WO2023100839A1 - 硬化性組成物、硬化物及びブロックイソシアネート化合物硬化用触媒 - Google Patents

硬化性組成物、硬化物及びブロックイソシアネート化合物硬化用触媒 Download PDF

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WO2023100839A1
WO2023100839A1 PCT/JP2022/043873 JP2022043873W WO2023100839A1 WO 2023100839 A1 WO2023100839 A1 WO 2023100839A1 JP 2022043873 W JP2022043873 W JP 2022043873W WO 2023100839 A1 WO2023100839 A1 WO 2023100839A1
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formula
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French (fr)
Japanese (ja)
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光貴 小野田
元嘉 宮城
将伍 永山
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Koei Chemical Co Ltd
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Koei Chemical Co Ltd
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Priority to KR1020247017040A priority Critical patent/KR20240112844A/ko
Priority to US18/714,360 priority patent/US20250034316A1/en
Priority to JP2023564985A priority patent/JPWO2023100839A1/ja
Priority to CN202280075734.9A priority patent/CN118234772A/zh
Publication of WO2023100839A1 publication Critical patent/WO2023100839A1/ja
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    • C07F11/00—Compounds containing elements of Groups 6 or 16 of the Periodic Table
    • C07F11/005—Compounds containing elements of Groups 6 or 16 of the Periodic Table compounds without a metal-carbon linkage
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/222—Catalysts containing metal compounds metal compounds not provided for in groups C08G18/225 - C08G18/26
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    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
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    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
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    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
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    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
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    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/28—Titanium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/095—Compounds containing the structure P(=O)-O-acyl, P(=O)-O-heteroatom, P(=O)-O-CN
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    • 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
    • C08G18/22—Catalysts containing metal compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • 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
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/285—Nitrogen containing compounds
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    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
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    • 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
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    • 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
    • C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
    • C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
    • C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
    • C08G18/6225—Polymers of esters of acrylic or methacrylic acid
    • C08G18/6229—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
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    • 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
    • C08G18/7806—Nitrogen containing -N-C=0 groups
    • C08G18/7818—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
    • C08G18/7831—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing biuret 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
    • C08G18/80—Masked polyisocyanates
    • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • 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
    • C08G18/80—Masked polyisocyanates
    • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
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    • 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

