Tri-substituted aromatic-containing additives and surfactants and methods for use

1. A surface active compound according to structure (D.I):

R 18 —R 14 —R 13 —R 12 —R 11   (D.I)

R 12 is absent or is a bivalent linking group,

R 13 is bivalent polyether group,

R 14 is absent or is a bivalent linking group;

R 18 is an anionic group, a cationic group or a nonionic group; and

R 11 is a tri-substituted aromatic group according to the structure D.XII

wherein R 1 , R 2 and R 3 are independently selected from the following structures D.XIIIa, D.XIIIb, D.XIIIc, D.XIIId:

or a C 4 -C 30 branched or linear alkyl group or alkenyl group;

wherein at least one of R 1 , R 2 and R 3 is the C 4 -C 30 branched or linear alkyl group or alkenyl group, and at least one of R 1 , R 2 and R 3 is selected from structure D.XIIIa, D.XIIIb, D.XIIIc, or D.XIIId.

2. The compound of claim 1 wherein R 18 is —OH, —OCH 3 , —OC 2 H 5 , —OC 3 H 7 , —OC 4 H 9 , —OC 5 H 11 , —OC 6 H 13 , —Cl, —Br, —CN, Phosphonate (—PO 3 − M + ), Phosphate (PO 4 − M + ), Sulfate (SO 4 − M + ), Sulfonate (SO 3 − M + ), carboxylate (COO − M + ), a nonionic group, or a quaternary ammonium ion, wherein M+ is a counterion.

3. The surface active compound of claim 1 wherein R 13 is —[CH(R 20 )CH(R 21 )O] x —, wherein x is an integer of from 0 to 100, and R 20 and R 21 are independently selected from any of the following:

H; —CH 2 OH; phenyl; —CH 2 Cl;

a C 1 -C 30 straight or branched alkyl or alkenyl;

—CH 2 OR 22 wherein R 22 is C 1 -C 30 straight or branched alkyl or alkenyl, phenyl, or alkyl substituted phenyl; or

R′COOCH 2 — where R′ is C 1 -C 30 straight or branched alkyl or alkenyl.

4. A surface active compound according to structure D.XXX:

wherein:

g is an integer from 2 to 4;

h is an integer from 2 to 4;

b is an integer from 0 to 1;

k is an integer from 0 to 100;

i is an integer from 0 to 40;

j is an integer from 0 to 40;

R 18 is an anionic group, a cationic group or a nonionic group;

R 11 is according to structure D.XII

wherein R 1 , R 2 and R 3 are independently selected from H, any of the following structures D.XIId, D.XIIIa, D.XIIIb, D.XIIIc, D.XIIId:

or a C 4 -C 30 branched or linear alkyl group or alkenyl group;

wherein at least one of R 1 , R 2 and R 3 is the C 4 -C 30 branched or linear alkyl group or alkenyl group and at least one of R 1 , R 2 and R 3 is selected from structure D.XIIIa, D.XIIIb, D.XIIIc, or D.XIIId.

5. The compound according to claim 4 wherein R 18 is —OH, —OCH 3 , —OC 2 H 5 , —OC 3 H 7 , —OC 4 H 9 , —OC 5 H 11 , —OC 6 H 13 , —Cl, —Br, —CN, Phosphonate (—PO 3 − M + ), Phosphate (PO 4 − M + ), Sulfate (SO 4 − M + ), Sulfonate (SO 3 − M + ), carboxylate (COO − M + ), a nonionic group, or a quaternary ammonium ion, wherein M+ is a cation including but not limited to H + , Na + , NH 4 + , K + or Li + .

6. The compound according to claim 4 wherein:

g is an integer from 2 to 4;

h is an integer from 2 to 4;

b is an integer from 0 to 1;

k is an integer from 0 to 25;

i is an integer from 0 to 40;

j is an integer from 0 to 40;

R 11 is a tri-substituted aromatic group according to the structure D.XII

wherein R 1 , R 2 and R 3 are independently selected from the following structures D.XIIIa, D.XIIIb, D.XIIIc, D.XIIId:

or a C 6 -C 30 branched or linear alkyl group or alkenyl group;

wherein at least one of R 1 , R 2 and R 3 is the C 6 -C 30 branched or linear alkyl group or alkenyl group and at least one of R 1 , R 2 and R 3 is selected from structure D.XIIIa, D.XIIIb, D.XIIIc, or D.XIIId.

