Acetylenic diol ethylene oxide/propylene oxide adducts and processes for their manufacture
View Patent ↗This invention provides water-based compositions, particularly coating, ink, fountain solution and agricultural compositions, manifesting reduced equilibrium and dynamic surface tension by the incorporation of a surface tension reducing amount of an acetylenic diol ethylene oxide/propylene oxide adduct of the structure: where r and t are 1 or 2, (n+m) is 1 to 30 and (p+q) is 1 to 30. Also disclosed is a method for making random and block EO/PO adducts of acetylenic diols by reacting an acetylenic diol with EO and/or PO in the presence of a trialkylamine or Lewis acid.
1. A method for making an acetylenic diol ethylene oxide/propylene oxide adduct which is capped with two propylene oxide units which comprises reacting an acetylenic diol ethylene oxide adduct with propylene oxide in the presence of a catalytically effective amount of a trialkylamine, the acetylenic diol moiety derived from 2,4,7,9-tetramethyl-5-decyne-4,7-diol or 2,5,8,11-tetramethyl-6-dodecyne-5,8-diol.
2. The method of claim 1 in which the resulting adduct has the structure:
where r and t are 1 or 2, (n+m) is 1.3 to 30 and p and q are each 1.
3. The method of claim 1 in which the trialkylamine is trimethylamine.
4. The method of claim 2 in which (n+m) is 1.3 to 15.
5. The method of claim 2 in which (n+m) is 1.3 to 10.
6. The method of claim 2 in which the acetylenic diol moiety is derived from 2,4,7,9-tetramethyl-5-decyne-4,7-diol.
7. The method of claim 2 in which the acetylenic diol moiety is derived from 2,5,8,11-tetramethyl-6-dodecyne-5,8-diol.
8. The method of claim 6 in which (n+m) is 1.3 to 10.
9. The method of claim 7 in which (n+m) is 1.3 to 10.
10. The method of claim 1 in which the temperature of the reaction is 40-150° C., the pressure is 2-20 bar and the trialkylamine is present at 0.001 to 10 wt % of the total reactant mass.
11. An acetylenic diol ethylene oxide/propylene oxide adduct of the structure:
where r and t are 1 or 2, (n+m) is 1.3 to 30 and (p+q) is 1 to 10, the ethylene oxide and propylene oxide units being distributed along the alkylene oxide chain in blocks or randomly.
12. An acetylenic diol ethylene oxide/propylene oxide adduct of the structure:
where r and t are 1 or 2, (n+m) is 1.3 to 30 and (p+q) is 1 to 10, the ethylene oxide and propylene oxide units being distributed along the alkylene oxide chain in blocks.
13. The acetylenic diol ethylene oxide/propylene oxide adduct of claim 12 in which the adduct is capped with the propylene oxide units.
14. The acetylenic diol ethylene oxide/propylene oxide adduct of claim 13 in which (n+m) is 1.3 to 15.
15. The acetylenic diol ethylene oxide/propylene oxide adduct of claim 13 in which (n+m) is 1.3 to 10 and (p+q) is 1 to 3.
16. The acetylenic diol ethylene oxide/propylene oxide adduct of claim 13 in which the acetylenic diol moiety is derived from 2,4,7,9-tetramethyl-5-decyne-4,7-diol.
17. The acetylenic diol ethylene oxide/propylene oxide adduct of claim 13 in which the acetylenic diol moiety is derived from 2,5,8,11-tetramethyl-6-dodecyne-5,8-diol.
18. The acetylenic diol ethylene oxide/propylene oxide adduct of claim 16 in which (n+m) is 1.3 to 10 and (p+q) is 1 to 3.
19. The acetylenic diol ethylene oxide/propylene oxide adduct of claim 17 in which (n+m) is 1.3 to 10 and (p+q) is 1 to 3.
20. The acetylenic diol ethylene oxide/propylene oxide adduct of claim 18 in which (p+q) is 2.
21. The acetylenic diol ethylene oxide/propylene oxide adduct of claim 19 in which (p+q) is 2.
22. The acetylenic diol ethylene oxide/propylene oxide adduct of claim 20 which is the 5 mole ethoxylate/2 mole propoxylate adduct of 2,4,7,9-tetramethyl-5-decyne-4,7-diol.