JP6681978B2 - ポリウレタン接着剤組成物 - Google Patents
ポリウレタン接着剤組成物 Download PDFInfo
- Publication number
- JP6681978B2 JP6681978B2 JP2018516808A JP2018516808A JP6681978B2 JP 6681978 B2 JP6681978 B2 JP 6681978B2 JP 2018516808 A JP2018516808 A JP 2018516808A JP 2018516808 A JP2018516808 A JP 2018516808A JP 6681978 B2 JP6681978 B2 JP 6681978B2
- Authority
- JP
- Japan
- Prior art keywords
- adhesive composition
- composition according
- dry weight
- polyurethane
- polyol
- 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.)
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- 239000000203 mixture Substances 0.000 title claims description 98
- 239000000853 adhesive Substances 0.000 title claims description 95
- 230000001070 adhesive effect Effects 0.000 title claims description 94
- 229920002635 polyurethane Polymers 0.000 title description 16
- 239000004814 polyurethane Substances 0.000 title description 14
- 229920003009 polyurethane dispersion Polymers 0.000 claims description 35
- 229920005862 polyol Polymers 0.000 claims description 34
- 150000003077 polyols Chemical class 0.000 claims description 33
- 239000003822 epoxy resin Substances 0.000 claims description 28
- 229920000647 polyepoxide Polymers 0.000 claims description 28
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims description 25
- -1 aliphatic polyol Chemical class 0.000 claims description 20
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 18
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 18
- 229920000570 polyether Polymers 0.000 claims description 18
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical group C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 16
- 229920001451 polypropylene glycol Polymers 0.000 claims description 12
- 229920005906 polyester polyol Polymers 0.000 claims description 11
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000003431 cross linking reagent Substances 0.000 claims description 8
- 239000002563 ionic surfactant Substances 0.000 claims description 8
- 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 7
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 4
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical group NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 4
- 229920000768 polyamine Polymers 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 150000007942 carboxylates Chemical class 0.000 claims description 3
- 235000021317 phosphate Nutrition 0.000 claims description 3
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 2
- 150000003871 sulfonates Chemical group 0.000 claims description 2
- 150000002924 oxiranes Chemical group 0.000 claims 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 description 20
- 239000004971 Cross linker Substances 0.000 description 15
