CN106661416B - 聚氨酯粘合剂组合物 - Google Patents
聚氨酯粘合剂组合物 Download PDFInfo
- Publication number
- CN106661416B CN106661416B CN201480081393.1A CN201480081393A CN106661416B CN 106661416 B CN106661416 B CN 106661416B CN 201480081393 A CN201480081393 A CN 201480081393A CN 106661416 B CN106661416 B CN 106661416B
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- Prior art keywords
- adhesive composition
- glycol
- polyurethane adhesive
- polyurethane
- group
- 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.)
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- 239000004814 polyurethane Substances 0.000 title claims abstract description 46
- 239000000853 adhesive Substances 0.000 title claims abstract description 43
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 42
- 239000000203 mixture Substances 0.000 title claims abstract description 42
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 34
- 150000003077 polyols Chemical class 0.000 claims abstract description 41
- 229920005862 polyol Polymers 0.000 claims abstract description 37
- 229920003009 polyurethane dispersion Polymers 0.000 claims abstract description 29
- 229920005906 polyester polyol Polymers 0.000 claims abstract description 24
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 22
- 229920000570 polyether Polymers 0.000 claims abstract description 22
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims abstract description 16
- 239000004971 Cross linker Substances 0.000 claims abstract description 15
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 15
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 15
- 239000002563 ionic surfactant Substances 0.000 claims abstract description 10
- 229920000768 polyamine Polymers 0.000 claims abstract description 9
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 15
- -1 polybutylene Polymers 0.000 claims description 9
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical group C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 8
- 239000002202 Polyethylene glycol Substances 0.000 claims description 7
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- 229920001223 polyethylene glycol Polymers 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 6
- 239000007859 condensation product Substances 0.000 claims description 5
- 150000002009 diols Chemical class 0.000 claims description 5
