T E C H N O L O G Y

Beta Amines No Longer "Curiosities" Now offered in development quantities, the liquid amines can be made economically by new Armour process

A new series of amines is now being offered in development quantities by Armour Industrial Chemical Co. (Chi­cago, 111.). They are n-alkyl-beta-amines, compounds in which the amino group is attached to the beta carbon of the straight chain.

Beta amines are liquids and, in many cases, they have better proper­ties than do the conventional solid n-alkyl-alpha-amines which Armour of­fers. Also beta amines should cost less than do most of the alpha amines. For these reasons, they should find wide use in such areas as cosmetics, elastomers, metalworking, mining, paints, petroleum, plastics, and tex­tiles, according to Karl M. Bierman, director of marketing at Armour.

For many years beta amines have been simply laboratory curiosities. But now, with a new process devel­oped by Armour, they can be prepared economically in commercial quanti­ties, according to Mr. Bierman. Ar­mour however, isn't disclosing any details about its new process; it has applied for patents.

Armour is now producing beta amines in pilot-plant facilities at Mc-Cook, 111. Plans for a full-scale plant haven't been made final yet.

Initially Armour is producing and marketing six beta amines—four pri­mary amines and two diamines. The company is designating its primary beta amines as Armeen L-7, L-9, L - l l , and L-15 (the numbers indi­cate the bottom of the range of chain lengths). Duomeen L - l l and L-15 are the two beta diamines. Development prices for these com­pounds haven't been established yet.

Low Melting. Armour's new amines function as cationic surface-active agents. They are saturated and range in chain length from 7 to 20 carbon atoms. The most significant physical properties of the compounds are their melting points and solubili­ties. Beta amines melt at very low temperatures. All of them, except the amine and the diamine with the

longer chains, stay liquid below 0° F. In contrast, n-alkyl-alpha-amines are solids at these tempera­tures.

Derivatives which are also liquids can be prepared from beta amines. Examples are water-soluble salts, such as acetates, and oil-soluble salts, such as oleates. Acetates are used as flo­tation agents; oleates find application as corrosion inhibitors and pigment-wetting agents.

The fact that these amines and their salts are liquids gives them a big advantage over other amines, ac­cording to Paul L. DuBrow, manager of market development at Armour. As liquids they are easier to trans­port, store, and use.

Beta amines are very soluble in a variety of organic solvents. This means they will stay in solution at high concentrations. Also they won't separate out so readily at subzero temperatures.

The new compounds should move

into applications now dominated by highly branched fatty amines. Beta amines have many properties of the branched fatty amines, are more bio­degradable, and are more reactive as chemical intermediates.

Beta amines differ in their behavior from alpha amines. Thus beta amines will open up new uses for amines, Mr. DuBrow believes.

Lower Cost. Costs of the beta amines when in commercial produc­tion will be generally lower than those of the alpha amines, particularly for the shorter-chain-beta amines. Price range of the alpha amines is 35 to 75 cents per pound. Although a C15 beta amine will cost about the same as its alpha amine counterpart, C7 to C9

beta amines will be priced 10 to 20 cents less than are the alpha amines. The reason for this, Mr. Bierman ex­plains, is that costs for the beta com­pounds fall in a narrower range for all chain lengths, short and long, than they do for the alpha amines. C 30

Mew beta amines, such as Armeen L-7 primary beta amine...

($<§ f f § f f

. . . and Duomeen L-11 beta diamine...

y u y & u u :M' « t "* r ' V if ,'*;

i i i i i i Y : * ; ;H; H H H « ' #

• . . show promise for use in mining, paints, petroleum, cosmetics, metalworking, plastics, rubber, and textiles

40 C & E N J A N . 11, 1965

Electrostatic Flocking Makes Gains Growing popularity of carpet-making technique could mean bigger markets for man-made fibers

With the introduction of a new car­peting last week electrostatic flocking got a stimulus that may push the process into high-volume use. This augurs well for producers of man-made fibers.

By electrostatic flocking, textile fi­bers are imbedded into adhesive-coated substrates to make a fur-like surface. Hence this is a way to make carpets, upholstery, and linings for garments.

Last week's spark came from Bar-wick Mills, of Chamblee, Ga. The firm will make 15-ft.-wide flocked ny­lon carpets; before, electrostatic flock­ing methods generally limited carpet widths to 6 ft. Barwick's carpet is made from 45-denier nylon 4.5 mm. long and imbedded into the backing at a density of roughly 175,000 fibers per square inch.

Electrostatically flocked products are also produced by J. P. Stevens, Deering Milliken, and Callaway Mills, among others. The technique seems destined to gain in popularity in the foreseeable future.

One probability is carpets for auto­

mobiles. Several carpet makers now are working with the technique to produce nylon, nylon-rayon combina­tions, and polypropylene carpets for this market. The hope here is that carpets so produced can replace tufted carpets used now in most cars. Last year, some flocked nylon carpets were produced for Volkswagen auto­mobiles by Callaway Mills. In Eng­land, British Motor Corp., Ltd., is using electrostatically flocked carpets which have a polyvinyl chloride back­ing and both acrylic and rayon fibers.

The potential for fiber in automo­tive carpets produced by this method runs from 12 to 15 million pounds per year. Last year only 12 million pounds of flocked fibers were con­sumed in the United States and these include both mechanically and elec­trostatically produced materials. Cot­ton flock amounted to about 60% and rayon 25%. Nylon and polyester were most of the balance.

Process. Electrostatic flocking is particularly applicable to making items such as carpets and upholstery, where high density and vertical orien-

FLOCKING. A 30-denier Chemstrand nylon flock falls from a hopper and is oriented by an electrostatic field be­tween a grid and a plate beneath ad­hesive-coated substrate. The horizon­tal bar is part of the charged grid '

tation of fibers are required. An electrostatic field guides and propels charged fiber from a hopper into an adhesive-coated substrate, such as acrylic adhesive on jute backing. The substrate moves continuously at 90° to the field's force lines. In flight, the fibers align with the field, thus hit the adhesive end-on. A charged ' screen in the hopper, or a grid be­low the hopper, forms the positive pole. A grounded plate over which the substrate passes is the negative pole.

The fibers charge positively either in the hopper, or as they pass a grid below the hopper. Some of the fibers catch in the already-forming flock coating without embedding in the ad­hesive, but they discharge and fly up for a new charge and another pass at the adhesive. Rotating beater bars striking the back of the substrate can be used to increase flock penetration into the adhesive, as well as to knock off loose flock. Loose flock on the pile surface is drawn off by vacuum, while drop-off is picked up in bins below the substrate for reuse.

Field voltages, which range be­tween 20,000 and 150,000 volts, are determined by the job to be done -and depend on fiber size, chargeabil-ity, and density desired on the sub­strate. Rectified alternating current is sometimes preferred over steady d.c. The a.c, pulsations reduce both flock chaining in flight and loose fiber build-up on top of the flocked surface.

Multiple hoppers can be used for higher substrate speed, or to feed fi­bers of different length, color, or type. Substrate speeds for over-all flock covers usually do not exceed 5 yards per minute.

Aid Growth. Acrylic and ure-thane adhesives deserve a large share of credit in the development of high-quality flocked carpets and textiles. These adhesives resist washing and dry-cleaning solvents, a significant ad­vantage over alkyd resin, neoprene, natural rubber-base, and many other adhesives.

Acrylic emulsions for carpet flock­ing are supplied by Rohm & Haas,

JAN. 11, 196 5 C&EN 41

ν! $OReTV'$WM FREE CATALOG features industry's most complete GUIDE FOR SELECTING PROTECTIVE GLOVES

1

You can quickly find the right glove material to protect against dangerous or deteriorating substances present on your job. . . plus the right one for resistance to heavy abrasion, cut­ting, puncturing, tearing and other physical factors. You'll find expert, easy-to-use guidance on size, length, style and thickness, too. It's all in the most complete Industrial Glove Selec­tor Guide ever researched and com* piled by a glove manufacturer.

To assure receipt of your copy of Surety's new General Catalog No. 65 at earliest possible date, why not write for it today. A wealth of other information and tips to help in the purchase and use of gloves, sleeves, aprons, leggings and spats is included in this attractive, 20-page product publication. It will win your praise for speed and ease of reference as well as usefulness.

PLEASE MAIL REQUEST ON COMPANY LETTERHEAD

THE SURETY RUBBER CO. B0X97-U-1, CARROLLTON, OHIO

B. F . Goodrich Chemical, and others. They contain 45 to 50% solids and sell for 38 to 40 cents a pound (dry basis) in bulk. To promote build-up and body on the substrate surface, the emulsion is thickened with car-boxymethylcellulose. A catalyst (such as ammonium chloride or oxalic acid) promotes cross-linking within several minutes at 280° to 300° F. after flocking.

Meanwhile, Thiokol and others are promoting urethane adhesives. Thio-kol's one-package urethane adhesive for carpet flocking is cut back with 30% of Cellosolve Acetate, sells for 42 cents a pound dry basis (truck-load, drums). This adhesive is also thickened before application to sub­strates. Curing after flocking occurs under about the same time and tem­perature conditions as it does with acrylics.

Organic solvents in the urethane adhesives present a fire hazard, and vapor must be disposed of during adhesive cure. But Thiokol hopes to develop water-emulsion urethanes to eliminate these problems.

Fiber Treatment. Flock cutting concerns, and the few users who cut their own, use guillotine cutters to produce uniform-length flock from tow (parallel-bundled fibers). Some tow, such as nylon, is cut wet to pre­vent fusing when the blade heats up. Fibers for electrostatic flocking are usually 1 to 6 mm. long. Flock fibers should be straight, free-flowing, and surface-conductive enough to be elec­trostatically active. This presents a major problem to producers of man-made fibers. Materials such as poly­propylene and nylon are nonconduc-tive, and must be chemically finished to accept an electric charge. Fiber producers will not discuss what the finishing materials are, however.

Products like the quaternary am­monium salts can be used. One such product, developed by Farbwerke Hoechst and called Leomine Kp, im­parts both conductivity and improved flow to cellulosic and nylon fibers. The material is a cationic aliphatic amine with amide and sulfonate groups. The finishes are applied by padding onto tow after dyeing, or to flock from a water bath.

Fiber moisture increases conductiv­ity, but too much moisture impairs flow. Thus, Indev, Inc. (Pawtucket, R.I.), makers of electrostatic equip­ment, recommends humidity control in the flocking area.

42 C & E N J A N . 11, 196 5

ALKYLBENZENES I

ί Ι

âÊÊk THE HUMPHREY CHEMICAL COMPANY

The N e w Beckman Zeromatic® I I p H M e t e r is an improved version of the time-tested Zeromatic. This new instrument has an easily-read 8.2" meter covering the full 0-14 pH range. It gives you relative accuracy of ±0.05 pH and repeatability to ±0.015 pH. It has push button convenience and is splash proofed in a die-cast aluminum case with reagent resistant finish. For more information or a demonstration of the Zeromatic II contact your local Beckman Sales Engineer or write for Data File LpH-13-165.

B e c k m a n I N S T R U M E N T S , I N C .

SCIENTIFIC AND PROCESS INSTRUMENTS DIVISION FULLERTON, CALIFORNIA* 92634

INTERNATIONAL SUBSIDIARIES: GENEVA, SWITZERLAND; MUNICH, GERMANY; GLENROTHES, SCOTLAND; PARIS, FRANCE; TOKYO, JAPAN; CAPETOWN, SOUTH AFRICA

C&EN PROGRESS REPORT

' " 1

EQUIPMENT

These items have all been mentioned editorially in C&EN in the past month. If you haven't already sent for information on them, just check the appropriate key numbers on the coupon on page 48, and C&EN's Readers' Information Service will forward your request to the manufacturer.

INSTRUMENT AND CONTROLS . . . Product

Gas chromatograph E60

Analyzer E61 (AMX)

Switches E62 (Series 675)

Controller E63 (Series 9100)

Micro instrument E64 (Micro-Hypo, Model MH/B-type 202)

Thermostat E65 (Model F28)

Magnetic field control E66 (Autogauss)

Dialysis cells E67

Particle size analyzer E68 (Cyclosizer)

Gas chromatograph E 69 (Aerograph Model 705)

EQUIPMENT AND LABWARE . . . Agitator kit E 70

Valves E 71

Filter membrane E 72

Tubing E 73

Wire mesh E 74

Company

Analytic Systems Co. Pasadena, Calif.

Applied Research Laboratories, Inc. Glendale, Calif.

Custom Component Switches, Inc. Chatsworth, Calif.

Hydor Therme Corp. Pennsauken, N.J.

J. T. Slocomb Co. South Glastonbury, Conn.

Robertshaw Controls Co. Youngwood, Pa.

Spectromagnetic Industries Hayward, Calif.

Technilab Instruments Los Angeles, Calif.

WEMCO Division, Arthur G. Mc-Kee & Co. San Francisco, Calif.

Wilkens Instrument & Research, Inc. Walnut Creek, Calif.

Bench Scale Equipment Co. Dayton, Ohio

Hoke, Inc. Cresskill, NJ .

Selas Flotronics Dresher, Pa.

Taylor Corp. Valley Forge, Pa.

Technical Wire Products, Inc. Cranford, N.J.

Features

For use in multiple- or single-stream detection and multicolumn systems

Low-cost microprobe unit with crystals for wave lengths from 1 to 10 A.

For purge alarms or purge control ap­plications

Portable thermostatic unit for tempera­ture control from ambient to 200° C.

For microtitration, density determina­tion, or repetitive displacement

To control temperature and movement of heavy liquids

For use with electromagnets and ion optical systems

To separate proteins and large non-dialyzable solutes

Designed to operate on sizes less than 50 microns

Fully automatic preparative instrument

Designed to investigate fluid agitation processes for scale-up data

Diaphragm-type for ultrahigh vacuum use at temperatures to 600° F.

Made of silver; developed by micro-filtration and microanalysis

Composite glass and paper base lami­nated plastic

Can be knitted of stainless steel, copper, aluminum, or other metals or plastics

NEW CHEMICALS

A one-package, water-repellent finish for cotton fabric is now being offered by Bryant Chemical Corp., of North Quincy, Mass. Brypel is a wax emul­sion-metallic salt and is supplied in an emulsion containing 22 to 24% active ingredient. The emulsion can be stored indefinitely and is easily diluted to a 4 to 8% solution at room temperature. C 31

Cyclopentadienyliron dicarbonyl di-mer is available in limited production quantities from Alpha Inorganics,

Inc., of Beverly, Mass. The chemical is highly reactive and has been stud­ied as a polymerization catalyst, the company says. It has also been found to be an efficient combustion catalyst and antiknock agent. Alpha Inorgan­ics suggests that it can be used where a nonaqueous solution containing iron is needed. It can also be used as an intermediate. C 32

Two methacrylate monomers are available in commercial quantities from Alcolac Chemical Corp., of Bal­timore, Md. Sipomer 2M1-M (di­methyl aminoethyl methacrylate) is

readily polymerizable and offers a means of incorporating amino groups in polymeric systems. Sipomer HEM-1 (hydroxyethyl methacrylate) was developed to satisfy the need for a hydroxyl-containing monomer with a low diester content. C 33

Naphthoresorcinol is now being of­fered in ampoules, packed under ni­trogen, by Gallard-Schlesinger Chem­ical Mfg. Corp. According to the Carle Place, N.Y., company, the chemical is used as a reagent in the colorimetric determination of glu­curonic acid in urine. The company

44 C&EN JAN. 11, 1965

now from

Mallinckrodt the quality

line of labware

designed with purpose

Your first glance at this new catalog will

tell you why Pioneer is the Preferred Plastic

Labware line. Each item is designed with

purpose. Manufactured with care.

Priced to cost you less—and save still

more each time it's dropped.

More than a hundred items are listed—

many with laboratory engineered features

that only Pioneer Preferred Plastics offer:

Measure-matic dispensers, quick connectors,

reagent dispensers, unique valves

and fittings for flexible tubing.

Ready-to-ship stocks of Pioneer labware are as

near as your Mallinckrodt Distributor. Ask

him for your copy of this new catalog

or mail the coupon today.

C3 <(y0rAMt&P [jD

Pioneer Plastics Division*Mallinckrodt Chemical Works Second and Mallinckrodt Streets • St. Louis, Missouri 63160

Please send new Preferred Plastic Labware Catalog

Name Company-

Address

City -State. -Zip Code_

PIONEER PLASTICS DIVISION /MALLIWCKRODT CHEMICAL WORKS / S t . Louis / N e w York / L o s Ahgeles

C & E N 45

Carol Dozier and Jameson Kaiser will be graduating in June from one of the best high schools in their state. They expect to build their professional careers around chemistry. Already Carol Dozier and Jameson Kaiser think of chemistry as the physics of electron probability clouds. Bubblers and test tubes they consider merely the operational arena. Carol and Jameson are pretty up-to-date. Imagine how much more up-to-date they will be four years from

now. W e hope to keep up with them, though, and to welcome them as customers for EASTMAN Organic Chemicals in 1969.

Mr. Brock graduated from a fine college in 1934 and has worked as a chemist ever since. To be perfectly candid, he seldom finds time to get down (or up) to the fundamentals that reign in cloud-land. But perhaps his eye will be caught by one of the following

To precipitate glycine selectively, use EASTMAN 9256 This compound, Potassium Ο xalatochrornate, we are led to believe, forms an insoluble complex with glycine and only glycine among all amino acids. Picks the glycine right out of a protein hydrolysate. See / . Biol. Chem. 10,317 (1935). Sorry we haven't offered the compound till now.

To get α red color with alcohols, yellow with amines, bright green with thiols, and blue with low-molecular-weight car-boxylic acids, use EASTMAN 9336 Known as "vanadium 8-hydroxyquinolate." Shortened to "vanadium oxinate" on basis that "oxine" is 8-hydroxyquino-line. Came to light in Barcelona. Story begins with straight­forward use of good old 8-hydroxyquinoline to determine vanadium. Then the Spaniards became intrigued with the effects of the solvent on the color of the complex. When they thought of the switch of using the complex to characterize the solvents, the conceptual elevator ascended to a new level. Some Londoners then got on and took to calling the complex The Black Acid.

It is black, by George ! That must mean it absorbs all wavelengths of visible light

until some functional group comes along and bleaches it in one part or another of the spectrum. Exactly what happens and how come are detailed in depth by the Londoners in Journal of Inorganic and Nuclear Chemistry 5, 316. On the basis of their elucidation of the structure, we figure we had better enter it in our catalog as Oxohydroxybis(8-hydroxy-quinolino)vanadium (V). Sounds more wholesome than The Black Acid. Or just think of it as EASTMAN 9336. Read Anal. Chim. Acta 13, 1, before accepting extended engagements for demonstrations.

To check how much aliphatic aldehyde is polluting the air, bubble some of it through a solution of EASTMAN 8443 1 p.p.m. by volume has been reported in some large cities. Too high for comfort? Get the facts first-hand. Ask us for free abstract of procedure developed by U. S. Public Health Serv­ice. Separately order your 3-Methyl-2-benzothiazolone Hydra-zone Hydrochloride. By specifying EASTMAN 8443 you show you not only keep up with the latest but leave no loopholes in a case. Abstract will also cover use of same reagent on ben­zene extracts of atmospheric particulates to measure another significant pollutant, carbazole. Xanthydrol (EASTMAN PI 559), the previous choice for carbazole detector, has only 1/20 the sensitivity. A chemist who makes chemicals that are used to keep other chemicals from becoming public nuisances goes home at night proud of his day's work.

To locate in tissue sections substances capable of serving as antigens, treat with serum in which you have induced the corresponding antibody and made the proteins fluorescent by coupling them to EASTMAN P9090 See "Physical Techniques in Biological Research," III, p. 134. Says that along with the successes of the method there have also been disappointments due to organic synthesis difficulties, among others. Mentions that Chemical and Engineering News carries advertisements of companies that undertake organic synthesis on order and could be approached to make fluores­cein isocyanate as the fluorescent dye. This could mean us. Suggest, however, first trying 5-Dimethylamino-l-naphthalene-sulfonyl Chloride. Evaluated for this use in Proc. Soc. Exptl. Biol. & Med. 98, 120. Order it right off the shelf as EASTMAN P9090.

Orders, requests, and price inquiries are handled by Distillation Products Industries, Roch­ester, Ν. Y. 14603. Local distributors carry large stocks of EASTMAN Organic Chemicals.

Distillation Products Industries is a division of Eastman Kodak Company

46 C & Ε Ν

on some EASTMAN Organic Chemicals

adds that because the reagent deteri­orates in air and light, the new offering will be of considerable importance to scientists. C 34

Deoxyribonucleosides uniformly la­beled with carbon-14 are now avail­able from Nuclear-Chicago Corp. The Des Plaines, 111., company says that it is now offering thymidine, de-oxyadenosine, deoxyquanosine, and deoxycytidine at specific activities in the range of 200 to 350 microcuries per millimole. C 35

Fatty acid with more than 75% lino-leic acid content has been introduced by A. Gross and Co. Linolenic acid content is less than 1%, according to the New York, N.Y., company. Gro-

co-19 linoleic acid is of special interest to the coatings field, the company says. C 36

Acetone semicarbazone is available in experimental quantities from Na­tional Poly chemicals, Inc., of Wil­mington, Mass. The company ex­pects the chemical to replace semi­carbazide hydrochloride in the syn­thesis of cortisone and other steroids and wherever free semicarbazide is required in a reaction. C 37

Further information on keyed | Chemicals and Equipment I items is readily available . . .

Use handy coupon on page 48 \

Readers' Information Service January 11, 1965

Use this handy self-mailer to obtain further information or literature. Simply mark the items desired, fill out the information requested, clip the coupon, fold, staple, and mail.

Name:

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CLIP COUPON—Fold along this line—fasten (staple, tape, glue) MAIL

Your Industry:

A ( ) Engineering and Construction B ( ) Food and Kindred Products C ( ) Textile Mill Products D ( ) Paper and Allied Products E ( ) Government F ( ) Chemicals and Allied Products G ( ) Elastomers, Polymers, Plasticizers H ( ) Drugs I ( ) Detergents, Cosmetics, Specialties J ( ) Paints, Varnishes, etc.

K ( ) Petroleum Ref., Asphalts, Lubricants

L ( ) Rubber and Plastic Products M ( ) Independent Laboratories N ( ) Consultants 0 ( ) Primary Metal Industries P ( ) Fabricated Metal Products Q ( ) Machinery and Equipment R ( ) Transportation Equipment S ( ) Instruments and Controls T ( ) Education

"pmfidci Averts Plant Shutdown, Provides Needed High Purity Water

Within five weeks after purification needs became known, a Penfield demineralizing system was com­pletely installed and supplying required production quantities of high purity water. Plant shutdown, threatened by impurities in process water, had been averted. System included pre-filters, two-bed de-mineralizers equipped for automatic shut-off at desired purity levels and fully automated regenera­tion cycles, including rinsing and recutting effluents into process; also special neutralizers for treating regenerant effluents. All units were delivered fully "packaged" — ready to operate as received.

"Packaged" Dl Equipment custom engineered

to your Purity Needs Need central demineralizing? Point-of-use polishing? Ultra high purity make­up or rinse water? Whatever the need, it will pay you to check Penfield.

Close to two decades of engineering Dl systems means that Penfield has hundreds of field-proven designs to draw upon.

And "Packaged" means that your Penfield equipment arrives fully unit­ized and ready to operate. Installation and start-up expense is held to a mini­mum.

For assured Dl performance — and important savings in time, trouble and total outlay, check Penfield. Phone today — Area Code 203, 235-1694.

New! Penfield CUBS

100% stainless steel, including distrib­utors. Snap-on covers for easy recharg­ing. Flow rates: 100, 200, 300 GPH. These inexpensive pressure units are ideal for small scale production, polish­ing, special ion exchange applications.

\f Send lor new eighty-page catalog.

PENFIELD MANUFACTURING CO., INC. 48B Britannia St., Meriden, Conn.

"Nineteen years of Dl equipment pioneering... Specialists in system design, automation"

J A N . 11, 196 5 C & E N 47