- 239000000126 substance Substances 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 229920001223 polyethylene glycol Polymers 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000002202 Polyethylene glycol Substances 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 239000011888 foil Substances 0.000 description 9
- 239000004698 Polyethylene Substances 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
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- 150000002118 epoxides Chemical group 0.000 description 8
- 239000012948 isocyanate Substances 0.000 description 7
- 229920000573 polyethylene Polymers 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000002318 adhesion promoter Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 229920000909 polytetrahydrofuran Polymers 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 239000003945 anionic surfactant Substances 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 150000004072 triols Chemical class 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 229920013701 VORANOL™ Polymers 0.000 description 3
- 238000012644 addition polymerization Methods 0.000 description 3
- 159000000032 aromatic acids Chemical class 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920001748 polybutylene Polymers 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- WXUAQHNMJWJLTG-UHFFFAOYSA-N 2-methylbutanedioic acid Chemical compound OC(=O)C(C)CC(O)=O WXUAQHNMJWJLTG-UHFFFAOYSA-N 0.000 description 2
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- 239000004386 Erythritol Substances 0.000 description 2
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 101001046686 Homo sapiens Integrin alpha-M Proteins 0.000 description 2
- 102100022338 Integrin alpha-M Human genes 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000032798 delamination Effects 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical group [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 2
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 2
- 229940009714 erythritol Drugs 0.000 description 2
- 235000019414 erythritol Nutrition 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N hexane carboxylic acid Natural products CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 229920006284 nylon film Polymers 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920001515 polyalkylene glycol Polymers 0.000 description 2
- 229920006267 polyester film Polymers 0.000 description 2
- 229940113116 polyethylene glycol 1000 Drugs 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 2
- 235000013772 propylene glycol Nutrition 0.000 description 2
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 230000005641 tunneling Effects 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- GOHPTLYPQCTZSE-UHFFFAOYSA-N 2,2-dimethylsuccinic acid Chemical compound OC(=O)C(C)(C)CC(O)=O GOHPTLYPQCTZSE-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- RNWKAIFTTVGWLK-UHFFFAOYSA-N 3,3-diethylpentanedioic acid Chemical compound OC(=O)CC(CC)(CC)CC(O)=O RNWKAIFTTVGWLK-UHFFFAOYSA-N 0.000 description 1
