Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Reexamination Certificate
1997-07-08
2001-11-13
Raymond, Richard L. (Department: 1624)
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
C252S405000
Reexamination Certificate
active
06316619
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to polyaminotriazine and to methods for its production and use.
2. Background Information
A polyaminotriazine is known as a light stabilizer for organic materials such as polyethylene and polypropylene. One method which is known for its production is that of reacting dichlorotriazine with diamine in an amount of about 1 to 1.2 mol per mol of said dichlorotriazine in the presence of a base (JP-A-52-71486 and JP-B-4-4329, both of which are incorporated herein by reference).
However, since polyaminotriazine obtained by the above method has a high melting point, it is difficult to mix with an organic material by feeding in liquid form and therefore a powder form must be used. This creates problems in handling it in the working environment (e.g., clouds of dust arising during feeding) and in weighing the polyaminotriazine if a continuous feeding process is used.
Because of these problems, the present inventors have studied intensively in order to provide a polyaminotriazine having low melting point. As a result, it has been found that a polyaminotriazine which has a low melting point and can be fed in a liquid form can be obtained by reacting a specific dichlorotriazine with a specific diamine under specific conditions or reacting a specific dichlorotriazine and a specific monochlorotriazine with a specific diamine under specific conditions. It has also been found that the above-mentioned polyaminotriazine compound which is obtained by reacting a specific dichlorotriazine and a specific monochlorotriazine with a specific diamine has the advantageous characteristic that very little bleeding occurs when it is contained in an organic material. Thus, the present invention has been accomplished.
SUMMARY OF THE INVENTION
The present invention provides a polyaminotriazine represented by the formula (I):
wherein
Q represents an alkyl amino group having 7 to 10 carbon atoms;
X
1
, X
2
, X
3
and X
4
, which can be identical or different from one another, each represent a 2,2,6,6-tetramethyl4-piperidyl group or hydrogen, provided that at least one of X
1
and X
2
and at least one of X
3
and X
4
represent a 2,2,6,6-tetramethyl4-piperidyl group;
Y and Z, which can be identical or different from one another, each represent hydrogen or a 4,6-bis(1,1,3,3-tetramethylbutylamino)-1,3,5-triazin-2-yl group; and n, which is calculated from the number average molecular weight measured with gel permutation chromatography and converted as polystyrene, assuming that all of Y and Z are hydrogen in the calculation, represents a number of 3 or less, provided that, when both of Y and Z represent hydrogen, n is not more than 2.
The present invention also provides an excellent industrial method for producing the polyaminotriazine represented by formula (I) which comprises reacting dichlorotriazine represented by the formula (II):
wherein Q is same as defined above, and monochlorotriazine represented by the formula (III):
wherein Q is the same as defined above, in an amount of 10 mol or less per mol of dichlorotriazine (II) with diamine represented by the formula (IV)
X—NHC
4
H
13
NH—X
5
(IV)
in which X represents a 2,2,6,6-tetramethyl-4-piperidyl group and X
5
represents hydrogen or a 2,2,6,6-tetramethyl4-piperidyl group, in an amount of 0.5 to 2 mol per total mol of dichlorotriazine (II) and monochlorotriazine (III) in the presence of a base and an organic solvent, provided that, when the amount of monochlorotriazine (III) is 0.1 mol or less per mol of the dichlorotriazine (II), the amount of diamine (IV) is 1.3 to 2 mol per total mol of said dichlorotriazine (II) and said monochlorotriazine (III).
The present invention further provides a method of using the polyaminotriazine represented by the formula (I). Aspects of the invention have been described in Japanese patent applications 08-179128, filed Jul. 9, 1996, 08-179127, filed Jul. 9, 1996, 09-105998, filed Apr. 23, 1997, and 09-105997, filed Apr. 23, 1997, all of which are incorporated herein by reference.
