DE1958639A1 - New organic tin compounds, their production and use - Google Patents

Description

DR.-ING. RICHARD GLAWE DIPL-ING. KLAUS DELFS DIPL-PHYS. DR. WALTER MOLL

MÖNCHEN HAMBURG MÖNCHEN

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REGARDS:

8000 Munich 22 ■ LiebherrstroBe 20 · Tel. (0811) 22 65 48 2000 Hamburg 52 - Waitzstraße 12 Tel. (0411) 89 22 55

YOUR MESSAGE FROM OUR SIGN

MUNICH

Unitika Ltd.

No. 1-50, Higashi Honmachi, Amagasaki-shi, Hyogo-ken, Japan

Norio Saito

No. 1019, Shimizudani, Takatori-cho, Takaichi-gun, Nara-ken, Japan

"New organic tin compounds, their production

and use ¹¹

The present invention relates to new organic tin compounds, their manufacture and use.

The organic tin compounds of the present invention

A 7

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POST CHECK ι HAMBURG 147iO7 BANKi COMMERZBANK, HAMBURG, 53/22904 TELEGR. ι SPECHTZIES HAMBURG or SPECHTZIES MÖNCHEN

are given by the general formula below

R ¹

I 2
A — 0 — Sn — IT [I]

R ¹

shown, in which A is a residue of compounds such as monoalkyl phosphate j dialkyl phosphate, monoalkyl phosphite, Dialkyl phosphite, alkanecarboxylic acid, alkanedicarboxylic acid, monoalkylalkanedicarboxylate, alkenedicarboxylic acid, monoalkylalkenedicarboxylate, Arene carboxylic acid, arene dicarboxylic acid, monoalkyl arene dicarboxylate, alkanesulfonic acid, arene sulfonic acid, Arene disulphonic acid, monoalkyl arene disulphonate or Alkylsulfuric acid exclusively of the hydroxyl group of the

1 2
means the same and R and R are each alkyl, aryl or aralkyl.

The number of carbon atoms in the "alkyl", "alkane", "Alkene", "aryl", "arene" and "aralkyl" moieties as used above are not greater than 20. The alkyl can be methyl, ethyl, propyl, butyl, isobutyl, t-butyl, pentyl, hexyl, octyl, nonyl, decyl or the like. be. Examples of the alkane are methane, ethane, propane, Butane, hexane, octane, etc. For the alkene can be used as an example Athens, propene, butene, etc. can be named. The aryl includes

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Phenyl, ToIyI, XyIyI, Naphthyl, etc. Examples of that Arenes include benzene, toluene, xylene, naphthalene, and the like. The aralkyl can be, for example, benzyl, phenethyl, phenylpropyl or tolylethyl. In general it is preferred

1 2 drawn that at least one of the groups A, R and R in the organic tin compounds [I] have a relatively long Has a chain, e.g., one which has not less than 8 carbon atoms.

It has now been found that the organic tin compounds [I] have excellent antistatic properties. It has also been found to be perfect or nearly in water and numerous organic solvents, including those that have such high solubility like trichlorethylene, are insoluble. Ks became further found to be easy on polymeric materials to form a well-adhering fixation thereupon by conversion between two specific reagents and these materials can be made permanent give antistatic properties. The present invention is based on these findings.

Accordingly, it is a basic object of the present invention to use the organic tin compounds [I] to embody. Another object of this invention

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BATH ORIGINAL

consists in carrying out a process for the production of the organic tin compounds [I]. Another object of the invention is to provide a method by which polymeric materials are imparted excellent permanent antistatic properties in both laundry and dry cleaning. Furthermore, there is still another object of the present * invention to embody polymeric materials which permanent antistatic properties are imparted both in the laundry as well as dry cleaning. These and other objects will become apparent to those skilled in the art to which the present invention pertains from the descriptions below.

According to the present invention, the organic tin compound [I] can normally be prepared by reacting a compound the formula

A-O-X [II]

in which X is hydrogen, lower alkyl (e.g. methyl, ethyl, propyl) or ammonium and A has the same meaning as above, with a compound of the formula

Y — 0 — Sn — R ² [III]

Ii

R ¹
where Y is hydrogen, lower alkanoyl (e.g. acetyl,

009825/2133 " ⁵ "

Propionyl) or a group of the formula

R ¹ "

I 2

—Sn — IT

1 2
and each R and R have the same meaning as above.

Examples of the compound [II] are monomethyl phosphate, Monoäthylphosphat, monobutyl phosphate, monooctyl phosphate, dimethyl phosphate, Diäthylphosphat, dibutyl phosphate, dioctyl phosphate, Dioctylmonomethylphosphat ₃ trimethyl phosphate, triethyl phosphate, tributyl phosphate, trioctyl phosphate, diethyl phosphite, dipropyl phosphite, dibutyl phosphite, Diheptylphosphitj pelargonic acid, lauric acid, myristic acid, palmitic acid, stearic acid, succinic acid, monomethyl, Monoäthylsuccinat, dimethyl succinate, diethyl succinate, Monoammoniummonomethylsuccinat, maleic acid, monomethyl maleate, monoethyl maleate, dimethyl maleate, diethyl maleate, Monoammoniummonomethylmaleat, Monoammoniummonobutylmaleat, phthalic acid, monomethyl phthalate, Monoäthylphthalat, Monooctylphthalat, dimethyl phthalate, dioctyl phthalate, naphthoic acid, Methylnaphthalincarboxylat, äthylnaphthalincarboxylat, Ammoniumnaphthalincarboxylat, naphthalenedicarboxylic acid,

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i-Ionomethylnaphthalenecarboxylate, airanonium butylsulphonate, ammonium laurylsulphonate, methyloctylsulphonate, ammonium octylsulphonate, toluenesulphonic acid. Methylbenzenesulfonate, Methyltoluolsulfonatj Äthyltoluolsulfonat, Methyldodecylbenzolsulfonat, methylnaphthalene Monomethylnaphthalindisulfonat, Monoäthylnaphthalindisulfonat, di - äthylnaphthalindisulfonat, Diammoniumnaphthalindisulfonat, ψ Monoammoniummonomethylnaphthalindisulfonat, Methyloctylsulfat, Methyllaurylsulfat, etc.

For the compound [III], for example, trimethyltin hydroxide, triisopropyltin hydroxide, triisobutyltin hydroxide, triphenyltin hydroxide, tritolyltin hydroxide, bis- (trimethyltin) oxide, bis- (triethyltin) oxide, bis- (triisobutyltin), bis- (triisobutyltin) , Trimethyltin acetate, triethyltin acetate, tributyltin acetate, trioctyl-. , tin acetate, 1,3-dioctyltetraethyldistannoxane, 1,3-dilauryltetrabutyldistannoxane, 1,3-myristyltetrabutyldistannoxane, 1,3-dipalmityl tetrabutyldistannoxane, etc. are listed.

The reaction between the compounds [II] and [III] can be carried out only by mixing them together but is usually in an organic solvent (e.g. methanol, ethanol, benzene, toluene, xylene, Ether, acetone, tetrahydrofuran) at room temperature or

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carried out at a slightly elevated temperature. Most easily, the compounds [II] and [III] are combined into one mixed organic solvents and evaporated the solvent from it at room temperature or with low heating, so that the desired organic tin compound

[I] is obtained.

Various methods can be used to impart antistatic properties to polymeric materials by using the organic tin compound [I]. For example, polymeric materials are immersed in a dispersion of the organic tin compound [I] in Kasser or in an organic solvent (for example methanol, ethanol, benzene), if desired, in the presence of an emulsifier (for example polyethylene glycol alkyl ethers, polyethylene glycol fatty acid esters , sorbitan fens acid esters, fatty acid monoglyides ), squeezed for 15 seconds is 15 Hinuten cured for dried to 5 minutes at 90 to 12O ⁰ C and then at 150 to 210 ⁰ C 15 seconds 1> for fixing the organic tin compound [I] thereon. For example, polymeric materials are also used with the compounds

[II] and [III] simultaneously or separately in a suitable medium (e.g. water, methanol, ethanol), if desired in the presence of a surface-active substance such as polyethylene glycol ether, treated, dried and,

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BATH ORIGINAL

if necessary, cured so that the reaction thereof to form the well fixed on the polymeric materials organic tin compound [I] progresses. Most preferably, the procedure is as follows carried out as described:

At least one of the formulas below

COOZ

[Ha]

[Hb]

[lic]

[lld]

R-SO ₂ -OZ

ZOOC-R'-COOZ

Tile]

