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4Deveo:? ct.,US

SAMtICATION OFg ~ A-RADIO-TRACER METHOD TOg THE DECOMPOSITION MECHANISM OFg POLYURETHANE PROPELLANT SYSTEMS (U)

I U.S. NAVAL PROPELLANT PLANT INDIAN HEAD MARYLAND

W1

IIiIII

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IIIII

• ° I"

Published by the ITechnical Information Department

(102/62/548)

I,I

CONFIDENTIAL

RESEARCH AND DEVELOPMENT DEPARTMENT

NavWeps Report 8021Technical Report 121

16 November 1962

APPLICATION OF A RADIO-TRACER METHOD TOTHE DECOMPOSITION MECHANISM OF POLYURETHANE

PROPELLANT SYSTEMS(U)

By

P. E. WilknissD. Levine

U. S. NAVAL PROPELLANT PLANTIndian Head, Maryland

0. A. WESCHECaptain, USNavy JOE L. BROWNINGCommanding Officer Technical Director

CONFIDENTIAL

CONFIDENTIAL NAVWEPS REPORT 8021

FOREWORD

The Naval Propellant Plant has been conducting research investigationsfor the past several years to improve methods of predicting the useful life ofsolid propellants. The experiments described in this report indicate that theradioactive tracer technique provides a convenient tool for following the degra-dation of polyurethane propellants. The data are as of 1 October 1962 and aresubject to modification or withdrawal.

The names of manufacturers are given to identify types of material andequipment and do not constitute an endorsement of the products.

t4

F. E. BrinckmanHead, Analytical

1 Chemistry Division

Approved by:

S'Bodo BartochaAssociate Director

I for Research

1Released by:

S.E. WilsonDirector, Research and

Development Department

1ICONFIDENTIAL iiI


I

CONTENTS

Foreword iiiAbstract viExperimental 2Results 7Discussion 11i References 13

i FIGURES

1. Apparatus for Preparation of Labeled Toluene Diisocyanate 42. Apparatus for Mixing of Labeled Propellant 53. Counting of Labeled Propellant 74. CO2 Evolution from A-1 Polaris Propellant 95. Evolution of Radioactive CO2 10

IiI]IIIICONFIDENTIAL vI

NAVWEPS REPORT 8021 CONFIDENTIAL

I

Abstract Confidential "

ABSTRACT

A new techniqve employing radio-tracer C14 has been used for followingthe thermal degradation of a polyurethane propellant. The described tracermethod is thought to be an effective tool to investigate the influence of suchparameters as moisture, pressure, other ingredients of the propellant, etc.,on the rate of carbon dioxide evolution and, therefore, the rate of binder break- "down. Extrapolation of the data obtained indicates that the half life of the pro-pellant is 6. 7 years.

vi CONFIDENTIAL

ICONFIDENTIAL NAVWEPS REPORT 8021

I

I APPLICATION OF A RADIO-TRACER METHOD TOTHE DECOMPOSITION MECHANISM OF POLYURETHANE

PROPELLANT SYSTEMS(U)

I Several techniques have been employed for following the decompo-sition of polyurethane propellants in order to predict their safe, useful lives.Among the techniques used are stress relaxation measurements,(1, 2) swellingmeasurements, (1) nuclear magnetic resonance measurements, (3) and extractionprocedures. (4,5)

dixOne paper(6) reports the evolution of gases consisting chiefly of carbon

dioxide and hydrogen during thermal decomposition of a polyurethane propellant.It is believed that the urethane linkage of the propellant binder is one sourceI.for the CO2 being evolved, according to

H1

I R-NC- O R - CO2 + decomposition products.

The purpose of the work described in this paper is (1) to determine un-equivocally whether or not the urethane linkage is mechanistically involved instorage decomposition of this selected prbpellant, and (2) to evaluate a sensitivemethod for determining the rates of such decomposition. Furthermore, it wasplanned to investigate the rate of CO2 evolution which is a measure of the rate ofdecomposition of urethane linkages; and therefore, also, a measure of decompo-sition of the propellant binder.

The approach in this problem involves using a radio-tracer method; L e.,I labeling the carbon atom of the urethane linkage with radioactive C14,

I R-N-C11-0 -R -- C1402 + decomposition products.