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 5
- 229920000909 polytetrahydrofuran Polymers 0.000 claims description 5
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 4
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 claims description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
- 229920001451 polypropylene glycol Polymers 0.000 claims description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 claims description 4
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 claims description 4
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 3
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims description 3
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 claims description 2
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 claims description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
- 239000005700 Putrescine Substances 0.000 claims description 2
- 235000019437 butane-1,3-diol Nutrition 0.000 claims description 2
- GKGXKPRVOZNVPQ-UHFFFAOYSA-N diisocyanatomethylcyclohexane Chemical compound O=C=NC(N=C=O)C1CCCCC1 GKGXKPRVOZNVPQ-UHFFFAOYSA-N 0.000 claims description 2
- WJRMGBWBIGOIOF-UHFFFAOYSA-N dodecyl benzenesulfonate;propan-2-amine Chemical compound CC(C)N.CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 WJRMGBWBIGOIOF-UHFFFAOYSA-N 0.000 claims description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 2
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 2
- 229920001748 polybutylene Polymers 0.000 claims description 2
- 229960004063 propylene glycol Drugs 0.000 claims description 2
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 claims description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000013638 trimer Substances 0.000 claims description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 description 14
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 11
- 239000004698 Polyethylene Substances 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 239000011888 foil Substances 0.000 description 8
- 229920000573 polyethylene Polymers 0.000 description 8
- 239000012948 isocyanate Substances 0.000 description 7
- 150000002513 isocyanates Chemical class 0.000 description 7
- 239000002318 adhesion promoter Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000758 substrate Substances 0.000 description 5
