US3671308A - Textile softening agents - Google Patents
Textile softening agents Download PDFInfo
- Publication number
- US3671308A US3671308A US845505A US3671308DA US3671308A US 3671308 A US3671308 A US 3671308A US 845505 A US845505 A US 845505A US 3671308D A US3671308D A US 3671308DA US 3671308 A US3671308 A US 3671308A
- Authority
- US
- United States
- Prior art keywords
- formaldehyde
- weight
- alkyl
- urea
- mols
- 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 - Lifetime
Links
- 239000004753 textile Substances 0.000 title abstract description 20
- 239000004902 Softening Agent Substances 0.000 title description 15
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract description 64
- 239000000463 material Substances 0.000 abstract description 23
- 239000007795 chemical reaction product Substances 0.000 abstract description 20
- 239000006185 dispersion Substances 0.000 abstract description 13
- 238000000034 method Methods 0.000 abstract description 10
- 239000000835 fiber Substances 0.000 abstract description 8
- 239000004202 carbamide Substances 0.000 abstract description 7
- 229920002678 cellulose Polymers 0.000 abstract description 2
- 239000001913 cellulose Substances 0.000 abstract description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- 239000004744 fabric Substances 0.000 description 12
- -1 aliphatic acid amides Chemical class 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 229920003043 Cellulose fiber Polymers 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 6
- 239000007859 condensation product Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 5
- GJNDMSSZEBNLPU-UHFFFAOYSA-N octadecylurea Chemical compound CCCCCCCCCCCCCCCCCCNC(N)=O GJNDMSSZEBNLPU-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 3
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- WRNOAELBRPKVHC-UHFFFAOYSA-N dodecylurea Chemical compound CCCCCCCCCCCCNC(N)=O WRNOAELBRPKVHC-UHFFFAOYSA-N 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- ZEYUSQVGRCPBPG-UHFFFAOYSA-N 4,5-dihydroxy-1,3-bis(hydroxymethyl)imidazolidin-2-one Chemical compound OCN1C(O)C(O)N(CO)C1=O ZEYUSQVGRCPBPG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000004519 grease Substances 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- IQDKUTQPYBHPJK-UHFFFAOYSA-N 1,3-bis(hydroxymethyl)-1,3-diazinan-2-one Chemical compound OCN1CCCN(CO)C1=O IQDKUTQPYBHPJK-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- 241001076939 Artines Species 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 239000005696 Diammonium phosphate Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920001407 Modal (textile) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 229910000388 diammonium phosphate Inorganic materials 0.000 description 1
- 235000019838 diammonium phosphate Nutrition 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- BPNWJLRQKKYVII-UHFFFAOYSA-N formaldehyde;octadecylurea Chemical compound O=C.CCCCCCCCCCCCCCCCCCNC(N)=O BPNWJLRQKKYVII-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- LCTOXAHEDJCUII-UHFFFAOYSA-N n-carbamoyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NC(N)=O LCTOXAHEDJCUII-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 description 1
- 229950005308 oxymethurea Drugs 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- 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
- the present invention relates to new textile softening agents.
- the present invention is based on the unexpected finding that the reaction products of at least 3 mols of formaldehyde with 1 mol of N-alkyl-ureas of N-alkyl-biuret compounds with long chain alkyl radicals, when applied onto textile materials, impart to these materials a soft full handle.
- the object of the invention is a process for the softening of cellulose fibers or of textile materials consisting of or containing such cellulose fibers, wherein these materials are treated with solutions or dispersions of reaction products of at least 3, preferably 3.2 to 4 mols, of N-alkyl-ureas or N-alikyl-biuret compounds which contain about 14 to 22 carbon atoms in the alkyl radical.
- reaction products of at least 3, preferably 3.2 to 4 mols, of N-alkyl-ureas or N-alikyl-biuret compounds which contain about 14 to 22 carbon atoms in the alkyl radical.
- the textile softening agents used according to the invention it is an absolute prerequisite that for their preparation the N-alkyl-urea or N-alkyl-biuret compounds are reacted with at least 3 mols of formaldehyde.
- the products obtained by the reaction with less than 3 mols of formaldehyde still have hydrophobising properties, but they rapidly lose
- reaction products used according to the present invention when applied in the form of aqueous dispersions or in the form of solutions in inert organic solvents onto textile materials such as fibers, filaments, fabrics or other products that consist of or contain cellulose, impart onto these materials an agreeable, very soft, flowing and smooth handle.
- textile materials which may be treated with the softening agents of the present invention may consist of or contain cotton, staple fibers, polynosic fibers or other fibers of regenerated cellulose, or mixture of such fibers with synthetic fibers such as polyamide, polyester, cellulose triacetate and similar fibers.
- the textile softening agents according to the invention may be prepared by known methods.
- a fatty amine containing about 14 to 22 carbon atoms for example octadecylamine
- urea or biuret under separation of ammonia.
- the condensation is effected generally at temperatures in the range of from about to C.
- 1 mol of the reaction products obtained is methylolised with at least 3 mols of formaldehyde or formaldehyde yielding substances, for example p-formaldehyde, formaline or trioxane.
- the methylolation can be effected in aqueous solution, in organic solvents, in the melt or according to other known methods.
- 3.2 to 4 mols of formaldehyde are used preferably per mol of the N-alkyl-urea compound or of the biuret compound.
- the use of higher amounts of formaldehyde does not bring further improvements, so that for economical reasons no more than about 4 mols of formaldehyde per mol of the alkyl-ureaor alkyl-biuret-compound are used.
- N-alkyl-ureaand N-alkyl-biuret compounds there may be used those which correspond to the general formula R NHCO-NH--R in which R, stands for an alkyl radical containing 14 to 22 carbon atoms and R stands for hydrogen or the radical CONH
- R stands for an alkyl radical containing 14 to 22 carbon atoms
- R stands for hydrogen or the radical CONH
- the softening agents of the invention are dissolved in suitable organic solvents or dispersed in water.
- the aqueous dispersions may be prepared with the aid of nonionic and/ or anionic dispersing agents or stabilized in this manner.
- the solutions or dispersions of the softening agents may be applied onto the textile material in any desired manner, for example by spraying or impregnation and squeezing.
- the quantity of softening agents of the invention applied may vary within wide limits and depends on the textile material to be treated and on the softening effect to be obtained. In general, the softening agents are applied onto the textile material in quantities ranging from about 0.01 to 1%, preferably 0.1 to 0.5%, referred to the weight of the textile material.
- the softening agents of the invention impart onto the textile material treated wash-resistant effects already when used alone and particularly also when used together with an acid catalyst which includes acids and acid-forming substances such as magnesium chloride, zinc chloride, zinc nitrate, diammonium phosphate, ammonium nitrate, and similar compounds.
- an acid catalyst which includes acids and acid-forming substances such as magnesium chloride, zinc chloride, zinc nitrate, diammonium phosphate, ammonium nitrate, and similar compounds.
- wash and wear resins for example dimethylol-urea, dimethyloldihydroxyethylene-urea, dimethylol-dihydroxyethyleneurea, dimethylol-propylene-urea and similar compounds, they improve the wet and dry crease resistance, the fastness to rubbing and the resistance to tearing and the tensile strength.
- softening agents of the invention are their particularly good compatibility with other finishing agents.
- the finishing bath containing the softening agents of the invention also other auxiliary agents, for example filling and smoothing agents, wetting agents, emulsifiers, water softeners, so-called soil releasers, optical brighteners, catalysts, synthetic resin precondensation products and other additives, without impairment of the original softening effect.
- the softening agents may be applied from one bath which also contains the additives or from a separate bath, i.e. separately from the additives; in the last case it is advantageous to apply the softening agent at last.
- the softening agents may also be applied onto fabrics, for example on 3 a foulard or a similar apparatus or by the exhaust method.
- the fibrous materials may be treated with an engraved or Schreiner calender, and, depending on their composition, at temperatures in the range of from about 20 to 220 C.
- EXAMPLE 1 A cotton fabric having a weight of 120 g. per square meter was immersed in a bath containing, per liter,
- the fabric was then squeezed to about 80% of weight increase and dried for 3 minutes at 110 C. The fabric showed then a soft flowing full handle.
- the fabric was then squeezed to 80% weight increase and dried at 110 C. The residual moisture was 6%. Finally, the fabric was calendered in the usual manner and condensation was effected for 5 minutes at C.
- the fabric showed a full supple handle and good crease resisting properties.
- DRY GREASE ANGLE ACCORDING TO GERMAN INDUS- TRIAL STANDARD 53 890 A fabric consisting of 35% of cotton and 65% of polyester fibers was impregnated with a solution containing, per liter 18 g. of 20% aqueous dispersion of a reaction product of N-octadecyl-biuret and formaldehyde, the preparation of which is described hereinafter, and
- the fabric was squeezed to 60% weight increase and dried at 110 C.
- the fabric showed an agreeable soft full handle.
- Process for the softening of textile materials containing cellulose fibers comprising applying to said materials a reaction product of at least 3 mols of formaldehyde and 1 mol of a N-alkyl-ureaor a N-alkyl biuret containing 14 to 22 carbon atoms in the alkyl radical.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT734768A AT287644B (de) | 1968-07-29 | 1968-07-29 | Verfahren zum Weichmachen von Textilmaterialien |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3671308A true US3671308A (en) | 1972-06-20 |
Family
ID=3595147
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US845505A Expired - Lifetime US3671308A (en) | 1968-07-29 | 1969-07-28 | Textile softening agents |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3671308A (fr) |
| AT (1) | AT287644B (fr) |
| BE (1) | BE736731A (fr) |
| BR (1) | BR6911126D0 (fr) |
| CH (2) | CH1143269A4 (fr) |
| DE (1) | DE1934177C3 (fr) |
| FR (1) | FR2013934B1 (fr) |
| GB (1) | GB1237612A (fr) |
| NL (1) | NL6911400A (fr) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3043570A1 (de) * | 1979-11-26 | 1981-05-27 | Colgate-Palmolive Co., 10022 New York, N.Y. | Dialkylharnstoffe, ihre verwendung als weichmachendeund antistatisch wirkende mittel fuer textilien sowie diese mittel enthaltende wschmittelzusammensetzungen |
| US4488974A (en) * | 1982-11-30 | 1984-12-18 | Cassella Aktiengesellschaft | Softener emulsion, a process for its preparation, and its application |
-
1968
- 1968-07-29 AT AT734768A patent/AT287644B/de not_active IP Right Cessation
-
1969
- 1969-07-05 DE DE1934177A patent/DE1934177C3/de not_active Expired
- 1969-07-24 NL NL6911400A patent/NL6911400A/xx unknown
- 1969-07-25 CH CH1143269D patent/CH1143269A4/xx unknown
- 1969-07-25 CH CH1143269A patent/CH510775A/de not_active IP Right Cessation
- 1969-07-28 US US845505A patent/US3671308A/en not_active Expired - Lifetime
- 1969-07-29 BE BE736731A patent/BE736731A/fr unknown
- 1969-07-29 BR BR211126/69A patent/BR6911126D0/pt unknown
- 1969-07-29 GB GB38031/69A patent/GB1237612A/en not_active Expired
- 1969-07-29 FR FR6925914A patent/FR2013934B1/fr not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3043570A1 (de) * | 1979-11-26 | 1981-05-27 | Colgate-Palmolive Co., 10022 New York, N.Y. | Dialkylharnstoffe, ihre verwendung als weichmachendeund antistatisch wirkende mittel fuer textilien sowie diese mittel enthaltende wschmittelzusammensetzungen |
| US4488974A (en) * | 1982-11-30 | 1984-12-18 | Cassella Aktiengesellschaft | Softener emulsion, a process for its preparation, and its application |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1934177A1 (de) | 1970-02-05 |
| AT287644B (de) | 1971-01-25 |
| DE1934177C3 (de) | 1975-09-04 |
| DE1934177B2 (de) | 1974-11-14 |
| CH1143269A4 (fr) | 1971-04-15 |
| BR6911126D0 (pt) | 1973-01-02 |
| FR2013934A1 (fr) | 1970-04-10 |
| CH510775A (de) | 1971-04-15 |
| GB1237612A (en) | 1971-06-30 |
| FR2013934B1 (fr) | 1976-10-15 |
| NL6911400A (fr) | 1970-02-02 |
| BE736731A (fr) | 1970-01-29 |
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