IP Library Granted Patent US 11,028,219
Granted Patent B2
US 11,028,219 · App. 16/574,691 · Granted Jun 8, 2021

Compositions for polyurethane applications

Inventors: Ganapathy S. Viswanathan (Louisville, KY); Anthony Maiorana (Louisville, KY); Stephan Schröter (Essen, DE); Pravin Kukkaia (Louisville, KY)
Assignee: HEXION INC.
C08G18/7621C07C251/64C08G18/10C08G18/1833C08G18/2081C08G18/4027C08G18/544C08G18/6511C08G18/73C08G18/755C08G18/7664C08G18/7671C08G18/791C08G18/80C08J9/141C08K3/016C08K5/3462C08K5/34922C08K5/49C08L75/04C08G2101/00C08G2110/005C08G2110/0008C08G2110/0025C08G2110/0083C08G2120/00C08G2170/20C08G2190/00C08G2350/00C08G2380/00C08G2410/00C08J9/0038C08J2375/04
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Quick Facts
Patent No.
US 11,028,219
App. No.
16/574,691
Granted
Jun 8, 2021
Kind
B2
Abstract

A process comprising, consisting of, or consisting essentially of: forming a reaction mixture containing at least one polyisocyanate and an isocyanate-reactive compound comprising at least one alkoxylated triazine-arylhydroxy-aldehyde condensate composition wherein the alkoxylated triazine-arylhydroxy-aldehyde condensate composition is a reaction product of a triazine-arylhydroxy-aldehyde condensate and at least one alkylene carbonate, is disclosed.

Claims (32)

1. A polyol composition formed from a reaction mixture, comprising:

a triazine-arylhydroxy-aldehyde condensate;

at least one alkylene carbonate; and

an optional catalyst.

2. The polyol composition of claim 1 , wherein the optional catalyst is present in the reaction mixture and is selected from the group consisting of sodium hydroxide, potassium hydroxide, lithium hydroxide, ammonium hydroxide, magnesium hydroxide, calcium hydroxide, barium hydroxide, sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, potassium phosphate, sodium phosphate, and lithium phosphate, and combinations thereof.

3. The polyol composition of claim 1 , wherein the triazine-arylhydroxy-aldehyde condensate is formed from a reaction mixture comprising:

a triazine monomer;

an arylhydroxy monomer;

an aldehyde monomer; and

a catalyst.

4. The polyol composition of claim 1 , wherein the polyol composition further comprises a diluent and comprises a viscosity in the range of 1 Pascal second to about 1,700 Pascal second at 25° C.

5. The polyol composition of claim 4 , wherein the diluent comprises polyglycols, etherified polyglycols, dibasic esters of acids, and combinations thereof.

6. The polyol composition of claim 1 , wherein the alkylene carbonate is selected from the group consisting of ethylene carbonate, propylene carbonate or combinations thereof.

7. The polyol composition of claim 3 , wherein the triazine is selected from the group consisting of melamine, benzoguanamine, acetoguanamine, and combinations thereof, the arylhydroxy compound is selected from the group consisting of phenol, cresols, bisphenol A, xylenols, bisphenols, alkylated bisphenols, alkoxy phenols, dihydroxy benzene, naphthols, biphenols, alkylated biphenols, trisphenols and combinations thereof, and the aldehyde is formaldehyde or a formaldehyde donor.

8. The polyol composition of claim 3 , wherein the catalyst for the formation of triazine-arylhydroxy-aldehyde condensate comprises acetic acid, formic acid, benzoic acid, oxalic acid, an organic amine, and combinations thereof.

9. The polyol composition of claim 1 , wherein the polyol composition comprises a nitrogen content of from 7 weight percent to 21 weight percent.

10. The polyol composition of claim 1 , wherein the polyol composition comprises an aromatic content of from 29 weight percent to 68 weight percent.

11. The polyol composition of claim 1 , wherein the polyol composition comprises a viscosity from 40 milli Pascal second to 650 milli Pascal seconds at 130° C.

12. A polymer composition comprising:

an isocyanate;

isocyanate-reactive compound;

an alkoxylated triazine-arylhydroxy-aldehyde condensate;

optionally one or more components selected from the group consisting of a catalyst, surfactant, blowing agent, cell opener, filler, pigment and/or colorant, desiccant, reinforcing agent, biocide, preservative, antioxidant, flame retardant, diluent, and combinations thereof.

13. The polymer composition of claim 12 , wherein the alkoxylated triazine-arylhydroxy-aldehyde condensate is a reaction product of a triazine-arylhydroxy-aldehyde condensate and at least one alkylene carbonate.

14. The polymer composition of claim 13 , wherein the alkylene carbonate is ethylene carbonate, propylene carbonate, or a combination thereof.

15. The polymer composition of claim 12 , wherein the composition is free of a catalyst, is free of a fire retardant, is free of Mannich polyols, or combinations thereof.

16. The polymer composition of claim 12 , wherein the alkoxylated triazine-arylhydroxy-aldehyde condensate comprises an ethoxylated triazine-phenol-formaldehyde, a propoxylated triazine-phenol-formaldehyde, an ethoxylated propoxylated triazine-phenol-formaldehyde, or a combination thereof.

17. A process comprising reacting a reaction mixture comprising:

polyisocyanates;

a polyether polyol obtained by reacting a triazine-arylhydroxy-aldehyde condensate with at least one alkylene carbonate; and

optionally one or more components selected from the group consisting of a catalyst, surfactant, blowing agent, cell opener, filler, pigment and/or colorant, desiccant, reinforcing agent, biocide, preservative, antioxidant, flame retardant, diluent, and combinations thereof.

18. The process of claim 17 , wherein the reaction mixture is free of a catalyst, is free of a fire retardant, is free of Mannich polyols, or combinations thereof.

Assignments (13)
SECURITY INTEREST Recorded May 12, 2025
From: BAKELITE CHEMICALS LLC; BAKELITE UK HOLDING LTD.; BAKELITE GMBH; BAKELITE SYNTHETICS UK
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 071090/0740 →
ASSIGNMENT OF PATENT AND TRADEMARK SECURITY INTEREST Recorded May 12, 2025
From: MACQUARIE CAPITAL FUNDING LLC
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 071276/0379 →
SECURITY INTEREST Recorded Jan 23, 2025
From: BAKELITE CHEMICALS LLC; BAKELITE UK HOLDING LTD.; BAKELITE GMBH; BAKELITE SYNTHETICS UK LIMITED
To: GOLDMAN SACHS BANK USA
Reel/Frame 069981/0468 →
RELEASE OF SECURITY INTEREST Recorded Jun 15, 2022
From: GOLDMAN SACHS SPECIALTY LENDING GROUP, L.P.
To: HEXION VAD LLC
Reel/Frame 060209/0558 →
SECURITY INTEREST Recorded Jun 9, 2022
From: GEORGIA-PACIFIC CHEMICALS LLC; GEORGIA-PACIFIC CONSUMER PRODUCTS LP; ENERG2 TECHNOLOGIES, INC.; KOCH AGRONOMIC SERVICES LLC; BAKELITE UK HOLDING LTD.
To: MACQUARIE CAPITAL FUNDING LLC, AS ADMINISTRATIVE AGENT
Reel/Frame 060328/0327 →
SECURITY INTEREST Recorded Jun 9, 2022
From: GEORGIA-PACIFIC CHEMICALS LLC; GEORGIA-PACIFIC CONSUMER PRODUCTS LP; ENERG2 TECHNOLOGIES, INC.; KOCH AGRONOMIC SERVICES LLC; BAKELITE UK HOLDING LTD.; SURFACE TECH LLC
To: GOLDMAN SACHS BANK USA, AS ADMINISTRATIVE AGENT
Reel/Frame 060328/0250 →
CHANGE OF NAME Recorded May 3, 2022
From: HEXION VAD LLC
To: BAKELITE LLC
Reel/Frame 059926/0973 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 3, 2022
From: BAKELITE LLC
To: BAKELITE UK HOLDING LTD.
Reel/Frame 060377/0699 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 30, 2021
From: HEXION INC.
To: HEXION VAD LLC
Reel/Frame 057323/0086 →
RELEASE OF SECURITY INTEREST Recorded May 12, 2021
From: JPMORGAN CHASE BANK, N.A.
To: HEXION INC.
Reel/Frame 056219/0582 →
RELEASE OF SECURITY INTEREST Recorded May 12, 2021
From: JPMORGAN CHASE BANK, N.A.
To: HEXION INC.
Reel/Frame 056219/0677 →
SECURITY INTEREST Recorded May 5, 2021
From: HEXION VAD LLC
To: GOLDMAN SACHS SPECIALTY LENDING GROUP, L.P., AS COLLATERAL AGENT
Reel/Frame 056145/0957 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 5, 2019
From: VISWANATHAN, GANAPATHY S.; MAIORANA, ANTHONY; SCHROETER, STEPHAN; KUKKALA, PRAVIN
To: HEXION INC.
Reel/Frame 050917/0968 →
Continuity (2)
Continuation 15713583 · Sep 22, 2017
Related Publication 20200010606A1 · Jan 9, 2020