US2466177A - Hydantoins and method fob obtaining - Google Patents
Hydantoins and method fob obtaining Download PDFInfo
- Publication number
- US2466177A US2466177A US2466177DA US2466177A US 2466177 A US2466177 A US 2466177A US 2466177D A US2466177D A US 2466177DA US 2466177 A US2466177 A US 2466177A
- Authority
- US
- United States
- Prior art keywords
- hydantoin
- allyl
- hydantoins
- solution
- phenyl
- 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 - Lifetime
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- 238000000034 method Methods 0.000 title description 8
- 150000001469 hydantoins Chemical class 0.000 title description 7
- -1 alkali metal salts Chemical class 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 13
- WHRGIOPIQZBECO-UHFFFAOYSA-N 5-phenyl-1-prop-2-enylimidazolidine-2,4-dione Chemical compound O=C1NC(=O)N(CC=C)C1C1=CC=CC=C1 WHRGIOPIQZBECO-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 125000005219 aminonitrile group Chemical group 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical group O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 229940091173 hydantoin Drugs 0.000 description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 description 6
- 239000011707 mineral Substances 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 6
- NNICRUQPODTGRU-UHFFFAOYSA-N mandelonitrile Chemical compound N#CC(O)C1=CC=CC=C1 NNICRUQPODTGRU-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 235000011118 potassium hydroxide Nutrition 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000001961 anticonvulsive agent Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 206010015037 epilepsy Diseases 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 238000004148 unit process Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 230000001773 anti-convulsant effect Effects 0.000 description 2
- 229960003965 antiepileptics Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 208000034308 Grand mal convulsion Diseases 0.000 description 1
- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 1
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 230000002082 anti-convulsion Effects 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 229940053195 antiepileptics hydantoin derivative Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 150000001913 cyanates Chemical class 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/74—Two oxygen atoms, e.g. hydantoin with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members
Definitions
- This invention relates to 1-allyl-5-phenylhydantoin and its alkali metal salts and also to a method for obtaining these products
- 1-allyl-5- phenylhydantoin has the formula
- the new compounds of'the present invention are powerful anticonvulsants and are particularly valuable in the treatment of the grand mal form of epilepsy.
- hydantoins in the treatment of epilepsy are well-known to the art.
- the most effective compounds of this type are probably those which contain two hydrocarbon substituents in the five position.
- Some other 5,'5-disubst'ituted hydantoins which have proved of value are those which have an additional substituent(s) in the one and/ or three positions of the ring.
- the hydantoins which have only one hydrocarbon substituent in the five position show very little or no anticonvulsive activity. I have found this to be particularly true of the l-alkyl- S-phenyl hydantoins.
- hydantoin derivatives possess no activity as anticanvulsants and are, in addition, very toxic compounds. It was surprising to find that 1-allyl-5- phenyl hydantoin is an extremely potent and nontoxic anticonvulsant since the only structural difierence between this compound and the inactive and toxic 1-alkyl-5-phenyl hydantoins is that the compounds of the present invention have an unsaturated alkyl rather than a saturated alkyl radical in the one position of the ring.
- 5,5-disubstituted hydantoins of the prior art suffer the disadvantage that they must be administered in the form of their alkali metal salts in order to obtain the maximal therapeutic eifect.
- I have found that it is not necessary to administer 1-allyl-5-phenyl hydantoin as its alkali metal salts since the free hydantoin produces just as beneficial a therapeutic effect as its alkali metal salts.
- the compounds of the present invention may be conveniently administered by the oral route to human patients suffering from-epilepsy.
- ,1-allyl-5-phenylhydantoin maybe prepared by a unit process starting with benzaldehyde cyanohydrin and allyl amine.
- the first step in this unit process is to react the benzaldehyde cyanohydrin and the allyl amine to obtain the corresponding aminonitrile,
- This phase or .step of the process is usually carried out by simply bringing the two reactants together in an inert organic solvent such as ether'or benzene.
- the water layer which separates from the mixture is withdrawn and the solvent distilled.
- the next step in the process is the treatment of the crude aminonitrile with potassium cyanate in the presence of acid at about 5 C.
- the alkali metal salts of 1-allyl-5-phenylhydantoin may be conveniently prepared by dissolving the hydantoin in excess sodium or potassium hydroxide and precipitating the salt from the solution by addition of a Water-miscible organic solvent such as methanol, ethanol, n-propanol, acetone, dioxane and the like, Alternatively, equivalent amounts of sodium or potassium hydroxide and the hydantoin may be reacted in aqueous solution and the resulting aqueous solution of the salt evaporated to dryness under reduced pressure.
- a Water-miscible organic solvent such as methanol, ethanol, n-propanol, acetone, dioxane and the like
- alkali metal salts of 1-ally1-5-phenyl hydantoin obtained by either of these two procedures are white, water-soluble, amphorous powders which are, because of their water-solubility, particularly useful for oral administration of this valuable therapeutic agent.
- the potassium salt By substituting an equivalent amount of potassium hydroxide for sodium hydroxide in this pro-' cedure, one obtains the potassium salt. Instead of evaporating the solution, the salt can be pre- Number cipitated from the reaction mixture by the addition of n-propanol.
- Another method of preparing the salts of the present invention consists in adding an alcoholic solution of the hydantoin to an alcoholic solution of sodium or potassium hydroxides or ethylates.
- an alcoholic solution of the hydantoin for example, 10 g. of thehydantoin dissolved in absolute ethanol is added to an absolute ethanol solution containing 4 g. of potassium ethylate.
- the white potassium salt which separates is removed by filtration, washed with alcohol and dried.
- a compound of the class consisting of l-allyl- 5-phenyl hydantoin and its corresponding alkali metal salts.
- a unit process for the preparation of l-allyl- 5-phenyl hydantoin which comprises reacting benzaldehyde cyanohydrin with allyl amine in an inert organic solvent, removing said solvent from the reaction mixture, reacting the crude aminonitrile so formed with an alkali metal cyanate at a temperature below about 10 C. and in the presence of aqueous mineral acid, hydrolyzing the intermediate ureido nitrile by heating the acidic reaction mixture and isolating the product so formed.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Patented Apr. 5, 1949 UNITED STATES PATENT OFFICE Loren M. Long, Detroit, Mich, 'assignor to Parke,
Davis & Company, Detroit, Mich., a corporation of Michigan No Drawing. Application March '11, 1946, Serial No. 653,711
Claims. 1 This invention relates to 1-allyl-5-phenylhydantoin and its alkali metal salts and also to a method for obtaining these products 1-allyl-5- phenylhydantoin has the formula,
QIH-n-ommhom The new compounds of'the present invention are powerful anticonvulsants and are particularly valuable in the treatment of the grand mal form of epilepsy.
The use of hydantoins in the treatment of epilepsy is well-known to the art. The most effective compounds of this type are probably those which contain two hydrocarbon substituents in the five position. Some other 5,'5-disubst'ituted hydantoins which have proved of value are those which have an additional substituent(s) in the one and/ or three positions of the ring. However, in general, the hydantoins which have only one hydrocarbon substituent in the five position show very little or no anticonvulsive activity. I have found this to be particularly true of the l-alkyl- S-phenyl hydantoins. These particular hydantoin derivatives possess no activity as anticanvulsants and are, in addition, very toxic compounds. It was surprising to find that 1-allyl-5- phenyl hydantoin is an extremely potent and nontoxic anticonvulsant since the only structural difierence between this compound and the inactive and toxic 1-alkyl-5-phenyl hydantoins is that the compounds of the present invention have an unsaturated alkyl rather than a saturated alkyl radical in the one position of the ring. Perhaps even more surprising was the discovery that replacing the hydrogen atom in the five position of the hydantoin ring in 1-allyl-5-phenyl hydantoin by an alkyl radical results in the formation of a class of hydantoin compounds which are almost completely devoid of anticonvulsant activity and which are extremely toxic.
Some of the 5,5-disubstituted hydantoins of the prior art, for example 5,5-diphenyl hydantoin, suffer the disadvantage that they must be administered in the form of their alkali metal salts in order to obtain the maximal therapeutic eifect. However, in accordance with my invention I have found that it is not necessary to administer 1-allyl-5-phenyl hydantoin as its alkali metal salts since the free hydantoin produces just as beneficial a therapeutic effect as its alkali metal salts. The compounds of the present invention may be conveniently administered by the oral route to human patients suffering from-epilepsy. In the case of children over the age of six the average daily dose is between about 0.2 and 0.4 gram per day while the dosage for adults is usually about -.0.6 gram per day. For best results and prolonged therapeutic effect about 0.2 gram of the drug should be taken before each meal.
