IP Library Granted Patent US 9,580,530
Granted Patent B2
US 9,580,530 · App. 13/435,985 · Granted Feb 28, 2017

Anaerobically curable compositions

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,580,530
App. No.
13/435,985
Granted
Feb 28, 2017
Kind
B2
Abstract

The present invention relates to anaerobically curable compositions containing a benzoxazine component and which demonstrates resistance to elevated temperature conditions and/or accelerated cure speed.

Claims (33)

1. An anaerobic curable composition, comprising:

(a) a (meth)acrylate component;

(b) an anaerobic cure system; and

(c) a benzoaxzine component,

wherein the benzoxazine component is embraced by

wherein o is 1-4, X is selected from the group consisting of a direct bond (when o is 2), alkyl (when o is 1), alkylene (when o is 2-4), carbonyl (when o is 2), thiol (when o is 1), thioether (when o is 2), sulfoxide (when o is 2), and sulfone (when o is 2), and R 1 is aryl, or

wherein p is 2, Y is selected from the group consisting of biphenyl (when p is 2), diphenyl methane (when p is 2), diphenyl isopropane (when p is 2), diphenyl sulfide (when p is 2), diphenyl sulfoxide (when p is 2), diphenyl sulfone (when p is 2), and diphenyl ketone (when p is 2), and R 4 is selected from the group consisting of hydrogen, halogen, alkyl and alkenyl.

2. An anaerobic curable composition comprising:

(a) a (meth)acrylate component;

(b) anaerobic cure system; and

(c) a benzoxazine component,

wherein the benzoxazine component is embraced by one or more of

wherein X is selected from the group consisting of a direct bond, CH 2 , C(CH 3 ) 2 , C═O, S, S═O and O═S═O, and R 1 , R 2 , and R 3 are the same or different aryl and R 4 is selected from the group consisting of hydrogen, alkyl, alkenyl and aryl.

3. A anaerobic curable composition comprising:

(a) a (meth)acrylate component;

(b) an anaerobic cure system; and

(c) a benzoxazine component,

wherein the benzoxazine component is embraced by one or more of

wherein X is selected from the group consisting of a direct bond, CH 2 , C(CH 3 ) 2 , C═O, S═O, O═S═O, and s, and R 1 and R 2 , are the same or different aryl.

4. An anaerobic curable composition comprising:

(a) a (meth)acrylate component;

(b) an anaerobic cure system; and

(c) a benzoxazine component, wherein the benzoxazine component is embraced by

wherein R 1 and R 2 are the same or different aryl.

5. The composition according to claim 1 , wherein the (meth)acrylate component is represented by H 2 C═CGCO 2 R 1 , wherein G is a member selected from the group consisting of H, halogen and alkyl having from 1 to about four carbon atoms, and R 1 is a member selected from the group consisting of alkyl, cycloalkyl, aklenyl, cycloalkenyl, alkaryl, and aryl groups having from 1 to about 16 carbon atoms, with or without substitution or interruption by a member selected from the group consisting of silane, silicon, oxygen, halogen, carbonyl, hydroxyl, ester, carboxylic acid, urea, urethane, carbamate, amine, amide, sulfur, sulfonate and sulfone.

6. The composition according to claim 1 , wherein the (meth)acrylate component is, selected from the group consisting of silicone (meth)acrylates, polyethylene glycol di(meth)acrylates, bisphenol-A-(meth)acrylates, ethoxylated bisphenol-A-(meth)acrylates, bisphenol-F-(meth)acrylates, ethoxylated bisphenol-F-(meth)acrylates, tetrahydrofuran (meth)acrylates and di(meth)acrylates, hydroxypropyl (meth)acrylate, hexanediol di(meth)acrylate, and trimethylol propane tri(meth)acrylate.

7. The composition according to claim 1 , wherein the benzoxazine component acts as a toughener.

8. The composition according to claim 1 , wherein the benzoxazine component acts as an accelerator.

9. Reaction products of the composition according to claim 1 .

10. A process for preparing a reaction product from an anaerobic curable composition, comprising the steps of:

apply an anaerobic curable composition according to claim 1 , to a desired substrate surface and

exposing the composition to an anaerobic environment for a time sufficient to cure the composition.

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

Assignments (12)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 26, 2015
From: HENKEL US IP LLC
To: HENKEL IP & HOLDING GMBH
Reel/Frame 035100/0151 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 7, 2014
From: HENKEL CORPORATION
To: HENKEL US IP LLC
Reel/Frame 034183/0611 →
CORRECTIVE ASSIGNMENT TO CORRECT INCORRECT PROPERTIES 6620263, 8168743, 8642709, 8632654, 7973158, 12765973, 12766112, 13836858, 12945256, 13785007, 13785477, 13799002, 13840063 AND 13770295 PREVIOUSLY RECORDED ON REEL 032326 FRAME 0121. ASSIGNOR(S HEREBY CONFIRMS THE ASSIGNMENT. Recorded Sep 26, 2014
From: HENKEL AG & CO. KGAA
To: HENKEL IP & HOLDING GMBH
Reel/Frame 033860/0888 →
MERGER Recorded Feb 28, 2014
From: HENKEL IRELAND LIMITED
To: HENKEL AG & CO. KGAA
Reel/Frame 032373/0281 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 28, 2014
From: HENKEL AG & CO. KGAA
To: HENKEL IP & HOLDING GMBH
Reel/Frame 032326/0121 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 24, 2014
From: HENKEL AG & CO. KGAA
To: HENKEL IP & HOLDING GMBH
Reel/Frame 032329/0172 →
MERGER Recorded Feb 24, 2014
From: HENKEL IRELAND LIMITED
To: HENKEL AG & CO. KGAA
Reel/Frame 032329/0132 →
MERGER Recorded Oct 22, 2013
From: HENKEL IRELAND HOLDING B.V.
To: HENKEL IRELAND LIMITED
Reel/Frame 031449/0882 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 22, 2013
From: HENKEL IRELAND LIMITED
To: LOCTITE (R&D) LIMITED
Reel/Frame 031449/0719 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 22, 2013
From: BIRKETT, DAVID P.; WYER, MARTIN; MULLEN, DAVID; MCGARRY, LEE
To: HENKEL IRELAND LIMITED
Reel/Frame 031449/0631 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 22, 2013
From: ATTARWALA, SHABBIR; ZHU, QINYAN
To: HENKEL CORPORATION
Reel/Frame 031449/0589 →
MERGER Recorded Oct 22, 2013
From: LOCTITE (R&D) LIMITED
To: HENKEL IRELAND HOLDING B.V.
Reel/Frame 031449/0841 →