CA1254692A - Water dispersible polyurethane adhesive compositions - Google Patents
Water dispersible polyurethane adhesive compositionsInfo
- Publication number
- CA1254692A CA1254692A CA000452458A CA452458A CA1254692A CA 1254692 A CA1254692 A CA 1254692A CA 000452458 A CA000452458 A CA 000452458A CA 452458 A CA452458 A CA 452458A CA 1254692 A CA1254692 A CA 1254692A
- Authority
- CA
- Canada
- Prior art keywords
- component
- groups
- composition
- oligourethane
- layer
- 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.)
- Expired
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 91
- 239000004814 polyurethane Substances 0.000 title claims abstract description 40
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 39
- 239000000853 adhesive Substances 0.000 title claims abstract description 33
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 239000010410 layer Substances 0.000 claims abstract description 44
- 238000000034 method Methods 0.000 claims abstract description 42
- 239000012790 adhesive layer Substances 0.000 claims abstract description 31
- 239000003125 aqueous solvent Substances 0.000 claims abstract description 31
- 238000002156 mixing Methods 0.000 claims abstract description 15
- 239000000758 substrate Substances 0.000 claims abstract description 9
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims description 22
- 125000002091 cationic group Chemical group 0.000 claims description 21
- 150000002894 organic compounds Chemical class 0.000 claims description 20
- -1 hydrogen amine Chemical class 0.000 claims description 14
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide group Chemical group NNC(=O)N DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 claims description 14
- 125000000129 anionic group Chemical group 0.000 claims description 13
- 239000012948 isocyanate Substances 0.000 claims description 13
- 150000002513 isocyanates Chemical class 0.000 claims description 13
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 229920000728 polyester Polymers 0.000 claims description 7
- 229920000570 polyether Polymers 0.000 claims description 7
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229920000642 polymer Polymers 0.000 claims description 4
- 150000002924 oxiranes Chemical class 0.000 claims 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract description 7
- 239000000047 product Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 229920001684 low density polyethylene Polymers 0.000 description 7
- 239000004702 low-density polyethylene Substances 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 229920005862 polyol Polymers 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000004677 Nylon Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000084 colloidal system Substances 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- 239000011888 foil Substances 0.000 description 4
- 229920001778 nylon Polymers 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- 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 4
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229920006267 polyester film Polymers 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- OWMNWOXJAXJCJI-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxymethyl)oxirane;phenol Chemical compound OC1=CC=CC=C1.OC1=CC=CC=C1.C1OC1COCC1CO1 OWMNWOXJAXJCJI-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920002799 BoPET Polymers 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical group S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- 239000005041 Mylar™ Substances 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 239000002313 adhesive film Substances 0.000 description 2
