GB977958A - A process for the preparation of partially esterified amino alcohols - Google Patents

A process for the preparation of partially esterified amino alcohols

Info

Publication number
GB977958A
GB977958A GB18529/62A GB1852962A GB977958A GB 977958 A GB977958 A GB 977958A GB 18529/62 A GB18529/62 A GB 18529/62A GB 1852962 A GB1852962 A GB 1852962A GB 977958 A GB977958 A GB 977958A
Authority
GB
United Kingdom
Prior art keywords
formula
specified
group
partially esterified
groups
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
Application number
GB18529/62A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Publication of GB977958A publication Critical patent/GB977958A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B60—VEHICLES IN GENERAL
    • B60K—ARRANGEMENT OR MOUNTING OF PROPULSION UNITS OR OF TRANSMISSIONS IN VEHICLES; ARRANGEMENT OR MOUNTING OF PLURAL DIVERSE PRIME-MOVERS IN VEHICLES; AUXILIARY DRIVES FOR VEHICLES; INSTRUMENTATION OR DASHBOARDS FOR VEHICLES; ARRANGEMENTS IN CONNECTION WITH COOLING, AIR INTAKE, GAS EXHAUST OR FUEL SUPPLY OF PROPULSION UNITS IN VEHICLES
    • B60K11/00—Arrangement in connection with cooling of propulsion units
    • B60K11/02—Arrangement in connection with cooling of propulsion units with liquid cooling
    • 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
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3271—Hydroxyamines
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/14—Polycondensates modified by chemical after-treatment
    • C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
    • C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
    • C08G59/145—Compounds containing one epoxy group
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/62—Alcohols or phenols
    • C08G59/64—Amino alcohols
    • 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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing 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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
    • C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy 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
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/44—Polyester-amides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Emergency Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Combustion & Propulsion (AREA)
  • Transportation (AREA)
  • Mechanical Engineering (AREA)
  • Epoxy Resins (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises partially esterified amino di-alcohols of the formula <FORM:0977958/C1/1> wherein R1 and R2 are similar or dissimilar saturated hydrocarbon radicals, which may also be directly attached to each other, R3 and R4 each represent an alkyl or cycloalkyl group or a hydrogen atom, A and B are similar or dissimilar alkylene groups, R5 represents a hydrogen atom, a group of the formula <FORM:0977958/C1/2> a monovalent hydrocarbon radical or a monovalent hydrocarbon radical substituted by hydroxyl or amino groups, said amino groups being substituted if desired by groups of the formula <FORM:0977958/C1/3> R6 represents the same group as specified for R5 or a group -NR7R8, and R7 and R8 represent a hydrogen atom, a monovalent hydrocarbon radical or a group of the formula <FORM:0977958/C1/4> The above compounds are prepared by reacting an amine of the formula R5R6NH with the intermediate product formed by reacting an epoxy halogen alkane or a halohydrin from which an epoxy halogen alkane may be formed by liberation of hydrogen halide on the one hand with a saturated aliphatic monocarboxylic acid of the formula <FORM:0977958/C1/5> or a salt thereof on the other hand. The reaction may be conducted in the presence of catalysts such as tributylamine.ALSO:Partially esterified amino di-alcohols of the formula <FORM:0977958/C3/1> , wherein R1 and R2 are similar or dissimilar saturated hydrocarbon radicals, which may also be directly attached to each other, R3 and R4 each represent a hydrogen atom or an alkyl or cycloalkyl group, A and B are similar or dissimilar alkylene groups, R5 represents a hydrogen atom, a group of the formula <FORM:0977958/C3/2> , a monovalent hydrocarbon radical or a monovalent hydrocarbon radical substituted by hydroxy or amino groups, said amino groups being substituted if desired by groups of the formula <FORM:0977958/C3/3> , R6 represents the same groups as specified for R5 or a group -NR7R8, and R7 and R8 represent a hydrogen atom, a monovalent hydrocarbon radical or a group of the formula <FORM:0977958/C3/4> , are used alone or in the form of complexes with boron trifluoride as plasticizers or curing agents for polyepoxy compounds, as components of polyurethanes and as components of alkyd resins. The polyepoxy compounds may be cured in the presence of further ingredients such as bitumens, cracked bitumens, talcum, titanium dioxide, organic solvents such as alcohol, benzene, toluene, xylene and methyl isobutyl ketone and/or monoepoxy compounds such as butyl glycidyl ether, phenyl glycidyl ether and glycidyl ethers of branched monocarboxylic acids to provide products which may be used as paints for concrete floors and for the interior of tanks, wet-strength and tear-resistance agents for cellulose and polyamide fabrics and paper (including nylon fibre paper), casting resins and laminates. Specified polyepoxy