Radiation-curable acrylates of polyol monoalkyl ethers

Abstract

Radiation-curable compositions containing monoalkyl or mono-aralkyl ether di-acrylates or di-methacrylates of particular ethoxylated and/or propoxylated polyols of formulae I and II have been developed. These polyol derivatives substituted with hydrophobic ether functionalities constitute UV-curable diluents that can be isolated in excellent yields with minimal losses during the manufacturing process.

What is claimed is: 
     
       1. A compound of formula I ##STR7## wherein: R 1  =C 2  -C 9  alkyl; R 2  =C 6  -C 18  alkyl, cycloalkyl, or (cycloalkyl)alkyl, phenyl-C 1-4  alkyl, or substituted phenyl-C 1-4  alkyl, in which the substituent is C 1-4  alkyl at the ortho- or para-position of the phenyl ring;   EO=OCH 2  CH 2  --;   PO=OCH 2  CH 2  CH 2  --;   a, b, c, d, e, and f each being an integer from 0-5, provided that the sum of a, b, c, d, e, and f=3-15; and   R 3  =H or CH 3 .   
     
     
       2. A compound according to claim 1 wherein R 1  =C 2  -C 9  alkyl and R 2  =C 6-14  alkyl, cycloalkyl, or cycloalkylmethyl, or phenyl-C 1-2  alkyl. 
     
     
       3. A compound according to claim 2 wherein R 1  =CH 3  CH 2 . 
     
     
       4. A compound according to claim 2 wherein R 1  =CH 3  CH 2  and R 2  =C 6-14  alkyl or phenyl-C 1-2  alkyl. 
     
     
       5. A compound according to claim 4 wherein the sum of a, b, c, d, e, and f is 3. 
     
     
       6. A compound according to claim 1 which is mono-O-hexyl tri-ethoxylated trimethylolpropane diacrylate. 
     
     
       7. A compound according to claim 1 which is mono-O-nonyl tri-ethoxylated trimethylolpropane diacrylate. 
     
     
       8. A compound according to claim 1 which is mono-O-decyl tri-ethoxylated trimethylolpropane diacrylate. 
     
     
       9. A compound according to claim 1 which is mono-O-dodecyl tri-ethoxylated trimethylolpropane diacrylate. 
     
     
       10. A compound according to claim 1 which is mono-O-tetradecyl tri-ethoxylated trimethylolpropane diacrylate. 
     
     
       11. A compound according to claim 1 which is mono-O-benzyl tri-ethoxylated trimethylolpropane diacrylate. 
     
     
       12. A compound according to claim 1 which is mono-O-cinnamyl tri-ethoxylated trimethylolpropane diacrylate. 
     
     
       13. A compound according to claim 1 wherein R 2  has at least seven carbon atoms. 
     
     
       14. A compound according to claim 1 wherein R 2  is C 7  -C 14  alkyl, cycloalkyl, or (cycloalkyl)alkyl, phenyl-C 1-4  alkyl, or substituted phenyl-C 1-4  alkyl, in which the substituent is C 1-14  alkyl at the ortho- or para-position of the phenyl ring. 
     
     
       15. A compound of claim 1 wherein R 2  is C 12  -C 16  alkyl, cycloalkyl, or (cycloalkyl)alkyl, phenyl-C 1-4  alkyl, or substituted phenyl-C 1-4  alkyl, in which the substituent is C 1-4  alkyl at the ortho- or para-position of the phenyl ring. 
     
     
       16. A compound of claim 15 wherein the each of a, b, and c is one and d, e, and f, are zero. 
     
     
       17. A compound of formula II ##STR8## wherein: R 1  =C 1  -C 6  alkyl; R 2  =C 6  -C 18  alkyl, cycloalkyl, or (cycloalkyl)alkyl, phenyl-C 1-4  alkyl, or substituted phenyl-C 1-4  alkyl, wherein the substituent is C 1-14  alkyl at the ortho- or para-position of the phenyl ring;   EO=OCH 2  CH 2  --;   PO=OCH 2  CH 2  CH 2  --;   s, t, u, v, w, x, y, and z being integers from 0-5, provided the sum of s, t, u, v, w, x, y, and z=3-20; and   R 3  =H or CH 3 .   
     
     
       18. A compound according to claim 17 wherein R 1  =C 1-6  alkyl; and R 2  =C 6-14  alkyl, cycloalkylmethyl, or phenyl-C 1-2  alkyl. 
     
     
       19. A compound according to claim 18 wherein R 1  =C 1 . 
     
     
       20. A compound according to claim 18 wherein R 1  =C 1  and R 2  =C 6-14  alkyl or phenyl-C 1-2  alkyl. 
     
     
       21. A compound according to claim 20 wherein the sum of s, t, u, v, w, x, y, and z is 3. 
     
     
       22. A compound according to claim 17 which is mono-O-hexyl tri-ethoxylated pentaerythrityl diacrylate. 
     
     
       23. A compound according to claim 17 which is mono-O-nonyl tri-ethoxylated pentaerythrityl diacrylate. 
     
     
       24. A compound according to claim 17 which is mono-O-decyl tri-ethoxylated pentaerythrityl diacrylate. 
     
     
       25. A compound according to claim 17 which is mono-O-dodecyl tri-ethoxylated pentaerythrityl diacrylate. 
     
     
       26. A compound according to claim 17 which is mono-O-tetradecyl tri-ethoxylated pentaerythrityl diacrylate. 
     
     
       27. A compound according to claim 17 which is mono-O-benzyl tri-ethoxylated pentaerythrityl diacrylate. 
     
     
       28. A compound according to claim 17 which is mono-O-cinnamyl tri-ethoxylated pentaerythrityl diacrylate. 
     
     
       29. A compound according to claim 17 wherein R 2  has at least seven carbon atoms. 
     
     
       30. A compound according to claim 17 wherein R 2  is C 7  -C 14  alkyl, cycloalkyl, or (cycloalkyl)alkyl, phenyl-C 1-4  alkyl, or substituted phenyl-C 1-4  alkyl, in which the substituent is C 1-14  alkyl at the ortho- or para-position of the phenyl ring. 
     
     
       31. A compound of claim 17 wherein R 2  is C 12  -C 16  alkyl, cycloalkyl, or (cycloalkyl)alkyl, phenyl-C 1-4  alkyl, or substituted phenyl-C 1-4  alkyl, in which the substituent is C 1-14  alkyl at the ortho- or para-position of the phenyl ring. 
     
     
       32. A compound according to claim 31 wherein the sum of s, t, u, and v is 3 and each of v, w, x, y, and z is zero.