DE2857281C2 - - Google Patents
Info
- Publication number
- DE2857281C2 DE2857281C2 DE2857281T DE2857281T DE2857281C2 DE 2857281 C2 DE2857281 C2 DE 2857281C2 DE 2857281 T DE2857281 T DE 2857281T DE 2857281 T DE2857281 T DE 2857281T DE 2857281 C2 DE2857281 C2 DE 2857281C2
- Authority
- DE
- Germany
- Prior art keywords
- coupling agent
- silane coupling
- glycol
- polyester
- adhesive according
- 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 88
- 229920000728 polyester Polymers 0.000 claims description 45
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 34
- 239000000853 adhesive Substances 0.000 claims description 29
- 230000001070 adhesive effect Effects 0.000 claims description 29
- 239000011888 foil Substances 0.000 claims description 20
- 229920005862 polyol Polymers 0.000 claims description 19
- 239000004814 polyurethane Substances 0.000 claims description 19
- 229920002635 polyurethane Polymers 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 18
- 150000003077 polyols Chemical class 0.000 claims description 18
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 16
- -1 amino, imino Chemical group 0.000 claims description 16
- 239000005056 polyisocyanate Substances 0.000 claims description 16
- 229920001228 polyisocyanate Polymers 0.000 claims description 16
- 229910052751 metal Inorganic materials 0.000 claims description 13
- 239000002184 metal Substances 0.000 claims description 13
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002131 composite material Substances 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 3
- 125000003700 epoxy group Chemical group 0.000 claims description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
- 238000004806 packaging method and process Methods 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Chemical group 0.000 claims description 2
- 229910052801 chlorine Chemical group 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 235000013305 food Nutrition 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 11
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 238000000605 extraction Methods 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
- 239000005022 packaging material Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- 239000003822 epoxy resin Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 229920000647 polyepoxide Polymers 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 125000005442 diisocyanate group Chemical group 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000004743 Polypropylene Substances 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000002985 plastic film Substances 0.000 description 5
- 229920006255 plastic film Polymers 0.000 description 5
- 229920000139 polyethylene terephthalate Polymers 0.000 description 5
- 239000005020 polyethylene terephthalate Substances 0.000 description 5
- 229920001155 polypropylene Polymers 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000005025 cast polypropylene Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-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
- 230000001954 sterilising effect Effects 0.000 description 4
- 238000004659 sterilization and disinfection Methods 0.000 description 4
- 239000000758 substrate Substances 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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 3
- 230000032798 delamination Effects 0.000 description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002334 glycols Chemical class 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 239000011147 inorganic material Substances 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 235000021485 packed food Nutrition 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920005749 polyurethane resin Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 239000004698 Polyethylene Substances 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
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 235000013372 meat Nutrition 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 125000000962 organic group Chemical group 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
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 235000015067 sauces Nutrition 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 239000004246 zinc acetate Substances 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
- ICLCCFKUSALICQ-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanato-3-methylphenyl)-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(C=2C=C(C)C(N=C=O)=CC=2)=C1 ICLCCFKUSALICQ-UHFFFAOYSA-N 0.000 description 1
- JAZQDYXZDBYZMB-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol;ethane-1,2-diol Chemical compound OCCO.OCC(C)(C)CO JAZQDYXZDBYZMB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FVKYHUBHBRJSDA-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol propane Chemical compound OC1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)O.CCC FVKYHUBHBRJSDA-UHFFFAOYSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- BKXMNUKVRJJTIO-UHFFFAOYSA-N OCC(C)(CO)C.C(CO)O.C(CCCCCCCCC(=O)O)(=O)O Chemical compound OCC(C)(CO)C.C(CO)O.C(CCCCCCCCC(=O)O)(=O)O BKXMNUKVRJJTIO-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QEZIKGQWAWNWIR-UHFFFAOYSA-N antimony(3+) antimony(5+) oxygen(2-) Chemical compound [O--].[O--].[O--].[O--].[Sb+3].[Sb+5] QEZIKGQWAWNWIR-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- HJGDYRSNVCPFKN-UHFFFAOYSA-N benzene-1,3-dicarboxylic acid;decanedioic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1.OC(=O)CCCCCCCCC(O)=O HJGDYRSNVCPFKN-UHFFFAOYSA-N 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GQVCNZBQZKXBMX-UHFFFAOYSA-N butan-2-one;toluene Chemical compound CCC(C)=O.CC1=CC=CC=C1 GQVCNZBQZKXBMX-UHFFFAOYSA-N 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- VEIOBOXBGYWJIT-UHFFFAOYSA-N cyclohexane;methanol Chemical compound OC.OC.C1CCCCC1 VEIOBOXBGYWJIT-UHFFFAOYSA-N 0.000 description 1
- SYXDQUUNOVESOP-UHFFFAOYSA-N decanedioic acid;dimethyl benzene-1,4-dicarboxylate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1.OC(=O)CCCCCCCCC(O)=O SYXDQUUNOVESOP-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000003944 halohydrins Chemical class 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 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
- 229940046892 lead acetate Drugs 0.000 description 1
- 229940071125 manganese acetate Drugs 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- HOVAGTYPODGVJG-ZFYZTMLRSA-N methyl alpha-D-glucopyranoside Chemical compound CO[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HOVAGTYPODGVJG-ZFYZTMLRSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- INJVFBCDVXYHGQ-UHFFFAOYSA-N n'-(3-triethoxysilylpropyl)ethane-1,2-diamine Chemical compound CCO[Si](OCC)(OCC)CCCNCCN INJVFBCDVXYHGQ-UHFFFAOYSA-N 0.000 description 1
- XFFPIAQRIDTSIZ-UHFFFAOYSA-N n'-[3-(dimethoxymethylsilyl)propyl]ethane-1,2-diamine Chemical compound COC(OC)[SiH2]CCCNCCN XFFPIAQRIDTSIZ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 239000011527 polyurethane coating Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 229910052719 titanium Inorganic materials 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
- 238000005809 transesterification reaction Methods 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960000314 zinc acetate Drugs 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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/181—Acids containing aromatic rings
- C08G63/183—Terephthalic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
-
- 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
-
- 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
- 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
- C08L2666/28—Non-macromolecular organic substances
- C08L2666/44—Silicon-containing compounds
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)
- Laminated Bodies (AREA)
- Wrappers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP52159178A JPS5811912B2 (ja) | 1977-12-27 | 1977-12-27 | プラスチツク金属箔複合包装材用接着剤組成物 |
| PCT/JP1978/000056 WO1979000439A1 (en) | 1977-12-27 | 1978-12-14 | Adhesive composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2857281T1 DE2857281T1 (de) | 1981-01-08 |
| DE2857281C2 true DE2857281C2 (en:Method) | 1989-05-18 |
Family
ID=15687992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE782857281T Granted DE2857281T1 (de) | 1977-12-27 | 1978-12-14 | Adhesive composition |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4206299A (en:Method) |
| JP (1) | JPS5811912B2 (en:Method) |
| CA (1) | CA1096094A (en:Method) |
| DE (1) | DE2857281T1 (en:Method) |
| FR (1) | FR2413456A1 (en:Method) |
| WO (1) | WO1979000439A1 (en:Method) |
Families Citing this family (58)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4400100A (en) * | 1981-03-02 | 1983-08-23 | International Business Machines Corp. | Four layered ribbon for electrothermal printing |
| US4408021A (en) * | 1981-08-12 | 1983-10-04 | Morton Thiokol, Inc. | Adhesive comprising reaction product of gamma-isocyanatopropyltriethoxy silane and a thermoplastic polyester |
| US4429005A (en) | 1981-08-12 | 1984-01-31 | Morton Thiokol, Inc. | Adhesive for solar control film |
| US4419476A (en) * | 1981-10-09 | 1983-12-06 | E. I. Du Pont De Nemours & Co. | Ternary adhesive systems |
| JPS58122977A (ja) * | 1982-01-18 | 1983-07-21 | Takeda Chem Ind Ltd | ポリウレタン接着剤用組成物 |
| DE3220866A1 (de) * | 1982-06-03 | 1983-12-08 | Dynamit Nobel Ag, 5210 Troisdorf | Vernetzbare harzmischungen |
| DE3220865C2 (de) * | 1982-06-03 | 1984-08-02 | Dynamit Nobel Ag, 5210 Troisdorf | Haftkleber auf der Basis von hydroxylgruppenhaltigen Polymermischungen |
| US4487909A (en) * | 1982-08-09 | 1984-12-11 | E. I. Du Pont De Nemours And Company | Ternary adhesive systems containing a polyester polyol, an isocyanate-polyester-urethane, and a crosslinking agent which is a polyisocyanate |
| US4486508A (en) * | 1982-08-09 | 1984-12-04 | E. I. Dupont De Nemours And Company | Laminates from an adhesive formed by a system containing an hydroxyl-terminated polymer, an isocyanate-terminated urethane and a polyisocyanate which is a cross-linking agent |
| JPS59115374A (ja) * | 1982-12-21 | 1984-07-03 | Takeda Chem Ind Ltd | 接着剤用組成物 |
| US4507447A (en) * | 1983-01-05 | 1985-03-26 | Takeda Chemical Industries, Ltd. | Polyurethane adhesive compositions containing oxyacid of phosphorus and silane coupling agent |
| JPS59187070A (ja) * | 1983-04-06 | 1984-10-24 | Toyobo Co Ltd | 接着用樹脂組成物 |
| JPS6084365A (ja) * | 1983-10-13 | 1985-05-13 | Dainippon Toryo Co Ltd | ステンレス用塗料組成物 |
| US4853267A (en) * | 1984-02-09 | 1989-08-01 | Minnesota Mining And Manufacturing Company | Easy open closure system |
| JPS6128543A (ja) * | 1984-06-19 | 1986-02-08 | Takeda Chem Ind Ltd | 樹脂組成物 |
| DE3431688A1 (de) * | 1984-08-29 | 1986-03-13 | Bayer Ag, 5090 Leverkusen | Verwendung von loesungen von polyisocyanaten und hydroxylgruppen aufweisenden oligourethanen als klebemittel fuer folienverbunde |
| DE3518357A1 (de) * | 1985-05-22 | 1986-11-27 | Dynamit Nobel Ag, 5210 Troisdorf | Feuchtigkeitshaertendes polyestergemisch |
| DE69009889T2 (de) * | 1989-07-27 | 1995-01-26 | Nippon Polyurethane Kogyo Kk | Klebfreie Verbundwerkstoffharzzusammensetzung und Verfahren zu ihrer Herstellung. |
| US5091239A (en) * | 1990-03-07 | 1992-02-25 | Cms Gilbreth Packaging Systems, Inc. | Methods and adhesives for bonding polyolefin film |
| JP3022924B2 (ja) * | 1990-03-30 | 2000-03-21 | エイチ．ビー．ヒュラー ライセンシング アンド ファイナンシング インコーポレイティド | ホットメルト湿分―硬化ポリウレタン接着剤 |
| US5260398A (en) * | 1990-04-05 | 1993-11-09 | The Dow Chemical Company | Aromatic cyanate-siloxane |
| US5218073A (en) * | 1990-10-15 | 1993-06-08 | E. I. Du Pont De Nemours And Compaany | Polyhydroxy urethanes formed by reaction of reduced sugars and organic diisocyanates |
| JPH0625636A (ja) * | 1992-03-25 | 1994-02-01 | Sanyo Chem Ind Ltd | 接着剤組成物 |
| JP2733180B2 (ja) * | 1993-02-09 | 1998-03-30 | 東洋製罐株式会社 | フレキシブル包装用ラミネート、その製造方法及びそれに用いる接着剤 |
| JP3406732B2 (ja) * | 1995-01-06 | 2003-05-12 | サンスター技研株式会社 | 二液架橋型水性接着剤 |
| JPH08283690A (ja) * | 1995-04-10 | 1996-10-29 | Dainichiseika Color & Chem Mfg Co Ltd | 硬化性接着剤 |
| DE19531586A1 (de) * | 1995-08-28 | 1997-03-06 | Basf Lacke & Farben | Schichtstoff |
| US5731397A (en) * | 1996-04-16 | 1998-03-24 | Huntman Petrochemical Corporation | Polyurea spray railcar lining systems |
| JPH09316422A (ja) * | 1996-05-28 | 1997-12-09 | Nippon Polyurethane Ind Co Ltd | ラミネート用接着剤組成物、およびそれを用いたラミネートフィルムの製造方法 |
| US5962618A (en) * | 1997-04-16 | 1999-10-05 | Huntsman Petrochemical Corporation | Polyurea spray railcar lining systems |
| JP3363355B2 (ja) * | 1997-07-30 | 2003-01-08 | 三洋化成工業株式会社 | 二液型ドライラミネート用接着剤組成物 |
| US6221978B1 (en) | 1998-04-09 | 2001-04-24 | Henkel Corporation | Moisture curable hot melt adhesive and method for bonding substrates using same |
| JP4572427B2 (ja) * | 1998-06-26 | 2010-11-04 | 凸版印刷株式会社 | ドライラミネーション用接着剤及びそれを用いた積層体 |
| JP2001107015A (ja) * | 1999-10-08 | 2001-04-17 | Kansai Paint Co Ltd | 熱硬化型接着剤 |
| KR100439625B1 (ko) * | 1999-11-05 | 2004-07-12 | 에스케이씨 주식회사 | 프라이머층이 형성된 폴리에스테르 필름 및 그 제조방법 |
| USH2047H1 (en) | 1999-11-10 | 2002-09-03 | Henkel Corporation | Reinforcement laminate |
| US7057000B2 (en) * | 2000-12-22 | 2006-06-06 | Bayer Materialscience Llc | Two-component coating compositions containing silane adhesion promoters |
| JP2002201453A (ja) * | 2000-12-28 | 2002-07-19 | Toyobo Co Ltd | 無機蒸着フィルム用接着剤 |
| JP2002275448A (ja) * | 2001-03-16 | 2002-09-25 | Toyobo Co Ltd | 無機蒸着フィルム用接着剤 |
| JP2002275447A (ja) * | 2001-03-16 | 2002-09-25 | Toyobo Co Ltd | 無機蒸着フィルム用接着剤 |
| DE60207316T2 (de) | 2001-03-16 | 2006-07-20 | Toyo Boseki K.K. | Compoundierte Folie |
| US6846894B2 (en) | 2001-07-31 | 2005-01-25 | Mitsui Takeda Chemicals, Inc. | Laminate adhesive and usage thereof |
| JP2004047246A (ja) * | 2002-07-11 | 2004-02-12 | Dainippon Printing Co Ltd | 電池用包装材料 |
| JP4420375B2 (ja) * | 2003-03-20 | 2010-02-24 | 東洋モートン株式会社 | ラミネートフィルム積層体 |
| CN101134885B (zh) * | 2007-07-26 | 2010-07-21 | 吉林省包装工程研究中心 | 一种酯溶性双组分聚氨酯耐蒸煮铝塑复合粘合剂及其制造方法 |
| US10252852B2 (en) | 2011-04-22 | 2019-04-09 | Jbt Food & Dairy Systems B.V. | Adaptive packaging for food processing systems |
| US9241510B2 (en) | 2011-04-23 | 2016-01-26 | Ics Solutions B.V. | Apparatus and method for optimizing and controlling food processing system performance |
| US8893518B2 (en) | 2011-04-25 | 2014-11-25 | Ics Solutions B.V. | Accelerating, optimizing and controlling product cooling in food processing systems |
| US9955711B2 (en) | 2011-05-20 | 2018-05-01 | Jbt Food & Dairy Systems B.V. | Method and apparatus for increased product throughput capacity, improved quality and enhanced treatment and product packaging flexibility in a continuous sterilizing system |
| EP2546274B1 (en) | 2011-07-15 | 2016-05-11 | Rohm and Haas Company | Flow additive for urethane system |
| EP2546273B1 (en) * | 2011-07-15 | 2014-05-21 | Rohm and Haas Company | Low-viscosity urethane system |
| US9131729B2 (en) | 2011-09-28 | 2015-09-15 | Ics Solutions B.V. | Safe and efficient thermal transfer media for processing of food and drink products |
| US20160152880A1 (en) * | 2013-07-19 | 2016-06-02 | Dic Corporation | Laminate adhesive composition |
| EP3067377B1 (en) * | 2015-03-12 | 2023-01-18 | Henkel AG & Co. KGaA | Ultralow monomer polyurethanes |
| JP6612147B2 (ja) * | 2015-07-22 | 2019-11-27 | 大日精化工業株式会社 | 接着剤組成物、該組成物を用いてなる包装材料、電池用外装材、成形ケース及び蓄電デバイス |
| DE102016205913A1 (de) * | 2016-04-08 | 2017-10-12 | Mitsubishi Polyester Film Gmbh | Biaxial orientierte Polyesterfolie für die Metalllaminierung |
| CN110121533B (zh) * | 2017-02-06 | 2022-06-21 | 尤尼吉可株式会社 | 聚酯树脂组合物、粘接剂和层叠体 |
| CN119907845A (zh) * | 2022-12-29 | 2025-04-29 | Dic株式会社 | 粘合剂、层压体和包装材料 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2216112A1 (de) * | 1971-04-03 | 1972-12-28 | Takeda Chemical Industries Ltd | Klebstoffe |
| DE2232445A1 (de) * | 1971-07-05 | 1973-01-18 | Takeda Chemical Industries Ltd | Klebstoffgemische |
| DE2318440A1 (de) * | 1972-04-14 | 1973-10-25 | Takeda Chemical Industries Ltd | Klebstoffe |
| DE2415467A1 (de) * | 1973-03-30 | 1974-10-10 | Usm Corp | Fluessiger klebstoff |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1192426A (fr) * | 1956-12-26 | 1959-10-26 | Thomson Houston Comp Francaise | Compositions résineuses de silicone et de polyester et leur fabrication |
| FR1438873A (fr) * | 1964-07-07 | 1966-05-13 | American Cyanamid Co | Adhésifs améliorés résistant à l'eau |
| US3448072A (en) * | 1965-06-14 | 1969-06-03 | Gen Electric | Silylurethane terminated polyester compositions |
| DE1629795A1 (de) * | 1965-07-26 | 1971-02-04 | Zimmer Plastic Gmbh | Laminiertes Flaechengebilde und Verfahren zu seiner Herstellung |
| US3309261A (en) * | 1966-04-21 | 1967-03-14 | American Cyanamid Co | Adhesion of urethane adhesives to metals |
| JPS4630711B1 (en:Method) * | 1967-03-16 | 1971-09-06 | ||
| DE1719120C3 (de) * | 1967-09-21 | 1979-11-08 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Hydroxylgruppen enthaltenden Polyurethanen und Klebemittel |
| US3658939A (en) * | 1968-12-11 | 1972-04-25 | Usm Corp | Polyurethane and adhesive solution of a polyurethane |
| GB1304072A (en:Method) * | 1970-04-29 | 1973-01-24 | ||
| US3711445A (en) * | 1970-10-08 | 1973-01-16 | Du Pont | Self-priming polyurethane compositions |
| JPS522440B2 (en:Method) * | 1972-07-22 | 1977-01-21 | ||
| JPS5230028B2 (en:Method) * | 1973-02-02 | 1977-08-05 | ||
| JPS50103583A (en:Method) * | 1974-01-22 | 1975-08-15 | ||
| DE2629535C3 (de) * | 1976-07-01 | 1979-10-11 | Beiersdorf Ag, 2000 Hamburg | Verfahren zur Herstellung von blatt- oder bahnförmigen Materialien, die mindestens auf einer Seite eine beschriftbare klebstoffabweisende Beschichtung tragen |
-
1977
- 1977-12-27 JP JP52159178A patent/JPS5811912B2/ja not_active Expired
-
1978
- 1978-12-14 WO PCT/JP1978/000056 patent/WO1979000439A1/ja unknown
- 1978-12-14 DE DE782857281T patent/DE2857281T1/de active Granted
- 1978-12-22 CA CA318,528A patent/CA1096094A/en not_active Expired
- 1978-12-26 FR FR7836339A patent/FR2413456A1/fr active Granted
-
1979
- 1979-02-12 US US06/022,561 patent/US4206299A/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2216112A1 (de) * | 1971-04-03 | 1972-12-28 | Takeda Chemical Industries Ltd | Klebstoffe |
| DE2232445A1 (de) * | 1971-07-05 | 1973-01-18 | Takeda Chemical Industries Ltd | Klebstoffgemische |
| DE2318440A1 (de) * | 1972-04-14 | 1973-10-25 | Takeda Chemical Industries Ltd | Klebstoffe |
| DE2415467A1 (de) * | 1973-03-30 | 1974-10-10 | Usm Corp | Fluessiger klebstoff |
Non-Patent Citations (2)
| Title |
|---|
| Adhäsion 1969, S.257-60 u. 278-80 * |
| US-Z.: Adhesives Agents, March 1972, S. 26-32 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1979000439A1 (en) | 1979-07-12 |
| JPS5490239A (en) | 1979-07-17 |
| US4206299A (en) | 1980-06-03 |
| FR2413456B1 (en:Method) | 1982-09-24 |
| FR2413456A1 (fr) | 1979-07-27 |
| CA1096094A (en) | 1981-02-17 |
| DE2857281T1 (de) | 1981-01-08 |
| JPS5811912B2 (ja) | 1983-03-05 |
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| Date | Code | Title | Description |
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| D2 | Grant after examination | ||
| 8363 | Opposition against the patent | ||
| 8365 | Fully valid after opposition proceedings | ||
| 8339 | Ceased/non-payment of the annual fee |