Aqueous adhesive composition comprising a ithermosetting resin

Patent metadata

Field	Value
Publication number	US-11268000-B2
Application number	US-201716090423-A
Country	US
Kind code	B2
Filing date	Apr 3, 2017
Priority date	Apr 1, 2016
Publication date	Mar 8, 2022
Grant date	Mar 8, 2022

Abstract

An aqueous adhesive composition comprises a thermosetting resin based on: at least one aromatic compound bearing at least two functions, one of these functions being a hydroxymethyl function and the other being an aldehyde function or a hydroxymethyl function, the aromatic compound comprising at least one aromatic ring; and at least aromatic polyphenol comprising at least one aromatic ring bearing at least two hydroxyl functions in the meta position relative to one another, the two positions ortho to at least one of the hydroxyl functions being unsubstituted. Such an adhesive composition may especially be used to join elements made of wood; it constitutes an advantageous alternative to the use of a formaldehyde-based phenolic resin adhesive.

First claim

The invention claimed is:

1. An aqueous adhesive composition comprising a thermosetting resin based on:
(A1) at least one aromatic compound comprising at least one aromatic ring bearing at least two functions, one of these functions being a hydroxymethyl function and the other being an aldehyde function or a hydroxymethyl function; and
(A2) at least one aromatic polyphenol comprising:
at least one aromatic ring bearing three hydroxyl functions in the meta position relative to one another, wherein, for at least one of the hydroxyl functions, the two positions ortho to the hydroxyl functions are unsubstituted; or
several aromatic rings, at least two of these each bearing at least two hydroxyl functions in the meta position relative to one another, wherein, for at least one of the hydroxyl functions of at least one aromatic ring, the two positions ortho to the hydroxyl function are unsubstituted.

2. The composition according to claim 1 , wherein the thermosetting resin is also based on:
(A2′) at least one aromatic monophenol comprising at least one six-membered aromatic ring bearing a single hydroxyl function, the two positions ortho to the hydroxyl function being unsubstituted, or at least one position ortho to and the position para to the hydroxyl function being unsubstituted.

3. The composition according to claim 1 , wherein the aromatic compound A1 corresponds to the general formula (II):

in which B represents CHO or CH 2 OH, X represents O, NR 1 , NO, S, SO, SO 2 , SR 2 R 3 , R 1 represents a hydrogen, an alkyl, aryl, arylalkyl, alkylaryl or cycloalkyl group, R 2 , R 3 each represent, independently of one another, a hydrogen, an alkyl, aryl, arylalkyl, alkylaryl or cycloalkyl group.

4. The composition according to claim 1 , wherein the aromatic compound A1 corresponds to the general formula (II′a1) or (II′a2):

5. The composition according to claim 1 , wherein the aromatic ring of the aromatic polyphenol bears three hydroxyl functions in the meta position relative to one another.

6. The composition according to claim 1 , wherein the two positions ortho to each hydroxyl function on the aromatic ring of the aromatic polyphenol are unsubstituted.

7. The composition according to claim 1 , wherein the remainder of the aromatic ring of the aromatic polyphenol is unsubstituted.

8. The composition according to claim 1 , wherein the aromatic polyphenol comprises several aromatic rings, at least two of these each bearing at least two hydroxyl functions in the meta position relative to one another, wherein, for at least one of the hydroxyl functions of at least one aromatic ring, the two positions ortho to the hydroxyl function are unsubstituted.

9. The composition according to claim 8 , wherein at least one of the aromatic rings of the aromatic polyphenol bears three hydroxyl functions in the meta position relative to one another.

10. The composition according to claim 8 , wherein the two positions ortho to each hydroxyl function of at least one aromatic ring of the aromatic polyphenol are unsubstituted.

11. The composition according to claim 8 , wherein the two positions ortho to each hydroxyl function of each aromatic ring of the aromatic polyphenol are unsubstituted.

12. The composition according to claim 1 , wherein each aromatic ring of the aromatic polyphenol is a benzene ring.

13. The composition according to claim 1 , wherein the aromatic polyphenol is selected from the group consisting of phloroglucinol, 2,2′,4,4′-tetrahydroxydiphenyl sulfide, 2,2′,4,4′-tetrahydroxybenzophenone and mixtures thereof.

14. The composition according to claim 1 , wherein the aromatic polyphenol is a pre-condensed resin based on:
at least one aromatic polyphenol comprising:
at least one aromatic ring bearing three hydroxyl functions in the meta position relative to one another, wherein, for at least one of the hydroxyl functions, the two positions ortho to the hydroxyl functions are unsubstituted, or
several aromatic rings, at least two of these each bearing at least two hydroxyl functions in the meta position relative to one another, wherein, for at least one of the hydroxyl functions of at least one aromatic ring, the two positions the hydroxyl function are unsubstituted; and
at least one compound capable of reacting with said aromatic polyphenol comprising at least one aldehyde function and/or a compound capable of reacting with said aromatic polyphenol comprising at least two hydroxymethyl functions borne by an aromatic ring.

15. The composition according to claim 1 , wherein the water content of the aqueous adhesive composition is between 20 and 80% by weight.

16. The composition according to claim 1 , wherein the total solids content of the aqueous adhesive composition is between 20 and 80% by weight.

17. An aqueous adhesive solution comprising a pre-condensed thermosetting resin based on:
(A1) at least one aromatic compound comprising at least one aromatic ring bearing at least two functions, one of these functions being a hydroxymethyl function and the other being an aldehyde function or a hydroxymethyl function; and
(A2) at least one aromatic polyphenol comprising:
at least one aromatic ring bearing three hydroxyl functions in the meta position relative to one another, wherein, for at least one of the hydroxyl functions, the two positions ortho to the hydroxyl function are unsubstituted, or
several aromatic rings, at least two of these each bearing at least two hydroxyl functions in the meta position relative to one another, wherein, for at least one of the hydroxyl functions of at least one aromatic ring, the two positions ortho to the hydroxyl function are unsubstituted.

18. The aqueous adhesive solution according to claim 17 , wherein the thermosetting resin is also based on:
(A2′) at least one aromatic monophenol comprising at least one six-membered aromatic ring bearing a single hydroxyl function, the two positions ortho to the hydroxyl function being unsubstituted, or at least one position ortho to and the position para to the hydroxyl function being unsubstituted.

19. A process for adhesively bonding two elements comprising the steps of:
applying a layer of the aqueous adhesive composition according to claim 1 to at least one of the two elements, and
joining the two elements to one another via the layer of the aqueous adhesive composition.

20. An adhesively bonded assembly of two elements comprising a layer of the aqueous adhesive composition according to claim 1 joining the two elements to one another.

21. The composition according to claim 1 , wherein the aromatic polyphenol is phloroglucinol.

Assignees

• Michelin & Cie

Inventors

• Doisneau David
• Michoud Clement

Classifications

• B27N3/002

  characterised by the type of binder (compositions of macromolecular compounds C08L) · CPC title

• C09J2400/303

  in the substrate · CPC title

• C08G8/04

  of aldehydes · CPC title

• C09J5/02

  involving pretreatment of the surfaces to be joined · CPC title

• C09J161/12 Primary

  with polyhydric phenols · CPC title