CLAIMS:
5. A compound as recited in Claim 4 wherein
6. A compound as recited in Claim 4 wherein
7. A compound as recited in Claim 4 wherein
8. A compound as recited in Claims 4, 5, 6 or 7 wherein 
= o .
9. A polymeric vehicle which when applied to a substrate provides binder having a Tg not greater than about 180ºC, a pencil hardness of at least about H, and a reverse impact resistance of at least about 30 inch-lbs. at a binder thickness of about 1 mil, said polymeric vehicle comprising:
(a) from about 100 to about 35 weight percent, based upon the weight of the polymeric vehicle, of a modified polymer, wherein said modified polymer is a first epoxy compound which has the formula
wherein
≥ o, but not greater than about 20,
and
and combinations thereof, or is a polymer which is selected from the group consisting of a second epoxy compound which is an epoxy polymer, an acrylic polymer or a polyester polymer, which polymers are covalently bound to at least one mesogenic group which has the formula
(g) g
wherein W is selected from the group consisting of
and
-and combinations thereof.
(b) 0 - 65 weight percent based upon the weight of the polymeric vehicle, of a composition selected from the group consisting of cross-linker resin,
unmodified polymer resin, and mixtures thereof.
10. A polymeric vehicle as recited in Claim 9 wherein the modified polymer is the first epoxy compound.
11. A polymeric vehicle as recited in Claim 9 wherein the modified polymer is the second epoxy compound which is a diglycidyl ether of Bisphenol A.
12. A polymeric vehicle as recited in Claim 9 wherein the modified polymer is the second epoxy compound which is a diglycidyl ether of 1, 4 butanediol.
13. A polymer vehicle as recited in Claim 9 wherein the modified polymer is an acrylic polymer or a polyester polymer and the polymeric vehicle provides a binder having a Tg not greater than about 60ºC.
14. A polymeric vehicle as recited in Claims 9, 10, 11, 12 or 13 wherein the polymeric vehicle includes a cross-linker resin which is a polyamine or an aminoplast resin.
15. A polymeric vehicle as recited in Claim 14 wherein the cross-linker resin is selected from the group consisting of hexakis (methoxy-methyl) melamine,
triethylenetetraamine or mixtures thereof.
16. A polymeric vehicle as recited in Claims 9, 10, 11, 12 or 13 wherein the modified polymer contains about 5 to about 50 weight percent roesogenic groups.
17. A polymeric vehicle as recited in Claim 14 wherein the modified polymer contains about 5 to about 50 weight percent mesogenic groups.
18. A polymeric vehicle as recited in Claims 15 wherein the modified polymer contains about 5 to about 50 weight percent mesogenic groups.
19. A coating binder having a Tg not greater than about 180ºC, a pencil hardness of at least about H, and a reverse impact resistance of at least about 50 inch-lbs. at a binder thickness of 1 mil, which is provided by application to a substrate of a polymeric vehicle in the presence of a solvent therefor, said polymeric vehicle comprising:
(a) from about 100 to about 35 weight percent of at least one modified polymer, wherein said modified polymer is a first epoxy compound which has the general formula 
wherein
> O, but not greater than about 20,
and
and combinations thereof, or is a polymer which is a second epoxy compound which is an epoxy polymer, an acrylic polymer or polyester polymer which polymers are covalently bound to at least one mesogenic group which has the formula
( >
wherein W is selected from the group consisting of
and
< > - and combinations thereof.
(b) from about 0 to about 65 weight percent of a composition selected from the group consisting of cross-linker resin, unmodified polymer resin, and mixtures thereof.
20. A coating binder as recited in Claim 19 wherein the modified polymer is the first epoxy compound.
21. A coating binder as recited in Claim 19 wherein the modified polymer is the second epoxy compound which is a diglycidyl ether of Bisphenol A.
22. A coating binder as recited in Claim 19 wherein the modified polymer is the second epoxy compound which is diglycidyl ether of 1, 4 butanediol.
23. A coating binder as recited in Claim 19 wherein the modified polymer is an acrylic polymer or a polyester polymer, the binder having a Tg not greater than about 60ºC.
24. A coating binder as recited in Claims 19, 20, 21, 22 or 23 wherein the polymeric vehicle includes a cross-linker resin which is a polyamine or an aminoplast resin.
25. A coating binder as recited in Claim 24 wherein the cross-linker resin is selected from the group consisting of hexakis (methoxy-methyl) melamine,
triethylenetetraamine or mixtures thereof.
26. A coating binder as recited in Claims 19, 20, 21, 22 or 23 wherein the modified polymer contains about 5 to about 50 weight percent mesogenic groups.
27. A coating binder as recited in Claims
24 wherein the modified polymer contains about 5 to about 50 weight percent mesogenic groups.
28. A coating binder as recited in Claim 25 wherein the modified polymer contains about 5 to about 50 weight percent mesogenic groups.
29. A process for the preparation of a compound having the formula
( ) ( )
wherein W is selected from the group consisting of
mixtures thereof,
the process comprising;
mixing hydroguinone, parahydroxybenzoic acid and paratoluene sulfonic acid to provide a mixture; and
heating the mixture to provide the compound.
30. A process recited in Claim 29 wherein the mixture is heated in a range of from about 175ºC to about 200ºC in an aromatic solvent.
31. A process as recited in Claim 30 wherein the mixture is heated for about 30 minutes.
32. A process for the preparation of a compound having the formula
wherein 
= 0, but not greater than about 20 and Y is selected from the group consisting of
/ and combinations thereof, the process comprising
mixing 4'-hydroxyphenyl 4-hydroxybenzoate, epichlorohydrin and dioxane and a base and heating the mixture to provide the compound.
33. A process as recited in Claim 32 wherein the base is NaOH.
34. A process as recited in Claims 32 or 33
O
wherein n = 0 and Y = C-O.
AMENDED CLAIMS
[received by the International Bureau
on 26 January 1990(26.01.90);
original claims 2 and 3 cancelled;
claim 1 amended; claims 4-34 amended and renumbered
as claims 2-32 ( 7 pages) ]
1. A compound having the formula
2 . A compound having the formula
wherein
> 0 , but not greater than about 20 ,
and
and combinations thereof.
3. A compound as recited in Claim 2 wherein
O
Y = - C - O -.
4. A compound as recited in Claim 2 wherein
5. A compound as recited in Claim 2 wherein
6. A compound as recited in Claims 2 , 3 , 4 or 5
wherein n = O .
7. A polymeric vehicle which when applied to a substrate provides binder having a Tg not greater than about 180°C, a pencil hardness of at least about H, and a reverse impact resistance of at least about 30 inch-lbs.
at a binder thickness of about 1 mil, said polymeric
vehicle comprising:
(a) from about 100 to about 35 weight percent, based upon the weight of the poly cle, of a
modified polymer, wherein said modified polymer is a first epoxy compound which has the formula
wherein
> o, but not greater than about 20,
and
and combinations thereof, or is a polymer which is selected from the group consisting of a second epoxy compound which is an epoxy polymer, an acrylic polymer or a polyester polymer, which polymers are covalently bound to at least one mesog group which has the formula
wherein W is selected from the group consisting of
0
- C - O -, and
- and combinations thereof. and 
(b) 0 - 65 weight percent based upon the weight of the polymeric vehicle, of a composition selecte from the group consisting of cross-linker resin,
unmodified polymer resin, and mixtures thereof.
8. A polymeric vehicle as recited in Claim 7 wherein the modified polymer is the first epoxy compound.
9. A polymeric vehicle as recited in Claim 7 wherein the modified polymer is the second epoxy compound which is a diglycidyl ether of Bisphenol A.
10. A polymeric vehicle as recited in Claim 7 wherein the modified polymer is the second epoxy compound which is a diglycidyl ether of 1, 4 butanediol.
11. A polymer vehicle as recited in Claim 7 wherein the modified polymer is an acrylic polymer or a polyester polymer and the polymeric vehicle provides a binder having a Tg not greater than about 60°C.
12. A polymeric vehicle as recited in Claims 7, 8, 9, 10 or 11 wherein the polymeric vehicle includes a cross-linker resin which is a polyamine or an aminoplast resin.
13. A polymeric vehicle as recited in Claim 12 wherein the cross-linker resin is selected from the group consisting of hexakis (methoxy-methyl) melamine,
triethylenetetraamine or mixtures thereof.
14. A polymeric vehicle as recited in Claims 7, 8, 9, 10 or 11 wherein the modified polymer contains about 5 to about 50 weight percent mesogenic groups.
15. A polymeric vehicle as recited in Claim 12 wherein the modified polymer contains about 5 to about 50 weight percent mesogenic groups.
16. A polymeric vehicle as recited in Claims 13 wherein the modified polymer contains about 5 to about 50 weight percent mesogenic groups.
17. A coating binder having a Tg not greater than about 180°C, a pencil hardness of at least about H, and a reverse impact resistance of at least about 50 inch-lbs. at a binder thickness of 1 mil, which is provided by application to a substrate of a polymeric vehicle in the presence of a solvent therefor, said polymeric vehicle comprising:
(a) from about 100 to about 35 weight percent of at least one modified polymer, wherein said modified polymer is a first epoxy compound which has the general formula
wherein
> O, but not greater than about 20,
and
and combinations thereof, or is a polymer which is a second epoxy compound which is an epoxy polymer, an acrylic polymer or polyester polymer which polymers are covalently bound to at least one mesogenic group which has the formula
- 
g g -wherein W is selected from the group consisting of
and
- 
- and combinations thereof, and
(b) from about 0 to about 65 weight percent of a composition selected from the group consisting of cross-linker resin, unmodified polymer resin, and mixtures thereof.
18. A coating binder as recited in Claim 17 wherein the modified polymer is the first epoxy compound.
19. A coating binder as recited in Claim 17 wherein the modified polymer is the second epoxy compound which is a diglycidyl ether of Bisphenol A.
20. A coating binder as recited in Claim 17 wherein the modified polymer is the second epoxy compound which is diglycidyl ether of 1, 4 butanediol.
21. A coating binder as recited in Claim 17 wherein the modified polymer is an acrylic polymer or a polyester polymer, the binder having a Tg not greater than about 60°C.
22. A coating binder as recited in Claims 17, 18, 19, 20 or 21 wherein the polymeric vehicle includes a cross-linker resin which is a polyamine or an aminoplast resin.
23. A coating binder as recited in Claim 22 wherein the cross-linker resin is selected from the group consisting of hexakis (methoxy-methyl) melamine,
triethylenetetraamine or mixtures thereof.
24. A coating binder as recited in Claims 17, 18, 19, 20 or 21 wherein the modified polymer contains about 5 to about 50 weight percent mesogenic groups.
25. A coating binder as recited in Claim 22 wherein the modified polymer contains about 5 to about 50 weight percent mesogenic groups.
26. A coating binder as recited in Claim 23 wherein the modified polymer contains about 5 to about 50 weight percent mesogenic groups.
27. A process for the preparation of a compound having the formula
® @
wherein W is selected from the group consisting of
-
- 
^ ) and
mixtures thereof,
the process comprising: mixing hydroguinone, parahydroxybenzoic acid and paratoluene sulfonic acid to provide a mixture; and
heating the mixture to provide the compound.
28. A process recited in Claim 27 wherein the mixture is heated in a range of from about 175ºC to about 200°C in an aromatic solvent.
29. A process as recited in Claim 28 wherein the mixture is heated for about 30 minutes.
30. A process for the preparation of a compound having the formula
wherein 
= o, but not greater than about 20 and Y is selected from the group consisting of
and
Qy and combinations thereof, the process comprising:
mixing 4'-hydroxyphenyl 4-hydroxybenzoate, epichlorohydrin and dioxane and a base and heating the mixture to provide the compound.
31. A process as recited in Claim 30 wherein the base is NaOH.
32. A process as recited in Claims 30 or 31
O
wherein 
= O and Y = C-O -.