Pyrrolidine-based catalysts for use in polyurethane materials

Patent metadata

Field	Value
Publication number	US-9988483-B2
Application number	US-201515126367-A
Country	US
Kind code	B2
Filing date	Jun 24, 2015
Priority date	Jun 27, 2014
Publication date	Jun 5, 2018
Grant date	Jun 5, 2018

Abstract

The present disclosure relates to pyrrolidine-based catalysts for use in a polyurethane formulation. The polyurethane formulation includes the pyrrolidine-based catalyst, a compound containing an isocyanate functional group, an active hydrogen-containing compound. The use of such catalysts produces high quality polyurethane foam while reducing environmental concerns that can arise during the production of polyurethane foam as well as in the foam that is produced.

First claim

What is claimed is:

1. A polyurethane formulation comprising:
(i) a pyrrolidine-based catalyst selected from pyrrolidine propanol, 1,1′-(oxybis(ethane-2-1-diyl) dipyrrolidine, 2-pyrrolidinyl-1-(2-pyrrolidinylethoxy)ethane, 2-(2-pyrrolidinylethoxy)ethan-1-ol), pyrrolidinylbutyl-morpholine, pyrrolidinylbutyl-pyrrolidine, imino-bis-4-aminobutyl pyrrolidine, 1,3-dipyrrolidinopropan-2-ol, and a mixture thereof;
(ii) a compound containing an isocyanate functional group; and
(iii) an active hydrogen-containing compound.

2. The polyurethane formulation of claim 1 wherein the compound containing an isocyanate functional group is at least one of a polyisocyanate and an isocyanate-terminated prepolymer.

3. The polyurethane formulation of claim 1 wherein the active hydrogen-containing compound is a polyol.

4. The polyurethane formulation of claim 3 wherein the polyol is a polyalkylene ether polyol, polyester polyols, polymer polyols, a non-flammable polyol, a halogen-containing polyol or a mixture thereof.

5. The polyurethane formulation of claim 1 further comprising at least one additional catalyst selected from an amine catalyst containing at least one tertiary amine group, a non-amine catalyst, and a combination thereof.

6. The polyurethane formulation of claim 5 , wherein the amine catalyst is selected from bis-(2-dimethylaminoethyl)ether, N,N,N′-trimethyl-N′-hydroxyethylbisaminoethylether, N-(3-dimethylaminopropyl)-N, N-diisopropanolamine, N, N-dimethylethanolamine, triethylene diamine, a blend of N,N-dimethylethanolamine and triethylene diamine, N,N-dimethylcyclohexylamine, benzyldimethylamine, pentamethyldiethylenetriamine, N,N,N′,N″,N″-pentamethyldipropylenetriamine, N,N-bis(3-dimethylaminopropyl)-N-isopropanolamine, N′-(3-(dimethylamino)propyl-N,N-dimethyl-1,3-propanediamine, 2-(2-dimethylaminoethoxy)ethanol, N,N,N′-trimethylaminoethyl-ethanolamine, N-ethylmorpholine, N-methylmorpholine, 4-methoxyethylmorpholine, N, N′dimethylpiperzine, 2,2′dimorpholinodiethylether, 1,3,5-tris(3-(dimethylamino)propyl)-hexahydro-s-triazine, 1-Propanamine, 3-(2-(dimethylamino)ethoxy), a substituted imidazole, N,N′-dimethylpiperazine, aminoethylpiperazine, N,N′,N′-trimethyl aminoethylpiperazine, bis-(N-methyl piperazine)urea, N-methylpyrrolidine, 2-aminoethyl-N-methylpyrrolidine, bis-(N-methylpyrrolidine)ethyl urea, 3-dimethylaminopropylamine, N,N,N″,N″-tetramethyldipropylenetriamine, tetramethylguanidine, 1,2 bis-diisopropanol, N-methylmorpholine, N-ethylmorpholine, N-butylmorpholine, dimorpholinodiethylether, N,N′-dimethylaminoethanol, N, N-dimethylamino ethoxyethanol, bis-(dimethylaminopropyl)-amino-2-propanol, bis-(dimethylamino)-2-propanol, bis-(N,N-dimethylamino)ethylether; N,N,N′-trimethyl-N′hydroxyethyl-bis-(aminoethyl)ether, N,N-dimethylaminoethyl-N′-methyl amino ethanol, tetramethyliminobispropylamine, a reactive acid blocked catalyst and a mixture thereof.

7. The polyurethane formulation of claim 5 wherein the weight ratio of the pyrrolidine-based catalyst of formula (I) to the at least one additional catalyst is at least 1:1.

8. The polyurethane formulation of claim 1 further comprising one or more auxiliary components selected from a cell stabilizer, surfactant, chain extender, pigment, filler, flame retardant, thermally expandable microsphere, blowing agent, water, thickening agent, smoke suppressant, reinforcement, antioxidant, UV stabilizer, antistatic agent, infrared radiation absorber, dye, mold release agent, antifungal agent, biocides and a combination thereof.

9. A method for producing a polyurethane material comprising contacting a compound containing an isocyanate functional group, an active hydrogen-containing compound and optional auxiliary components in the presence of a pyrrolidine-based catalyst selected from pyrrolidine propanol, 1,1′-(oxybis(ethane-2-1-diyl) dipyrrolidine, 2-pyrrolidinyl-1-(2-pyrrolidinylethoxy)ethane, 2-(2-pyrrolidinylethoxy)ethan-1l-ol), pyrrolidinylbutyl-morpholine, pyrrolidinylbutyl-pyrrolidine, imino-bis-4-aminobutyl pyrrolidine, 1,3-dipyrrolidinopropan-2-ol, and a mixture thereof.

10. A polyurethane material produced according to the method of claim 9 .

11. The polyurethane material of claim 10 , wherein the polyurethane material is a rigid foam or a flexible foam.

12. The polyurethane material of claim 10 , wherein the polyurethane material is substantially free of at least one of DMF, formaldehyde and dimethyl amine.

13. The polyurethane material produced according to the method of claim 9 for use as a precoat, a backing material for carpet, a building composite, insulation, a spray foam insulation, a urethane/urea hybrid elastomers; in vehicle interior and exterior parts, a flexible foam, an integral skin foam, a rigid spray foam, a rigid pour-in-place foam; a coating; an adhesive, a sealant, or a filament winding.

Assignees

• Huntsman Petrochemical Llc

Inventors

• Forkner Matthew W
• Grigsby Jr Robert A
• Wiltz Jr Eugene P
• Rister Jr Ernest L
• Rodriguez Frank
• Klein Howard P

Classifications

• C08G18/161

  containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22 · CPC title

• C08G2190/00

  Compositions for sealing or packing joints · CPC title

• C08G18/1825

  having hydroxy or primary amino groups · CPC title

• C08G18/4829

  Polyethers containing at least three hydroxy groups (C08G18/4833 - C08G18/5096 take precedence) · CPC title

• C08G2150/60

  Compositions for foaming; Foamed or intumescent coatings · CPC title