[Hg]

R-OSO ₂ OZ

R-COOZ

[Hf]

[Hh]

compounds shown in which R is alkyl, phenyl, alkylphenyl, phenylalkyl or alkylphenylalkyl, R ^{1 is} alkylene with or without a double bond and Z is lower alkyl (e.g. methyl, ethyl, propyl) or ammonium, but not the number of carbon atoms in the groups mentioned

0 09825/2133

is higher than 20, and at least one of the compounds represented by the formulas

R ¹ R ¹

R ² —Sn — 0 — Sn-R ² [HIa]

R —Sn — O — Z · ^ [IHb]

R ¹ /

wherein Z ^{1 is} lower alkanoyl (e.g. acetyl, propionyl)

1 2
and each R - and R - group has the same meaning as above (the compound [IHb] is prepared, for example, by concentrating a mixture of the compound [HIa] with an alkanoic acid under reduced pressure) in a suitable medium (e.g. water, methanol, Ethanol), if desired in the presence of a surface-active agent (eg polyethylene glycol ether), dispersed or dissolved and epoxy resin, methoxy nylon, vinyl acetate or the like preferably added. The mixture obtained is padded onto polymeric materials, and the polymeric materials are squeezed off and dried. The drying can be carried out at room temperature, if necessary at an elevated temperature which does not have any adverse effect on the polymeric materials.

009825/2133

Apart from the above procedure, the following procedure can advantageously be used to polymeric materials antistatic properties due to the organic tin compound of the following general formula

R ¹ R "CO-O-Sn-R ²

in which R ^{1 is} an alkyl group with 8 to 20 carbon -

1 represents 2 atoms and each R and R radical has the same meaning as above. Be accordingly polymeric materials in a solution or dispersion of a polyethylene glycol fatty acid ester or a sorbitan fatty acid ester, in which the carbon atoms of the fatty acid moiety have 9 to 21 carbon atoms and the compound [purple] or [HIb] in a suitable medium (e.g. water, methanol, ethanol), if desired, in the presence of a surfactant, dipped, squeezed and dried so as to be the aforementioned organic To make tin compound on it.

The polymeric materials obtained in this way have excellent permanent antistatic properties as well in laundry as well as in dry cleaning.

009825/2133

The term "polymeric material" used above is understood to mean that the material consists of a polymer is made and fibers, films, molded articles and other materials made of polyester, polymides, polyacrylonitrile or polyolefin.

Practical and presently preferred embodiments of the present invention are shown by way of illustration in the following examples, wherein parts are parts by weight. In these examples, the electrical resistance was measured as a test of the effectiveness of the treatment. It is known that the tendency for static charges to accumulate can be determined by measuring the resistance of the object to be examined. It is also known that items of clothing are almost insensitive to static charges when worn, or that generated static charges can flow away from them if they have a resistance which is less than 10 ohms at 20 ^° C. and 65% relative humidity.

Thus, the present invention encompasses an organic one Tin compound of the general formula

R ¹

• 2
A-0-Sn-R

R ¹

009825/2133 - 12 -

wherein A is a residue of compounds such as monoalkyl phosphate, Dialkyl phosphate, monoalkyl phosphite, dialkyl phosphite, alkanecarboxylic acid, Alkanedicarboxylic acid, monoalkylalkanedicarboxylate, alkenedicarboxylic acid, monoalkylalkenedicarboxylate, arene carboxylic acid, Arene dicarboxylic acid, monoalkyl arene dicarboxylate, alkanesulf onic acid, arenesulfonic acid, arene disulphonic acid, monoalkyl arene disulphonate or alkyl sulfuric acid, excluding

1 represents 2 hydroxyl thereof, and each R and R groups Is alkyl, aryl, or aralkyl, which is used on the polymeric materials to form a good fixation thereon and has excellent permanent antistatic properties both in the wash and in the dry cleaning gives.

example 1

Triisobutyl tin hydroxide (1 mole) and diisooctyl phosphate (1 mol) v / earth dissolved in ethanol and the solvent from the resulting solution below atmospheric pressure removed. After recrystallization from ethanol, the residue gives crystals of triisobutyltin diisooctyl phosphate in quantitative yield with a melting point of 85 C.

The resulting triisobutyltin diisooctyl phosphate (1 part) is dissolved in water (100 parts) in the presence of the nonionic

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surfactant dispersed in polyethylene glycol ether (2 parts). A fabric made from polycapramid is immersed in the dispersion obtained, squeezed off and air-dried. The electrical resistance of the so obtained tissue, which contained 0.0025 to 0.0030 g of the mentioned compound per gram, was 4.3 χ ίο "ohm,

12 whereas that of the untreated tissue was measured to be more than 10 ohms. Even after 5 times dry cleaning with trichlorethylene at room temperature for 10 minutes there was no substantial change in electrical Resistance of the first tissue. Accordingly, this fabric was permanently antistatic equipped with dry cleaning.

Example 2

Triisobutyltin hydroxide (3.0 parts), diisooctyl phosphate (30 parts), polyethylene glycol nonionic surfactant (12.0 parts) and water (285.0 parts) were uniformly mixed. A fabric made of polyethylene terephthalate was immersed in the mixture obtained, squeezed off to achieve an absorption of h0% and then dried in air. The electrical resistance of the tissue

was 7 _a 0 χ 10- ^ ohm, whereas that of the untreated

12th

Tissue was higher than 10 ohms. Even after multiple washes with a 50-fold amount of a $ 0.5 aqueous soap solution at 60 ° C. for 1 hour, it showed one

electrical resistance of 8.2 χ 3Xr ohm. Accordingly

- 14 -CS L2 / SZ860Q

the fabric was therefore permanently antistatic against washing.

Example 3

Triisobutyltin hydroxide (1 mol) and monoisooctyl-o-phthalate (1 hol) were dissolved in ethanol and the solvent was removed from the resulting solution below atmospheric pressure. The residue was fractionally distilled and gave a quantitative yield of triisobutyltin monoisooctyl-o-phthalate as a fraction with a boiling point of 165 to 172 ^° C. at 9 mm Hg.

The triisobutyltin monoisooctyl-o-phthalate thus obtained is dispersed in water in the presence of nonionic surface-active polyethylene glycol ether. A Tissue made of polyethylene terephthalate is immersed in the dispersion obtained, squeezed off and getrock- ' .net. The electrical resistance of the tissue obtained in this way, which is 0.0020 to 0.0025 g of the mentioned compound

Q per gram was 7.5 χ ICr ohm, whereas the

12 Resistance of the untreated tissue higher than 10 ohm

was. Even after repeated washings with the 50-fold amount of a 0.5 # aqueous solution of the synthetic detergent Natrxumdodecylbenzolsulfonat at 6O ⁰ C for 20 minutes, it showed an electric resistance of

9.0 χ 10 ^ ohm. Thus, the antistatic finish is

009825/2133 -15-

Fabric is very durable against repeated washes.

Example ^

Triisobutylzinnhydroxyd (3.0 parts), ^ -Butylbenzolsulfonsäure (2.2 parts), nonionic surfactants polyethylene glycol ether (10.0 parts) and water (285O O ₅ parts) were uniformly mixed. A fabric made of polycapramide was immersed in the resulting mixture at room temperature, squeezed and dried. This fabric was then repeatedly washed with 100 times the amount of a 0.5% strength aqueous solution of the synthetic detergent sodium dodecylbenzenesulfonate at room temperature and then rinsed with water. The electrical resistance of the fabric containing 0.0018 to 0.0020 g of triisobutyltin-IJ-butylbenzenesulfonate per gram,

was 5> 2 χ 10 ^? ohm, whereas that of the untreated

12th

Tissue was higher than 10 ohms. Thus, the antistatic treatment of the fabric against vüschen is very durable.

Example 5

Triisobutyltin hydroxide (1 mole) and triisooctyl phosphate (1 mole) were dissolved in ethanol and the solvent below atmospheric pressure. The residue was recrystallized from ethanol and gave triisobutyl

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BATH ORIGINAL

zinndiisooctylphosphat .in a quantitative yield in the form of crystals having a melting point of 85 ⁰ C. The thus obtained compound gives excellent antistatic properties of polymeric materials.

Example 6

Triisobutyltin hydroxide (1 mole) and diisooctyl-o-phthalate (1 mole) were dissolved in ethanol and the solvent removed below atmospheric pressure. The residue was fractionally distilled to give Triisob.utylzinnmonoisooctyl-o-phthalate as a fraction having a boiling point of I65 to 172 ^O C at 9 mm Hg in quantitative yield. The compound thus obtained imparts excellent antistatic properties to polymeric materials.

