Gemini surfactant and their use
View Patent ↗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.
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)—.