Nanotextured surfaces
The invention describes novel compositions that include a cross linking compound, a polymer and a 1 nm to about a 25 micron sized particle optionally with an oxide layer. In particular, the particle is a silica and one which has been pretreated with a silane.
1. A composition comprising a cross linking compound of formula:
L-(D-T-C(R 1 )(XP)CHR 2 GR 3 C(═O)R 4 ) m
wherein
L is a linking group comprising
a formula according to structure (I):
A, B and J form a ring, wherein A and J are C═O;
B is NR 11 ;
R 11 is a hydrogen atom, an alkyl group, an aryl group or denotes a bond with T;
D is CR 6 R 7 ;
T is (—CH 2 —) x , (—CH 2 CH 2 —O—) x , (—CH 2 CH 2 CH 2 —O—) x or (—CH 2 CH 2 CH 2 CH 2 —O—) x or forms a bond;
R 1 is a hydrogen atom, an alkyl, alkyloxyalkyl, aryl, aryloxyalkyl or aryloxyaryl group;
X is O, S, or NR 8 R 9 ;
P is a hydrogen atom or a protecting group, with the proviso that P is absent when X is NR 8 R 9 ;
R 2 is a hydrogen atom, an alkyl, alkyloxyalkyl, aryl, aryloxyalkyl or aryloxyaryl group;
G is —C(═O)O—, —O—, —NHC(═O)O—, —NHC(═O)S—, —SO 2 —, —CONH—, —NHCONH—, —NHC(═S)NH—, —NR 10 —, —SO 2 NH—, —C(═N)—,—C(═O)— or —(CH 2 ) t —O—;
R 3 and R 4 are each independently an alkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl group, wherein R 3 and R 4 can be tethered together via (—CH 2 —) q , (—CH 2 —) r C═O(—CH 2 —) s , (—CH 2 —) r S(—CH 2 —) s , (—CH 2 —) r S═O(—CH 2 —) s or (—CH 2 —) r S(O) 2 (—CH 2 —) s , (—CH 2 —) r NR(—CH 2 —) s ;
R 10 is a hydrogen atom or an alkyl, aryl or arylalkyl group;
R 6 and R 7 are each independently a hydrogen atom, an alkyl, aryl, arylalkyl, heteroaryl or heteroarylalkyl group;
R 8 and R 9 are each independently a hydrogen atom, an alkyl, aryl, or arylalkyl group;
R is a hydrogen atom, an alkyl or an aryl group;
q is an integer from 1 to about 7;
r is an integer from 0 to about 3;
s is an integer from 0 to about 3;
m is an integer from 2 to about 10;
t is an integer from 1 to about 10; and
x is an integer from 1 to about 500;
a polymer; and
a particle having a particle size of between about 1 nm to about 25 microns.
2. A composition comprising a cross linking compound of formula:
L-(T-C(R 1 )(XP)CHR 2 GR 3 C(═O)R 4 ) m
wherein L is a linking group comprising
a formula according to structure (I):
A, B and J form a ring, wherein A and J are C═O;
B is NR 11 ;
R 11 is a hydrogen atom, an alkyl group, an aryl group or denotes a bond with T;
T is (—CH 2 —) x , (—CH 2 CH 2 —O—) x , (—CH 2 CH 2 CH 2 O—) x or (—CH 2 CH 2 CH 2 CH 2 —O—) x or forms a bond;
R 1 is a hydrogen atom, an alkyl, alkyloxyalkyl, aryl, aryloxyalkyl or aryloxyaryl group;
X is O, S, or NR 8 R 9 ;
P is a hydrogen atom or a protecting group, with the proviso that P is absent when X is NR 8 R 9 ;
R 2 is a hydrogen atom, an alkyl, alkyloxyalkyl, aryl, aryloxyalkyl or aryloxyaryl group;
G is —C(═O)O—, —O—, —NHC(═O)O—, —NHC(═O)S—, —SO 2 —, —CONH—, —NHCONH—, —NHC(═S)NH—, —NR 10 —, —SO 2 NH—, —C(═N)—,—C(═O)— or —(CH 2 ) t —O—;
R 3 and R 4 are each independently an alkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl group, wherein R 3 and R 4 can be tethered together via (—CH 2 —) q , (—CH 2 —) r C═O(—CH 2 —) s , (—CH 2 —) r S(—CH 2 —) s , (—CH 2 —) r S═O(—CH 2 —) s or (—CH 2 —) r S(O) 2 (—CH 2 —) s , (—CH 2 —) r NR(—CH 2 —) s ;
R 10 is a hydrogen atom or an alkyl, aryl or arylalkyl group;
R 8 and R 9 are each independently a hydrogen atom, an alkyl, aryl, or arylalkyl group;
R is a hydrogen atom, an alkyl or aryl group;
q is an integer from 1 to about 7;
r is an integer from 0 to about 3;
s is an integer from 0 to about 3;
m is an integer from 2 to about 10;
t is an integer from 1 to about 10; and
x is an integer from 1 to about 500;
a polymer; and
a particle having a particle size between about 1 nm to about 25 microns.
