Use of a composition of low-viscosity bis-anhydrohexitol ethers as a reactive diluent for crosslinkable resin, adhesive, coating and matrix compositions for composites

Patent metadata

Field	Value
Publication number	US-10913817-B2
Application number	US-201615752203-A
Country	US
Kind code	B2
Filing date	Aug 8, 2016
Priority date	Aug 13, 2015
Publication date	Feb 9, 2021
Grant date	Feb 9, 2021

Abstract

The present invention relates to the use of bis-anhydrohexitol ethers as reactive diluents in a crosslinkable resin, adhesive, coating or composite matrix composition. Not only do these products make it possible to advantageously reduce the viscosity of the mixtures obtained, but they also lead to a very small reduction in the glass transition temperature of the crosslinked mixtures, compared to other reactive diluents, while spectacularly improving the mechanical properties of the latter such as the Young's modulus, the tensile strength, the elongation at break and the toughness.

First claim

The invention claimed is:

1. A process for the preparation of a diluted polymerizable and/or crosslinkable resin, adhesive, coating, or composite matrix composition based on a polymerizable organic epoxy matrix, comprising
adding (i) at least one hardener and/or at least one accelerator and (ii), as a reactive diluent, at least one bis-anhydrohexitol ether of formula (I):

and having a Brookfield viscosity, measured at 20° C., of less than 500 mPa·s to a first composition based on a polymerizable organic epoxy matrix to obtain the diluted polymerizable and/or crosslinkable resin, adhesive, coating or composite matrix composition;
wherein said diluted polymerizable and/or crosslinkable resin, adhesive, coating or composite matrix composition has a lower viscosity than a viscosity of the first composition.

2. The process as claimed in claim 1 , wherein the compound of formula (I) has a Brookfield viscosity, measured at 20° C., of less than 400 mPa·s.

3. The process as claimed in claim 1 , wherein the compound of formula (I) has a Brookfield viscosity, measured at 20° C., of less than 300 mPa·s.

4. The process as claimed in claim 1 , wherein the compound of formula (I) has a Brookfield viscosity, measured at 20° C. of between 50 and 300 mPa·s.

5. The process as claimed in claim 1 , wherein the compound of formula (I) has a Brookfield viscosity, measured at 20° C. of between 100 and 300 mPa·s.

6. The process as claimed in claim 1 , wherein the compound of formula (I) has an epoxy equivalent weight of between 129 and 145 g/eq.

7. The process as claimed in claim 1 , wherein the compound of formula (I) has an epoxy equivalent weight of between 129 and 136 g/eq.

8. The process as claimed in claim 1 , wherein the compound of formula (I) has a weight content of chlorine of less than 0.5%.

9. The process as claimed in claim 1 , wherein the compound of formula (I) has a weight content of chlorine of less than 0.3%.

10. The process as claimed in claim 1 , wherein the polymerizable organic epoxy matrix is selected from the group consisting of bisphenol A glycidyl ethers (DGEBA), phenol novolac resins, cresol novolac resins, bisphenol F-based epoxy resins, cycloaliphatic epoxy resins, and brominated epoxy resins.

11. The process as claimed in claim 10 , wherein the polymerizable organic epoxy matrix is a bisphenol A diglycidyl ether resin.

12. A polymerizable and/or crosslinkable resin, adhesive, coating, or composite matrix composition, said composition comprising:
an epoxy resin as polymerizable and/or crosslinkable organic matrix;
at least one hardener and/or at least one accelerator; and
at least one bis-anhydrohexitol ether of formula (I):

and having a Brookfield viscosity, measured at 20° C., of less than 500 mPa·s and having a role of a reactive diluent in said composition, reducing the viscosity of the epoxy resin as polymerizable and/or crosslinkable organic matrix.

13. The polymerizable and/or crosslinkable composition as claimed in claim 12 , wherein the compound of formula (I) has a Brookfield viscosity, measured at 20° C., of less than 400 mPa·s.

14. The polymerizable and/or crosslinkable composition as claimed in claim 12 , wherein the compound of formula (I) has a Brookfield viscosity, measured at 20° C., of less than 300 mPa·s.

15. The polymerizable and/or crosslinkable composition as claimed in claim 12 , wherein the compound of formula (I) has a Brookfield viscosity, measured at 20° C., of between 50 and 300 mPa·s.

16. The polymerizable and/or crosslinkable composition as claimed in claim 12 , wherein the compound of formula (I) has a Brookfield viscosity, measured at 20° C., of between 100 and 300 mPa·s.

17. The polymerizable and/or crosslinkable composition as claimed in claim 12 , wherein the compound of formula (I) has an epoxy equivalent weight of between 129 and 145 g/eq.

18. The polymerizable and/or crosslinkable composition as claimed in claim 12 , wherein the compound of formula (I) has an epoxy equivalent weight of between 129 and 136 g/eq.

19. The polymerizable and/or crosslinkable composition as claimed in claim 12 , wherein the compound of formula (I) has a weight content of chlorine of less than 0.5%.

20. The polymerizable and/or crosslinkable composition as claimed in claim 12 , wherein the compound of formula (I) has a weight content of chlorine of less than 0.3%.

21. The polymerizable and/or crosslinkable composition as claimed in claim 12 , wherein the epoxy resin as polymerizable and/or crosslinkable organic matrix is selected from the group consisting of bisphenol A glycidyl ethers (DGEBA), phenol novolac resins, cresol novolac resins, bisphenol F-based epoxy resins, cycloaliphatic epoxy resins, and brominated epoxy resins.

22. The polymerizable and/or crosslinkable composition as claimed in claim 21 , wherein the epoxy resin as polymerizable and/or crosslinkable organic matrix is a bisphenol A diglycidyl ether resin.

23. A crosslinked composition obtained from the composition as claimed in claim 12 .

Assignees

• Roquette Freres

Inventors

• Buffe Clothilde
• Pascault Jean-Pierre
• Roi Meizoso Loureiro
• Prendes Gonzales Pilar
• Paz Abuin Senén

Classifications

• C08G59/5026

  cycloaliphatic · CPC title

• C09D163/00

  Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins · CPC title

• C09J11/06

  organic · CPC title

• C09D7/20

  Diluents or solvents · CPC title

• C09J163/00

  Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins · CPC title