IP Library Granted Patent US 7,678,847
Granted Patent B2
US 7,678,847 · App. 11/451,833 · Granted Mar 16, 2010

Encapsulated structural adhesive

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Quick Facts
Patent No.
US 7,678,847
App. No.
11/451,833
Granted
Mar 16, 2010
Kind
B2
Abstract

The invention teaches an encapsulated curable adhesive composition especially adapted for use as a structural adhesive. The adhesive composition enables formation of a thin layer reactive composition of microcapsules and a two-part curative. The adhesive composition comprises a first population of microcapsules encasing a monomer and a first-part curative comprising an initiator. The adhesive composition further comprises a second-part curative. The second-part curative comprises an activator and a catalyst. At least the activator of the second-part curative is preferably encapsulated in a second population of microcapsules. The catalyst and the second population of microcapsules can be dispersed in a binder material, along with the first population of microcapsules. The first population of microcapsules contain encapsulated within the core a monomer having a Tg 35° C. or less and the first-part curative. The first population microcapsules contain encapsulated within the core a monomer having a Tg 35° C. or less along with the first-part curative. The encapsulated monomer and first-part curative constitute a blend which is a free flowing liquid having a viscosity of less than 500 Cp (milliPascal-second), and more preferably less than 10 Cp (milliPascal-second). The first population of microcapsules with first-part curative, and a second-part curative and second population of microcapsules are dispersed in a binder material. Reactive contact of the monomer and first-part curative with the second-part curative is affected by exuding the respective capsule contents into reactive contact through breakage of the microcapsules such as an interference fit of the substrate or substrates to which the composition is applied.

Claims (33)

1. An encapsulated curable adhesive composition comprising:

a) a two part curative, comprising a first-part curative comprising a free radical initiator and a second-part curative,

b) a first population of polymeric microcapsules encasing both a monomer and the first-part curative forming a monomer and free radical initiator blend, the monomer being reactive with the second part curative, the first population of polymeric microcapsules being substantially impermeable to both parts of the curative,

the monomer being a mixture of a first monomer component having a viscosity greater than 500 milliPascal-second selected from the group consisting of 50 parts of melamine acrylate, 40 parts of epoxy acrylate, 50 parts of urethane dimethacrylate and 50 parts of polybutadiene; and a second monomer component being the balance to make 100 parts by weight of monomer, the second monomer component being a 50/50 ratio by weight of a blend of hexane diol dimethacrylate and tetrahydrofurfuryl methacrylate, wherein the viscosity of the mixture of the first monomer component and the second monomer component is less than 500 milliPascal-second,

wherein the monomer and the free radical initiator blend has a viscosity of a free flowing liquid of less than 500 milliPascal-second at 25° C.,

c) the second-part curative comprising a catalyst and an activator, the second-part curative being external to the first population of microcapsules and

wherein the activator of the second-part curative is separately encapsulated forming a second population of polymeric microcapsules.

2. The adhesive according to claim 1 wherein the encapsulated monomer and initiator blend has a viscosity of a flowing liquid of 25 Centipoise or less.

3. The encapsulated curable adhesive according to claim 1 wherein the catalyst is selected from the group consisting of a transition metal, a transition metal salt and an organic acid.

4. The encapsulated adhesive according to claim 3 Wherein the catalyst is selected from the group consisting of a copper salt and an organo copper compound.

5. The encapsulated adhesive according to claim 1 wherein the activator is an organonitrogen compound.

6. The encapsulated adhesive according to claim 5 wherein the activator is selected from the group consisting of diphenyl carbazine, diphenyl carbazone, propyl dihydropyridine, and diethyl-1,2-dihydro-1-phenyl-2-propyl pyridine.

7. The encapsulated adhesive according to claim 1 further comprising a binder for the first population of microcapsules and the second-part curative.

8. The encapsulated adhesive according to claim 1 wherein the initiator is a peroxy initiator.

9. The encapsulated curable adhesive according to claim 1 further comprising one or more binder materials in which the microcapsules, and second-part curative are dispersed.

