1,3-Disubstituted 6-aminouracils for stabilizing halogenated...

Details 1,3-Disubstituted 6-aminouracils for stabilizing halogenated... 1,3-Disubstituted 6-aminouracils for stabilizing halogenated...

1999-06-22

2001-08-14

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...

Reexamination Certificate

active

06274654

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Technical Field
The invention relates to the compositions consisting of chlorine-containing polymers and aminouracils of the formula I depicted below for stabilizing said 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. Gächter/H. Müller, 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”, 4th 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. Nos. 3,436,362, 4,656,209, 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-aminouracils of the general formula I
where Y is S or O, and
R
1
and R
2
independently of one another are unsubstituted or C
1
-C
4
-alkyl-, C
1
-C
4
-alkoxy- and/or hydroxyl-substituted phenyl, phenyl-C
1
-C
4
-alkyl which is unsubstituted or substituted on the phenyl ring by C
1
-C
4
-alkyl, C
1
-C
5
-alkoxy and/or hydroxyl, or are C
3
-C
6
-alkenyl, C
5
-C
8
-cycloalkyl, or C
2
-C
10
-alkyl interrupted by at least 1 oxygen atom, or, if R
1
and R
2
are different from one another, one of the two radicals can be C
2
-C
12
-alkyl and the other can be C
2
-C
12
-alkyl or one of the above radicals, or, if R
1
and R
2
are identical, both can also be C
5
-C
12
-alkyl, and, if Y is sulfur, R
1
and R
2
cannot be octyl, 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
12
-alkyl is, for example, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, i-octyl, decyl, nonyl, undecyl or dodecyl. Preference is given to n-butyl and octyl.
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
-alkylphenyl is, for example, tolyl or mesityl, especially tolyl. 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, methoxy or ethoxy. If the alkyl radicals are interrupted, they necessarily contain at least 2 carbon atoms. Examples of —O— interrupted C
2
-C
10
-alkyl radicals are branched or straight-chain radicals such as, for example, methoxymethyl, methoxyethyl, methoxypropyl, methoxybutyl, methoxyhexyl, methoxyoctyl, ethoxymethyl, ethoxyethyl, ethoxypropyl, ethoxybutyl, ethoxyhexyl, ethoxyoctyl, n-propoxymethyl, n-propoxethyl, n-propoxybutyl, n-propoxyhexyl, i-propoxymethyl, i-propoxyethyl, i-propoxybutyl, i-propoxyhexyl, n-butoxymethyl, n-butoxyethyl, n-butoxybutyl, n-butoxyhexyl or t-butoxymethyl, etc. Preference is given, for example, to ethoxypropyl. The alkyl chain can also be interrupted by more than one —O—. Examples of such radicals are —CH
2
—O—CH
2
—CH
2
—O—CH
3
, —CH
2
—O—CH
2
—CH
2
—CH
2
—O—CH
3
, —CH
2
—O—CH
2
—CH
2
—CH
2
—CH
2
—O—CH
3
, —CH
2
—CH
2
—O—CH
2
—CH
2
—O—CH
2
—CH
3
, —CH
2
—CH
2
—O—CH
2
—CH
2
—O—CH
2
—CH
2
—O—CH
2
—CH
3
, etc. Here too, structural isomers are possible.
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
are identical and, in particular, where R
1
and R
2
are both C
8
-C
12
-alkyl. Further advantageous compounds are those in which Y is sulfur. Preference is also given to compounds of the formula I in which R
1
and R
2
independently of one another are phenyl, C
1
-C
4
-alkylphenyl, benzyl, 2-phenethyl, allyl or C
3
-C
10
-alkyl interrupted by 1 to 3 oxygen atoms. Preference is likewise given to compounds of the formula I in which R
1
and R
2
are C
2
-C
12
-alkyl with the proviso that R
1
and R
2
are not the same alkyl radical, and especially those where R
1
and R
2
are C
4
-C
8
-alkyl. Very particular preference is given to compounds of the formula I in which R
1
and R
2
independently of one another are phenyl, 2-phenylethyl, benzyl or alkyl, or one of the two substituents is C
2
-C
6
-alkyl and the other is phenyl, 2-phenylethyl, benzyl or 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.
DETAILED DESCRIPTION OF THE INVENTION
Polyols and Disaccharide Alcohols
Examples of suitable compounds of this type are: pentaerythritol, dipentaerythritol, tripentaerythritol, trimethylolethane, bistrimethylolpropane, inositol (cyclitols), polyvinyl alcohol, bistrimethylolethane, trimethylolpropane, sorbitol (hexitols), maltitol, isomaltitol, cellobiitol, lactitol, lycasine, mannitol, lactose, leucrose, tris(hydroxyethyl) isocyanurate, tris(hydroxypropyl)isocyanurate, palatinitol, tetramethylolcyclohexanol, tetramethylolcyclopentanol, tetramethylolcyclopyranol, xylitol, arabinitol (pentitols), tetritols, glycerol, diglycerol, polyglycerol, thiodiglycerol or 1-O-&agr;-D-glycopyranosyl-D-mannitol dihydrate. Of these, preference is given to the disaccharide alcohols. It is also possible to use polyol syrups, such as sorbitol, mannitol and maltitol syrup. The polyols can be employed in an amount of, for example, from 0.01 to 20, judiciously from 0.1 to 20 and, in particular, from 0.1 to 10 parts by weight per 100 parts by weight of PVC.
Perchlorate Compounds
Examples are those of the formula M(ClO
4
)
n
, in which M is Li, Na, K, Mg, Ca, Sr, Ba, Zn, Al, La or Ce. Depending on the valency of M, the index n is 1, 2 or 3. The perchlorate salts can be present as solutions or can have been complexed with alcohols (polyols, cyclodextrins) or ether alcohols or ester alcohols. The ester alcohols also include the polyol partial esters. In the case of polyhydric alcohols or polyols, their dimers, trimers, oligomers and polymers are also suitable, such as di-, tri-, tetra- and polyglycols and also di-, tri- and tetrapentaerythritol or polyvinyl alcohol in various degrees of polymerization. Other suitable solvents are phosphate esters and also cyclic and acyclic carbonates. In this context, the perchlorate salts can be employed in various common forms of presentation; for example, as a salt or solution in water or an organic solvent as such, or adsorbed on a support material such as PVC, Ca silicate, zeolites or hydrotalcites, or bound by chemical reaction into a hydrotalcite or into another layered lattice compound. As polyol partial ethers, preference is given to glycerol monoethers and glycerol monothioethers. Further embodiments are described in EP 0 394 547, EP 0 457 471 and WO 94/24200. The perchlorates can be empl

Affiliated with

Also associated with

Rating

1,3-Disubstituted 6-aminouracils for stabilizing halogenated... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with 1,3-Disubstituted 6-aminouracils for stabilizing halogenated..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and 1,3-Disubstituted 6-aminouracils for stabilizing halogenated... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2540925