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 230000032798 delamination Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical class CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 125000003010 ionic group Chemical group 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000005026 oriented polypropylene Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- 229920001228 polyisocyanate Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 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 2
- NGZXDRGWBULKFA-NSOVKSMOSA-N (+)-Bebeerine Chemical compound C([C@@H]1N(C)CCC=2C=C(C(=C(OC3=CC=C(C=C3)C[C@H]3C=4C=C(C(=CC=4CCN3C)OC)O3)C=21)O)OC)C1=CC=C(O)C3=C1 NGZXDRGWBULKFA-NSOVKSMOSA-N 0.000 description 1
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- GFNDFCFPJQPVQL-UHFFFAOYSA-N 1,12-diisocyanatododecane Chemical compound O=C=NCCCCCCCCCCCCN=C=O GFNDFCFPJQPVQL-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- DNMWKVLCHRNMFF-UHFFFAOYSA-N 1,5,5-trimethylcyclohexane-1,3-diamine Chemical compound CC1(C)CC(N)CC(C)(N)C1 DNMWKVLCHRNMFF-UHFFFAOYSA-N 0.000 description 1
- CUUNWWCQMKJKRR-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol;hexanedioic acid;hexane-1,1-diol Chemical compound OCC(C)(C)CO.CCCCCC(O)O.OC(=O)CCCCC(O)=O CUUNWWCQMKJKRR-UHFFFAOYSA-N 0.000 description 1
- IVGRSQBDVIJNDA-UHFFFAOYSA-N 2-(2-aminoethylamino)ethanesulfonic acid Chemical compound NCCNCCS(O)(=O)=O IVGRSQBDVIJNDA-UHFFFAOYSA-N 0.000 description 1
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 1
- SDHQGBWMLCBNSM-UHFFFAOYSA-N 2-[2-(2-methoxyethoxy)ethoxy]ethyl acetate Chemical compound COCCOCCOCCOC(C)=O SDHQGBWMLCBNSM-UHFFFAOYSA-N 0.000 description 1
- JSGVZVOGOQILFM-UHFFFAOYSA-N 3-methoxy-1-butanol Chemical compound COC(C)CCO JSGVZVOGOQILFM-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- 229920000134 Metallised film Polymers 0.000 description 1
- AKNUHUCEWALCOI-UHFFFAOYSA-N N-ethyldiethanolamine Chemical compound OCCN(CC)CCO AKNUHUCEWALCOI-UHFFFAOYSA-N 0.000 description 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229930182556 Polyacetal Natural products 0.000 description 1
- DUFKCOQISQKSAV-UHFFFAOYSA-N Polypropylene glycol (m w 1,200-3,000) Chemical class CC(O)COC(C)CO DUFKCOQISQKSAV-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 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 1
- 238000010438 heat treatment Methods 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical class CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- GPCIDUIBGGUBJG-UHFFFAOYSA-N hexanedioic acid;hexane-1,1-diol Chemical compound CCCCCC(O)O.OC(=O)CCCCC(O)=O GPCIDUIBGGUBJG-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- REOJLIXKJWXUGB-UHFFFAOYSA-N mofebutazone Chemical group O=C1C(CCCC)C(=O)NN1C1=CC=CC=C1 REOJLIXKJWXUGB-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical class CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols 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
- 229920000768 polyamine Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 230000005641 tunneling Effects 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-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
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- 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
- C08G18/0804—Manufacture of polymers containing ionic or ionogenic 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—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
-
- 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
- C08G2170/00—Compositions for adhesives
- C08G2170/80—Compositions for aqueous adhesives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/14—Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Lining Or Joining Of Plastics Or The Like (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/486,728 US4540633A (en) | 1983-04-20 | 1983-04-20 | Water dispersible polyurethane adhesive compositions and adhesive layer formed therefrom |
| US486,728 | 1983-04-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1254692A true CA1254692A (en) | 1989-05-23 |
Family
ID=23933030
