CN110300770A - 低温固化粘合剂组合物 - Google Patents
低温固化粘合剂组合物 Download PDFInfo
- Publication number
- CN110300770A CN110300770A CN201880010558.4A CN201880010558A CN110300770A CN 110300770 A CN110300770 A CN 110300770A CN 201880010558 A CN201880010558 A CN 201880010558A CN 110300770 A CN110300770 A CN 110300770A
- Authority
- CN
- China
- Prior art keywords
- group
- adhesive composition
- groups
- alkyl
- lactamide
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 194
- 239000000853 adhesive Substances 0.000 title claims abstract description 177
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 177
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 97
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 97
- 230000000903 blocking effect Effects 0.000 claims abstract description 55
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 42
- 239000000758 substrate Substances 0.000 claims abstract description 39
- 150000002148 esters Chemical class 0.000 claims abstract description 32
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 30
- 150000007970 thio esters Chemical class 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 17
- -1 alkyl alcohol amide Chemical class 0.000 claims description 98
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 52
- 125000003118 aryl group Chemical group 0.000 claims description 44
- SXQFCVDSOLSHOQ-UHFFFAOYSA-N lactamide Chemical compound CC(O)C(N)=O SXQFCVDSOLSHOQ-UHFFFAOYSA-N 0.000 claims description 40
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
- 229920001971 elastomer Polymers 0.000 claims description 29
- 150000001408 amides Chemical class 0.000 claims description 28
- 229920000570 polyether Chemical group 0.000 claims description 28
- 229920000728 polyester Chemical group 0.000 claims description 27
- 239000000463 material Substances 0.000 claims description 26
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 24
- 239000004814 polyurethane Chemical group 0.000 claims description 24
- 229920002635 polyurethane Chemical group 0.000 claims description 24
- 238000005259 measurement Methods 0.000 claims description 23
- 125000004001 thioalkyl group Chemical group 0.000 claims description 21
- 239000002245 particle Substances 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000000806 elastomer Substances 0.000 claims description 15
- 150000001412 amines Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 230000010355 oscillation Effects 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000010008 shearing Methods 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 230000008859 change Effects 0.000 claims description 5
- 239000006071 cream Substances 0.000 claims description 5
- 238000005227 gel permeation chromatography Methods 0.000 claims description 4
- 239000004519 grease Substances 0.000 claims description 4
- 150000002989 phenols Chemical class 0.000 claims description 4
- 230000008929 regeneration Effects 0.000 claims description 4
- 238000011069 regeneration method Methods 0.000 claims description 4
- 238000000518 rheometry Methods 0.000 claims description 4
- 238000005496 tempering Methods 0.000 claims description 4
- 150000002923 oximes Chemical group 0.000 claims description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical group ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000012745 toughening agent Substances 0.000 claims description 2
- 239000004793 Polystyrene Substances 0.000 claims 1
- 229920002223 polystyrene Polymers 0.000 claims 1
- 238000001723 curing Methods 0.000 description 41
- 239000011541 reaction mixture Substances 0.000 description 25
- 239000012948 isocyanate Substances 0.000 description 18
- 125000000962 organic group Chemical group 0.000 description 17
- 239000002253 acid Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 150000002513 isocyanates Chemical class 0.000 description 16
- 239000004593 Epoxy Substances 0.000 description 15
- ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 description 15
- 239000006185 dispersion Substances 0.000 description 15
- 239000005060 rubber Substances 0.000 description 14
- 229920003048 styrene butadiene rubber Polymers 0.000 description 14
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 12
- 150000002430 hydrocarbons Chemical class 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 150000003973 alkyl amines Chemical class 0.000 description 10
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 10
- 229920000647 polyepoxide Polymers 0.000 description 10
- 238000007711 solidification Methods 0.000 description 10
- 230000008023 solidification Effects 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- 239000008199 coating composition Substances 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 8
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- 239000002174 Styrene-butadiene Substances 0.000 description 7
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 239000011258 core-shell material Substances 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 229920002857 polybutadiene Polymers 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N Lactic Acid Natural products CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
- 229940106691 bisphenol a Drugs 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 5
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 5
- 229920006309 Invista Polymers 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000012975 dibutyltin dilaurate Substances 0.000 description 5
- 239000003822 epoxy resin Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 235000014655 lactic acid Nutrition 0.000 description 5
- 239000004310 lactic acid Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229920001451 polypropylene glycol Polymers 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- JJTUDXZGHPGLLC-ZXZARUISSA-N (3r,6s)-3,6-dimethyl-1,4-dioxane-2,5-dione Chemical compound C[C@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-ZXZARUISSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 4
- 239000003292 glue Substances 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 239000003643 water by type Substances 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N butyl alcohol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229920006389 polyphenyl polymer Polymers 0.000 description 3
- 239000012763 reinforcing filler Substances 0.000 description 3
- 239000013008 thixotropic agent Substances 0.000 description 3
- 239000013638 trimer Substances 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-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
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000004594 Masterbatch (MB) Substances 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000010960 cold rolled steel Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
