EP2895520A1 - Two-component polyurethane compositions, in particular suitable for use as viscoplastic structural adhesives - Google Patents
Two-component polyurethane compositions, in particular suitable for use as viscoplastic structural adhesivesInfo
- Publication number
- EP2895520A1 EP2895520A1 EP13763008.3A EP13763008A EP2895520A1 EP 2895520 A1 EP2895520 A1 EP 2895520A1 EP 13763008 A EP13763008 A EP 13763008A EP 2895520 A1 EP2895520 A1 EP 2895520A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- component
- polyurethane composition
- component polyurethane
- groups
- sum
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 58
- 239000004814 polyurethane Substances 0.000 title claims abstract description 50
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 50
- 239000000853 adhesive Substances 0.000 title claims abstract description 32
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 31
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 36
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 36
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 27
- 239000004359 castor oil Substances 0.000 claims abstract description 26
- 235000019438 castor oil Nutrition 0.000 claims abstract description 25
- 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 claims abstract description 25
- 229920005862 polyol Polymers 0.000 claims abstract description 20
- 150000003077 polyols Chemical class 0.000 claims abstract description 20
- 125000003118 aryl group Chemical group 0.000 claims abstract description 18
- 235000011187 glycerol Nutrition 0.000 claims abstract description 15
- 239000000758 substrate Substances 0.000 claims description 12
- 238000005304 joining Methods 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 5
- 239000011368 organic material Substances 0.000 claims description 4
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 16
- 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 24
- -1 MDI carbodiimides Chemical class 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000005259 measurement Methods 0.000 description 7
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 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 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 229910052797 bismuth Inorganic materials 0.000 description 3
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- VNTDZUDTQCZFKN-UHFFFAOYSA-L zinc 2,2-dimethyloctanoate Chemical compound [Zn++].CCCCCCC(C)(C)C([O-])=O.CCCCCCC(C)(C)C([O-])=O VNTDZUDTQCZFKN-UHFFFAOYSA-L 0.000 description 3
- 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 2
- YXRKNIZYMIXSAD-UHFFFAOYSA-N 1,6-diisocyanatohexane Chemical compound O=C=NCCCCCCN=C=O.O=C=NCCCCCCN=C=O.O=C=NCCCCCCN=C=O YXRKNIZYMIXSAD-UHFFFAOYSA-N 0.000 description 2
- QZWKEPYTBWZJJA-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine-4,4'-diisocyanate Chemical compound C1=C(N=C=O)C(OC)=CC(C=2C=C(OC)C(N=C=O)=CC=2)=C1 QZWKEPYTBWZJJA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 235000004443 Ricinus communis Nutrition 0.000 description 2
- 240000000528 Ricinus communis Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 229920005839 ecoflex® Polymers 0.000 description 2
- 229920005845 ecovio® Polymers 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000021588 free fatty acids Nutrition 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000005846 sugar alcohols Chemical class 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
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- HUFIHLDYTVSJID-UHFFFAOYSA-N 1,3,5-tris(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC(CN=C=O)=CC(CN=C=O)=C1 HUFIHLDYTVSJID-UHFFFAOYSA-N 0.000 description 1
- LGLNTUFPPXPHKF-UHFFFAOYSA-N 1,4-diisocyanato-2,3,5,6-tetramethylbenzene Chemical compound CC1=C(C)C(N=C=O)=C(C)C(C)=C1N=C=O LGLNTUFPPXPHKF-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
- LTIKIBFTASQKMM-UHFFFAOYSA-N 1-[bis(4-isocyanatophenyl)methyl]-4-isocyanatobenzene Chemical compound C1=CC(N=C=O)=CC=C1C(C=1C=CC(=CC=1)N=C=O)C1=CC=C(N=C=O)C=C1 LTIKIBFTASQKMM-UHFFFAOYSA-N 0.000 description 1
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 1
- ICLCCFKUSALICQ-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanato-3-methylphenyl)-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(C=2C=C(C)C(N=C=O)=CC=2)=C1 ICLCCFKUSALICQ-UHFFFAOYSA-N 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 235000012043 Euphorbia helioscopia Nutrition 0.000 description 1
- 229920002430 Fibre-reinforced plastic Polymers 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000011138 biotechnological process Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000006229 carbon black Substances 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
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000011151 fibre-reinforced plastic Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 230000006855 networking Effects 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 229910052615 phyllosilicate Inorganic materials 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- KGLSETWPYVUTQX-UHFFFAOYSA-N tris(4-isocyanatophenoxy)-sulfanylidene-$l^{5}-phosphane Chemical compound C1=CC(N=C=O)=CC=C1OP(=S)(OC=1C=CC(=CC=1)N=C=O)OC1=CC=C(N=C=O)C=C1 KGLSETWPYVUTQX-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B37/00—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
- B32B37/12—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
- B32B7/04—Interconnection of layers
- B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B40/00—Processes, in general, for influencing or modifying the properties of mortars, concrete or artificial stone compositions, e.g. their setting or hardening ability
- C04B40/06—Inhibiting the setting, e.g. mortars of the deferred action type containing water in breakable containers ; Inhibiting the action of active ingredients
- C04B40/0641—Mechanical separation of ingredients, e.g. accelerator in breakable microcapsules
- C04B40/065—Two or more component mortars
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/36—Hydroxylated esters of higher fatty acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7621—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring being toluene diisocyanate including isomer mixtures
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/06—Polyurethanes from polyesters
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B37/00—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
- B32B37/12—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives
- B32B2037/1253—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives curable adhesive
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2375/00—Polyureas; Polyurethanes
-
- 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.]
Definitions
- the invention relates to the field of two-component polyurethane compositions, in particular the tough-elastic structural two-component polyurethane adhesives with adjustable hydrolytic
- Two-component polyurethane adhesives based on polyols and polyisocyanates have been used for a long time.
- Two-component polyurethane adhesives have the advantage that they cure quickly after mixing and therefore can absorb and transmit high forces quickly after a short time.
- high demands are placed on such adhesives in terms of strength and ductility, since such adhesives represent elements of load-bearing structures.
- Object of the present invention is therefore, a
- a two-component polyurethane composition in particular a structural two-component polyurethane adhesive, which at the same time has a high elongation at high strength and is controlled hydrolytically degradable. This is done by the
- the present invention relates to a two-component
- Polyurethane composition consisting of a polyol component K1 and a polyisocyanate component K2;
- Weight loss is measured after drying the composition under vacuum until constant weight is achieved, expressed as a percentage of the weight of the cured composition prior to storage in demineralised water.
- poly in substance names such as “polyol”, “polyisocyanate”, “polyether” or “polyamine” indicates in this document that the respective substance formally contains more than one functional group per molecule occurring in its name
- polyol component K1 comprises castor oil A1
- Castor oil may contain traces of water.
- the water content in the castor oil is ⁇ 5% by weight, preferably ⁇ 1% by weight, particularly preferably ⁇ 0.5% by weight.
- castor oil also known as castor oil or castor oil
- castor oil is understood to mean in particular castor oil in the present document, as described in CD Römpp Chemie Lexikon, Version 1 .0, Thieme Verlag.
- Suitable castor oils are also commercially available, for example, under the trade name Alberdingk® Castor Oil Low Acid 0.7 from Alberdingk Boley, Germany or under the trade name # 1 Grade Castor Oil from Vertellus Specialties Inc, USA.
- castor oil is a naturally renewable raw material and is extracted from the seed of the castor bean (Ricinus communis,
- the castor oil can be used raw or purified.
- the use of castor oil with a reduced content of free fatty acids has proved particularly suitable.
- castor oil with a content of free fatty acids of less than 5 wt .-%, in particular between 1 and 4 wt .-%, is used. This is to the advantage of that thereby a better
- the polyol component K1 comprises 1,2,3-propanetriol (also called glycerol) A2. Suitable 1,2,3-propanetriols are, for example, commercially available from ecoMotion GmbH, Germany.
- the present polyisocyanate component K2 comprises at least one aromatic polyisocyanate B1.
- Suitable aromatic polyisocyanates B1 are in particular monomeric di- or triisocyanates, as well as oligomers, polymers and derivatives of monomeric di- or triisocyanates, as well as any mixtures thereof.
- Suitable aromatic monomeric di- or triisocyanates are in particular 2,4- and 2,6-toluene diisocyanate and any desired mixtures of these isomers (TDI), 4,4'-, 2,4'- and 2,2'-diphenylmethane diisocyanate and any mixtures of these Isomeric (MDI), 1,3- and 1,4-phenylenediisocyanate, 2,3,5,6-tetramethyl-1,4-diisocyanatobenzene, naphthalene-1,5-diisocyanate (NDI), 3,3'-dimethyl- 4,4'-diisocyanatodiphenyl (TODI), dianisidine diisocyanate (DADI), 1,3,5-tris (isocyanatomethyl) benzene, tris (4-isocyanatophenyl) methane and tris (4-isocyanatophenyl) thiophosphate.
- Suitable oligomers, polymers and derivatives of said monomeric di- and triisocyanates are in particular derived from MDI and TDI. Of these, especially suitable are commercially available types of TDI oligomers such as Desmodur ® IL (Bayer); continue to be suitable for
- modified MDI Room temperature liquid forms of MDI (so-called "modified MDI"), which are mixtures of MDI with MDI derivatives, in particular MDI carbodiimides or MDI uretonimines, known under
- oligomeric polyisocyanates are usually mixtures of substances having different degrees of oligomerization and / or chemical structures. They preferably have an average NCO functionality of 2.1 to 4.0.
- Preferred aromatic polyisocyanates B1 are MDI and / or TDI which have> 40% by weight of monomeric MDI and / or monomeric TDI, based on the total weight of MDI and / or TDI.
- polyisocyanate B1 is MDI, in particular MDI comprising> 40% by weight of monomeric MDI, this is among others
- Tensile shear strength values and high E-modules can be achieved. Further, the use of MDI is conducive to rapid hydrolytic degradability.
- polyisocyanate B1 is TDI, in particular TDI comprising> 40% by weight of monomeric TDI, this is among others
- the ratio of the weight% of (A1 / A2) is 4-50.
- the ratio of the weight% of (A1 / A2) is 30-4, in particular 20-4, particularly preferably 13-4, most preferably 8-4, this is advantageous in that high tensile strength values are thereby obtained.
- aromatic polyisocyanate B1 is MDI and the ratio of the weight% of (A1 / A2) is 50-13, especially 50-20, it is advantageous in that high elongation at break values are obtained.
- aromatic polyisocyanate B1 is TDI and the ratio of the weight% of (A1 / A2) is 30-4, in particular 13-4, this is advantageous in that high values of elongation at break are obtained. If the ratio of the weight% of (A1 / A2) is 30-4, in particular
- B1 all OH groups of the sum of (A1 + A2) is 1, 15: 1 - 0.85: 1.
- the ratio of all NCO groups of the aromatic polyisocyanates B1 all OH groups of the sum of (A1 + A2) 1, 1: 1 - 0.9: 1.
- the ratio described above is understood to mean the molar ratio of mentioned groups.
- Polyol component K1 more than 7% OH groups (which are not from (A1 + A2)), based on the sum of all OH groups of the two-component polyurethane composition, so that leads to an insufficient hydrolytic degradability, as for example in Table 6 and FIG. 3 from example 50, with a value of about 8.6% (OH groups not derived from (A1 + A2)).
- Polyurethane composition the sum of all OH groups of (A1 + A2)> 95%, in particular> 98%, particularly preferably> 99%, most preferably> 99.5%, the sum of all OH groups of the two-component polyurethane composition. This is a better hydrolytic
- the two-part polyurethane composition is substantially free of OH groups which are not derived from (A1 + A2).
- the term "essentially free” in this case means that the sum of the OH groups which do not originate from (A1 + A2) is ⁇ 5%, in particular ⁇ 2%, particularly preferably ⁇ 1%, most preferably ⁇ 0.5%, based on the sum of all OH groups of the two-component polyurethane composition, which contributes to better hydrolytic degradability.
- the two-part polyurethane composition is substantially free of OH groups of the following substances:
- Low molecular weight aliphatic triols having a molecular weight of 120 to 2000 g / mol (excluding 1, 2,3-propanetriol).
- low molecular weight aliphatic triols may contain urethane and / or urea and / or ether groups.
- the shape of the triole can be very different. For example, star-shaped or comb-shaped triols are possible. It is also possible that both primary and secondary hydroxyl groups are present in the triol.
- mentioned low molecular weight aliphatic triols can be prepared from an aliphatic triisocyanate, in particular from an isocyanurate, which is formed from three diisocyanate molecules, in excess of aliphatic diols, in particular of
- Polyetherdiols optionally by further extension by means of aliphatic diisocyanates and aliphatic diols reach.
- Other exemplary low molecular weight aliphatic triols may be selected from low molecular weight aliphatic triols, such as
- Trimethylolpropane or glycerol, and an aliphatic diisocyanate and subsequent reaction with an aliphatic diol can be obtained.
- Further exemplary low molecular weight aliphatic triols are products of an alkoxylation reaction of low molecular weight
- triols such as trimethylolpropane or glycerol.
- low molecular weight diols having a molecular weight of 120 to 2000 g / mol.
- polystyrene resin having 5 to 8 hydroxyl groups with a molecular weight of 120 to 3000 g / mol.
- Such polyols are typically sugar alcohols and sugar alcohol-based polyols having a corresponding number of OH groups, in particular pentitols or hexitols, or those based on
- Disaccharides It can also be used the corresponding sugars.
- natural oils excluding castor oil
- natural oils which are reaction products with ketone resins, in particular reaction products of castor oil with ketone resins, in particular those marketed, for example, by Bayer under the name Desmophen® 1 150 and by Cognis under the name Sovermol® 805.
- natural oils in this document refers to esters of fatty acids with glycerol which are liquid at 23 ° C. These esters are naturally occurring, but can also be produced by synthesis or by technical and biotechnological processes all carboxylic acids, their carboxyl groups are connected to saturated, unsaturated, branched or unbranched alkyl radicals having more than 9 carbon atoms.
- the two-part polyurethane composition is substantially free of aliphatic polyisocyanates.
- the term "substantially free” is understood to mean that the sum of the NCO groups which does not originate from B1 is ⁇ 5%, in particular ⁇ 2%, particularly preferably ⁇ 1%, most preferably ⁇ 0.5%, In the majority of cases, using aliphatic polyisocyanates, it is not possible to produce a cured product which is suitable as an adhesive In the case of Examples 15-24 and 30-34, it is not possible to obtain a cured product within a period of 7 days and to prepare test specimens therefrom.
- the proportion of the sum of castor oil A1 and 1,2,3-propanetriol A2 is> 90% by weight, in particular> 95% by weight, particularly preferably> 99% by weight, based on the total weight of the oil
- the proportion of the aromatic polyisocyanate B1 is preferably> 90% by weight, in particular> 95% by weight, particularly preferably> 99% by weight, based on the total weight of the polyisocyanate component K2.
- components K1 and K2 are advantageously formulated such that the volume ratio of component K1 and K2 is between 1: 3 and 3: 1, in particular between 1: 2 and 2: 1. This ratio is particularly preferably about 1: 1.
- Both components K1 and K2 can, in addition to the other components already mentioned, as they are the expert from polyurethane chemistry ago knows, have. These can be present in only one component or in both.
- additional constituents are solvents, plasticizers and / or extenders, fillers such as carbon black, chalk, talc, baryth, phyllosilicates, adhesion promoters such as in particular trialkoxysilanes, thixotropic agents such as amorphous silicas, drying agents such as zeolites and color pigments.
- the components K1 and K2 are stored separately from each other before use and mixed together only at or just before use.
- the components are advantageously present in a package consisting of two separate chambers in such a way that the polyol component K1 is present in one chamber and the polyisocyanate component K2 in the other chamber.
- the components K1 and K2 are filled into the chambers of the packaging and sealed air and moisture-tight.
- the invention comprises a package consisting of a package having two separate chambers and a two-part polyurethane composition.
- Preferred packages of this kind are, on the one hand, side-by-side double cartridges or coaxial cartridges, in which two tubular chambers are arranged side by side or one inside the other and are sealed in air and moisture-tight manner with pistons.
- the components K1 and K2 are advantageously filled and stored in barrels or pails.
- the components are conveyed via feed pumps via lines
- any package it is important that at least the polyisocyanate component K2 be sealed in a hermetic and moisture-proof manner, so that both components remain stable over a long period, i. typically longer than 6 months, storable.
- the invention includes a method of bonding.
- the method of bonding comprises the following steps:
- the mixing is typically done by static mixers or by means of dynamic mixers.
- the mixed polyurethane composition is applied to at least one of the substrate surface to be bonded.
- the substrate to be bonded preferably comprises or consists of a biodegradable material.
- biodegradable is used in the present
- the substrate to be bonded preferably comprises or consists of an organic material, preferably a renewable one
- organic material more preferably a polysaccharide such as starch or cellulose based material or
- renewable raw materials based polyester material Preferably, it is a cellulose fiber fleece, paper or wood.
- Other possible substrates are metal, plastic, glass or ceramic or fiber-reinforced plastics.
- the joining partner i. the second substrate is identical or different from the first substrate.
- the adhesive application can take place on the first and / or the second joining partner. After adhesive application, the joining partners are joined within the open time.
- the substrates consist of more than 80% by weight of biodegradable material.
- Such an article is another aspect of the invention.
- the polyurethane composition is preferably as structural
- Adhesive used therefore comprises the use of a two-component polyurethane composition as an adhesive, in particular as a structural adhesive.
- a two-component polyurethane composition as an adhesive, in particular as a structural adhesive.
- a hydrolytically degradable adhesive in particular as a hydrolytically degradable structural adhesive.
- such a structural adhesive in the cured state at room temperature has a tensile strength of> 5 MPa, in particular of> 6 MPa.
- a structural adhesive in the cured state at room temperature has an elongation at break of> 30%, in particular of> 60%.
- a structural adhesive in the cured state preferably has an E-modulus of> 10 MPa at room temperature.
- the cured adhesive is part of a supporting structure and thus forms an important link on whose mechanical properties high demands are made.
- the present invention meets these high standards perfectly.
- the polyurethane composition of the invention is characterized by a hydrolytic degradability, preferably a controlled hydrolytic degradability.
- compositions 2-6 and 11-14 exemplified in Table 1 are examples according to the invention, while the others are reference examples.
- Weight ratio A1 / A2 gravimetrically weighed and mixed in a SpeedMixer® (DAC 150 FV, Hauschild) for 30 seconds at 3000 rpm.
- SpeedMixer® DAC 150 FV, Hauschild
- Example 50 in addition to component A1, non-inventive component A1 "in weight ratio A1 / A1" of 75/20 was also added.
- the components K2 (B1 -1, B1 -2, or the non-inventive ⁇ ', B “, ⁇ '", B “") according to Table 2 were weighed gravimetrically to the components K1 and 30 seconds in the SpeedMixer at 3000 rpm mixed.
- the components K1 and K2 were mixed in the weight ratio of K1: K2 so that in each case an NCO / OH ratio of 1 .07 resulted.
- the cured curing composition was poured into 20 cm diameter Teflon dishes and sampled with a thickness of 2 mm.
- Example 2 the raw materials used (and those listed in Table 1) are marked by an "X", which were mixed as described above for Examples 1-50, For example, to prepare Example 2, 65.3 g of castor oil, 1.36 g 1, 2,3-propanetriol and 33.7 g MDI
- Examples 7-9 gave a brittle foam from which no samples could be made. In the case of Examples 15-24 and 30-34, it was not possible to obtain a cured product within a period of 7 days and to prepare test pieces therefrom.
- Table 3 examples in which a specimen (P.k.) was prepared were marked with a (+). Examples in which no specimen (P.k.) was produced are marked with a (-).
- the mixed components K1 and K2 were dumbbell-shaped according to ISO 527, Part 2, 1 B and cured for 24 h at 25 ° C and then for 3 h at 80 ° C.
- the blended components K1 and K2 were laminated to isopropyl alcohol degreased KTL-coated steel (ZSF1) 20 minutes after blending, respectively, to polyester material extruded into sheets (Ecoflex, Ecoflex F BX 701 1, BASF Germany (ZSF2) or Ecovio, Ecovio L BX 8145, BASF Germany (ZSF3)), in a layer thickness of 2.0 mm and applied to an overlapping adhesive surface of 20 x 45 mm and for 7 days at 23 ° C. and 50% humidity cured.
- the tensile shear strength was determined at a temperature of 23.0 ° C with a test speed of 20 mm / min according to DIN EN 1465. The results are shown in Table 3.
- the hydrolytic degradation was carried out on samples with a thickness of 2 mm and a diameter of 20 mm in demineralised water at 40 ° C over a period of 60d.
- the samples to be examined were dried after removal from the water at 40 ° C and under vacuum until constant weight was reached.
- the results can be found in Tables 4-6. The values refer to the weight of the sample in% of
- A2 '1 1, 1-trimethylolpropane (also called trimethylolpropane or 2- (hydroxymethyl) -2-ethylpropane-1,3-diol)
- Desmodur® VKS 20 Bayer Material Science, (including 1% by weight of catalyst * )
- organometallic catalyst based on bismuth and zinc neodecanoate, 35% solution.
Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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EP13763008.3A EP2895520A1 (en) | 2012-09-14 | 2013-09-06 | Two-component polyurethane compositions, in particular suitable for use as viscoplastic structural adhesives |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP12184554.9A EP2708565A1 (en) | 2012-09-14 | 2012-09-14 | Dual component polyurethane compounds on the basis of renewable resources, particularly suitable for use as tough elastic adhesives with adjustable hydrolytic degradability |
EP13763008.3A EP2895520A1 (en) | 2012-09-14 | 2013-09-06 | Two-component polyurethane compositions, in particular suitable for use as viscoplastic structural adhesives |
PCT/EP2013/068433 WO2014040916A1 (en) | 2012-09-14 | 2013-09-06 | Two-component polyurethane compositions, in particular suitable for use as viscoplastic structural adhesives |
Publications (1)
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EP2895520A1 true EP2895520A1 (en) | 2015-07-22 |
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Application Number | Title | Priority Date | Filing Date |
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EP12184554.9A Withdrawn EP2708565A1 (en) | 2012-09-14 | 2012-09-14 | Dual component polyurethane compounds on the basis of renewable resources, particularly suitable for use as tough elastic adhesives with adjustable hydrolytic degradability |
EP13763008.3A Withdrawn EP2895520A1 (en) | 2012-09-14 | 2013-09-06 | Two-component polyurethane compositions, in particular suitable for use as viscoplastic structural adhesives |
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EP12184554.9A Withdrawn EP2708565A1 (en) | 2012-09-14 | 2012-09-14 | Dual component polyurethane compounds on the basis of renewable resources, particularly suitable for use as tough elastic adhesives with adjustable hydrolytic degradability |
Country Status (6)
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US (1) | US9809732B2 (en) |
EP (2) | EP2708565A1 (en) |
JP (1) | JP6235593B2 (en) |
CN (1) | CN104755519B (en) |
BR (1) | BR112015005679A2 (en) |
WO (1) | WO2014040916A1 (en) |
Families Citing this family (10)
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EP2708566A1 (en) * | 2012-09-14 | 2014-03-19 | Sika Technology AG | Dual component polyurethane compounds, particularly suitable for use as tough elastic structural adhesives or sealing compounds |
US20170334183A1 (en) * | 2015-03-20 | 2017-11-23 | Dic Corporation | Solvent-free laminating adhesive, cured product of same, polyol composition for lamination adhesives, and multilayer film |
JP6820280B2 (en) | 2015-06-18 | 2021-01-27 | ダウ グローバル テクノロジーズ エルエルシー | Potential two-component polyurethane adhesive that can be cured by infrared radiation |
EP3339343A1 (en) * | 2016-12-23 | 2018-06-27 | Sika Technology Ag | Two-component polyurethane composition |
EP3415544A1 (en) * | 2017-06-12 | 2018-12-19 | Sika Technology Ag | Two-component polyurethane composition |
WO2019013917A1 (en) | 2017-07-11 | 2019-01-17 | Dow Global Technologies Llc | Three-component polyurethane adhesive compositions |
FR3075214B1 (en) * | 2017-12-19 | 2019-12-27 | Bostik Sa | BI-COMPONENT POLYURETHANE ADHESIVE FOR LAMINATION |
EP3732222B1 (en) * | 2017-12-27 | 2022-08-17 | Dow Global Technologies LLC | Two-component solventless adhesive compositions for adhesion to polymeric barrier substrates |
CN111379045B (en) * | 2020-05-15 | 2022-07-26 | 中原工学院 | Elasticity-controllable spandex and preparation method thereof |
JP2023092738A (en) * | 2021-12-22 | 2023-07-04 | 中央発條株式会社 | flocked spring |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
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JPS59197466A (en) * | 1983-04-25 | 1984-11-09 | Dai Ichi Kogyo Seiyaku Co Ltd | Coating composition for metal |
JPS60147426A (en) * | 1984-01-13 | 1985-08-03 | Mitui Toatsu Chem Inc | Curable composition |
JPS60166353A (en) * | 1984-02-09 | 1985-08-29 | Dai Ichi Kogyo Seiyaku Co Ltd | Polyurethane metal corrosion-proof coating composition |
US4877829A (en) * | 1988-05-19 | 1989-10-31 | W. R. Grace & Co.-Conn. | Liquid coatings for bridge deckings and the like |
US4870142A (en) * | 1988-06-07 | 1989-09-26 | Genesco Inc. | Novel urethane polymer alloys with reactive epoxy functional groups |
DE4401572B4 (en) * | 1994-01-20 | 2006-07-06 | Henkel Kgaa | Two-component polyurethane adhesives with improved adhesion |
DE10108025A1 (en) | 2001-02-19 | 2002-09-05 | Henkel Kgaa | Two-component polyurethane adhesive for wood materials |
JP2002249745A (en) * | 2001-02-27 | 2002-09-06 | Mitsui Takeda Chemicals Inc | Two-part curable solventless adhesive composition |
EP1690880A1 (en) | 2005-02-11 | 2006-08-16 | Sika Technology AG | Two component polyurethane compositions, especially suitable for use in structural adhesives |
US7538236B2 (en) * | 2006-01-04 | 2009-05-26 | Suresh Narine | Bioplastics, monomers thereof, and processes for the preparation thereof from agricultural feedstocks |
EP2708566A1 (en) * | 2012-09-14 | 2014-03-19 | Sika Technology AG | Dual component polyurethane compounds, particularly suitable for use as tough elastic structural adhesives or sealing compounds |
-
2012
- 2012-09-14 EP EP12184554.9A patent/EP2708565A1/en not_active Withdrawn
-
2013
- 2013-09-06 CN CN201380056316.6A patent/CN104755519B/en not_active Expired - Fee Related
- 2013-09-06 WO PCT/EP2013/068433 patent/WO2014040916A1/en active Application Filing
- 2013-09-06 US US14/428,190 patent/US9809732B2/en not_active Expired - Fee Related
- 2013-09-06 EP EP13763008.3A patent/EP2895520A1/en not_active Withdrawn
- 2013-09-06 JP JP2015531521A patent/JP6235593B2/en not_active Expired - Fee Related
- 2013-09-06 BR BR112015005679A patent/BR112015005679A2/en not_active IP Right Cessation
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None * |
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US20150247073A1 (en) | 2015-09-03 |
US9809732B2 (en) | 2017-11-07 |
BR112015005679A2 (en) | 2017-07-04 |
JP6235593B2 (en) | 2017-11-22 |
CN104755519A (en) | 2015-07-01 |
JP2015535862A (en) | 2015-12-17 |
EP2708565A1 (en) | 2014-03-19 |
CN104755519B (en) | 2017-06-20 |
WO2014040916A1 (en) | 2014-03-20 |
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