GB875134A - Adducts of heterocyclic amides and thioamides with ª-,ª--unsaturated compounds - Google Patents
Adducts of heterocyclic amides and thioamides with ª-,ª--unsaturated compoundsInfo
- Publication number
- GB875134A GB875134A GB37697/57A GB3769757A GB875134A GB 875134 A GB875134 A GB 875134A GB 37697/57 A GB37697/57 A GB 37697/57A GB 3769757 A GB3769757 A GB 3769757A GB 875134 A GB875134 A GB 875134A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- carbon atoms
- alkyl
- adducts
- chain
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
-
- 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
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
-
- 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
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
- C07D233/36—One oxygen atom with hydrocarbon radicals, substituted by nitrogen atoms, attached to ring nitrogen atoms
-
- 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
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
- C07D233/38—One oxygen atom with acyl radicals or hetero atoms directly attached to ring nitrogen atoms
-
- 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
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/30—Oxygen or sulfur atoms
- C07D233/42—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon only
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/223—Five-membered rings containing nitrogen and carbon only
- C10M2215/224—Imidazoles
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
- C10M2215/226—Morpholines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/30—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
- C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
- C10M2219/064—Thiourea type compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
- C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
- C10M2219/066—Thiocarbamic type compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Polyvinyl chloride is plasticized by means of a heterocyclic amide or thioamide containing two nitrogen atoms in the hetero cycle, both of which bear substituents, the compounds being adducts of heterocyclic amides or thioamides with a : b -ethylenically unsaturated compounds, all of specified types (see Group IV(b)). The compounds also have fungicidal properties.ALSO:The invention comprises heterocyclic amides and thioamides containing two nitrogen atoms in the ring both of which are substituted, the compounds being adducts of (A) a heterocyclic compound of the formula <FORM:0875134/IV (b)/1> and (B) an unsaturated compound of the formula <FORM:0875134/IV (b)/2> wherein L is a divalent chain of 2 or 3 carbon atoms and one nitrogen atom which, considered in a counter-clockwise direction, is separated by at least 2 carbon atoms from the other nitrogen atom in the ring, the remaining valencies of the 2 or 3 carbon atoms in the L chain being satisfied by hydrogen atoms or alkyl groups which may or may not be joined together to form a carbocyclic system embracing the said 2 or 3 carbon atoms and whose total carbon content is no greater than 18, with the proviso that when the nitrogen atom in the L chain is vicinal to the carbon atom shown in the formula and the L chain contains 3 carbon atoms, the middle carbon of the chain may contain a hydroxy substituent; the available valency of the N atom in the L chain is satisfied by a hydrogen atom, or an alkyl, cycloalkyl, or alkyl cycloalkyl group each containing up to 18 carbon atoms, or an aryl, alkaryl, aralkyl or alkyl arylalkyl group each containing 6-18 carbon atoms, or a C2-C8 hydroxy- or amino-alkyl group in which the hydroxy or amino group is no closer than the b -position to the said nitrogen atom in the chain L, a C2-C18 alkenyl group, an alkoxyalkyl group containing up to 19 carbon atoms in which the alkoxy group contains up to 16 and the alkyl portion at least 2 carbon atoms. an alkenoxyalkyl group containing up to 19 carbon atoms in which the alkenoxy portion contains up to 17 and the alkyl portion at least 2 carbon atoms or a cyano or cyanoalkyl group in which the alkyl group contains up to 8 carbon atoms; Y is oxygen or sulphur; and T and T1, which may be the same or different, represent a cyano group, the group -CONZ2, where Z is hydrogen or C1-C8 alkyl, or the group -COOR in which R is a C1-C14 alkyl group, a C2-14 alkoxyalkyl group, an aralkyl or alkaryl group containing 7-14 carbon atoms or R is a cycloalkyl or alkyl cycloalkyl group containing up to 14 carbon atoms. The adducts are prepared by an addition reaction between the two components at about 0 DEG -200 DEG C. in the presence of a strongly alkaline catalyst and, if desired, an inert volatile solvent. One equivalent of the a :b unsaturated reactant combines with the heterocyclic reactant if the nitrogen atom in the L chain of the latter is substituted; otherwise two equivalents of the unsaturated reactant react with the heterocyclic compound. Also, when the unsaturated reactant is an ester and the N atom in the L chain bears a hydroxy alkyl substituent. in addition to adduct formation there may occur esterification of the hydroxy group by transesterification. Those adducts containing an ester group wherein the group R is derived from a higher alcohol may be obtained advantageously by first forming the corresponding adducts wherein R represents a lower alkyl group and then subjecting the adduct to a transesterification to obtain the higher molecular weight ester, preferably by refluxing the reaction mixture in the presence of a strongly acid catalyst and, if desired, a volatile solvent. The adduct products may be used as synthetic lubricants, fungicides and plasticizers. In an example, 1 : 3-bis(dimethoxy carbonyl hexyl)-2-imidazolidinone is prepared from dimethyl a -methylene-a 1-methyl adipate and ethylene urea. A large number of other examples of adducts and adduct forming materials including imidazolidinthiones, piperazinones, piperazinthiones, piperimidinones and piperimidinthiones are listed.ALSO:Fungicidal compositions comprise an inert carrier containing up to 1% of a heterocyclic amide or thio amide containing two nitrogen atoms in the ring, both bearing substituents, the compounds being adducts of heterocyclic amides or thioamides with a : b -ethylenically unsaturated compounds, all of specified types (see Group IV (b)). Typical adducts are 1 : 3-bis (2 : 5 - dimethoxycarbonyl hexyl) - 2 - imidazolidinone, 1 - (8 - amino octyl) - 3 - (2 : 5 - dibenzyloxy carbonyl hexyl) - 2 - imidazolidinthione, 1 - benzyl - 4 - (2 : 5 - dibutoxycarbonyl hexyl) - 5 - octyl - 6 - hexyl - 2 - piperidinthione, 1 - cyclohexyl - 3 - (2 - cyclohexoxycarbonyl - 5-cyanohexyl) - 5 : 5 - dimethyl - 2 - imidazolidinone and 1 - (2 - butenyl) - 3 - (2 - methoxy carbonyl - 5 - benzoxycarbonyl hexyl) - 4 : 5-diethyl - 2 - piperimidinone. Many other adducts and starting materials therefor are given.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US626294A US3021338A (en) | 1956-12-05 | 1956-12-05 | Adducts of heterocyclic amides |
Publications (1)
Publication Number | Publication Date |
---|---|
GB875134A true GB875134A (en) | 1961-08-16 |
Family
ID=24509783
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB37697/57A Expired GB875134A (en) | 1956-12-05 | 1957-12-03 | Adducts of heterocyclic amides and thioamides with ª-,ª--unsaturated compounds |
Country Status (3)
Country | Link |
---|---|
US (1) | US3021338A (en) |
FR (1) | FR1195270A (en) |
GB (1) | GB875134A (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1218455B (en) * | 1964-01-30 | 1966-06-08 | Asta Werke Ag Chem Fab | Process for the preparation of basic substituted cyclic ureas and their salts |
US4314067A (en) * | 1976-07-29 | 1982-02-02 | Air Products And Chemicals, Inc. | Monomeric compounds having vinyl and imidazolidin-2-one terminal groups |
NO890522L (en) * | 1988-02-25 | 1989-08-28 | Bayer Ag | SUBSTITUTED IMIDAZOLINONES AND IMIDAZOLINTHIONES. |
US5663053A (en) * | 1992-02-11 | 1997-09-02 | Smithkline Beecham Corporation | Inhibition of inflammatory lipid mediators |
ES2149201T3 (en) * | 1992-02-11 | 2000-11-01 | Smithkline Beecham Corp | COA-IT AND PAF INHIBITORS. |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB722541A (en) * | 1951-03-06 | 1955-01-26 | Cassella Farbwerke Mainkur Ag | Dipropionic acids of the heterocyclic series, and derivatives thereof |
CH306990A (en) * | 1951-03-06 | 1955-05-15 | Cassella Farbwerke Mainkur Ag | Process for the preparation of ethylene urea-N, N'-dipropionic acid. |
DE859314C (en) * | 1951-03-07 | 1952-12-11 | Cassella Farbwerke Mainkur Ag | Process for the preparation of dipropionic acids of the heterocyclic series |
-
1956
- 1956-12-05 US US626294A patent/US3021338A/en not_active Expired - Lifetime
-
1957
- 1957-12-03 GB GB37697/57A patent/GB875134A/en not_active Expired
- 1957-12-05 FR FR1195270D patent/FR1195270A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
FR1195270A (en) | 1959-11-16 |
US3021338A (en) | 1962-02-13 |
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