10. The encapsulated curable adhesive according to claim 9 wherein the binder material is UV curable, and includes a UV initiator.

11. A coated substrate with a preapplied encapsulated curable adhesive composition comprising a substrate and one or more layers of an encapsulated curable adhesive composition, wherein the encapsulated curable adhesive composition comprises:

a) a two part curative, comprising a first-part curative comprising a free radical initiator and a second-part curative,

b) a first population of polymeric microcapsules encasing both a monomer and the first-part curative forming a monomer and free radical initiator blend, the monomer being reactive with the second part curative, the first population of polymeric microcapsules being substantially impermeable to both parts of the curative,

the monomer being a mixture of a first monomer component having a viscosity greater than 500 milliPascal-second selected from the group consisting of 50 parts of melamine acrylate, 40 parts of epoxy acrylate, 50 parts of urethane dimethacrylate and 50 parts of polybutadiene; and a second monomer component being the balance to make 100 parts by weight of monomer, the second monomer component being a 50/50 ratio by weight of a blend of hexane diol dimethacrylate and tetrahydrofurfuryl methacrylate, wherein the viscosity of the mixture of the first monomer component and the second monomer component is less than 500 milliPascal-second,

wherein the monomer and the free radical initiator blend has a viscosity of a free flowing liquid of less than 500 milliPascal-second at 25° C.,

c) the second-part curative comprising a catalyst and an activator, the second-part curative being external to the first population of microcapsules and

wherein the activator of the second-part curative is separately encapsulated forming a second population of polymeric microcapsules.

12. Coated substrate with adhesive composition according to claim 11 wherein the binder layers comprise at least three layers, with a first binder layer having dispersed therein at least the first population of microcapsules, with a second binder layer having dispersed therein one or more of activator, catalyst or the second population of microcapsules, with a third binder layer having dispersed therein one or more of activator or catalyst, wherein the binder layers have the same or different binders.

13. Coated substrate with adhesive composition according to claim 12 wherein at least two of the binder layers are each individually applied to one or more surfaces of substrates intended to be adhered, and the third binder layer is applied as an overcoat layer over either of the first two binder layers.

14. Coated substrate with adhesive according to claim 11 wherein the monomer and initiator blend has a viscosity of a flowing liquid of 25 milliPascal-second or less.

15. Coated substrate with adhesive according to claim 11 wherein the catalyst is selected from the group consisting of a transition metal, transition metal salt, and organic acid.

16. Coated substrate with adhesive according to claim 15 wherein the catalyst is selected from the group consisting of a copper salt and an organo copper compound.

17. Coated substrate with adhesive according to claim 11 wherein the activator is an organonitrogen compound.

18. Coated substrate with adhesive according to claim 17 wherein the activator is selected from the group consisting of diphenyl carbazine, diphenyl carbazone, propyl dihydropyridine and 3,5-diethyl-1,2-dihydro-1-phenyl-2-pyropyl pyridine.

19. Coated substrate with adhesive according to claim 11 wherein the initiator is a peroxy initiator.

20. Coated substrate with adhesive according to claim 11 further comprising one or more binder materials in which the microcapsules, and second-part curative are dispersed.

21. The encapsulated curable adhesive according to claim 11 wherein the binder is UV curable, and includes a UV initiator.

