US3442905A - N-methylol-n'-substituted-4,5-dihydroxy-2-imidazolidinones - Google Patents

N-methylol-n'-substituted-4,5-dihydroxy-2-imidazolidinones Download PDF

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US3442905A
US3442905A US577845A US3442905DA US3442905A US 3442905 A US3442905 A US 3442905A US 577845 A US577845 A US 577845A US 3442905D A US3442905D A US 3442905DA US 3442905 A US3442905 A US 3442905A
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dihydroxy
methylol
imidazolidinone
fabric
bath
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US577845A
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William Frank Herbes
John Peter Dundon
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Wyeth Holdings LLC
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American Cyanamid Co
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/30—Oxygen or sulfur atoms
    • C07D233/40—Two or more oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
    • C08G12/10—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with acyclic compounds having the moiety X=C(—N<)2 in which X is O, S or —N
    • C08G12/12—Ureas; Thioureas
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/423—Amino-aldehyde resins

Definitions

  • This invention relates to novel imidazolidinones, their use in the treatment of cellulosic textile materials, and the treated cellulosic substrates obtained thereby.
  • Another object is to produce a composition containing novel compounds suitable for the treatment of cellulosic textile materials.
  • Another object is to produce novel compounds which when employed in the treatment of cellulosic textile materials obtains a high order of resistance to creasing, to
  • Another object is a process of applying said novel compounds or compositions to a cellulosic substrate.
  • Another object is to produce a cellulosic substrate characterized by a high order of resistance to creasing, to discoloration, and to strength loss due to chlorine retention and scorch.
  • the objects of this invention are obtained by synthesizing and applying the novel aminoplast compound of this invention, in a suitable solvent, to a cellulosic substrate in an amount sufficient to be effective, and thereafter curing the substrate preferably in the presence of any conventional acid-curing catalyst.
  • novel aminoplast compounds of this invention are represented by the formula:
  • R contains at least two carbon atoms and is selected from the group consisting of lower alkyl, allyl, aryl, aralkyl, cycloalkyl, and the substituted forms of each of the preceding members, the substituted forms typically including at least one substituent of the group consisting of halogen, hydroxy, and cyano, providing an alpha carbon atom of R is not substituted by hydroxy, and in which R R R R R and R are each selected from the group consisting of hydrogen, lower alkyl, allyl, aryl, aralkyl, cycloalkyl, and the substituted forms of each of the preceding members, the substituents typically including at least one substituent of the group consisting of halogen, hydroxy, and cyano.
  • a novel cellulosic material is obtained by applying to a cellulosic substrate a solution of a compound selected from the group consisting of (1) the above-described novel aminoplast compound, and (2) an N-methyl-N- substituted imidazolidinone of the formula:
  • R R R and R are each selected from the group consisting of the members of R as defined above.
  • the preferred composition includes at least one of the above-described novel compounds of this invention.
  • the novel cellulosic material of this invention is characterized by a high order of resistance to creasing, to dis coloration such as yellowing, and to strength loss due to chlorine retention and scorch.
  • the crease resistance i.e. wrinkle recovery properties
  • the novel cellulosic substrate of this invention resulting from the above treatment is superior in other characteristics such as the low formaldehyde liberation during curing, low strength loss due to chlorine retention and scorch, and good non-yellowing properties.
