Polylactone-polyurethanes and aqueous dispersions thereof

• US 4,098,743 A
• Filed: 05/26/1976
• Issued: 07/04/1978
• Est. Priority Date: 05/26/1976
• Status: Expired due to Term

• Current Assignee: PPG Industries Incorporated (Nouryon BV)
• Original Assignee: PPG Industries Incorporated (Nouryon BV)
• Inventors: Scriven, Roger L., Chang, Wen-Hsuan
• Primary Examiner(s): Cockeram, H.S.
• Application Number:
  US05/690,338
• Time in Patent Office: 769 Days
• Field of Search: 260/29.2 R, 260/29.2 TN, 260/78.3 R, 260/77.5 AN, 260/849, 260/29.2 N
• US Class Current: 524/590
• CPC Class Codes: C08G 18/0819 containing anionic or anionogenic groups
• CPC Class Codes: C08G 18/4269 Lactones
• CPC Class Codes: C08G 63/08 Lactones or lactides

Abstract

Water-soluble polylactones and poly(lactone-urethanes) are disclosed. The polylactones are prepared by ring opening a lactone such as epsilon-caprolactone with a low equivalent weight active hydrogen-containing material having at least two active hydrogen groups per molecule selected from the class consisting of hydroxyl, primary amine, secondary amine and thiol, and having anionic water-solubilizing groups or groups which are readily reacted to form anionic water-solubilizing groups. The resulting polylactone can be combined with curatives such as amine-aldehyde condensates to form water-soluble coating compositions and can be reacted with polyisocyanates to form unique water-soluble poly(lactone-urethanes, ureas or thiolurethanes) which are also useful for coating applications.

Surprisingly, it has been found that the polyurethanes prepared by reacting organic polyisocyanates with the novel polylactone adducts of the present invention and optionally low molecular weight diols are more water dispersible and form coatings with greater adhesion to the substrate and less water sensitivity than comparable polyurethanes prepared by reacting organic polyisocyanates with conventional polylactone diols and low equivalent weight active hydrogen-containing materials which also have anionic water-solubilizing groups.

Claims

1. In a process which comprises reactting a lactone of the formula:

##STR7## wherein n is an integer of from 4 to 6, and wherein at least (n+2) R'"'"'s are hydrogen and wherein the remaining R'"'"'s are of the group consisting of hydrogen, alkyl, cycloalkyl, alkoxy and single ring aromatic hydrocarbon radicals with an active hydrogen-containing material so as to produce a polylactone having recurring ##STR8## moieties in the polymer backbone, wherein the variables n and R have the aforesaid meanings, the improvement comprising;

reacting the lactone with an active hydrogen-containing material having at least 2 active hydrogen groups per molecule selected from the class consisting of hydroxyl, primary amine, secondary amine and thiol and having anionic water-solubilizing groups or groups which are readily reacted to form anionic water-solubilizing groups;

said active hydrogen-containing material having an ionic equivalent weight of less than 1000, the equivalent ratio of lactone to active hydrogen-containing material being at least 0.5;

1.

2. The process of claim 1 in which the lactone is epsilon-caprolactone.

3. The process of claim 1 in which the active hydrogen-containing material has the following structural formula:

##STR9## where R is hydrogen, an alkyl group containing from 1 to 12 carbon atoms or CH₂ OH.

4. The process of claim 1 in which the polylactone has as ionic equivalent weight of less than 4000.

5. The polylactone prepared by the process of claim 1 in combination with at least one percent of an amine-aldehyde condensate.

6. The combination of claim 5 containing 25 to 95 percent by weight of polylactone and 5 to 75 percent by weight of amine-aldehyde condensate, the percentage by weight being based on total weight of polylactone and amine-aldehyde condensate.

7. An aqueous dispersion of the polylactone prepared by the process of claim 1 in which the polylactone constitutes from 20 to 85 percent by weight of the dispersion based on total weight of the polylactone and aqueous medium.

8. The aqueous dispersion of claim 7 which contains about 30 to 80 percent by weight polylactone based on total weight of the polylactone and aqueous medium.

9. The product prepared by the process of claim 1.

10. In an ungelled polyurethane comprising the reaction product of an organic polyisocyanate and a polylactone, the improvement comprising employing a polylactone formed from reacting a lactone of the formula:

##STR10## where n is an integer of from 4 to 6, and where at least (n+2) R'"'"'s are hydrogen, and the remaining R'"'"'s are of the group consisting of hydrogen, alkyl, cycloalkyl, alkoxy and single ring aromatic hydrocarbon radicals with an active hydrogen-containing material so as to produce a polylactone having recurring ##STR11## moieties in the polymer backbone, wherein the variables n and R have the aforesaid meanings;

said active hydrogen-containing material having at least 2 active hydrogen groups per molecule selected from the class consisting of hydroxyl, primary amine, secondary amine and thiol and having anionic water-solubilizing groups or groups which are readily reacted to form anionic water-solubilizing groups and having an ionic equivalent weight of less than 1000, the equivalent ratio of lactone to active hydrogen-containing material being at least 0.5;

1.

11. The polyurethane of claim 10 in which the lactone is epsilon-caprolactone.

12. The polyurethane of claim 10 in which the active hydrogen-containing material has the following structural formula:

##STR12## where R is hydrogen, an alkyl group containing from 1 to 12 carbon atoms or CH₂ OH.

13. The polyurethane of claim 10 in which the polylactone has an ionic equivalent weight less than 4000.

14. The polyurethane of claim 10 combination with at least one percent of an amine-aldehyde condensate.

15. The combination of claim 14 containing from about 25 to 95 percent by weight of polyurethane and 5 to 75 percent by weight of amine-aldehyde condensate;

the percentages by weight being based on total weight of the polyurethane and amine-aldehyde condensate.

16. An aqueous dispersion of the polyurethane of claim 10 in which the polyurethane constitutes from 20 to 85 percent by weight of the dispersion based on total weight of the polyurethane and aqueous medium.

17. The aqueous dispersion of claim 16 which contains from about 30 to 80 percent by weight polyurethane based on total weight of the polyurethane and aqueous medium.

18. A coating composition comprising the polyurethane of claim 10, in combination with pigment.

19. The coating composition of claim 18 which contains a curing agent for the polyurethane in which the curing agent is capable of reacting with the reactive hydrogens of the polyurethane to bring about chemical crosslinking after a film of the polyurethane is deposited on a substrate at room temperature or elevated temperature.

20. The coating compositon of claim 19 in which the crosslinker is an amine-aldehyde condensate.