CN102803416A - 含有多官能二烯和亲二烯体化合物的热可逆热熔性粘合剂 - Google Patents
含有多官能二烯和亲二烯体化合物的热可逆热熔性粘合剂 Download PDFInfo
- Publication number
- CN102803416A CN102803416A CN2010800255301A CN201080025530A CN102803416A CN 102803416 A CN102803416 A CN 102803416A CN 2010800255301 A CN2010800255301 A CN 2010800255301A CN 201080025530 A CN201080025530 A CN 201080025530A CN 102803416 A CN102803416 A CN 102803416A
- Authority
- CN
- China
- Prior art keywords
- gathering
- hot
- diene
- prepolymer
- dienophile
- 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
- 230000002441 reversible effect Effects 0.000 title claims abstract description 51
- 239000004831 Hot glue Substances 0.000 title claims abstract description 49
- 239000000203 mixture Substances 0.000 title claims abstract description 47
- 150000001993 dienes Chemical class 0.000 title claims description 54
- 150000001875 compounds Chemical class 0.000 title description 8
- 239000004753 textile Substances 0.000 claims abstract description 6
- 239000000178 monomer Substances 0.000 claims description 65
- 239000000463 material Substances 0.000 claims description 62
- 239000003795 chemical substances by application Substances 0.000 claims description 47
- -1 siloxanes Chemical class 0.000 claims description 45
- 150000002148 esters Chemical class 0.000 claims description 31
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 24
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 22
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 20
- 150000002240 furans Chemical class 0.000 claims description 20
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 17
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 16
- 238000001816 cooling Methods 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 14
- 150000003949 imides Chemical class 0.000 claims description 13
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 12
- 239000004202 carbamide Substances 0.000 claims description 12
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 claims description 12
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 12
- 229920000570 polyether Polymers 0.000 claims description 12
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 12
- 238000010494 dissociation reaction Methods 0.000 claims description 11
- 230000005593 dissociations Effects 0.000 claims description 11
- 229920005906 polyester polyol Polymers 0.000 claims description 11
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 10
- 150000001408 amides Chemical class 0.000 claims description 10
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 10
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 10
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 9
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 9
- 230000001464 adherent effect Effects 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 9
- 229920003023 plastic Polymers 0.000 claims description 9
- 239000004033 plastic Substances 0.000 claims description 9
- 229920001169 thermoplastic Polymers 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 7
- 150000001336 alkenes Chemical class 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 claims description 6
- PGTKVMVZBBZCKQ-UHFFFAOYSA-N Fulvene Chemical compound C=C1C=CC=C1 PGTKVMVZBBZCKQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000002015 acyclic group Chemical group 0.000 claims description 6
- 125000001118 alkylidene group Chemical group 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 150000003233 pyrroles Chemical class 0.000 claims description 6
- WELKBINNNXKQQS-UHFFFAOYSA-N 1,4-benzoquinone imine Chemical compound N=C1C=CC(=O)C=C1 WELKBINNNXKQQS-UHFFFAOYSA-N 0.000 claims description 5
- ZLPORNPZJNRGCO-UHFFFAOYSA-N 3-methylpyrrole-2,5-dione Chemical compound CC1=CC(=O)NC1=O ZLPORNPZJNRGCO-UHFFFAOYSA-N 0.000 claims description 5
- 229920001651 Cyanoacrylate Polymers 0.000 claims description 5
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 claims description 5
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 claims description 5
- 229930192627 Naphthoquinone Natural products 0.000 claims description 5
- 150000001345 alkine derivatives Chemical class 0.000 claims description 5
- 150000004054 benzoquinones Chemical class 0.000 claims description 5
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 5
- 239000004744 fabric Substances 0.000 claims description 5
- 230000036541 health Effects 0.000 claims description 5
- 239000011976 maleic acid Substances 0.000 claims description 5
- 150000002791 naphthoquinones Chemical class 0.000 claims description 5
- 239000011521 glass Substances 0.000 claims description 4
- 238000012856 packing Methods 0.000 claims description 4
- 239000002987 primer (paints) Substances 0.000 claims description 4
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 239000006260 foam Substances 0.000 claims description 3
- 239000011159 matrix material Substances 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 2
- 238000003860 storage Methods 0.000 claims description 2
- 238000005034 decoration Methods 0.000 claims 2
- 239000000853 adhesive Substances 0.000 abstract description 8
- 230000001070 adhesive effect Effects 0.000 abstract description 8
- 238000004806 packaging method and process Methods 0.000 abstract description 3
- 238000010276 construction Methods 0.000 abstract 1
- 239000002585 base Substances 0.000 description 37
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 31
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 22
- 125000001931 aliphatic group Chemical group 0.000 description 18
- 239000003973 paint Substances 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- 125000000524 functional group Chemical group 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- 239000011230 binding agent Substances 0.000 description 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 10
- 229920000647 polyepoxide Polymers 0.000 description 10
- 239000004814 polyurethane Substances 0.000 description 10
- 229920002635 polyurethane Polymers 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000003822 epoxy resin Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000000023 Kugelrohr distillation Methods 0.000 description 7
- 239000000539 dimer Substances 0.000 description 7
- 239000012943 hotmelt Substances 0.000 description 7
- 239000012948 isocyanate Substances 0.000 description 7
- 238000013008 moisture curing Methods 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical class CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 6
- 238000001723 curing Methods 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 230000037452 priming Effects 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 229920005862 polyol Polymers 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 4
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 235000005513 chalcones Nutrition 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 230000000875 corresponding effect Effects 0.000 description 4
- 239000012975 dibutyltin dilaurate Substances 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- 230000004927 fusion Effects 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 229960002725 isoflurane Drugs 0.000 description 4
