4-aminopyrimidinones and oxazolidino-4-aminopyrimidinones,...

Details 4-aminopyrimidinones and oxazolidino-4-aminopyrimidinones,... 4-aminopyrimidinones and oxazolidino-4-aminopyrimidinones,...

2000-04-04

2001-05-15

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...

C524S100000, C524S114000, C524S379000, C524S400000, C524S427000, C524S430000, C524S493000, C544S235000

Reexamination Certificate

active

06232375

ABSTRACT:

The invention relates to 4-aminopyrimidinones and oxazolidino-4-aminopryimidinones of the formulae I and II given below, a process for their preparation, their use for stabilizing halogen-containing polymers, and compositions composed of compounds of the formula I and II and of chlorine-containing polymers, in particular PVC.
BACKGROUND OF THE INVENTION
There is a wide variety of additives for of stabilizing PVC. Particularly suitable for this purpose are compounds of lead, of barium and of cadmium, but nowadays these are contentious for environmental reasons or due to their heavy metal content (cf.,pages 303-311, and “Kunststoff Handbuch PVC” [“Plastics Handbook PVC”], Vol. 2/1, W. Becker/D.Braun, Carl Hanser Verlag, 2
nd
Ed., 1985, pages 531-538; and also Kirk-Othmer: “Encyclopedia of Chemical Technology”, 4
th
Ed., 1994, Vol. 12, Heat Stabilizers, pp. 1071-1091). Further attempts are therefore being made to find effective stabilizers or stabilizer combinations which are free from lead, barium and cadmium.
1,3-disubstituted aminopyrimidinediones 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) steps.
It has now been found that 1,3-disubstituted 4-aminopyrimidinediones and oxazolidino-4-aminopyrimidinediones of the general formulae I and II and particularly suitable for stabilizing chlorine-containing polymers, in particular PVC.
SUMMARY OF THE INVENTION
The present invention therefore provides compounds of the general formulae I and II
where X=O or S, preferably O, R
2
=H, or the radicals C
1
-C
14
-alkyl, C
2
-C
4
-alkenyl, unsubstituted or substituted C
4
-C
8
-cycloalkyl, C
6
-C
10
-aryl, C
7
-C
10
-alkaryl, C
7
-C
10
-aralkyl, —CH
2
—X—R
4
, with R
4
=H, C
1
-C
10
-alkyl, C
2
-C
4
-alkenyl or C
4
-C
8
-cycloalkyl, if desired containing an oxirane ring or, if desired, substituted 1-3 times with C
1
-C
4
-alkyl, and unsubstituted or substituted benzoyl or C
2
-C
18
-acyl radical, and preferably R
2
=H, methyl, ethyl, allyl, phenyl, —CH
2
—X—R
4
, with R
4
=H, an n-propyl, isopropyl, 2-ethylhexyl, n-butyl, isobutyl, sec-butyl, tert-butyl, allyl, methallyl, phenyl, cresyl radical; in particular R
2
=ethyl, —CH
2
—X—R
4
, where R
4
=H, n-propyl, isopropyl, allyl, R
3
=R
2
, R
4
or C
2
-C
6
-alkyl substituted with at least 1 to 5 OH groups and/or interrupted by at least 1 to not more than 4 oxygen atoms, or C
3
-C
8
-alkenyl or —CH
2
—CH(OH)R
2
, preferably R
3
=a methyl, phenyl, benzyl radical, in particular the methyl radical.
DETAILED DESCRIPTION OF THE INVENTION
with R
3
=—CH
2
CH
2
OH, —CH
2
—CHOH—CH
3
, —CH
2
—CHOH—C
2
H
5
, —CH
2
—CHOH—
n
C
3
H
7
, —CH
2
—CHOH—
n
C
4
H
9
;
—CH
2
—CHOH—CH
2
—O—
n
C
3
H
7
, —CH
2
—CHOH—CH
2
—O—
i
C
3
H
7
,
—CH
2
—CHOH—CH
2
—O—
n
C
4
H
9
, —CH
2
—CHOH—CH
2
—O—
i
C
4
H
9
,
—CH2—CHOH—CH
2
—O—
sec
C
4
H
9
, —CH
2
—CHOH—CH
2
—O—
i
C
4
H
9
,
—CH
2
—CHOH—CH
2
—O—2-ethylhexyl, -allyl, -phenyl, -o-cresyl, -m-cresyl, -p-cresyl; -pentanoyl, -neohexanoyl, -neoheptanoyl, -neooctanoyl, -neononanoyl, -neodecanoyl.
According to the invention, particular preference is given to the compounds with
R
2
=alkyl=pentyl, hexyl, heptyl, octyl, nonyl, decal, undecyl, dodecyl, tridecyl, and tetradecyl, preferably hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl, and particularly preferably methyl and ethyl;
R
2
=C
6
-C
10
-aryl or C
7
-C
10
-alkaryl=tolyl, xylyl, mesityl, propylphenyl, butylphenyl, trimethoxyphenyl, diethoxyphenyl, propoxyphenyl, or butoxyphenyl, preferably phenyl.
R
2
=C
7
-C
10
-aralkyl=benzyl, &agr;- or &bgr;-phenylethyl, phenylpropyl or phenylbutyl.
Preference is given to benzyl and &bgr;-phenylethyl, particularly preferably benzyl.
R
2
=C
4
-C
8
