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( 12 ) United States Patent US009902815B2 (12 ) United States Patent ( 10 ) Patent No. : US 9 ,902 , 815 B2 Tamminen et al. ( 45 ) Date of Patent: Feb . 27 , 2018 ( 54 ) FUNCTIONALIZED LIGNIN AND METHOD ( 58 ) Field of Classification Search OF PRODUCING THE SAME ??? . .. C07G 1 / 00 See application file for complete search history . @(71 ) Applicant : Teknologian tutkimuskeskus VTT , VTT (FI ) ( 56 ) References Cited U . S . PATENT DOCUMENTS @(72 ) Inventors : Tarja Tamminen , Espoo (FI ) ; Jarmo Ropponen , Espoo (FI ) ; Eva - Lena Hult , 2 ,429 , 102 A 10 / 1947 Lewis et al. Espoo ( FI) ; Kristiina Poppius- Levlin , 3 , 149 , 085 A 9 / 1964 Ball et al . Espoo (FI ) 4 ,017 ,430 A * 4 / 1977 Briggs .. .. .. 530 / 502 5 ,773 , 590 A * 6 / 1998 Hart 530 / 500 6 ,172 ,204 B1 * 1 /2001 Sarkanen et al. 530 /500 @(73 ) Assignee : Teknologian tutkimuskeskus VTT Oy, 2010 /0105798 A1 * 4 /2010 Hasegawa . .. .. 522 / 99 Espoo (FI ) 2010 /0152428 A1* 6 / 2010 Gifford et al . .. .. .. 530 / 504 2010 / 0204368 A1 * 8 / 2010 Benko et al. .. .. .. .. .. .. .. 524 / 73 ( * ) Notice : Subject to any disclaimer, the term of this 2010 / 0331531 A1 * 12 / 2010 Mykytka .. .. 530 / 501 patent is extended or adjusted under 35 2011/ 0263836 A1 * 10 / 2011 Vuorenpalo et al. .. .. 530 / 500 U . S . C . 154 ( b ) by 33 days. 2012 /0012035 A1 * 1 / 2012 Blank et al. .. .. 106 / 802 ( 21) Appl. No. : 14 /348 , 904 OTHER PUBLICATIONS (22 ) PCT Filed : Oct. 8 , 2012 Holmbom ( Journal of the American Oil Chemists Society , 1977 , p . 289 - 293 ) . * Stenberg et al . (Surface Coatings International Part B : Coatings ( 86 ) PCT No. : PCT/ FI2012 /050965 Transactions , vol. 88 , B2 , 83 - 156 , 2005 ) . * $ 371 ( c ) ( 1 ) , Antonsson , Stefan . The use of lignin derivatives to improve selected paper properties . Licenciate Thesis , Stockholm : Royal Institute of ( 2 ) Date : Apr. 1, 2014 Technology , 2007 . (87 ) PCT Pub. No. : W02013 /050661 * cited by examiner PCT Pub . Date : Apr. 11 , 2013 Primary Examiner — Liam J Heincer (65 ) Prior Publication Data (74 ) Attorney , Agent, or Firm — Seppo Laine Oy US 2014 / 0243511 A1 Aug . 28 , 2014 (57 ) ABSTRACT In this study, commercially available softwood lignin was esterified with tall oil fatty acid ( TOFA ) and tested as barrier Related U . S . Application Data material in fiber -based packaging material . The modified (60 ) Provisional application No. 61/ 544 , 303 , filed on Oct . lignin samples were applied with a bar coater forming an 7 , 2011 . even coating on the paperboard substrate . A significant decrease in WVTR and OTR value was observed for paper ( 51 ) Int. Cl. board coated with the modified lignin as well as pure TOFA CO7G 1 /00 ( 2011. 01 ) used as a reference . In contrast to the TOFA coating , the C08H 7700 ( 2011 . 01 ) modified lignin coatings exhibited a high and stable contact C09D 197 / 00 (2006 .01 ) angle . The coating material did not affect the tensile strength CO9J 197 / 00 ( 2006 . 01 ) of the paperboard . According to the results , the demonstra C08L 97 / 00 ( 2006 .01 ) tion of the conversion of lignin into a value added product D21H 17 / 23 ( 2006 .01 ) has been shown. Furthermore , the novel coating material (52 ) U . S . CI. shows promising properties for the development as sustain CPC . .. C08H 6 / 00 (2013 . 01 ) ; COZG 1/ 00 able barrier material in fiber -based packaging material to ( 2013 .01 ) ; C08L 97 /005 ( 2013 .01 ) ; C09D replace oil - placed barriers . 197/ 005 ( 2013 .01 ) ; C09J 197 / 005 (2013 .01 ) ; D21H 17 /23 (2013 . 01 ) 11 Claims, 8 Drawing Sheets atent Feb . 27 , 2018 Sheet 1 of 8 US 9 ,902 , 815 B2 Molar mass distributions of TOFA - lignins GPC 1 Jrop 028 Waters Styragel RH4E / THF wa M ngere * * erwwwe perpresesqueenspompierspoppypagpupu . * WwWTTAUX *** ** * *** * * y * rrrrr trengerpart wwwww Paramparcapanayamanganya na may pinay * * * * * waponyuma N * rrrrrr w w www on. inglese ontant ores m yapamatyrapetyanyimpang pirert w wwwwwwwwwwwwwwwwwwwwwwwwwww ERIA EXCAZZ owalimwona k li . wwo w wildernemendamentimientowalu Fig . W1 U . S . Patent Feb . 27 , 2018 Sheet 2 of 8 US 9 , 902 ,815 B2 FTIR spectra of TOFA - lignins concino - Singlechannel Carbonyl band of free TOFA not present in TOFA - lignins O nunla Lo verem haben .. , , VAAN. , wwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwww * * um* * * * * * * ** * * ** ** ** * * * * * * * * * * * * * * * * ** * * * * * * * * * * * * * * * * * * * * ** 4000 3500 3000 2500 2000 i 1500 1000 Wavenumber cm - } - w - Long chain - 0 - alkyl chains - - - 0 Aliphatic - . ester Aromatic lignin band (normalised ) Singlechannel w Aromatic ester wwwwwwwwwwwwww www. wait Port Bewer 4000 3500 3000 2500 2000 1500 1000 Wavenumber cm - Fig . 2 * medan m? catevaate barcabanedamdamin . - 50 50 350150 2012 ? ?? ??fatL??{ { Fig . 3 atent Feb . 27 , 2018 Sheet 3 of 8 US 9 ,902 , 815 B2 Contact angle measurements as a measure of surface hydrophobicity @ 83 m i ni rin naman sinh ? * * * TOFA 11. 4 gir2 Contactangle1"} * * ** * TOFA _ L _ 50 TOFA _ L100 _22 g /m2 82 # wwwn - TOFA _ L100 _ 3. 9 gim2 mul wigo ** w TOFA _ 5 .0 g m2 @ mw Paperboard owwwwwwwwwww W w wwwwwwwwwwwwwwwwwwwwwwwwwwwwwwww 0 20 40 60 80 100 Time ( seconds ) Fig . 4 GPC ! Jrop 028 Waters Styragel RH4E / THE 16.118 Norm . 1 36712.* * 37. erininbirininminimum *wwwwwwwwwwwwwwww nde 44* * 16.623com * * u 6622 * detardea * * * 21.043 * W** . * . winninamminiminiminementionn * * . wwwwwwwwwwwwww $19.70219.737 ? massawwww Westeroscope * . 21.953 . muhimninindian . weeewwwwwwwwwwwwwwwwwww Sample w PS Std wwwww Mw114 000 24 000 3700 680 NA oJmännismama www mannya yang sama 10 1515 20 2525 min Fig . 5 U . S . Patent Feb . 27, 2018 Sheet 4 of 8 US 9 , 902 ,815 B2 i LOLComomai 2924im38mm con Singlechannel mccare sepoate m1$ 6008-meteor 6951. .1284 -940 EZL.-* 0 . 0 milioni * * * * * * * * 4000 3500 3000 2500 2000 1500 1000 Wavenumoerom - 1 Fig . 6a ** ** * w ww w wwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwww and w as 000299 ww wwwwwwww* W * Singlechannel * . wwwwwww.w * * - * - * nawem niewww W 00: - AM minnitinn wwwww ado miriminim +000 ??se ??? ??? ??? 7500 jaqumanem 10- 1 Fig . 6b U . S . Patent Feb . 27 , 2018 Sheet 5 of 8 US 9 ,902 ,815 B2 *** Xx000000 ** * - -- TOFA 11 . 4 g /m2 ** - TOFA L 50 Contactangle(9 ** TOFAL 100 _ 2 . 2 g /m2 ### # # .. TOFA L 100 _ 3 . 3 g /m2 TOFA 5 . 0 g /m2 -- -- Paperboard - - - - - - - - - 00 20 40 60 80 100 Time sends } Fig . 7 U . S . Patent Feb . 27, 2018 Sheet 6 of 8 US 9 ,902 ,815 B2 Fig . 8a Fig . 8b atent Feb . 27 , 2018 Sheet 7 of 8 US 9 ,902 ,815 B2 » W an * Fig . 8c : 53 Fig . 8d U . S . Patent Feb . 27, 2018 Sheet 8 of 8 US 9 ,902 , 815 B2 Compounding of TOFA esterified lignin Fig . 9 US 9 ,902 ,815 B2 FUNCTIONALIZED LIGNIN AND METHOD It is another aim to provide functionalized lignin with OF PRODUCING THE SAME barrier properties. It is still a further aim to improve the properties of lignin FIELD OF INVENTION and , in particular lignin polymers , so as to allow for the use 5 of the material in areas, such as applications relating to The present invention relates to modification of natural insulation , adhesion , binding , as well as composites . products . In particular the present invention concerns a In the present context it has been found that hydroxyl method of modifying lignin , comprising the step of reacting groups present in lignin , preferably aliphatic or aromatic at least a part of the hydroxyl groups present in the lignin in hydroxyl groups, can be esterified with mixtures of fatty order to form a derivative thereof. 10 acids, such as a mixture of natural fatty acids . In particular, the hydroxyl groups of lignin can be esterified with a DESCRIPTION OF RELATED ART mixture of fatty acids containing C16 to C20 unsaturated fatty acids . Suitable compositions are formed by Tall Oil Fiber- based packaging materials have many advantages Fatty Acid fraction or similar compositions. over their plastic candidates such as renewability , recycla - 15 Esterification is carried out in order to completely or bility and compostability . However , their application is partially esterify the hydroxyl groups to provide a modified restricted due to poor barrier properties and high sensitivity lignin product which has interesting properties . to moisture . In order to improve the barrier properties , Thus, modification of lignin with fatty acids improves the packaging material is laminated with aluminium or petro - film forming ability of lignin and the barrier properties of the leum based polymers such as PE , EVOH and PVC derivate . 20 film . Since both the plastic film and the aluminium are problem - More specifically , the method according to the present atic for sorting , recycling and recovery, replacing one or invention is characterized by what is stated in the charac more barrier layers thereof in demanding packaging with terizing part of claim 1 . bio - based polymers should be much desired from an envi- The modified lignin according to the invention is charac ronmental point of view . Examples of bio polymers which 25 terized by what is stated in the characterizing portion of have been evaluated for packaging applications are chitosan , claim 12 . hemicelluloses , microfibrillated cellulose and starch . How ever , many of the bio polymers are hydrophilic and films Advantageous Effects of Invention produced from these materials are often hygroscopic , result ing in partial loss of their barrier properties at high humidity . 30 The present invention provides considerable advantages . Lignin is one of the most abundant natural polymers on Thus , as shown in the below examples , TOFA - esterified earth . Presently lignin is separated from wood during pulp - lignin forms a film with high and stable contact angle on ing processes . Only a small amount ( 1 - 2 % ) is utilized in paper board . It has good barrier properties against oxygen speciality products whereas the rest primary serves as fuel. and water vapour and medium barrier properties for aromas. Even if burning lignin is a valuable way to reduce usage of 35 The active multiple double bond functionalities in TOFA fossil fuel, lignin has significant potential as raw material for enable further tailoring of the film properties .
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