3. A composition comprising a cross linking compound of formula:
L-(GTZR 3 C(═O)R 4 ) m
wherein
L is a linking group comprising
a formula according to structure (I):
A, B and J form a ring, wherein A and J are C═O;
B is NR 11 ;
R 11 is a hydrogen atom, an alkyl group, an aryl group or denotes a bond;
T is (—CH 2 —) x , (—CH 2 CH 2 —O—) x , (—CH 2 CH 2 CH 2 —O—) x , (—CH 2 CH 2 CH 2 CH 2 —O—) x or forms a bond;
G is —C(═O)O—, —NHC(═O)O—, —NHC(═O)S—, —CONH—, —NHCONH—, —NHC(═S)NH—, —C(═N)—, —C(═O)— or —(CH 2 ) t —O—;
Z is C═O, COO, or CONH when T is (—CH 2 —) x ;
R 3 and R 4 are each independently an alkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl group, wherein R 3 and R 4 can be tethered together via (—CH 2 —) q , (—CH 2 —) r C═O(—CH 2 —) s , (—CH 2 —) r S(—CH 2 —) s , (—CH 2 —) r S═O(—CH 2 —) s or (—CH 2 —) r S(O) 2 (—CH 2 —) s , (—CH 2 —) r NR(—CH 2 —) s ;
R is a hydrogen atom or an alkyl or aryl group;
q is an integer from 1 to about 7;
r is an integer from 0 to about 3;
s is an integer from 0 to about 3;
m is an integer from 2 to about 10;
t is an integer from 1 to about 10; and
x is an integer from 1 to about 500;
a polymer; and
a particle having a particle size of between about 1 nm to about 25 microns.
4. A composition comprising a cross linking compound of formula:
L-(TGQR 3 C(═O)R 4 ) m
wherein
L is a linking group comprising
a formula according to structure (I):
A, B and J form a ring, wherein A and J are C═O;
B is NR 11 ;
R 11 is a hydrogen atom, an alkyl group, an aryl group or denotes a bond with T;
T is (—CH 2 —) x , (—CH 2 CH 2 —O—) x , (—CH 2 CH 2 CH 2 —O—) x , (—CH 2 CH 2 CH 2 CH 2 —O—) x or forms a bond;
G is —C(═O)O—, —O—, —NHC(═O)O—, —NHC(═O)S—, —SO 2 —, —CONH—, —NHCONH—, —NHC(═S)NH—, —NR 10 —, —SO 2 NH—, —C(═N)—,—C(═O)— or —(CH 2 ) t —O—;
Q is (—CH 2 —) p , (—CH 2 CH 2 —O—) p , (—CH 2 CH 2 CH 2 —O—) p or (—CH 2 CH 2 CH 2 CH 2 —O—) p ;
R 3 and R 4 are each independently an alkyl, aryl, arylalkyl, heteroaryl, or a heteroarylalkyl group, wherein R 3 and R 4 can be tethered together via (—CH 2 —) q , (—CH 2 —) r C═O(—CH 2 —) s , (—CH 2 —) r S(—CH 2 —) s , (—CH 2 —) r S═O(—CH 2 —) s or (—CH 2 —) r S(O) 2 (—CH 2 —) s , (—CH 2 —) r NR(—CH 2 —) s ;
R 10 is a hydrogen atom or an alkyl, aryl, or an arylalkyl group;
R is a hydrogen atom or an alkyl or aryl group;
q is an integer from 1 to about 7;
r is an integer from 0 to about 3;
s is an integer from 0 to about 3;
m is an integer from 2 to about 10;
p is an integer from 1 to about 10;
t is an integer from 1 to about 10; and
x is an integer from 1 to about 500;
a polymer; and
a particle having a particle size of between about 1 nm to about 25 microns.
