Mixtures of triazine derivatives free from polyalkylene oxide

Details Mixtures of triazine derivatives free from polyalkylene oxide Mixtures of triazine derivatives free from polyalkylene oxide

2002-07-25

2004-11-16

Balasubramanian, Venkataraman (Department: 1624)

Organic compounds -- part of the class 532-570 series

Organic compounds

Four or more ring nitrogens in the bicyclo ring system

C544S197000, C544S204000, C544S205000, C544S206000

Reexamination Certificate

active

06818768

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to mixtures of triazine derivatives with hydroxy groups free from polyalkylene oxide and a method of producing them.
2. Description of the Related Art
Triazine derivatives with hydroxy groups of the methylol melamine or methylol guanamine types that can be produced by reacting melamine or guanamine with formaldehyde are known (Ullmanns Encyclopedia of Industrial Chemistry (1987), Vol. A2, pp. 130-131; Duroplaste, Kunststoff-Handbuch Bd. 10, 994-997, Carl Hanser-Verlag München 1988]. These methylol melamines or methylol guanamines share the disadvantage of limited stability which may result in partial breaking back into melamine or guanamine and formaldehyde.
Also known are hydroxyoxaalkyl melamines in which the melamine amino group(s) are replaced by groups of the formula H—(—O—CHR′—CHR′—)
n
wherein R′=C
1
-C
4
alkyl groups and n=2 or 3, and where said hydroxyoxaalkyl melamines are produced by reacting aminoethoxy ethanol with cyanuric chloride, dichloroaminotriazine or diaminochlorotriazine (EP 0 225 433). In addition to the great effort it takes to produce hydroxyoxaalkyl melamines, the general disadvantage is that this method cannot be used to produce hydroxyalkyl melamines with n=1.
Other known processes are reacting melamine with ethylene oxide in the presence of alkali metal hydroxides (DE 21 18 868) or reacting N,N′-hydroxyethyl melamines or N,N′-hydroxyaryl melamines with ethylene oxide or propylene oxide in the presence of sulfuric acid (U.S. Pat. No. 4,356,304). The disadvantage of these melamines modified by alkylene oxide to become melamine alkylpropylene oxide block copolymers lies in their long polyalkylene oxide sequences and in the interfering portions of unbound polyalkylene oxide.
SUMMARY OF THE INVENTION
The problem of this invention is to provide triazine derivatives with hydroxy groups that contain a high portion of hydroxyalkyl groups and no portion of polyalkylene oxides.
The problem of this invention was solved by polyalkylene oxide free mixtures of triazine derivatives with hydroxy groups consisting of
a) 20 to 70 percent by weight of triazine derivatives with hydroxyalkyl amino groups of the formula
R
1
=H or C
1
-C
4
alkyl
R
2
=—H; —OH; C
1
-C
4
alkyl, —C
6
H
5
; —NH
2
; —NH—CH
2
—CHR
1
—OH; —NH—CH
2
—OR
1
, or —N(—CH
2
—OR
1
)
2
,
R
3
=—H; —OH; C
1
-C
4
alkyl, —C
6
H
5
; —NH
2
, —NH—CH
2
—CHR
1
—OH; —NH—CH
2
—OR
1
, or —N(—CH
2
—OR
1
)
2
, and
b) 80 to 30 percent by weight of triazine derivatives with bis(hydroxyalkyl)imino groups of the formula
R
1
=H or C
1
-C
4
alkyl
R
2
=—H; —OH; C
1
-C
4
alkyl, —C
6
H
5
; —NH
2
; —NH—CH
2
—CHR
1
—OH, —N[CH
2
—CHR
1
—OH]
2
, —NHCH
2
—OR
1
, or —N(—CH
2
—OR
1
)
2
,
R
3
=—H; —OH; C
1
-C
4
alkyl, —C
6
H
5
; —NH
2
; —NH—CH
2
—CHR
1
—OH, —N[CH
2
—CHR
1
—OH]
2
, —NHCH
2
—OR
1
, or —N(—CH
2
—OR
1
)
2
.


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Ullmanns Encyclopedia of Industrial Chemistry (1997), vol. A2, pp. 130-131.
Duroplaste, Kunststoff-Handbuch Bd. 10, pp. 994-997, Carl Hanser-Verlag Munchen 1999.
Rhodes et al.; “Synethesis of titanium(IV)complexes 2,6-dimethylaniline substituted amino alcohols and their utilization in ethylene polymerizations”—Journal of Organometallic Chemistry, Elsevier-Sequoia S.A. Lausanne, Switzerland, Bd. 625, Nr. 1, 15. Apr. 2001, pp. 95-100.

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