IP Library › Granted Patent US 6,887,950
Granted Patent B2
US 6,887,950 · App. 10/317,587 · Granted May 3, 2005

Phosphine oxide hydroxyaryl mixtures with novolac resins for co-curing epoxy resins

Assignee: PABU Services, Inc.
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Quick Facts
Patent No.
US 6,887,950
App. No.
10/317,587
Granted
May 3, 2005
Kind
B2
Abstract

A mixture of hydroxyarylphosphine oxides comprising (a) a mono(hydroxyaryl)phosphine oxide, (b) a bis(hydroxyaryl)phosphine oxide, (c) a tris((hydroxyaryl)phosphine oxide, and, optionally (d) a tri- aryl, alkyl, or aralkyl-substituted phosphine oxide combined with a phenolic co-crosslinking composition is useful as a polyhtdroxy mixture for co-crosslinking an epoxy resin which also imparts flame resistance.

Claims (30)

1. A flame-retardant curable epoxy composition comprising:

(a) an epoxy resin;

(b) a co-crosslinking polyhydroxy mixture including:

(i) a mixture of phosphine oxides including hydroxyaryl phosphine oxides of the formulae:

(A) a mono(hydroxyaryl)phosphine oxide of the formula:

wherein R 1 is a divalent, substituted or unsubstituted arylene moiety and R 2 is a monovalent, substituted or unsubstituted aryl moiety or is an alkyl moiety or is an aralkyl moiety; and

(B) a bis(hydroxyaryl)phosphine oxide of the formula:

wherein R 1 and R 2 are defined as above; and

(C) a tris(hydroxyaryl)phosphine oxide of the formula:

wherein R 1 is defined as above; and

(D) optionally containing minor amounts of a pentavalent phosphine oxide of the formula:

wherein R 2 is defined as above; and

(ii) a phenolic co-crosslinking composition comprising a phenolic component having a hydroxyfunctionality of two or more.

2. The curable epoxy composition according to claim 1 , wherein the epoxy resin is based on epichlorohydrin and bisphenol A.

3. The curable epoxy composition according to claim 1 , wherein the epoxy resin is based on epichlorohydrin and bisphenol F.

4. The curable epoxy composition according to claim 1 , wherein the epoxy resin is a novolac epoxy resin.

5. The curable epoxy composition according to claim 1 , having a phosphorous content of from about 0.2 wt. percent to about 5 wt. percent.

6. The curable epoxy composition according to claim 5 , having a phosphorous content of from about 1 wt. percent to about 4 wt. percent.

7. The curable epoxy composition according to claim 6 , having a phosphorous content of from about 2 wt. percent to about 3 wt. percent.

8. The curable epoxy composition according to claim 1 , wherein the polyhydroxy mixture has a hydroxy content of from about 50 mole % to about 150 mole % of the stoichiometric amount required to cure the epoxy resin.

9. The curable epoxy composition according to claim 8 , wherein the polyhydroxy mixture has a hydroxy content of from about 75 mole % to about 125 mole % of the stoichiometric amount required to cure the epoxy resin.

10. The curable epoxy composition according to claim 9 , wherein the polyhydroxy mixture has a hydroxy content of from about 85 mole % to about 110 mole % of the stoichiometric amount required to cure the epoxy resin.

11. The curable epoxy composition according to claim 1 , wherein from 1 mole % to about 99 mole % of the hydroxy moieties in the mixture are novolac resin hydroxyl groups.

12. The curable epoxy composition according to claim 1 , wherein from 25 mole % to about 75 mole % of the hydroxy moieties in the mixture are novolac resin hydroxyl groups.

13. The curable epoxy composition according to claim 1 , wherein from about 1 mole % to about 99 mole % of the hydroxy moieties in the mixture are phosphine oxide hydroxyaryl moieties.

14. The curable epoxy composition according to claim 13 , wherein from about 25 mole % to about 75 mole % of the hydroxy moieties in the mixture are phosphine oxide hydroxyaryl moieties.

15. The curable epoxy composition according to claim 1 , wherein said co-crosslinking composition comprises a novolac resin.

16. The curable epoxy composition according to claim 15 , wherein said novolac resin comprises a nitrogen heteroaryl aldehyde copolymer.