compounds are poly (epoxyalkyl) ethers of diphenylol propane, -ethane and -methane, diphenylol sulphone, hydroquinone, resorcinol, dihydroxydiphenyl, dihydroxynaphthalenes, novolacs, resols, ethylene glycol, glycerol and trimethylolpropane; diglycidyl esters of phthalic, terephthalic and adipic acids; epoxidized linseed and soybean oils; diepoxybutane; epoxidized vinylcyclohexane; diglycidyl ether; and the (3, 4-epoxy-6-methylcyclohexyl)-methyl ester of 3, 4-epoxy-6-methyl-cyclohexane carboxylic acid. The above partially esterified. Polyurethanes are prepared by reacting the above specified partially esterified amino-dialcohols with the following polyisocyanates:-toluene, hexamethylene, diphenylmethane, naphthalene, meta-phenylene, diphenyl, diphenyl ether, dianisidine, ethylene and diethyl ether diisocyanates, triphenylmethane triisocyanate, mixtures of 2, 4- and 2, 6-toluene diisocyanate, and polyisocyanates formed by reacting ethylene glycol, glycerol and 1, 2, 6-hexane triol with any of the above-specified isocyanates. The polyurethanes may be formulated into foam, paint and lacquer compositions together with fillers, pigments and solvents such as xylene and ethyl acetate. Polyesters are prepared by reacting the above specified partially esterified amino-dialcohols, alone or in conjunction with diethylene glycol, dipropylene glycol or glycerol, with citric, trimellitic, pyromellitic, phthalic, isophthalic, terephthalic, succinic, adipic, maleic, tetrahydrophthalic or diglycolic acids or their anhydrides, dimerized fatty acids of drying oils and Diels-Alder adducts of maleic acid with terpenes, cyclopentadienes, hexachlorocyclopentadiene or mixtures thereof, using temperatures of between 120-270 DEG C. and, if desired, a xylene solvent. The resulting polyester resins may be used for paints, lacquers and varnishes in combination with pigments such as titanium white, diluents such as xylene, phenol-form-aldehyde resins, urea-formaldehyde resins, melamine-formaldehyde resins and thickeners.ALSO:Polyepoxide resins cured with specified partially esterified amino alcohols and containing as further ingredients cracked bitumen, titanium dioxide or talcum are spread on to concrete floors to provide a surface which cures within 24 hours to give a hard, flexible and wear-resistant coating. A polyurethane lacquer based on the reaction product of a polyisocyanate and a specified partially esterified amino alcohol is made up to brushing consistency with water-free xylene or ethyl acetate and applied to steel test panels and either cured at room temperature for 2-3 days or baked at 100-150 DEG C. for 30-40 minutes to provide a colourless, hard and flexible coating. Alkyd resins prepared from phthalic anhydride, specified partially esterified amino alcohols, glycerol or triethylene glycol and xylene are formulated into stoving enamels with urea formaldehyde resin and titanium white and are applied to steel panels and baked at 150 DEG C. to provide hard, flexible coatings.ALSO:Improved wet-strength and non-tearing characteristics are imparted to cellulose and polyamide fabrics and to paper, including paper formed from nylon fibres, by impregnation with a 5% by volume solution of a polyepoxy compound in an organic solvent such as alcohol, benzene, toluene, xylene or methyl isobutyl ketone, which solution also contains from 10 to 30% by volume of a specified partially esterified aminodi-alcohol curing agent, followed by a curing treatment, e.g. by heating to 100 DEG C. Alternatively, monoepoxy compounds may be used to reduce the viscosity of the uncured polypoxy compound in place of the organic solvent. Specified monoepoxy compounds are butyl glycidyl ether, benzyl glycidyl ether and glycidyl ethers of branched monocarboxylic acids. The specified partially esterified aminodi-alcohol curing agent is represented by the formula:- <FORM:0977958/D1-D2/1> wherein R1 and R2 are similar or dissimilar saturated hydrocarbon radicals, which may also be directly attached to each other, R3 and R4 each represent an alkyl group, a cylcoalkyl group or a hydrogen atom, A and B are similar or dissimilar alkylene groups, R5 represents a hydrogen atom, a group of the formula:- <FORM:0977958/D1-D2/2> a monovalent hydrocarbon radical or a monovalent hydrocarbon radical substituted by hydroxy or amino groups, said amino groups being substituted if desired by groups of the formula:- <FORM:0977958/D1-D2/3> R6 represents the same groups as specified for R5 or a group -NR7R8, and R7 and R8 represents a hydrogen atom, a monovalent hydrocarbon radical or a group of the formula:- <FORM:0977958/D1-D2/4> Specified polyepoxy compounds are poly (epoxyalkyl) ethers of diphenylol propane, diphenylolethane, diphenyldimethane, diphenylolsulphone, hydroquinone, resorcinol, dihydroxydiphenyl, dihydroxynaphthalenes novolacs, resols, ethylene glycol, glycerol and trimethylopropane; diglycidyl esters of phthalic, terephthalic and adipic acids; epoxidized linseed and soybean oils; diepoxybutane; epoxidized vinylcyclohexane; diglycidyl ether; and the (3, 4-epoxy-6-methyl-cyclohexyl)-methyl ester of 3,4-epoxy-6-methyl-cyclohexane carboxylic acid.
GB18529/62A 1961-05-16 1962-05-14 A process for the preparation of partially esterified amino alcohols Expired GB977958A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL264794 1961-05-16

