WO1998031662A1 - Composes aliphatiques de triisocyanate, leur procede d'obtention et resines de polyurethane en etant faites - Google Patents
Composes aliphatiques de triisocyanate, leur procede d'obtention et resines de polyurethane en etant faites Download PDFInfo
- Publication number
- WO1998031662A1 WO1998031662A1 PCT/JP1998/000115 JP9800115W WO9831662A1 WO 1998031662 A1 WO1998031662 A1 WO 1998031662A1 JP 9800115 W JP9800115 W JP 9800115W WO 9831662 A1 WO9831662 A1 WO 9831662A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- compound
- diisocyanate
- aminomethyl
- polyurethane resin
- polyurethane
- Prior art date
Links
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- -1 isocyanate compound Chemical class 0.000 claims abstract description 83
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- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000000447 dimerizing effect Effects 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- BXKDSDJJOVIHMX-UHFFFAOYSA-N edrophonium chloride Chemical compound [Cl-].CC[N+](C)(C)C1=CC=CC(O)=C1 BXKDSDJJOVIHMX-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000009503 electrostatic coating Methods 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 1
- 229960000218 etynodiol Drugs 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- HLJDOURGTRAFHE-UHFFFAOYSA-N isocyanic acid;3,5,5-trimethylcyclohex-2-en-1-one Chemical class N=C=O.N=C=O.CC1=CC(=O)CC(C)(C)C1 HLJDOURGTRAFHE-UHFFFAOYSA-N 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- YMQPOZUUTMLSEK-UHFFFAOYSA-L lead(2+);octanoate Chemical compound [Pb+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O YMQPOZUUTMLSEK-UHFFFAOYSA-L 0.000 description 1
- 239000002649 leather substitute Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- UQKAOOAFEFCDGT-UHFFFAOYSA-N n,n-dimethyloctan-1-amine Chemical compound CCCCCCCCN(C)C UQKAOOAFEFCDGT-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 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 description 1
- 125000005628 tolylene group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical group OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- 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
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/02—Derivatives of isocyanic acid having isocyanate groups bound to acyclic carbon atoms
- C07C265/04—Derivatives of isocyanic acid having isocyanate groups bound to acyclic carbon atoms of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
Definitions
- the present invention relates to a novel aliphatic triisocyanate compound and a method for producing the same.
- the present invention also relates to a polyurethane resin produced using the isocyanate compound, and a paint or an adhesive containing the polyurethane resin.
- Is used as a curing agent for resins containing active hydrogen for example, it can be used in a wide range of applications such as paints for metals, plastics, woodwork, magnetic recording media, etc., and adhesives. It is applied to various uses.
- the drying and curing properties of the coating film and the physical properties of the coating film are important factors for paints and adhesives.These properties include the functionality of the polyurethane polyisocyanate in the paint or adhesive. The reactivity of the group contributes greatly.
- an organic diisocyanate compound such as hexamethylene diisocyanate disophorone diisocyanate has been used.
- an organic diisocyanate compound such as hexamethylene diisocyanate disophorone diisocyanate
- a reaction product of such an organic diisocyanate compound and a short-chain polyol compound, a polyisocyanurate of the organic diisocyanate compound, and the like are used.
- these polyurethane polyisocyanates have a high viscosity. As it is inconvenient to handle, it is generally necessary to use it after dilution with a solvent.
- the demand for polyurethane polyols as coatings for coating various materials such as metals, plastics, and wood has been rapidly increasing. Perethane polyols have been proposed.
- a polyol compound having three or more functional groups is often used.
- glycerin has a secondary hydroxyl group and therefore has a low reactivity with the isocyanate group, and has a problem that the reaction does not easily proceed.
- trimethylolpropane and the like are solid, and therefore, glycerin is difficult to produce. There is a problem that handling is inconvenient.
- the isocyanate compound used for producing the polyurethane resin is harmful to the human body, it is desirable that the vapor pressure of the isocyanate compound is low.
