NH2-modified 6-aminouracils as stabilizers for halogenated...

Details NH2-modified 6-aminouracils as stabilizers for halogenated... NH2-modified 6-aminouracils as stabilizers for halogenated...

1999-06-18

2001-01-16

Sanders, Kriellion (Department: 1714)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Processes of preparing a desired or intentional composition...

C524S114000, C524S399000, C524S400000, C524S413000, C524S423000, C524S430000, C524S450000, C524S056000, C544S312000

Reexamination Certificate

active

06174941

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Technical Field
The invention relates to 1,3-disubstituted 6-aminouracils which are of the formula I depicted below and are intended for stabilizing chlorine-containing polymers, especially PVC.
2. Prior Art
PVC can be stabilized by a range of additives. Compounds of lead, of barium and of cadmium are particularly suitable for this purpose but are nowadays controversial on ecological grounds or because of their heavy metal content (cf. “Kunststoffadditive”, R. G{umlaut over (a)}chter/H. M{umlaut over (u)}ller, Carl Hanser Verlag, 3rd ed., 1989, pages 303-311, and “Kunststoff Handbuch PVC”, volume 2/1, W. Becker/D. Braun, Carl Hanser Verlag, 2nd ed., 1985, pages 531-538; and also Kirk-Othmer: “Encyclopedia of Chemical Technology”, 4
th
ed., 1994, Vol. 12, Heat Stabilizers, pp. 1071-1091). The search therefore continues for effective stabilizers and stabilizer combinations which are free from lead, barium and cadmium.
1,3-disubstituted aminouracils have already been described in U.S. Pat. No. 3,436,362, U.S. Pat. No. 4,656,209, U.S. Pat. No. 4,352,903 and EP-A-0 768 336 and can be prepared by known methods in one (or more) process steps.
SUMMARY OF THE INVENTION
It has now been found that the 1,3-disubstituted 6-aminoruacils of the general formula I
where
Y is oxygen or sulfur, and
R
1
and R
2
independently of one another are C
1
-C
18
-alkyl, C
3
-C
6
-alkenyl, unsubstituted or C
1
-C
4
-alkoxy-, C
5
-C
8
-cycloalkyl-, —OH— and/or Cl-substituted C
1
-C
18
-alkyl, C
5
-C
8
-cycloalkyl, phenyl or C
7
-C
9
-phenylalkyl which is unsubstituted or substituted on the phenyl ring by C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
5
-C
8
-cycloalkyl, —OH and /or Cl, and
R
3
is unsubstituted C
9
-C
18
-alkyl or is C
1
-C
18
-alkyl substituted up to 5 times by —OH, C
1
-C
12
-alkoxy, phenoxy, C
6
-C
8
-alkylphenoxy, C
7
-C
9
-alkoxyphenyl, —C═O(OR
4
) and/or —O—COR
4
, or is C
3
-C
6
-alkenyl, C
5
-C
8
-cycloalkyl, or mono- to tri-OH—, —C
1
-C
4
-alkyl-, —C
1
-C
4
-alkoxy-, —C═O(OR
4
)— and/or —O—COR
4
-substituted phenyl or naphthyl, and where
R
4
is C
1
-C
12
-alkyl,
are particularly suitable for stabilizing chlorine-containing polymers such as PVC, for example.
For compounds of the formula I,
C
1
-C
4
-alkyl is, for example, methyl, ethyl, n-propyl, isopropyl, n-, i-, sec- or t-butyl.
C
5
-C
18
-alkyl is, for example, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, i-octyl, decyl, nonyl, undecyl, dodecyl, pentadecyl, hexadecyl, etc.
Preference is given to methyl, ethyl, propyl and butyl, especially methyl.
C
1
-C
12
-Alkoxy is, for example, methoxy, ethoxy, propoxy, n-, i- and tert-butoxy, n-, i-, tert- and neo-pentoxy, hexoxy etc.
Methoxy and ethoxy are preferred.
C
6
-C
8
-Alkylphenoxy is, for example, methylphenoxy, dimethylphenoxy or ethylphenoxy.
C
7
-C
9
-Alkoxyphenyl is, for example, methoxyphenyl, dimethoxyphenyl, trimethoxypenyl, ethoxyphenyl, propoxyphenyl, etc.
C
3
-C
6
-alkenyl is allyl, 1-butenyl, 2-butenyl, 3-butenyl, isobutenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl and their isomers. Preference is given to allyl.
C
5
-C
8
-cycloalkyl is, for example, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl, preferably cyclohexyl.
C
7
-C
10
-phenylalkyl is, for example, benzyl, 1- or 2-phenylethyl, 3-phenylpropyl, &agr;,&agr;-dimethylbenzyl or 2-phenylisopropyl, preferably benzyl and 2-phenethyl, especially benzyl.
If the aromatic radical is substituted then it is preferably substituted by three, two or, in particular, one substituent and the substituents are, in particular, hydroxyl, methyl, ethyl, tert-butyl, methoxy or ethoxy.
Preference is given to compounds of the formula I in which Y is oxygen and to those in which the radicals R
1
and R
2
independently of one another are C
1
-C
8
-alkyl, allyl or C
7
-C
9
-phenylalkyl.
Further advantageous compounds are those in which Y is sulfur.
Preference is also given to compounds of the formula I in which R
3
is C
9
-C
18
-alkyl or —OH-substituted C
1
-C
12
-alkyl, cyclohexyl, allyl, C
7
-C
9
-phenylalkyl, or —OH—, C
1
-C
4
-alkyl-, C
1
-C
4
-alkoxy-, —C═O(OR
4
)— and/or —O—COR
4
-substituted phenyl or naphthyl. Very particular preference is given to compounds of the formula I in which R
1
and R
2
are C
1
-C
4
-alkyl and R
3
is —OH-substituted C
1
-C
4
-alkyl, benzyl, phenyl, —OH-substituted phenyl, or phenyl which is substituted by —OH and from 1 to 3 times by C
1
-C
4
-alkyl.
In order to achieve stabilization in the chlorine-containing polymer, the compounds of the formula I are to be used in a proportion of judiciously from 0.01 to 10% by weight, preferably from 0.05 to 5% by weight and, in particular, from 0.1 to 3% by weight.
It is also possible to employ combinations of compounds of the general formula I with other customary additives and stabilizers, for example with polyols and disaccharide alcohols and/or perchlorate compounds and/or glycidyl compounds and/or zeolite compounds and/or layered lattice compounds (hydrotalcites) and also, for example, light stabilizers. Examples of such additional components are listed and elucidated below.


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