IP Library Granted Patent US 10,590,311
Granted Patent B2
US 10,590,311 · App. 13/785,477 · Granted Mar 17, 2020

Accelerators for two part curable compositions

Inventors: David P. Birkett (Kildare, IE); Anthony F. Jacobine (Meriden, CT); Andrew D. Messana (Newington, CT); Joel D. Schall (Hamden, CT); David Mullen (Navan Co. Meath, IE); Martin Wyer (Ontario, CA); Lynnette Hurlburt (Manchester, CT)
Assignees: Henkel IP & Holding GmbH; Henkel AG & Co. KGaA
C09J11/06B32B7/12C08F220/18C08K5/405C09J4/00C09J133/14Y10T428/31551Y10T428/31935
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Quick Facts
Patent No.
US 10,590,311
App. No.
13/785,477
Granted
Mar 17, 2020
Kind
B2
Abstract

Benzoylthiourea or benzoylthiourethane derivatives as cure accelerators for two part curable compositions are provided.

Claims (13)

1. A two part curable composition comprising:

Part A: a cure accelerator consisting of at least one of:

Part B: an oxidant,

wherein at least one of Part A or Part B further comprises a (meth)acrylate component.

2. A combination comprising a bond formed between two mated substrates with the composition of claim 1 .

3. The composition of claim 1 , wherein the (meth)acrylate component is within the general structure H 2 C═CGCO 2 R 1 , wherein G may be hydrogen or alkyl groups having from 1 to about 4 carbon atoms, and R 1 may be a member selected from the group consisting of alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkaryl, aralkyl, and aryl groups having from 1 to about 16 carbon atoms, any of which may be optionally substituted or interrupted as the case may be with the group consisting of silane, silicon, oxygen, halogen, carbonyl, hydroxyl, ester, carboxylic acid, urea, urethane, carbonate, amine, amide, sulfur, sulfonate, and sulfone.

4. The composition of claim 1 , wherein the (meth)acrylate component is selected from the group consisting of polyethylene glycol di(meth)acrylates, tetrahydrofuran (meth) acrylates and di(meth)acrylates, hydroxypropyl (meth)acrylate, hexanediol di(meth)acrylate, trimethylol propane tri(meth)acrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, dipropylene glycol dimethacrylate, di-(pentamethylene glycol) dimethacrylate, tetraethylene diglycol diacrylate, diglycerol tetramethacrylate, tetramethylene dimethacrylate, ethylene dimethacrylate, neopentyl glycol diacrylate, trimethylol propane triacrylate and bisphenol-A mono and di(meth)acrylates, and bisphenol-F mono and di(meth)acrylates.

5. The composition of claim 1 , wherein the oxidant is selected from the group consisting of cumene hydroperoxide, para-menthane hydroperoxide, t-amyl hydroperoxide, 1,1,3,3-tetramethylbutyl 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, 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, and combinations thereof.

6. A two part curable composition comprising:

Part A: a cure accelerator consisting of one or more derivatives of benzoyl thiourea or thiourethane within structure I or IA below:

wherein Z is O or N—R, wherein R is a member selected from the group consisting of hydrogen, alkyl, alkenyl, hydroxyalkyl, hydroxyalkenyl, alkylene (meth)acrylate, carbonyl, carboxyl, or sulfonato, R′ is a member selected from the group consisting of hydrogen, alkyl, alkenyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene (meth)acrylate, carbonyl, carboxyl, or sulfonate, or R or R′ is a direct bond attaching to the phenyl ring; wherein X is optional, but when X is present, X is a member selected from the group consisting of alkenyl, cycloalkyl, hydroxyalkyl, hydroxyalkenyl, amino, alkylene- or alkenylene-ether, alkylene (meth)acrylate, carbonyl, carboxyl, nitroso, sulfonate, hydroxyl or haloalkyl; and Y is a member selected from the group consisting of —SO 2 NH—, —CONH—, —NH—, and —PO(NHCONHCSNH 2 )NH—; and n is 0 or 1 and m is 1 or 2, or

wherein R and R′ are independent members selected from the group consisting of alkenyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene (meth)acrylate, carbonyl, carboxyl, or sulfonato, or R and R′ taken together form a carbocyclic or hetero atom-containing ring, or R′ is a direct bond attaching to the phenyl ring; wherein X is optional, but when X is present, X is a member selected from the group consisting of alkenyl, cycloalkyl, hydroxyalkyl, hydroxyalkenyl, amino, alkylene or alkenylene-ether, alkylene (meth)acrylate, carbonyl, carboxyl, sulfonate, hydroxyl or haloalkyl; and Y is a member selected from a group consisting of —SO 2 NH—, —CONH—, —NH—, and —PO(NHCONHCSNH 2 )NH—; and n is 0 or 1 and m is 1 or 2; and

Part B: an oxidant selected from the group consisting of cumene hydroperoxide, para-menthane hydroperoxide, t-amyl hydroperoxide, 1,1,3,3-tetramethylbutyl 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, 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, and combinations thereof, wherein at least one of Part A or Part B further comprises a (meth)acrylate component.

Assignments (6)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 9, 2022
From: HENKEL IP & HOLDING GMBH
To: HENKEL AG & CO. KGAA
Reel/Frame 059357/0267 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 26, 2015
From: HENKEL US IP LLC
To: HENKEL IP & HOLDING GMBH
Reel/Frame 035100/0776 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 7, 2014
From: HENKEL CORPORATION
To: HENKEL US IP LLC
Reel/Frame 034184/0396 →
MERGER Recorded Feb 28, 2014
From: HENKEL IRELAND LIMITED
To: HENKEL AG & CO. KGAA
Reel/Frame 032373/0281 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 22, 2013
From: JACOBINE, ANTHONY F.; MESSANA, ANDREW D.; SCHALL, JOEL D.; HURLBURT, LYNNETTE
To: HENKEL CORPORATION
Reel/Frame 031454/0561 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 22, 2013
From: BIRKETT, DAVID P.; MULLEN, DAVID; WYER, MARTIN
To: HENKEL IRELAND LIMITED
Reel/Frame 031454/0777 →