US3446620A - Process for developing diazotype materials - Google Patents

Process for developing diazotype materials Download PDF

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Publication number
US3446620A
US3446620A US440752A US3446620DA US3446620A US 3446620 A US3446620 A US 3446620A US 440752 A US440752 A US 440752A US 3446620D A US3446620D A US 3446620DA US 3446620 A US3446620 A US 3446620A
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Prior art keywords
developer
developing
copy
liquid
component
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Expired - Lifetime
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US440752A
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English (en)
Inventor
Konrad Parker
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AB Dick Co
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Multigraphics Inc
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Priority claimed from GB1185565A external-priority patent/GB1102762A/en
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Publication of US3446620A publication Critical patent/US3446620A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
    • C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/76—Benzo[c]pyrans
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
    • G03C5/18—Diazo-type processes, e.g. thermal development, or agents therefor

Definitions

  • This invention relates to methods and compositions for developing diazotype materials. More particularly, it relates to the development of two-component diazotype materials by the application of controlled amounts of a concentrated alkaline liquid producing a finished dry copy directly after said development.
  • Diazo reproduction processes based on light sensitive diazo compounds and their ability to form azo dyes with a coupling component under proper pH conditions are generally well known.
  • the various techniques for carrying out the development include the moist or semi-moist process, the dry or ammonia process, and more recently the thermal process.
  • the copying materials adapted for the moist process are referred to as one-component materials since they contain only the light sensitive com-pounds and the coupling component is provided in a separate buffered developing solution and applied at the time of development.
  • Diazotype materials developed in an atmosphere of water vapor and ammonia gas are generally referred to as two-component materials since they contain both the diazonium salt and the coupling component stabilized against premature coupling in an acidic medium.
  • the one-component systems have effectively eliminated the odor problem by applying liquid developers directly to the copy sheet.
  • Reproduction equipment for use with the one-component type papers requires the use of heating elements in order to dry the copy sheet after development.
  • Another object of this invention is to provide an improved method and compositions for developing two-component diazotype materials by supplying controlled amounts of a concentrated amine solution to a developing region so that the diazo print is rapidly developed, emerging from the developing region in a condition that is dry to the touch.
  • FIGURE 2 is a diagrammatic elevational view of the developing apparatus employed in carrying out the purpose of this invention.
  • the limited quantity of liquid is applied under pressure being spread out uniformly over its entire surface in a layer having a thickness of about 1 micron, which is sufiicient to cause rapid image development.
  • the azo dye image is found to develop up evenly and uniformly everywhere across the copy area indicating the effectiveness of the method.
  • a visible, readable image begins to form instantaneously as the copy emerges from the developing region and increases in density attaining its maximum image density well within one minute and usually within 15 seconds. Understandably, the rate at which maximum density is reached will depend in part on the couplers and diazonium compounds comprising the sensitizing formulation used in making the copy sheets.
  • the condition of the sheet described as being dry may be defined as being dry to the touch as soon as it emerges from the developing region. No further drying is required and the copy may be used immediately.
  • the copies are free of any objectionable odors. They are flat lying, free of curl, cockles or other irregularities that are normally attendant upon paper surfaces to which liquids have been applied. Further, the copies are not limp due to the presence of excess moisture that would prevent them from being filed, folded or handled by the automatic stacking devices of copying equipment.
  • the emerging copies may be written upon with pen or pencil and otherwise handled.
  • reaction is a two-step process, namely:
  • the second reaction or coupling proceeds at a rate determined solely by the particular reactants once the proper pH has been provided.
  • the alkaline liquid developer In any practical developing process the developer must penetrate the surface of the sheet and neutralize the acid uniformly and evenly. It will be appreciated that incomplete neutralization in certain areas will leave the diazo uncoupled and result in an irregularly developed copy. Accordingly, it is critical that the alkaline liquid developer be applied over the entire surface uniformly so as to achieve an even and uniform treatment.
  • the liquid must react rapidly with the acid component; it should not discolor the print "background; and it should not be absorbed into the body of copy material but remain only at the surface thereof. This presents the problem of applying just the right amount of fluid to accomplish development wtihout excessively wetting or saturating the sheet.
  • the composition of the developer liquid will be considered further in greater detail hereinafter.
  • FIGURE 1 there is shown the flow diagram setting forth the steps embodying this invention.
  • a two-component diazotype copy sheet is first exposed to actinic radiation through a suitable translucent original in the conventional manner.
  • the novel developer liquid of this invention is continuously fed to a carrier; thereafter the amount of said liquid is metered to provide the optimum quantity necessary for development; the metered amount of developer is conveyed to the developing region; in the developing region the metered liquid is transferred under pressure to the exposed copy sheet as the latter passes through the developing region from whence it emerges dry and ready for handling.