- 125000005265 dialkylamine group Chemical group 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical class CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 2
- 229910001092 metal group alloy Inorganic materials 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 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
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 230000006340 racemization Effects 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000013558 reference substance Substances 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- FDYWJVHETVDSRA-UHFFFAOYSA-N 1,1-diisocyanatobutane Chemical compound CCCC(N=C=O)N=C=O FDYWJVHETVDSRA-UHFFFAOYSA-N 0.000 description 1
- WOGVOIWHWZWYOZ-UHFFFAOYSA-N 1,1-diisocyanatoethane Chemical compound O=C=NC(C)N=C=O WOGVOIWHWZWYOZ-UHFFFAOYSA-N 0.000 description 1
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- IKYNWXNXXHWHLL-UHFFFAOYSA-N 1,3-diisocyanatopropane Chemical compound O=C=NCCCN=C=O IKYNWXNXXHWHLL-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- ZHLHLPGSZRUSQQ-UHFFFAOYSA-N 1-isocyanato-2-(isocyanatomethyl)benzene Chemical class O=C=NCC1=CC=CC=C1N=C=O ZHLHLPGSZRUSQQ-UHFFFAOYSA-N 0.000 description 1
- FENFUOGYJVOCRY-UHFFFAOYSA-N 1-propoxypropan-2-ol Chemical compound CCCOCC(C)O FENFUOGYJVOCRY-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- WCOXQTXVACYMLM-UHFFFAOYSA-N 2,3-bis(12-hydroxyoctadecanoyloxy)propyl 12-hydroxyoctadecanoate Chemical compound CCCCCCC(O)CCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCC(O)CCCCCC)COC(=O)CCCCCCCCCCC(O)CCCCCC WCOXQTXVACYMLM-UHFFFAOYSA-N 0.000 description 1
- AFTBJQDQENGCPC-UHFFFAOYSA-N 2,5-ditert-butyl-4-methylphenol Chemical compound CC1=CC(C(C)(C)C)=C(O)C=C1C(C)(C)C AFTBJQDQENGCPC-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- HRXNWQMMTLLJJQ-UHFFFAOYSA-N 3,3,5-trimethylhexan-1-ol Chemical class CC(C)CC(C)(C)CCO HRXNWQMMTLLJJQ-UHFFFAOYSA-N 0.000 description 1
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 1
- 229920002972 Acrylic fiber Polymers 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- XQCAHHQYJQNIPE-UHFFFAOYSA-N C1C2(C(C1=CC=C2)N=C=O)N=C=O Chemical compound C1C2(C(C1=CC=C2)N=C=O)N=C=O XQCAHHQYJQNIPE-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 1
- 241000790917 Dioxys <bee> Species 0.000 description 1
- 239000005510 Diuron Substances 0.000 description 1
- 229920000965 Duroplast Polymers 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- CJKRXEBLWJVYJD-UHFFFAOYSA-N N,N'-diethylethylenediamine Chemical compound CCNCCNCC CJKRXEBLWJVYJD-UHFFFAOYSA-N 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N N-butylamine Natural products CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- PEOBCPVLDYQFQT-UHFFFAOYSA-N N1C=CC=C1.CC1=NNC(=C1)C Chemical class N1C=CC=C1.CC1=NNC(=C1)C PEOBCPVLDYQFQT-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229910003978 SiClx Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001334 alicyclic compounds Chemical class 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- WGSGKLSYPKUZAD-UHFFFAOYSA-N bicyclo[3.1.1]hepta-1(6),2,4-triene Chemical compound C=1C2=CC=CC=1C2 WGSGKLSYPKUZAD-UHFFFAOYSA-N 0.000 description 1
- 238000005842 biochemical reaction Methods 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 239000002041 carbon nanotube Substances 0.000 description 1
- 229910021393 carbon nanotube Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 235000005513 chalcones Nutrition 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000011353 cycloaliphatic epoxy resin Substances 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 235000011868 grain product Nutrition 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 238000009863 impact test Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 229960002725 isoflurane Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000013035 low temperature curing Methods 0.000 description 1
- 208000030208 low-grade fever Diseases 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 1
- MWKFXSUHUHTGQN-UHFFFAOYSA-N n-decyl alcohol Natural products CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 150000003573 thiols Chemical group 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
- C09D201/02—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
- C08G18/0809—Manufacture of polymers containing ionic or ionogenic groups containing cationic or cationogenic groups
- C08G18/0814—Manufacture of polymers containing ionic or ionogenic groups containing cationic or cationogenic groups containing ammonium groups or groups forming them
-
- 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
- C08G18/10—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
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/20—Heterocyclic amines; Salts thereof
- C08G18/2045—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings
- C08G18/2072—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings having at least three nitrogen atoms in the condensed ring system
-
- 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
- C08G18/227—Catalysts containing metal compounds of antimony, bismuth or arsenic
-
- 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
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/285—Nitrogen containing compounds
- C08G18/2855—Lactams
-
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3253—Polyamines being in latent form
- C08G18/3256—Reaction products of polyamines with aldehydes or ketones
-
- 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
- C08G18/3271—Hydroxyamines
-
- 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
-
- 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
- C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
- C08G18/6415—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63 having nitrogen
- C08G18/643—Reaction products of epoxy resins with at least equivalent amounts of amines
-
- 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
-
- 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
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7621—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring being toluene diisocyanate including isomer mixtures
-
- 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
-
- 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
- C08G18/80—Masked polyisocyanates
-
- 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
- C08G18/80—Masked polyisocyanates
- C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
- C08G18/8006—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32
- C08G18/8009—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203
- C08G18/8022—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203 with polyols having at least three hydroxy groups
- C08G18/8029—Masked aromatic polyisocyanates
-
- 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
