CN107646043A - 用于环氧粘合剂的封闭的聚氨酯增韧剂 - Google Patents
用于环氧粘合剂的封闭的聚氨酯增韧剂 Download PDFInfo
- Publication number
- CN107646043A CN107646043A CN201680029849.9A CN201680029849A CN107646043A CN 107646043 A CN107646043 A CN 107646043A CN 201680029849 A CN201680029849 A CN 201680029849A CN 107646043 A CN107646043 A CN 107646043A
- Authority
- CN
- China
- Prior art keywords
- reaction product
- toughener
- weight
- epoxy
- product 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.)
- Pending
Links
- 229920006332 epoxy adhesive Polymers 0.000 title claims abstract description 31
- 239000004814 polyurethane Substances 0.000 title claims description 36
- 229920002635 polyurethane Polymers 0.000 title claims description 18
- 239000012745 toughening agent Substances 0.000 claims abstract description 126
- 239000000853 adhesive Substances 0.000 claims abstract description 60
- 230000001070 adhesive effect Effects 0.000 claims abstract description 60
- 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 claims abstract description 44
- 229930185605 Bisphenol Natural products 0.000 claims abstract description 35
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 34
- 239000007788 liquid Substances 0.000 claims abstract description 22
- OWMNWOXJAXJCJI-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxymethyl)oxirane;phenol Chemical compound OC1=CC=CC=C1.OC1=CC=CC=C1.C1OC1COCC1CO1 OWMNWOXJAXJCJI-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 119
- 229920000647 polyepoxide Polymers 0.000 claims description 53
- 239000003822 epoxy resin Substances 0.000 claims description 40
- 239000004593 Epoxy Substances 0.000 claims description 39
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 229920000642 polymer Polymers 0.000 claims description 18
- 239000012948 isocyanate Substances 0.000 claims description 17
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 14
- 235000013824 polyphenols Nutrition 0.000 claims description 14
- 150000002513 isocyanates Chemical class 0.000 claims description 13
- -1 aliphatic isocyanate Chemical class 0.000 claims description 12
- 229920000909 polytetrahydrofuran Polymers 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 150000008442 polyphenolic compounds Chemical class 0.000 claims description 9
- 150000002009 diols Chemical class 0.000 claims description 8
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 6
- 230000001588 bifunctional effect Effects 0.000 claims description 4
- 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 claims description 3
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 239000005062 Polybutadiene Substances 0.000 claims description 2
- 229920002857 polybutadiene Polymers 0.000 claims description 2
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 15
- 238000000034 method Methods 0.000 abstract description 13
- 238000002360 preparation method Methods 0.000 description 43
- 238000009472 formulation Methods 0.000 description 19
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 17
- 239000003054 catalyst Substances 0.000 description 17
- 229920001971 elastomer Polymers 0.000 description 17
- 239000005060 rubber Substances 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 14
- 125000003700 epoxy group Chemical group 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- 238000003860 storage Methods 0.000 description 11
- 239000011258 core-shell material Substances 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 229920002396 Polyurea Polymers 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 6
- 229940106691 bisphenol a Drugs 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 150000002118 epoxides Chemical class 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- 230000006870 function Effects 0.000 description 6
- 239000003349 gelling agent Substances 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 239000011159 matrix material Substances 0.000 description 6
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 5
- BRIXOPDYGQCZFO-UHFFFAOYSA-N 4-ethylphenylsulfonic acid Chemical compound CCC1=CC=C(S(O)(=O)=O)C=C1 BRIXOPDYGQCZFO-UHFFFAOYSA-N 0.000 description 5
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000004952 Polyamide Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000001118 alkylidene group Chemical group 0.000 description 4
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- 235000012222 talc Nutrition 0.000 description 4
- 239000013008 thixotropic agent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 3
- HSKNIMOEWAXVTR-UHFFFAOYSA-N CC(O)=O.CC(O)=O.CC(O)=O.P Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.P HSKNIMOEWAXVTR-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 3
- 239000000292 calcium oxide Substances 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 229910021485 fumed silica Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012764 mineral filler Substances 0.000 description 3
- 230000003014 reinforcing effect Effects 0.000 description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 2
- 229910002012 Aerosil® Inorganic materials 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 241000579895 Chlorostilbon Species 0.000 description 2
- 241000871495 Heeria argentea Species 0.000 description 2
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 2
- 241000736199 Paeonia Species 0.000 description 2
- 235000006484 Paeonia officinalis Nutrition 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 229910052876 emerald Inorganic materials 0.000 description 2
- 239000010976 emerald Substances 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000012744 reinforcing agent Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- HNSDLXPSAYFUHK-UHFFFAOYSA-N 1,4-bis(2-ethylhexyl) sulfosuccinate Chemical compound CCCCC(CC)COC(=O)CC(S(O)(=O)=O)C(=O)OCC(CC)CCCC HNSDLXPSAYFUHK-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 239000004970 Chain extender Substances 0.000 description 1
- 206010011416 Croup infectious Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- 229920001665 Poly-4-vinylphenol Polymers 0.000 description 1
- 229920002732 Polyanhydride Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 239000011805 ball Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229940072282 cardura Drugs 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- RUZYUOTYCVRMRZ-UHFFFAOYSA-N doxazosin Chemical compound C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 RUZYUOTYCVRMRZ-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000008450 motivation Effects 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 125000004402 polyphenol group Chemical group 0.000 description 1
- 229920003226 polyurethane urea Polymers 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/08—Polyurethanes from polyethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- 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
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/24—Catalysts containing metal compounds of tin
- C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
- C08G18/246—Catalysts containing metal compounds of tin tin salts of carboxylic acids containing also tin-carbon 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
-
- 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
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3215—Polyhydroxy compounds containing aromatic groups or benzoquinone 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
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene 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
- C08G18/28—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
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6204—Polymers of olefins
-
- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
- C08G18/6677—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
-
- 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
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
Q | R | S | |
重量% | [%] | [%] | [%] |
聚THF 2000 | 63.11 | 64.89 | 79.31 |
HDI | 10.61 | 9.98 | 13.29 |
三羟甲基丙烷 | 0.33 | 0.54 | |
DBTL | 0.06 | 0.05 | 0.06 |
ODBA 93% | 26.22 | 24.75 | |
二异丙基胺 | 6.8 | ||
总量 | 100.00 | 100.00 | 100 |
Mn[Da] | 4400 | 6200 | 5100 |
Mw[Da] | 8200 | 13900 | 10500 |
AA | AB | AC | AD | AE | AU | AV | |
粘度,Casson,45℃[Pas] | 323 | 327 | 507 | 439 | 430 | 152 | 299 |
在10s-1下的粘度[Pas] | 577 | 575 | 819 | 799 | 754 | 300 | 490 |
屈服应力,Casson,45℃[Pa] | 375 | 357 | 371 | 461 | 340 | 245 | 231 |
AA | AB | AC | AD | AE | AU | AV | |
在RT下的冲击剥离强度[N/mm] | 32 | 34 | 28 | 17 | 30 | 31 | 28 |
在-40℃下的冲击剥离强度[N/mm] | 23 | 24 | 9 | 0 | 24 | ||
搭接剪切强度[MPa] | 19 | 19 | 20 | 19 | 17 | ||
E-模量[MPa] | 1940 | 1780 | 2284 | 2717 | 1480 | 2092 | 1992 |
拉伸强度[MPa] | 36.7 | 38.7 | 46.6 | 54.9 | 33 | 37 | 34 |
伸长率[%] | 6.5 | 7.4 | 6.2 | 5.8 | 11.7 | 4.9 | 6.1 |
Tg,DSC[℃] | 108 | 103 | 100 | 93 | 112 |
BF | BG | BH | BI | BJ | BT | |
粘度,Casson,45℃[Pas] | 221 | 286 | 229 | 529 | 302 | 180 |
在10s-1下的粘度[Pas] | 455 | 580 | 519 | 958 | 573 | 308 |
屈服应力,Casson,45℃[Pa] | 358 | 438 | 528 | 505 | 331 | 163 |
30℃ | 40℃ | 50℃ | 60℃ | |
1周(所计算的粘度Casson) | 247 | 291 | 311 | 360 |
系数增加 | 1.1 | 1.3 | 1.4 | 1.6 |
差值 | 26 | 70 | 90 | 139 |
1周(在10s-1下的粘度) | 465 | 524 | 593 | 638 |
系数增加 | 1 | 1.2 | 1.3 | 1.4 |
差值 | 10 | 69 | 138 | 183 |
2周(所计算的粘度Casson) | 257 | 293 | 358 | 592 |
系数增加 | 1.2 | 1.3 | 1.6 | 2.7 |
差值 | 36 | 72 | 137 | 371 |
2周(在10s-1下的粘度) | 496 | 540 | 651 | 1036 |
系数增加 | 1.1 | 1.2 | 1.4 | 2.3 |
差值 | 41 | 85 | 196 | 581 |
3周(所计算的粘度Casson) | 273 | 306 | 412 | 999 |
系数增加 | 1.2 | 1.4 | 1.9 | 4.5 |
差值 | 52 | 85 | 191 | 778 |
3周(在10s-1下的粘度) | 516 | 580 | 693 | 1466 |
系数增加 | 1.1 | 1.3 | 1.5 | 3.2 |
差值 | 61 | 125 | 1.5 | 1011 |
4周(所计算的粘度Casson) | 281 | 317 | 457 | 1773 |
系数增加 | 1.3 | 1.4 | 2.1 | 8 |
差值 | 60 | 96 | 236 | 1552 |
4周(在10s-1下的粘度) | 493 | 611 | 785 | 2137 |
系数增加 | 1.1 | 1.3 | 1.7 | 4.7 |
差值 | 38 | 156 | 330 | 1682 |
BF | BG | BH | BI | BJ | BT | |
在RT下的冲击剥离强度[N/mm] | 29 | 26 | 22 | 12 | 26 | 27 |
在-40℃下的冲击剥离强度[N/mm] | 17 | 18 | 1 | 1 | 20 | |
搭接剪切强度[MPa] | 19 | 19 | 19 | 18 | 18 | |
E-模量[MPa] | 2296 | 2446 | 2670 | 3220 | 1773 | 2389 |
拉伸强度[MPa] | 45 | 46 | 54 | 59 | 36 | 38 |
伸长率[%] | 6.8 | 5.3 | 6.6 | 4.0 | 8.0 | 4.6 |
Tg,DSC[℃] | 98 | 90 | 91 | 92 | 106 |
RQ | RR | RS | |
粘度,Casson,45℃[Pas] | 73 | 102 | 39 |
在10s-1下的粘度[Pas] | 219 | 247 | 817 |
屈服应力,Casson,45℃[Pa] | 367 | 301 | 430 |
RQ | RR | RS | |
在RT下的冲击剥离强度[N/mm] | 34 | 30 | 38 |
在-40℃下的冲击剥离强度[N/mm] | 18 | 22 | 21 |
搭接剪切强度[MPa] | 19 | 24 | 20 |
E-模量[MPa] | 2305 | 2152 | 1844 |
拉伸强度[MPa] | 42 | 37 | 33 |
伸长率[%] | 5.0 | 3.8 | 4.1 |
Tg,DSC[℃] | 93 | 99 | 94 |
Claims (17)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202310865521.2A CN116891712A (zh) | 2015-06-02 | 2016-05-31 | 用于环氧粘合剂的封闭的聚氨酯增韧剂 |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201562169742P | 2015-06-02 | 2015-06-02 | |
US62/169,742 | 2015-06-02 | ||
PCT/US2016/034988 WO2016196448A1 (en) | 2015-06-02 | 2016-05-31 | Blocked polyurethane tougheners for epoxy adhesives |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202310865521.2A Division CN116891712A (zh) | 2015-06-02 | 2016-05-31 | 用于环氧粘合剂的封闭的聚氨酯增韧剂 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN107646043A true CN107646043A (zh) | 2018-01-30 |
Family
ID=56116588
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202310865521.2A Pending CN116891712A (zh) | 2015-06-02 | 2016-05-31 | 用于环氧粘合剂的封闭的聚氨酯增韧剂 |
CN201680029849.9A Pending CN107646043A (zh) | 2015-06-02 | 2016-05-31 | 用于环氧粘合剂的封闭的聚氨酯增韧剂 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202310865521.2A Pending CN116891712A (zh) | 2015-06-02 | 2016-05-31 | 用于环氧粘合剂的封闭的聚氨酯增韧剂 |
Country Status (7)
Country | Link |
---|---|
US (3) | US20180163104A1 (zh) |
EP (1) | EP3303432A1 (zh) |
JP (1) | JP6753868B2 (zh) |
KR (1) | KR102641039B1 (zh) |
CN (2) | CN116891712A (zh) |
BR (1) | BR112017024945B1 (zh) |
WO (1) | WO2016196448A1 (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110467712A (zh) * | 2019-08-14 | 2019-11-19 | 中国建筑材料科学研究总院有限公司 | 聚氨酯树脂材料及其制备方法和应用 |
CN111320838A (zh) * | 2018-12-13 | 2020-06-23 | 惠州佳鼎固化工有限公司 | 增韧剂组合物及环氧组合物 |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11820922B2 (en) * | 2017-10-18 | 2023-11-21 | Ddp Specialty Electronic Materials Us, Llc | Adhesive composition |
US11306178B2 (en) * | 2018-03-30 | 2022-04-19 | Nippon Steel Chemical & Material Co., Ltd. | Epoxy resin composition and cured product |
KR20210087444A (ko) * | 2018-11-08 | 2021-07-12 | 가부시키가이샤 아데카 | 경화성 수지 조성물 |
CN113308207B (zh) * | 2021-05-31 | 2022-10-28 | 东莞市雄林新材料科技股份有限公司 | 一种防泼水tpu热熔胶薄膜及其制备方法 |
Citations (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4788224A (en) * | 1986-12-24 | 1988-11-29 | Bayer Aktiengesellschaft | Two stage process for the production of molded articles |
EP0307666A1 (de) * | 1987-08-26 | 1989-03-22 | Ciba-Geigy Ag | Phenol-terminierte Polyurethane oder Polyharnstoffe und Epoxidharze enthaltend diese Verbindungen |
CN1726242A (zh) * | 2002-12-17 | 2006-01-25 | Sika技术股份公司 | 具有改善的低温冲击韧性的、可热硬化的环氧树脂组合物 |
CN1930206A (zh) * | 2004-03-12 | 2007-03-14 | 陶氏环球技术公司 | 环氧粘合剂组合物 |
CN101595134A (zh) * | 2006-12-22 | 2009-12-02 | Sika技术股份公司 | 酯预增长的环氧基封端的韧性改进剂及其制备方法 |
CN101679579A (zh) * | 2007-06-20 | 2010-03-24 | 陶氏环球技术公司 | 对温度变化的敏感性非常低的耐碰撞环氧粘合剂 |
CN101815734A (zh) * | 2007-10-05 | 2010-08-25 | 陶氏环球技术公司 | 异氰酸酯改性环氧树脂及其环氧粉末涂料组合物 |
EP2436712A1 (de) * | 2010-10-01 | 2012-04-04 | Sika Technology AG | Schlagzähigkeitsmodifikatoren für Epoxidharzzusammensetzungen |
CN103649154A (zh) * | 2011-07-04 | 2014-03-19 | 陶氏环球技术有限责任公司 | 在可热固化的环氧树脂体系中作为增韧剂的加合物 |
CN103732647A (zh) * | 2011-08-22 | 2014-04-16 | 陶氏环球技术有限责任公司 | 增韧剂和增韧的环氧粘合剂 |
WO2014072426A1 (de) * | 2012-11-12 | 2014-05-15 | Sika Technology Ag | Reaktive flüssigkautschuke aus blockierten isocyanat-terminierten präpolymeren mit glycolfänger |
WO2014072515A1 (de) * | 2012-11-12 | 2014-05-15 | Sika Technology Ag | Neue schlagzähigkeitsmodifikatoren für epoxy-basierte klebstoffe |
CN104497271A (zh) * | 2014-12-24 | 2015-04-08 | 济南圣泉集团股份有限公司 | 一种改性环氧树脂和改性环氧树脂组合物 |
CN104662057A (zh) * | 2012-09-24 | 2015-05-27 | Sika技术股份公司 | 用于风力机的耐裂粘合剂的预聚物抗冲剂 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4612156A (en) * | 1985-02-26 | 1986-09-16 | The Dow Chemical Company | Solventless process for producing resinous materials |
CA1259897A (en) | 1985-04-02 | 1989-09-26 | Madan M. Bagga | Bonding process using curable epoxide resin adhesive |
US5278257A (en) | 1987-08-26 | 1994-01-11 | Ciba-Geigy Corporation | Phenol-terminated polyurethane or polyurea(urethane) with epoxy resin |
EP2258773A1 (en) | 2003-06-09 | 2010-12-08 | Kaneka Corporation | Epoxy resin |
US7557168B2 (en) | 2003-07-07 | 2009-07-07 | Dow Global Technologies, Inc. | Applying adhesive stream of epoxy resin, rubber modified epoxy resin and capped isocyanate prepolymer |
EP1498441A1 (de) | 2003-07-16 | 2005-01-19 | Sika Technology AG | Hitzehärtende Zusammensetzungen mit Tieftemperatur-Schlagzähigkeitsmodifikatoren |
US7642316B2 (en) | 2004-10-14 | 2010-01-05 | Dow Global Technologies, Inc. | Rubber modified monovinylidene aromatic polymers and fabricated articles prepared therefrom |
DE602005020260D1 (de) | 2005-06-02 | 2010-05-12 | Dow Global Technologies Inc | Schlagzähmodifizierter Strukturklebstoff auf Epoxid Basis |
JP5258290B2 (ja) | 2005-06-09 | 2013-08-07 | 株式会社Adeka | 硬化性樹脂組成物 |
EP1741734A1 (de) | 2005-07-05 | 2007-01-10 | Sika Technology AG | Tieftemperaturschlagzähe hitze-härtbare Epoxidharzzusammensetzung mit Epoxidfestharzen |
WO2012000171A1 (en) | 2010-06-29 | 2012-01-05 | Dow Global Technologies Llc | Storage-stable heat-activated tertiary amine catalysts for epoxy resins |
EP2888331B1 (en) * | 2012-08-27 | 2019-03-20 | Dow Global Technologies LLC | Accelerated and toughened two-part epoxy adhesives |
EP3009461A1 (de) * | 2014-10-13 | 2016-04-20 | Sika Technology AG | Polyester-Präpolymere als Schlagzähigkeitsverbesserer in Epoxyformulierungen |
-
2016
- 2016-05-31 WO PCT/US2016/034988 patent/WO2016196448A1/en active Application Filing
- 2016-05-31 CN CN202310865521.2A patent/CN116891712A/zh active Pending
- 2016-05-31 JP JP2017560658A patent/JP6753868B2/ja active Active
- 2016-05-31 US US15/574,601 patent/US20180163104A1/en not_active Abandoned
- 2016-05-31 EP EP16728201.1A patent/EP3303432A1/en active Pending
- 2016-05-31 KR KR1020177036372A patent/KR102641039B1/ko active IP Right Grant
- 2016-05-31 CN CN201680029849.9A patent/CN107646043A/zh active Pending
- 2016-05-31 BR BR112017024945-6A patent/BR112017024945B1/pt active IP Right Grant
-
2021
- 2021-08-06 US US17/396,069 patent/US20210371717A1/en not_active Abandoned
-
2023
- 2023-08-28 US US18/456,677 patent/US20230407154A1/en active Pending
Patent Citations (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4788224A (en) * | 1986-12-24 | 1988-11-29 | Bayer Aktiengesellschaft | Two stage process for the production of molded articles |
EP0307666A1 (de) * | 1987-08-26 | 1989-03-22 | Ciba-Geigy Ag | Phenol-terminierte Polyurethane oder Polyharnstoffe und Epoxidharze enthaltend diese Verbindungen |
CN1726242A (zh) * | 2002-12-17 | 2006-01-25 | Sika技术股份公司 | 具有改善的低温冲击韧性的、可热硬化的环氧树脂组合物 |
CN1930206A (zh) * | 2004-03-12 | 2007-03-14 | 陶氏环球技术公司 | 环氧粘合剂组合物 |
CN101595134A (zh) * | 2006-12-22 | 2009-12-02 | Sika技术股份公司 | 酯预增长的环氧基封端的韧性改进剂及其制备方法 |
CN101679579A (zh) * | 2007-06-20 | 2010-03-24 | 陶氏环球技术公司 | 对温度变化的敏感性非常低的耐碰撞环氧粘合剂 |
CN101815734A (zh) * | 2007-10-05 | 2010-08-25 | 陶氏环球技术公司 | 异氰酸酯改性环氧树脂及其环氧粉末涂料组合物 |
EP2436712A1 (de) * | 2010-10-01 | 2012-04-04 | Sika Technology AG | Schlagzähigkeitsmodifikatoren für Epoxidharzzusammensetzungen |
CN103649154A (zh) * | 2011-07-04 | 2014-03-19 | 陶氏环球技术有限责任公司 | 在可热固化的环氧树脂体系中作为增韧剂的加合物 |
CN103732647A (zh) * | 2011-08-22 | 2014-04-16 | 陶氏环球技术有限责任公司 | 增韧剂和增韧的环氧粘合剂 |
CN104662057A (zh) * | 2012-09-24 | 2015-05-27 | Sika技术股份公司 | 用于风力机的耐裂粘合剂的预聚物抗冲剂 |
WO2014072426A1 (de) * | 2012-11-12 | 2014-05-15 | Sika Technology Ag | Reaktive flüssigkautschuke aus blockierten isocyanat-terminierten präpolymeren mit glycolfänger |
WO2014072515A1 (de) * | 2012-11-12 | 2014-05-15 | Sika Technology Ag | Neue schlagzähigkeitsmodifikatoren für epoxy-basierte klebstoffe |
CN104497271A (zh) * | 2014-12-24 | 2015-04-08 | 济南圣泉集团股份有限公司 | 一种改性环氧树脂和改性环氧树脂组合物 |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111320838A (zh) * | 2018-12-13 | 2020-06-23 | 惠州佳鼎固化工有限公司 | 增韧剂组合物及环氧组合物 |
CN110467712A (zh) * | 2019-08-14 | 2019-11-19 | 中国建筑材料科学研究总院有限公司 | 聚氨酯树脂材料及其制备方法和应用 |
CN110467712B (zh) * | 2019-08-14 | 2021-09-03 | 中国建筑材料科学研究总院有限公司 | 聚氨酯树脂材料及其制备方法和应用 |
Also Published As
Publication number | Publication date |
---|---|
JP6753868B2 (ja) | 2020-09-09 |
JP2018522963A (ja) | 2018-08-16 |
EP3303432A1 (en) | 2018-04-11 |
WO2016196448A1 (en) | 2016-12-08 |
BR112017024945A2 (pt) | 2018-07-31 |
CN116891712A (zh) | 2023-10-17 |
BR112017024945B1 (pt) | 2022-05-24 |
KR102641039B1 (ko) | 2024-02-28 |
US20230407154A1 (en) | 2023-12-21 |
US20210371717A1 (en) | 2021-12-02 |
KR20180022673A (ko) | 2018-03-06 |
US20180163104A1 (en) | 2018-06-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US9181463B2 (en) | Structural epoxy resin adhesives containing chain-extended elastomeric tougheners capped with phenol, polyphenol or aminophenol compounds | |
CN107646043A (zh) | 用于环氧粘合剂的封闭的聚氨酯增韧剂 | |
US20240110085A1 (en) | High modulus, toughened one-component epoxy structural adhesives with high aspect ratio fillers | |
US20050070634A1 (en) | Process for applying a streamable epoxy adhesive | |
US7557168B2 (en) | Applying adhesive stream of epoxy resin, rubber modified epoxy resin and capped isocyanate prepolymer | |
EP3347391B1 (en) | Blocked polyurethane tougheners for epoxy adhesives | |
WO2009094295A1 (en) | Structural epoxy resin adhesives containing epoxide-functional, polyphenol-extended elastomeric tougheners | |
US20220195267A1 (en) | One-component toughened epoxy adhesives with improved humidity resistance | |
CN113853399B (zh) | 环氧粘合剂组合物及使用方法 | |
US20230365845A1 (en) | One-component structural adhesive | |
WO2023033919A1 (en) | Two-component structural adhesive | |
EP4396249A1 (en) | Two-component structural adhesive |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
TA01 | Transfer of patent application right | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20230327 Address after: Delaware Applicant after: DDP special electronic materials American Co. Address before: Delaware Applicant before: THE DOW CHEMICAL Co. Effective date of registration: 20230327 Address after: Delaware Applicant after: DDP special electronic materials USA Co.,Ltd. Address before: Delaware Applicant before: DDP special electronic materials American Co. Effective date of registration: 20230327 Address after: Delaware Applicant after: THE DOW CHEMICAL Co. Address before: Michigan, USA Applicant before: Dow Global Technologies Llc |
|
RJ01 | Rejection of invention patent application after publication | ||
RJ01 | Rejection of invention patent application after publication |
Application publication date: 20180130 |