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US4454317A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for the trimerization of diisocyanates

Assignee: Evonik Operations GmbH
•
Filing: 1982-07-23
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Granted: 1984-06-12
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Expires: 2002-07-23
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Abstract

Abstract In a process for the trimerization of diisocyanates in the presence of a catalyst comprising quaternary ammonium salts of organic acids having the formula: ##STR1## wherein X represents the same or different radicals selected from the group consisting of C 1 -C 20 alkyl, C 3 -C 8 cycloalkyl, and C 2 -C 20 aralkyl; two X radicals taken together with at least one other heteroatom forming a hetero-ring and three X radicals taken together with the quaternary nitrogen atoms forming a hetero-ring through a common hetero-atom such that said heterocyclic ring structure is selected from the group consisting of triethylene diamine, methyl triethylene diamine, quinuclidine, N-methylmorpholine, N-ethylmorpholine, and N,N'-dimethylpiperazine; R is alkyl, cycloalkyl or aralkyl, R" is R or hydrogen; R+R" together form a C 1 -C 12 alkyl radical; R' is hydrogen, hydroxyl or a C 1 -C 12 alkyl radical, optionally containing a CH.sub.(3-b) Z b group, wherein b=1 to 3 and Z is OH, the improvement comprising: reacting said diisocyanate with said catalyst in an amount of 0.02 to 0.1% by weight calculated on the weight of the compound to be trimerized at a temperature ranging from 40° to 120° C.

Inventors

  • 👤 Josef Disteldorf
  • 👤 Werner Hubel
  • 👤 Elmar Wolf

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-02 20:23
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/72; C08G18/77; C08G18/78; C08G18/79; C08G18/791; C07; C07D; C07D251/00; C07D251/02; C07D251/12; C07D251/26; C07D251/30; C07D251/34; C08G18/02; C08G18/022; C08G18/08; C08G18/16; C08G18/18; C08G18/1875; C08G18/73; C08G18/74; C08G18/75; C08G18/751; C08G18/752; C08G18/753; C08G18/755; C08G18/757; C08G18/758

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 190 words
In a process for trimerization of diisocyanates in the presence of a catalyst comprising quaternary ammonium salts of organic acids having the formula: ##STR10## wherein X represents the same or different radicals selected from the group consisting of C 1 -C 20 alkyl, C 3 -C 8 cycloalkyl, and C 2 -C 20 aralkyl; two X radicals taken together with at least one other heteroatom forming a hetero-ring and three X radicals taken together with the quarternary nitrogen atoms forming a heteroring through a common heteroatom such that said heterocyclic ring structure is selected from the group consisting of triethylene diamine, methyl triethylene diamine, quinuclidine, N-methylmorpholine, N-ethylmorpholine and N,N'-dimethylpiperazine; R is alkyl, cycloalkyl or aralkyl, R" is R or hydrogen; R+R" together form a C 1 -C 12 alkyl radical; R' is hydrogen, hydroxyl or a C 1 -C 12 alkyl radical optionally containing a CH.sub.(3-b) Z b group, wherein b=1 to 3 and Z is OH, the improvement comprising: reacting said diisocyanate with said catalyst in an amount of 0.02-0.1% by weight calculated on the weight of the compound to be trimerized at a temperature ranging from 40°-120° C.
Claim 2
Dependent Claim 190 words
In a process for trimerization of diisocyanates in the presence of a catalyst comprising quaternary ammonium salts of organic acids having the formula: ##STR10## wherein X represents the same or different radicals selected from the group consisting of C 1 -C 20 alkyl, C 3 -C 8 cycloalkyl, and C 2 -C 20 aralkyl; two X radicals taken together with at least one other heteroatom forming a hetero-ring and three X radicals taken together with the quarternary nitrogen atoms forming a heteroring through a common heteroatom such that said heterocyclic ring structure is selected from the group consisting of triethylene diamine, methyl triethylene diamine, quinuclidine, N-methylmorpholine, N-ethylmorpholine and N,N'-dimethylpiperazine; R is alkyl, cycloalkyl or aralkyl, R" is R or hydrogen; R+R" together form a C 1 -C 12 alkyl radical; R' is hydrogen, hydroxyl or a C 1 -C 12 alkyl radical optionally containing a CH.sub.(3-b) Z b group, wherein b=1 to 3 and Z is OH, the improvement comprising: reacting said diisocyanate with said catalyst in an amount of 0.02-0.1% by weight calculated on the weight of the compound to be trimerized at a temperature ranging from 40°-120° C.
Claim 3
Dependent Claim 22 words
The process according to claim 1, wherein said trimerization reaction is conducted at a temperature in the range of 60° C.-90° C.
Claim 4
Dependent Claim 20 words
A process according to claim 1, characterized in that the trimerization is carried out up to a conversion of 45%.
Claim 5
Dependent Claim 30 words
A process according to claim 1 or 2, characterized in that the trimerization is carried out continuously in a coolable tube-shaped reactor with simultaneous addition of monomeric isocyanate containing catalyst.
Claim 6
Dependent Claim 23 words
A process according to claims 1 or 3, characterized in that the unconverted monomeric isocyanate is removed by means of a thin-film distillation.
Claim 7
Dependent Claim 15 words
A process according to claims 1 or 3, characterized in that aromatic diisocyanates are trimerized.
Claim 8
Dependent Claim 15 words
A process according to claims 1 or 3, characterized in that aliphatic diisocyanates are trimerized.
Claim 9
Dependent Claim 15 words
A process according to claims 1 or 3, characterized in that cycloaliphatic diisocyanates are trimerized.
Claim 10
Dependent Claim 15 words
A process according to claim 8, characterized in that the cycloaliphatic diisocyanate is isophorone diisocyanate.

References Cited (Backward Citations)

US4040992A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1987-06-12 1987-12-12 1988-06-12 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1991-06-12 1991-12-12 1992-06-12 $3760.00 Window Closed / Lapsed
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