Curable (meth)acrylate compositions

Patent metadata

Field	Value
Publication number	US-12503541-B2
Application number	US-202217676039-A
Country	US
Kind code	B2
Filing date	Feb 18, 2022
Priority date	Aug 24, 2017
Publication date	Dec 23, 2025
Grant date	Dec 23, 2025

Abstract

A two-part curable (adhesive) composition comprising a Part A and a Part B:
Part A comprising:
(i) a curable (meth)acrylate component; (ii) a peroxide; and (iii) a phenolic lipid; and

Part B comprising:
(i) a curable (meth)acrylate component; and (ii) a transition metal component. These compositions are tack free, demonstrate good cure through volume and desirable bond strengths on both active and passive substrates. The two-part curable (adhesive) composition can cure across relatively large bond gaps and are non-volatile.

First claim

The invention claimed is:

1 . A two-part curable composition comprising a Part A and a Part B:
Part A comprising: (i) a curable (meth)acrylate component; (ii) a peroxide; and (iii) a phenolic lipid in an amount of about 10-30 wt % based on the total weight of the composition; and Part B comprising: (i) a curable (meth)acrylate component; and (ii) a transition metal component.

2 . The curable composition according to claim 1 wherein the phenolic lipid comprises a polyol comprising one or more moieties having the following structure:

wherein R is C 10 -C 30 aliphatic, optionally substituted with heteroatoms selected from O, N or S, and wherein R may be optionally substituted with at least one of a hydroxyl, a C 1 -C 6 alkyl, a C 1 -C 6 alkoyl, a C 1 -C 6 ether, oxo, epoxy or glycidoxy; R 1 may be hydrogen or hydroxyl; R 2 may be hydrogen, a carboxyl group or an ester.

3 . The curable composition according to claim 1 wherein the phenolic lipid comprises one or more moieties having the following structure:

wherein R is a C 10 -C 30 aliphatic group.

4 . The curable composition according to claim 1 , wherein the phenolic lipid comprises a cashew nutshell liquid based polyol.

5 . The curable composition according to claim 4 , wherein the cashew nutshell liquid based polyol is selected from the group consisting of a cashew nutshell liquid based polyether polyol, a cashew nutshell liquid based polyester polyol, a cashew nutshell liquid based Mannich polyol, a cashew nutshell liquid based polyester diol and/or combinations of two or more of these.

6 . The curable composition according to claim 1 , wherein the phenolic lipid comprises a cashew nutshell liquid based polyester diol comprising one or more moieties having the following structure:

wherein R is C 10 -C 30 aliphatic, optionally substituted with heteroatoms selected from O, N or S, and wherein R may be optionally substituted with at least one of a hydroxyl, a C 1 -C 6 alkyl, a C 1 -C 6 alkoyl, a C 1 -C 6 ether, oxo, epoxy or glycidoxy; R 1 may be hydrogen or hydroxyl; R 2 may be hydrogen, a carboxyl group or an ester.

7 . The curable composition according to claim 6 , wherein the polyester diol comprises one or more moieties having the following structure:

wherein R is a C 10 -C 30 aliphatic group.

8 . The curable composition according to claim 1 wherein the phenolic lipid comprises a resorcinol lipid.

9 . The curable composition according to claim 1 wherein the phenolic lipid comprises an oligomer having up to 10 repeating phenolic lipid units.

10 . The curable composition according to claim 1 wherein the phenolic lipid comprises a phenolic lipid dimer.

11 . The curable composition according to claim 1 wherein the phenolic lipid comprises a phenolic ring with at least one C 5 to a C 30 side chain attached to the ring.

12 . The curable composition according to claim 1 wherein the phenolic lipid component comprises a phenolic ring with at least one C 10 to a C 20 side chain attached to the ring.

13 . The curable composition according to claim 1 wherein the phenolic lipid component comprises a phenolic ring with at least one C 15 side chain attached to the ring.

14 . The curable composition according to claim 1 wherein the phenolic lipid component is derived from cashew nutshell oil.

15 . The curable composition according to claim 11 wherein the side chain terminates in an allyl group.

16 . The curable composition according to claim 11 wherein the side chain comprises at least two double bonds.

17 . The curable composition according to claim 16 wherein at least two double bonds are conjugated.

18 . The curable composition according to claim 1 wherein the phenolic lipid component comprises cardol or an oligomer having up to 10 repeating units of cardol:

19 . The curable composition according to claim 18 wherein the phenolic lipid component comprises a dimer of cardol:

20 . The curable composition according to claim 1 wherein the phenolic lipid component comprises cardanol or an oligomer having up to 10 repeating units of cardanol:

21 . The curable composition according to claim 20 wherein the phenolic lipid component comprises a dimer of cardanol:

22 . The curable composition according to claim 1 wherein the phenolic lipid comprises anarcardic acid or an oligomer having up to 10 repeating units of anarcardic acid:

23 . The curable composition according to claim 22 wherein the phenolic lipid comprises a dimer of anarcardic acid:

24 . The curable composition according to claim 1 wherein phenolic lipid component comprises a phenolic lipid diol.

25 . The curable composition according to claim 1 wherein the phenolic lipid component contains a cardanol glycidyl ether.

26 . The curable composition according to claim 20 , wherein the cardanol glycidyl ether has the following structure:

27 . The curable composition according to claim 1 wherein the phenolic lipid is present in an amount of from about 12 to about 25% by weight based on the total weight of the composition.

28 . The curable composition according to claim 1 wherein the phenolic lipid is present in an amount of from about 15 to about 20% by weight based on the total weight of the composition.

29 . The curable composition according to claim 1 wherein the transition metal in the transition metal component is cobalt and the transition metal component is a cobalt compound.

30 . The curable composition according to claim 1 wherein the transition metal in the transition metal component is cobalt in a cobalt (II) form.

31 . The curable composition according to claim 1 wherein the transition metal component includes polymer bound cobalt, cobalt salt, cobalt naphthenate, and any combination thereof.

32 . The curable composition according to claim 1 wherein the transition metal component includes cobalt neodecanoate.

33 . The curable composition according to claim 1 wherein the transition metal component is present in an amount from about 0.1 to about 5%.

34 . The curable compositi

Assignees

• Henkel Ag & Co Kgaa

Inventors

• Mullen David
• Sheerin Lynne
• Loane Mark

Classifications

• C08K13/02

  Organic and inorganic ingredients · CPC title

• C09J133/10

  Homopolymers or copolymers of methacrylic acid esters · CPC title

• C09J11/06 Primary

  organic · CPC title

• C08K5/08

  Quinones · CPC title

• C08K5/20

  Carboxylic acid amides · CPC title