- C08G18/80—Masked polyisocyanates
- C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
-
- 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
- C08G18/80—Masked polyisocyanates
- C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
- C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
-
- 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
- C08G18/80—Masked polyisocyanates
- C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
- C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
- C08G18/8074—Lactams
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/24—Electrically-conducting paints
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/44—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications
-
- 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/08—Macromolecular additives
-
- 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
- C09J175/06—Polyurethanes from polyesters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2207/00—Properties characterising the ingredient of the composition
- C08L2207/53—Core-shell polymer
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Manufacturing & Machinery (AREA)
- Molecular Biology (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Sealing Material Composition (AREA)
Abstract
本文公开了一种粘合剂组合物,其包含:含环氧基的组分;封闭的多异氰酸酯固化剂,其包含衍生自的封闭剂的封闭基团,该封闭剂包含α‑羟基酰胺,酯或硫酯,或其组合。还公开了用粘合剂组合物形成粘合基材的方法。还公开了包含第一和第二基材和粘合剂组合物的制品。
Description
相关申请的交叉引用
本申请要求于2017年2月7日提交的名称为“LOW-TEMPERATURE CURINGELECTRODEPOSITABLE COATING COMPOSITIONS”的美国临时申请No.62/455,778的优先权,该临时申请通过引用整体明确地并入本文。
领域
本发明涉及粘合剂组合物和粘合剂。
背景
结构粘合剂用于广泛多种应用中以将两种或更多种基材材料粘合在一起。例如,结构粘合剂可用于将汽车或工业部件粘合在一起。
本发明涉及粘合剂组合物,其提供足够的粘合强度并且易于应用于将基材材料粘合在一起。
概述
本文公开了一种粘合剂组合物,其包含:含环氧基的组分;和封闭的多异氰酸酯固化剂,其包含衍生自包含α-羟基酰胺,酯或硫酯,或其组合的封闭剂的封闭基团。
本文还公开了一种在两个基材之间形成粘合的方法,包括:施加粘合剂,其包含含环氧基团的组分,和包含衍生自包含α-羟基酰胺,酯或硫酯,或其组合的封闭剂的封闭基团的封闭的多异氰酸酯固化剂;使第二基材与粘合剂组合物接触,使粘合剂组合物位于第一和第二基材之间;并固化粘合剂组合物。
还公开了通过至少部分地固化包含以下的粘合剂形成的粘合剂:含环氧基的组分和包含衍生自包含α-羟基酰胺,酯或硫酯或其组合的封闭剂的封闭基团的封闭的多异氰酸酯固化剂。
还公开了一种制品,其包含第一基材,第二基材和包含含环氧基的组分的粘合剂,和包含衍生自包含α-羟基酰胺,酯或硫酯或其组合的封闭剂的封闭基团的封闭的多异氰酸酯固化剂。
详细说明
出于以下详细说明的目的,应当理解本发明可以采取不同的可选择的变化和步骤次序,除了有明确的相反规定之处。此外,除了任何操作实施例或者另有指示外,全部数字例如表示值,量,百分比,范围,子范围和分数的那些可以解读为是用措词“大约”作为前序的,即使该术语没有明确出现。因此,除非有相反的指示,否则下面的说明书和附加的权利要求中阐明的数字参数是近似值,其可以根据本发明所寻求获得的期望的性能而变化。最起码,和并非打算将等价原则的应用限制到权利要求的范围,每个数字参数应当至少按照所报告的有效数字的数目和通过使用普通的四舍五入技术来解释。在本文描述封闭或者开放式数字范围的情况下,处于或者包含于所述数字范围内的全部数字,值,量,百分比,子范围和分数被认为明确包括于和属于本申请的初始公开内容,如同这些数字,值,量,百分比,子范围和分数明确以它们的整体写出一样。
虽然阐明本发明宽的范围的数字范围和参数是近似值,但是在具体实施例中所述的数值是尽可能精确来报告的。但是任何数值本质上包含了由它们各自的测试测量中存在的标准偏差所必然形成的某些误差。
如本文中使用的,除非另有说明,复数术语可以包含其单数对应物,反之亦然,除非另有说明。例如,尽管这里提到“一种”环氧基和“一种”封闭基团,但是可以使用这些组分的组合(即多种)。
此外,在本申请中,“或”的使用是指“和/或”,除非另有明确说明,即使“和/或”可能明确地用于某些情况。
如本文使用的,“包括”,“含有”和类似术语在本申请上下文中被理解为是与“包含”同义的和所以是开放式的,并且不排除存在另外的未描述或未叙述的要素,材料,成分或方法步骤。如本文使用的,“组成为”在本申请上下文中被理解为排除存在着任何未指明的要素,成分或方法步骤。如本文使用的,“本质上组成为”在本申请上下文中被理解为包括所规定的要素,材料,成分或方法步骤“和对于所描述的基本和新颖的特性(一个或多个)没有实质性影响的那些”。
如本文使用的,术语“其上”,“在其上”,“施涂到其上”,“施涂到其上面”,“形成于其上”,“沉积于其上”,“沉积于其上面”表示形成,覆盖,沉积或者提供于表面上,但不必需与表面接触。例如,将粘合剂组合物“施涂到”基材上并不排除位于粘合剂组合物和基材之间的相同或不同组成的一个或多个其它介入涂层。
如本文所用,术语“结构粘合剂”是指具有至少10N/mm(通过CEAST 9350根据ISO11343测量)的楔形冲击强度的粘合剂。
如本文所用,“芳族”是指具有离域共轭π-体系的烃,其在碳原子之间具有交替的双键和单键,形成一个或多个共面的烃环。
如本文所定义,“1K”或“单组分”粘合剂组合物是这样的组合物,其中所有成分可以预混和储存,并且其中反应性组分在环境温度或略微热的条件下不容易反应,而是仅在被外部能源活化时反应。在没有来自外部能源的活化的情况下,组合物将在大程度上保持未反应(当在25℃下储存90天时粘度增加小于100%,其中在以下剪切条件下,粘度用AntonPaar Physica MCR 301流变仪测量,其具有25mm平行板和1mm间隙:调节:在0.1s-1剪切速率下旋转60秒;回火:240秒无剪切;振幅测试:在90秒内,从0.01到10%的对数增加应变的振荡(每3秒测量数据);剪切阶段(shear phase):在10Hz下的10%应变(y)的振荡120秒(每10秒测量数据);重新调节:在0.1s-1剪切速率下旋转60秒;再生模式:0.05%应变(y)的振荡120秒(每10秒测量数据))。可用于促进固化反应(即,环氧组分和固化剂的交联)的外部能源包括例如辐射(即,光化辐射,诸如紫外光)和/或热。
如本文所定义的,“2K”或“双组分”粘合剂组合物是这样的组合物,当混合时,其中至少一部分反应性组分容易反应和固化而没有来自外部能源的活化,例如在环境温度或略微热的条件下。本领域技术人员理解,粘合剂组合物的两种组分彼此分开储存,并在即将施用粘合剂组合物之前混合。
如本文进一步定义的,环境条件通常是指室温和湿度条件或这样的温度和湿度条件,其通常在将粘合剂施加到基材的区域中发现,例如在20℃至40℃的温度和20%至80%相对湿度下,而略微热的条件是略高于环境温度,但通常低于粘合剂组合物的固化温度的温度(即换句话说,在这样的温度和湿度条件下,低于其,反应性组分将容易反应并且固化,例如>40℃且小于100℃,在20%至80%相对湿度下)。
如本文所用,术语“聚合物”是指预聚物,低聚物,均聚物,共聚物,以及它们的共混物或混合物。
如本文所用,“Mw”是指重均分子量并且是指通过凝胶渗透色谱法相对于线型聚苯乙烯标准物测定的理论值800至900,000Da并且可以使用Waters 2695分离模块和Waters2414差示折光计(RI检测器)进行。使用四氢呋喃(THF)作为洗脱液,流速为1ml min-1,并且使用两个PL Gel Mixed C柱在室温下分离。
如本文所用,术语“催化剂”是指在本身没有经历任何永久性化学变化的情况下提高化学反应速率的物质。
如本文所用,除非另有说明,术语“基本上不含”是指特定材料不是有目的地分别添加到混合物或组合物中,并且仅作为杂质存在,其痕量小于1重量%,分别基于混合物或组合物的总重量计。如本文所用,除非另有说明,术语“完全不含”是指混合物或组合物分别不包含特定材料,即该混合物或组合物包含0重量%的此类材料。
本发明涉及一种固化组分,其包含或在一些情况下由或基本上由封闭的多异氰酸酯固化剂组成,所述封闭的多异氰酸酯固化剂包含衍生自包含α-羟基酰胺,酯或硫酯,或其组合的封闭剂的封闭基团。固化组分可以在由外部能量源(例如,在至少100℃的温度下施加热)活化时与含环氧基的组分反应。在不存在外部能源的情况下,多异氰酸酯可以用上述封闭基团封闭。在施加外部能量源时,由于除去多异氰酸酯的封闭基团,固化组分可与含环氧基的组分反应。如本文中使用的,“封闭的多异氰酸酯”表示其中至少一部分的异氰酸基基团被通过游离异氰酸基基团与封闭剂的反应引入的封闭基团封闭的多异氰酸酯。因此,封闭的多异氰酸酯可包括与一种或多种封闭剂反应的多异氰酸酯。如本文中使用的,“封闭剂”是指这样的化合物,其包含与存在于多异氰酸酯上的异氰酸基基团有反应性的官能团,使得将封闭剂的残余结构部分结合到异氰酸基基团,从而其在室温(即23℃)对活性氢官能团来说是稳定的。封闭剂的结合的残余结构部分,其提供了对活性氢官能团在室温的稳定性,在本文被称为“封闭基团”。封闭基团可通过参考通过与异氰酸基基团反应而衍生的封闭剂来确定。封闭基团可在合适的条件,比如升高的温度下被去除,从而游离的异氰酸基基团可由封闭的异氰酸基基团产生。因此,与封闭剂的反应可在升高的温度下逆转,从而之前封闭的异氰酸基基团能自由地与活性氢官能团反应。如本文中使用的,关于封闭的多异氰酸酯的封闭基团的术语“衍生自”意图指在封闭基团中存在封闭剂的残基,并且不意图限制为多异氰酸酯的异氰酸基基团与封闭剂的反应产生的封闭基团。因此,得自不包括异氰酸基基团与封闭剂的直接反应的合成途径的本发明的封闭基团,如下文更详细解释的,将仍被视为“衍生自”封闭剂。如本文中使用的,术语“封闭的”多异氰酸酯共同表示完全封闭的多异氰酸酯和至少部分封闭的多异氰酸酯。如本文中使用的,“完全封闭的多异氰酸酯”是指其中每个异氰酸基基团都被封闭基团封闭的多异氰酸酯。如本文中使用的,“至少部分封闭的多异氰酸酯”是指其中至少一部分的异氰酸基基团已经被封闭基团封闭,而其余异氰酸基基团与聚合物骨架的一部分反应的多异氰酸酯。
可用于制备本发明的封闭的多异氰酸酯的多异氰酸酯包括本领域已知的任何合适的多异氰酸酯。多异氰酸酯为包含至少两个、至少三个、至少四个或更多个异氰酸基官能团的有机化合物。例如,多异氰酸酯可包括脂族和/或芳族多异氰酸酯。如将理解的,芳族多异氰酸酯具有共价结合到芳族基团中存在的碳的异氰酸酯基团的氮原子,而脂族多异氰酸酯可含有通过非芳族烃基团间接结合到异氰酸基基团的芳族基团。脂族多异氰酸酯可包括例如(i)亚烷基异氰酸酯,比如三亚甲基二异氰酸酯,四亚甲基二异氰酸酯,五亚甲基二异氰酸酯,六亚甲基二异氰酸酯(“HDI”),1,2-亚丙基二异氰酸酯,1,2-亚丁基二异氰酸酯,2,3-亚丁基二异氰酸酯,1,3-亚丁基二异氰酸酯,亚乙基二异氰酸酯(ethylidenediisocyanate),以及亚丁基二异氰酸酯(butylidene diisocyanate),以及(ii)环亚烷基异氰酸酯,比如1,3-环戊烷二异氰酸酯,1,4-环己烷二异氰酸酯,1,2-环己烷二异氰酸酯,异氟尔酮二异氰酸酯,亚甲基双(4-环己基异氰酸酯)(“HMDI”),1,6-六亚甲基二异氰酸酯的环状三聚体(cyclo-trimer)(亦称为HDI的异氰脲酸酯三聚体,可作为Desmodur N3300商购自Convestro AG),以及间四甲基苯二甲基二异氰酸酯(可作为商购自AllnexSA)。芳族多异氰酸酯可包括,例如,(i)亚芳基异氰酸酯,比如m-亚苯基二异氰酸酯,p-亚苯基二异氰酸酯,1,5-萘二异氰酸酯和1,4-萘二异氰酸酯,以及(ii)烷基亚芳基异氰酸酯,比如4,4′-二亚苯基甲烷二异氰酸酯(“MDI”),2,4-亚甲苯或2,6-亚甲苯二异氰酸酯(“TDI”),或它们的混合物,4,4-甲苯胺二异氰酸酯和苯二甲基二异氰酸酯。三异氰酸酯,比如三苯基甲烷-4,4′,4″-三异氰酸酯,1,3,5-三异氰酸基苯和2,4,6-三异氰酸基甲苯,四异氰酸酯,比如4,4′-二苯基二甲基甲烷-2,2′,5,5′-四异氰酸酯,以及聚合的多异氰酸酯,比如亚甲苯二异氰酸酯二聚体和三聚体等,也可使用。可使用多异氰酸酯的组合。
根据本发明,封闭的多异氰酸酯固化剂包含封闭基团,其衍生自包含α羟基酰胺、酯或硫酯的封闭剂。如本文中使用的,术语“α羟基酰胺”是指具有至少一个包含共价键接到酰胺基团的α碳的羟基官能团的α羟基酰胺结构部分的有机化合物。如本文中使用的,术语“α羟基酯”是指具有至少一个包含共价键接到酯基团的α碳的羟基官能团的α羟基酯结构部分的有机化合物。如本文中使用的,术语“α羟基硫酯”是指具有至少一个包含共价键接到硫酯基团的α碳的羟基官能团的α羟基硫酯结构部分的有机化合物。包含α羟基酰胺、酯或硫酯的封闭剂可包括结构(I)的化合物:
其中X为N(R2),O,S;n为1至4;当n=1且X=N(R2)时,R为氢,C1-C10烷基基团,芳基基团,聚醚,聚酯,聚氨酯,羟基烷基基团,或硫代烷基基团;当n=1且X=O或S时,R为C1-C10烷基基团,芳基基团,聚醚,聚酯,聚氨酯,羟基烷基基团,或硫代烷基基团;当n=2至4时,R为多价C1-C10烷基基团,多价芳基基团,多价聚醚,多价聚酯,多价聚氨酯;每个R1独立地为氢,C1-C10烷基基团,芳基基团,或环脂族基团;每个R2独立地为氢,C1-C10烷基基团,芳基基团,环脂族基团,羟基烷基基团,或硫代烷基基团;以及R和R2可以一起形成环脂族、杂环结构。该环脂族、杂环结构可包括例如吗啉,哌啶,或吡咯烷。应注意,如果X为N(R2),则R只能为氢。
如本文中使用的,“烷基”是指可为直链或支化的并可包含一个或多个不是芳族的烃环的烃链。如本文中使用的,“芳基”是指这样的烃,其具有离域共轭π-体系,碳原子间交替的双键和单键形成一个或多个共平面烃环。如本文中使用的,“环脂族”是指包含一个或多个不是芳族的烃环的烃。如本文中使用的,术语“聚醚”是指具有多于一个醚基团并且可任选地包含其它官能团,比如羟基或氨基基团的烃。如本文中使用的,术语“聚酯”是指具有多于一个酯基团并且可任选地包含其它官能团,比如羟基或氨基基团的烃化合物。如本文中使用的,术语“聚氨酯”是指具有多于一个氨基甲酸酯基团并且可任选地包含其它官能团,比如羟基或氨基基团的烃化合物。如本文中使用的,术语“羟基-烷基基团”是指具有羟基官能团的烷基基团。如本文中使用的,术语“硫代烷基基团”是指具有硫醇官能团的烷基基团。
α羟基酰胺封闭剂可包含取代的乙醇酰胺。如本文中使用的,术语“取代的乙醇酰胺”是指具有至少一个键接到氮原子的氢原子被取代基,比如单价有机基团取代的乙醇酰胺化合物。取代的乙醇酰胺,参考结构(I),包括以下化合物,其中X为N(R2);R1为氢;每个R2独立地为氢,C1-C10烷基基团,芳基基团,环脂族基团,羟基烷基基团,或硫代烷基基团;以及R为C1-C10烷基基团,芳基基团,环脂族基团,聚醚,聚酯,聚氨酯,羟基烷基基团,或硫代烷基基团。因此,取代的乙醇酰胺可包含烷基乙醇酰胺,芳基乙醇酰胺,聚醚乙醇酰胺,聚酯乙醇酰胺,聚氨酯乙醇酰胺,羟基烷基乙醇酰胺,或硫代烷基乙醇酰胺。这些化合物的每一种可为单或二取代的,比如,例如,参考烷基乙醇酰胺,单烷基乙醇酰胺或二烷基乙醇酰胺。单烷基乙醇酰胺的非限制性具体实例包括,例如,甲基乙醇酰胺,乙基乙醇酰胺,丙基乙醇酰胺,异丙基乙醇酰胺,丁基乙醇酰胺,戊基乙醇酰胺,己基乙醇酰胺,庚基乙醇酰胺,辛基乙醇酰胺,乙基-己基乙醇酰胺,壬基乙醇酰胺,癸基乙醇酰胺等等,并且二烷基乙醇酰胺的具体实例包含具有另外的烷基取代基的任何单烷基乙醇酰胺,比如二甲基乙醇酰胺,二乙基乙醇酰胺,二丁基乙醇酰胺,二戊基乙醇酰胺等等。
另外,取代的乙醇酰胺封闭剂可包含多于一个乙醇酰胺基团,比如,参考结构(I),当n大于1时。应理解的是,当n为1时,R基团为单价的,而当n大于1时,R基团为多价的,比如多价C1-C10烷基基团,芳基基团,环脂族基团,聚醚,聚酯,或聚氨酯聚合物。
α羟基酰胺封闭剂可备选地或另外地包含取代的乳酰胺。如本文中使用的,术语“取代的乳酰胺”是指具有至少一个键接到氮原子的氢原子被取代基,比如单价有机基团取代的乳酰胺化合物。取代的乳酰胺,参考结构(I),包括以下化合物,其中X为N(R2);R1为甲基;每个R2独立地为氢,C1-C10烷基基团,芳基基团,环脂族基团,羟基烷基基团,或硫代烷基基团;以及R为C1-C10烷基基团,芳基基团,环脂族基团,聚醚,聚酯,聚氨酯,羟基烷基基团,或硫代烷基基团。因此,取代的乳酰胺可包含烷基乳酰胺,芳基乳酰胺,聚醚乳酰胺,聚酯乳酰胺,聚氨酯乳酰胺,羟基烷基乳酰胺,或硫代烷基乳酰胺。这些化合物的每一种可为单或二取代的,比如,例如,参考烷基乳酰胺,单烷基乳酰胺或二烷基乳酰胺。单烷基乳酰胺的非限制性具体实例包括甲基乳酰胺,乙基乳酰胺,丙基乳酰胺,异丙基乳酰胺,丁基乳酰胺,戊基乳酰胺,己基乳酰胺,庚基乳酰胺,辛基乳酰胺,乙基-己基乳酰胺,壬基乳酰胺,癸基乳酰胺等等,以及二烷基乳酰胺的具体实例包括二甲基乳酰胺,二乙基乳酰胺,二丙基乳酰胺,二丁基乳酰胺,二戊基乳酰胺,二己基乳酰胺等等。
另外,取代的乳酰胺封闭剂可包含多于一个乳酰胺基团,比如,参考结构(I),当n大于1时。应理解的是,当n为1时,R基团为单价的,而当n大于1时,R基团为多价的,比如多价C1-C10烷基基团,芳基基团,环脂族基团,聚醚,聚酯,或聚氨酯聚合物。
本发明的烷基乙醇酰胺或烷基乳酰胺封闭基团可包括例如如下结构的化合物:
其中R1为氢或甲基基团;R2为C1-C10烷基基团;以及R3为氢,C1-C10烷基基团。将理解的是,R1在该烷基乳酰胺中为甲基基团。
根据本发明,可用于制备封闭的多异氰酸酯的封闭剂可为外消旋乳酰胺封闭剂。如本文中使用的,术语“外消旋乳酰胺”或“外消旋乳酰胺封闭剂”是指乳酰胺立体异构体的混合物,其可包含20%至80重量%,比如30%至70重量%,比如40%至60重量%,比如约50重量%的具有R立构中心的乳酰胺,以及20%至80重量%,比如30%至70重量%,比如40%至60重量%,比如约50重量%的具有S立构中心的乳酰胺,基于乳酰胺立体异构体混合物的总重量。因此,封闭的多异氰酸酯可包含衍生自外消旋乳酰胺封闭剂的封闭基团,即衍生自乳酰胺立体异构体的混合物的乳酰胺的封闭基团。为简单起见,衍生自外消旋乳酰胺封闭剂的封闭基团可被称为“外消旋乳酰胺封闭基团”。
外消旋乳酰胺可通过使内消旋丙交酯与烷基胺反应来制备。丙交酯的通式为3,6-二甲基-1,4-二噁烷-2,5-二酮,并且包括在甲基取代基处的两个立构中心。如本领域技术人员将领会的,内消旋丙交酯不是手性的,因此,没有光学活性,因为它包含一个R立构中心和一个S立构中心。相反,D-丙交酯和L-丙交酯异构体包行两个R或两个S立构中心,并且可排他性地形成分别具有R或S立构中心的乳酰胺。该烷基胺化合物不受限制,并可包括任何合适的包含伯或仲氨基基团的化合物。例如,该烷基胺可包含具有通式R1N(H)R2的单烷基或二烷基胺,其中R1为氢或脂族、环脂族或芳族基团,以及R2为脂族、环脂族或芳族基团。该烷基基团可包括例如甲基,乙基,丙基,异丙基,丁基,仲丁基,戊基,己基基团等,以及该烷基基团可被其它官能团取代,比如硫醇或羟基官能团,硫连接基,醚连接基或酯连接基等。例如,取代的单烷基胺可包括聚醚胺,比如可以商品名获自HuntsmanCorporation的单胺。二烷基胺包含两个烷基基团并可包含两种不同烷基基团的组合,比如,例如甲基乙基胺。通过内消旋丙交酯与烷基胺反应制备的外消旋乳酰胺可产生两种乳酰胺化合物,一种具有R立构中心,一种具有S立构中心,并且每种化合物都包含该烷基胺的残基。例如,以下方案1所示的内消旋丙交酯与丁基胺的反应产生具有R立构中心的丁基乳酰胺和具有S立构中心的丁基乳酰胺,并且这两种分子可一起被称为外消旋丁基乳酰胺。类似地,选择不同的烷基胺将产生具有所选胺的烷基基团的外消旋乳酰胺。因此,外消旋乳酰胺可包括外消旋烷基乳酰胺或外消旋二烷基乳酰胺。外消旋烷基和二烷基乳酰胺的非限制性实例可包括外消旋甲基乳酰胺,外消旋乙基乳酰胺,外消旋丙基乳酰胺,外消旋丁基乳酰胺,外消旋丙基乳酰胺,外消旋己基乳酰胺,外消旋二甲基乳酰胺,外消旋二乙基乳酰胺,外消旋二丙基乳酰胺,外消旋二丁基乳酰胺,外消旋二丙基乳酰胺,外消旋二己基乳酰胺,外消旋甲基乙基乳酰胺,外消旋乙基丙基乳酰胺,外消旋丙基丁基乳酰胺,外消旋丁基丙基乳酰胺,外消旋丙基己基乳酰胺,以及外消旋环己基乳酰胺。
方案1
外消旋乳酰胺还可通过使乳酸烷基酯的外消旋混合物与烷基胺反应来制备。乳酸烷基酯具有通式X-2-羟基丙酸酯,其中X表示烷基基团,比如甲基,乙基,丙基,丁基,戊基,己基等。每个单独的乳酸烷基酯分子将具有R或S立构中心,并且该外消旋混合物将共同具有大致等比例的R和S异构体,从而该外消旋混合物不是光学活性的。使用乳酸烷基酯的外消旋混合物能通过与烷基胺反应来制备本文定义的“外消旋乳酰胺”。例如,以下方案2所示的乳酸乙酯的外消旋混合物与甲基胺的反应产生甲基乳酰胺的外消旋混合物(其在本文可被称为外消旋甲基乳酰胺)及乙醇副产物。任何以上列出的烷基胺都可与乳酸烷基酯反应形成外消旋乳酰胺。
方案2
已令人惊奇地发现,使用外消旋乳酰胺封闭基团产生非结晶的封闭的多异氰酸酯。如本文中使用的,“非结晶”的封闭的多异氰酸酯是指封闭的多异氰酸酯,其当处于静止状态时,在室温(例如25℃)处于液态,并且在室温保持液态至少30天的时间。相反,“结晶的”封闭的多异氰酸酯是指在室温处于固体晶体形式的封闭的多异氰酸酯,或如果在室温处于液态,将在室温历经少于30天,比如例如少于7天形成固体晶体。
本领域技术人员将理解,至少部分封闭的多异氰酸酯借助于引入聚合物型骨架也将是非结晶的。因此,由手性的丙交酯或乳酸酯产生并用作用于封闭至少部分封闭的多异氰酸酯的异氰酸基基团的封闭剂的乳酰胺可形成非结晶的至少部分封闭的多异氰酸酯。
包含衍生自封闭剂的封闭基团的封闭的多异氰酸酯固化剂还可通过不包括异氰酸基基团与封闭剂的直接反应的合成方法来制备,该封闭剂包括α羟基酰胺、酯或硫酯。例如,包含衍生自包括α羟基酰胺的封闭剂的封闭基团的封闭的多异氰酸酯固化剂可通过两步合成法制备,其中在第一步中,多异氰酸酯与α羟基酯反应,以及在第二步中,所得产物进一步与烷基胺反应。被标记为方案3的示例的反应途径如下给出,其中在第一步中,被标记为R-NCO(其中R为包括至少一个其它异氰酸基基团(未视出)的多价有机结构部分)的多异氰酸酯与α羟基酯(其中R为单价有机基团)反应,以及反应产物进一步与伯或仲胺(RN(H)R(其中每个R单独地对应于如上定义的R或R2)反应以产生根据本发明的封闭的多异氰酸酯固化剂。
方案3
制备包含衍生自包括α羟基酰胺的封闭剂的封闭基团的封闭的多异氰酸酯固化剂的另一示例的备选合成途径包括两步合成法,其中在第一步中,碳酸二烷基酯与α羟基酰胺反应,以及在第二步骤中,所得产物进一步与烷基胺反应。被标记为方案4的示例的反应途径如下给出,其中在第一步中,碳酸酯(其中每个R单独地为单价有机基团)与α羟基酰胺(其中每个R单独地对应于如上定义的R或R2)反应,以及反应产物进一步与伯或仲胺(其中一个R对应于多价有机结构部分,一个R对应于氢)反应以产生根据本发明的封闭的多异氰酸酯固化剂。
方案4
包括α羟基酰胺、酯或硫酯的封闭剂可封闭封闭的多异氰酸酯的至少10%的总封闭的异氰酸基基团,比如至少50%的总封闭的异氰酸基基团,比如至少65%的总封闭的异氰酸基基团,比如至少80%的总封闭的异氰酸基基团,比如至少95%的总封闭的异氰酸基基团,比如100%的总封闭的异氰酸基基团。包括α羟基酰胺、酯或硫酯的封闭剂可封闭封闭的多异氰酸酯的10%至100%的总封闭的异氰酸基基团,比如50%至100%的总封闭的异氰酸基基团,比如65%至100%的总封闭的异氰酸基基团,比如80%至100%的总封闭的异氰酸基基团,比如95%至100%的总封闭的异氰酸基基团。如本文中使用的,“总封闭的异氰酸基基团”是指多异氰酸酯的被封闭基团封闭的,否则将是未封闭的或能自由反应的异氰酸基基团。
根据本发明,封闭的多异氰酸酯可任选地包含除了且不同于衍生自包括α羟基酰胺、酯或硫酯的封闭剂的封闭基团的第二封闭基团。如本文中使用的,术语“第二封闭基团”是指除了被α羟基酰胺、酯或硫酯封闭剂封闭的封闭基团之外的一种或多种另外的封闭基团,并且不意图限制存在于封闭的多异氰酸酯中的不同封闭基团的数量。第二封闭基团可包括本领域已知的任何合适的封闭基团。例如,第二封闭基团可衍生自作为封闭剂的醇或酚类化合物。可用作第二封闭基团的封闭剂的醇包括脂族、环脂族和芳族烷基单醇和酚类化合物,比如,例如,低级脂族醇,比如甲基,乙基,氯乙基,丙基,丁基,戊基,己基,庚基,辛基,或壬基醇,3,3,5-三甲基己醇,癸基和月桂基醇等;芳族烷基醇,比如苯基甲醇,甲基苯基甲醇等等;二醇化合物,比如乙二醇单乙基醚,乙二醇单丁基醚等;以及羟基酮化合物,比如羟基丙酮等。可用作第二封闭基团的封闭剂的酚类化合物可包括苯酚,甲酚,二甲苯酚,硝基苯酚,氯苯酚,乙基苯酚,叔丁基苯酚和2,5-二叔丁基-4-羟基甲苯。如需要,可使用少量甚至更高分子量的、相对来说非挥发性的单醇,以在本发明提供的涂层中起增塑剂的作用。第二封闭基团还可衍生自其它封闭剂,包括叔羟基胺,比如二乙基乙醇胺,肟,比如甲基乙基酮肟,丙酮肟和环己酮肟,以及胺,比如二异丙基胺,丙二酸二乙酯(“DEM”)和二甲基吡唑(“DMP”)。第二封闭基团还可衍生自两种或更多种任何上述封闭剂的组合。
第二封闭基团,如果存在的话,可封闭封闭的多异氰酸酯的至少0.1%的总封闭的异氰酸基基团,以及可封闭不超过90%的总封闭的异氰酸基基团,比如不超过50%的总封闭的异氰酸基基团,比如不超过35%的总封闭的异氰酸基基团,比如不超过20%的总封闭的异氰酸基基团,比如不超过5%的总封闭的异氰酸基基团。第二封闭基团,当存在时,可封闭封闭的多异氰酸酯的0.1%至90%的总封闭的异氰酸基基团,比如0.1%至50%的总封闭的异氰酸基基团,比如0.1%至35%的总封闭的异氰酸基基团,比如0.1%至20%的总封闭的异氰酸基基团,比如0.1%至5%的总封闭的异氰酸基基团。
如上所述,封闭的多异氰酸酯可为完全封闭的多异氰酸酯,其中多异氰酸酯的异氰酸基基团被一种或多种上述封闭基团封闭。根据本发明,完全封闭的多异氰酸酯可具有封闭多异氰酸酯的每个异氰酸基基团的封闭基团,即100%的异氰酸基基团被封闭基团封闭,并且没有异氰酸基基团保持未封闭或能自由反应。然而,封闭的多异氰酸酯可具有少于100%的封闭的异氰酸基基团,只要该涂料组合物保持稳定的分散体,如本文定义。
另外,封闭的多异氰酸酯还可为以上所述的至少部分封闭的多异氰酸酯。至少部分封闭的多异氰酸酯可被上述一种或多种封闭基团部分封闭,剩余的异氰酸基基团与聚合物骨架反应,比如描述于美国专利No.3,947,338第2栏第65行至第5栏第33行,引述的部分通过引用并入本文。为测定仅存在于封闭的多异氰酸酯中的封闭基团的百分比,已与聚合物骨架反应的异氰酸基基团不应包括作为封闭的多异氰酸酯的总封闭的异氰酸基基团的一部分。因此,封闭封闭的多异氰酸酯的100%的总异氰酸基基团的包含例如衍生自包括α羟基酰胺、酯或硫酯的封闭剂的封闭基团的封闭的多异氰酸酯包括至少部分封闭的多异氰酸酯,其中衍生自包括α羟基酰胺、酯或硫酯的封闭剂的封闭基团封闭100%的未与聚合物骨架反应的异氰酸基基团。至少部分封闭的多异氰酸酯可具有封闭多异氰酸酯的每个未与聚合物骨架反应的异氰酸基基团的封闭基团,即100%的总异氰酸基基团被封闭基团封闭,并且没有异氰酸基基团保持未封闭或能自由反应。然而,至少部分封闭的多异氰酸酯还可具有少于100%的总封闭的异氰酸基基团,只要该涂料组合物保持稳定的分散体,如本文定义。
封闭的多异氰酸酯可选择为提供在低温固化的涂料组合物。如本领域技术人员将理解的,涂料组合物固化时所处的温度取决于许多因素,包括,例如,用于封闭多异氰酸酯的封闭基团,用于封闭多异氰酸酯的封闭基团的比例,以及存在于分散体中的任何固化催化剂。如将在以下讨论的,上述封闭的多异氰酸酯及下述固化催化剂的组合产生由于出乎意料的和令人惊奇的协同效应而在低温固化的涂料组合物。如本文中使用的,关于涂料组合物的固化所说的“低温”是指130℃或更低的温度。
如本文中使用的,术语“固化”、“固化的”或相似术语,在与本文所述的粘合剂组合物关联使用时是指,至少一部分的形成该粘合剂组合物的组分交联形成涂层。另外,粘合剂组合物的固化是指,使所述组合物经历固化条件(例如升高的温度),引起该粘合剂组合物的组分的反应性官能团反应,以及使得该组合物的组分交联并形成至少部分固化的涂层。如本文中使用的,关于粘合剂的术语“至少部分固化的”是指,如下形成的粘合剂,其通过使该粘合剂组合物经历固化条件从而该粘合剂组合物的组分的至少一部分的反应性基团发生化学反应而形成粘合剂。粘合剂组合物可被视为“至少部分固化的”,如果粘合剂组合物具有至少10N/mm的楔形冲击(通过CEAST 9350根据ISO 11343测量)。该涂料组合物还可经历固化条件从而获得基本上完全固化,并且其中进一步固化不产生涂层性能,比如,例如增加的楔形冲击性能。
本发明的封闭的多异氰酸酯固化剂可根据以下结构:
其中Y表示多价有机结构部分;m≥1;以及p≥0;X为N(R2),O,S;当X=N(R2)时,R为氢,C1-C10烷基基团,芳基基团,聚醚,聚酯,聚氨酯,羟基烷基基团,或硫代烷基基团;当X=O或S时,R为C1-C10烷基基团,芳基基团,聚醚,聚酯,聚氨酯,羟基烷基基团,或硫代烷基基团;每个R1独立地为氢,C1-C10烷基基团,芳基基团,或环脂族基团;当m≥2时,R任选地为多价C1-C10烷基基团,多价芳基基团,多价聚醚,多价聚酯,多价聚氨酯;每个R2独立地为氢,C1-C10烷基基团,芳基基团,环脂族基团,羟基烷基基团,或硫代烷基基团;R和R2可以一起形成环脂族、杂环结构;以及O-Z表示第二封闭剂的残基。
如本文中使用的,术语“多价”是指具有两个或更多个键接位点的有机结构部分,该有机结构部分通过该键接位点共价键接到其它有机结构部分。例如,多异氰酸酯是多价的,因为它包含两个或更多个异氰酸基基团,它通过该异氰酸基基团与其它有机结构部分共价键接。该有机结构部分可例如为烷基基团,环脂族基团,芳基基团,聚醚,聚酯,聚氨酯等等。
如本文中使用的,术语“单价”是指具有一个键接位点的有机结构部分,该有机结构部分通过该键接位点共价键接到另一有机结构部分。虽然单价用于指仅具有一个键接位点的有机结构部分,但并不排除存在其它官能团,比如,例如,在固化期间,有机结构部分可通过该其它官能团结合到另外的有机结构部分。
本发明还涉及粘合剂组合物,例如单组分粘合剂组合物,其包含以下或在一些情况下由以下组成,或在一些情况下基本上由以下组成:含环氧基的组分;和上述固化组分。应当理解,选择固化组分以便在由外部能源活化时与含环氧基的组分发生化学反应。
可使用的有用的含环氧基的组分包括多环氧化物,环氧加合物或其组合。合适的多环氧化物包括双酚A的多缩水甘油醚,例如828和1001环氧树脂,和双酚F二环氧化物,例如862,其可从Hexion Specialty Chemicals,Inc.商购获得。其它有用的多环氧化物包括多元醇的多缩水甘油醚,多元羧酸的多缩水甘油基酯,衍生自烯属不饱和脂环族化合物环氧化的多环氧化物,环氧分子中含有氧化烯基的多环氧化物,和环氧酚醛清漆树脂。仍其他非限制性环氧化合物包括环氧化双酚A酚醛清漆,环氧化苯酚酚醛清漆,环氧化甲酚酚醛清漆和三缩水甘油基对氨基苯酚双马来酰亚胺。
其它合适的含环氧基的组分包括环氧加合物,例如环氧聚酯,其形成为包含含环氧基的化合物,多元醇和酸酐的反应物的反应产物,如美国专利No.8,796,361,第3栏,第42行到第4栏第65行,其引用部分通过引用并入本文。
根据本发明,含环氧基的组分在粘合剂组合物中的存在量可为基于总组合物重量的至少50重量%,例如至少60%,例如至少70%,和在一些情况下,在粘合剂组合物中可存在的量基于总组合物重量不超过95重量%,例如不超过90%,例如不超过80%。根据本发明,含环氧基的组分在粘合剂组合物中的存在量可以为组合物总重量的50%至95%,例如70%至90%或60%至80%。
根据本发明,粘合剂组合物的含环氧基的组分的环氧当量重量可以是至少99g/eq,例如至少180g/eq,例如至少520g/eq,例如至少至少1,000g/eq,并且在一些情况下可以不超过2,000g/eq,例如不超过1,000g/eq,例如不超过560g/eq,例如不超过200g/eq。根据本发明,粘合剂组合物的含环氧基组分的环氧当量重量可以为99g/eq至2,000g/eq,例如180g/eq至1,000g/eq,例如520g/eq至560g/eq。如本文所用,“环氧当量重量”是通过将含环氧基组分的分子量除以含环氧基组分中存在的环氧基团的数量来确定的。
根据本发明,粘合剂组合物的含环氧基的组分的分子量(Mw)(如上所述进行)可以为至少198g/mol,例如至少222g/mol,例如至少370g/mol,例如至少1,000g/mol,并且在一些情况下不超过20,000g/mol,例如不超过4,000g/mol,例如不超过2,000g/mol,例如不超过1,100g/mol,例如不超过400g/mol,例如不超过300g/mol。根据本发明,粘合剂组合物的含环氧基的组分的分子量可以为198g/mol至20,000g/mol,例如222g/mol至4,000g/mol,例如370g/mol至2,000g/mol,例如1,000g/mol至1,100g/mol。
根据本发明的粘合剂组合物可任选地进一步包含弹性体颗粒。如本文所用,“弹性体颗粒”是指玻璃化转变温度(Tg)为-70℃至0℃的颗粒。弹性体颗粒可具有核/壳结构。合适的核-壳弹性体颗粒可以包含丁二烯橡胶或其他合成橡胶,例如苯乙烯-丁二烯和丙烯腈-丁二烯等,丙烯酸丁酯和/或丙烯酸2-乙基己酯。弹性体颗粒的类型及其浓度不受限制,只要粒度落入如下所示的特定范围内即可。
根据本发明,弹性体颗粒的平均粒度可以为0.02-500微米(20nm-500,000nm),例如,由Kanekea Texas Corporation提供的报告的橡胶颗粒的粒度,通过在工业上已知的标准技术测量,例如,根据ISO 13320和ISO 22412。
根据本发明,弹性体颗粒可任选地包含在环氧载体树脂中以引入粘合剂组合物中。合适的细分散的平均粒度为50nm至250nm的核-壳弹性体颗粒可以在环氧树脂中进行母料处理(master-batched),该环氧树脂例如芳族环氧化物,酚醛清漆环氧树脂,双酚A和/或双酚F二环氧化物,和/或脂族环氧化物,其包括环脂族环氧化物,其浓度范围为的5%-40%橡胶颗粒(重量),基于橡胶分散体的总重量,例如20%-35%。合适的环氧树脂还可包括环氧树脂的混合物。当使用时,环氧载体树脂可以是本发明的含环氧基的组分,使得存在于结构粘合剂组合物中的含环氧基的组分的重量包括环氧载体树脂的重量。
使用可用于本发明的粘合剂组合物的聚(丁二烯)橡胶颗粒的示例性非限制性商业核-壳弹性体颗粒产品包括双酚F中的核-壳聚(丁二烯)橡胶分散体(25%的橡胶,按重量计)(以Kane Ace MX 136商购),在828中的核壳聚(丁二烯)橡胶分散体(33%橡胶,按重量计)(以Kane Ace MX 153商购),在双酚A中的核-壳聚(丁二烯)橡胶分散体(37%橡胶,以重量计)(以Kane Ace MX 257商购)和在双酚F中的核-壳聚(丁二烯)橡胶分散体(37%橡胶,以重量计)(以Kane Ace MX 267市售),每个都可从Kaneka Texas Corporation获得。
使用可用于粘合剂组合物的苯乙烯-丁二烯橡胶颗粒的示例性非限制性商业核-壳弹性体颗粒产品包括在低粘度双酚A中的核-壳苯乙烯-丁二烯橡胶分散体(33%橡胶,按重量计)(可以Kane Ace MX 113商购),在双酚A中的核壳苯乙烯-丁二烯橡胶分散体(25%橡胶,按重量计)(以Kane Ace MX 125商购),在D.E.N.TM-438酚醛清漆环氧树脂中的核壳苯乙烯-丁二烯橡胶分散体(25%橡胶,按重量计)(以Kane Ace MX 215商购),在MY-721多官能环氧树脂中的核壳苯乙烯-丁二烯橡胶分散体(25%橡胶,按重量计)(以Kane Ace MX 416商购),在MY-0510多官能环氧树脂中的核壳苯乙烯-丁二烯橡胶分散体(25%橡胶,按重量计)(以Kane Ace MX 451商购),来自Synasia的Syna Epoxy 21环脂族环氧树脂中的核壳苯乙烯-丁二烯橡胶分散体(25%橡胶,按重量计)(以Kane AceMX 551商购)和聚丙二醇(MW 400)中的核壳苯乙烯-丁二烯橡胶分散体(25%橡胶,按重量计)(以Kane Ace MX 715商购),每个都可从Kaneka Texas Corporation获得。
基于总组合物重量,弹性体颗粒可以以至少1重量%的量存在于粘合剂组合物中,例如至少6%,例如至少11%,并且在一些情况下可以基于总组合物重量不超过42重量%,例如不超过37%,例如不超过32%的量存在于粘合剂组合物中。根据本发明,基于总组合物重量,弹性体颗粒在粘合剂组合物中的存在量可以为1%至42%(以重量计),例如6%至37%,例如11%至32%。
根据本发明,在粘合剂组合物中包含封闭多异氰酸酯的固化组分包括上述固化组分,因此这里不再重复。
基于粘合剂组合物的总重量,封闭的多异氰酸酯可以以至少5重量%,例如至少10重量%,例如至少20重量%的量存在于本发明的粘合剂组合物中,并且可以以不超过50重量%,例如不超过40重量%,例如不超过30重量%的量存在。基于粘合剂组合物的总重量,封闭的多异氰酸酯可以以5重量%至50重量%,例如20重量%至40重量%或10重量%至30重量%的量存在于粘合剂组合物中。
将本文公开的量的固化组分引入本发明的粘合剂组合物中可以为两个基材之间形成的接合处提供改进的机械性能,例如楔形冲击。
根据本发明,粘合剂组合物任选还可包含潜伏性固化催化剂。如本文所用,术语“潜伏性固化催化剂”是指由外部能源活化的催化剂。
有用的潜伏性固化催化剂可包括酰氨基胺或聚酰胺催化剂,例如可从AirProducts获得的产品之一,胺,二酰肼或双氰胺加合物和络合物,例如,可从Ajinomoto Fine Techno Company获得的产品之一,可从Alz Chem获得的双氰胺(A.K.A.),可从Alz Chem获得的3,4-二氯苯基-N,N-二甲基脲(A.K.A.Diuron),或其组合。
根据本发明,当使用时,基于总组合物重量计,潜伏性固化催化剂在粘合剂组合物中的存在量可以为至少0.1重量%,例如至少2重量%,例如至少5重量%,在一些情况下,基于总组合物重量计,在粘合剂组合物中可存在的量不超过10重量%,例如不超过5重量%,例如不超过2重量%。根据本发明,当使用时,基于总组合物重量计,次要的(secondary)潜伏性固化催化剂在粘合剂组合物中的存在量可以为0.1重量%至10重量%,例如2重量%至5重量%。
根据本发明,粘合剂组合物可任选地进一步包含溶剂,例如醇,甲基异丁基酮,丙二醇甲醚或丙二醇丙基醚。基于粘合剂组合物的总组合物重量,溶剂在粘合剂组合物中的存在量可以为1至5重量%。或者,根据本发明,粘合剂组合物可以基本上不含溶剂,或者在某些情况下完全不含溶剂。如果溶剂的存在量小于2重量%,则粘合剂组合物基本上不含溶剂,基于粘合剂组合物的总组合物重量。
根据本发明,可任选地将增强填料添加到粘合剂组合物中。可以引入本发明的粘合剂组合物以提供改进的机械性能的有用的增强填料包括纤维材料,例如玻璃纤维,纤维状二氧化钛,晶须型碳酸钙(文石)和碳纤维(其包括石墨和碳纳米管)。另外,研磨至5微米或更宽并且研磨至50微米或更长的玻璃纤维也可提供额外的拉伸强度。如果使用的话,这种增强填料可以占组合物总重量的0.5重量%至25重量%。
任选地,根据本发明,还可以向粘合剂组合物中加入另外的填料,触变剂,着色剂,调色剂和/或其他材料。
可以使用的有用的触变剂包括未处理的气相法二氧化硅和处理过的气相法二氧化硅,蓖麻蜡,粘土,有机粘土及其组合。另外,也可以使用诸如合成纤维如纤维和纤维,丙烯酸纤维和/或工程纤维素纤维的纤维。
有用的着色剂或调色剂可包括红铁颜料,二氧化钛,碳酸钙和酞菁蓝及其组合。
可与触变剂结合使用的有用填料可包括无机填料,例如无机粘土或二氧化硅及其组合。
可以使用的示例性其他材料包括例如氧化钙和炭黑及其组合。
本发明还涉及制备如上所述的本发明粘合剂组合物的方法,该方法包括或在某些情况下由以下组成,或者在某些情况下基本上由以下组成:混合含环氧基的组分和固化组分和任选的任何其他成分(如果使用的话),在低于50℃的温度下,例如0℃至50℃,例如25℃至40℃。
本发明还涉及一种在两个基材之间形成粘合的方法,所述方法包括或者在一些情况下由以下组成,或者在一些情况下基本上由以下组成:将上述粘合剂组合物施加到第一基材;使第二基材与粘合剂组合物接触,使得粘合剂组合物位于第一基材和第二基材之间;并且固化粘合剂组合物,例如通过施加外部能量源。
上述粘合剂组合物可以单独施用或作为粘合剂体系的一部分施用,所述粘合剂体系可以以许多不同的方式沉积在许多不同的基材上。粘合剂体系可包含许多相同或不同的粘合剂层,并且还可包含其他涂料组合物,例如预处理组合物等。当通过本领域普通技术人员已知的方法(例如,通过暴露于热加热)至少部分地固化沉积在基材上的粘合剂组合物时,通常形成粘合剂层。
粘合剂组合物可以以任何数量的不同方式施加到基材表面上,其非限制性实例包括刷涂,辊涂,膜,粒料,喷枪和涂布机枪。
在施加到基材之后,粘合剂组合物可以固化,例如通过在升高的温度下烘烤和/或固化,例如在至少80℃的温度,例如至少100℃,例如至少120℃,例如至少125℃,例如至少130℃,在某些情况下温度不超过200℃,例如不超过180℃,例如不超过170℃,例如不超过165℃,在某些情况下温度从80℃到200℃,从120℃到180℃,从125℃到170℃,从130℃到165℃,以及足以至少部分地固化基材上的粘合剂组合物的任何所需时间段(例如,5分钟到1小时)。
在将粘合剂组合物施加到基材上并至少部分固化之后,可以评估粘合的基材的楔形冲击。楔形冲击试验评估粘合性粘合的接合处在受到冲击时的断裂行为。楔形冲击根据ISO 11343测量。例如,汽车工业中的可接受值可以是至少10N/mm,例如至少15N/mm。在将粘合剂组合物施加到基材上并且至少部分固化之后,粘合的基材可以表现出至少15N/mm的楔形冲击(通过CEAST 9350根据ISO 11343测量),例如至少16N/mm,例如至少17N/mm。因此,令人惊讶地发现,与不包括封闭的多异氰酸酯固化剂的粘合剂组合物相比,在本发明的粘合剂组合物中使用包含封闭的多异氰酸酯固化剂的固化组分导致改善的楔形冲击性能。例如,与不包含封闭的多异氰酸酯固化剂的对比粘合剂组合物相比,楔形冲击可以改善至少50%,例如至少60%,例如至少75%,例如至少90%,例如至少100%。
如上所述,本公开涉及粘合剂组合物,其用于将两种基材材料粘合在一起,用于广泛的各种潜在应用,其中基材材料之间的粘合提供与搭接剪切强度和/或T-剥离强度相关的特定机械性能。粘合剂组合物可以施加到被粘合的基材材料中的一者或两者上,例如,作为非限制性实例,汽车框架的部件。对齐这些部件并且可以加入压力和/或间隔件以控制粘合厚度。粘合剂组合物可使用外部源如烘箱(或其他热方法)或通过使用光化辐射(UV光等)固化。
可以通过本发明的粘合剂组合物粘合的合适的基材材料包括但不限于材料,诸如金属或金属合金,玻璃,诸如木材的天然材料,诸如硬塑料的聚合材料,或复合材料。本发明的粘合剂特别适用于各种汽车或工业应用。
以下实施例用于说明本发明,该实施例不应视为将本发明限制于其细节。除非另有说明,实施例以及整个说明书中的所有份数和百分比均以重量计。
实施例
固化组分制备
实施例1
由以下装料制备封闭异氰酸酯:
1Mondur MLQ可从Covestro商购获得。
2DBTDL是二月桂酸二丁基锡,可从Arkema Inc商购获得
3Epon 828可从Hexion Specialty Chemicals商购获得。
4Terathane 1000可从Invista商购获得。
5二丁基乙醇酰胺可从PPG获得。
将装料1加入到1000mL的4颈烧瓶中,该烧瓶配备有马达驱动的不锈钢搅拌叶片,水冷冷凝器,氮气层和带有通过温度反馈控制装置连接的温度计的加热套。将反应混合物加热至80℃。在80℃下,经30分钟将装料2滴加到反应混合物中。添加后,将反应混合物保持在80℃直至异氰酸酯当量停止(stall)(NCO EQ WT=1200)。然后将反应混合物冷却至70℃,然后经1小时加入装料3。将反应混合物保持在70℃,直到IR光谱显示使用ThermoScientific Nicolet iS5 FT-IR不存在特征性NCO带(2269cm-1)。在70℃将反应产物倒出。通过凝胶渗透色谱法测定的封闭异氰酸酯的Mw为7402,相对于800至900,000Da的线型聚苯乙烯标准物,并且可以使用Waters 2695分离模块和Waters 2414差示折射计(RI检测器)进行。使用四氢呋喃(THF)作为洗脱液,流速为1ml min-1,并且使用两个PL Gel Mixed C柱在室温下分离。
实施例2
由以下装料制备封闭异氰酸酯:
1Mondur MLQ可从Covestro商购获得。
2DBTDL是二月桂酸二丁基锡,可从Arkema Inc商购获得
3Epon 828可从Hexion Specialty Chemicals商购获得。
4Terathane 1000可从Invista商购获得。
5丁基乙醇酰胺可从PPG获得。
将装料1加入到1000mL的4颈烧瓶中,该烧瓶配备有马达驱动的不锈钢搅拌叶片,水冷冷凝器,氮气层和带有通过温度反馈控制装置连接的温度计的加热套。将反应混合物加热至80℃。在80℃下,经30分钟将装料2滴加到反应混合物中。添加后,将反应混合物保持在80℃直至异氰酸酯当量停止(NCO EQ WT=1200.9)。然后将反应混合物冷却至70℃,然后经1小时加入装料3。将反应混合物保持在70℃,直到IR光谱显示使用Thermo ScientificNicolet iS5 FT-IR不存在特征性NCO带(2269cm-1)。在70℃将反应产物倒出。封闭的异氰酸酯的Mw为7168,如实施例1中所述测定。
实施例3
由以下装料制备封闭异氰酸酯:
1Mondur MLQ可从Covestro商购获得。
2DBTDL是二月桂酸二丁基锡,可从Arkema Inc商购获得
3Epon 828可从Hexion Specialty Chemicals商购获得。
4Terathane 1000可从Invista商购获得。
5丁基乳酰胺可从PPG获得。
将装料1加入到1000mL的4颈烧瓶中,该烧瓶配备有马达驱动的不锈钢搅拌叶片,水冷冷凝器,氮气层和带有通过温度反馈控制装置连接的温度计的加热套。将反应混合物加热至80℃。在80℃下,经30分钟将装料2滴加到反应混合物中。添加后,将反应混合物保持在80℃直至异氰酸酯当量停止(NCO EQ WT=1139.6)。然后将反应混合物冷却至70℃,然后经1小时加入装料3。将反应混合物保持在70℃,直到IR光谱显示使用Thermo ScientificNicolet iS5 FT-IR不存在特征性NCO带(2269cm-1)。在70℃将反应产物倒出。封闭的异氰酸酯的Mw为7532,如实施例1中所述测定。
实施例4
由以下装料制备封闭异氰酸酯:
1Mondur TDS Grade E可从Covestro商购获得。
2DBTDL是二月桂酸二丁基锡,可从Arkema Inc商购获得
3Epon 828可从Hexion Specialty Chemicals商购获得。
4Terathane 1000可从Invista商购获得。
5丁基乳酰胺可从PPG获得。
将装料1加入到1000mL的4颈烧瓶中,该烧瓶配备有马达驱动的不锈钢搅拌叶片,水冷冷凝器,氮气层和带有通过温度反馈控制装置连接的温度计的加热套。将反应混合物加热至80℃。在80℃下,经30分钟将装料2滴加到反应混合物中。添加后,将反应混合物保持在80℃直至异氰酸酯当量停止(NCO EQ WT=826.1)。然后将反应混合物冷却至70℃,然后经1小时加入装料3。将反应混合物保持在70℃,直到IR光谱显示使用Thermo ScientificNicolet iS5 FT-IR不存在特征性NCO带(2269cm-1)。在70℃将反应产物倒出。封闭的异氰酸酯的Mw为5092,如实施例1中所述测定。
比较例5
由以下装料制备封闭异氰酸酯:
1Mondur TDS Grade E可从Covestro商购获得。
2DBTDL是二月桂酸二丁基锡,可从Arkema Inc.商购获得
3Epon 828可从Hexion Specialty Chemicals商购获得。
4Terathane 1000可从Invista商购获得。
5丁醇可从BASF商购获得。
将装料1加入到1000mL的4颈烧瓶中,该烧瓶配备有马达驱动的不锈钢搅拌叶片,水冷冷凝器,氮气层和带有通过温度反馈控制装置连接的温度计的加热套。将反应混合物加热至80℃。在80℃下,经30分钟将装料2滴加到反应混合物中。添加后,将反应混合物保持在80℃直至异氰酸酯当量停止(NCO EQ WT=1149.1)。然后将反应混合物冷却至70℃,然后经1小时加入装料3。将反应混合物保持在70℃,直到IR光谱显示使用Thermo ScientificNicolet iS5 FT-IR不存在特征性NCO带(2269cm-1)。倒出反应产物。封闭的异氰酸酯的Mw为5447,如实施例1中所述测定。
粘合剂组合物制备
通过混合表1中列出的成分制备结构粘合剂母料组合物。使用DAC600.1 FVZSpeedmixerTM不对称离心混合器在20℃至40℃的室温下在塑料容器中进行混合以形成粘合剂组合物。
表1.材料
通过将Epon Resin 828(改性粘合剂#1)或乙醇酰胺封闭的异氰酸酯(改性粘合剂#2至#6)混合到粘合剂母料(如上制备)中制备粘合剂实施例#1至#6,如下表2中所示。通过使用DAC600 FVZ SpeedmixerTM不对称离心混合器在20℃至40℃的温度下在塑料容器中进行混合以形成粘合剂组合物。
楔形冲击强度试验
根据ISO 11343测试粘合剂组合物的楔形冲击强度。对于每种测试条件制备三个样品。使用的基材是0.73mm厚的冷轧钢(CRS)(购自ACT Test Panels LLC),其形成测试试样,如ISO方法中详述。将粘合剂施加到试样的凸起端部至20mm×30mm的区域。使用玻璃间隔珠保持粘合剂的厚度为0.25mm直径。用弹簧加载的夹子将粘合组件夹在一起,并用刮刀除去多余的粘合剂。将测试片在135℃的烘箱中固化17分钟。使用在环境温度下运行的Instron型CEAST 9350测试粘合。
数据记录在表2中,并证明与对比例#6相比,包含本发明的固化剂(实施例#2至#5)改善了楔形冲击强度,包含实施例#2至#5的固化剂的粘合剂组合物显著优于对比例#6。
表2粘合剂组合物
改性粘合剂 | #1 | #2 | #3 | #4 | #5 | #6 |
母料粘合剂 | 89.1 | 89.1 | 89.1 | 89.1 | 89.1 | 89.1 |
Epon树脂828* | 10.0 | |||||
实施例#1 | 10.0 | |||||
实施例#2 | 10.0 | |||||
实施例#3 | 10.0 | |||||
实施例#4 | 10.0 | |||||
实施例#5 | 10.0 | |||||
楔形冲击N/mm | 17.3 | 16.1 | 15.7 | 15.7 | 15.9 | 1.0** |
*Epon Resin 828可从Hexion获得
**没有明显的耐性(resistance)
粘度测量
使用具有25mm平行板和1mm间隙的Anton Paar Physica MCR 301流变仪测量粘合剂粘度。测量的剪切条件如下:调节:以0.1s-1的剪切速率旋转60秒;回火:240秒无剪切;振幅测试:在90秒内从0.01到10%的对数增加应变y的振荡(每3秒测量数据);剪切阶段:在10Hz下10%应变(y)的振荡120秒(每10秒测量数据);再调节:以0.1s-1的剪切速率旋转60秒;再生模式:0.05%应变(y)的振荡120秒(每10秒测量数据)。
对于在y=0.05%(在21秒)的条件下测量的粘合剂#2的复数粘度17*Al在40℃下3天后测量其初始值。在每个测量之前将样品调节至35℃。那些测量的结果显示在表3中,并证明本发明的粘合剂组合物在40℃下储存三天后保持稳定。
表3粘度(mPa.s)
40℃储存 | 天数=0粘度mPa·s | 天数=3粘度mPa·s |
粘合剂#1 | 1.70E+05 | 1.95E+05 |
本发明的方面
在下文中,总结了本发明的一些非限制性方面:
1.粘合剂组合物,包含:
含环氧基的组分;和
封闭的多异氰酸酯固化剂,其包含衍生自包含α-羟基酰胺,酯或硫酯或其组合的封闭剂的封闭基团。
2.根据前述方面1的粘合剂组合物,其中基于总组合物重量,含环氧基的组分的存在量为50重量%至95重量%。
3.根据前述方面1或2中任一项的粘合剂组合物,其中含环氧基的组分包含环氧封端的增韧剂。
4.根据前述方面中任一项的粘合剂组合物,其中基于总组合物重量,封闭的多异氰酸酯固化剂的存在量为5%至50%。
5.根据前述方面中任一项的粘合剂组合物,其中封闭的多异氰酸酯包含衍生自封闭剂的第二封闭基团,该封闭剂包含醇,酚类化合物,叔羟基胺,肟,胺或其组合的。
6.根据前述方面中任一项的粘合剂组合物,其中包含α-羟基酰胺,酯或硫酯的封闭剂包含以下结构的化合物:
其中X为N(R2),O,S;n为1至4;当n=1且X=N(R2)时,R为氢,C1-C10烷基基团,芳基基团,聚醚,聚酯,聚氨酯,羟基烷基基团,或硫代烷基基团;当n=1且X=O或S时,R为C1-C10烷基基团,芳基基团,聚醚,聚酯,聚氨酯,羟基烷基基团,或硫代烷基基团;当n=2至4时,R为多价C1-C10烷基基团,多价芳基基团,多价聚醚,多价聚酯,多价聚氨酯;每个R1独立地为氢,C1-C10烷基基团,芳基基团,或环脂族基团;每个R2独立地为氢,C1-C10烷基基团,芳基基团,环脂族基团,羟基烷基基团,或硫代烷基基团;以及R和R2可以一起形成环脂族、杂环结构。
7.根据前述方面中任一项的粘合剂组合物,其中所述封闭剂包含α-羟基酰胺封闭剂。
8.根据方面7的粘合剂组合物,其中α-羟基酰胺封闭剂包括烷基乙醇酰胺和/或烷基乳酰胺。
9.根据方面8的粘合剂组合物,其中烷基乙醇酰胺或烷基乳酰胺包含以下结构的化合物:
其中R1是氢或甲基;R2是C1至C10烷基;R3为C1至C10烷基。
10.根据方面8或9中任一项的粘合剂组合物,其中烷基乙醇酰胺或烷基乳酰胺包含以下结构的化合物:
其中R1是氢或甲基;R2是C1至C10烷基;R3是氢。
11.根据方面8至10中任一项的粘合剂组合物,其中烷基乙醇酰胺包含C1至C10单烷基乙醇酰胺。
12.根据方面8至11中任一项的粘合剂组合物,其中烷基乳酰胺包含C1至C10单烷基乳酰胺。
13.根据方面8至12中任一项的粘合剂组合物,其中烷基乳酰胺包含外消旋乳酰胺。
14.根据方面8-13中任一项的粘合剂组合物,其中衍生自α-羟基酰胺,酯或硫酯封闭剂的封闭基团占封闭多异氰酸酯的总封闭异氰酸基的至少10%。
15.根据前述方面中任一项的粘合剂组合物,其中通过凝胶渗透色谱法使用聚苯乙烯校准标准测量,封闭的多异氰酸酯固化剂具有250至10,000的Mw。
16.根据前述方面中任一项的粘合剂组合物,其中粘合剂组合物的粘度为102MPa.s至105MPa.s(在以下剪切条件下,使用具有25mm平行板和1mm间隙的Anton PaarPhysica MCR 301流变仪测量:调节:以0.1s-1的剪切速率旋转60秒;回火:无剪切240秒;振幅测试:,在90秒内从0.01到10%的对数增加应变的振荡(每3秒测量数据);剪切阶段:在10Hz下10%应变(y)的振荡120秒(每10秒测量数据);重新调节:以0.1s-1剪切速率旋转60秒;再生模式:0.05%应变(y)的振荡120秒(每10秒测量数据))。
17.根据前述方面中任一项的粘合剂组合物,还包含弹性体颗粒。
18.根据方面17的粘合剂组合物,其中弹性体颗粒具有核/壳结构。
19.根据前述方面中任一项的粘合剂组合物,还包含固化催化剂。
20.根据前述方面中任一项的粘合剂组合物,其中粘合剂组合物是单组分组合物。
21.一种粘合剂,其包含处于固化状态的根据前述方面中任一项的组合物。
22.一篇制品,包括:
第一基材;
第二基材;
粘合剂,其包含处于第一和第二基材之间的处于固化状态的根据方面1至20中任一项的粘合剂组合物。
23.根据方面22所述的制品,其中所述粘合剂具有至少15N/mm的楔形冲击强度(通过CEAST 9350根据ISO 11343测量)。
24.一种在两个基材之间形成粘合的方法,包括:
将方面1至20中任一项的粘合剂组合物施加到第一基材;
使第二基材与粘合剂组合物接触,使得粘合剂组合物位于第一基材和第二基材之间;和
施加外部能量源以固化粘合剂组合物。
25.方面24的方法,其中固化包括热加热至至少80℃的温度。
26.一种粘合剂组合物,包含:
含环氧基的组分;和
根据以下结构的封闭的多异氰酸酯固化剂:
其中Y代表多异氰酸酯的残基;m≥1;并且n≥0;X为N(R2),O,S;当X=N(R2)时,R为氢,C1-C10烷基基团,芳基基团,聚醚,聚酯,聚氨酯,羟基烷基基团,或硫代烷基基团;当X=O或S时,R为C1-C10烷基基团,芳基基团,聚醚,聚酯,聚氨酯,羟基烷基基团,或硫代烷基基团;每个R1独立地为氢,C1-C10烷基基团,芳基基团,或环脂族基团;当m≥2时,R任选地为多价C1-C10烷基基团,多价芳基基团,多价聚醚,多价聚酯,多价聚氨酯;每个R2独立地为氢,C1-C10烷基基团,芳基基团,环脂族基团,羟基烷基基团,或硫代烷基基团;R和R2可以一起形成环脂族、杂环结构;以及O-Z表示第二封闭剂的残基。
本领域技术人员将理解,在不脱离本文描述和示例的广泛发明构思的情况下,根据上述公开内容可以进行多种修改和变化。因此,应当理解,前述公开内容仅仅是对本申请的各种示例性方面的说明,并且本领域技术人员可以容易地做出许多修改和变化,这些修改和变化在本申请以及所附权利要求的精神和范围内中。
Claims (26)
1.粘合剂组合物,包含:
含环氧基的组分;和
封闭的多异氰酸酯固化剂,其包含衍生自封闭剂的封闭基团,该封闭剂包括α-羟基酰胺,酯或硫酯,或其组合。
2.权利要求1的粘合剂组合物,其中基于总组合物重量,含环氧基的组分的存在量为50-95重量%。
3.权利要求1的粘合剂组合物,其中含环氧基的组分包括环氧封端的增韧剂。
4.权利要求1的粘合剂组合物,其中基于总组合物重量,封闭的多异氰酸酯固化剂的存在量为5%至50%。
5.权利要求1的粘合剂组合物,其中封闭的多异氰酸酯包含衍生自封闭剂的第二封闭基团,所述封闭剂包括醇,酚类化合物,叔羟胺,肟,胺或其组合。
6.权利要求1的粘合剂组合物,其中包括α-羟基酰胺,酯或硫酯的封闭剂包含以下结构的化合物:
其中X为N(R2),O,S;n为1至4;当n=1且X=N(R2)时,R为氢,C1-C10烷基基团,芳基基团,聚醚,聚酯,聚氨酯,羟基烷基基团,或硫代烷基基团;当n=1且X=O或S时,R为C1-C10烷基基团,芳基基团,聚醚,聚酯,聚氨酯,羟基烷基基团,或硫代烷基基团;当n=2至4时,R为多价C1-C10烷基基团,多价芳基基团,多价聚醚,多价聚酯,多价聚氨酯;每个R1独立地为氢,C1-C10烷基基团,芳基基团,或环脂族基团;每个R2独立地为氢,C1-C10烷基基团,芳基基团,环脂族基团,羟基烷基基团,或硫代烷基基团;以及R和R2可以一起形成环脂族、杂环结构。
7.权利要求1的粘合剂组合物,其中封闭剂包括α-羟基酰胺封闭剂。
8.权利要求7的粘合剂组合物,其中α-羟基酰胺封闭剂包括烷基乙醇酰胺和/或烷基乳酰胺。
9.权利要求8的粘合剂组合物,其中该烷基乙醇酰胺或烷基乳酰胺包含以下结构的化合物:
其中R1为氢或甲基;R2为C1-C10烷基基团;以及R3为C1-C10烷基基团。
10.权利要求8的粘合剂组合物,其中烷基乙醇酰胺或烷基乳酰胺包含以下结构的化合物:
其中R1为氢或甲基;R2为C1-C10烷基基团;以及R3为氢。
11.权利要求8的粘合剂组合物,其中该烷基乙醇酰胺包括C1-C10单烷基乙醇酰胺。
12.权利要求8的粘合剂组合物,其中该烷基乳酰胺包括C1-C10单烷基乳酰胺。
13.权利要求8的粘合剂组合物,其中该烷基乳酰胺包括外消旋乳酰胺。
14.权利要求8的粘合剂组合物,其中衍生自α-羟基酰胺、酯或硫酯封闭剂的封闭基团占封闭的多异氰酸酯的总封闭的异氰酸基基团的至少10%。
15.权利要求1的粘合剂组合物,其中通过凝胶渗透色谱法使用聚苯乙烯校准标准测量,封闭的多异氰酸酯固化剂的Mw为250至10,000。
16.权利要求1的粘合剂组合物,其中所述粘合剂组合物的粘度为102MPa.s至105MPa.s(在以下剪切条件下,使用具有25mm平行板和1mm间隙的Anton Paar Physica MCR 301流变仪测量:调节:以0.1s-1的剪切速率旋转60秒;回火:240秒无剪切;振幅测试:在90秒内从0.01到10%的对数增加应变的振荡(每3秒测量数据);剪切阶段:在10Hz下10%应变(y)的振荡120秒(每10秒测量数据);重新调节:以0.1s-1剪切速率旋转60秒;再生模式:0.05%应变(y)的振荡持续120秒(每10秒测量数据))。
17.权利要求1的粘合剂组合物,还包含弹性体颗粒。
18.权利要求17的粘合剂组合物,其中该弹性体颗粒具有核/壳结构。
19.权利要求1的粘合剂组合物,还包含固化催化剂。
20.权利要求1的粘合剂组合物,其中该粘合剂组合物是单组分组合物。
21.粘合剂,其包含处于固化状态的权利要求1的组合物。
22.制品,包括:
第一基材;
第二基材;
粘合剂,其包含处于第一和第二基材之间的处于固化状态的权利要求1的粘合剂组合物。
23.根据权利要求22所述的制品,其中该粘合剂具有至少15N/mm的楔形冲击强度(通过CEAST 9350根据ISO 11343测量)。
24.在两个基材之间形成粘合的方法,包括:
将权利要求1的粘合剂组合物施加到第一基材;
使第二基材与粘合剂组合物接触,使得粘合剂组合物位于第一基材和第二基材之间;和
施加外部能量源以固化粘合剂组合物。
25.权利要求24的方法,其中所述固化包括热加热至至少80℃的温度。
26.粘合剂组合物,包含:
含环氧基的组分;和
根据以下结构的封闭的多异氰酸酯固化剂:
其中Y代表多异氰酸酯的残基;m≥1;并且n≥0;X为N(R2),O,S;当X=N(R2)时,R为氢,C1-C10烷基基团,芳基基团,聚醚,聚酯,聚氨酯,羟基烷基基团,或硫代烷基基团;当X=O或S时,R为C1-C10烷基基团,芳基基团,聚醚,聚酯,聚氨酯,羟基烷基基团,或硫代烷基基团;每个R1独立地为氢,C1-C10烷基基团,芳基基团,或环脂族基团;当m≥2时,R任选地为多价C1-C10烷基基团,多价芳基基团,多价聚醚,多价聚酯,多价聚氨酯;每个R2独立地为氢,C1-C10烷基基团,芳基基团,环脂族基团,羟基烷基基团,或硫代烷基基团;R和R2可以一起形成环脂族、杂环结构;以及O-Z表示第二封闭剂的残基。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201762455778P | 2017-02-07 | 2017-02-07 | |
US62/455,778 | 2017-02-07 | ||
PCT/US2018/017283 WO2018148323A1 (en) | 2017-02-07 | 2018-02-07 | Low-temperature curing adhesive compositions |
Publications (2)
Publication Number | Publication Date |
---|---|
CN110300770A true CN110300770A (zh) | 2019-10-01 |
CN110300770B CN110300770B (zh) | 2022-03-01 |
Family
ID=61244802
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201880010558.4A Active CN110300770B (zh) | 2017-02-07 | 2018-02-07 | 低温固化粘合剂组合物 |
CN201880010569.2A Active CN110249013B (zh) | 2017-02-07 | 2018-02-07 | 低温固化涂料组合物 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201880010569.2A Active CN110249013B (zh) | 2017-02-07 | 2018-02-07 | 低温固化涂料组合物 |
Country Status (9)
Country | Link |
---|---|
US (2) | US11952514B2 (zh) |
EP (2) | EP3580253B1 (zh) |
KR (2) | KR102337432B1 (zh) |
CN (2) | CN110300770B (zh) |
CA (2) | CA3052051C (zh) |
ES (1) | ES2868245T3 (zh) |
MX (2) | MX2019008831A (zh) |
RU (2) | RU2730918C1 (zh) |
WO (2) | WO2018148323A1 (zh) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP4085088A1 (en) * | 2019-12-31 | 2022-11-09 | PPG Industries Ohio Inc. | Electrodepositable coating compositions |
CN112358599B (zh) * | 2020-11-12 | 2022-12-27 | 佛山市哲宝科技有限公司 | 热塑性聚氨酯弹性体及其制备方法和应用 |
WO2022187845A1 (en) | 2021-03-05 | 2022-09-09 | Prc-Desoto International, Inc. | Corrosion inhibiting coating compositions |
EP4301816A1 (en) | 2021-03-05 | 2024-01-10 | PRC-Desoto International, Inc. | Coating compositions comprising a polysulfide corrosion inhibitor |
EP4347252A1 (en) | 2021-05-25 | 2024-04-10 | PRC-Desoto International, Inc. | Composite structures comprising metal substrates |
CA3218854A1 (en) | 2021-06-24 | 2022-12-29 | Elizabeth Anne FURAR | Systems and methods for coating multi-layered coated metal substrates |
EP4363511A1 (en) | 2021-07-01 | 2024-05-08 | PPG Industries Ohio Inc. | Electrodepositable coating compositions |
WO2024002477A1 (en) * | 2022-06-29 | 2024-01-04 | Transitions Optical, Ltd. | Curable photochromic compositions including isocyanate and imine functional components |
CN116535613A (zh) * | 2022-11-16 | 2023-08-04 | 江苏奥斯佳材料科技股份有限公司 | 聚氨酯固化剂的制备方法 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4452681A (en) * | 1983-02-10 | 1984-06-05 | Ppg Industries, Inc. | Method of electrodeposition of coating compositions containing novel urethane curing agents |
EP0254044A1 (en) * | 1986-06-23 | 1988-01-27 | Ashland Oil, Inc. | Adhesive composition |
EP0726284A1 (de) * | 1995-02-11 | 1996-08-14 | Hüls Aktiengesellschaft | Blockierte Polyisocyanate, Verfahren zu ihrer Herstellung und daraus hergestellte Lacke und Beschichtungssysteme |
CN102532477A (zh) * | 2010-11-08 | 2012-07-04 | Ems专利股份公司 | 织物增强插入物用的粘合剂及其用途 |
CN104520344A (zh) * | 2012-06-25 | 2015-04-15 | Ppg工业俄亥俄公司 | 包括锌(ii)脒配合物的水性树脂分散体及其制造方法 |
CN105452320A (zh) * | 2013-08-23 | 2016-03-30 | 三井化学株式会社 | 封端异氰酸酯、涂料组合物、粘接剂组合物和物品 |
Family Cites Families (43)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1546840C3 (de) | 1965-02-27 | 1975-05-22 | Basf Ag, 6700 Ludwigshafen | Verfahren zum Herstellen von Überzügen |
US3975346A (en) | 1968-10-31 | 1976-08-17 | Ppg Industries, Inc. | Boron-containing, quaternary ammonium salt-containing resin compositions |
US3799854A (en) | 1970-06-19 | 1974-03-26 | Ppg Industries Inc | Method of electrodepositing cationic compositions |
US3962165A (en) | 1971-06-29 | 1976-06-08 | Ppg Industries, Inc. | Quaternary ammonium salt-containing resin compositions |
US3947338A (en) | 1971-10-28 | 1976-03-30 | Ppg Industries, Inc. | Method of electrodepositing self-crosslinking cationic compositions |
US3793278A (en) | 1972-03-10 | 1974-02-19 | Ppg Industries Inc | Method of preparing sulfonium group containing compositions |
US3928157A (en) | 1972-05-15 | 1975-12-23 | Shinto Paint Co Ltd | Cathodic treatment of chromium-plated surfaces |
US4001156A (en) | 1972-08-03 | 1977-01-04 | Ppg Industries, Inc. | Method of producing epoxy group-containing, quaternary ammonium salt-containing resins |
CA1111598A (en) | 1976-01-14 | 1981-10-27 | Joseph R. Marchetti | Amine acide salt-containing polymers for cationic electrodeposition |
DE2963277D1 (en) | 1978-12-11 | 1982-08-19 | Shell Int Research | Thermosetting resinous binder compositions, their preparation, and use as coating materials |
US4432850A (en) | 1981-07-20 | 1984-02-21 | Ppg Industries, Inc. | Ungelled polyepoxide-polyoxyalkylenepolyamine resins, aqueous dispersions thereof, and their use in cationic electrodeposition |
US4370461A (en) * | 1981-07-27 | 1983-01-25 | The Dow Chemical Company | Organo phosphorus-containing compounds as catalysts for deblocking blocked isocyanates |
US4452963A (en) | 1983-02-10 | 1984-06-05 | Ppg Industries, Inc. | Low temperature urethane curing agents |
US4452930A (en) | 1983-02-10 | 1984-06-05 | Ppg Industries, Inc. | Curable compositions containing novel urethane curing agents |
CA1229338A (en) * | 1983-02-10 | 1987-11-17 | Thomas C. Moriarity | Urethanes, curable compositions containing the novel urethanes, and the use of the compositions in electrodeposition |
US4793867A (en) | 1986-09-26 | 1988-12-27 | Chemfil Corporation | Phosphate coating composition and method of applying a zinc-nickel phosphate coating |
US4846946A (en) * | 1987-12-11 | 1989-07-11 | Ppg Industries, Inc. | Process for reducing attendant color shift in coatings containing blocked isocyanates |
US5588989A (en) | 1994-11-23 | 1996-12-31 | Ppg Industries, Inc. | Zinc phosphate coating compositions containing oxime accelerators |
US6017432A (en) | 1997-07-03 | 2000-01-25 | Ppg Industries Ohio, Inc. | Electrodepositable coating compositions and their use in a method of cationic electrodeposition |
US6156823A (en) * | 1998-12-04 | 2000-12-05 | E. I. Du Pont De Nemours And Company | Bismuth oxide catalyst for cathodic electrocoating compositions |
US6190524B1 (en) * | 1999-03-26 | 2001-02-20 | Ppg Industries Ohio, Inc. | Organosulfur bismuth compounds and their use in electrodepositable coating compositions |
WO2000071337A1 (en) * | 1999-05-26 | 2000-11-30 | Henkel Corporation | Autodeposition coatings and process therefor |
ATE253096T1 (de) * | 1999-07-02 | 2003-11-15 | Rhein Chemie Rheinau Gmbh | Katalysator-system für die nco/oh-reaktion (polyurethanbildung) |
WO2001030880A1 (en) * | 1999-10-26 | 2001-05-03 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of a rigid polyurethane foam |
CA2400603A1 (en) * | 2000-02-18 | 2001-08-23 | Henkel Kommanditgesellschaft Auf Aktien | Rubber-metal composites |
US20030054193A1 (en) | 2001-02-05 | 2003-03-20 | Mccollum Gregory J. | Photodegradation-resistant electrodepositable coating compositions and processes related thereto |
US6875800B2 (en) | 2001-06-18 | 2005-04-05 | Ppg Industries Ohio, Inc. | Use of nanoparticulate organic pigments in paints and coatings |
US6894086B2 (en) | 2001-12-27 | 2005-05-17 | Ppg Industries Ohio, Inc. | Color effect compositions |
DE10328994A1 (de) * | 2003-06-27 | 2005-01-13 | Bayer Materialscience Ag | Blockierte Polyisocyanate |
US20070015873A1 (en) * | 2005-07-13 | 2007-01-18 | Fenn David R | Electrodepositable aqueous resinous dispersions and methods for their preparation |
US7749368B2 (en) | 2006-12-13 | 2010-07-06 | Ppg Industries Ohio, Inc. | Methods for coating a metal substrate and related coated substrates |
EP1946995A1 (de) | 2006-12-22 | 2008-07-23 | Sika Technology AG | Verstärkungssystem zur Verstärkung eines Hohlraumes eines Bauelements |
US8673091B2 (en) | 2007-08-03 | 2014-03-18 | Ppg Industries Ohio, Inc | Pretreatment compositions and methods for coating a metal substrate |
US7842762B2 (en) * | 2007-08-08 | 2010-11-30 | Ppg Industries Ohio, Inc. | Electrodepositable coating composition containing a cyclic guanidine |
ES2420882T3 (es) | 2008-10-01 | 2013-08-27 | Purac Biochem Bv | Proceso para la fabricación de N,N-dialquil lactamida |
KR20110094211A (ko) * | 2008-12-09 | 2011-08-22 | 바스프 에스이 | 폴리메틸올의 정제 방법 |
US8486538B2 (en) * | 2009-01-27 | 2013-07-16 | Ppg Industries Ohio, Inc | Electrodepositable coating composition comprising silane and yttrium |
CA2803851A1 (en) * | 2010-06-25 | 2011-12-29 | Dow Global Technologies Llc | Curable epoxy resin compositions and composites made therefrom |
US8796361B2 (en) | 2010-11-19 | 2014-08-05 | Ppg Industries Ohio, Inc. | Adhesive compositions containing graphenic carbon particles |
CN104136492B (zh) * | 2012-03-01 | 2016-03-23 | 三菱瓦斯化学株式会社 | 光学材料用聚合性组合物 |
US9688874B2 (en) | 2013-10-25 | 2017-06-27 | Ppg Industries Ohio, Inc. | Method of making a bicyclic guanidine-cured acrylic coating |
US10808152B2 (en) * | 2014-11-28 | 2020-10-20 | Dai Nippon Printing Co., Ltd. | Adhesive composition and adhesive sheet using same |
JP2016160286A (ja) * | 2015-02-27 | 2016-09-05 | 三洋化成工業株式会社 | 耐チッピング塗料 |
-
2018
- 2018-02-07 CN CN201880010558.4A patent/CN110300770B/zh active Active
- 2018-02-07 RU RU2019128017A patent/RU2730918C1/ru active
- 2018-02-07 EP EP18706138.7A patent/EP3580253B1/en active Active
- 2018-02-07 US US16/484,345 patent/US11952514B2/en active Active
- 2018-02-07 KR KR1020197026106A patent/KR102337432B1/ko active IP Right Grant
- 2018-02-07 WO PCT/US2018/017283 patent/WO2018148323A1/en unknown
- 2018-02-07 EP EP18706132.0A patent/EP3580290B1/en active Active
- 2018-02-07 MX MX2019008831A patent/MX2019008831A/es unknown
- 2018-02-07 KR KR1020197026108A patent/KR102325094B1/ko active IP Right Grant
- 2018-02-07 CA CA3052051A patent/CA3052051C/en active Active
- 2018-02-07 CA CA3052049A patent/CA3052049C/en active Active
- 2018-02-07 RU RU2019128021A patent/RU2759543C2/ru active
- 2018-02-07 WO PCT/US2018/017259 patent/WO2018148306A1/en unknown
- 2018-02-07 CN CN201880010569.2A patent/CN110249013B/zh active Active
- 2018-02-07 MX MX2019009265A patent/MX2019009265A/es unknown
- 2018-02-07 ES ES18706138T patent/ES2868245T3/es active Active
- 2018-02-07 US US16/484,288 patent/US20190359867A1/en active Pending
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4452681A (en) * | 1983-02-10 | 1984-06-05 | Ppg Industries, Inc. | Method of electrodeposition of coating compositions containing novel urethane curing agents |
EP0254044A1 (en) * | 1986-06-23 | 1988-01-27 | Ashland Oil, Inc. | Adhesive composition |
EP0726284A1 (de) * | 1995-02-11 | 1996-08-14 | Hüls Aktiengesellschaft | Blockierte Polyisocyanate, Verfahren zu ihrer Herstellung und daraus hergestellte Lacke und Beschichtungssysteme |
CN102532477A (zh) * | 2010-11-08 | 2012-07-04 | Ems专利股份公司 | 织物增强插入物用的粘合剂及其用途 |
CN104520344A (zh) * | 2012-06-25 | 2015-04-15 | Ppg工业俄亥俄公司 | 包括锌(ii)脒配合物的水性树脂分散体及其制造方法 |
CN105452320A (zh) * | 2013-08-23 | 2016-03-30 | 三井化学株式会社 | 封端异氰酸酯、涂料组合物、粘接剂组合物和物品 |
Also Published As
Publication number | Publication date |
---|---|
MX2019008831A (es) | 2019-10-07 |
ES2868245T3 (es) | 2021-10-21 |
KR20190115061A (ko) | 2019-10-10 |
RU2019128021A3 (zh) | 2021-03-09 |
EP3580253B1 (en) | 2021-04-07 |
WO2018148323A1 (en) | 2018-08-16 |
CA3052051C (en) | 2021-10-26 |
CA3052049C (en) | 2021-08-31 |
US11952514B2 (en) | 2024-04-09 |
EP3580290B1 (en) | 2024-05-01 |
RU2730918C1 (ru) | 2020-08-26 |
CA3052049A1 (en) | 2018-08-16 |
WO2018148306A1 (en) | 2018-08-16 |
KR102337432B1 (ko) | 2021-12-09 |
CN110300770B (zh) | 2022-03-01 |
US20190390092A1 (en) | 2019-12-26 |
RU2759543C2 (ru) | 2021-11-15 |
EP3580290A1 (en) | 2019-12-18 |
RU2019128021A (ru) | 2021-03-09 |
CA3052051A1 (en) | 2018-08-16 |
EP3580253A1 (en) | 2019-12-18 |
KR102325094B1 (ko) | 2021-11-10 |
MX2019009265A (es) | 2019-09-19 |
US20190359867A1 (en) | 2019-11-28 |
CN110249013A (zh) | 2019-09-17 |
CN110249013B (zh) | 2022-08-30 |
KR20190113926A (ko) | 2019-10-08 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN110300770A (zh) | 低温固化粘合剂组合物 | |
DK2917260T3 (en) | AMIN COMPOSITION FOR A CRASH FAST 2K epoxy adhesive | |
CN105899565B (zh) | 双组分组合物 | |
CN101861345B (zh) | 包含非芳族脲作为促进剂的热固化性环氧树脂组合物 | |
US20120322938A1 (en) | Composition Of Secondary Amine Adducts, Amine Diluents and Polyisocyanates | |
EP3495442B1 (en) | Two-pack type curable urethane adhesive composition | |
JP6275144B2 (ja) | 環状カルボナート構造を有する結合剤 | |
CN103524714B (zh) | 作为用于环氧树脂组合物的可热活化固化剂的硅烷化合物/脲化合物 | |
DK2917254T3 (en) | REACTIVE LIQUID CAUTION OF BLOCKED ISOCYANATE TERMINATED PREPOLYMERS WITH GLYCOL CATCHERS | |
JP2018510933A (ja) | Ptmeg系ポリウレタン耐衝撃改良剤における向上した低温耐衝撃性 | |
EP3317329B1 (en) | Process for cold bonding rubber on metal substrates | |
JP2008001789A (ja) | 硬化性樹脂組成物及び室温硬化性接着剤組成物 | |
US20200248050A1 (en) | Two-Component Structural Adhesives | |
EP3387079B1 (en) | Aminimide compositions | |
KR20220011129A (ko) | 에폭시 접착제 조성물 및 사용 방법 | |
CN112771092A (zh) | 聚乙酸乙烯酯聚合物或共聚物用于增加双组分可固化聚合物体系的异氰酸酯组分的粘度的用途 | |
JP4037102B2 (ja) | 硬化性樹脂組成物 | |
US20220162375A1 (en) | Two component coating compositions | |
US11359119B2 (en) | Method for connecting molded bodies by injecting a single-component heat-curing epoxy resin composition into cavities | |
CN117881713A (zh) | 双组分聚氨酯粘合剂组合物 | |
JP2023509281A (ja) | 硬化性組成物およびその基材を接着するための方法 |
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 | ||
GR01 | Patent grant | ||
GR01 | Patent grant |