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000452458A Expired CA1254692A (en) | 1983-04-20 | 1984-04-19 | Water dispersible polyurethane adhesive compositions |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4540633A (enExample) |
| EP (1) | EP0126297B1 (enExample) |
| JP (1) | JPS59223776A (enExample) |
| AT (1) | ATE30332T1 (enExample) |
| CA (1) | CA1254692A (enExample) |
| DE (1) | DE3466889D1 (enExample) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3344693A1 (de) * | 1983-12-10 | 1985-06-20 | Bayer Ag, 5090 Leverkusen | Waessrige loesungen oder dispersionen von polyisocyanat-polyadditionsprodukten, ein verfahren zu ihrer herstellung, sowie ihre verwendung als bzw. zur herstellung von klebemittel |
| US4762880A (en) * | 1987-05-05 | 1988-08-09 | Uniroyal Plastics Co., Inc. | Water-based thermoforming adhesives |
| US5888654A (en) * | 1988-02-08 | 1999-03-30 | Courtaulds Performance Films | High performance epoxy based laminating adhesive |
| US5049249A (en) * | 1988-11-23 | 1991-09-17 | E. I. Du Pont De Nemours And Company | Low cure cathodic electrodeposition coatings |
| US4900415A (en) * | 1988-11-23 | 1990-02-13 | E. I. Du Pont De Nemours & Company | Low cure cathodic electrodeposition coatings |
| US4976833A (en) * | 1989-10-04 | 1990-12-11 | E. I. Du Pont De Nemours And Company | Electrodeposition coatings containing blocked tetramethylxylene diisocyanate crosslinker |
| EP0436746B1 (en) * | 1989-11-30 | 1996-06-12 | Courtaulds Performance Films | Process of manufacture for high performance epoxy based laminating adhesives |
| DE4015858A1 (de) * | 1990-05-17 | 1991-11-21 | Henkel Kgaa | Heisssiegelbeschichtung auf dispersionsbasis |
| US5532058A (en) * | 1990-12-10 | 1996-07-02 | H. B. Fuller Licensing & Financing, Inc. | Dry-bonded film laminate employing polyurethane dispersion adhesives with improved crosslinkers |
| US5494960A (en) * | 1990-12-10 | 1996-02-27 | H.B. Fuller Licensing & Financing, Inc. | Aqueous polyurethane dispersions and adhesives based thereon |
| JP3478343B2 (ja) * | 1991-04-30 | 2003-12-15 | 大日本インキ化学工業株式会社 | 水性接着剤及び接着方法 |
| EP0552420A3 (en) * | 1992-01-24 | 1993-09-15 | H.B. Fuller Licensing & Financing, Inc. | Water dispersed polyurethane polymer for improved coatings and adhesives |
| DE4308079A1 (de) * | 1993-03-13 | 1994-09-15 | Basf Ag | Verwendung von wäßrigen Polyurethandispersionen als Verbundfolienklebstoff |
| US5608000A (en) * | 1993-09-24 | 1997-03-04 | H. B. Fuller Licensing & Financing, Inc. | Aqueous polyurethane dispersion adhesive compositions with improved heat resistance |
| US5703158A (en) * | 1993-09-24 | 1997-12-30 | H.B. Fuller Licensing & Financing, Inc. | Aqueous anionic poly (urethane/urea) dispersions |
| US5610232A (en) * | 1993-09-24 | 1997-03-11 | H.B. Fuller Licensing & Financing, Inc. | Aqueous non-gelling, anionic polyurethane dispersions and process for their manufacture |
| EP0769492B1 (en) | 1994-07-04 | 1999-12-08 | Asahi Kasei Kogyo Kabushiki Kaisha | Semicarbazide derivative and coating composition containing the derivative |
| US5872182A (en) * | 1994-09-09 | 1999-02-16 | H. B. Fuller Licensing & Financing, Inc. | Water-based polyurethanes for footwear |
| US5616400A (en) * | 1995-11-20 | 1997-04-01 | Century International Adhesives & Coating Corporation | Cold seal adhesives, cold sealable films and packages formed therewith |
| US5834554A (en) * | 1996-03-05 | 1998-11-10 | H. B. Fuller Licensing & Financing, Inc. | Laminating adhesives for flexible packaging |
| US5861470A (en) * | 1997-03-07 | 1999-01-19 | H. B. Fuller Licensing & Financing, Inc. | Two component water-based adhesives for use in dry-bond laminating |
| PL335694A1 (en) | 1997-03-17 | 2000-05-08 | Dow Chemical Co | Polyurethane latexes, methods of obtaining them and polymers produced from such latexes |
| AU6681198A (en) | 1997-10-15 | 1999-05-03 | Minnesota Mining And Manufacturing Company | Abrasion-resistant ink compositions and methods of use |
