Diethyloctandioldicarbamates and diethyloctandioldiallophanates, method for the production and use thereof

• US 20030023017A1
• Filed: 07/22/2002
• Published: 01/30/2003
• Est. Priority Date: 02/02/2000
• Status: Active Grant

• Current Assignee: BASF Coatings AG (BASF SE)
• Original Assignee: BASF Coatings AG (BASF SE)
• Inventors: Rink, Heinz-Peter, Harris, Paul J, Henkelmann, Jochem, Jung, Werner-Alfons, Ramesh, Swaminathan
• Granted Patent: US 6,878,841 B2
• Time in Patent Office: Days
• US Class Current: 526/301
• CPC Class Codes: C07C 271/12 to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
• CPC Class Codes: C07C 275/60 Y being an oxygen atom, e.g. allophanic acids
• CPC Class Codes: C08K 5/205 Compounds containing groups, e.g. carbamates
• CPC Class Codes: C08K 5/21 Urea; Derivatives thereof, e.g. biuret

Abstract

The invention relates to positional isomer diethyloctandioldicarbamates and diethyloctandioldiallophanates, to a method for the production thereof and to the use thereof as synthetic building blocks and constituents of adhesives, luting compounds and coating materials.

Claims

1. Positionally isomeric diethyloctanediol dicarbamates and diethyloctanediol diallophanates.

2. The positionally isomeric diethyloctanediol dicarbamates and diethyloctanediol diallophanates as claimed in claim 1, which contain primary carbamate or allophanate groups.

3. The positionally isomeric diethyloctanediol dicarbamates and diethyloctanediol diallophanates as claimed in claim 1 or 2, whose linear C8 carbon chain has the following substitution pattern with regard to the two ethyl groups:

2,3, 2,4, 2,5, 2,6, 2,7, 3,4, 3,5, 3,6 or 4,5.

4. The positionally isomeric diethyloctanediol dicarbamates and diethyloctanediol diallophanates as claimed in claim 3, wherein the two ethyl groups are in positions 2 and 4.

5. The positionally isomeric diethyloctanediol dicarbamates and diethyloctanediol diallophanates as claimed in any of claims 1 to 4, whose C8 carbon chain has the following substitution pattern with regard to the two carbamate groups or allophanate groups:

1,2, 1,3, 1,4, 1,5, 1,6, 1,7, 1,8, 2,3, 2,4, 2,5, 2,6, 2,7, 2,8, 3,4, 3,5, 3,6, 3,7, 3,8, 4,5, 4,6, 4,8, 5,6, 5,7, 5,8, 6,7, 6,8 or 7,8.

6. The positionally isomeric diethyloctanediol dicarbamates and diethyloctanediol diallophanates as claimed in claim 5, wherein the two carbamate groups or allophanate groups are in positions 1 and 5.

7. The positionally isomeric diethyloctanediol dicarbamates and diethyloctanediol diallophanates as claimed in claim 6, which are 2,4-diethyloctane-1,5-diol dicarbamate and 2,4-diethyloctane-1,5-diol diallophanate.

8. A process for preparing positionally isomeric diethyloctanediol dicarbamates as claimed in any of claims 1 to 7 from diethyloctanediols, which comprises reacting positionally isomeric diethyloctanediols with alkyl, cycloalkyl or aryl carbamates.

9. A process for preparing positionally isomeric diethyloctanediol dicarbamates as claimed in any of claims 1 to 7 from diethyloctanediols, which comprises the reaction of positionally isomeric diethyloctanediols with phosgene to give the corresponding chloroformates and reacting these intermediates with ammonia and/or amines.

10. A process for preparing positionally isomeric diethyloctanediol diallophanates as claimed in any of claims 1 to 7 from diethyloctanediols, which comprises the reaction of positionally isomeric diethyloctanediols with alkyl, cycloalkyl or aryl allophanates.

11. The process as claimed in any of claims 8 to 10, wherein the linear C8 carbon chain of the positionally isomeric diethyloctanediols has the following substitution pattern with regard to the two ethyl groups:

2,3, 2,4, 2,5, 2,6, 2,7, 3,4, 3,5, 3,6 or 4,5.

12. The process as claimed in claim 11, wherein the two ethyl groups are in positions 2 and 4.

13. The process as claimed in any of claims 8 to 12, wherein the C8 carbon chain of the positionally isomeric diethyloctanediols has the following substitution pattern with regard to the two hydroxyl groups:

1,2, 1,3, 1,4, 1,5, 1,6, 1,7, 1,8, 2,3, 2,4, 2,5, 2,6, 2,7, 2,8, 3,4, 3,5, 3,6, 3,7, 3,8, 4,5, 4,6, 4,8, 5,6, 5,7, 5,8, 6,7, 6,8 or 7,8.

14. The process as claimed in claim 13, wherein the two hydroxyl groups are in positions 1 and 5.

15. The process as claimed in claim 14, wherein 2,4-diethyloctane-1,5-diol is used.

16. The use of the positionally isomeric diethyloctanediol dicarbamates and diethyloctanediol diallophanates as claimed in any of claims 1 to 7, of the positionally isomeric diethyloctanediol dicarbamates prepared with the aid of the process as claimed in any of claims 8, 9 and 11 to 15, and of the diethyloctanediol diallophanates prepared with the aid of the process as claimed in any of claims 10 to 15 as synthesis building blocks in low-molecular and high-molecular organic chemistry and in organometallic chemistry.

17. The use of the positionally isomeric diethyloctanediol dicarbamates and diethyloctanediol diallophanates as claimed in any of claims 1 to 7, of the positionally isomeric diethyloctanediol dicarbamates prepared with the aid of the process as claimed in any of claims 8, 9 and 11 to 15, and of the diethyloctanediol diallophanates prepared with the aid of the process as claimed in any of claims 10 to 15 for the preparation of adhesives, sealing compounds, and coating materials curable thermally, or thermally and with actinic radiation.

18. Adhesives, sealing compounds and coating materials curable thermally, or thermally and with actinic radiation, comprising at least one of the diethyloctanediol dicarbamates and/or at least one of the diethyloctanediol diallophanates as claimed in any of claims 1 to 7 and/or at least one of the diethyloctanediol dicarbamates prepared with the aid of the process as claimed in any of claims 8, 9 and 11 to 15 and/or at least one of the diethyloctanediol diallophanates prepared with the aid of the process as claimed in any of claims 10 to 15.

19. Adhesive films, seals, and coatings on and in primed and unprimed substrates, which can be produced from the adhesives, sealing compounds, and coating materials, as claimed in claim 18, curable thermally, or thermally and with actinic radiation.

20. Primed and unprimed substrates with adhesive films, seals and/or coatings as claimed in claim 19.