NO133452B - - Google Patents
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- Publication number
- NO133452B NO133452B NO2683/70A NO268370A NO133452B NO 133452 B NO133452 B NO 133452B NO 2683/70 A NO2683/70 A NO 2683/70A NO 268370 A NO268370 A NO 268370A NO 133452 B NO133452 B NO 133452B
- Authority
- NO
- Norway
- Prior art keywords
- resin
- phenol
- mol
- formaldehyde
- reaction
- Prior art date
Links
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 75
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 45
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 239000003054 catalyst Substances 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 23
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 238000010521 absorption reaction Methods 0.000 claims description 10
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 10
- 239000007859 condensation product Substances 0.000 claims description 10
- 239000004246 zinc acetate Substances 0.000 claims description 10
- 229940011182 cobalt acetate Drugs 0.000 claims description 5
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 claims description 5
- 229940071125 manganese acetate Drugs 0.000 claims description 5
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- SRWMQSFFRFWREA-UHFFFAOYSA-M zinc formate Chemical compound [Zn+2].[O-]C=O SRWMQSFFRFWREA-UHFFFAOYSA-M 0.000 claims description 4
- 238000000862 absorption spectrum Methods 0.000 claims description 2
- 239000012431 aqueous reaction media Substances 0.000 claims description 2
- PFQLIVQUKOIJJD-UHFFFAOYSA-L cobalt(ii) formate Chemical compound [Co+2].[O-]C=O.[O-]C=O PFQLIVQUKOIJJD-UHFFFAOYSA-L 0.000 claims description 2
- BHVPEUGTPDJECS-UHFFFAOYSA-L manganese(2+);diformate Chemical compound [Mn+2].[O-]C=O.[O-]C=O BHVPEUGTPDJECS-UHFFFAOYSA-L 0.000 claims description 2
- 229920005989 resin Polymers 0.000 description 97
- 239000011347 resin Substances 0.000 description 97
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 238000012360 testing method Methods 0.000 description 18
- 239000012071 phase Substances 0.000 description 17
- 239000000203 mixture Substances 0.000 description 16
- 239000011120 plywood Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 229920003987 resole Polymers 0.000 description 14
- 238000001723 curing Methods 0.000 description 13
- 238000002329 infrared spectrum Methods 0.000 description 13
- 229920003986 novolac Polymers 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 11
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical group C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 9
- 125000001033 ether group Chemical group 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 229920001568 phenolic resin Polymers 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 7
- 238000003825 pressing Methods 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 5
- 229920002522 Wood fibre Polymers 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 5
- 239000000920 calcium hydroxide Substances 0.000 description 5
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000012467 final product Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000002025 wood fiber Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000005060 rubber Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000000084 colloidal system Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 2
- 229910001863 barium hydroxide Inorganic materials 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000011094 fiberboard Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 235000020354 squash Nutrition 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- KIZFHUJKFSNWKO-UHFFFAOYSA-M calcium monohydroxide Chemical compound [Ca]O KIZFHUJKFSNWKO-UHFFFAOYSA-M 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000004414 compression moulding compound Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000004413 injection moulding compound Substances 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012430 organic reaction media Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- -1 polyoxymethylene groups Polymers 0.000 description 1
- 239000002990 reinforced plastic Substances 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C08G8/10—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with phenol
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA56613 | 1969-07-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO133452B true NO133452B (fr) | 1976-01-26 |
| NO133452C NO133452C (fr) | 1976-05-05 |
Family
ID=4085442
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2683/70A NO133452C (fr) | 1969-07-09 | 1970-07-08 |
Country Status (11)
| Country | Link |
|---|---|
| AT (1) | AT307046B (fr) |
| CA (1) | CA927041A (fr) |
| CH (1) | CH552645A (fr) |
| DE (1) | DE2034136A1 (fr) |
| ES (1) | ES381565A1 (fr) |
| FR (1) | FR2051635B1 (fr) |
| GB (1) | GB1265465A (fr) |
| NL (1) | NL163806C (fr) |
| NO (1) | NO133452C (fr) |
| SE (1) | SE383352B (fr) |
| ZA (1) | ZA704749B (fr) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4036816A (en) | 1972-12-14 | 1977-07-19 | Cor Tech Research Limited | Production of novel thermosetting phenol-formaldehyde resins by controlled acid reaction |
| DE2436893A1 (de) * | 1972-12-14 | 1976-02-19 | Cor Tech Res Ltd | Thermisch haertbare phenol/formaldehyd-harze und verfahren zur herstellung derselben |
| US4045411A (en) | 1973-12-03 | 1977-08-30 | Cor Tech Research Limited | Mobile room-temperature stable acid catalyzed phenol formaldehyde resin compositions |
| US4122144A (en) | 1973-12-03 | 1978-10-24 | Cor Tech Research Ltd. | Production of rigid shaped articles using phenol-formaldehyde resins |
| US4086125A (en) | 1974-04-17 | 1978-04-25 | Cor Tech Research Ltd. | Wood lamination method utilizing emulsified phenol-formaldehyde resins |
| US4184032A (en) | 1977-03-21 | 1980-01-15 | Cor Tech Research Ltd. | Control of procedures for formation of water-immiscible thermosetting phenol-formaldehyde resins |
| US4219634A (en) | 1977-03-21 | 1980-08-26 | Cor Tech Research Ltd. | Control of procedures for formation of water-immiscible thermosetting phenol-formaldehyde resins |
| US4140845A (en) | 1977-03-21 | 1979-02-20 | Cor Tech Research Ltd. | Control of procedures for formation of water-immiscible thermosetting phenol-formaldehyde resins |
| US4235989A (en) | 1978-12-22 | 1980-11-25 | Cor Tech Research Ltd. | Production of thermosetting phenol-formaldehyde resins |
| US4668759A (en) * | 1985-07-31 | 1987-05-26 | Acme Resin Corporation | Phenolic resin binders for foundry and refractory uses |
| DE3919756A1 (de) * | 1989-06-16 | 1990-12-20 | Hoechst Ag | Vorzugsweise plattenfoermiger formkoerper |
| US5290843A (en) * | 1993-04-29 | 1994-03-01 | Georgia-Pacific Resins, Inc. | Phenolic resins for reinforced composites |
| US6432254B1 (en) | 1997-11-26 | 2002-08-13 | Georgia-Pacific Resins Inc. | Wood composite prepared with a B-stageable resin |
-
1969
- 1969-07-09 CA CA927041A patent/CA927041A/en not_active Expired
-
1970
- 1970-07-08 NO NO2683/70A patent/NO133452C/no unknown
- 1970-07-08 ES ES381565A patent/ES381565A1/es not_active Expired
- 1970-07-08 GB GB1265465D patent/GB1265465A/en not_active Expired
- 1970-07-08 SE SE7009500A patent/SE383352B/xx unknown
- 1970-07-09 CH CH1041470A patent/CH552645A/xx not_active IP Right Cessation
- 1970-07-09 FR FR707025424A patent/FR2051635B1/fr not_active Expired
- 1970-07-09 AT AT627970A patent/AT307046B/de not_active IP Right Cessation
- 1970-07-09 ZA ZA704749A patent/ZA704749B/xx unknown
- 1970-07-09 DE DE19702034136 patent/DE2034136A1/de not_active Ceased
- 1970-07-09 NL NL7010201.A patent/NL163806C/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2034136A1 (de) | 1971-12-09 |
| NO133452C (fr) | 1976-05-05 |
| FR2051635A1 (fr) | 1971-04-09 |
| GB1265465A (fr) | 1972-03-01 |
| FR2051635B1 (fr) | 1973-04-27 |
| AT307046B (de) | 1973-05-10 |
| CA927041A (en) | 1973-05-22 |
| SE383352B (sv) | 1976-03-08 |
| DE2034136B2 (fr) | 1974-10-24 |
| CH552645A (de) | 1974-08-15 |
| NL163806B (nl) | 1980-05-16 |
| NL7010201A (fr) | 1971-01-12 |
| ES381565A1 (es) | 1973-04-01 |
| NL163806C (nl) | 1980-10-15 |
| ZA704749B (en) | 1971-03-31 |
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