Preparation of (meth)acrylic esters of polyalkoxy-containing alcohols

Patent metadata

Field	Value
Publication number	US-9353043-B2
Application number	US-201514620579-A
Country	US
Kind code	B2
Filing date	Feb 12, 2015
Priority date	Feb 18, 2014
Publication date	May 31, 2016
Grant date	May 31, 2016

Abstract

In a process for preparing (meth)acrylic esters (E) of polyalkoxy-containing alcohols which comprises reacting polyalkoxy-containing alcohols (P) of formula (I)

where
R 1 is hydrogen, a hydroxyl group or a straight-chain or branched, saturated or unsaturated alcohol of 1 to 30 carbon atoms, R 2 and R 3 are each independently H or methyl, and m and n are each independently an integer between 0 and 100, with the proviso that m and n cannot both be 0,

with a (meth)acrylic anhydride (A) in the presence of at least one basic catalyst (K) having a pK B value of not more than 7.0 and of at least one sterically hindered polymerization inhibitor, the reaction mixture is quenched with a C 1 -C 6 alkanol after the reaction has ended.

First claim

We claim:

1. A process for preparing a (meth)acrylic ester (E) of a polyalkoxy-containing alcohol, the process comprising reacting a polyalkoxy-containing alcohol (P) of formula (I)

wherein
R 1 is hydrogen, a hydroxyl group or a straight-chain or branched, saturated or unsaturated alcohol of 1 to 30 carbon atoms,
R 2 and R 3 are each independently H or methyl, and
m and n are each independently an integer between 0 and 100, with the proviso that m and n cannot both be 0,
with a (meth)acrylic anhydride (A) in the presence of a basic catalyst (K) having a pK B value of not more than 7.0 and of a sterically hindered polymerization inhibitor,
wherein the reaction mixture is quenched with a C 1 -C 6 alkanol after the reaction has ended.

2. The process according to claim 1 , wherein R 2 and R 3 are each hydrogen in formula (I).

3. The process according to claim 1 , wherein m and n in formula (I) are each independently integers in the range from 5 to 90.

4. The process according to claim 3 , wherein m and n in formula (I) are each independently integers in the range from 5 to 50.

5. The process according to claim 1 , wherein the substituent R 1 is a straight-chain, saturated or unsaturated primary alcohol of 6 to 22 carbon atoms.

6. The process according to claim 1 , wherein the basic catalyst (K) has a pK B value of not more than 3.0.

7. The process according to claim 6 , wherein the basic catalyst is selected from the group consisting of alkali metal and alkaline earth metal hydroxides and inorganic salts.

8. The process according to claim 7 , wherein the basic catalyst is lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide or calcium hydroxide.

9. The process according to claim 7 , wherein the inorganic salt comprises at least one anion selected from the group consisting of carbonate (CO 3 2− ), bicarbonate (HCO 3− ), phosphate (PO 4 3− ), hydrogenphosphate (HPO 4 2− ), dihydrogenphosphate (H 2 PO 4− ), sulfate (SO 4 2− ), sulfite (SO 3 2− ) and carboxylate (R 4 —COO—), where R 4 is C 1 -C 18 alkyl; C 2 -C 18 alkyl optionally interrupted by an oxygen atom, a sulfur atom, a substituted or unsubstituted imino group, or any combination thereof; or C 6 -C 14 aryl.

10. The process according to claim 9 , wherein the inorganic salt is selected from the group consisting of Li 3 PO 4 , K 3 PO 4 , Na 3 PO 4 , K 2 CO 3 and Na 2 CO 3 and also hydrates thereof.

11. The process according to claim 1 , wherein the amount of (meth)acrylic anhydride (A) is reacted at not more than 1.35 mol per mole of the polyalkoxy-containing alcohol (P).

12. The process according to claim 11 , wherein the amount of (meth)acrylic anhydride (A) is reacted at not more than 1.15 mol per mole of the polyalkoxy-containing alcohol (P).

13. The process according to claim 1 wherein the sterically hindered polymerization inhibitor does not degrade during the course of the reaction.

14. The process according to claim 13 , wherein the sterically hindered polymerization inhibitor is selected from the group consisting of 2,6-di-tert-butylphenol, 2,6-di-tert-butyl-4-methylphenol and phenothiazine.

15. The process according to claim 1 , wherein the C 1 -C 6 alkanol is selected from the group consisting of methanol, ethanol, propanol and isopropanol.

16. The process according to claim 15 , wherein the C 1 -C 6 alkanol is selected from the group consisting of methanol and ethanol.

17. The process according to claim 1 , wherein the quench time is up to 2 h, but not less than 30 minutes.

18. The process according claim 1 , wherein the C 1 -C 6 alkanol is added to the reaction medium in amounts of up to 5 wt %, based on total reaction medium.

19. A method for producing a dispersion, comprising employing a (meth)acrylic ester (E) of a polyalkoxy-containing alcohol as a monomer or comonomer.

Assignees

• Basf Se

Inventors

• Misske Andrea
• Meisenburg Uwe
• Petzoldt Jochen
• Bette Virginie
• Urtel Bolette
• Ballin Jean-Marc

Classifications

• C09D7/20

  Diluents or solvents · CPC title

• C08G65/3322 Primary

  acyclic · CPC title

• C08K5/13

  Phenols; Phenolates · CPC title

• C08G63/83

  Alkali metals, alkaline earth metals, beryllium, magnesium, copper, silver, gold, zinc, cadmium, mercury, manganese, or compounds thereof {(C08G63/823 takes precedence)} · CPC title

• C07C67/08 Primary

  by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds · CPC title