EP0026744B2 - Mittel und Verfahren zur Behandlung und Verbesserung des Aussehens von Textilien - Google Patents

Mittel und Verfahren zur Behandlung und Verbesserung des Aussehens von Textilien Download PDF

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Publication number
EP0026744B2
EP0026744B2 EP80810299A EP80810299A EP0026744B2 EP 0026744 B2 EP0026744 B2 EP 0026744B2 EP 80810299 A EP80810299 A EP 80810299A EP 80810299 A EP80810299 A EP 80810299A EP 0026744 B2 EP0026744 B2 EP 0026744B2
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EP
European Patent Office
Prior art keywords
detergent
soaking
liquor
rinsing
hydrogen
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
EP80810299A
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German (de)
English (en)
French (fr)
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EP0026744A1 (de
EP0026744B1 (de
Inventor
Claude Dr. Eckhardt
Richard Dr. von Rütte
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis AG
Original Assignee
Ciba Geigy AG
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Publication date
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Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Priority to AT80810299T priority Critical patent/ATE974T1/de
Publication of EP0026744A1 publication Critical patent/EP0026744A1/de
Publication of EP0026744B1 publication Critical patent/EP0026744B1/de
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0063—Photo- activating compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/40—Dyes ; Pigments
    • C11D3/42—Brightening agents ; Blueing agents

Definitions

  • the present invention relates to an agent for improving the appearance of used, in particular soiled textiles, especially soaking, washing or rinsing agents, and to a method for improving the appearance of textiles with the aid of the agents according to the invention.
  • photosensitizing compounds i.e. especially dyes that catalyze oxidation processes under the influence of light can be used for bleaching textiles. These compounds can be contained in soaking, washing, rinsing or other cleaning agents or they are used in a separate bleaching process. See British Patent 1372036, US Patent 3,927,967, German Offenlegungsschriften 2613936 and 2812278.
  • the corresponding photosensitizing compound or a soaking, washing, rinsing or cleaning agent containing it is added to an aqueous liquor in which the bleached fabrics soaked, washed, rinsed or otherwise cleaned.
  • the textiles must be irradiated with light during the treatment.
  • a corresponding lamp can be used for this purpose, or, particularly advantageously, in particular with regard to energy consumption, daylight can be used for the irradiation.
  • Irradiation can take place during the treatment of the textiles in the bathroom (e.g. in the bleaching, soaking, washing or rinsing bath) or after the treatment outside the bath.
  • the still damp textiles can be exposed to sunlight, e.g. while drying on a leash. Irradiation can also be carried out, if necessary, with repeated rewetting of the textiles.
  • the present invention accordingly consists first of all in a means of improving the appearance of used, in particular soiled, textiles, which comprises 0.0001 to 1%, preferably 0.001 to 0.1% of a photoactivator and 0.005 to 1.5%, preferably 0.01 to 0.5%, based in each case on the total weight of the composition, sulfonic acids distyrylbiphenyl of an optical brightener of the class of acids and salts thereof and / or the 4,4 1- bis- (1,2,3-triazot-2-yl) -2.2 1- stilbene-sulfonic acids or their salts, it also being possible for mixtures of several brighteners to be present, and excluding those agents which are a combination of zinc phthalocyanitri- and tetrasulfonate and 4,4'-bis- ( Contain 2-sulfostyryl) biphenyl.
  • Both metal-free phthalocyanines and metal complexes of phthalocyanines can be used as water-soluble phthalocyanines.
  • those of Al, Zn, Mg, Ca, Fe, Na, K, preferably Al and Zn, are used as metal complexes.
  • mixtures of photoactivators can also be used, e.g. Mixtures of various phthalocyanine compounds, such as mixtures of water-soluble Zn and Al phthalocyanines.
  • X and Y are preferably -NH- or -N-alkyl.
  • Halogen is preferably chlorine or bromine, especially chlorine.
  • the morpholine, piperidine, pyrazolidine, piperazine and oxazolidine radical are preferred.
  • the number of substituents present in the molecule is determined by achieving sufficient water solubility. If there are several water-solubilizing groups in the molecule, these can be the same or different. As is common in phthalocyanine chemistry, the degree of substitution does not necessarily have to be an integer, since the manufacturing method, e.g. Sulfonation does not always result in uniform products. In general, the total number of water-solubilizing substituents per molecule is between 1 and 4.
  • the phthalocyanines which can be used in the agents according to the invention can also contain other substituents, for example reactive residues customary in dye chemistry, such as chloropyrazine, chloropyrimidine and especially chlorotriazine residues.
  • any other substituents can also be present in addition to the water-solubilizing groups, at most in a number such that they do not fall below the required water solubility. However, they can also only be present in very small amounts, for example about 0.1 mol per mol of phthalocyanine compound.
  • substituents are: halogen atoms (including F and J), cyano, optionally substituted alkyl, alkoxy, optionally substituted phenyl and other substituents customary in phthalocyanine chemistry.
  • Preferred additional substituents are fluorine, chlorine, bromine, iodine and cyano, especially chlorine.
  • the molecule contains an anion X to saturate the third valence of the aluminum ion, which is not important for the bleaching effect.
  • This anion is mostly identical to that of the aluminum compound used to make the complex.
  • Particularly preferred photoactivators are aluminum and zinc phthalocyanine di, tri and tetrasulfonates and their salts, which optionally also have an additional substituent, e.g. contain a halogen, especially chlorine.
  • Phthalocyanine compounds which are contained in agents according to the invention as a photoactivator and which contain other substituents in addition to the water-solubilizing groups can also be obtained by customary methods.
  • these substituents may already be present in the starting materials used for the construction of the phthalocyanine ring structure (for example phthalic anhydride, phthalonitrile or imide).
  • the water-solubilizing groups can be introduced (for example by sulfonation), provided that these were not already present in the starting materials.
  • the water-solubilizing substituents can be before or before are preferably introduced subsequently, for example by sulfonation, provided that the phthalocyanine ring system is built up from phthalic anhydride or phthalodinitrile in the presence of chlorides, for example AICI 3 , ZnC1 2 and others, chlorinated phthalocyanines are formed, especially with a chlorine content of 0.5-1.5 Moles of chlorine per mole of phthalocyanine.
  • the water-solubilizing groups can also be introduced subsequently into such products, for example by sulfonation.
  • the methods mentioned can be combined in a suitable manner for the production of mixed-substituted phthalocyanine compounds. All methods are well known in phthalocyanine chemistry and are described in detail there.
  • Brighteners from the class of distyrylbiphenylsulfonic acids which are contained in the agents according to the invention are, above all, those of the formula mentioned, wherein X, hydrogen, chlorine, bromine or alkyl or alkoxy each having 1 to 4 carbon atoms, X 2 hydrogen or alkyl having 1 to 4 carbon atoms and M hydrogen, an alkali metal, ammonium or amine salt ion.
  • alkali metal ions M in formula (20) Na and K are preferred.
  • Suitable amine salt ions M are mainly those of the formula -HNR 1 R 2 R 3 , in which R 1 and R 2 are hydrogen or optionally substituted alkyl and R 3 is optionally substituted alkyl.
  • R 1 and R 2 are hydrogen or optionally substituted alkyl
  • R 3 is optionally substituted alkyl.
  • substituted alkyl radicals which preferably have 1 to 4 carbon atoms in the alkyl part, particular mention should be made of hydroxyalkyl, cyanoalkyl, haloalkyl and benzyl.
  • M is preferably hydrogen, sodium, potassium or ammonium.
  • Brighteners of the formula are preferred used, wherein X, hydrogen or chlorine and M 'is hydrogen, sodium, potassium or ammonium, in particular the brightener of the formula where M "is hydrogen, sodium or potassium.
  • the brightener As a brightener from the class of 4,4'-bis- (1,2,3-triazol-2-yl) -2,2'-stilbenesulfonic acids, which are also contained in agents according to the invention, the brightener of the formula in particular mentioned, wherein M represents hydrogen, an alkali metal, ammonium or amine salt ion.
  • M represents hydrogen, an alkali metal, ammonium or amine salt ion.
  • Mixtures of the aforementioned brighteners can of course also be incorporated into the agents according to the invention, in particular mixtures of the brighteners of the formulas (22) and (24), but also mixtures of the brighteners of the formulas (22) and (23).
  • brighteners from other classes can also be included in the agents according to the invention.
  • the agents according to the invention which are used to improve the appearance of used, in particular soiled, textiles are, for example, soaking, washing, rinsing or other cleaning agents. Accordingly, the agents according to the invention contain, in addition to brighteners and photoactivators, as a supplement to 100% constituents, as are customary in such agents. In general, such constituents are primarily anionic, non-ionic or mixtures of anionic and nonionic surface-active substances.
  • Detergents according to the invention which can be liquid or solid, preferably contain, in addition to brightener and photoactivator, an organic detergent or mixtures of several detergents (preferably anionic and / or nonionic), so-called “builders” (in the case of solid detergents), redeposition inhibitors and, if appropriate, foam stabilizers , Enzymes, antimicrobials, perfumes, additional bleaches and / or additional optical brighteners and water (especially in the case of liquid detergents).
  • Soaking agents according to the invention contain, in addition to brighteners and photoactivators, similar components to those mentioned above for the corresponding detergents. Soaking agents may contain enzymes in larger quantities than corresponding detergents. -
  • the salt content e.g. Na sulfate
  • the salinity By varying the salinity, an optimal effect of the photoactivator can be set.
  • the agents according to the invention can be produced without problems by all methods customary in the detergent industry, be they liquid formulations or powders or granules.
  • the good heat resistance of the components essential to the invention also allows them to be added to the slurry of washing powder, which can be dried by spray drying.
  • the invention further relates to aqueous soaking, washing or rinsing liquors which contain 0.001 to 100 ppm, preferably 0.01 to 10 ppm of a photoactivator and 0.05 to 150 ppm, preferably 0.1 to 50 ppm, in each case based on the total liquor, an optical brightener from the class of distyrylbiphenylsulfonic acids and their salts and / or 4,4'-bis (1,2,3-triazol-2-yl) -2,2'- stilbene sulfonic acids or their salts, which may also contain mixtures of several brighteners, and excluding soaking, washing and rinsing liquors which contain a combination of zinc phthalocyanine tri and tetrasulfonate and 4,4'-bis (2- contain sulfostyryl) biphenyl.
  • an optical brightener from the class of distyrylbiphenylsulfonic acids and their salts and / or 4,4'-
  • Brighteners and photoactivators in the fleets according to the invention are the same as those defined above for the agents according to the invention.
  • the fleets according to the invention are e.g. obtained by dissolving or dispersing the agents according to the invention in water.
  • the individual constituents can be dissolved or dispersed individually or in groups in water, whereupon the liquors according to the invention are formed.
  • a known soaking, washing or rinsing agent can be processed into a corresponding liquor and the photoactivator (s) and the brightener (s) added subsequently in the amount defined above. It is essential that the finished liquors contain photo activator and brightener in the specified concentration.
  • the invention also relates to a process for improving the appearance of used, in particular soiled, textiles, which is characterized in that the textiles are treated in the presence of oxygen with a liquor which contains an agent according to the invention and the textiles are directly in the liquor or in irradiated with light when wet outside the fleet.
  • the textiles are soaked, washed or rinsed in an aqueous liquor according to the invention (as described above).
  • the exposure required to develop the effect of the photoactivator can be achieved with an artificial light source that emits light e.g. supplies in the visible and / or infrared range (e.g. incandescent lamp, infrared lamp), whereby the bathroom can be directly irradiated, either by a light source inside the container in which the liquor is located (e.g. lamp in the washing machine), or by a light source outside the container.
  • the irradiation can also take place only after the textiles have been removed from the treatment bath. In this case, however, the textiles should still be damp or they must be moistened again afterwards.
  • sunlight can also serve as the light source, the textiles preferably being exposed to the sunlight in a moist state after treatment in the washing or bleaching bath.
  • the textiles can preferably be exposed to daylight during drying, for example on a clothesline.
  • the ancestor according to the invention is expediently carried out at temperatures in the range from about 10 to 100, in particular from 10 to 85 ° C., for a period of from 15 minutes to 5 hours, preferably from 15 minutes to 60 minutes.
  • a detergent slurry consisting of 50 parts of deionized water and 50 parts of a detergent of the following composition is produced:
  • the zinc phthalocyanine tetrasulfonate, hereinafter referred to as ZnPCS is used in a concentration of 0.07%.
  • an aluminum phthalocyanine of the formula is used as the photoactivator instead of aluminum phthalocyanine tetrasulfonate (AI PC) - unsubstituted aluminum phthalocyanine) used (concentration also 0.03%).
  • AI PC aluminum phthalocyanine tetrasulfonate
  • AIPCS is always also to be understood as the compound of the formula (25).
  • the photoactivator and brightener are added to the above-defined detergent slurry, which does not yet contain these two components, with largely no light and dried in a drying box and a vacuum of approx. 400 torr at 80 ° C. for 4 hours.
  • the detergent crusts obtained are then pressed through a sieve, beneath which another sieve is located, so that a uniform-grain washing powder is produced.
  • Test strips from the soiled fabrics just described are each washed in a liquor containing 4 g per liter of the detergent defined above at a liquor ratio of 1:20 for 30 minutes at 50 ° C., then rinsed briefly and suspended on a leash in the daylight and then Let dry for 6 hours (equivalent to about 250 Langley).
  • An alkaline solution (pH 9, corresponds to that of the wash liquor) is sprayed every 40 minutes.
  • the washing tests are carried out by varying the photoactivator and / or the optical brightener, with all tests to be compared being carried out in parallel and simultaneously for each type of soiling.
  • the following table lists the composition of the detergent with regard to photoactivator and optical brightener (photoactivator / brightener combinations).
  • Example 1 The same detergent compositions are used under the same test conditions as in Example 1. However, a cotton fabric is washed which has been soiled with a brown dye in accordance with Example 9 of German Offenlegungsschrift 2812278. Because of the coloration achieved in this way, bleaching results which are very reproducible are obtained.
  • the rags from Example 4 are also examined for their basic white in order to check the actual dirt removal. This is done by measuring the reflection at 460 nm (R value) with xenon lighting with the addition of a UV blocking filter, in accordance with DIN 44983. The brightener is therefore not excited and only the basic white is determined. The results are shown in the following table IV specified. While there is no influence on the base whiteness of the brightener C, on the other hand, surprisingly, the two brighteners which are contained in the agents according to the invention surprisingly produce an additional bleaching effect which is significantly higher than that achieved by the photoactivator.
  • Examples 1 to 5 aluminum phthalocyanine tetrasulfonate or the compound of the formula (25) (AIPCS) is replaced by a photoactivator of the formula (AlPC) Br (SO 3 H) 3.5-4 , (AlPC) F (SO 3 H) 3.5-4, (AlPC) J (SO 3 H) 3.5-4 , (ZnPC) -Br (SO 3 H) 3.5-4 or (ZnPC) J (SO 3 H) 3, 5-4 replaced (AIPC and ZnPC means the Al- and Zn-phthalocyanine ring system), you get similar results as those given in Examples 1 and 2 and in Tables II to IV.
  • the 6 cotton flaps are then subjected to a 10th wash cycle (as described), which is however stopped after spinning.
  • the 6 spin-damp cloths are now observed in bundle form, also looking into the bundle (according to the process when the housewife takes the washed bundle of laundry from the washing machine and looks at it).
  • the damp bundle of the 6 cotton flaps which was washed with the detergent containing the combination (5), shows an unsightly yellowish aspect (both after washing at 30 ° C. and after washing at 60 ° C.).

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
EP80810299A 1979-09-28 1980-09-22 Mittel und Verfahren zur Behandlung und Verbesserung des Aussehens von Textilien Expired EP0026744B2 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT80810299T ATE974T1 (de) 1979-09-28 1980-09-22 Mittel und verfahren zur behandlung und verbesserung des aussehens von textilien.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH878979 1979-09-28
CH8789/79 1979-09-28

Publications (3)

Publication Number Publication Date
EP0026744A1 EP0026744A1 (de) 1981-04-08
EP0026744B1 EP0026744B1 (de) 1982-05-05
EP0026744B2 true EP0026744B2 (de) 1984-10-10

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ID=4344750

Family Applications (1)

Application Number Title Priority Date Filing Date
EP80810299A Expired EP0026744B2 (de) 1979-09-28 1980-09-22 Mittel und Verfahren zur Behandlung und Verbesserung des Aussehens von Textilien

Country Status (23)

Country Link
US (1) US4311605A (el)
EP (1) EP0026744B2 (el)
JP (1) JPS5679199A (el)
AR (1) AR225462A1 (el)
AT (1) ATE974T1 (el)
AU (1) AU538198B2 (el)
BR (1) BR8006210A (el)
CA (1) CA1151807A (el)
CS (1) CS214758B2 (el)
DE (1) DE3060373D1 (el)
DK (1) DK408080A (el)
ES (1) ES8105421A1 (el)
GR (1) GR70214B (el)
IE (1) IE50316B1 (el)
IL (1) IL61138A (el)
IN (1) IN153407B (el)
MA (1) MA19033A1 (el)
MX (1) MX152717A (el)
NZ (1) NZ195065A (el)
PH (1) PH19186A (el)
PL (1) PL125119B1 (el)
PT (1) PT71815B (el)
ZA (1) ZA805979B (el)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IN155696B (el) * 1980-09-09 1985-02-23 Ciba Geigy Ag
EP0054992B1 (en) * 1980-12-22 1985-03-20 Unilever N.V. Composition containing a photo-activator for improved bleaching
JPS5842699A (ja) * 1981-09-07 1983-03-12 花王株式会社 衣料用洗剤組成物
CH654121A5 (de) * 1983-03-25 1986-01-31 Ciba Geigy Ag Verfahren zur herstellung von festen photoaktivatorpraeparaten.
US4549980A (en) * 1983-10-11 1985-10-29 Mobay Chemical Corporation White modification of a bis-triazinyl amino stilbene optical brightener and a process for making the same
US4526700A (en) * 1983-11-04 1985-07-02 The Procter & Gamble Company Hypochlorite bleach compositions containing optical brighteners
CH657864A5 (de) * 1984-02-17 1986-09-30 Ciba Geigy Ag Wasserloesliche phthalocyaninverbindungen und deren verwendung als photoaktivatoren.
EP0165115B1 (fr) * 1984-05-15 1987-10-14 Rhone-Poulenc Chimie Composition détergente pour blanchiment par photoactivation et son procédé d'utilisation
DE3585512D1 (de) * 1984-12-28 1992-04-09 Procter & Gamble Fluessiges hypochlorit-bleichmittel, enthaltend optische aufheller, geloest in aminoxid.
US4900469A (en) * 1986-10-21 1990-02-13 The Clorox Company Thickened peracid precursor compositions
US4764302A (en) * 1986-10-21 1988-08-16 The Clorox Company Thickening system for incorporating fluorescent whitening agents
US4925595A (en) * 1987-07-03 1990-05-15 Ciba-Geigy Corporation Liquid detergent compositions containing disulfonated fluorescent whitening agents: di-styryl-biphenyl or di-styryl-benzene derivatives
DE4230655A1 (de) * 1992-09-14 1994-03-17 Ciba Geigy Verfahren zur Verbesserung von Weißgrad, Helligkeit und Farbort von Faserstoffen
DE4230656A1 (de) * 1992-09-14 1994-03-17 Ciba Geigy Verfahren zur Verbesserung von Weissgrad, Helligkeit und Farbort von Füllstoffen und Pigmenten
ATE190087T1 (de) * 1994-08-30 2000-03-15 Procter & Gamble Mittels chelatbildnern verbessertes photobleichen
WO1997031994A1 (en) * 1996-03-01 1997-09-04 The Procter & Gamble Company Chelant enhanced photobleaching
US6099589A (en) * 1997-12-30 2000-08-08 Kay Chemical Company Presoak detergent with optical brightener
WO2001066681A1 (en) * 2000-03-08 2001-09-13 Ciba Specialty Chemicals Holding Inc. Use of optical brighteners from the class of the stilbene compounds as antimicrobially active substances
EP1651744A1 (en) * 2003-08-06 2006-05-03 The Procter & Gamble Company Composition for treating textilescomprising a photo bleaching component and a fluorescent whitening component
US20050288200A1 (en) * 2004-06-24 2005-12-29 Willey Alan D Photo Bleach Compositions
KR102332837B1 (ko) 2012-05-16 2021-12-01 테크필즈 파마 코., 엘티디. 폐 병태의 치료를 위한 고침투 전구약물 조성물 및 그의 약제학적 조성물

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH1275170A4 (el) * 1970-08-26 1975-03-27
GB1372035A (en) * 1971-05-12 1974-10-30 Procter & Gamble Ltd Bleaching process
US4033718A (en) * 1973-11-27 1977-07-05 The Procter & Gamble Company Photoactivated bleaching process
CH630127A5 (de) * 1977-03-25 1982-05-28 Ciba Geigy Ag Verfahren zum bleichen von textilien.
GR65653B (en) * 1978-01-11 1980-10-16 Procter & Gamble Composition for combined washing and whitening cloths
US4298490A (en) * 1978-12-22 1981-11-03 Ciba-Geigy Corporation Process for the production of washing powders of stabilized or enhanced appearance which contain fluorescent whitening agents
US4309316A (en) * 1978-12-22 1982-01-05 Ciba-Geigy Corporation Process for the production of washing powders of stabilized or enhanced appearance which contain fluorescent whitening agents

Also Published As

Publication number Publication date
NZ195065A (en) 1982-09-07
ATE974T1 (de) 1982-05-15
IL61138A (en) 1984-06-29
DE3060373D1 (en) 1982-06-24
CA1151807A (en) 1983-08-16
EP0026744A1 (de) 1981-04-08
ES495431A0 (es) 1981-06-01
AU538198B2 (en) 1984-08-02
BR8006210A (pt) 1981-04-07
ES8105421A1 (es) 1981-06-01
IN153407B (el) 1984-07-14
PH19186A (en) 1986-01-23
PL226937A1 (el) 1981-07-10
PL125119B1 (en) 1983-03-31
ZA805979B (en) 1981-09-30
DK408080A (da) 1981-03-29
AU6275980A (en) 1981-04-09
IE802015L (en) 1981-03-28
GR70214B (el) 1982-08-31
IE50316B1 (en) 1986-04-02
US4311605A (en) 1982-01-19
CS214758B2 (en) 1982-05-28
MX152717A (es) 1985-10-21
JPS5679199A (en) 1981-06-29
IL61138A0 (en) 1980-11-30
EP0026744B1 (de) 1982-05-05
PT71815A (en) 1980-10-01
PT71815B (en) 1981-07-07
MA19033A1 (fr) 1981-04-01
AR225462A1 (es) 1982-03-31

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