Other Compounds 



Experiment 1 . Poly(vinylmethyl ether /maleic anhydride) (1 g.) was 

 dissolved in 2-butanone (9 g.) and ethylene glycol (0.4 g.) was added 

 and stirred in. A quantity of this solution was poured into a Petri 

 dish, carefully evaporated to dryness, and heated under an infrared lamp 

 at 140° for 15 minutes. The thin friable film which was produced 

 resisted water at ambient temperature, but broke up in boiling water. 



Similar results were obtained when ethylene glycol (0.4 g.) was 

 mixed with 10 g. of a ten percent aqueous solution of poly(vinylmethyl 

 ether /maleic anhydride) . 



Experiment 2 . Poly(vinylmethyl ether/maleic anhydride) (20 g.) 

 was dissolved in hot (90-96°) water. 2-Butyne-l,4-diol (11 g.), 

 N-vinylpyrrolidone (7 g.) and benzoyl peroxide (0.9 g.) were added and 

 the mixture was stirred vigorously. Heating a sample of this material 

 on a Teflon^^ sheet at 160 for ten minutes with an infrared lamp yielded 

 a dark brown, water-soluble solid. 



Experiment 3 . To 20 g. of a ten percent aqueous solution of 

 poly(vinylmethyl ether/maleic anhydride) were added 1.1 g. of 2-butene- 

 1,4-diol, 0.7 g. N-vinylpyrrolidone and 0.1 g. of cx,oi'-azodiisobutyro- 

 nitrile. After stirring, a portion of the resulting mixture was poured 

 into a Petri dish, evaporated to dryness, and heated to 140 for 

 approximately 30 minutes under a heat lamp. The dark brown, friable 

 film which was produced was resistant to cold and boiling water. 



Experiment 4 . A two percent aqueous solution of sodium carboxjnnethyl 

 celluose (10 g.) and a ten percent aqueous solution of poly (vlnylme thy 1 

 ether/maleic anhydride) were mixed. A disc of filter paper was dipped 

 into the resulting solution, dried, and then heated at 150 for ten 

 minutes under an infrared heat lamp. The paper was placed in boiling 

 water for 15 minutes. The film remained in the paper, but was not 

 impervious to water. 



Experiment 5 . Succinic acid (0.1 g.) was added to a copoljnner of 

 vinylpyrrolidone and ethyl aery late (20 g.) and stirred. A sample was 

 poured on a Teflon^ sheet, warmed with an infrared heat lamp to drive 

 off moisture, then heated at 140° for 45 minutes. The film which 

 formed was softened by but not dissolved by boiling water or by cold 

 water. 



Experiment 6 . Dimethylol urea (120 g.) was mixed with formalin 

 solution (110 g., 36.6%), butanol (30 ml.) and 28 percent sodium hydrox- 

 ide solution (6 ml.) in a 1 1. round-bottomed flask and refluxed for 45 

 minutes. Urea (9 g.) was added and refluxing was continued for an addi- 

 tional 45 minutes, after which butanol (100 ml.) was added and the solu- 

 tion was refluxed for 20 minutes. Oxalic acid solution (6 ml., 6.15%) 



