High performance acrylamide adhesives
View Patent ↗Disclosed are derivatives of (tetrahydropyranyl)methyl acrylamide and polymers derived therefrom, as well as methods of making such compounds and polymers. Adhesives, coatings, and plastics which include such polymers are also described.
1. A compound of Formula I:
and stereoisomers thereof, wherein
Y is —C(H)(R 3 )— or —C(H)(R 3 )—C(H)(R 4 )—;
R 1 , R 2 , R 3 , and R 4 are independently an —OH, a protected hydroxyl group, or a group of Formula II:
wherein one of R 1 , R 2 , R 3 , and R 4 is a group of Formula II; and
R 5 , R 6 , R 7 and R 8 are independently selected from hydrogen and a substituted or unsubstituted alkyl group.
2. The compound of claim 1 wherein the protected hydroxyl group is selected from trimethylsilyl, t-butyldimethylsilyl, acetyl, benzyl, benzoyl, or methoxymethyl.
3. The compound of claim 1 wherein R 5 and R 6 are independently selected from the group consisting of H and a methyl group.
4. The compound of claim 1 wherein R 7 and R 8 are independently selected from the group consisting of H, a methyl group and an ethyl group.
5. The compound of claim 1 having Formula IB:
6. The compound of claim 1 selected from
N-((3,4,6-trihydroxy-5-methacrylamidotetrahydro-2H-pyran-2-yl)methyl)methacrylamide,
N-((5-acrylamido-3,4,6-trihydroxytetrahydro-2H-pyran-2-yl)methyl)methacrylamide,
N-(6-(acrylamidomethyl)-2,4,5-trihydroxytetrahydro-2H-pyran-3-yl)methacrylamide, or
N-((5-acrylamido-3,4,6-trihydroxytetrahydro-2H-pyran-2-yl)methyl)acrylamide.
7. A polymer comprising one or more repeating units derived from the compound of Formula I:
and stereoisomers thereof, wherein
Y is —C(H)(R 3 )— or —C(H)(R 3 )—C(H)(R 4 )—;
R 1 , R 2 , R 3 , and R 4 are independently an —OH, a protected hydroxyl group, or a group of Formula II:
wherein one of R 1 , R 2 , R 3 , and R 4 is a group of Formula II; and
R 5 , R 6 , R 7 and R 8 are independently selected from the group consisting of hydrogen and a substituted or unsubstituted alkyl group.
8. The polymer of claim 7 wherein R 5 and R 6 are independently selected from the group consisting of H and a methyl group.
9. The polymer of claim 7 wherein R 7 and R 8 are independently selected from the group consisting of H, a methyl group and an ethyl group.
10. The polymer of claim 7 wherein the one or more repeating units are derived from the compound of Formula IB:
11. The polymer of claim 7 wherein the one or more repeating units are derived from one or more compounds selected from
N-((3,4,6-trihydroxy-5-methacrylamidotetrahydro-2H-pyran-2-yl)methyl)methacrylamide,
N-((5-acrylamido-3,4,6-trihydroxytetrahydro-2H-pyran-2-yl)methyl)methacrylamide,
N-(6-(acrylamidomethyl)-2,4,5-trihydroxytetrahydro-2H-pyran-3-yl)methacrylamide, or
N-((5-acrylamido-3,4,6-trihydroxytetrahydro-2H-pyran-2-yl)methyl)acrylamide.
12. The polymer of claim 7 comprising from 2 to about 1,000,000 repeating units derived from the compound of Formula I.
13. The polymer of claim 7 selected from a polyacrylamide, a polyacrylate, a polyvinyl, an epoxy, a polyurea, a polyurethane, an alkyd resin, or a copolymer of any of the foregoing.
14. A method of making a compound of Formula I comprising:
contacting a compound of Formula III,
with a compound of Formula IV,
optionally in the presence of a base, wherein
R is hydrogen or a substituted or unsubstituted alkyl group;
Y is —C(H)(R 3 )— or —C(H)(R 3 )—C(H)(R 4 )—;
R 1 , R 2 , R 3 , and R 4 are independently an —OH, a protected hydroxyl group, or an —NHR 8 wherein R 8 is hydrogen or a substituted or unsubstituted alkyl group, wherein one of R 1 , R 2 , R 3 , and R 4 is an —NHR 8 ;
R 7 is hydrogen or a substituted or unsubstituted alkyl group; and
LG is a leaving group.
15. The method of claim 14 wherein the protected hydroxyl group is selected from trimethylsilyl, t-butyldimethylsilyl, acetyl, benzyl, benzoyl, or methoxymethyl.
16. The method of claim 14 wherein R 7 and R 8 are hydrogen.
17. The method of claim 15 wherein LG is chloride, and the base is selected from pyridine, dimethylaminopyridine, triethylamine, diisopropylethylamine or a mixture of any two or more thereof.