Photochemical crosslinkers for polymer coatings and substrate tie-layer
The invention describes novel crosslinking compounds that include photoactivatable moieties. Several families of compounds are disclosed that can include one or more hydrophilic moieties that help to solubilize the compounds in aqueous environments.
1. A compound of formula:
L-((T-C(R 1 )(XP 1 )CHR 2 GR 3 C(═O)R 4 )) m wherein L is (—OCH 2 CH 2 O—) qq , (—OCH 2 CH 2 CH 2 O—) qq , (—O—(CH 2 ) ii —O—) qq , (—OCH 2 —CH(OP 2 )—CH 2 —O—) qq or (—O(CH 2 ) ii —O—(CH 2 ) jj —O—) qq ;
T is (—CH 2 —) 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 1 is a hydrogen atom or a protecting group, with the proviso that P 1 is absent when X is NR 8 R 9 ;
P 2 is a hydrogen atom or a protecting group;
R 2 is a hydrogen atom, an alkyl, alkyloxyalkyl, aryl, aryloxyalkyl or aryloxyaryl group;
G is 0, S, SO, SO 2 , NR 10 , (CH 2 ) t —O— or C═O;
R 3 and R 4 are aryl,
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;
ii is an integer from 1 to about 500;
jj is an integer from 1 to about 500;
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;
x is an integer from 1 to about 500; and
qq is an integer from 1 to about 500.
2. The compound of claim 1 , wherein R 1 is H, X is O, P 1 is H, P 2 is H, R 2 is H, G is O, m is 2, x is an integer from 1 to 10 and qq is an integer from 1 to about 10.
3. The compound of claim 1 , wherein L is diethylene glycol.
4. The compound of claim 1 , wherein L is tetraethylene glycol.
5. The compound of claim 1 , wherein L is hexaethylene glycol.
6. A method to modify a substrate comprising the step of applying a compound of formula:
L-4T-C(R 1 )(XP 1 )CHR 2 GR 3 C(═O)R 4 )) m of claim 1 to the surface of the substrate, such that the substrate surface is modified.
7. The method of claim 6 , wherein the compound is photoactivated such that at least one photoactivatable group within the compound forms a bond with the surface of the substrate.
8. The method of claim 6 , wherein L comprises diethylene glycol, tetraethylene glycol, or hexaethylene glycol.
9. The compound of claim 1 , wherein P 1 or P 2 or both are either hydrogen or alkyl groups.
10. The compound of claim 9 , wherein P 1 or P 2 or both are ethyl or methyl groups.
11. A compound of formula:
L-(D-CH 2 CH(OH)CH 2 GR 3 C(═O)R 4 ) m
wherein L is a C2 to a C6 alkyl linking group;
D is O;
G is O;
R 3 and R 4 are aryl; and
m is an integer from 2 to about 10.
12. The compound of claim 11 , wherein L is
13. The compound of claim 11 , wherein L is (—CH 2 —) y and y is an integer from 2 to 6.
14. A method to modify a substrate comprising the step of applying a compound comprising a formula:
L-(D-CH 2 CH(OH)CH 2 GR 3 C(═O)R 4 ),
wherein L is a C2 to a C6 alkyl linking group;
D is O;
G is O;
R 3 and R 4 are aryl; and
m is an integer from 2 to about 10, to the surface of a substrate, such that the substrate surface is modified.
15. A method to modify the substrate according to claim 14 , wherein L is
16. A method to modify the substrate according to claim 14 , wherein L is (—CH 2 —) y and y is an integer from 2 to 6.
17. The method of claim 14 , wherein the compound is photoactivated such that at least one photoactivatable group within the compound forms a bond with the surface of the substrate.