- a low vapor pressure aliphatic isocyanate compound 41-isocyanatomethyl-1,8-otatamethylene diisocyanate (Japanese Unexamined Patent Publication No. 56-61341, Japanese Patent Application Laid-Open No. 60-233334), 4-isocyanatopropyl-1,7-heptamethylenediisocyanate (see Japanese Patent Application Laid-Open No. 2-1455556), 1, 6, 11-Dendecamethylene triisocyanate (see Japanese Patent Application Laid-Open No. 55-327) have been proposed.
- isocyanate compounds require distillation purification during the production process. Therefore, if the vapor pressure of the isocyanate compound is too low, its production becomes difficult. Therefore, an isocyanate compound having a low vapor pressure not harmful to the human body and capable of being purified by distillation on an industrial scale is desired. Disclosure of the invention
- An object of the present invention is to provide an isocyanate compound having a low vapor pressure not harmful to the human body and capable of being purified by distillation on an industrial scale, and a method for producing the same.
- Another object of the present invention is to provide a polyurethane resin produced using an isocyanate compound having the above characteristics. More specifically, it is to provide a polyurethane resin suitable for use in forms, paints, adhesives, coatings, films, elastomers, and the like.
- the isocyanate compound provided by the present invention is 3-isocyanatomethyl-11,6-hexamethylene diisocyanate represented by the following formula (I).
- This isocyanate compound has a boiling point of 150 ° C./2 mmHg, and is characterized in that it can be easily vacuum distilled on an industrial scale.
- the vapor pressure at 25 ° C is 0.0007 mmHg, and the vapor pressure of hexamethylene diisocyanate, a widely used aliphatic isocyanate, is 0.015 O mmHg. It is sufficiently low, about one-twentieth that of, and hardly vaporizes at room temperature.
- the process for producing 3-isocyanatomethyl-1,6-hexamethylenediisocyanate comprises the steps of: It is characterized by reacting hexamethylene diamine with phosgene.
- This method is preferably carried out by reacting 3-aminomethyl-16-xamethylenediamine with phosgene at 40 ° C or lower in an inert solvent in the presence of a tertiary amine.
- a slurry in which the tertiary amine hydrochloride is precipitated is generated, and then the slurry is heated to form a slurry containing 3-aminomethyl-16-xamethylene diisocyanate, which is filtered to mainly produce tertiary amine hydrochloride.
- the method may further comprise a step of separating the filter cake containing the filtrate and a filtrate mainly containing an inert solvent and 3-aminomethyl-16-xamethylene diisocyanate, and then distilling the filtrate in the presence of a hydrochloric acid scavenger.
- a polyurethane resin provided from still another viewpoint of the present invention is a polyurethane resin obtained by reacting 3-isocyanatomethyl-16-xamethylene diisocyanate with a polyol compound, and is preferably a polyurethane polyisocyanate. Or, it is provided as a polyurethane polyol. Paints or adhesives containing these polyurethane resins are also provided by the present invention. BRIEF DESCRIPTION OF THE FIGURES
- FIG. 1 is a view showing an IR spectrum of 3-isocyanatomethyl-xamethylene diisocynate obtained in Example 1.
- FIG. 2 is a view showing the NMR spectrum of 3-isocyanatomethy 6-xamethylene'socyanate obtained in Example 1.
- 3-isocyanatomethinole 16-xamethylene diisocyanate represented by the above formula (I) is obtained by reacting the corresponding triamine, ie, 3-aminomethyl-16-hexamethylene diamine, with phosgene by a conventional method. It can be manufactured by The raw material 3-aminomethyl-1,6-xamethylenediamine is a compound with a boiling point of 122 ° C / 8 mmHg, obtained by dimerizing acrylonitrile It can be produced by adding hydrogen cyanide to methylene glutaronitrile and then reducing it with hydrogen.
- the following two methods can be used as a method for producing an isocyanate group by reacting phosgene with amine.
- One is to add an acid such as hydrochloric acid, sulfuric acid, phosphoric acid, or acetic acid to the amine to form a salt, preferably a hydrochloride, and then add phosgene at 60 to 230 ° C in an inert solvent. Is reacted to produce an isocyanate compound.
- the other is to react phosgene with phosgene at a low temperature, usually below 40 ° C, preferably below 10 ° C, to form fulvaminic chloride, which is then reacted with 60-230
- a low temperature usually below 40 ° C, preferably below 10 ° C
- This is a method of dehydrochlorinating at 100 ° C., preferably at 100 to 180 ° C., to obtain an isocyanate compound. All of these methods are well known to those skilled in the art.
- the 3-isocyanatomethyl-1,6-hexamethylene diisocyanate according to the present invention can be produced by any of the above methods.
- the former method has an advantage that it is possible to suppress the generation of a urea compound due to the reaction between the produced isocyanate compound and the unreacted amine during the reaction between the amine and phosgene.
- the amine hydrochloride is obtained as large particles or aggregates, it is troublesome to pulverize the amine and react it with phosgene. Therefore, it is usually desirable to employ the latter method for the production of the isocyanate compound of the present invention.
- phosgene is converted to 3-aminoamino-1,6-hexamethylenediamine at low temperature in a solvent inert to the reaction of benzene, tonolen, xylene, monochlorobenzene, o-dichlorobenzene, decalin, etc. by a conventional method.
- pyridine trimethylamine, triethylamine, tributylamine, quinol
- tertiary amines such as glycine, picoline, N-methyl monoreforin, N-ethyl monoreforin, and pyrazine makes it possible to avoid the formation and adhesion of aggregates in the subsequent heating step.
- Tertiary amine may be previously added to the inert solvent, or may be added to the reaction system together with the starting material, 3-aminomethyl-1,6-hexamethylenediamine.
- Tertiary amine reacts with hydrogen chloride produced from the reaction of 3-aminomethyl-1,6-hexamethylenediamine and phosgene in the reaction system to form amine hydrochloride, which acts as a hydrochloric acid scavenger.
- the tertiary amine can be used usually in an amount of at least 3 times, and preferably about 4 to 5 times, the amount of 3-aminomethyl-1,6-hexamethylenediamine.
- phosgene present in the reaction system always be at least equivalent to the amino group of the raw material.
- phosgene is dissolved in an inert solvent in advance and charged into the reaction system, and the power to supply the raw material 3-aminomethyl-1,6-xamethylenediamine, or the raw material amine
- the two may be supplied simultaneously to the reaction system by setting the molar ratio of phosgene to water to 3 or more.
- the reaction between the raw materials, 3-aminomethyl-1,6-hexamethylenediamine, and phosgene is preferably carried out at 40 ° C. or less, particularly at 10 ° C. or less, according to a conventional method. Then, the reaction product was heated to 40 to 230 ° C, particularly 100 to 180 ° C, in the presence of phosgene in a usual manner to cause a dehydrochlorination reaction, and 3isocyanatomethyl Converted to 1,6-hexamethylene diisocyanate. After completion of the reaction, the remaining phosgene is removed, and the reaction mixture is filtered to remove the suspended tertiary amine hydrochloride.
- tertiary amine hydrochloride Although a small amount of tertiary amine hydrochloride is dissolved in the filtrate after the filtration of tertiary amine hydrochloride, tertiary amine hydrochloride remaining during the distillation of the filtrate is dissociated and tertiary amine hydrochloride is dissociated. Distilled out as an acid salt and mixed into the product, it may become tertiary amine hydrochloride again and deteriorate the quality of the product. Therefore, when distilling the filtrate, it is preferable to add calcium oxide, potassium carbonate, sodium carbonate, or the like to the filtrate to capture hydrochloric acid generated by dissociation.
- the 3-isocyanatomethyl-1,6-hexamethylene didisocyanate thus obtained has a boiling point of 150 ° C./2 mmHg and is an extremely fluid liquid at room temperature.
- polyol compound used in the production of polyurethane polyisocyanate having a terminal isocyanate group in the polyurethane resin examples include glycerin, trimethylolpropane, trimethylonoleethane, 1,2,6-hexanetriol, and the like.
- 1,2,4 Polyhydric alcohols with three or more functional groups such as butantrione, erythritol, sonorebitone, pentaerythritol, dipentaerythritol, etc., monomeric glycols such as ethylene glycol, methylene glycol, etc.
- high molecular weight polyols such as Dalicol, an adduct of bisph:!: Nor A with ethylene oxide or propylene oxide, polyether polyols, polyester polyols, polyether polyols, and polycarbonates Polyol compounds such as polyols and polyacryl polyols may be used.
- polyether polyols examples include dalicols such as ethylene glycol, propylene glycol, and diethylene glycol; diols having 3 or more functional groups such as glycerin, trimethylolethane, trimethylolonepropane, and pentaerythritol; ethylenediamine; and triendiamine.
- Hydroxyl-containing polyether polyols obtained by addition-polymerization of alkylene oxides such as ethylene oxide and propylene oxide to the polyamines described above, and polytetramethylene ether glycol obtained by ring-opening polymerization of tetrahydrofuran, etc. Is mentioned.
- Polyester polyols include succinic acid, adipic acid, sebacic acid, azelaic acid, phthalic acid and other dicarboxylic acids, trimellitic acid, pyromellitic acid, and other tricarboxylic acids, and ethylene glycol, propylene glycol, and the like.
- 1,4-butanediol 1,5-pentanediol, 3-methyl-1,5-pentanedionole, 2,2-getylpropanediole, 2-ethynole 2-butynolepropanediol, 1, 6-Hexanediole, neopentinolegricorne, diethylene glycolone, 1,4-cyclohexanediole, diols such as 1,4-cyclohexanedimethanol, or triols such as trimethylolpropane and glycerin, or bisphenol A, bisphenol Obtained by polycondensation reaction with F etc. And others.
- polyetherester polyol examples include reacting a mixture with an ether group-containing diol or another glycolone with the above-mentioned dicarboxylic acid or anhydride thereof, or reacting an alkylene oxide with polyester glycol. And poly (polytetramethylene ether) adipate.
- polycarbonate polyol examples include a dealcoholization condensation reaction between a polyhydric alcohol and a dialkyl carbonate such as dimethyl carbonate and getyl carbonate, a dephenol condensation reaction between a polyhydric alcohol and diphenyl carbonate, and a polyhydric alcohol. Those obtained by the de-ethylene dalicol condensation reaction with ethylene carbonate or the like can be used.
- polyhydric alcohol examples include 1,6-hexanediole, diethyleneglyconele, propyleneglyconele, 1,4-butanediole, 1,5-pentanedionole, 3-methinoleole1,5-pentanole Diol, 2, 2-getylpropanediol, 2-ethyl 2-butylprono.
- aliphatic polyols such as 1,4-cyclohexanediol and 1,4-cyclohexanedimethanol.
- Polycarbonate polyols using aliphatic diols such as 1,4-cyclohexanediol and 1,4-cyclohexanedimethanol.
- Diamines include hexamethylene diamine, xylene diamine, isophorone diamine, N, N-dimethylethylene diamine, and the like
- amino alcohols include monoethanolamine, diethanolamine, and the like.
- the preferred molecular weight of these polyol compounds is about 500 to 500.
- a polyol compound having a molecular weight of more than 500 is used, the crosslink density may decrease and the strength of the coating film may decrease.
- isocyanate compounds include 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, xylene 1,1,4-diisocyanate, xylene 1,1,3-diisocyanate, 4, ⁇ ′— Diphenylmethane diisocyanate, 2, 4'-Diphenylmethane diisocyanate, 4,4 'Diphenyl ether diisocyanate, 3, 3'-Dimethyldiphenylmethane-1,4' Isocyanate, m-Phenylene diisocyanate, p-Phenylene diisocyanate, naphthylene-1,4 diisocyanate, naphthylene-1,5-diisocyanate, 3, 3'-Dimethoxydiphenyl 4, A ' —Aromatic diisocyanates
- modified isocyanurates modified bullets, modified uretonimines, modified karposimids, and the like may be used.
- modified isocyanate compounds may be used alone or in combination of two or more.
- a polyisocyanate compound having three or more functionalities may be used.
- the reaction temperature in the production (urethane-forming reaction) of the polyurethane polyisocyanate of the present invention can be usually selected from a range of 10 to 90 ° C., and a catalyst for the reaction is generally unnecessary.
- a catalyst for the reaction is generally unnecessary.
- an organotin catalyst such as dibutyltin dilaurate / dibutyltindioctate, an organic lead catalyst such as lead octanoate, or a tertiary amine based catalyst such as triethylamine, dimethyloctylamine, diazabicycloundecene, etc. It is also effective to use a compound catalyst.
- the progress of the urethanization reaction can be monitored by measuring the NCO content during the reaction, and the reaction can be stopped when the target NCO content is reached.
- the urethanization reaction can be performed in a solvent.
- the solvent used include inert solvents commonly used in polyurethane production, for example, aromatic solvents such as toluene and xylene, ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone, ethyl acetate, and the like.
- Ester solvents such as butyl acetate and isobutyl acetate; Dalicol ether ester solvents such as Tylene glycolone ethino oleate acetate, propylene darico oleno methinooleate teracetate, 3-methyl-3-methoxybutyl acetate, ethyl 3-ethoxypropionate, tetrahi
- Examples thereof include ether solvents such as drofuran and dioxane, and these may be used in combination of two or more.
- the molecular weight is from 350 to 10 in terms of weight average molecular weight. It is preferably 0000, preferably 650 to 2000. If the weight-average molecular weight is more than 1000, the molecular weight between crosslinks may be too long to lower the strength of the coating, or the viscosity may be too high to lower the workability.
- a polyurethane polyol which is one of the polyurethane resins
- the molecular terminal functional group becomes (isosinate group / active hydrogen group) 1 What should I do?
- a dialkylamine such as di-n-butylamine, a monoalkylamine such as butynoleamine, a monoalkylamine such as ethanolinol, isopropinoleanolone, a monoethanolamine such as butanolinone, a monoethanolanolamine, a diethanolamine, etc.
- Monoamino alcohol such as amine may be used.
- the molecular weight of the polyurethane polyol of the present invention is preferably from 500 to 300,000, more preferably from 1500 to 2000, in terms of weight average molecular weight. If the weight average molecular weight is less than 50,000, the strength of the coating film may be low. If the weight average molecular weight exceeds 3,000, the viscosity may be too high and the workability may be reduced.
- the polyurethane polyol of the present invention may be blended with an existing polyurethane polyisocyanate alone or in combination of two or more, if necessary.
- Polyurethane polyisocyanates used for such purposes include, for example, tolylene diisocyanate, diphenylmethane diisocyanate, Examples include adducts of diisocyanates with trimethylolpropane, such as succinates and isophorondiisocyanates, trimerized diisocyanate compounds, and modified bullets obtained by reaction with water.
- the paint, coating agent, and adhesive of the present invention containing the above polyurethane resin may further contain a polyol compound.
- a polyol compound used for such a purpose for example, a compound having a weight average molecular weight of 50 to 300 000 having two or more hydroxyl groups in the molecule can be suitably used.
- the above-mentioned monomeric dalicols, polyols having three or more functional groups saturated or unsaturated polyester polyols, saturated or unsaturated oil-modified or fatty acid-modified alkyd polyols, amino alkyd polyols, polycarbonate polyols, acrylics Horio Nole, Horie Tenore Polio Nole, Polyestenole Noe Polle Nole, Jeho.
- Examples include xylene polyol, polyurethane polyol, cenorellose acetate butyrate polyol, and fluorinated polyol.
- saturated or unsaturated polyester polyols, saturated resins, etc. in terms of coating film performance (gloss, thinness, hardness, viability, durability, etc.), workability (drying, curability, etc.), cost, etc.
- unsaturated oil-modified or fatty acid-modified alkyd vorols and ataryl polyols are preferred. If the weight-average molecular weight of these polyol compounds exceeds 3,000,000, the crosslink density may decrease and the strength of the coating may decrease.
- the (isosocyanate group Z active hydrogen group) is 0.1 or less, the cross-linking of the cured product is insufficient and the coating film strength is low, and the physical properties such as chemical resistance and solvent resistance may be reduced. If it exceeds, the cured product is brittle, and the impact resistance may be reduced.
- the paints, coating agents, and adhesives of the present invention may be used, if necessary, as a curing accelerator, a curing retarder, an ultraviolet absorber, an antioxidant, a plasticizer, a leveling agent, etc. , Various additives and various pigments.
- the paint of the present invention containing the cisocyanate curing agent for paint can be applied by a usual coating method. For example, paint using an airless sprayer, air sprayer, electrostatic coating, dipping, roll coating machine, rake, collision mixing sprayer, paper injection cure (VIC) type coating machine, etc. Can be.
- a polyurethane polyisocyanate having excellent reactivity, properties of a coating film, and the like.
- the polyurethane paint and polyurethane adhesive containing the polyurethane resin of the present invention have better coating performance or better adhesiveness than conventional paints and adhesives. Therefore, it can be applied to a wide range of fields such as paints for metals, plastics, concrete and wood, magnetic recording media such as audio tapes, video tapes and floppy disks, inks, synthetic leathers, adhesives and fibers.
- a glass reactor equipped with a stirrer, a thermometer, a condenser, and a gas injection tube was charged with 530 g of orthodichlorobenzene and 98 g of pyridine, and cooled to 10 ° C.
- 125 g of phosgene gas was supplied into the reaction system to dissolve it. While keeping this solution at 10 ° C or lower, a solution of 40 g of 3-aminomethyl-1,6-hexamethylenediamine dissolved in 100 g of orthodichlorobenzene was stirred under stirring for 2 hours. It was dropped. After completion of the dropwise addition, stirring was continued for another 2 hours.
- the reaction system became a relatively fluid slurry of pyridine hydrochloride.
- the slurry was heated to 130 ° C. over about 2 hours while supplying phosgene at 30 g / Hr, and the supply of phosgene was continued at 30 g / Hr for 5 hours at this temperature.
- the reaction system eventually became a small particle slurry of pyridine hydrochloride.
- nitrogen gas was blown into the reaction mixture to remove residual phosgene, the mixture was filtered to remove pyridin hydrochloride.
- After distilling off the orthodichlorobenzene benzene was distilled under a pressure of the filtrate 1 O OmniHg, to obtain a fraction 40 g of boiling 1 50 ° C / 2mmH g further raising the vacuum degree.
- the obtained fraction was identified as 3-isocyanatomethyl-1,6-hexamethylene diisocyanate.
- VEST AN AT T 1 890/1 00 (Product name: Isophorone diisocyanate polyisocyanurate (trimer) manufactured by Huls Co., Ltd., resin solid content: 100%) Viscosity measuring method>
- the viscosity of the isocyanate compound was measured according to JIS-1603 using a ⁇ -type viscometer (VISCONIC EHD-R, manufactured by TOK IMEC). The measurement temperature was 25 ° C, the sample volume was 1.5 ml, and the measurement was performed using a standard rotor (1 ° 34,). NCO content measurement method>
- the NCO content of the isocyanate compound was measured in accordance with JISK-1603.
- Comparative Example 8> The following evaluation tests were performed using VE STANAT T 1890/100 and polyol, and the results are shown in Table 2.
- Reaction rate-An isocyanate compound and a polyol compound are mixed in an amount such that the number of functional groups of isocyanate groups and hydroxyl groups is 1.1 to 1, and the resulting mixture is dried on a glass plate having a thickness of 2 mm. Apply the solution to a thickness of 3 ⁇ , leave it at 23 ° C for 5 minutes, sandwich the coating with another glass plate, and use an infrared absorption spectrum (FTIRH-230, manufactured by Nippon Bunko Co., Ltd.). The absorbance of the isocyanate group at 227 Ocm- 1 was measured.
- FTIRH-230 infrared absorption spectrum
- the isocyanate compound and the polyol compound are mixed in an amount such that the number of functional groups of the isocyanate group and the hydroxyl group becomes 1.1 to 1, applied on release paper, heated at 80 ° C for 24 hours, and cured to form a film. A coating film of 100 ⁇ was obtained.
- the film properties of the obtained coating film were measured using Tensilon UTM-II100 (manufactured by Toyo Baldwin Co., Ltd.) according to JIS 6301, at a temperature of 23 ° C. and a relative humidity of 65%.
- the isocyanate compound and the polyol compound are mixed in an amount such that the number of functional groups of the isocyanate group and the hydroxyl group is 1.1 to 1, applied to a glass plate, heated at 80 ° C for 24 hours, cured, and cured. Obtained a coating film of 100 ⁇ m.
- the solvent shown in Table 2 was dropped on the surface of the coating film, and after 30 seconds, the solvent was wiped off, and the surface condition was visually observed and judged according to the following criteria.
- Example 1 Comparison of Example 1 and Comparative Examples 2 to 4 shows that 3-isocyanatomethyl-1,6-hexamethylene diisocyanate used in Example 1 is a bifunctional hexamethylene
- the NC ⁇ content is higher than the polyfunctional hexamethylene diisocyanate ⁇ isophorone disocinate, albeit with the same viscosity as the diisocyanate.
- Example 2 Comparing Example 2 with Comparative Examples 5 to 8, the 3 isocyanatomethyl-1,6-hexamethylene diisocyanate used in Example 2 is the same as that used in Comparative Examples 2 and 3. It has a reactivity equal to or higher than that of the functional diisocyanate compound, shows higher reactivity than the polyfunctional isocyanate compound used in Comparative Examples 7 and 8, and is also excellent in curability.
- Example 2 When Example 2 is compared with Comparative Examples 7 and 8, in Example 2, the solvent resistance of the obtained coating films is the same despite the small amount of the isocyanate compound added.
- the 3 isocyanatomethyl-1,6-hexamethylene diisocyanate of the present invention has low viscosity and excellent workability, and has a high NCO content.
- the same coating film properties can be obtained by adding a smaller amount than the conventionally used isocyanate compound.
- the 3-isocyanatomethyl 1,6-hexamethylene diisocyanate of the present invention is excellent in reactivity, has a high curing speed, and has a high cross-linking density of the cured product, so that foams, metals, and plastics can be obtained. It is suitable for applications in the fields of paints such as wood, woodwork, magnetic recording media, etc., and in the field of adhesives.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polyurethanes Or Polyureas (AREA)
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP98900367A EP1020435A4 (en) | 1997-01-16 | 1998-01-14 | ALIPHATIC TRIISOCYANATE COMPOUNDS, PROCESS FOR OBTAINING SAME, AND POLYURETHANE RESINS THEREOF |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP580097 | 1997-01-16 | ||
JP9/5800 | 1997-01-16 |
Publications (1)
Publication Number | Publication Date |
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WO1998031662A1 true WO1998031662A1 (fr) | 1998-07-23 |
Family
ID=11621164
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/JP1998/000115 WO1998031662A1 (fr) | 1997-01-16 | 1998-01-14 | Composes aliphatiques de triisocyanate, leur procede d'obtention et resines de polyurethane en etant faites |
Country Status (3)
Country | Link |
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US (1) | US20020123644A1 (ja) |
EP (1) | EP1020435A4 (ja) |
WO (1) | WO1998031662A1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7584629B2 (en) | 2002-12-19 | 2009-09-08 | Basf Aktiengesellschaft | Separation of a substance mixture consisting of hydrogen chloride and phosgene |
JP2019070068A (ja) * | 2017-10-06 | 2019-05-09 | 旭化成株式会社 | 塗料組成物 |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8399012B2 (en) * | 2006-04-17 | 2013-03-19 | Kimberly-Clark Worldwide, Inc. | Degradable therapeutic delivery device |
US7504533B2 (en) * | 2006-04-24 | 2009-03-17 | Bayer Materialscience Llc | Process for the production of isocyanates |
WO2009026387A1 (en) * | 2007-08-20 | 2009-02-26 | Vanderbilt University | Poly(ester urethane) urea foams with enhanced mechanical and biological properties |
DE102008009761A1 (de) | 2008-02-19 | 2009-08-27 | Bayer Materialscience Ag | Verfahren zur Herstellung von Isocyanaten |
US20100068171A1 (en) * | 2008-05-27 | 2010-03-18 | Vanderbilt University | Injectable bone/polymer composite bone void fillers |
WO2017030545A1 (en) | 2015-08-17 | 2017-02-23 | Transitions Optical, Inc. | Curable photochromic compositions |
EP3882235A4 (en) * | 2018-11-15 | 2022-08-10 | National University Corporation Kobe University | PROCESS FOR MANUFACTURING ISOCYANATE COMPOUND |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS57200419A (en) * | 1981-06-02 | 1982-12-08 | Asahi Chem Ind Co Ltd | Composition for forming novel polyurethane resin |
JPS617321A (ja) * | 1984-06-21 | 1986-01-14 | Asahi Chem Ind Co Ltd | 新規プレポリマ−及びその樹脂と製造方法 |
JPH0859592A (ja) * | 1994-08-25 | 1996-03-05 | Aibaitsu Kk | ロイシン−アルキルエステルイソシアナート、その製法およびその重合体 |
JPH0912525A (ja) * | 1995-06-23 | 1997-01-14 | Bayer Ag | トリイソシアネートの製造方法 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR8003393A (pt) * | 1979-06-04 | 1980-12-30 | Du Pont | Processo para preparar um isocianato de arilsulfonila |
CH688861A5 (de) * | 1994-12-08 | 1998-04-30 | Lonza Ag | 4,4'-(Phenylendiisopropyl)-bis(2,6-dialkylphenylisocyanate). |
-
1998
- 1998-01-14 WO PCT/JP1998/000115 patent/WO1998031662A1/ja not_active Application Discontinuation
- 1998-01-14 US US09/341,599 patent/US20020123644A1/en not_active Abandoned
- 1998-01-14 EP EP98900367A patent/EP1020435A4/en not_active Withdrawn
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS57200419A (en) * | 1981-06-02 | 1982-12-08 | Asahi Chem Ind Co Ltd | Composition for forming novel polyurethane resin |
JPS617321A (ja) * | 1984-06-21 | 1986-01-14 | Asahi Chem Ind Co Ltd | 新規プレポリマ−及びその樹脂と製造方法 |
JPH0859592A (ja) * | 1994-08-25 | 1996-03-05 | Aibaitsu Kk | ロイシン−アルキルエステルイソシアナート、その製法およびその重合体 |
JPH0912525A (ja) * | 1995-06-23 | 1997-01-14 | Bayer Ag | トリイソシアネートの製造方法 |
Non-Patent Citations (1)
Title |
---|
See also references of EP1020435A4 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7584629B2 (en) | 2002-12-19 | 2009-09-08 | Basf Aktiengesellschaft | Separation of a substance mixture consisting of hydrogen chloride and phosgene |
JP2019070068A (ja) * | 2017-10-06 | 2019-05-09 | 旭化成株式会社 | 塗料組成物 |
Also Published As
Publication number | Publication date |
---|---|
EP1020435A4 (en) | 2000-12-13 |
EP1020435A1 (en) | 2000-07-19 |
US20020123644A1 (en) | 2002-09-05 |
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