JP7391031B2 - 2成分ポリウレタン接着剤組成物 - Google Patents
2成分ポリウレタン接着剤組成物 Download PDFInfo
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- JP7391031B2 JP7391031B2 JP2020551586A JP2020551586A JP7391031B2 JP 7391031 B2 JP7391031 B2 JP 7391031B2 JP 2020551586 A JP2020551586 A JP 2020551586A JP 2020551586 A JP2020551586 A JP 2020551586A JP 7391031 B2 JP7391031 B2 JP 7391031B2
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- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- HGQSXVKHVMGQRG-UHFFFAOYSA-N dioctyltin Chemical compound CCCCCCCC[Sn]CCCCCCCC HGQSXVKHVMGQRG-UHFFFAOYSA-N 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000002296 dynamic light scattering Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000010881 fly ash Substances 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000012978 lignocellulosic material Substances 0.000 description 1
- 238000003754 machining Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 239000002923 metal particle Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012764 mineral filler Substances 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- KPADFPAILITQBG-UHFFFAOYSA-N non-4-ene Chemical compound CCCCC=CCCC KPADFPAILITQBG-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920005629 polypropylene homopolymer Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000002990 reinforced plastic Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 238000012956 testing procedure Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004634 thermosetting polymer Substances 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000010457 zeolite Substances 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
- 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
- C08G18/797—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing carbodiimide and/or uretone-imine groups
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
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- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B37/00—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
- B32B37/12—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives
-
- B—PERFORMING OPERATIONS; TRANSPORTING
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- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
- B32B7/04—Interconnection of layers
- B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
-
- 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
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation 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
- C08G18/28—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
- C08G18/4825—Polyethers containing two hydroxy 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
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4833—Polyethers containing oxyethylene units
- C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
- C08G18/4841—Polyethers containing oxyethylene units and other oxyalkylene units containing oxyethylene end 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
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4833—Polyethers containing oxyethylene units
- C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
- C08G18/4845—Polyethers containing oxyethylene units and other oxyalkylene units containing oxypropylene or higher oxyalkylene end 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
- C08G18/40—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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
-
- 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
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing 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
- C08G18/28—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
- C08G18/69—Polymers of conjugated dienes
-
- 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
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7628—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group
- C08G18/7642—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group containing at least two isocyanate or isothiocyanate groups linked to the aromatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate groups, e.g. xylylene diisocyanate or homologues substituted on the aromatic ring
-
- 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
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B37/00—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
- B32B37/12—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives
- B32B2037/1269—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives multi-component adhesive
Description
(a)ポリイソシアネートを含む1種以上のイソシアネート化合物と、ポリ(ブチレンオキシド)ポリオール、ポリブタジエンポリオール、アクリルポリオール、及びそれらの混合物からなる群から選択される1種以上の疎水性ポリオールを含む1種以上のイソシアネート反応性成分と、の反応生成物であるプレポリマーを含むイソシアネート成分であって、1種以上の疎水性ポリオールが1.6~3.5の官能基数及び500g/mol~10,000g/molの数平均分子量を有するイソシアネート成分;及び
(b)1種以上のポリオール鎖延長剤;
を含有し、少なくとも10重量%の疎水性含有量を有する、2成分ポリウレタン接着剤組成物が提供される。
(a)(i)ポリイソシアネートを含む1種以上のイソシアネート化合物と、ポリ(ブチレンオキシド)ポリオール、ポリブタジエンポリオール、アクリルポリオール、及びそれらの混合物からなる群から選択される1種以上の疎水性ポリオールを含む1種以上のイソシアネート反応性成分と、の反応生成物であるプレポリマーを含むイソシアネート成分であって、疎水性ポリオールが1.6~3.5の官能基数及び500g/mol~10,000g/molの数平均分子量を有するイソシアネート成分;及び(ii)1種以上のポリオール鎖延長剤;を含有し、
少なくとも10重量%の疎水性含有量を有する2成分ポリウレタン接着剤組成物を、第1の基材の少なくとも一部に塗布すること;
(b)第2の基材を前記第1の基材と接触させること;並びに
(c)2成分ポリウレタン接着剤組成物を硬化させて、第1の基材と第2の基材との間に接着剤結合を形成すること;
を含む。
硬化した接着剤(50%±5%の相対湿度で23℃±2℃)組成物のヤング率、引張強さ、及び破断点伸びは、ASTM D638に従って測定した。
「ISO1」から「ISO10」として表されるイソシアネート成分についての以下の原料及び量は、下の表1に示される。列挙されている全ての量は、重量パーセントによる。
比較例A~Hのポリウレタン接着剤組成物は、スタティックミキサーを備えた2成分空気圧縮塗布ガンを使用して、1:1の体積混合比で表1及び2に列挙されている配合物(すなわち成分(a)及び(b))をブレンドすることによって調製する。配合物をそれらの物理的特性及び接着性能と共に下の表3に示す。比較例AはBETA-SEALTM 1Kポリウレタン接着剤組成物である。
実施例1~6のポリウレタン接着剤組成物は、スタティックミキサーを備えた2成分空気圧縮塗布ガンを使用して、1:1の体積混合比で表1及び2に列挙されている配合物(すなわち成分(a)及び(b))をブレンドすることによって調製する。配合物をそれらの物理的特性及び接着性能と共に下の表4に示す。
本願発明には以下の態様が含まれる。
項1.