DETAILED DESCRIPTION OF THE INVENTION
As “Q” in the formula (I), an octylamino group is preferred and particularly 1,1,3,3-tetramethylbutyl amino group is preferred.
The dichlorotriazine (II) and monochlorotriazine (III), which are used as starting material of the present invention, can be produced, for example, by reacting cyanuric chloride with an alkylamine having 7-10 carbon atoms according to the method described in JP-A-52-71486.
According to the method described in JP-A-52-71486, a mixture of the dichlorotriazine (II) and monochlorotriazine (III) can be obtained. The mixture may be used without further isolation. Alternatively, the dichlorotriazine (II) and monochlorotriazine (III) in the mixture may isolated and separated before being used for producing the polyaminotriazine of the present invention. The separated compounds may be further purified by a method such as recrystallization.
Examples of the dichlorotriazine (II) include 2,4-dichloro-6-(1,1,3,3-tetramethylbutylamino)-1,3,5-triazine, 2,4-dichloro-6-(n-octylamino)-1,3,5-triazine and mixtures thereof. Among these, 2,4-dichloro-6-(1,1,3,3-tetramethylbutylamino)-1,3,5-triazine is preferred.
Examples of the monochlorotriazine (III) include 2-chloro-4,6-bis(1,1,3,3-tetramethylbutylamino)-1,3,5-triazine, 2-chloro-4,6-bis(n-octylamino)-1,3,5-triazine and mixtures thereof. Among these, 2-chloro-4,6-bis(1,1,3,3-tetramethylbutylamino)-1,3,5-triazine is preferred.
The monochlorotriazine (III) is preferably used in an amount of 0.1 to 10 mol, more preferably 0.25 to 5 mol, per mol of the dichlorotriazine (II).
The diamine (IV), which is another raw material of the present invention, can be produced, for example, by reacting triacetoneamine with octylamine according to the method described in JP-A-64-50858, (which is incorporated herein by reference). The diamine (IV) can be used directly without further isolation, but is preferably isolated before use. The isolated diamine may be further purified by a purifying method such as distillation or recrystallization.
Examples of the diamine (IV) include N,N
1
-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine, N-(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and mixtures thereof. It is particularly preferred to use the former alone or a mixture of the former and the latter wherein the amount of the latter is not more than ¼ mol per mol of the former as this results in polyaminotriazines which have much better performance characteristics as photostabilizers.
The diamine (IV) is used in an amount of about 0.5 to 2 mol, preferably about 1 to 2 mol, per mol of the total amount of the dichlorotriazine (II) and a monochlorotriazine (III), provided that, when monochlorotriazine (III) is not used, i.e., for producing a polyaminotriazine of formula (I) wherein Y and Z both represent hydrogen, the amount of diamine (IV) is from 1.3 to 2 per mol of the amount of the dichlorotriazine (II). When the amount is less than 0.5 mol or more than 2 mol, the resultant polyaminotriazine is liable to bleed from the organic material in which the polyaminotriazine mixture is contained. When the amount is less than 1.3 mol in the case of not using monochlorotriazine (III), polyaminotriazine having a high melting point is obtained, and the object of the present invention is thus not achieved.
The base is preferably an inorganic base. Examples of the inorganic bases include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, and alkali metal carbonates such as sodium carbonate and potassium carbonate. Among these, sodium hydroxide and potassium hydroxide are particularly preferred.
The base is normally used in an amount of about 1 to 3 times equivalent or greater based on the total equivalents of the dichlorotriazine (II) and monochlorotriazine (III), provided that, when monochlorotriazine (III) is not used, the amount of base is normally from 2 to 3 equivalents, preferably 2.2 to 2.5 equivalents. When the amount of the base used is less tha
Kimura Kenji
Miyake Kunihito
Ohta Chikara
Balasubramanian Venkataraman
Fitch Even Tabin & Flannery
Raymond Richard L.
Sumitomo Chemical Company Ltd.
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