DE903631C - Softening and gelatinizing agents - Google Patents

Description

(WiGBl. P. 175)

ISSUED FEBRUARY 8, 1954

F 3782 IVc j 39b

(Ges. V. 15, 7. 51)

It is known that amides of aromatic sulfonic acids, such as. B. p-toluenesulfamide, as Plasticizers can be used.

It has now been found that in the series of water-insoluble amides of aliphatic sulfonic acids Number of representatives is present, the said amides of aromatic sulfonic acids in their Effectiveness as a plasticizer is far superior, and in part as a high-quality gelatinizing agent are to be addressed. The compounds have the general formula

R ₁ -SO ₂ -N:

'R,

where R _{1 is} an aliphatic or cycloaliphatic radical with a maximum of 8 carbon atoms, R _{2 is} an aliphatic, cycloaliphatic, aromatic or araliphatic radical, R _{8 is} hydrogen, an aliphatic, cycloaliphatic, araliphatic or ao aromatic radical, and R ₁ , R ₂ and R ₃ together contain no more than 20 carbon atoms.

For example, the following sulfamides are mentioned:

n-butanesulfonyl-n-octylamide,

n-octanesulfonyl-methylamide,

n-octanesulfonyl-dimethylamide,

n-propanesulfonyl anilide,

isopropanesulfonyl anilide,

n-propanesulfonyl-o-toluidide,
iso-propanesulfonyl-p-toluidide,
n-propanesulfonyl-ethylanilide,
n-butanesulfonyl-methylanilide,
n-butanesulfonyl-benzylamide,

n-octanesulfonyl anilide,
Ethylsulfonyl-diisobutylamide,
n-propanesulfonyl-di-n-butylamide,
Cyclonexanesulfonyl diethylamide,
ίο n-propanesulfonyl-p-chloroanilide,

n-Butylsulfonyl-cyclohexyl-isopropanesulfonyl-p-phenetidide.

Amides which are obtained by using aliphatic or cycloaliphatic compounds are particularly advantageous Hydrocarbons with 2 to 8 carbon atoms exposed to sulfur dioxide and chlorine are useful under irradiation with photoactive light, subjects and the obtained as sulfochlorides to be addressed products with suitable amines to amides.

The compounds identified above have one Surprisingly wide field of application, since it is used for a wide variety of synthetic polymerization products Show gelatinizing ability, while those mentioned above, known as plasticizers Amides of aromatic sulfonic acids can only be used to a limited extent, e.g. B. the p-toluenesulfamide only for acetone soluble acetyl cellulose.

In particular, it has been found that they can be used to soften emulsion polymers of vinyl compounds are eminently suitable, as they are inherently hydrophilic fins or spreads from such Give emulsions increased water resistance.

This effect is quite surprising because, for example Tricresyl phosphate, which is also water-insoluble, in connection with such emulsions not nearly as waterproof films. One advantage of the products is their low volatility.

If the plasticizers are heated to 90 ° for 11 days in open glass dishes with renewed air, one finds Weight loss between 0.5 and 1.5%

The products have gelatinizing properties for the following film formers, for example:

Polystyrenes, polyvinyl chlorides, polyvinyl alcohols including their acetals, polyvinyl acetates, polyvinyl ethers, Polyacrylic acid derivatives including numerous copolymers. It is also possible that claimed plasticizers in combination with already known plasticizers, e.g. B. tricresyl phosphate or phthalic acid or adipic acid esters

Claims (2)

PATENT CLAIM: Turn R1-SO2-N. The plasticizing of cellulose derivatives does not come under the subject of this invention. Examples 1. 100 parts of an aqueous polyvinyl acetate emulsion with a dry matter content of 50% are mixed with 25 parts of a mixture of approximately the same Parts of n- and iso-propanesulfanilide, dissolved in 5 parts Alcohol, intimately mixed in a high speed mixer. The emulsion is used to produce leather substitutes from ground leather waste. In the same way, instead of propanesulfanilide, you can use the corresponding one Use o-toluidide. 2. 100 parts of a polyvinyl isobutyraldehydacetals, which still contains about 40 ° / ₀ of the originally present in the polyvinyl alcohol hydroxyl groups is mixed in the moist state with 100 parts Butansulfanilid in a kneading machine. The crumbly mass is drawn down to a warmed to 6o ° roll to rinds and then pulled out in an extruder, the head of which is heated to 120 to 130 to ⁰ hoses. The hoses are soft and rubber-like elastic. For example, they can be used as gas hoses. The butanesulfanilide was obtained from η-butane by treatment with sulfur dioxide and chlorine and subsequent reaction of the sulfochloride formed with aniline. Use of water-insoluble sulfamides of the general formula ., R ₂ where R _{1 is} an aliphatic or cycloaliphatic radical with a maximum of 8 carbon atoms, R _{2 is} an aliphatic, cycloaliphatic, aromatic or araliphatic radical, R _{3 is} hydrogen, an aliphatic, cycloaliphatic, araliphatic or aromatic radical, and R ₁ , R ₂ and R ₃ together contain no more than 20 carbon atoms, as a plasticizer for synthetic high polymers. Cited publications: German Patent No. 657 467; French Patent No. 844709; U.S. Patent Nos. 3,138,934, 2,214,405. O 3740 1.54