JP5000498B2 - 未硬化ゴムに硬化ポリウレタンを直接結合するための接着システム - Google Patents
未硬化ゴムに硬化ポリウレタンを直接結合するための接着システム Download PDFInfo
- Publication number
- JP5000498B2 JP5000498B2 JP2007519712A JP2007519712A JP5000498B2 JP 5000498 B2 JP5000498 B2 JP 5000498B2 JP 2007519712 A JP2007519712 A JP 2007519712A JP 2007519712 A JP2007519712 A JP 2007519712A JP 5000498 B2 JP5000498 B2 JP 5000498B2
- Authority
- JP
- Japan
- Prior art keywords
- adhesive
- primer
- vinyl ester
- resin
- polyurethane
- 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 - Fee Related
Links
- 239000000853 adhesive Substances 0.000 title claims abstract description 91
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 91
- 239000004814 polyurethane Substances 0.000 title claims abstract description 81
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 79
- 229920001971 elastomer Polymers 0.000 title claims abstract description 47
- 239000005060 rubber Substances 0.000 title abstract description 25
- 229920005989 resin Polymers 0.000 claims abstract description 69
- 239000011347 resin Substances 0.000 claims abstract description 69
- 239000000203 mixture Substances 0.000 claims abstract description 61
- 229920003244 diene elastomer Polymers 0.000 claims abstract description 58
- 229920001567 vinyl ester resin Polymers 0.000 claims abstract description 39
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 34
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 34
- 125000000524 functional group Chemical group 0.000 claims abstract description 23
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229920006241 epoxy vinyl ester resin Polymers 0.000 claims abstract description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 229920002857 polybutadiene Polymers 0.000 claims abstract description 7
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 5
- 229920002717 polyvinylpyridine Polymers 0.000 claims abstract description 5
- 239000002131 composite material Substances 0.000 claims description 31
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 28
- 239000000806 elastomer Substances 0.000 claims description 22
- 239000012790 adhesive layer Substances 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 13
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- -1 diisocyanate compound Chemical class 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002430 hydrocarbons Chemical group 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 abstract description 19
- 238000004519 manufacturing process Methods 0.000 abstract description 11
- 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 abstract description 8
- 229930185605 Bisphenol Natural products 0.000 abstract description 6
- 239000003292 glue Substances 0.000 description 24
- 150000001993 dienes Chemical class 0.000 description 23
- 238000000034 method Methods 0.000 description 18
- 239000010410 layer Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 11
- 230000002787 reinforcement Effects 0.000 description 11
- 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 11
- 239000004816 latex Substances 0.000 description 9
- 229920000126 latex Polymers 0.000 description 9
- 229920001225 polyester resin Polymers 0.000 description 9
- 239000004645 polyester resin Substances 0.000 description 9
- 239000000654 additive Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 229920003986 novolac Polymers 0.000 description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 239000011593 sulfur Substances 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 244000043261 Hevea brasiliensis Species 0.000 description 6
- 239000005062 Polybutadiene Substances 0.000 description 6
- 229920003052 natural elastomer Polymers 0.000 description 6
- 229920001194 natural rubber Polymers 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000006229 carbon black Substances 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 238000004073 vulcanization Methods 0.000 description 5
- 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 4
- 239000004970 Chain extender Substances 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 238000010276 construction Methods 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 229920003051 synthetic elastomer Polymers 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000001680 brushing effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 239000012936 vulcanization activator Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 2
- IBOFVQJTBBUKMU-UHFFFAOYSA-N 4,4'-methylene-bis-(2-chloroaniline) Chemical compound C1=C(Cl)C(N)=CC=C1CC1=CC=C(N)C(Cl)=C1 IBOFVQJTBBUKMU-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 239000000370 acceptor Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 230000003712 anti-aging effect Effects 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002148 esters Chemical group 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- NTMXFHGYWJIAAE-UHFFFAOYSA-N n,n-diethyl-3-oxobutanamide Chemical compound CCN(CC)C(=O)CC(C)=O NTMXFHGYWJIAAE-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920003192 poly(bis maleimide) Polymers 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 229920003225 polyurethane elastomer Polymers 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 230000003014 reinforcing effect Effects 0.000 description 2
- 239000012763 reinforcing filler Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 230000008093 supporting effect Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000007751 thermal spraying Methods 0.000 description 2
- 229920006337 unsaturated polyester resin Polymers 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 1
- CBXRMKZFYQISIV-UHFFFAOYSA-N 1-n,1-n,1-n',1-n',2-n,2-n,2-n',2-n'-octamethylethene-1,1,2,2-tetramine Chemical compound CN(C)C(N(C)C)=C(N(C)C)N(C)C CBXRMKZFYQISIV-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- PISLZQACAJMAIO-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine Chemical compound CCC1=CC(C)=C(N)C(CC)=C1N PISLZQACAJMAIO-UHFFFAOYSA-N 0.000 description 1
- BNCADMBVWNPPIZ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound COCN(COC)C1=NC(N(COC)COC)=NC(N(COC)COC)=N1 BNCADMBVWNPPIZ-UHFFFAOYSA-N 0.000 description 1
- AOFIWCXMXPVSAZ-UHFFFAOYSA-N 4-methyl-2,6-bis(methylsulfanyl)benzene-1,3-diamine Chemical compound CSC1=CC(C)=C(N)C(SC)=C1N AOFIWCXMXPVSAZ-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 229920013646 Hycar Polymers 0.000 description 1
- 102000006835 Lamins Human genes 0.000 description 1
- 108010047294 Lamins Proteins 0.000 description 1
- 241001112258 Moca Species 0.000 description 1
- 241000282376 Panthera tigris Species 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000010692 aromatic oil Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000701 coagulant Substances 0.000 description 1
- QAEKNCDIHIGLFI-UHFFFAOYSA-L cobalt(2+);2-ethylhexanoate Chemical compound [Co+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O QAEKNCDIHIGLFI-UHFFFAOYSA-L 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000013536 elastomeric material Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 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
- 230000001976 improved effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000002955 isolation Methods 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
- 229920003049 isoprene rubber Polymers 0.000 description 1
- 210000005053 lamin Anatomy 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- YPEWWOUWRRQBAX-UHFFFAOYSA-N n,n-dimethyl-3-oxobutanamide Chemical compound CN(C)C(=O)CC(C)=O YPEWWOUWRRQBAX-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001902 propagating effect Effects 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011208 reinforced composite material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000013040 rubber vulcanization Methods 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000001391 thioamide group Chemical group 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
-
- 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
- C08G18/58—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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/6705—Unsaturated polymers not provided for in the groups C08G18/671, C08G18/6795, C08G18/68 or C08G18/69
-
- 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
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/68—Unsaturated polyesters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyurethanes Or Polyureas (AREA)
- Tires In General (AREA)
- Paints Or Removers (AREA)
- Laminated Bodies (AREA)
- Lining Or Joining Of Plastics Or The Like (AREA)
- Liquid Crystal Substances (AREA)
- Lubricants (AREA)
- Steroid Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Processing And Handling Of Plastics And Other Materials For Molding In General (AREA)
- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0407666 | 2004-07-07 | ||
| FR0407666A FR2872820B1 (fr) | 2004-07-07 | 2004-07-07 | Systeme adhesif pour le collage direct d'un polyurethane cuit a du caoutchouc cru |
| PCT/EP2005/007287 WO2006002998A1 (fr) | 2004-07-07 | 2005-07-06 | Systeme adhesif pour le collage direct d'un polyurethanne cuit a du caoutchouc cru |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008505238A JP2008505238A (ja) | 2008-02-21 |
| JP2008505238A5 JP2008505238A5 (enExample) | 2008-08-21 |
| JP5000498B2 true JP5000498B2 (ja) | 2012-08-15 |
Family
ID=34946987
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007519712A Expired - Fee Related JP5000498B2 (ja) | 2004-07-07 | 2005-07-06 | 未硬化ゴムに硬化ポリウレタンを直接結合するための接着システム |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US20080029215A1 (enExample) |
| EP (1) | EP1765952B1 (enExample) |
| JP (1) | JP5000498B2 (enExample) |
| CN (1) | CN1981011B (enExample) |
| AT (1) | ATE463547T1 (enExample) |
| BR (1) | BRPI0513006A (enExample) |
| DE (1) | DE602005020449D1 (enExample) |
| FR (1) | FR2872820B1 (enExample) |
| WO (1) | WO2006002998A1 (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101939349B (zh) * | 2007-10-30 | 2013-08-14 | 米其林集团总公司 | 聚氨酯脲体系 |
| FR2962938B1 (fr) * | 2010-07-20 | 2013-06-14 | Michelin Soc Tech | Bandage flexible non pneumatique dont la structure porteuse comporte des lames metalliques |
| TWI534256B (zh) * | 2011-05-16 | 2016-05-21 | Showa Denko Kk | Hardened heat dissipation composition |
| JP2015533689A (ja) * | 2012-09-07 | 2015-11-26 | キャタピラー インコーポレイテッドCaterpillar Incorporated | 非空気式タイヤを形成するためのシステム及び方法 |
| WO2014070703A1 (en) * | 2012-10-30 | 2014-05-08 | SuperSprings International, Inc. | Vehicular suspension enhancement |
| FR3005054B1 (fr) * | 2013-04-26 | 2016-07-01 | Michelin & Cie | Polymere utilisable notamment comme primaire d'adhesion pour le collage de metal a du caoutchouc |
| WO2014201368A1 (en) | 2013-06-15 | 2014-12-18 | Ronald Thompson | Annular ring and non-pneumatic tire |
| CN103966853B (zh) * | 2014-05-15 | 2016-01-20 | 河北寰宇橡胶科技有限公司 | 一种聚酯钢化棕丝粘合活化剂及聚酯钢化棕丝的处理工艺 |
| WO2016019110A2 (en) | 2014-08-01 | 2016-02-04 | Utex Industries, Inc. | High pressure seal with composite anti-extrusion mechanism |
| WO2016126983A1 (en) | 2015-02-04 | 2016-08-11 | Advancing Mobility, Llc. | Non-pneumatic tire and other annular devices |
| WO2017106750A1 (en) | 2015-12-16 | 2017-06-22 | Thompson Ronald H | Track system for traction of a vehicle |
| CN108884208B (zh) | 2016-04-06 | 2021-09-21 | 三菱化学株式会社 | 热固性树脂组合物、片状模塑料及其制造方法、以及纤维增强复合材料 |
| US10569600B2 (en) | 2017-06-02 | 2020-02-25 | Bridgestone Americas Tire Operations, Llc | Adhesive systems for preparing composites of rubber and polar thermosets |
| US11179969B2 (en) | 2017-06-15 | 2021-11-23 | Camso Inc. | Wheel comprising a non-pneumatic tire |
| JP6785194B2 (ja) * | 2017-06-16 | 2020-11-18 | 株式会社ブリヂストン | タイヤ用樹脂金属複合部材、及びタイヤ |
| JP6785196B2 (ja) * | 2017-06-16 | 2020-11-18 | 株式会社ブリヂストン | タイヤ用樹脂金属複合部材、及びタイヤ |
| CN109337634B (zh) * | 2018-09-26 | 2021-04-27 | 上海维凯光电新材料有限公司 | 用于铝塑复合标签的高耐水解抗粘背胶黏剂及其制备 |
| KR102188669B1 (ko) * | 2019-02-01 | 2020-12-08 | 한국타이어앤테크놀로지 주식회사 | 무용매 반응형 접착 조성물 및 이를 이용한 타이어의 제조방법 |
| DE102020207204A1 (de) * | 2020-06-09 | 2021-12-09 | Rema Tip Top Ag | Reparaturpflaster für ein elastomeres Bauteil mit verbesserter Verbindungsschicht |
| CN114907791B (zh) * | 2021-02-08 | 2024-04-26 | 北京化工大学 | 一种非充气轮胎黏合材料及其制备方法及应用 |
| JP7783722B2 (ja) * | 2021-11-01 | 2025-12-10 | Toyo Tire株式会社 | 非空気圧タイヤの製造方法 |
| CN114058312A (zh) * | 2021-11-26 | 2022-02-18 | 中国科学院长春应用化学研究所 | 一种粘合体系、聚氨酯/橡胶复合材料及其制备方法 |
| KR102677597B1 (ko) * | 2022-09-06 | 2024-06-21 | 주식회사 대동농기계 | 트레드부와 스포크부 접합공정효율이 향상된 비공기압 타이어와 이의 제조방법 |
| CN115926714B (zh) * | 2022-12-01 | 2025-06-20 | 广东粤港澳大湾区黄埔材料研究院 | 一种单组分聚氨酯胶粘剂及其制备方法与应用 |
| CN118995083B (zh) * | 2024-08-13 | 2025-06-27 | 青岛朗道轮履技术有限公司 | 轮幅式非充气轮胎及其制备方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1000998B (de) * | 1954-07-16 | 1957-01-17 | Bayer Ag | Verfahren zur Herstellung hochvernetzter Kunststoffe |
| US2905582A (en) * | 1955-04-29 | 1959-09-22 | Lord Mfg Co | Method of bonding polyurethanes to rubbers |
| BE633030A (enExample) * | 1962-06-02 | |||
| JPS5133599B2 (enExample) * | 1972-11-29 | 1976-09-20 | ||
| WO1984000170A1 (en) | 1982-06-28 | 1984-01-19 | Dow Chemical Co | Stable aqueous dispersions of curable resinous compositions and adhesive and coating compositions prepared therefrom |
| JPS60250023A (ja) * | 1984-05-28 | 1985-12-10 | Dainippon Ink & Chem Inc | 活性エネルギ−線硬化性樹脂組成物 |
| US4804691A (en) * | 1987-08-28 | 1989-02-14 | Richards Medical Company | Method for making a biodegradable adhesive for soft living tissue |
| JPH01141908A (ja) * | 1987-11-30 | 1989-06-02 | Dainippon Ink & Chem Inc | 活性エネルギー線硬化性樹脂組成物 |
| US4942093A (en) * | 1988-09-09 | 1990-07-17 | Bridgestone/Firestone, Inc. | Adhesive system for bonding uncured rubber to cured polyurethane |
| JPH0737594B2 (ja) * | 1990-05-30 | 1995-04-26 | バンドー化学株式会社 | 繊維材料とゴム配合物との接着方法 |
| US5462617A (en) * | 1991-05-30 | 1995-10-31 | Bandag Licensing Corporation | Tire bonding systems |
| FR2787388B1 (fr) * | 1998-12-18 | 2001-01-12 | Conception & Dev Michelin Sa | Bandage elastique utilisable de facon non pneumatique |
| FR2812653A1 (fr) * | 2000-08-03 | 2002-02-08 | Michelin Soc Tech | Colle pour compositions de caoutchouc, son procede de preparation et articles comportant cette colle |
| FR2839015A1 (fr) * | 2002-04-29 | 2003-10-31 | Conception & Dev Michelin Sa | Bandage flexible non pneumatique |
-
2004
- 2004-07-07 FR FR0407666A patent/FR2872820B1/fr not_active Expired - Fee Related
-
2005
- 2005-07-06 BR BRPI0513006-9A patent/BRPI0513006A/pt not_active IP Right Cessation
- 2005-07-06 CN CN2005800229772A patent/CN1981011B/zh not_active Expired - Fee Related
- 2005-07-06 AT AT05763403T patent/ATE463547T1/de not_active IP Right Cessation
- 2005-07-06 US US11/631,701 patent/US20080029215A1/en not_active Abandoned
- 2005-07-06 EP EP05763403A patent/EP1765952B1/fr not_active Expired - Lifetime
- 2005-07-06 WO PCT/EP2005/007287 patent/WO2006002998A1/fr not_active Ceased
- 2005-07-06 JP JP2007519712A patent/JP5000498B2/ja not_active Expired - Fee Related
- 2005-07-06 DE DE602005020449T patent/DE602005020449D1/de not_active Expired - Lifetime
-
2012
- 2012-06-05 US US13/489,194 patent/US8623169B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1765952A1 (fr) | 2007-03-28 |
| FR2872820A1 (fr) | 2006-01-13 |
| WO2006002998A1 (fr) | 2006-01-12 |
| CN1981011B (zh) | 2012-03-14 |
| JP2008505238A (ja) | 2008-02-21 |
| US20130000841A1 (en) | 2013-01-03 |
| FR2872820B1 (fr) | 2008-09-05 |
| US8623169B2 (en) | 2014-01-07 |
| EP1765952B1 (fr) | 2010-04-07 |
| CN1981011A (zh) | 2007-06-13 |
| US20080029215A1 (en) | 2008-02-07 |
| BRPI0513006A (pt) | 2008-04-22 |
| ATE463547T1 (de) | 2010-04-15 |
| DE602005020449D1 (de) | 2010-05-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5000498B2 (ja) | 未硬化ゴムに硬化ポリウレタンを直接結合するための接着システム | |
| JP5039836B2 (ja) | ポリウレタン尿素系 | |
| EP1283151B1 (en) | Endless two part rubber track comprised of polyurethane based tread component and rubber carcass component and vehicle containing such track | |
| JP4995282B2 (ja) | ポリ尿素接着剤 | |
| JP5175587B2 (ja) | ポリウレタン・ゴム複合体、該ポリウレタン・ゴム複合体の製造方法、及び該ポリウレタン・ゴム複合体を使用した非空気圧タイヤ | |
| US6012498A (en) | Tires having belts of high modulus composites | |
| JP2019507817A (ja) | 変性ポリマー及び前記変性ポリマーを含む安定なエマルジョン | |
| JP5442443B2 (ja) | ポリウレタン尿素系 | |
| CN113727834B (zh) | 注塑成型期间粘合橡胶和塑料表面 | |
| US4774142A (en) | Multi-layer or laminated compound body, in particular vehicle tire, and process and coupling mass for its production | |
| US8261798B2 (en) | Polyurethaneurea system | |
| EP4349581B1 (en) | Method for producing a non-pneumatic tire and non-pneumatic tire | |
| WO2016135264A1 (en) | Pur/rubber tyre and method of its manufacture | |
| EP0157717B1 (en) | Polyurethane bonded to cured rubber | |
| US20160001619A1 (en) | Tire comprised of rubber tread interlocked with polyurethane carcass | |
| NL2003748C2 (en) | Tire and method for manufacturing a tire. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20080707 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20080707 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20110920 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20111207 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20111214 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120321 |
|
| 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: 20120416 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20120516 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20150525 Year of fee payment: 3 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |