CN114096578A - 无溶剂组合物 - Google Patents
无溶剂组合物 Download PDFInfo
- Publication number
- CN114096578A CN114096578A CN202080048141.4A CN202080048141A CN114096578A CN 114096578 A CN114096578 A CN 114096578A CN 202080048141 A CN202080048141 A CN 202080048141A CN 114096578 A CN114096578 A CN 114096578A
- Authority
- CN
- China
- Prior art keywords
- solvent
- polyol
- acid compound
- isocyanate
- composition
- 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 87
- 229920005862 polyol Polymers 0.000 claims abstract description 71
- 150000003077 polyols Chemical class 0.000 claims abstract description 67
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 37
- 239000002253 acid Substances 0.000 claims abstract description 31
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 239000012948 isocyanate Substances 0.000 claims description 40
- 150000002513 isocyanates Chemical class 0.000 claims description 40
- -1 ethylenediaminetetraacetic acid compound Chemical class 0.000 claims description 13
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 2
- 239000010408 film Substances 0.000 description 19
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 14
- 239000000463 material Substances 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 239000000853 adhesive Substances 0.000 description 9
- 230000001070 adhesive effect Effects 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- POLIXZIAIMAECK-UHFFFAOYSA-N 4-[2-(2,6-dioxomorpholin-4-yl)ethyl]morpholine-2,6-dione Chemical compound C1C(=O)OC(=O)CN1CCN1CC(=O)OC(=O)C1 POLIXZIAIMAECK-UHFFFAOYSA-N 0.000 description 8
- 235000011037 adipic acid Nutrition 0.000 description 8
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 8
- 239000011104 metalized film Substances 0.000 description 8
- 239000005056 polyisocyanate Substances 0.000 description 8
- 229920001228 polyisocyanate Polymers 0.000 description 8
- 239000004721 Polyphenylene oxide Substances 0.000 description 7
- 239000001361 adipic acid Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 229920000570 polyether Polymers 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000004698 Polyethylene Substances 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 description 5
- 239000011888 foil Substances 0.000 description 5
- 229920005906 polyester polyol Polymers 0.000 description 5
- 235000015067 sauces Nutrition 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 238000003475 lamination Methods 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 150000003142 primary aromatic amines Chemical class 0.000 description 4
- 229940043375 1,5-pentanediol Drugs 0.000 description 3
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 3
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 150000002924 oxiranes Chemical class 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 2
- JIABEENURMZTTI-UHFFFAOYSA-N 1-isocyanato-2-[(2-isocyanatophenyl)methyl]benzene Chemical compound O=C=NC1=CC=CC=C1CC1=CC=CC=C1N=C=O JIABEENURMZTTI-UHFFFAOYSA-N 0.000 description 2
- 229920002799 BoPET Polymers 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000001465 metallisation Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- GFNDFCFPJQPVQL-UHFFFAOYSA-N 1,12-diisocyanatododecane Chemical compound O=C=NCCCCCCCCCCCCN=C=O GFNDFCFPJQPVQL-UHFFFAOYSA-N 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 1
- OHTRJOZKRSVAOX-UHFFFAOYSA-N 1,3-diisocyanato-2-methylcyclohexane Chemical compound CC1C(N=C=O)CCCC1N=C=O OHTRJOZKRSVAOX-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 229940035437 1,3-propanediol Drugs 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- AHBNSOZREBSAMG-UHFFFAOYSA-N 1,5-diisocyanato-2-methylpentane Chemical compound O=C=NCC(C)CCCN=C=O AHBNSOZREBSAMG-UHFFFAOYSA-N 0.000 description 1
- KHXVVWQPIQVNRH-UHFFFAOYSA-N 1-isocyanato-3-(isocyanatomethyl)-1-methylcyclohexane Chemical compound O=C=NC1(C)CCCC(CN=C=O)C1 KHXVVWQPIQVNRH-UHFFFAOYSA-N 0.000 description 1
- LYDHLGJJJAWBDY-UHFFFAOYSA-N 1-isocyanato-4-[2-(4-isocyanatocyclohexyl)propan-2-yl]cyclohexane Chemical compound C1CC(N=C=O)CCC1C(C)(C)C1CCC(N=C=O)CC1 LYDHLGJJJAWBDY-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- RAZLJUXJEOEYAM-UHFFFAOYSA-N 2-[bis[2-(2,6-dioxomorpholin-4-yl)ethyl]azaniumyl]acetate Chemical compound C1C(=O)OC(=O)CN1CCN(CC(=O)O)CCN1CC(=O)OC(=O)C1 RAZLJUXJEOEYAM-UHFFFAOYSA-N 0.000 description 1
- CRRPFYHGOTWPQJ-UHFFFAOYSA-N 4-[2-[2-(2,6-dioxomorpholin-4-yl)ethoxy]ethyl]morpholine-2,6-dione Chemical compound C1C(=O)OC(=O)CN1CCOCCN1CC(=O)OC(=O)C1 CRRPFYHGOTWPQJ-UHFFFAOYSA-N 0.000 description 1
- 239000004970 Chain extender Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- XTPWKTDOZRVFAT-UHFFFAOYSA-N [4-methyl-1,3-bis(6-methylheptyl)cyclohexyl] cyanate Chemical compound CC(C)CCCCCC1CC(CCCCCC(C)C)(OC#N)CCC1C XTPWKTDOZRVFAT-UHFFFAOYSA-N 0.000 description 1
- ZAVYDEIAQPCPMJ-UHFFFAOYSA-L [dibutyl(3H-dithiole-3-carbonyloxy)stannyl] 3H-dithiole-3-carboxylate Chemical compound S1SC(C=C1)C(=O)[O-].C(CCC)[Sn+2]CCCC.S1SC(C=C1)C(=O)[O-] ZAVYDEIAQPCPMJ-UHFFFAOYSA-L 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- NBJODVYWAQLZOC-UHFFFAOYSA-L [dibutyl(octanoyloxy)stannyl] octanoate Chemical compound CCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCC NBJODVYWAQLZOC-UHFFFAOYSA-L 0.000 description 1
- 150000001279 adipic acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000021028 berry Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical group NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000003851 corona treatment Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000032798 delamination Effects 0.000 description 1
- 125000006159 dianhydride group Chemical group 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 150000002311 glutaric acids Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 150000005165 hydroxybenzoic acids Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000012939 laminating adhesive Substances 0.000 description 1
- 229920001684 low density polyethylene Polymers 0.000 description 1
- 239000004702 low-density polyethylene Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- IJSMDZFKMKEIRX-UHFFFAOYSA-N morpholine-2,6-dione Chemical compound O=C1CNCC(=O)O1 IJSMDZFKMKEIRX-UHFFFAOYSA-N 0.000 description 1
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- 229910052759 nickel Inorganic materials 0.000 description 1
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Abstract
本公开的实施方案涉及包含通过使多元醇和氨基多羧酸化合物反应形成的反应产物的无溶剂组合物。
Description
技术领域
本公开的实施方案涉及无溶剂组合物,更具体地,实施方案涉及包含通过使多元醇和氨基多羧酸化合物反应形成的反应产物的无溶剂组合物。
背景技术
无溶剂组合物可以包含多元醇和异氰酸酯以及其他可能的成分。例如,当用于粘合剂应用时,可以使无溶剂组合物与两种基材接触,使得多元醇和异氰酸酯可以彼此反应以形成固化产物并在两种基材之间形成粘结。例如,当用于涂层应用时,可以使无溶剂组合物与一种基材接触,使得多元醇和异氰酸酯可以彼此反应以形成固化产物。
发明内容
本公开提供无溶剂组合物,其包含:通过使多元醇和氨基多羧酸化合物反应制备的反应产物和异氰酸酯
本公开的以上发明内容不旨在描述本公开的每个公开的实施方案或每个实施方式。以下描述更具体地示范说明性实施方案。在本申请整篇的若干处,通过实例列表提供指导,所述实例可以各种组合形式使用。在每种情况下,所列举的列表仅充当代表性群组并且不应解释为排它性列表。
具体实施方式
本文公开了多元醇和氨基多羧酸化合物的反应产物。反应产物可以用于无溶剂组合物中,所述无溶剂组合物可以理想地提供一种或多种改善的特性。例如,无溶剂组合物也可以被称为无溶剂粘合剂组合物或无溶剂涂层组合物。
例如,与包含与用于制备反应产物的多元醇相似的多元醇的其他组合物相比,在7天时,包含所述反应产物的无溶剂组合物可以提供改善的,即增加的T型剥离粘结强度。在7天时增加的T型剥离粘结强度指示更大粘合剂强度,这是许多应用所希望的。
另外,与包含与用于制备反应产物的多元醇相似的多元醇的其他组合物相比,包含所述反应产物的无溶剂组合物可以提供提高的,即增加的连袋煮值(boil in bagvalue)。当用本文公开的无溶剂组合物制备的包装产品与消费品结合使用时,提高的连袋煮值可以指示更大的粘合强度。更大的粘合强度是许多应用所希望的。
如本文所用,“无溶剂组合物”是指基于组合物的总重量具有0重量百分比至5重量百分比的溶剂例如有机溶剂或水的组合物。一个或多个实施方案规定无溶剂组合物不包含溶剂和/或在没有溶剂的情况下施加。在本文中,利用基于无溶剂组合物的总重量的0重量百分比至5重量百分比的溶剂被认为是标称量的溶剂,并且因此可以被称为无溶剂。
如所提及的,多元醇和氨基多羧酸化合物的反应产物在本文中公开。如本文所用,“氨基多羧酸化合物”包括其衍生物和/或结构类似物。一个或多个实施方案规定氨基多羧酸化合物是乙二胺四乙酸化合物。氨基多羧酸化合物、衍生物和/或结构类似物的实例包括但不限于乙二胺四乙酸酐、乙二胺四乙酸、二乙烯三胺五乙酸二酐、4,4′-(丙烷-1,2-二基)双(吗啉-2,6-二酮)、4,4′-(丙烷-1,3-二基)双((吗啉-2,6-二酮)和4,4′-(氧基双(乙烷-2,1-二基))双(吗啉-2,6-二酮)。本公开的一个或多个实施方案规定乙二胺四乙酸化合物可以选自乙二胺四乙酸酐、乙二胺四乙酸及其组合。
乙二胺四乙酸二酐可以由下式表示:
本公开的实施方案规定与氨基多羧酸化合物反应的多元醇可以是聚醚多元醇、聚酯多元醇或其组合。
多元醇可以通过已知方法,例如通过使用已知组分、已知设备和已知反应条件来制备。多元醇可以商购获得。
可商购获得的多元醇的实例包括但不限于以商品名VORANOLTM、TERCAROLTM、MOR-FREETM、PRIPLASTTM和VORATECTM等销售的多元醇。
本公开的一个或多个实施方案规定多元醇可以包括聚醚多元醇。聚醚多元醇可以通过已知方法制备。例如,聚醚多元醇可以通过起始化合物的烷氧基化来制备。烷氧基化是至少一种环氧烷例如环氧乙烷、1,2-环氧丙烷或1,2-环氧丁烷的阴离子加聚。可以被称为引发剂的起始化合物是在聚合反应中被烷氧基化的任何有机化合物。引发剂可以含有2个或更多个羟基和/或胺基团。可以使用起始化合物/引发剂的混合物。引发剂化合物的实例包括但不限于乙二醇、二甘醇、三甘醇、丙二醇、二丙二醇、三丙二醇、1,4-丁二醇、1,6-己二醇、1,8-辛二醇、环己烷二甲醇、甘油、三羟甲基丙烷、三羟甲基乙烷、季戊四醇、山梨醇、蔗糖以及这些中的任一种的烷氧基化物(尤其是乙氧基化物和/或丙氧基化物)、多胺和二或三链烷醇胺。如果多种环氧化物用于合成聚醚多元醇,则后者可以具有所需的氧亚烷基部分的任何排列。它们可以是均聚物(如果仅使用一种环氧化物)、共聚物、无规共聚物、封端聚合物或用不同环氧化物的混合物合成的聚合物,以实现所需的伯羟基含量。
本公开的一个或多个实施方案规定多元醇组合物可以包括聚酯多远醇。聚酯多元醇可以由例如具有2至12个碳原子的有机二羧酸(包括具有8至12个碳原子的芳香族二羧酸)和多元醇(包括具有2至12个碳原子的二醇)制备。合适的二羧酸的实例是丁二酸、戊二酸、己二酸、辛二酸、壬二酸、癸二酸、癸烷二羧酸、顺丁烯二酸、反丁烯二酸、邻苯二甲酸、间苯二甲酸、对苯二甲酸和异构萘二羧酸。二羧酸可以单独或彼此混使用。游离二羧酸可以被对应的二羧酸衍生物(例如具有1至4个碳原子的醇的二羧酸酯或二羧酸酐)代替。一些特定实例可以利用二羧酸混合物,其包括以例如20至35∶35至50∶20至32重量份比率的丁二酸、戊二酸和己二酸,和己二酸,和邻苯二甲酸和/或邻苯二甲酸酐和己二酸的混合物、邻苯二甲酸或邻苯二甲酸酐、间苯二甲酸和己二酸的混合物或丁二酸、戊二酸和己二酸的二羧酸混合物和对苯二甲酸和己二酸的混合物或丁二酸、戊二酸和己二酸的二羧酸混合物。二元醇和多元醇的实例是乙二醇、二乙二醇、1,2-和1,3-丙二醇、二丙二醇、1,4-丁二醇、1,5-戊二醇、1,6-己二醇、1,10-癸二醇、丙三醇、三羟甲基丙烷等。一些特定实例提供乙二醇、二乙二醇、1,4-丁二醇、1,5-戊二醇、1,6-己二醇或所述二醇中的至少两种的混合物,具体地1,4-丁二醇、1,5-戊二醇和1,6-己二醇的混合物。此外,还可以采用由内酯(例如,ε-己内酯)或羟基羧酸(例如,ω-羟基己酸和羟基苯甲酸)制备的聚酯-多元醇。
聚酯多元醇可以通过使有机多羧酸和/或其衍生物与多元醇以例如1∶1至1∶1.8,例如1∶1.05至1∶1.2的摩尔比缩聚来制备。
用于制备本文公开的反应产物的多元醇可以具有300至12,000g/mol重均分子量。包括300至12,000g/mol的所有个别值和子范围;例如,多元醇可以具有300、400、500、750或1000g/mol下限至12,000、10,000、8000、5000或3000g/mol上限的重均分子量。
用于制备本文公开的反应产物的多元醇可以具有1.5至5.0的平均官能度,即羟基官能度。包括1.5至5.0的所有个别值和子范围;例如,多元醇可以具有1.5、1.7或2.0下限至5.0、4.0或3.0上限的平均官能度。
多元醇和氨基多羧酸化合物的反应产物可以通过使多元醇和氨基多羧酸化合物以多元醇羟基摩尔数相对于氨基多羧酸化合物官能团摩尔数的100∶0.5至100∶10摩尔比反应来制备。包括多元醇羟基摩尔数相对于氨基多羧酸化合物官能团摩尔数的100∶0.5至100∶10的所有个别值和子范围;例如多元醇可以与乙二胺四乙酸化合物以多元醇羟基摩尔数相对于氨基多羧酸化合物官能团摩尔数的100∶0.5、100∶1、100∶2、100∶3、100∶4、100∶5、100∶6、100∶7、100∶8、100∶9或100∶10的摩尔比反应。氨基多羧酸化合物官能团包括二酐、单酐二酸、四酸及其组合。
可以使用已知的设备和反应条件来形成反应产物。例如,可以将反应物,即多元醇和氨基多羧酸化合物加热至任何希望的温度,持续足以实现希望的化学/物理转化的特定时间。例如,反应产物可以在50℃至200℃的温度下形成;反应可以发生,例如维持约5分钟至约48小时;并且反应可以在惰性环境,诸如氮气环境中发生。反应产物可以任选地用催化剂形成。
多元醇和氨基多羧酸化合物的反应产物可以包含基于反应产物的总重量0.03至10.0重量百分比的衍生自氨基多羧酸化合物的单元。包括0.03至10.0重量百分比的衍生自氨基多羧酸化合物的单元的所有个别值和子范围;例如反应产物可以包含基于反应产物的总重量0.03、0.05、0.08或1.0下限至10.0、8.0、6.0或5.0上限重量百分比的衍生自氨基多羧酸化合物的单元。
本公开的实施方案提供了无溶剂组合物,其包含多元醇和氨基多羧酸化合物的反应产物和异氰酸酯。无溶剂组合物可以利用已知条件和已知设备来制备,例如混合,其可以针对不同应用而变化。
异氰酸酯可以是聚异氰酸酯。如本文所用,“聚异氰酸酯”是指具有平均大于1.0个异氰酸酯基团/分子,例如大于1.0的平均异氰酸酯官能度的分子。
例如,异氰酸酯可以是脂肪族聚异氰酸酯、环脂肪族聚异氰酸酯、芳基脂肪族聚异氰酸酯、芳香族聚异氰酸酯或其组合。异氰酸酯的实例包括但不限于甲苯2,4-/2,6-二异氰酸酯(TDI)、亚甲基二苯基二异氰酸酯(MDI)、聚合MDI、三异氰酸基壬烷(TIN)、萘基二异氰酸酯(NDI)、4,4′-二异氰酸基二环己基甲烷、3-异氰酸基甲基-3,3,5-三甲基环己基异氰酸酯(异佛尔酮二异氰酸酯IIPDI)、四亚甲基二异氰酸酯、六亚甲基二异氰酸酯(HDI)、2-甲基五亚甲基二异氰酸酯、2,2,4-三甲基六亚甲基二异氰酸酯(THDI)、十二碳亚甲基二异氰酸酯、1,4-二异氰酸基环己烷、4,4′-二异氰酸基-3,3′-二甲基二环己基甲烷、4,4′-二异氰酸基-2,2-二环己基丙烷、3-异氰酸基甲基-1-甲基-1-异氰酸基环己烷(MCI)、1,3-二异辛基氰酸基-4-甲基环己烷、1,3-二异氰酸基-2-甲基环己烷及其组合等。除上文所提及的异氰酸酯之外,可以利用部分改性的聚异氰酸酯,包括脲二酮、异氰尿酸酯、碳二亚胺、脲酮亚胺、脲基甲酸酯或缩二脲结构及其组合等。
异氰酸酯可以是聚合的。如本文所用,在描述异氰酸酯时,“聚合的”是指具有较高分子量的同系物和/或异构体。例如,聚合的亚甲基二苯基异氰酸酯是指亚甲基二苯基异氰酸酯的较高分子量同系物和/或异构体。
异氰酸酯可以是预聚物。例如,异氰酸酯可以是异氰酸酯封端的预聚物,例如异氰酸酯封端的聚氯酯预聚物。预聚物可以通过使异氰酸酯和多元醇反应来制备。
如所提及的,异氰酸酯可以具有大于1.0个异氰酸酯基团/分子的平均官能度。例如,异氰酸酯可以具有1.75至3.50的平均官能度。包括1.75至3.50的所有个别值和子范围;例如,异氰酸酯可以具有1.75、1.85或1.95下限至3.50、3.40或3.30上限的平均官能度。
异氰酸酯可以具有125g/eq至300g/eq的异氰酸酯当量。包括125至300g/eq的所有个别值和子范围;例如,异氰酸酯可以具有125、135或145g/eq下限至300、290或280g/eq上限的异氰酸酯当量。
异氰酸酯可以通过已知方法制备。例如,可以通过使对应的多元胺光气化并且形成聚氯基甲酰氯并且对其进行热分解以提供聚异氰酸酯和氯化氢或通过无光气的方法,诸如通过使对应的多元胺与脲和醇反应以得到聚氯基甲酸酯并且对其进行热分解以得到异氰酸酯和醇来制备异氰酸酯。
异氰酸酯可以商购获得。可以利用的商业异氰酸酯和/或NCO封端的预聚物的实例包括但不限于商品名为MOR-FREETM、VORANATETM和PAPITM的可从Dow Chemical Company获得的异氰酸酯等。
可以利用异氰酸酯,使得无溶剂组合物具有1.0至1.6范围内的异氰酸酯指数。异氰酸酯指数可以确定为异氰酸酯的当量除以无溶剂组合物的异氰酸酯反应性组分例如异氰酸酯反应性氢的总当量,乘以。换言之,异氰酸酯指数可以确定为异氰酸酯基团与异氰酸酯反应性氢的比率。包括1.0至1.6的所有个别值和子范围;例如,无溶剂组合物可以具有1.0、1.05或1.1下限至1.6、1.5或1.45上限的异氰酸酯指数。
无溶剂组合物可以包含催化剂,例如用于形成聚氯酯的已知催化剂。催化剂的实例包括铝催化剂、铋催化剂、锡催化剂、钒催化剂、锌催化剂、锆催化剂、钛催化剂、胺催化剂及其组合。一个或多个实施方案规定催化剂选自二乙酸二丁基锡、二月桂酸二丁基锡、二乙酰丙酮二丁基锡、二硫醇二丁基锡、二辛酸二丁基锡、二马来酸二丁基锡、乙酰丙酮酸二丁基锡、氧化二丁基锡及其组合。当使用时,基于无溶剂组合物的总重量,催化剂可以是百万分之0.001(ppm)至100pm。例如,基于无溶剂组合物的总重量,催化剂可以是0.005ppm至10ppm。
无溶剂组合物是本领域已知的并且可以用于许多应用,例如作为粘合剂,诸如层压粘合剂,或作为涂料。本公开的实施方案规定无溶剂组合物可以包含一种或多种额外组分,例如像与粘合剂组合物一起使用的已知组分和/或与涂料组合物一起使用的已知组分。可以针对不同应用利用不同的额外组分和/或不同量的额外组分。额外组分的实例包括多元醇、表面活性剂、螯合剂、交联剂、扩链剂、抗氧化剂及其组合以及其他已知的组分。
有利地,无溶剂组合物可以施加至材料。例如,可以将无溶剂组合物施加至第一材料并且可以将第二材料与无溶剂组合物接触;此后,可以将无溶剂组合物固化以形成层压板。另外,可以将无溶剂组合物施加至第一材料,并且然后可以将组合物固化以形成涂层。无溶剂组合物可以通过已知方法,例如通过使用已知组件、已知设备和已知的应用施加条件,诸如凹版层压、柔版层压等来施加。另外,可以将无溶剂组合物和异氰酸酯施加在不同的基材上,并且然后层压在一起.
可以将本文公开的无溶剂组合物固化,例如,多元醇和氨基多羧酸化合物的反应产物和异氰酸酯可以彼此反应,以形成固化产物。可以利用已知的固化条件,诸如温度、湿度和持续时间来固化本文公开的无溶剂组合物。
有利地,与包含与用于制备反应产物的多元醇相似的多元醇的其他组合物相比,在7天时,本文公开的无溶剂组合物可以提供(例如,固化时)改善的T型剥离粘结强度。如所提及的,7天时增加的T型剥离粘结强度指示更大粘合剂强度。此更大的粘合剂强度可以理想地帮助为用本文公开的无溶剂组合物制备的产物提供更大的密封。
有利地,与包含与用于制备反应产物的多元醇相似的多元醇的其他组合物相比,本文公开的无溶剂组合物可以提供(例如,固化时)提高的连袋煮值。提高的连袋煮值指示用本文公开的无溶剂组合物制备的包装产品与消费品(诸如酱汁等)结合使用时更大的粘合强度。换言之,提高的连袋煮值可以指示消费品对包装失效的希望的改善耐受性。
另外,与包含与用于制备反应产物的多元醇相似的多元醇的其他组合物相比,包含所述反应产物的无溶剂组合物可以提供改善的,例如更快的固化。有利地,相对更快的固化可以帮助提供更快的芳香族伯胺(PAA)衰减。更快的芳香族伯胺(PAA)衰减对于许多应用,诸如与食品法规遵从性相关联的应用可以是希望的。此外,另外,与包含与用于制备反应产物的多元醇相似的多元醇的其他组合物相比,包含所述反应产物的无溶剂组合物可以提供提高的,例如延长的储放时间。
如本文所用,与用于制备反应产物的多元醇相似的多元醇是指与用于制备反应产物的多元醇相同的多元醇;或与用于制备反应产物的多元醇相比,具有±10%的重均分子量和±10%的平均羟基官能度的多元醇。
实施方案规定无溶剂组合物可以与各种材料,例如基材一起使用。可以与本文公开的无溶剂组合物一起使用的材料的实例包括聚合物材料,诸如聚对苯二甲酸乙二醇酯、聚乙烯、聚丙烯及其组合。例如,聚合物材料可以是膜。实施方案规定可以与无溶剂组合物一起使用的材料可以包括金属,例如箔或金属化膜。箔和金属化膜是熟知的。例如,聚合物材料可以在金属化之前进行预处理,诸如通过电晕处理和等离子体处理进行预处理。然后,可以通过物理气相沉积工艺进行金属化。在此类过程中,金属在真空下被加热并蒸发。然后金属在聚合物材料上凝结以形成金属化膜。合适金属的实例包括但不限于铝、镍、铬及其组合。实施方案规定粘合剂组合物可以例如用于膜对膜层压和膜对箔层压。
实例
在实例中,使用材料的各种术语和名称,包括例如以下:
氨基多羧酸化合物(乙二胺四乙酸二酐;从Aldrich获得);
多元醇#1(多元醇;70wt%聚醚多元醇/30wt%蓖麻油共混物;聚醚多元醇具有2.0至3.0的平均官能度和1280g/mol的重均当量);
多元醇#2(63wt%多元醇/27wt%蓖麻油/10wt%硅烷共混物;多元醇具有2.0至3.0的平均官能度和1200g/mol的重均当量);
PAACEL L-75-191(NCO封端的无溶剂聚氯酯粘合剂;从Dow Chemical Company获得);
金属化PET膜(金属化48g PET膜;从Filmquest Group获得);PET膜(48LBT;聚酯膜[聚(乙二醇-对苯二甲酸酯];从DuPont获得);PET/箔层压膜(PET Al箔膜;从FILM TECHInc.获得);低密度聚乙烯膜(GF-19膜;高滑度低密度膜;厚度1.5密耳;从Berry PlasticsCorp获得)。
如下制备实例1,多元醇和乙二胺四乙酸二酐的反应产物。将多元醇#1(99.5克)添加到容器中并在大约120℃在氮气下干燥60分钟。然后,将容器中的内容物冷却至大约80℃,并且将乙二胺四乙酸二酐(0.5克)添加到容器中。将容器中的内容物缓慢加热至150℃并在此温度下维持大约1小时;此后,将容器的内容物缓慢加热至160℃并在此温度下维持大约1小时;此后,将容器中的内容物缓慢加热至180℃并在此温度下维持大约3小时。然后,将容器的内容物冷却至大约60℃并过滤以提供实例1。实例1包含基于实例1的总重量0.5重量百分比的衍生自乙二胺四乙酸二酐的单元。
如实例1制备实例2,多元醇和乙二胺四乙酸二酐的反应产物,但使用多元醇#1(99克)。实例2包含基于实例2的总重量1.0重量百分比的衍生自乙二胺四乙酸二酐的单元。
实例1-2和多元醇#1的多种特性。根据ASTM E 1899-08确定OH数;根据ASTMD4274-16确定酸值;经由如下所述的SEC分析确定数均分子量(Mn)和重均分子量(Mw)。将各个样品(0.01克)溶解在四氢呋喃(4.0mL)以提供样品浓度(2.5mg/mL)。分离模块:Waterse2695;柱:Polymer Labs PLGel Mixed E柱×2,3μm粒径和Mixed C柱×1,5μm粒径;柱温:40℃;洗脱液:四氢呋喃(不稳定的);流速:1mL/min;注射量:50μL;分析时间:40分钟;检测器:Waters2414折射率检测器(40℃);校准:安捷伦科技聚苯乙烯(PS)-Medium EasiVials,批号0006386106;软件:Agilent OpenLAB CDS(EZChrome Edition)A.04.06版本。
结果报告在表1中。
表1
表1的数据表明,对于实例1-2,制备了多元醇和乙二胺四乙酸二酐的反应产物。
如下形成实例3,无溶剂组合物。将实例1和PACACEL L75-191以1.3的异氰酸酯指数用滚筒混合器混合10分钟以提供实例3。
如下形成实例4,无溶剂组合物。将实例2和PACACEL L75-191以1.3的异氰酸酯指数用滚筒混合器混合10分钟以提供实例4。
如下利用实例3来制备层压板。利用油加热辊手动层压机(夹区温度150°F;运行速度20ft/min)和大约1.05磅/令的涂层重量。逐片制备层压板,其具有大约12英寸×10英寸的涂覆区域。将实例3配制成在乙酸乙酯中的35重量百分比固体,并且然后涂覆到原膜上;将涂覆的原膜烘箱干燥(90℃;大约1分钟)。然后用油加热辊手动层压机(大约40psi)将涂覆的原膜层压到二次膜上;然后将层压板在大约20℃下固化7天。
如上所讨论,利用对比实例A制备层压板,其由多元醇#1和PACACEL L75-191组成以提供1.3的异氰酸酯指数。
对层压板进行T型剥离粘结强度测试和连袋煮测试。结果报告在表2中。
在具有50N加载单元的Instron拉伸测试仪上以10英寸/分钟的速率在1英寸条带上测量T型剥离粘结强度。针对每个层压板测试三个条带,并且记录高强度和平均强度以及失效模式。在膜撕裂和膜拉伸的情况下,报告高值,并且在其他失效模式中,报告平均T型剥离粘结强度。
如下进行层压板的连袋煮测试。将固化的层压板(9英寸×11英寸)折叠以形成双层,使得一层的PE膜与另一层的PE膜接触。然后用切纸机修整边缘以获得折叠片(大约5英寸×7英寸)。然后将边缘热密封以形成内部尺寸为4英寸×6英寸的小袋。然后通过开口边缘将100mL等重量份的番茄酱、醋和植物油的酱汁共混物装入小袋中。装填之后,以使小袋内的空气滞留最小化的方式密封小袋。然后将装填的小袋小心地置于沸水中并保持浸入在水中30分钟或60分钟。完成之后,将隧道形成、分层或泄漏的程度与标记的预先存在的缺陷进行比较。
表2
表2的数据表明,与对比实例A相比,对于包括金属化膜的两种层压板,实例3在7天时有利地具有改善的T型剥离粘结强度。
另外,表2的数据表明,与对比实例A相比,对于包括金属化膜的两种层压板,实例3在30分钟时有利地具有提高的连袋煮值。提高的连袋煮值有利地表明对于所测试的酱汁共混物具有更大的粘合强度。
如上所讨论,利用实例4制备层压板。利用对比实例B制备层压板,其由多元醇#2和PAACEL L75-191组成以提供1.3的异氰酸酯指数,如上所讨论。如上所讨论,对层压板进行T型剥离粘结强度测试和连袋煮测试。结果报告在表3中。
表3
表3的数据表明,与对比实例B相比,对于包括金属化膜的两种层压板,实例4在7天时有利地具有改善的T型剥离粘结强度。
另外,表3的数据表明,与对比实例B相比,对于包括金属化膜的两种层压板,实例4在30分钟时有利地具有提高的连袋煮值。提高的连袋煮值有利地表明对于所测试的酱汁共混物具有更大的粘合强度。
另外,表3的数据表明,与对比实例B相比,对于包括金属化膜的层压板,实例4在60分钟时有利地具有提高的连袋煮值。提高的连袋煮值有利地表明对于所测试的酱汁共混物具有更大的粘合强度。
如下确定芳香族伯胺(“PAA”)衰减。将样品在25℃和50%相对湿度下固化2天。然后,将固化的层压结构折叠以形成双层,使得一层的聚乙烯膜与另一层的聚乙烯膜接触。然后用切纸机修整边缘以提供折叠片(6.5英寸×7英寸)。然后将边缘热封以形成内部尺寸为5.5英寸×5.6英寸的小袋。然后将100mL的3重量百分比的乙酸溶液装入小袋中。将小袋在空气循环烘箱中在70℃下萃取2小时,并且然后在冷自来水中骤冷,以使测试溶液在室温下平衡,将100ml测试溶液转移到烧杯中。用比色法确定萃取到3重量百分比的乙酸溶液中的芳香族伯胺的量。结果报告在表4中。
表4
表4的数据表明,与对比实例A相比,实例4有利地具有改善的,即减少的芳香族伯胺衰减。
此外,表4的数据表明,与对比实例A相比,实例4有利地具有小于2.0ppb的芳香族伯胺浓度。德国联邦风险评估研究所(BfR)在一份立场文件中建议使用小于2.0ppb的芳香族伯胺浓度。
Claims (9)
1.一种无溶剂组合物,其包含
通过使多元醇和氨基多羧酸化合物反应制备的反应产物;和
异氰酸酯。
2.根据权利要求1所述的无溶剂组合物,其中所述氨基多羧酸化合物是乙二胺四乙酸化合物。
3.根据权利要求1—2中任一项所述的无溶剂组合物,其中所述氨基多羧酸化合物选自乙二胺四乙酸酐、乙二胺四乙酸及其组合。
4.根据权利要求1-3中任一项所述的无溶剂组合物,其中所述反应产物具有基于所述反应产物的总重量0.03至10.0重量百分比的衍生自所述氨基多羧酸化合物的单元。
5.根据权利要求1-4中任一项所述的无溶剂组合物,其中所述多元醇具有300至12,000g/mol的重均分子量。
6.根据权利要求1-5中任一项所述的无溶剂组合物,其中所述多元醇具有1.5至5.0的平均官能度。
7.根据权利要求1-6中任一项所述的无溶剂组合物,其中所述多元醇和氨基多羧酸化合物以多元醇羟基摩尔数相对于氨基多羧酸化合物官能团摩尔数的100∶0.5至100∶10摩尔比反应。
8.根据权利要求1-7中任一项所述的无溶剂组合物,其中所述无溶剂组合物具有在1.0至1.6范围内的异氰酸酯指数。
9.一种由根据权利要求1-8中任一项所述的无溶剂组合物形成的层压板。
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