WO1986001812A1

WO1986001812A1 - Stabilizer of chlorine-containing thermoplasts with nitrogen-containing organic compounds

Info

Publication number: WO1986001812A1
Application number: PCT/CH1984/000144
Authority: WO
Inventors: Wolfgang Wehner; Rainer Schneider; Horst MÜLLER (deceased)
Original assignee: Ciba-Geigy Ag; MÜLLER, Anneliese (Heiress of MÜLLER, Horst (decea; MÜLLER, Sylvia (heiress of MÜLLER, Horst (deceased; MÜLLER, Werner, Josef (heir of MÜLLER, Horst (dece; MÜLLER, Rainer, Robert (heir of MÜLLER, Horst (dec
Priority date: 1984-09-12
Filing date: 1984-09-12
Publication date: 1986-03-27
Also published as: JPS62500665A

Abstract

Chlorine-containing thermoplasts are disclosed which contain as stabilizer at least one compound of formula (I) wherein m is 0, 1 or 2, n is 1, 2 or 3 and P = 1 or 2, Y represents -F, -Cl, -Br, -I, -CH3 or C2H5, X represents -NH2, -NHCH3, -NHNH2, -OCH3 or -OC2H5 and R is -H, -HO, -NH2 or substituted alkyl. A process for the preparation of (substituted) anthranilic acid amide is also disclosed.

Description

Stabilization of chlorine-containing thermoplastics with nitrogen-containing organic compounds.

The present invention relates to chlorine-containing thermoplastics containing organic nitrogen-containing compounds and to a process for the preparation of (substituted) anthranilic acid (2-hydroxyethyl) amides.

Thermoplastics containing chlorine must be protected against the damaging effects of light and heat. In particular, the processing of the plastic into molded parts is associated with a heat load which causes darkening and embrittlement if suitable additives are not added. Up to now, organotin compounds, metal carboxylates and phenolates, phosphites and mixtures thereof have been used as additives. The stabilization achieved with these additives is not always sufficient in practice, so there is certainly a need for improved, in particular metal-free, thermal stabilizers.

Various nitrogen-containing organic compounds have already been proposed for the stabilization of chlorine-containing polymers. Examples of these are phenylurea derivatives, such as those e.g. in "Stabilization and Aging of Plastic Materials" by Kurt Thinius, pp. 358-359, (1969), and various aminophenols, as described in EP patent application 0048 222.

Furthermore, the DD patent 652 describes aminobenzenesulfonic acid amides or aminobenzoic acid esters as PVC stabilizers From DE-PS 871834 aromatic amines are known as PVC stabilizers which, among other things, carry carboxamide residues as substituents.

It has now been found that certain nitrogen-containing organic compounds are particularly well suited for the stabilization of chlorine-containing thermoplastics and are very effective against their damage by the thermal load during their processing.

The invention relates to chlorine-containing thermoplastics containing at least one nitrogen-containing organic compound of the formula I.

(I) in which

m is a number 0, 1 or 2, n is a number 1, 2 or 3 and p is a number 1 or 2,

Y represents -F, -Cl, -Br, -I, -CH ₃ or -C ₂ H ₅ ,

X denotes -NH ₂ , -NHCH ₃ , -NHNH ₂ , -OCH ₃ , -OC ₂ H ₅ , where X can be different within the given definition if it occurs several times, and

R is -H, -OH, -NH ₂ , or C ₁ -C ₁₈ alkyl substituted by one to three HO and / or C ₁ -C ₄ alkoxy or phenoxy groups, or R is also a group of the formula II

(II),

in which Z is -NH- or -0-, q is an integer from 0 to 6, where Y, X, m and n are as defined above, and where R is hydrogen only when p is 1. If R represents alkyl substituted by -OH and / or alkoxy or phenoxy, this is, for example, 2-hydroxyethyl, 2-hydroxy-n-propyl, 3-hydroxy-n-propyl, 2,3-dihydroxy-n- propyl, 2-methoxyethyl, 2-ethoxyethyl, 2-n-butyloxyethyl, 2-isopropyloxyethyl, 2-phenoxyethyl, 2-hydroxy-1-phenoxyethyl, 3-methoxypropyl, 2-hydroxy-3-n-butyloxypropyl, 2-hydroxy- 3-phenoxypropyl or 2-hydroxy-1,1-di (hydroxymethyl) ethyl.

2-Hydroxyethyl and 2-hydroxypropyl are preferred, but in particular 2-hydroxyethyl.

Y is preferably bromine, iodine, fluorine and especially chlorine, and the

Number m preferably 0 or 1, particularly preferably 0. The number n is in particular 1.

The thermoplastics according to the invention preferably contain such

Derivatives of formula I, wherein n and p 1 and m represent the number 0.

Also preferred are thermoplastics containing compounds of the formula I in which X is -NH ₂ , R -OH, -NH ₂ , C ₂ -C ₃ alkyl substituted by -OH and / or C ₁ -C ₄ alkoxy or phenoxy, m is the number 0 and n and p denote the number 1.

The thermoplastics according to the invention very particularly preferably comprise compounds of the formula I in which X is —NH ₂ , R —OH, —NH ₂ or —C ₂ H ₄ OH, m is the number 0 and n and p is the number 1.

Compounds of the formula I in which X is -NH ₂ or -NHCH ₃ or -NH-NH ₂ or -OCH ₃ or -OC ₂ H _{5 are} particularly preferred, but in particular -NH ₂ .

Likewise preferred are compounds of the formula I in which R is -OH or -NH ₂ or C ₁ -C ₁₈ alkyl substituted by one to three HO and / or C ₁ -C ₄ alkoxy or phenoxy groups.

Also of interest are compounds of the formula I in which R is a radical of the formula II.

The preferred compounds of the formula I also include those in which R is -OH or -NH ₂ or -C ₂ H ₄ OH. Also of interest are compounds of the formula I in which Z is -O-.

Also preferred are compounds of the formula I in which R is C ₂ -C ₄ alkyl substituted by one or two OH groups, only one OH group being present per C atom and the C atom bonded to the amide nitrogen being no OH Group wears.

The following may be mentioned as examples of compounds of the formula I:

Anthranilic acid hydroxylamide

5-chloroanthranilic acid hydroxylamide

Anthranilic acid N-d ', 1'-di-hydroxymethyl-2'-hydroxyethyl) amide

Anthranilic acid N- (2 ', 3'-dihydroxy-propyl) amide

Anthranilic acid N- (2'-hydro-cyethyl) amide

5-chloroanthranilic acid N- (2'-hydroxyethyl) amide

3,5-dichloroanchranilic acid N- (2'-hydroxyethyl) amide

Anthranilic acid N- (2'-hydroxy-n-propyl) amide

Anthranile spits-N- (3'-hydroxy-n-propyl) amide

Anthranilic acid N- (2'-hydroxy-2'-phenyl-ethyl) amide

Anthranilic acid N- (2'-hydroxy-3'-n-butyloxy-n-propyl) amide

3-aminobenzoic acid N- (2'-hydroxyethyl) amide

4-aminobenzoic acid N- (2'-hydroxyethyl) amide

2-N-methylamino-benzoic acid N- (2'-hydroxyethyl) amide

2-aminobenzoic acid hydrazide

3-aminobenzoic acid hydrazide

4-aminobenzoic acid hydrazide

2-, 3- or 4-methoxybenzoic acid hydrazide

2,4-dimethoxybenzoic acid hydrazide

3,4-diaminobenzoic acid hydrazide

3,4-dimethoxybenzoic acid hydrazide

3,4,5-trimethoxybenzoic acid hydrazide

2-amino-5-chlorobenzoic acid hydrazide

2-amino-3,5-dichlorobenzoic acid hydrazide

2-methoxy-4-aminobenzoic acid hydrazide Anthranilic acid N- [2 '- (o-aminobenzoyloxy) ethyl] amide Anthranilic acid N- [2' - (p-aminobenzoyloxy) ethyl] amide 3-amino-4-chlorobenzoic acid N- (2'- hydroxyethyl) amide 3-amino-4-chlorobenzoic acid hydrazide 4-amino-2-chlorobenzoic acid N- (2'-hydroxyethyl) amide 4-amino-2-chlorobenzoic acid hydrazide 4-amino-2-chlorobenzoic acid N- (2'- hydroxyethyl) amide 3-aminobenzoic acid N- (2'-hydroxyethyl) amide 4-amino-2-chlorobenzoic acid hydrazide 4-aminobenzoic acid N- (2'-hydroxyethyl) amide 4-chloroanthranilic acid N- (2'-hydroxyethyl ) -amide 3,5-dichloroanthranilic acid-N- (2-hydroxyethyl) -amide 4-chloroanthranilic acid hydrazide

