Polyether-modified polybutadienes and processes for preparation thereof
A process can be used for preparing polyether-modified polybutadienes. The process involves reacting at least one polybutadiene (A) with at least one epoxidizing reagent (B) to give at least one epoxy-functional polybutadiene (C). The at least one epoxy-functional polybutadiene (C) is then reacted with at least one hydroxy-functional compound (D) to give at least one hydroxy-functional polybutadiene (E). The at least one hydroxy-functional polybutadiene (E) is finally reacted with at least one epoxy-functional compound (F) to give at least one polyether-modified polybutadiene (G).
1. A process for preparing one or more polyether-modified polybutadienes, comprising:
a) reacting at least one polybutadiene (A) with at least one epoxidizing reagent (B) to give at least one epoxy-functional polybutadiene (C);
b) reacting the at least one epoxy-functional polybutadiene (C) with at least one hydroxy-functional compound (D) to give at least one hydroxy-functional polybutadiene (E); and
c) reacting the at least one hydroxy-functional polybutadiene (E) with at least one epoxy-functional compound (F) to give at least one polyether-modified polybutadiene (G);
wherein the reacting in b) is an addition reaction of the at least one hydroxy-functional compound (D) onto the at least one epoxy-functional polybutadiene (C), and said at least one hydroxy-functional compound (D) is at least one compound selected from the group consisting of a mono-alcohol, a carboxylic acid or water.
2. The process according to claim 1 , further comprising:
d) reacting the at least one polyether-modified polybutadiene (G) with at least one end-capping reagent (H) to give at least one polyether-modified polybutadiene (K) containing end-capped polyether radicals.
3. The process according to claim 2 , further comprising:
e) lightening a colour of the at least one polyether-modified polybutadiene (G) or the at least one polyether-modified polybutadiene (K).
4. The process according to claim 1 , wherein the at least one polybutadiene (A) has double bonds which are 0% to 80% 1,2-vinyl double bonds and 20% to 100% 1,4-double bonds.
5. The process according to claim 1 , wherein a number-average molar mass M n of the at least one polybutadiene (A) is from 200 g/mol to 20,000 g/mol.
6. The process according to claim 1 , wherein >0% to 70% of double bonds of the at least one polybutadiene (A) are epoxidized.
7. The process according to claim 1 , wherein the at least one epoxidizing reagent (B) contains performic acid.
8. The process according to claim 1 , wherein the at least one hydroxy-functional compound (D) is at least one monofunctional alcohol having 1 to 6 carbon atoms.
9. The process according to claim 1 , wherein in b), a total number of hydroxyl groups in the at least one hydroxy-functional compound (D) to a total number of epoxy groups in the at least one epoxy-functional polybutadiene (C) is from >1:1 to 50:1.
10. The process according to claim 1 , wherein in b), an acid is used as a catalyst.
11. The process according to claim 1 , wherein the at least one epoxy-functional compound (F) used in c) is selected from the group consisting of an alkylene oxide having 2 to 18 carbon atoms, a glycidyl compound, and a mixture thereof.
12. The process according to claim 1 , wherein c) further includes an alkoxylation catalyst.
13. The at least one polyether-modified polybutadiene (G), obtained by the process according to claim 1 ,
wherein the at least one hydroxy-functional compound (D) is a mono-alcohol or a carboxylic acid.
14. A polyether-modified polybutadiene, comprising repeat units selected from the group consisting of divalent radicals
wherein
OA is in each case independently derived from a mono-alcohol HO—A or —O— acyl,
B is in each case independently a radical of the formula (4a)
R 1 is in each case independently a monovalent hydrocarbon radical having 1 to 16 carbon atoms,
R 2 is a radical of the formula —CH 2 —O—R 3 ;
R 3 is in each case independently a monovalent hydrocarbon radical having 3 to 18 carbon atoms;
R 4 is in each case independently a monovalent organic radical having 1 to 18 carbon atoms or hydrogen; and
m, n, o, p and q are each independently 0 to 300, with the proviso that the sum total of m, n, o, p and q is greater than 1;
for every permutation of the repeat units (U), (V), (W), (X), (Y) and (Z) and of repeat units in B.
15. The polyether-modified polybutadiene according to claim 14 , wherein a sum total of all repeat units (U), (V) and (W) divided by a sum total of all repeat units (U), (V), (W), (X), (Y) and (Z) is from >0% to 70%.
16. The polyether-modified polybutadiene according to claim 14 , wherein the polyether-modified polybutadiene is of the formula (5)
wherein a proportion of polyether-modified repeat units shown in formula (5), based on a sum total of all repeat units shown in formula (5), is >0% to 70%, where the proportion is calculated as [(d+e+f)/(a+b+c+d+e+f)]*100%.
17. The polyether-modified polybutadiene according to claim 14 , wherein a number-average molar mass M n of a polybutadiene moiety is from 200 g/mol to 20,000 g/mol.
18. The polyether-modified polybutadiene according to claim 14 , wherein 0% to 80% of double bonds present are 1,2 vinyl double bonds, and 20% to 100% of the double bonds present are 1,4 double bonds.
19. The polyether-modified polybutadiene according to claim 14 , wherein an average molar mass of B is from 100 g/mol to 20,000 g/mol.
20. The at least one polyether-modified polybutadiene (K), obtained by the process according to claim 2 .
21. The process according to claim 1 , wherein the at least one polyether-modified polybutadiene (G) is a linear polybutadiene with pendant polyether radicals.
22. The process according to claim 1 , wherein the process is performed without an organolithium compound.
23. The polyether-modified poly butadiene according to claim 14 , wherein —OA is derived from a mono-alcohol with 1 to 6 carbon atoms.