NO117133B - - Google Patents
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- Publication number
- NO117133B NO117133B NO16768367A NO16768367A NO117133B NO 117133 B NO117133 B NO 117133B NO 16768367 A NO16768367 A NO 16768367A NO 16768367 A NO16768367 A NO 16768367A NO 117133 B NO117133 B NO 117133B
- Authority
- NO
- Norway
- Prior art keywords
- cyclohexyl
- methyl
- phenol
- acid
- formaldehyde
- Prior art date
Links
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 21
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- YWCLFFKWGMUSPB-UHFFFAOYSA-N 4-cyclohexyl-2-methylphenol Chemical class C1=C(O)C(C)=CC(C2CCCCC2)=C1 YWCLFFKWGMUSPB-UHFFFAOYSA-N 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 125000002147 dimethylamino group Chemical class [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- TYGUFBGQHKKFKB-UHFFFAOYSA-N 4-cyclohexyl-2-[(dimethylamino)methyl]-6-methylphenol Chemical compound CC1=C(C(=CC(=C1)C1CCCCC1)CN(C)C)O TYGUFBGQHKKFKB-UHFFFAOYSA-N 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- -1 rt-trioxymethylene Polymers 0.000 description 3
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 229960002703 undecylenic acid Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OAHMVZYHIJQTQC-UHFFFAOYSA-N 4-cyclohexylphenol Chemical compound C1=CC(O)=CC=C1C1CCCCC1 OAHMVZYHIJQTQC-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 208000007163 Dermatomycoses Diseases 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 241000223221 Fusarium oxysporum Species 0.000 description 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- 241001480037 Microsporum Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241000223238 Trichophyton Species 0.000 description 1
- 241001609979 Trichophyton quinckeanum Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 1
- 229960002327 chloral hydrate Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 201000003929 dermatomycosis Diseases 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 235000019640 taste Nutrition 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B61—RAILWAYS
- B61F—RAIL VEHICLE SUSPENSIONS, e.g. UNDERFRAMES, BOGIES OR ARRANGEMENTS OF WHEEL AXLES; RAIL VEHICLES FOR USE ON TRACKS OF DIFFERENT WIDTH; PREVENTING DERAILING OF RAIL VEHICLES; WHEEL GUARDS, OBSTRUCTION REMOVERS OR THE LIKE FOR RAIL VEHICLES
- B61F5/00—Constructional details of bogies; Connections between bogies and vehicle underframes; Arrangements or devices for adjusting or allowing self-adjustment of wheel axles or bogies when rounding curves
- B61F5/26—Mounting or securing axle-boxes in vehicle or bogie underframes
- B61F5/30—Axle-boxes mounted for movement under spring control in vehicle or bogie underframes
- B61F5/305—Axle-boxes mounted for movement under spring control in vehicle or bogie underframes incorporating rubber springs
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60G—VEHICLE SUSPENSION ARRANGEMENTS
- B60G11/00—Resilient suspensions characterised by arrangement, location or kind of springs
- B60G11/22—Resilient suspensions characterised by arrangement, location or kind of springs having rubber springs only
Landscapes
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Vehicle Body Suspensions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Fremgangsmåte til fremstilling av et basisk derivat av 2-metyl-4-cykloheksyl-fenol.
Det er funnet at 2-metyl-4-cykloheksyl-6-dimetyl-aminometyl-fenol og salter av dette med anorganiske og organiske syrer in vitro og in vivo viser sterk fungisid virkning.
2-metyl-4-cykloheksyl-6-dimetylami-nometyl-fenolet utvinnes ifølge forelig-gende oppfinnelse ved at 2-metyl-4-cykloheksyl-fenol omsettes med formaldehyd
eller formaldehydpolymerisater, som rt-trioksymetylen, paraformaldehyd og lignende, og dimetylamin eller dettes salter, f. eks. dets hydroklorid, sulfat osv., i et oppløsningsmiddel, fortrinsvis i varme,
hvorpå det slik dannede reaksjonsprodukt isoleres enten i form av den fri base eller, hvis ønsket, på vanlig måte overføres i salter, f. eks. i hydrokloridet.
Det nye 2-metyl-4-cykloheksyl-6-dime-tylaminometylfenol smelter ved 70—71 nC, er lett oppløselig i de vanlige organiske oppløsningsmidler og likeledes i en til salt-dannelse tilstrekkelig mengde av en anorganisk syre, som f. eks. saltsyre, svovelsyre, fosforsyre osv., eller en organisk syre, f. eks. vinsyre eller lignende.
Den fri base ed luktfri og smaker bit-tert. Såvel basen som også saltene egner seg godt for anvendelse som fungisid. Hen-siktsmessig anvender man det i form av salver, tinkturer eller pudder.
Forsøk har vist at 2-metyl-4-cykloheksyl-6-dimetyl-aminometyl-fenol-hydroklorid ennu i vandige forkynninger på 1 : 100 000 formår å hemme formeringen av hudpatogene sopper av følgende arter: Trichophyton mentagrophytes
Achorion quinckeanum.
Microsporum felineum.
Fusarium oxysporum. Undecylensyren, et kjent og til be-handling av Dermatomycosen klinisk egnet preparat, er overfor dette omtrent 100 gan-ger mindre virksom på Trichophyton-stammer.
Ved marssvin-infeksjon av Trichophyton mentagrophytes lykkes det å for-korte varigheten av soppinfeksjonen med en 10 pst.-ig salve av 2-metyl-4-cykloheksyl-6-dimetylaminometyl-fenol-hydroklorid vesentlig, mens ved analoge forsøK med 10 pst.-ig undecylensyresalve ingen forkorting av infeksjonsvarigheten er å iakta.
Oppfinnelsen forklares ved følgende eksempler:
Eksempel 1.
240 vektsdeler 2-metyl-4-cykloheksyl-fenol, som lett er å utvinne ved Mannich-reaksjon av dialkylaminer med formaldehyd og 4-cykloheksyl-fenol og etterføl-gende hydrering, oppløses i 600 volumdeler alkohol og blandes under omrøring med
150 volumdeler vandig dimetylamin-opp-løsning (22 pst.-ig). Derpå innfører man 115 volumdeler vandig formaldehyd (ca.
38 pst.-ig) i løpet av en time dråpevis i
den alkoholiske oppløsning og holder tem-peraturen i 6 timer ved 35—40° C. Herpå oppvarmer man ytterligere en time under omrøring til 80° C. og destillerer alkoholen til sist av i vakuum. Derunder går også
uforbrukt formaldehyd og ikke omsatt dimetylamin over. Resten tilsettes nu i 1000 volumdeler vann den nødvendige mengde konsentrert saltsyre inntil kongo-sur reaksjon, og uforbrukt 2-metyl-4-cykloheksyl-fenol fjernes ved tregangers utrysting med hver gang 200 volumdeler eter eller bensol. Man innstiller med konsentrert ammoniakk akkurat fenolftalein-alkalisk og ryster den slik erholdte Man-nich-base med 600 volumdeler eter eller bensol ut i 3 porsjoner. Ved avdestillering av eteren krystalliserer 2-metyl-4-cykloheksyl-6-dimetylaminometylfenol tilnær-met rent ut. Ved omkrystallisering fra alkohol kan man få basen i ren form, smelte-punkt 70—71° C. Den nye forbindelse er hvit, krystallinsk og løser seg lett i de fleste organiske oppløsningsmidler, i vann deri-mot bare meget vanskelig.
Eksempel 2.
Det ifølge eksempel 1 erholdte 2-metyl-4-cykloheksyl-6-dimetylaminometyl-fenol
overføres med den ekvimolekylare mengde saltsyre på vanlig måte i det tilsvarende klorhydrat.
Istedenfor saltsyre kan man også om-sette en annen vilkårlig anorganisk syre, som f. eks. svovelsyre, fosforsyre osv., eller en organisk syre, som f. eks. vinsyre, med 2-metyl-4-cykloheksyl-6-dimetylaminome-tyl-fenol, hvorved man får de tilsvarende salter.
Claims (1)
- Fremgangsmåte for fremstilling av et basisk derivat av 2-metyl-4-cykloheksyl-fenol, karakterisert ved at man omsetter 2-metyl-4-cykloheksyl-fenol med formaldehyd eller et formaldehydpolymerisat og dimetylamin eller et dimetylaminsalt, og hvis ønsket overfører det oppståtte reaksjonsprodukt ved hjelp av en anorganisk eller organisk syre i et salt av dette.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DER0044084 | 1966-09-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO117133B true NO117133B (no) | 1969-07-07 |
Family
ID=7407176
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO16768367A NO117133B (no) | 1966-09-08 | 1967-04-11 |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT282684B (no) |
| BE (1) | BE695746A (no) |
| CH (1) | CH454940A (no) |
| DE (1) | DE1605108A1 (no) |
| ES (1) | ES339198A1 (no) |
| GB (1) | GB1161839A (no) |
| NL (1) | NL6704878A (no) |
| NO (1) | NO117133B (no) |
| SE (1) | SE334382B (no) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2023523B (en) * | 1978-06-10 | 1982-09-15 | Dunlop Ltd | Vehicle suspension |
| EP0086578B1 (en) * | 1982-02-11 | 1988-10-19 | Dunlop Limited | Vehicle axle suspension |
| CN104828106B (zh) * | 2015-05-25 | 2018-02-06 | 株洲市源创科技有限公司 | 一种铁路货车转向架轴箱弹性定位方法及装置 |
| CN105818829B (zh) * | 2016-06-08 | 2017-11-10 | 江苏瑞铁轨道装备股份有限公司 | 一种快速铁路货车转向架 |
-
1966
- 1966-09-08 DE DE19661605108 patent/DE1605108A1/de active Pending
-
1967
- 1967-03-14 CH CH372967A patent/CH454940A/de unknown
- 1967-03-20 BE BE695746D patent/BE695746A/xx unknown
- 1967-03-29 AT AT299967A patent/AT282684B/de not_active IP Right Cessation
- 1967-04-06 NL NL6704878A patent/NL6704878A/xx unknown
- 1967-04-11 NO NO16768367A patent/NO117133B/no unknown
- 1967-04-12 ES ES339198A patent/ES339198A1/es not_active Expired
- 1967-05-11 GB GB2185767A patent/GB1161839A/en not_active Expired
- 1967-06-27 SE SE934667A patent/SE334382B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES339198A1 (es) | 1968-04-16 |
| GB1161839A (en) | 1969-08-20 |
| CH454940A (de) | 1968-04-30 |
| NL6704878A (no) | 1968-03-11 |
| AT282684B (de) | 1970-07-10 |
| BE695746A (no) | 1967-09-01 |
| DE1605108A1 (de) | 1970-07-16 |
| SE334382B (no) | 1971-04-26 |
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