PL84B1 - A method of making water-soluble, insoluble or sparingly soluble organic materials. - Google Patents
A method of making water-soluble, insoluble or sparingly soluble organic materials. Download PDFInfo
- Publication number
- PL84B1 PL84B1 PL84A PL8419A PL84B1 PL 84 B1 PL84 B1 PL 84B1 PL 84 A PL84 A PL 84A PL 8419 A PL8419 A PL 8419A PL 84 B1 PL84 B1 PL 84B1
- Authority
- PL
- Poland
- Prior art keywords
- soluble
- insoluble
- organic materials
- making water
- soluble organic
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims 2
- 239000011368 organic material Substances 0.000 title claims 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 8
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 4
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000003673 urethanes Chemical class 0.000 description 3
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 2
- FTOAOBMCPZCFFF-UHFFFAOYSA-N 5,5-diethylbarbituric acid Chemical compound CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 235000001258 Cinchona calisaya Nutrition 0.000 description 2
- 241000723346 Cinnamomum camphora Species 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 239000005844 Thymol Substances 0.000 description 2
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 2
- 229930008380 camphor Natural products 0.000 description 2
- 229960000846 camphor Drugs 0.000 description 2
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 description 2
- 229960003868 paraldehyde Drugs 0.000 description 2
- CPJSUEIXXCENMM-UHFFFAOYSA-N phenacetin Chemical compound CCOC1=CC=C(NC(C)=O)C=C1 CPJSUEIXXCENMM-UHFFFAOYSA-N 0.000 description 2
- 229960000948 quinine Drugs 0.000 description 2
- ZMQAAUBTXCXRIC-UHFFFAOYSA-N safrole Chemical compound C=CCC1=CC=C2OCOC2=C1 ZMQAAUBTXCXRIC-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- CESKLHVYGRFMFP-UHFFFAOYSA-N sulfonmethane Chemical compound CCS(=O)(=O)C(C)(C)S(=O)(=O)CC CESKLHVYGRFMFP-UHFFFAOYSA-N 0.000 description 2
- 229960000790 thymol Drugs 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 description 1
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 1
- 239000005792 Geraniol Substances 0.000 description 1
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 1
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 229960000212 aminophenazone Drugs 0.000 description 1
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 229960002319 barbital Drugs 0.000 description 1
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 1
- CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 description 1
- 229940116229 borneol Drugs 0.000 description 1
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000010630 cinnamon oil Substances 0.000 description 1
- 229940043350 citral Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- CLLOFODTUXGHHT-UHFFFAOYSA-N ethyl n-acetylcarbamate Chemical compound CCOC(=O)NC(C)=O CLLOFODTUXGHHT-UHFFFAOYSA-N 0.000 description 1
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 1
- 229940113087 geraniol Drugs 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- SUWZHLCNFQWNPE-LATRNWQMSA-N optochin Chemical compound C([C@H]([C@H](C1)CC)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OCC)C=C21 SUWZHLCNFQWNPE-LATRNWQMSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229960003893 phenacetin Drugs 0.000 description 1
- 229960005222 phenazone Drugs 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- RCIMBBZXSXFZBV-UHFFFAOYSA-N piromidic acid Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CN=C1N1CCCC1 RCIMBBZXSXFZBV-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
Description
Znaleziono, ze estry karbaminowych kwasów, uretany, przedstawiaja znakomi¬ te srodki rozpuszczajace dla trudno roz¬ puszczalnych, wzglednie nierozpuszczal¬ nych zwiazków organicznych. Zalety tych rozpuszczalników polegaja na ich neu¬ tralnym charakterze i na. pozadanej dla niektórych celów, nieobecnosci skladni¬ ków nieorganicznych.Ponadto w wielu wypadkach innemi rozpuszczalnikami wzgl. woda mozna osia¬ gnac daleko idace wzgl. nieograniczone rozcienczenie uzyskanych uretanami roz¬ tworów.Rozpuszczalnoscia w uretanach odzna¬ czaja sie zwiazki nastepujacych ty¬ pów. 1. Alkohole, (amylowy alkohol, ben¬ zylowy alkohol, cykloheicsanol, geraniol). 2. Zasady (anilina, fenylohydrozyna* chinolina i izochinolina). 3. Alkaloidy (chinina, optochina, mor¬ fina). 