WO2023190307A1 - ブタンジイソシアネート誘導体、ブタンジイソシアネート誘導体の製造方法、ポリイソシアネート組成物、ポリウレタン樹脂形成性組成物、塗料組成物及び塗膜 - Google Patents

ブタンジイソシアネート誘導体、ブタンジイソシアネート誘導体の製造方法、ポリイソシアネート組成物、ポリウレタン樹脂形成性組成物、塗料組成物及び塗膜 Download PDF

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Publication number
WO2023190307A1
WO2023190307A1 PCT/JP2023/012145 JP2023012145W WO2023190307A1 WO 2023190307 A1 WO2023190307 A1 WO 2023190307A1 JP 2023012145 W JP2023012145 W JP 2023012145W WO 2023190307 A1 WO2023190307 A1 WO 2023190307A1
Authority
WO
WIPO (PCT)
Prior art keywords
bdi
butane diisocyanate
isocyanurate
reaction
composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2023/012145
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
侑也 和田
雄次 中島
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Tosoh Corp
Original Assignee
Tosoh Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Tosoh Corp filed Critical Tosoh Corp
Priority to US18/850,805 priority Critical patent/US20250230134A1/en
Priority to CN202380029545.2A priority patent/CN118946552A/zh
Priority to JP2024512440A priority patent/JP7670233B2/ja
Priority to EP23780317.6A priority patent/EP4488266A4/en
Publication of WO2023190307A1 publication Critical patent/WO2023190307A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C07D251/30—Only oxygen atoms
    • C07D251/34—Cyanuric or isocyanuric esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D229/00—Heterocyclic compounds containing rings of less than five members having two nitrogen atoms as the only ring hetero 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
    • C08G18/08—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
    • C08G18/70—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
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
    • C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic 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
    • 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
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/798—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing urethdione groups
    • 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
    • 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
    • C08G18/62—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
    • 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
    • C08G2150/00—Compositions for coatings

Definitions

  • a BDI derivative is a mixture of multiple types of compounds derived from BDI monomers.
  • BDI derivatives include, for example, isocyanurate BDI and uretdione BDI.
  • the isocyanurate form of BDI is a compound having an isocyanurate group (a group formed by cyclopolymerization of three BDI monomer molecules) among compounds derived from BDI monomers.
  • the uretdione form of BDI is a compound having a uretdione group (a group formed by cyclization polymerization of two BDI monomer molecules) among compounds derived from BDI monomers.
  • the polyisocyanate composition may contain an organic solvent described below as another component, but the content of the organic solvent in the polyisocyanate composition is preferably 50% by mass or less, and 20% by mass or less. (substantially containing no organic solvent) is more preferable. The above content is based on the total mass of solids in the polyisocyanate composition.
  • the BDI derivative and polyisocyanate composition described above are suitably used as a curing agent component of a coating composition. That is, another embodiment of the present disclosure is a curing agent for paint containing the above-mentioned BDI derivative, and yet another embodiment of the present disclosure is a curing agent for paint comprising the above-mentioned polyisocyanate composition.
  • a curing agent for paint containing the above-mentioned BDI derivative
  • a curing agent for paint comprising the above-mentioned polyisocyanate composition.
  • isocyanate-reactive compounds polyols, etc.
  • the isocyanurate catalyst it is preferable to use an aminosilyl group-containing compound such as aminosilane or silyl urea from the viewpoint of suppressing the production of high molecular weight substances, and it is preferable to use disilazane such as hexamethyldisilazane or heptamethyldisilazane. More preferably, hexamethyldisilazane is used.
  • the isocyanurate reaction and the uretdione reaction may be performed in the absence of an organic solvent or in the presence of an organic solvent.
  • an organic solvent that does not affect the reaction and has a boiling point higher than the reaction temperature.
  • organic solvents include aliphatic hydrocarbons such as octane, alicyclic hydrocarbons such as cyclohexane and methylcyclohexane, ketones such as methyl isobutyl ketone and cyclohexanone, esters such as butyl acetate and isobutyl acetate, and ethylene glycol.
  • the heating conditions for the first heating step are the same as the preferred heating temperature range for the uretdiionization reaction described above, and the heating conditions for the second heating step are the same as the preferred range for the reaction temperature for the isocyanurate reaction described above. .
  • the uretdione-forming reaction may proceed simultaneously with the isocyanurate-forming reaction.
  • Examples of (meth)acrylic esters include alkyl esters having 1 to 20 carbon atoms. Examples of such (meth)acrylic esters include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, pentyl (meth)acrylate, and (meth)acrylate.
  • An olefin resin such as polyethylene or polypropylene that has been subjected to corona discharge treatment or other surface treatment, or an adherend on which a coating layer that can be formed as an intermediate layer is formed on the surface of the adherend can be used.
  • the curing conditions for the coating composition are not particularly limited, but preferably the curing temperature is -5 to 150°C, the humidity is 10 to 95% RH, and the curing time is 0.5 to 336 hours.

Landscapes

  • 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)
PCT/JP2023/012145 2022-03-31 2023-03-27 ブタンジイソシアネート誘導体、ブタンジイソシアネート誘導体の製造方法、ポリイソシアネート組成物、ポリウレタン樹脂形成性組成物、塗料組成物及び塗膜 Ceased WO2023190307A1 (ja)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US18/850,805 US20250230134A1 (en) 2022-03-31 2023-03-27 Butane diisocyanate derivative, method for producing butane diisocyanate derivative, polyisocyanate composition, polyurethane resin forming composition, coating composition and coating film
CN202380029545.2A CN118946552A (zh) 2022-03-31 2023-03-27 丁烷二异氰酸酯衍生物、丁烷二异氰酸酯衍生物的制造方法、多异氰酸酯组合物、聚氨酯树脂形成性组合物、涂料组合物及涂膜
JP2024512440A JP7670233B2 (ja) 2022-03-31 2023-03-27 ブタンジイソシアネート誘導体、ブタンジイソシアネート誘導体の製造方法、ポリイソシアネート組成物、ポリウレタン樹脂形成性組成物、塗料組成物及び塗膜
EP23780317.6A EP4488266A4 (en) 2022-03-31 2023-03-27 BUTANE DIISOCYANATE DERIVATIVE, PROCESS FOR PRODUCING A BUTANE DIISOCYANATE DERIVATIVE, POLYISOCYANATE COMPOSITION, POLYURETHANE RESIN FORMING COMPOSITION, COATING COMPOSITION AND COATING FILM

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2022058721 2022-03-31
JP2022-058721 2022-03-31

Publications (1)

Publication Number Publication Date
WO2023190307A1 true WO2023190307A1 (ja) 2023-10-05

Family

ID=88201707

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2023/012145 Ceased WO2023190307A1 (ja) 2022-03-31 2023-03-27 ブタンジイソシアネート誘導体、ブタンジイソシアネート誘導体の製造方法、ポリイソシアネート組成物、ポリウレタン樹脂形成性組成物、塗料組成物及び塗膜

Country Status (5)

Country Link
US (1) US20250230134A1 (https=)
EP (1) EP4488266A4 (https=)
JP (1) JP7670233B2 (https=)
CN (1) CN118946552A (https=)
WO (1) WO2023190307A1 (https=)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024202990A1 (ja) * 2023-03-31 2024-10-03 東ソー株式会社 ポリウレタン塗膜用表面平滑化剤、組成物、硬化剤、ポリウレタン樹脂形成性組成物、塗料組成物及び塗膜
WO2025204587A1 (ja) * 2024-03-27 2025-10-02 東ソー株式会社 ブタンジイソシアネート組成物、ポリイソシアネート組成物、ポリウレタン樹脂形成性組成物、塗料組成物及び塗膜
WO2025204589A1 (ja) * 2024-03-27 2025-10-02 東ソー株式会社 ブタンジイソシアネート組成物、ポリイソシアネート組成物、ポリウレタン樹脂形成性組成物、塗料組成物及び塗膜

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN119505173A (zh) * 2024-12-12 2025-02-25 万华化学集团股份有限公司 一种多异氰酸酯组合物、涂料组合物和应用

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04298522A (ja) * 1990-09-20 1992-10-22 Bayer Ag ポリイソシアネート混合物、その製造方法およびポリウレタン被覆組成物におけるその使用
JPH04305566A (ja) * 1990-10-19 1992-10-28 Bayer Ag ウレットジオン基及び／又はイソシアヌレート基を含有するポリイソシアネート並びにそれらの製造方法
JPH09132751A (ja) 1995-08-31 1997-05-20 Bayer Ag １，４−ジイソシアナトブタンから作成されたイソシアヌレート基含有ポリイソシアネートを含有する被覆組成物およびその使用
JPH09268212A (ja) * 1996-03-26 1997-10-14 Bayer Ag イミノオキサジアジンジオン基を含むイソシアネート三量体、その製造及び使用
JP2015127368A (ja) 2013-12-27 2015-07-09 旭化成ケミカルズ株式会社 ポリイソシアネート組成物、コーティング組成物、及び硬化物
JP2016053127A (ja) * 2014-09-04 2016-04-14 旭化成ケミカルズ株式会社 ポリイソシアネート組成物、塗料組成物及び塗膜

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DE10123416A1 (de) * 2001-05-14 2002-11-21 Bayer Ag Verfahren zur Herstellung von Polyisocyanaten

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04298522A (ja) * 1990-09-20 1992-10-22 Bayer Ag ポリイソシアネート混合物、その製造方法およびポリウレタン被覆組成物におけるその使用
JPH04305566A (ja) * 1990-10-19 1992-10-28 Bayer Ag ウレットジオン基及び／又はイソシアヌレート基を含有するポリイソシアネート並びにそれらの製造方法
JPH09132751A (ja) 1995-08-31 1997-05-20 Bayer Ag １，４−ジイソシアナトブタンから作成されたイソシアヌレート基含有ポリイソシアネートを含有する被覆組成物およびその使用
JPH09268212A (ja) * 1996-03-26 1997-10-14 Bayer Ag イミノオキサジアジンジオン基を含むイソシアネート三量体、その製造及び使用
JP2015127368A (ja) 2013-12-27 2015-07-09 旭化成ケミカルズ株式会社 ポリイソシアネート組成物、コーティング組成物、及び硬化物
JP2016053127A (ja) * 2014-09-04 2016-04-14 旭化成ケミカルズ株式会社 ポリイソシアネート組成物、塗料組成物及び塗膜

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Title
See also references of EP4488266A4

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024202990A1 (ja) * 2023-03-31 2024-10-03 東ソー株式会社 ポリウレタン塗膜用表面平滑化剤、組成物、硬化剤、ポリウレタン樹脂形成性組成物、塗料組成物及び塗膜
JP7613642B1 (ja) * 2023-03-31 2025-01-15 東ソー株式会社 ポリウレタン塗膜用表面平滑化剤、組成物、硬化剤、ポリウレタン樹脂形成性組成物、塗料組成物及び塗膜
WO2025204587A1 (ja) * 2024-03-27 2025-10-02 東ソー株式会社 ブタンジイソシアネート組成物、ポリイソシアネート組成物、ポリウレタン樹脂形成性組成物、塗料組成物及び塗膜
WO2025204589A1 (ja) * 2024-03-27 2025-10-02 東ソー株式会社 ブタンジイソシアネート組成物、ポリイソシアネート組成物、ポリウレタン樹脂形成性組成物、塗料組成物及び塗膜

Also Published As

Publication number Publication date
JP7670233B2 (ja) 2025-04-30
EP4488266A1 (en) 2025-01-08
US20250230134A1 (en) 2025-07-17
JPWO2023190307A1 (https=) 2023-10-05
CN118946552A (zh) 2024-11-12
EP4488266A4 (en) 2026-03-04

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