DE1595679C3 - - Google Patents

Description

4-methacryloylamino-pheny-sulfazide

100 parts of 4-aminobenzenesulfonic acid azide are dissolved in 300 parts by volume of chloroform to which 0.5 part of hydroquinone is added. This solution is covered with a layer of a solution of 42 parts of sodium hydrogen carbonate in 450 parts of water. While stirring, 60 parts of methacrylic acid chloride are added dropwise at 0 to 5 ° C. over the course of 2 hours. After 16 hours stirring, the Chlorolösung is separated, the chloroform is distilled off at a maximum bath temperature of 3O ⁰ C, and the oily distillation residue (130 parts) in. 150 parts by volume of alcohol dissolved. When standing in the refrigerator, 85 parts of 4-methacryloyl-15 aminophenyl sulfazide crystallize from the alcoholic solution, corresponding to 64% of theory. After crystallization from benzene, this compound melts at 95 ° C.

Example 1 ^a °

2 parts of 4-methacryloylaminophenyl sulfazide are dissolved in a mixture of toluene and n-butanol in a ratio of 200: 400. At 75 ° C., 100 parts of methyl methacrylate are added to the reaction mixture. The polymerization is then initiated by adding 0.8 part of azodisis-butyronitrile (ADBN) and completed for a further 3 hours by adding a further 0.5 part of ADBN. The polymerization is complete after 6 hours. The reaction mixture is cooled, poured into about 1000 parts of methanol and the deposited precipitate is filtered off. Polymethyl methacrylate containing sulfazide groups is obtained in a yield of 71 percent by weight, as can be seen from a band in the ultra spectrum at 2.125 to 2.130 cm " ¹ .

Example 2

3000 parts by weight of water, 12 parts by weight of sodium lauroyl sulfate and 500 parts by weight of butadiene are emulsified in an autoclave. The atmospheric oxygen is displaced by nitrogen and a mixture of 5 parts by weight of dodecyl mercaptan, 350 parts by weight of ethyl acrylate and 50 g of 4-methacryloylamino-phenylsulfazide and 10 parts by weight of azodiisobutyrolonitrile is introduced into the emulsion at room temperature. It then adjusts a temperature of 7O ⁰ C and follows the course of the polymerization. The reaction is terminated at a conversion of 65%. After degassing, a latex is obtained from which the polymer can be precipitated by adding methyl alcohol. The polymer is a; in '. Benzene soluble rubber. After conversion into a film and subsequent exposure, an elastic, insoluble film is obtained.

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Claims (1)