It is obvious that if the urethane linkage breaks, C140 2 should be evolved

which can be easily detected by its radioactivity. This, in turn, is a demonstra-tion for the decomposition of the urethane linkage.

I CONFIDENTIAL

I


As an example of a polyurethane propellant, the formulation of the Aerojet-General Polaris urethane propellant (ANP 2639 AF) was used. The basic ingredi-ents of this propellant are ammonium perchlorate, 60%; aluminum, 15%; and apolyurethane binder, 24%.

The binder itself consists of a three-dimensional network, made up of a2,4-toluenediisocyanate (TDI) -polypropylene glycol (PPG) chain, crosslinkedwith monohydroxyethyl-tris-hydroxypropyl N, N, N', N'-ethylenediamine (MTDA).

The results obtained by employing this propellant system to study thedecomposition of its urethane binder linkage by the radio-tracer method aredescribed in the following sections.

EXPERIMENTAL

Preparation of Toluenediisocyanate Labeled with C14

In order to prepare a propellant which is labeled with C14 at the urethanelinkage of its binder, TDI labeled in one or both of its isocyanate groups isneeded. Because it appears very difficult to label both isocyanate groups in awell defined way, TDI labeled in only one isocyanate group was prepared. Themethod reported by Siefken(7) for the preparation of isocyanates in general wasemployed. This method and the apparatus used were modified to meet thespecial requirements in synthesizing the desired labeled compound. The prepa-ration of the labeled TDI is a two-step reaction as follows:

CH3 CH3

NH 2 + C14 0C12 , K.. NHC1 4OCI

NH2 • HCl

() (I1) (I)

COC 2I 1300 C

ONC1 4 0NCO

(Iv)

2 CONFIDENTIAL


Toluenediamine (TDA, I) dissolved in methylene chloride is reacted at 0 0 Cwith labeled phosgene1 which is also dissolved in methylene chloride. The inter-mediate compound (Hi) precipitates and is completely freed of methylene chlorideIand excess phosgene by evacuation.

In the second reaction step, compound III is suspended in high-boilingAroclor 12482 and is reacted with unlabeled phosgene at 1300 C until a clear solu-tion is obtained. Finally, the labeled TDI is recovered from this solution byvacuum distillation. The apparatus shown in Figure 1 was used in this procedure.

jTwo batches of radioactive TDI were prepared by the following procedure:For batch no. 1, 3.66 g of TDA (recrystallized from benzene) dissolved in

45 ml methylene chloride was reacted with 2. 7 ml liquid phosgene carrier plus0. 1 millicurie of C14-phosgene (specific activity 1. 52 millicuries per millimol)dissolved in 15 ml methylene chloride. The intermediate salt precipitate was1freed from phosgene and methylene chloride, suspended in Aroclor, and reactedwith phosgene gas until a clear solution was obtained. The TDI was recoveredby vacuum distillation and analyzed for purity by reacting a sample with di-n-Ibutylamine, and titrating the excess amine with hydrochloric acid. (8)

Batch no. 2 was prepared in the same way as batch no. 1 except 0.5 milli-curie (specific activity 1.52 millicuries per millimol) radioactive phosgene wasused.

Data of batch no. 1 and batch no. 2 are given below:

Batch no. 1 Batch no. 2

Yield: 3.0 g TDI (57% of the theory) 3.0 g TDI (57% of the theory)Boiling point: 900 C/2 mm Hg 900 C/2 mm HgMelting point: 21. 30 - 21. 60 C 20. 80 - 21. 30 CPurity: 94. 7% 97. 8% (after two distillations)Specific activity: 14.8 microcuries/gram TDI 51.0 microcuries/gram TDITotal activity: 44. 4 microcuries 153 microcuries

(44% of applied amount) (30% of applied amount)

I In order to obtain a purer product, 4 ml of inactive TDI (purity 99%) wasadded to the 3 g of labeled TDI (Batch no. 2) and the mixture distilled again.1 Results were as follows:

Yield: 5.74 g TDIBoiling point: 90 ° C/2 mm HgMelting point: 20. 80 - 21. 50 CPurity: 98.6%Specific activity: 21.0 microcuries/gram