Example 7

Triphenyltin hydroxide (1 mol) and methyl p-toluenesulfonate (1 mol) were dissolved in methanol and the solvent was removed at room temperature under reduced pressure. The residue was recrystallized from toluene and triphenyltin p-toluenesulfonate was obtained in quantitative yield in the form of crystals with a melting point of 152 ° C. The triphenyltin p-toluenesulfonate obtained in this way (I ₃ O parts) was dissolved in water (90.0 parts) in the presence of non-

009825/2133 - 17 -

Ionic surfactant polyethylene glycol ether (9.0 Parts). · A manufactured from polyethylene terephthalate Cloth (0.3 part) was immersed in the obtained dispersion and air-dried so as to be antistatic Equipment to achieve.

Example 8

Triisobutyltin hydroxide (3 »0 parts), methyl p-butylbenzenesulfonate (2.3 parts), nonionic surfactant polyethylene glycol ether (10.0 parts) and water (2850.0 parts) were mixed evenly. A fabric made of polyacrylonitrile was immersed in the resulting mixture at room temperature and dried at 75 ° C. The dried tissue was then 20 times with 100 times the amount of a 0.5 # ~ igen aqueous solution of the synthetic detergent sodium dodecylbenzenesulfonate Washed at room temperature for 10 minutes and rinsed with water. After drying in air a fabric was thus obtained with an antistatic finish caused by triisobutyltin-p-butylbenzenesulfonate became.

Example 9

Triisobutylzinnhydroxyd (3 _s 0 parts), Triisooctylphosphat (3J7 parts), nonionic surfactants polyethylene glycol ether (12.0 parts) and water (285.0 parts) were

009825/21 33

- 18 -

evenly mixed. A fabric made of polyethylene terephthalate is immersed in the mixture obtained, squeezed off to achieve an absorption of 10% and then dried in air. The fabric obtained has antistatic properties which are brought about by the triisobutyltin diisooctyl phosphate.

Example Io

Diammonium naphthalene-1,5-disulfonate (2 parts) is dissolved in water to produce a 1.9 $ strength aqueous solution, which is adjusted to a p "value of 8.5 with ammonia water. The aqueous solution is added to a mixture of bis (trioctyltin) oxide (3 parts) and nonionic surface-active polyethylene glycol ether (20 parts) and then made up to 500 parts with water. A polycapramide fabric is immersed in the mixture obtained at room temperature, squeezed off to achieve an absorption of 80% , dried in air at room temperature and then heated at 135 ° C. for 3 minutes. It is then washed with water, dried and then cured at 110 ⁰ C for 1 minute at room temperature and is obtained a woven fabric having anti-static properties, caused by the Trioetylzinnnaphthalin-l, 5-disulfonate.

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Example·!!

Diammonium naphthalene-1,5-disulfonate (2 parts) are dissolved in water to produce a 1.9% strength aqueous solution, which is adjusted to a p value of 8.5 with ammonia water. The aqueous solution is added to a mixture of bis (trioctyltin) oxide (3 parts) and methanol (100 parts) and vinyl acetate (12 parts) and methanol (600 parts) are gradually added. A fabric made of polyacrylonitrile is immersed in the mixture obtained at room temperature, squeezed off to achieve an absorption of ^ O% , dried in air and cured at 135 ° C. for 3 minutes. After washing with water, drying and heating at 110 ° C. for 1 minute, an antistatic fabric is obtained, the properties of which are brought about by the trioctyltin naphthalene-1,5-disulfonate .

Example 12

DiaHBnoniumnaphthalin-l, 5-disulfonate (2 parts) is dissolved in water to prepare a 1.9? Aqueous solution that is adjusted with ammonia water to a p ~ value of _H. 9 The aqueous solution is added to a mixture of trioctyltin acetate (3 parts) and nonionic boundary

- 2o 009825/213 3

Surface-active polyethylene glycol ether (12 parts) was added and then made up to 500 parts with water. A Polyethylene terephthalate fabric is immersed in the mixture obtained to achieve an absorption of 80% squeezed off, dried in air and heated to 135 ° C. for 3 minutes. After washing with water, drying and hardening at 110 ° C. for 1 minute, a fabric is obtained whose antistatic properties are due to the trioethyltin naphthalene-1,5-disulfonate be effected.

Example 13

Diammonium naphthalene-1,5-disulfonate (2 parts) are dissolved in V / water to produce a 1.9 $ aqueous solution, which is adjusted to a p ^ value of 9 with ammonia water. The aqueous solution is added to a mixture of trioctyltin acetate (3 parts), methanol (100 parts) and Hethoxynylon (methanol-soluble nylon) (12 parts), followed by the addition of methanol (600 parts). A fabric of polycapramide is immersed in the mixture, squeezed off to obtain a recording of kO%, dried, and cured in air for 3 minutes at 135 ⁰ C. After rinsing with water, drying and heating to 110 ° C. for 1 minute, an antistatic fabric is obtained, the antistatic properties of which are caused by the trioctyltin naphthalene-iS-aiov.ifonate.

009825/2133 ~ -. »

BATH ORIGINAL

example Ik

Methylammonium succinate (2 parts) and bis (trioctyltin) oxide (1 part) are emulsified in water (600 parts) with polyethylene glycol (molecular weight 220), oleyl ether (3 parts) and polyethylene glycol (molecular weight 2000) (3 parts). The emulsion obtained in this way is padded onto a fabric made of polyethylene terephthalate and the fabric is squeezed off to achieve an absorption of 70% and dried at 130 ° C. for 5 minutes. After rinsing with water, the fabric is dried and cured at 170 ° C. for 1 minute. The fabric obtained has excellent permanent antistatic properties against both laundry and dry cleaning.

Example 15

Polyethylene glycolyl monopalmitate (5 parts) and bis (trioctyltin) oxide (1 part) are dispersed in water (600 parts). The dispersion obtained is used for treating a fabric of polyethylene terephthalate instead of the emulsion used in Example 14.

009825/2133 " ²² "

Claims (1)

Claims Il organic tin compound of the general formula R ¹
A-O-Sn-R ² wherein A is a residue of a compound such as monoalkyl phosphate,
Dialkyl phosphate, monoalkyl phosphite, dialkyl phosphite _s alkanecarboxylic acid, alkanedicarboxylic acid, monoalkylalkanedicarboxylate, alkenedicarboxylic acid, monoalkylalkenedicarboxylate, arenecarboxylic acid, arendicarboxylic acid, monoalkylarenedicarboxylate, alkanesulfonic acid, sulfonatesulfonic acid, exclusively arenesulfonic acid of the alkylsulfonatesulfonic acid
Hydroxyl group thereof
Are aryl or aralkyl. 1 2
Hydroxy group thereof and R and R each alkyl, 2, process for the preparation of the organic tin compound according to claim 1, characterized in that a compound the general formula in which X is hydrogen, lower alkyl or ammonium
and A has the same meaning as above, with - 23 - 00982 5/2133 a compound of the general formula 2 -Sn -R in which Y is hydrogen, lower alkanoyl or a group of the general formula R ¹ 1 — Sn — R 1 ? represents and each R - and R * ~ group has the same meaning as above has implemented. 3 · The method according to claim 2, characterized in that the reaction is carried out on polymeric materials. k. A process for antistatic finishing polyrcerer materials gekennzeiahnest by ύ & Ά treating the materials with a polyneren lispersion oüer I / Jsun ^ the organic tin compound according to claim 1 in a suitable liquid Mediun. 009825/2133 BATH ORIGINAL 5. A process for the antistatic treatment of polymeric materials, characterized in that the polymeric Materials with a dispersion or solution of a compound of the general formula A-0-X wherein X is hydrogen, lower alkyl or ammonium and A has the same meaning as above and a compound the general formula R ¹ f 2
Y-0-Sn-R wherein Y is hydrogen, lower alkanoyl or a group of the general formula R ¹ I 2
—Sn — IT 1 2
is and every h - and R group has the same meaning as above on '. ·; ·: .is, treated in a suitable liquid medium and the polymeric materials dried to cause the mentioned compounds to react, thereby forming the organic tin compound according to Claim 1 is made. 009825/2133. _ ~ ²⁵ BATH ORIGINAL 6. Polymeric materials on which the organic Tin compound according to claim 1 is firmly fixed to cause antistatic properties thereon. 009825/2133