US 5,314,938 AGranted

Amelinic compounds and use thereof in self-extinguishing polymeric compositions

AssigneeMinistereo Dell'Universita' E Della Ricerca Scientifica E Technologica

InventorsRoberto Cipolli, Gilberto Nucida, Enrico Masarati, Roberto Oriani, Mario Pirozzi

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Abstract

Amelinic compounds of general formula (I) ##STR1## obtained by subsequent condensation reaction of 1 mol of a cyanuric acid lide with 1 mol of amine and of a polyamine and by hydrolysis reaction of the thus obtained intermediate. Compounds of general formula (I) are used, in particular, as antiflame additives.

Claims14

Dependent claims

Self-extinguishing polymeric compositions comprising:

a) from 90 to 40 parts by weight of a thermoplastic polymer or of a polymer showing elastomeric properties;
b) from 6 to 33 parts by weight of one or more phosphates and/or phosphonates of ammonium or of an amine;
c) from 3 to 27 parts by weight of one or more polycondensed compounds derived from 2,4-diamino-6-hydroxy-1,3,-5-triazine, having the formula (I):
##STR103## wherein n is an integer comprised between 1 and 8;
Y is H;
CN;
--O--(C.sub.1 -C.sub.4)-alkyl;
--O--(C.sub.2 -C.sub.4)-alkenyl;
(C.sub.6 -C.sub.12)-cycloalkyl or -alkylcycloalkyl;
--O--(C.sub.6 -C.sub.12)-aryl;
##STR104## wherein radicals R.sub.4, which may be the same or different, are:
(C.sub.1 -C.sub.4)-alkyl or (C.sub.3 -C.sub.4)-alkenyl or the group:
##STR105## is replaced by a heterocyclic radical selected from the group consisting of pyrrolidine, piperidine, morpholine, thiomorpholine, piperazine, 4-methylpiperazine, or 4-ethylpiperazine, said heterocyclic radical being bound to the alkyl chain through a nitrogen atom;
(C.sub.2 -C.sub.6)-alkenyl;
(C.sub.6 -C.sub.12)-cycloalkyl or -alkylcycloalkyl;
(C.sub.6 -C.sub.12)-aryl or -aralkyl;
radicals R.sub.1 and R.sub.2, which may be the same or different and which can have different meanings on each triazine ring, are:
H;
(C.sub.1 -C.sub.18)-alkyl;
(C.sub.2 -C.sub.8)-alkenyl;
(C.sub.6 -C.sub.16)-cycloalkyl or -alkylcycloalkyl;
##STR106## with:
m=integer comprised between 2 and 8;
p=integer comprised between 2 and 6;
R.sub.5 =H;
(C.sub.1 -C.sub.8)-alkyl;
(C.sub.2 -C.sub.6)-alkenyl;
--O--R.sub.7 wherein q is an integer comprised between 1 and 4 and R.sub.7 is H or (C.sub.1 -C.sub.4)-alkyl;
(C.sub.6 -C.sub.12)-cycloalkyl or -alkylcycloalkyl;
radicals R.sub.6, which may be the same or different, are:
H;
(C.sub.1 -C.sub.8)-alkyl;
(C.sub.2 -C.sub.6)-alkenyl;
(C.sub.6 -C.sub.12)-cycloalkyl or -alkylcycloalkyl;
(C.sub.1 -C.sub.4)-hydroxyalkyl;
or the group:
##STR107## is replaced by a heterocyclic radical selected from the group consisting of aziridine, pyrrolidine, piperidine, morpholine, thiomorpholine, piperazine, 4-methylpiperazine, or 4-ethylpiperazine, said heterocyclic radical being bound to the alkyl chain through the nitrogen atom;
or in the formula (I) the group:
##STR108## is replaced by a heterocyclic radical selected from the group consisting of aziridine, pyrrolidine, piperidine, morpholine, thiomorpholine, piperazine, 4-methylpiperazine, 4-ethylpiperazine, 2-methylpiperazine, or 2,5-dimethylpiperazine, said heterocyclic radical being bound to the triazinic ring through a nitrogen atom;
a is 0 or 1;
b is 0 or an integer comprised between 1 and 5;
R.sub.3 is hydrogen or:
##STR109## and its meaning may vary within each repeating unit;
when b is O, Z is a divalent radical comprised in one of the following formulas:
##STR110## wherein radicals R.sub.8, which may be the same or different, are hydrogen or (C.sub.1 -C.sub.4)-alkyl;
##STR111## wherein r is an integer comprised between 2 and 14;
R.sub.9 is hydrogen;
(C.sub.1 -C.sub.4)-alkyl;
(C.sub.2 -C.sub.6)-alkenyl;
(C.sub.1 -C.sub.4)-hydroxyalkyl;
##STR112## wherein s is an integer comprised between 2 and 5 and t is an integer comprised between 1 and 3;
##STR113## wherein:
X is C--C;
O;
S;
S--S;
SO;
SO.sub.2 ;
NH;
NHSO.sub.2 ;
NHCO;
N.dbd.N;
CH.sub.2 ;
R.sub.10 is hydrogen;
hydroxy;
(C.sub.1 -C.sub.4)-alkyl;
(C.sub.1 -C.sub.4)-alkoxy;
##STR114## wherein A may be either a saturated or an unsaturated ring;
##STR115## wherein s has the previously defined meaning;
when on the contrary b is an integer comprised between 1 and 5 the group:
##STR116## is a polyvalent radical comprised in one of the following formulas:
##STR117## ##STR118## wherein:
R.sub.11 is hydrogen or (C.sub.1 -C.sub.4)-alkyl;
c is an integer comprised between 1 and 5;
indexes s, which may be the same or different, have the meaning previously defined;
##STR119## ##STR120## wherein:
R.sub.11 has the previously defined meaning;
w is an integer comprised between 2 and 4;
d is 1 or 2.

