Trimerization catalysts from sterically hindered salts

Patent metadata

Field	Value
Publication number	US-9890236-B2
Application number	US-201314012155-A
Country	US
Kind code	B2
Filing date	Aug 28, 2013
Priority date	May 4, 2006
Publication date	Feb 13, 2018
Grant date	Feb 13, 2018

Abstract

The present invention provides trimerization catalyst compositions having a sterically hindered carboxylate salt and methods to produce a polyisocyanurate/polyurethane foam using such trimerization catalyst compositions.

First claim

The invention claimed is:

1. A composition comprising:
i) at least one polyol, wherein the polyol includes a reaction product of at least one of ethylene oxide or propylene oxide with at least one of ethylene glycol, propylene glycol, 1,3-butane diol, 1,4-butane diol, 1,6-hexane diol, neopentyl glycol, diethylene glycol, dipropylene glycol, pentaerythritol, glycerol, diglycerol, trimethylol propane, cyclohexane diol, sucrose, ethylenediamine, diethylenetriamine, or a reaction product of at least one of adipic acid, phthalic acid, or phthalic anhydride with at least one of ethylene glycol, propylene glycol, 1,3-butane diol, 1,4-butane diol, 1,6-hexane diol, neopentyl glycol, diethylene glycol, dipropylene glycol, pentaerythritol, glycerol, diglycerol, trimethylol propane, or butanediol;
ii) about 10 to about 80 parts by weight per hundred weight parts of polyol of at least one hydrocarbon blowing agent, wherein the at least one hydrocarbon blowing agent comprising at least one member selected from the group consisting of n-pentane, iso-pentane and cyclopentane, with the proviso that the at least one blowing agent is not a chlorofluorocarbon;
iii) about 0.5 to about 10 pphp of at least one silicon surfactant;
iv) greater than zero to about 10 pphp water;
v) greater than zero to about 50 pphp flame retardant;
vi) greater than zero to about 10 pphp of at least one urethane catalyst, wherein the urethane catalyst includes pentamethyldiethylenetriamine or pentamethyldipropylenetriamine; and
vii) about 0.05 to about 10 pphp of a catalyst composition comprising at least one sterically hindered carboxylate salt selected from the group consisting of potassium triethylacetate, potassium pivalate, potassium neoheptanoate, potassium neodecanoate, tetramethyl ammonium pivalate, dimethyldiallylammonium pivalate, tetramethylammonium neoheptanoate, tetramethylammonium neodecanoate, and combinations thereof.

2. A composition comprising the contact product of:
(a) at least one active hydrogen-containing compound selected from the group consisting of at least one polyether polyol, at least one polyester polyol, and combinations thereof;
(b) a catalyst composition comprising at least one sterically hindered carboxylate salt selected from the group consisting of potassium pivalate, tetramethylammonium pivalate, 2-hydroxyl-propyltrimethylammonium pivalate, 2-hydroxylpropyltriethylammonium pivalate, tetraethylammonium pivalate; and
(c) at least one blowing agent comprising at least one member selected from the group consisting of water, n-pentane, iso-pentane and cyclopentane, with the proviso that the at least one blowing agent is not a chlorofluorocarbon;
(d) at least one polyisocyanate selected from the group consisting of 2,4-toluene diisocyanate or 2,6-toluene diisocyanate; and
wherein the isocyanate index is between 150 to 270.

3. The composition of claim 2 , wherein the at least one sterically hindered carboxylate salt includes tetramethylammonium pivalate.

4. The composition of claim 2 , wherein the at least one active hydrogen-containing compound includes a reaction product of at least one of ethylene oxide or propyleneoxide, with at least one of ethylene glycol, propylene glycol, 1,3-butane diol, 1,4-butane diol, 1,6-hexane diol, neopentyl glycol, diethylene glycol, dipropylene glycol, pentaerythritol, glycerol, diglycerol, trimethylol propane, cyclohexane diol, sucrose, ethylenediamine, diethylenetriamine, tolylenediamine, diphenylmethanediamine, or triethanolamine.

5. The composition of claim 2 , wherein the at least one active hydrogen-containing compound includes a reaction product of at least one of adipic acid, phthalic acid, or phthalic anhydride, with at least one of ethylene glycol, propylene glycol, 1,3-butanediol, 1,4-butane diol, 1,6-hexane diol, neopentyl glycol, diethylene glycol, dipropylene glycol, pentaerythritol, glycerol, diglycerol, trimethylol propane, or butanediol.