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 239000003945 anionic surfactant 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
- 239000004094 surface-active agent Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- WXUAQHNMJWJLTG-UHFFFAOYSA-N 2-methylbutanedioic acid Chemical compound OC(=O)C(C)CC(O)=O WXUAQHNMJWJLTG-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-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
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 159000000032 aromatic acids Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N hexane carboxylic acid Natural products CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 229920006284 nylon film Polymers 0.000 description 2
- 239000000123 paper 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
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920006267 polyester film Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-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
- 150000004072 triols Chemical class 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-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
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- GOHPTLYPQCTZSE-UHFFFAOYSA-N 2,2-dimethylsuccinic acid Chemical compound OC(=O)C(C)(C)CC(O)=O GOHPTLYPQCTZSE-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- WZHHYIOUKQNLQM-UHFFFAOYSA-N 3,4,5,6-tetrachlorophthalic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(O)=O WZHHYIOUKQNLQM-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- 229920006309 Invista Polymers 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 229920013701 VORANOL™ Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007970 homogeneous dispersion 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002523 polyethylene Glycol 1000 Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- ZNZJJSYHZBXQSM-UHFFFAOYSA-N propane-2,2-diamine Chemical compound CC(C)(N)N ZNZJJSYHZBXQSM-UHFFFAOYSA-N 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical class S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/08—Polyurethanes from polyethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—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
- C08G18/4833—Polyethers containing oxyethylene units
-
- 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
- C08G18/0838—Manufacture of polymers in the presence of non-reactive compounds