Assignments (29)
RELEASE OF SECURITY INTEREST Recorded Oct 7, 2021
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS COLLATERAL AGENT
To: ENCAPSYS, LLC; IPS STRUCTURAL ADHESIVES, INC.; IPS CORPORATION; WATERTITE PRODUCTS, INC.; WELD-ON ADHESIVES, INC.; IPS ADHESIVES LLC
Reel/Frame 057750/0945 →
CORRECTIVE ASSIGNMENT TO CORRECT THE APPLICATION NUMBER SERIAL NUMBER PREVIOUSLY RECORDED AT REEL: 44444 FRAME: 0905. ASSIGNOR(S) HEREBY CONFIRMS THE FIRST LIEN SECURITY AGREEMENT. Recorded Aug 8, 2019
From: ENCAPSYS, LLC; IPS STRUCTURAL ADHESIVES, INC.; IPS CORPORATION; WATERTITE PRODUCTS, INC.; WELD-ON ADHESIVES, INC.; IPS ADHESIVES LLC
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS FIRST LIEN COLLATERAL AGENT
Reel/Frame 050021/0307 →
CORRECTIVE ASSIGNMENT TO CORRECT THE APPLICATION NUMBER SERIAL NUMBER PREVIOUSLY RECORDED AT REEL: 44444 FRAME: 0932. ASSIGNOR(S) HEREBY CONFIRMS THE SECOND LIEN SECURITY AGREEMENT. Recorded Aug 8, 2019
From: ENCAPSYS, LLC; IPS STRUCTURAL ADHESIVES, INC.; IPS CORPORATION; WATERTITE PRODUCTS, INC.; WELD-ON ADHESIVES, INC.; IPS ADHESIVES LLC
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS SECOND LIEN COLLATERAL AGENT
Reel/Frame 050021/0359 →
CORRECTIVE ASSIGNMENT TO CORRECT THE PROPERTY NUMBER PREVIOUSLY RECORDED AT REEL: 49891 FRAME: 807. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Aug 8, 2019
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS ADMINISTRATIVE AGENT
To: ENCAPSYS, LLC; IPS STRUCTURAL ADHESIVES, INC.; IPS CORPORATION; WATERTITE PRODUCTS, INC.; WELD-ON ADHESIVES, INC.; IPS ADHESIVES LLC
Reel/Frame 050003/0400 →
RELEASE OF SECURITY INTEREST IN PATENTS Recorded Jul 1, 2019
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS ADMINISTRATIVE AGENT
To: ENCAPSYS, LLC; IPS STRUCTURAL ADHESIVES, INC.; IPS CORPORATION; WATERTITE PRODUCTS, INC.; WELD-ON ADHESIVES, INC.; IPS ADHESIVES LLC
Reel/Frame 049891/0807 →
RELEASE OF SECOND LIEN PATENT COLLATERAL AGREEMENT Recorded Jun 17, 2018
From: U.S. BANK NATIONAL ASSOCIATION, AS COLLATERAL AGENT
To: APPVION, INC.; PAPERWEIGHT DEVELOPMENT CORP.
Reel/Frame 046377/0179 →
RELEASE OF SECURITY INTEREST Recorded Jun 17, 2018
From: JEFFERIES FINANCE LLC, AS ADMINISTRATIVE AGENT
To: APPVION, INC.; PAPERWEIGHT DEVELOPMENT CORP.
Reel/Frame 046392/0438 →
FIRST LIEN SECURITY AGREEMENT Recorded Nov 14, 2017
From: ENCAPSYS, LLC; IPS STRUCTURAL ADHESIVES, INC.; IPS CORPORATION; WATERTITE PRODUCTS, INC.; WELD-ON ADHESIVES, INC.; IPS ADHESIVES LLC
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS FIRST LIEN COLLATERAL AGENT
Reel/Frame 044444/0905 →
RELEASE OF SECURITY INTEREST Recorded Nov 14, 2017
From: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
To: ENCAPSYS, LLC
Reel/Frame 044123/0160 →
SECOND LIEN SECURITY AGREEMENT Recorded Nov 14, 2017
From: ENCAPSYS, LLC; IPS STRUCTURAL ADHESIVES, INC.; IPS CORPORATION; WATERTITE PRODUCTS, INC.; WELD-ON ADHESIVES, INC.; IPS ADHESIVES LLC
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS SECOND LIEN COLLATERAL AGENT