17. The curable epoxy composition according to claim 16 , wherein said nitrogen heteroaryl aldehyde copolymer is selected from the group consisting of benzoguanamine phenol formaldehyde resins, acetoguanamine phenol formaldehyde resins, melamine phenol formaldehyde resins, benzoguanamine cresol formaldehyde resins, acetoguanamine cresol formaldehyde resins, melamine cresol formaldehyde resins, and mixtures thereof.

18. The curable polyhydroxy mixture according to claim 15 , wherein said novolac resin is selected from the group consisting of phenol formaldehyde resins, cresol formaldehyde resins and mixtures thereof.

Assignments (12)
RELEASE OF AMENDED AND RESTATED SECOND LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded May 12, 2017
From: BANK OF AMERICA, N.A.
To: CHEMTURA CORPORATION; CROMPTON COLORS INCORPORATED; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION
Reel/Frame 042452/0759 →
RELEASE OF THIRD LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded May 12, 2017
From: BANK OF AMERICA, N.A.
To: CHEMTURA CORPORATION; CROMPTON COLORS INCORPORATED; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION
Reel/Frame 042452/0894 →
RELEASE OF FIRST LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded May 11, 2017
From: BANK OF AMERICA, N.A.
To: CHEMTURA CORPORATION; BIOLAB FRANCHISE COMPANY, LLC; BIO-LAB, INC.; CROMPTON COLORS INCORPORATED; CROMPTON HOLDING CORPORATION; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION; GREAT LAKES CHEMICAL GLOBAL, INC.; GT SEED TREATMENT, INC.; HOMECARE LABS, INC.; LAUREL INDUSTRIES HOLDINGS, INC.; RECREATIONAL WATER PRODUCTS, INC.; WEBER CITY ROAD LLC
Reel/Frame 042447/0508 →
RELEASE OF SECOND LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded May 11, 2017
From: BANK OF AMERICA, N.A.
To: CHEMTURA CORPORATION; BIOLAB FRANCHISE COMPANY, LLC; BIO-LAB, INC.; CROMPTON COLORS INCORPORATED; CROMPTON HOLDING CORPORATION; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION; GREAT LAKES CHEMICAL GLOBAL, INC.; GT SEED TREATMENT, INC.; HOMECARE LABS, INC.; LAUREL INDUSTRIES HOLDINGS, INC.; RECREATIONAL WATER PRODUCTS, INC.; WEBER CITY ROAD LLC
Reel/Frame 042449/0001 →
AMENDED AND RESTATED SECOND LIEN INTELLECTUAL PROPERY SECURITY AGREEMENT Recorded Jul 18, 2014
From: CHEMTURA CORPORATION; CROMPTON COLORS INCORPORATED; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION
To: BANK OF AMERICA, N.A.
Reel/Frame 033360/0225 →
THIRD LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Jul 18, 2014
From: CHEMTURA CORPORATION; CROMPTON COLORS INCORPORATED; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION
To: BANK OF AMERICA, N.A.
Reel/Frame 033360/0325 →
FIRST LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT. Recorded Mar 21, 2011
From: CHEMTURA CORPORATION; BIOLAB FRANCHISE COMPANY, LLC; BIO-LAB, INC.; CROMPTON COLORS INCORPORATED; CROMPTON HOLDING CORPORATION; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION; GREAT LAKES CHEMICAL GLOBAL, INC.; GT SEED TREATMENT, INC.; HOMECARE LABS, INC.; LAUREL INDUSTRIES HOLDINGS, INC.; RECREATIONAL WATER PRODUCTS, INC.; WEBER CITY ROAD LLC
To: BANK OF AMERICA, N.A.
Reel/Frame 026028/0622 →
INTELLECTUAL PROPERTY SECURITY RELEASE AGREEMENT Recorded Mar 21, 2011
From: CITIBANK, N.A.
To: CHEMTURA CORPORATION; A & M CLEANING PRODUCTS, LLC; ASCK, INC; BIOLAB COMPANY STORE, LLC; AQUA CLEAR INDUSTRIES, LLC; ASEPSIS, INC.; BIOLAB TEXTILES ADDITIVES, LLC; BIOLAB, INC.; CROMPTON COLORS INCORPORATED; CROMPTON MONOCHEM, INC.; CNK CHEMICAL REALTY CORPORATION; CROMPTON HOLDING CORPORATION; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION; GT SEED TREATMENT, INC.; ISCI, INC; GREAT LAKES CHEMICAL GLOBAL, INC.; HOMECARE LABS, INC.; KEM MANUFACTURING CORPORATION; LAUREL INDUSTRIES HOLDINGS, INC.; NAUGATUCK TREATMENT COMPANY; UNIROYAL CHEMICAL COMPANY LIMITED (DELAWARE); MONOCHEM, INC.; RECREATIONAL WATER PRODUCTS, INC.; WEBER CITY ROAD LLC; WRL OF INDIANA, INC.; BIOLAB FRANCHISE COMPANY, LLC
Reel/Frame 026039/0142 →
SECDOND LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Mar 21, 2011
From: CHEMTURA CORPORATION; BIOLAB FRANCHISE COMPANY, LLC; BIO-LAB, INC.; CROMPTON COLORS INCORORATED; CROMPTON HOLDING CORPORATION; CLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION; GREAT LAKES CHEMICAL GLOBAL, INC.; GT SEED TREATMENT, INC.; HOMECARE LABS, INC.; HAOMECARE LABS, INC.; LAUREL INDUSTRIES HOLDINGS, INC.; RECREATIONAL WATER PRODUCTS, INC.; WEBER CITY ROAD LLC
To: BANK OF AMERICA, N. A.
Reel/Frame 027881/0347 →
AMENDED AND RESTATED INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Feb 22, 2010
From: CHEMTURA CORPORATION; A & M CLEANING PRODUCTS, LLC; AQUA CLEAR INDUSTRIES, LLC; ASCK, INC.; ASEPSIS, INC.; BIOLAB COMPANY STORE, LLC; BIOLAB FRANCHISE COMPANY, LLC; BIOLAB TEXTILE ADDITIVES, LLC; BIO-LAB, INC.; CNK CHEMICAL REALTY CORPORATION; CROMPTON COLORS INCORPORATED; CROMPTON HOLDING CORPORATION; CROMPTON MONOCHEM, INC.; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION; GREAT LAKES CHEMICAL GLOBAL, INC.; GT SEED TREATMENT, INC.; HOMECARE LABS, INC.; ISCI, INC.; KEM MANUFACTURING CORPORATION; LAUREL INDUSTRIES HOLDINGS, INC.; MONOCHEM, INC.; NAUGATUCK TREATMENT COMPANY; RECREATIONAL WATER PRODUCTS, INC.; UNIROYAL CHEMICAL COMPANY LIMITED (DELAWARE); WEBER CITY ROAD LLC; WRL OF INDIANA, INC.
To: CITIBANK, N.A.
Reel/Frame 023998/0001 →
SECURITY AGREEMENT Recorded May 12, 2009
From: CHEMTURA CORPORATION; A & M CLEANING PRODUCTS, LLC; AQUA CLEAR INDUSTRIES, LLC; ASCK, INC.; ASEPSIS, INC.; BIOLAB TEXTILE ADDITIVES, LLC; BIO-LAB, INC.; CNK CHEMICAL REALTY CORPORATION; CROMPTON HOLDING CORPORATION; CROMPTON COLORS INCORPORATED; CROMPTON MONOCHEM, INC.; GREAT LAKES CHEMICAL CORPORATION; GREAT LAKES CHEMICAL GLOBAL, INC.; GT SEED TREATMENT, INC.; HOMECARE LABS, INC.; ISCI, INC.; KEM MANUFACTURING CORPORATION; LAUREL INDUSTRIES HOLDINGS, INC.; MONOCHEM, INC.; NAUGATUCK TREATMENT COMPANY; RECREATIONAL WATER PRODUCTS, INC.; UNIROYAL CHEMICAL COMPANY LIMITED (DELAWARE); WEBER CITY ROAD LLC; WRL OF INDIANA, INC.; BIOLAB COMPANY STORE, LLC; BIOLAB FRANCHISE COMPANY, LLC; GLCC LAUREL, LLC
To: CITIBANK, N.A.
Reel/Frame 022668/0658 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 12, 2002
From: TIMBERLAKE, LARRY D.; HANSON, MARK V.; EDWARDS, E. BRADLEY
To: PABU SERVICES, INC.
Reel/Frame 013579/0787 →
Continuity (3)
Continuation In Part 1007770100 · Feb 14, 2002
Provisional Application 6026897500 · Feb 15, 2001
Related Publication 20030148109A1 · Aug 7, 2003