76 more elements

Dependencies are inferred from the claim text.

Facts

Application: 08/015,856Filed 10 Feb 1993 · division
Priority: IT 21420 A/9011 Sep 1990
Granted: 24 May 1994
Term ends: Not estimatedThe source records don’t support an estimate.

Classification6 codes

C08K 5/3492
Six-membered rings: triazines
C07D 251/52
Two nitrogen atoms: with an oxygen or sulfur atom attached to the third ring carbon atom
C08K 3/32
Use of inorganic substances as compounding ingredients: phosphorus-containing compounds
C08K 5/5317
Bound to oxygen and to carbon only: phosphonic compounds, e.g. R—P2

Family

Serial756,921Parent of this division · filed 9 Sep 1991
US 5,314,938 AThis patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

Self-extinguishing polymeric compositions comprising:

a) from 90 to 40 parts by weight of a thermoplastic polymer or of a polymer showing elastomeric properties;
b) from 6 to 33 parts by weight of one or more phosphates and/or phosphonates of ammonium or of an amine;
c) from 3 to 27 parts by weight of one or more polycondensed compounds derived from 2,4-diamino-6-hydroxy-1,3,-5-triazine, having the formula (I):
##STR103## wherein n is an integer comprised between 1 and 8;
Y is H;
CN;
--O--(C.sub.1 -C.sub.4)-alkyl;
--O--(C.sub.2 -C.sub.4)-alkenyl;
(C.sub.6 -C.sub.12)-cycloalkyl or -alkylcycloalkyl;
--O--(C.sub.6 -C.sub.12)-aryl;
##STR104## wherein radicals R.sub.4, which may be the same or different, are:
(C.sub.1 -C.sub.4)-alkyl or (C.sub.3 -C.sub.4)-alkenyl or the group:
##STR105## is replaced by a heterocyclic radical selected from the group consisting of pyrrolidine, piperidine, morpholine, thiomorpholine, piperazine, 4-methylpiperazine, or 4-ethylpiperazine, said heterocyclic radical being bound to the alkyl chain through a nitrogen atom;
(C.sub.2 -C.sub.6)-alkenyl;
(C.sub.6 -C.sub.12)-cycloalkyl or -alkylcycloalkyl;
(C.sub.6 -C.sub.12)-aryl or -aralkyl;
radicals R.sub.1 and R.sub.2, which may be the same or different and which can have different meanings on each triazine ring, are:
H;
(C.sub.1 -C.sub.18)-alkyl;
(C.sub.2 -C.sub.8)-alkenyl;
(C.sub.6 -C.sub.16)-cycloalkyl or -alkylcycloalkyl;
##STR106## with:
m=integer comprised between 2 and 8;
p=integer comprised between 2 and 6;
R.sub.5 =H;
(C.sub.1 -C.sub.8)-alkyl;
(C.sub.2 -C.sub.6)-alkenyl;
--O--R.sub.7 wherein q is an integer comprised between 1 and 4 and R.sub.7 is H or (C.sub.1 -C.sub.4)-alkyl;
(C.sub.6 -C.sub.12)-cycloalkyl or -alkylcycloalkyl;
radicals R.sub.6, which may be the same or different, are:
H;
(C.sub.1 -C.sub.8)-alkyl;
(C.sub.2 -C.sub.6)-alkenyl;
(C.sub.6 -C.sub.12)-cycloalkyl or -alkylcycloalkyl;
(C.sub.1 -C.sub.4)-hydroxyalkyl;
