10 alkyl group, and R 6 is a C 1 -C 10 alkyl, aryl, or is —CH 2 -C 6 H 5 .
2. The compound according to claim 1 , wherein X is NH.
3. The compound according to claim 1 , wherein X is O.
4. The compound of claim 1 , wherein R 1 is the unsubstituted or substituted linear C 5 -C 30 alkyl, alkenyl, or alkynyl group.
5. The compound of claim 1 , wherein R 2 is H or CH 3 .
6. The compound of claim 1 , wherein Y is —NR 4 R 5 R 6(+) , N(CH 3 ) 3 + , or N(CH 3 ) 2 R 6+ .
7. The compound of claim 1 , wherein R 3 is C(CH 3 ) 2 or the unsubstituted linear C 2 -C 10 alkylene group.
8. The compound of claim 1 , wherein R 1 is the unsubstituted or substituted C 5 -C 30 alkenyl group with at least one trans or cis double bond.
9. A method to synthesize the compound according to claim 1 , comprising:
contacting a primary amine with an activated olefin having a cationic group to generate a compound;
wherein the primary amine is R 11 —NH 2 ; and
wherein the activated olefin is
wherein,
X is NH or O;
R 11 is R 1 —Z—(CH 2 ) m —;
R 1 is an unsubstituted or substituted linear or branched C 5 -C 30 alkyl, cyclic alkyl, alkenyl, or alkynyl group;
Z is O;
R 2 is H, CH 3 , or an unsubstituted linear or branched C 2 -C 10 alkyl, alkenyl, or alkynyl group;
m is an integer of 1 to 4;
R 3 is absent, an unsubstituted linear C 1 -C 30 alkylene group, or C(CH 3 ) 2 ;
Y is —NR 4 R 5 R 6(+) , or a salt thereof; and
R 4 and R 5 are independently a C 1 -C 10 alkyl group, and R 6 is a C 1 -C 10 alkyl, aryl, or is —CH 2 —C 6 H 5 .
10. The method of claim 9 , wherein the contacting step is done in the presence of a reaction solvent, of a reaction solvent and alkalinity source, of a reaction solvent and acid, or of a reaction solvent and a catalyst.
11. The method of claim 10 , wherein the reaction solvent is water, methanol, ethanol, propanol, glycol, PEG, or a mixture thereof.
12. The method of claim 9 , wherein the contacting step is done in the presence of benzyltrimethylammonium hydroxide.
13. An article, product, or composition comprising one or more compounds according to Formula I:
wherein,
X is NH or O;
R 11 is R 1 —Z—(CH 2 ) m —;
R 1 is an unsubstituted or substituted, linear or branched C 5 -C 30 alkyl, cyclic alkyl, alkenyl, or alkynyl group;
Z is O;
R 2 is H, CH 3 , or an unsubstituted, linear or branched C 2 -C 10 alkyl, alkenyl, or alkynyl group;
m is an integer of 1 to 4;
R 3 is absent, an unsubstituted linear C 1 -C 30 alkylene group, or C(CH 3 ) 2 ;
Y is —NR 4 R 5 R 6 (+) or a salt thereof; and
R 4 and R 5 are independently a C 1 -C 10 alkyl group, and R 6 is a C 1 -C 10 alkyl, aryl, or is —CH 2 —C 6 H 5 .
14. The article, product, or composition of claim 13 , wherein the article, product or composition further comprises a carrier solvent and is an aqueous article, product, or composition.
15. The article, product, or composition of claim 14 , wherein the carrier solvent is water, an alcohol, an alkylene glycol, an alkylene glycol alkyl ether, or a combination thereof.
16. The article, product, or composition of claim 13 , wherein the article, product, or composition further comprises a primary alkalinity source and is a detergent composition.
17. The article, product, or composition of claim 16 , wherein the article, product, or composition further comprises a chelant.
18. The article, product, or composition of claim 16 , wherein the article, product, or composition further comprises an enzyme.
19. The article, product, or composition of claim 16 , wherein the article, product, or composition further comprises an additional detergent composition agent.
20. The article, product, or composition of claim 13 , further comprising an additional surfactant, wherein the additional surfactant is a nonionic, semi-nonionic, cationic, anionic, amphoteric, zwitterionic, Gemini, surfactant or mixtures thereof.