Definitions

  • R 8 and R 9 are the same or different and are a hydrocarbon group having 1 to 20 carbon atoms optionally having at least one selected from the group consisting of hetero atoms and halogen atoms, or -X 3 Re (R f ) a3 group
  • X 3 is an oxygen atom or a nitrogen atom
  • a3 is 0 or 1
  • a3 is 0 when X3 is an oxygen atom
  • a3 is 1 when X3 is a nitrogen atom
  • R e and R f are the same or different and represent a hydrocarbon group having 1 to 20 carbon atoms which may contain at least one selected from the group consisting of a hetero atom and a halogen atom).
  • R 10 O ⁇ (4) R 10 is a C 1-20 hydrocarbon group optionally having at least one selected from the group consisting of a hetero atom, a halogen atom, a hydroxy group and an oxyanion group (—O 2 — group).
  • the metal complex compounds are MoO2 (acac) 2 , MoO2 (DPh) 2 , MoO2 ( NEt2 ) 2 , MoO2 (DtBu) 2 , TiO(acac) 2 , Ti(acac) 2 (OiPr) 2 , Ti (OiPr) 4 , Ti(acac) 4 , (Ti(OiPr) 2 (OAc) 2 ) 2O , Ti(O2 (acac) 2 , MoO2 (DPh) 2 , MoO2 ( NEt2 ) 2 , MoO2 (DtBu) 2 , TiO(acac) 2 , Ti(acac) 2 (OiPr) 2 , Ti (OiPr) 4 , Ti(acac) 4 , (Ti(OiPr) 2 (OAc) 2 ) 2O , Ti(O
  • R e and R f are alkyl groups having 1 to 20 carbon atoms which may have at least one selected from the group consisting of heteroatoms and halogen atoms, heteroatoms and halogen atoms.
  • an aryl group having 6 to 20 carbon atoms which may have at least one selected from the group consisting of an aryl group having 7 to 20 carbon atoms which may have at least one selected from the group consisting of hetero atoms and halogen atoms is an aralkyl group, preferably an alkyl group having 1 to 10 carbon atoms which may have at least one selected from the group consisting of hetero atoms and halogen atoms, at least selected from the group consisting of hetero atoms and halogen atoms
  • alkyl group having 1 to 20 carbon atoms includes methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, Examples include heptyl group, octyl group, 2-ethylhexyl group and the like. Preferred are methyl group, ethyl group, isopropyl group and tert-butyl group.
  • pentyl group hexyl group, heptyl group, octyl group, nonyl group, decyl group, dodecyl group, octadecyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, phenyl group, naphthyl group, benzyl group, phenethyl group, tolyl group , an allyl group, and the like.
  • R 11 is an alkyl group having 1 to 20 carbon atoms optionally having at least one selected from the group consisting of a hetero atom and a halogen atom, or a hetero atom and a halogen atom.
  • an aryl group having 6 to 20 carbon atoms which may have at least one selected from the group consisting of an aryl group having 7 to 20 carbon atoms which may have at least one selected from the group consisting of hetero atoms and halogen atoms is an aralkyl group, preferably at least selected from the group consisting of an alkyl group having 1 to 10 carbon atoms or a hetero atom and a halogen atom which may have at least one selected from the group consisting of a hetero atom and a halogen atom
  • An aryl group having 6 to 10 carbon atoms which may have one species or an aralkyl group having 7 to 10 carbon atoms which may have at least one selected from the group consisting of hetero atoms and halogen atoms, more preferably has at least one selected from the group consisting of an alkyl group having 1 to 6 carbon atoms which may have at least one selected from the group consisting of a hetero atom and a halogen atom, or a
  • the hydrocarbon group contains at least one heteroatom such as an oxygen atom, a nitrogen atom, a sulfur atom
  • the hydrocarbon group is, for example, -O-, -N ⁇ , -NH-, -S-, -SO 2 -, etc., and the hydrocarbon chain may be interrupted by these groups.
  • an alkyl group having 1 to 10 carbon atoms which may have at least one selected from the group consisting of a hetero atom and a halogen atom, an alkyl group having 6 to 10 carbon atoms which may have a hetero atom or a halogen atom
  • It is an aryl group or an aralkyl group having 7 to 10 carbon atoms which may have a hetero atom or a halogen atom. More preferably, it has at least one selected from the group consisting of an alkyl group having 1 to 6 carbon atoms or a hetero atom and a halogen atom, which may have at least one selected from the group consisting of a hetero atom and a halogen atom.
  • Examples of the “aryl group having 6 to 20 carbon atoms” for R 13 and R 14 include a phenyl group, a naphthyl group and a tolyl group. A phenyl group and a tolyl group are preferred, and a phenyl group is more preferred.
  • reaction solution is concentrated, liquid-separated or filtered to remove the solvent, thereby obtaining the metal complex compound. Purification such as recrystallization or column separation may be performed as necessary. . Alternatively, the reaction liquid may be blended directly into the curable composition without removing the solvent.
  • a mono- to hexahydric alcohol compound can be used in combination.
  • the polyisocyanate having a biuret bond examples include biuret-modified 1,6-hexamethylene diisocyanate (HDI), biuret-modified isophorone diisocyanate (IPDI), and biuret-modified toluene diisocyanate (TDI) shown below.
  • Commercially available products include Desmodur N75, Desmodur N100, and Desmodur N3200 manufactured by Sumika Covestro Urethane Co., Ltd., and Duranate 24A-100, Duranate 22A-75P, and Duranate 21S-75E manufactured by Asahi Kasei Corporation. is mentioned.
  • R 1 , R 2 , R 3 and R 4 are the same or different and are hydrocarbon groups having 1 to 20 carbon atoms which may contain at least one selected from the group consisting of hetero atoms and halogen atoms, hydrogen atom, halogen atom, or -X 1 R a (R b ) a1 group
  • X 1 is an oxygen atom or a nitrogen atom
  • a1 is 0 or 1
  • R a and R b are the same or different and represent a hydrocarbon group having 1 to 20 carbon atoms which may contain a heteroatom or a halogen atom.
  • the "hydrocarbon group having 1 to 20 carbon atoms" for R a and R b includes methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, tert-butyl group, pentyl group and hexyl group. , heptyl group, octyl group, nonyl group, decyl group, dodecyl group, octadecyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, phenyl group, naphthyl group, benzyl group, phenethyl group, tolyl group, allyl group, etc.
  • the hydrocarbon group having 1 to 20 carbon atoms which may contain at least one selected from the group consisting of hetero atoms and halogen atoms in R c and R d contains a hetero atom
  • the hetero atom is an oxygen atom
  • Nitrogen atoms and sulfur atoms are mentioned, and the number of heteroatoms is preferably 1 to 5, more preferably 1 to 3, still more preferably 1 to 2.
  • the hydrocarbon group may contain one heteroatom, or may contain two or three heteroatoms.
  • the blocked isocyanate compound can be produced by reacting the isocyanate compound with the nitrogen-containing compound of formula (1) or formula (2) in the presence of a urethanization catalyst and solvent, if necessary.
  • reaction solution is concentrated or filtered to remove the solvent and the unreacted nitrogen-containing compound represented by formula (1) or (2), thereby obtaining a blocked isocyanate compound. Purification such as recrystallization or column fractionation may be carried out as required.
  • the curable composition of the present invention comprises one or more metal complex compounds containing at least one metal of Groups 4 to 13, and an isocyanate group of the isocyanate compound of formula (1) or (2) Contains a blocked isocyanate compound blocked by a nitrogen-containing compound represented by. Furthermore, it may contain a compound having an isocyanate-reactive group.
  • the dissociated nitrogen-containing compound represented by the formula (1) acts as an acid for an amine catalyst such as bis(2-dimethylaminoethyl) ether to form a salt, and the activity of the amine catalyst is presumably related to the decline.
  • an amine catalyst such as bis(2-dimethylaminoethyl) ether
  • the blocked isocyanate compound curing catalyst of the present invention does not form a salt with the dissociated nitrogen-containing compound represented by formula (1), it is considered that the catalytic activity does not decrease.
  • the blocked isocyanate compound curing catalyst of the present invention can be suitably used particularly in curing of the blocked isocyanate compound blocked by the nitrogen-containing compound represented by formula (1).
  • Polyether polyols include active hydrogen compounds such as aliphatic amine polyols, aromatic amine polyols, Mannich polyols, polyhydric alcohols, polyhydric phenols, and bisphenols, and compounds obtained by adding alkylene oxide thereto. These polyether polyols may be a mixture of two or more. Examples of aliphatic amine polyols include alkylenediamine-based polyols and alkanolamine-based polyols. These polyol compounds are polyfunctional polyol compounds with terminal hydroxyl groups obtained by ring-opening addition of at least one cyclic ether such as ethylene oxide or propylene oxide using alkylenediamine or alkanolamine as an initiator.
  • active hydrogen compounds such as aliphatic amine polyols, aromatic amine polyols, Mannich polyols, polyhydric alcohols, polyhydric phenols, and bisphenols, and compounds obtained by adding alkylene oxide thereto. These polyether polyo
  • Mannich polyol is an active hydrogen compound obtained by the Mannich reaction of phenol and/or its alkyl-substituted derivatives, formaldehyde and alkanolamine, or obtained by ring-opening addition polymerization of this compound with at least one of ethylene oxide and propylene oxide. It is a polyol compound. These Mannich polyols may be a mixture of two or more. Polyhydric alcohols include dihydric alcohols (eg, ethylene glycol, propylene glycol, 1,4-butanediol, 1,6-hexanediol, diethylene glycol, triethylene glycol, dipropylene glycol, neopentyl glycol, etc.) and trihydric alcohols.
  • dihydric alcohols eg, ethylene glycol, propylene glycol, 1,4-butanediol, 1,6-hexanediol, diethylene glycol, triethylene glycol, dipropylene glycol, neopen

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PCT/JP2022/043873 2021-11-30 2022-11-29 硬化性組成物、硬化物及びブロックイソシアネート化合物硬化用触媒 Ceased WO2023100839A1 (ja)

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KR1020247017040A KR20240112844A (ko) 2021-11-30 2022-11-29 경화성 조성물, 경화물 및 블록 이소시아네이트 화합물 경화용 촉매
US18/714,360 US20250034316A1 (en) 2021-11-30 2022-11-29 Curable composition, cured product and curing catalyst for blocked isocyanate compound
JP2023564985A JPWO2023100839A1 (https=) 2021-11-30 2022-11-29
CN202280075734.9A CN118234772A (zh) 2021-11-30 2022-11-29 固化性组合物、固化物和封端异氰酸酯化合物固化用催化剂

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115819723A (zh) * 2022-10-17 2023-03-21 浙江工业大学 一种封闭型异氰酸酯固化剂及其制备方法
CN121399218A (zh) * 2024-05-23 2026-01-23 日涂汽车涂料有限公司 阳离子电沉积涂料组合物和固化电沉积涂膜的形成方法
WO2026074800A1 (ja) * 2024-10-01 2026-04-09 東ソー株式会社 塗料組成物及び塗膜
WO2026074799A1 (ja) * 2024-10-01 2026-04-09 東ソー株式会社 水性塗料組成物及び塗膜

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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