Trimerization catalysts

Abstract

The present invention relates to ammonium salts of formula (I)

##STR00001##

where R=H, CH.sub.3, CH.sub.2CH.sub.3; n=1, 2, 3, 4, 5; m=2, 3; R, R, R=CH.sub.3, CH.sub.2CH.sub.3; R.sup.IV=H, CH.sub.3, CH.sub.2CH.sub.3 and X=monovalent counterion, to a process for their production and to the use thereof.

Claims

1. Ammonium salt of formula (I) ##STR00005## where R=H, CH.sub.3, CH.sub.2CH.sub.3 n=1, 2, 3, 4, 5 m=2, 3, R, R, R=CH.sub.3, CH.sub.2CH.sub.3 R.sup.IV=H, CH.sub.3, CH.sub.2CH.sub.3 and X=a monovalent counterion.

2. Ammonium salt according to claim 1, wherein the ammonium salt comprises the formula (II) ##STR00006## where R.sup.V=C.sub.rH.sub.2r+1 and r=1-9.

3. Ammonium salt according to claim 1, wherein R=H.

4. Ammonium salt according to claim 1, wherein n=2 or 3.

5. Ammonium salt according to claim 1, wherein m=2.

6. Ammonium salt according to claim 1, wherein R=R=R=CH.sub.3.

7. Ammonium salt according to claim 1, wherein R.sup.IV=CH.sub.2CH.sub.3.

8. Process for producing an ammonium salt according to claim 1, wherein a ditertiary amine, where one of the tertiary amino groups is substituted with a hydroxyalkyl group, is reacted with an alkylene oxide and an acid HX.

9. Process according to claim 8, wherein the alkylene oxide is employed in a molar ratio of 0.9-1.1 and the acid in a molar ratio of 0.9-1.1, in each case based on the molar amount of the ditertiary amine.

10. Process according to claim 8, wherein the ditertiary amine has the formula ##STR00007## where R=H, CH.sub.3, CH.sub.2CH.sub.3 n=1, 2, 3, 4, 5, m=2, 3 and R, R, R=CH.sub.3, CH.sub.2CH.sub.3.

11. Process according to claim 10, wherein the acid HX is an alkanoic acid selected from the group of alkanoic acids having the formula R.sup.VCOOH where R.sup.V=C.sub.rH.sub.2r+1 where r=1-9.

12. Process according to claim 11, wherein the alkylene oxide is selected from ethylene oxide, propylene oxide and -butylene oxide.

13. A method for trimerization of isocyanates to isocyanurates or for conversion of isocyanates and hydroxy-containing compounds to urethane-containing compounds comprising applying the ammonium salt of claim 1 as a catalyst to the isocyanates or the hydroxy-containing compound.

Description

EXAMPLES

Inventive Example A

[0045] 146 parts of N,N,N-trimethyl-N-(hydroxyethyl)-ethylenediamine (1 mol of diamine) are mixed with 116 parts (1 mol) of hexanoic acid and then admixed portionwise with 72 parts (1 mol) of 1,2-butylene oxide at 40 C. under reflux and stirring. After complete addition the mixture is stirred at 40 C. for a further 96 h after which 1,2-butylene oxide is no longer detectable in the GC. According to NMR only the dimethylamine nitrogen reacted.

Noninventive Example B (According to DE4115102)

[0046] 146 parts of N,N,N-trimethyl-N-(hydroxyethyl)-ethylenediamine (1 mol of diamine) are mixed with 232 parts (2 mol) of hexanoic acid and then admixed portionwise with 144 parts (2 mol) of 1,2-butylene oxide at 40 C. under reflux and stirring. After complete addition the mixture is stirred at 40 C. for a further 96 h after which 1,2-butylene oxide is no longer detectable in the GC.

Trimerization

General Procedure:

[0047] 1500 g of isophorone diisocyanate (IPDI) are heated to 70 C. and only then mixed with 3 g of catalyst before stirring. The duration of exothermicity, the maximum of the temperature curve and the final NCO number are determined.

TABLE-US-00001 Duration of Maximum of NCO number exothermicity temperature after reaction [min] curve [ C.] (start 37.8) example A 2:30 156 24.5 example B 2:43 137 28.6

[0048] The resulting partial trimerizates are not only stable and colourless but also low-odour. The catalyst according to the invention having one ammonium and one tertiary amino group in the cationic proportion is markedly more active than the catalyst of the comparative example with two ammonium groups in the cationic proportion.