Reel/Frame 044444/0932 →
RELEASE OF SECURITY INTEREST Recorded Feb 1, 2017
From: WILMINGTON TRUST, NATIONAL ASSOCIATION
To: ENCAPSYS, LLC
Reel/Frame 041144/0570 →
SECURITY INTEREST Recorded Aug 27, 2015
From: ENCAPSYS, LLC
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS ADMINISTRATIVE AGENT
Reel/Frame 036437/0821 →
SECURITY INTEREST Recorded Aug 7, 2015
From: ENCAPSYS, LLC
To: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 036275/0792 →
CHANGE OF NAME Recorded Aug 6, 2015
From: RISE ACQUISTION, LLC
To: ENCAPSYS, LLC
Reel/Frame 036303/0617 →
RELEASE OF SECURITY INTEREST Recorded Aug 4, 2015
From: JEFFERIES FINANCE LLC, AS ADMINISTRATIVE AGENT
To: APPVION, INC.; PAPERWEIGHT DEVELOPMENT CORP.
Reel/Frame 036251/0893 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 4, 2015
From: APPVION, INC.
To: RISE ACQUISTION, LLC
Reel/Frame 036245/0688 →
RELEASE OF SECURITY INTEREST Recorded Aug 4, 2015
From: U.S. BANK NATIONAL ASSOCIATION, AS COLLATERAL AGENT
To: APPVION, INC.; PAPERWEIGHT DEVELOPMENT CORP.
Reel/Frame 036249/0419 →
RELEASE OF SECURITY INTEREST Recorded Aug 4, 2015
From: JEFFERIES FINANCE LLC, AS ADMINISTRATIVE AGENT
To: APPVION, INC.; PAPERWEIGHT DEVELOPMENT CORP.
Reel/Frame 036250/0466 →
RELEASE OF SECURITY INTEREST Recorded Nov 20, 2013
From: U.S. BANK NATIONAL ASSOCIATION
To: APPLETON PAPERS INC.
Reel/Frame 031690/0774 →
SECOND LIEN PATENT COLLATERAL AGREEMENT Recorded Nov 19, 2013
From: APPVION, INC.; PAPERWEIGHT DEVELOPMENT CORP.
To: U.S. BANK NATIONAL ASSOCIATION
Reel/Frame 031689/0593 →
SECURITY AGREEMENT Recorded Jul 3, 2013
From: APPVION, INC.; PAPERWEIGHT DEVELOPMENT CORP.
To: JEFFERIES FINANCE LLC, AS ADMINISTRATIVE AGENT
Reel/Frame 030740/0153 →
RELEASE OF SECURITY INTEREST Recorded Jul 1, 2013
From: U.S. BANK NATIONAL ASSOCIATION
To: APPLETON PAPERS, INC.; PAPERWEIGHT DEVELOPMENT CORP.; AMERICAN PLASTICS COMPANY; NEW ENGLAND EXTRUSIONS, INC.
Reel/Frame 030724/0312 →
RELEASE OF SECURITY INTEREST Recorded Jun 28, 2013
From: FIFTH THIRD BANK
To: APPLETON PAPERS, INC.
Reel/Frame 030712/0054 →
CHANGE OF NAME Recorded Jun 17, 2013
From: APPLETON PAPERS INC.
To: APPVION, INC.
Reel/Frame 030641/0381 →
RELEASE OF SECURITY INTEREST Recorded Feb 11, 2010
From: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
To: APPLETON PAPERS INC.
Reel/Frame 023915/0760 →
SECURITY AGREEMENT Recorded Feb 9, 2010
From: PAPERWEIGHT DEVELOPMENT CORP.; APPLETON PAPERS INC.; AMERICAN PLASTICS COMPANY, INC.; NEW ENGLAND EXTRUSION INC.
To: U.S. BANK NATIONAL ASSOCIATION
Reel/Frame 023905/0953 →
SECURITY AGREEMENT Recorded Feb 8, 2010
From: APPLETON PAPERS INC.
To: FIFTH THIRD BANK, AS ADMINISTRATIVE AGENT
Reel/Frame 023905/0532 →
NOTICE OF GRANT OF SECURITY INTEREST Recorded Jun 29, 2007
From: APPLETON PAPERS INC.
To: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 019489/0751 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 13, 2006
From: YAN, NIANXI; SANDS, PEGGY DOROTHY; GUINEBRETIERE, SANDRA JACQUELINE
To: APPLETON PAPERS INC.
Reel/Frame 017975/0157 →