WO2022200974A1 - Mélange adhésif biosourcé et utilisation dudit mélange adhésif - Google Patents
Mélange adhésif biosourcé et utilisation dudit mélange adhésif Download PDFInfo
- Publication number
- WO2022200974A1 WO2022200974A1 PCT/IB2022/052525 IB2022052525W WO2022200974A1 WO 2022200974 A1 WO2022200974 A1 WO 2022200974A1 IB 2022052525 W IB2022052525 W IB 2022052525W WO 2022200974 A1 WO2022200974 A1 WO 2022200974A1
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- WO
- WIPO (PCT)
- Prior art keywords
- lignin
- adhesive mixture
- tackifier
- adhesive
- plasticizer
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 68
- 239000000853 adhesive Substances 0.000 title claims abstract description 61
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 61
- 229920005610 lignin Polymers 0.000 claims abstract description 55
- 239000004014 plasticizer Substances 0.000 claims abstract description 28
- 239000001993 wax Substances 0.000 claims abstract description 25
- 239000007787 solid Substances 0.000 claims abstract description 23
- 239000004831 Hot glue Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 11
- 238000004026 adhesive bonding Methods 0.000 claims description 8
- 229920000223 polyglycerol Polymers 0.000 claims description 7
- 238000007789 sealing Methods 0.000 claims description 7
- 238000009472 formulation Methods 0.000 claims description 6
- 239000002202 Polyethylene glycol Substances 0.000 claims description 4
- 238000002372 labelling Methods 0.000 claims description 4
- 238000010030 laminating Methods 0.000 claims description 4
- 239000011087 paperboard Substances 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- 150000003505 terpenes Chemical class 0.000 claims description 4
- 235000007586 terpenes Nutrition 0.000 claims description 4
- 238000009408 flooring Methods 0.000 claims description 3
- 238000009434 installation Methods 0.000 claims description 3
- 239000004745 nonwoven fabric Substances 0.000 claims description 3
- 229920001451 polypropylene glycol Polymers 0.000 claims description 3
- 239000002759 woven fabric Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- 239000004820 Pressure-sensitive adhesive Substances 0.000 abstract description 13
- 239000012943 hotmelt Substances 0.000 abstract description 6
- 239000000758 substrate Substances 0.000 description 13
- 239000011521 glass Substances 0.000 description 10
- 238000001816 cooling Methods 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 7
- 238000003303 reheating Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000003292 glue Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 6
- 239000002023 wood Substances 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 238000004806 packaging method and process Methods 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000123 paper Substances 0.000 description 4
- 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
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 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
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 239000001087 glyceryl triacetate Substances 0.000 description 3
- 235000013773 glyceryl triacetate Nutrition 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002245 particle 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
- 229960002622 triacetin Drugs 0.000 description 3
- 239000001069 triethyl citrate Substances 0.000 description 3
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 3
- 235000013769 triethyl citrate Nutrition 0.000 description 3
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 2
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 2
- ZFOZVQLOBQUTQQ-UHFFFAOYSA-N Tributyl citrate Chemical compound CCCCOC(=O)CC(O)(C(=O)OCCCC)CC(=O)OCCCC ZFOZVQLOBQUTQQ-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 235000013871 bee wax Nutrition 0.000 description 2
- 239000012166 beeswax Substances 0.000 description 2
- 229940092738 beeswax Drugs 0.000 description 2
- 239000008035 bio-based plasticizer Substances 0.000 description 2
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- -1 fatty acid esters Chemical class 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical class CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 239000012178 vegetable wax Substances 0.000 description 2
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 description 1
- KMZHZAAOEWVPSE-UHFFFAOYSA-N 2,3-dihydroxypropyl acetate Chemical compound CC(=O)OCC(O)CO KMZHZAAOEWVPSE-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- JFMGYULNQJPJCY-UHFFFAOYSA-N 4-(hydroxymethyl)-1,3-dioxolan-2-one Chemical compound OCC1COC(=O)O1 JFMGYULNQJPJCY-UHFFFAOYSA-N 0.000 description 1
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
- QZCLKYGREBVARF-UHFFFAOYSA-N Acetyl tributyl citrate Chemical compound CCCCOC(=O)CC(C(=O)OCCCC)(OC(C)=O)CC(=O)OCCCC QZCLKYGREBVARF-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 1
