GB965474A - Esters of di-isocyanate carboxylic acids - Google Patents
Esters of di-isocyanate carboxylic acidsInfo
- Publication number
- GB965474A GB965474A GB4332261A GB4332261A GB965474A GB 965474 A GB965474 A GB 965474A GB 4332261 A GB4332261 A GB 4332261A GB 4332261 A GB4332261 A GB 4332261A GB 965474 A GB965474 A GB 965474A
- Authority
- GB
- United Kingdom
- Prior art keywords
- isocyanato
- caproate
- acid
- esters
- alkaryl
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
-
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/771—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur oxygen
-
- 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Emergency Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention comprises esters of di-isocyanato carboxylic acids having the general formula: <FORM:0965474/C1/1> where R is an unsubstituted or halogenated alkyl, aryl, alkaryl or aralkyl group, R* is a hydrogen atom or the radical -CO2Y, where Y is an unsubstituted or halogenated alkyl, aryl, alkaryl or aralkyl group, and R11 is a C1-8 alkylene radical. These compounds may be produced by reacting the corresponding diamino carboxylic acid ester or the acid-addition salt of such a compound, with phosgene in the presence of a suitable solvent. A preferred method uses the dihydrochloride salt of the diamino carboxylic acid ester. The temperature of the reaction is maintained within the range of 50-200 DEG C., depending on the ester used. Solvents mentioned as suitable for the reaction are chlorobenzene, orthodichlorobenzene, bromotoluene, chlorotoluene, 4-chloro-1,3-xylene, benzene, toluene, dioxane, and dialkyl ethers of glycols and polyether glycols. Examples are given, illustrating the preparation of the following compounds: 2,6-diisocyanato methyl caproate, 2,6-di-isocyanato ethyl caproate, 2,6-di-isocyanato propyl caproate, 2,6-di-isocyanato butyl caproate, 2,6-di-isocyanato octyl caproate, 2,6-di-isocyanato benzyl caproate, 2,5-di-isocyanato methyl valerate, 1,5-dicarbo-methoxy-1,5-di-isocyanato pentane, 1,8-dicarbethoxy-1,8-di-isocyanato octane, and 2,6-di-isocyanato stearyl caproate. Also specified are the phenyl, o-tolyl, 2-chloro-5-methylphenyl, 2,3-dichloropropyl and isopropyl esters of 2,6-di-isocyanato caproic acid and 2,6-di-isocyanato valeric acid; the ethyl, propyl, butyl, octyl, stearyl, 2-chloropropyl, and benzyl esters of 2,6-di-isocyanato valeric acid; the 1,2-dichloropropyl ester of 2,6-di-isocyanato caproic acid; the dimethyl, diethyl, dipropyl, dibutyl, dioctyl, distearyl, diphenyl, dibenzyl, di (o-tolyl), di (2-chloro-5-methylphenyl), di (2-chloropropyl), di (2,3-chloropropyl), and di-isopropyl diesters of 2,6-di-isocyanato pimelic acid and of 2,9-di-isocyanato sebacic acid; and the methyl-propyl diesters, phenyl-octyl diesters, and benzyl-stearyl diesters of 2,6-di-isocyanato pimelic acid and of 2,9-di-isocyanato sebacic acid. The preparation of esters of diamino carboxylic acids used as the starting material is described.ALSO:Esters of di-isocyanato carboxylic acids, having the general formula: <FORM:0965474/C3/1> where R is an unsubstituted or halogenated alkyl, aryl, alkaryl or aralkyl group, R* is a hydrogen atom or the radical -CO2Y, where Y is an unsubstituted or halogenated alkyl, aryl, alkaryl or aralkyl group, and R11 is a C1-8 alkylene radical, are employed as intermediates for the manufacture of polymers such as polyurethanes which may be obtained in the form of foams, adhesives, elastomers, films and moulded objects. Polymers may be produced by the reaction of these compounds with polyols, polyamines or polycarboxylic acids. Thus clear, colourless, elastic polymers are produced by reacting these di-isocyanate compounds with glycols in the presence of a catalyst such as dibutyl tin dilaurate.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7348360A | 1960-12-05 | 1960-12-05 | |