- WZHHYIOUKQNLQM-UHFFFAOYSA-N 3,4,5,6-tetrachlorophthalic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(O)=O WZHHYIOUKQNLQM-UHFFFAOYSA-N 0.000 description 1
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- 239000004970 Chain extender Substances 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 229920006309 Invista Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- WJRMGBWBIGOIOF-UHFFFAOYSA-N dodecyl benzenesulfonate;propan-2-amine Chemical compound CC(C)N.CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 WJRMGBWBIGOIOF-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
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 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
- 239000011976 maleic acid Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002523 polyethylene Glycol 1000 Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- ZNZJJSYHZBXQSM-UHFFFAOYSA-N propane-2,2-diamine Chemical compound CC(C)(N)N ZNZJJSYHZBXQSM-UHFFFAOYSA-N 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material 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
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical class S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
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Description
ポリウレタン分散液は、イオン性界面活性剤の助けを借りて、ポリウレタンプレポリマーを水中に分散させることによって調製される。
エポキシ樹脂は、安定した混合物を形成するために撹拌しながら、ポリウレタン分散液に添加される。
脂肪族アミン架橋剤は、本発明の接着剤組成物を調製するために撹拌しながら、ポリウレタン分散液とエポキシ樹脂との混合物に添加される。
ポリウレタン分散液は、ポリウレタンプレポリマーの主鎖に反応的に結合する接着促進剤を更に含み得る。接着促進剤はまた、後の添加剤として接着剤組成物に添加され得る。適切な接着促進剤の選択は当該技術分野において周知であり、それはポリウレタンプレポリマーの総乾燥重量に基づいて、乾燥重量で、0.1%〜3%、好ましくは0.1%〜2%、及びより好ましくは0.1%〜1%の範囲の量で使用される。
本接着剤組成物は、金属箔、ポリエステルフィルム、及びナイロンフィルムを含む基材の表面上に適用される。好ましくは、それは、金属箔の表面上に適用される。より好ましくは、金属箔は、アルミニウム(Al)箔である。
モノマー性芳香族ジイソシアネート:
ISONATE(商標)125Mイソシアネート(125M)は、The Dow Chemical Companyから市販されている純粋な4,4’−MDIである。
VORANOL(商標)V1010ポリオール(V1010)は、ポリエーテルポリオールであり、The Dow Chemical Companyから市販されている。
HSM−822−3ポリオール(HSM)は、ポリエステルポリオールであり、Xuchuan Chemical(Suzhou)Co.Ltdから市販されている。
D.E.R.(商標)736は、ポリグリコールジ−エポキシド液体樹脂であり、The Dow Chemical Companyから市販されている。
D.E.H.(商標)26は、The Dow Chemical Companyから市販されている脂肪族アミン架橋剤である。
CR3Aは、The Dow Chemical Companyから市販されている脂肪族ポリイソシアネートである。
PRIMAL(商標)Binder U−51は、脂肪族イソシアネート系ポリウレタン分散液であり、The Dow Chemical Companyから市販されている。
RHODACAL(商標)DS−4界面活性剤(DS−4)は、23%の固形分を有する陰イオン性界面活性剤であり、Rhodia Companyから市販されている。
1.接着強度(BS)
接着剤組成物から調製した積層体を、T字剥離試験のために、Instron Corporationから入手可能な5940シリーズシングルコラム卓上システムを使用して、250mm/分のクロスヘッド速度で幅15mmの条片に切断した。試験中、各条片の末尾を指でわずかに引っ張って、末尾が剥離方向に対して90度に保たれるようにした。各試料につき3つの条片を試験し、平均値を計算した。結果をN/15mmの単位で示した。値が高いほど、接着強度が良好である。
接着剤組成物から調製した積層体を、Brugger Companyから入手可能なHSG−C熱シール機を使用して、140℃のシール温度及び300Nの圧力で1秒間熱シールした後、冷まして、熱シール強度試験のために、Instron Corporationから入手可能な5940シリーズシングルコラム卓上システムを使用して、250mm/分のクロスヘッド速度で15mm幅の条片に切断した。各試料につき3つの条片を試験し、平均値を計算した。結果をN/15mmの単位で示した。値が高いほど、熱シール強度が良好である。