-cycloalkyl cyclopentyl and cyclohexyl, methylcyclohexyl or trimethylcyclohexyl, preferably cyclohexyl.
R
4
=H, C
1
-C
10
-alkyl, C
2
-C
4
-alkenyl, phenyl or benzyl, preferably ethyl, propyl, butyl, allyl, methallyl. Particular preference is given to propyl, butyl, allyl.
R
4
=C
2
-C
18
-acyl=acetyl, propionyl, butyryl, caproyl, decanoyl, lauryl, myristoyl, palmitoyl or stearoyl. Unsubstituted or substituted benzoyl is trimethylbenzoyl or trimethoxybenzoyl; preference is given to acetyl, propionyl, decanoyl and benzoyl and neodecanoyl is particularly preferred.
R
4
=cycloaklyl=cyclohexylmethyl, cyclohexylethyl, cyclohexylpropyl or cyclohexylbutyl
R
4
=butenyl, hexenyl, heptenyl or octenyl; preferably allyl or methallyl.
Other preferred compounds of the formula I or II are those with X=O or of the formula I with X=S, and particular preference is given to compounds of the formula I with X=O.
The invention also provides a process for preparing the compounds of the general formulae I and II.
The invention also provides the use of the compounds of the general formulae I and II for stabilizing chlorine-containing polymers, in particular polyvinyl chloride (PVC) and recycled materials from these.
The invention therefore also provides compositions made from at least one of the compounds of the general formula I and/or at least one of the compounds of the general formula II and from chlorine-containing polymers, in particular PVC, and recycles materials from these.
The remaining subject matter of the invention is given in the claims.
The novel compounds of the formula I may be prepared from compounds of the general formula III or IV
where R
1
is a branched or unbranched C
1
-C
4
-alkyl radical, in particular the methyl or ethyl radical, with an epoxy compound of the general formula V
where R
2
is as defined above, in a solvent, if desired at elevated pressure, and with a catalytic amount of base.
The compounds of the formulae III and IV are prepared by known methods (e.g. V. Papesch and E. F. Schroeder, J. Org. Chem., 1951 (16), 1879-1890; A. H. Nathan and M. T. Bogert, JACS 63, 2567 (1941); W. Pfleiderer, Chem. Ber., 90, 2272 (1957) or DRP 155 732 (1903) Farbenfabriken Bayer).
The compounds of the general formula (V) are aliphatic, cycloaliphatic, aromatic, araliphatic or alkaromatic epoxy compounds, where R
2
is as defined above, for example ethylene oxide, propylene oxide, butylene oxide,
hexylene oxide, styrene oxide, glycidol, glycidyl ethers or glycidyl thioethers, such as ethyl, propyl, butyl, hexyl, octyl, allyl, or phenyl ethers, or glycidyl esters based on aliphatic and/or aliphatic aromatic alcohols, in particular unbranched or branched aliphatic monofunctional alcohols, such as methanol, ethanol, n-propanol, isopropanol, butanol, sec-butanol, 2-methyl-1-propanol, 2-methyl-2-propanol, 2-ethylhexanol; or aromatic alcohols, such as phenol, cresol, p-tert-butylphenol, thymol, benzyl alcohol.
These are commercially available products which are sold by their chemical designation or by the respective trade name, such as EUREPOX® RV-K, EUREPOX® RV-P, EUREPOXS RV-A (EUREPOX®=trademark of Witco GmbH) or Grilonit® V 51-54, Grilonit® RV 1802, Grilonit® 1804, Grilonit® 1805, Grilonit® 1807 (Grilonit®=trademark of EMS-Chemie) or Araldit® DY 0390, Araldit® DY 0391 (Araldit®=trademark of CIBA Spezialitäten Chemie).
According to the invention, the process for preparing the novel compounds of the general formulae I and II is preferably carried out by reacting a mixture of one mole of a compound of the general formula III or IV, 200-500 ml of a solvent, 0.01-0.3 mol of a base and 1-2, preferably 1-1.5 mol of a compound of the general formula V for 1-10 h at 20-150° C., preferably 40-90° C., if desired under elevated pressure.
The solvents used preferably comprise polar, protic and/or aphotic solvents, such as water, methanol, ethanol, propanol or other water-miscible solvents, such as acetone, tetrahydrofuran (THF), dioxane, dimethylformamide (DMF), dimethylacetamide (DMA) or mixtures of these. These selection depends on the na

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