1 2 a
are: Acrylic and methacrylic compounds such as B. Claim: acrylic acid, acrylic acid ester, acrylamide, acrylonitrile, the corresponding methacrylic compounds as well Process for the preparation of with ultraviolet styrene, alkyl styrenes, vinyl chloride, vinyl esters such as Light-crosslinkable polymers, thus 5 vinyl acetate and vinyl propionate and conjugated diols characterized in that one organic Verfine, preferably with 4 to 8 carbon atoms such as bonds containing a polymerizable ethylenic butadiene, isoprene and chlorobutadiene, Unsaturated double bond and a sulfazide The polymerization can be in solution, dispersion or group, optionally carried out in the presence of an emulsion. As a solvent or Another suitable uhgeio dispersant copolymerizable therewith are water, aliphatic aliphatic saturated compound, in the presence of a radical alcohol or ketone, and also the esters of aliphatic calcium-forming catalyst at temperatures of alcohols and carboxylic acids, also hydrocarbons -20 to + 150 ⁰ C polymerized. substances such as B. toluene or solvents such as Dimethylformamide or dimethyl sulfoxide. Preferred : - 15 is water. The polymerizations are carried out 150 ⁰ C at temperatures from -20 to +. Below -20 ° C Polymers which contain azide groups, the reaction proceeds too slowly and can be crosslinked above due to the action of light. Are c to _{+ 50} ° _l SuIfazidgruppen no longer stable. In general, the energy of daylight is sufficient. _ao preferably is, temperatures from -15 to Polymers were 12O ⁰ C to using +. Azide group-containing monomers z. B. Azido _The initiation of the polymerization takes place through styrene, vinyl azidobenzoic acid and vinyl azidophthalic radical-forming compounds, such as peroxidic acid esters. The polymers obtained in this way are compounds or aliphatic azo compounds. Than have crucial shortcomings. One hand, the azide 35 peroxidic compounds are for example very Pergruppe hydrqlyseempfindlich so that the unen- _{oxyde w} j _e H ₂ O ,, Benzolperoxyd, Laurylperoxyd or crosslinked, that is called the exclusion of moisture manufactured cumene hydroperoxide. An example of an aliphatic azo compound which cannot be used as a polymer or which can only be used with a special initiator is precautionary measures that can be stored, ande-azodiisobutyronitrile. On the other hand, the networking is already through daylight _3o Of course it is possible to increase the effectiveness triggered. One must, therefore, the work-up and encryption _e j _nes peroxidic initiator by the addition of Re Formation of the uncrosslinked polymers under light-reducing agents such as ascorbic acid, reducing agents exclusion and exclusion of water from sulfur compounds or heavy metal ions to take. improve. The subject of the invention is a process for _{35 D} j _e polymerization itself can also with addition Preparation of crosslinkable with ultraviolet light _of emulsifiers or dispersing agents in aqueous Polymer which is characterized in that dispersion or emulsion are carried out. To the one organic compounds that polymerize- Achievement of special polymers, it is possible bare ethylenically unsaturated double bond and one by adding regulators such as dodecyl mercaptan, Contain sulfazide group, optionally in the presence of ₄₀ to control the polymerization. is called a further interpolymerizable therewith in _{order to achieve the} most favorable crosslinking effect possible saturated compound, in the presence of a free radical _to len _{erz e} j, in the copolymers should the SuIf- forming catalyst at temperatures from ^ -20 to azide-containing monomers to at least + 150 C polymerized. 0.5 percent by weight bound be included. To the Not to alter the obtainable by the process of the invention ₄₅ substance properties, it is often Products are polymers crosslinkable with UV light, attached, a certain amount of crosslinker, im which are stable to hydrolysis in the uncrosslinked state and generally do not exceed 15 percent by weight, which are not networked with daylight. This means that particularly good results are achieved when the Given their shelf life, and the work-up and said comonomers in about an amount of Deformation can occur in daylight. ₅₀ o, 75 to 10 percent by weight can be used. Compounds which contain an ethylenically unsaturated one, as already stated, are the poly-double bonds obtained and contain a sulfazide group, merisate which can be crosslinked with ultraviolet light. The products suitable for carrying out the process are mostly thermoplastic or elastic, for example vinyl, vinylidene and styryl plastics. It is possible to localize on articles made from compounds containing a sulfazide group in molecule _{55 of} these materials. Specific examples are: styrene sulfazide, to make crosslinks. For example, in the case of p-methacryloylaminobenzene sulfazide and reaction irradiation with UV light, the surface of molded products of 3-sulfazidophenyl isocyanate with hydrocarbons is changed so that they become _{stable against solvents containing xyl groups or amino groups and vinyl and} fats. This is of particular or vinylidene monomers, such as. B. the implementation value in the production of films for packaging product of isocyanato-phenylsulfazids with hydroxyl _of food. It is also possible to use the elastic propyl acrylate or hydroxypropyl methacrylate or properties at certain points of a molded body reaction product of 3-sulfazide isocyanate with z. B. to change pers.
2-aminoethyl methacrylate. The parts given are parts by weight, provided With these compounds copolymerizable 65 not otherwise noted. Monomers are, for example, vinyl, vinylidene and rj _{as a} ls starting material in Examples 1 and 2, the styryl compounds, which polymerize alkynes _nen d _e sulfonic acid azide-containing comono- can be. Examples of such compounds _mere is made as follows: