IP Library Granted Patent US 7,390,839
Granted Patent B2
US 7,390,839 · App. 11/333,398 · Granted Jun 24, 2008

Blends of alkyl substituted triaryl phosphate esters with phosphorus-containing flame retardants for polyurethane foams

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Quick Facts
Patent No.
US 7,390,839
App. No.
11/333,398
Granted
Jun 24, 2008
Kind
B2
Abstract

Flame retardant flexible polyurethane foam compositions, methods of flame retarding flexible polyurethane foam compositions, articles made therefrom and flame retardants that comprise blends of (alkyl substituted) triaryl phosphate ester and phosphorus-containing flame retardant having at least about 5 wt. % phosphorus additives. The combined weight of the (alkyl substituted) triaryl phosphate ester and the phosphorus-containing flame retardant comprises about 5 to about 40% by weight of the flexible polyurethane foam compositions or reaction mixtures. The ratio of the (alkyl substituted) triaryl phosphate ester to the phosphorus-containing flame retardant is from about 95:5 to about 50:50 percent by weight.

Claims (42)

1. A flame retardant polyurethane composition comprising:

an alkyl substituted triaryl phosphate ester;

a phosphorous-containing flame retardant having at least about 5 wt. % phosphorus selected from the group consisting of: tris(2-ethylhexyl) phosphate, resorcinol bis(diphenyl phosphate), tri-n-butyl phosphate, tri-isobutyl phosphate, and mixtures thereof, wherein the combined weight of the alkyl substituted triaryl phosphate ester and the phosphorus-containing flame retardant comprises about 5 to about 40% by weight of polyol, and wherein the ratio of the alkyl substituted triaryl phosphate ester to the phosphorus-containing flame retardant is from about 95:5 to about 80:20 percent by weight; and

a flexible polyurethane foam reaction mixture including at least one polyol and at least one isocyanate.

2. The flame retardant polyurethane composition of claim 1 , wherein the alkyl substituted triaryl phosphate ester includes one or more compounds having the general formula:

where each R is independently either a linear or branched C 1 to C 6 alkyl group, and n is independently an integer of 0, 1 or 2, but n may not be 0 in at least one instance.

3. The flame retardant polyurethane composition of claim 2 , wherein the alkyl substituted triaryl phosphate ester comprises at least one of tricresyl phosphate, butylated triphenyl phosphate, and isopropylated triphenyl phosphate.

4. The flame retardant polyurethane composition of claim 3 , wherein the alkyl substituted triaryl phosphate ester comprises a mixed isopropylated triphenyl phosphate containing about 8.6% phosphorus and also having about 35 wt. % of non-alkylated triphenyl phosphate.

5. The flame retardant polyurethane composition of claim 1 , wherein the phosphorus-containing flame retardant comprises resorcinol bis(diphenyl phosphate).

6. The flame retardant polyurethane composition of claim 1 , wherein the phosphorus-containing flame retardant comprises tris(2-ethylhexyl) phosphate.

7. The flame retardant polyurethane composition of claim 1 , wherein the phosphorus-containing flame retardant consists of at least one of tri-n-butyl phosphate and tri-isobutyl phosphate.

8. A flame retardant polyurethane composition comprising:

a flexible polyurethane foam reaction mixture including at least one polyol and at least one isocyanate; and

a flame retardant additive comprising an alkyl substituted triaryl phosphate ester; and a phosphorous-containing flame retardant selected from the group consisting of: tris(2-ethylhexyl) phosphate, resorcinol bis(diphenyl phosphate), tri-n-butyl phosphate, tri-isobutyl phosphate and mixtures thereof wherein the ratio of the alkyl substituted triaryl phosphate ester to the phosphorus-containing flame retardant is from about 95:5 to about 80:20 percent by weight, and wherein the combined weight of the alkyl substituted triaryl phosphate ester and the phosphorus-containing flame retardant comprises about 5 to about 40% by weight of polyol.

9. The flame retardant polyurethane composition of claim 8 , wherein the phosphorus-containing flame retardant includes at least about 5 wt. % phosphorus.

10. The flame retardant polyurethane composition of claim 8 , wherein the alkyl substituted triaryl phosphate ester includes one or more compounds having the general formula:

where each R is independently either a linear or branched C 1 to C 6 alkyl group, and n is independently an integer of 0, 1 or 2, but n may not be 0 in at least one instance.

11. The flame retardant polyurethane composition of claim 10 , wherein the alkyl substituted triaryl phosphate ester comprises at least one of tricresyl phosphate, butylated triphenyl phosphate, and isopropylated triphenyl phosphate.

12. The flame retardant polyurethane composition of claim 11 , wherein the alkyl substituted triaryl phosphate ester comprises a mixed isopropylated triphenyl phosphate containing about 8.6% phosphorus and also having about 35 wt. % of non-alkylated triphenyl phosphate.

13. The flame retardant polyurethane composition of claim 8 , wherein the phosphorus-containing flame retardant comprises resorcinol bis(diphenyl phosphate).

14. The flame retardant polyurethane composition of claim 8 , wherein the phosphorus-containing flame retardant comprises tris(2-ethylhexyl) phosphate.

15. The flame retardant polyurethane composition of claim 8 , wherein the phosphorus-containing flame retardant consists of at least one of tri-n-butyl phosphate and tri-isobutyl phosphate.

16. A flame retardant additive for use in flame retarding a flexible polyurethane foam reaction mixture including at least one polyol and at least one isocyanate, the flame retardant additive comprising:

an alkyl substituted triaryl phosphate ester; and

a phosphorous-containing flame retardant having at least about 5 wt. % phosphorus and including at least one monomeric phosphorus-containing compound selected from the group consisting of: tris(2-ethylhexyl) phosphate, resorcinol bis(diphenyl phosphate), tri-n-butyl phosphate, tri-isobutyl phosphate and mixtures thereof wherein the combined weight of the alkyl substituted triaryl phosphate ester and the phosphorus-containing flame retardant comprises about 5 to about 40% by weight of the polyol, and wherein the ratio of the alkyl substituted triaryl phosphate ester to the phosphorus-containing flame retardant is from about 95:5 to about 80:20 percent by weight.

17. The flame retardant additive of claim 16 , wherein the alkyl substituted triaryl phosphate ester has the general formula:

where each R is independently either a linear or branched C 1 to C 6 alkyl group, and n is independently an integer of 0, 1 or 2, but n may not be 0 in at least one instance.

18. The flame retardant additive of claim 17 , wherein the alkyl substituted triaryl phosphate ester comprises at least one of tricresyl phosphate, butylated triphenyl phosphate, and isopropylated triphenyl phosphate.

19. The flame retardant additive of claim 18 , wherein the alkyl substituted triaryl phosphate ester comprises a mixed isopropylated triphenyl phosphate containing about 8.6% phosphorus and also having about 35 wt. % of non-alkylated triphenyl phosphate.

20. The flame retardant additive of claim 16 , wherein the phosphorus-containing flame retardant comprises resorcinol bis(diphenyl phosphate).

21. The flame retardant additive of claim 16 , wherein the phosphorus-containing flame retardant comprises tris(2-ethylhexyl) phosphate.

22. The flame retardant additive of claim 16 , wherein the phosphorus-containing flame retardant consists of at least one of tri-n-butyl phosphate and tri-isobutyl phosphate.

23. A method of making flame retarded flexible polyurethane compositions comprising the step of:

adding to a flexible polyurethane foam reaction mixture about 5 to about 40% by weight of polyol of a flame retardant additive comprising: an alkyl substituted triaryl phosphate ester; and a phosphorus-containing flame retardant having at least about 5 wt. % phosphorus selected from the group consisting of: tris(2-ethylhexyl) phosphate, resorcinol bis(diphenyl phosphate), tri-n-butyl phosphate, tri-isobutyl phosphate and mixtures thereof, wherein the ratio of the alkyl substituted triaryl phosphate ester to the phosphorus-containing flame retardant is from about 95:5 to about 80:20 percent by weight.

24. The method of claim 23 , further comprising the step of pre-combining the alkyl substituted triaryl phosphate ester and the phosphorus-containing flame retardant prior to the step of adding the flame retardant additive to the flexible polyurethane foam reaction mixture.

25. The method of claim 23 , wherein the alkyl substituted triaryl phosphate ester has the general formula:

where each R is independently either a linear or branched C 1 to C 6 alkyl group, and n is independently an integer of 0, 1 or 2, but n may not be 0 in at least one instance.

26. The method of claim 25 , wherein the alkyl substituted triaryl phosphate ester comprises at least one of tricresyl phosphate, butylated triphenyl phosphate, and isopropylated triphenyl phosphate.

27. The method of claim 26 , wherein the alkyl substituted triaryl phosphate ester comprises a mixed isopropylated triphenyl phosphate containing about 8.6% phosphorus and also having about 35 wt. % of non-alkylated triphenyl phosphate.

28. The method of claim 27 , wherein the phosphorus-containing flame retardant comprises resorcinol bis(diphenyl phosphate).

29. The method of claim 27 , wherein the phosphorus-containing flame retardant comprises tris(2-ethylhexyl) phosphate.

30. The method of claim 27 , wherein the phosphorus-containing flame retardant consists of at least one of tri-n-butyl phosphate and tri-isobutyl phosphate.

Assignments (9)
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 →
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 →