  • FIGURE 2 there is shown one form of apparatus, identified by the general reference character 20, capable of carrying out the processing steps of the instant invention as shown on the flow diagram in FIG- URE 1.
  • apparatus may be modeled after a conventional offset duplicator such as described in U.S. Patent 2,165,235 which utilizes multiple rollers in conjunction with transfer drums or cylinders to achieve the application of very small quantities of a liquid spread uniformly and evenly over large areas.
  • a pair of rubber covered rolls 22, 24 in conjunction with the rotatable larger diameter drums or cylinders 26, 28 are disposed with their axes in parallel alignment so that their respective surfaces may be brought into rolling contact.
  • Roller 22 is partially immersed along its length in a trough 30 containing a supply of developer liquid 32.
  • Means (not shown) are provided for driving the cylinder 26 and by suitable gearing (not shown), in timed relation with rollers 22, 24 and cylinder 28.
  • Roller 24 oscillates making contact alternately with the surface of rollers 22 and 26 providing a controlled quantity of the developer 32 to the liquid receptive surface of the carrier cylinder 26, which is further controlled at the nip between cylinders 26 and 28.
  • the developer composition must be such that it can rapidly react with the acid component in the diazo coating shifting the pH to the level where the coupling reaction can proceed.
  • the developer should remain stable during use in the apparatus and not undergo degradation due to oxidation caused by atmospheric exposure.
  • the background area of developed prints should not appreciably discolor upon aging so as to reduce print contrast.
  • the image dye lines should correspond to the hues obtainable with ammonia and not be off shade.
  • the concentration of the various ingredients in the composition should not vary due to evaporation at ordinary temperatures or the absorption of water from the atmosphere.
  • the developer should, of course, not have an objectionable odor, be non-toxic, and simple to handle and use.
  • R R and R are members selected from the group consisting of alkyl, cycloalkyl, alkyl-aryl, alkylol, alkoxy, polyol and hydrogen, and
  • amines have been eminently successful in the practice of the method: monoethanolamine; isopropanolamine; 2-(2-aminoethoxy) ethanol; 'triethanolamine; diethanolamine; 2-amino, -2.-methyl, l-propanol; N-methylethanolamine; dime-thylethanolamine; monoisopropanol amine; hexylamine; cyclohexylamine.
  • Other amines have demonstrated the ability to develop the diazo print such as beta hydroxyethyl trimethyl amine; N- aminoethylethanolamine; alkyl substituted morpholine and piperidine; but are somewhat less desirable because they have a detectable odor or they tend to adversely affect the dye shade.
  • a developer comprising 100% amine can be successfully employed in the practice of the aforedescribed method, it has been found advantageous to employ a diluent to bring the concentration of amine within the preferred limits. At 100% concentrations greater demands are placed on the process of this invention to control the amount of developer applied per square meter of the copy paper at the lower part of the range.
  • the use of a diluent provides a greater latitude for the amount of developer liquid that may be applied within the specified range and still provide the optimum amount of amine.
  • the use of a diluent also aids in the spreadability and wetting out of the developer across the area to which it is applied.
  • the diluent may be comprised of a polyhydric alcohol selected from the following:
  • ethylene glycol monoethyl ether diethylene glycol monoethyl ether butyl Cellosolve or a mono-functional alcohol such as:
  • the diluent will range from 20% to by weight of the developer formulation and preferably in the range of 40% to 60% by weight.
  • polyhydric alcohols which are completely compatible with the aliphatic amines and do not adversely affect the print quality.
  • polyhydric alcohols such as, for example, hexylene glycol; and glycol-ethers enhance the spreadability of the developer liquid.
  • the formulation of the diluent depends on the type of equipment employed. Thus, it may be desirable to decrease the viscosity by adding water, a mono-functional alcohol, or mixtures thereof.
  • Example I A diazotype paper was prepared with the following twocomponent sensitizing solution:
  • the above values represent an average of several readings taken on the image using a standard reflectance densitometer and the values are reflectance density units with the instrument calibrated against a magnesium oxide block.
  • the copy was immediately readable upon emerging from the last processing step. Moderate amounts of heat applied at the time of development such as by warming the developer solution or heating the emerging copy will accelerate the azo dye image formation. In the case of black line prints this may be desirable. However, it should be pointed out that use of heat is optional and not neces sary to the successful operation of the process.
  • the copy was dry to the touch, measuring less than 10% in moisture content; it could be handled, written upon with ink or pencil, folded or filed, as required. An examination of the copy after it was aged for a period of several weeks showed no undue discoloration of the background, that is, it was comparable in all respects to diazo prints processed by known conventional developing techniques.
  • Example II A developer of the following formulation was prepared:
  • Example III The developer in this example comprised monoethanolamine.
  • a two-component diazotype copy paper of the type described in Example I was properly exposed. Development was accomplished by the method depicted in FIGURE 1.
  • the print developed in about 8 to 10 seconds showing a pickup of about 0.70 to 0.86 gram per square meter of imaged surface. It had a density of 1.0.
  • Example VII Diethanolamine percent- 40 Diethyleneglycol do- 30 4-methoxy-4 methyl-pentanol-Z do 20 Water do 10 pH 11.7
  • R is alkyl, cycloalkyl, alkyl-aryl, alkylol, alkoxy or polyol and R and R are alkyl, cycloalkyl, alkyl-aryl, alkylol, alkoxy, polyol or hydrogen, to a copy developing region,
  • a method for making reproductions of an original on a two-component diazotype copying material comprising the steps of (a) exposing the copying material to an actinic radiation pattern corresponding to the light and dark areas on said original, producing a latent image thereon,

