Reactive amine catalysts for polyurethane applications

Patent metadata

Field	Value
Publication number	US-2016347901-A1
Application number	US-201615170142-A
Country	US
Kind code	A1
Filing date	Jun 1, 2016
Priority date	Jun 1, 2015
Publication date	Dec 1, 2016
Grant date	—

Abstract

Tertiary amine catalysts having isocyanate reactive groups that are capable of forming thermally stable covalent bonds able to withstand temperatures up to 120° C. are disclosed. These catalyst can be used to produce polyurethane foam having the following desirable characteristics: a) very low chemical emissions over a wide range of environmental conditions and isocyanate indexes (e.g. indexes as low as 65 but higher than 60) while meeting all physical property requirements; b) sufficient hydrolytic stability to maintain the catalyst covalently bound to foam without leaching of tertiary amine catalyst when foam is exposed to water or aqueous solutions even at temperatures higher than ambient (temperature range 25° C. to 90° C.); and c) stable contact interface between the polyurethane polymer and other polymers (for example polycarbonate) with minimal migration of tertiary amine catalyst from polyurethane polymer to other polymers yielding no noticeable polymer deterioration at the point of contact even under conditions of heat and humidity.

First claim

The following is claimed:

1 ) A catalyst composition comprising at least one compound with the general formula A-NR1R2 wherein A=[Me2N—(CH2)3] 2N—(CH2)3- and R1=R2=—CH2-CH(R3)OH or R 1 =H and R 2 =—CH 2 —CH(R 3 )OH with R3=H. C1-C6 or A=[Me2N—(CH2) 3] 2N—(CH2)3- and R1=H and R2=—CO—NH-A or R1=H and R2=—CO—NH2.

2 ) The composition of claim 1 wherein the compound comprises at least one member selected from the group consisting of N.N′-bis[bis-N″.N″-(3-dimethylaminopropyl)-N″-(3-aminopropyl)]urea; N.N-bis(3-dimethylaminopropyl)-N-(3-aminopropyl)] urea; N.N-bis(3-dimethylaminopropyl)-N-[3-aminopropyl-N′.N′-bis(2-hydroxypropyl)]amine; N.N-bis(3-dimethylaminopropyl)-N-[3-aminopropyl-N′N′-bis[2-hydroxyethyl)amine; N.N-bis(3-dimethylaminopropyl)-N-[3-aminopropyl-N′-(2-hydroxyethyl)]amine; N.N-bis(3-dimethylaminopropyl)-N-[3-aminopropyl-N′(2-hydroxyethylk)]amine.

3 ) The composition of claim 1 further comprising at least one blowing catalyst.

4 ) The composition of claim 3 wherein the blowing catalyst comprises at least one member selected from the group consisting of N.N.N′-trimethyl-N′-3-aminopropyl-bis(aminoethyl) ether or 2-[N-(dimethylaminoethoxyethyl)-N-methylamino]ethanol and N.N.N′-trimethyl-N′-3-aminopropyl-bis(aminoethyl) ether.

5 ) A composition comprising at least one polyol and at least one gelling catalyst having at least functionality selected from the group consisting of a secondary OH functionality functionality and urea functionality.

6 ) The composition of claim 5 wherein the gelling catalyst comprises the catalyst of claim 1 .

7 ) The composition of claim 6 wherein the composition further comprises the blowing catalyst of claim 4 .

8 ) A method comprising contacting acrylonitrile and bis(dimethylaminopropyl)amine under conditions sufficient to obtain bis(dimethylaminopropyl)-cyanoethyl-amine; and contacting bis(dimethylaminopropyl)-cyanoethyl-amine with hydrogen under conditions sufficient to obtain N.N-bis(dimethylaminopropyl)-N-(3-aminopropyl)-amine and reacting N.N-bis(dimethylaminopropyl)-N-(3-aminopropyl)-amine under conditions sufficient to produce a compound having urea functionality.

9 ) The method of claim 8 wherein N.N-bis(dimethylaminopropyl)-N-(3-aminopropyl)-amine is reacted with at least one member selected from the group consisting of ethylene oxide and propylene oxide.

10 ) The method of claim 8 wherein N.N-bis(dimethylaminopropyl)-N-(3-aminopropyl)-amine is reacted with urea.

11 ) A method for making a polyurethane foam comprising contacting at least one polyol and at least one isocyanate in the presence of at least one gelling catalyst of claim 1 and at least one blowing catalyst.

12 ) A method for making a polyurethane foam comprising combining at least one polyol at least one gelling catalyst of claim 1 and at least one blowing catalyst and reacting the combination with at least one isocyante.

13 ) A foam produced in accordance with claim 11 or 12 .

14 ) The foam of claim 14 wherein the foam complies with VDA 278.

Assignees

• Air Prod & Chem

Inventors

• Burdeniuc Juan Jesus
• Panitzsch Torsten
• Xi Kai
• Keller Renee Jo

Classifications

• C08J9/142

  Compounds containing oxygen but no halogen atom · CPC title

• C08G18/3203

  Polyhydroxy compounds · CPC title

• C08G18/7621

  being toluene diisocyanate including isomer mixtures · CPC title

• C07C273/1809

  with formation of the N-C(O)-N moiety · CPC title

• C08G18/1841

  having carbonyl groups which may be linked to one or more nitrogen or oxygen atoms · CPC title