Surface primer compositions and methods of use
In one embodiment, the present application discloses a surface binding compound of the Formula I or Formula II: wherein the variables EG, EG1, SP1, SP2, SP3, Ar and BG are as defined herein. In another embodiment, the application discloses a method for forming a coating on a surface of a substrate using the surface binding compound of the Formula I or Formula II.
1. A surface binding compound of the Formula I:
wherein:
each a is independently 1, 2, or 3;
m is 1, or 2;n is 1, or 2; i is 1, 2 or 3;
each EG is an end group independently selected from the group consisting of a C 1-12 alkyl, CH 2 ═CHC(O)O—, CH 2 ═C(C 1-3 alkyl)C(O)O—, isocyanate, epoxy, —N + R 1 R 2 R 3 , and —PO 4 − , wherein each R 1 , R 2 and R 3 is independently H and C 1-3 alkyl, X − is Cl − , Br − and I − and Y + is H + or N + R 1 R 2 R 3 ;
each of SP1, SP2 and SP3 is a spacer independently selected from the group consisting of —O—, —C(O)—, —N—, —NH—,—NCH 3 —, —C—, —CH—, —(CH 2 ) q —, —OC(O)—, —CO 2 —,—NHCH 2 C(O)—, —NHC(O)—, —C(O)NH—, —NCH 3 C(O)—, —C(O)NCH 3 —, —(CH 2 CH 2 O) p —, —(CH 2 ) q —N + R 1 R 2 —, —(CH 2 ) q —PO 4 − —, —N + R 1 R 2 —, —PO 4 −—, —(CH 2 ) q —N + R 1 R 2 —X − —, —(CH 2 ) q —PO 4 − Y + —, —N + R 1 R 2 —X − —, —PO 4 − Y + —, —O—PO − (O)O—(CH 2 ) 2-4 —N + (R 1 R 2 )—, aryl, p is 1-6, and q is 1-6;
Ar is an aryl group;
each BG is a bonding group independently selected from the group consisting of —OH, —Si(R) 2 OH, —COOH, —SO 3 H, and —P(O) 3 OH, wherein each R is independently H and C 1-3 alkyl;
provided that when —SP3 is —CH 2 — or —C(O)—, then Ar-(BG) a is not 3,4-dihydroxyphenyl or 3,4-dicarboxyphenyl.
2. A surface binding compound of the Formula II:
wherein:
m is 1, or 2; n is 1, or 2; i is 1, 2 or 3;
each EG and EG1 is an end group independently selected from the group consisting of a CH 2 ═CH—, CH 2 ═C(C 1-3 alkyl)—, CH 2 ═CHC(O)—, CH 2 ═C(C 1-3 alkyl)C(O)—, CH 2 ═CHC(O)O—, CH 2 ═C(C 1-3 alkyl)C(O)O—, —N + R 1 R 2 R 3 , —PO 4 31 , wherein each R, R 1 , R 2 and R 3 is independently H and C 1-3 alkyl or optionally substituted C 1-3 alkyl, − and Y + is H + or N + R 1 R 2 R 3 ;
each of SP1, SP2 and SP3 is a spacer independently selected from the group consisting of —O—, —C(O)—, —N—, —NH—, —NCH 3 —, —C—, —CH—, —(CH 2 ) q —, —(CH(OH)) q —, —(CH 2 CH(OH)CH 2 ) q —, —(C(CH 3 ) 2 ) q —, —(CH(CH 3 )) q —, —OC(O)—, —CO 2 —, —NHCH 2 CH 2 C(O)—, —OCH 2 CH 2 C(O)—, —C(O)CH 2 CH 2 C(O)—, —NHC(O)—, —C(O)NH—, —NCH 3 C(O)—, —C(O)NCH 3 —, —(CH 2 CH 2 O) p —, —(CH 2 ) q —N + R 1 R 2 —, —(CH 2 ) q —PO 4 − —, —N + R 1 R 2 —, —PO 4 31 —, —(CH 2 ) q —N + R 1 R 2 —X − —, —(CH 2 ) q —PO 4 − Y + —, —N + R 1 R 2 —X − —, —PO 4 − Y + —, —O—PO − (O)O—(CH 2 ) 2-4 —N + (R 1 R 2 )—, p is 1-6, and q is 1-6.
3. The surface binding compound of claim 1 , wherein each EG is independently selected from the group consisting of a CH 2 ═CHC(O)O—, CH 2 ═C(C 1-3 alkyl)C(O)O—, CH 2 ═C(phenyl)C(O)O—, CH 2 ═CHS(O) n O—, isocyanate, epoxy, oxetanyl, styrenyl, and vinyl ether.
4. The surface binding compound of claim 1 , wherein each EG is independently selected from the group consisting of —N + R 1 R 2 R 3 , —PO 4 − , wherein each R 1 , R 2 and R 3 is independently H and C 1-3 alkyl and C 1-3 alkyl substituted with 1, 2 or 3 —OH, 1, 2 or 3 —SH or 1, 2 or 3 —NH 2 , X − is Cl − , Br − and I − and Y + is H + or —N + R 1 R 2 R 3 .
5. The surface binding compound of claim 1 , wherein each of SP1, SP2 and SP3 is a spacer independently selected from the group consisting of —(CH 2 ) q —, —NHCH 2 C(O)—, —NHC(O)—, —C(O)NH—, —NCH 3 C(O)—, —C(O)NCH 3 —, and —(CH 2 CH 2 O) p —.
6. The surface binding compound of claim 1 , wherein each of SP1, SP2 and SP3 is a spacer independently selected from the group consisting of —N + R 1 R 2 —, —PO 4 − —, —N + R 1 R 2 X − —, —PO 4 31 Y + —, —(CH 2 ) q —N + R 1 R 2 —, —(CH 2 ) q —PO 4 − —, —(CH 2 ) q —N + R 1 R 2 —X − —, —(CH 2 ) q —PO 4 − Y + — and —O—PO − (O)O—(CH 2 ) 2-4 —N + (R 1 R 2 )—.
7. The surface binding compound of claim 1 , wherein SP1, SP2 and SP3 comprise of a group selected from —CH 2 CH 2 —C(O)NHCH 2 CH 2 NH—C(O)NCH 3 —, —NHC(O)—(CH 2 CH 2 O) p —(CH 2 ) q —, —(CH 2 CH 2 O) p CH 2 CH 2 —C(O)NCH 3 —(CH 2 CH 2 O) p CH 2 CH 2 —, —NHCH 2 CH 2 C(O)—(CH 2 ) q —PO 4 − —, —PO 4 − —(CH 2 ) q —N + R 1 R 2 X − —, —(CH 2 CH 2 O) p —(CH 2 ) q —PO 4 − , —N + R 1 R 2 X − —(CH 2 ) q —PO 4 − and —PO 4 − —(CH 2 CH 2 O) p —N + R 1 R 2 X − —.
8. The surface binding compound of any one of claim 1 , wherein Ar is an aryl group selected from the group consisting of:
9. The surface binding compound of claim 1 , wherein Ar is an aryl group selected from the group consisting of:
10. The surface binding compound of claim 1 , wherein Ar is an aryl group selected from the group consisting of:
11. The surface binding compound of claim 1 , wherein Ar is an aryl group selected from the group consisting of:
12. The surface binding compound of claim 1 , wherein Ar is an aryl group selected from the group consisting of:
13. The surface binding compound of claim 1 , wherein each BG is a bonding group independently selected from the group consisting of —OH, —Si(R) 2 OH, —COOH, —SO 3 H, and —P(O) 3 OH.
14. The surface binding compound of claim 1 , wherein —SP3— is —CH 2 —and Ar-(BG) a is selected from the group consisting of 2,3-dihydroxyphenyl,2,3,4-trihydroxyphenyl 3,4,5-trihydroxyphenyl, 2,3,4,5-tetrahydroxyphenyl, 2,3,4,5,6-pentahydroxyphenyl, and 2,3-dicarboxyphenyl.
15. The surface binding compound of claim 1 , wherein each EG is an aryl group independently selected from the group consisting of:
wherein the aryl group is optionally substituted by 1 or 2 substituents selected from halo, CF 3 —, CF 3 O—, CH 3 O—, —C(O)OH, —C(O)OC 1-3 alkyl, —C(O)CH 3 , —CN, —NH 2 , —OH, —Si(R) 2 OH, —NHCH 3 , —N(CH 3 ) 2 and C 1-3 alkyl.
16. The surface binding compound of claim 1 wherein the compound is selected from the group: