IP Library Granted Patent US 8,986,847
Granted Patent B2
US 8,986,847 · App. 13/795,713 · Granted Mar 24, 2015

Accelerator/oxidant/proton source combinations for two part curable compositions

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Quick Facts
Patent No.
US 8,986,847
App. No.
13/795,713
Granted
Mar 24, 2015
Kind
B2
Abstract

Benzoylthiourea or benzoylthiourethane derivatives, together with oxidants and a source of protons, acting as cure accelerators for two part curable compositions are provided.

Claims (16)

1. A two part curable composition comprising:

Part A: A proton source and one or more benzoyl thiourea or benzoyl thiourethane compounds within structures I or IA below:

wherein Z is O or N—R, where R is selected from hydrogen, alkyl, alkenyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene (meth)acrylate, carbonyl, carboxyl, or sulfonato, 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 present X is halogen, alkyl, alkenyl, cycloalkyl, hydroxyalkyl, hydroxyalkenyl, alkoxy, amino, alkylene- or alkenylene-ether, alkylene (meth)acrylate, carbonyl, carboxyl, nitroso, sulfonate, hydroxyl or haloalkyl; and Y is —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 independently selected from hydrogen, alkyl, 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 present X is halogen, alkyl, alkenyl, cycloalkyl, hydroxyalkyl, hydroxyalkenyl, alkoxy, amino, alkylene- or alkenylene-ether, alkylene (meth)acrylate, carbonyl, carboxyl, sulfonate, hydroxyl or haloalkyl; and Y is —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,

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

2. The composition of claim 1 , wherein the (meth)acrylate component is represented by 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 selected from alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkaryl, aralkyl or 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 silane, silicon, oxygen, halogen, carbonyl, hydroxyl, ester, carboxylic acid, urea, urethane, carbonate, amine, amide, sulfur, sulfonate, and sulfone.

3. The composition of claim 1 , wherein the oxidant is a member 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.

4. The composition of claim 1 , wherein the proton source is selected from the group consisting of water, alcohols, acids, and aldehydes.

5. The composition of claim 1 , wherein the proton source is an alcohol selected from the group consisting of hydroxy alkyl (meth)acrylates, alkanols, alkane di- and polyols.

6. The composition of claim 1 , wherein the proton source is an acid selected from the group consisting of acrylic acid and polymeric versions thereof, lactic acid, citric acid and combinations thereof.

7. The composition of claim 1 , wherein the proton source is an aldehyde selected from the group consisting of formaldeyde, acetaldehyde, ethyl aldehyde, propyl aldehydes, butyl aldehydes and benzaldehyde.

8. The composition of claim 1 , wherein the proton source is a silanol.

9. The composition of claim 1 , wherein the proton source is a silanol found on the surface of a glass substrate.

10. A bond formed between two mated substrates with the composition of claim 1 .

11. The composition of claim 1 , wherein the benzoyl thiourea or benzoyl thiourethane compound is selected from one or more of

Assignments (4)
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 5, 2014
From: JACOBINE, ANTHONY F.; MESSANA, ANDREW D.; SCHALL, JOEL D.; HURLBURT, LYNNETTE
To: HENKEL CORPORATION
Reel/Frame 033675/0385 →