I Obtained from Nichem Company.2Obtained from Monsanto Chemical Company.

i CONFIDENTIAL 3

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4 CONFIDENTIAL

IICONFIDENTIAL NAVWEPS REPORT 8021

3 Specific activity of the TDI was determined in two ways. One was by pre-paring very thin counting samples of solid material obtaine(i by reacting TDI withdi-n-butylamine and evaporating the solvent. The other was by reacting TDI withBa(OH) 2 solution and counting the resulting BaCO3 in an "infinitely thick" layer.In both cases adequate samples of standardized BaC14O3 were used as standards.The results for the specific activity of TDI were in agreement within 20%.

I Mixing and Curing of Labeled Propellant

The Aerojet-General Polaris urethane propellant formulation ANP 2639 AFwas used. The apparatus used for mixing the radioactive propellant is shown inFigure 2. The entire propellant mixing procedure was carried out under a pres-sure of 10 mm Hg. When material had to be added the mixer was flushed withprepurified nitrogen. Gases evolved on mixing, including C140 2, were caught in

I the cooling traps (liquid nitrogen) of the apparatus. All ingredients used werecarefully dried. The operation was started by mixing a premix of PPG, MDTA,and lecithin for 10 minutes. Coarse and fine ammonium perchlorate (blendedtogether) was added in three equal portions, the mixing time after each additionbeing 10 minutes. In the next step, a premix of aluminum, carbon black, copperchromite, and phenyl beta-naphthylamine was added in two equal portions; mixingtime again was 10 minutes after introducing each portion. The TDI (labeled di-luted with unlabeled) together with ferric acetyl acetonate were added; the totalbatch was mixed for 25 minutes. The mixture was cast in an aluminumcylinder and cured for 4 days at 430 C. Two batches of labeled propellant weigh-ing 250 g each were prepared.

I2

4 7 8 9

1 ARC-35-Z-blade mixer 6. Three-way stopcock2. Stock valve 7-8. Ba(OH)2 traps3. Three-way stopcock 9. Stock valve

i 4-5. Cooling traps

FIGURE 2. APPARATUS FOR MIXNG OF LABELED PROPELLANT

I CONFIDENTIAL 5

i

INAVWEPS REPORT 8021 CONFIDENTIAL

In the first batch, an activity of 44 microcuries of TDI was incorporated.During curing the temperature went out of control, up to at least 1300 C. Thisis thought to be the reason the propellant did not cure completely. Therefore,this batch was used only for a qualitative study.

In the second batch, 34 microcuries of labeled TDI was included. After4 days of curing, a good rubbery propellant was obtained.

Counting of C1402 Evolved from Propellant

Radioactive carbon dioxide was expected to be evolved on mixing (becauseof traces of moisture causing hydrolysis of the TDI) and on storage of the pro-pellant as a result of decomposition of the urethane linkages.

C140, Evolved on Mixing:

The CO2 evolved on mixing was condensed with liquid nitrogen, reactedwith Ba(OH) 2 solution to form BaCO3, and finally the BaCO counted with aGeiger-Mueller Counter after usual sample preparation (as an "infinitely thick"BaCO3 layer).

C1402 Evolved on Storage:

Continuously Working Counting System: The first approach was to use acontinuously working counting system as shown in Figure 3 and similar to onedescribed by Basolo. (9) The propellant sample is contained in flask 3. The gasover the propellant is circulated in a closed system by means of a pump (1). Itpasses a counting window (4) made of a very thin Mylar film, which allows theC14 beta-radiation to penetrate into the Geiger-Mueller Counter (5) directlyattached to the counting window. The counts are registered in the scaler (7).The stopcocks (2) and (6) serve to change the atmosphere in the closed system,if necessary.

The results obtained on testing this system showed that its counting effi-ciency is too low for the activities of the C0 2 evolved from the propellant sample.Therefore, a second technique of counting the activity was chosen.

