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Acrylates comprising several quaternary amino groups in the alcohol part, their process of manufacture and the (co) polymers obtained from these monomers

Imported: 23 Feb '17 | Published: 22 Oct '02

Alain Riondel, Vladimir Chaplinski

USPTO - Utility Patents

Abstract

These compounds are represented by the formulae (Ia) and (Ib). To prepare them, in a first stage, p-xylylene dichloride is reacted with a compound (II) to produce a compound (III) and, in a second stage, the compound (III) thus obtained is reacted with a compound of formula (IVa) or (IVb), resulting in an aqueous solution of the compound (Ia) or (Ib) respectively, the water of which is removed, if appropriate.

Claims

1. Compound of formula (Ia) or (Ib):

in which:

2. An aqueous solution of at least one compound according to claim 1, having a concentration of compound (Ia) or (Ib) of from 60 to 80% by weight.

3. A process for the manufacture of a compound of formula (Ia) or (Ib) as defined in claim 1 comprising:

4. Process according to claim 3, characterized in that in the first stage, the reaction is carried out in a solvent medium.

5. Process according to claim 4, characterized in that the solvent is tetrahydrofuran.

6. A process according to claim 3, wherein the first stage is carried out with a molar ratio of the p-xylylene dichloride to the compound of formula (II) of 0.8 to 1.2.

7. A process according to claim 3, wherein the first stage is carried out at a temperature of 5 to 60° C. for a period of time of 8 to 144 hours.

8. A process according to claim 3, wherein the compound of formula (III) is obtained in the form of colorless crystals.

9. A process according to claim 3, wherein the second stage is carried out with a molar ratio of the compound of formula (III) to the compound of formulae (IVa) or (IVb) of between 0.95 and 2.1.

10. A process according to claim 3, wherein the second stage is carried out at a temperature of 30 to 40° C. for a period of time of 1 to 6 hours.

11. A process according to claim 3, wherein the second stage is carried out in the presence of at least one stabilizer selected from the group consisting of hydroquinone methyl ether, 3,5-di (tert-butyl)-4-hydroxytoluene and hydroquinone, and mixtures of these stabilizers, in a proportion of 100 to 2 000 ppm with respect to the charge.

12. A homopolymer or copolymer comprising units of at least one monomer of formula (Ia) or (Ib) as defined in claim 1.

13. A compound of formula III

14. A compound according to claim 13, wherein said compound is in the form of colorless crystals.

15. A process for producing a compound of claim 1, comprising reacting a compound of formula III

wherein R

2 is ethyl or isopropyl,

16. A compound according to claim 1, being compound (Ia).

17. A compound according to claim 1, wherein said compound is of formula (Ib).

18. A compound according to claim 14, wherein R

2 is ethyl.

19. A compound according to claim 14, wherein R

2 is isopropyl.

20. A process according to claim 15, wherein R

2 is ethyl.

21. A process according to claim 15, wherein R

2 is isopropyl.