  • novel compound of this invention is characterized by the desirable property of being suitable for use with magnesium chloride as the curing catalyst whereby the employment of other conventional catalysts such as zinc nitrate may be avoided, thereby avoiding interference with brightener activity on white goods (cellulosic).
  • any compatible conventional solvent may be employed, including for example, alcohols such as isopropyl alcohol, etc.
  • cellulosic substrate fibers, filaments, yarns, fabrics, whether woven or non-woven, knitted, felted or otherwise formed, containing at least about 50% of cellulose fibers such as cotton, rayon, linen, hemp, jute or the like.
  • the cellulose fibers may be present in combination with other natural or synthetic fibers, such as wool, silk, acetate, nylon, polyester fibers, acrylic fibers and the like.
  • the textile material is formed, woven cotton fabric.
  • the preferred compound of this invention is N-methylol-N-beta-hydroxyethyl-imidazolidinone of the above formula.
  • R, R and R are each hydrogen substituents
  • Suitable N-substituted ureas which typically may be used include l-methylurea, l-ethylurea, l-n-propylurea, l-isopropylurea, l-n-butylurea, l-tertiary butylurea, l-allylurea, l-phenylurea, etc.
  • the alkyl and phenyl groups may be substituted by inert substituents such as alkyl, hydroxyl (not in the alpha-positions), halogen, cyano, etc. as exemplified by 1-(2-hydroxyethyl)urea, l-p-tolylurea, l-(p-chlorophenyDurea, l-(l-cyanisopropyl)urea, etc.
  • alpha, beta-dicarbonyl compounds which typically may be used include, for example, glyoxal, methylglyoxal, ethylglyoxal, n-propylglyoxal, isobutylglyoxal, dimethylglyoxal, methylethylglyoxal, ethylpropylglyoxal, etc. Of these, glyoxal is preferred.
  • Formaldehyde in any of its forms can be used; but formalin is preferred.
  • Reaction of the N-substituted urea can be made first with the alpha, beta-dicarbonyl compound and then with formaldehyde, or the reverse procedure can be used. Also, the reaction can be carried out in a single step with both the alpha, beta-dicarbonyl compound and formaldehyde present. Approximately stoichiometric amounts of the three reactants are normally used. From neutral to alkaline reaction conditions are suitably employed. Suitable alkalies include sodium hydroxide, potassium hydroxide etc. An aqueous medium is normally used, but an inert water-miscible solvent may also be present. Temperatures between 0 and 100 C., preferably between and 70 C., may be employed.
  • Lower aliphatic alcohols which may be used in the alkylation step, include, for example, methanol, ethanol, the propanols, the butanols, etc.
  • Suitable acids for use in the alkylation step include, for example, the inorganic acids such as hydrochloric, sulfuric, and phosphoric acids, and the organic acids, such as formic and oxalic acids.
  • At least a stoichiometric amount of alcohol must be used. A substantial excess is normally desirable.
  • Sufficient acid is employed to provide a pH below 4. Reaction temperatures between 0 and C., preferably between 15 and 30 C., are used.
  • exemplary creaseproofing resins may be employed singly or in combination with each other and with other creaseproofing resins known to those skilled in the art, in accordance with the present invention.
  • novel resinous composition of this invention containing the imidazolidinone may be applied to cellulosic .4 textile materials by any of the conventional techniques such as immersion, padding, spraying and the like followed where necessary by squeezing, hydroextraction or similar processes in order to aflix the desired amount of solids on the fabric.
  • the method of application should be such that from about 1 to about 25% and in some instances higher amounts of the product of this invention based on the weight of the fabric are deposited thereon. Within certain limits, the amount of agent applied depends upon the particular type of fabric being treated. Thus, when treating fabric consisting of fibrous cellulosic materials, the concentration of the order of about 1% to 25%, and preferably from 3 to 10% solids, based on the dry weight of the fabric, normally should be employed.
  • the catalyst or accelerator employed is an acidic type catalyst and may be a free acid, acid salt, alkanolamine salt, metal salt and the like of the type well known to those in the textile finishing art.
  • concentration of catalyst employed may range from about 0.1 to about 25 or higher, based on the weight of the novel aminoplast solids, depending upon the particular catalyst type employed. Thus, for example, from between about 0.1% and about 10% of a free acid such as phosphoric, tartaric, oxalic or the like may be employed, while in the case of ammonium chloride amounts of from between 0.5 and about 10% are used.
  • amine salts including alkanolamine salts, such as diethanolamine hydrochloride
  • salts such as magnesium chloride amounts of from between aobut 5 to 25% have been successfully employed.
  • magnesium chloride optionally zinc nitrate, aluminum chloride and other conventional metal salts may alternatively be employed alone or in combination in amounts corresponding to between about 5 and 25% based on the weight of aminoplast solids.
  • an aqueous bath containing 7.5% of 1-methyl-3-methylol-4,5-dihydroxy-2-imidazolidinone and 0.9% of magnesium chloride is applied to x 80 cotton percale by a padding procedure.
  • the 0.9% of magnesium chloride in the bath is equivalent to 12.0% based on the weight of the imidazolidinone in the bath.
  • An 80% wet pickup by the fabric is normally obtained, thereby depositing about 6% of the imidazolidinone on the fabric.
  • the fabric is dried at a temperature of about 225 F. for one minute and is then heated at about 350 F. for about 1.5 minutes.
  • the material is subject to drying and curing operations in order to affect wrinkle resistance and shrinkage control thereon.
  • the drying and curing operation may be carried out in a single step or in separate steps.
  • the temperatures at which the drying and curing operations are effected vary widely and are influenced to some extent by the type of catalyst employed. Normally, the range of temperature extends from about 180 F. to about 450 F. or even higher. Generally speaking, the time of the drying and/or curing operations is inversely proportional to the temperatures employed and of course is influenced by whether or not separate or combined drying and curing steps are employed.
  • a time of from about one minute to about 10 minutes may be employed at temperatures from 450 to 250 F., respectively.
  • curing times of the order of 5 minutes to about /1 minute at a temperature of from between 250 and 450 F., respectively, have been successfully employed.
  • the pH of a solution of 70 parts (1.2 mole) of glyoxal in 104 parts of water is adjusted to 6.7 by addition of sodium bicarbonate.
  • the pH of the solution is adjusted to slightly above 9' with sodium hydroxide, and 68.2 parts (1.0 mole) of 44% formalin is added. Reaction is maintained at a temperature of 35-50 C. and at a pH of above 9 until the unreacted formaldehyde is 2.0% or below of the total composition.
  • the resulting solution is adjusted to a solids content of 50% of the total composition by adding water and to a pH of about 5.2 by adding hydrochloric acid.
  • EXAMPLE VII 1-tertiary-butyl-3-methylol-4,5-dihydroxy-2-irnidazolidinone
  • EXAMPLE VIII Three aqueous pad baths (A, B, C) are prepared, each bath containing 7.5% of one of the methylol Z-imidazolidinones listed below, 0.84% (11.2% based on the weight of the aminoplast solids) of zinc nitrate, 0.07% (0.93% based on the weight of the aminoplast solids) of acetic acid, and 0.1% of the non-ionic surface active agent obtained by condensing 1 mole of nonylphenol with an average of 9.5 moles of ethylene oxide. The above percentages are based on the weight of the bath.
  • Pad bath A -l-methyl-3-methylol-4,S-dihydroxy-Z- imidazolidinone (product of Example I).
  • the three pad baths are applied to swatches of 80 x 80 bleached cotton percale by standard padding procedure using 80% wet pickup.
  • the swatches, containing 6% O.W.F. of the reactants, are dried at 225 F. for one minute and are then heated at 350 F. for 1.5 minutes.
  • the washes under Damage by Retained Chlorine are carried out at about 212 F. as described in AATCC Tentative Test Method 961960F, Procedure IV.
  • Fabrics A, B, and C correspond to pad baths A, B, and C, respectively.
  • Table I illustrates the superiority of A as compared to B and C, as to damage from chlorine retention.
  • EXAMPLE IX Two aqueous pad baths (A, B) are prepared, each bath containing 7.5% of one of the methylol Z-imidazolidinones listed below, 0.9% (12.0% based on the weight of the aminoplast solids) of magnesium chloride and 0.1% of the nonionic surface active agent obtained by condensing 1 mole of nonylphenol with an average of 9.5 moles of ethylene oxide. The above percentages are based on the weight of the bath.
  • the two pad baths are applied to swatches f 80 X 80 bleached cotton percale by standard padding procedure using 80% wet pickup.
  • the swatches, containing 6% O.W.F. of the reactants, are dried at 225 F. for 1 minute and the fabrics are then heated at 35 0 F. for 1.5 minutes.
  • Table II illustrates the superiority of A as compared to B, as to damage from clorine retention.
  • EXAMPLE X Two pad baths (A, B) are prepared, each bath containing 7.5% of one of the methylol Z-irnidazolidinones listed below, 0.84% (11.2% based on the weight of the aminoplast solids) of zinc nitrate, 0.07% (0.93% based on the weight of the aminoplast solids) of acetic acid, and 0.1% of the non-ionic surface active agent obtained by condensing 1 mole of nonylphenol with an average of 9.5 moles of ethylene oxide. The above percentages are based on the weight of the bath.
  • Pad bath A.1 (2 hydroxyethyl)-3-methylol-4,5-dihydroxy-2-imidazolidinone (Product of Example II).
  • the two pad baths are applied to swatches of x 80 bleached cotton percale by standard padding procedure using 80% wet pickup.
  • the swatches, containing 6% O.W.F. of the reactants, are dried at 225 F. for 1 minute and are then heated at 350 F. for 1.5 minutes.
  • Fabrics A and B correspond to pad baths A and B, respectively.
  • Table III illustrates the superiority of A as compared to B, as to damage by chlorine retention, and discoloration.
  • EXAMPLE XI An aqueous pad bath is prepared containing 7.5% of 1 (2 hydroxyethyl) 3 methylol 4,5 dihydroxy 2- imidazolidinone (product of Example II), 0.9% (12.0% based on the aminoplast solids) of magnesium chloride and 0.1% of the non-ionic surface active agent obtained by condensing 1 mole of nonylphenol with an average of 9.5 moles of ethylene oxide. The above percentages are based on the weight of the bath.
  • the pad bath is applied to a swatch of 80 x 80 bleached cotton percale by standard padding procedure using 80% wet pickup.
  • the swatch containing 6% O.W.F. of the reactant, is dried at 225 F. for 1 minute and is then heated at 350 F. for 1.5 minutes.
  • Example VIII Measurements for wrinkle recovery and damage caused by retained chlorine are measured by the procedure of Example VIII.
  • the yellowness index is calculated by the procedure described in Example X.
  • magnesium chloride instead of a catalyst such as zinc nitrate. Particularly note less yellowing with magnesium chloride, this being opposite of the conventional effect of magnesium chloride.
  • EXAMPLE XII Three pad baths (A, B, C) are prepared using water or dimethylformamide as the medium. Each pad bath contains 7.6% of a 3-methylol-4,5-dihydroxy-2-imidazolidinone and 0.9% (12.0% based on the aminoplast solids) of magnesium chloride.
  • Pad bath A.1 isopropyl 3 methylol 4,5 dihydroxy 2 imidazolidinone (Produce of Example III) and water.
  • Pad bath C.-1 tertiary butyl 3 methylol 4,5- dihydroxy 2 imidazolidinone (Product of Example VII) and dimethylformamide.
  • the pad baths are applied to swatches of 80 X 80 bleached cotton percale by standard padding procedure using 80% wet pickups.
  • the swatches, containing 6% O.W.F. of the reactants, are dried at 225 F, for 2 minutes and the fabrics are then heated at 350 F. for 1.5 minutes.
  • Fabrics A, B, and C correspond to pad baths A, B, and C, respectively.
  • R is hydroxy lower alkyl of at least two carbon atoms, provided that an alpha carbon of R is not substituted by hydroxy, and in which R and R are each selected from the group consisting of hydrogen and lower alkyl, and R R and R are hydrogen.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US577845A 1966-09-08 1966-09-08 N-methylol-n'-substituted-4,5-dihydroxy-2-imidazolidinones Expired - Lifetime US3442905A (en)

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US57784566A 1966-09-08 1966-09-08
US69271267A 1967-12-22 1967-12-22

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US577845A Expired - Lifetime US3442905A (en) 1966-09-08 1966-09-08 N-methylol-n'-substituted-4,5-dihydroxy-2-imidazolidinones
US692712A Expired - Lifetime US3488701A (en) 1966-09-08 1967-12-22 Use of n-methylol-n'-substituted-4,5-dihydroxy - 2-imidazolidinones as textile finishing agents

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US (2) US3442905A (en, 2012)
BE (1) BE703580A (en, 2012)
CH (1) CH1258167D (en, 2012)
DE (1) DE1594895A1 (en, 2012)
FR (1) FR1535271A (en, 2012)
NL (1) NL6711787A (en, 2012)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3920881A (en) * 1973-07-02 1975-11-18 American Cyanamid Co Textile finish using a combination of an aminoplast resin and monomethyloldicyandiamide

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* Cited by examiner, † Cited by third party
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US4167501A (en) * 1978-04-13 1979-09-11 Dow Corning Corporation Process for preparing a textile-treating composition and resin-silicone compositions therefor
US4295846A (en) * 1980-03-18 1981-10-20 Basf Aktiengesellschaft Process for the production of formaldehyde-free finishing agents for cellulosic textiles and the use of such agents
US4622374A (en) * 1983-03-10 1986-11-11 National Starch And Chemical Corporation Imidazolidinone polymers useful as nonwoven binders
US5882357A (en) * 1996-09-13 1999-03-16 The Regents Of The University Of California Durable and regenerable microbiocidal textiles
US6241783B1 (en) 1996-09-13 2001-06-05 The Regents Of The University Of California Formaldehyde scavenging in microbiocidal articles
US7541398B2 (en) * 2005-01-03 2009-06-02 Board Of Regents, The University Of Texas System Method for transformation of conventional and commercially important polymers into durable and rechargeable antimicrobial polymeric materials
US20070062884A1 (en) * 2005-08-11 2007-03-22 Board Of Regents, The University Of Texas System N-halamines compounds as multifunctional additives
US7998886B2 (en) * 2005-10-24 2011-08-16 Milliken & Company Hindered amine treated textiles
US20070218562A1 (en) * 2006-03-20 2007-09-20 Shulong Li Color indicator for halamine treated fabric
US8486428B2 (en) * 2006-03-27 2013-07-16 Board Of Regents, The University Of Texas System Compositions and methods for making and using acyclic N-halamine-based biocidal polymeric materials and articles
US8211361B2 (en) * 2007-03-26 2012-07-03 Board Of Regents, The University Of Texas System N-halamine-based rechargeable biofilm-controlling tubular devices, method of making and using
US7858539B2 (en) * 2007-04-09 2010-12-28 Milliken & Company Processes for generating halamine compounds on textile substrates to produce antimicrobial finish
CA2700259A1 (en) * 2007-09-19 2009-03-26 Board Of Regents, The University Of Texas System Colorants based n-halamines compositions and method of making and using

Citations (7)

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US2731364A (en) * 1951-08-18 1956-01-17 Basf Ag Process for improving cellulose textile materials and product thereof
US3029164A (en) * 1959-03-12 1962-04-10 Sumitomo Chemical Co Production of crease resistance in cellulosic fabrics with the aid of 1, 3-dimethylol-4, 5-bis(alkoxy)-2-imidazolidinones
US3079279A (en) * 1961-02-03 1963-02-26 American Cyanamid Co Blends of imidazolidinones and aminoplasts and method for finishing cellulose containing textile material
DE1171438B (de) * 1962-09-19 1964-06-04 Basf Ag Verfahren zur Herstellung von Imidazolidinonen
DE1172265B (de) * 1962-09-19 1964-06-18 Basf Ag Verfahren zur Herstellung von Imidazolidinonen
US3209010A (en) * 1961-11-13 1965-09-28 Gagliardi Res Corp Polyalkylated monoureins
US3304312A (en) * 1966-07-08 1967-02-14 American Cyanamid Co Imidazolidinones

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2731364A (en) * 1951-08-18 1956-01-17 Basf Ag Process for improving cellulose textile materials and product thereof
US3029164A (en) * 1959-03-12 1962-04-10 Sumitomo Chemical Co Production of crease resistance in cellulosic fabrics with the aid of 1, 3-dimethylol-4, 5-bis(alkoxy)-2-imidazolidinones
US3079279A (en) * 1961-02-03 1963-02-26 American Cyanamid Co Blends of imidazolidinones and aminoplasts and method for finishing cellulose containing textile material
US3209010A (en) * 1961-11-13 1965-09-28 Gagliardi Res Corp Polyalkylated monoureins
DE1171438B (de) * 1962-09-19 1964-06-04 Basf Ag Verfahren zur Herstellung von Imidazolidinonen
DE1172265B (de) * 1962-09-19 1964-06-18 Basf Ag Verfahren zur Herstellung von Imidazolidinonen
US3304312A (en) * 1966-07-08 1967-02-14 American Cyanamid Co Imidazolidinones

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3920881A (en) * 1973-07-02 1975-11-18 American Cyanamid Co Textile finish using a combination of an aminoplast resin and monomethyloldicyandiamide

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FR1535271A (fr) 1968-08-02
DE1594895A1 (de) 1969-08-28
US3488701A (en) 1970-01-06
BE703580A (en, 2012) 1968-03-07
NL6711787A (en, 2012) 1968-03-11
CH1258167D (en, 2012)

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