IP Library Granted Patent US 12,286,495
Granted Patent B2
US 12,286,495 · App. 17/346,368 · Granted Apr 29, 2025

(Meth)acrylate-functionalized waxes and curable compositions made therewith

Inventors: David Dworak (Middletown, CT); Deirdre Ledwith (Dublin, IE)
Assignee: Henkel AG & Co. KGaA
C08F222/225C07C271/16C08F220/36C08F222/22C09J4/00C09J133/14C09J135/02C08F2800/20
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Quick Facts
Patent No.
US 12,286,495
App. No.
17/346,368
Granted
Apr 29, 2025
Kind
B2
Abstract

The present invention relates to (meth)acrylate-functionalized waxes and curable compositions, such as anaerobic adhesive compositions, made therewith.

Claims (28)

1. A compound having a formula:

wherein n is 0 to 3; t is 1 to 4; Z is H or Me;

R is a C 2 -C 12 aliphatic group optionally substituted with one or more: C 1 -C 6 alkyl, C 1 -C 6 alkoxy, hydroxyl, acrylate, methacrylate, oxo and where said C 2 -C 12 aliphatic group is optionally substituted with one or more heteroatoms selected from O, N or S;

R 1 has the structure:

wherein o is from 15 to 30;

R 2 comprises a C 2 -C 20 aliphatic group, a C 5 -C 20 aryl group, or a C 6 -C 20 alkaryl group optionally substituted with one or more C 1 -C 6 alkyl, C 1 -C 6 alkoxy, hydroxyl, and optionally substituted with one or more heteroatoms selected from O, N or S.

2. A compound having a formula:

wherein n is 0 to 3; t is 1 to 4; Z is H or Me;

R is a C 2 -C 12 aliphatic group optionally substituted with one or more: C 1 -C 6 alkyl, C 1 -C 6 alkoxy, hydroxyl, acrylate, methacrylate, oxo and where said C 2 -C 12 aliphatic group is optionally substituted with one or more heteroatoms selected from O, N or S;

R 1 has the structure:

wherein p is from 10 to 30;

R 2 comprises a C 2 -C 20 aliphatic group, a C 5 -C 20 aryl group, or a C 5 -C 20 alkaryl group optionally substituted with one or more C 1 -C 6 alkyl, C 1 -C 6 alkoxy, hydroxyl, and optionally substituted with one or more heteroatoms selected from O, N or S.

3. A compound having a structure selected from:

4. An anaerobic curable composition comprising:

(a) a (meth)acrylate component;

(b) an anaerobic cure-inducing composition; and

(c) a compound according to claim 1 .

5. The anaerobic curable composition of claim 4 , wherein the anaerobic cure-inducing composition comprises a peroxide or hydroperoxide selected from the group consisting of cumene hydroperoxide, para-menthane hydroperoxide, t-butyl hydroperoxide, t-butyl perbenzoate, benzoyl peroxide, dibenzoyl peroxide, 1,3-bis(t-butylperoxyisopropyl)benzene, diacetyl peroxide, butyl 4,4-bis(t-butylperoxy)valerate, p-chlorobenzoyl peroxide, t-butyl cumyl peroxide, lauryl peroxide, urea-hydrogen peroxide, n-vinyl pyrrolidone-hydrogen peroxide, bis(tert-butylcyclohexyl peroxydicarbonate, t-butyl perbenzoate, di-t-butyl peroxide, dicumyl peroxide, 2,5-dimethyl-2,5-di-t-butylperoxyhexane, 2,5-dimethyl-2,5-di-t-butyl-peroxyhex-3-yne, 4-methyl-2,2-di-t-butylperoxypentane, t-amyl hydroperoxide, 1,2,3,4-tetramethylbutyl hydroperoxide and combinations thereof.

6. The anaerobic curable composition of claim 4 , wherein the compound is present in an amount of from about 10% by weight to about 60% by weight by weight based on the total weight of the composition.

7. The anaerobic curable composition of claim 4 , wherein the compound is present in an amount of from about 25% by weight to about 50% by weight based on the total weight of the composition.

8. An anaerobic curable composition comprising:

(a) a (meth)acrylate component;

(b) an anaerobic cure-inducing composition; and

(c) a compound according to claim 2 .

9. An anaerobic curable composition comprising:

(a) a (meth)acrylate component;

(b) an anaerobic cure-inducing composition; and

(c) a compound according to claim 3 .

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 5, 2025
From: LEDWITH, DEIRDRE
To: HENKEL IRELAND OPERATIONS AND RESEARCH LIMITED
Reel/Frame 070407/0457 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 5, 2025
From: DWORAK, DAVID
To: HENKEL IP & HOLDING GMBH
Reel/Frame 070409/0405 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 5, 2025
From: HENKEL IRELAND OPERATIONS AND RESEARCH LIMITED
To: HENKEL IP & HOLDING GMBH
Reel/Frame 070409/0513 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 22, 2022
From: HENKEL IP & HOLDING GMBH
To: HENKEL AG & CO. KGAA
Reel/Frame 059207/0627 →