| US285888A US3281378A (en) | 1963-06-06 | 1963-06-06 | Diisocyanato substituted aliphatic carboxylic acid ester urethane reaction products |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB965474A true GB965474A (en) | 1964-07-29 |
Family
ID=26754524
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4332261A Expired GB965474A (en) | 1960-12-05 | 1961-12-04 | Esters of di-isocyanate carboxylic acids |
| GB534467A Expired GB1072958A (en) | 1960-12-05 | 1964-06-04 | Diaminocarboxylic acid esters |
| GB2320364A Expired GB1072956A (en) | 1960-12-05 | 1964-06-04 | Esters of diisocyanato carboxylic acids and reaction products thereof |
| GB681966A Expired GB1072957A (en) | 1960-12-05 | 1964-06-04 | Diaminocarboxylic acid esters |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB534467A Expired GB1072958A (en) | 1960-12-05 | 1964-06-04 | Diaminocarboxylic acid esters |
| GB2320364A Expired GB1072956A (en) | 1960-12-05 | 1964-06-04 | Esters of diisocyanato carboxylic acids and reaction products thereof |
| GB681966A Expired GB1072957A (en) | 1960-12-05 | 1964-06-04 | Diaminocarboxylic acid esters |
Country Status (5)
| Country | Link |
|---|---|
| CH (2) | CH433253A (en) |
| DE (2) | DE1418995A1 (en) |
| GB (4) | GB965474A (en) |
| NL (3) | NL6406398A (en) |
| SE (1) | SE310422B (en) |
Cited By (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4469653A (en) * | 1981-07-04 | 1984-09-04 | Basf Aktiengesellschaft | Process for the preparation of molded parts of polyurethane or polyurethane-polyurea employing monocyclic amidines |
| US5294445A (en) * | 1991-08-21 | 1994-03-15 | Bayer Aktiengesellschaft | Pesticidal shaped articles |
| US5552507A (en) * | 1994-05-17 | 1996-09-03 | Bayer Aktiengesellschaft | Diisocyanates and processes for their production and use |
| DE102007046187A1 (en) | 2007-09-26 | 2009-04-09 | Bayer Materialscience Ag | roof module |
| WO2009142899A1 (en) | 2008-05-22 | 2009-11-26 | Dow Global Technologies Inc. | Thermoset polyurethanes comprising cis, trans-1, 3- and 1, 4-cyclohexanedimethylether groups |
| EP2177555A2 (en) | 2008-10-16 | 2010-04-21 | Bayer MaterialScience AG | Method for manufacturing polyether ester polyols |
| EP2202256A1 (en) | 2008-12-23 | 2010-06-30 | Bayer MaterialScience LLC | Polymer polyols comprising a natural oil base polyol, polyurethane foams comprising these polymer polyols and processes for their preparation |
| WO2012084760A1 (en) | 2010-12-20 | 2012-06-28 | Bayer Materialscience Ag | Method for producing polyether ester polyols |
| WO2013127850A1 (en) | 2012-02-29 | 2013-09-06 | Bayer Intellectual Property Gmbh | 2-k pultrusion formulation and process |
| DE102012209598A1 (en) | 2012-06-06 | 2013-12-12 | Cht R. Beitlich Gmbh | Textile auxiliaries and thus refined textile product |
| DE102012222045A1 (en) | 2012-12-03 | 2014-06-05 | Cht R. Beitlich Gmbh | Coating of luminophores |
| EP2762508A1 (en) | 2007-07-23 | 2014-08-06 | Dow Global Technologies LLC | Two part polyurethane curable composition having substantially consistent G-modulus across the range of use temperatures |
| WO2015100128A1 (en) | 2013-12-23 | 2015-07-02 | Dow Global Technologies Llc | Adhesive containing high solid copolymer polyol polyurethane prepolymer |
| EP2894180A1 (en) | 2014-01-08 | 2015-07-15 | Bayer MaterialScience AG | Polymer Polyols comprising a Polyether Carbonate Polyol as the Base Polyol |
| WO2017112012A2 (en) | 2015-09-17 | 2017-06-29 | Jerez Roberto Velozzi | Load-bearing composite panels, materials, products, and processes to make and use same |
| WO2019149672A2 (en) | 2018-02-02 | 2019-08-08 | Basf Se | Simultaneous optimization of fiber sizing in-line with the pultrusion process |
| EP3741788A1 (en) | 2019-05-24 | 2020-11-25 | Covestro Deutschland AG | Method for the preparation of polyoxyalkylenpolyol mixtures |
| EP3838963A1 (en) | 2019-12-17 | 2021-06-23 | Covestro Deutschland AG | Method for producing polyoxyalkylene polyesterpolyols |
| US11173224B2 (en) | 2017-07-21 | 2021-11-16 | The Procter & Gamble Company | Gels comprising a hydrophobic material |
| US20210403417A1 (en) * | 2020-06-26 | 2021-12-30 | Evonik Operations Gmbh | Process for preparing diisocyanates based on lysine |
| WO2022060685A1 (en) | 2020-09-15 | 2022-03-24 | Dow Global Technologies Llc | Low odor polyurethane adhesives |
| WO2022090358A1 (en) | 2020-10-28 | 2022-05-05 | Basf Se | Production of a polyester polyol with low voc emission |
| WO2022096390A1 (en) | 2020-11-06 | 2022-05-12 | Covestro Deutschland Ag | Method for producing a polyol mixture |
| WO2023057328A1 (en) | 2021-10-07 | 2023-04-13 | Covestro Deutschland Ag | Process for preparing polyoxyalkylene polyester polyols |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3001013A1 (en) * | 1980-01-12 | 1981-07-23 | Basf Ag, 6700 Ludwigshafen | VINYLPYRROLIDONE POLYMERISATES, THEIR PRODUCTION AND THEIR USE FOR THE PRODUCTION OF BLOOD REPLACEMENT LIQUIDS |
| US4749694A (en) * | 1984-04-26 | 1988-06-07 | Merck & Co., Inc. | Novel lysine esters used as absorption |
| DE4334873A1 (en) * | 1993-10-13 | 1995-04-20 | Nycomed Arzneimittel Gmbh | Asymmetrically substituted diaminodicarboxylic acid derivatives and process for their preparation |
-
0
- NL NL133051D patent/NL133051C/xx active
- NL NL272185D patent/NL272185A/xx unknown
-
1961
- 1961-12-04 GB GB4332261A patent/GB965474A/en not_active Expired
- 1961-12-04 DE DE19611418995 patent/DE1418995A1/en active Pending
- 1961-12-05 CH CH1406661A patent/CH433253A/en unknown
-
1964
- 1964-04-21 SE SE494664A patent/SE310422B/xx unknown
- 1964-05-05 DE DE19641520384 patent/DE1520384B2/en not_active Withdrawn
- 1964-06-04 GB GB534467A patent/GB1072958A/en not_active Expired
- 1964-06-04 GB GB2320364A patent/GB1072956A/en not_active Expired
- 1964-06-04 GB GB681966A patent/GB1072957A/en not_active Expired
- 1964-06-05 CH CH738464A patent/CH471184A/en not_active IP Right Cessation
- 1964-06-05 NL NL6406398A patent/NL6406398A/xx unknown
Cited By (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4469653A (en) * | 1981-07-04 | 1984-09-04 | Basf Aktiengesellschaft | Process for the preparation of molded parts of polyurethane or polyurethane-polyurea employing monocyclic amidines |
| US5294445A (en) * | 1991-08-21 | 1994-03-15 | Bayer Aktiengesellschaft | Pesticidal shaped articles |
| US5552507A (en) * | 1994-05-17 | 1996-09-03 | Bayer Aktiengesellschaft | Diisocyanates and processes for their production and use |
| EP2762508A1 (en) | 2007-07-23 | 2014-08-06 | Dow Global Technologies LLC | Two part polyurethane curable composition having substantially consistent G-modulus across the range of use temperatures |
| DE102007046187A1 (en) | 2007-09-26 | 2009-04-09 | Bayer Materialscience Ag | roof module |
| WO2009142899A1 (en) | 2008-05-22 | 2009-11-26 | Dow Global Technologies Inc. | Thermoset polyurethanes comprising cis, trans-1, 3- and 1, 4-cyclohexanedimethylether groups |
| EP2177555A2 (en) | 2008-10-16 | 2010-04-21 | Bayer MaterialScience AG | Method for manufacturing polyether ester polyols |
| EP2202256A1 (en) | 2008-12-23 | 2010-06-30 | Bayer MaterialScience LLC | Polymer polyols comprising a natural oil base polyol, polyurethane foams comprising these polymer polyols and processes for their preparation |
| WO2012084760A1 (en) | 2010-12-20 | 2012-06-28 | Bayer Materialscience Ag | Method for producing polyether ester polyols |
| WO2013127850A1 (en) | 2012-02-29 | 2013-09-06 | Bayer Intellectual Property Gmbh | 2-k pultrusion formulation and process |
| DE102012209598A1 (en) | 2012-06-06 | 2013-12-12 | Cht R. Beitlich Gmbh | Textile auxiliaries and thus refined textile product |
| WO2013182568A2 (en) | 2012-06-06 | 2013-12-12 | Cht R. Beitlich Gmbh | Textile auxiliary agent and textile product finished therewith |
| DE102012222045A1 (en) | 2012-12-03 | 2014-06-05 | Cht R. Beitlich Gmbh | Coating of luminophores |
| WO2014086579A1 (en) | 2012-12-03 | 2014-06-12 | Cht R. Beitlich Gmbh | Luminophore coating |
| WO2015100128A1 (en) | 2013-12-23 | 2015-07-02 | Dow Global Technologies Llc | Adhesive containing high solid copolymer polyol polyurethane prepolymer |
| EP2894180A1 (en) | 2014-01-08 | 2015-07-15 | Bayer MaterialScience AG | Polymer Polyols comprising a Polyether Carbonate Polyol as the Base Polyol |
| EP3766686A1 (en) | 2015-09-17 | 2021-01-20 | Roberto Velozzi Jerez | Load-bearing composite panels, materials, products, and processes to make and use same |
| WO2017112012A2 (en) | 2015-09-17 | 2017-06-29 | Jerez Roberto Velozzi | Load-bearing composite panels, materials, products, and processes to make and use same |
| US11173224B2 (en) | 2017-07-21 | 2021-11-16 | The Procter & Gamble Company | Gels comprising a hydrophobic material |
| WO2019149672A2 (en) | 2018-02-02 | 2019-08-08 | Basf Se | Simultaneous optimization of fiber sizing in-line with the pultrusion process |
| WO2020239525A1 (en) | 2019-05-24 | 2020-12-03 | Covestro Intellectual Property Gmbh & Co. Kg | Process for producing polyoxyalkylene-polyol mixtures |
| EP3741788A1 (en) | 2019-05-24 | 2020-11-25 | Covestro Deutschland AG | Method for the preparation of polyoxyalkylenpolyol mixtures |
| US12091543B2 (en) | 2019-05-24 | 2024-09-17 | Covestro Intellectual Property Gmbh & Co. Kg | Process for producing polyoxyalkylene-polyol mixtures |
| EP3838963A1 (en) | 2019-12-17 | 2021-06-23 | Covestro Deutschland AG | Method for producing polyoxyalkylene polyesterpolyols |
| WO2021122401A1 (en) | 2019-12-17 | 2021-06-24 | Covestro Intellectual Property Gmbh & Co. Kg | Process for preparing polyoxyalkylene polyester polyols |
| US20210403417A1 (en) * | 2020-06-26 | 2021-12-30 | Evonik Operations Gmbh | Process for preparing diisocyanates based on lysine |
| US11739055B2 (en) * | 2020-06-26 | 2023-08-29 | Evonik Operations Gmbh | Process for preparing diisocyanates based on lysine |
| WO2022060685A1 (en) | 2020-09-15 | 2022-03-24 | Dow Global Technologies Llc | Low odor polyurethane adhesives |
| WO2022090358A1 (en) | 2020-10-28 | 2022-05-05 | Basf Se | Production of a polyester polyol with low voc emission |
| WO2022096390A1 (en) | 2020-11-06 | 2022-05-12 | Covestro Deutschland Ag | Method for producing a polyol mixture |
| WO2023057328A1 (en) | 2021-10-07 | 2023-04-13 | Covestro Deutschland Ag | Process for preparing polyoxyalkylene polyester polyols |
Also Published As
| Publication number | Publication date |
|---|---|
| NL272185A (en) | |
| DE1418995A1 (en) | 1968-12-12 |
| NL6406398A (en) | 1964-12-07 |
| CH433253A (en) | 1967-04-15 |
| SE310422B (en) | 1969-04-28 |
| CH471184A (en) | 1969-04-15 |
| GB1072957A (en) | 1967-06-21 |
| DE1520384B2 (en) | 1972-04-20 |
| NL133051C (en) | |
| DE1520384A1 (en) | 1969-03-20 |
| GB1072958A (en) | 1967-06-21 |
| GB1072956A (en) | 1967-06-21 |
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