4-amino-3-methoxybenzoic acid N- (2'-hydroxyethyl) amide 4-amino-3-methoxybenzoic acid hydrazide 3,4-diaminobenzoic acid N- (2'-hydroxyethyl) amide 3,4-diaminobenzoic acid hydrazide. 3,5-diaminobenzoic acid N- (2'-hydroxyethyl) amide 3,5-diaminobenzoic acid hydrazide

2,3-, 2,4-, 2,6-, 3,4- or 3,5-dimethoxybenzoic acid N- (2'-hydroxyethyl) amide

2,3-, 2,4-, 2,6-, 3,4- or 3,5-dimethoxybenzoic acid hydrazide 2,3,4-, 2,4,5-, 3,4,5- or 2, 4, 6-Trimethoxybenzoic acid N- (2'-hydroxyethyl) amide 2,3,4-, 2,4,5-, 3,4,5- or 2,4,6-trimethoxybenzoic acid hydrazide.

Many of the compounds of the formula I are known and can be prepared by processes known per se.

Compounds of formula I can, for example, by reacting an isatoic anhydride derivative with an amine of formula III

H ₂ NR (III) or be produced with hydrazine, such as, for example, according to the method described in Synthesis 1980, pp. 516-523 or the process described in US Pat. No. 3,351,659. They can also be obtained by reacting a benzene carboxylic acid ester with an amine of the formula III or with hydrazine.

Such compounds can also be prepared by reacting a nitrobenzene carboxylic acid chloride with an amine of the formula III and then reducing the nitro group to the amine.

In formula III, the radical R has the meaning given above.

The invention further relates to a process for the preparation of compounds of formula IV

wherein R, Y and m have the meaning already defined above, but R is preferably -CH ₂ -CH ₂ -OH, by reacting a suitably substituted isatoic anhydride with a primary amine RNH ₂ , characterized in that butyl acetate or a butyl acetate is used as the reaction medium / Water mixture or the reaction product used.

The compounds of the formula I can be added in the usual amounts to chlorine-containing thermoplastics. 0.01 to 10% by weight, particularly 0.05 to 5 and in particular 0.2 to 2.5% by weight, based on the chlorine-containing thermoplastics, are preferably incorporated. Mixtures of the compounds of formula I can also be used.

Vinyl chloride polymers or copolymers are preferably used as chlorine-containing thermoplastics. Suspension and bulk polymers and washed-out, ie low-emulsifier, emulsion polymers are preferred. Examples of suitable comonomers for the copolymers are: vinyl acetate, vinylidene chloride, transdichlorethylene, ethylene, propylene, butylene, maleic acid, acrylic acid, fumaric acid, itadonic acid. Other suitable chlorine-containing thermoplastics are post-chlorinated PVC and chlorinated polyolefins, as well as graft polymers of PVC with EVA (ethylene-vinyl acetate) and MBS (methyl acrylate-butadiene-styrene).

The thermoplastics stabilized according to the invention are produced by known processes. The stabilizers of the formula I are incorporated into the chlorine-containing thermoplastics to be stabilized before processing in conventional facilities. A homogeneous mixture can e.g. with the help of a two-roller mixer at 150 to 210 °.

The compounds of the formula I according to the invention can advantageously also be used in combination in customary amounts with at least one of the conventional PVC stabilizers and / or other additives, such as epoxy compounds, preferably epoxidized fatty acid esters, such as epoxidized soybean oil, phosphites, metal carboxylates and metal phenolates of metals of the second Main and sub-group of the periodic table, or also inorganic salts of metals of the second sub-group of the periodic table, such as ZnCl ₂ or further also organotin compounds, in particular mono- or diorganotin compounds, antimony trimercaptocarboxylic acid esters, and antioxidants.

Costabilizers are preferably incorporated in amounts of 0.05 to 3, in particular 0.1 to 3,% by weight, based on the overall composition. Suitable conventional phosphites are phosphites of the general formulas V and VI

(VI),

in which R ² , R ³ and R ^{4 are} identical or different and are C ₆ -C ₁₈ alkyl, a phenyl radical which is substituted or unsubstituted by C ₁ -C ₉ alkyl or C ₁ -C ₉ alkoxy, or C ₅ -C ₇ cycloalkyl , and in what

R _{5 is} C ₆ -C ₁₈ alkyl.

If R ² , R ³ , R ⁴ and R ^{5 are} C ₆ -C ₁₈ alkyl, this is, for example, n-hexyl, n-octyl, n-nonyl, decyl, dodecyl, tetradecyl, hexadecyl or octadecyl. Alkyl groups with 8 to 12 carbon atoms are preferred.

As substituted phenyl, R ² , R ³ and R ⁴ mean, for example, tolyl,

Ethylphenyl, xylyl, nonyl, cymyl, cresyl, 4-methoxyphenyl, 2,4-dimethoxyphenyl, ethoxyphenyl, butoxyphenyl, p-n-octylphenyl or p-n-nonylphenyl.

Particularly suitable phosphites are trioctyl, tridecyl, tridodecyl, tritetradecyl, tristearyl, trioleyl, triphenyl, tricresyl, tris-p-nonylphenyl or tricyclohexyl phosphite and the aryl dialkyl and alkyl are particularly preferred. Diaryl phosphites such as Phenyldidecyl-, nonylphenyl-didecyl-, (2,4-di-tert-butyl-phenyl) -di-dodecyl-phosphite, (2,6-di-tert-butyl-phenyl) -didodecyl phosphite.

Examples of metal carboxylates are the metal salts of saturated, unsaturated or hydroxyl-substituted aliphatic carboxylic acids having 6 to 20 carbon atoms, such as hexanoic acid, heptanoic acid, octanoic acid, 2-ethylhexanoic acid, undecylic acid, lauric acid, myristin acid, palmitic acid, stearic acid, 12-0xystearic acid, oleic acid, linoleic acid or ricinoleic acid. Also of interest are the metal salts of aromatic carboxylic acids such as

C ₁ -C ₈ alkyl substituted benzoates. Metals from the Ba series are preferred. Sr, Ca, Mg and Zn. Preferred metal carboxylates are, for example, Ca, Ba or Zn stearate or oleate.

Suitable metal phenolates are, in particular, the metal salts of phenols with 6-20 C atoms, for example alkylphenols such as p-tert. Butyl, p-octyl, p-nonyl or p-dodecylphenol.

Examples of organotin compounds are (polymeric) organotin oxides or sulfides such as butylstannonic acid and thiostannonic acid, organotin carboxylates such as dibutyltin dilaurate, organotin alcoholates and phenolates, organotin mercaptides such as dibutyltin didodecyl mercaptide, or organotonic acid ester diaptapt octyltin di (2ethylhexyl thioglycolate) or di-n-butyltin di (mercaptopropionic acid n-dodecyl ester). Mono- and diorganotin thioglycol esters and mixtures thereof are particularly suitable.

Examples of antioxidants are alkylated monophenols and hydroquinones, hydroxylated thiodiphenyl ethers, 1,4-alkylidene bisphenols, benzyl compounds, acylaminophenols, esters or amides of β- (3,5-ditert.-butyl-4-hydroxyphenyl) propionic acid and esters β- (5-tert-butyl-4-hydroxy-3-methylphenyl) propionic acid.

