Phosphonate bonding compositions
View Patent ↗The present invention provides for compounds comprising at least one phosphonate or phosphinate moiety; and at least one moiety selected from an aromatic nitroso or an aromatic nitroso precursor and combinations thereof. Adhesive compositions comprising the compounds may find utility in bonding polymers to metal and or hydroxylated surfaces such as glass. Suitable polymers include natural and synthetic rubbers. The aromatic nitroso precursor may be a nitrosobenzene precursor such as at least one of a quinone dioxime or a quinone oxime.
1. A compound comprising:
(a) at least one phosphonate moiety; or
(b) at least one phosphinate moiety; and
(c) at least one moiety selected from an aromatic nitroso or an aromatic nitroso precursor and combinations thereof
wherein the compound is of the general formula:
wherein X can be C, O, N, or S;
n can be 0-20;
R 3 can be C 1 -C 24 alkyl, C 3 -C 24 acyl or OR 2 ;
R 1 and R 2 can be the same or different and are selected from the group consisting of H, C 1 -C 24 alkyl, and C 3 -C 24 acyl; and
R 4 is selected from the group consisting of (showing linkage through X):
wherein R 5 can be C 1 to C 10 alkyl; and
Z indicates that the rings of the above structures can optionally be mono-, di-, tri- or tetrasubstituted with the group consisting of C 1 -C 20 alkyl, C 3 -C 20 cycloalkyl, C 1 -C 20 alkoxy, C 3 -C 20 aralkyl, C 3 -C 20 alkaryl, C 5 -C 20 arylamine, C 5 -C 20 arylnitroso, amino, hydroxy, halogen and combinations thereof, and further wherein the substituents can either be the same or different on each carbon atom of the ring.
2. A compound of the general formula:
wherein R 3 can be C 1 -C 24 alkyl, C 3 -C 24 acyl or OR 2 ;
R 1 and R 2 can be the same or different and are selected from the group consisting of H, C 1 -C 24 alkyl, and C 3 -C 24 acyl.
3. An oligomer or co-oligomer of a compound comprising
(a) at least one phosphonate moiety; or
(b) at least one phosphinate moiety; and
(c) at least one moiety selected from an aromatic nitroso or an aromatic nitroso precursor and combinations thereof.
4. A polymer or co-polymer of a compound comprising
(a) at least one phosphonate moiety; or
(b) at least one phosphinate moiety; and
(c) at least one moiety selected from an aromatic nitroso or an aromatic nitroso precursor and combinations thereof.
5. An oligomer or co-oligomer according to claim 2 of the following general formula:
wherein m can be 1-100; n can be 0-20; p can be 1-10; q can be 0-50; and if q=0, m≧2;
R 3 and R 6 can be the same or different and may be selected from C 1 -C 24 alkyl, C 3 -C 24 acyl or OR 2 ;
R 2 can be selected from the group consisting of H, C 1 -C 24 alkyl, and C 3 -C 24 acyl; X can be C, O, N, or S;
R 4 may be a moiety comprising nitrosoaromatic, or a nitrosoaromatic precursor; and
R 7 can be selected from the group consisting of acrylate, aldehyde, amino, anhydride, azide, maleimide, carboxylate, sulfonate, epoxide, ester functional, halogens, hydroxyl, isocyanate or blocked isocyanate, sulphur functional, vinyl and olefin functional, or polymeric structures.
6. A composition for bonding substrates together, the composition comprising:
i) at least one compound comprising
(a) at least one phosphonate moiety; or
(b) at least one phosphinate moiety; and
(c) at least one moiety selected from an aromatic nitroso or an aromatic nitroso precursor and combinations thereof, and
ii) a silane.
7. A composition according to claim 6 wherein the silane is an amino silane.
8. A process for bonding two substrates together comprising:
a) applying a composition comprising:
at least one compound comprising
(a) at least one phosphonate moiety; or
(b) at least one phosphinate moiety; and
(c) at least one moiety selected from an aromatic nitroso or an aromatic nitroso precursor and combinations thereof to at least one of the substrates and mating the substrates together so as to form a bond therebetween.
9. A process according to claim 8 further comprising the step of heating subsequent to mating the first and second substrates.
10. A process according to claim 8 further comprising the step of abrasively cleaning at least one of the substrates prior to application of the composition thereto.
11. A process according to claim 8 wherein the first substrate is a polymer and the second substrate is a metal or a hydroxylated surface.
12. An assembly of at least two substrates bound together by an adhesive composition comprising:
at least one compound comprising
(a) at least one phosphonate moiety; or
(b) at least one phosphinate moiety; and
(c) at least one moiety selected from an aromatic nitroso or an aromatic nitroso precursor and combinations thereof.
13. A cure product comprising a substrate and a composition comprising:
at least one compound comprising
(a) at least one phosphonate moiety; or
(b) at least one phosphinate moiety; and
(c) at least one moiety selected from an aromatic nitroso or an aromatic nitroso precursor and combinations thereof.