4. Dalej srodki lecznicze, nalezace do róznych klas cial, jak paraldehyd, sulfonal, antipiryna, tymol, fenacetyna, ane¬ stezyna, kamfora, puryny i t. d. 5. Olejki- eteryczne* Takze rozpuszczaja sie naturalne i sztuczne barwniki. Opisane zachowanie moze byc stwierdzone równiez na etylo- uretanie jak i na wyzszych i nizszych estrach kwasów karbominowych, jak me¬ tylowy, propylowy, izoamylowy, allylowy i glicerynowy ester.• Roztwory otrzymane z pomoca tych estrów sa trwale i daja sie wyjalowiac.Przez odparowanie takich roztworówmozna dojsc takze do preparatów sta- fych, przedstawiajacych mieszanine sub¬ stancji rozpuszczajacej i rozpuszczonej i dajacych sie latwo przez przyjecie wo¬ dy zpowrotem przeprowadzic w roztwór.Przyklady: 1.W 40%-wym wodnym roztworze ety- louretanu rozpuszcza sie w zwyklej tem¬ peraturze 20% alkoholu amylowego. 2. 50%_wy roztwór metylouretanu przyj¬ muje okolo 16% chinoliny. 3.W wodnym roztworze etylouretanu (75%-wy) rozpuszcza sie gladko 2% chi¬ niny; otrzymany roztwór mazna dowolnie rozcienczac woda, przyczem nie wyste¬ puje zmetnienie lub wydzielenie.Wieksze ilosci, az do 4%, zasady sa równiez utrzymywane w roztworze.Moznosc rozcienczania woda jest jed¬ nak wtedy ograniczona.W 50%-wym roztworze etylouretanu rozpuszcza sie latwo 2% optochininy. 4.Ze srodków leczniczych, które moga byc latwo utrzymywane w roztworze uretanu (75%-wy) i które mozna nieo- graniczenie woda rozcienczac, wymienia sie: antyfebryna w 3%, weronal w 3%, salipiryna w 25%, piramidon w 30%, sulfonal w 15%; paraldehyd w 30%, »en- - tol i borneol w 2%, tymol w 5%, kam¬ fora w 5%. 5.Cytral, safrol i olejek cynamonowy rozpuszczaja sie 2%-wo w 40%«wym roztworze metylouretanu. 6.Nierozpuszczalne barwniki jak nigro- zyna i alizaryna, barwniki azowe jak su- dan I i II rozpuszczaja sie w 5% w wod¬ nym roztworze acetylouretanu (50%-wy)- PL PLIt has been found that the carbamic acid esters of urethanes represent excellent dissolving agents for sparingly soluble, relatively insoluble organic compounds. The advantages of these solvents lie in their neutral nature and in their nature. desirable for some purposes, the absence of inorganic ingredients, and in many cases with other solvents or water can be achieved far-reaching or unlimited dilution of the solutions obtained with urethanes. Compounds of the following types show solubility in urethanes. 1. Alcohols (amyl alcohol, benzyl alcohol, cycloheicsanol, geraniol). 2. Bases (aniline, phenylhydrosine * quinoline and isoquinoline). 3. Alkaloids (quinine, optoquine, morphine). 4. Further medications belonging to different classes of the body, such as paraldehyde, sulfonal, antipyrin, thymol, phenacetin, anesthesin, camphor, purines, etc. 5. Essential oils * Also, natural and artificial dyes dissolve. The described behavior can also be observed on ethyl-urethane as well as on higher and lower esters of carbomic acids, such as methyl, propyl, isoamyl, allyl and glycerol esters. Such solutions can also result in solid preparations, which present a mixture of dissolving and dissolved substances and can be easily reconstituted by ingesting water. Examples: 1. In a 40% aqueous solution of ethylurethane, it is dissolved in the usual 20% amyl alcohol. 2. A 50% solution of methyl urethane absorbs about 16% of quinoline. 3. 2% of quinine is smoothly dissolved in an aqueous solution of ethylurethane (75%); The resulting solution can be diluted with water as desired, but there is no turbidity or separation. Larger amounts, up to 4%, are also kept in solution. The dilution capacity with water is limited, however. 50% ethylurethane solution dissolves. easily 2% optoquinine. (4) Medicines that can be easily kept in a urethane solution (75%) and that can be diluted indefinitely with water are: 3% antifebrin, 3% veronal, 25% salipirin, 30% pyramidone %, sulfonal at 15%; 30% paraldehyde, 2% enterol and borneol, 5% thymol, 5% camphor. 5. Citral, safrole and cinnamon oil dissolve 2% by weight in 40% methylurethane solution. 6. Insoluble dyes such as nigrosin and alizarin, azo dyes such as soda I and II dissolve in 5% in an aqueous solution of acetylurethane (50%) - PL EN
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Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL84B1 true PL84B1 (en) | 1924-05-26 |
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