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
  • Lift Valve (AREA)
US440752A 1965-03-18 1965-03-18 Process for developing diazotype materials Expired - Lifetime US3446620A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US44075265A 1965-03-18 1965-03-18
GB1185565A GB1102762A (en) 1965-03-19 1965-03-19 Phthalane, isochromane and isochromene derivatives
US75950368A 1968-09-12 1968-09-12

Publications (1)

Publication Number Publication Date
US3446620A true US3446620A (en) 1969-05-27

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Application Number Title Priority Date Filing Date
US440752A Expired - Lifetime US3446620A (en) 1965-03-18 1965-03-18 Process for developing diazotype materials
US540438A Expired - Lifetime US3467675A (en) 1965-03-18 1966-03-03 Antidepressant basic derivatives of phthalanes,iso-chromanes and iso-chromenes
US759503A Expired - Lifetime US3578452A (en) 1965-03-18 1968-09-12 Developing compositions for diazotype materials

Family Applications After (2)

Application Number Title Priority Date Filing Date
US540438A Expired - Lifetime US3467675A (en) 1965-03-18 1966-03-03 Antidepressant basic derivatives of phthalanes,iso-chromanes and iso-chromenes
US759503A Expired - Lifetime US3578452A (en) 1965-03-18 1968-09-12 Developing compositions for diazotype materials

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US (3) US3446620A (ru)
BE (2) BE677903A (ru)
BR (3) BR6677980D0 (ru)
CH (2) CH491102A (ru)
DE (3) DE1543715C3 (ru)
DK (3) DK134415B (ru)
FI (2) FI48731C (ru)
FR (1) FR5873M (ru)
GB (2) GB1143702A (ru)
MY (2) MY7300009A (ru)
NL (3) NL6603604A (ru)
NO (3) NO123675B (ru)
SE (3) SE326193B (ru)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3661590A (en) * 1970-08-14 1972-05-09 Addressograph Multigraph Two component diazo-type developing process
US4035186A (en) * 1974-11-20 1977-07-12 Allan Robert Andrew Beeber Process for the development of diazotype materials
US4043816A (en) * 1972-05-26 1977-08-23 Oce-Van Der Grinten N.V. Photographic process for making diazotype copies utilizing small quantity of liquid developer
US4053314A (en) * 1974-08-09 1977-10-11 Kabushiki Kaisha Bunshodo Amine developer liquid for diazotype reproduction
JPS5344036A (en) * 1976-10-04 1978-04-20 Mita Industrial Co Ltd Developing device of wet copying machine
US4090879A (en) * 1976-11-15 1978-05-23 Gaf Corporation Developing solutions for 2-component diazo-type materials
US20090069582A1 (en) * 2007-09-11 2009-03-12 H. Lundbeck A/S Method for manufacture of escitalopram

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US3883551A (en) * 1969-08-25 1975-05-13 Little Inc A Thienobenzopyrans and thiopyranobenzopyrans
US3670088A (en) * 1969-10-14 1972-06-13 Ayerst Mckenna & Harrison Method of treating hyperchlorhydria and/or associated conditions
US3880885A (en) * 1971-11-23 1975-04-29 Sandoz Ag Tertiary aminoethyl isochromans and isocoumarins
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US3934024A (en) * 1971-12-20 1976-01-20 Sharps Associates Method of producing analgesia and compositions useful therein
BE794081A (fr) * 1972-01-27 1973-05-16 Cortial Nouveaux produits de reaction entre une amine primaire et un aldehyde
NL172373C (nl) * 1972-05-26 1983-08-16 Oce Van Der Grinten Nv Werkwijze voor het vervaardigen van diazotypkopieen.
NL176020C (nl) * 1974-09-13 1985-02-01 Oce Van Der Grinten Nv Werkwijze voor het vervaardigen van diazotypkopieen, alsmede diazotypmateriaal voor het uitvoeren van deze werkwijze.
DE2628094A1 (de) * 1975-06-30 1977-01-27 Ricoh Kk Nassentwickler zum entwickeln von zweikomponenten-diazotypiematerialien
JPS5919549B2 (ja) * 1976-01-01 1984-05-07 武田薬品工業株式会社 異節環状化合物
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US4487774A (en) * 1977-10-31 1984-12-11 The Upjohn Company Isochromans
US4153612A (en) * 1977-10-31 1979-05-08 The Upjohn Company 2-Benzoxepins
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GB8419963D0 (en) * 1984-08-06 1984-09-12 Lundbeck & Co As H Intermediate compound and method
AU684874B2 (en) * 1993-12-28 1998-01-08 Pharmacia & Upjohn Company Heterocyclic compounds for the treatment of cns and cardiovascular disorders
US5752121A (en) * 1995-09-27 1998-05-12 Eastman Kodak Company Photographic processing apparatus
DK1015416T3 (da) 1997-07-08 2001-11-05 Lundbeck & Co As H Fremgangsmåde til fremstilling af citalopram
UA62985C2 (en) 1997-11-10 2004-01-15 Lunnbeck As H A method for the preparation of citalopram
EA002770B1 (ru) 1997-11-11 2002-08-29 Х.Лундбекк А/С Способ получения циталопрама
KR100411505B1 (ko) 1998-10-20 2003-12-18 하. 룬트벡 아크티에 셀스카브 시탈로프람의 제조방법
AR021509A1 (es) * 1998-12-08 2002-07-24 Lundbeck & Co As H Derivados de benzofurano, su preparacion y uso
CA2356188C (en) 1998-12-23 2006-05-23 H. Lundbeck A/S Method for the preparation of 5-cyanophthalide
AR022329A1 (es) 1999-01-29 2002-09-04 Lundbeck & Co As H Metodo para la preparacion de 5-cianoftalida
ATE237604T1 (de) * 1999-04-14 2003-05-15 Lundbeck & Co As H Verfahren zur herstellung von citalopram
ITMI991579A1 (it) 1999-06-25 2001-01-15 Lundbeck & Co As H Metodo per la preparazione di citalopram
ITMI991581A1 (it) * 1999-06-25 2001-01-15 Lundbeck & Co As H Metodo per la preparazione di citalopram
AR021155A1 (es) * 1999-07-08 2002-06-12 Lundbeck & Co As H Tratamiento de desordenes neuroticos
DE69920526T2 (de) 1999-10-25 2006-02-23 H. Lundbeck A/S Verfahren zur herstellung von citalopram
ES2229774T3 (es) 1999-10-25 2005-04-16 H. Lundbeck A/S Metodo para la preparacion de citalopram.
AR026063A1 (es) 1999-11-01 2002-12-26 Lundbeck & Co As H Metodo para la preparacion de 5-carboxiftalida.
SI1246812T1 (en) 1999-12-28 2004-08-31 H. Lundbeck A/S Method for the preparation of citalopram
HUP0203840A3 (en) 1999-12-30 2005-02-28 Lundbeck & Co As H Method for the preparation of citalopram
IL150561A0 (en) * 2000-01-14 2003-02-12 Lundbeck & Co As H Method for the preparation of 5-cyanophthalide
NL1017415C1 (nl) 2000-02-24 2001-05-18 Lundbeck & Co As H Werkwijze voor de bereiding van Citalopram.
IES20010157A2 (en) 2000-03-03 2002-03-06 Lundbeck & Co As H Method for the preparation of citalopram
CN1429219A (zh) * 2000-03-13 2003-07-09 H·隆德贝克有限公司 制备西酞普兰的方法
IES20010206A2 (en) 2000-03-13 2002-03-06 Lundbeck & Co As H Method for the preparation of citalopram
CA2402553A1 (en) * 2000-03-13 2001-09-20 H. Lundbeck A/S Stepwise alkylation of 5-substituted 1-(4-fluorophenyl)-1,3-dihydroisobenzofurans
GB2357762B (en) * 2000-03-13 2002-01-30 Lundbeck & Co As H Crystalline base of citalopram
ATE257832T1 (de) 2000-03-14 2004-01-15 Lundbeck & Co As H Verfahren zur herstellung von citalopram
TR200202168T2 (tr) * 2000-03-16 2002-12-23 H. Lundbeck A/S 5-Siyano-1-(4-Florofenil)-1,3-Dihidroizobenzofuranların preparasyon metodu
AR032455A1 (es) 2000-05-12 2003-11-12 Lundbeck & Co As H Metodo para la preparacion de citalopram, un intermediario empleado en el metodo, un metodo para la preparacion del intermediario empleado en el metodo y composicion farmaceutica antidepresiva
FI20011621A (fi) 2000-08-18 2002-02-19 Lundbeck & Co As H Menetelmä sitalopraamin valmistamiseksi
EA003581B1 (ru) 2000-12-22 2003-06-26 Х.Лундбекк А/С Способ получения чистого циталопрама
EA003459B1 (ru) * 2000-12-28 2003-06-26 Х.Лундбекк А/С Способ получения чистого циталопрама
EA200301195A1 (ru) * 2001-05-01 2004-04-29 Х. Лундбекк А/С Применение энантиомерно чистого эсциталопрама
EA006213B1 (ru) * 2001-07-31 2005-10-27 Х. Лундбекк А/С Кристаллическая композиция, содержащая эсциталопрам
IN192863B (ru) * 2001-11-13 2004-05-22 Ranbaxy Lab Ltd
CA2381341A1 (en) * 2002-04-09 2003-10-09 Torcan Chemical Ltd. Process and intermediates for preparing escitalopram
AU2003237492A1 (en) * 2002-06-10 2003-12-22 Acadia Pharmaceuticals Inc. Urotensin ii receptor modulators
US6812355B2 (en) 2002-10-22 2004-11-02 Sekhsaria Chemicals Limited Process for the manufacture of citalopram hydrobromide from 5-bromophthalide
JP2006520328A (ja) * 2003-02-19 2006-09-07 アカディア ファーマシューティカルズ，インコーポレーテッド ウロテンシンｉｉとソマトスタチン５受容体に対するリガンドの活性基に対する組み合わせ足場アプローチ

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US3661590A (en) * 1970-08-14 1972-05-09 Addressograph Multigraph Two component diazo-type developing process
US4043816A (en) * 1972-05-26 1977-08-23 Oce-Van Der Grinten N.V. Photographic process for making diazotype copies utilizing small quantity of liquid developer
US4053314A (en) * 1974-08-09 1977-10-11 Kabushiki Kaisha Bunshodo Amine developer liquid for diazotype reproduction
US4035186A (en) * 1974-11-20 1977-07-12 Allan Robert Andrew Beeber Process for the development of diazotype materials
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US4090879A (en) * 1976-11-15 1978-05-23 Gaf Corporation Developing solutions for 2-component diazo-type materials
US20090069582A1 (en) * 2007-09-11 2009-03-12 H. Lundbeck A/S Method for manufacture of escitalopram
US8022232B2 (en) 2007-09-11 2011-09-20 H. Lundbeck A/S Method for manufacture of escitalopram

Also Published As

Publication number Publication date
BE677903A (ru) 1966-09-01
SE326194B (ru) 1970-07-20
DE1543715B2 (de) 1973-09-20
GB1143703A (ru)
DK114981B (da) 1969-08-25
DK134415C (ru) 1977-04-04
NO118710B (ru) 1970-02-02
MY7300009A (en) 1973-12-31
DE1543714B2 (de) 1974-11-14
FI48731C (fi) 1974-12-10
FI48730C (fi) 1974-12-10
US3467675A (en) 1969-09-16
DE1543714C3 (de) 1975-07-24
FR5873M (ru) 1968-03-18
NL6603606A (ru) 1966-09-20
BR6677980D0 (pt) 1973-09-11
SE327141B (ru) 1970-08-10
DK134415B (da) 1976-11-01
DE1543714A1 (de) 1970-01-02
SE326193B (ru) 1970-07-20
DK112531B (da) 1968-12-23
GB1143702A (ru)
FI48730B (ru) 1974-09-02
NL6603604A (ru) 1966-09-19
MY7300010A (en) 1973-12-31
CH491102A (de) 1970-05-31
DE1522449A1 (de) 1970-07-30
BR6677982D0 (pt) 1973-09-11
CH475232A (de) 1969-07-15
FI48731B (ru) 1974-09-02
DE1543715A1 (de) 1971-12-02
NL6603603A (ru) 1966-09-20
NO118709B (ru) 1970-02-02
NO123675B (ru) 1971-12-27
BE678035A (ru) 1966-09-19
BR6677971D0 (pt) 1973-03-08
DE1543715C3 (de) 1974-04-18
DE1522449C3 (de) 1981-09-03
DE1522449B2 (de) 1975-03-06
US3578452A (en) 1971-05-11

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