N-substituted acrylamides, preparation method and use thereof
This invention relates to new monomers prepared from phosphorus-containing diene monomers and (meth)acrylonitrile via Ritter reactions, and the preparation method thereof. The polymer of these monomers can be utilized in various applications such as water treatment, rheology modifier, surface modification, etc. The monomers have the following structure (II), Wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 represent, independently, hydrogen, alkyl, aryl, alkaryl, aralkyl, cycloalkyl, heterocycloalkyl, or alkenyl groups; R 6 and R 7 represents R 9 O, and R 10 respectively wherein R 9 and R 10 represents hydrogen, alkyl, aryl, alkaryl, aralkyl, cycloalkyl, alkenyl groups, or metals selected from the group consisting of Na, Li, Ca; R 8 represents H, or CH 3 .
1. Compounds of formula II,
Wherein,
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 represent, independently, hydrogen, alkyl, aryl, alkaryl, aralkyl, cycloalkyl, heterocycloalkyl, or alkenyl groups;
R 6 and R 7 represents R 9 O, and R 10 O respectively wherein R 9 and R 10 represents hydrogen, alkyl, aryl, alkaryl, aralkyl, cycloalkyl, alkenyl groups, or metals selected from the group consisting of Na, Li, Ca;
R 8 represents H, or CH 3 ; and
wherein any two of R 1 , R 2 , R 3 , R 4 and R 5 are together formed into a cycloalkyl, or heterocycloalkyl group.
2. The compounds of claim 1 , wherein the said alkyl, alkenyl comprise from 1˜24 carbon atoms, said aryl comprises from 6˜24 carbon atoms, said alkaryl, aralkyl comprise from 7˜24 carbon atoms, and said cycloalkyl, heterocycloalkyl comprise from 3˜24 carbon atoms.
3. The compounds of claim 1 , wherein the said alkyl, alkenyl comprise from 1˜18 carbon atoms, said aryl comprises from 6˜18 carbon atoms, said alkaryl, aralkyl comprise from 7˜18 carbon atoms, and said cycloalkyl, heterocycloalkyl comprise from 3˜18 carbon atoms.
4. The compounds of claim 1 , wherein R 1 and/or R 2 represent hydrogen.
5. The compounds of claim 1 , wherein said cycloalkyl or heterocycloalkyl group is selected from 3˜8 membered rings.
6. The compounds according to claim 1 , wherein R 1 , R 2 , and R 4 represent hydrogen.
7. The compounds according to claim 1 , wherein R 3 and R 5 represent methyl.
8. The compounds according to claim 1 , wherein R 6 and R 7 represent R 9 O and R 10 O, R 9 =R 10 =H.
9. The compounds according to claim 1 , wherein R 1 , R 2 , and R 4 represent hydrogen, R 3 , R 5 represent methyl and wherein R 6 and R 7 represent R 9 O and R 10 O R 9 =R 10 =H.
10. A method for preparing a compound of formula II, which comprises the step of reacting a compound of formula I with (meth)acrylonitrile,
Wherein,
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 represent, independently, hydrogen, alkyl, aryl, alkaryl, aralkyl, cycloalkyl, heterocycloalkyl, or alkenyl groups;
R 6 and R 7 represents R 9 O, and R 10 O respectively wherein R 9 and R 10 represents hydrogen, alkyl, aryl, alkaryl, aralkyl, cycloalkyl, alkenyl groups, or metals selected from the group consisting of Na, Li, Ca;
R 8 represents H, or CH 3 ; and
wherein any two of R 1 , R 2 , R 3 , R 4 and R 5 are together formed into a cycloalkyl, or heterocycloalkyl group.
11. The method of claim 10 , wherein the said alkyl, alkenyl comprise from 1˜24 carbon atoms, said aryl comprises from 6˜24 carbon atoms, said alkaryl, aralkyl comprise from 7˜24 carbon atoms, and said cycloalkyl, heterocycloalkyl comprise from 3˜24 carbon atoms.
12. The method of claim 10 , wherein the said alkyl, alkenyl comprise from 1˜18 carbon atoms, said aryl comprises from 6˜18 carbon atoms, said alkaryl, aralkyl comprise from 7˜18 carbon atoms, and said cycloalkyl, heterocycloalkyl comprise from 3˜18 carbon atoms.
13. The method of claim 10 , wherein R 1 and/or R 2 represent hydrogen.
14. The method of claim 10 , wherein said cycloalkyl or heterocycloalkyl group is selected from 3˜8 membered rings.
15. The method according to claim 10 , wherein R 1 , R 2 , and R 4 represent hydrogen.
16. The method according to claim 10 , wherein R 3 and R 5 represent methyl.
17. The method according to claim 10 , wherein R 6 and R 7 represent R 9 O and R 10 , R 9 =R 10 =H.
18. The method according to claim 10 , wherein R 1 , R 2 , and R 4 represent hydrogen, R 3 , R 5 represent methyl and wherein R 6 and R 7 represent R 9 O and R 10 , R 9 =R 10 =H.
19. The method according to claim 10 , wherein said compound I is added in the molar ratio of (0.1˜1):1 relative to said (meth)acrylonitrile.
20. The method according to claim 19 , wherein said compound I is added in the molar ratio of (0.8˜1):1 relative to said (meth)acrylonitrile.
21. The method according to claim 10 , wherein the reaction time remains 4˜24 hours.
22. The method according to claim 21 , wherein the reaction time remains 5˜18 hours.
23. The method according to claim 10 , wherein the reaction temperature remains 0˜100° C.
24. The method according to claim 23 , wherein the reaction temperature remains 30˜60° C.
25. A polymer or co-polymer of the compounds of formula II according to claim 1 .
26. A method for water treatment, rheology modifier applications, surface treatment applications, oilfield applications, mining applications, dental applications, plastics, and/or as flame retardants comprising the step of using compounds of formula II according to claim 1 .
27. A method for water treatment, rheology modifier applications, surface treatment applications, oilfield applications, mining applications, dental applications, plastics, and/or as flame retardants comprising the step of using a polymer or co-polymer according to claim 25 .