Preferred antioxidants are alkylated monophenols, alkylidene bisphenols and phenyl-substituted propionic acid esters, but in particular 2,6-di-tert-butyl-p-cresol, 2,2-bis (4'-hydroxyphenyl) propane and β- (3,5- Di-tert-butyl-4-hydroxyphenyl) propionic acid n-octadecyl ester. The compounds of formula I can also be used with other nitrogen-containing organic stabilizers. Examples include cyanamide, dicyandiamide, guanamines such as benzoguanamine, indoles such as phenylindole, pyrroles (for example according to EP application No. 22087), pyrazoles (for example as described in GB-PS 866936), ureas and thioureas such as monophenylurea and diphenylthiourea, aminocrotonic acid esters, ß -Diketones such as stearoylbenzoylmethane, polyols such as pentaerythritol. Those are preferred

Urea compounds, but especially dicyandiamide. Dicyandiamide with a grain size of less than 10 μm is very particularly preferred.

Depending on the intended use of the thermoplastics stabilized according to the invention, other additives can also be incorporated before or during the incorporation of the stabilizer, such as e.g. Lubricants (preferably montan waxes or glycerol esters), fatty acid esters, paraffins, plasticizers, fillers, carbon black, asbestos, kaolin, talc, glass fibers, modifiers (such as impact additives), optical brighteners, pigments, light stabilizers, UV absorbers, flame retardants or Antistatic.

The thermoplastics according to the invention can be shaped, e.g. processed into molded parts by extrusion, injection molding or calendering. Use as piastisole is also possible.

The thermal stabilization with the stabilizers considered according to the invention is very good in the thermoplastics considered according to the invention.

The following examples serve to explain the invention in more detail. Unless otherwise defined, parts are parts by weight and percentages are percentages by weight Example 1: 48 parts of NaOH are placed in 300 parts of water. 41.6 parts of NH ₂ OH.HCl and then 45.2 parts of methylanthranilate are added in portions with cooling. After standing for 3 days at room temperature, the solution is concentrated and the residue thus obtained is treated with concentrated hydrochloric acid up to pH 6. After filtration and washing with ethanol, anthranilic acid hydroxylamide is obtained as colorless crystals of mp. 140-142 ° C. with a yield of 85%.

Example 2: 165.2 parts of p-aminobenzoic acid ethyl ester are dissolved in 150 parts of ethanolamine and ethanol is then distilled off at 160.degree. The volatile constituents are then stripped off in vacuo and the resulting residue is recrystallized from isopropanol. P-Aminobenzoic acid-β-hydroxyethylamide with a melting point of 116 ° C. is obtained.

Example 3: a) 1039 parts of isatoic anhydride (96%) are introduced in portions into a solution of 410.5 parts of ethanolamine and 2000 parts of H ₂ O at room temperature and, after the CO ₂ evolution has ended, a further 1/2 hour at 60 ° C. touched. The brown solution obtained is concentrated to a residue, this is taken up in CHCl ₃ , adhering water is removed azeotropically and again concentrated to a residue, anthranilic acid-β-hydroxyethylamide having a melting point of 90-92 ° C. is obtained.

1H-NMR (in DMSO; ppm vs. TMS):

6.5, 6.7, 7.1, 7.5 (4H);

3.3 udd 3.5 (4H, 2> ₂ ); 4.7 (1H, -OH); 6.4 (2H, -NH ₂ ) and

8.1 (1H, -NH-). b) 85.6 parts of isatoic anhydride are suspended in 300 parts of butyl acetate and 12 parts of water. While stirring, 30.6 parts of ethanolamine are added dropwise at 40 to 50 ° C. (CO ₂ evolution) and the mixture is left to react at 100 ° C. for 30 minutes. After separating the organic phase and removing the volatile constituents, 69.7 parts of the end product are obtained. By further dilution of the aqueous phase with 10 parts of water and cooling to 0 ° C., a further 9.0 parts are obtained after filtration and drying, so that the overall yield of the final product is 88% of theory. is.

c) 85.6 parts of isatoic anhydride are suspended in 250 ml of butyl acetate at 40 ° C. A mixture of 30.5 parts of ethanolamine and 50 parts of butyl acetate is added dropwise with stirring. The reaction is held at reflux for one hour. After adding 10 parts of filter aid, the product is filtered off with suction and washed with 40 parts of hot butyl acetate. It is cooled to 0 ° C and the reaction product is separated by filtration and dried. The filtrates are used in a further four cycles, the procedure being as described above. The final yield is 82% of theory

d) 32.6 parts of isatoic anhydride are introduced in portions at 110 ° C. into a melt of 56.0 parts of anthranilic acid N- (2'-hydroxyethyl) amide and 12.2 parts of ethanolamine. It is held at 115 ° C for one hour. After adding 250 parts of butyl acetate and 10 parts of filter aid, the mixture is stirred at 100 ° C. for one hour. After filtration and removal of the volatile constituents, the reaction product remains in a yield of

96% of theory

e) Analogously to the method given in example 3a) above, further compounds of the formula I are prepared, which are listed in Table I below.

Examples of use:

Example 8: A dry mixture consisting of the composition specified in the following recipe is rolled on a mixing roll mill at 180 ° C. for 5 minutes. Test film pieces with a thickness of 0.3 mm are removed from the rolled sheet formed. The film samples are thermally stressed in an oven at 180 ° C. and determined at intervals of 10 minutes on a sample of the Yellowness Index (YI) according to ASTM D 1925-70. The results are summarized in Table II below.

Recipe: Solvic ^® 264 GA (K value 64) 100.0 g Ca stearate 0.35 g

Zn stearate 0.15 g Rheoplast ^® 39 (epoxidized soybean oil) 3.0 g

Irgastab ^® CH 300 (didecylphenyl 0.55 g phosphite)

Compound of formula I 2.5 mmol

These test results clearly show an improvement in the basic formulation (without stabilizer) by adding the stabilizers of the formula I considered according to the invention, in particular with regard to the initial color.

Example 9;

100 parts E-PVC (Vestolit ^® E 6507), 2.0 parts Loxiol ^® GS 1 and

3 parts of titanium dioxide RN 57 ^® (titanium company) are mixed with 0.3 parts of anthranilic acid ethanolamide (example No. 3a) and subjected to a static heat test according to application example 8 and the degree of yellowing on a sample at intervals of 5 minutes using the yellowness index (YI) determined according to ASTM D 1925-70. The results are shown in Table III.

Example 10:

100 parts Vestolit ^® E 6507 are plasticized with 40 parts of di-2-ethylhexyl phthalate, pigmented with 3 parts of titanium dioxide and stabilized with 0.4 parts of the compound of formula I used in Example. 9 The following Table IV contains the result of a static heat test carried out according to Example 9 at 180 ° C.

Example 11:

100 parts Vestolit ^® E 6507, 3.5 parts Loximol ^® GS 1 and an inventive combination of 0.5 parts of an organotin stabilizer (dibutyltin-bis-isooctylthioglycolate), 0.5 parts Anthranilsäureethanolamid (Example 3a), 2.0 parts of epoxidized soybean oil and 0.5 part of monophenyldidecyl phosphite are subjected to a continuous rolling test on a laboratory rolling mill at 190 ° C., pieces of film (0.3 mm thickness) being removed at intervals of 5 minutes and the degree of yellowing of these samples using the Yellowness Index (YI) according to ASTM D 1925-70 is determined. The results are shown in Table V.

Example 12;

Further compounds of the formula I considered according to the invention are tested in the following recipes according to the method given in Example 8 at 190 ° C. (oven temperature). The results are shown in the next Table VI.

Recipes: A Vestolit ^® E 6507 (100 parts); Loxiol ^® GS 1 (2 parts);

TiO ₂ (4 parts); Stabilizer of formula I (0.8 parts). A ₁ Vestolit ^® 6507 (100 parts); Loxiol ^® GS 1 (2 parts);

TiO ₂ (4 parts); Stabilizer of formula I (0.6 parts). Vestolit B ^® E 8019 (100 parts); Wachs ^® E (Hoechst, 0.4 parts);

Stabilizer of formula I (0.6 parts). C Hostalit ^® E 2078 (100 parts); Wachs ^® OP (0.4 parts);

Rheoplast ^® 39 (2 parts); Stabilizer of formula I (0.8 parts)

Example 26: Further compounds of the formula I considered according to the invention are tested in the following recipe (rolling time 10 minutes at 180 ° C.) according to Example 8 at 200 ° C. (oven temperature).

Recipe: Vestolit ^® E 8019 (100 parts); Wachs ^® E (company Hoechst,

4 pieces); Stabilizer of formula I (0.6 parts).

The results are shown in the next Table VII.

Example 37; 100 parts of alkaline pre-stabilized E-PVC (Vestolιt ^®

E 6507), 40 parts diisooctyl phthalate (DOP), 3 parts titanium dioxide

(Kronos ^® RN 57 p) and 0.4 part of a stabilizer mixture consisting of 70 parts by weight of dicyandiamide and 30 parts by weight of anthranilic acid ethanolamide (Example No. 3a) are mixed and subjected to a static heat test according to Application Example 8 at 180 ° C. The yellowness index of a sample is determined at intervals of 5 minutes by measuring the Yellowness Index (YI) in accordance with ASTM D 1925-70. The results are shown in Table VIII.

Example 38: 100 parts of PVC (Hostali ^® E 2078), 4 parts of wax E and 0.6 part of a stabilizer mixture consisting of 70 parts by weight Anthranilsäureethanolamid (Example 3A on) and 30 parts by weight of dicyandiamide are mixed and at 200 ° C subjected to a static heat test according to Example 8. The yellowness index of the sample is determined at intervals of 5 minutes by measuring the Yellowness Index (YI) in accordance with ASTM D 1925-70. The results are shown in Table IX.

Claims

1. Chlorine-containing thermoplastics containing at least one nitrogen-containing organic compound of the formula I.

(I) in which

m is a number 0, 1 or 2, n is a number 1, 2 or 3 and

P is a number 1 or 2,

Y represents -F, -Cl, -Br, -I, -CH ₃ or C ₂ H ₅ ,

^ (II),

in which Z is -NH- or -0-, q is an integer from 0 to 6, where Y, X, m and n are as defined above, and where R is hydrogen only when p is 1.

2. Chlorine-containing thermoplastics according to claim 1, wherein in the compound of the formula I n and p represent the number 1 and m the number 0.

3. Chlorine-containing thermoplastics according to claim 1, comprising at least one compound of the formula I, in which X -NH ₂ , R -OH, -NH ₂ , C ₂ -C ₃ substituted by -OH and / or C ₁ -C ₄ alkoxy or phenoxy Alkyl, m is the number 0 and n and p is the number 1.

4. Chlorine-containing thermoplastics according to claim 1, containing at least one compound of formula I, wherein X is -NH ₂ , R -OH, -NH ₂ or -C ₂ H ₄ OH, m is the number 0 and n and p is the number 1.

5. Chlorine-containing thermoplastics according to claim 1, containing the compound anthranilic acid ethanolamide.

6. Chlorine-containing thermoplastics according to claim 1, containing at least one compound of formula I in an amount of 0.01 to 10 wt .-% based on the chlorine-containing thermoplastics.

7. Chlorine-containing thermoplastics according to claim 1, characterized in that they are emulsion PVC.

8. Chlorine-containing thermoplastics according to claim 1, containing a urea compound.

9. Chlorine-containing thermoplastics according to claim 1, containing dicyandiamide.

10. Chlorine-containing thermoplastics according to claim 9, wherein the dicyandiamide has a grain size of less than 10 microns.

11. Chlorine-containing thermoplastics according to claim 9, containing a stabilizer mixture of 30 parts by weight of anthranilic acid ethanolamide and 70 parts by weight of dicyandiamide.

12. Chlorine-containing thermoplastics according to claim 9, containing a stabilizer mixture of 70 parts by weight of anthranilic acid ethanolamide and 30 parts by weight of dicyandiamide.

13. Process for the preparation of compounds of formula IV

(IV)

wherein R, Y and m have the meaning already defined in claim 1, by reacting a suitably substituted isatoic anhydride with a primary amine R-NH ₂ , characterized in that butyl acetate or a butyl acetate / water mixture or the reaction product is used as the reaction medium.

14. The method according to claim 13, wherein R is -CH ₂ -CH ₂ -OH.