- C08G18/0842—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents
- C08G18/0861—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers
- C08G18/0866—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers the dispersing or dispersed phase being an aqueous medium
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4205—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups
- C08G18/4208—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups
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Abstract
提供聚氨酯粘合剂组合物,其包含聚氨酯分散体和1.2wt%至20wt%的聚异氰酸酯交联剂。所述聚氨酯分散体是10wt%至40wt%的单体芳香族二异氰酸酯、30wt%至65wt%的聚醚多元醇、15wt%至30wt%的具有至少一个芳香族基团和一个脂族基团的聚酯多元醇、0.1%至8%的多胺和0.5%至10%的离子表面活性剂的反应产物。
Description
技术领域
本发明涉及用于制造层压体的粘合剂组合物。具体地讲,本发明涉及包含聚氨酯分散体的粘合剂组合物。
背景技术
粘合剂组合物被用于将例如聚乙烯(PE)、聚丙烯、聚酯、聚酰胺、金属、纸或玻璃纸的基材粘结在一起以形成复合膜,即层压体。层压体通常被用于包装工业,尤其用于食品包装。出于环境、健康和安全原因,粘合剂优选地为水性或无溶剂。聚氨酯分散体是用于无溶剂粘合剂的常用组分。
不同基材通常对涂布到其上的粘合剂具有不同要求。为了将PE基材与金属基材粘结,例如,需要粘合剂在粘结强度(BS)、热封强度(HS)和低摩擦系数(COF)上表现特别好。期望提供在BS、HS、和COF上具有良好性能的聚氨酯粘合剂组合物,并因此特别适于将PE和金属粘结。
发明内容
本发明提供聚氨酯粘合剂组合物,其包含聚氨酯分散体和以聚氨酯分散体的总干重计按干重1.2%至20%的聚异氰酸酯交联剂。
聚氨酯分散体是以聚氨酯分散体的总干重计按干重10%至40%的单体芳香族二异氰酸酯、30%至65%的聚醚多元醇、15%至30%的具有至少一个芳香族基团和一个脂族基团的聚酯多元醇、0.1%至8%的多胺和0.5%至10%的离子表面活性剂的反应产物。
具体实施方式
聚氨酯粘合剂组合物包含聚氨酯分散体。
聚氨酯分散体优选地具有25%至60%,优选地30%至55%,以及更优选地35%至50%的固体含量,即聚氨酯聚合物颗粒的含量。
聚氨酯分散体是单体芳香族二异氰酸酯、聚醚多元醇、具有至少一个芳香族基团和一个脂族基团的聚酯多元醇、多胺和离子表面活性剂的反应产物。聚氨酯分散体包含以聚氨酯分散体的总干重计按干重10%至40%,优选地12%至38%,以及更优选地15%至35%的单体芳香族二异氰酸酯;30%至65%,优选地35%至60%,以及更优选地40%至55%的聚醚多元醇;15%至30%,优选地18%至28%,以及更优选地20%至25%的具有至少一个芳香族基团和一个脂族基团的聚酯多元醇;0.1%至8%,优选地0.2%至6%,以及更优选地0.5%至5%的多胺;以及0.5%至10%,优选地1%至8%,以及更优选地1.5%至6%的离子表面活性剂。
每一多元醇具有500g/mol至4000g/mol,优选地750g/mol至3500g/mol,以及更优选地800g/mol至3000g/mol的分子量(Mw)。每一多元醇具有1.8至4,优选地1.9至3,以及更优选地2至2.5的官能度(每分子的异氰酸酯反应位点的平均数)。
聚氨酯粘合剂组合物进一步包含以聚氨酯分散体的总干重计按干重1.2%至20%,优选地1.5%至15%,以及更优选地2.5%至10%的聚异氰酸酯交联剂。
聚氨酯分散体
本发明的聚氨酯分散体由聚氨酯预聚物制得。本发明的聚氨酯预聚物利用单体芳香族二异氰酸酯、聚醚多元醇和具有至少一个芳香族基团和一个脂族基团的聚酯多元醇以该领域的普通技术人员熟知的任意方式,包括缩聚来制备。聚氨酯预聚物优选地是NCO基团封端的预聚物。有机溶剂优选地不用于制备聚氨酯预聚物。
单体芳香族二异氰酸酯优选地具有小于300g/mol,以及优选地小于275g/mol的分子量Mw。单体芳香族二异氰酸酯选自二苯基甲烷二异氰酸酯(MDI)、甲苯二异氰酸酯(TDI)和其组合。一般地可以使用具有任何普遍出售的异构体配比的TDI。最普遍出售的TDI具有80%的2,4-异构体和20%的2,6-异构体的异构体配比。也可使用具有其它异构体配比的TDI。当使用MDI时,优选地是纯4,4′-MDI或MDI异构体的任意组合。更优选地,其是纯4,4′-MDI和4,4′-MDI与其它MDI异构体的任意组合。当使用4,4′-MDI与其它MDI异构体的组合时,4,4′-MDI的优选浓度是所有MDI异构体的25%至75%。