Noncontinuous Counting System: This second method is based on a non-continuous counting procedure. The propellant sample is stored in a 100-mlflask with an outlet closed by means of a three-way stopcock. Through thisthree-way stopcock, the flask containing the sample is first evacuated and thenfilled with inert gas containing a certain amount of inactive CO2 (approximately10 ml C0 2) which serves as carrier for the CO2 evolved from the propellant

6 CONFIDENTIAL

CONFIDENTIAL NAVWEPS REPSORT 8021

sample. In this way it is possible to sample even the very small amounmts of CO2coming from the propellant because they mix with the added carrier.

4 5

I !

1. Pump 5. Geiger-Mueller counter2. Stopcock 6. Stopcock3. Flask 7. Scaler

~4. Counting window

FIGURE 3. COUNTING OF LABELED PROPELLANT

jFrom time to time the storage flask is evacuated; all the CO 2 cont7ained istrapped with liquid nitrogen and reacted with Ba(OH) 2 solution. The preecipitatedBaCO3 is then prepared as usual for counting with a Geiger-Mueller Cox.Mter (asan "infinitely thick" layer). This method, as described, worked satisfnctorily,the counting efficiency being high enough for the counted activities.

The activity of the BaCO3 obtained from the samples was compareed tostandardized BaC14q for calculating the specific and absolute activity.

RESULTS

Qualitative Results

Evolution of C140, on Mixing:

The counting of the gases evolved on mixing after treating showed that theBaCOq obtained was radioactive. This indicates that TDI is decomposek on niLx-ing. No quantitative investigation of this result has been done so far.

Evolution of C140, on Storage:

The BaCO3 samples obtained from the propellant on storage were :found tobe radioactive. Because the carbon atom of the urethane linkage of the 1propel-lant is the only site labeled, this indicates that the urethane linkage is d ecom-posed on storage of the propellant. It is therefore a source for the C02 evolvedon storage as reported. (6)

CONFIDENTIAL 7

I


Checking of Continuous Counting System:

The continuous counting system was checked with a specimen of the unsatis-factorily cured propellant (approximately 125 g of batch no. 1, containing 22 micro-curies of C14-labeled TDI). The entire propellant sample (a viscous slurry) wasstored under air at 770 C. The results of this experiment are plotted in Figure 4.The counting rates obtained were rather low; and, because of this low countingefficiency, the system was not used for other experiments. Figure 4 also showsthat evolution of CO2 from the uncured propellant is rapid at the beginning, whileit slows markedly to a steady rate after 3 days of storage.

Quantitative Results

The noncontinuous counting procedure was used to investigate the C02 evolu-tion rate from the radioactive propellant (batch no. 2).

The propellant (169. 3 g), containing 23. 1 microcuries of TDI was cut inrectangles (1/4 x 1/2 X 3/4 inch) and stored in three equal portions in 100-mlflasks. An inert atmosphere of 40 ml nitrogen and 10 ml carbon dioxide wasused, thus maintaining a pressure of about 0.5 atm in the storage flasks. Thestorage temperature was maintained at 710 C. Figure 5 shows the resultsobtained.

As shown in Figure 5, the C02 evolution rate becomes steady at about the50th day of storage. The flat point in the curve between the 33rd and 35th day iscaused by a breakdown of the heating system. It was found that the heating systemwas not completely adjusted at the beginning, causing a temperature difference of30 C between Samples 1 and 2 and a temperature difference of about 10 C betweenSamples land 3. This is thought to be thecause of thedifferent rates of C02 evolutionamong the three samples. The difference in the evolution rate disappeared aftersome time. From the 60th day on, the CO2 is evolved at an activity rate of0. 75 count per minute per day per gram of propellant.

Further, the following calculations can be made: 34. 2 microcuries of C1

as labeled TDI was incorporated in the original 250-g propellant mix; 169.3 g ofpropellant, containing 23. 1 microcuries of labeled TDI, was recovered for storage.Therefore, 1 gram of propellant contained 0. 14 microcurie of C14-TDL

If the 75th day of storage is taken then there is an accumulated average(over all three samples) of 100 counts per minute per gram of propellant. Thisis a total activity of 4 X 10 - 3 microcuries (converted from counts per minute tomicrocuries by means of BaC140 standard).

8 CONFIDENTIAL


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I CONFIDENTIAL9


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10 CONFIDENTIAL


I As indicated above, at the beginning of storage each gram of propellantcontained 1. 4 x 10-1 microcuries of C14-TDI. Until the 75th day, 4 x 10- 3 micro-curies or 2. 86% of this initial activity evolved from the sample as CO2. As every

C402-molecule urethane linkage and as the other (C12) urethane linkages behavethe same way, this means also that 2. 86% of all the urethane linkages of thebinder have been cleaved. If it is now assumed that the C02 evolution rate re-mains constant at 0. 75 count per minute per day per gram of propellant (fromthe 60th day), then the useful life or half life of the propellant can be roughlypredicted.

A C14 activity evolved at a rate of 0. 75 count per minute per gram per daymeans 3 x 10 - 5 microcuries per gram per day or 0. 02% of the originally intro-duced activity. So if the rate stayed constant for the rest of the year, then thepropellant binder would degrade 2. 86% (first 75 days) plus 5. 8% (0. 02 x 290)which would equal 8. 66% in the first year. Assuming constant rate, the follow-ing years would bring 7. 3% degradation of the binder. Fifty percent of thebinder would be decomposed after 6.7 years, thus the useful life or half lifeof the propellant is 6.7 years.I

DISCUSSION

I The experiments showed radioactive C02 is evolved on mixing, the onlysource of which is the labeled TDI. So far, no quantitative investigation has beenmade nor has the mechanism of the TDI decomposition been studied. It is be-lieved, however, that the C02 evolution is from hydrolysis of the TDI caused bytraces of moisture contained in the other propellant ingredients. It should be

I possible to investigate thoroughly the C02 evolution on mixing by this method.This method should also be a valuable tool in investigating the C02 evolu-

tion on curing and furthering the optimal conditions of curing. Experimentshave not yet been carried out.

It has been proven by the experiments performed in this study that cleavageof the urethane linkage of the propellant binder is one source for the C02 evolu-tion observed on thermal decomposition of urethane propellants. The results donot at this point indicate whether this is the only source for CO 2 evolution; furtherexperiments will be required to investigate this. The mechanism of the cleavageof the urethane linkage has not been determined yet. It is believed, however,that hydrolysis is not the only cause. The described tracer method is thoughtto be an effective tool to investigate the influence of such parameters as moisture,pressure, other ingredients of the propellant, etc., on the rate of CO2 evolutionand, therefore, rate of binder breakdown.

j CONFIDENTIAL 11

I


Furthermore, the method is thought to be of special value in predictingthe stability and useful lifetime of a polyurethane propellant in advance. As thesensitivity of the method can be increased by a factor of 104 (by using a onehundred times higher C14 activity and gas counting of the C140 2, which givesanother factor of approximately 102), it should be possible to investigate the sta-bility of polyurethane propellant binders at room temperature, a more realisticsituation than the high temperature-accelerated cycle.

An additional advantage of the method is that only small amounts of pro-pellant are required for surveillance. Additional experiments are required todetermine broader applicability of the method.

1

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REFERENCES

1(1) J. G. Tuono and W. M. Vogel. "Two Apparatuses for InvestigatingElastomers - 1. Relaxameter; 2. Vapor Pressure Apparatus." Bulletin of the18th Meeting of the Joint Army-Navy-Air Force on Physical Properties ofJSolid Propellants. June 1959. SPIA/PP12. CONFIDENTIAL.(2) J. G. Tuono and W. M. Vogel. "Studies on the Thermal Degradation ofPolaris Binders ANP 2639 and ANP 2655." Bulletin of the Fourth Meeting ofthe Joint Army-Navy-Air Force Solid Propellant Surveillance Panel. pp. 71-83.December 10, 1959. CONFIDENTIAL.

1(3) D. Levine, et al. "Polymer Degradation Studies of the PolyurethanePropellants." Bulletin of the 17th Meeting of the Joint Army-Navy-Air ForcePanel on Analytical Chemistry of Solid Propellants. pp. 75-83. October 3,4,5, 1961. CONFIDENTIAL.

(4) U. S. Naval Propellant Plant. THE STORAGE DEGRADATION OF POLARISPROPELLANT. By C. Boyars, et al. Technical Memorandum Report 153.29 September 1958. CONFIDENTIAL.

(5) U. S. Naval Propellant Plant. THE STORAGE DEGRADATION OFJPOLARIS PROPELLANT II (U). By J. G. Tuono and W. M. Vogel. TechnicalMemorandum Report 176. 12 February 1960. CONFIDENTIAL.

(6) U. S. Naval Propellant Plant. INVESTIGATIONS ON THE EVOLUTION OFGASES FROM AEROJET POLARIS PROPELLANTS DURING STORAGE. ByW. M. Vogel and W. K. A. Gallant. Technical Memorandum Report 187.

1June 1961. CONFIDENTIAL.(7) W. Siefken. "Mono- and Polyisocyanate." Ann. 562:75 (1949).

1 (8) Ibid. Ann. 562:99 (1949).(9) F. Basolo and A. Wojcicki. "Metal Carbonyls. I. Carbon Monoxide Ex-change with Nickel Tetracarbonyl and Dicobalt Octacarbonyl. 11 J. Am. Chem.

ISoc. 83:520 (1961).

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I CONFIDENTIAL 13

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Atlantic Research CorporationShirley Highway and Edsall RoadAlexandria, Virginia 2

!II

Monsanto Research CorporationBoston LaboratoriesEverett 49, MassachusettsAttn: Library

Allied Chemical CorporationGeneral Chemical DivisionResearch Laboratory, P.O. Box 405Morristown, New JerseyAttn: L. J. Wiltrakis, Security Officer

National Cash Register Co.Dayton 9, OhioAttn: Mr. B. Treadwell

Callery Chemical CompanyResearch and DevelopmentCallery, Pennsylvania3Attn: Document ControlPennsalt Chemicals CorporationBox 4388Philadelphia 18, PennsylvaniaAttn: Dr. G. Barth-Wehrenalp

Space Technology Laboratory, Inc.5730 Arbor-Vitae StreetLos Angeles 45, CaliforniaAttn: Mr. Robert C. Anderson

Aeroprojects, Inc.310 East Rosedale AvenueWest Chester, PennsylvaniaAttn: C. D. McKinney

United Technology Corp.P. 0. Box 358Sunnyvale, CaliforniaAttn: Librarian

Aerojet-General Corporation11711 South Woodruff AvenueDowney, CaliforniaAttn: FlorenceWalsh, LibrarianI

I

Aerospace CorporationP. 0. Box 95085Los Angeles 45, CaliforniaAttn: Library-Documents 2

Thiokol Chemical CorporationRocket Operations CenterP.O. Box 1640Ogden, UtahAttn: Librarian 1

Bureau of Naval WeaponsDepartment of the NavyWashington 25, D. C.Attn: NPP Representative

Room 3002 1

DirectorAdvanced Research Projects AgencyThe Pentagon, Room 3D159Washington 25, D. C.Attn: Advanced Propellant

Chemistry Office 1

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Rocket Power, Inc.3016 Foothill Blvd.Pasadena, California 1

Amcel Propulsion CompanyBox 3049Asheville, N. C. 1

SuperintendentU. S. Naval Weapons Plant (Code 752)Washington 25, D. C. 1

Quality Assurance Department, NPP 1

Production Department, NPP 1

Safety Department, NPP 1

Research and Development Department, NPP 20

Technical Library, NPP 2

NPP Files 5t !I

Commanding GeneralAberdeen Proving GroundMarylandAttn: Ballistic Research Laboratories

ORDBG-BLI 2

Commanding GeneralUSA Ordnance Arsenal, FrankfordPhiladelphia 37, PennsylvaniaAttn: Propellant and Explosives

Section, 1331

Commanding OfficerPicatinny ArsenalDover, New JerseyAttn: Library 2

Commanding GeneralU. S. Army Ordnance Missile CommandRedstone Arsenal, AlabamaAttn: Technical Library 5

Commanding GeneralWhite Sands Missile RangeNew MexicoAttn: ORDBS-OM-TL 3

Commanding OfficerRadford Ordnance PlantRadford, Virginia

Commanding GeneralOrdnance Ammunition CommandJoliet, IllinoisAttn: ORDLY-AREL, Engr. Library

Commanding OfficerDiamond Ordnance Fuze LaboratoriesWashington 25, D. C.Attn: ORDTL (012)

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