ES2665759T3 - Composición curable - Google Patents
Composición curable Download PDFInfo
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- ES2665759T3 ES2665759T3 ES14187164.0T ES14187164T ES2665759T3 ES 2665759 T3 ES2665759 T3 ES 2665759T3 ES 14187164 T ES14187164 T ES 14187164T ES 2665759 T3 ES2665759 T3 ES 2665759T3
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- 239000000203 mixture Substances 0.000 title abstract description 13
- 150000001875 compounds Chemical class 0.000 abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 150000003335 secondary amines Chemical group 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 229920000909 polytetrahydrofuran Polymers 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000004448 titration Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- -1 glycerin polyol Chemical class 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
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- 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
- C08G71/00—Macromolecular compounds obtained by reactions forming a ureide or urethane link, otherwise, than from isocyanate radicals in the main chain of the macromolecule
- C08G71/04—Polyurethanes
-
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/26—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of rings other than six-membered aromatic rings
-
- 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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/1816—Catalysts containing secondary or tertiary amines or salts thereof having carbocyclic groups
-
- 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
- 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
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/83—Chemically modified polymers
-
- 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
- C08G71/00—Macromolecular compounds obtained by reactions forming a ureide or urethane link, otherwise, than from isocyanate radicals in the main chain of the macromolecule
- C08G71/02—Polyureas
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
- C08L75/08—Polyurethanes from polyethers
-
- 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
- C09D175/02—Polyureas
-
- 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
- C09D175/08—Polyurethanes from polyethers
-
- 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
- C09D175/12—Polyurethanes from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/02—Polyureas
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/08—Polyurethanes from polyethers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/12—Polyurethanes from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group
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)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Polyurethanes Or Polyureas (AREA)
- Sealing Material Composition (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Una composición curable que comprende una primera unidad que comprende al menos dos grupos -(NH-C>=O)-, una segunda unidad que comprende al menos dos grupos -(C>=O)-C≡C-R1, y un catalizador, en la que R1 representa hidrógeno o un grupo que tiene de 1 a 12 átomos de carbono, preferentemente hidrógeno o CH3, y lo más preferente hidrógeno; en la que el término "unidad" se refiere a un compuesto o una parte de un compuesto que comprende la unidad; y en la que el catalizador es una amina secundaria o terciaria y en la que los grupos -(NH-C>=O)- son proporcionados por grupos urea y/o uretano.
Description
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La temperatura de descomposición (Td) de las composiciones curadas se midió usando análisis termogravimétrico (TGA). A la Td se observó una pérdida de peso del 5 %. La temperatura de descomposición se registró calentando a 10 °C/min.
Síntesis de compuestos
Ejemplo 1: Síntesis de diisocianato de isoforona (IPDI) conjugado con diéster PTHF (denominado en lo sucesivo en el presente documento PITHF)
Se añadieron 40 g de politetrahidrofurano (PTHF, Mn = 1000 g/mol) a un matraz de fondo redondo de 3 bocas de 250 ml y se calentó a 120 °C al vacío durante 1,5 h. Después, la temperatura se redujo hasta 90 °C y la mezcla de reacción se purgó con nitrógeno (o un gas inerte comparable), y se añadieron 4,45 g de diisocianato de isoforona (IPDI), y la temperatura se aumentó hasta 110 °C. La mezcla de reacción se agitó durante al menos 12 h, hasta que se consumieron todos los grupos NCO, tal como se determinó mediante valoración (el contenido de isocianato libre se puede medir fácilmente, por ejemplo, mediante valoración del isocianato libre con una amina y valoración por retroceso de la amina sin reaccionar).
Se añadieron 42,6 g del intermedio a un matraz de fondo redondo equipado con un aparato Dean-Stark, junto con 0,43 g de ácido p-toluenosulfónico (p-TsOH) disuelto en 100 ml de tolueno. La mezcla se agitó a una temperatura de 40 a 50 °C hasta que se observó una solución homogénea, y después se añadieron 5,37 g (4,7 ml) de ácido propiólico. La solución final se calentó hasta 140 °C y se agitó a esta temperatura durante 48 horas. Cuando la reacción finalizó (tal como se detectó mediante RMN 1H), la mezcla se enfrió hasta temperatura ambiente, y se diluyó con otros 100 ml de tolueno. La solución orgánica se lavó seguidamente tres veces con una solución de bicarbonato de sodio en agua (2 % en peso de bicarbonato en agua), hasta que se neutralizó el exceso de ácido propiólico. La fase orgánica se trató a continuación con salmuera, se secó sobre sulfato de magnesio, se filtró y se concentró al vacío, dando como resultado el compuesto de la invención.
Ejemplo 2: Síntesis de diisocianato de hexametileno (HDI) conjugado con diéster PTHF (denominado en lo sucesivo en el presente documento PHTHF)
Se añadieron 50 g de PTHF (Mn = 1000 g/mol) a un matraz de fondo redondo de 3 bocas de 250 ml y se calentó a 120 °C al vacío durante 1,5 h. Después, tras reducir la temperatura hasta 90 °C y purgar la mezcla de reacción con nitrógeno, se añadieron 4,21 g de diisocianato de hexametileno (HDI), y la temperatura se aumentó hasta 110 °C. La mezcla de reacción se agitó durante al menos 12 h, hasta que se consumieron todos los grupos NCO, tal como se determinó mediante valoración.
Se añadieron 52,47 g del intermedio a un matraz de fondo redondo equipado con un aparato Dean-Stark, junto con 0,52 g de ácido p-toluenosulfónico (p-TsOH) disuelto en 100 ml de tolueno. La mezcla se agitó a una temperatura de 40 a 50 °C hasta que se observó una solución homogénea, y después se añadieron 6,38 g (5,67 ml) de ácido propiólico. La solución final se calentó hasta 140 °C y se agitó a esta temperatura durante 48 horas. Cuando la reacción finalizó (tal como se detectó mediante RMN 1H), la mezcla se enfrió hasta temperatura ambiente, y se diluyó con otros 100 ml de tolueno. La solución orgánica se lavó seguidamente tres veces con una solución de bicarbonato de sodio en agua (2 % de bicarbonato en agua), hasta que se neutralizó el exceso de ácido propiólico. La fase orgánica se trató a continuación con salmuera, se secó sobre sulfato de magnesio, se filtró y se concentró al vacío, dando el compuesto de la invención. Rendimiento final: 70 %.
Composición de la invención / Curado de la composición
Ejemplo 3: Composición con el compuesto del ejemplo 1 (PITHF) y compuesto adicional
Se añadieron 2 g del compuesto del ejemplo 1 y 0,048 g de un compuesto adicional que comprendía tres grupos -O(C=O)-C≡C-H (Mn de aproximadamente 1000 g/mol) a una solución de DABCO (0,0058 g) en acetato de etilo (0,4 ml), y la mezcla se dejó expuesta al aire a temperatura ambiente. Al cabo de 2 horas, se obtuvo un polímero no pegajoso de color marrón (la composición curada de la invención).
El compuesto adicional se obtuvo haciendo reaccionar un poliol de glicerina propoxilada con ácido propiólico, en el que la relación OH:ácido propiólico es de al menos 1:1. El poliol de glicerina propoxilada se obtuvo haciendo reaccionar glicerina con óxido de propileno. La glicerina actúa como iniciador.
Ensayos de tracción (velocidad de tensión 50 mm/min):
Alargamiento a la rotura: 330 % Resistencia a la tracción: 3,38 MPa
Ejemplo 4: Composición con el compuesto del ejemplo 1 (PITHF)
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Claims (1)
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imagen1 imagen2
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14187164.0A EP3002302B1 (en) | 2014-09-30 | 2014-09-30 | Curable composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2665759T3 true ES2665759T3 (es) | 2018-04-27 |
Family
ID=51626453
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES14187164.0T Active ES2665759T3 (es) | 2014-09-30 | 2014-09-30 | Composición curable |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US10577463B2 (es) |
| EP (1) | EP3002302B1 (es) |
| JP (1) | JP6703529B2 (es) |
| KR (1) | KR20170063583A (es) |
| CN (1) | CN106795268B (es) |
| BR (1) | BR112017002039B1 (es) |
| ES (1) | ES2665759T3 (es) |
| PL (1) | PL3002302T3 (es) |
| WO (1) | WO2016050878A1 (es) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USD1044825S1 (en) | 2018-09-14 | 2024-10-01 | Boxkingz | Display screen with a graphical user interface for a grid for an online gaming application |
| PL3677616T3 (pl) | 2019-01-04 | 2022-10-31 | Henkel Ag & Co. Kgaa | Sposób wytwarzania bezizocyjanianowych poliuretanów |
| CN112011049A (zh) * | 2019-05-30 | 2020-12-01 | 中国科学院化学研究所 | 一种热塑性聚脲弹性体及其制备方法 |
| CN113845656B (zh) * | 2021-11-08 | 2023-09-15 | 江苏富琪森新材料有限公司 | 一种用于制备类玻璃体的组合物、类玻璃体及其制备方法和应用 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3383403A (en) | 1963-11-07 | 1968-05-14 | Monsanto Co | Dimerization process |
| US3872152A (en) * | 1970-05-26 | 1975-03-18 | Clifton L Kehr | Terminally unsaturated liquid polyene having internally unreactive carbon-to-carbon unsaturation |
| DE2200268A1 (de) * | 1971-01-05 | 1972-07-27 | Ciba Geigy Ag | Dichtungszusammensetzungen |
| DE2854192A1 (de) * | 1978-12-15 | 1980-06-26 | Basf Ag | Polyurethan-beschichtungsmittel |
| US5591890A (en) | 1995-11-03 | 1997-01-07 | E. I. Du Pont De Nemours And Company | Process for producing ortho-nitro aromatic acids by oxidation of ortho-nitroalkylaromatic compounds |
| EP1146061A4 (en) | 1999-08-30 | 2003-06-18 | Toyo Ink Mfg Co | URETHANE-UREA RESIN BY MICHAEL-ADDITION, METHOD FOR PRODUCING THE SAME, ADHESIVE, METHOD FOR PRODUCING THE SAME, COATING MATERIAL FOR PRODUCING AN INK-ABSORBING LAYER AND RECORDING DEVICE |
| JP2002161126A (ja) * | 2000-11-27 | 2002-06-04 | Nippon Paint Co Ltd | 樹脂組成物及びカチオン電着塗料組成物 |
| JP4619068B2 (ja) * | 2003-09-04 | 2011-01-26 | 日本ペイント株式会社 | 水性樹脂組成物及び電着塗料組成物 |
| EP1955712A1 (en) * | 2007-02-09 | 2008-08-13 | Scil proteins GmbH | Multimeric conjugate |
| DE102010030437A1 (de) | 2010-06-23 | 2011-12-29 | Henkel Ag & Co. Kgaa | TPU-Kaschierklebstoff |
| WO2013065009A1 (en) * | 2011-11-01 | 2013-05-10 | National Institute Of Immunology | A sortase-click reaction suite for synthesis of multivalent dendrimeric protein assembly |
| EP2610263A1 (de) * | 2011-12-30 | 2013-07-03 | Brossmer, Reinhard | Sialinsäure-Dimere |
-
2014
- 2014-09-30 PL PL14187164T patent/PL3002302T3/pl unknown
- 2014-09-30 EP EP14187164.0A patent/EP3002302B1/en active Active
- 2014-09-30 ES ES14187164.0T patent/ES2665759T3/es active Active
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2015
- 2015-09-30 CN CN201580048110.8A patent/CN106795268B/zh not_active Expired - Fee Related
- 2015-09-30 WO PCT/EP2015/072622 patent/WO2016050878A1/en not_active Ceased
- 2015-09-30 KR KR1020177007484A patent/KR20170063583A/ko not_active Ceased
- 2015-09-30 BR BR112017002039-4A patent/BR112017002039B1/pt not_active IP Right Cessation
- 2015-09-30 JP JP2017517344A patent/JP6703529B2/ja not_active Expired - Fee Related
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2017
- 2017-03-29 US US15/472,523 patent/US10577463B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP3002302A1 (en) | 2016-04-06 |
| KR20170063583A (ko) | 2017-06-08 |
| EP3002302B1 (en) | 2018-02-28 |
| PL3002302T3 (pl) | 2018-07-31 |
| US10577463B2 (en) | 2020-03-03 |
| US20170198095A1 (en) | 2017-07-13 |
| WO2016050878A1 (en) | 2016-04-07 |
| CN106795268B (zh) | 2021-01-26 |
| JP6703529B2 (ja) | 2020-06-03 |
| BR112017002039B1 (pt) | 2022-04-26 |
| BR112017002039A2 (pt) | 2017-12-26 |
| CN106795268A (zh) | 2017-05-31 |
| JP2017537988A (ja) | 2017-12-21 |
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