Gemini surfactant and their use

Patent metadata

Field	Value
Publication number	US-10106494-B2
Application number	US-201315101396-A
Country	US
Kind code	B2
Filing date	Dec 2, 2013
Priority date	Dec 2, 2013
Publication date	Oct 23, 2018
Grant date	Oct 23, 2018

Abstract

Disclosed herein are gemini surfactants, and methods for making and using these gemini surfactants. These gemini surfactants may be incorporated in paints and coatings to provide hydrophilic and/or self-cleaning properties.

First claim

What is claimed is:

1. A compound of formula I:

wherein A 1 is —H, —N[CH 2 —N + (Z—CH 3 ) 3 .X − ] 2 , —N + H 3 .X − , —N[Z—CH 3 ] 2 , —NH—CH 2 —CH 2 —OH, —N + (CH 2 —CH 2 —OH) 3 .X − , —O—Z—CH 3 , —N + [Z—CH 3 ] 3 .X − , —O—C(═O)—COO − .Na + , —N + (—CH 3 ) 2 —Z—CH 3 .X − , or salt thereof;
A 2 is —H, —N[CH 2 —N + (Z—CH 3 ) 3 .X − ] 2 , —N + H 3 .X − , —N[Z—CH 3 ] 2 , —NH—CH 2 —CH 2 —OH, —N + (CH 2 —CH 2 —OH) 3 .X − , —O—Z—CH 3 , —N + (Z—CH 3 ) 3 .X − , —O—C(═O)—COO − .Na + , —N + (—CH 3 ) 2 —Z—CH 3 .X − , or salt thereof;
A 3 is —N[CH 2 —N + (Z—CH 3 ) 3 .X − ] 2 , —N + H 3 .X − , —N[Z—CH 3 ] 2 , —NH—CH 2 —CH 2 —OH, —N + (CH 2 —CH 2 —OH) 3 .X − , —O—Z—CH 3 , —N + (Z—CH 3 ) 3 .X − , —O—C(═O)—COO − .Na + , —N + (—CH 3 ) 2 —Z—CH 3 .X − , or salt thereof;
A 4 is —N[CH 2 —N + (Z—CH 3 ) 3 .X − ] 2 , —N + H 3 .X − , —N[Z—CH 3 ] 2 , —NH—CH 2 —CH 2 —OH, —N + (CH 2 —CH 2 —OH) 3 .X − , —O—Z—CH 3 , —N + (Z—CH 3 ) 3 .X − , —O—C(═O)—COO − .Na + , —N + (—CH 3 ) 2 —Z—CH 3 .X − , or salt thereof;
each Z is, independently, C 1 -C 25 alkylene, C 1 -C 25 substituted alkylene, C 6 -C 25 arylene, C 6 -C 25 substituted arylene, C 2 -C 25 alkenylene, C 2 -C 25 substituted alkenylene, C 2 -C 25 alkynylene, C 2 -C 25 substituted alkynylene, or absent;
Q is —C(═O)—, —CH 2 —CH 2 —, —CH 2 —(CH 2 ) k —CH 2 —, —C(═O)—NH—C(═O)—, or polyurea, where k is an integer from 1 to 10; and
X is Cl, Br, F, I, or OH; and
wherein two of A 1 , A 2 , A 3 , or A 4 are hydrophilic groups selected from —H, —N[CH 2 —N + (Z—CH 3 ) 3 .X − ] 2 , —N + H 3 .X − —NH—CH 2 —CH 2 —OH, —N + (CH 2 —CH 2 —OH) 3 .X − , —N + [Z—CH 3 ] 3 .X − , —O—C(═)—COO − .Na + , —N + (—CH 3 ) 2 —Z—CH 3 .X − , or salt thereof, and other two of A 1 , A 2 , A 3 , or A 4 are hydrophobic groups selected from —N[Z—CH 3 ] 2 and —O—Z—CH 3 .

2. The compound of claim 1 , wherein A 1 is —H, —N[CH 2 —N + (Z—CH 3 ) 3 .X − ] 2 , —N + H 3 .X − , —N[Z—CH 3 ] 2 , —NH—CH 2 —CH 2 —OH, —N + (CH 2 —CH 2 —OH) 3 .X − , or —O—Z—CH 3 .

3. The compound of claim 1 , wherein A 2 is —H, —N[CH 2 —N + (Z—CH 3 ) 3 .X − ] 2 , —N + H 3 .X − , —N[Z—CH 3 ] 2 , —NH—CH 2 —CH 2 —OH, —N + (CH 2 —CH 2 —OH) 3 .X − , or —O—Z—CH 3 .

4. The compound of claim 1 , wherein A 3 is —N[CH 2 —N + (Z—CH 3 ) 3 .X − ] 2 , —N + H 3 .X − , —N[Z—CH 3 ] 2 , —NH—CH 2 —CH 2 —OH, —N + (CH 2 —CH 2 —OH) 3 .X − , or —O—Z—CH 3 .

5. The compound of claim 1 , wherein A 4 is —N[CH 2 —N + (Z—CH 3 ) 3 .X − ] 2 , —N + H 3 .X − , —N[Z—CH 3 ] 2 , —NH—CH 2 —CH 2 —OH, —N + (CH 2 —CH 2 —OH) 3 .X − , or —O—Z—CH 3 .

6. The compound of claim 1 , wherein:
A 1 is —N[Z—CH 3 ] 2 or —O—Z—CH 3 ;
A 2 is —N[Z—CH 3 ] 2 or —O—Z—CH 3 ;
A 3 is —N[CH 2 —N + (CH 3 ) 3 .Br − ] 2 or —N + (Z—CH 3 ) 3 .Br − ;
A 4 is —N[CH 2 —N + (CH 3 ) 3 .Br − ] 2 or —N + (Z—CH 3 ) 3 .Br − ; and
Q is —C(═O)— or —CH 2 —(CH 2 ) k —CH 2 —.

7. The compound of claim 1 , wherein A 1 is —N[Z—CH 3 ] 2 , A 2 is —N[Z—CH 3 ] 2 , A 3 is —N[CH 2 —N + (CH 3 ) 3 .Br − ] 2 , A 4 is —N[CH 2 —N + (CH 3 ) 3 .Br − ] 2 , and Q is —C(═)—.

8. The compound of claim 1 , wherein A 1 is —O—C(═O)—COO − .Na + , A 2 is —O—Z—CH 3 , A 3 is —O—C(═O)—COO − .Na + , A 4 is —O—Z—CH 3 , and Q is —C(═O)—.

9. The compound of claim 1 , wherein A 1 is —N + (Z—CH 3 ) 3 .Br − , A 2 is —O—Z—CH 3 , A 3 is —N + (Z—CH 3 ) 3 .Br − , A 4 is —O—Z—CH 3 , and Q is —C(═O)—.

Assignees

• Empire Technology Dev Llc

Inventors

• Adam Georgius Abidal

Classifications

• C07C275/14 Primary

  being further substituted by nitrogen atoms not being part of nitro or nitroso groups · CPC title

• C07C217/32

  the six-membered aromatic ring or condensed ring system containing that ring being further substituted · CPC title

• C07C217/58

  with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain · CPC title

• C07C215/14

  the nitrogen atom of the amino group being further bound to hydrocarbon groups substituted by amino groups · CPC title

• C07C273/1854

  by reactions not involving the formation of the N-C(O)-N- moiety · CPC title