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US4433085A Expired / Lapsed US ⏱️ 0.0 years remaining

Triazolidine-3,5-dione/formaldehyde/amine condensates and compositions thereof

Assignee: Bayer AG
•
Filing: 1981-06-29
•
Granted: 1984-02-21
•
Expires: 2001-06-29
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Abstract

Abstract A triazolidine-3,5-dione/formaldehyde/amine condensate is disclosed of the formula ##STR1## in which wherein the terms R 1 , R 2 and R 5 are defined hereinafter in the specification a process for the preparation of such condensate by reaction of a triazolidine-3,5-dione with formaldehyde and a suitable nitrogen compound and the use of the condensate as a flame-proofing agent for thermoplastics, especially polyamide and as an auxiliary for modifying polymeric substances.

Inventors

  • 👤 Ludwig Rottmaier
  • 👤 Rudolf Merten

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 02:29
CPC Classifications
C; C08; C08G; C08G12/00; C07; C07D; C07D249/00; C07D249/02; C07D249/08; C07D249/10; C07D249/12; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3467; C08K5/3472

Claims Analysis

Total Claims: 19
Claim 1
Independent Claim 644 words
A compound of the formula ##STR45## wherein R 1 and R 2 , independently of one another are each hydrogen, alkylcarbonyl having 2 to 21 carbon atoms or ##STR46## wherein R 3 is hydrogen, alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, unsubstituted aralkyl having up to 14 carbon atoms in the aryl moiety and up to 2 carbon atoms in the alkyl moiety, unsubstituted aryl having 6 to 14 carbon atoms, or a heterocyclic radical selected from the group consisting of a radical of pyrrolidine, piperidine, pyrazolidine, imidazolidine, oxazolidine, thiazolidine, piperazine, morpholine, thiomorpholine, hydantoin, 5,5-dimethylhydantoin, parabanic acid, barbituric acid and cyanuric acid and R 4 is alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, unsubstituted aralkyl having up to 14 carbon atoms in the aryl moiety and up to 2 carbon atoms in the alkyl moiety, unsubstituted aryl having 6 to 14 carbon atoms, or a heterocyclic radical selected from the group consisting of a radical of pyrrolidine, piperidine, pyrazolidine, imidazolidine, oxazolidine, thiazolidine, piperazine, morpholine, thiomorpholine, hydantoin, 5,5-dimethylhydantoin, parabanic acid, barbituric acid and cyanuric acid, alkylcarbonyl having 2 to 21 carbon atoms, alkenylcarbonyl having 3 to 21 carbon atoms or alkoxycarbonyl having 2 to 20 carbon atoms, or wherein R 3 and R 4 , together with the nitrogen atom to which they are attached, form a nitrogen-containing heterocyclic radical selected from the group consisting of a radical of pyrrolidine, pyrazolidine, imidazolidine, oxazolidine, thiazolidine, triazolidine, tetrazolidine, thiodiazolidine, piperidine, piperazine, morpholine, thiomorpholine, azacyclobutane and azacycloheptane, and R 5 is alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, unsubstituted aralkyl having up to 14 carbon atoms in the aryl moiety and up to 2 carbon atoms in the alkyl moiety, unsubstituted aryl having 6 to 14 carbon atoms, alkylcarbonyl having 2 to 21 carbon atoms or ##STR47## wherein R 3 and R 4 are as aforesaid or R 5 is of the formula ##STR48## wherein R 6 is a (n+1)-valent C 1 -C 20 aliphatic, C 3 -C 10 cycloaliphatic, C 8 -C 16 araliphatic or C 6 -C 14 aromatic hydrocarbon radical or one of said hydrocarbon radicals mono- or di-substituted by halogen, hydroxyl, C 1 -C 4 -alkoxy, cyano, amino, C 1 -C 4 -alkylamino, bis-(C 1 -C 4 -alkyl)-amino, C 2 -C 4 -alkoxycarbonyl or C 1 -C 4 -alkyl, R 1 and R 2 are as aforesaid and n is 1 or 2 or R 5 is of the formula ##STR49## wherein R 7 is hydrogen, alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, unsubstituted aralkyl having up to 14 carbon atoms in the aryl moiety and up to 2 carbon atoms in the alkyl moiety, unsubstituted aryl having 6 to 14 carbon atoms, a heterocyclic radical selected from the group consisting of a radical of pyrrolidine, piperidine, pyrazolidine, imadazolidine, oxazolidine, thiazolidine, piperazine, morpholine, thiomorpholine, hydantoin, 5,5-dimethylhydantoin, parabanic acid, barbituric acid and cyanuric acid or ##STR50## R 8 is a (m+1)-valent C 1 -C 20 -aliphatic, C 3 -C 10 -cycloaliphatic, C 8 -C 16 -araliphatic, C 6 -C 14 -aromatic hydrocarbon radical or one of said hydrocarbon radicals mono- or di-substituted by halogen, hydroxyl, C 1 -C 4 -alkoxy, cyano, amino, C 1 -C 4 -alkylamino, bis-(C 1 -C 4 -alkyl)-amino, C 2 -C 4 -alkoxycarbonyl or C 1 -C 4 -alkyl, R 1 and R 2 are as aforesaid and m is 0, 1 and 2, a hydrogen atom being present instead of the radical in brackets if m is 0 and it being possible for R 8 to be a carbonyl group when m is 1, said R 1 , R 2 and R 5 being selected so that said compound of said formula contains at least one group of the formula >N--CH.sub.2 --N<
Claim 2
Dependent Claim 644 words
A compound of the formula ##STR45## wherein R 1 and R 2 , independently of one another are each hydrogen, alkylcarbonyl having 2 to 21 carbon atoms or ##STR46## wherein R 3 is hydrogen, alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, unsubstituted aralkyl having up to 14 carbon atoms in the aryl moiety and up to 2 carbon atoms in the alkyl moiety, unsubstituted aryl having 6 to 14 carbon atoms, or a heterocyclic radical selected from the group consisting of a radical of pyrrolidine, piperidine, pyrazolidine, imidazolidine, oxazolidine, thiazolidine, piperazine, morpholine, thiomorpholine, hydantoin, 5,5-dimethylhydantoin, parabanic acid, barbituric acid and cyanuric acid and R 4 is alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, unsubstituted aralkyl having up to 14 carbon atoms in the aryl moiety and up to 2 carbon atoms in the alkyl moiety, unsubstituted aryl having 6 to 14 carbon atoms, or a heterocyclic radical selected from the group consisting of a radical of pyrrolidine, piperidine, pyrazolidine, imidazolidine, oxazolidine, thiazolidine, piperazine, morpholine, thiomorpholine, hydantoin, 5,5-dimethylhydantoin, parabanic acid, barbituric acid and cyanuric acid, alkylcarbonyl having 2 to 21 carbon atoms, alkenylcarbonyl having 3 to 21 carbon atoms or alkoxycarbonyl having 2 to 20 carbon atoms, or wherein R 3 and R 4 , together with the nitrogen atom to which they are attached, form a nitrogen-containing heterocyclic radical selected from the group consisting of a radical of pyrrolidine, pyrazolidine, imidazolidine, oxazolidine, thiazolidine, triazolidine, tetrazolidine, thiodiazolidine, piperidine, piperazine, morpholine, thiomorpholine, azacyclobutane and azacycloheptane, and R 5 is alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, unsubstituted aralkyl having up to 14 carbon atoms in the aryl moiety and up to 2 carbon atoms in the alkyl moiety, unsubstituted aryl having 6 to 14 carbon atoms, alkylcarbonyl having 2 to 21 carbon atoms or ##STR47## wherein R 3 and R 4 are as aforesaid or R 5 is of the formula ##STR48## wherein R 6 is a (n+1)-valent C 1 -C 20 aliphatic, C 3 -C 10 cycloaliphatic, C 8 -C 16 araliphatic or C 6 -C 14 aromatic hydrocarbon radical or one of said hydrocarbon radicals mono- or di-substituted by halogen, hydroxyl, C 1 -C 4 -alkoxy, cyano, amino, C 1 -C 4 -alkylamino, bis-(C 1 -C 4 -alkyl)-amino, C 2 -C 4 -alkoxycarbonyl or C 1 -C 4 -alkyl, R 1 and R 2 are as aforesaid and n is 1 or 2 or R 5 is of the formula ##STR49## wherein R 7 is hydrogen, alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, unsubstituted aralkyl having up to 14 carbon atoms in the aryl moiety and up to 2 carbon atoms in the alkyl moiety, unsubstituted aryl having 6 to 14 carbon atoms, a heterocyclic radical selected from the group consisting of a radical of pyrrolidine, piperidine, pyrazolidine, imadazolidine, oxazolidine, thiazolidine, piperazine, morpholine, thiomorpholine, hydantoin, 5,5-dimethylhydantoin, parabanic acid, barbituric acid and cyanuric acid or ##STR50## R 8 is a (m+1)-valent C 1 -C 20 -aliphatic, C 3 -C 10 -cycloaliphatic, C 8 -C 16 -araliphatic, C 6 -C 14 -aromatic hydrocarbon radical or one of said hydrocarbon radicals mono- or di-substituted by halogen, hydroxyl, C 1 -C 4 -alkoxy, cyano, amino, C 1 -C 4 -alkylamino, bis-(C 1 -C 4 -alkyl)-amino, C 2 -C 4 -alkoxycarbonyl or C 1 -C 4 -alkyl, R 1 and R 2 are as aforesaid and m is 0, 1 and 2, a hydrogen atom being present instead of the radical in brackets if m is 0 and it being possible for R 8 to be a carbonyl group when m is 1, said R 1 , R 2 and R 5 being selected so that said compound of said formula contains at least one group of the formula >N--CH.sub.2 --N<