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 239000004348 Glyceryl diacetate Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 238000006701 autoxidation reaction Methods 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 229920001222 biopolymer Polymers 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000011111 cardboard Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000012707 chemical precursor Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 150000002193 fatty amides Chemical class 0.000 description 1
- 239000011094 fiberboard Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 235000019443 glyceryl diacetate Nutrition 0.000 description 1
- 239000007954 growth retardant Substances 0.000 description 1
- 239000011121 hardwood Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920001600 hydrophobic polymer Polymers 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229920005611 kraft lignin Polymers 0.000 description 1
- 239000002655 kraft paper Substances 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000010665 pine oil Substances 0.000 description 1
- 239000011120 plywood Substances 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 239000011122 softwood Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- WEAPVABOECTMGR-UHFFFAOYSA-N triethyl 2-acetyloxypropane-1,2,3-tricarboxylate Chemical compound CCOC(=O)CC(C(=O)OCC)(OC(C)=O)CC(=O)OCC WEAPVABOECTMGR-UHFFFAOYSA-N 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J197/00—Adhesives based on lignin-containing materials
- C09J197/005—Lignin
Definitions
- the adhesive composition can for example be used in packaging, for carton board, textile, metal, glass, wood etc. as well as labels, where the adhesive can provide either permanent or removable attachment.
- Other applications include wood working, assembly, book binding and tapes.
- Hot-melt adhesives are common for example in packaging for take-away products, lamination for tissue paper and textiles as well as in boxes made of bio-based materials.
- Lignin an aromatic polymer
- Lignin being a polyaromatic network
- Lignin has been extensively investigated as a suitable substitute for phenol during production of phenol-formaldehyde adhesives.
- Hot melt adhesives are a form of thermoplastic adhesive that are liquid when hot and then solidify in a period of from a few seconds to a few minutes, when cooled.
- Pressure-sensitive adhesives are adhesives that typically adhere to substrates when pressure is applied. The glue seam that is formed is normally not permanent, and the substrate is removable.
- pressure-sensitive adhesives can be used to produce bonds that are permanent, but not creep resistant.
- the PSAs can also be used to give rise to temporary or serial temporary bonds.
- Hot-melt adhesives provide several advantages over solvent- based adhesives. Volatile organic compounds are reduced or eliminated, and the drying or curing step is eliminated. Hot melt adhesives have a long shelf life and can usually be disposed of without special precautions. HMAs also maintain their thickness when solidifying. Hot melt adhesives are useful for example in the environmentally sensitive areas of packaging.
- Lignin is non-linear phenolic biopolymer with rather low molar mass, and thus generally not considered suitable for use as a strength providing cohesive polymer for use in hot-melt adhesives.
- WO2018/122470 A1 discloses the use of lignins as tackifiers or waxy components in biobased hot-melt or pressure sensitive adhesives.
- the compositions also comprise hydrophobic cohesive polymers, such as EVA copolymers or polyolefins.
- DE102012207868A1 discloses pressure-sensitive adhesive compositions comprising up to 20% by weight of lignin.
- Kraft lignin has a high glass transition temperature and does not flow well at elevated temperatures, not even above its glass transition temperature.
- plasticizers such as triacetin, triethyl citrate, propylene carbonates, ethylene carbonate, polyethylene glycol, polypropylene glycol, ethylene glycol or propylene glycol.
- the type of the plasticizers and their amount controls the lignin melt viscosity and softening point of the adhesive formulations.
- the bonding strength of the molten lignin normally requires another cohesive polymer.
- a formulation comprising lignin, biobased plasticizers, optionally tackifiers (non-biobased or biobased, mainly based on rosins or terpenes) and optionally waxes (preferably biobased), in the lignin hot-melt formulations significantly improves the bonding strength of the adhesives.
- hot melt adhesive formulations according to the present invention showed good performance in the packaging applications without requiring any another hydrophobic polymer other than lignin.
- the present invention is thus directed to an adhesive mixture comprising 25-85 wt-% lignin, 10-75 wt-% plasticizer, 0-50 wt-% tackifier and 0-40 wt-% waxes, by solid weight, wherein the combined amount of lignin, plasticizer, tackifier and waxes is at least 90 wt-%, by solid weight, of the adhesive mixture.