or the group:
##STR107## is replaced by a heterocyclic radical selected from the group consisting of aziridine, pyrrolidine, piperidine, morpholine, thiomorpholine, piperazine, 4-methylpiperazine, or 4-ethylpiperazine, said heterocyclic radical being bound to the alkyl chain through the nitrogen atom;
or in the formula (I) the group:
##STR108## is replaced by a heterocyclic radical selected from the group consisting of aziridine, pyrrolidine, piperidine, morpholine, thiomorpholine, piperazine, 4-methylpiperazine, 4-ethylpiperazine, 2-methylpiperazine, or 2,5-dimethylpiperazine, said heterocyclic radical being bound to the triazinic ring through a nitrogen atom;
a is 0 or 1;
b is 0 or an integer comprised between 1 and 5;
R.sub.3 is hydrogen or:
##STR109## and its meaning may vary within each repeating unit;
when b is O, Z is a divalent radical comprised in one of the following formulas:
##STR110## wherein radicals R.sub.8, which may be the same or different, are hydrogen or (C.sub.1 -C.sub.4)-alkyl;
##STR111## wherein r is an integer comprised between 2 and 14;
R.sub.9 is hydrogen;
(C.sub.1 -C.sub.4)-alkyl;
(C.sub.2 -C.sub.6)-alkenyl;
(C.sub.1 -C.sub.4)-hydroxyalkyl;
##STR112## wherein s is an integer comprised between 2 and 5 and t is an integer comprised between 1 and 3;
##STR113## wherein:
X is C--C;
O;
S;
S--S;
SO;
SO.sub.2 ;
NH;
NHSO.sub.2 ;
NHCO;
N.dbd.N;
CH.sub.2 ;
R.sub.10 is hydrogen;
hydroxy;
(C.sub.1 -C.sub.4)-alkyl;
(C.sub.1 -C.sub.4)-alkoxy;
##STR114## wherein A may be either a saturated or an unsaturated ring;
##STR115## wherein s has the previously defined meaning;
when on the contrary b is an integer comprised between 1 and 5 the group:
##STR116## is a polyvalent radical comprised in one of the following formulas:
##STR117## ##STR118## wherein:
R.sub.11 is hydrogen or (C.sub.1 -C.sub.4)-alkyl;
c is an integer comprised between 1 and 5;
indexes s, which may be the same or different, have the meaning previously defined;
##STR119## ##STR120## wherein:
R.sub.11 has the previously defined meaning;
w is an integer comprised between 2 and 4;
d is 1 or 2.

76 more elements

Facts

Application

08/015,856Filed 10 Feb 1993 · division

Priority

IT 21420 A/9011 Sep 1990

Granted

24 May 1994

Term ends

Not estimatedThe source records don’t support an estimate.

Classification6 codes

C08K 5/3492
Six-membered rings: triazines
C07D 251/52
Two nitrogen atoms: with an oxygen or sulfur atom attached to the third ring carbon atom
C08K 3/32
Use of inorganic substances as compounding ingredients: phosphorus-containing compounds
C08K 5/5317
Bound to oxygen and to carbon only: phosphonic compounds, e.g. R—P2