接着剤組成物から調製した積層体を、8cm×12cmの小片に切断し、中に水が入った状態で、熱シールによって袋を作製した。その後、沸騰したお湯の中に袋を置き、そこに30分間放置し、沸騰プロセス全体にわたって、全ての袋が常に水中に浸漬していることを確実にする。完了時、トンネリング、層間剥離、または漏出の程度を記録する。試験を通過した試料は、いかなるトンネリング、層間剥離、または漏出の証拠も示さないだろう。その後、袋を開いて空にし、冷ました後、15mm幅の条片に切断して、Instron5943機でT字剥離接着強度を試験する。これらの条片を試験して、平均値を取得した。
1.比較ポリウレタン分散液1〜3(比較PU1〜3)及び本発明のポリウレタン分散液4〜6(PU4〜6)の調製
異なる量のイソシアネートを、表1に従うポリオールの混合物に添加し、混合物が理論的イソシアネート基(NCO)含有量に到達し、ポリウレタンプレポリマーが作製されるまで、65〜90℃で4〜5時間反応させた。調製したポリウレタンプレポリマーをプラスチック瓶に移動させ、このプラスチック瓶にRHODACAL(商標)DS−4界面活性剤を2000〜3000rpmで1〜3分間撹拌しながら添加した。撹拌しながら、5℃のDI水を同じ瓶に添加して、均一分散液を作製した。その後、この分散液に1,2−プロパンジアミン(PDA)(20%水溶液)を1000〜1500rpmで15〜30分間撹拌しながら緩徐に添加して、ポリウレタン分散液を作製した。本発明のポリウレタン分散液のために、追加のエポキシ樹脂を、10〜15分間撹拌しながら、ポリウレタン分散液に添加した。各ポリウレタン分散液の詳細な構成成分を、表1に列挙した。
ポリウレタン分散液を、ポリウレタン分散液の総乾燥重量に基づいて、乾燥重量で、0.7%のD.E.H.26エポキシ硬化剤(本発明のポリウレタン分散液(PU4〜6)及び比較ポリウレタン分散液8(比較PU8)の場合)、またはポリウレタン分散液の総乾燥重量に基づいて、乾燥重量で、2%のCR3A架橋剤(比較ポリウレタン分散液(比較PU1〜3及び7))の場合)のいずれかと混合して、比較接着剤組成物1〜3及び7〜8(比較AC1〜3及び7〜8)ならびに本発明の接着剤組成物4〜6(AC4〜6)を形成した。その後、接着剤組成物をポリエチレンテレフタレート(PET)裏打ちAl箔上に適用し、炉内で、80℃で40秒間乾燥させた。その後、Al箔上に適用した接着剤組成物を炉内から取り出し、Cheminstruments,Incから入手可能なHL−101積層機を使用して、40umの厚のPEフィルムで被覆(または積層)した。Al箔−接着剤組成物−PEフィルム積層体を50℃で48時間硬化させ、試験した。
本願発明には以下の態様が含まれる。
[1]
接着剤組成物であって、前記接着剤組成物の総乾燥重量に基づいて、乾燥重量で、70%〜96%のポリウレタン分散液と、1%〜20%のエポキシ樹脂と、0.5%〜15%の脂肪族アミン架橋剤と、を含む、前記接着剤組成物。
[2]
前記ポリウレタン分散液が、ポリウレタンプレポリマーと、前記ポリウレタン分散液の総乾燥重量に基づいて、乾燥重量で、0.5%〜10%のイオン性界面活性剤と、0.1%〜8%のポリアミンと、を含む、上記[1]に記載の接着剤組成物。
[3]
前記ポリウレタンプレポリマーが、重合単位として、前記ポリウレタンプレポリマーの総乾燥重量に基づいて、乾燥重量で、10%〜40%のモノマー性芳香族ジイソシアネートと、20%〜85%のポリエーテルポリオールと、を含む、上記[2]に記載の接着剤組成物。
[4]
前記ポリウレタンプレポリマーが、重合単位として、前記ポリウレタンプレポリマーの総乾燥重量に基づいて、乾燥重量で、0.1%〜30%のポリエステルポリオールを更に含む、上記[3]に記載の接着剤組成物。
[5]
前記モノマー性芳香族ジイソシアネートが、500g/mol未満の分子量Mwを有する、上記[3]に記載の接着剤組成物。
[6]
前記モノマー性芳香族ジイソシアネートが、メチレンジフェニルジイソシアネート、トルエンジイソシアネート、及びこれらの組み合わせから選択される、上記[3]に記載の接着剤組成物。
[7]
前記ポリエーテルポリオールが、400〜4000g/molの分子量Mw、及び1.8〜4の官能価を有する、上記[3]に記載の接着剤組成物。
[8]
前記ポリエステルポリオールが、400〜4000g/molの分子量Mw、及び1.8〜4の官能価を有する、上記[4]に記載の接着剤組成物。
[9]
前記イオン性界面活性剤が、スルホン酸塩、リン酸塩、カルボン酸塩、及びこれらの組み合わせから選択される、上記[2]に記載の接着剤組成物。
[10]
前記ポリウレタン分散液が、25%〜60%の固形分を有する、上記[1]に記載の接着剤組成物。
[11]
前記エポキシ樹脂が、少なくとも2つのエポキシド基を有する化合物である、上記[1]に記載の接着剤組成物。
[12]
前記エポキシ樹脂が、エピクロロヒドリンと脂肪族ジオールまたはポリオールとの反応によって取得可能である、上記[1]に記載の接着剤組成物。
[13]
前記ポリオールが、ポリプロピレングリコールである、上記[12]に記載の接着剤組成物。
[14]
前記脂肪族アミン架橋剤が、ジエチレントリアミン、トリエチレンペンタミン、トリエチレンテトラミン、ポリエーテルアミン、及びこれらの任意の組み合わせから選択される、上記[1]に記載の接着剤組成物。
[15]
上記[1]に記載の接着剤組成物を含む、積層体。
Claims (13)
- 接着剤組成物であって、前記接着剤組成物の総乾燥重量に基づいて、乾燥重量で、70%〜96%のポリウレタン分散液と、1%〜20%のエポキシ樹脂と、0.5%〜15%の脂肪族アミン架橋剤と、を含み、
前記エポキシ樹脂が、エピクロロヒドリンと、脂肪族ジオールまたは脂肪族ポリオールとの反応によって得られる、前記接着剤組成物。 - 前記ポリウレタン分散液が、ポリウレタンプレポリマーと、前記ポリウレタン分散液の総乾燥重量に基づいて、乾燥重量で、0.5%〜10%のイオン性界面活性剤と、0.1%〜8%のポリアミンと、を含む、請求項1に記載の接着剤組成物。
- 前記ポリウレタンプレポリマーが、重合単位として、前記ポリウレタンプレポリマーの総乾燥重量に基づいて、乾燥重量で、10%〜40%のモノマー性芳香族ジイソシアネートと、20%〜85%のポリエーテルポリオールと、を含む、請求項2に記載の接着剤組成物。
