EP0043790B1 - Procédé d'augmentation ou d'amélioration de l'effet de blanchiment lors du blanchiment optique de compositions d'enduction - Google Patents

Procédé d'augmentation ou d'amélioration de l'effet de blanchiment lors du blanchiment optique de compositions d'enduction Download PDF

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Publication number
EP0043790B1
EP0043790B1 EP81810008A EP81810008A EP0043790B1 EP 0043790 B1 EP0043790 B1 EP 0043790B1 EP 81810008 A EP81810008 A EP 81810008A EP 81810008 A EP81810008 A EP 81810008A EP 0043790 B1 EP0043790 B1 EP 0043790B1
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Prior art keywords
formula
acid
coating
amine
fluorescent whitening
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Expired
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EP81810008A
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German (de)
English (en)
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EP0043790A1 (fr
Inventor
Werner Dr. Fringeli
Max Flubacher
Alain Dr. Lauton
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Novartis AG
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Ciba Geigy AG
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Priority to AT81810008T priority Critical patent/ATE8516T1/de
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Classifications

    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
    • D21H21/30—Luminescent or fluorescent substances, e.g. for optical bleaching
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H19/00—Coated paper; Coating material
    • D21H19/36—Coatings with pigments
    • D21H19/44—Coatings with pigments characterised by the other ingredients, e.g. the binder or dispersing agent
    • D21H19/62—Macromolecular organic compounds or oligomers thereof obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds

Definitions

  • the present invention relates to a method for increasing or improving the white effect in the optical brightening of coating slips for the coating of paper or cardboard with the aid of brighteners of the bis-triazinylaminostilbene-2,2'-disulfonic acid series and optically brightened coating slips and paper coated with these coating slips or box.
  • Brighteners from the class of bis-triazinylaminostilbene-2,2'-disulfonic acids are also suitable for lightening paper.
  • problems occur depending on the brightener and the composition of the coating slip, so that either insufficient white effects are obtained or that some brighteners are out of the question for application in certain coating slips.
  • Particularly at higher brightener concentrations there is often a sharp decrease in the degree of whiteness instead of an increase in the degree of whiteness, with the coating composition often becoming greener. This undesirable effect occurs in some of the brighteners mentioned, particularly in the case of coating slips with artificial binders.
  • DE-A-2 806 194 and 2 806 195 disclose coating compositions to which a dispersion brightener, but also bis-triazinylaminostilbene-2,2'-disulfonic acid brightener, mixed with water, an organic liquid boiling above 150 ° C., e.g. B. triethyl phosphate, trioctyl phosphate, tricresyl phosphate or trichloroethyl phosphate, and a solubilizer, for. B. a nonionic emulsifier is added.
  • This method is mainly suitable for dispersion brighteners.
  • the use of relatively expensive, high-boiling organic solvents is not advantageous for various reasons.
  • DE-A-2 412 785 describes a process for optically brightening cellulose and polyamide textiles in which certain oxyalkylation products of fatty amines, optionally esterified with sulfuric acid, are used as auxiliaries. By using these aids, the maximum white that can be achieved on textiles can be increased slightly. An application in the paper sector is not mentioned.
  • this object was achieved by adding an acidic phosphoric acid ester of a fatty amine oxalkylation product of the formula (1) below to the coating slip in addition to the brightener.
  • This measure significantly improves the whiteness of the lightened coating slips, in particular at higher brightener concentrations, and the undesired greening is avoided.
  • the degree of whiteness increases practically linearly with the logarithm of the increasing brightener concentration, so that very high degrees of whiteness can be achieved.
  • the process for increasing or improving the white effect in the optical brightening of coating slips for the coating of paper or cardboard with the aid of brighteners of the bis-triazinylamino-2,2'-disutonic acid series is now characterized in that the coating slips are in addition to the respective Brightener an acidic phosphoric acid ester of a fatty amine oxyalkylation product of FormAl or incorporates its alkali metal, ammonium or amine salt, in which R is an aliphatic hydrocarbon radical having 8-22 carbon atoms, Y 1 and Y 2 are both hydrogen or one of these two symbols is hydrogen and the other methyl, X is the acid radical of phosphoric acid, the acidic hydrogen atoms of this radical can be replaced by alkali metal, ammonium or amine salt ions, and m and n are integers, the sum n + m being between 2 and 30.
  • the aliphatic radical R preferably denotes an alkyl or alkenyl radical (branched or unbranched) having 10 to 18 carbon atoms.
  • R ' is an alkyl or alkenyl radical having 10 to 18 carbon atoms
  • X' is the acid radical of phosphoric acid
  • the acidic hydrogen atoms of this radical can also be replaced by alkali metal or ammonium ions
  • n 'and m' are integers, where the sum n '+ m' is between 4 and 20.
  • the radical R need not have a certain number of carbon atoms, but can also be a mixture of hydrocarbon chains of different lengths, as is the case with many fatty amines derived from natural fats.
  • a preferred residue of this type is the hydrocarbon residue of tallow fatty amine.
  • V I and Y 2 are preferably hydrogen.
  • the acid component of the ester of formula (1) is phosphoric acid.
  • X is therefore the rest of the phosphoric acid, and the terminal OH groups of the ethylene oxide or propylene oxide chains can be completely or only partially esterified.
  • the number of acidic hydrogen atoms in the phosphoric acid residue X depends on the degree of esterification, which need not be an integer. These acidic hydrogen atoms can also be replaced by alkali metal, ammonium or amine salt ions, so that the residue X is in salt form. However, the radical X is preferably in its acidic form.
  • a brightener of the formula is preferably used wherein R;
  • R 2 or and M ' represents hydrogen or an alkali metal ion, ammonium, diethanolammonium or triethanolammonium.
  • M denotes an alkali metal ion, in particular a sodium, potassium ion, an ammonium ion or an, amine salt ion, e.g. B. a primary or secondary alkylamine, the alkyl group (s) by halogen.
  • Hydroxy e.g. ethanolamine, diethanolamine, triethanolamine
  • alkoxy may be substituted or a cyclic amine e.g. B. a piperidine, pyrrolidine, piperazine or morpholine.
  • the acidic hydrogen atoms in the phosphoric acid residue X of the compounds of formula (1) or (2) can optionally be replaced by the same ions as defined for M above.
  • the rest X is then in salt form.
  • Non-ionic or anionic surfactants, organic solubilizers and / or certain organic polar compounds can be considered as such additional aids.
  • the acidic phosphoric acid esters of fatty amine oxalkylation products of the formula (1) used in the process according to the invention are known and can be obtained simply by esterification of a fatty amine oxalkylation product of the formula wherein the general symbols as defined in formula (1) can be obtained with phosphoric acid, phosphorus pentoxide or a halide of phosphoric acid.
  • the reaction with phosphorus pentoxide is preferred.
  • the esterification is advantageously carried out by simply mixing the reaction 'partner under heating, z. B. to 50-100 "C.
  • the acidic esters can be converted into the corresponding salts (alkali metal, ammonium or amine salts), for example in a customary manner by adding the appropriate bases, for example Ammonia, monoethanolamine, triethanolamine, alkali metal hydroxides.
  • the addition products of the formula (5) are known and can be obtained in a known manner from Anla tion of 2 to 30 moles of ethylene or propylene oxide to an aliphatic amine with a hydrocarbon radical of 8 to 22 carbon atoms.
  • the process according to the invention is expediently carried out in such a way that, for example, the brightener, an acidic phosphoric acid ester of a fatty amine oxyalkylation product of the formula (1) and, if appropriate, one or more of the above-mentioned additional auxiliaries, individually and for the respective coating liquor which is prepared in the customary manner admixed in any order and finely divided therein, for example at temperatures between 10 and 150 ° C.
  • the whitener can also be mixed with an acidic phosphoric acid ester of a fatty amine oxalkylation product of the formula (1) and optionally with one or more of the above before the coating liquor is added the additional auxiliaries mentioned, advantageously with the addition of water, and the brightener preparation obtained can then, as described above, be added to the coating liquor, and paper or cardboard can then be coated with conventional coating apparatus with the finished coating composition with, for example, an air knife, a doctor knife, a brush, a roller, a doctor blade, a rod or any other coating apparatus customary in the paper industry.
  • the amount of compound of the formula (1) used in the process according to the invention can vary within wide limits. Even at a ratio of brightener to compound of formula (1) of 1: 0.5, positive effects are observed. This ratio is preferably 1: 1 to 15, in particular 1: 1 to 1: 3. Particularly good effects are achieved at a ratio of 1: 2. It would also be entirely possible to use more compound of the formula (1) than corresponds to the ratio 1: 5; however, this is not practical either for economic reasons or because of the associated influence on the consistency of the coating slip.
  • the amount of optional aids can vary within wide limits. The ratio of brightener to these aids can be between 1: 0.1 to 1:10, depending on the type of aid used (see also examples).
  • the amount of brightener that is added to the coating slips is within the normal range in the paper industry. For example, amounts between 1 g and 50 g / l of coating liquor are considered, preferably those between 4 and 20 g / l.
  • the method according to the invention also allows brightener concentrations higher than they are usually used (for example 4 to 8 g / l). Without the addition of compounds of formula (1), a drop in whiteness or severe greening often occurs, for example, at concentrations of more than 10 g of brightener per liter. On the other hand, this effect is eliminated when compounds of the formula (1) are added according to the invention: with an increasing brightener concentration, the attainable degree of whiteness also increases.
  • the process according to the invention is suitable for the optical brightening of the coating slips usually used in the paper industry, specifically of unpigmented, but in particular pigmented coating slips.
  • These coating slips contain a polymeric binder, an inorganic pigment (in the case of pigmented coating slips) and optionally other additives such as.
  • Suitable polymeric binders are the customary polymeric adhesive binder systems used in the paper industry.
  • any of the known, modified or converted types of starch such as extra oxidized, hydrolyzed or hydroxyethylated starches, can be used.
  • other natural or synthetic polymeric binder systems can be used alone or in particular in the case of synthetic polymeric binders in combination with one another.
  • the coating liquors can be used to eliminate undesirable traces of metal (e.g. Fe (III)) metal-binding agents such as. B. water-soluble poly- or metaphosphates and polycarboxylic acid salts.
  • metal e.g. Fe (III)
  • metal-binding agents such as. B. water-soluble poly- or metaphosphates and polycarboxylic acid salts.
  • an alkaline coating liquor is used for the pigment coat.
  • the alkaline reaction is expediently set with ammonia or with NaOH or KOH or with Na or K carbonates or borates or mixtures thereof.
  • the present invention further relates to the coating compositions lightened by the process according to the invention, that is to say an optical brightener of the bis-triazinylaminostilbene-2,2'-disulfonic acid series, preferably one of the formula (3), in particular one of the formula (4) and contain an acidic phosphoric acid ester of a fatty aminoxyalkylation product of the formula (1), preferably one of the formula (2).
  • an optical brightener of the bis-triazinylaminostilbene-2,2'-disulfonic acid series preferably one of the formula (3), in particular one of the formula (4) and contain an acidic phosphoric acid ester of a fatty aminoxyalkylation product of the formula (1), preferably one of the formula (2).
  • the coating compositions according to the invention can additionally contain nonionic or anionic surfactants, organic solubilizers and / or polar organic compounds, for. B.
  • hydrophilic organic solvents for example lower monohydric alcohols, polyhydric alcohols, ether alcohols, glycols, polyglycols, glycol and polyglycol ethers, amides and / or amines or as polar organic compounds dimethyl sulfoxide, dimethyl sulfone, ethylene or propylene carbonate and / or urea , or nonionic surfactants such as adducts of alkylene oxides with higher fatty acids, fatty acid amides, aliphatic alcohols, mercaptans or amines, with alkylphenols, alkylthiophenols or phenylphenols, block polymers from ethylene oxides and higher alkylene oxides, nonionic esters of the adducts with alkylene oxides, esters of polyalcohols and their addition products with ethylene oxide and reaction products from higher fatty acids with an alkanolamine and / or as anionic surfactants alkylene
  • the present invention relates to paper and cardboard coated with coating slips according to the invention (as described above).
  • example 1 is repeated, but instead of the brightener of the formula (10), the corresponding amount of a brightener of the following formulas is used: , paper with a similarly high degree of whiteness is obtained.
  • example 2 is repeated, but instead of using the brightener of formula (10), the corresponding amount of a brightener of formula (11), (12), (13), (14) or (15) is used, paper with similar results high whiteness.
  • the coating slip is finished and the paper is coated as described in Examples 1b) and 1c).
  • paper with a high degree of whiteness is obtained, which is considerably higher than that which is achieved with the individual brightener formulations A) to E), but without the compound of the formula (6).
  • the coating slip is finished and the paper is coated as described in Examples 1b) and 1c).
  • paper with a high degree of whiteness is obtained, which is considerably higher than that which is achieved with the individual brightener formulations A) to F), but without the compound of the formulas (6), (6a), (6b) or (6c).
  • Process B is repeated, but instead of the acidic ester of the formula (6c), the same amount of an ester of the formula (6a) is used.
  • Process B is repeated, but instead of the acidic ester of the formula (6c), the same amount of an ester of the formula (6b) is used.
  • Example 8 If Example 8 is repeated, but instead of using the brightener of the formula (10), the corresponding amount of a brightener of the formula (11), (12), (13), (14) or (15) is used, paper with similar is obtained high whiteness.
  • Example 9 If Example 9 is repeated, but instead of using the brightener of formula (10), the corresponding amount of a brightener of formula (11), (12), (13), (14) or (15) is used, paper with similar results high whiteness.
  • Example 5 5 ml each of the brightener solutions A) to E) defined in Example 5 are added to 15 ml of a pigment coating liquor obtained according to Example 8a). The coating slip is finished and the paper is coated as described in Examples 8b) and 8c). In each case paper with a high degree of whiteness is obtained, which is considerably higher than that which is achieved with the individual brightener formulations A) to E), but without the compound of the formula (6).
  • the mixture obtained is slowly stirred for 3 minutes Any pigment adhering to the wall is scraped off with a scraper, then slowly stirred for another 2 minutes, then 3 ml of concentrated ammonia and 80 ml of styrene-butadiene latex are added with stirring and the mixture is slowly stirred for a further 3 minutes 9.7 mol of ethylene oxide ethoxylated 4-nonylphenol (1:25) were added and the mixture was stirred for about 15 seconds again.
  • the fleet thus produced is vented through a nickel sieve and freed of agglomerates and coarser impurities.
  • the mass is then placed in a 1 liter Erlenmeyer flask and adjusted to a weight of 1260 g per liter with deionized water.
  • the coating slip obtained according to b) is stirred again and strips of coating base paper prepared therewith are coated in the customary manner. In this way a paper is obtained whose whiteness is significantly higher than that of a comparison paper which is coated with a coating liquor which contains no compound of the formula (6).
  • Example 13 is repeated, but 14 g of the compound of the formula (6) were additionally added in the preparation of the art print coating slip according to Example 13a). 15 ml of the coating slip otherwise prepared as described in Example 13a) are then mixed with 5 ml of a brightener solution consisting of 11.6 g of the brightener of the formula (10) and 88.4 g of water. Further workup is carried out as described in Example 13. A paper with a much higher degree of whiteness than that obtained by coating with a corresponding coating liquor which does not contain the compound of the formula (6) is likewise obtained.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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Claims (12)

1. Procédé pour augmenter ou améliorer l'effet de blanchiment lors de l'azurage optique de compositions d'enduction pour le couchage du papier ou duocarton, à l'aide d'azurants de la famille des acides bis-triazinylaminostilbéne-2,2'-disulfoniques, caractérisé par le fait qu'on incorpore aux compositions d'enduction, en plus de l'azurant en question, un ester phosphorique acide d'un produit d'oxyalkylation d'amine grasse de formule
Figure imgb0064
ou son sel de métal alcalin, d'ammonium ou d'amine, formule dans laquelle R est un reste hydrocarboné aliphatique ayant 8 à 22 atomes de carbone; Y, et Y2 sont tous deux des atomes d'hydrogène ou un de ces deux symboles représente un atome d'hydrogene et l'autre le radical méthyle; X est le reste acide de l'acide phosphorique, les atomes d'hydrogène acides de ce reste pouvant être remplacés par des ions de métaux alcalins, ammonium ou de sels d'amine, et m et n représentent des nombres entiers, la somme + n étant comprise entre 2 et 30.
2. Procédé selon la revendication 1, caractérisé par le fait qu'on utilise comme ester phosphorique acide d'un produit d'oxyalkylation d'amine grasse un de ceux ayant la formule
Figure imgb0065
dans laquelle R' est un reste alkyle ou alcényle ayant 10 à 18 atomes de carbone, de préférende le reste lauryle ou le reste hydrocarboné de l'amine du suif; X' est le reste acide de l'acide phosphorique, les atomes d'hydrogène acides de ce reste pouvant être remplacés par des ions de métaux alcalins ou ammonium, et n' et m' représentent des nombres entiers, la somme n' + m' étant comprise entre 4 et 20, en particulier entre 6 et 8.
3. Procédé selon la revendication 1, caractérisé par le fait qu'on utilise comme azurant un de ceux de formule
Figure imgb0066
dans laquelle R1 et R2 sont
Figure imgb0067
Figure imgb0068
Figure imgb0069
Figure imgb0070
Figure imgb0071
Figure imgb0072
ou
Figure imgb0073
et M est un atome d'hydrogène, un ion de métal alcalin, ammonium ou de sel d'amine, de préférence ceux de formule
Figure imgb0074
dans laquelle R'1 est
Figure imgb0075
ou
Figure imgb0076
R'2
Figure imgb0077
ou
Figure imgb0078
et M' est un atome d'hydrogène, ou un ion de métal alcalin, un ion ammonium, diéthylammonium ou triéthylammonium.
4. Procédé selon l'une quelconque des revendications 1 à 3, caractérisé par le fait qu'on ajoute aux compositions d'enduction, en plus de l'azurant et de l'ester phosphorique acide d'un produit d'oxyal- kylation d'amine grasse, encore des tensio-actifs non ioniques ou anioniques, des unisseurs organiques et/ou des composés organiques polaires.
5. Procédé selon la revendication 4, caractérisé par le fait qu'on ajoute comme unisseur, des solvants organiques hydrophiles tels que des alcools monovalents inférieurs, des polyols, des étheral- cools, des glycols, des polyglycols des glycol- et polyglycoléthers, des amides, des amines, et/ou comme composés organiques polaires le diméthylsulfoxyde, le diméthylméthanephosphonate, la diméthylsulfonate, le sulfolane, le carbonate d'éthylène ou le carbonate de propylène et l'urèe pu des urées substituées.
6. Procédé selon la revendication 4, caractérisé par le fait qu'on ajoute comme tensio-actifs non ioniques des produits d'addition d'oxydes d'alkylène sur des acides aliphatiques supérieurs, des amides gras, des alcools aliphatiques, des mercaptans ou des amines, sur des alkylphénols, des alkylthiophénols ou des phénylphénols, des polymères séquences d'oxyde d'éthylène et d'oxydes d'alkylène supérieurs, des esters non ioniques de produits d'addition d'oxydes d'alkylène, des esters de polyols, des alcanolamines N-acylées et leurs produits d'addition avec l'oxyde d'éthylène, et des produits de réaction d'acides aliphatiques supérieurs avec une alcanolamine, et/ou comme tensio-actifs anioniques des adducts d'oxydes d'alkylène avec des restes sulfate ou d'autres restes d'acide, des sulfates d'alcanolamines N-acylées et des composés polyoxy estérifiés sulfatés.
7. Procédé selon l'une quelconque des revendications 1 à 6, caractérisé par le fait qu'on mélange l'azurant avec l'ester phosphorique acide d'un produit d'oxyalkylation d'amine grasse et éventuellement avec des adjuvants facultatifs déffinis dans l'une quelconque des revendications 4 à 6 et éventuellement de l'eau, puis qu'on incorpore ce mélange aux compositions d'enduction.
8. Procédé selon l'une quelconque des revendications 1 à 6, caractérisé par le fait qu'on incorpore séparément et indépendamment l'un de l'autre, aux compositions d'enduction l'azurant, l'ester phosphorique acide d'un produit d'oxyalkylation d'amine grasse et éventuellement les adjuvants facultatifs définis dans l'une quelconque des revendications 4 à 6.
9. Composition d'enduction azurée optiquement pour le couchage du papier et du carton contenant un azurant optique de la famille des acides bis-triazinylaminostilbène-2,2'-disulfoniques, de préférence un de ceux de formule (3), en particulier un de ceux de formule (4) selon la revendication (3) et un ester phosphorique acide d'un produit d'oxyalkylation d'amine grasse de formule (1), de préférence un de ceux de formule (2) selon les revendications 1 et 2.
10. Composition d'enduction selon la revendication 9, qui contient, en plus de l'azurant optique et de l'ester phosphorique acide d'un produit d'oxyalkylation d'amine grasse, des tensio-actifs non ioniques ou anioniques, de préférence ceux qui sont définis dans la revendication 6, des unisseurs organiques et/on des composés organiques polaires, de préférence ceux qui sont définis dans la revendication 5.
11. Papier ou carton couchés avec une composition d'enduction définie dans les revendications 9 ou 10.
EP81810008A 1980-07-03 1981-01-08 Procédé d'augmentation ou d'amélioration de l'effet de blanchiment lors du blanchiment optique de compositions d'enduction Expired EP0043790B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT81810008T ATE8516T1 (de) 1980-07-03 1981-01-08 Verfahren zur erhoehung bzw. verbesserung des weisseffekts beim optischen aufhellen von streichmassen.

Applications Claiming Priority (2)

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CH5140/80 1980-07-03
CH514080 1980-07-03

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EP0043790A1 EP0043790A1 (fr) 1982-01-13
EP0043790B1 true EP0043790B1 (fr) 1984-07-18

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US (1) US4386965A (fr)
EP (1) EP0043790B1 (fr)
JP (1) JPS5716995A (fr)
AT (1) ATE8516T1 (fr)
AU (1) AU6617581A (fr)
BR (1) BR8100171A (fr)
CA (1) CA1158002A (fr)
DE (1) DE3164785D1 (fr)
ES (1) ES8205909A1 (fr)
PT (1) PT72351B (fr)
ZA (1) ZA81201B (fr)

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CN102887005A (zh) * 2007-05-21 2013-01-23 国际纸业公司 具有改善的图像耐水性、表面强度和运行性的记录片材
CA2710804C (fr) 2007-12-26 2013-07-02 International Paper Company Substrat de papier contenant un agent mouillant et presentant une marbrure d'impression amelioree
US8460511B2 (en) * 2008-10-01 2013-06-11 International Paper Company Paper substrate containing a wetting agent and having improved printability
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CN103194086B (zh) * 2013-03-14 2014-07-02 浙江传化华洋化工有限公司 一种含氨基丙酸衍生物荧光增白剂的合成方法
CN103254660B (zh) * 2013-05-20 2014-07-30 浙江传化华洋化工有限公司 一种不含尿素的二磺酸三嗪基类荧光增白剂液体的制备方法

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CN103558172B (zh) * 2013-11-22 2015-11-25 江南大学 一种用于荧光增白材料白度目测评估的方法

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JPS5716995A (en) 1982-01-28
BR8100171A (pt) 1982-08-17
PT72351B (en) 1983-09-01
ES498461A0 (es) 1982-07-01
ATE8516T1 (de) 1984-08-15
ZA81201B (en) 1982-02-24
PT72351A (en) 1981-02-01
EP0043790A1 (fr) 1982-01-13
AU6617581A (en) 1982-01-07
JPH0159395B2 (fr) 1989-12-18
CA1158002A (fr) 1983-12-06
DE3164785D1 (en) 1984-08-23
US4386965A (en) 1983-06-07
ES8205909A1 (es) 1982-07-01

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