Publications (1)

Publication Number Publication Date
GB977958A true GB977958A (en) 1964-12-16

Family

ID=19753040

Family Applications (2)

Application Number Title Priority Date Filing Date
GB18530/62A Expired GB983516A (en) 1961-05-16 1962-05-14 Fluid epoxide compositions
GB18529/62A Expired GB977958A (en) 1961-05-16 1962-05-14 A process for the preparation of partially esterified amino alcohols

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB18530/62A Expired GB983516A (en) 1961-05-16 1962-05-14 Fluid epoxide compositions

Country Status (5)

Country Link
BE (1) BE617618A (en)
CH (1) CH413361A (en)
DE (1) DE1520764B1 (en)
GB (2) GB983516A (en)
NL (3) NL264294A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2425424A1 (en) * 1978-05-12 1979-12-07 Nattermann A & Cie SYNTHETIC COMPOUNDS WITH ANALOGUE STRUCTURE TO THAT OF NATURAL GLYCERIDES, THEIR PREPARATION AND THEIR THERAPEUTIC USES
DE3217723A1 (en) * 1981-05-11 1982-12-02 Sumitomo Chemical Co., Ltd., Osaka CONDUCTIVE ADHESIVE PASTE
CN116179012A (en) * 2022-12-23 2023-05-30 杭州柏盛印刷有限公司 Water-based UV (ultraviolet) ink and preparation method thereof

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL297207A (en) * 1963-08-28
US3714112A (en) * 1971-04-15 1973-01-30 Fmc Corp Glycidyl acetate as viscosity modifier for liquid epoxy resins
DE2861731D1 (en) * 1977-06-13 1982-05-27 Shell Int Research Resin binders containing amino groups and process for their preparation
JPH0648266B2 (en) * 1984-02-08 1994-06-22 日本エクスラン工業株式会社 Method for producing packing material for liquid chromatography
CA2138077A1 (en) * 1993-12-21 1995-06-22 Dilipkumar N. Shah Flexibilized polyepoxide resins

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2425424A1 (en) * 1978-05-12 1979-12-07 Nattermann A & Cie SYNTHETIC COMPOUNDS WITH ANALOGUE STRUCTURE TO THAT OF NATURAL GLYCERIDES, THEIR PREPARATION AND THEIR THERAPEUTIC USES
DE3217723A1 (en) * 1981-05-11 1982-12-02 Sumitomo Chemical Co., Ltd., Osaka CONDUCTIVE ADHESIVE PASTE
CN116179012A (en) * 2022-12-23 2023-05-30 杭州柏盛印刷有限公司 Water-based UV (ultraviolet) ink and preparation method thereof
CN116179012B (en) * 2022-12-23 2023-10-20 杭州柏盛印刷有限公司 Water-based UV (ultraviolet) ink and preparation method thereof

Also Published As

Publication number Publication date
NL112652C (en)
GB983516A (en) 1965-02-17
DE1520764B1 (en) 1970-05-14
BE617618A (en)
CH413361A (en) 1966-05-15
NL264294A (en)
NL264794A (en)

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