5. A composition comprising a cross linking compound of formula:
L-(—CH 2 —) xx C(R 1 )(GR 3 C(═O)R 4 ) m
wherein
L is a linking group comprising
a formula according to structure (I):
A, B and J form a ring, wherein A and J are C═O;
B is NR 11 ;
R 11 is a hydrogen atom, an alkyl group, an aryl group or denotes a bond;
R 1 is a hydrogen atom, an alkyl, alkyloxyalkyl, aryl, aryloxyalkyl, or aryloxyaryl group;
G is —C(═O)O—, —O—, —NHC(═O)O—, —NHC(═O)S—, —SO 2 —, —CONH—, —NHCONH—, —NHC(═S)NH—, —NR 10 —, —SO 2 NH—, —C(═N)—,—C(═O)— or —(CH 2 ) t —O—;
each R 3 and R 4 are each independently an alkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl group, wherein R 3 and R 4 can be tethered together via (—CH 2 —) q , (—CH 2 —) r C═O(—CH 2 —) s , (—CH 2 —) r S(—CH 2 —) s , (—CH 2 —) r S═O(—CH 2 —) s or (—CH 2 —) r S(O) 2 (—CH 2 —) s , (—CH 2 —) r NR(—CH 2 —) s ;
each R 10 is a hydrogen atom or an alkyl, aryl, or an arylalkyl group;
each R is a hydrogen atom or an alkyl or aryl group;
each q is an integer from 1 to about 7;
each r is an integer from 0 to about 3;
each s is an integer from 0 to about 3;
m is an integer from 2 to about 10;
each t is an integer from 1 to about 10; and
xx is an integer from 1 to about 10;
a polymer; and
a particle having a particle size of between about 1 nm to about 25 microns.
6. A composition comprising a cross linking compound of formula:
L-C(R 1 )(XP)CHR 2 GR 3 C(═O)R 4 ) m
wherein
L is a linking group comprising
a formula according to structure (I):
A, B and J form a ring, wherein A and J are C═O;
B is NR 11 ;
R 11 is a hydrogen atom, an alkyl group, an aryl group or denotes a bond;
R 1 is a hydrogen atom, an alkyl, alkyloxyalkyl, aryl, aryloxyalkyl or aryloxyaryl group;
X is O, S, or NR 8 R 9 ;
P is a hydrogen atom or a protecting group, with the proviso that P is absent when X is NR 8 R 9 ;
R 2 is a hydrogen atom, an alkyl, alkyloxyalkyl, aryl, aryloxyalkyl or aryloxyaryl group;
G is —C(═O)O—, —O—, —NHC(═O)O—, —NHC(═O)S—, —SO 2 —, —CONH—, —NHCONH—, —NHC(═S)NH—, —NR 10 —, —SO 2 NH—, —C(═N)—,—C(═O)— or —(CH 2 ) t —O—;
R 3 and R 4 are each independently an alkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl group, wherein R 3 and R 4 can be tethered together via (—CH 2 —) q , (—CH 2 —) r C═O(—CH 2 —) s , (—CH 2 —) r S(—CH 2 —) s , (—CH 2 —) r S═O(—CH 2 —) s or (—CH 2 —) r S(O) 2 (—CH 2 —) s , (—CH 2 —) r NR(—CH 2 —) s ;
R 8 and R 9 are each independently a hydrogen atom, an alkyl, aryl, or arylalkyl group;
R 10 is a hydrogen atom or an alkyl, aryl, or an arylalkyl group;
R is a hydrogen atom, an alkyl or an aryl group;
q is an integer from 1 to about 7;
r is an integer from 0 to about 3;
s is an integer from 0 to about 3;
m is an integer from 2 to about 10; and
t is an integer from 1 to about 10;
a polymer; and
a particle having a particle size of between about 1 nm to about 25 microns.
7. A composition comprising a cross linking compound of formula:
L-(GR 3 C(═O)R 4 ) m ;
wherein
L is a linking group comprising
a formula according to structure (I):
A, B and J form a ring, wherein A and J are C═O;
B is NR 11 ;
R 11 is a hydrogen atom, an alkyl group, an aryl group or denotes a bond;
G is —C(═O)O—, —NHC(═O)O—, —NHC(═O)S—, —CONH—, —NHCONH—, —NHC(═S)NH—, —C(═N)—, —C(═O)— or —(CH 2 ) t —O—;
R 3 and R 4 are each independently an alkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl group, wherein R 3 and R 4 can be tethered together via (—CH 2 —) q , (—CH 2 —) r C═O(—CH 2 —) s , (—CH 2 —) r S(—CH 2 —) s , (—CH 2 —) r S═O(—CH 2 —) s or (—CH 2 —) r S(O) 2 (—CH 2 —) s , (—CH 2 —) r NR(—CH 2 —) s ;
R is a hydrogen atom, an alkyl or an aryl group;
q is an integer from 1 to about 7;
r is an integer from 0 to about 3;
s is an integer from 0 to about 3;
m is an integer from 2 to about 10; and
t is an integer from 1 to about 10;
a polymer; and
a particle having a particle size of between about 1 nm to about 25 microns.
8. A composition comprising a cross linking compound of formula:
L-(ZZ-D-T-C(R 1 )(XP)CHR 2 GR 3 C(═O)R 4 ) m
wherein
L is a linking group comprising
a formula according to structure (I):
A, B and J form a ring, wherein A and J are C═O;
B is NR 11 ;
R 11 is a hydrogen atom, an alkyl group, an aryl group or denotes a bond with T;
ZZ is a phenyl group;
D is CR 6 R 7 ;
T is (—CH 2 —) x , (—CH 2 CH 2 —O—) x , (—CH 2 CH 2 CH 2 —O—) x or (—CH 2 CH 2 CH 2 CH 2 —O—) x ;
R 1 is a hydrogen atom, an alkyl, alkyloxyalkyl, aryl, aryloxyalkyl or aryloxyaryl group;
X is O, S, or NR 8 R 9 ;
P is a hydrogen atom or a protecting group, with the proviso that P is absent when X is NR 8 R 9 ;
R 2 is a hydrogen atom, an alkyl, alkyloxyalkyl, aryl, aryloxyalkyl or aryloxyaryl group;
G is —C(═O)O—, —O—, —NHC(═O)O—, —NHC(═O)S—, —SO 2 —, —CONH—, —NHCONH—, —NHC(═S)NH—, —NR 10 —, —SO 2 NH—, —C(═N)—,—C(═O)— or —(CH 2 ) t —O—;
R 3 and R 4 are each independently an alkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl group, wherein R 3 and R 4 can be tethered together via (—CH 2 —) q , (—CH 2 —) r C═O(—CH 2 —) s , (—CH 2 —) r S(—CH 2 —) s , (—CH 2 —) r S═O(—CH 2 —) s or (—CH 2 —) r S(O) 2 (—CH 2 —) s , (—CH 2 —) r NR(—CH 2 —) s ;
R 10 is a hydrogen atom or an alkyl, aryl or arylalkyl group;
R 6 and R 7 are each independently a hydrogen atom, an alkyl, aryl, arylalkyl, heteroaryl or heteroarylalkyl group;
R 8 and R 9 are each independently a hydrogen atom, an alkyl, aryl, or arylalkyl group;
R is a hydrogen atom, an alkyl or an aryl group;
q is an integer from 1 to about 7;
r is an integer from 0 to about 3;
s is an integer from 0 to about 3;
m is an integer from 2 to about 10;
t is an integer from 1 to about 10; and
x is an integer from 1 to about 500;
a polymer; and
a particle having a particle size of between about 1 nm to about 25 microns.
9. A super hydrophobic composition comprising a photoreactive cross linking compound comprising a triazine the formula:
L-(D-T-C(R 1 )(XP)CHR 2 GR 3 C(═O)R 4 ) m as claimed in claim 1 , a polymer and a particle having a particle size of between about 1 nm to 25 microns.
10. An ultra hydrophobic composition comprising a photoreactive cross linking compound comprising a triazine the formula:
L-(D-T-C(R 1 )(XP)CHR 2 GR 3 C(═O)R 4 ) m as claimed in claim 1 , a polymer and a particle having a particle size of between about 1 nm to 25 microns.
11. A composition comprising a crosslinking compound of formula:
a polymer; and
a particle having a particle size of between about 1 nm to about 25 microns.
12. A super hydrophobic composition comprising a photoreactive cross linking compound comprising the formula:
L-(T-C(R 1 )(XP)CHR 2 GR 3 C(═O)R 4 ) m as claimed in claim 2 , a polymer and a particle having a particle size of between about 1 nm to 25 microns.
13. An ultra hydrophobic composition comprising a photoreactive cross linking compound comprising the formula:
L-(T-C(R 1 )(XP)CHR 2 GR 3 C(═O)R 4 ) m as claimed in claim 2 , a polymer and a particle having a particle size of between about 1 nm to 25 microns.
14. A super hydrophobic composition comprising a photoreactive cross linking compound comprising the formula:
L-(GTZR 3 C(═O)R 4 ) m as claimed in claim 3 , a polymer and a particle having a particle size of between about 1 nm to 25 microns.
15. An ultra hydrophobic composition comprising a photoreactive cross linking compound comprising the formula:
L-(GTZR 3 C(═O)R 4 ) m as claimed in claim 3 , a polymer and a particle having a particle size of between about 1 nm to 25 microns.
16. A super hydrophobic composition comprising a photoreactive cross linking compound comprising the formula:
L-(TGQR 3 C(═O)R 4 ) m as claimed in claim 4 , a polymer and a particle having a particle size of between about 1 nm to 25 microns.
17. An ultra hydrophobic composition comprising a photoreactive cross linking compound comprising the formula:
L-(TGQR 3 C(═O)R 4 ) m as claimed in claim 4 , a polymer and a particle having a particle size of between about 1 nm to 25 microns.
18. A super hydrophobic composition comprising a photoreactive cross linking compound comprising the formula:
L-(—CH 2 —) xx C(R 1 )(GR 3 C(═O)R 4 ) m as claimed in claim 5 , a polymer and a particle having a particle size of between about 1 nm to 25 microns.
19. An ultra hydrophobic composition comprising a photoreactive cross linking compound comprising the formula:
L-(—CH 2 —) xx C(R 1 )(GR 3 C(═O)R 4 ) m as claimed in claim 5 , a polymer and a particle having a particle size of between about 1 nm to 25 microns.
20. A super hydrophobic composition comprising a photoreactive cross linking compound comprising the formula:
L-(—C(R 1 )(XP)CHR 2 GR 3 C(═O)R 4 ) m as claimed in claim 6 , a polymer and a particle having a particle size of between about 1 nm to 25 microns.
21. An ultra hydrophobic composition comprising a photoreactive cross linking compound comprising the formula:
L-(—C(R 1 )(XP)CHR 2 GR 3 C(═O)R 4 ) m as claimed in claim 6 , a polymer and a particle having a particle size of between about 1 nm to 25 microns.
22. A super hydrophobic composition comprising a photoreactive cross linking compound comprising the formula:
L-(GR 3 C(═O)R 4 ) m as claimed in claim 7 , a polymer and a particle having a particle size of between about 1 nm to 25 microns.
23. An ultra hydrophobic composition comprising a photoreactive cross linking compound comprising the formula:
L-(GR 3 C(═O)R 4 ) m as claimed in claim 7 , a polymer and a particle having a particle size of between about 1 nm to 25 microns.
24. A super hydrophobic composition comprising a photoreactive cross linking compound comprising the formula:
L-(ZZ-D-T-C(R 1 )(XP)CHR 2 GR 3 C(═O)R 4 ) m as claimed in claim 8 , a polymer and a particle having a particle size of between about 1 nm to 25 microns.
25. An ultra hydrophobic composition comprising a photoreactive cross linking compound comprising the formula:
L-(ZZ-D-T-C(R 1 )(XP)CHR 2 GR 3 C(═O)R 4 ) m as claimed in claim 8 , a polymer and a particle having a particle size of between about 1 nm to 25 microns.