JP6748732B2 - 2成分無溶剤接着剤組成物及びそれらを作製する方法 - Google Patents
2成分無溶剤接着剤組成物及びそれらを作製する方法 Download PDFInfo
- Publication number
- JP6748732B2 JP6748732B2 JP2018550684A JP2018550684A JP6748732B2 JP 6748732 B2 JP6748732 B2 JP 6748732B2 JP 2018550684 A JP2018550684 A JP 2018550684A JP 2018550684 A JP2018550684 A JP 2018550684A JP 6748732 B2 JP6748732 B2 JP 6748732B2
- Authority
- JP
- Japan
- Prior art keywords
- component
- weight
- isocyanate
- polyol
- branched
- 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.)
- Active
Links
- 239000000203 mixture Substances 0.000 title claims description 63
- 239000000853 adhesive Substances 0.000 title claims description 47
- 230000001070 adhesive effect Effects 0.000 title claims description 47
- 238000000034 method Methods 0.000 title claims description 22
- 229920005862 polyol Polymers 0.000 claims description 68
- 150000003077 polyols Chemical class 0.000 claims description 68
- 239000012948 isocyanate Substances 0.000 claims description 66
- 150000002513 isocyanates Chemical class 0.000 claims description 60
- -1 alkane diol Chemical class 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 229920000570 polyether Polymers 0.000 claims description 11
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 9
- 239000000376 reactant Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 claims description 7
- 229920005906 polyester polyol Polymers 0.000 claims description 7
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 claims description 5
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 3
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- 125000005442 diisocyanate group Chemical group 0.000 claims description 2
- 238000012360 testing method Methods 0.000 description 16
- 239000012939 laminating adhesive Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 6
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000004814 polyurethane Substances 0.000 description 5
- 229920002635 polyurethane Polymers 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 230000005641 tunneling Effects 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000011888 foil Substances 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 3
- 230000032798 delamination Effects 0.000 description 3
- 239000005001 laminate film Substances 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical class CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- 238000003475 lamination Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920006254 polymer film Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- ZMSQJSMSLXVTKN-UHFFFAOYSA-N 4-[2-(2-morpholin-4-ylethoxy)ethyl]morpholine Chemical compound C1COCCN1CCOCCN1CCOCC1 ZMSQJSMSLXVTKN-UHFFFAOYSA-N 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 1
- WWEXBGFSEVKZNE-UHFFFAOYSA-N N=C=O.N=C=O.C1=CC=CC2=CC=CC=C21 Chemical class N=C=O.N=C=O.C1=CC=CC2=CC=CC=C21 WWEXBGFSEVKZNE-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 235000015197 apple juice Nutrition 0.000 description 1
- 239000008365 aqueous carrier Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Classifications
-
- 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
- C08G18/4829—Polyethers containing at least three 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
- C08G18/08—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
- C08G18/28—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
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
-
- 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
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
-
- 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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4205—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups
- C08G18/4208—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups
- C08G18/4211—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups derived from aromatic dicarboxylic acids and dialcohols
- C08G18/4216—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups derived from aromatic dicarboxylic acids and dialcohols from mixtures or combinations of aromatic dicarboxylic acids and aliphatic dicarboxylic acids and dialcohols
-
- 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
- C08G18/6212—Polymers of alkenylalcohols; Acetals thereof; Oxyalkylation products thereof
-
- 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
- C08G18/6603—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6607—Compounds of groups C08G18/42, 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
- C08G18/65—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
- C08G18/6633—Compounds of group C08G18/42
- C08G18/6637—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/664—Compounds of group C08G18/42 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
- C08G18/70—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
-
- 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
-
- 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
- C09J175/06—Polyurethanes from polyesters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/08—Polyurethanes from polyethers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
-
- 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
- C09J2475/00—Presence of polyurethane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyurethanes Or Polyureas (AREA)
- Laminated Bodies (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
Description
イソシアネート成分は、少なくとも1つのイソシアネートと、少なくとも1つのポリオールと、分枝鎖アルカンジオールとを含む反応体(「プレポリマー反応体」)の反応生成物である少なくとも1つのイソシアネートプレポリマーを含む。
無溶剤接着剤組成物は、少なくとも1つのポリオールと分枝鎖アルカンジオールとを含むポリオール成分をさらに含む。
例示の実施例(「IE」)及び比較例(「CE」)で使用するための原料を以下の表1に詳述する。
実施例組成物を使用するコーティング及びラミネーションはNordmeccanica Labo−Combi 400ラミネート機で行う。ニップ温度は、全ラミネーションプロセス中、100m/分の速度において、40℃に保つ。コーティング重量は1.8〜2.0g/m2である。コーティング後、試験前に、ラミネートフィルムを、室温(23〜25℃)またはオーブン中において高温で硬化させる。
本願発明には以下の態様が含まれる。
項1.
