JP2017518400A - リン酸接着促進剤 - Google Patents
リン酸接着促進剤 Download PDFInfo
- Publication number
- JP2017518400A JP2017518400A JP2016563171A JP2016563171A JP2017518400A JP 2017518400 A JP2017518400 A JP 2017518400A JP 2016563171 A JP2016563171 A JP 2016563171A JP 2016563171 A JP2016563171 A JP 2016563171A JP 2017518400 A JP2017518400 A JP 2017518400A
- Authority
- JP
- Japan
- Prior art keywords
- polyol
- composition
- adhesive
- polyols
- film
- 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.)
- Granted
Links
- 229910019142 PO4 Inorganic materials 0.000 title claims abstract description 28
- 239000010452 phosphate Substances 0.000 title claims abstract description 28
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 title claims abstract description 25
- 239000002318 adhesion promoter Substances 0.000 title description 11
- 229920005862 polyol Polymers 0.000 claims abstract description 118
- 150000003077 polyols Chemical class 0.000 claims abstract description 115
- 239000000203 mixture Substances 0.000 claims abstract description 102
- 230000001070 adhesive effect Effects 0.000 claims abstract description 57
- 239000000853 adhesive Substances 0.000 claims abstract description 56
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 32
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 32
- 239000000758 substrate Substances 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 22
- 239000002243 precursor Substances 0.000 claims description 35
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 32
- -1 phosphate ester Chemical class 0.000 claims description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 150000001875 compounds Chemical class 0.000 description 28
- 229920000137 polyphosphoric acid Polymers 0.000 description 23
- 238000012360 testing method Methods 0.000 description 23
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 22
- 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 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 19
- 239000002904 solvent Substances 0.000 description 18
- 239000002253 acid Substances 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 229910052698 phosphorus Inorganic materials 0.000 description 16
- 229920000570 polyether Polymers 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- 239000004721 Polyphenylene oxide Substances 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 13
- 239000011574 phosphorus Substances 0.000 description 13
- 229920005989 resin Polymers 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 235000011187 glycerol Nutrition 0.000 description 9
- 239000012948 isocyanate Substances 0.000 description 9
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 9
- 150000002513 isocyanates Chemical class 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 8
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 235000011007 phosphoric acid Nutrition 0.000 description 8
- 229920000139 polyethylene terephthalate Polymers 0.000 description 8
- 239000005020 polyethylene terephthalate Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 7
- 230000007547 defect Effects 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000004698 Polyethylene Substances 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 229920005906 polyester polyol Polymers 0.000 description 6
- 229920000573 polyethylene Polymers 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 229920013701 VORANOL™ Polymers 0.000 description 5
- 239000013256 coordination polymer Substances 0.000 description 5
- 230000032798 delamination Effects 0.000 description 5
- 230000004927 fusion Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 5
- 125000004437 phosphorous atom Chemical group 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
- 229920006254 polymer film Polymers 0.000 description 4
- 239000000565 sealant Substances 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 235000021028 berry Nutrition 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 235000008960 ketchup Nutrition 0.000 description 3
- 238000010030 laminating Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 229920000620 organic polymer Polymers 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 239000000052 vinegar Substances 0.000 description 3
- 235000021419 vinegar Nutrition 0.000 description 3
- 239000002023 wood Substances 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical group CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 229920005830 Polyurethane Foam Polymers 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000029087 digestion Effects 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 150000002483 hydrogen compounds Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000003880 polar aprotic solvent Substances 0.000 description 2