7. The compound of claim 1 wherein the C 4 -C 30 branched or linear alkyl group or alkenyl group is a C 6 -C 14 branched or linear alkyl group.

8. The compound of claim 4 wherein the C 4 -C 30 branched or linear alkyl group or alkenyl group is a C 6 -C 14 branched or linear alkenyl group.

9. The compound of claim 1 wherein the C 4 -C 30 branched or linear alkyl group or alkenyl group is a C 8 -C 12 branched or linear alkyl group.

10. The compound of claim 4 wherein the C 4 -C 30 branched or linear alkyl group or alkenyl group is a C 8 -C 12 branched or linear alkenyl group.

11. The compound of claim 1 wherein the C 4 -C 30 branched or linear alkyl group or alkenyl group is a C 4 -C 12 branched or linear alkyl group or alkenyl group.

12. The compound of claim 4 wherein the C 4 -C 30 branched or linear alkyl group or alkenyl group is a C 4 -C 12 branched or linear alkenyl group.

13. The compound of claim 6 wherein R 11 is a tri-substituted aromatic group according to the structure D.XII

wherein R 1 , R 2 and R 3 are independently selected from:

a styryl group, or

a C 6 -C 30 branched or linear alkyl group or alkenyl group;

wherein at least one of R 1 , R 2 and R 3 is the C 6 -C 30 branched or linear alkyl group or alkenyl group, and at least one of R 1 , R 2 and R 3 is the styryl group.

14. The compound of claim 1 wherein R 11 is a tri-substituted aromatic group according to the structure D.XII-1

wherein R 1 , is the C 4 -C 30 branched or linear alkyl group or alkenyl group.

15. The compound of claim 14 wherein the C 4 -C 30 branched or linear alkyl group or alkenyl group is a C 4 -C 12 branched or linear alkyl group or alkenyl group.

16. A low VOC latex coating composition comprising:

(a) at least one latex polymer;

(b) optionally, at least one pigment;

(c) water; and

(d) an additive present in an amount effective to impart freeze-thaw stability, having structure D.XII

wherein R 1 , R 2 and R 3 are independently selected from H, any of following structures D.XIIIa, D.XIIIb, D.XIIIc, D.XIIId:

or a C 4 -C 30 branched or linear alkyl group or alkenyl group;

wherein at least one of R 1 , R 2 and R 3 is the C 4 -C 30 branched or linear alkyl group or alkenyl group, and at least one of R 1 , R 2 and R 3 is selected from structure D.XIIIa, D.XIIIb, D.XIIIc, or D.XIIId.

17. A method for imparting freeze-thaw stability on a low VOC coating composition comprising adding to the composition an effective amount of an additive according to structural formula D.XII

wherein R 1 , R 2 and R 3 are independently selected from H, any of following structures D.XIIIa, D.XIIIb, D.XIIIc, D.XIIId:

or a C 4 -C 30 branched or linear alkyl group or alkenyl group;

wherein at least one of R 1 , R 2 and R 3 is the C 4 -C 30 branched or linear alkyl group or alkenyl group, and at least one of R 1 , R 2 and R 3 is selected from structure D.XIIIa, D.XIIIb, D.XIIIc, or D.XIIId

wherein the coating composition comprises a latex polymer.

18. The method of claim 17 wherein the effective amount is an amount of the additive greater than about 0.5% by weight of the polymer.

19. The method of claim 17 wherein the effective amount is an amount of the additive greater than about 1.3% by weight of the polymer.

20. The method of claim 17 wherein the effective amount is an amount of the additive greater than about 1.6% by weight of the polymer.

21. The method of claim 17 wherein the effective amount is an amount of the additive greater than about 1% by weight of the polymer.