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WO2017195927A1 - Nouveau composé de type uréthane-acrylate à base de 2,4,6-triaminotriazine et procédé pour sa préparation - Google Patents

Nouveau composé de type uréthane-acrylate à base de 2,4,6-triaminotriazine et procédé pour sa préparation Download PDF

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Publication number
WO2017195927A1
WO2017195927A1 PCT/KR2016/005656 KR2016005656W WO2017195927A1 WO 2017195927 A1 WO2017195927 A1 WO 2017195927A1 KR 2016005656 W KR2016005656 W KR 2016005656W WO 2017195927 A1 WO2017195927 A1 WO 2017195927A1
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formula
triaminotriazine
urethane acrylate
novel
acrylate compound
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Ceased
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English (en)
Korean (ko)
Inventor
박형남
서순용
이종민
이환표
진귀숙
최원석
윤도우
최광식
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Aekyung Chemical Co Ltd
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Aekyung Chemical Co Ltd
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Publication of WO2017195927A1 publication Critical patent/WO2017195927A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/54—Three nitrogen atoms
    • 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
    • C08G18/3823—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups
    • C08G18/3831—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups containing urethane 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
    • C08G18/28—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
    • C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
    • C08G18/343—Polycarboxylic acids having at least three carboxylic acid groups
    • C08G18/346—Polycarboxylic acids having at least three carboxylic acid groups having four carboxylic acid 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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67—Unsaturated compounds having active hydrogen
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—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
    • 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
    • C08G18/81—Unsaturated isocyanates or isothiocyanates
    • 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
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/13—Morphological aspects

Definitions

  • the present invention relates to a novel 2,4,6-triaminotriazine-based urethane acrylate compound and a preparation method thereof, and more particularly to an isocyanate group (-NCO) in the mother nucleus of 2,4,6-triaminotriazine.
  • -NCO isocyanate group
  • the present invention relates to a novel 2,4,6-triaminotriazine-based urethane acrylate compound which is excellent in bending strength and can be used in photocuring compositions for high-resolution 3D printing.
  • photocuring resins are formed by applying a thin film to a surface of a material in various industries, including display substrates, ships, automobile exterior parts, construction materials, paper, wood, furniture, soundproof walls, optical materials, cosmetic containers, and the like. It is widely used as a coating agent to supplement the surface properties.
  • the photocurable resin is widely used as a 3D printer ink for forming a master model by printing three-dimensionally and photocuring with a 3D printer controlled based on three-dimensional CAD data, and research on this is actively conducted. It is becoming.
  • a photocurable resin which can print the master model by a 3D printer is a cured product of a composition comprising (i) 100 parts by weight of organopolysiloxane and ii) 0.01-5 parts by weight of a photoinitiator according to Korean Patent No. 10-0357785.
  • the organopolysiloxane (i) is (A) 30 to 100% by weight of the organopolysiloxane of the average composition formula (1); R a R 1 b SiO (4-ab) / 2 (1) wherein the same or different R is a substituted or unsubstituted monovalent hydrocarbon group without an aliphatic unsaturated bond or an alkoxy group; Same or different R1 is a photoreactor selected from (meth) acryloyl-containing groups, vinyloxyalkyl groups and epoxy-containing groups; Letters a and b are positive numbers satisfying 1.90 ⁇ a ⁇ 2.40, 0.0003 ⁇ b ⁇ 0.10 and 1.90 ⁇ a + b ⁇ 2.40, organopolysiloxane contains at least two photoreactive groups in the molecule and 100 to 1,000,000 at 25 ° C has a viscosity of cp and, and (B) R p R 1 q SiO 1/2 units (M), SiO 2 units (q
  • Korean Patent Laid-Open Publication No. 2003-0009435 which is a chemical composition for forming a three-dimensional object in a three-dimensional printer, wherein the component comprises a non-aqueous organic monomer compound, and the compound is an alcohol, an ester, an ether, a silane, a vinyl monomer, an acrylic monomer or a meta.
  • At least one of a acrylate monomer wherein the acrylic monomer comprises at least one of tri (propylene glycol) diacrylate, ethylene glycol phenyl ether acrylate or 1,6 hexanediol diacrylate, or wherein the methacryl monomer is At least one of 1,3 butylene glycol dimethacrylate, neopentyl glycol dimethacrylate, butyl methacrylate, 1,6 hexanediol dimethacrylate or di (propylene glycol) allyl ether methacrylate BACKGROUND OF THE INVENTION Photocuring compositions for three-dimensional printers are known.
  • Korean Patent Laid-Open Publication No. 10-2012-0055242 discloses 50 to 80 parts by weight of an acrylic compound, 10 to 50 parts by weight of silsesquioxane, 0.5 to 5 parts by weight of a photocurable release agent, and an ultraviolet initiator based on 100 parts by weight of a photocurable resin composition. 1 to 5 parts by weight, wherein the acrylic compound is selected from the group consisting of monofunctional monomers, difunctional monomers, trifunctional monomers, polyfunctional monomers, and mixtures thereof, wherein the silsesquioxane is acrylate or methacrylate Photocurable resin compositions are known which are selected from the group consisting of silsesquioxanes having groups and mixtures thereof.
  • the photocurable resin compositions have excellent heat resistance due to siloxane network bonds, but the hardness and bending strength are weak, so that copolymerization of other acrylic monomers to siloxane groups should be used to supplement physical properties.
  • Korean Patent Laid-Open No. 10-2012-0137258 is a photocurable inkjet ink having excellent wettability with respect to substrates such as an acrylic resin substrate, and is a photocurable inkjet ink capable of forming a surface-repellent cured film having excellent adhesion to a substrate.
  • An organic solvent (A), a bifunctional or less (meth) acrylate (B) having a hydroxy group, a urethane (meth) acrylate (C), a surfactant (D) and a photopolymerization initiator (E) are contained, and the urethane Photocurable inkjet inks in which (meth) acrylate (C) is represented by the formula (2) are known.
  • R1, R2 and R3 are each independently a divalent organic group having 1 to 20 carbon atoms
  • R4 and R5 are each independently hydrogen or alkyl having 1 to 6 carbon atoms
  • m and n are each independently Is an integer of 1 to 3.
  • Korean Patent Publication No. 10-2016-0045095 discloses a photocurable resin composition capable of forming a hard coat layer having improved blocking resistance and excellent printability without deteriorating transparency, and a hydroxyl group thereof.
  • Is 10-350 mgKOH / g, (meth) acrylic equivalent is 100-800 g / eq, weight average molecular weight is 10,000-200,000, glass transition point is 50-110 degreeC, and it has a photopolymerizable group and a hydroxyl group in a side chain.
  • the photocurable resin composition which contains the photopolymerizable polyfunctional compound (D) which has the above photopolymerizable group is known.
  • the photocurable compositions of the Korean Patent Publication No. 10-2012-0137258 and the Korean Patent Publication No. 10-2016-0045095 also copolymerize a photopolymerizable polyfunctional compound or use inorganic particles, so that the adhesiveness is excellent but heat resistance and hardness are insufficient. There was a problem.
  • Korean Patent No. 10-1569344 forms a film having excellent hardness and transparency at the same time, such as a liquid crystal display screen and a plasma display for displaying an electronic image in addition to general use such as the surface of window glass and glasses.
  • the photocurable triazine monomer compound represented by the above [Formula 1a] or [Formula 1b] is slightly improved in hardness than the conventional photocurable resin, the hardness is still not satisfactory for use as the photocurable composition for 3D printing, and heat resistance. , Lack of bending strength and tensile strength.
  • the present inventors urethane-react a methacrylate having an isocyanate group (-NCO) to the mother nucleus of 2,4,6-triaminotriazine, thereby obtaining a 2,4,6-triaminotriazine-based urethane acrylate backbone (back bone).
  • a methacrylate having an isocyanate group (-NCO)
  • the present invention is excellent in hardness, heat resistance and bending strength than the existing 2,4,6-triaminotriazine methacrylate, and 2,4,6- for use in photocurable compositions and photocurable coating compositions for high-resolution 3D printing
  • New 2,4,6 having 2,4,6-triaminotriazine-based urethane acrylate backbone structure by urethane reaction of methacrylate having isocyanate group (-NCO) to the nucleus of triaminotriazine It is a technical problem to provide a triamino triazine urethane acrylate compound.
  • the present invention provides a novel 2,4,6-triaminotriazine-based urethane acrylate compound represented by the following [Formula 1] as a technical solution.
  • R1, R2, R3, R4, R5 and R6 are the same or different alkyl groups of the same or different C1 ⁇ C3 or methacrylate having an isocyanate group (-OCN) at the terminal, wherein, R1, R2, At least three or more of R3, R4, R5 and R6 are methacrylates having an isocyanate group (-OCN) at the terminal.
  • the methacrylate having an isocyanate group (-OCN) at the terminal is 2-isocyanatoethyl methacrylate represented by the following [Formula 2] as a technical solution.
  • the novel 2,4,6-triaminotriazine-based urethane acrylate compound represented by the above [Formula 1] is a novel 2,4,6-triaminotriazine-based urethane acrylate compound represented by the following [Formula 3] This is a technical solution.
  • the novel 2,4,6-triaminotriazine-based urethane acrylate compound represented by the above [Formula 1] is a novel 2,4,6-triaminotriazine-based urethane acrylate compound represented by the following [Formula 4] This is a technical solution.
  • the present invention comprises the steps of homogeneously stirring the triazine-triethanol represented by the following [Formula 5] or triazine-hexaethanol represented by the [Formula 6] and the polymerization inhibitor and the reaction catalyst at room temperature; and the homogeneous 2-isocyanatoethyl methacrylate was added dropwise to the stirred mixture to increase the temperature and dropping at 50-70 ° C .; and checking the NCO with FT-IR and reacting when there was no -OH group.
  • a method for producing a novel 2,4,6-triaminotriazine-based urethane acrylate compound comprising the step of terminating;
  • novel 2,4,6-triaminotriazine-based urethane acrylate compound of the present invention is urethane-reacted with 2-isocyanatoethyl methacrylate to the mother nucleus of 2,4,6-triaminotriazine.
  • 6-triaminotriazine-based urethane acrylate backbone (back bone) structure higher hardness, heat resistance, bending strength, tensile strength than conventional 2,4,6-triaminotriazine methacrylate, high resolution 3D printing
  • Figure 4 is an optical microscope and SEM comparison picture showing the print resolution of the 2,4,6-triaminotriazine-based urethane acrylate of the present invention
  • the present invention is characterized by a novel 2,4,6-triaminotriazine-based urethane acrylate compound represented by the following [Formula 1].
  • R1, R2, R3, R4, R5 and R6 are the same or different alkyl groups of the same or different C1 ⁇ C3 or methacrylate having an isocyanate group (-OCN) at the terminal, wherein, R1, R2, At least three or more of R3, R4, R5 and R6 are methacrylates having an isocyanate group (-OCN) at the terminal.
  • the methacrylate which has an isocyanate group (-OCN) at the said terminal is characterized by the technical structure of 2-isocyanatoethyl methacrylate represented by following [Formula 2].
  • the novel 2,4,6-triaminotriazine-based urethane acrylate compound represented by the above [Formula 1] is a novel 2,4,6-triaminotriazine-based urethane acrylate compound represented by the following [Formula 3] It is characterized by the technical configuration.
  • the novel 2,4,6-triaminotriazine-based urethane acrylate compound represented by the above [Formula 1] is a novel 2,4,6-triaminotriazine-based urethane acrylate compound represented by the following [Formula 4] It is characterized by the technical configuration.
  • the present invention comprises the steps of homogeneously stirring the triazine-triethanol represented by the following [Formula 5] or triazine-hexaethanol represented by the [Formula 6] and the polymerization inhibitor and the reaction catalyst at room temperature; and the homogeneous 2-isocyanatoethyl methacrylate was added dropwise to the stirred mixture to increase the temperature and dropping at 50-70 ° C .; and checking the NCO with FT-IR and reacting when there was no -OH group. Terminating step; characterized in that the manufacturing method of the novel 2,4,6-triaminotriazine-based urethane acrylate compound comprising a technical configuration.
  • the novel 2,4,6-triaminotriazine-based urethane acrylate compound of the present invention is a urethane methacrylate having an isocyanate group (-OCN) at its terminal in the mother nucleus of 2,4,6-triaminotriazine.
  • the reaction is synthesized to have a 2,4,6-triaminotriazine-based urethane acrylate backbone structure.
  • methacrylic acid 2- (O- [1'-methylpropylideneamino] carboxyamino) ethyl, 2-[(3,5-dimethylpyrazolyl) carbonylamino] ethyl methacrylate, etc. are mentioned. .
  • 2-isocyanatoethyl methacrylate represented by [Formula 2] is preferable.
  • the compound having a mother nucleus of 2,4,6-triaminotriazine which is urethane-reacted with 2-isocyanatoethyl methacrylate represented by the above [Formula 2] is a triazine represented by the following [Formula 5] -Triethanol or triazine-hexaethanol represented by [Formula 6].
  • the triazine-triethanol represented by the above [Formula 5] was added with cyanuric chloride, acetone and potassium carbonate under a nitrogen atmosphere, followed by stirring. Then, 2- (methylamino) ethanol was slowly added to the mixture and stirred for 48 hours at 60 ° C. After refluxing, cooling may be carried out at room temperature, filtration and distillation under reduced pressure, and solvent removal.
  • the synthesis process is as follows.
  • Korean Patent No. 10-1569344 has a pencil hardness of 5H ⁇ 6H by reacting triazine-triethanol represented by [Formula 5] or triazine-hexaethanol represented by [Formula 6] with methacrylic anhydride 2,4,6-triaminotriazine methacrylate used in the photocurable coating composition is prepared as follows, and the synthesis process thereof is shown in [Scheme 3] and [Scheme 4].
  • the 2,4,6-triaminotriazine methacrylate compound is a 3D print by introducing methacrylate by reacting methacrylate anhydride to -OH of triazine-triethanol or triazine-hexaethanol.
  • methacrylate anhydride to reacting methacrylate anhydride to -OH of triazine-triethanol or triazine-hexaethanol.
  • the present invention has been studied to improve the above-mentioned shortcomings, as a result of urethane reaction of -NCO of 2-isocyanatoethyl methacrylate to -OH of the triazine-triethanol or triazine-hexaethanol to heat resistance, hardness, bending
  • the novel 2,4,6-triaminotriazine-based urethane acrylate compound represented by [Formula 3] or [Formula 4] having excellent strength and tensile strength was synthesized, and the synthesis process was described in [Scheme 5] and It is the same as [Scheme 6].
  • the novel 2,4,6-triaminotriazine-based urethane acrylate compound is prohibited from polymerization with triazine-triethanol represented by [Formula 5] or triazine-hexaethanol represented by [Formula 6] under a nitrogen atmosphere. And homogeneously stirring the agent and the reaction catalyst at room temperature; and dropping 2-isocyanatoethyl methacrylate dropwise to the homogeneously stirred mixture to drop the reaction at 50 to 70 ° C.
  • the mixture may be prepared by a manufacturing method including a; checking NCO with FT-IR and terminating the reaction when there is no -OH group.
  • hydroquinone monomethyl ether is used as the polymerization inhibitor, and as the reaction catalyst, for example, dibutyl tin dilaurate, dioctyl tin laurate, dioctyl tin dilaurate, and tri Phenylphosphine, bismuth type catalyst, etc. can be used, A dibutyl tin dilaurate (DIBUTYLTIN DILAURATE) is preferred.
  • the final structure of the synthesized 2,4,6-triaminotriazine-based urethane acrylate compound is 2,4,6-triamino via 13 C-NMR of [FIG. 1] and 1 H-NMR of [FIG. 2] It was confirmed that triazine-based trifunctional urethane acrylate group was formed.
  • the 2,4,6-triaminotriazine-based urethane acrylate compound (TU) of the present invention is a conventional 2,4,6-triaminotriazine trimethacrylate (TA) Compared with the hardness, the hardness, heat resistance and bending strength is significantly improved, it can be seen that excellent properties.
  • the resolution of the 2,4,6-triaminotriazine-based urethane acrylate compound (TU) of the present invention can be confirmed that the excellent 22 ⁇ m horizontal, zirconia surface
  • the organic-inorganic hybridization (20 Wt% content) and dispersion control (30 nm possible) can be applied to the light-curing 3D ink with improved light scattering and dispersibility.
  • the inorganic inorganic hybridization and dispersion control within 45 ⁇ m showed a stable improvement effect, and as a result of evaluation of the influence of the monomer functional group, in the case of the compound (TU) of the present invention, the print resolution is improved in the printing top portion The results could be confirmed.
  • the surface roughness of the 2,4,6-triaminotriazine-based urethane acrylate compound (TU) of the present invention is zirconia-MPTMS synthesis through the compound alone (TU)) and zirconia surface treatment as shown in FIG. All of the inks were improved in dispersibility and shelf life to confirm the surface roughness of 20 ⁇ m or less.
  • novel 2,4,6-triaminotriazine-based urethane acrylate compound of the present invention is urethane-reacted with 2-isocyanatoethyl methacrylate to the mother nucleus of 2,4,6-triaminotriazine.
  • 6-triaminotriazine-based urethane acrylate backbone (back bone) structure higher hardness, heat resistance, bending strength, tensile strength than conventional 2,4,6-triaminotriazine methacrylate, high resolution 3D printing Since there is an excellent effect that can be usefully used in a photocurable composition or a photocurable coating composition for the industrial application.

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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)
  • Polyurethanes Or Polyureas (AREA)

Abstract

La présente invention concerne un nouveau composé de type uréthane-acrylate à base de 2,4,6-triaminotriazine et un procédé pour sa préparation et, plus particulièrement, un nouveau composé de type uréthane-acrylate à base de 2,4,6-triaminotriazine présentant une dureté, une résistance à la chaleur et une résistance à la flexion supérieures à celles d'un méthacrylate de 2,4,6-triaminotriazine conventionnel, et utilisable dans une composition durcissable par rayonnement pour une impression 3D haute définition par le fait de présenter une structure de chaîne principale d'uréthane-acrylate à base de 2,4,6-triaminotriazine obtenue à partir d'une réaction d'uréthane de méthacrylate, présentant un groupe isocyanate (-NCO), avec un noyau mère de 2,4,6-triaminotriazine.
PCT/KR2016/005656 2016-05-13 2016-05-27 Nouveau composé de type uréthane-acrylate à base de 2,4,6-triaminotriazine et procédé pour sa préparation Ceased WO2017195927A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020160058958A KR101790579B1 (ko) 2016-05-13 2016-05-13 신규한 2,4,6-트리아미노트리아진계 우레탄아크릴레이트 화합물 및 그 제조방법
KR10-2016-0058958 2016-05-13

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109694460A (zh) * 2018-12-11 2019-04-30 万华化学集团股份有限公司 多官能度不饱和异氰酸酯三聚体及其制备和在分散体稳定剂中的应用
CN110872372A (zh) * 2019-11-29 2020-03-10 鞍山润德精细化工有限公司 含三嗪环的六官能团丙烯酸聚氨酯及其制备方法和应用
CN115093541A (zh) * 2022-07-21 2022-09-23 马鞍山寅丰新材料科技有限公司 基于聚氨酯弹性体的体育场地铺装材料及其制备方法

Citations (5)

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