- the present invention is also directed to a method for preparing the adhesive mixture.
- the present invention is thus also directed to the use of the adhesive mixture in carton sealing and labeling, paperboard assembling and sealing, spine gluing in the bookbinding industry, profile-wrapping, product assembly and laminating applications in the woodworking industry, installation of flooring and ceiling panels, gluing of woven and non-woven fabrics, disposable diapers, affixing of parts and wires in electronic devices, or to secure, insulate, and protect the device’s components.
- lignin embraces any kind of lignin, e.g. lignin originated from hardwood, softwood or annular plants.
- the lignin is an alkaline lignin generated in e.g. the Kraft process.
- the lignin has been purified or isolated before being used in the process according to the present invention.
- the lignin may be isolated from black liquor and optionally be further purified before being used in the process according to the present invention.
- the purification is typically such that the purity of the lignin is at least 90%, preferably at least 95%, more preferably at least 98% or 99%.
- the lignin used according to the method of the present invention preferably contains less than 10%, preferably less than 5%, more preferably less than 2% or 1% impurities.
- the lignin may then be separated from the black liquor by using the process disclosed in W02006031175.
- the lignin may then be separated from the black liquor by using the process referred to as the LignoBoost process.
- the lignin may be provided in the form of particles, such as particles having an average particle size of from 50 micrometers to 500 micrometers.
- the lignin may be chemically modified using methods known in the art. Preferably, the lignin used according to the present invention has not been chemically modified.
- monomeric plasticizers include the following: ethylene glycol, propylene glycol, glycerol, propylene carbonate, ethylene carbonate, glycerol carbonate, vinyl carbonate, triacetin, diacetin, monoacetin, triethyl citrate, tributyl citrate, acetyl triethyl citrate, acetyl tributyl citrate, dimethyl succinate, diethyl succinate, ethyl lactate, methyl lactate, fatty acid esters of glycerol or polyglycerol (such as polyglycerol caprylate) or polyethylene glycol, diethyl phthalate, and mixtures thereof.
- Polyglycerol is one example suitable for reducing the Tg (glass transition temperature) as well as the viscosity of the adhesive mixture. Its content in these mixtures is typically from about 10 to about 75 wt-% by weight of the mixture, based on the dry weight.
- the plasticizers used are polymeric plasticizers or bio based plasticizer or more preferably, bio-based polymeric plasticizers.
- the plasticizer is a fatty acid ester of polyglycerol, such as polyglycerol caprylate.
- tackifier refers to the component of an adhesive mixture that provides the adhesive with external strength, i.e. that is capable of holding the adhesive and the substrate together.
- the tackifier may be synthetic or biobased.
- the tackifier is a biobased tackifier, such as a tackifier mainly based on rosins or terpenes, such as rosin acid, rosin ester, hydrogenated rosin ester, terpene phenolic resin etc.
- the adhesive mixture according to the present invention optionally comprises waxes, e.g., synthetic waxes, bees wax, vegetable oil-based wax, fatty amide waxes or oxidized Fischer-Tropsch waxes.
- the wax is bio-based wax such as vegetable-oil based wax, soy-based wax or bees wax etc. These waxes function by increasing the setting rate, and by lowering the melt viscosity. Further, they can improve bond strength and temperature resistance.
- the adhesives (also called glues) of the present invention include hot-melt adhesives (HMA), which are soft and tacky when hot, and solidify upon cooling, as well as pressure-sensitive adhesives (PSA), which adhere to substrates when pressure is applied.
- HMA hot-melt adhesives
- PSA pressure-sensitive adhesives
- the adhesive mixture according to the present invention optionally comprises extenders such as antioxidants and stabilizers (e.g., hindered phenols, butylated hydroxytoluene (BHT), phosphites, phosphates, hindered aromatic amines), added in small amounts ( ⁇ 1 wt-%), not influencing physical properties, but protecting the material from degradation or ageing (caused, e.g., by autoxidation), or UV stabilizers, or biocides for hindering bacterial growth, or flame retardants.
- antioxidants and stabilizers e.g., hindered phenols, butylated hydroxytoluene (BHT), phosphites, phosphates, hindered aromatic amines
- the adhesive mixture according to the present invention optionally comprises pigments, dyes and/or glitter.
- the adhesive mixture according to the present invention may optionally comprise antistatic agents.
- the adhesive mixture according to the present invention may optionally comprise organic carboxylic acids having at least two carboxyl groups, such as citric acid.
- the adhesive mixture according to the present invention may optionally comprise agents that make the mixture more hydrophobic, such as cellulose acetate.
- the adhesive mixture comprises 40-55 wt-% lignin, 25-40 wt-% plasticizer, 15-25 wt-% tackifier and 0-5 wt-% waxes, by solid weight.
- the combined amount of lignin, plasticizer, tackifier and waxes is at least 90 wt-%, by solid weight, of the adhesive mixture.
- the combined amount of lignin, plasticizer, tackifier and waxes is at least 92 wt-%, more preferably at least 95 wt-%, by solid weight, of the adhesive mixture.
- the adhesive mixture may be prepared by mixing the selected components in the desired ratios at an elevated temperature, particularly varying from about 60° to about 200°C, preferably at a temperature of from 100° to 150°C.
- hot-melt adhesive mixtures are applied to the selected substrates by jet application in various forms (extrusion, spray, slot, spot).
- the high melt viscosity makes them ideal for porous and permeable substrates.
- HMAs are capable of bonding an array of different substrates including: rubbers, ceramics, metals, plastics, glass and wood.
- the prepared adhesive mixture is applied and glued on a suitable substrate selected from rubbers, ceramics, metals, plastics, glass, wood, paper and board substrates, with paper and board substrates being the most suitable alternatives, such as sack paper and coated board.
- the important gluing parameters in industrial processes are the open time related to the setting behavior, and compression phase (close time/pressure).
- elevated temperature and pressure are used during the application of the adhesive mixture.
- suitable parameters include an application temperature of 100° to 200°C, preferably 120° to 190°C, and most suitably about 120° to 170°C.
- the adhesives of the present invention can be used in a wide variety of applications, e.g., carton sealing and labeling, paperboard assembling and sealing, spine gluing in the bookbinding industry, profile-wrapping, product assembly and laminating applications in the woodworking industry, installation of flooring and ceiling panels, gluing of woven and non-woven fabrics, disposable diapers, affixing of parts and wires in electronic devices, or to secure, insulate, and protect the device's components.
- Example 1 Lignin powder (solid content 95%), polyglycerol-4 and vegetable wax was mixed in a weight ratio of 100:150:33 in a 400ml glass beaker, the beaker was then immersed in the heated oil bath on a hot plate, the mixture was melt compounded (hot blended) for 4 hours at 160°C under over-head stirring using 3 blade propeller central shaft. The homogeneous molten product was formed visually, the product made was able to solidify upon cooling and turned to the molten state again when undergo reheating.
- Granulated lignin powder (solid content 98%), polyglycerol-4 and vegetable wax was mixed in a weight ratio of 100:150:33 in a 400ml glass beaker, the beaker was then immersed in the heated oil bath on a hot plate, the mixture was melt compounded (hot blended) for 4 hours at 160°C under over-head stirring using 3 blade propeller central shaft. The homogeneous molten product was formed visually, the product made was able to solidify upon cooling and turned to the molten state again when undergo reheating.
- Example 4 Lignin powder (solid content 95%), polyglycerol-4 and PEG 400 was mixed in a weight ratio of 100:33:33 in a 400ml glass beaker, the beaker was then immersed in the heated oil bath on a hot plate, the mixture was melt compounded (hot blended) for 4 hours at 160°C under over-head stirring using 3 blade propeller central shaft. The homogeneous molten product was formed visually, the product made was able to solidify upon cooling and turned to the molten state again when undergo reheating.
- Lignin powder solid content 95%), triacetin, 2,5-furandicarboylic acid was hand mixed 5 min in a glass beaker with weight ratio of 50:41:10, the beaker was then baked in the oven at 160°C for 20 min. The homogeneous molten product was formed visually, the product made was able to solidify upon cooling and turned to the molten state again when undergo reheating.
- the dispersion of lignin was continued for another 30 min. After the dispersion step, the heating temperature was set to rapidly ramp up to 150°C. The homogeneous molten product was formed visually in an hour with mild stirring at 180 rpm. the product made was able to solidify upon cooling and turned to the molten state again when undergo reheating.
- the automated bonding evaluation system was used to determine the dry shear strength on a lap shear test.
- the test sample, D flute (2mm) corrugated cardboard was cut to 20 mm wide and 105 mm in length.
- two corrugated strips were glued together with an overlapping joint area of 20x5 mm 2 .
- the glue was added to the tank of the hand-held applicator either in its solid form or at its molten state. 45 min stabilization time was allowed for the hand-held applicator to reach the operating temperature at 150°C.
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- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
La présente invention concerne des mélanges adhésifs. En particulier, l'invention concerne l'utilisation de lignine dans des adhésifs thermofusibles (non sensibles à la pression) et sensibles à la pression biosourcés, ainsi que de nouveaux mélanges adhésifs appropriés pour être utilisés en tant que tels adhésifs. Le mélange adhésif comprend 25 à 85 % en poids de lignine, 10 à 75 % en poids de plastifiant, 0 à 50 % en poids d'agent poisseux et 0 à 40 % en poids de cires, par poids solide. La quantité combinée de lignine, de plastifiant, d'agent poisseux et de cires est d'au moins 90 % en poids, par poids solide, du mélange adhésif.
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EP0634466A2 (fr) * | 1993-07-16 | 1995-01-18 | National Starch and Chemical Investment Holding Corporation | Adhésifs thermofusibles et hydrophiles |
US20110054154A1 (en) * | 2009-08-31 | 2011-03-03 | Weyerhaeuser Nr Company | Lignothermoplastic |
JP2011219728A (ja) * | 2010-02-10 | 2011-11-04 | Hitachi Chem Co Ltd | 粘着剤 |
WO2018122470A1 (fr) * | 2017-01-02 | 2018-07-05 | Teknologian Tutkimuskeskus Vtt Oy | Adhésif thermofusible d'origine biologique comprenant de la lignine en tant que composant |
EP3530710A1 (fr) * | 2018-02-23 | 2019-08-28 | MAGNA STEYR Fahrzeugtechnik AG & Co KG | Adhésif, fabrication et utilisation d'un adhésif |
EP3632866A1 (fr) * | 2018-10-05 | 2020-04-08 | Rockwool International A/S | Composition de liant aqueux |
US20210040273A1 (en) * | 2018-02-09 | 2021-02-11 | Fpinnovations | Meltable lignin compositions, method for producing them and their uses |
CN112625652A (zh) * | 2020-12-21 | 2021-04-09 | 华南理工大学 | 一种木质素/聚醚多元醇超分子复合胶黏剂及其制备方法 |
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2022
- 2022-03-21 WO PCT/IB2022/052525 patent/WO2022200974A1/fr active Application Filing
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US4702496A (en) * | 1984-04-16 | 1987-10-27 | H. B. Fuller Company | Book binding process involving primer adhesive containing starch |
EP0634466A2 (fr) * | 1993-07-16 | 1995-01-18 | National Starch and Chemical Investment Holding Corporation | Adhésifs thermofusibles et hydrophiles |
US20110054154A1 (en) * | 2009-08-31 | 2011-03-03 | Weyerhaeuser Nr Company | Lignothermoplastic |
JP2011219728A (ja) * | 2010-02-10 | 2011-11-04 | Hitachi Chem Co Ltd | 粘着剤 |
WO2018122470A1 (fr) * | 2017-01-02 | 2018-07-05 | Teknologian Tutkimuskeskus Vtt Oy | Adhésif thermofusible d'origine biologique comprenant de la lignine en tant que composant |
US20210040273A1 (en) * | 2018-02-09 | 2021-02-11 | Fpinnovations | Meltable lignin compositions, method for producing them and their uses |
EP3530710A1 (fr) * | 2018-02-23 | 2019-08-28 | MAGNA STEYR Fahrzeugtechnik AG & Co KG | Adhésif, fabrication et utilisation d'un adhésif |
EP3632866A1 (fr) * | 2018-10-05 | 2020-04-08 | Rockwool International A/S | Composition de liant aqueux |
CN112625652A (zh) * | 2020-12-21 | 2021-04-09 | 华南理工大学 | 一种木质素/聚醚多元醇超分子复合胶黏剂及其制备方法 |
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