- 239000011496 polyurethane foam Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 235000015067 sauces Nutrition 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
- 230000005641 tunneling Effects 0.000 description 2
- 239000002759 woven fabric Substances 0.000 description 2
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
- 0 CC(C)(*)NOC(C)(C)*C(C)(C)O*1(CC1)C(C)(C)OC=C Chemical compound CC(C)(*)NOC(C)(C)*C(C)(C)O*1(CC1)C(C)(C)OC=C 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XYZZKVRWGOWVGO-UHFFFAOYSA-N Glycerol-phosphate Chemical compound OP(O)(O)=O.OCC(O)CO XYZZKVRWGOWVGO-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005370 alkoxysilyl group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002118 epoxides Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 229920002457 flexible plastic Polymers 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000005001 laminate film Substances 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 239000002984 plastic foam Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000011120 plywood Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 239000012748 slip agent Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B27/08—Layered products comprising a layer of synthetic resin 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
-
- 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
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/36—Layered products comprising a layer of synthetic resin comprising polyesters
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B37/00—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
- B32B37/12—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives
-
- 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
- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
- B32B7/04—Interconnection of layers
- B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3878—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus
- C08G18/3882—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus having phosphorus bound to oxygen only
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4205—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups
- C08G18/4208—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups
- C08G18/4211—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups derived from aromatic dicarboxylic acids and dialcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4804—Two or more polyethers of different physical or chemical nature
- C08G18/4812—Mixtures of polyetherdiols with polyetherpolyols having at least three hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5075—Polyethers having heteroatoms other than oxygen having phosphorus
- C08G18/5081—Polyethers having heteroatoms other than oxygen having phosphorus having phosphorus bound to oxygen only
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/721—Two or more polyisocyanates not provided for in one single group C08G18/73 - C08G18/80
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/797—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing carbodiimide and/or uretone-imine groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/08—Polyurethanes from polyethers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B37/00—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
- B32B37/12—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives
- B32B2037/1253—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives curable adhesive
-
- 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
- B32B2307/00—Properties of the layers or laminate
- B32B2307/50—Properties of the layers or laminate having particular mechanical properties
- B32B2307/54—Yield strength; Tensile strength
-
- 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
- B32B2375/00—Polyureas; Polyurethanes
-
- 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
- B32B2439/00—Containers; Receptacles
- B32B2439/70—Food packaging
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)
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
Mhy=前駆体ポリオールの1分子当たりのヒドロキシル基の数
Nx=Mhy−2
Mx=(前駆体ポリオールのモル)× Nx
Mp=リン型酸中に含有されるリン原子のモル
好ましくは、Mp:Mxの比は、0.1:1以上、より好ましくは、0.2:1以上、より好ましくは、0.5:1以上、より好ましくは、0.75:1以上である。好ましくは、Mp:Mxの比は、1.1:1以下である。
OHN=OH数。ASTM D 4274−88によって測定される。
AV=酸価。ASTM D 3644−83によって測定される(「酸価(acid number)」と同義)。
VISC=粘度。スピンドルSC−27を使用した、サーモスタット少量サンプルアダプタを有するBrookfield DVII+粘度計を用いて測定される。回転速度は、粘度測定値を得るために必要に応じて、6〜60rpmと異なった。
粘度(C&P)=40mmのコーン及び温度制御のためのペルチェプレートを使用した、TA INSTRUMENTS AR 2000レオメータを用いて測定される粘度。コーン角度=0°30分4秒、せん断速度=10秒−1
%NCOは、ASTM 2572−70によって測定される。
分子量は、液体サイズ排除クロマトグラフィASTM D3536−76またはD3593−80によって測定される。
Tg=中点法及び10℃/分のランプ速度を使用した、示差走査熱量測定法によって測定されるガラス転移。
pbw=重量部
PPA=ポリリン酸、115%グレード
PA=リン酸、100%(固体)
DPG=ジプロピレングリコール(ALDRICH Chemical Co.)