I have found that ,1-allyl-5-phenylhydantoin maybe prepared by a unit process starting with benzaldehyde cyanohydrin and allyl amine. The first step in this unit process is to react the benzaldehyde cyanohydrin and the allyl amine to obtain the corresponding aminonitrile, This phase or .step of the process is usually carried out by simply bringing the two reactants together in an inert organic solvent such as ether'or benzene. After the formation of the aminonitrile is complete, the water layer which separates from the mixture is withdrawn and the solvent distilled. The next step in the process is the treatment of the crude aminonitrile with potassium cyanate in the presence of acid at about 5 C. .to obtain the corresponding ureido nitrile which is then hydrolyzed by boiling with acid to obtain the desired hydantoin. In the prior art the reaction between similar aminonitriles and potassium cyanate has always been carried out in the presence of weak acids such as acetic acid while the subsequent hydrolytic reaction has been effected by boiling the ureido nitrile with mineral acid. However, in this particular case I have found that the reaction between the aminonitrile and the cyanate salt may also be carried out below about 10 C. in the presence of a strong mineral acid such as hydrochloric or hydrobromic acid and the resultant ureido nitrile subsequently hydrolyzed by merely boiling the solution. In general, it is not necessary to add any more mineral acid before hydrolyzing the ureido nitrile although if rather dilute mineral acid is used in the cyanate-aminonitrile reaction, it is sometimes advisable to add a small amount of mineral acid to insure completeness of the hydrolysis reaction. The chief advantages of my modified process over the analogous processes of the prior art lie principally in its simplicity and lower cost.
The alkali metal salts of 1-allyl-5-phenylhydantoin may be conveniently prepared by dissolving the hydantoin in excess sodium or potassium hydroxide and precipitating the salt from the solution by addition of a Water-miscible organic solvent such as methanol, ethanol, n-propanol, acetone, dioxane and the like, Alternatively, equivalent amounts of sodium or potassium hydroxide and the hydantoin may be reacted in aqueous solution and the resulting aqueous solution of the salt evaporated to dryness under reduced pressure. The alkali metal salts of 1-ally1-5-phenyl hydantoin obtained by either of these two procedures are white, water-soluble, amphorous powders which are, because of their water-solubility, particularly useful for oral administration of this valuable therapeutic agent.
The invention is illustrated by the following specific example without limitingit thereto.
39.9 g. of benzaldehyde cyanohydrin dissolved in 50- cc. of ether is mixed with 17.1 g. of allyl amine. The solution turns yellow and becomes quite warm and as the reaction proceeds the water which is formed separates. After the reaction is complete, the water is drawn off and the ether evaporated. The thick liquid residue which consists of the intermediate aminonitrile is added to a solution of 42 cc. of concentrated hydrochloric acid and 300 cc. of water. The resulting solution is cooled to 5 C. and a total of 30 got potassium cyanate added in small portions with frequent shaking. After all the cyanate is added, the mixture is allowed to stand in an ice bath for one-half hour and then heated on a steam bath for one-half hour. 300 cc. of concentrated hydrochloric acid is added and the mixture evaporated to dryness. The residue which consists of the crude 1-allyl-5-phenylhydantoin is washed with 300 cc. of cold water and then dissolved in dilute sodium hydroxide solution. The alkaline solution is decolorized by treatment with activated charcoal, filtered and the product reprecipitated by acidifying the filtrate with hydrochloric acid. The crude hydantoin is finally purified by recrystallization from alcohol-water mixture to yield 32 g. of th pure white crystalline product; M. P. 955 C.
g. of 1-allyl-5-phenyl hydantoin is dissolved in a small amount of water containing 1.85 of sodium hydroxide and the resulting solution evaporated to dryness under reduced pressure. The light colored, amphorous residue consists of the desired sodium salt of 1-allyl-5-phenyl hydantoin.
' By substituting an equivalent amount of potassium hydroxide for sodium hydroxide in this pro-' cedure, one obtains the potassium salt. Instead of evaporating the solution, the salt can be pre- Number cipitated from the reaction mixture by the addition of n-propanol.
Another method of preparing the salts of the present invention consists in adding an alcoholic solution of the hydantoin to an alcoholic solution of sodium or potassium hydroxides or ethylates. For example, 10 g. of thehydantoin dissolved in absolute ethanol is added to an absolute ethanol solution containing 4 g. of potassium ethylate. The white potassium salt which separates is removed by filtration, washed with alcohol and dried.
What I claim as my invention is:
1. A compound of the class consisting of l-allyl- 5-phenyl hydantoin and its corresponding alkali metal salts.
2. 1-Allyl-5-phenyl hydantoin.
3. The sodium salt of l-allyl-5-phenyl hydantoin.
4. The potassium salt of 1-ally1-5-phenyl hydantoin. 1
5. A unit process for the preparation of l-allyl- 5-phenyl hydantoin which comprises reacting benzaldehyde cyanohydrin with allyl amine in an inert organic solvent, removing said solvent from the reaction mixture, reacting the crude aminonitrile so formed with an alkali metal cyanate at a temperature below about 10 C. and in the presence of aqueous mineral acid, hydrolyzing the intermediate ureido nitrile by heating the acidic reaction mixture and isolating the product so formed.
LOREN M. LONG.
REFERENCES CITED FOREIGN PATENTS Country Date France June 11, 19 34 OTHER REFERENCES Jour. fur Praktische Chemie (2) vol. 66 (1902), page 236.
Karrer, Organic Chemistry, (1946), page 283.
2nd edition
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2466177A true US2466177A (en) | 1949-04-05 |
Family
ID=3436312
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2466177D Expired - Lifetime US2466177A (en) | Hydantoins and method fob obtaining |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2466177A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2917541A (en) * | 1954-08-03 | 1959-12-15 | Roussel Uclaf | New n,n-dibenzyl amino acid compounds and process of making same |
| US3197477A (en) * | 1961-05-01 | 1965-07-27 | Sterling Drug Inc | Allylhydantoins |
| US4091223A (en) * | 1976-08-04 | 1978-05-23 | Ciba-Geigy Corporation | Unsaturated hydantoin coagents |
| US4167465A (en) * | 1976-08-04 | 1979-09-11 | Ciba-Geigy Corporation | Unsaturated hydantoin coagents |
| US4256867A (en) * | 1977-07-07 | 1981-03-17 | Ciba-Geigy Corporation | Novel vinyl ethers, process for their preparation, and their use for the preparation of polymers |
| US4258149A (en) * | 1978-03-13 | 1981-03-24 | Ciba-Geigy Corporation | Process for curing saturated polymers using divinyl hydantoin coagents |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR769667A (en) * | 1932-12-16 | 1934-08-31 | Prod Chim Ci Devant Sandoz Fab | Process for the preparation of mono- and di-n-alkyl- or aralkyl-5, 5-phenyl-ethylhydantoins |
-
0
- US US2466177D patent/US2466177A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR769667A (en) * | 1932-12-16 | 1934-08-31 | Prod Chim Ci Devant Sandoz Fab | Process for the preparation of mono- and di-n-alkyl- or aralkyl-5, 5-phenyl-ethylhydantoins |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2917541A (en) * | 1954-08-03 | 1959-12-15 | Roussel Uclaf | New n,n-dibenzyl amino acid compounds and process of making same |
| US3197477A (en) * | 1961-05-01 | 1965-07-27 | Sterling Drug Inc | Allylhydantoins |
| US4091223A (en) * | 1976-08-04 | 1978-05-23 | Ciba-Geigy Corporation | Unsaturated hydantoin coagents |
| US4167465A (en) * | 1976-08-04 | 1979-09-11 | Ciba-Geigy Corporation | Unsaturated hydantoin coagents |
| US4256867A (en) * | 1977-07-07 | 1981-03-17 | Ciba-Geigy Corporation | Novel vinyl ethers, process for their preparation, and their use for the preparation of polymers |
| US4258149A (en) * | 1978-03-13 | 1981-03-24 | Ciba-Geigy Corporation | Process for curing saturated polymers using divinyl hydantoin coagents |
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