Reaction product of mixed uretdiones and a disecondary diamine

• US 5,912,314 A
• Filed: 03/17/1997
• Issued: 06/15/1999
• Est. Priority Date: 03/16/1996
• Status: Expired due to Fees

• Current Assignee: Degussa AG (Rag-Stiftung)
• Original Assignee: Huels Aktiengesellschaft
• Inventors: Wolf, Elmar
• Primary Examiner(s): SERGENT, RABON A
• Application Number:
  US08/819,365
• Time in Patent Office: 820 Days
• Field of Search: 540/202, 528/271, 528/220, 528/228, 528/229, 528/230, 528/45, 528/61, 528/67, 528/68, 528/59, 528/73, 525/452, 548/951, 548/952, 564/57, 564/59, 564/60, 564/61
• US Class Current: 528/45
• CPC Class Codes: C08G 18/325 containing secondary or tertiary amino groups C08G18/3228, C08G18/3234, C08G18/3246 take precedence
• CPC Class Codes: C08G 18/798 containing urethdione groups
• CPC Class Codes: C08G 18/8038 with compounds of C08G18/3225
• CPC Class Codes: C08G 18/8061 masked with compounds having only one group containing active hydrogen
• CPC Class Codes: C08G 2150/20 Compositions for powder coatings

Abstract

A Polyaddition product, containing uretdione groups, which is obtainable by reaction of (A) a diisocyanate mixture which contains uretdione groups and comprises (1) at least 40 mol % to not more than 80 mol % of isophorone diisocyanate containing uretdione groups and (2) not more than 60 mol % and not less than 20 mol % of hexamethylene diisocyanate containing uretdione groups, with (B) a disecondary diamine, in an NCO/NH ratio of 1:0.5 to 1:0.9 at room temperature to 60° C. in a solvent which is inert towards isocyanates.

Claims

1. A polyaddition product, containing uretdione groups, which is prepared by reacting (A) a diisocyanate mixture which contains uretdione groups and comprises (1) at least 40 mol. % to not more than 80 mol. % of isophorone diisocyanate containing uretdione groups and (2) not more than 60 mol. % and not less than 20 mol. % of hexamethylene diisocyanate containing uretdione groups, the mol. % amounts based on the total molar amount of diisocyanate mixture (A), with (B) a disecondary diamine, in an NCO/NH ratio of 1:

0.5-1;

0.9 at room temperature to 60°

C. in a solvent which is inert towards isocyanates.

2. The polyaddition product as claimed in claim 1, wherein the polyaddition product is completely or partly blocked with a blocking agent selected from at least one of monoalcohols and monoamines.

3. The polyaddition product as claimed in claim 1, wherein the disecondary diamine is prepared by condensation of a diamine selected from the group consisting of ethylenediamine, 1,2-diaminopropane, 2-methylpentamethylenediamine, hexamethylenediamine, 2,2,4(2,4,4)-trimethylhexamethylenediamine, isophoronediamine (IPD), 1,2diaminocyclohexane and 1,3-bis(aminomethyl)-benzene with a carbonyl-containing compound selected from the group consisting of isobutyraldehyde, 2-ethylhexanal, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone and 3,5,5-trimethylcyclohexanone, to form a Schiff'"'"'s base, and subsequent hydrogenation of the Schiff'"'"'s base.

4. The polyaddition product as claimed in claim 2, wherein the disecondary diamine is prepared by condensation of a diamine selected from the group consisting of ethylenediamine, 1,2-diaminopropane, 2-methylpentamethylenediamine, hexamethylenediamine, 2,2,4(2,4,4)-trimethylhexamethylenediamine, isophoronediamine (IPD), 1,2diaminocyclohexane and 1,3-bis(aminomethyl)-benzene with a carbonyl-containing compound selected from the group consisting of isobutyraldehyde, 2-ethylhexanal, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone and 3,5,5-trimethylcyclohexanone, to form a Schiff'"'"'s base, and subsequent hydrogenation of the Schiff'"'"'s base.

5. The polyaddition product as claimed in claim 1, wherein the disecondary diamine is prepared by reacting a diprimary diamine with an acrylic acid ester.

6. The polyaddition product as claimed in claim 2, wherein the disecondary diamine is prepared by reacting a diprimary diamine with an acrylic acid ester.

7. The polyaddition product as claimed in claim 5, wherein the acrylic acid ester is methyl, ethyl, butyl or 2-ethylhexyl acrylate.

8. The polyaddition product as claimed in claim 6, wherein the acrylic acid ester is methyl, ethyl, butyl or 2-ethylhexyl acrylate.

9. The polyaddition product as claimed in claim 1 which has a molecular weight range of 1200-10000, a melting point of 70-150°

C., and a latent NCO content of 8-18%.

10. The polyaddition product as claimed in claim 2 which has a molecular weight range of 1200-10000, a melting point of 70-150°

C., and a latent NCO content of 8-18%.

11. The polyaddition product as claimed in claim 1 which has a molecular weight range of 2500-6500, a melting point of 80-130°

C., and a latent NCO content of 10-16%.

12. The polyaddition product as claimed in claim 2 which has a molecular weight range of 2500-6500, a melting point of 80-130°

C., and a latent NCO content of 10-16%.

13. The polyaddition product as claimed in claim 2, wherein the blocking agent is selected from the group consisting of n-butanol, 2-ethylhexanol, butylamine, hexylamine, 2-ethylhexylamine, dibutylamine dihexylamine.

14. The polyaddition product as claimed in claim 4, wherein the blocking agent is selected from the group consisting of n-butanol, 2-ethylhexanol, butylamine, hexylamine, 2-ethylhexylamine, dibutylamine dihexylamine.

15. The polyaddition product as claimed in claim 6, wherein the blocking agent is selected from the group consisting of n-butanol, 2-ethylhexanol, butylamine, hexylamine, 2-ethylhexylamine, dibutylamine dihexylamine.

16. The polyaddition product as claimed in claim 8, wherein the blocking agent is selected from the group consisting of n-butanol, 2-ethylhexanol, butylamine, hexylamine, 2-ethylhexylamine, dibutylamine dihexylamine.

18. A method of hardening a compound which is at least difunctional and contains Zerewittinoff-active hydrogen atoms, which comprises reacting said compound with the polyaddition product as claimed in claim 1.

19. A method of hardening a compound which is at least difunctional and contains Zerewittinoff-actve hydrogen atoms, which comprises reacting said compound with the polyaddition product as claimed in claim 2.

20. A composition for use in a polyurethane powder coating comprising the polyaddition product claimed in claim 1 and a hardener which is at least difunctional and contains Zerewittinoff-active hydrogen atoms.

17. A process for the preparation of a polyaddition product, containing uretdione groups, which comprises reacting (A) a diisocyanate mixture which contain s uretdione groups and comprises (1) at least 40 mol % to not more than 80 mol % of isophorone diisocyanate containing uretdione groups and (2) not more than 60 mol % and not less than 20 mol % of hexamethylene diisocyanate containing uretdione groups, the mol. % amounts based on the total molar amount of diisocyanate mixture (A), with (B) a disecondary diamine, in an NCO/NH ratio of 1:

0.5-1;

09 at room temperature to 60°

C. in a solvent which is inert towards isocyanates, and optionally further reacting the polyaddition product thus obtained, completely or partly, with at least one blocking agent selected from the group consisting of monoalcohols and monoamines.