EtAc=酢酸エチル
試験されたフィルムは、以下の通りである。
・PET=厚さ24マイクロメートルのポリエチレンテレフタレート(92LBT)
・ADCOTE(商標)550/COREACTANT F(Dow Chemical Co.)と共に、ソフトラミネーショングレードグレードAMCORアルミホイル(厚さ9μm)にラミネートされたポリエチレンテレフタレート(PET、厚さ12ミクロン(μm))から作製される、予めラミネートされたフィルム。このラミネートされた構造は、AMPAC Company(Cary,IL)から得られ、「プレラム」またはPET−Alと称される。
・Pliant 808.24=Berry Plasticsからのポリエチレンシーラントフィルム
・GF−19=Berry Plasticsからの大量のスリップ剤を含有するポリエチレンシーラントフィルム
・PET=ポリエチレンテレフタレート
15mmまたは25.4mm(1インチ)幅の片に切り分けられ、25.4mm(1インチ)の片に対して25.4cm/分(10インチ/分)、または15mmの片に対して10.2cm(4インチ)の速度で、Thwing Albert(商標)引張試験機上で引っ張られるラミネート試料に対して、90°のT字剥離試験を行った。ラミネート中の2つのフィルムが分離(剥離)したとき、引張中の力の平均を記録した。フィルムのうちの1つが延伸したか、または破断した場合、最大力または破断力を記録した。値は、3つの別々の試料片の平均であった。破壊モード(「FM」)を以下の通り記録した。
PFS=部分的フィルム延伸(フィルムは延伸し、かつ同時に、ある程度まで剥離する)
FT=フィルム裂けまたは破断
1°=一次ウェブ(接着剤は、一次ウェブまたはフィルム上にコーティングされる)
2°=二次ウェブ(一次ウェブにラミネートされるフィルム、多くの場合、ポリエチレンのようなシーラントフィルム)
AF=接着剤破壊(接着剤は、一次フィルム上にあり、二次フィルムに接着できない)
AT=接着剤移動(接着剤は、一次フィルムに接着できず、二次フィルムに移動される)
AS=接着剤分裂または凝集破壊(接着剤は、一次及び二次フィルムの両方の上に見られる)
Delam=試験中(例えば、ボイルインバッグ試験中)に分離されたラミネートフィルムで、フィルム間にほとんどまたは全く接着がない。
上記のように、ポリエチレンシーラントフィルム(Berry plasticsからのPliant 808.24)に結合した「プレラム」フィルムPET−Alから、ラミネートを作製した。9”×12”(23cm×30.5cm)のラミネートシートのうちの1つを折り畳んで、約9”×6”(23cm×15.25cm)の二重層を得た。縁部をペーパーカッターで整えて、折り畳まれた一片約5”×7”(12.7×17.8cm)を得た。2つの長い側面及び1つの短い側面を縁部で熱融着して、10.2cm×15.2cm(4インチ×6インチ)の内部サイズを有する完成パウチを得た。276kpa(40PSI)の油圧で、1秒間、177℃(350°F)で熱融着を行った。2つまたは3つのパウチを各試験のために作製した。パウチを、開放縁部を通して、100±5mLの1:1:1ソース(等しい重量部のケチャップ、酢、及び植物油のブレンド)で充填した。熱融着領域上への充填物の飛び散りは、試験中の熱融着の失敗を引き起こす可能性があるため、これを回避した。充填後、パウチの頂部を、パウチ内の空気の閉じ込めを最小限に抑える方法で密閉した。パウチの4面全てに対して、シールの完全性を検査して、試験中にパウチを漏れさせる密封の欠陥がなかったことを確実にした。いかなる疑わしいパウチも廃棄及び交換した。場合によっては、ラミネートの欠陥に印を付けて、新しい追加の欠陥が試験中にもたらされたかどうかを識別した。
所望の最終濃度を得るために、溶媒の添加後に(示される場合)、接着剤のポリオール部分を表に示される添加剤と組み合わせて、次いで、イソシアネート官能性部分を添加し、約15分間混合することによって、以下の実施例における試料を調製した。
国際公開第WO 2013/053555号に使用される方法を使用した。2011.0g(7.89mol)のVORANOL(商標)CP260トリオールポリエーテルポリオール、1520.4g(10.25mol)の無水フタル酸、及び0.20gの2−エチル−4−メチル−イミダゾール(EMI、生成物の重量に基づき41ppm)を5Lのステンレス鋼アルコキシル化反応器内で、50rpmにおいて撹拌しながら混合した。反応混合物を600kPa(6バール)の窒素(N2)圧力で、10回洗い流した。反応器を600kPa(6バール)のN2圧力で、130℃において温度調節した。得られたスラリーは、徐々に反応器内で溶解し、この温度で、0.5時間後に主に液体になった。撹拌速度は、50〜200rpmに徐々に増加した。反応器内容物をさらに1.5時間撹拌した。反応器内のN2圧力を1.0バールまで低減し、攪拌速度を300rpmまで上げた。PO(1246.0g、21.46mol)を、85分間、15g/分の供給速度で反応器に供給した。発熱によって、即時の反応開始は発熱を伴った。供給の完了時に、反応器内の総圧力は、490kPa(4.9バール)に達した。3.0時間のさらなる消化時間を可能にした。反応器内の総圧力は、430kPa(4.3バール)まで減少した。反応器温度を100℃まで減少させた。エタノール中6.80gのトリフルオロメタンスルホン酸の10%溶液(TFA、生成物の重量に基づき142ppm)を、反応器に接続された加圧ステンレス鋼ボンベを用いて、反応器内に注入した。反応器内の即時の圧力降下及び発熱が観察され、30分間のさらなる消化時間を可能にした。残留窒素圧力を放出し、反応混合物を600kPa(6バール)のN2圧力で、10回洗い流した。水酸化カリウム(7.16g、エタノール中0.5mol/1溶液)を、反応器に接続された加圧ステンレス鋼ボンベを用いて、反応器内に注入して、残りのトリフルオロメタンスルホン酸を中和させた。次いで、生成物を120℃で、1時間、真空中で取り除いた。無色の粘性液体を得た。
反応物質の量は、以下の表に示される。1Lの多口丸底フラスコをオーブン内で乾燥させ、乾燥N2で30分間洗い流し、次いで、ポリエーテルポリオールを充填し、70mL/分のN2スイープ下に置いた。注射器にALDRICH CHEMICAL Companyからの115%のポリリン酸(PPA)を充填した。PPAを、注射器からポリエーテルポリオールに強く撹拌しながら滴下添加した。温度の最小上昇を記述した。次いで、反応器内容物を1時間100℃まで加熱し(粘度の有意な増加が観察された)、透明かつ無色の生成物を包装した。
