Patent GB-976394-A (GB)
Title: Photographic silver halide emulsions of increased sensitivity
IPC: G03C1/043
Filed: 1960-11-09
Abstract: Poly (oxyethylene) sorbitan monolaurate tris (methane sulphonate) is prepared by adding methane sulphonyl chloride to a dried solution of poly (oxyethylene) sorbitan monolaurate in pyridine.  A similar product is prepared from poly (oxyethylene) sorbitan monostearate. By heating the monostearate formed with 5-ethyl-2-methylpyridine, poly (oxyethylene) sorbitan monostearate tris (2-methyl-5-ethylpyridinium methane sulphonate is obtained. Similarly, the monostearate is heated with pyridine and the monolaurate is heated with pyridine, triethylamine or dimethylaminomethanol to give quaternary ammonium salts.  Sucrose octakis-[2-methylethyl poly (oxyethylene) methane sulphonate] is prepared by bubbling ethylene oxide into a heated mixture of octakis (2-hydroxypropyl) sucrose and a boron-tri-fluoride-etherate catalyst. The product is dissolved in pyridine and reacted with methane sulphonyl chloride.  By heating the product with dry pyridine, sucrose octakis-[2-methylethyl-poly (oxyethylene) pyridinium methane sulphonate] is obtained. Similarly, the product may be heated with triethylamine to give a quaternary ammonium compound.  Sucrose octakis-[2-methylethyl-poly (oxyethylene)-oxy-2-hydroxy-propyl-3-pyridinium perchlorate] is prepared by reacting sucrose octakis-[2-methylethoxy-polyethoxy-ethyl alcohol] with epichlorohydrin in the presence of a boron tri-fluoride catalyst, and then refluxing the product with pyridine.  The pyridinium salt produced is converted into the perchlorate by treatment with sodium perchlorate in acetone.  Specifications 541,589 and 791,219 are referred to.ALSO:Poly(oxyethylene) sorbitan monolaurate tris (methane sulphonate) is prepared by adding methane sulphonyl chloride to a dried solution of polyoxyethylene) sorbitan monolaurate in pyridine.  A similar product is prepared from poly(oxyethylene) sorbitan monostearate.  By heating the monostearate formed with 5-ethyl-2-methylpyridine, poly(oxyethylene) sorbitan monostearate tris (2-methyl -5- ethyl pyridinium methane sulphonate) is obtained. Similarly, the monostearate is heated with pyridine and the monolaurate is heated with pyridine, triethylamine, or dimethylaminomethanol to give quaternary ammonium salts.  Sucrose octakis-[2-methylethyl poly(oxyethylene) methane sulphonate] is prepared by bubbling ethylene oxide into a heated mixture of octakis (2-hydroxypropyl) sucrose and a boron-trifluoride-etherate catalyst until a total of 30 or 70 molar equivalents of ethylene oxide have reacted. The product in each case is dissolved in pyridine and reacted with methane sulphonyl chloride. By heating the product with dry pyridine, sucrose octakis-[2-methylethyl-poly(oxyethylene) pyridinium methane sulphonate] is obtained. Similarly, the product may be heated with triethylamine to give a quaternary ammonium compound.  Sucrose octakis-[2-methylethyl-poly (oxyethylene)-oxy -2- hydroxy-propyl -3- pyridinium perchlorate] wherein the oxyethylene groups in each molecule have a total molecular weight of 1,320 or 3,080, is prepared by reacting the appropriate sucrose octakis-[2-methylethoxypoly (ethoxy) ethyl alcohol] with epichlorohydrin in the presence of a boron trifluoride catalyst, and then refluxing the product with pyridine. The pyridinium salt produced is converted into the perchlorate by treatment with sodium perchlorate in acetone.  Specifications 541,589 and 791,219 are referred to.