(a)ポリイソシアネートを含む1種以上のイソシアネート化合物と、ポリ(ブチレンオキシド)ポリオール、ポリブタジエンポリオール、アクリルポリオール、及びそれらの混合物からなる群から選択される1種以上の疎水性ポリオールを含む1種以上のイソシアネート反応性化合物と、の反応生成物であるプレポリマーを含むイソシアネート成分であって、前記1種以上の疎水性ポリオールが1.6~3.5の官能基数及び500g/mol~10,000g/molの数平均分子量を有する、イソシアネート成分;及び
(b)1種以上のポリオール鎖延長剤成分;
を含有し、少なくとも10重量%の疎水性含有量を有する、2成分ポリウレタン接着剤組成物。
項2.
前記プレポリマーが、前記プレポリマーの1重量%~20重量%の遊離イソシアネート含有量を有する、項1に記載の2成分ポリウレタン接着剤組成物。
項3.
前記ポリイソシアネートが、モノメリックジフェニルメタンジイソシアネート、ポリカルボジイミド変性ジフェニルメタンジイソシアネート、ポリメリックジフェニルメタンジイソシアネート、キシレンジイソシアネート、又はそれらの組み合わせである、項1に記載の2成分ポリウレタン接着剤組成物。
項4.
前記1種以上の疎水性ポリオールが1.6~3.5の官能基数を有するポリ(ブチレンオキシド)ポリオールを含む、項1に記載の2成分ポリウレタン接着剤組成物。
項5.
前記1種以上の疎水性ポリオールが、800g/mol~3,000g/molの数平均分子量を有するポリ(ブチレンオキシド)ポリオールと、1,000g/mol~10,000g/molの数平均分子量を有するアクリルポリオールとを含む、項1に記載の2成分ポリウレタン接着剤組成物。
項6.
前記1種以上のイソシアネート反応性化合物が、20重量%未満のエチレンオキシド含有量、2~6の公称ヒドロキシル官能基数、及び1,000g/mol超6,000g/molまでの数平均分子量を有する1種以上のポリオキシプロピレン-ポリオキシエチレンポリエーテルポリオールを更に含む、項1に記載の2成分ポリウレタン接着剤組成物。
項7.
前記1種以上のイソシアネート反応性化合物が、800g/mol~3,000g/molの数平均分子量を有するポリ(ブチレンオキシド)ポリオールと、20重量%未満のエチレンオキシド含有量、2~6の公称ヒドロキシル官能基数、及び1,000g/mol超6,000g/molまでの数平均分子量を有するポリオキシプロピレン-ポリオキシエチレンポリエーテルポリオールとを含む、項1に記載の2成分ポリウレタン接着剤組成物。
項8.
前記1種以上のイソシアネート反応性化合物が、1,000g/mol~10,000g/molの数平均分子量を有するアクリルポリオールと、20重量%未満のエチレンオキシド含有量、2~6の公称ヒドロキシル官能基数、及び1,000g/mol超6,000g/molまでの数平均分子量を有するポリオキシプロピレン-ポリオキシエチレンポリエーテルポリオールとを含む、項1に記載の2成分ポリウレタン接着剤組成物。
項9.
