α-(unsaturated alkoxyalkyl) acrylate composition and process for production thereof
An α-(unsaturated alkoxyalkyl)acrylate composition is provided which enables an α-(unsaturated alkoxyalkyl)acrylate product to be stored at a high purity for an extended period of time and can fully suppress problems such as discoloration and gelation from arising during polymerization, and a method of safely preparing α-(unsaturated alkoxyalkyl)acrylate compositions industrially, with high purity. The composition includes an α-(unsaturated alkoxyalkyl)acrylate of a specific structure and an antioxidant, the content of the antioxidant being from 0.03 to 0.5 wt % per 100 wt % of the α-(unsaturated alkoxyalkyl)acrylate.
1. An α-(unsaturated alkoxyalkyl)acrylate composition comprising: an α-(unsaturated alkoxyalkyl)acrylate represented by general formula (1) below
where R 2 , R 3 and R 4 are identically or independently a hydrogen atom or a C 1-30 organic group;
R 5 and R 6 are identically or independently a hydrogen atom or a C 1-18 alkyl group which may be substituted; and Z is an n-valent organic group, with n being an integer greater than or equal to 1;
and an antioxidant,
wherein the antioxidant content is from 0.03 to 0.5 wt. % relative to 100 wt. % of the α-(unsaturated alkoxyalkyl)acrylate; and
wherein the composition has a nitrogen content, per 100 wt. % of the α-(unsaturated alkoxyalkyl)acrylate, of 100 ppm or less.
2. The α-(unsaturated alkoxyalkyl)acrylate composition according to claim 1 , wherein the composition has a content of unsaturated alkyl ester or of acrylate having a hydroxyalkyl group at the α-position, per 100 wt. % of the α-(unsaturated alkoxyalkyl)acrylate, of 1 wt. % or less.
3. The α-(unsaturated alkoxyalkyl)acrylate composition according to claim 2 , wherein the α-(unsaturated alkoxyalkyl)acrylate content is at least 95 wt. % per 100 wt. % of the composition.
4. The α-(unsaturated alkoxyalkyl)acrylate composition according to claim 1 , wherein R 5 and R 6 in the general formula (1) are hydrogen atoms.
5. The α-(unsaturated alkoxyalkyl)acrylate composition according to claim 1 , wherein the α-(unsaturated alkoxyalkyl)acrylate comprises an α-(allyloxymethyl)acrylate.
6. The α-(unsaturated alkoxyalkyl)acrylate composition according to claim 1 , wherein the antioxidant comprises a phenolic antioxidant and/or a phosphorus-based antioxidant.
7. The α-(unsaturated alkoxyalkyl)acrylate composition according to claim 1 , wherein the α-(unsaturated alkoxyalkyl)acrylate has a boiling point at 1333 Pa of at least 95° C.
8. The α-(unsaturated alkoxyalkyl)acrylate composition according to claim 1 , wherein n in the general formula (1) is 1.
9. The α-(unsaturated alkoxyalkyl)acrylate composition according to claim 8 , wherein Z in the general formula (1) is a group represented by the general formula —OR 1 , where R 1 is a hydrogen atom or a C 1-30 organic group.
10. The α-(unsaturated alkoxyalkyl)acrylate composition according to claim 1 , wherein Z in the general formula (1) is an n-valent linkage, with n being an integer greater than or equal to 2.
11. The α-(unsaturated alkoxyalkyl)acrylate composition of claim 1 , wherein the composition has an amount of peroxide per 100 wt. % of the α-(unsaturated alkoxyalkyl)acrylate of 50 ppm or less.
12. A radical curable composition comprising the α-(unsaturated alkoxyalkyl)acrylate composition according to claim 1 .
13. The α-(unsaturated alkoxyalkyl)acrylate composition according to claim 1 , wherein the nitrogen content is 80 ppm or less, per 100 wt. % of the α-(unsaturated alkoxyalkyl)acrylate.
14. The α-(unsaturated alkoxyalkyl)acrylate composition according to claim 1 , wherein the nitrogen content is 50 ppm or less, per 100 wt. % of the α-(unsaturated alkoxyalkyl)acrylate.
15. A method for producing the α-(unsaturated alkoxyalkyl)acrylate composition according to claim 1 ,
wherein the method comprises reacting an acrylate having a hydroxyalkyl group at the α-position with an unsaturated alcohol represented by general formula (7) below
where R 2 , R 3 and R 4 are the same as in the general formula (1); and
purifying crude α-(unsaturated alkoxyalkyl)acrylate to obtain purified α-(unsaturated alkoxyalkyl)acrylate, and then adding an antioxidant to the purified α-(unsaturated alkoxyalkyl)acrylate.
16. The method for producing the α-(unsaturated alkoxyalkyl)acrylate composition according to claim 15 , wherein the unsaturated alcohol comprises allyl alcohol.
17. The method for producing the α-(unsaturated alkoxyalkyl)acrylate composition according to claim 15 , wherein the method comprises carrying out a reaction in the presence of an amine catalyst.
18. A method for producing the α-(unsaturated alkoxyalkyl)acrylate composition according to claim 15 , wherein the purifying comprises treating the crude α-(unsaturated alkoxyalkyl)acrylate composition with an inorganic alkali, and
wherein the crude α-(unsaturated alkoxyalkyl)acrylate composition contains the acrylate having a hydroxyalkyl group at the α-position.
19. A method for producing the α-(unsaturated alkoxyalkyl)acrylate composition according to claim 15 , wherein the method comprises reacting a polyfunctional compound with a monofunctional α-(unsaturated alkoxyalkyl)acrylate.
20. The method for producing the α-(unsaturated alkoxyalkyl)acrylate composition according to claim 15 , wherein the reacting comprises transesterification of a polyhydric compound with the monofunctional α-(unsaturated alkoxyalkyl)acrylate.