Claim 3
Dependent Claim 92 words
A compound according to claim 1 of the formula ##STR51## wherein R 9 is alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, unsubstituted aralkyl having up to 14 carbon atoms in the aryl moiety and up to 2 carbon atoms in the alkyl moiety, unsubstituted aryl having 6 to 14 carbon atoms, alkylcarbonyl having 2 to 21 carbon atoms or ##STR52## said R 1 , R 2 and R 9 being selected so that said compound contains at least one group of the formula >N--CH.sub.2 --N<
Claim 4
Dependent Claim 10 words
A compound according to claim 1 of the formula ##STR53##
Claim 5
Dependent Claim 10 words
A compound according to claim 1 of the formula ##STR54##
Claim 6
Dependent Claim 218 words
A compound according to claim 1 of the formula ##STR55## in which R 11 and R 12 independently of one another denote hydrogen, C 2 -C 8 -alkylcarbonyl or ##STR56## wherein R 13 represents hydrogen, C 1 -C 8 -alkyl, C 5 -C 6 -cycloalkyl, benzyl or phenyl and R 14 denotes C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl, benzyl, phenyl a heterocyclic radical selected from the group consisting of a radical of pyrrolidine, piperidine, pyrazolidine, imidazolidine, oxazolidine, thiazolidine, piperazine, morpholine, thiomorpholine, hydantoin, 5,5-dimethylhydantoin, parabanic acid, barbituric acid and cyanuric acid, C 2 -C 8 -alkylcarbonyl, C 3 -C 8 -alkenylcarbonyl or C 2 -C 8 -alkoxycarbonyl, and in which R 13 and R 14 , together with the nitrogen atom to which they are attached, form a nitrogen-containing heterocyclic radical selected from the group consisting of a radical of pyrrolidine, pyrazolidine, imidazolidine, oxazolidine, thiazolidine, triazolidine, tetrazolidine, thiodiazolidine, piperidine, piperazine, morpholine, thiomorpholine, azacyclobutane and azacycloheptane, and R 19 represents C 1 -C 8 -alkyl, C 5 -C 6 -cycloalkyl, benzyl, phenyl, C 2 -C 8 -alkylcarbonyl or ##STR57## wherein R 13 and R 14 are as aforesaid, said R 11 , R 12 and R 19 being selected so that said compound of said formula contains at least one group of the formula >N--CH.sub.2 --N<
Claim 7
Dependent Claim 194 words
A compound according to claim 1 of the formula ##STR58## in which R 21 and R 22 independently of one another are each hydrogen, C 2 -C 4 -alkylcarbonyl or ##EQU1## wherein R 23 represents hydrogen or C 1 -C 4 -alkyl and R 24 represents C 1 -C 4 -alkyl, a heterocyclic radical selected from the group consisting of a radical of pyrrolidine, piperidine, pyrazolidine, imidazolidine, oxazolidine, thiazolidine, piperazine, morpholine, thiomorpholine, hydantoin, 5,5-dimethylhydantoin, parabanic acid, barbituric acid and cyanuric acid, C 2 -C 4 -alkylcarbonyl or C 3 -C 4 -alkenylcarbonyl, and wherein R 23 and R 24 , together with the nitrogen atom to which they are attached form a nitrogen-containing heterocyclic radical selected from the group consisting of a radical of pyrrolidine, pyrazolidine, imidazolidine, oxazolidine, thiazolidine, triazolidine, tetrazolidine, thiodiazolidine, piperidine, piperazine, morpholine, thiomorpholine, azacyclobutane and azacycloheptane, and R 29 denotes C 1 -C 4 -alkyl, cyclohexyl, benzyl, phenyl C 2 -C 4 -alkylcarbonyl or ##STR59## wherein R 23 and R 24 are as aforesaid, R 21 , R 22 and R 29 being selected so that said compound of said formula contains at least one group of the formula >N--CH.sub.2 --N<
Claim 8
Dependent Claim 146 words
A compound according to claim 1 of the formula ##STR60## in which R 11 and R 12 independently denote hydrogen, C 2 -C 8 alkylcarbonyl or ##STR61## wherein R 13 represents hydrogen, C 1 -C 8 alkyl, C 5 -C 6 cycloalkyl, benzyl or phenyl and R 14 denotes C 1 -C 8 alkyl, C 2 -C 8 alkenyl, benzyl, phenyl a heterocyclic radical selected from the group consisting of a radical of pyrrolidine, piperidine, pyrazolidine, imidazolidine, oxazolidine, thiazolidine, piperazine, morpholine, thiomorpholine, hydantoin, 5,5-dimethylhydantoin, parabanic acid, barbituric acid and cyanuric acid, C 2 -C 8 -alkoxycarbonyl, C 2 -C 8 alkylcarbonyl or C 3 -C 8 alkenylcarbonyl, R 16 denotes alkylene, phenylene, toluylene or one of the groups ##STR62## R 11 , R 12 and R 16 being selected so that said compound of said formula contains at least one group of the formula >N--CH.sub.2 --N<
Claim 9
Dependent Claim 324 words
A compound according to claim 1 of the formula ##STR63## in which R 11 and R 12 independently of one another are each hydrogen, C 2 -C 8 -alkylcarbonyl or ##STR64## wherein R 13 represents hydrogen, C 1 -C 8 -alkyl, C 5 -C 6 -cycloalkyl, benzyl or phenyl and R 14 denotes C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl, benzyl, phenyl a heterocyclic radical selected from the group consisting of a radical of pyrrolidine, piperidine, pyrazolidine, imidazolidine, oxazolidine, thiazolidine, piperazine, morpholine, thiomorpholine, hydantoin, 5,5-dimethylhydantoin, parabanic acid, barbituric acid and cyanuric acid, C 2 -C 8 -alkylcarbonyl, C 3 -C 8 -alkenylcarbonyl or C 2 -C 8 -alkoxycarbonyl, and in which R 13 and R 14 together with the nitrogen atom to which they are attached form a nitrogen-containing heterocyclic radical selected from the group consisting of a radical of pyrrolidine, pyrazolidine, imidazolidine, oxazolidine, thiazolidine, triazolidine, tetrazolidine, thiodiazolidine, peperidine, piperazine, morpholine, thiomorpholine, azacyclobutane and azacycloheptane, and R 19 represents C 1 -C 8 -alkyl, C 5 -C 6 -cycloalkyl, benzyl, phenyl, C 2 -C 8 -alkylcarbonyl or ##STR65## wherein R 13 and R 14 are as aforesaid, R 17 represents hydrogen, C 1 -C 4 -alkyl, cyclohexyl, benzyl, phenyl, a heterocyclic radical selected from the group consisting of a radical of pyrrolidine, piperidine, pyrazolidine, imidazolidine, oxazolidine, thiazolidine, piperazine, morpholine, thiomorpholine, hydantoin, 5,5-dimethylhydantoin, parabanic acid, barbituric acid and cyanuric acid or ##STR66## R 18 represents a (o+1)-valent aliphatic radical, cyclohexane radical, benzene radical or heterocyclic radical selected from the group consisting of a radical of pyrrolidine, piperidine, pyrazolidine, imidazolidine, oxazolidine, thiazolidine, piperazine, morpholine, thiomorpholine, hydantoin, 5,5-dimethylhydantoin, parabanic acid, barbituric acid and cyanuric acid and o denotes the number 1 or 2, it also being possible for R 18 to be the carbonyl group if o=1, R 11 , R 12 and R 18 being selected so that said compound of said formula contains at least one group of the formula >N--CH.sub.2 --N<
Claim 10
Dependent Claim 10 words
A compound according to claim 1 of the formula ##STR67##
Claim 11
Dependent Claim 10 words
A compound according to claim 1 of the formula ##STR68##
Claim 12
Dependent Claim 10 words
A compound according to claim 1 of the formula ##STR69##
Claim 13
Dependent Claim 10 words
A compound according to claim 1 of the formula ##STR70##
Claim 14
Dependent Claim 10 words
A compound according to claim 1 of the formula ##STR71##
Claim 15
Dependent Claim 10 words
A compound according to claim 1 of the formula ##STR72##
Claim 16
Dependent Claim 10 words
A compound according to claim 1 of the formula ##STR73##
Claim 17
Dependent Claim 10 words
A compound according to claim 1 of the formula ##STR74##
Claim 18
Dependent Claim 10 words
A compound according to claim 1 of the formula ##STR75##
Claim 19
Dependent Claim 14 words
A polyamide molding composition containing, as a flame-proofing agent, a compound of claim 1.

References Cited (Backward Citations)

FR1330401A Cited
DE2936842A1 Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1987-02-20 1987-08-22 1988-02-21 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1991-02-20 1991-08-22 1992-02-21 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1995-02-20 1995-08-22 1996-02-21 $7700.00 Window Closed / Lapsed

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