Water-dispersible allyl urethanes and their use for the production of paints

• US 5,089,586 A
• Filed: 08/16/1989
• Issued: 02/18/1992
• Est. Priority Date: 09/01/1988
• Status: Expired due to Fees

• Current Assignee: Wolff Walsrode AG (Dow, Inc.)
• Original Assignee: Wolff Walsrode AG (Dow, Inc.)
• Inventors: Piepho, Michael, Luhmann, Erhard, Hoppe, Lutz
• Primary Examiner(s): Kight, III, John
• Assistant Examiner(s): Truong, Duc
• Application Number:
  US07/394,601
• Time in Patent Office: 916 Days
• Field of Search: 528/75, 528/49, 528/60, 528/65, 528/66
• US Class Current: 528/75
• CPC Class Codes: C08G 18/42 Polycondensates having carboxylic or carbonic ester groups in the main chain
• CPC Class Codes: C08G 18/48 Polyethers
• CPC Class Codes: C08G 18/4833 Polyethers containing oxyethylene units
• CPC Class Codes: C08G 18/4887 containing carboxylic ester groups derived from carboxylic acids other than acids of higher fatty oils or other than resin acids
• CPC Class Codes: C08G 18/6715 Unsaturated monofunctional alcohols or amines
• CPC Class Codes: C08G 18/675 Low-molecular-weight compounds
• CPC Class Codes: C08G 18/6795 Unsaturated polyethers
• CPC Class Codes: C08G 18/68 Unsaturated polyesters
• CPC Class Codes: C09D 175/14 Polyurethanes having carbon-to-carbon unsaturated bonds

Abstract

Improved water-dispersible allyl urethanes are obtainable by reaction of a polyglycol mixture with a hydroxyallyl compound and an isocyanate containing at least two NCO groups, the allyl urethane being nonionic.

Claims

1. Water-dispersible allyl urethanes prepared from an allyl compound, a polyol and an isocyanate, characterized in that they are obainable by reaction of

A) a polyglycol mixture I or its reaction product with a polycarboxylic acid II or a derivative IIa thereof with

B) a hydroxyallyl compound III and an isocyanate IV containing at least two isocyanate groups,

the allyl urethanes being nonionic.

2. Water-dispersible allyl urethanes as claimed in claim 1, characterized in that the molar ratio of polyglycols having a molecular weight below 1000 to polyglycols having a molecular weight of at least 1000 in the polyglycol mixture I is between 10 and 50.

3. Water-dispersible allyl urethanes as claimed in claim 1, characterized in that a non-aromatic α

,β

-unsaturated carboxylic acid II or a derivative IIa thereof is used in the production process.

4. Water-dispersible allyl urethanes as claimed in claim 1 obtainable by reaction of 0.15 mol hydroxyl groups of starting product A built up of0.03-0.1 mol of a polyethylene glycol having a molecular weight of at least 200, but below 1000,0.002-0.02 mol of a polyethylene glycol having a molecular weight of 1000 to 5000,0.00-0.3 mol of an optionally branched polypropylene glycol having a molecular weight of 200 to 1000 and0.0-0.25 mol of a polycarboxylic acid II or a derivative IIa thereof

with

0.05-0.35 mol of the hydroxyallyl compound III and0.1-0.5 mol isocyanate groups of the isocyanate compound IV

in a reaction step B, all the isocyanate groups being reacted with hydroxyl groups.

5. Water-dispersible allyl urethanes as claimed in claim 1, characterized in that maleic anhydride and/or adipic acid, fumaric acid, malonic acid, phthalic acid, phthalic anhydride, hydrogenated phthalic acid derivatives, itaconic acid, succinic acid, valeric acid and/or citric acid is/are used as the polycarboxylic acid II or derivatives IIa thereof.

6. Water-dispersible allyl urethanes as claimed in claim 1, characterized in that isophorone diisocyanate, hexamethylene diisocyanate, dicyclohexyl methane diisocyanate, MDI or TDI, is used, optionally in prepolymer form, as the isocyanate IV.

7. Water-dispersible allyl urethanes as claimed in claim 1, characterized in that trimethylolpropane diallyl ether and/or trimethylolpropane monoallyl ether, pentaerythritol triallyl ether, glycerol monoallyl ether, glycerol diallyl ether, pentaerythritol diallyl ether, is used as the hydroxyallyl compound III.

8. A process for the production of a water-dispersible allyl urethane as claimed in claim 1 by reaction of

A) a polyglycol mixture I or reaction products thereof with a polycarboxylic acid II or a derivative IIa thereof with

B) a hydroxyallyl compound III and an isocyanate IV containing at least two NCO groups,

the reaction being carried out in such a way that no ionic groups are obtained in the allyl urethane.

9. A process for the production of a lacquer, characterized in that an allyl urethane of the type claimed in claim 1 is dispersed in water and the resulting dispersion is provided with standard additives.

10. A process for coating rigid or flexible substrates, characterized in that a lacquer obtained by the process claimed in claim 9 is used.