聚醚多元醇是环氧乙烷、环氧丙烷、四氢呋喃和环氧丁烷的加聚、共加成和接枝产物,多元醇的缩合产物以及其任意组合。聚醚多元醇的适宜实例包括聚丙二醇(PPG)、聚乙二醇(PEG)、聚丁二醇(PBG)、聚四亚甲基醚二醇(PTMEG)以及其任意组合。优选地,聚醚多元醇是PEG与上述至少另一种聚醚多元醇的组合。更优选地,聚醚多元醇是PEG与PPG、聚丁二醇和PTMEG中的至少之一的组合。
具有至少一个芳香族基团和一个脂族基团的聚酯多元醇是二醇与二羧酸的缩合产物。
二醇的适宜实例是乙二醇、丁二醇、二乙二醇、三乙二醇、聚亚烷基二醇例如聚乙二醇、1,2-丙二醇、1,3-丙二醇、1,3-丁二醇、1,4-丁二醇、1,6-己二醇、新戊二醇和其任意组合。为了实现大于2的多元醇官能度,也可使用三醇和/或四醇。三醇的适宜实例包括三羟甲基丙烷和丙三醇。四醇的适宜实例包括赤藓醇和季戊四醇。
二羧酸是芳香族酸和脂族酸的混合物。芳香族酸的适宜实例是邻苯二甲酸、间苯二甲酸和对苯二甲酸;而脂族酸的适宜实例是己二酸、壬二酸、癸二酸、戊二酸、四氯邻苯二甲酸、马来酸、富马酸、衣康酸、丙二酸、辛二酸、2-甲基琥珀酸、3,3-二乙基戊二酸和2,2-二甲基琥珀酸。同样也可使用这些酸的酸酐。优选地,脂族酸和芳香族酸是饱和的,并分别地是己二酸和间苯二甲酸。单羧酸(例如苯甲酸和己烷羧酸)应最少或不包括。
借助于离子表面活性剂将聚氨酯预聚物分散在水中,然后分散在多胺中以制得聚氨酯分散体。
优选地,离子表面活性剂是阴离子的。阴离子表面活性剂的适宜实例选自磺酸盐、磷酸盐、羧酸盐和其任意组合。优选地,阴离子表面活性剂是磺酸盐,例如十二烷基苯磺酸钠、十二烷基磺酸钠、十二烷基二苯醚二磺酸钠、正癸基二苯醚二磺酸钠、十二烷基苯磺酸异丙胺和己基二苯醚二磺酸钠。更优选地,阴离子表面活性剂是十二烷基苯磺酸钠。
优选地,在加水前将离子表面活性剂引入聚氨酯预聚物中,但是在添加聚氨酯预聚物前将表面活性剂注入水中不超出本发明的范围。
然后在添加离子表面活性剂后添加多胺,和水以用于链延伸目的。
优选地,多胺是二胺,其中每一胺基是伯胺或仲胺。二胺的适宜实例包括乙二胺、1,2-和1,3-二氨基丙烷、1,4-二氨基丁烷、1,6-二氨基己烷、异佛尔酮二胺和其任意组合。
聚异氰酸酯交联剂
本发明的聚异氰酸酯交联剂每分子具有两个或更多个异氰酸酯基团。优选的聚异氰酸酯交联剂每分子具有三个或更多个异氰酸酯基团。更优选的聚异氰酸酯交联剂是单体二异氰酸酯的三聚体。
用于制得聚异氰酸酯交联剂的优选的单体二异氰酸酯是单体脂族二异氰酸酯。单体脂族二异氰酸酯的适宜实例包括1,6-六亚甲基二异氰酸酯(HDI)、1-异氰酸根合-3-异氰酸根合甲基-3,5,5-三甲基-环己烷(IPDI)、4,4′-二异氰酸根合二环己基甲烷(H12MDI)、二异氰酸根合甲基-环己烷(ADI)和其任意组合。优选的单体脂族二异氰酸酯是HDI和ADI,以及最优选的单体脂族二异氰酸酯是HDI。上述单体芳香族二异氰酸酯可任选地用于制备聚异氰酸酯交联剂。
优选地,聚异氰酸酯交联剂是亲水改性的。亲水改性是其中一个或多个异氰酸酯基团与化合物反应以将亲水基团附接到其主链的过程。优选的亲水基团是阴离子基团或包含至少一个环氧乙烷单元的基团。
在搅拌下将聚异氰酸酯交联剂加入聚氨酯分散体中以制备本发明的聚氨酯粘合剂组合物。
其它添加剂
聚氨酯分散体可进一步包含反应性结合到聚氨酯预聚物的主链的粘合促进剂。也可将粘合促进剂作为后添加剂加入聚氨酯粘合剂组合物中。在该领域中熟知选择适宜的粘合促进剂,并且以以聚氨酯预聚物的总干重计按干重0.1%至3%,优选地0.1%至2%,以及更优选地0.1%至1%的量使用。
任意粘合促进剂可用于本发明,但是硅烷粘合促进剂是优选的。硅烷粘合促进剂的适宜实例包括氨基硅烷例如氨基丙基三乙氧基硅烷、环氧硅烷例如3-环氧丙氧基丙基三乙氧基硅烷和巯基硅烷例如γ-巯基丙基三甲氧基硅烷。
层压体
将聚氨酯粘合剂组合物涂布在包括金属箔、聚酯膜和尼龙膜的基材的表面上。优选地,将其涂布在金属箔的表面上。更优选地,金属箔是铝(Al)箔。
然后,将所涂布的聚氨酯粘合剂组合物干燥以形成干层。当残余水少于所涂布的聚氨酯粘合剂组合物的10%时,所涂布的聚氨酯粘合剂组合物被视为是干燥的。
将聚乙烯膜的表面覆盖在所涂布的聚氨酯粘合剂组合物的干层上以形成聚乙烯膜-聚氨酯粘合剂-金属箔复合物(复合膜,也称为层压体)。在不同应用中,金属箔可被聚酯膜或尼龙膜替换。优选地,使层压体经受机械力以将膜按压得甚至更紧密。优选地通过使层压体通过辊之间来施加此机械力。
层压体可以是包含额外膜和额外粘合剂组合物的较厚层压体的一部分。该额外膜可以是常用于层压体工业的任意膜,包括聚合物膜、纸和金属箔。该额外粘合剂组合物可以与本发明的聚氨酯粘合剂组合物相同或不同,并可以是层压体工业中任意常用的粘合剂组合物。
实例
I.原材料
异氰酸酯:
ISONATETM 50O,P′异氰酸酯(50O,P′)是可购自陶氏化学公司(The Dow ChemicalCompany)的2,4-MDI和4,4′-MDI的混合物。
ISONATETM 125M异氰酸酯(125M)是可购自陶氏化学公司的纯4,4′-MDI。
聚酯多元醇:
BESTERTM 104多元醇(BESTER 104)是具有一个脂族基团和一个芳香族基团的聚酯多元醇,并可购自陶氏化学公司。
HSM-822-3多元醇(HSM)是具有一个脂族基团和一个芳香族基团的聚酯多元醇,并可购自旭川化学(苏州)有限公司(Xuchuan Chemical(Suzhou)Co.,Ltd)。
XCP-940AD多元醇(XCP)是具有一个脂族基团和一个芳香族基团的聚酯多元醇,并可购自旭川化学(苏州)有限公司。
BESTERTM 127多元醇(BESTER 127)是具有一个脂族基团,但没有芳香族基团的聚酯多元醇,并可购自陶氏化学公司。
BESTERTM264多元醇(BESTER 264)是具有一个脂族基团,但没有芳香族基团的聚酯多元醇,并可购自陶氏化学公司。
聚醚多元醇:
VORANOLTM CP750多元醇(CP750)是聚醚多元醇,并可购自陶氏化学公司。
VORANOLTM 2120多元醇(VORANOL 2120)是聚醚多元醇,并可购自陶氏化学公司。
VORANOLTM WD2139多元醇(WD2139)是聚醚多元醇,并可购自陶氏化学公司。
VORANOLTM V1010多元醇(V1010)是聚醚多元醇,并可购自陶氏化学公司。
CARBOWAXTM聚乙二醇1000(PEG 1000)是聚醚多元醇,并可购自陶氏化学公司。
TERATHANETM PTMEG 2000多元醇(PTMEG 2000)是聚醚多元醇,并可购自英威达公司(Invista Company)。
交联剂:
CR3A交联剂(CR3A)是可购自陶氏化学公司的亲水性改性的聚异氰酸酯交联剂。
其它:
RHODACALTM DS-4表面活性剂(DS-4)是可购自罗地亚公司(Rhodia Company)的具有24%固体含量的阴离子表面活性剂。
1,2-丙二胺(PDA)是可购自西格玛-奥德里奇公司(Sigma-Aldrich Company)的二胺。
II.试验方法
1.粘结强度(BS)
将本发明的层压体切成15mm宽条带用以利用可购自英斯特朗集团(InstronCorporation)的5940系列单柱台面系统(5940Series Single Column Table Top System)在250mm/min十字头速度下进行T-剥离试验。在试验期间,通过手指轻轻地拉每个条带的尾部以确保尾部相对于剥离方向保持90度。每个样品测试三个条带并计算平均值。结果利用N/15mm的单位表示。值越高,粘结强度越好。
2.热封强度(HS)
将层压体在可购自Brugger Company的HSG-C热封机中在140℃密封温度和300N压力下热封1秒,然后冷却并切成15mm宽条带用以利用可购自英斯特朗集团的5940系列单柱台面系统在250mm/min十字头速度下进行热封强度试验。每个样品测试三个条带并计算平均值。结果利用N/15mm的单位表示。值越高,热封强度越好。
3.摩擦系数(COF)
将层压体放入50℃烘箱中48小时,然后取出,冷却,并切成64mm×64mm和10cm×10cm的片。将64mm×64mm的片粘在滑块上并将10cm×10cm片粘在可购自广州标际包装设备有限公司的GM-1摩擦系数测试器(GM-1测试器)的平台上,两种片的聚乙烯侧彼此相对。在测试前将GM-1测试器校准。每个样品测试三对片(一个64mm×64mm的片和一个10cm×10cm的片)并计算平均值。将结果以纯数值表示。数值越低,COF性能越好。
III.实例
1.本发明的聚氨酯分散体1至5(PU 1至5)和比较用聚氨酯分散体6至11(比较用PU6至11)的制备
将异氰酸酯加入多元醇的混合物中,并在65-90℃下反应4-5小时,直到混合物达到理论异氰酸酯基团(NCO)含量并制得聚氨酯预聚物。将聚氨酯预聚物转移到塑料罐中,并将RHODACAL DS-4表面活性剂加入塑料罐中,以2000-3000rpm搅拌1-3分钟。在搅拌下,将5℃去离子水加入同一罐中以制得均质分散体。然后将1,2-丙二胺(PDA)水溶液(20%)缓慢地加入分散体中,以1000-1500rpm搅拌15-30分钟以制造聚氨酯分散体。每个PU分散体的组分详细地列在表1中。
表1
2.聚氨酯粘合剂组合物和层压体的制备
将每一以上聚氨酯分散体与以PU分散体的总重量计按重量2%的CR3A交联剂混合15分钟以制得聚氨酯粘合剂组合物。将该聚氨酯粘合剂组合物涂布到聚对苯二甲酸乙二酯(PET)做底衬的铝箔,在80℃下在烘箱中干燥40秒,然后从烘箱中取出并利用可购自化学仪器公司(Cheminstruments,Inc.)的HL-101层压机覆盖(或层压)40μm厚的PE膜。将铝箔-聚氨酯粘合剂组合物-PE膜层压体在50℃下固化48小时并测试。
IV.结果
表2
粘合剂 | PU | BS(N/15mm) | HS(N/15mm) | COF |
1 | PU 1 | 5.4 | 51 | 0.2 |
2 | PU 2 | 5.1 | 44 | 0.23 |
3 | PU 3 | 4.8 | 40 | 0.28 |
4 | PU 4 | 4.3 | 42 | 0.26 |
5 | PU 5 | 4.5 | 56 | 0.25 |
比较用6 | 比较用PU 6 | 3.4 | 35 | 0.45 |
比较用7 | 比较用PU 7 | 2.3 | 30 | 0.38 |
比较用8 | 比较用PU 8 | 2.0 | 20 | 0.46 |
比较用9 | 比较用PU 9 | 1.6 | 18 | 0.5 |
比较用10 | 比较用PU 10 | 2.5 | 28 | 0.27 |
比较用11 | 比较用PU 11 | 2.2 | 29 | 0.25 |
比较用PU6是非推荐的聚酯多元醇(具有一个脂族基团但没有芳香族基团的聚酯多元醇)和不充分的聚醚多元醇的反应产物。比较用PU7使用非推荐的聚酯多元醇(具有一个脂族基团但没有芳香族基团的聚酯多元醇)。比较用PU8使用比PU1-5更高的异氰酸酯。比较用PU9使用比PU1-5更高的聚醚多元醇,但不使用任何聚酯多元醇。比较用PU10使用更高的非推荐的聚酯多元醇(具有一个脂族基团但没有芳香族基团的聚酯多元醇),和不充足的聚醚多元醇。而比较用PU11使用非推荐的异氰酸酯和比PU1-5更高的聚酯多元醇。所有这些比较用聚氨酯分散体当制成比较用聚氨酯粘合剂组合物(粘合剂)时,提供比由本发明的聚氨酯分散体(即PU1-5)制得的那些更差的BS、HS和COF。
结果表明了本发明的关键技术特征,即,聚氨酯粘合剂组合物的组分和它们的浓度。
Claims (11)
1.一种聚氨酯粘合剂组合物,其包含聚氨酯分散体和以所述聚氨酯分散体的总干重计按干重1.2%至20%的聚异氰酸酯交联剂;其中所述聚氨酯分散体是以所述聚氨酯分散体的总干重计按干重10%至40%的单体芳香族二异氰酸酯、30%至65%的聚醚多元醇、15%至30%的具有至少一个芳香族基团和一个脂族基团的聚酯多元醇、0.1%至8%的多胺和0.5%至10%的离子表面活性剂的反应产物,其中所述聚醚多元醇是聚乙二醇与聚丙二醇、聚丁二醇和聚四亚甲基醚二醇中的至少之一的组合,其中所述单体芳香族二异氰酸酯是二苯基甲烷二异氰酸酯,并且其中所述离子表面活性剂选自十二烷基苯磺酸钠、十二烷基磺酸钠、十二烷基二苯醚二磺酸钠、正癸基二苯醚二磺酸钠、十二烷基苯磺酸异丙胺、己基二苯醚二磺酸钠以及它们的混合物。
2.根据权利要求1所述的聚氨酯粘合剂组合物,其中每一所述多元醇具有500至4000g/mol的分子量,和1.8至4的官能度。
3.根据权利要求1所述的聚氨酯粘合剂组合物,其中所述聚酯多元醇是二醇与二羧酸的缩合产物。
4.根据权利要求3所述的聚氨酯粘合剂组合物,其中所述二醇选自乙二醇、丁二醇、二乙二醇、三乙二醇、聚亚烷基二醇、1,2-丙二醇、1,3-丙二醇、1,6-己二醇、新戊二醇和其任意组合。
5.根据权利要求4所述的聚氨酯粘合剂组合物,其中所述丁二醇选自1,3-丁二醇和1,4-丁二醇。
6.根据权利要求1所述的聚氨酯粘合剂组合物,其中所述聚酯多元醇是二醇、三醇和二羧酸的缩合产物。
7.根据权利要求1所述的聚氨酯粘合剂组合物,其中所述聚酯多元醇是二醇、四醇和二羧酸的缩合产物。
8.根据权利要求1所述的聚氨酯粘合剂组合物,其中所述离子表面活性剂是十二烷基苯磺酸钠。
9.根据权利要求1所述的聚氨酯粘合剂组合物,其中所述多胺选自乙二胺、1,2-二氨基丙烷、1,3-二氨基丙烷、1,4-二氨基丁烷、1,6-二氨基己烷、异佛尔酮二胺和其任意组合。
10.根据权利要求1所述的聚氨酯粘合剂组合物,其中所述聚异氰酸酯交联剂是选自1,6-六亚甲基二异氰酸酯、1-异氰酸根合-3-异氰酸根合甲基-3,5,5-三甲基-环己烷、4,4'-二异氰酸根合二环己基甲烷、二异氰酸根合甲基-环己烷和其任意组合的单体脂族二异氰酸酯的三聚体。
11.根据权利要求10所述的聚氨酯粘合剂组合物,其中所述聚异氰酸酯交联剂是亲水改性的。
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1723226A (zh) * | 2002-12-11 | 2006-01-18 | 陶氏环球技术公司 | 聚氨酯预聚物,含有该预聚物的稳定的高固体分水分散体、以及使用和制备该水分散体的方法 |
CN101007934A (zh) * | 2007-01-25 | 2007-08-01 | 南京工业大学 | 一种复合薄膜用水性聚氨酯胶粘剂及其制备方法 |
CN100344667C (zh) * | 2003-05-28 | 2007-10-24 | 大日本油墨化学工业株式会社 | 水性涂层试剂 |
CN101443379A (zh) * | 2006-05-16 | 2009-05-27 | 陶氏环球技术公司 | 非离子型亲水聚氨酯水分散体及其连续制备方法 |
CN103975034A (zh) * | 2011-12-09 | 2014-08-06 | 巴斯夫欧洲公司 | 水性聚氨酯分散体用于复合膜层压的用途 |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3521618A1 (de) * | 1985-06-15 | 1986-12-18 | Bayer Ag, 5090 Leverkusen | In wasser dispergierbare polyisocyanat-zubereitung und ihre verwendung als zusatzmittel fuer waessrige klebstoffe |
EP0490026A3 (en) * | 1990-12-10 | 1992-09-30 | H.B. Fuller Licensing & Financing, Inc. | Improved aqueous emulsion dispersion adhesives based on a polyol and a hindered isocyanate compound |
US5532058A (en) * | 1990-12-10 | 1996-07-02 | H. B. Fuller Licensing & Financing, Inc. | Dry-bonded film laminate employing polyurethane dispersion adhesives with improved crosslinkers |
JP3448691B2 (ja) * | 1993-10-29 | 2003-09-22 | コニシ株式会社 | ウレタン樹脂組成物 |
JPH1161082A (ja) * | 1997-08-22 | 1999-03-05 | Nippon Polyurethane Ind Co Ltd | ポリウレタン系接着剤 |
JP5358863B2 (ja) * | 2000-11-15 | 2013-12-04 | Dic株式会社 | ポリウレタン水性分散体 |
JP3885531B2 (ja) * | 2001-08-17 | 2007-02-21 | 日本ポリウレタン工業株式会社 | 水性ポリウレタン系エマルジョン、並びにこれを用いた水性接着剤及び水性塗料 |
JP4106996B2 (ja) * | 2002-07-19 | 2008-06-25 | Dic株式会社 | ポリウレタン樹脂水性分散体及び水性接着剤 |
DE102006048926A1 (de) * | 2006-10-17 | 2008-04-24 | Bayer Materialscience Ag | Wässriges Beschichtungsmittel auf Basis eines Bindemittelgemisches als Basislack |
CL2008003125A1 (es) * | 2007-11-07 | 2009-11-27 | Bayer Materialscience Ag | Dispersion poliuretano-poliuretano urea acuosa de uno o mas polioles, di o poliisocianato y mezcla de monoaminos d1 y diamino primarios y/o secundarios d2 donde al menos d1 y/o d2 tiene sulfonato y/o carboxilato, funcionalidad amino 1,65 a 1,95, relacion nco 1,04 a 1,9; procedimiento de preparacion; composiciones; uso; y compuesto. |
PL2242784T3 (pl) * | 2008-01-25 | 2014-04-30 | Henkel Corp | Ciekłe poliuretanowe prepolimery użyteczne do bezrozpuszczalnikowych klejów |
JP2010007043A (ja) * | 2008-05-29 | 2010-01-14 | Tosoh Corp | 水性複合樹脂分散体 |
CN101649039B (zh) * | 2008-08-15 | 2012-05-02 | 段友芦 | 高固体含量、低活化温度的水性聚氨酯分散液,制备方法及其用途 |
CN101899277B (zh) * | 2010-04-30 | 2013-01-09 | 华烁科技股份有限公司 | 一种rfid天线基材用水性聚氨酯胶粘剂 |
US9005762B2 (en) * | 2011-12-09 | 2015-04-14 | Basf Se | Use of aqueous polyurethane dispersions for composite foil lamination |
TW201430075A (zh) * | 2012-09-21 | 2014-08-01 | Dow Global Technologies Llc | 具增強之可移除性之聚胺酯分散體系塗層 |
CN105722894A (zh) * | 2013-12-04 | 2016-06-29 | 尤尼吉可株式会社 | 聚烯烃树脂水性分散体 |
-
2014
- 2014-08-25 BR BR112017003584-7A patent/BR112017003584B1/pt active IP Right Grant
- 2014-08-25 US US15/506,576 patent/US20170247588A1/en not_active Abandoned
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-
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Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1723226A (zh) * | 2002-12-11 | 2006-01-18 | 陶氏环球技术公司 | 聚氨酯预聚物,含有该预聚物的稳定的高固体分水分散体、以及使用和制备该水分散体的方法 |
CN100344667C (zh) * | 2003-05-28 | 2007-10-24 | 大日本油墨化学工业株式会社 | 水性涂层试剂 |
CN101443379A (zh) * | 2006-05-16 | 2009-05-27 | 陶氏环球技术公司 | 非离子型亲水聚氨酯水分散体及其连续制备方法 |
CN101007934A (zh) * | 2007-01-25 | 2007-08-01 | 南京工业大学 | 一种复合薄膜用水性聚氨酯胶粘剂及其制备方法 |
CN103975034A (zh) * | 2011-12-09 | 2014-08-06 | 巴斯夫欧洲公司 | 水性聚氨酯分散体用于复合膜层压的用途 |
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