WO2012141675A1 - Rosin esters for non-wovens - Google Patents
Rosin esters for non-wovens Download PDFInfo
- Publication number
- WO2012141675A1 WO2012141675A1 PCT/US2011/031884 US2011031884W WO2012141675A1 WO 2012141675 A1 WO2012141675 A1 WO 2012141675A1 US 2011031884 W US2011031884 W US 2011031884W WO 2012141675 A1 WO2012141675 A1 WO 2012141675A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- rosin
- rosin ester
- pentaerythritol
- less
- relative
- Prior art date
Links
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- 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 title claims abstract description 188
- 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 title claims abstract description 188
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F1/00—Obtaining purification, or chemical modification of natural resins, e.g. oleo-resins
- C09F1/04—Chemical modification, e.g. esterification
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L93/00—Compositions of natural resins; Compositions of derivatives thereof
- C08L93/04—Rosin
-
- 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
- C09J193/00—Adhesives based on natural resins; Adhesives based on derivatives thereof
- C09J193/04—Rosin
Definitions
- the present invention relates to rosin esters, to products made from or comprising rosin esters, and to methods of making and using such rosin esters or products.
- the present invention relates to rosin esters useful for non-woven applications, to non-woven products made from and/or comprising rosin esters, and to methods of making and using such rosin esters and products.
- the present invention relates to rosin esters having suitable color, color stability and/or odor to make them useful for non- woven applications, to non-woven products made from and/or comprising rosin esters, and to methods of making and using such rosin esters and products.
- rosin esters are not acceptable for the non-woven adhesives industry.
- hydrogenated hydrocarbon resin based tackifiers are most commonly accepted for utilization in non-woven applications.
- the main ones are presently that previous and current tall oil rosin based rosin esters neither have the color, color stability nor the low odor for use in non-woven adhesives.
- U.S. Patent No. 4,302,371 discloses a stabilized rosin ester and pressure-sensitive adhesive and hot-melt composition based thereon.
- the process for preparing a stabilized rosin ester having a higher softening point comprises subjecting a rosin to disproportionation and purification, and esteri tying the resulting purified disproportionated rosin with a tri- or more valent polyhydric alcohol to give a rosin ester having a softening point (according to ring and ball method) of 65. degree, to 140.degree. C.
- the resulting rosin ester has superior heat resistance and aging resistance as well as a high softening point and is suitably employed as a tackifier for pressure-sensitive adhesive compositions and hot-melt compositions.
- U. S. Patent No. 4,643,848, issued February 17, 1987, to Thomas , et al discloses a modified rosin ester preparation.
- Phosphinic acid also called hypophosphorous acid
- a rosin is reacted with an unsaturated dibasic acid such as maleic anhydride or fumaric acid in the presence of phosphinic acid at a temperature of from about ISO.degree. C. to about
- the modified rosin ester exhibits improved color, softening point, and viscosity in a specified solution.
- U. S. Patent No. 4,657,703, issued April 14, 1987, to Durkee discloses a method of improving the color of tall oil rosin esters.
- the method of improving the color of tall oil rosin esters comprises the sequential steps of (a) heating and stirring a tall oil rosin in the presence of a Lewis acid catalyst to form a mixture, (b) distilling the mixture to provide a tall oil rosin distillate, and (c) esterifying the tall oil rosin distillate with a polyol in the presence of a phenol sulfide compound.
- the improved tall oil rosin esters produced thereby are useful in the manufacture of a variety of products, such as paper and textile sizes, plasticizers for polyolefin films, paints, varnishes, hot melt adhesives and pressure sensitive adhesives.
- the catalytic combination of a phosphite ester and a phenol sulfide accelerates and mediates the esierificaiion reaction of rosin with a polyhydric alcohol, resulting in estenfied rosins having numerous advantageous characteristics and particular utility as tackifiers in hot melt adhesives.
- U. S. Patent No. 5,504, 52, issued April 2, 1996, to Schluenz , et al. discloses esterification of rosin.
- the method for esterifying rosins with a polyol which comprises contacting rosin with the polyol in the presence of a bleaching mixture which includes both an alkaline earth hypophosphite and hypophosphorous acid and, preferably also, an organic sulfide, under esterification conditions to produce a rosin ester.
- the method enables production of rosin esters which have a color of less than about 5 Gardner neat.
- the preferred bleaching mixture includes from about 0.01% to about 0.10% of the alkaline earth hypophosphite and from about 0.10% to about 0.15% of active hypophosphorous acid, where the amounts are based on the weight of the rosin.
- the most preferred alkaline earth hypophosphite is calcium hypophosphite.
- the specification also describes a method for preparing an adhesive from the rosin ester.
- U. S. Patent No. 5,969,092, issued October 19, 1999, to Karvo discloses preparation of a tall oil rosin ester with a low odor level.
- This process for the preparation of a tall oil rosin ester with a low odor level comprises an esterification step wherein a tall oil rosin is esterified with a polyol in order to form a product which contains a tall oil rosin ester, and evaporation is carried out on this product in order to remove odor components and other volatile components from the product, which evaporation is carried out in a short-path evaporator which has an evaporation surface and, in the vicinity of this surface, a condenser on which the vaporized components to be removed condense, whereupon a tall oil rosin ester with a low odor level is recovered from the evaporator.
- U. S. Patent No. 6,562,888 issued May 13, 2003, to Frihart, et a!., discloses light-colored rosin esters and adhesive compositions. These rosin esters are both light- colored and color stable may be produced by reacting rosin with an organic compound containing two or more hydroxyl groups each separated from each other by at least four carbon atoms. With appropriate choices for the esterification catalyst and antioxidant(s), the rosin ester may be useful as a tackifier, and can be formulated into an adhesive composition.
- the adhesive compositions will further comprise an appropriate adhesive polymer.
- 20070179277 pubished August 2, 2007, both to Anthony Dallavia disclosed a rosin ester with low color and process for preparing same.
- the process for producing light color rosins ester resin, preferably based on tall rosin is conducted in the presence of less than 10 weight % of an acid functional organic compound and avoids the need for use of a stoichiometric excess of rosin acid, or a stoichiometric excess of polyol hydroxy groups.
- the process allows for the use of lower colored or darker tall oil rosin in the production of low color rosin esters.
- EVA packaging adhesives that give increased viscosity stability to the adhesive.
- PSA pressure sensitive adhesives
- the method may include any one or more of the following steps in any order: contacting a rosin having PAN isomers with disproportionation agent to provide a rosin having a PAN number less than 45 providing a disproportionated rosin; contacting the disproportionated rosin with an adduction agent to further reduce the PAN number to provide an adducted rosin; and/or contacting the adducted rosin with a poiyhydric polyol to form a rosin ester.
- a method of producing a rosin ester may include one or more of the following steps in any order: contacting rosin having a PAN number less than 45 with an adduction agent to further reduce the PAN number to provide an adducted rosin; contacting the adducted rosin with a polyhydric polyol to form a rosin ester.
- a rosin ester composition having an odor intensity of less than 80% relative to comparison rosin ester made from 100% pentaerythritol.
- an adhesive comprising a rosin ester composition having an odor intensity of less than 80% relative to comparison rosin ester made from 100% pentaerythritol.
- a non-woven product comprising an adhesive comprising a rosin ester composition having an odor intensity of less than 80% relative to comparison rosin ester made from 100% pentaerythritol.
- rosin esters with lower odor, lighter color, and/or improved color stability compared to prior art technology.
- Certain embodiments of the rosin ester compositions of the present invention have substantially improved color stability at temperatures up to 150C and/or these compositions impart excellent thermal stability to a hot melt adhesive upon aging at temperatures up to 150C.
- These certain resulting rosin esters are suitable for use in conventional packaging and pressure sensitive adhesives, and unlike conventional rosin esters it can also be used for odor and color sensitive applications such as non-woven adhesives (diaper construction adhesives) or other high-end packaging adhesives.
- one non-limiting embodiment of the present invention provides fumaric-niodified esters based upon a polyol component that may be a blend of polyols, a non-limiting example of which includes glycerol and PE. Some of the embodiments may provide lighter color and lower odor as compared to commercial SYLVALITETM Rosin Ester and may also provide superior color stability and viscosity stability upon aging or storage at elevated temperatures simulating warehouse conditions. [00041] Some of the embodiments of the present invention will provide an adhesive with the lower initial color and lower aged color as compared to commercial adhesives. Some of the embodiments of the present invention provide smaller viscosity change on aging as compared to commercial adhesives. As a non-limiting example, the viscosity change of adhesives made from some embodiments of the rosin esters of the present invention may be less than 5%, 4%, 3%, 2% or 1%, after aging for 96 hours at 350F.
- Some embodiments of the present invention may utilize a partial disproportion step. It was also noticed that the rosin color may decreases during this step, although the final ester may not necessarily be unusually light in color.
- Disproportionation agents may fall into several classes. Some embodiments of the present invention utilize phenol sulfide type of agents. As specific non-limiting examples, OSINOXTM (poJy-t-butyJphenoldisulfide available from Arkema, Inc.), LOWINOXTM TBM-6 (4,4'-thiobis(2-t-butyi-5-methylphenol available from Chemtura), ETHANOXTM 323 (nonylphenol disulfide oligomer available from Albemarle Corp.), and/or VULTACTM 2 (amylphenol disulfide polymer available from Sovereign Chemical Co.).
- OSINOXTM poJy-t-butyJphenoldisulfide available from Arkema, Inc.
- LOWINOXTM TBM-6 4,4'-thiobis(2-t-butyi-5-methylphenol available from Chemtura)
- ETHANOXTM 323 nonylphenol disulfide oligomer available from
- Suitable disproportionation agents include thiobisnaphthols in general. Suitable non-limiting examples include but are not limited to 2,2'-thiobis phenols, 3.3 ! -thiobisphenols, 4,4'-thiobis(resorcinol) and t,t'-thiobis(pyrogalloi), 4,4'-thiobis(6-t-butyl-m-cresoi) and 4/4'-thiobis(6-t-butyl-o-cresol) thiobisnaphthols, 2,2'- thio-bis phenols, 3,3'-thio-bis phenols, and the like.
- Suitable disproportionation agents incl de metals include but are not limited to palladium, nickel, platinum ) or iodine or iodides (a non limiting ex ample of which includes but is not limited to iron iodide) or sulfides (a non limiting example of which includes but is not limited to like iron sulfide).
- the rosin prior to disproportionation may have a PAN number on the order of about 50.
- the PAN number is the sum of the percentage of rosin acids in the rosin that are Palustric Acid, Abietic Acid, and Neoabietic Acid.
- disproportionation will result in a final PAN number from about 20 - 25. In other embodiments of the present invention
- disproportionation will result in a final PAN number from 10 - 40.
- Disproportionation may result in a final PAN number that is 0.1, 1, 2, 5, 10, 15, 20, 25, 35, 35, 40, or 45, or in any range from/to or between any two of the foregoing numbers.
- Some embodiments of the present invention exhibit color improvement in disproportionated rosin and improved oxidation resistance of esters made from such rosin combined with the discovery that a fumaric acid adducted glyceroL'pentaerythritol ester may exhibit improved odor and color stability.
- Certain embodiments of the present invention may provide a suitable low odor light color rosin ester that may be suitable for use in non-woven adhesives by implementing a proper combination of process and synthetic conditions.
- rosin esters may be prepared from rosin, catalyst(s), bleaching agent(s), polyhydric alcohol(s) also as known as a polyols, and a stabilizer and/or antioxidant.
- catalyst, stabilizers and/or bleaching agents are known is the art as described, for example, in U.S. Pat. Nos. 2729660, 3310575, 3423389, 3780013, 4172070, 4548746, 4690783, 4693847, 4725384, 4744925, 4788009, 5021548 and 5049652.
- the process for making the rosin esters of the present invention may include contacting a rosin, preferably a molten rosin, with a polyhydric alcohol.
- Suitable examples of rosins useful in the process of the invention may include but are not limited to gum rosin, wood rosin or tall oil rosin or any subsets or mixtures thereof.
- the preferred rosin is tall oil rosin.
- the tall oil rosin may be an isomeric mixture primarily composed of C20 fused-ring, monocarboxylic acid
- hydrocarbons may be typified by levopimaric acid, abietic acid, pimaric acid and dehydroabietic acid.
- the amount of rosin used will vary depending on the end use application.
- the gum. wood, tall oil and other rosins may be employed in the processes of the present invention as is, or alternatively may be subjected to other treatments prior to use in the present esterification process.
- the rosin material may be subjected to distillation, disproportionation, hydrogenation or polymerization, or some combination of these and/or other treatments, prior to use in the subject processes.
- Polyhydric alcohols also sometimes referred to as polyols, the other reactant employed in the subject process, are also well known.
- exemplary of such compounds are ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, trimethylene glycol, glycerol, pentaerythritoL dipentaerythritol, tripentaerythritol, irimethylolethane, trimethylolpropane, mannitol and sorbitol.
- Some embodiments of the present invention may utilize combinations of 2 or more of the above.
- some embodiments may utilize combinations of two or more of glycerol, pentaerythritol, and trimethylolpropane.
- Some embodiments of the present invention will utilize a polyol combination of pentaerythritol and at least 1 , 2, 3, 4, 5 or more other polyols, a non-limiting example of which includes pentaerythritol and at least one of glycerol or trimethylolpropane (TMP).
- the combination may be added as a mixture of the pentraeythritol and the other polyol(s), or may the combination may be added as a sequential additional of the pentraeythritol followed by the other polyol(s), or the one or more of the polyol) s) followed by the pentraeythritol.
- some embodiments of the present invention may utilize a sequential addition of
- pentaerythritol followed by at least 1, 2, 3, 4, 5 or more other polyols non-limiting example of which include pentaerythritol followed by glycerol, pentaerythritol followed by trimethylolpropane, pentraeythriol followed by glycerol then trimethylolpropane, pentraeythriol followed by trimethylolpropane then glycerol, or pentraeythriol followed by a mixture of glycerol and trimethylolpropane.
- Some embodiments of the present invention may utilize the addition of a mixture of pentaerythritol and glycerol, a mixture of pentraeythriol and trimethylolpropane, or a mixture of pentraeythriol, glycerol and trimethylolpropane.
- Some embodiments of the present invention will utilize a combination of a glycerol and/or trimethylolpropane and at least ⁇ , 2, 3, 4, or 5 other polyols.
- the combination may be added as a mixture of the glycerol and/or trimethylolpropane and the other polyol(s), or may the combination may be added as a sequential additional of the glycerol and/or trimethylolpropane followed by the other polyol(s), or the one or more of the polyol(s) followed by the glycerol
- some embodiments of the present invention may utilize a sequential addition of glycerol and/or trimethylolpropane at least 1, 2, 3, 4, 5 or more other polyols followed by the glycerol, a non-limiting example of which includes glycerol followed by pentaerythritol, trimetliylolpropane followed by peniaerythritol, or gly
- the polyol combinations described above may comprise weight percent pentaerythritol (based on the total weight of the polyols in the combination) at or below 0, 0.001, 0.01, 0.1, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 17.5, 20, or in any range from/to or between any two of the foregoing numbers.
- the amount of the alcohol employed in the esterification process may be varied widely. Generally, however, at least about an equivalent amount of polyhydric alcohol, based on the amount of rosin, is employed, with the upper limit generally being about 50% excess over the equivalent.
- the rosin may be subjected to an adduction step prior to contracting the alcohol.
- the adduction agents may be selected to react most readily with the PAN isomers of the rosin through a Diels-Alder reaction or an Ene reaction.
- suitable adduction agents include, but is not limited to, unsaturated acids or their equivalents like anhydrides.
- a sufficient amount of PAN isomers may be present in the rosin after the disproportionation step to allow reaction with the adduction agent.
- a sufficiently low PAN isomers may be required as too many unreacted PAN acid isomers (either free acids or esterified acids) present in the final rosin ester may in some circumstances lead to poor oxidation stability upon storage which may result in poor color stability and poor odor.
- Non-limiting examples of suitable PAN numbers for rosin to be subjected to adduction include 0.1 , 1, 2, 5, 10, 15, 20, 25, 35, 35, 40, or 45, or in any range from/to or between any two of the foregoing numbers.
- suitable ranges includes but is not limited to, 20 25, 15 - 30, and 10 - 40.
- Non-limiting examples of suitable adducting agents include but are not limited to furnaric acid, maleic anhydride, acrylic acid, and other unsaturated acids or their equivalents like anhydrides.
- the adduction step is may be utilized to further reduce the level of the PAN rosin isomers left after the disproportionation.
- the adduction step may increase the molecular weight and the softening point of the rosin ester. In some embodiments, this may allow replacement of pentaerythritol (PE) with other polyols like glycerol or TMP that may provide lower odor esters but may also have lower softening points than PE esters.
- PE pentaerythritol
- a furnaric acid adducted glycerol ester may have a similar softening point to a PE ester and may be used for similar applications but may possess greater oxidation resistance and a lower odor.
- a partial disproportionation step may further increase the oxidation resistance and may lower the odor of the final rosin ester.
- the higher levels of fumaric acid provide lower odor rosin esters as judged by our odor panel when compared to a standard commercial PE rosin ester.
- the adduction agent may be utilized at or above 0.1, 1 , 1.5, 2, 2.5, 3, 3.5, 4, 4.5, 5, 5.5, 6, 10, 20, 30 weight percent of the formulation, or in any range from/to or between any two of the foregoing numbers.
- the fumaric acid levels of about 2 - 2.8% of the formulation raises the weight average molecular weight Mw of the resultant rosin ester to about 1200 - 1600 Daltons as compared to about 900 - 1000 Daltons for a PE rosin ester.
- 2.4 - 2.8% fumaric acid may be desired.
- Some embodiments of the rosin ester may exhibit reduced odor intensity when compared to PE rosi esters.
- the odor intensity of certain embodiments of rosin esters (which utilize less then 100% PE), will have relative intensities (relative to rosin esters utilizing 100% PE) that are at or below 80%, 75%, 65%, 60%, 55%, 50%, 45%, 40%, 35%, 30% of rosin esters utilizing 100% PE, or in any range from/to or between any two of the foregoing numbers.
- the odor intensity is determined as shown below in the Examples.
- Some embodiments of the rosin esters of the present invention may find use as tackifier resins in hot melt adhesives and as binding resins in low color, overprint varnishes used in the printing, for example, high gloss magazines, advertising and corporate annual reports.
- TNPP tris-(nonylphenyl) phosphite
- a reactor sample had an 85.2°C softening point, a 24.5 acid number, and a 2 neat Gardner color.
- the reaction was heated to 275°C and sparged with nitrogen for 4 hours.
- the reaction was next cooled and 0.14 g. of 50% aq. KOH, 0.99 g. of irganox l M 1010, and 0.35 g of IrganoxTM 565 were added.
- the 200°C resin was poured into pans to cool.
- samples D and E had the highest fumaric acid content
- Table 2 shows odor panel data on test resin formulations made with a constant 2% fumarie acid (FA) adduction and consistent process conditions but with varying levels of peniaerythritol replacing some of the glycerol.
- Table 3 shows the high oxidation resistance of certain embodiments of the present inventive with the disproportionation step included in the process.
- the inventive tackifier resins especially favored formulations C and D, showed much less color darkening than the control.
- disproportionation provides a resin ester having properties more desirable in some circumstances.
- certain embodiment of the present inventive tackifier resins showed better color than in the control.
- DSC differential Scanning Calorimetry. In oxidative DSC the sample is heated under oxygen pressure at 128°C until the sample oxidizes as shown by its heat emission.
- EVA ethylene vinyl acetate copolymer
- Table 4 shows an odor comparison made between a commercial SIS / hydrogenated hydrocarbon resin tackified adhesive and SIS adhesives made with rosin ester tackifiers.
- adhesives made with a top grade of commercially available (Arizona Chemical) pentaerythritol rosin ester and adhesives made certain embodiments of the present inventive ester without the disproportionation step showed similar or stronger odors than the commercial adhesive.
- adhesives made with sample resins from certain embodiments of the present invention were judged by an odor panel to have a significantly lower odor than the commercial SIS adhesive.
- Table 4 Odor comparison of SIS Adhesives using New Rosin Ester Tackifiers '
- Rosin ester C from certain embodiments of the present invention was also evaluated in a standard pressure-sensitive adhesive formulation based on Styrene-Isoprene- Styrene (SIS) for label applications. The results were compared to those obtained for a standard commercial rosin ester, SYLVALITE' M Rosin Ester. The results are shown in Table 5. Although the rosin ester of the invention exhibited a lower loop tack, overall it performed comparably or better than the commercial rosin ester; and therefore would be expected to be an acceptable tackifier for such adhesives.
- SIS Styrene-Isoprene- Styrene
- Rosin ester C from the present invention was also evaluated in a standard hot melt packaging adhesive formulation based on EVA , The results of the thermal stability (Color and viscosity stability) were compared to those obtained for a standard commercial rosin ester, SYLVALITETM Rosin Ester, The results are shown in Table 6.
- the adhesive made with the rosin ester of the invention exhibited comparable stability to the commercial product; and therefore the rosin ester of this invention would be expected to be an acceptable tackifier for such ad!iesives.
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Abstract
Description
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KR1020137029360A KR20140022059A (en) | 2011-04-11 | 2011-04-11 | Rosin esters for non-wovens |
JP2014505109A JP2014517091A (en) | 2011-04-11 | 2011-04-11 | Rosin ester for nonwovens |
BR112013026297A BR112013026297A2 (en) | 2011-04-11 | 2011-04-11 | nonwoven rosin resin esters |
AU2011365712A AU2011365712A1 (en) | 2011-04-11 | 2011-04-11 | Rosin esters for non-wovens |
CA2833114A CA2833114A1 (en) | 2011-04-11 | 2011-04-11 | Rosin esters for non-woven applications, methods of making and using and products therefrom |
RU2013145603/05A RU2569081C2 (en) | 2011-04-11 | 2011-04-11 | Colophony ethers for nonwoven materials |
CN201180070558.1A CN103517957B (en) | 2011-04-11 | 2011-04-11 | Rosin esters for non-wovens |
EP11863683.6A EP2697322A4 (en) | 2011-04-11 | 2011-04-11 | Rosin esters for non-wovens |
PCT/US2011/031884 WO2012141675A1 (en) | 2011-04-11 | 2011-04-11 | Rosin esters for non-wovens |
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- 2011-04-11 WO PCT/US2011/031884 patent/WO2012141675A1/en active Application Filing
- 2011-04-11 BR BR112013026297A patent/BR112013026297A2/en not_active IP Right Cessation
- 2011-04-11 AU AU2011365712A patent/AU2011365712A1/en not_active Abandoned
- 2011-04-11 CN CN201180070558.1A patent/CN103517957B/en not_active Expired - Fee Related
- 2011-04-11 CA CA2833114A patent/CA2833114A1/en not_active Abandoned
- 2011-04-11 EP EP11863683.6A patent/EP2697322A4/en not_active Withdrawn
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Also Published As
Publication number | Publication date |
---|---|
CN103517957B (en) | 2015-06-10 |
BR112013026297A2 (en) | 2017-06-06 |
EP2697322A4 (en) | 2015-08-05 |
EP2697322A1 (en) | 2014-02-19 |
RU2569081C2 (en) | 2015-11-20 |
JP2014517091A (en) | 2014-07-17 |
AU2011365712A1 (en) | 2013-10-31 |
RU2013145603A (en) | 2015-05-20 |
KR20140022059A (en) | 2014-02-21 |
CA2833114A1 (en) | 2012-10-18 |
CN103517957A (en) | 2014-01-15 |
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