6. The composition of claim 2 , further comprising at least one silicon surfactant and at least one flame retardant.

7. The composition of claim 6 , wherein the at least one blowing agent is present in about 10 to about 80 parts by weight per hundred parts (pphp) of polyol; and
wherein the catalyst composition is present in an amount between about 0.05 to about 10 pphp; and
wherein the at least one silicon surfactant is present in an amount between about 0.5 to about 10 pphp; and
wherein the at least one flame retardant is present in an amount greater than zero to about 50 pphp.

8. The composition of claim 7 , wherein the at least one blowing agent includes water and at least one of n-pentane, iso-pentane, or cyclopentane; and
wherein the water is present in an amount greater than zero and less than about 10 pphp.

9. The composition of claim 8 , wherein the at least one blowing agent is present in about 16 to about 40 parts by weight per hundred weight parts (pphp) of polyol; and wherein the catalyst composition is present in an amount between about 0.8 to about 8 pphp; and
wherein the at least one silicon surfactant is present in an amount between about 0.7 to about 4 pphp; and
wherein the at least one flame retardant is present in an amount greater than zero to about 7 pphp; and
wherein the water is present in an amount greater than zero and less than about 4 pphp.

10. The composition of claim 2 , wherein the at least one active hydrogen-containing compound includes a reaction product of at least one of ethylene oxide or propyleneoxide with at least one of ethylene glycol, propylene glycol, 1,3-butane diol, 1,4-butane diol, 1,6-hexane diol, neopentyl glycol, diethylene glycol, dipropylene glycol, pentaerythritol, glycerol, diglycerol, trimethylol propane, cyclohexane diol, sucrose, ethylenediamine, diethylenetriamine, tolylenediamine, diphenylmethanediamine, or triethanolamine.

11. The composition of claim 2 , wherein the at least one active hydrogen-containing compound includes a reaction product of at least one of adipic acid, phthalic acid, or phthalic anhydride with at least one of ethylene glycol, propylene glycol, 1,3-butane diol, 1,4-butane diol, 1,6-hexane diol, neopentyl glycol, diethylene glycol, dipropylene glycol, pentaerythritol, glycerol, diglycerol, trimethylol propane, or butanediol.

12. The composition of claim 2 , further comprising a urethane catalyst selected from the group consisting of 1,2-dimethylimidazole, N-methylmorpholine, N-ethylmorpholine, triethylamine, N,N′-dimethylpiperazine, 1,3,5-tris(dimethylaminopropyl)hexahydrotriazine, 2,4,6-tris(dimethylaminomethyl)phenol, pentamethyldipropylene triamine, N-methyl-N′-(2-dimethylamino)-ethyl-piperazine, tributylamine, pentamethyldiethylenetriamine, hexamethyltriethylenetetramine, heptamethyltetraethylenepentamine, pentamethyldipropylenetriamine, dimethylethanolamine, bis(dimethylaminoethyl)ether, tris(3-dimethylamino)propylamine, 1,8-diazabicyclo[5.4.0]undecene, and combinations thereof.

13. The composition of claim 12 , wherein the urethane catalyst includes pentamethyldiethylenetriamine or pentamethyldipropylenetriamine.

14. The composition of claim 2 , further comprising at least one alkali metal a,B-unsaturated carboxylate salt, at least one alkali metal carboxylate salt, at least one quaternary ammonium a,B-unsaturated carboxylate salt, or at least one quaternary ammonium carboxylate salt, or any combination thereof.

15. The composition of claim 2 , further comprising at least one diluent.

Assignees

• Evonik Degussa Gmbh

Inventors

• Burdeniuc Juan Jesus
• Panitzsch Torsten
• Dewhurst John Elton

Classifications

• C08G18/1808

  having alkylene polyamine groups · CPC title

• C08G18/225

  of alkali or alkaline earth metals · CPC title

• C08G18/42

  Polycondensates having carboxylic or carbonic ester groups in the main chain · CPC title

• C08G18/092 Primary

  oligomerisation to isocyanurate groups · CPC title

• C08G18/168 Primary

  Organic compounds · CPC title