少なくとも1つのイソシアネート、少なくとも1つのポリオール、及び分枝鎖アルカンジオールを含む反応体の反応生成物である少なくとも1つのイソシアネートプレポリマーを含むイソシアネート成分と、
少なくとも1つのポリオール及び分枝鎖アルカンジオールを含むポリオール成分と、を含む、2成分無溶剤接着剤組成物。
項2.
前記少なくとも1つのイソシアネートが、4,4−メチレンジフェニルジイソシアネート、2,4−トルエンジイソシアネート、2,6−トルエンジイソシアネート、2,4−メチレンジフェニルジイソシアネート、2,2−メチレンジフェニルジイソシアネート、ヘキサメチレンジイソシアネート、イソホロンジイソシアネート、キシレンジイソシアネート、及びそれらの組み合わせからなる群から選択される、項1に記載の組成物。
項3.
前記少なくとも1つのポリオールが、ポリエステルポリオール、ポリエーテルポリオール、及びそれらの組み合わせからなる群から選択される、項1または項2のいずれかに記載の組成物。
項4.
前記分枝鎖アルカンジオールが、3〜10個の炭素原子を含む主鎖アルキル鎖と、1〜6個の炭素原子を含む単一の分枝鎖アルキル鎖と、を含む、項1〜3のいずれか一項に記載の組成物。
項5.
前記分枝鎖アルカンジオールが、3−メチル−1,5−ペンタンジオール、2−メチル−1,3−プロパンジオール、及びそれらの組み合わせから選択される、項1〜4のいずれか一項に記載の組成物。
項6.
前記イソシアネート成分対前記ポリオール成分のモル比が、1:1〜1.8:1である、項1〜5のいずれか一項に記載の組成物。
項7.
前記組成物が、前記組成物の総重量に基づいて3〜15重量%の分枝鎖アルカンジオールを含む、項1〜6のいずれか一項に記載の組成物。
項8.
ラミネートを形成するための方法であって、
少なくとも1つのイソシアネート、少なくとも1つのポリオール、及び分枝鎖アルカンジオールを含む反応体の反応生成物である少なくとも1つのイソシアネートプレポリマーを含むイソシアネート成分と、少なくとも1つのポリオール及び分枝鎖アルカンジオールを含むポリオール成分と、を含む反応体を接触させることによって無溶剤接着剤組成物を形成することと、
前記接着剤組成物の層をフィルムの表面に塗布することと、
前記層を別のフィルムの表面と接触させてラミネートを形成することと、
前記接着剤組成物を硬化させることと、を含む、方法。
項9.
前記接着剤組成物が、前記接着剤成分の総重量に基づいて3〜15重量%の分枝鎖アルカンジオールを含む、項8に記載の方法。
項10.
項8に記載の方法によって形成されるラミネート。
Claims (10)
- 少なくとも1つのイソシアネート、少なくとも1つのポリオール、及び単一の分枝鎖アルキル鎖を有する分枝鎖アルカンジオールを含む反応体の反応生成物である少なくとも1つのイソシアネートプレポリマーを含むイソシアネート成分と、
少なくとも1つのポリオール及び単一の分枝鎖アルキル鎖を有する分枝鎖アルカンジオールを含むポリオール成分と、を含む、2成分無溶剤接着剤組成物。 - 前記少なくとも1つのイソシアネートが、4,4−メチレンジフェニルジイソシアネート、2,4−トルエンジイソシアネート、2,6−トルエンジイソシアネート、2,4−メチレンジフェニルジイソシアネート、2,2−メチレンジフェニルジイソシアネート、ヘキサメチレンジイソシアネート、イソホロンジイソシアネート、キシレンジイソシアネート、及びそれらの組み合わせからなる群から選択される、請求項1に記載の組成物。
- 前記少なくとも1つのポリオールが、ポリエステルポリオール、ポリエーテルポリオール、及びそれらの組み合わせからなる群から選択される、請求項1または請求項2のいずれかに記載の組成物。
- 前記分枝鎖アルカンジオールが、3〜10個の炭素原子を含む主鎖アルキル鎖と、1〜6個の炭素原子を含む単一の分枝鎖アルキル鎖と、を含む、請求項1〜3のいずれか一項に記載の組成物。
- 前記分枝鎖アルカンジオールが、3−メチル−1,5−ペンタンジオール、2−メチル−1,3−プロパンジオール、及びそれらの組み合わせから選択される、請求項1〜4のいずれか一項に記載の組成物。
- 前記イソシアネート成分対前記ポリオール成分の重量比が、100:100〜100:30である、請求項1〜5のいずれか一項に記載の組成物。
- 前記イソシアネート成分中の分枝鎖アルカンジオールの量がイソシアネート成分の重量に基づいて0.1〜10重量%であり、前記ポリオール成分中の分枝鎖アルカンジオールの量がポリオール成分の重量に基づいて3〜30重量%である、請求項1〜6のいずれか一項に記載の組成物。
- ラミネートを形成するための方法であって、
少なくとも1つのイソシアネート、少なくとも1つのポリオール、及び単一の分枝鎖アルキル鎖を有する分枝鎖アルカンジオールを含む反応体の反応生成物である少なくとも1つのイソシアネートプレポリマーを含むイソシアネート成分と、少なくとも1つのポリオール及び単一の分枝鎖アルキル鎖を有する分枝鎖アルカンジオールを含むポリオール成分と、を含む反応体を接触させることによって無溶剤接着剤組成物を形成することと、
前記接着剤組成物の層をフィルムの表面に塗布することと、
前記層を別のフィルムの表面と接触させてラミネートを形成することと、
前記接着剤組成物を硬化させることと、を含む、方法。 - 前記イソシアネート成分中の分枝鎖アルカンジオールの量がイソシアネート成分の重量に基づいて0.1〜10重量%であり、前記ポリオール成分中の分枝鎖アルカンジオールの量がポリオール成分の重量に基づいて3〜30重量%である、請求項8に記載の方法。
- 請求項8に記載の方法によって形成されるラミネート。
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/CN2016/077477 WO2017166003A1 (en) | 2016-03-28 | 2016-03-28 | Two-component solventless adhesive compositions and methods of making same |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2019513854A JP2019513854A (ja) | 2019-05-30 |
JP6748732B2 true JP6748732B2 (ja) | 2020-09-02 |
Family
ID=59963246
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2018550684A Active JP6748732B2 (ja) | 2016-03-28 | 2016-03-28 | 2成分無溶剤接着剤組成物及びそれらを作製する方法 |
Country Status (10)
Country | Link |
---|---|
US (1) | US11312888B2 (ja) |
EP (1) | EP3436541A4 (ja) |
JP (1) | JP6748732B2 (ja) |
CN (1) | CN108884373B (ja) |
AR (1) | AR107865A1 (ja) |
BR (1) | BR112018069664B1 (ja) |
MX (1) | MX2018011803A (ja) |
RU (1) | RU2741774C2 (ja) |
TW (1) | TWI839322B (ja) |
WO (1) | WO2017166003A1 (ja) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2020199175A1 (en) | 2019-04-04 | 2020-10-08 | Dow Global Technologies Llc | Solventless adhesive composition and method for preparing thereof |
JP6892036B1 (ja) * | 2019-08-26 | 2021-06-18 | Dic株式会社 | 2液型接着剤、積層体、成型体、包装材 |
CN112189042B (zh) * | 2019-12-04 | 2022-05-03 | 杭州之江新材料有限公司 | 双组分聚氨酯粘合剂组合物及其粘合方法 |
WO2023013425A1 (ja) * | 2021-08-05 | 2023-02-09 | Dic株式会社 | 接着剤、積層体、包装材 |
Family Cites Families (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4704445A (en) | 1985-10-14 | 1987-11-03 | Kuraray Co., Ltd. | Polyurethane compositions |
JPS62115019A (ja) * | 1985-11-13 | 1987-05-26 | Honny Chem Ind Co Ltd | ポリウレタンの製造方法 |
JPH05117363A (ja) * | 1991-10-29 | 1993-05-14 | Dainippon Ink & Chem Inc | ポリウレタン樹脂組成物 |
DE4232015A1 (de) * | 1992-09-24 | 1994-03-31 | Bayer Ag | Lösungsmittelfreie Zweikomponentenpolyurethanklebstoffsysteme |
DE4401572B4 (de) * | 1994-01-20 | 2006-07-06 | Henkel Kgaa | Zweikomponenten-Polyurethanklebstoffe mit verbessertem Klebevermögen |
MX9701338A (es) * | 1994-08-22 | 1997-05-31 | Henkel Kgaa | Composiciones de poliuretano con bajo contenido endiisocianatos monomeros. |
US5719252A (en) * | 1996-12-18 | 1998-02-17 | Bayer Corporation | Unfilled two-component polyurethane adhesive |
JP2000336142A (ja) * | 1999-05-28 | 2000-12-05 | Asahi Glass Co Ltd | ポリウレタン樹脂およびその製造方法 |
CN1115370C (zh) * | 2000-04-04 | 2003-07-23 | 蒋勤军 | 一种双组份聚氨酯胶粘剂及其制备方法 |
JP3915371B2 (ja) | 2000-05-29 | 2007-05-16 | 大日本インキ化学工業株式会社 | 耐熱水性に優れるラミネート用接着剤組成物 |
JP2002275449A (ja) * | 2001-03-15 | 2002-09-25 | Yokohama Rubber Co Ltd:The | 二液分離塗布型アクリルウレタン接着剤組成物 |
EP1329469A1 (de) * | 2002-01-18 | 2003-07-23 | Sika Schweiz AG | Polyurethanzusammensetzung |
JP4310687B2 (ja) * | 2003-10-08 | 2009-08-12 | ソニー株式会社 | アンテナ装置 |
CN1989217B (zh) * | 2004-07-30 | 2010-08-25 | 三井化学株式会社 | 二液固化型无溶剂系粘接剂 |
CN1244662C (zh) * | 2004-10-29 | 2006-03-08 | 东华大学 | 一种干式复合聚氨酯胶粘剂及其制造方法 |
US20100136347A1 (en) * | 2006-08-07 | 2010-06-03 | Simons J Brandon Simons | Two component solventless polyurethane laminating adhesives based on 1,4:3,6 dianhydrohexitols |
JP4948507B2 (ja) * | 2007-12-19 | 2012-06-06 | ローム アンド ハース カンパニー | ラミネート接着剤 |
JP5142871B2 (ja) * | 2008-07-28 | 2013-02-13 | 三井化学株式会社 | 二液硬化型無溶剤系接着剤 |
CN101747488A (zh) * | 2008-12-06 | 2010-06-23 | 周建明 | 无溶剂固化剂二苯基甲烷二异氰酸酯预聚物及其制备方法和应用 |
JP5362341B2 (ja) * | 2008-12-11 | 2013-12-11 | 大日精化工業株式会社 | 高耐久性ポリウレタン系接着剤の主剤および高耐久性ポリウレタン系接着剤 |
JP5546799B2 (ja) | 2009-06-04 | 2014-07-09 | ロックペイント株式会社 | 水分の影響を受け難い2液ラミネート用接着剤組成物 |
US8022164B1 (en) | 2010-03-04 | 2011-09-20 | Microvast, Inc. | Two-component solvent-free polyurethane adhesives |
EP2588312B1 (en) * | 2010-06-29 | 2020-08-05 | Ashland Licensing And Intellectual Property LLC | Solventless laminating adhesive for flexible packaging laminations and laminated structures made with the adhesive |
JP2013203946A (ja) * | 2012-03-29 | 2013-10-07 | Toyo Ink Sc Holdings Co Ltd | ポリエステル樹脂およびそれを含むドライラミネート用接着剤 |
CN114774053A (zh) | 2012-04-16 | 2022-07-22 | 沙特阿美技术公司 | 粘合剂组合物和方法 |
CN103059260B (zh) * | 2012-12-10 | 2015-06-17 | 浙江亿诚聚氨酯制造有限公司 | 一种采用鞋底原液异氰酸酯组分制备热塑型聚氨酯弹性体的方法 |
JP5787202B2 (ja) * | 2013-09-06 | 2015-09-30 | Dic株式会社 | ポリエステルポリオール、ラミネート接着剤用ポリオール剤、樹脂組成物、硬化性樹脂組成物、ラミネート用接着剤、及び太陽電池用バックシート |
CN103820069A (zh) | 2014-03-18 | 2014-05-28 | 新东方油墨有限公司 | 双组分无溶剂聚氨酯胶黏剂及其制备方法 |
-
2016
- 2016-03-28 US US16/089,075 patent/US11312888B2/en active Active
- 2016-03-28 JP JP2018550684A patent/JP6748732B2/ja active Active
- 2016-03-28 CN CN201680084079.8A patent/CN108884373B/zh active Active
- 2016-03-28 RU RU2018136079A patent/RU2741774C2/ru active
- 2016-03-28 MX MX2018011803A patent/MX2018011803A/es unknown
- 2016-03-28 BR BR112018069664-1A patent/BR112018069664B1/pt active IP Right Grant
- 2016-03-28 EP EP16895784.3A patent/EP3436541A4/en active Pending
- 2016-03-28 WO PCT/CN2016/077477 patent/WO2017166003A1/en active Application Filing
-
2017
- 2017-03-09 TW TW106107842A patent/TWI839322B/zh active
- 2017-03-13 AR ARP170100620A patent/AR107865A1/es active IP Right Grant
Also Published As
Publication number | Publication date |
---|---|
EP3436541A1 (en) | 2019-02-06 |
JP2019513854A (ja) | 2019-05-30 |
TWI839322B (zh) | 2024-04-21 |
WO2017166003A1 (en) | 2017-10-05 |
BR112018069664B1 (pt) | 2022-10-04 |
BR112018069664A2 (pt) | 2019-02-05 |
CN108884373B (zh) | 2022-01-25 |
RU2018136079A (ru) | 2020-04-13 |
EP3436541A4 (en) | 2019-12-18 |
US20190127616A1 (en) | 2019-05-02 |
MX2018011803A (es) | 2019-01-24 |
US11312888B2 (en) | 2022-04-26 |
RU2741774C2 (ru) | 2021-01-28 |
TW201805397A (zh) | 2018-02-16 |
RU2018136079A3 (ja) | 2020-04-13 |
CN108884373A (zh) | 2018-11-23 |
AR107865A1 (es) | 2018-06-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP3574031B1 (en) | Two-component solventless adhesive compositions | |
TWI782012B (zh) | 雙組分無溶劑黏著劑組合物 | |
TWI758278B (zh) | 雙組分無溶劑黏著劑組合物及製造其之方法 | |
EP3455274B1 (en) | Two-component solventless adhesive compositions comprising an amine-initiated polyol | |
CN114921215A (zh) | 不含聚酯的层合粘合剂组合物 | |
CN111032718B (zh) | 溶剂型粘合剂组合物 | |
JP6748732B2 (ja) | 2成分無溶剤接着剤組成物及びそれらを作製する方法 | |
CN109642005B (zh) | 双组分粘着剂组合物和其制备方法 | |
BR112017003584B1 (pt) | Composição adesiva de poliuretano | |
CN113748182B (zh) | 无溶剂粘合剂组合物和其制备方法 | |
TW202202549A (zh) | 多元醇化合物及用其製備之黏著劑組合物 | |
CN117425569A (zh) | 双包装聚氨酯组合物 | |
WO2022082575A1 (en) | Two-component solventless adhesive compositions and methods of making same | |
TW201912753A (zh) | 雙組分溶劑類黏合劑組合物及其製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
RD03 | Notification of appointment of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7423 Effective date: 20181004 |
|
RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20190104 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20190315 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20200108 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20200121 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20200420 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20200518 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20200609 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20200709 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20200807 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6748732 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |