Heat-curable coating compositions

• US 5,276,125 A
• Filed: 11/21/1990
• Issued: 01/04/1994
• Est. Priority Date: 12/02/1989
• Status: Expired due to Fees

• Current Assignee: Bayer AG
• Original Assignee: Bayer AG
• Inventors: Kling, Waldemar, Schroer, Walter, Dietrich, Manfred, Pedain, Josef, Thoma, Wilhelm
• Primary Examiner(s): Kight, III, John
• Assistant Examiner(s): Truong, Duc
• Application Number:
  US07/616,546
• Time in Patent Office: 1,140 Days
• Field of Search: 528/44, 528/45, 528/49, 528/77, 528/81, 528/83, 525/113, 525/114, 525/116
• US Class Current: 528/45
• CPC Class Codes: C08G 18/0819 containing anionic or anionogenic groups
• CPC Class Codes: C08G 18/10 Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
• CPC Class Codes: C08G 18/286 Oximes
• CPC Class Codes: C08G 18/3234 cycloaliphatic
• CPC Class Codes: C08G 18/40 High-molecular-weight compounds C08G18/2805 takes precedence
• CPC Class Codes: C08G 18/409 Dispersions of polymers of C08G in organic compounds having active hydrogen
• CPC Class Codes: C08L 2666/20 Macromolecular compounds having nitrogen in the main chain according to C08L75/00 - C08L79/00; Derivatives thereof
• CPC Class Codes: C09D 175/04 Polyurethanes

Abstract

The present invention relates to heat-curable coating compositions containing

A) a prepolymer having an average of 2-4 ketoxime-blocked NCO groups, having an average moleculer weight of 500-15,000 and prepared from aliphatic, cycloaliphatic and aromatic polyisocyanates and one or more polyhydroxy components which contain 0 to 30% by weight of ethylene oxide units and

B) a crosslinking agent of the formula ##STR1## wherein R and R¹ represent H or C₁ -C₄ -alkyl, the ratio of equivalents of blocked NCO groups in A) to NH₂ groups in B) being 1.35:1 to 0.95:1, characterized in that at least one of the polyhydroxy compounds used for the preparation of the prepolymer contains, in stable dispersion, a polyurethane, a polyurethane-urea and/or a polyurea, which is substantially free from NCO groups, hydroxyl groups and amino groups and which are synthesized from aromatic, aliphatic and/or cycloaliphatic diisocyanates and from diamines, hydrazine and/or diols, provided that at least one of these components carries a radical having hydrophilic characteristics.

The present invention also relates to the use of these coating compositions in a process for the coating, particularly water vapor-permeable coating, of substrates, preferably textile sheet-like structures and leather.

Claims

1. A heat-curable coating composition comprising

A) a prepolymer which has an average of 2-4 ketoxime-blocked NCO groups and an average molecular weight of 500-15,000 and which is prepared from

i) an aliphatic, cycloaliphatic or aromatic polyisocyanate and

ii) a polyhydroxy component having an average ethylene oxide content of 0 to 30% by weight and comprising at least one polyhydroxy compound containing a stable dispersion of a member selected from the group consisting of polyurethanes, polyurethane-ureas and polyureas, which are substantially free from NCO groups, hydroxyl groups and amino groups and which are based on the reaction product of

a) a diisocyanate having aromatically-, aliphatically- and/or cycloaliphatically-bound isocyanate groups and

b) a compound selected from the group consisting of diamines, hydrazine, diols and mixtures thereof, wherein at least one of these compounds contains a hydrophillic group and

iii) a ketoxime blocking agent, and

B) a crosslinking agent of the formula ##STR3## wherein R and R¹ represent H or C₁ -C₄ -alkyl group, the equivalent ratio of blocked NCO groups in A) to NH₂ groups in B) being 1.35:

1 to 0.95;

1.

2. The composition of claim 1 wherein component a), comprises a toluylene diisocyanate or isophorone diisocyanate;

component b) comprises isophoronediamine or hydrazine hydrate; and

the hydrophilic group is present in a compound selected from the group consisting of diaminopolyethers having ethylene oxide units, dihydroxy polyethers having ethylene oxide units, and alkali metal and ammonium salts of dimethylolpropionic acid, ethylene diamine ethyl sulphonic acid, glutamic acid and lysine.

3. The composition of claim 1 wherein component B) comprises 4,4'"'"'-diamino-3,3'"'"'-dimethyl-dicyclohexylmethane.

4. The composition of claim 1 wherein 5-100 mole percent of component b) comprises a salt of a dihydroxycarboxylic acid, a diaminoalkylsulphonic acid, a diaminocarboxylic acid or mixtures thereof.

5. The composition of claim 1 wherein the ratio of hydrophilic polyurethanes, polyurethane-ureas and polyureas to hydrophobic polyurethanes, polyurethane-ureas and polyureas is 95:

5 to 10;

90.

6. The composition of claim 1 wherein the solids content is 70-100 % by weight.

7. The composition claim 1 wherein polyhydroxy component ii) comprises a mixture of a polyhydroxy polyether and a polyhydroxy polyester.

8. The composition of claim 7 wherein 30 to 99% by weight of the mixture comprises a polyhydroxy polyether.

9. The composition of claim 1 wherein component a) comprises a mixture of 2,4- and 2,6-toluylene diisocyanate in an isomer ratio of 80:

20 and component b) comprises a mixture of hydrazine hydrate and sodium ethylene diamine-β

-ethylsulphonate.

10. A water vapor-permeable coating prepared from the composition of claim 1.