- 230000002045 lasting effect Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 229920003192 poly(bis maleimide) Polymers 0.000 description 4
- 238000010008 shearing Methods 0.000 description 4
- 238000004448 titration Methods 0.000 description 4
- 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 4
- 0 *=C(C*CCCCOC(c(cc1)ccc1N(C1OC1C=C1)C1=O)=O)c(cc1)ccc1N(C(C=C1)=O)C1=O Chemical compound *=C(C*CCCCOC(c(cc1)ccc1N(C1OC1C=C1)C1=O)=O)c(cc1)ccc1N(C(C=C1)=O)C1=O 0.000 description 3
- PYCNXFLQHZMWJL-UHFFFAOYSA-N 3-(2-hydroxyethyl)pyrrole-2,5-dione Chemical compound OCCC1=CC(=O)NC1=O PYCNXFLQHZMWJL-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
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 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 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 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 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- WOGVOIWHWZWYOZ-UHFFFAOYSA-N 1,1-diisocyanatoethane Chemical compound O=C=NC(C)N=C=O WOGVOIWHWZWYOZ-UHFFFAOYSA-N 0.000 description 2
- IKYNWXNXXHWHLL-UHFFFAOYSA-N 1,3-diisocyanatopropane Chemical compound O=C=NCCCN=C=O IKYNWXNXXHWHLL-UHFFFAOYSA-N 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- FVCSARBUZVPSQF-UHFFFAOYSA-N 5-(2,4-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1C(=O)COC1=O FVCSARBUZVPSQF-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- KGWDUNBJIMUFAP-KVVVOXFISA-N Ethanolamine Oleate Chemical compound NCCO.CCCCCCCC\C=C/CCCCCCCC(O)=O KGWDUNBJIMUFAP-KVVVOXFISA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-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
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 150000001263 acyl chlorides Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 239000004411 aluminium Substances 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
- 239000012298 atmosphere Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229940043232 butyl acetate Drugs 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000002596 correlated effect Effects 0.000 description 2
- KRHOUGAQUGCCJI-UHFFFAOYSA-N cyclopenta-1,3-diene-1-carboxylic acid Chemical compound OC(=O)C1=CC=CC1 KRHOUGAQUGCCJI-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- GFMIDCCZJUXASS-UHFFFAOYSA-N hexane-1,1,6-triol Chemical compound OCCCCCC(O)O GFMIDCCZJUXASS-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 230000002028 premature Effects 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 230000008439 repair process Effects 0.000 description 2
- 239000013557 residual solvent Substances 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
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 238000010557 suspension polymerization reaction Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- SVTBMSDMJJWYQN-RXMQYKEDSA-N (4r)-2-methylpentane-2,4-diol Chemical compound C[C@@H](O)CC(C)(C)O SVTBMSDMJJWYQN-RXMQYKEDSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- XXMCAWSEVMOGLO-UHFFFAOYSA-N 1,1-dichloro-1,6-diisocyanatohexane Chemical compound O=C=NC(Cl)(Cl)CCCCCN=C=O XXMCAWSEVMOGLO-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-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
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 1
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 1
- GILMNGUTRWPWSY-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CC(O)COC(=O)C=C GILMNGUTRWPWSY-UHFFFAOYSA-N 0.000 description 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-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
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical class C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 229920003319 Araldite® Polymers 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 1
- XLUUIAPHFPWCON-UHFFFAOYSA-N C(CCCC)(O)O.[Cl] Chemical compound C(CCCC)(O)O.[Cl] XLUUIAPHFPWCON-UHFFFAOYSA-N 0.000 description 1
- YNSSPVZNXLACMW-UHFFFAOYSA-N CCc1cc(Cc(cc2C)cc(CC)c2N(C(C=C2)=O)C2=O)cc(C)c1N(C(C=C1)=O)C1=O Chemical compound CCc1cc(Cc(cc2C)cc(CC)c2N(C(C=C2)=O)C2=O)cc(C)c1N(C(C=C1)=O)C1=O YNSSPVZNXLACMW-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 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 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 229920005479 Lucite® Polymers 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- XCUYMWPLHXCTNA-UHFFFAOYSA-N OC(C=CC1=O)N1c1ccccc1 Chemical compound OC(C=CC1=O)N1c1ccccc1 XCUYMWPLHXCTNA-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920002176 Pluracol® Polymers 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- 229920013701 VORANOL™ Polymers 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000004844 aliphatic epoxy resin Substances 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical group 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 150000003818 basic metals Chemical class 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- FYXKZNLBZKRYSS-UHFFFAOYSA-N benzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(Cl)=O FYXKZNLBZKRYSS-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 description 1
- 229940106691 bisphenol a Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- ZPFKRQXYKULZKP-UHFFFAOYSA-N butylidene Chemical group [CH2+]CC[CH-] ZPFKRQXYKULZKP-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 125000002897 diene group Chemical group 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- GTZOYNFRVVHLDZ-UHFFFAOYSA-N dodecane-1,1-diol Chemical compound CCCCCCCCCCCC(O)O GTZOYNFRVVHLDZ-UHFFFAOYSA-N 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 229960005082 etohexadiol Drugs 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 238000007757 hot melt coating Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 229960004232 linoleic acid Drugs 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical class [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 239000004200 microcrystalline wax Substances 0.000 description 1
- 235000019808 microcrystalline wax Nutrition 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 1
- 229960002969 oleic acid Drugs 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 150000002924 oxiranes Chemical group 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 229940059574 pentaerithrityl Drugs 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 230000035924 thermogenesis Effects 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 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
- 229960004418 trolamine Drugs 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
-
- 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
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
-
- 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
- C08G18/28—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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/674—Unsaturated compounds containing the unsaturation at least partially in a cyclic ring having at least one oxygen atom in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/757—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing at least two isocyanate or isothiocyanate groups linked to the cycloaliphatic ring by means of an aliphatic 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