| DE69901893T2 (de) | 1998-04-01 | 2003-01-09 | The Dow Chemical Co., Midland | Verfahren zur beschichtung von substraten mit polaren oberflächen mit polyurethanlatex |
| US6127514A (en) * | 1998-11-23 | 2000-10-03 | Bayer Corporation | One-component thermoset coating compositions |
| NO20001904L (no) | 1999-04-14 | 2000-10-16 | Dow Chemical Co | Polyuretanfilmer fremstilt ved elektrolytisk utfelling fra polyuretandispersjoner |
| NO20001903L (no) | 1999-04-14 | 2000-10-16 | Dow Chemical Co | Polyuretan-filmer fremstilt fra polyuretan-dispersjoner |
| KR20030048376A (ko) * | 2000-05-16 | 2003-06-19 | 다우 글로벌 테크놀로지스 인크. | 폴리우레탄 분산액 및 이를 사용하여 제조한 필름 |
| US6455631B1 (en) * | 2000-12-01 | 2002-09-24 | Bayer Corporation | Aqueous polyurethane dispersions containing modified hydrazide groups and their use in one-component thermoset compositions |
| EP2039734A1 (en) * | 2007-09-03 | 2009-03-25 | Tombow Pencil Co., Ltd. | Aqueous adhesive and use thereof in a ballpoint pen type bonding utensil |
| US11124682B2 (en) | 2017-12-21 | 2021-09-21 | Covestro Deutschland Ag | Frost-resistant adhesives based on polyisocyanates |
| WO2020026935A1 (ja) * | 2018-08-01 | 2020-02-06 | Dic株式会社 | 粘着剤組成物及び表面保護フィルム |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1495745C3 (de) * | 1963-09-19 | 1978-06-01 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung wäßriger, emulgatorfreier Polyurethan-Latices |
| FR1499121A (enExample) * | 1964-12-08 | 1968-01-12 | ||
| DE1694129B2 (de) * | 1967-02-01 | 1974-02-07 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung sedimentierender redispergierbarer Polyurethandi spersionen |
| DE1770068C3 (de) * | 1968-03-27 | 1981-01-15 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Polyurethanen Bayer AG, 5090 Leverkusen |
| US3796678A (en) * | 1970-08-17 | 1974-03-12 | Minnesota Mining & Mfg | Highly branched,capped polyurethanes for pressure sensitive adhesives |
| US4039517A (en) * | 1974-05-29 | 1977-08-02 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | Hydrophilic and thermoreactive urethane compositions with improved properties |
| US4061618A (en) * | 1975-05-07 | 1977-12-06 | National Starch And Chemical Corporation | Process for preparing stable polyurethane latices |
| JPS5213599A (en) * | 1975-07-22 | 1977-02-01 | Kao Corp | Preparation of aqueous polyurethane emulsion |
| US4160065A (en) * | 1976-12-14 | 1979-07-03 | Witco Chemical Corporation | Polyurethane latexes from NCO prepolymers chain extended with polyepoxides, polyanhydrides or polyaldehydes, and layered products |
| DE2734576A1 (de) * | 1977-07-30 | 1979-02-08 | Bayer Ag | Verfahren zur herstellung von waessrigen dispersionen oder loesungen von isocyanat-polyadditionsprodukten |
| DE2804609A1 (de) * | 1978-02-03 | 1979-08-09 | Bayer Ag | Waessrige loesungen oder dispersionen von polyisocyanat-polyadditionsprodukten, ein verfahren zu ihrer herstellung, sowie ihre verwendung als klebemittel |
| US4301053A (en) * | 1980-01-29 | 1981-11-17 | General Electric Company | Polyurethane resin coating composition |
-
1983
- 1983-04-20 US US06/486,728 patent/US4540633A/en not_active Expired - Fee Related
-
1984
- 1984-04-17 EP EP84104339A patent/EP0126297B1/en not_active Expired
- 1984-04-17 DE DE8484104339T patent/DE3466889D1/de not_active Expired
- 1984-04-17 AT AT84104339T patent/ATE30332T1/de not_active IP Right Cessation
- 1984-04-19 CA CA000452458A patent/CA1254692A/en not_active Expired
- 1984-04-20 JP JP59079999A patent/JPS59223776A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US4540633A (en) | 1985-09-10 |
| EP0126297B1 (en) | 1987-10-21 |
| JPH034592B2 (enExample) | 1991-01-23 |
| ATE30332T1 (de) | 1987-11-15 |
| JPS59223776A (ja) | 1984-12-15 |
| EP0126297A1 (en) | 1984-11-28 |
| DE3466889D1 (en) | 1987-11-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |