IP Library Granted Patent US 9,481,790
Granted Patent B2
US 9,481,790 · App. 14/737,879 · Granted Nov 1, 2016

Marine foam

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Quick Facts
Patent No.
US 9,481,790
App. No.
14/737,879
Granted
Nov 1, 2016
Kind
B2
Abstract

The invention generally pertains to the use of polyurethane foam blown by at least one blowing agent having a boiling point at atmospheric pressure of between ˜5° C. to ˜50° C., including miscible blends thereof, which passes all United States Coast Guard Title 33, Part 183 specifications wherein the buoyant force of the froth polyurethane or polyisocyanurate foam is not reduced more than 5% after exposure to being immersed in a fully saturated gasoline vapor atmosphere, in reference fuel B, in reference oil No. 2, and in a 5% solution of Na 3 PO 4 .

Claims (180)

1. A two component polyurethane or polyisocyanurate foam blown by at least one hydrofluorocarbon blowing agent having a boiling point at atmospheric pressure of between ˜5° C. to ˜50° C. and miscible blends thereof, which passes all United States Coast Guard Title 33, Part 183 specifications wherein the buoyant force of the foam is not reduced more than 5% after exposure to all of the conditions identified in the United States Coast Guard Title 33, Part 183 specifications, namely:

the two component polyurethane foam synthesized from two sets of pressurized reactant components which comprise an A-side and a B-side:

the B-side reactant components comprising a polyol blend:

25-45 wt. % of at least one polyether polyol in the polyol blend present in a major amount;

10-30 wt. % of at least one phthalic anhydride based aromatic polyester polyol present in a minor amount in the polyol blend, the at least one phthalic anhydride based aromatic polyester polyol comprising at least 35% of the polyol blend;

30-65 wt. % of at least one other additive selected from the group comprising at least one flame retardant and at least one plasticizer;

1-5 wt. % of at least one surfactant;

1-5 wt. % of at least one catalyst;

0.5-3 wt. % of water;

the at least one hydrofluorocarbon blowing agent having a boiling point at atmospheric pressure of between ˜5° C. to ˜50° C. and miscible blends thereof; and

the weight percentages of all of the B-side reactant components combining to total 100%;

the A-side reactive components comprising:

a poly- or diisocyanate; and

the at least one hydrofluorocarbon blowing agent having a boiling point at atmospheric pressure of between ˜5° C. to ˜50° C. and miscible blends thereof.

2. The polyurethane foam of claim 1 wherein

the at least one phthalic anhydride based aromatic polyester is

wherein

R 1 is selected from the group consisting of an alkylene group of from 2 to 10 carbon atoms, —CH 2 —R 3 —CH 2 —, and —(R 4 O) m —R 4 —;

R 2 and R 5 are independently —[CH 2 CH 2 O] x —, [CH 2 CH(CH 3 )O] x —, —[CH 2 CH 2 CH(CH 3 )O] x —, or a random combination thereof;

R 3 is selected from the group consisting of

each R 4 is independently an alkylene group of from 2 to 4 carbon atoms; and

x, m, and n are independently from 1-200.

3. The polyurethane foam of claim 2 wherein

the at least one phthalic anhydride based aromatic polyester polyol is

and further wherein

an hydroxyl number in mg KOH/g is between 230-250 inclusive;

a viscosity value at 25° C. is between 2,000-4,500 cP inclusive;

an equivalent average weight is approximately 234; and

an average molecular weight is approximately 468.

4. The polyurethane foam of claim 2 wherein

the at least one polyether polyol is

and further wherein

an hydroxyl number in mg KOH/g is approximately 600;

a viscosity value at 25° C. is approximately 380 cP; and

an average molecular weight is approximately 280.

5. The polyurethane foam of claim 4 wherein

the at least one other additive is selected from the group comprising

6. The polyurethane foam of claim 5 wherein

the at least one catalyst is at least two catalysts selected from the group comprising

7. The polyurethane foam of claim 6 wherein

the water is added in an amount of approximately 1% by weight.

8. The polyurethane foam of claim 7 wherein

the at least one blowing agent has a boiling point at atmospheric pressure of between ˜10° C. to ˜40° C.

9. The polyurethane foam of claim 8 wherein

the at least one blowing agent is 1,1,1,3,3-pentafluoropropane.

10. A process of synthesizing a two-component polyurethane or polyisocyanurate foam blown by at least one hydrofluorocarbon blowing agent having a boiling point at atmospheric pressure of between ˜5° C. to ˜50° C., and miscible blends thereof, which passes all United States Coast Guard Title 33, Part 183 specifications wherein the buoyant force of the foam is not reduced more than 5% after testing pursuant to the United States Coast Guard Title 33, Part 183 specifications:

the two-component polyurethane foam synthesized from two sets of pressurized reactant components which comprise an A-side and a B-side:

the B-side reactant components comprising a polyol blend:

25-45 wt. % of at least one polyether polyol in the polyol blend present in a major amount;

10-30 wt. % of at least one phthalic anhydride based aromatic polyester polyol present in a minor amount in the polyol blend;

30-65 wt. % of at least one other additive selected from the group comprising at least one flame retardant and at least one plasticizer;

1-5 wt. % of at least one surfactant;

1-5 wt. % of at least one catalyst;

0.5-3 wt. % of water;

the at least one hydrofluorocarbon blowing agent having a boiling point at atmospheric pressure of between ˜5° C. to ˜50° C. and miscible blends thereof; and

the weight percentages of all of the B-side reactant components combining to total 100%;

the A-side reactive components comprising:

a poly- or diisocyanate; and

the at least one hydrofluorocarbon blowing agent having a boiling point at atmospheric pressure of between ˜5° C. to ˜50° C. and miscible blends thereof,

the process comprising the step of adding at least one phthalic anhydride based aromatic polyester polyol comprising at least 35% of the polyol blend, the ortho substitution on the phenyl ring providing additional thermal, hydrolytic and chemical stability to a polyurethane without the added amount of the at least one phthalic anhydride based aromatic polyester polyol.

11. The process of claim 10 wherein

The at least one phthalic anhydride based aromatic polyester polyol is

wherein

R 1 is selected from the group consisting of an alkylene group of from 2 to 10 carbon atoms, —CH 2 —R 3 —CH 2 —, and —(R 4 O) m —R 4 —;

R 2 and R 5 are independently —[CH 2 CH 2 O] x —, [CH 2 CH(CH 3 )O] x —, —[CH 2 CH 2 CH(CH 3 )O] x —, or a random combination thereof;

R 3 is selected from the group consisting of

each R 4 is independently an alkylene group of from 2 to 4 carbon atoms; and

x, m, and n are independently from 1-200.

12. The process of claim 11 wherein

the at least one phthalic anhydride based aromatic polyester polyol is

and further wherein

an hydroxyl number in mg KOH/g is between 230-250 inclusive;

a viscosity value at 25° C. is between 2,000-4,500 cP inclusive;

an equivalent average weight is approximately 234; and

an average molecular weight is approximately 468.

13. The process of claim 11 wherein

the at least one polyether polyol is

and further wherein

an hydroxyl number in mg KOH/g is approximately 600;

a viscosity value at 25° C. is approximately 380 cP; and

an average molecular weight is approximately 280.

14. The process of claim 13 wherein

the at least one other additive is selected from the group comprising

15. The polyurethane foam of claim 14 wherein

the at least one catalyst is at least two catalysts selected from the group comprising

16. The process of claim 15 wherein

the water is added in an amount of approximately 1% by weight.

17. The process of claim 16 wherein

the at least one blowing agent has a boiling point at atmospheric pressure of between ˜10° C. to ˜40° C.

18. The process of claim 17 wherein

the at least one blowing agent is 1,1,1,3,3-pentafluoropropane.

19. A two-component polyurethane or polyisocyanurate foam blown by at least one hydrofluoroolefin blowing agent having a boiling point at atmospheric pressure of between ˜5° C. to ˜50° C. and miscible blends thereof, which passes all United States Coast Guard Title 33, Part 183 specifications wherein the buoyant force of the foam is not reduced more than 5% after testing pursuant to the United States Coast Guard Title 33, Part 183 specifications:

the two-component polyurethane foam synthesized from two sets of pressurized reactant components which comprises an A-side and a B-side:

the B-side reactant components comprising a polyol blend:

25-45 wt. % of at least one polyether polyol in the polyol blend present in a major amount;

10-30 wt. % of at least one phthalic anhydride based aromatic polyester polyol present in a minor amount in the polyol blend, the at least one phthalic anhydride based aromatic polyester polyol comprising at least 35% of the polyol blend;

30-65 wt. % of at least one other additive selected from the group comprising at least one flame retardant and at least one plasticizer;

1-5 wt. % of at least one surfactant;

1-5 wt. % of at least two catalysts, one of which is a tin-based catalyst;

essentially no water;

the least one hydrofluoroolefin blowing agent having a boiling point at atmospheric pressure of between ˜5° C. to ˜50° C. and miscible blends thereof; and

the weight percentages of all of the B-side reactant components combining to total 100%;

the A-side reactive components comprising:

a poly- or diisocyanate; and

the least one hydrofluoroolefin blowing agent having a boiling point at atmospheric pressure of between ˜5° C. to ˜50° C. and miscible blends thereof.

20. The polyurethane foam of claim 19 wherein

the at least one phthalic anhydride based aromatic polyester polyol is

wherein

R 1 is selected from the group consisting of an alkylene group of from 2 to 10 carbon atoms, —CH 2 —R 3 —CH 2 —, and —(R 4 O) m —R 4 —;

R 2 and R 5 are independently —[CH 2 CH 2 O] x —, [CH 2 CH(CH 3 )O] x —, —[CH 2 CH 2 CH(CH 3 )O] x —, or a random combination thereof;

R 3 is selected from the group consisting of

each R 4 is independently an alkylene group of from 2 to 4 carbon atoms; and

x, m, and n are independently from 1-200.

21. The polyurethane foam of claim 20 wherein

the at least one phthalic anhydride based aromatic polyester polyol is

and further wherein

an hydroxyl number in mg KOH/g is between 230-250 inclusive;

a viscosity value at 25° C. is between 2,000-4,500 cP inclusive;

an equivalent average weight is approximately 234; and

an average molecular weight is approximately 468.

22. The polyurethane foam of claim 20 wherein

the at least one polyether polyol is

and further wherein

an hydroxyl number in mg KOH/g is approximately 600;

a viscosity value at 25° C. is approximately 380 cP; and

an average molecular weight is approximately 280.

23. The polyurethane foam of claim 22 wherein

the at least one other additive is selected from the group comprising

24. The polyurethane foam of claim 23 wherein

the at least two catalysts comprise

and at least one of

25. The polyurethane foam of claim 24 wherein

the at least one blowing agent has a boiling point at atmospheric pressure of between ˜10° C. to ˜40° C.

26. The polyurethane foam of claim 25 wherein

the at least one blowing agent is 1,1,1,4,4,4 hexafluoro-2-butene.

27. A process of synthesizing a two-component polyurethane or polyisocyanurate foam blown by at least one hydrofluoroolefin blowing agent having a boiling point at atmospheric pressure of between ˜5° C. to ˜50° C., and miscible blends thereof, which passes all United States Coast Guard Title 33, Part 183 specifications wherein the buoyant force of the foam is not reduced more than 5% after testing pursuant to the United States Coast Guard Title 33, Part 183 specifications:

the two-component polyurethane foam synthesized from two sets of pressurized reactant components which comprises an A-side and a B-side:

the B-side reactant components comprising a polyol blend:

25-45 wt. % of at least one polyether polyol in the polyol blend present in a major amount;

10-30 wt. % of at least one phthalic anhydride based aromatic polyester polyol present in a minor amount in the polyol blend;

25-45 wt. % of at least one plasticizer;

30-65 wt. % of at least one other additive selected from the group comprising at least one flame retardant and at least one plasticizer;

1-5 wt. % of at least two catalysts, one of which is a tin-based catalyst;

no added water;

the at least one hydrofluoroolefin blowing agent having a boiling point at atmospheric pressure of between ˜5° C. to ˜50° C., and miscible blends thereof; and

the weight percentages of all of the B-side reactant components combining to total 100%;

the A-side reactive components comprising:

a poly- or diisocyanate; and

the at least one hydrofluoroolefin blowing agent having a boiling point at atmospheric pressure of between ˜5° C. to ˜50° C., and miscible blends thereof,

the process comprising the step of adding at least one phthalic anhydride based aromatic polyester polyol comprising at least 35% of the polyol blend, the ortho substitution on the phenyl ring providing additional thermal, hydrolytic and chemical stability to a polyurethane without the added amount of the at least one phthalic anhydride based aromatic polyester polyol.

28. The process of claim 27 wherein

the at least one phthalic anhydride based aromatic polyester polyol is

wherein

R 1 is selected from the group consisting of an alkylene group of from 2 to 10 carbon atoms, —CH 2 —R 3 —CH 2 —, and —(R 4 O) m —R 4 —;

R 2 and R 5 are independently —[CH 2 CH 2 O] x —, [CH 2 CH(CH 3 )O] x —, —[CH 2 CH 2 CH(CH 3 )O] x —, or a random combination thereof;

R 3 is selected from the group consisting of

each R 4 is independently an alkylene group of from 2 to 4 carbon atoms; and

x, m, and n are independently from 1-200.

29. The process of claim 28 wherein

the at least one phthalic anhydride based aromatic polyester polyol is

and further wherein

an hydroxyl number in mg KOH/g is between 230-250 inclusive;

a viscosity value at 25° C. is between 2,000-4,500 cP inclusive;

an equivalent average weight is approximately 234; and

an average molecular weight is approximately 468.

30. The process of claim 28 wherein

the at least one polyether polyol is

and further wherein

an hydroxyl number in mg KOH/g is approximately 600;

a viscosity value at 25° C. is approximately 380 cP; and

an average molecular weight is approximately 280.

31. The process of claim 30 wherein

the at least one other additive is selected from the group comprising

32. The process of claim 31 wherein

the at least two catalysts comprise

and at least one of

33. The process of claim 32 wherein

the at least one blowing agent has a boiling point at atmospheric pressure of between ˜10° C. to ˜40° C.

34. The process of claim 33 wherein

the at least one blowing agent is 1,1,1,4,4,4 hexafluoro-2-butene.

Assignments (16)
ASSIGNMENT OF 2ND LIEN SECURITY INTEREST (REEL 054888 / FRAME 0048) Recorded Sep 15, 2023
From: ANTARES CAPITAL LP
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 064923/0317 →
SECURITY AGREEMENT (SECOND LIEN) Recorded Jan 4, 2021
From: ICP CONSTRUCTION, INC.; GARDNER-GIBSON, INC.; GARDNER ASPHALT CORPORATION; PLI-DEK, LLC; SUN COATINGS, INC.
To: ANTARES CAPITAL, L.P., AS COLLATERAL AGENT
Reel/Frame 054888/0048 →
SECURITY AGREEMENT (FIRST LIEN) Recorded Dec 31, 2020
From: ICP CONSTRUCTION, INC.; GARDNER-GIBSON, INC.; GARDNER ASPHALT CORPORATION; PLI-DEK, LLC; SUN COATINGS, INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 054883/0265 →
MERGER Recorded Dec 30, 2020
From: ICP ADHESIVES AND SEALANTS, INC.
To: ICP MERGER OPCO, LLC
Reel/Frame 054775/0076 →
MERGER Recorded Dec 30, 2020
From: ICP MERGER HOLDCO, LLC; ICP MERGER OPCO, LLC
To: ICP CONSTRUCTION, INC.
Reel/Frame 054775/0198 →
RELEASE OF SECURITY INTEREST : RECORDED AT REEL/FRAME - 044037-0515; 044037-0590; 045792-0510 AND 050426-0086 Recorded Dec 30, 2020
From: GOLDMAN SACHS MIDDLE MARKET LENDING CORP.
To: ICP ADHESIVES AND SEALANTS, INC.; LENOX ACQUISITION, LLC; PLI-DEK, LLC; ICP CONSTRUCTION, INC.
Reel/Frame 054871/0203 →
RELEASE OF SECURITY INTEREST Recorded Dec 29, 2020
From: ANTARES CAPITAL LP, AS AGENT
To: ICP ADHESIVES AND SEALANTS, INC.; LENOX ACQUISITION, LLC; PLI-DEK, LLC; ICP CONSTRUCTION, INC.
Reel/Frame 054866/0395 →
SECURITY INTEREST Recorded Nov 6, 2017
From: ICP ADHESIVES AND SEALANTS, INC.
To: GOLDMAN SACHS MIDDLE MARKET LENDING CORP., AS COLLATERAL AGENT
Reel/Frame 044037/0515 →
RELEASE OF SECURITY INTEREST RECORDED AT REEL/FRAME 038247/0001 Recorded Nov 4, 2017
From: NXT CAPITAL, LLC
To: ICP ADHESIVES AND SEALANTS, INC.
Reel/Frame 044682/0157 →
RELEASE OF SECURITY INTEREST RECORDED AT REEL/FRAME 038365/0461 Recorded Nov 4, 2017
From: MARANON CAPITAL, L.P.
To: ICP ADHESIVES AND SEALANTS, INC. (F/K/A FOMO PRODUCTS)
Reel/Frame 044367/0168 →
SECURITY INTEREST Recorded Nov 3, 2017
From: ICP ADHESIVES AND SEALANTS, INC.
To: ANTARES CAPITAL LP, AS COLLATERAL AGENT
Reel/Frame 044026/0202 →
MERGER AND CHANGE OF NAME Recorded Sep 27, 2016
From: FOMO PRODUCTS, INC.; ICP ADHESIVES AND SEALANTS, INC.
To: ICP ADHESIVES AND SEALANTS, INC.
Reel/Frame 039868/0587 →
CHANGE OF NAME Recorded Aug 18, 2016
From: FOMO PRODUCTS, INC.
To: ICP ADHESIVES AND SEALANTS, INC.
Reel/Frame 039479/0889 →
SECURITY INTEREST Recorded Apr 25, 2016
From: FOMO PRODUCTS, INC.
To: MARANON CAPITAL, L.P., AS AGENT
Reel/Frame 038365/0461 →
SECURITY INTEREST Recorded Apr 11, 2016
From: FOMO PRODUCTS, INC.
To: NXT CAPITAL, LLC, AS AGENT
Reel/Frame 038247/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 12, 2015
From: TAYLOR, ANTHONY J.
To: FOMO PRODUCTS, INC.
Reel/Frame 035828/0380 →