CA1044397A - Aromatic polyketones - Google Patents
Aromatic polyketonesInfo
- Publication number
- CA1044397A CA1044397A CA204,546A CA204546A CA1044397A CA 1044397 A CA1044397 A CA 1044397A CA 204546 A CA204546 A CA 204546A CA 1044397 A CA1044397 A CA 1044397A
- Authority
- CA
- Canada
- Prior art keywords
- polymer
- formula
- inherent viscosity
- units
- recurring
- 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
Links
- 229920001470 polyketone Polymers 0.000 title abstract description 12
- 125000003118 aryl group Chemical group 0.000 title abstract description 8
- 229920000642 polymer Polymers 0.000 claims description 63
- 239000000203 mixture Substances 0.000 claims description 12
- 238000000748 compression moulding Methods 0.000 claims description 9
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- ITVUPWDTDWMACZ-UHFFFAOYSA-N (4-phenoxyphenyl)-phenylmethanone Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 ITVUPWDTDWMACZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims 1
- 239000011810 insulating material Substances 0.000 claims 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 abstract description 8
- UVGPELGZPWDPFP-UHFFFAOYSA-N 1,4-diphenoxybenzene Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1OC1=CC=CC=C1 UVGPELGZPWDPFP-UHFFFAOYSA-N 0.000 abstract description 4
- 238000010292 electrical insulation Methods 0.000 abstract description 3
- 230000000269 nucleophilic effect Effects 0.000 abstract description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 13
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- -1 isophthaloyl units Chemical group 0.000 description 9
- 229910015900 BF3 Inorganic materials 0.000 description 8
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 5
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- ZSBDGXGICLIJGD-UHFFFAOYSA-N 4-phenoxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC=C1 ZSBDGXGICLIJGD-UHFFFAOYSA-N 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 229920001577 copolymer Chemical class 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012834 electrophilic reactant Substances 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229920002493 poly(chlorotrifluoroethylene) Polymers 0.000 description 2
- 239000005023 polychlorotrifluoroethylene (PCTFE) polymer Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 1
- YAWIAFUBXXPJMQ-UHFFFAOYSA-N 1-bromo-4-(4-bromophenoxy)benzene Chemical compound C1=CC(Br)=CC=C1OC1=CC=C(Br)C=C1 YAWIAFUBXXPJMQ-UHFFFAOYSA-N 0.000 description 1
- HTUCJWIGUOMFRO-UHFFFAOYSA-N 1-phenoxy-2,3-diphenylbenzene Chemical compound C=1C=CC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C=1OC1=CC=CC=C1 HTUCJWIGUOMFRO-UHFFFAOYSA-N 0.000 description 1
- QSBDJCHYJZOIPJ-UHFFFAOYSA-N 2-(2-phenylphenoxy)benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1OC1=CC=CC=C1C1=CC=CC=C1 QSBDJCHYJZOIPJ-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- VUJPBQLLLURKBZ-UHFFFAOYSA-N 2-chlorobenzene-1,4-disulfonyl chloride Chemical compound ClC1=CC(S(Cl)(=O)=O)=CC=C1S(Cl)(=O)=O VUJPBQLLLURKBZ-UHFFFAOYSA-N 0.000 description 1
- LSQARZALBDFYQZ-UHFFFAOYSA-N 4,4'-difluorobenzophenone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=C(F)C=C1 LSQARZALBDFYQZ-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- IYRWEQXVUNLMAY-UHFFFAOYSA-N carbonyl fluoride Chemical compound FC(F)=O IYRWEQXVUNLMAY-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000010128 melt processing Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000010905 molecular spectroscopy Methods 0.000 description 1
- NFBOHOGPQUYFRF-UHFFFAOYSA-N oxanthrene Chemical compound C1=CC=C2OC3=CC=CC=C3OC2=C1 NFBOHOGPQUYFRF-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- MHAUGLFOVCQYNR-UHFFFAOYSA-N pentaphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 MHAUGLFOVCQYNR-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- KTQYWNARBMKMCX-UHFFFAOYSA-N tetraphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 KTQYWNARBMKMCX-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- LEMQFBIYMVUIIG-UHFFFAOYSA-N trifluoroborane;hydrofluoride Chemical compound F.FB(F)F LEMQFBIYMVUIIG-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- 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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/127—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from carbon dioxide, carbonyl halide, carboxylic acids or their derivatives
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyethers (AREA)
- Organic Insulating Materials (AREA)
- Polyesters Or Polycarbonates (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37861673A | 1973-07-12 | 1973-07-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1044397A true CA1044397A (en) | 1978-12-12 |
Family
ID=23493843
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA204,546A Expired CA1044397A (en) | 1973-07-12 | 1974-07-11 | Aromatic polyketones |
Country Status (11)
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5216360A (en) * | 1975-07-21 | 1977-02-07 | Kazuichi Hirano | Automatic stopper for grain dryer |
| CA1112393A (en) * | 1975-11-07 | 1981-11-10 | Klaus J. Dahl | Ketone and sulfone polymers |
| JPS52106197U (enrdf_load_stackoverflow) * | 1976-02-10 | 1977-08-12 | ||
| JPS5840691B2 (ja) * | 1976-02-18 | 1983-09-07 | 静岡製機株式会社 | 穀類処理装置における穀類含水率測定装置 |
| DE2861696D1 (en) * | 1977-09-07 | 1982-04-29 | Ici Plc | Thermoplastic aromatic polyetherketones, a method for their preparation and their application as electrical insulants |
| US4371554A (en) | 1979-11-09 | 1983-02-01 | Ashland Food Technology Holdings S.A. | Method of making skinless sausage using reusable porous polytetrafluoroethylene casing |
| JPS56141547A (en) * | 1980-04-04 | 1981-11-05 | Hitachi Metals Ltd | Moisture measuring method of molding sand |
| EP0063874A1 (en) | 1981-04-29 | 1982-11-03 | Imperial Chemical Industries Plc | Production of aromatic polyketones |
| GB8408082D0 (en) * | 1983-03-31 | 1984-05-10 | Raychem Corp | Preparing poly-(arylene ketones) |
| DE3416455A1 (de) * | 1984-05-04 | 1985-11-07 | Lorenz-Polygon-Ausbau Gmbh, 4600 Dortmund | Fuer aus stahlprofilen, insbesondere aus gi-profilen zusammengesetzte tuerstoecke des streckenausbaus im berg- und tunnelbau zur kraftschluessigen verbindung je eines kappenendes mit einem schraeggeneigten stempel vorgesehener sicherheitskappschuh |
| DE3416445A1 (de) * | 1984-05-04 | 1985-11-07 | Basf Ag, 6700 Ludwigshafen | Unvernetzte, thermoplastisch verarbeitbare polyetherketone und verfahren zu ihrer herstellung |
| EP0163464A1 (en) * | 1984-05-18 | 1985-12-04 | RAYCHEM CORPORATION (a California corporation) | Blends of poly (aryl ether) ketones |
| US4859715A (en) * | 1984-05-18 | 1989-08-22 | Raychem Corporation | Microporous poly (arylether ketone) article |
| CA1260187A (en) * | 1984-12-14 | 1989-09-26 | Isaburo Fukawa | Crystalline aromatic polyketone and process for producing the same |
| US4908425A (en) * | 1985-06-21 | 1990-03-13 | Amoco Corporation | Chain-extended poly(aryl ether ketones) |
| US4613645A (en) * | 1985-08-12 | 1986-09-23 | Union Carbide Corporation | Silicon carbide reinforcement of poly(aryl ether ketones) |
| EP3744751B1 (en) * | 2018-01-22 | 2022-08-17 | DIC Corporation | Polyarylene ether ketone resin and production method therefor, and molded article |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1086021A (en) * | 1964-01-22 | 1967-10-04 | Ici Ltd | Process for the production of aromatic polyketones |
| UST869003I4 (en) * | 1968-02-05 | 1969-12-16 | Defensive publication | |
| BE791798A (fr) * | 1971-11-24 | 1973-05-23 | Du Pont | Polycetones |
-
1974
- 1974-07-11 CA CA204,546A patent/CA1044397A/en not_active Expired
- 1974-07-11 SE SE7409131A patent/SE407419B/xx not_active IP Right Cessation
- 1974-07-11 JP JP49079705A patent/JPS604210B2/ja not_active Expired
- 1974-07-11 DE DE2433278A patent/DE2433278A1/de active Granted
- 1974-07-11 IT IT25086/74A patent/IT1030589B/it active
- 1974-07-11 NL NLAANVRAGE7409407,A patent/NL186451C/xx not_active IP Right Cessation
- 1974-07-12 GB GB3098874A patent/GB1471171A/en not_active Expired
- 1974-07-12 AT AT0578074A patent/AT363255B/de not_active IP Right Cessation
- 1974-07-12 FR FR7424375A patent/FR2236884B1/fr not_active Expired
- 1974-07-12 BE BE146539A patent/BE817628A/xx not_active IP Right Cessation
- 1974-07-12 IL IL45249A patent/IL45249A/xx unknown
-
1983
- 1983-09-07 JP JP58165828A patent/JPS59113030A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| AU7119774A (en) | 1976-01-15 |
| FR2236884A1 (enrdf_load_stackoverflow) | 1975-02-07 |
| JPS5039399A (enrdf_load_stackoverflow) | 1975-04-11 |
| NL186451C (nl) | 1990-12-03 |
| ATA578074A (de) | 1980-12-15 |
| JPS6254341B2 (enrdf_load_stackoverflow) | 1987-11-14 |
| NL7409407A (nl) | 1975-01-14 |
| IL45249A0 (en) | 1974-10-22 |
| SE7409131L (sv) | 1975-01-13 |
| GB1471171A (en) | 1977-04-21 |
| JPS59113030A (ja) | 1984-06-29 |
| SE407419B (sv) | 1979-03-26 |
| DE2433278A1 (de) | 1975-02-13 |
| IL45249A (en) | 1978-01-31 |
| AT363255B (de) | 1981-07-27 |
| FR2236884B1 (enrdf_load_stackoverflow) | 1979-08-03 |
| NL186451B (nl) | 1990-07-02 |
| BE817628A (fr) | 1975-01-13 |
| IT1030589B (it) | 1979-04-10 |
| DE2433278C2 (enrdf_load_stackoverflow) | 1987-06-11 |
| JPS604210B2 (ja) | 1985-02-02 |
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