Process for the production of polyisocyanates containing isocyanurate groups from aliphatic and aromatic isocyanate compounds

• US 5,798,431 A
• Filed: 07/15/1996
• Issued: 08/25/1998
• Est. Priority Date: 07/24/1995
• Status: Expired due to Term

• Current Assignee: Bayer AG
• Original Assignee: Bayer AG
• Inventors: Dieris, Carl-gerd, Halpaap, Reinhard, Brahm, Martin, Schmalstieg, Lutz
• Primary Examiner(s): SERGENT, RABON A
• Application Number:
  US08/679,888
• Time in Patent Office: 771 Days
• Field of Search: 544/193, 544/221, 544/222, 528/52, 528/67, 528/73
• US Class Current: 528/73
• CPC Class Codes: C07D 251/34 Cyanuric or isocyanuric esters
• CPC Class Codes: C08G 18/795 formed by oligomerisation of mixtures of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates with aromatic isocyanates or isothiocyanates

Abstract

A process for the production of polyisocyanates containing isocyanurate groups by the catalytic trimerization of a mixture of low molecular weight isocyanate components having aliphatically and aromatically bound isocyanate groups in the presence of aminosilyl compounds, the resulting polyisocyanates and their use in coating compositions.

Claims

1. A process for the production of an isocyanurate group-containing polyisocyanate which comprises catalytically trimerizing a mixture of

a) 10 to 90 parts by weight of a low molecular weight isocyanate component A) having aliphatically and/or cycloaliphatically bound isocyanate groups, an average molecular weight of 128 to 800 and an average NCO functionality of 1.7 to 2.2 and

b) 10 to 90 parts by weight of a low molecular weight isocyanate component B) having aromatically bound isocyanate groups, an average molecular weight of 148 to 800 and an average NCO functionality of 1.7 to 2.2,

in the presence of 0.1 to 10 parts by weight, per 100 parts by weight of isocyanate components A) and B), of an aminosilyl compound C) corresponding to the formula ##STR2## wherein R¹ represents hydrogen or a saturated or unsaturated C₁ -C22 aliphatic, C₅ -C₂₀ cycloaliphatic or C₆ -C₂₄ aromatic hydrocarbons optionally substituted with Cl or Br,

R² represents a saturated or unsaturated C₁ -C₂₂ aliphatic, C₅ -C₂₀ cycloaliphatic or C₆ -C₂₄ aromatic hydrocarbons optionally substituted with Cl or Br or represents the group SiR³ R⁴ R⁵ group, provided that R¹ and R² may also form a heterocyclic ring having 2 to 6 carbon atoms in which carbon atoms present in the ring may be replaced by heteroatoms and

R³, R⁴ and R⁵ are the same or different and represent saturated or unsaturated C₁ -C₂₂ aliphatic, C₁ -C₂₀ cycloaliphatic or C₆ -C₂₄, aromatic hydrocarbons optionally substituted with Cl or Br,

and subsequently removing excess, distillable isocyanate components A) and B) to obtain a polyisocyanate having a monomer content of less than 0.7%, based on the weight of polyisocyanate solids.

2. The process of claim 1 in which isocyanate components A) and B) are diisocyanates.

3. The process of claim 1 wherein isocyanate component A) comprises 1,6-diisocyanatohexane and isocyanate component B) comprises 2,4- and/or 2,6-tolylene diisocyanate.

4. The process of claim 1 wherein isocyanate component A) is present in an amount of 20 to 70 parts by weight and isocyanate component B) is present in an amount of 30 to 80 parts by weight.

5. The process of claim 2 wherein isocyanate component A) is present in an amount of 20 to 70 parts by weight and isocyanate component B) is present in an amount of 30 to 80 parts by weight.

6. The process of claim 3 wherein isocyanate component A) is present in an amount of 20 to 70 parts by weight and isocyanate component B) is present in an amount of 30 to 80 parts by weight.

7. The process of claim 1 wherein 0.8 to 5 parts by weight of an aminosilyl compound C) are present per 100 parts by weight of isocyanate components A) and B).

8. The process of claim 1 wherein catalyst C) comprises an N-silylated heterocyclic.

9. The process of claim 2 wherein catalyst C) comprises an N-silylated heterocyclic.

10. The process of claim 6 wherein catalyst C) comprises an N-silylated heterocyclic.

11. The process of claim 1 wherein catalyst C) comprises an N-silylated cyclic amine containing at least one heteroatom in the ring in addition to nitrogen.

12. The process of claim 2 wherein catalyst C) comprises an N-silylated cyclic amine containing at least one heteroatom in the ring in addition to nitrogen.

13. The process of claim 6 wherein catalyst C) comprises an N-silylated cyclic amine containing at least one heteroatom in the ring in addition to nitrogen.

14. An isocyanurate group-containing polyisocyanate which is prepared by a process comprising catalytically trimerizing a mixture of

a) 10 to 90 parts by weight of a low molecular weight isocyanate component A) having aliphatically and/or cycloaliphatically bound isocyanate groups, an average molecular weight of 128 to 800 and an average NCO functionality of 1.7to 2.2 and

b) 10 to 90 parts by weight of a low molecular weight isocyanate component B) having aromatically bound isocyanate groups, an average molecular weight of 148 to 800 and an average NCO functionality of 1.7 to 2.2,

in the presence of 0.1 to 10 parts by weight, per 100 parts by weight of isocyanate components A) and B), of an aminosilyl compound C) corresponding to the formula ##STR3## wherein R¹ represents hydrogen or a saturated or unsaturated C₁ -C₂₂ aliphatic, C₅ -C₂₀ cycloaliphatic or C₆ -C₂₄ aromatic hydrocarbons optionally substituted with Cl or Br,

R² represents a saturated or unsaturated C₁ -C₂₂ aliphatic, C₅ -C₂₀ cycloaliphatic or C₆ -C₂₄ aromatic hydrocarbons optionally substituted with Cl or Br or represents the group SiR³ R⁴ R⁵ group, provided that R¹ and R² may also form a heterocyclic ring having 2 to 6 carbon atoms in which carbon atoms present in the ring may be replaced by heteroatoms and

R³, R⁴ and R⁵ are the same or different and represent saturated or unsaturated C₁ -C22 aliphatic, C₅ -C₂₀ cycloaliphatic or C₆ -C₂₄ aromatic hydrocarbons optionally substituted with Cl or Br,

and subsequently removing excess, distillable isocyanate components A) and B) to obtain a polyisocyanate having a monomer content of less than 0.7%, based on the weight of polyisocyanate solids.

15. The polyisocyanate of claim 14 in which isocyanate components A) and B) are diisocyanates.

16. The polyisocyanate of claim 14 wherein isocyanate component A) comprises 1,6-diisocyanatohexane and isocyanate component B) comprises 2,4- and/or 2,6-tolylene diisocyanate.

17. The polyisocyanate of claim 14 wherein isocyanate component A) is present in an amount of 20 to 70 parts by weight and isocyanate component B) is present in an amount of 30 to 80 parts by weight.

18. The polyisocyanate of claim 15 wherein isocyanate component A) is present in an amount of 20 to 70 parts by weight and isocyanate component B) is present in an amount of 30 to 80 parts by weight.

19. The polyisocyanate of claim 16 wherein isocyanate component A) is present in an amount of 20 to 70 parts by weight and isocyanate component B) is present in an amount of 30 to 80 parts by weight.

20. A coating composition in which the binder comprises the polyisocyanate of claim 14.