- 前記ポリウレタンプレポリマーが、重合単位として、前記ポリウレタンプレポリマーの総乾燥重量に基づいて、乾燥重量で、0.1%〜30%のポリエステルポリオールを更に含む、請求項3に記載の接着剤組成物。
- 前記モノマー性芳香族ジイソシアネートが、500g/mol未満の分子量Mwを有する、請求項3又は4に記載の接着剤組成物。
- 前記モノマー性芳香族ジイソシアネートが、メチレンジフェニルジイソシアネート、トルエンジイソシアネート、及びこれらの組み合わせから選択される、請求項3〜5のいずれか一項に記載の接着剤組成物。
- 前記ポリエーテルポリオールが、400〜4000g/molの分子量Mw、及び1.8〜4の官能価を有する、請求項3〜6のいずれか一項に記載の接着剤組成物。
- 前記イオン性界面活性剤が、スルホン酸塩、リン酸塩、カルボン酸塩、及びこれらの組み合わせから選択される、請求項2〜7のいずれか一項に記載の接着剤組成物。
- 前記ポリウレタン分散液が、25%〜60%の固形分を有する、請求項1〜8のいずれか一項に記載の接着剤組成物。
- 前記エポキシ樹脂が、少なくとも2つのエポキシド基を有する化合物である、請求項1〜9のいずれか一項に記載の接着剤組成物。
- 前記脂肪族ジオールまたは前記脂肪族ポリオールが、ポリプロピレングリコールである、請求項1〜10のいずれか一項に記載の接着剤組成物。
- 前記脂肪族アミン架橋剤が、ジエチレントリアミン、テトラエチレンペンタミン、トリエチレンテトラミン、ポリエーテルアミン、及びこれらの任意の組み合わせから選択される、請求項1〜11のいずれか一項に記載の接着剤組成物。
- 請求項1〜12のいずれか一項に記載の接着剤組成物を含む、積層体。
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PCT/CN2015/092829 WO2017070820A1 (en) | 2015-10-26 | 2015-10-26 | Polyurethane adhesive composition |
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JP (1) | JP6681978B2 (ja) |
CN (1) | CN108138021B (ja) |
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BR (1) | BR112018006395B1 (ja) |
MX (1) | MX2018004384A (ja) |
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EP3694898A4 (en) | 2017-10-12 | 2021-07-14 | Swimc LLC | POLYURETHANE COATING COMPOSITION |
US20220025227A1 (en) * | 2018-12-03 | 2022-01-27 | Lord Corporation | Adhesive for castable urethanes |
EP4004113A1 (en) * | 2019-07-25 | 2022-06-01 | Lord Corporation | One-part adhesive for thermoplastic urethanes |
WO2021173301A2 (en) * | 2020-02-27 | 2021-09-02 | Illinois Tool Works Inc. | Heat transfer label and process for the use thereof |
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EP0490026A3 (en) * | 1990-12-10 | 1992-09-30 | H.B. Fuller Licensing & Financing, Inc. | Improved aqueous emulsion dispersion adhesives based on a polyol and a hindered isocyanate compound |
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DE4137660A1 (de) * | 1991-11-15 | 1993-05-19 | Basf Ag | Waessrige polyurethandispersionen |
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CN1093377A (zh) * | 1994-01-11 | 1994-10-12 | 青岛化工学院 | 高强度、高韧性和高耐磨性的聚氨酯-环氧树脂复合材料的制备方法 |
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JPH11335651A (ja) * | 1998-05-28 | 1999-12-07 | Nippon Nsc Ltd | 水系接着剤組成物 |
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BR112018006395B1 (pt) | 2022-05-31 |
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CN108138021B (zh) | 2021-05-04 |
TW201718812A (zh) | 2017-06-01 |
MX2018004384A (es) | 2018-05-11 |
EP3368628B1 (en) | 2022-01-26 |
BR112018006395A2 (pt) | 2018-10-09 |
JP2018538375A (ja) | 2018-12-27 |
AR106382A1 (es) | 2018-01-10 |
RU2018117539A (ru) | 2019-11-11 |
EP3368628A1 (en) | 2018-09-05 |
WO2017070820A1 (en) | 2017-05-04 |
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