前記1種以上のポリオール鎖延長剤成分が脂肪族ジオールを含む、項1に記載の2成分ポリウレタン接着剤組成物。
項10.
前記脂肪族ジオールが、200以下のヒドロキシル当量及び1分子あたり2つの脂肪族ヒドロキシル基を有する、項9に記載の2成分ポリウレタン接着剤組成物。
項11.
前記1種以上のポリオール鎖延長剤成分が、800g/mol~3,000g/molの数平均分子量を有するポリ(ブチレンオキシド)ポリオール、800g/mol~3,000g/molの数平均分子量を有するポリブタジエンポリオール、及び20重量%未満のエチレンオキシド含有量と、2~6の公称ヒドロキシル官能基数と、1,000g/mol超6000g/molまでの数平均分子量とを有するポリオキシプロピレン-ポリオキシエチレンポリエーテルポリオール、のうちの1種以上を更に含む、項9に記載の2成分ポリウレタン接着剤組成物。
項12.
前記イソシアネート成分(a)及び1種以上のポリオール鎖延長剤成分(b)が、1種以上の潜在性室温有機金属触媒、1種以上の粒子状充填剤、1種以上の可塑剤、及びそれらの組み合わせを更に含む、項1に記載の2成分ポリウレタン接着剤組成物。
項13.
10~80重量%の疎水性含有量を有する、項1に記載の2成分ポリウレタン接着剤組成物。
項14.
(a)
(i)ポリイソシアネートを含む1種以上のイソシアネート化合物と、ポリ(ブチレンオキシド)ポリオール、ポリブタジエンポリオール、アクリルポリオール、及びそれらの混合物からなる群から選択される1種以上の疎水性ポリオールを含む1種以上のイソシアネート反応性化合物と、の反応生成物であるプレポリマーを含むイソシアネート成分であって、前記1種以上の疎水性ポリオールが1.6~3.5の官能基数及び500g/mol~10,000g/molの数平均分子量を有する、イソシアネート成分;及び
(ii)1種以上のポリオール鎖延長剤成分;を含有し、
少なくとも10重量%の疎水性含有量を有する2成分ポリウレタン接着剤組成物を、第1の基材の少なくとも一部に塗布すること;
(b)第2の基材を前記第1の基材と接触させること;並びに
(c)前記2成分ポリウレタン接着剤組成物を硬化させて、前記第1の基材と第2の基材との間に接着剤結合を形成すること;
を含む方法。
項15.
前記1種以上のイソシアネート反応性化合物が、800g/mol~3,000g/molの数平均分子量を有するポリ(ブチレンオキシド)ポリオールと、20重量%未満のエチレンオキシド含有量、2~6の公称ヒドロキシル官能基数、及び1,000g/mol超6,000g/molまでの数平均分子量を有するポリオキシプロピレン-ポリオキシエチレンポリエーテルポリオールとを含む、項14に記載の方法。
項16.
前記1種以上のイソシアネート反応性化合物が、1,000g/mol~10,000g/molの数平均分子量を有するアクリルポリオールと、20重量%未満のエチレンオキシド含有量、2~6の公称ヒドロキシル官能基数、及び1,000g/mol超6,000g/molまでの数平均分子量を有するポリオキシプロピレン-ポリオキシエチレンポリエーテルポリオールとを含む、項14に記載の方法。
項17.
前記1種以上のポリオール鎖延長剤成分が脂肪族ジオールを含む、項14に記載の方法。
項18.
前記1種以上のポリオール鎖延長剤成分が、800g/mol~3,000g/molの数平均分子量を有するポリ(ブチレンオキシド)ポリオール、800g/mol~3,000g/molの数平均分子量を有するポリブタジエンポリオール、及び20重量%未満のエチレンオキシド含有量と、2~6の公称ヒドロキシル官能基数と、1,000g/mol超6,000g/molまでの数平均分子量とを有するポリオキシプロピレン-ポリオキシエチレンポリエーテルポリオール、のうちの1種以上を更に含む、項17に記載の方法。
項19.
前記第1の基材と前記第2の基材がポリプロピレン基材である、項14に記載の方法。
項20.
前記ポリプロピレン基材が火炎処理されたポリプロピレン基材である、項19に記載の方法。
Claims (21)
- (a)ポリイソシアネートを含む1種以上のイソシアネート化合物と、ポリ(ブチレンオキシド)ポリオール、ポリブタジエンポリオール、アクリルポリオール、及びそれらの混合物からなる群から選択される1種以上の疎水性ポリオールを含む1種以上のイソシアネート反応性化合物と、の反応生成物であるプレポリマーを含むイソシアネート成分であって、前記1種以上の疎水性ポリオールが1.6~3.5の官能基数及び500g/mol~10,000g/molの数平均分子量を有する、イソシアネート成分;及び
(b)1種以上のポリオール鎖延長剤成分;
を含有し、少なくとも10重量%の疎水性含有量を有する、2成分ポリウレタン接着剤組成物であり、
前記1種以上の疎水性ポリオールがアクリルポリオールを含む、2成分ポリウレタン接着剤組成物。 - 前記プレポリマーが、前記プレポリマーの1重量%~20重量%の遊離イソシアネート含有量を有する、請求項1に記載の2成分ポリウレタン接着剤組成物。
- 前記ポリイソシアネートが、モノメリックジフェニルメタンジイソシアネート、ポリカルボジイミド変性ジフェニルメタンジイソシアネート、ポリメリックジフェニルメタンジイソシアネート、キシレンジイソシアネート、又はそれらの組み合わせである、請求項1に記載の2成分ポリウレタン接着剤組成物。
- 前記1種以上の疎水性ポリオールが1.6~3.5の官能基数を有するポリ(ブチレンオキシド)ポリオールを含む、請求項1に記載の2成分ポリウレタン接着剤組成物。
- 前記1種以上の疎水性ポリオールが、800g/mol~3,000g/molの数平均分子量を有するポリ(ブチレンオキシド)ポリオールと、1,000g/mol~10,000g/molの数平均分子量を有するアクリルポリオールとを含む、請求項1に記載の2成分ポリウレタン接着剤組成物。
- 前記1種以上のイソシアネート反応性化合物が、20重量%未満のエチレンオキシド含有量、2~6の公称ヒドロキシル官能基数、及び1,000g/mol超6,000g/molまでの数平均分子量を有する1種以上のポリオキシプロピレン-ポリオキシエチレンポリエーテルポリオールを更に含む、請求項1に記載の2成分ポリウレタン接着剤組成物。
- 前記1種以上のイソシアネート反応性化合物が、800g/mol~3,000g/molの数平均分子量を有するポリ(ブチレンオキシド)ポリオールと、20重量%未満のエチレンオキシド含有量、2~6の公称ヒドロキシル官能基数、及び1,000g/mol超6,000g/molまでの数平均分子量を有するポリオキシプロピレン-ポリオキシエチレンポリエーテルポリオールとを含む、請求項1に記載の2成分ポリウレタン接着剤組成物。
- 前記1種以上のイソシアネート反応性化合物が、1,000g/mol~10,000g/molの数平均分子量を有するアクリルポリオールと、20重量%未満のエチレンオキシド含有量、2~6の公称ヒドロキシル官能基数、及び1,000g/mol超6,000g/molまでの数平均分子量を有するポリオキシプロピレン-ポリオキシエチレンポリエーテルポリオールとを含む、請求項1に記載の2成分ポリウレタン接着剤組成物。
- 前記1種以上のポリオール鎖延長剤成分が脂肪族ジオールを含む、請求項1に記載の2成分ポリウレタン接着剤組成物。
- 前記脂肪族ジオールが、200以下のヒドロキシル当量及び1分子あたり2つの脂肪族ヒドロキシル基を有する、請求項9に記載の2成分ポリウレタン接着剤組成物。
- 前記1種以上のポリオール鎖延長剤成分(b)が、800g/mol~3,000g/molの数平均分子量を有するポリ(ブチレンオキシド)ポリオール、800g/mol~3,000g/molの数平均分子量を有するポリブタジエンポリオール、及び20重量%未満のエチレンオキシド含有量と、2~6の公称ヒドロキシル官能基数と、1,000g/mol超6,000g/molまでの数平均分子量とを有するポリオキシプロピレン-ポリオキシエチレンポリエーテルポリオール、のうちの1種以上を更に含む、請求項9に記載の2成分ポリウレタン接着剤組成物。
- 前記イソシアネート成分(a)及び1種以上のポリオール鎖延長剤成分(b)が、1種以上の潜在性室温有機金属触媒、1種以上の粒子状充填剤、1種以上の可塑剤、及びそれらの組み合わせを更に含む、請求項1に記載の2成分ポリウレタン接着剤組成物。
- 10~80重量%の疎水性含有量を有する、請求項1に記載の2成分ポリウレタン接着剤組成物。
- (i)
(a)ポリイソシアネートを含む1種以上のイソシアネート化合物と、ポリ(ブチレンオキシド)ポリオール、ポリブタジエンポリオール、アクリルポリオール、及びそれらの混合物からなる群から選択される1種以上の疎水性ポリオールを含む1種以上のイソシアネート反応性化合物と、の反応生成物であるプレポリマーを含むイソシアネート成分であって、前記1種以上の疎水性ポリオールが1.6~3.5の官能基数及び500g/mol~10,000g/molの数平均分子量を有する、イソシアネート成分;及び
(b)1種以上のポリオール鎖延長剤成分;を含有し、
少なくとも10重量%の疎水性含有量を有する2成分ポリウレタン接着剤組成物であり、前記1種以上の疎水性ポリオールがアクリルポリオールを含む2成分ポリウレタン接着剤組成物を、第1の基材の少なくとも一部に塗布すること;
(ii)第2の基材を前記第1の基材と接触させること;並びに
(iii)前記2成分ポリウレタン接着剤組成物を硬化させて、前記第1の基材と第2の基材との間に接着剤結合を形成すること;
を含む方法。 - 前記1種以上の疎水性ポリオールが、800g/mol~3,000g/molの数平均分子量を有するポリ(ブチレンオキシド)ポリオールと、1,000g/mol~10,000g/molの数平均分子量を有するアクリルポリオールとを含む、請求項14に記載の方法。
- 前記1種以上のイソシアネート反応性化合物が、800g/mol~3,000g/molの数平均分子量を有するポリ(ブチレンオキシド)ポリオールと、20重量%未満のエチレンオキシド含有量、2~6の公称ヒドロキシル官能基数、及び1,000g/mol超6,000g/molまでの数平均分子量を有するポリオキシプロピレン-ポリオキシエチレンポリエーテルポリオールとを含む、請求項14に記載の方法。
- 前記1種以上のイソシアネート反応性化合物が、1,000g/mol~10,000g/molの数平均分子量を有するアクリルポリオールと、20重量%未満のエチレンオキシド含有量、2~6の公称ヒドロキシル官能基数、及び1,000g/mol超6,000g/molまでの数平均分子量を有するポリオキシプロピレン-ポリオキシエチレンポリエーテルポリオールとを含む、請求項14に記載の方法。
- 前記1種以上のポリオール鎖延長剤成分(b)が脂肪族ジオールを含む、請求項14に記載の方法。
- 前記1種以上のポリオール鎖延長剤成分(b)が、800g/mol~3,000g/molの数平均分子量を有するポリ(ブチレンオキシド)ポリオール、800g/mol~3,000g/molの数平均分子量を有するポリブタジエンポリオール、及び20重量%未満のエチレンオキシド含有量と、2~6の公称ヒドロキシル官能基数と、1,000g/mol超6,000g/molまでの数平均分子量とを有するポリオキシプロピレン-ポリオキシエチレンポリエーテルポリオール、のうちの1種以上を更に含む、請求項18に記載の方法。
- 前記第1の基材と前記第2の基材がポリプロピレン基材である、請求項14に記載の方法。
- 前記ポリプロピレン基材が火炎処理されたポリプロピレン基材である、請求項20に記載の方法。
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EP3774970A1 (en) | 2021-02-17 |
CN112236461A (zh) | 2021-01-15 |
KR20200140840A (ko) | 2020-12-16 |
WO2019195045A1 (en) | 2019-10-10 |
US20210024795A1 (en) | 2021-01-28 |
CN112236461B (zh) | 2022-08-02 |
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