1,3-PROPANEDIOL ACRYLATES, DIACRYLATES, MONOACRYLATES, METHACRYLATES, AND DIGLYCIDYL ETHER AND USES THEREOF

1 . A reactive diluent comprising a 1,3-propanediol diacrylate component, 1,3-propanediol monoacrylate component, and/or a 1,3-propanediol di-glycidylether component.

2 . A coating composition comprising the reactive diluent of claim 1 , a resin, and a reaction initiator.

3 . The coating composition of claim 2 , wherein the resin is an acrylic resin.

4 . The coating composition of claim 3 , wherein the acrylic resin is a urethane acrylate.

5 . The coating composition of claim 2 , wherein the reaction initiator is a photoinitiator.

6 . A coated article comprising the coating composition of claim 2 on at least of portion of one surface of the article.

7 . The coated article of claim 6 , wherein the coated article is a metal coated article or a wood coated article.

8 . The coating composition of claim 2 , wherein the coating composition has a chemical resistance of at least about 20 s.

9 . The coating composition of claim 2 , wherein the coating composition has a Persoz hardness of at least about 40%.

10 . The coating composition of claim 2 , wherein the coating composition has an impact resistance of at least about 950 mm on a substrate side an object coated with the coating composition.

11 . A process for preparing a coating composition comprising:

(a) mixing a resin with a reactive diluent comprising a 1,3-propanediol diacrylate component, 1,3-propanediol monoacrylate component, and/or a 1,3-propanediol di-glycidylether component; and

(b) reacting the resin with the reactive diluent in the presence of a reaction initiator.

12 . The process of claim 11 , wherein the resin is an acrylic resin.

13 . The process of claim 12 , wherein the acrylic resin is a urethane acrylate.

14 . The process of claim 11 , wherein the reaction initiator is a photoinitiator.

15 . A process for coating an article comprising:

(a) mixing a resin, a reaction initiator, and a reactive diluent comprising a 1,3-propanediol diacrylate component, 1,3-propanediol monoacrylate component, and/or a 1,3-propanediol di-glycidylether component to produce a coating mixture;

(b) applying the coating mixture to at least a portion of one surface of an article; and

(c) curing the coating mixture to form a cured coating layer on the article.

16 . The process of claim 15 , wherein the resin is an acrylic resin.

17 . The process of claim 16 , wherein the acrylic resin is a urethane acrylate.

18 . The process of claim 15 , wherein the reaction initiator is a photoinitiator.

19 . A process for preparing 1,3-propanediol acrylate comprising:

(a) reacting acrylic acid and 1,3-propanediol in a reactor in the presence of an esterification catalyst, with water formed by the reaction being entrained by distillation in a column in the form of a heteroazeotropic mixture with 1,3-propanediol;

(b) condensing the heteroazeotropic mixture of step (a);

(c) separating the condensed heteroazeotropic mixture of step (b) in a decanter thereby yielding an upper organic phase and a lower aqueous phase;

(d) optionally recycling the upper organic phase to the top of the distillation column; and

(e) drawing off the lower aqueous phase.

20 . A process for preparing 1,3-propanediol dimethacrylate comprising transesterifying 1,3-propanediol with an ester of methacrylic acid in the presence of at least one catalyst comprising LiNH 2 and LiCl.

21 . A process for preparing 1,3-propanediol diacrylate comprising:

(a) mixing 1,3-propanediol with triethylamine;

(b) adding acryloyl chloride to the mixture of step (a) to produce triethylamine hydrochloride;

(c) filtering the triethylamine hydrochloride from the mixture of step (b) to produce a filtrate without triethylamine hydrochloride;

(d) drying the filtrate of step (c) over anhydrous magnesium sulfate;

(e) distilling the filtrate of step (d) under reduced pressure thereby removing ether and producing a distilled filtrate; and

(f) vacuum distilling the distilled filtrate in the presence of cuprous chloride to produce 1,3-propanediol diacrylate.

22 . A process for preparing 1,3-propanediol diglycidyl ether comprising:

(a) reacting epichlorohydrin and 1,3-propanediol in a reactor in the presence of a catalyst and toluene;

(b) dehydrochlorinating the product of step (a);

(c) filtering the dehydrochlorinated product of step (b);

(d) neutralizing the filtered product of step (c);

(e) distilling the neutralized product of step (d); and

(f) filtering the distilled product of step (e).

23 . A composite comprising a 1,3-propanediol di-glycidylether component.