GB1334890A - Process for preparing triketoimidazolidines - Google Patents
Process for preparing triketoimidazolidinesInfo
- Publication number
- GB1334890A GB1334890A GB5874171A GB5874171A GB1334890A GB 1334890 A GB1334890 A GB 1334890A GB 5874171 A GB5874171 A GB 5874171A GB 5874171 A GB5874171 A GB 5874171A GB 1334890 A GB1334890 A GB 1334890A
- Authority
- GB
- United Kingdom
- Prior art keywords
- azomethine
- bis
- reacted
- acid
- group
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 abstract 6
- KBZFDRWPMZESDI-UHFFFAOYSA-N 5-aminobenzene-1,3-dicarboxylic acid Chemical compound NC1=CC(C(O)=O)=CC(C(O)=O)=C1 KBZFDRWPMZESDI-UHFFFAOYSA-N 0.000 abstract 5
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 abstract 3
- 229920000642 polymer Polymers 0.000 abstract 3
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 239000013522 chelant Substances 0.000 abstract 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- MMEDJBFVJUFIDD-UHFFFAOYSA-N 2-[2-(carboxymethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1CC(O)=O MMEDJBFVJUFIDD-UHFFFAOYSA-N 0.000 abstract 1
- LDOMKUVUXZRECL-UHFFFAOYSA-N 2-aminobenzene-1,3-dicarboxylic acid Chemical compound NC1=C(C(O)=O)C=CC=C1C(O)=O LDOMKUVUXZRECL-UHFFFAOYSA-N 0.000 abstract 1
- ZCUTYLSQFUTKEX-UHFFFAOYSA-N 5-(5-carboxy-1,3-dioxoisoindol-2-yl)benzene-1,3-dicarboxylic acid Chemical compound O=C1C2=CC(C(=O)O)=CC=C2C(=O)N1C1=CC(C(O)=O)=CC(C(O)=O)=C1 ZCUTYLSQFUTKEX-UHFFFAOYSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003368 amide group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 abstract 1
- -1 azo compound Chemical class 0.000 abstract 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- WNXYUELEECUMPA-UHFFFAOYSA-N ethyl 2-[3-[amino(phenyl)methyl]-2-(2-ethoxy-2-oxoacetyl)phenyl]-2-oxoacetate Chemical compound C(=O)(C(=O)OCC)C=1C(=C(C=CC1)C(C1=CC=CC=C1)N)C(=O)C(=O)OCC WNXYUELEECUMPA-UHFFFAOYSA-N 0.000 abstract 1
- 150000003949 imides Chemical class 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- 239000000155 melt Substances 0.000 abstract 1
- ZFLIKDUSUDBGCD-UHFFFAOYSA-N parabanic acid Chemical class O=C1NC(=O)C(=O)N1 ZFLIKDUSUDBGCD-UHFFFAOYSA-N 0.000 abstract 1
- 150000007519 polyprotic acids Polymers 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 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
- C07D233/96—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
- C08G18/3821—Carboxylic acids; Esters thereof with monohydroxyl compounds
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/83—Chemically modified polymers
- C08G18/838—Chemically modified polymers by compounds containing heteroatoms other than oxygen, halogens, nitrogen, sulfur, phosphorus or silicon
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0605—Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0616—Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only two nitrogen atoms 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
1334890 Triketoimidazolidine polymers REICHHOLD-ALBERT-CHEMIE AG 17 Dec 1971 [4 Aug 1971] 58741/71 Addition to 1309190 Heading C3R Modified N,N<SP>1</SP>-substituted 2,4,5-triketoimidazolidine polymers are obtained by reacting (i) an oxamidic ester having the group where R<SP>V</SP> is an aliphatic, cycloaliphatic or aromatic hydrocarbon group, (ii) an isocyanate or isocyanate-forming compound and (iii) an azomethine of formula or metal chelate thereof or an azo compound of formula or metal chelate thereof, where R<SP>VI</SP> is an aromatic group containing a hydroxy group ortho to the azomethine group and may contain other substituents and R<SP>VII</SP> is an aromatic group containing a hydroxy group ortho to the azo group and may contain other substituents. The polymers contain chelate-forming groups. A polybasic carboxylic acid may be used as an additional reaction component; the polybasic acid may be used in combination with an amine or may be one containing imide or amide groups. Some of the reactants may be reacted in a first stage and the remainder subsequently. The reaction may be carried out in a melt or in a solvent. In examples 4,4<SP>1</SP>-bis-(4-carboxyphthalimido)-diphenylsulphone and 4,4<SP>1</SP>-bis-(4-carboxyphthalimido) - diphenylether are reacted with the azomethine of 2-hydroxynaphthaldehyde-1 and 5-aminoisophthalic acid, 4,4-bis- (ethoxalylamino) - diphenylmethane, 4,4-diisocyanato - diphenylether and 4,4<SP>1</SP> - diisocyanatodiphenylmethane ; 4,4 - diaminodiphenylmethane is reacted with trimellitic anhydride, then with 4,4<SP>1</SP> - bis - ethoxalylaminodiphenylmethane and the azomethine of 5-aminoisophthalic acid and salicylaldehyde, and then with 4,4<SP>1</SP> - diisocyanato - diphenylmethane; 4,4 - diaminodiphenylmethane is reacted with trimellitic anhydride, then with 4,41-diisocyanatodiphenylmethane, and then with 4,4<SP>1</SP>-bisethoxalylaminodiphenylinethane and the azomethine of aminoisophthalic acid and salicylaldehyde; 4,4<SP>1</SP> - bis - (4 - carboxyphthalimido)- diphenylmethane and 5-(4-carboxyphthalimido)-isophthalic acid are reacted with 4,4<SP>1</SP>- bisethoxalylaminodiphenylmethane, then with 4,4<SP>1</SP>-diisocyanatodiphenylmethane, then with the azomethine of 5-aminoisophthalic acid and salicylaldehyde and then with cobalt octoate; 4,4-diaminodiphenylmethane is reacted with trimellitic anhydride, then with 4,4<SP>1</SP>-bis-(ethoxalylamino)-diphenylmethane and the azomethine of 5-aminoisophthalic acid and 2 hydroxy-naphthaldehyde-1, and then with 4,4<SP>1</SP>- diisocyanatodiphenylmethane; and bis-ethoxalyl-aminodiphenylmethane is reacted with the azomethine of 2-hydroxy-naphthaldehyde-1 and 5-aminoisophthalic acid, and then with 4,4<SP>1</SP>- diisocyanatodiphenylether.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2139005A DE2139005C2 (en) | 1970-06-19 | 1971-08-04 | Process for the preparation of modified N, N'-substituted 2,4,5-triketoimidazolidines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1334890A true GB1334890A (en) | 1973-10-24 |
Family
ID=5815753
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5874171A Expired GB1334890A (en) | 1971-08-04 | 1971-12-17 | Process for preparing triketoimidazolidines |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5411840B1 (en) |
| AT (1) | AT311957B (en) |
| CA (1) | CA988526A (en) |
| CH (1) | CH598227A5 (en) |
| FR (1) | FR2149713A6 (en) |
| GB (1) | GB1334890A (en) |
| IT (1) | IT976372B (en) |
| NL (1) | NL157920B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4074007A (en) | 1974-03-26 | 1978-02-14 | Hoechst Aktiengesellschaft | Coating composition |
| USRE30067E (en) * | 1973-10-26 | 1979-08-07 | Exxon Research & Engineering Co. | Iminoimidazolidinedione and parabanic acid polymers containing imide groups |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3027618A1 (en) | 1980-07-21 | 1982-02-25 | Bayer Ag, 5090 Leverkusen | METHOD FOR PRODUCING IMIDAZOLIDINE TRIONS |
-
1971
- 1971-12-08 CH CH1790371A patent/CH598227A5/xx not_active IP Right Cessation
- 1971-12-13 FR FR7144629A patent/FR2149713A6/fr not_active Expired
- 1971-12-13 AT AT1067771A patent/AT311957B/en not_active IP Right Cessation
- 1971-12-17 IT IT3257771A patent/IT976372B/en active
- 1971-12-17 NL NL7117419A patent/NL157920B/en not_active IP Right Cessation
- 1971-12-17 GB GB5874171A patent/GB1334890A/en not_active Expired
- 1971-12-18 JP JP10231671A patent/JPS5411840B1/ja active Pending
-
1972
- 1972-01-26 CA CA133,213A patent/CA988526A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE30067E (en) * | 1973-10-26 | 1979-08-07 | Exxon Research & Engineering Co. | Iminoimidazolidinedione and parabanic acid polymers containing imide groups |
| US4074007A (en) | 1974-03-26 | 1978-02-14 | Hoechst Aktiengesellschaft | Coating composition |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2149713A6 (en) | 1973-03-30 |
| AT311957B (en) | 1973-12-10 |
| IT976372B (en) | 1974-08-20 |
| JPS5411840B1 (en) | 1979-05-17 |
| NL157920B (en) | 1978-09-15 |
| NL7117419A (en) | 1973-02-06 |
| CA988526A (en) | 1976-05-04 |
| CH598227A5 (en) | 1978-04-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |