Water soluble, high solids urethane coating compositions

• US 4,124,552 A
• Filed: 05/26/1976
• Issued: 11/07/1978
• Est. Priority Date: 05/26/1976
• Status: Expired due to Term

• Current Assignee: Union Carbide Corporation (Dow, Inc.)
• Original Assignee: Union Carbide Corporation (Dow, Inc.)
• Inventors: Smith, Oliver W., Koleske, Joseph V.
• Primary Examiner(s): DE Benedictis, Thomas
• Application Number:
  US05/690,277
• Time in Patent Office: 895 Days
• Field of Search: 260/29.2 TN, 260/29.2 N, 260/29.2 E, 260/77.5 AN
• US Class Current: 524/839
• CPC Class Codes: C08G 18/0823 containing carboxylate salt groups or groups forming them
• CPC Class Codes: C08G 18/4277 Caprolactone and/or substituted caprolactone
• CPC Class Codes: Y10S 528/904 Isocyanate polymer having stated hydrophilic or hydrophobic property

Abstract

Water soluble, high solids urethane coating compositions comprising a polycaprolactone derivative, an aliphatic polyisocyanate and water. The polycaprolactone derivative is a water soluble, carboxyl modified oligomer addition reaction product mixture obtained by the reaction of polycaprolactone polyol and an anhydride of a polycarboxylic acid to produce a water insoluble adduct that on reaction with an inorganic or organic base produces the water soluble, carboxyl modified oligomer addition reaction product mixtures which are eminently suitable for the production of urethane coating compositions of this invention. The polycaprolactone polyol reacted with the polycarboxylic acid has an average at least two hydroxyl groups in the molecule, a hydroxyl number of from about 15 to about 600 and an average molecular weight of from about 290 to about 6,000. The carboxylic acid anhydride has at least one intramolecular carboxylic anhydride group.

Claims

1. A water based high solids urethane coating composition comprising:

(a) an aliphatic polyisocyanate,

(b) a water soluble, carboxyl modified oligomer addition reaction product mixture of the reaction of a polycaprolactone polyol and an intramolecular anhydride of a polycarboxylic acid, wherein said polycaprolactone polyol has at least two hydroxyl groups in the molecule, a hydroxyl number of from 15 to 600 and an average molecular weight of from 290 to about 6,000, and wherein said anhydride has at least one intramolecular carboxylic anhydride group and an inorganic or organic base in an amount sufficient to neutralize the free carboxyl groups of said-addition reaction product mixture, and

(c) water.

2. A water based high solids urethane coating composition as claimed in claim 1, wherein in said component (b) said polycaprolactone polyol has from 2 to 6 hydroxyl groups and said base is an organic amine.

3. A water based high solids urethane coating composition as claimed in claim 1, wherein in said component (b) said polycaprolactone polyol has from 2 to 4 hydroxyl groups and said base is an organic amine.

4. A water based high solids urethane coating composition as claimed in claim 1, wherein in said component (b) said polycaprolactone polyol has a molecular weight of from 290 to 3,000 and said base is an organic amine.

5. A water based high solids urethane coating composition as claimed in claim 1, wherein in said component (b) said polycaprolactone polyol is a triol having an average molecular weight of from 290 to about 500 and said base is an organic amine.

6. A water based high solids urethane coating composition as claimed in claim 1, wherein in said component (b) said polycaprolactone polyol is a mixture of polycaprolactone polyols and said base is an organic amine.

7. A water based high solids urethane coating composition as claimed in claim 1, wherein in said component (b) said anhydride is phthalic anhydride and said base is an organic amine.

8. A water based high solids urethane coating composition as claimed in claim 1, wherein in said component (b) said base is triethylamine.

9. A water based high solids urethane coating composition as claimed in claim 1, wherein in said component (b) said base is N,N-dimethyl ethanolamine.

10. A water based high solids urethane coating composition as claimed in claim 1 wherein said component (a) is 4,4'"'"'-methylene bis(cyclohexyl isocyanate).

11. A water based high solids urethane coating composition as claimed in claim 1 wherein said component (a) is the triisocyanate produced from hexamethylene diisocyanate and water.

12. A water based high solids urethane coating composition as claimed in claim 1 wherein said component (a) is 4,4'"'"'-methylene bis(cyclohexyl isocyanate), said component (b) is the adduct of a mixture of a polycaprolactone triol having an average molecular weight of 540 and a polycaprolactone triol having an average molecular weight of 300 and phthalic anhydride neutralized with N,N-dimethyl ethanolamine.