CHEMICALS whiten! brighten!
N o w in c o m m e r c i a l production, c o m p o u n d offers e n t i r e l y n e w m e t h o d of preparing 4-substitutea pyridines
YOUR
overprint coatings ADD BRILLIANCE £ BRING OUT COLOR RICHNESS OF LABELS, BOOKCOVERS, FINE PRINTING, CARTONS, & DISPLAYS!
Clear overprint varnishes a n d lacquers a r e lightened a n d re lieved of yellowish casts by a d d ing M . D . A . C . t o t h e plastics, resins, a n d c o m b i n a t i o n s of these solids used in t h e systems. M . D . A . C . provides crystal clear coatings t h a t i m p a r t a high gloss. T h e glistening effect of t h e M . D . A . C . gives d e p t h a n d rich ness of t o n e t o color printing where whites a n d light areas a p p e a r whiter a n d colors m o r e vivid. E x t r e m e l y thin coatings applied b y rolling or s p r a y i n g a r e given added a t t r a c t i v e n e s s b y M . D . A . C . Coatings t r e a t e d with M . D . A . C . a r e effective o n label papers, c o a t e d papers, cover stock, car t o n stock, foils, a n d clear plastic films. Easily incorporated into m o s t varnish o r lacquer systems, M . D . A . C . has good solubility in all well k n o w n organic solvents. M . D . A . C . is economical t o use a n d is frequently effective in a m o u n t s of 0 . 0 0 1 % t o 0 . 0 5 % . T r y M . D . A . C . in your overprint c o a t i n g u n d e r y o u r o w n labora t o r y conditions—write for your sample now! CARLISLE FLUORESCENT COMPOUNDS OF DIFFERENT TYPES: • BETA METHYL UMBELUFERONE • COUMASOL • LUMISOL
Carlisle CHEMICAL WORKS, INC READING,
OHIO
manufacturers of f i n e i n d u s t r i a l chemicals
33O0
Pyridine-N-Oxide
A LTHOUGH it is still too early to pre-
-**-dict the full impact that pyridine-Noxide will have on making pyridine derivatives, its manufacture in com mercial quantities by Reilly Tar & Chemical calls for a new look into ex isting processes. Main· pyridine chem ists are already using t h e compound, first made in 1926, as an important intermediate in the preparation of electrophilically substituted pyridines. Ac cording to F . E. Cislak, research and development director at Reilly, some changes in the syntheses of pyridine derivatives are in the offing. The outstanding characteristic of pyridine is its inertness. It is brominated, nitrated, or sulfonated only with great difficulty. T h e reason is that the nitrogen atom in pyridine lowers the availability of electrons at all points in t h e pyridine ring, making pyridine re sistant to electrophilic attack. Convert i n g pyridine to'its N-oxide results in a redistribution of electron density. The result is that pyridine-TV-oxide readily reacts with electrophilic reagents.
I ο In 100% sulfuric acid with a mixture of potassium and sodium nitrate, and a t temperatures varying between 300° a n d 450° C , pyridine gives only a 6 % yield of 2-nitro- a n d 3-nitropyridine. In contrast, pyridine-N-oxide, w h e n nitrated with a mixture of fuming nitric acid and concentrated sulfuric acid at a temperature of 90° C , gives a 90 to 95% yield of 4-nitropyridine-ZVoxide. 4-Nitropyridine-IV-oxide is a good intermediate for the synthesis of pyri dine compounds. T h e ease and simplic ity of its preparation also enhance its usefulness. T h e elusive 4-aminopyridine is obtained in good yields b y re ducing 4-nitropyridine-2V-oxide. Heat i n g a solution of 4-nitropyridine-2Voxide with concentrated aqueous hydro chloric acid gives 4-chloropyridine-2Voxide; this is readily converted to 4chloropyridine. A mixture of 2-chloropyridine and 4-chloropyridine is also obtained by re acting sulfuryl chloride with pyridine2V-oxide. A modification of the reaction results in 2,4-dichloropyridine.
2-Hydroxypyridine and 4-hydroxypyridine may also b e made from pyridine-IV-oxide. Effect of the A/-oxide grouping is observed in 2-picoline-ZV-oxide, 3-picoline-iV-oxide, a n d in 2,6-lutidine-Noxide. Nitration of each of these com pounds results in a good yield of t h e 4-nitro- derivative. A. methyl-substituted pyridine-Noxide, 4-picoline-iV-oxide, is a good starting point for the preparation of 4-pvridylmethanol, while 2-picoline-Noxide may b e used for t h e synthesis of 2-pyTidylmethanol. However, 4-picoline-iV-oxide resists nitration to a greater extent than does pyridine. The N-oxide group of pyridine-Noxide is easily deoxidized; usefulness of the compound as a starting compound for the synthesis of pyridine compounds is thereby increased. T h e oxygen m a y he removed by catalytic reductive oxi dation; by treatment with phosphorus trichloride; or b v treatment with silver. CS Ϊ
• C I 4 -tagged a m i n o acids offered by Bio-Rad come in 1-millicurie standard packages. Compounds are: DL-norleucine-2-C14, DL-norvaline-1-C 14 , and DLnorvaline-2-C 14 . Latter two compounds, with specific labels in two different positions, are expected to be useful in studies involving t h e mechanism of amino acid metabolism. CS 2 M p o x y c o a t i n g , called Nepoxide, offered by Atlas Mineral Products, cures at room temperature. Company says coating has excellent adhesion and re sistance to a wide variety of chemicals. CS 3
• Self-emulsifying w a x traditionally kntrwn in England a n d continental Europe as Lanette W a x is being made in U. S. by Aceto Chemical. This cream and ointment base will b e offered under Aceto's brand name of Ceramol. CS4
• Well cleaning compound offered by Calgon was developed in response to need for a package well cleaning prep aration that could d o complete job of well cleaning. Called Weltone, prod uct contains Calgon, a water condi tioning agent, plus a disinfecting agent, a wetting agent for better penetration, and other chemicals. New product
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P R O G R E S S THRU RESEARCH
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a t GENERAL Ml LLS
N o n - V o l a t i l e Resin M a k e s Strong Glass Fiber
Laminate
lirfr Fatty Acids Improve A l k y d Color 'Anfir Fatty Nitrogens for Textiles yellowing enamels and varnishes with water-white properties. Because of their excellent color stability and rapid baking qualities, Aliphats 16-A and 16-BW aire also suitable for alkyd resins used as plasticizers in air-drying la-cquers and enamels, and in baked finishes in conjunction with urea or melamine resins. Typical composition of Aliphat 16-A is 55 per cent linoleic a « d (91 percent oleic and linoleic) sand of Aliphat 16-BW, 56 per cent linoleic acid (88 per cent oleic and limoleic). If you would like more ir*forrnation on General Mills fatty acids, please mail the coupon below. A smashing b l o w w i t h a h e a v y s l e d g e h a m m e r fails to d a m a g e impact-resistant, glass reinforced l a m i n a t e s m a d e w i t h a new b l e n d of P o l y a m i d e a n d e p o x y resins.
Producers of glass laminates appreciate the new Polyamide-epoxy resin blends because they show physical properties superior to other thermosetting materials. These new resin blends have a natural affinity for glass, in either sheet or fiber form. This affinity helps wet the glass quickly and thoroughly, leading to fewer voids and a better bond of resin to glass. Their water resistance, too, is important to makers of glass reinforced plastic pipe or surface coatings for laboratory furniture and equipment. Polyamide-epoxy resin blends are resistant to alkali and to a wide range of corrosive chemicals and solvents. Laboratory test results have shown greatly superior impact strength, especially for the Polyamide Resin 115-epoxy resin blends. Polyamide Resins are non-volatile and have no unpleasant odor. Also, over a year of experimental work has been carried on with no toxic effects to personnel. Tests show that Polyamide Resin is practically unextractable by water or lard oil. The low shrinkage of Polyamideepoxy resin blends permits close conformation to the mold, with less tendency to crack during the curing cycle. Low exotherm and low shrinkage are properties which promise a bright future for Polyamide-epoxy
blends in the potting and casting* and in the tool and die fields . . . especially automotive and aircraft. For added information, mail the coupon below. Did You Ever Notice that the subdued-light side of a white-painted object is often yellower than the exposed side? The action of linolenic acids in the alkyds causes this yellowing. Such discoloring does not happen with alkyds made from General Mills Aliphats (fatty acids) 16-A and 16-BW. Each is a fractionally distilled and refined combination of oleic and linoleic acids, with no linolenic acids present. This feature, and the high unsaturated acid content, makes these fatty acids excellent raw materials for p r o d u c i n g g l y c e r o l phthalate resins for superior non-
Fatty Nitrogen Compounds Ibecame an even larger part of the General Mills chemical picture recently with the commercial introduction, of two new fatty nitrogens—General Mills Alitrile 7 JD and Alamide H 2 6 . Alitrile 7 D (distilled ste=aro-nitrile) and Alamide H 26 (hydrogenated tallow amide) are aïhemical intermediates in making textile finishes which impart durable waterrepellency to articles such SLS hats, raincoats and play clothes. They also afford certain antistatic, wrinkle resistant properties; help improve the "hand" of the cloth. Durable water repellents derived from Alamide H 26 work exceptionally well on cottons and rayons. The excellent color and color stability of Alamide H 26 carry over into the textile finish. For more information about General Mills fatty nitrogen compounds, just mail the coupon below.
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CHEMICAL DIVISION KANKAKEE, IUIÎNOIS
Please s e n d m e a d d i t i o n a l technical i n f o r m a t i o n for the p r o d u c t s checlced below. Π Polyamide Resin 1 1 5 (for use with e p o x y resins) D Aliphat 16-A D Aliphat 16-BW D Alitrile 7 Ό G Alamide H 2 6 Name.. , — _ Firm-
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CHEMICALS, eliminates necessity for well driller or owner to purchase and assemble r e quired chemicals from different sources. Company says Weltone retains all the well cleaning properties of Calgon; it is also an effective sterilizing or disinfecting agent. Weltone does not h a r m metals or concrete and can b e used in concrete c a s e d . wells with p u m p in place. It does not generate any dangerous fumes. CS 5 • Flame r e s i s t a n t a g e n t , called N y lon-No-Glow, is durable to washing. Developed b y Chemical Products, com-
pound, w h e n used with company's amine-aldehyde synthetic resin, r e t a r d s complete combustion and imparts distinct flame resistant character, says company. It is adaptable over a w i d e p H range and is compatible with nearly all resins and finishing compounds. CS 6
• Ultron vinyl s h e e t r e c o m m e n d e d for advertising specialties, displays, decorations, and calendar cards is offered b y Monsanto's plastics division. Formulation is designated as Ultron R 309, and company says it has good light stability,
high h e a t distortion point, and that indications point tô a very low static charge. Material is offered in various gages in either a m a t t e finish, o p a q u e white, or i n calendered translucent white. CS 7 • Phenylfluorone is offered by Jasonols Chemical as a very sensitive and selective reagent for the determination of germanium. CS 8 • Pigments for thermoplastic resins are offered by R h o d e Island Laboratories, These Violite pigments are of t h e phosphorescent t y p e . CS 9 • Two h i g h e r alcohol p h t h a l a t e p l a s ticizers for vinyl chloride resins a r e offered b y C a r b i d e a n d Carbon Chemicals in tank car quantities. Known as Flexol plasticizers 8 1 0 a n d 812, compounds are derived from distinctly different higher alcohols. Both a r e completely compatible with vinyl chloride resins, and c o m p a n y says t h e y are outstanding for r e d u c e d volatility, improved low t e m p e r a t u r e properties, and excellent electrical properties. T h e y are light-colored and chemically stable. In vinyl plastics they exhibit excellent h e a t and light stability, freedom from odor, resistance to extraction: by water, a n d good resistance to "ruboff" from upholstery sheeting. CS 10 For further information on items mentioned here, see coupon on page 3308
Who Makes If? T h e National Registry of Rare Chemicals, Armour Research Foundation, Illinois Institute of Technology, 35 West 3 3 r d St., Chicago, 111., is interested in locating sources of supply for the following chemicals: Potassium thioplatinate Dilauryl selenide Tetraphenylgermanium Zinc nydride Potassium monoxide Truxillic acid 3,3,3-Trichloropropene 1,2,3-Butanetriol Tri ( p-nitrophenyl ) carbinol 2,3,5,6-Tetramethylbenzoic acid Succindialdehyde Piperidine-4-acetic acid 4-Nitrohydrindene 2,4-Dichlorobenzyl alcohol IV-Laurylpiperidine Chroman~5,6-quinone Phthalazone Scyllitol Cymarin -y-Tocopherol 3302
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