GB977958A - A process for the preparation of partially esterified amino alcohols - Google Patents
A process for the preparation of partially esterified amino alcoholsInfo
- 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
Links
- 150000001414 amino alcohols Chemical class 0.000 title abstract 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 15
- 150000001875 compounds Chemical class 0.000 abstract 10
- 239000004215 Carbon black (E152) Substances 0.000 abstract 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 9
- 229930195733 hydrocarbon Natural products 0.000 abstract 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract 7
- 239000008096 xylene Substances 0.000 abstract 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 6
- 125000003277 amino group Chemical group 0.000 abstract 6
- -1 halogen alkane Chemical class 0.000 abstract 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract 4
- 239000003795 chemical substances by application Substances 0.000 abstract 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 abstract 4
- 239000004814 polyurethane Substances 0.000 abstract 4
- 229920002635 polyurethane Polymers 0.000 abstract 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 abstract 4
- 235000010215 titanium dioxide Nutrition 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000002947 alkylene group Chemical group 0.000 abstract 3
- 238000000576 coating method Methods 0.000 abstract 3
- 239000004922 lacquer Substances 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- 239000003960 organic solvent Substances 0.000 abstract 3
- 239000003973 paint Substances 0.000 abstract 3
- 229920001228 polyisocyanate Polymers 0.000 abstract 3
- 239000005056 polyisocyanate Substances 0.000 abstract 3
- 229920005989 resin Polymers 0.000 abstract 3
- 239000011347 resin Substances 0.000 abstract 3
- 229930195734 saturated hydrocarbon Natural products 0.000 abstract 3
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 abstract 2
- KPOXQAKDFUYNFA-UHFFFAOYSA-N 3-methyl-7-oxabicyclo[4.1.0]heptane-4-carboxylic acid Chemical compound C1C(C(O)=O)C(C)CC2OC21 KPOXQAKDFUYNFA-UHFFFAOYSA-N 0.000 abstract 2
- ZFIVKAOQEXOYFY-UHFFFAOYSA-N Diepoxybutane Chemical compound C1OC1C1OC1 ZFIVKAOQEXOYFY-UHFFFAOYSA-N 0.000 abstract 2
- 239000004593 Epoxy Substances 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 240000006240 Linum usitatissimum Species 0.000 abstract 2
- 235000004431 Linum usitatissimum Nutrition 0.000 abstract 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 abstract 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 abstract 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 2
- 239000004677 Nylon Substances 0.000 abstract 2
- 239000004952 Polyamide Substances 0.000 abstract 2
- 229910000831 Steel Inorganic materials 0.000 abstract 2
- 229920001807 Urea-formaldehyde Polymers 0.000 abstract 2
- 235000011037 adipic acid Nutrition 0.000 abstract 2
- 150000001279 adipic acids Chemical class 0.000 abstract 2
- 229920000180 alkyd Polymers 0.000 abstract 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 abstract 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract 2
- 239000001913 cellulose Substances 0.000 abstract 2
- 229920002678 cellulose Polymers 0.000 abstract 2
- 239000011248 coating agent Substances 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- LDLDYFCCDKENPD-UHFFFAOYSA-N ethenylcyclohexane Chemical compound C=CC1CCCCC1 LDLDYFCCDKENPD-UHFFFAOYSA-N 0.000 abstract 2
- 150000002170 ethers Chemical class 0.000 abstract 2
- 239000004744 fabric Substances 0.000 abstract 2
- 235000004426 flaxseed Nutrition 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 2
- 239000004615 ingredient Substances 0.000 abstract 2
- 239000000944 linseed oil Substances 0.000 abstract 2
- 150000002763 monocarboxylic acids Chemical class 0.000 abstract 2
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical class C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 abstract 2
- 229920003986 novolac Polymers 0.000 abstract 2
- 229920001778 nylon Polymers 0.000 abstract 2
- 150000003022 phthalic acids Chemical class 0.000 abstract 2
- 239000000049 pigment Substances 0.000 abstract 2
- 229920002647 polyamide Polymers 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 239000003549 soybean oil Substances 0.000 abstract 2
- 235000012424 soybean oil Nutrition 0.000 abstract 2
- 239000010959 steel Substances 0.000 abstract 2
- 239000000454 talc Substances 0.000 abstract 2
- 235000012222 talc Nutrition 0.000 abstract 2
- 229910052623 talc Inorganic materials 0.000 abstract 2
- 150000003504 terephthalic acids Chemical class 0.000 abstract 2
- 239000004408 titanium dioxide Substances 0.000 abstract 2
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 abstract 1
- QNYBOILAKBSWFG-UHFFFAOYSA-N 2-(phenylmethoxymethyl)oxirane Chemical compound C1OC1COCC1=CC=CC=C1 QNYBOILAKBSWFG-UHFFFAOYSA-N 0.000 abstract 1
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 abstract 1
- 229910015900 BF3 Inorganic materials 0.000 abstract 1
- 238000005698 Diels-Alder reaction Methods 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- 229920000877 Melamine resin Polymers 0.000 abstract 1
- OGWDLDBWRGCPBU-UHFFFAOYSA-N N=C=O.N=C=O.CCOCC Chemical class N=C=O.N=C=O.CCOCC OGWDLDBWRGCPBU-UHFFFAOYSA-N 0.000 abstract 1
- QORUGOXNWQUALA-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 Chemical compound N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 QORUGOXNWQUALA-UHFFFAOYSA-N 0.000 abstract 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 abstract 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 239000010426 asphalt Substances 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 125000006267 biphenyl group Chemical group 0.000 abstract 1
- 230000001680 brushing effect Effects 0.000 abstract 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 1
- 238000005266 casting Methods 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 abstract 1
- 210000003298 dental enamel Anatomy 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 abstract 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- 239000000835 fiber Substances 0.000 abstract 1
- 239000000945 filler Substances 0.000 abstract 1
- 239000006260 foam Substances 0.000 abstract 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 abstract 1
- 150000003944 halohydrins Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- VUNCWTMEJYMOOR-UHFFFAOYSA-N hexachlorocyclopentadiene Chemical compound ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C1Cl VUNCWTMEJYMOOR-UHFFFAOYSA-N 0.000 abstract 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 abstract 1
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 1
- 239000012433 hydrogen halide Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000005470 impregnation Methods 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
- 239000011976 maleic acid Substances 0.000 abstract 1
- 239000003921 oil Substances 0.000 abstract 1
- 235000019198 oils Nutrition 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- 229920000647 polyepoxide Polymers 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 229920001225 polyester resin Polymers 0.000 abstract 1
- 239000004645 polyester resin Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001174 sulfone group Chemical group 0.000 abstract 1
- 150000003505 terpenes Chemical class 0.000 abstract 1
- 235000007586 terpenes Nutrition 0.000 abstract 1
- 239000002562 thickening agent Substances 0.000 abstract 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 abstract 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002966 varnish Substances 0.000 abstract 1
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.
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 |
|---|---|---|---|
| GB18529/62A Expired GB977958A (en) | 1961-05-16 | 1962-05-14 | A process for the preparation of partially esterified amino alcohols |
| GB18530/62A Expired GB983516A (en) | 1961-05-16 | 1962-05-14 | Fluid epoxide compositions |
Family Applications After (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) | GB977958A (en) |
| NL (3) | NL264294A (en) |
Cited By (3)
| 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)
| 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 |
| EP0000086B1 (en) * | 1977-06-13 | 1982-04-14 | Shell Internationale Researchmaatschappij B.V. | 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 |
-
0
- NL NL264794D patent/NL264794A/xx unknown
- NL NL112652D patent/NL112652C/xx active
- BE BE617618D patent/BE617618A/xx unknown
- NL NL264294D patent/NL264294A/xx unknown
-
1962
- 1962-05-14 CH CH576662A patent/CH413361A/en unknown
- 1962-05-14 GB GB18529/62A patent/GB977958A/en not_active Expired
- 1962-05-14 DE DE19621520764D patent/DE1520764B1/en active Pending
- 1962-05-14 GB GB18530/62A patent/GB983516A/en not_active Expired
Cited By (4)
| 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 |
|---|---|
| NL264794A (en) | |
| DE1520764B1 (en) | 1970-05-14 |
| CH413361A (en) | 1966-05-15 |
| BE617618A (en) | |
| GB983516A (en) | 1965-02-17 |
| NL112652C (en) | |
| NL264294A (en) |
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