- C08G18/74—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
-
- 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
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
-
- 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
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; 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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
- C09J133/16—Homopolymers or copolymers of esters containing halogen atoms
-
- 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
- C09J135/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J135/06—Copolymers with vinyl aromatic monomers
-
- 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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J201/00—Adhesives based on unspecified macromolecular compounds
-
- 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
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
-
- 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
- C08G2170/00—Compositions for adhesives
- C08G2170/20—Compositions for hot melt adhesives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
-
- 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
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/304—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being heat-activatable, i.e. not tacky at temperatures inferior to 30°C
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/249921—Web or sheet containing structurally defined element or component
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31507—Of polycarbonate
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31663—As siloxane, silicone or silane
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31721—Of polyimide
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31725—Of polyamide
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31725—Of polyamide
- Y10T428/31736—Next to polyester
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31931—Polyene monomer-containing
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Laminated Bodies (AREA)
- Paints Or Removers (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Abstract
本发明涉及热可逆热熔性粘合剂，其不含异氰酸酯、不受水分影响、可交联和热可逆。热可逆热熔性粘合剂可以重复加热和冷却而没有对粘合剂性能的负面影响。热可逆组合物还可以用作底漆层。热可逆热熔性粘合剂和底漆可以特别适于终端应用中，如包装、平面艺术、建筑、鞋类、纺织品、总装、汽车和消费品。
Description
发明领域
本发明涉及热可逆热熔性粘合剂，特别是用至少一种多官能二烯和至少一种多官能亲二烯体制备的不含异氰酸酯的、不受水分影响的、热可逆的热熔性粘合剂，其中至少一种多官能二烯单体/预聚物或多官能亲二烯体单体/预聚物的活性官能度大于2.1。
发明背景
热熔性粘合剂在室温下是固体，但是，在施加热后，熔融成液体或流体形态。在其液体或流体形态期间，将热熔性粘合剂施加在基材上。冷却后，粘合剂重回固体形式。通过冷却粘合剂形成的硬质相赋予最终的粘合剂以全部粘合力(强度、韧性、蠕变和耐热性)。“活性”或可交联热熔性粘合剂，其也以熔融形式施加，经冷却固化，随后通过化学交联反应固化。可固化热熔性粘合剂比传统液体固化粘合剂的优势在于其可以在固化前通过冷却提供“湿强度”。可固化热熔性粘合剂比非固化热熔性粘合剂的优势包括改善的耐温性和耐化学性。
大多数“活性”或可交联热熔性粘合剂基于水分固化氨基甲酸酯粘合剂。这些粘合剂主要由异氰酸酯端基的聚氨基甲酸酯预聚物组成，其与表面或外界的水分反应，以使链扩链，形成新的聚氨基甲酸酯/脲聚合物。聚氨基甲酸酯预聚物可以通过多羟基化合物与异氰酸酯反应而方便地得到。通过水分从大气或基材中扩散到粘合剂中，并随后反应而得到固化。水分与残基异氰酸酯反应形成氨基甲酸。该酸不稳定，分解成胺和二氧化碳。胺迅速与异氰酸酯反应形成脲。最终的粘合剂产品是主要通过脲与氨基甲酸酯基团的聚合得到的可逆材料。
这些“活性”热熔组合物具有若干缺点。典型地通过过量二异氰酸酯与多羟基化合物反应制备材料。组合物通常含有百分之二到五的未反应二异氰酸酯，如MDI(亚甲基二苯基二异氰酸酯)，其是呼吸和皮肤敏感的。而且，水分可固化活性热熔性粘合剂必须无水分保存，以防止过早固化，典型地在在氮气下，或在惰性气层下储存，使用昂贵的包装，如聚烯烃涂布的铝袋，以防止水分侵入。而且，水分可固化活性热熔性粘合剂需要昂贵的专业加工应用设备，以保持隔离水分。而且，所述活性热熔性粘合剂的固化率不稳定，高度依赖于渗透进粘合剂的水分。因此，大气湿度、基材的含水量、粘合剂的水蒸气透过率和粘结线的厚度都对活性热熔组合物的固化率产生影响。另外，聚氨基甲酸酯水分固化产生CO2，这可以导致粘合线中产生气泡，使粘合剂强度弱化，而且这可以导致美观问题，特别是在塑料基材上。另外，活性热熔性粘合剂的固化不可逆，因而不能再维修或再修复。如果发生过早固化，所述粘合剂不能使用，或者在固化发生后，其不能改变位置或去除。
需要对活性热熔技术的改善，以扩展所述粘合剂的应用以及其在所述应用中的效率。本发明致力于此需求。
发明概述
本发明提供一种热可逆热熔性粘合剂。本发明的粘合剂包含多官能二烯单体/预聚物和多官能亲二烯体单体/预聚物，其中至少一种多官能二烯单体/预聚物或多官能亲二烯体单体/预聚物的活性官能度大于2.1。
在一个实施方案中，热可逆热熔性粘合剂由至少一种多官能二烯单体/预聚物和至少一种多官能亲二烯体单体/预聚物组成，其中至少一种多官能二烯单体/预聚物或多官能亲二烯体单体/预聚物的活性官能度大于2.1，以形成非线性聚合物网络。热可逆热熔性粘合剂可以在环境温度下运输和储存。通过加热至特定温度之上，粘合剂离解成由多官能二烯单体/预聚物或多官能亲二烯体单体/预聚物构成的非交联态。通过冷却粘合剂，或低于特定温度，二烯和亲二烯体间的键(bonds)重新形成其起初的交联态。热可逆热熔性粘合剂可以重复加热和冷却，没有对热可逆性或粘合剂性能的负面影响。
在另一个实施方案中，热可逆热熔组合物包含
至少一种多官能二烯单体或预聚物，其具有以下通式结构：
L-(X)P；
其中L独立地是单体单元、低聚单元或聚合单元，具有选自但不限于以下组中的骨架：(聚)氨基甲酸酯、(聚)脲、(聚)酯、(聚)碳酸酯、(聚)酰胺、(聚)酰亚胺、(聚)苯乙烯、(聚)醚、(聚)(甲基)丙烯酸酯、(聚)烯烃、(聚)硅氧烷、以上成分的共聚物，包括马来酸酐的共聚物；X独立地是二烯，该二烯含有一个或多个非环的1，3-二烯、环戊二烯、环己二烯、呋喃、富烯、吡咯、萘、蒽；而P大于零；
(II)至少一种多官能亲二烯体单体或预聚物，具有通式结构：
L-(Y)Q；
其中L如上所确定；Y是由选自以下组中的一种或多种得到的官能团：马来酰亚胺、异马来酰亚胺、柠康酰亚胺、衣康酰亚胺、马来酸酯、富马酸酯、丙烯酸酯、甲基丙烯酸酯、氰基丙烯酸酯、苯醌、苯醌肟、苯醌亚胺、萘醌、亚烷基丙二酸酯和含吸电子基团的炔；而Q大于零；以及
(III)其中P和Q分别是二烯和亲二烯体之一的最高官能度，P和Q的至少其一的值大于2.1。在另一个实施方案中，P和Q的至少其一的值小于3.0。还在另一个实施方案中，P和Q的加和具有大于或等于5.0的值。
在另一个实施方案中，热可逆热熔组合物任选可以包含热塑性聚合物或树脂。
本发明的另一个实施方案涉及制备热可逆热熔性粘合剂的方法。通过至少一种多官能二烯单体/预聚物与至少一种多官能亲二烯体单体/预聚物反应制备热可逆热熔性粘合剂，其中至少一种多官能二烯单体/预聚物或多官能亲二烯体单体/预聚物的活性官能度大于2.1。
本发明的另一个实施方案涉及将材料粘合在一起的方法，其包含将本发明的热可逆热熔性粘合剂组合物加热成熔融形式，将所述粘合剂施加在第一基材上，将第二基材与施加在第一基材上的组合物接触，和冷却施加的组合物，从而组合物固化成固体形式。
本发明的另一个实施方案涉及一种将材料粘合在一起的方法，其包含在导致熔融形式的温度下，将未反应的多官能二烯单体/预聚物与多官能亲二烯体单体/预聚物混合在一起，保持混合物在熔融温度下，将所述粘合剂施加在第一基材上，将第二基材与施加在第一基材上的组合物接触，和冷却施加的组合物，从而组合物固化成固体形式。
另外，本发明提供用本发明的粘合剂制造的制品。可以制备粘合剂配制物，其特别良好地适于粘合纸张、木材、塑料、织物、泡沫、玻璃、金属、复合材料和陶瓷的终端应用。
另一个实施方案涉及作为粘合剂和基材间的底漆层的热可逆组合物。所述底漆由至少一种多官能二烯单体/预聚物、至少一种多官能亲二烯体单体/预聚物和任选存在的至少一种溶剂组成，其中至少一种多官能二烯单体/预聚物或多官能亲二烯体单体/预聚物的活性官能度大于2.1，以形成非线性聚合物网络。热可逆底漆组合物可以在环境温度下运输和/或储存。通过加热至特定温度之上，底漆组合物离解成由多官能二烯单体/预聚物和多官能亲二烯体单体/预聚物构成的非交联态。通过冷却底漆组合物，或低于特定温度，二烯和亲二烯体间的键重新形成其起初的交联态。热可逆底漆可以重复加热和冷却而没有对热可逆性或底漆性能的负面影响。
发明详述
除非另外陈述，所有百分数为粘合剂组合物的重量百分数。
现在已经发现，热可逆热熔性粘合剂的使用可以被制备并用于将基材粘合在一起，而无需水分对粘合剂进行交联。本发明的粘合剂包含多官能二烯单体/预聚物和多官能亲二烯体单体/预聚物。在此，预聚体被定义为单体和最终聚合物间的中间体化合物，分子量为约1000-约10000g/mol(典型地为1000-6000g/mol)，通常具有重复单元，并能够进一步进行反应和/或聚合。多官能二烯单体/预聚物或多官能亲二烯体单体/预聚物的至少其一的官能度大于2.1，以形成非线性聚合物网络。
热可逆活性热熔组合物包含：
至少一种多官能二烯单体/预聚物，具有通式：
L-(X)P
其中L独立地是单体单元、低聚单元或聚合单元，具有选自但不限于以下组中的骨架：(聚)氨基甲酸酯、(聚)脲、(聚)酯、(聚)碳酸酯、(聚)酰胺、(聚)酰亚胺、(聚)苯乙烯、(聚)醚、(聚)(甲基)丙烯酸酯、(聚)烯烃、(聚)硅氧烷、以上的共聚物，包括马来酸酐的共聚物；X独立地是二烯，该二烯含非环的1，3-二烯、环戊二烯、环己二烯、呋喃、富烯、吡咯、萘、蒽中的一种或多种；而P大于零；
(II)至少一种多官能亲二烯体单体或预聚物，具有通式结构：
L-(Y)Q
其中L如上所确定；Y是由选自以下组中的一种或多种得到的官能团：马来酰亚胺、异马来酰亚胺、柠康酰亚胺、衣康酰亚胺、马来酸酯、富马酸酯、丙烯酸酯、甲基丙烯酸酯、氰基丙烯酸酯、苯醌、苯醌肟、苯醌亚胺、萘醌、亚烷基丙二酸酯和含吸电子基团的炔；而Q大于零；以及
(III)其中P和Q分别是二烯和亲二烯体之一的最高官能度，而不是平均官能度，并且P和Q的至少其一的值大于2.1。在另一个方面，P和Q的至少其一小于3.0。还在另一个实施方案中，P和Q的加和具有等于或大于5.0的值。
具有骨架的低聚或聚合单元可以是脂族烃部分或芳香烃部分，并还可以包括杂原子。二烯或亲二烯体或两者可以任选地含有其他官能团，所述官能团可以进行非共价相互作用。
在一个方面，多官能二烯含有一种或多种非环的1，3-二烯、环戊二烯、环己二烯、呋喃、富烯、吡咯。在另一个实施方案中，多官能二烯是多官能呋喃。多官能呋喃可以包括氨基甲酸酯、脲、酯、酰胺、酰亚胺、苯乙烯、(甲基)丙烯酸酯、醚、硅氧烷或上述的组合或酸酐官能团。依据多官能呋喃上的取代基，呋喃是单体或预聚物。示例性多官能呋喃单体和预聚物包括下列：
其中n＝10-60
多官能亲二烯体单体/预聚物包括具有以下通式结构的那些：
其中n是1-3，X1是脂族或芳族基团。示例性X1包括聚丁二烯、聚碳酸酯、聚氨基甲酸酯、聚脲、聚醚、聚酯、聚(甲基)丙烯酸酯、聚烯烃、简单的烃、和简单的含有官能团的烃，所述官能团例如为羰基、羧基、酰胺、氨基甲酸酯、脲、酯、或醚。多官能亲二烯体单体/预聚物可以购得，例如购自Dainippon Ink and Chemical，Inc.。
亲二烯体任选地可以含有可以进行非共价相互作用的其他官能团。
适合的多官能亲二烯体单体/预聚物包括，但不限于，固态芳香双马来酰亚胺(BMI)树脂，特别是具有以下结构的那些：
其中Q是芳族基团。示例性芳族基团包括：
具有上述Q桥连基团的双马来酰亚胺可以购得，并可以尤其从Sartomer(USA)或HOS-Technic GmbH(奥地利)得到。
其他适合的马来酰亚胺树脂包括但不限于以下：
其中C36表示36个碳原子的直链或支化的烃链(有或没有环状部分)；
另外，也可以使用类似前面例举的呋喃官能单体/预聚物的组合物，除了所有呋喃官能基团被马来酰亚胺官能基团代替的那些。
多异氰酸酯单体可以用于制备多官能呋喃(例如与取代糠醇或糠胺反应)，以及多官能马来酰亚胺(例如与具有羟基或羧基的马来酰亚胺反应，如羟乙基马来酰亚胺)。这包括芳香二异氰酸酯，如2，4-和2，6-甲苯二异氰酸酯(TDI)；2，2′-、2，4′-、和4，4′-亚甲基二亚苯基二异氰酸酯(MDI)；以及1，4-亚苯基二异氰酸酯；环脂族二异氰酸酯，如异氟尔酮二异氰酸酯(IPDI)和氢化亚甲基二亚苯基二异氰酸酯(HMDI)；以及脂族二异氰酸酯，如1，6-二异氰酸酯己烷和1，8-二异氰酸酯辛烷。适合的多异氰酸酯包括平均官能度为2.2-2.4的聚MDI，和特别是三异氰酸酯，例如1，3，5-三异氰酸酯基苯，通过二或多异氰酸酯与其本身在三聚(异氰尿酸酯-促进催化剂)的存在下反应制备三异氰酸酯和更高官能度的异氰尿酸酯。所述异氰尿酸酯三异氰酸酯可以购得，例如标示官能度为3.0的异氟尔酮二异氰酸酯的异氰尿酸酯购自Huls America，商标名为Vestanat IPDI 1890/100。所述异氰酸酯的熔点为约110℃-115℃。多官能异氰酸酯的其他实例包括购自Bayer的Desmodur N75、Desmodur Z4470、Desmodur N3300、Desmodur N3600。
异氰酸酯官能预聚物也可以用于制备多官能呋喃(例如与取代糠醇或糠胺反应)，以及多官能马来酰亚胺(例如与具有羟基或羧基的马来酰亚胺反应，如羟乙基马来酰亚胺)。最通常的，通过过量的多异氰酸酯与多元醇的聚合制备预聚物，最优选二异氰酸酯与二醇的聚合。有机多异氰酸酯，其可以用于实施本发明，包括亚烷基二异氰酸酯、亚环烷基二异氰酸酯、芳香二异氰酸酯和脂族-芳香二异氰酸酯。适合的含异氰酸酯的化合物的特别实例包括，但不限于，亚乙基二异氰酸酯、乙叉二异氰酸酯、亚丙基二异氰酸酯、亚丁基二异氰酸酯、三亚甲基二异氰酸酯、六亚甲基二异氰酸酯、2，4-甲苯二异氰酸酯、亚环戊基-1，3-二异氰酸酯、亚环己基-1，4-二异氰酸酯、亚环己基-1，2-二异氰酸酯、2，6-甲苯二异氰酸酯、4，4′-二苯甲烷二异氰酸酯、2，4′-二苯甲烷二异氰酸酯、2，2-二苯丙烷-4，4′-二异氰酸酯、亚二甲苯基二异氰酸酯、三甲基亚二甲苯基二异氰酸酯、1，4-萘二异氰酸酯、1，5-萘二异氰酸酯、间苯二异氰酸酯、对苯二异氰酸酯、二苯基-4，4′-二异氰酸酯、偶氮苯-4，4′-二异氰酸酯、二苯砜-4，4′二异氰酸酯、2，4-甲苯撑二异氰酸酯、二氯六亚甲基二异氰酸酯、呋喃甲叉二异氰酸酯、1-氯苯-2，4-二异氰酸酯、4，4′，4″-三异氰酸酯基三苯甲烷、1，3，5-三异氰酸酯基苯、2，4，6-三异氰酸酯基甲苯、4，4′-二甲基二苯基甲烷-2，2′，5，5-四四异氰酸酯等。尽管所述化合物可以购得，但是合成所述化合物的方法是本领域内众所周知的。优选的含异氰酸酯化合物是亚甲基双苯基二异氰酸酯(MDI)、异氟尔酮二异氰酸酯(IPDI)、氢化亚甲基双苯基二异氰酸酯(HMDI)和甲苯二异氰酸酯(TDI)。
所用的多元醇包括多羟基醚(取代或未取代的聚亚烷基醚二醇或多羟基聚亚烷基醚)、多羟基聚醚、多元醇的环氧乙烷或环氧丙烷加成物、和甘油的单取代酯，及其混合物。
聚醚多元醇的实例包括具有多个醚键和至少两个羟基的直链和/或支化的聚醚，并基本上不含除羟基外的其他官能团。聚醚多元醇的实例可以包括聚氧代亚烷基多元醇，如聚乙二醇、聚丙二醇、聚丁二醇等。另外，还可以使用聚氧代亚烷基多元醇的均聚物和共聚物。特别优选的聚氧代亚烷基多元醇的共聚物可以包括选自乙二醇、丙二醇、二乙二醇、二丙二醇、三乙二醇、2-乙基己二醇-1，3、甘油、1，2，6-己烷三醇、三羟甲基丙烷、三羟甲基乙烷、三(羟苯基)丙烷、三乙醇胺、三异丙醇胺、乙二胺和乙醇胺的化合物的用至少一个选自环氧乙烷、环氧丙烷和环氧丁烷的至少一种化合物的加成物。大量适合的聚醚多元醇可以购得。非限制性实例包括Voranol P400、P725、P1000、P2000、P4000(Dow)、PolyG 20-56(Arch)和Pluracol P-2010(BASF)、Acclaim 4200(Bayer)。聚醚多元醇的典型分子量为约1000-约18000。另一个适合的马来酰亚胺树脂包括：
其中聚醚多元醇链段的分子量为约1000-约18000。
由一个或多个具有2-15的碳原子的多元醇与一个或多个具有2-14个碳原子的多元羧酸的缩合形成聚醚多元醇。适合的多元醇的实例包括乙二醇、诸如1，2-丙二醇和1，3-丙二醇的丙二醇、甘油、季戊四醇、三羟甲基丙烷、丁二醇、戊二醇、己二醇、十二烷二醇、辛二醇、氯戊二醇、甘油单烯丙基醚、甘油单乙醚、二乙二醇、2-乙基己二醇-1，4、环己二醇-1，4、1，2，6-己三醇、1，3，5-己三醇、1，3-双-(2-羟乙氧基)丙烷等。多元羧酸的实例包括邻苯二甲酸、间苯二甲酸、对苯二甲酸、四氯酞酸、马来酸、十二烷基马来酸、油基马来酸、富马酸、偏苯三酸、均丙三酸、3，3′-硫代二丙酸、琥珀酸、己二酸、辛二酸、壬二酸、丙二酸、戊二酸、庚二酸、癸二酸、环己烷-1，2-二羧酸、1，4-环己二烯-1，2-二羧酸、3-甲基-3，5-环己二烯-1，2-二羧酸和相应的酸酐、酰氯和酯，如邻苯二甲酸酐、邻苯二甲酰氯和邻苯二甲酸的二甲酯。优选的多元羧酸是含有不超过14个碳原子的脂族和环脂族二羧酸，和含有不超过14个碳原子的芳香二羧酸。也可以使用二聚体脂族酸，其中其为单或聚不饱和酸和/或其酯的二聚产物。优选的二聚体脂族酸是C10-C30的二聚体，更优选C12-C24，特别是C14-C22和尤其是C18烷基链。适合的二聚体脂族酸包括油酸、亚油酸、亚麻酸、棕榈酸和反油酸的二聚产物。还可以使用在天然脂族和油的水解作用中得到的不饱和脂族酸混合物的二聚产物，例如葵花油、大豆油、橄榄油、菜籽油、棉花子油和妥尔油。除了二聚体脂族酸外，二聚作用通常导致存在不同量的低聚脂族酸(被称为“三聚体”)和残留的单体脂族酸(被称为“单体”)，或其酯。适合的二聚体脂族酸的二聚体酸含量大于60％，优选大于75％，更优选90-99.5％，特别是95-99％，和尤其是97-99％。可以用于实施本发明的市售聚酯包括晶体和无定形材料，诸如Dynacoll 7360、7380、7330、7231、7250(Evonik)、RucoflexS-105-10(Bayer)、Stepanpol PN110(Stepan)、Priplast 3196(Croda)。典型分子量为约2000-约7000。另一个适合的马来酰亚胺树脂包括：
其中聚酯多元醇链段的分子量为约2000-约7000。
另外，可以使用少量的低分子量二羟基、二氨基、或氨基羟基化合物，如饱和或不饱和二醇，例如乙二醇或其缩合物，如二乙二醇、三乙二醇等；乙二胺、六亚甲基二胺等；乙醇胺、丙醇胺、N-甲基二乙醇胺等。
多官能呋喃和马来酰亚胺也可以由在先提及的聚酯多元醇和聚醚多元醇通过直接与马来酰亚胺或具有羧酸官能团的呋喃酯化而合成。另外，通过使用过量的多元醇，多异氰酸酯与多元醇加成制备的聚氨基甲酸酯二醇也可以用于制备多官能呋喃和马来酰亚胺，其制备是通过与马来酰亚胺或具有羧酸官能团的呋喃的酯化完成的。
适合的环氧树脂，其也可以用于通过与具有羧酸的马来酰亚胺的开环反应合成双马来酰亚胺，包括但不限于双酚、萘、和脂族型环氧树脂。市售材料包括购自Dainippon Ink&Chemicals，Inc.的双酚型环氧树脂(Epiclon830LVP、830CRP、835LV、850CRP)；购自Dainippon Ink&Chemicals，Inc.的萘型环氧树脂(Epiclon HP4032)；购自Ciba Specialty Chemicals(AralditeCY179、184、192、175、179)、购自Dow Corporation(Epoxy 1234、249、206)、和购自Daicel Chemical Industries，Ltd(EHPE-3150)的脂族环氧树脂。其他实例包括六氢邻苯二甲酸酐的二缩水甘油酯，以CY-184购买(Ciba-Geigy)；双酚-A型环氧树脂、双酚-F型环氧树脂、环氧酚醛树脂、双苯型环氧树脂、萘型环氧树脂、二环戊二烯苯酚型环氧树脂。
所述环戊二烯基化合物可以通过如下方式制备，将环戊二烯与诸如钠的碱金属在适合的溶剂中反应，所述溶剂例如为四氢呋喃、五氢吡喃、二氧六环或其与芳香烃的混合物，以形成环戊二烯的碱金属盐，而后将盐直接或间接与亲电试剂反应，所述亲电试剂例如为烷基二卤代物或二酸的酰氯。通过环戊二烯的碱金属盐与二氧化碳反应，形成环戊二烯羧酸，而后将所述酸与醇的酯化反应或通过缩水甘油基环氧树脂的开环，制备环戊二烯羧酸的烯基或缩水甘油基酯。具有环戊二烯的预聚物/聚合物可以以类似方式合成。
组合物中的二烯官能基团对亲二烯体官能基团的化学计量比为0.5∶2.0-2.0∶0.5，优选1.0∶2.0-2.0∶1.0，更优选0.9∶1.1-1.1∶0.9。
热可逆热熔性粘合剂可以任选地含有热塑性聚合物，分子量典型地为，但不限于，Mn＝5,000-100,000g/mole。这可以是通过任何普通的乙烯基单体的自由基共聚得到的聚合物，所述乙烯基单体例如为乙烯、丙烯、丁二烯、苯乙烯、醋酸乙烯酯、甲基丙烯酸酯、丙烯酸酯、马来酸酐和醋酸乙烯酯。这还包括诸如乙烯-醋酸乙烯酯(EVA)或乙烯-醋酸乙烯酯-马来酸酐三元共聚物的共聚物。可选的，可以由梯级生长或官能基团的加成形成所述聚合物，包括，但不限于聚酯、聚碳酸酯、聚氨基甲酸酯、聚酰胺、聚硅氧烷。热塑性聚合物可以含有侧基官能基团，如酸、酸酐、羟基或环氧基团。基于粘合剂的总重量，所用的水平典型地为1-50wt％的热塑性聚合物，优选5-40wt％，和最优选10-30wt％。
在本发明的另一个实施方案中，热塑性聚合物是(甲基)丙烯酸聚合物。聚(甲基)丙烯酸酯链段可以是直链或支化的，具有约-48℃～105℃的宽范围的Tg值，优选约-20℃～85℃，和更优选15℃～85℃。聚合物包含共聚的(甲基)丙烯酸烷基酯单体。适合的共聚单体包括甲基丙烯酸和丙烯酸的C1-C12酯，包括，但不限于，甲基丙烯酸甲酯、甲基丙烯酸乙酯、甲基丙烯酸正丙酯、甲基丙烯酸异丙酯、甲基丙烯酸正丁酯、甲基丙烯酸异丁酯、甲基丙烯酸正己酯、甲基丙烯酸正辛酯、甲基丙烯酸2-乙基己酯、甲基丙烯酸十二烷酯(月桂醇酯)、甲基丙烯酸环己酯、甲基丙烯酸降冰片酯或相应的丙烯酸酯。也可以使用能共存的(甲基)丙烯酸酯单体的混合物。还可以使用基于甲基丙烯酸和丙烯酸与聚乙二醇和/或聚丙二醇和/或乙二醇醚的酯的甲基丙烯酸和丙烯酸共聚单体。
功能性共聚单体还可以用于聚(甲基)丙烯酸酯中，例如酸、羟基或环氧官能化的(甲基)丙烯酸共聚单体，但所述列表是非排他性的。可以并入丙烯酸聚合物的适合的羟基官能化共聚单体包括，但不限于，甲基丙烯酸2-羟乙酯、甲基丙烯酸2-羟丙酯和甲基丙烯酸2-羟丁酯或相应的丙烯酸酯。可以并入丙烯酸聚合物的适合的酸官能共聚单体包括，但不限于，甲基丙烯酸和丙烯酸。
实际上，任何烯键式不饱和单体都可以用作(甲基)丙烯酸聚合物中的共聚单体。其他可以使用的额外的乙烯基共聚单体包括乙烯酯(例如醋酸乙烯酯和丙酸乙烯酯)、乙烯基醚；巴豆酸、马来酸、富马酸和衣康酸的酯；苯乙烯；烷基苯乙烯；丙烯腈；丁二烯；以及其共聚单体。
可以通过本领域内众所周知的自由基聚合技术，用偶氮或过氧化物引发剂，以溶剂聚合、本体聚合、悬浮聚合和乳液聚合形成聚(甲基)丙烯酸酯。特别使用悬浮聚合，因为这对于随后配制进热可逆热熔涂层组合物而言，是提供小球形式的聚合物的容易的方式。
任选地可以将抗氧剂添加至热可逆热熔性粘合剂中。提供基于不同化学过程的各种抗氧剂，例如Ciba的商标名为Irganox、Irgafos或Irgastab的产品。对于粘合剂而言，抗氧剂的混合物是优选的，因为所述组合具有协同效应。基于粘合剂的总重量，可以使用的抗氧剂的浓度范围为0.1-10％，优选0.5-5％。
组合物还可以包括增粘树脂，其是低分子量的天然或基于石油的材料。适合的增粘剂包括，但不限于，松香、松香衍生物、松香酯、脂族烃、芳香烃、芳香改性脂族烃、脂族改性芳香烃、萜烯、酚醛改性萜烯树脂。基于粘合剂的总重量，增粘树脂的典型用量至多50wt％，优选5-30wt％，和最优选10-25wt％。
如果期望，还可以用与粘合剂兼容的传统添加剂配制热可逆热熔性粘合剂。所述添加剂包括增塑剂、固化催化剂、分解催化剂、石蜡或微晶蜡、填料、颜料、粘合促进剂、稳定剂、氢化蓖麻油、有机硅烷粘合促进剂。添加剂的典型用量为0.1-10wt％，优选0.5-5.0wt％。
热可逆热熔性粘合剂可以在环境温度下以交联态运输和储存。
为了热可逆热熔性粘合剂的施用，将粘合剂加热至二烯和亲二烯体间形成的键的解离温度之上。通过将粘合剂加热至适合的温度，所述共价键断裂，材料的粘度降低至足以用传统方式施用，例如通过狭缝涂布、辊涂或喷涂。粘合剂的施用温度典型地比二烯/亲二烯体键的解离温度高20-60℃，尽管这不是限制条件。解离温度可以通过多官能二烯和多官能亲二烯体的骨架结构、官能度和配制物组分调整。优选的，对于某些应用，所述离解温度高于80℃，更优选在其他应用中高于100℃，更优选在其他应用中高于120℃，和更优选在某些应用中高于140℃。
另一方面，多官能二烯单体/预聚物和多官能亲二烯体单体/预聚物可以单独储存，并在施用在基材上前不久合并。需要保持温度足够高，以限制二烯和亲二烯体间形成显著的键合，并防止交联。例如，可以分别供给多官能二烯单体/预聚物和多官能亲二烯体单体/预聚物至施用单元，并在混合后的数秒或数分钟内分散。或可选的，可以在施加之前混合多官能二烯单体/预聚物和多官能亲二烯体单体/预聚物，并在施加前保持于热釜中若干分钟或若干小时。两种组分在共价键的离解温度之上结合，所述共价键在二烯和亲二烯体之间形成，或者(1)在将粘合剂冷却至交联形式并重新加热之后，或者(2)保持粘合剂温热之后，对粘合剂施加热，以使其在储存和应用期间不发生交联，而在冷却时交联下应用。
在粘合剂冷却后，多官能二烯单体/预聚物和多官能亲二烯体单体/预聚物间的键重新形成。粘合剂可以重复加热和冷却，而不会对粘合剂的性能产生负面影响。
本发明的一个实施方案涉及一种将材料粘合在一起的方法，包含(1)将热可逆熔融组合物加热至熔融形式，(2)将组合物施加在第一基材上，(3)将第二基材与施加在第一基材上的组合物接触，和(4)冷却施加的组合物，从而形成粘合的基材。
热可逆热熔性粘合剂可以特别用于许多应用中，如包装、平面艺术、建筑、鞋类、纺织品、总装、汽车和消费品。包装应用包括，例如但不限于，用于粘合塑料薄膜的软包装。平面艺术应用包括，例如但不限于，用于纸/涂布纸的装订的书脊胶。建筑应用包括，例如但不限于，木材和塑料、家具和窗的硬质板层压和封边。鞋类应用包含鞋底中的聚合物粘合。总装包括，例如但不限于，工业应用中的塑料组分的装配。汽车应用包括，例如但不限于，涉及塑料组件的车前灯粘合和诸如织物/纤维的各种基材的内部装饰应用。织物粘合包括，例如但不限于，用于户外服装的透气膜的软层压。消费者应用包括，例如但不限于，在住宅中用于装修的粘合剂和密封剂。
本发明的热可逆组合物还可以用作底漆层。底漆通常是聚合物薄层，其涂布在基材上，以增强粘合剂与基材的附着力。热可逆底漆组合物可以以100％固体形式直接涂布，或可以用溶剂稀释，以产生非常薄的层，例如0.1-10微米。
本发明的另一方面涉及一种将材料粘合在一起的方法，包含(1)加热热可逆底漆组合物，(2)将底漆组合物施加在基材上，(3)冷却底漆组合物，(4)将粘合剂组合物施加在底漆上，(5)将第二基材与粘合剂组合物接触，和(6)如果必要，冷却粘合剂组合物，从而形成粘合的基材。粘合剂组合物可以是任何类型的粘合剂组合物，包括热熔、液态、溶剂基和水基的。粘合剂可以是单组份或双组份的，并可以是非活性的(非固化的)或活性的(固化的)。另外，本发明提供用本发明的组合物制造的制品，作为粘合剂和基材间的底漆层。通过将粘合的接头加热至高于热可逆底漆中的二烯和亲二烯体间形成的粘合剂的离解温度之上，粘合的粘合剂可以容易地从包含热可逆底漆的表面上分离。
对本发明的许多修饰和改变不背离本发明的精神和范围，这对于本领域内的技术人员是显而易见的。在此所述的特定实施方案仅作为实施例的方式提供，本发明仅通过附属权利要求限制，同时受限于与授权的所述权利要求等价的全部范围。
实施例
下列多官能呋喃(MFF)和多官能马来酰亚胺(MFM)的使用和制备如下。还列出了预估的P和Q值。
MFF-1(P＝3.0)
MFF-1的合成如下。在0℃下，向冰冷却的1，3，5-均苯三甲酰氯(20g，75.3mmol)在CH2Cl2(200mL)的溶液中添加三乙胺(26.7g，263mmol)。在所述温度下搅拌15min后，使用加料漏斗滴加糠醇(22.2g，226mmol)。小心控制所述放热反应，防止CH2Cl2沸腾。用机械搅拌将反应混合物搅拌约2h。TLC检测表明反应完毕。蒸发CH2Cl2，将乙酸乙酯添加至混合物中。过滤溶液，并用乙酸乙酯洗涤。滤液用水洗涤，通过无水MgSO4干燥。蒸发溶剂后，在Kugelrohr中干燥，得到棕色固体MFF-1(43g，83％)。
1H NMR(CDCl3)：δ8.8(s，3H)，7.45(s，3H)，6.5(m，3H)，6.4(t，3H)，5.35(s，6H)
MFF-2(P＝3.0-3.6)
MFF-2的合成如下。向异氟尔酮二异氰酸酯三聚物的乙酸丁酯溶液(Desmodur Z 4470，作为乙酸丁酯溶液提供，142.87g溶液，活性组分100g，410mmol)中添加糠醇(40.2g，410mmol)和4滴二丁基二月桂酸锡。用机械搅拌器搅拌得到的混合物，并加热到85℃下持续4h，直到IR显示异氰酸酯谱带消失。当冷却至RT后，添加100ml甲苯，在旋转蒸发器中真空挥发溶剂。用Kugelrohr蒸馏设备在70℃下蒸发残留的溶剂，产品在真空烘箱中在真空下，于60℃下进一步干燥过夜。这样得到淡棕色粉末MFF-2(130g，92％)。
1H NMR(CDCl3)：δ7.35(s，1H)，6.3-6.4(m，2H)，5.0(brs，2H)，3.7(m，2H)，2.0-0.6(m).
MFF-3(P＝3.0-3.4)
MFF-3的合成如下。向Desmodur N3300(150g，220mmol)在甲苯(300ml)的溶液中添加糠醇(65g，661mmol)和4滴DBTL。将得到的混合物加热至85℃下持续3h，直到IR显示异氰酸酯谱带消失。挥发掉甲苯，用Kugelrohr蒸馏设备去除残留的溶剂，这样得到MFF-3(215g，定量的)。
1H NMR(CDCl3)：δ7.5(s，1H)，6.3-6.4(m，2H)，3.9-3.6(m，2H)，3.3-3.0(m，2H)，1.7-1.2(m，8H).
MFF-4(P＝2.0)
MFF-4的合成如下。将二聚二异氰酸酯DDI-1410(50g，85mmol)，糠醇(16.7g，170mmol)和DBTL在甲苯中的混合物加热至85℃下持续3h。通过IR检测反应至异氰酸酯谱带消失。约3h后，停止反应，在真空下挥发溶剂。通过Kugelrohr蒸馏设备去除最后的痕量溶剂。这样定量产生MFF-4(16.7g，170mmol)。
1H NMR(CDCl3)：δ7.45(s，2H)，6.4-6.6(m，4H)，5.1(s，4H)，3.1-3.3(m，4H)，1.6-0.5(m)
MFF-5(P＝2.0)
MFF-5的合成如下。在RT下，将DDI 1410(50g，85mmol)的甲苯(250ml)溶液中添加糠胺(16.5g，169.7mmol)并搅拌2h。用旋转蒸发器挥发溶剂。通过Kugelrohr蒸馏设备去除残留的溶剂。这样得到低熔点固体MFF-5(60g，90％)。
1H NMR(CDCl3)：δ7.35(s，2H)，6.3(s，2H)，6.2(s，2H)，4.3(s，4H)，3.15(m，4H)1.8-0.8(m)
MFF-6(P＝3.0-3.2)
其中n＝2-5
MFF-6的合成如下。向聚苯基异氰酸酯-甲醛共聚物(100g，250mmol)的甲苯溶液(500ml)中添加糠醇(78.5g，1.2mol)和两滴二丁基二月桂酸锡。将得到的溶液加热到85℃下持续3h，直到IR显示异氰酸酯谱带消失。用旋转蒸发器蒸发甲苯，通过Kugelrohr蒸馏在50℃下蒸馏2h去除残余的溶剂。这样得到棕色固体MFF-6(160g)。
1H NMR(CDCl3)：δ7.6-6.7(m)，6.5-6.2(m)，5.2-5.0(m)，3.9-3.6(m).
MFF-7(P＝4.0)
MFF-7的合成如下。向Desmodur N3300(70g，103mmol)在甲苯(500ml)的溶液中添加糠醇(24.2g，124mmol)。在加热至85℃持续3h后，添加Priplast 1838聚酯多元醇(103g，25.7mmol)，将得到的混合物在85℃下加热3h，直到IR显示异氰酸酯谱带完全消失。蒸发甲苯，通过在Kugelrohr蒸馏设备中蒸馏去除残余的溶剂，得到MFF-7(196g，定量的)。
MFF-8(P＝4)，衍生自Desmodur XP 2599的四官能呋喃，其合成如下。在2L的四颈烧瓶上配有机械搅拌、回流冷凝管、氮气进口和加料漏斗，向烧瓶中加入Desmodur XP 2599(1014g，363mmol，通过异氰酸酯滴定测定的异氰酸酯为1.57meq/g)。在油浴中，搅拌下，在氮气存在下，加热烧瓶(油浴温度84-86℃)。一旦釜温达到恒定值(约80℃)，就滴加10滴DBTL。用恒压滴液漏斗缓慢滴加糠醇(通过异氰酸酯滴定定量，148.7g，1.52摩尔)。依据加料速率，反应温度范围为80-97℃。控制滴加速率，使反应温度不超过100℃。一旦IR表明异氰酸酯官能团耗尽(约1h的滴加时间，而后是额外的30min搅拌)，就将内容物转移至样品容器中。
MFM-1(Q＝2.0)
SRM-1，购自Henkel Corporation(Rocky Hill，CT，USA)
MFM-2(Q＝2.0)
BMI-5100，购自Daiwakasei Industry(日本)
MFM-3(Q＝2.0)
MFM-3的合成如下。将马来酸酐(30g，305mmol)和丙酮(125ml)添加至烘干的、充入氮气的500ml三颈圆底烧瓶中，配有聚四氟乙烯/玻璃搅拌器、加料漏斗、含有热偶的Y形接合器、冷凝器和进气口。1h内，将Versalink P650(126g，303mmol)滴加至马来酸酐溶液中。将反应混合物温热至室温，保持直到FTIR证明酸酐键不存在为止。添加乙酸酐(78g，765mmol)、三乙胺(13.5g，133mmol)和四水合醋酸锰(II)，加热反应混合物至40℃下2h，50℃下1h。冷却至室温过夜后，用旋转蒸发仪浓缩反应混合物，溶入CH2Cl2中，用水洗涤，通过无水MgSO4干燥。蒸发溶剂，用Kugelrohr蒸馏设备干燥产品，得到MFM-3(142g，89％)。
1H NMR(CDCl3)：δ8.2(d，4H)，7.5(d，4H)，6.9(s，4H)，4.4(t，4H)，3.5(m)，1.9-1.6(m)
MFM-4(Q＝2.0)
MFM-4(Q＝2)的合成如下。称取Dynacoll 7360(聚酯多元醇，购自Evonik，Mn＝3500g/mol)至玻璃烧瓶中，在120℃搅拌，并施加1小时的真空。添加MDI，在120℃下与羟基反应1小时(2/1NCO/OH)，部分反应时间在真空下，从而制备MDI封端预聚物。在配有机械搅拌的2升四颈烧瓶中，加入MDI封端的Dynacol 7360预聚物(1kg，12.5wt％的MDI，通过滴定确定的异氰酸酯含量为2.274％)。使用机械搅拌器(搅拌速度200rpm)加热混合物至110℃。一旦反应温度达到110℃，添加500ppm的Irganox 1010，随后添加8滴DBTL。分批添加2-羟乙基马来酰亚胺(76g，通过异氰酸酯滴定计算为539mmol)。IR显示异氰酸酯谱带几乎消失(约1.5小时)。此时，添加1ml乙醇(21mmol)，搅拌30分钟以猝灭任何残留的异氰酸酯。定量得到产物。
MFM-5(Q＝2)的合成类似MFM-4，只是基于聚酯多元醇Dynacoll 7380(Evonik)。
MFM-6(Q＝2)的合成类似MFM-4，只是基于聚酯多元醇Dynacoll 7490(Evonik)。
MFM-7(Q＝2)的合成类似MFM-4，只是基于聚酯多元醇Dynacoll 7250(Evonik)。
MFM-8(Q＝2)的合成类似MFM-4，只是基于聚酯多元醇Dynacoll 7231(Evonik)。
MFM-9(Q＝2)的合成类似MFM-4，只是基于聚酯多元醇Priplast 3196(Croda)。
配制物和搭接剪切
如表1所示制备样品。将MFF和MFM混合在一起，在120-160℃的范围内的固定温度下加热15-30min。
为了测定粘合剂的粘合强度，在尺寸为115×25×3mm的山毛榉材试样上进行搭接剪切测试。在固定的温度(120-160℃)下，使用预处理的涂层料，将250微米的粘合剂施加在六个山毛榉材条的末端上的25×25mm的面积上。尽可能快地，将第二个山毛榉材条置于每个的顶部，以使接头的交叠面积为25×25mm。在金属板材间，将6个搭接剪切接头置于彼此顶部上。向6个搭接剪切接头施加10秒的50psi的压力，金属板材被固定。在测试之前，将粘合的接头静置最少3天。用相同的方式制备用对比样品12(水分固化聚氨基甲酸酯热熔性粘合剂PF-9021)粘合的接头，只是在测试前，在23℃/50％RH下固化1周。
使用JJ Lloyd张力计测量剪切强度，使用125mm/分钟的十字头速度。通过力除以搭接剪切交叠的面积(N/mm2＝MPa)记录断裂剪切强度。对于方法1和方法2，分别在室温/湿度和在空气循环烘箱中80℃下，测量搭接剪切强度。结果见表1。
表1
a样品11另外还含有15.9％的热塑性丙烯酸聚合物Elvacite 4044，购自Lucite International
上述结果表明，可以将广泛的二烯和亲二烯体组合，产生具有比对比的热塑性热熔性粘合剂C13和C14更好的性能，尤其是耐热性。热可逆热熔性粘合剂的性能通常类似于或更好于对比的水分固化聚氨基甲酸酯热熔性粘合剂C12。
在从Rocholl GmBH得到的面积为100×25mm的各种基材(厚2mm的塑料基材，厚1.5mm的金属基材)上评价样品12(22.3％的MFF-2、5.0％的MFM-2、25％的MFM-4和47.7％的MFM-7的混合物，在与样品1-11相同的条件下)。在去除保护膜后，在使用前用异丙醇清洗每个塑料。在使用前，研磨金属表面，而后用丙酮冲洗。在固定温度下，在六个基材块的区域的末端，使用预处理的涂层料，将250微米的粘合剂施加在25×25mm的面积上。尽可能快地，将第二个基材条置于每个的顶部，以使接头的交叠面积为25×25mm。在金属板材间，将6个搭接剪切接头置于彼此顶部上。在每个搭接剪切接头上施加夹子。在移除夹子和测试之前，将粘合的接头静置最少3天。用相同的方式制备用对比样品12(水分固化聚氨基甲酸酯热熔性粘合剂PF-9021)粘合的接头，只是在测试前，在23℃/50％RH下固化1周。使用JJ Lloyd张力计测量剪切强度，使用125mm/分钟的十字头速度。通过力除以搭接剪切交叠的面积(N/mm2＝MPa)记录断裂剪切强度。在表2中对样品12(在150℃下施加，熔融粘度为10000mPa.s)和对比样品12(在120℃下施加PF-9021，熔融粘度为12000mPa.s)进行比较。基材故障标为(S)，而粘合剂故障标为(A)。
表2
熔融粘度和稳定性
在120℃下，将表3中所列的抗氧剂添加至样品1中，评价熔融粘度和热稳定性。在保持高温后，测量粘度作为时间的函数，并与HenkelCorporation提供的水分固化聚氨基甲酸酯热熔性粘合剂PF-375B对比。
在Model 74R温度控制器和加热器单元中，使用RVDV-1+型Brookfield粘度计，用27号转子测量熔融粘度。在烘箱中将粘合剂加热至135℃。称取14g粘合剂至一次性铝粘度计管中。将管插入粘度计中，在135℃的固定温度下持续20分钟，平衡至恒定粘度并读取。粘合剂在固定温度下保持若干小时后，再测量粘度。结果见表3.
表3
测试证明，对于热可逆粘合剂的组合物，粘度随时间的增加类似于水分固化的聚氨基甲酸酯热熔性粘合剂。
可逆性和熔融粘度
为了证明可逆性，再制造样品1+2％Irgastab UV-10，使其处于各种条件下，测量相应的的熔融粘度。条件和熔融粘度概述于表4中。
表4
表4显示，热可逆热熔性粘合剂可以被加热、冷却至室温持续不同的时间，而后再重复加热产生低熔融粘度。
Claims (20)
1.热可逆热熔性粘合剂，其包括：
a)至少一种多官能二烯单体/预聚物L-(X)P，其中
i)L选自以下组中：(聚)氨基甲酸酯、(聚)脲、(聚)酯、(聚)碳酸酯、(聚)酰胺、(聚)酰亚胺、(聚)苯乙烯、(聚)醚、(聚)(甲基)丙烯酸酯、(聚)烯烃、(聚)硅氧烷、以上物质的共聚物、以及它们的混合物，所述共聚物包括马来酸酐的共聚物；
ii)X是二烯，包含非环的1，3-二烯、环戊二烯、环己二烯、呋喃、富烯、吡咯、萘和蒽中的一种或多种；以及
iii)P大于零；
b)至少一种多官能亲二烯体单体/预聚物L-(Y)Q，其中
i)L选自以下组中：(聚)氨基甲酸酯、(聚)脲、(聚)酯、(聚)碳酸酯、(聚)酰胺、(聚)酰亚胺、(聚)苯乙烯、(聚)醚、(聚)(甲基)丙烯酸酯、(聚)烯烃、(聚)硅氧烷、以上物质的共聚物、以及它们的混合物，所述共聚物包括马来酸酐的共聚物；以及
ii)Y是亲二烯体，包含一种或多种以下物质：马来酰亚胺、异马来酰亚胺、柠康酰亚胺、衣康酰亚胺、马来酸酯、富马酸酯、丙烯酸酯、甲基丙烯酸酯、氰基丙烯酸酯、苯醌、苯醌肟、苯醌亚胺、萘醌、亚烷基丙二酸酯、含吸电子基团的炔和它们的混合物；以及
iii)Q大于零；以及
其中P或Q至少之一的值大于2.1。
2.权利要求1的热可逆热熔性粘合剂，其中P或Q至少之一的值小于3.0。
3.权利要求2的热可逆热熔性粘合剂，其中P和Q的加和的值等于或大于5.0。
4.权利要求1的热可逆热熔性粘合剂，其中多官能二烯单体/预聚物是以下物质或它们的组合：
5.权利要求4的热可逆热熔性粘合剂，其中多官能二烯单体/预聚物是以下物质或它们的组合：
6.权利要求1的热可逆热熔性粘合剂，其中多官能亲二烯体单体/预聚物是以下物质或它们的组合：
其中n＝5-10，
其中聚酯多元醇链段的分子量为约2000-约7000，
其中聚醚多元醇链段的分子量为约1000-18000。
7.权利要求6的热可逆热熔性粘合剂，其中多官能亲二烯体单体/预聚物是以下物质或它们的组合：
其中聚酯多元醇链段的分子量为约2000-约7000，
其中聚醚多元醇链段的分子量为约1000-18000。
8.权利要求1的粘合剂，其还包括热塑性聚合物。
9.权利要求8的粘合剂，其中热塑性聚合物包含酸、酸酐或羟基。
10.权利要求8的粘合剂，其中热塑性聚合物是聚(甲基)丙烯酸酯。
11.权利要求1的粘合剂，其还包括增粘剂、固化催化剂、粘合促进剂、抗氧剂、和/或填料。
12.一种制备热可逆热熔性粘合剂的方法，包括：
a)使至少一种多官能二烯单体/预聚物L-(X)P与至少一种多官能亲二烯体单体/预聚物L-(Y)Q混合，其中
i)L选自以下组中：(聚)氨基甲酸酯、(聚)脲、(聚)酯、(聚)碳酸酯、(聚)酰胺、(聚)酰亚胺、(聚)苯乙烯、(聚)醚、(聚)(甲基)丙烯酸酯、(聚)烯烃、(聚)硅氧烷、以上物质的共聚物、以及它们的混合物，所述共聚物包括马来酸酐的共聚物；
ii)X是二烯，包含非环的1，3-二烯、环戊二烯、环己二烯、呋喃、富烯、吡咯、萘和蒽中的一种或多种；
iii)Y是亲二烯体，包含一种或多种以下物质：马来酰亚胺、异马来酰亚胺、柠康酰亚胺、衣康酰亚胺、马来酸酯、富马酸酯、丙烯酸酯、甲基丙烯酸酯、氰基丙烯酸酯、苯醌、苯醌肟、苯醌亚胺、萘醌、亚烷基丙二酸酯、含吸电子基团的炔和它们的混合物；以及
iv)P或Q至少之一的值大于2.1；
b)将混合物加热至高于二烯/亲二烯体的键离解温度。
13.权利要求12的方法，其还包括：
c)冷却混合物至低于二烯/亲二烯体的键离解温度，
d)在低于二烯/亲二烯体的键离解温度下储存和/或运输混合物。
14.将基材粘合在一起的方法，其包括：将权利要求1的热可逆热熔性粘合剂组合物加热至高于二烯/亲二烯体的键离解温度，形成非交联加成物，将该非交联加成物施加在第一基材上，使第二基材与施加在第一基材上的加成物接触，并冷却施加的加成物，从而将加成物固化，以使所述第一基材粘合到所述第二基材。
15.权利要求14的方法，其中至少一种基材是纸张、塑料、木材、纺织品、泡沫、玻璃、金属、复合材料或陶瓷。
16.使用权利要求1的粘合剂制造的制品，其为书、包装膜、硬质板、家具、窗、鞋类、车头灯、用于汽车装饰或服装的粘合的纺织品/织物。
17.热可逆底漆层组合物，其包括：
a)至少一种多官能二烯单体/预聚物L-(X)P，其中
i)L选自以下组中：(聚)氨基甲酸酯、(聚)脲、(聚)酯、(聚)碳酸酯、(聚)酰胺、(聚)酰亚胺、(聚)苯乙烯、(聚)醚、(聚)(甲基)丙烯酸酯、(聚)烯烃、(聚)硅氧烷、以上物质的共聚物、以及它们的混合物，所述共聚物包括马来酸酐的共聚物；以及
ii)X是二烯，包含非环的1，3-二烯、环戊二烯、环己二烯、呋喃、富烯、吡咯、萘和蒽中的一种或多种；以及
iii)P大于零；
b)至少一种多官能亲二烯体单体/预聚物L-(Y)Q，其中
i)L选自以下组中：(聚)氨基甲酸酯、(聚)脲、(聚)酯、(聚)碳酸酯、(聚)酰胺、(聚)酰亚胺、(聚)苯乙烯、(聚)醚、(聚)(甲基)丙烯酸酯、(聚)烯烃、(聚)硅氧烷、以上物质的共聚物、以及它们的混合物，所述共聚物包括马来酸酐的共聚物；以及
ii)Y是亲二烯体，包含一种或多种以下物质：马来酰亚胺、异马来酰亚胺、柠康酰亚胺、衣康酰亚胺、马来酸酯、富马酸酯、丙烯酸酯、甲基丙烯酸酯、氰基丙烯酸酯、苯醌、苯醌肟、苯醌亚胺、萘醌、亚烷基丙二酸酯、含吸电子基团的炔和它们的混合物；以及
iii)Q大于0；以及
c)任选存在的溶剂，
其中P或Q至少之一的值大于2.1。
18.一种施加热可逆底漆层的方法，包括：将权利要求17的组合物加热至高于二烯/亲二烯体的键离解温度，形成非交联加成物，将该非交联加成物作为底漆涂层施加在基材上，冷却加成物，从而将加成物固化为交联的底漆层。
19.权利要求18的方法，其中至少基材是纸张、塑料、木材、纺织品、泡沫、玻璃、金属、复合材料或陶瓷。
20.使用权利要求17的底漆层组合物制造的制品，其中所述制品是书、包装膜、硬质板、家具、窗、鞋类、车头灯、用于汽车装饰或服装的粘合纺织品/织物。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18612709P | 2009-06-11 | 2009-06-11 | |
| US61/186,127 | 2009-06-11 | ||
| PCT/US2010/038270 WO2010144774A2 (en) | 2009-06-11 | 2010-06-11 | Thermally reversible hot melt adhesive composition containing multifunctional diene and dienophile compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102803416A true CN102803416A (zh) | 2012-11-28 |
| CN102803416B CN102803416B (zh) | 2016-01-20 |
Family
ID=43309478
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201080025530.1A Active CN102803416B (zh) | 2009-06-11 | 2010-06-11 | 含有多官能二烯和亲二烯体化合物的热可逆热熔性粘合剂 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8734939B2 (zh) |
| EP (1) | EP2440627B1 (zh) |
| JP (1) | JP5759987B2 (zh) |
| KR (1) | KR20120029421A (zh) |
| CN (1) | CN102803416B (zh) |
| AU (1) | AU2010260018B2 (zh) |
| BR (1) | BRPI1010733A2 (zh) |
| CL (1) | CL2011003114A1 (zh) |
| ES (1) | ES2539184T3 (zh) |
| RU (1) | RU2555883C2 (zh) |
| WO (1) | WO2010144774A2 (zh) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104877580A (zh) * | 2014-02-28 | 2015-09-02 | 罗伯特·博世有限公司 | 利用聚合物链改建的粘接 |
| CN106893503A (zh) * | 2015-12-18 | 2017-06-27 | 斯沃奇集团研究和开发有限公司 | 使用可重新配置热熔粘合剂装配的钟表部件的装置以及装配和重新配置这类部件的方法 |
| CN107075072A (zh) * | 2014-07-31 | 2017-08-18 | 路博润先进材料公司 | 热可逆交联聚氨酯 |
| CN107337748A (zh) * | 2017-08-02 | 2017-11-10 | 四川大学 | 一种带可逆交联键的苯乙烯类共聚物及其制备方法 |
| CN109206994A (zh) * | 2018-08-03 | 2019-01-15 | 浩力森涂料（上海）有限公司 | 自愈合的底面合一水性涂料 |
| CN109748998A (zh) * | 2017-11-02 | 2019-05-14 | 财团法人工业技术研究院 | 呋喃改性的化合物及低聚物 |
| CN111194342A (zh) * | 2017-10-27 | 2020-05-22 | 太阳精机株式会社 | 热可逆性交联型热熔粘接剂 |
| CN113897165A (zh) * | 2021-11-26 | 2022-01-07 | 韦尔通(厦门)科技股份有限公司 | 一种可拆卸聚氨酯热熔胶和制备原料及其制备方法和粘接方法 |
| US11247978B2 (en) | 2017-11-02 | 2022-02-15 | Industrial Technology Research Institute | Reversible crosslinking reactant composition |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102010001987A1 (de) * | 2010-02-16 | 2011-08-18 | Evonik Röhm GmbH, 64293 | Funktionsmaterialien mit reversibler Vernetzung |
| DE102010001992A1 (de) | 2010-02-16 | 2011-08-18 | Evonik Röhm GmbH, 64293 | Funktionsmaterialien mit steuerbarer Viskosität |
| US8802801B1 (en) * | 2011-03-25 | 2014-08-12 | Oceanit Laboratories, Inc. | Reconfigurable polymeric self-healing coating |
| DE102011080131A1 (de) * | 2011-07-29 | 2013-01-31 | Evonik Degussa Gmbh | Niedermolekulare Produkte, und deren Verwendung als reversible oder permanente Niedertemperatur-Vernetzer bei Diels-Alder-Reaktionen |
| EP2570450A1 (de) * | 2011-09-14 | 2013-03-20 | Sika Technology AG | Formgedächtnis-Material auf Basis eines Strukturklebstoffs |
| CN104053738B (zh) * | 2011-12-27 | 2016-10-05 | 朴喜大 | 粘合膜组合物 |
| KR101840906B1 (ko) * | 2012-01-25 | 2018-03-21 | 헨켈 아이피 앤드 홀딩 게엠베하 | 시아노아크릴레이트 조성물 |
| US9550883B2 (en) | 2012-01-25 | 2017-01-24 | Henkel IP & Holding GmbH | Cyanoacrylate compositions |
| US10239301B2 (en) * | 2012-07-03 | 2019-03-26 | 3M Innovative Properties Company | Heat-activatable siloxane-based adhesives |
| JP2014062050A (ja) * | 2012-09-19 | 2014-04-10 | Fujifilm Corp | 多価官能マレイミド系重合性化合物、これを含む硬化組成物およびインク組成物 |
| US9708509B2 (en) | 2012-10-09 | 2017-07-18 | Avery Dennison Corporation | Adhesives and related methods |
| US8877868B2 (en) * | 2013-02-26 | 2014-11-04 | Henkel IP & Holding GmbH | Hot melt adhesive comprising cyanoacrylate curing compounds |
| CN103173180B (zh) * | 2013-03-23 | 2015-06-24 | 广东新展化工新材料有限公司 | 一种热塑性胶黏剂及其制备方法 |
| US9193139B2 (en) * | 2013-05-30 | 2015-11-24 | Xerox Corporation | Reversible polymer adhesive composition |
| US8999444B2 (en) * | 2013-05-30 | 2015-04-07 | Xerox Corporation | Overcoat composition for ink jet printing |
| US9005708B2 (en) * | 2013-05-30 | 2015-04-14 | Xerox Corporation | Undercoat composition for ink jet printing |
| JP6613649B2 (ja) * | 2014-06-23 | 2019-12-04 | 東洋インキＳｃホールディングス株式会社 | 接着剤組成物、積層シート、太陽電池用裏面保護シート |
| AU2016215123B2 (en) | 2015-02-05 | 2018-08-09 | Avery Dennison Corporation | Label assemblies for adverse environments |
| US20160326408A1 (en) * | 2015-05-08 | 2016-11-10 | Henkel lP & Holding GmbH | Moisture curable hot melt adhesive with high adhesion strength and fast set time |
| WO2017027525A1 (en) * | 2015-08-11 | 2017-02-16 | The Arizona Board Of Regents On Behalf Of The University Of Arizona | Method of forming of a robust network of epoxy material through diels-alder reaction |
| EP3150648A1 (en) * | 2015-10-01 | 2017-04-05 | Henkel AG & Co. KGaA | Aqueous functionalized polyurethane dispersions |
| EP3380535B1 (en) | 2015-11-23 | 2020-09-16 | Rohm and Haas Company | Thermally reversible polymer crosslinking for pressure sensitive adhesives |
| EP3181652B1 (fr) * | 2015-12-18 | 2019-02-27 | The Swatch Group Research and Development Ltd. | Procédé d'assemblage et de repositionnement de pièces horlogères en utilisant un adhésif repositionnable à chaud |
| WO2017132497A1 (en) | 2016-01-29 | 2017-08-03 | The Arizona Board Of Regents On Behalf Of The University Of Arizona | Coumarin-modified epoxy adhesives |
| EP3411447A4 (en) * | 2016-02-04 | 2019-10-23 | Henkel IP & Holding GmbH | SOLUBLE ADHESIVES AND HIGH TEMPERATURE USE THEREOF |
| WO2018118767A1 (en) | 2016-12-22 | 2018-06-28 | Avery Dennison Corporation | Convertible pressure sensitive adhesives comprising urethane (meth) acrylate oligomers |
| WO2019216279A1 (ja) * | 2018-05-11 | 2019-11-14 | 株式会社クラレ | ポリウレタンの改質方法，ポリウレタン，研磨パッド及び研磨パッドの改質方法 |
| JP2021529859A (ja) | 2018-06-28 | 2021-11-04 | ヘンケル アイピー アンド ホールディング ゲゼルシャフト ミット ベシュレンクテル ハフツング | 低硬化温度を示す潜在的な還元剤を含む、カチオン硬化性組成物 |
| EP3632948A1 (en) * | 2018-10-04 | 2020-04-08 | Basf Se | Thermally reversible crosslinking strategy for thermoplastic polyurethane |
| US11820926B1 (en) * | 2020-10-27 | 2023-11-21 | Geisys Ventures, LLC | Programmable adhesive based upon Diels-Alder chemistry |
| CN113667362B (zh) * | 2021-08-27 | 2022-04-12 | 浙江东方齐心钢业集团有限公司 | 一种耐高温不锈钢无缝钢管及其表面处理工艺 |
| WO2023083248A1 (en) * | 2021-11-11 | 2023-05-19 | Ddp Specialty Electronic Materials Us, Llc | Adhesive system |
| US11732159B1 (en) | 2022-06-30 | 2023-08-22 | CreateMe Technologies LLC | Methods of disassembling apparel products having boronate adhesives |
| US11542413B1 (en) | 2022-06-30 | 2023-01-03 | CreateMe Technologies LLC | Methods of disassembling apparel products having imine adhesives |
| US11857013B1 (en) | 2022-06-30 | 2024-01-02 | Createme Technologies Inc. | Methods of assembling apparel products having shape memory adhesives |
| US11655397B1 (en) | 2022-06-30 | 2023-05-23 | CreateMe Technologies LLC | Methods of assembling apparel products having cycloalkene adhesives |
| US11629272B1 (en) | 2022-06-30 | 2023-04-18 | CreateMe Technologies LLC | Methods of assembling apparel products having thioester adhesives |
| US11530340B1 (en) | 2022-06-30 | 2022-12-20 | CreateMe Technologies LLC | Cyclodextrin-azobenzene adhesives for apparel products |
| US11730217B1 (en) | 2022-06-30 | 2023-08-22 | CreateMe Technologies LLC | Methods of disassembling apparel products having cycloalkene adhesives |
| US11712873B1 (en) | 2022-06-30 | 2023-08-01 | CreateMe Technologies LLC | Boronate adhesives for apparel products |
| US11632995B1 (en) | 2022-06-30 | 2023-04-25 | CreateMe Technologies LLC | Methods of assembling apparel products having disulfide adhesives |
| US11530336B1 (en) | 2022-06-30 | 2022-12-20 | CreateMe Technologies LLC | Methods of assembling apparel products having cyclodextrin-azobenzene adhesives |
| US11542412B1 (en) | 2022-06-30 | 2023-01-03 | CreateMe Technologies LLC | Methods of disassembling apparel products having cyclodextrin-azobenzene adhesives |
| US11653709B1 (en) | 2022-06-30 | 2023-05-23 | CreateMe Technologies LLC | Methods of disassembling apparel products having disulfide adhesives |
| US11713405B1 (en) | 2022-06-30 | 2023-08-01 | CreateMe Technologies LLC | Methods of disassembling apparel products having thioester adhesives |
| US11634616B1 (en) | 2022-06-30 | 2023-04-25 | CreateMe Technologies LLC | Methods of assembling apparel products having boronate adhesives |
| US11752234B1 (en) | 2022-06-30 | 2023-09-12 | CreateMe Technologies LLC | Shape memory adhesives for apparel products |
| US11849791B1 (en) | 2022-06-30 | 2023-12-26 | Createme Technologies Inc. | Methods of assembling apparel products having imine adhesives |
| US11692111B1 (en) | 2022-06-30 | 2023-07-04 | CreateMe Technologies LLC | Methods of disassembling apparel products having shape memory adhesives |
| US11905440B1 (en) | 2022-06-30 | 2024-02-20 | Createme Technologies Inc. | Disulfide adhesives for apparel products |
| US11730215B1 (en) | 2022-06-30 | 2023-08-22 | CreateMe Technologies LLC | Thioester adhesives for apparel products |
| WO2024039874A1 (en) | 2022-08-18 | 2024-02-22 | Sun Chemical Corporation | Low bond-temperature hot melt adhesive with high impact strength and chemical resistance |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5912282A (en) * | 1996-12-16 | 1999-06-15 | Shell Oil Company | Die attach adhesive compositions |
| CN1239970A (zh) * | 1996-12-13 | 1999-12-29 | 亨克尔两合股份公司 | 基于共轭二烯和亲二烯组份的聚合物 |
| CN1323335A (zh) * | 1998-10-20 | 2001-11-21 | 汉高两合股份公司 | 粘结dvd的热熔性粘合剂 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3435003A (en) | 1966-06-01 | 1969-03-25 | Du Pont | Cross-linked thermally reversible polymers produced from condensation polymers with pendant furan groups cross-linked with maleimides |
| US4391961A (en) * | 1981-04-09 | 1983-07-05 | Exxon Research & Engineering Co. | Process for preparing light colored petroleum resins and resins produced thereby (CS-203) |
| US4617364A (en) | 1982-12-09 | 1986-10-14 | Desoto, Inc. | Wet adhesion promoters for emulsion polymers |
| IT1197270B (it) * | 1986-09-25 | 1988-11-30 | Ausimont Spa | Composizioni adesive termofusibili a base di poliesteri |
| WO1995000576A1 (en) | 1993-06-22 | 1995-01-05 | Akzo Nobel N.V. | Novel phthalimides and reversibly crosslinked imide polymers |
| JPH07247364A (ja) * | 1994-03-10 | 1995-09-26 | Toyota Central Res & Dev Lab Inc | オリゴマー分解性高分子、その製造方法、回収方法及び再生方法 |
| GB9410867D0 (en) * | 1994-05-31 | 1994-07-20 | Ucb Sa | Radiation curable compositions |
| MY114204A (en) | 1994-11-15 | 2002-08-30 | Shell Int Research | A cross-linked resin |
| JP3453913B2 (ja) * | 1995-03-03 | 2003-10-06 | 株式会社豊田中央研究所 | オリゴマー分解性架橋型高分子、オリゴマー分解性架橋型高分子の成形体の製造方法及びオリゴマー分解性架橋型高分子の再利用方法 |
| US5726391A (en) | 1996-12-16 | 1998-03-10 | Shell Oil Company | Thermosetting Encapsulants for electronics packaging |
| US6512051B2 (en) * | 1998-01-22 | 2003-01-28 | The Yokohama Rubber Co., Ltd. | Elastomer composition |
| US6720387B1 (en) | 1998-02-18 | 2004-04-13 | 3M Innovative Properties Company | Hot-melt adhesive compositions comprising acidic polymer and basic polymer blends |
| JP4125452B2 (ja) * | 1999-07-23 | 2008-07-30 | 横浜ゴム株式会社 | 熱可逆架橋ポリマー組成物を用いたタイヤ |
| JP4087602B2 (ja) * | 2001-12-14 | 2008-05-21 | 横浜ゴム株式会社 | 硬化性化合物およびそれを含む硬化性樹脂組成物 |
| US6825315B2 (en) * | 2001-12-21 | 2004-11-30 | Sandia Corporation | Method of making thermally removable adhesives |
| AU2003241667A1 (en) | 2002-06-17 | 2003-12-31 | Nec Corporation | Biodegradable resin, biodegradable resin composition, biodegradable molded object, and process for producing biodegradable resin |
| US6933361B2 (en) | 2002-07-12 | 2005-08-23 | The Regents Of The University Of California | Thermally re-mendable cross-linked polymers |
| WO2004065615A2 (en) | 2003-01-15 | 2004-08-05 | University Of Washington | Reversible crosslinking method for making an electro-optic polymer |
| US7262238B2 (en) * | 2003-01-20 | 2007-08-28 | Hexion Specialty Chemicals, Inc. | Resin composition |
| JP2005097447A (ja) * | 2003-09-25 | 2005-04-14 | Mikasa Seiyaku Co Ltd | 粘着剤及びそれを用いた貼付用温熱材 |
| JP2006193628A (ja) * | 2005-01-14 | 2006-07-27 | Yokohama Rubber Co Ltd:The | 共役ジエン化合物、硬化性組成物およびその硬化物 |
| JP2006335861A (ja) * | 2005-06-01 | 2006-12-14 | Nippon Zeon Co Ltd | 接着剤、接着剤フィルム、半導体部品パッケージ、および半導体部品パッケージの製造方法 |
| JP5114864B2 (ja) * | 2006-04-20 | 2013-01-09 | 日本電気株式会社 | 多官能マレイミド化合物の製造方法 |
-
2010
- 2010-06-11 AU AU2010260018A patent/AU2010260018B2/en not_active Ceased
- 2010-06-11 CN CN201080025530.1A patent/CN102803416B/zh active Active
- 2010-06-11 KR KR20117029574A patent/KR20120029421A/ko not_active Application Discontinuation
- 2010-06-11 JP JP2012515173A patent/JP5759987B2/ja active Active
- 2010-06-11 RU RU2011154144/05A patent/RU2555883C2/ru not_active IP Right Cessation
- 2010-06-11 WO PCT/US2010/038270 patent/WO2010144774A2/en active Application Filing
- 2010-06-11 ES ES10786894.5T patent/ES2539184T3/es active Active
- 2010-06-11 EP EP20100786894 patent/EP2440627B1/en not_active Not-in-force
- 2010-06-11 BR BRPI1010733A patent/BRPI1010733A2/pt not_active IP Right Cessation
-
2011
- 2011-12-07 CL CL2011003114A patent/CL2011003114A1/es unknown
- 2011-12-12 US US13/323,090 patent/US8734939B2/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1239970A (zh) * | 1996-12-13 | 1999-12-29 | 亨克尔两合股份公司 | 基于共轭二烯和亲二烯组份的聚合物 |
| US5912282A (en) * | 1996-12-16 | 1999-06-15 | Shell Oil Company | Die attach adhesive compositions |
| CN1323335A (zh) * | 1998-10-20 | 2001-11-21 | 汉高两合股份公司 | 粘结dvd的热熔性粘合剂 |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104877580A (zh) * | 2014-02-28 | 2015-09-02 | 罗伯特·博世有限公司 | 利用聚合物链改建的粘接 |
| CN107075072A (zh) * | 2014-07-31 | 2017-08-18 | 路博润先进材料公司 | 热可逆交联聚氨酯 |
| CN106893503A (zh) * | 2015-12-18 | 2017-06-27 | 斯沃奇集团研究和开发有限公司 | 使用可重新配置热熔粘合剂装配的钟表部件的装置以及装配和重新配置这类部件的方法 |
| CN106893503B (zh) * | 2015-12-18 | 2021-02-19 | 斯沃奇集团研究和开发有限公司 | 使用可重新配置热熔粘合剂装配的钟表部件的装置以及装配和重新配置这类部件的方法 |
| CN107337748B (zh) * | 2017-08-02 | 2019-11-26 | 四川大学 | 一种带可逆交联键的苯乙烯类共聚物及其制备方法 |
| CN107337748A (zh) * | 2017-08-02 | 2017-11-10 | 四川大学 | 一种带可逆交联键的苯乙烯类共聚物及其制备方法 |
| CN111194342A (zh) * | 2017-10-27 | 2020-05-22 | 太阳精机株式会社 | 热可逆性交联型热熔粘接剂 |
| CN109748998A (zh) * | 2017-11-02 | 2019-05-14 | 财团法人工业技术研究院 | 呋喃改性的化合物及低聚物 |
| TWI709602B (zh) * | 2017-11-02 | 2020-11-11 | 財團法人工業技術研究院 | 可逆交聯反應組成物 |
| US10858471B2 (en) | 2017-11-02 | 2020-12-08 | Industrial Technology Research Institute | Reversible crosslinking reactant composition |
| CN109748998B (zh) * | 2017-11-02 | 2021-08-31 | 财团法人工业技术研究院 | 呋喃改性的化合物及低聚物 |
| US11247978B2 (en) | 2017-11-02 | 2022-02-15 | Industrial Technology Research Institute | Reversible crosslinking reactant composition |
| CN109206994A (zh) * | 2018-08-03 | 2019-01-15 | 浩力森涂料（上海）有限公司 | 自愈合的底面合一水性涂料 |
| CN113897165A (zh) * | 2021-11-26 | 2022-01-07 | 韦尔通(厦门)科技股份有限公司 | 一种可拆卸聚氨酯热熔胶和制备原料及其制备方法和粘接方法 |
| CN113897165B (zh) * | 2021-11-26 | 2023-05-26 | 韦尔通科技股份有限公司 | 一种可拆卸聚氨酯热熔胶和制备原料及其制备方法和粘接方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2010144774A3 (en) | 2011-03-24 |
| AU2010260018A1 (en) | 2011-12-15 |
| RU2555883C2 (ru) | 2015-07-10 |
| JP5759987B2 (ja) | 2015-08-05 |
| ES2539184T3 (es) | 2015-06-26 |
| EP2440627A2 (en) | 2012-04-18 |
| BRPI1010733A2 (pt) | 2016-03-15 |
| KR20120029421A (ko) | 2012-03-26 |
| EP2440627B1 (en) | 2015-03-04 |
| US20120082840A1 (en) | 2012-04-05 |
| CL2011003114A1 (es) | 2012-07-20 |
| JP2012530150A (ja) | 2012-11-29 |
| EP2440627A4 (en) | 2013-11-13 |
| AU2010260018B2 (en) | 2015-04-09 |
| CN102803416B (zh) | 2016-01-20 |
| WO2010144774A2 (en) | 2010-12-16 |
| US8734939B2 (en) | 2014-05-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102803416A (zh) | 含有多官能二烯和亲二烯体化合物的热可逆热熔性粘合剂 | |
| US8277601B2 (en) | Reactive hot melt adhesive | |
| EP1727845B1 (en) | Novel reactive hot melt adhesives | |
| US10190029B2 (en) | Removable polyurethane hot melt adhesive and the use thereof | |
| JP5773652B2 (ja) | 湿気硬化性ホットメルト接着剤 | |
| US7625963B2 (en) | Reactive hot melt adhesive with bituminous additive | |
| CN105899614B (zh) | 具有改进粘合性的反应性热熔性粘合剂 | |
| US20130020025A1 (en) | Silane moisture curable hot melts | |
| CN108431068A (zh) | 基于高耐热聚丙烯酸酯的聚氨酯热熔粘合剂 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| ASS | Succession or assignment of patent right |
Owner name: HENKEL US IP LLC Free format text: FORMER OWNER: HENKEL CORP. Effective date: 20141126 |
|
| C41 | Transfer of patent application or patent right or utility model | ||
| TA01 | Transfer of patent application right |
Effective date of registration: 20141126 Address after: American Connecticut Applicant after: Henkel American Intellectual Property LLC Address before: American Connecticut Applicant before: Henkel Corp. |
|
| ASS | Succession or assignment of patent right |
Owner name: HENKEL CORP. Free format text: FORMER OWNER: HENKEL US IP LLC Effective date: 20150423 |
|
| C41 | Transfer of patent application or patent right or utility model | ||
| TA01 | Transfer of patent application right |
Effective date of registration: 20150423 Address after: Dusseldorf Applicant after: HENKEL IP & HOLDING GmbH Address before: American Connecticut Applicant before: Henkel American Intellectual Property LLC |
|
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20220810 Address after: Dusseldorf Patentee after: HENKEL AG & Co.KGaA Address before: Dusseldorf Patentee before: HENKEL IP & HOLDING GmbH |
|
| TR01 | Transfer of patent right |