Surfactant
A compound of the formula R 1 .[(AO) n .—R 2 ] m (I) where: R 1 is the residue of a group having at least m active hydrogen atoms; AO is an alkylene oxide residue; each n is independently from 1 to 100; m is at least 2; and each R 2 is independently H, a C 1 to C 21 hydrocarbyl, or an acyl group —OC.R 3 , where R 3 is a C 1 to C 21 hydrocarbyl group, wherein on average greater than one of the R 2 groups is or comprises a C 4 to C 21 hydrocarbyl group comprising at least two ethylenic double bonds. The compounds are particularly suitable for use in preparing aqueous emulsions or dispersions of resins and polymers, especially alkyd resins.
1. A method of forming an aqueous alkyd resin emulsion, comprising:
i) combining the alkyd resin and a mixture of alkyd resin emulsifying compounds represented by formula (I):
R 1 .[(AO) n .R 2 ] m (I)
wherein:
R 1 independently represents the residue of, or derived from, a sugar having a linear C 4 to C 7 chain and at least m active hydrogen atoms in hydroxyl groups;
AO independently represents an alkylene oxide residue;
each n is independently from 5 to 50;
m is from 3 to 6;
total n is from 30 to 300; and
R 2 independently represents a hydrogen atom, or an acyl group —(CO)R 3 ;
R 3 independently represents a C 15 to C 19 hydrocarbyl group;
wherein:
a) on average each compound comprises from 2 to 6 acyl groups; and
b) on average at least 1.2 of the R 2 groups per compound comprises a C 15 to C 19 hydrocarbyl group comprising at least two ethylenic double bonds;
ii) including water to form a water-in-oil (resin) emulsion.
2. The method of claim 1 , wherein the method further comprises subsequently adding water to the water-in-oil (resin) emulsion at least until the emulsion inverts to form an oil(resin)-in-water emulsion.
3. The method of claim 2 , wherein the method further comprises adding further water to adjust the disperse phase content of the emulsion to that desired.
4. The method of claim 1 , wherein R 2 represents an acyl group.
5. The method of claim 1 , wherein on average each compound comprises from 4 to 6 acyl groups.
6. The method of claim 1 , wherein on average each compound comprises from 3 to 4 acyl groups.
7. The method of claim 1 , wherein the C 15 to C 19 hydrocarbyl group comprising at least two ethylenic double bonds is derived from linoleic acid.
8. The method of claim 1 , wherein at least one of the ethylenic double bonds is reactive during curing of an alkyd resin film formed from the formed emulsion.
9. The method of claim 1 , wherein the average number of double bonds present in the C 15 to C 19 hydrocarbyl group comprising at least two double bonds is in the range from 2.0 to 2.4.
10. The method of claim 1 , wherein the ratio of R 2 groups comprising C 15 to C 19 hydrocarbyl groups comprising at least two ethylenic double bonds to C 15 to C 19 hydrocarbyl groups not comprising at least two ethylenic double bonds is on average in the range from 0.7:1 to 6:1.
11. An aqueous emulsion or dispersion, comprising: i) polymeric particles comprising an alkyd resin; and ii) a mixture of alkyd resin emulsifying compounds represented by formula (I):
R 1 .[(AO) n .R 2 ] m (I)
wherein:
R 1 independently represents the residue of, or derived from, a sugar having a linear C 4 to C 7 chain and at least m active hydrogen atoms in hydroxyl groups;
AO independently represents an alkylene oxide residue; each n is independently from 5 to 50; m is from 3 to 6; total n is from 30 to 300; and R 2 independently represents a hydrogen atom, or an acyl group —(CO)R 3 ; R 3 independently represents a C 15 to C 19 hydrocarbyl group; wherein a) on average each compound comprises from 2 to 6 acyl groups; and b) on average at least 1.2 of the R 2 groups per compound comprises a C 15 to C 19 hydrocarbyl group comprising at least two ethylenic double bonds.
12. The aqueous emulsion or dispersion of claim 11 , wherein the aqueous emulsion or dispersion further comprises an anionic surfactant comprising an alkyl ether carboxylate, an alkyl aryl sulphonate, a phosphate ester, an alkyl ether sulfate, or a mixture of at least two such anionic surfactants.
13. An alkyd resin film, comprising the aqueous emulsion or dispersion of claim 11 .
14. The alkyd resin film of claim 13 , wherein at least one of the ethylenic double bonds is reactive during curing of the alkyd resin film.
15. A mixture of alkyd resin emulsifying compounds represented by formula (I):
R 1 .[(AO) n .R 2 ] m (I)
wherein:
R 1 independently represents the residue of, or derived from, a sugar having a linear C 4 to C 7 chain and at least m active hydrogen atoms in hydroxyl groups;
AO independently represents an alkylene oxide residue;
each n is independently from 5 to 50;
m is from 3 to 6;
total n is from 30 to 300; and
R 2 independently represents a hydrogen atom, or an acyl group —(CO)R 3 ;
R 3 independently represents a C 15 to C 19 hydrocarbyl group;
wherein:
a) on average each compound comprises from 2 to 6 acyl groups; and
b) on average at least 1.2 of the R 2 groups per compound comprises a C 15 to C 19 hydrocarbyl group comprising at least two ethylenic double bonds; and
c) at least one of the ethylenic double bonds is reactive during curing of an alkyd resin.
16. The mixture of compounds of claim 15 , wherein R 1 independently represents the residue of sorbitol.
17. The mixture of compounds of claim 15 , wherein on average each compound comprises from 3 to 4 acyl groups.
18. The mixture of compounds of claim 15 , wherein the C 15 to C 19 hydrocarbyl group comprising at least two ethylenic double bonds is derived from linoleic acid.
19. The mixture of compounds of claim 15 , wherein the at least two ethylenic double bonds are conjugated.
20. The mixture of compounds of claim 15 , wherein the average number of double bonds present in the C 15 to C 19 hydrocarbyl group comprising at least two double bonds is in the range from 2.0 to 2.4.
21. The mixture of compounds of claim 15 , wherein the mixture of alkyd resin emulsifying compounds are formed by reacting a fatty acid or derivative thereof having an iodine value in the range from 100 to 250 g/100 g with an alkoxylated R 1 group.
22. The mixture of compounds of claim 15 , wherein the mixture of alkyd resin emulsifying compounds has an iodine value in the range from 45 to 75 g/100 g.
23. A paint, comprising:
i) an aqueous or mixed aqueous organic continuous phase;
ii) an alkyd resin emulsion discontinuous phase;
iii) the mixture of alkyd resin emulsifying compounds of claim 15 ; and
iv) at least one pigment.