反応物質の量は、以下の表にある。1Lの多口丸底フラスコをオーブン内で乾燥させ、乾燥N2で30分間洗い流し、次いで、VORANOL(商標)CP 450ポリエーテルポリオールを充填し、70mL/分のN2スイープ下に置いた。注射器にALDRICH CHEMICAL Co.からの115%のポリリン酸(PPA)を充填した。PPAをポリエーテルポリオールに強く撹拌しながら滴下添加した。最小温度上昇を観察した。反応器内容物を1時間100℃まで加熱し、次いで、45℃まで冷却した。ISONATE(商標)125Mポリイソシアネートを添加した。温度は、反応の熱から約95℃まで上昇した。また、粘度の増加及び黄色の発現があった。次いで、反応器を65℃にし、酢酸エチルを添加して、粘度を低減し、撹拌を改善した。1時間後、反応器を冷却し、内容物を包装した。
接着剤のポリオール部分を表に示される添加剤と組み合わせ、続いて、所望の最終濃度を得るための溶媒を添加し、次いで、イソシアネート官能性部分を添加し、約15分間勘合することによって、以下の表中の試料を調製した。
成分は以下の通りであった。
ポリリン酸(Aldrich Chemical Co.からの40グラムの115%)を、撹拌器、温度計、及び窒素入口/出口を有する三口フラスコ内に配置した。乾燥窒素のゆっくりとした流れを、反応時間全体を通して反応器に通した。グリセリン(69.4グラム、Aldrich)を攪拌しながら添加した。反応の熱によって、温度は10分以内に24℃から69℃まで上昇した。溶液は、45分間、60〜70℃で保持した。透明、無色、粘性液体生成物を冷却し、ガラス容器内に包装した。
接着剤のポリオール部分を添加剤と組み合わせ、完全に混合し、得られた溶液を室温で少なくとも24時間置くことによって、以下の表の試料を調製した。ラミネートを調製したとき、ポリオールブレンドを、表に示される割合で、共反応物質(NCO末端プレポリマー)と組み合わせた。酢酸エチルを十分な量でブレンドに添加して、35〜40%の固体を有する溶液を得て、すでに述べたように、ラミネートを調製及び試験した。表14の全ての試料に対して、NCO当量/OH当量の比は、約1.4であった。
Claims (8)
- 1つ以上のポリイソシアネートと、1つ以上のリン酸官能性ポリオールと、を含む、接着剤組成物。
- 前記リン酸官能性ポリオールは、前駆体ポリオールのリン酸エステルである、請求項1に記載の接着剤組成物。
- 前記前駆体ポリオールは、アルキルトリオールまたはアルコキシル化アルキルトリオールのいずれかである、請求項2に記載の接着剤。
- 前記前駆体ポリオールは、グリセロールまたはアルコキシル化グリセロールのいずれかである、請求項2に記載の接着剤。
- 前記前駆体ポリオールは、プロポキシル化グリセロールである、請求項2に記載の接着剤。
- 2つの基板を一緒に結合して、結合物品を形成する方法であって、請求項1に記載の組成物の層を前記基板のうちの1つに適用するステップと、請求項1に記載の組成物の前記層を第2の基板に接触させるステップと、請求項1に記載の組成物を硬化するか、または硬化させるステップと、を含む、前記方法。
- 請求項6に記載の方法によって形成される結合物品。
- 前記結合物品は、ラミネートである、請求項6に記載の結合物品。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201461987530P | 2014-05-02 | 2014-05-02 | |
US61/987,530 | 2014-05-02 | ||
PCT/US2015/028981 WO2015168670A1 (en) | 2014-05-02 | 2015-05-04 | Phosphate adhesion promoters |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2017518400A true JP2017518400A (ja) | 2017-07-06 |
JP6700195B2 JP6700195B2 (ja) | 2020-05-27 |
Family
ID=53190037
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2016563171A Active JP6700195B2 (ja) | 2014-05-02 | 2015-05-04 | リン酸接着促進剤 |
Country Status (10)
Country | Link |
---|---|
US (1) | US10155890B2 (ja) |
EP (1) | EP3137528B1 (ja) |
JP (1) | JP6700195B2 (ja) |
CN (1) | CN106232661B (ja) |
AR (1) | AR100394A1 (ja) |
BR (1) | BR112016024609B1 (ja) |
MX (1) | MX2016013671A (ja) |
RU (1) | RU2712450C1 (ja) |
TW (1) | TWI558779B (ja) |
WO (1) | WO2015168670A1 (ja) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2020532610A (ja) * | 2017-08-30 | 2020-11-12 | ダウ グローバル テクノロジーズ エルエルシー | 溶剤系接着剤組成物 |
JP2021519366A (ja) * | 2018-03-28 | 2021-08-10 | ダウ グローバル テクノロジーズ エルエルシー | リン酸エステル変性イソシアネートに基づく二成分接着剤組成物、およびそれを作製するための方法 |
JP2022510872A (ja) * | 2018-11-28 | 2022-01-28 | ダウ グローバル テクノロジーズ エルエルシー | ラミネートを形成するためのプロセス |
