US 20190030101A1 ( 19) United States (12 ) Patent Application Publication ( 10) Pub . No. : US 2019 / 0030101 A1 COOPER et al. (43 ) Pub . Date : Jan . 31, 2019 ( 54 ) PRINTABLE CANNABINOID AND TERPENE Publication Classification COMPOSITIONS (51 ) Int. Cl. A61K 36 / 185 ( 2006 .01 ) ( 71 ) Applicant : ebbu , LLC , Evergreen , CO (US ) A61K 31 / 35 ( 2006 . 01) ( 72 ) Inventors : Jonathan Michael COOPER , Denver , A61K 31 / 122 (2006 . 01 ) CO (US ) ; Kurt Aron LEVY , Dillon , A61K 31 /015 ( 2006 .01 ) CO (US ) A61K 31/ 352 ( 2006 . 01 ) A61K 31 /045 ( 2006 . 01) A61K 31 /01 (2006 . 01 ) (21 ) Appl. No. : 16 / 060, 007 A61K 31/ 05 (2006 . 01) (22 ) PCT Filed : Dec . 7 , 2016 A61K 33 / 00 (2006 . 01 ) A61K 31 /353 (2006 . 01) ( 86 ) PCT No. : PCT /US2016 / 065455 (52 ) U . S . CI. CPC . .. A61K 36 / 185 (2013 . 01) ; A61K 31 / 35 $ 371 ( C ) ( 1 ), (2013 . 01 ) ; A61K 31/ 122 ( 2013 . 01 ) ; A61K ( 2 ) Date : Jun . 6 , 2018 31 /015 ( 2013 .01 ) ; A61K 31/ 352 ( 2013 .01 ) ; A61K 31/ 045 (2013 . 01 ) ; A61K 2300 / 00 Related U . S . Application Data ( 2013 .01 ) ; A61K 31/ 05 (2013 . 01 ) ; A61K 33 / 00 (63 ) Continuation of application No . 15 /055 , 499, filed on (2013 .01 ) ; A61K 31/ 353 ( 2013 . 01 ) ; A61K Feb . 26 , 2016 . 31 /01 ( 2013. 01 ) (60 ) Provisional application No. 62/ 349 , 932, filed on Jun . (57 ) ABSTRACT 14 , 2016 , provisional application No . 62 / 354 , 463 , This disclosure relates to new printable cannabinoid and filed on Jun . 24 , 2016 , provisional application No . terpene compositions, and method for making and using the 62/ 348 , 114 , filed on Jun . 9 , 2016 , provisional appli same. Inkjet printer technology is used to dose precise cation No . 62 / 347 ,558 , filed on Jun . 8 , 2016 , provi amounts of purified cannabinoids such that a user may select sional application No . 62/ 264 ,281 , filed on Dec. 7 , the type of effect desired and in the amount they want. 2015 , provisional application No . 62 / 264, 281 , filed Various methods include inhaling and ingesting through the on Dec . 7 , 2015 . use of different substrates . US 2019 /0030101 A1 Jan . 31, 2019 PRINTABLE CANNABINOID AND TERPENE 22 weeks, depending on the type of cannabis plant. Can COMPOSITIONS nabis indica plants are generally believed to require shorter flowering times than Cannabis sativa plants . During flow CROSS REFERENCE TO RELATED ering , unpollinated female plants produce buds containing APPLICATIONS sticky, white resin glands, aka trichomes. [ 0001 ] This application is being filed under 35 U . S . C . 371 [0010 ]. Most extractions of cannabis aim to extract can and is the National Stage of International Application No . nabinoids, particularly tetrahydrocannabinol ( THC ) . THC PCT /US2016 / 065455 filed Dec. 7 , 2016 , which claims pri has many known effects including relieving pain , treating ority under 35 U . S . C . 119 to U . S . Provisional Application glaucoma, relieving nausea , and inducing vomiting during No. 62 /349 , 932 filed Aug . 2 , 2016 ; 62 /354 ,463 filed Jun . 24 , cancer treatments . THC ' s most well - known property is the 2016 ; 62 /348 , 114 filed Jun . 9 , 2016 ; and 62 /347 ,558 filed psychoactive effect that creates the " high " often associated Jun . 8 , 2016 ; and is a continuation of U . S . application Ser . with cannabis . However , each cannabinoid has their own No . 15 /055 , 499 filed Feb . 26 , 2016 , which claims priority to effects and properties that make them a compound of inter U . S . Provisional Application No. 62/ 264 , 281 filed Dec. 7 , est. Examples include , Cannabigerol (CBG ) , Cannabigerolic Acid (CBGA ) , Cannabidiol (CBD ) , Cannabinol (CBN ) , 2015 , which are herein incorporated by reference in their Cannabichromene (CBC ) , Tetrahydrocannabivarin ( THCV ) , entireties . Cannabigerovarin (CBGV ) , and Cannabigerovarinic Acid TECHNICAL FIELD (CBGVA ) . [0011 ] Cannabinoids are difficult to prescribe because [0002 ] This disclosure relates to the cannabis industry. In people react to cannabinoids differently . Also , most doses of particular , this disclosure relates to using inkjet technology cannabinoids are in fixed amounts, e . g ., 5 mg, 25 mg, 100 to print cannabinoid and / or terpene compositions onto sub mg, etc . , making it difficult to prescribe . Besides ingestion , strates , ink compositions for printing onto substrates, and the most common method is smoking . Smoking poses a methods for making and using printed substrates. number of difficulties . First, is the unpredictability of the dosage of cannabinoids since most methods involve burning BACKGROUND cannabis . The same mass of cannabis will have different [ 0003 ] Inkjet technology is used in most everyday tasks. levels of cannabinoids compared to other plants of the same Inkjet printers are easy to use , precise, and widely available . mass because of different species , strains , age, etc . Second , Most inkjet printers are used in the academic and work inhaling smoke is not healthy and can pose a number of environment , printing reports , essays, spreadsheets , etc . different health problems. However, inkjet technology is not limited to the printing [0012 ] There exists a need for compositions comprising industry . new combinations of purified cannabinoids for either inges [ 0004 At a fundamental level, inkjet printers work by tion or inhalation . There also exists a particular need for propelling droplets of ink onto a substrate . Meaning, inkjet compositions providing one or more purified cannabinoids printers are capable of printing a number of different com in combination with a purified terpene . Furthermore , there positions on a number of different surfaces . Printing differ exists a need to provide precise amounts of one or more ent “ inks ” onto different substrates allows for a wide variety purified cannabinoids with or without one or more purified of uses in a number of fields , e . g . , the medical industry , terpenes . There exists a need to supply these compounds as culinary arts , textiles, etc . layered compositions on inert substrates for either adminis [ 0005 ] One unique application is the creation of certain tering orally or via inhalation . inks containing chemical positions. Inkjet printers are capable of quickly processing precise dosages of chemical DETAILED DESCRIPTION compositions onto a substrate of choice . One particular area of interest is cannabinoids from cannabis . [0013 ] Disclosed herein are new printable compositions [0006 Cannabis is a genus of flowering plants that and ink compositions comprising a purified cannabinoid include the species: Cannabis sativa , Cannabis indica , and and /or a purified terpene . Cannabis ruderalis. Cannabis has long been used for hemp [0014 ] Disclosed herein are new methods for making a fibers , seed and seed oils , medicinal purposes , and recre cannabinoid and /or terpene composition having precise dos ational purposes . ages. In one embodiment, the composition is ingested . In [ 0007 ] Cannabis is composed of 483 known chemical one embodiment, the composition is inhaled . compounds, which include cannabinoids, terpenoids, fla [00151 Disclosed herein are new printable compositions vonoids, nitrogenous compounds , amino acids , proteins, comprising more than one purified cannabinoid and with glycoproteins , enzymes , sugars and related compounds , more than one purified terpene . In one embodiment, the hydrocarbons, simple alcohols , aldehydes, ketones , simple compositions are printed onto a digestible substrate . In one acids , fatty acids , simple esters , lactones , steroids , terpenes , embodiment, the compositions are printed onto a burnable non -cannabinoid phenols , vitamins, pigments , and elements . substrate . [ 0008 ] Harvesting secondary compounds from a plant of [ 0016 ] Disclosed herein are new methods of printing pre genus cannabis typically requires harvesting trichomes. cise amounts of a purified cannabinoid and / or a purified Trichomes contain the largest amounts of secondary com terpene onto a substrate . pounds , such as cannabinoids , like THC , CBN , CBC , [0017 ] Disclosed herein are new compositions printed CBGV, CBGVA , CBDV , CBCV , THCV , CBDVA , CBGA , with an inkjet printer comprising : CBCV, CBCVA CBL , CBG , CBD . [ 0018 ] a purified cannabinoid ; 10009 ] Trichomes come from the flowering parts of the [0019 ] a purified terpene; cannabis plant . The flowering stage varies from about 6 to [0020 ] an excipient; US 2019 /0030101 A1 Jan . 31, 2019 [0021 ] a solvent; and [0028 ] In one embodiment the purified cannabinoid is chosen from Cannabigerolic Acid (CBGA ), Cannabigerolic [0022 ] a substrate . Acid monomethylether (CBGAM ) , Cannabigerol ( CBG ) , [ 0023 ] As used herein , the term “ purified ” means isolated Cannabigerol monomethylether (CBGM ) , Cannabigero from the plant ( e . g ., by using chromatography , distillation , varinic Acid ( CBGVA ) , Cannabigerovarin (CBGV ) , Can extractions, or similar technique ) resulting in a greater than nabichromenic Acid (CBCA ), Cannabichromene (CBC ) , 60 % purity . In some embodiments, the " purified ” composi Cannabichromevarinic Acid ( CBCVA ), Cannabichrom tions disclosed herein are greater than 70 % purity . In some evarin (CBCV ) , Cannabidiolic Acid (CBDA ) , Cannabidiol embodiments , the " purified ” compositions disclosed herein (CBD ) , Cannabidiol monomethylether (CBDM ) , Canna are greater than 80 % purity . In some embodiments , the bidiol- C4 (CBD -C4 ) , Cannabidivarinic Acid (CBDVA ) , " purified ” compositions disclosed herein