IL40234A - The manufacture of phosphorus-containing condensation products,the products and their use as flameproofing agents - Google Patents
The manufacture of phosphorus-containing condensation products,the products and their use as flameproofing agentsInfo
- Publication number
- IL40234A IL40234A IL40234A IL4023472A IL40234A IL 40234 A IL40234 A IL 40234A IL 40234 A IL40234 A IL 40234A IL 4023472 A IL4023472 A IL 4023472A IL 40234 A IL40234 A IL 40234A
- Authority
- IL
- Israel
- Prior art keywords
- process according
- tetrakis
- manufacture
- hydroxymethyl
- component
- Prior art date
Links
- 239000007859 condensation product Substances 0.000 title claims abstract 10
- 239000003795 chemical substances by application Substances 0.000 title claims abstract 5
- 238000004519 manufacturing process Methods 0.000 title claims 12
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title abstract 2
- 229910052698 phosphorus Inorganic materials 0.000 title abstract 2
- 239000011574 phosphorus Substances 0.000 title abstract 2
- 239000000047 product Substances 0.000 title abstract 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract 9
- 239000000463 material Substances 0.000 claims abstract 9
- 238000009833 condensation Methods 0.000 claims abstract 7
- 230000005494 condensation Effects 0.000 claims abstract 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract 6
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims abstract 6
- 239000000835 fiber Substances 0.000 claims abstract 5
- 238000010438 heat treatment Methods 0.000 claims abstract 5
- -1 tetrakis-(hydroxymethyl)- phosphonium compound Chemical class 0.000 claims abstract 5
- 239000004744 fabric Substances 0.000 claims abstract 4
- 229910021529 ammonia Inorganic materials 0.000 claims abstract 3
- 150000002118 epoxides Chemical class 0.000 claims abstract 3
- 239000003960 organic solvent Substances 0.000 claims abstract 3
- 229920000728 polyester Polymers 0.000 claims abstract 3
- YTVQIZRDLKWECQ-UHFFFAOYSA-N 2-benzoylcyclohexan-1-one Chemical compound C=1C=CC=CC=1C(=O)C1CCCCC1=O YTVQIZRDLKWECQ-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 2
- 210000002268 wool Anatomy 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims 30
- 239000002904 solvent Substances 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 3
- FAUOSXUSCVJWAY-UHFFFAOYSA-N tetrakis(hydroxymethyl)phosphanium Chemical class OC[P+](CO)(CO)CO FAUOSXUSCVJWAY-UHFFFAOYSA-N 0.000 claims 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 2
- 229920002678 cellulose Polymers 0.000 claims 2
- 239000001913 cellulose Substances 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 238000006266 etherification reaction Methods 0.000 claims 2
- 150000004679 hydroxides Chemical class 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 239000007858 starting material Substances 0.000 claims 2
- IOIHFHNPXJFODN-UHFFFAOYSA-M tetrakis(hydroxymethyl)phosphanium;hydroxide Chemical compound [OH-].OC[P+](CO)(CO)CO IOIHFHNPXJFODN-UHFFFAOYSA-M 0.000 claims 2
- 239000008096 xylene Substances 0.000 claims 2
- 241000237519 Bivalvia Species 0.000 claims 1
- VGGLHLAESQEWCR-UHFFFAOYSA-N N-(hydroxymethyl)urea Chemical compound NC(=O)NCO VGGLHLAESQEWCR-UHFFFAOYSA-N 0.000 claims 1
- 239000004952 Polyamide Substances 0.000 claims 1
- MBHRHUJRKGNOKX-UHFFFAOYSA-N [(4,6-diamino-1,3,5-triazin-2-yl)amino]methanol Chemical compound NC1=NC(N)=NC(NCO)=N1 MBHRHUJRKGNOKX-UHFFFAOYSA-N 0.000 claims 1
- 229920003180 amino resin Polymers 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 235000020639 clam Nutrition 0.000 claims 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 claims 1
- 229920002647 polyamide Polymers 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract 3
- 229920000742 Cotton Polymers 0.000 abstract 2
- SUPOBRXPULIDDX-UHFFFAOYSA-N [[4-amino-6-(hydroxymethylamino)-1,3,5-triazin-2-yl]amino]methanol Chemical compound NC1=NC(NCO)=NC(NCO)=N1 SUPOBRXPULIDDX-UHFFFAOYSA-N 0.000 abstract 1
- 229940077445 dimethyl ether Drugs 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 229910017464 nitrogen compound Inorganic materials 0.000 abstract 1
- 150000002830 nitrogen compounds Chemical class 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 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
- D06M15/667—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing phosphorus in the main chain
- D06M15/673—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing phosphorus in the main chain containing phosphorus and nitrogen in the main chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5407—Acyclic saturated phosphonium compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08L61/32—Modified amine-aldehyde condensates
-
- 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
- D06M15/43—Amino-aldehyde resins modified by phosphorus compounds
- D06M15/431—Amino-aldehyde resins modified by phosphorus compounds by phosphines or phosphine oxides; by oxides or salts of the phosphonium radical
-
- 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
- D06M15/667—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing phosphorus in the main chain
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K2240/00—Purpose of the treatment
- B27K2240/30—Fireproofing
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/02—Processes; Apparatus
- B27K3/15—Impregnating involving polymerisation including use of polymer-containing impregnating agents
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
1388605 Phosphorus-containing condensation polymers CIBA-GEIGY AG 5 Sept 1972 [10 Sept 1971] 41096/72 Heading C3R [Also in Division D1] Condensation products are obtained by condensing 1 mol. of a tetrakis-(hydroxymethyl)- phosphonium compound with 0 02 to 0 5 mol. of cyanamide at 40 to 120 C., optionally in the presence of formaldehyde or a formaldehydedonating agent and optionally in an inert organic solvent. The condensation optionally may be continued at 100 to 150 C. and free hydroxyl groups may be etherified. Organic fibre materials may be flameproofed by applying to them aqueous compositions of the condensation products together with polyfunctional epoxides or nitrogen compounds, and curing by heating the materials either when dry or while still moist or by contacting them with ammonia. In examples condensation products are obtained by reacting tetrakis-(hydroxymethyl)-phosphonium chloride and hydroxide with cyanamide; in one instance the product is etherified with methanol and in another formaldehyde is included in the condensation; fabrics of polyester-cotton, polyester, cotton and wool are flameproofed by applying to them aqueous compositions containing the condensation products together with dimethylolmelamine and trimethylolmelamine-dimethyl-ether, the compositions being cured by drying and heating the fabrics, by heating them while moist and by contacting them with ammonia.
[GB1388605A]
Claims (2)
1. WHAT ¥E CLAIM IS: 1. Process for the manufacture of water-soluble condensation products from hydroxyme hyl-phosphonium compounds and cyanamide, characterised in that 1 mol of a tetrak±s-(hydroxy-methyl)-phosphonium compound is condensed with 0.02 to 0.5 mol of cyanamide at 40 to 120°0, optionally in the presence of formaldehyde or a formaldehyde-donating agent and optionally in the presence of an inert organic solvent and optionally subsequently further condensed at temperatures of 100 up to 150°c and, if appropriate, free hydroxyl groups are at least partially etherified with at least one alkanol with 1 to 4-carbon atoms.
2. Process according to Claim 1, characterised in that the condensation is carried out at 70 to 110°C · 3. Process according to Claim 1 or 2 , characterised in that the condensation is carried out in the presence of at-least one inert aromatic hydrocarbon as the solvent* * ·. ' ;.. 4. Process according to Claim 3, characterised in that at least one xylene is used as the solvent. 5. Process according to one of Claims 1 to 4, characterised in that the two starting materials are condensed with one another in a molar ratio of 1:0.1 to 1:0.3· 6. Process according to one of Claims 1 to 5, character- r ised in that a tetrakis-(hydroxymethyl)-phosphonium salt or tetrakis-(hydroxymethyl)-phosphonium hydroxide is used. 7. Process according to Claim 6, characterised in that' a tetrakis-(hydroxymethyl)-phosphonium salt is used. 8. Process according to Claim 7, characterised in that a 40234/2 tetrakis-(hydrox methyl)-phosphonium halide is used. 9. Process according to Claim 8. characterised in that a tetrakis- (hydroxymethyl-)-phosphoni- in- chioride-is - used * 10. Process according to one of Claims 1 to 9, characterised in that etherification is carried out v/ith methanol. 11. Process according to one of Claims 1 to 10, characterised in that after completion of- the reaction the salts of the condensation products are converted into the corresponding hydroxides, 12. The condensation products obtainable according to the process of one of Claims 1 to 11. 13. Process for flameproofing organic fibre materials, characterised in that these materials are treated with an aqueous preparation which contains at least (1) a water-soluble condensation product of a hydroxymethyl-phosphonium compound and cyanamide, which is obtained by condensing 1 mol of a tetrakis-(hydroxymethyl)-phosphonium compound with 0.02 to 0.5 mol of cyanamide at 40 to 120°C, optionally in the presence of formaldehyde or a formaldehyde-donating agent and optionally in the presence of an inert organic solvent, and optionally subsequently further condensing at temperatures of 100 to 150°C, and, if appropriate, etherifying free hydro yl groups at least partially v/ith at least one alkanol with 1 to 4 carbon atoms, and (2) a polyfunctional epoxide having at least two epoxide groups which is derived from polyh dric phenols, a polyalkylenepolyamine , an aminoplast-forming agent or an aminoplast precondensate, and tha the materials treated in this way are finished by the thermofixing, moist batch, wet batch or ammonia fixing process. the treated materials are dried and subjected to a heat treatment. 15. Process according to Claim 1 , characterised in that in the manufacture of the component (1) the condensation is carried out at 70 to 110°C. 16. Process according to Claim 14 or 15, characterised in that in the manufacture of the component (1) the condensation is carried out in the presence of at least one inert aromatic hydrocarbon as the solvent. 17. Process according to Claim 16, characterised in that in the manufacture of the component (l) at least one xylene is used as the solvent. 18. Process according to one of Claims 14 to 17, characterised in that in the manufacture of the component (1) the two starting materials are condensed with one another in a molar ratio of 1:0.1 to 1:0,3* 19. Process according to one of Claims 14 to 18, characterised in that in the manufacture of the component (1) a tetrakis-(hydroxymethyl)-phosphonium salt or tetrakis-(hydroxy-methyl) -phosphonium hydroxide is used. 20. Process according to Claim 19, characterised in that in the manufacture of the component (l) a tetrakis-(hydroxy- .· methyl) -phospho.nium salt is used, 21. Process according to Claim 20, characterised in that in the manufacture of the component (1) a tetrakis-(hydroxymethyl)-phosphonium halide is used.. 22. Process according to Claim 21, characterised in that in the manufacture of the component (l) tetrakis-(hydroxymethyl)-phosphonium chloride is used. 40234/2 23. Process according to one of Claims 14 to 22, characterised in that in the manufacture of the component (1) etheri-fication' is -carried" out "v/ith" methanol. 24. Process according to one of Claims 14 to 23, characterised in that in the manufacture of the component (1) the salts of the condensation products are converted, after completion of the reaction, into the corresponding hydroxides. 25. Process according to Claim 14, characterised in that a methylolurea or a methylolmelamine is used as the component (2). 26. Process according to one of Claims 14 to 25, characterised in that fibre material of polyamides, cellulose, cellulose-poD.yester or polyester is flameproofed . 27. Process according to Claim 26, characterised in that fabrics of wool or polyester or mixed fabrics of polyester-cellulose are rendered flameproof. 28. Process according to one of Claims 13 to 27, characterised in that the fibre material is dried at temperatures of up to 100°C and is subjected to a heat treatment above 100°C. 29. The organic fibre materials provided wit a flameproof finish by the process according to one of Clams 13 to 28. 30. The aqueous preparations used to carry out the process according to one of Claims 13 to 28. HE :mr
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1330371A CH547895A (en) | 1971-09-10 | 1971-09-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL40234A0 IL40234A0 (en) | 1972-10-29 |
| IL40234A true IL40234A (en) | 1976-02-29 |
Family
ID=4391233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL40234A IL40234A (en) | 1971-09-10 | 1972-08-29 | The manufacture of phosphorus-containing condensation products,the products and their use as flameproofing agents |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS4836489A (en) |
| AR (1) | AR197578A1 (en) |
| AT (1) | AT317827B (en) |
| AU (1) | AU467686B2 (en) |
| BE (1) | BE788584A (en) |
| BR (1) | BR7206209D0 (en) |
| CA (1) | CA1008879A (en) |
| CH (2) | CH1330371A4 (en) |
| CS (1) | CS158735B2 (en) |
| DE (1) | DE2242683A1 (en) |
| FR (1) | FR2152694B1 (en) |
| GB (1) | GB1388605A (en) |
| IL (1) | IL40234A (en) |
| IT (1) | IT965260B (en) |
| NL (1) | NL7212251A (en) |
| SU (1) | SU518149A3 (en) |
| ZA (1) | ZA725943B (en) |
-
0
- BE BE788584D patent/BE788584A/en unknown
-
1971
- 1971-09-10 CH CH1330371D patent/CH1330371A4/xx unknown
- 1971-09-10 CH CH1330371A patent/CH547895A/xx unknown
-
1972
- 1972-08-08 AR AR243976A patent/AR197578A1/en active
- 1972-08-29 IL IL40234A patent/IL40234A/en unknown
- 1972-08-30 ZA ZA725943A patent/ZA725943B/en unknown
- 1972-08-30 DE DE2242683A patent/DE2242683A1/en active Pending
- 1972-08-31 AU AU46187/72A patent/AU467686B2/en not_active Expired
- 1972-08-31 CA CA150,637A patent/CA1008879A/en not_active Expired
- 1972-09-05 GB GB4109672A patent/GB1388605A/en not_active Expired
- 1972-09-06 BR BR6209/72A patent/BR7206209D0/en unknown
- 1972-09-06 SU SU1827455A patent/SU518149A3/en active
- 1972-09-07 FR FR7231656A patent/FR2152694B1/fr not_active Expired
- 1972-09-08 NL NL7212251A patent/NL7212251A/xx unknown
- 1972-09-08 CS CS617272A patent/CS158735B2/cs unknown
- 1972-09-08 AT AT771472A patent/AT317827B/en not_active IP Right Cessation
- 1972-09-08 IT IT52614/72A patent/IT965260B/en active
- 1972-09-09 JP JP47090041A patent/JPS4836489A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4836489A (en) | 1973-05-29 |
| CH1330371A4 (en) | 1973-07-31 |
| AR197578A1 (en) | 1974-04-23 |
| AU4618772A (en) | 1974-03-07 |
| BR7206209D0 (en) | 1973-09-25 |
| GB1388605A (en) | 1975-03-26 |
| AU467686B2 (en) | 1975-12-11 |
| BE788584A (en) | 1973-03-08 |
| AT317827B (en) | 1974-09-10 |
| IT965260B (en) | 1974-01-31 |
| FR2152694A1 (en) | 1973-04-27 |
| ZA725943B (en) | 1973-06-27 |
| NL7212251A (en) | 1973-03-13 |
| CS158735B2 (en) | 1974-11-25 |
| CH547895A (en) | 1974-04-11 |
| IL40234A0 (en) | 1972-10-29 |
| DE2242683A1 (en) | 1973-03-15 |
| SU518149A3 (en) | 1976-06-15 |
| FR2152694B1 (en) | 1974-08-19 |
| CA1008879A (en) | 1977-04-19 |
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