JP2022519151A (ja) * | 2018-11-22 | 2022-03-22 | ダウ グローバル テクノロジーズ エルエルシー | 接着剤組成物 |
JP7420825B2 (ja) | 2019-03-05 | 2024-01-23 | ダウ グローバル テクノロジーズ エルエルシー | 2成分無溶剤接着剤組成物 |
JP7473561B2 (ja) | 2019-03-05 | 2024-04-23 | ダウ グローバル テクノロジーズ エルエルシー | 2成分溶媒ベースの接着剤組成物 |
Families Citing this family (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10597559B2 (en) | 2016-06-06 | 2020-03-24 | Crane Composites, Inc. | Method of manufacturing a composite panel containing lauan or other moisture-carrying or moisture-absorbing material using adhesion promoter and panel made using the method |
CN109642013B (zh) * | 2016-07-11 | 2022-06-21 | 陶氏环球技术有限责任公司 | 高固体含量的基于溶剂的粘着剂组合物和其制造方法 |
CN109890929A (zh) * | 2016-09-19 | 2019-06-14 | 陶氏环球技术有限责任公司 | 双组分无溶剂粘合剂组合物和制造其的方法 |
EP3574031B1 (en) * | 2017-01-27 | 2023-12-27 | Dow Global Technologies LLC | Two-component solventless adhesive compositions |
EP3630858A1 (en) * | 2017-05-30 | 2020-04-08 | Dow Global Technologies LLC | Two-component solventless adhesive compositions |
EP3630862A1 (en) | 2017-05-31 | 2020-04-08 | Dow Global Technologies LLC | Solvent-based adhesive compositions |
WO2019060026A1 (en) * | 2017-09-22 | 2019-03-28 | Dow Global Technologies Llc | LAMINATED FILM STRUCTURES COMPRISING A BARRIER ADHESIVE LAYER |
WO2019130612A1 (en) * | 2017-12-28 | 2019-07-04 | Nitto Denko Corporation | Method for producing glass unit and pressure-sensitive adhesive sheet |
JP7443362B2 (ja) | 2018-11-16 | 2024-03-05 | ダウ グローバル テクノロジーズ エルエルシー | 無溶剤接着剤組成物ならびに作製するためのプロセスおよび積層体の形成における使用 |
AR118229A1 (es) | 2019-03-05 | 2021-09-22 | Dow Global Technologies Llc | Composición adhesiva de dos componentes sin solventes |
US20220213363A1 (en) * | 2019-05-15 | 2022-07-07 | Dow Global Technologies Llc | Two-component adhesive compositions, articles prepared with same and preparation methods thereof |
CN113825816B (zh) * | 2019-05-15 | 2023-11-24 | 陶氏环球技术有限责任公司 | 双组分粘合剂组合物、用其制备的制品及其制备方法 |
WO2020227964A1 (en) * | 2019-05-15 | 2020-11-19 | Dow Global Technologies Llc | Two-component adhesive compositions, articles prepared with same and preparation methods thereof |
MX2021016021A (es) | 2019-06-18 | 2022-02-21 | Dow Global Technologies Llc | Composición adhesiva de retorta. |
EP3986946A1 (en) * | 2019-06-18 | 2022-04-27 | Dow Global Technologies LLC | Retort adhesive composition |
EP4081565A1 (en) * | 2019-12-23 | 2022-11-02 | Dow Global Technologies LLC | Method of making zipper pouch |
CN115515783A (zh) | 2020-06-05 | 2022-12-23 | 陶氏环球技术有限责任公司 | 环氧磷酸酯 |
CN116134065A (zh) | 2020-07-30 | 2023-05-16 | 陶氏环球技术有限责任公司 | 无溶剂粘合剂组合物 |
WO2022082576A1 (en) * | 2020-10-22 | 2022-04-28 | Dow Global Technologies Llc | Isocyanate compounds and adhesive compositions comprising the same |
TW202224929A (zh) * | 2020-12-25 | 2022-07-01 | 律勝科技股份有限公司 | 積層板及其製造方法 |
CN116888182A (zh) | 2021-03-12 | 2023-10-13 | 陶氏环球技术有限责任公司 | 层压复合薄膜结构 |
KR20240034207A (ko) | 2021-07-13 | 2024-03-13 | 다우 글로벌 테크놀로지스 엘엘씨 | 내습성 2성분 접착제 조성물 |
CN114806144B (zh) * | 2022-05-11 | 2023-08-08 | 尼伦化学(上海)有限公司 | 分步交联结构tpu的制备方法及其护套线缆的制备方法 |
TW202346392A (zh) | 2022-05-16 | 2023-12-01 | 美商陶氏全球科技有限責任公司 | 快速固化及高效能層壓黏著劑 |
TW202346526A (zh) | 2022-05-16 | 2023-12-01 | 美商陶氏全球科技有限責任公司 | 具有低游離單體之高效能層壓黏著劑 |
WO2024098320A1 (en) | 2022-11-10 | 2024-05-16 | Dow Global Technologies Llc | Polyurethane adhesive |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3664975A (en) * | 1970-04-13 | 1972-05-23 | Monsanto Co | Flame resistant polyurethane prepared by adding an ethane diphosphonate into the urethane-forming mixture |
JPH04288380A (ja) * | 1991-03-15 | 1992-10-13 | Dai Ichi Kogyo Seiyaku Co Ltd | 被覆樹脂 |
JPH08507732A (ja) * | 1993-03-16 | 1996-08-20 | ダブリュ.エル.ゴア アンド アソシエィツ,インコーポレイティド | 難燃性で防水性でありかつ透湿性のラミネート |
JP2002003813A (ja) * | 2000-06-22 | 2002-01-09 | Toyo Mooton Kk | 接着剤組成物 |
JP2005089734A (ja) * | 2003-08-08 | 2005-04-07 | Mitsui Takeda Chemicals Inc | 2液硬化型無溶剤系接着剤および2液硬化型無溶剤系接着剤用組成物 |
JP2013253133A (ja) * | 2012-06-05 | 2013-12-19 | Dic Corp | リン酸変性化合物含有接着剤用樹脂組成物、及び接着剤 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2541027A (en) | 1948-05-11 | 1951-02-13 | Shell Dev | Compositions of matter containing epoxy ethers and phosphorus-containing compounds |
US3251828A (en) | 1962-10-23 | 1966-05-17 | Fmc Corp | Polyphosphoric acid esters of polyether polyols |
US3309427A (en) | 1963-01-15 | 1967-03-14 | Atlas Chemicals Ind Inc | Polyhydroxy phosphate esters |
US3580855A (en) | 1969-04-09 | 1971-05-25 | Rohm & Haas | Process for inhibition of scale and corrosion using a polyfunctional phosphated polyol ester having at least 75% primary phosphate ester groups |
US4507447A (en) | 1983-01-05 | 1985-03-26 | Takeda Chemical Industries, Ltd. | Polyurethane adhesive compositions containing oxyacid of phosphorus and silane coupling agent |
US5202391A (en) | 1988-06-28 | 1993-04-13 | Takeda Chemical Industries, Ltd. | Polyurethane adhesive of epoxy resin, polyisocyanate, phosphorus oxy acid, and carboxylic acid |
US5096980A (en) | 1988-06-28 | 1992-03-17 | Takeda Chemical Industries, Ltd. | Polyurethane adhesive of epoxy resin, polyisocyanate, phosphorus oxy acid, and carboxylic acid |
US5478897A (en) | 1993-04-26 | 1995-12-26 | Takeda Chemical Industries, Ltd. | Polyurethane adhesive compositions |
CN101370890B (zh) | 2006-02-17 | 2012-05-23 | 三井化学株式会社 | 层合用粘合剂 |
US8129492B1 (en) * | 2006-07-27 | 2012-03-06 | Ppg Industries Ohio, Inc. | Coating compositions comprising polyurea and a phosphorous-containing polyol |
DE102006045041A1 (de) * | 2006-09-25 | 2008-03-27 | Evonik Degussa Gmbh | Strahlenhärtbare Formulierung, die zu flexiblen Beschichtungen mit erhöhtem Korrosionsschutz auf Metalluntergründen führt |
DE102006054197A1 (de) * | 2006-11-15 | 2008-05-21 | Henkel Kgaa | Hochfeste Polyurethan-Klebstoffe |
DE102009014699A1 (de) * | 2009-03-27 | 2010-10-07 | Carl Freudenberg Kg | Verfahren zur Herstellung einer reaktiven Polyurethan-Emulsion |
CN101792465B (zh) * | 2009-12-11 | 2012-09-05 | 四川大学 | 磷酸多元醇酯与多异氰酸酯改性物及其制备方法和用途 |
ES2841988T3 (es) | 2011-10-14 | 2021-07-12 | Dow Global Technologies Llc | Polioles poliéster-poliéter híbridos para una expansión del desmoldo en espumas rígidas de poliuretanos mejorada |
-
2015
- 2015-04-17 AR ARP150101165A patent/AR100394A1/es active IP Right Grant
- 2015-04-17 TW TW104112376A patent/TWI558779B/zh active
- 2015-05-04 US US15/306,117 patent/US10155890B2/en active Active
- 2015-05-04 MX MX2016013671A patent/MX2016013671A/es unknown
- 2015-05-04 EP EP15723610.0A patent/EP3137528B1/en active Active
- 2015-05-04 RU RU2016145274A patent/RU2712450C1/ru active
- 2015-05-04 BR BR112016024609-8A patent/BR112016024609B1/pt active IP Right Grant
- 2015-05-04 WO PCT/US2015/028981 patent/WO2015168670A1/en active Application Filing
- 2015-05-04 JP JP2016563171A patent/JP6700195B2/ja active Active
- 2015-05-04 CN CN201580021259.7A patent/CN106232661B/zh active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3664975A (en) * | 1970-04-13 | 1972-05-23 | Monsanto Co | Flame resistant polyurethane prepared by adding an ethane diphosphonate into the urethane-forming mixture |
JPH04288380A (ja) * | 1991-03-15 | 1992-10-13 | Dai Ichi Kogyo Seiyaku Co Ltd | 被覆樹脂 |
JPH08507732A (ja) * | 1993-03-16 | 1996-08-20 | ダブリュ.エル.ゴア アンド アソシエィツ,インコーポレイティド | 難燃性で防水性でありかつ透湿性のラミネート |
JP2002003813A (ja) * | 2000-06-22 | 2002-01-09 | Toyo Mooton Kk | 接着剤組成物 |
JP2005089734A (ja) * | 2003-08-08 | 2005-04-07 | Mitsui Takeda Chemicals Inc | 2液硬化型無溶剤系接着剤および2液硬化型無溶剤系接着剤用組成物 |
JP2013253133A (ja) * | 2012-06-05 | 2013-12-19 | Dic Corp | リン酸変性化合物含有接着剤用樹脂組成物、及び接着剤 |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2020532610A (ja) * | 2017-08-30 | 2020-11-12 | ダウ グローバル テクノロジーズ エルエルシー | 溶剤系接着剤組成物 |
JP7145206B2 (ja) | 2017-08-30 | 2022-09-30 | ダウ グローバル テクノロジーズ エルエルシー | 溶剤系接着剤組成物 |
JP2021519366A (ja) * | 2018-03-28 | 2021-08-10 | ダウ グローバル テクノロジーズ エルエルシー | リン酸エステル変性イソシアネートに基づく二成分接着剤組成物、およびそれを作製するための方法 |
JP7405762B2 (ja) | 2018-03-28 | 2023-12-26 | ダウ グローバル テクノロジーズ エルエルシー | リン酸エステル変性イソシアネートに基づく二成分接着剤組成物、およびそれを作製するための方法 |
JP2022519151A (ja) * | 2018-11-22 | 2022-03-22 | ダウ グローバル テクノロジーズ エルエルシー | 接着剤組成物 |
JP7404364B2 (ja) | 2018-11-22 | 2023-12-25 | ダウ グローバル テクノロジーズ エルエルシー | 接着剤組成物 |
JP2022510872A (ja) * | 2018-11-28 | 2022-01-28 | ダウ グローバル テクノロジーズ エルエルシー | ラミネートを形成するためのプロセス |
JP7504096B2 (ja) | 2018-11-28 | 2024-06-21 | ダウ グローバル テクノロジーズ エルエルシー | ラミネートを形成するためのプロセス |
JP7420825B2 (ja) | 2019-03-05 | 2024-01-23 | ダウ グローバル テクノロジーズ エルエルシー | 2成分無溶剤接着剤組成物 |
JP7473561B2 (ja) | 2019-03-05 | 2024-04-23 | ダウ グローバル テクノロジーズ エルエルシー | 2成分溶媒ベースの接着剤組成物 |
Also Published As
Publication number | Publication date |
---|---|
WO2015168670A1 (en) | 2015-11-05 |
US10155890B2 (en) | 2018-12-18 |
TWI558779B (zh) | 2016-11-21 |
MX2016013671A (es) | 2017-01-23 |
TW201602273A (zh) | 2016-01-16 |
AR100394A1 (es) | 2016-10-05 |
CN106232661B (zh) | 2019-07-09 |
BR112016024609B1 (pt) | 2022-01-11 |
CN106232661A (zh) | 2016-12-14 |
US20170226391A1 (en) | 2017-08-10 |
EP3137528A1 (en) | 2017-03-08 |
BR112016024609A2 (pt) | 2017-08-15 |
EP3137528B1 (en) | 2020-12-16 |
JP6700195B2 (ja) | 2020-05-27 |
RU2712450C1 (ru) | 2020-01-29 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6700195B2 (ja) | リン酸接着促進剤 | |
TWI782012B (zh) | 雙組分無溶劑黏著劑組合物 | |
JP5889887B2 (ja) | Tpu貼合せ用接着剤 | |
TWI786161B (zh) | 溶劑基黏著劑組合物 | |
RU2757011C2 (ru) | Двухкомпонентная адгезивная композиция и способ её изготовления | |
JP2023536709A (ja) | 無溶剤接着剤組成物 | |
WO2015088764A1 (en) | Aminosilane adhesion promoter for urethane system | |
US20190127616A1 (en) | Two-component solventless adhesive compositions and methods of making same | |
JP2022536966A (ja) | レトルト接着剤組成物 | |
US11891480B2 (en) | Laminating adhesives using polyester from transesterification of polylactic acid with natural oils | |
JP2022536962A (ja) | レトルト接着剤組成物 | |
WO2019195066A1 (en) | Laminating adhesives using polyester from transesterification of polylactic acid with natural oils | |
US20230174835A1 (en) | Epoxy phosphate ester | |
TWI839322B (zh) | 雙組分無溶劑黏著劑組合物及製造其之方法 | |
TW202346526A (zh) | 具有低游離單體之高效能層壓黏著劑 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20161024 |
|
RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20170125 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20180416 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20190215 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20190215 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20190515 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20191011 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20200110 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20200305 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20200407 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20200430 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6700195 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
S531 | Written request for registration of change of domicile |
Free format text: JAPANESE INTERMEDIATE CODE: R313531 |
|
S802 | Written request for registration of partial abandonment of right |
Free format text: JAPANESE INTERMEDIATE CODE: R311802 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |