WO2020044343A1 - Produits en papier aromatisés et parfumés comprenant des terpènes et des cannabinoïdes - Google Patents

Produits en papier aromatisés et parfumés comprenant des terpènes et des cannabinoïdes Download PDF

Info

Publication number
WO2020044343A1
WO2020044343A1 PCT/IL2019/050965 IL2019050965W WO2020044343A1 WO 2020044343 A1 WO2020044343 A1 WO 2020044343A1 IL 2019050965 W IL2019050965 W IL 2019050965W WO 2020044343 A1 WO2020044343 A1 WO 2020044343A1
Authority
WO
WIPO (PCT)
Prior art keywords
paper product
terpene
terpenoid
paper
composition
Prior art date
Application number
PCT/IL2019/050965
Other languages
English (en)
Inventor
Gil LUXENBOURG
Raphael Luxenbourg
Daniela Ilieva Batovska
Julian Simeonov Karadjov
Original Assignee
Iiw Entourage Delivery Systems Ltd.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Iiw Entourage Delivery Systems Ltd. filed Critical Iiw Entourage Delivery Systems Ltd.
Publication of WO2020044343A1 publication Critical patent/WO2020044343A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D1/00—Cigars; Cigarettes
    • A24D1/02—Cigars; Cigarettes with special covers
    • A24D1/022—Papers for roll-your-own cigarettes
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D1/00—Cigars; Cigarettes
    • A24D1/02—Cigars; Cigarettes with special covers
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
    • A24D3/04—Tobacco smoke filters characterised by their shape or structure
    • A24D3/048—Tobacco smoke filters characterised by their shape or structure containing additives
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
    • A24D3/06—Use of materials for tobacco smoke filters
    • A24D3/14—Use of materials for tobacco smoke filters of organic materials as additive
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/05—Phenols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/15—Oximes (>C=N—O—); Hydrazines (>N—N<); Hydrazones (>N—N=) ; Imines (C—N=C)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
    • A61K31/355—Tocopherols, e.g. vitamin E
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/45—Non condensed piperidines, e.g. piperocaine having oxo groups directly attached to the heterocyclic ring, e.g. cycloheximide
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/02—Material of vegetable origin
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/03—Non-macromolecular organic compounds
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/03—Non-macromolecular organic compounds
    • D21H17/04—Hydrocarbons
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H27/00—Special paper not otherwise provided for, e.g. made by multi-step processes
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H27/00—Special paper not otherwise provided for, e.g. made by multi-step processes
    • D21H27/08—Filter paper

Definitions

  • the present invention relates to paper products, inter alia, smoking paper products, stably enriched with active cannabinoids and aroma and/or flavor compounds.
  • the invention relates to paper products enriched with a cannabinoid profile and a terpene profile, mimicking effect of cannabis.
  • Terpenes represent an ample group of organic compounds, widely-spread in plants. They are substantial components of volatile oils, aromatic substances of different parts of plants, mainly in flowers, fmits, and leaves, but also in stalks and roots.
  • Terpenes are hydrocarbons occurring widely in plants and animals and built up from isoprene (i.e., C 5 Hs) units. Terpenoids are regarded as modified terpenes, for example, when methyl groups are moved or removed, or when oxygen atoms added. The term "terpenes”, in many occasions is used to broadly include terpenoids.
  • Terpenes are typically present in small amounts in living organisms, where they play numerous vital roles in plant physiology as well as important functions in cellular membranes. Terpenes are naturally formed by the combination of two molecules of acetic acid to give mevalonic acid (C6H12O4) and conversion of the latter to isopentenyl pyrophosphate, which contains the five-carbon isoprene skeleton. Additional transformations of the isopentenyl compound yield the various terpenes and terpenoids.
  • mevalonic acid C6H12O4
  • isopentenyl pyrophosphate which contains the five-carbon isoprene skeleton. Additional transformations of the isopentenyl compound yield the various terpenes and terpenoids.
  • Terpenes are typically classified according to the number of isoprene units in the molecule.
  • Monoterpenes (CioHie) contain two isoprene units
  • sesquiterpenes (C15H24) contain three
  • diterpenes (C20H32) contain four
  • triterpenes (C30H48) contain six
  • tetraterpenes (C40H64) contain eight isoprene units.
  • Polyterpenes a.k.a. rubber and gutta-percha
  • Monoterpenes, sesquiterpenes, and diterpenes are abundant in essential oils of plants.
  • Terpenes possess desirable properties for use in foods, cosmetics, pharmaceuticals and biotechnology industries. Attempts to use terpenes as flavorants added to tobacco articles, such as cigarettes, is known in the art. Nevertheless, due to the high volatility of terpenes and terpenoids, application of those molecules onto such smoking articles is ineffective.
  • Various solutions for overcoming such obstacle include the use of a flavor-releasing agent which attempts to suppress the volatilization of the flavorant to a low level.
  • the present invention pertains to novel and advantageous methods and compositions for stably applying flavorant(s) to paper products.
  • the invention pertains, in one or more embodiments, to methods and compositions wherein the stabilizing agent is odorless, flavorless, and non-toxic, rendering the terpenes and terpenoids as the predominant smell and flavor components in the paper.
  • Objects of the invention are achieved by providing a paper product, such as, a smoking rolling paper, stably enriched with aroma and/or flavor compounds and/or with cannabinoid compounds.
  • Objects of the invention are achieved by providing a rolling paper, stably enriched with one or more cannabinoids and/or at least two or more terpene and/or terpenoid compounds.
  • the present invention is based in part on the unexpected discovery that cannabinoids, e.g., cannabidiol (CBD), efficiently provide a stabilizing effect on terpenes and terpenoids within paper products, thereby reducing the evaporation of those molecules from papers products.
  • CBD cannabidiol
  • cannabinoids also act as antioxidants and many of those molecules also possess active beneficial physiological effects. Further, the activity of cannabinoids can be modulated by terpenes and terpenoids, resulting in an entourage effect provided within smoking papers.
  • cannabinoids applied onto paper products can allow a triple effect of stabilizing the binding of terpenes and terpenoids onto paper products, preventing oxidation of those molecules in the paper products, and allowing a modulated physiological effect elicited by the combination of the cannabinoids and terpenes and/or terpenoids.
  • an aspect of the invention pertains to a paper product infused with an effective amount of a composition comprising at least one of: a flavor compound, an aroma compound, and a cannabinoid compound.
  • the aroma compound and/or flavor compound and/or cannabinoid compound originate from a plant, such as a cannabis plant.
  • the aroma compound and/or flavor compound is a terpene and/or a terpenoid.
  • the aroma compound and/or flavor compound is a synthetic compound.
  • the paper products further comprise a fixative agent.
  • the fixative agent is a cannabinoid.
  • the fixative agent is a compound other than a cannabinoid.
  • the fixative agent is a combination of a cannabinoid and another fixative agent.
  • the fixative agent affords or mediates binding or incorporation of the flavor and/or aroma compound within the paper product.
  • the paper products further comprise an antioxidant agent.
  • the antioxidant agent is a cannabinoid.
  • the antioxidant agent is a compound other than a cannabinoid.
  • the antioxidant agent is a combination of a cannabinoid and another antioxidant agent.
  • the antioxidant agent reduces or prevents oxidation of the terpenes and terpenoids, resulting with an enhanced stability of the aroma and/or flavor of the paper products.
  • the present invention provides an aromatized and/or flavored paper product, the paper product comprising, one or more terpene(s) and/or one or more terpenoid(s), and at least one of a fixative agent and an antioxidant.
  • the amount and/or choice of antioxidant is of great importance in maintaining stability of the terpenes/terpenoids in the herein disclosed paper products.
  • Essential oils, such as terpenes, and terpenoids are prone to oxidation, resulting in smell deterioration.
  • the herein disclosed inventors successfully devised and prepared paper products with terpenes and/or terpenoids, wherein the terpenes and/or terpenoids stably maintained in the paper products.
  • antioxidants presenting one or more features as defined below exhibited longer stability of the terpenes and/or terpenoids infused into the paper products.
  • the antioxidants increased substantially the stability of terpenes and their mixtures by slowing down their decomposition by oxygen.
  • the antioxidant exhibits one or more features effective in stabilizing the terpenes and/or terpenoids in the papers.
  • the antioxidant is a cannabinoid which exhibits one or more features effective in stabilizing the terpenes and/or terpenoids in the papers.
  • the features are selected from: oil solubility, chemical inertness or non-reactivity with compounds in the paper product, odorless, flavorless, low toxicity, not producing toxic and irritating substances during smoking or burning.
  • the antioxidant is selected from a tocopherol (e.g., vitamin E, E306-E309), vitamin C (E300), a natural cannabinoid (e.g., a mono- and diphenols), and a synthetic antioxidant (e.g., butylated hydroxyanisole (BHA, E320), butylated hydroxytoluene (BHT, E321), propyl gallate (PG, E310), e / /-butyl hydroquinone (TBHQ, E319) and any combination thereof.
  • a tocopherol e.g., vitamin E, E306-E309
  • vitamin C E300
  • a natural cannabinoid e.g., a mono- and diphenols
  • a synthetic antioxidant e.g., butylated hydroxyanisole (BHA, E320), butylated hydroxytoluene (BHT, E321), propyl gallate (PG, E310), e /
  • the antioxidant is one or more of a phenol selected from a cannabidiol, tetrahydrocannabinol, phenolic acids, flavonoids, gingerol, curcumin, vitamin E, butylated hydroxyanisole, a derivative thereof and a combination thereof.
  • the herein disclosed paper products further comprise a fixative agent which imparts substantially increased stability of the terpenes and terpenoids in the paper products.
  • the fixative agent exhibits one or more features effective in stabilizing the terpenes and/or terpenoids in the papers.
  • the fixative agent is a cannabinoid which exhibits one or more features effective in stabilizing the terpenes and/or terpenoids in the papers.
  • the fixative agent does not include a compound other than a cannabinoid.
  • the fixative agent is characterized by at least one of the features: odorless, flavorless, low volatility (e.g., with vapor pressure less than 0.1 mm Hg at 20°C), easy penetration through the cellulose pores and binding capacity to cellulose, binding capacity to terpene(s) and/or terpenoid(s), essential oil and terpene solubility with Hansen Solubility Parameters (HSPs) between the cellulose and terpenes, reduction in the vapor pressure of the fragrances, preservation of lasting quality and end notes of fragrance mixtures, lack of toxicity, burning without producing any bad smelling/toxic/irritating products in the side stream smoke, and any combination thereof.
  • HSPs Hansen Solubility Parameters
  • the fixative agent contains oxygen atoms spaced or separated by 2 or more carbon atoms.
  • the fixative agent is having Hansen Solubility Parameters (HSPs) below the cellulose of the paper product.
  • the fixative agent is having Hansen Solubility Parameters (HSPs) above terpene(s) and terpenoid(s) applied onto the paper product.
  • the fixative agent is having Hansen Solubility Parameters (HSP) between the cellulose and terpene(s) and/or terpenoid(s) applied onto the papers.
  • the fixative agent is selected from the group consisting of: a polypropylene glycol, a PPG-20 methyl glucose ether, diprolylene glycol, polyethylene glycol PEG-400, an ester of citric acid (e.g., triethyl citrate, and acetyl triethyl citrate), a derivative thereof, and any combination thereof.
  • the polypropylene glycol is having a M.W. of about 160 Da to about 10,000 Da. In one or more embodiments, the polypropylene glycol is having a M.W. selected from about 160 Da to about 400, and about 4,000 to about 10,000 Da. In one or more embodiments, the polypropylene glycol is a branched polypropylene glycol. In one or more embodiments, the branched polypropylene glycol is Glucam P-20, or a derivative thereof. In one or more embodiments, the fixative agent is a crystalline substance or oil able to dissolve in terpenes.
  • the fixative agent may, in some embodiments, be an antioxidant.
  • cannabinoids may act concomitantly as antioxidants and as pseudo-fixatives.
  • the terpene and/or terpenoid is maintained in the paper product for a substantially longer time as compared to a paper product without a fixative agent and an antioxidant or compared to a paper product with an antioxidant and without a fixative agent.
  • the present invention provides aromatized and/or flavored paper product, the paper product comprising,
  • terpenes and/or terpenoids one or more terpenes and/or terpenoids
  • fixative agent one or more of a fixative agent, wherein at least one of the fixative agent is a cannabinoid
  • the one or more of cannabinoids chemically stabilizes the terpenes and/or terpenoids in the paper product, thereby maintaining the terpenes and/or terpenoids in the paper product for a longer time as compared to a paper product without cannabinoids and antioxidants.
  • the antioxidant is one or more of a cannabinoid.
  • the fixative agent is one or more of a cannabinoid.
  • the cannabinoid is having Hansen Solubility Parameters (HSPs) below the cellulose of the paper product. In one or more embodiments, the cannabinoid is having Hansen Solubility Parameters (HSPs) above terpenes and terpenoids applied onto the paper product. In one or more embodiments, the cannabinoid is having Hansen Solubility Parameters (HSPs) between the cellulose and terpenes and/or terpenoids.
  • HSPs Hansen Solubility Parameters
  • cannabinoids include without limitation, cannabidiol (CBD), D 9 -tet rah yd roc an n ab i no 1 (THC), cannabigerol (CBG), cannabinol (CBN), cannabichromene (CBC), cannabichromevarin (CBCV), cannabivarin (CBV), cannabidivarin (CBDV), tetrahydrocannabivarin (THCV), cannabigerovarin (CBGV), cannabicyclol (CBL), cannabielsoin (CBE), and any combination thereof.
  • CBD cannabidiol
  • CBD cannabidiol
  • CBD cannabidiol
  • CBD cannabichromevarin
  • CBV cannabivarin
  • CBDV cannabidivarin
  • THCV cannabigerovarin
  • CBL cannabicyclol
  • CBE cannabielsoin
  • cannabinoid acids include, without limitation, cannabidiolic acid (CBDA), A 9 -tetrahydrocannabinolic acid (THCA), cannabigerolic acid (CBGA), cannabichromenenic acid (CBCA), cannabichromevarinic acid (CBCV A), tetrahydrocanabivarinic acid (THCV A), cannabigerovarinic acid (CBGV A), cannabidivarinic acid (CBDV A), cannabicyclolic acid (CBLA), a derivative thereof, and a combination thereof.
  • CBDDA cannabidiolic acid
  • THCA cannabidiolic acid
  • CBDA cannabigerolic acid
  • CBCV A cannabichromenenic acid
  • CBCV A cannabichromevarinic acid
  • THCV A cannabigerovarinic acid
  • CBDV A cannabidivarinic acid
  • CBDLA cannabicyclolic acid
  • compositions and methods effectively produced paper products comprising relatively high levels of cannabinoids.
  • the fixative agent weight per paper area is about 2.2 mg/cm 2 .
  • the amount of the cannabinoid per each paper product is at least about 0.18 mg/cm 2 .
  • at least about 0.2 mg/cm 2 at least about 0.25 mg/cm 2 , at least about 0.3 mg/cm 2 , at least about 0.4 mg/cm 2 , or at least about 0.5 mg/cm 2 .
  • the amount of the cannabinoid per each paper product is about 116 mg/g.
  • the amount of the cannabinoid per each paper product is at least about 15 mg, at least about 20 mg, at least about 30 mg, at least about 40 mg, at least about 50 mg, at least about 60 mg, at least about 70 mg, at least about 80 mg, or at least about 90 mg per gram paper.
  • the amount of the cannabinoid per each paper product is up to about 120 mg.
  • the amount of the cannabinoid per each paper product is at least about 10 mg and up to about 120 mg.
  • Such high concentration of cannabinoids within smoking papers is novel and affords consumption of those products with a viable effective dose of the cannabinoids.
  • the capability to infuse such high amounts of cannabinoids and terpenes and/or terpenoids within a paper allows controlling their concentration in those products and thereby devises and produces papers having cannabinoids as active ingredients with specified controlled doses.
  • the cannabinoid binds both cellulose of the paper and the terpenes and/or terpenoids, thereby creating a chemical interaction that prolongs the retention time of the terpenes and/or terpenoids on the paper product.
  • the terpene and/or the terpenoid is provided as a natural cannabis plant extract. In one or more embodiments, the terpene and/or the terpenoid is an isolated terpene and/or terpenoid. In one or more embodiments, the terpene and/or the terpenoid is a synthetic compound.
  • the herein disclosed paper products include selected terpenes/terpenoids profile produced from purified terpenes/terpenoids combined to create a new profile of those molecules, that may or may not contain an amount of plant extract.
  • the paper product is a smoking paper product.
  • the smoking paper product is selected from a rolling paper, a tip and a filter.
  • the paper is porous presenting pores having a diameter of about lxlO 3 pm to about 2xl0 3 pm.
  • the paper product is manufactured by applying onto the paper a composition comprising one or more terpene(s) and/or one or more terpenoid(s), and at least one of a fixative agent and an antioxidant.
  • the one or more terpene(s) and/or one or more terpenoid(s) is present within the composition in an amount of about 15% to about 70%, by weight of the composition.
  • the one or more terpene(s) and/or one or more terpenoid(s) is present within the composition in an amount of about 20% to about 60%, by weight of the composition.
  • the antioxidant is present within the composition in an amount of about 0.1% to about 3% by weight of the composition.
  • the antioxidant is present within the composition in an amount of about 0.5% to about 2.5% by weight of the composition.
  • the fixative agent is present within the composition in an amount of about 20% to about 80% by weight of the composition.
  • the fixative agent is present within the composition in an amount of about 40% to about 75% by weight of the composition.
  • the composition comprises:
  • one or more terpene(s) and/or one or more terpenoid(s) in an amount of at least about 20% by weight of the composition; and one or more of a cannabinoid in an amount of at least about 5% by weight of the composition.
  • the composition comprises:
  • one or more terpene(s) and/or one or more terpenoid(s) in an amount of at least about 20% by weight of the composition
  • a cannabinoid in an amount of at least about 20% by weight of the composition.
  • the composition comprises:
  • one or more terpene(s) and/or one or more terpenoid(s) in an amount of at least about 20% by weight of the composition
  • a cannabinoid in an amount of at least about 5% by weight of the composition
  • fixative agent other than cannabinoid in an amount of at least about 20% by weight of the composition.
  • the weight ratio between the fixative agent and the terpene and/or terpenoid is about 4: 1 to about 1:4. In one or more embodiments, the weight ratio between the fixative agent and the terpene and/or terpenoid is about 3: 1 to about 1:3. In one or more embodiments, the ratio is about 1: 1.
  • evaporation of the terpene and/or terpenoid is substantially reduced as compared to a paper product without a fixative agent and an antioxidant, or as compared to a paper product with an antioxidant and without a fixative agent.
  • the overall amount of the terpene and/or terpenoid remains within the paper for at least about 10 minutes following exposure of the paper to the environment.
  • the paper product comprises a terpene and/or terpenoid profile presenting substantial similarity to the terpene and/or terpenoid profile present naturally within a cannabis strain. In one or more embodiments, the paper product comprises a cannabinoid profile presenting substantial similarity to the terpene and/or terpenoid profile present naturally within a cannabis strain.
  • the profile is stably maintained for at least about 10 minutes at ambient environment. In one or more embodiments, at least about 50% of the terpenes/terpenoids molecules remain in the paper product, following 5 minutes or even 10 minutes exposure to ambient air. In one or more embodiments, more than 70% of the terpenoids and terpenes are maintained in the paper products following 10 minutes exposure to the environment.
  • the paper further comprises a cellulose coat provided on top of said paper product.
  • the paper product is manufactured by applying pressure onto the paper following the step of applying the terpenes/terpenoids composition as herein disclosed.
  • the pressure is at least about 16 g/cm 2 . In one or more embodiments, the pressure is about 16 g/cm 2 to about 775 g/cm 2 .
  • the terpene(s) and/or terpenoid(s) is present in the paper product in an amount of about 0.2 mg/cm 2 to about 1 mg/cm 2 .
  • the fixative agent is present in the paper product in an amount of about 0.2 mg/cm 2 to about 1 mg/cm 2 .
  • the present invention provides a method of producing an aromatized and/or flavored paper product, the method comprising:
  • composition comprising one or more terpene(s) and/or one or more terpenoid(s);
  • the composition further comprises at least one of a fixative agent and an antioxidant.
  • the method further comprises applying a cellulose layer over said paper product.
  • the step of applying the composition onto the paper product occurs concomitantly to applying pressure onto the paper product.
  • the method further comprises packing the paper product within a hermetically sealed package.
  • applying pressure is conducted using a roller.
  • the pressure is at least about 16 g/cm 2 . In one or more embodiments, the pressure is within the range of about 16 g/cm 2 to about 775 g/cm 2 .
  • the paper product is a smoking paper product.
  • the smoking paper product is selected from a rolling paper, a tip and a filter.
  • the smoking paper product is a rolling paper and wherein applying the composition onto the paper product is conducted on both sides of the rolling paper.
  • Yet a further aspect of the invention pertains to a method of producing the herein disclosed aroma and/or flavor compound-enriched paper product, the method comprising:
  • composition comprising predetermined amounts of an aroma and/or a flavor compound
  • the methods comprise applying an amount of the composition on the other side of the paper, and spreading the composition on top of the paper, optionally with a roller(s).
  • inserting the composition within the paper is made by physical means, such as by pressure, to thereby press and insert the composition into the pores of the paper.
  • the method further comprises packing the terpene/terpenoid enriched paper.
  • the method further comprises sealing the package.
  • FIG. 1 is a line graph showing retention of a mixture containing CBD and terpenoids in a ratio of 1: 1 during 10 minutes period at ambient conditions, according to some embodiments of the invention.
  • FIG. 2 is a line graph showing the weight of terpenoids (mg) retained on papers during 10 minutes period at ambient conditions following application of a mixture containing CBD and terpenoids in a ratio of 1: 1, according to some embodiments of the invention.
  • FIG. 3 is a line graph showing retention (weight %) of various amounts (m ⁇ ) of a mixture of CBD and terpenoids in an initial ratio of 1 : 1 during 10 minutes period at ambient conditions, according to some embodiments of the invention.
  • FIG. 4 is a line graph illustrating retention (weight %) of b-caryophyllene on rolling papers in the presence of CBD for 30 minutes, according to some embodiments of the invention.
  • FIG. 5 is a line graph illustrating retention (weight %) of linalool on rolling papers in the presence of CBD for 30 minutes, according to some embodiments of the invention.
  • the present invention provides novel smoking paper products comprising flavor and/or aroma compounds.
  • the present invention is particularly useful for smoking products and provides, for example, rolling papers that are flavored and/or aromatized with a flavor and/or aroma compound.
  • Terpenes and terpenoids are known in their relatively high volatile characteristics. Accordingly, in typical cases, terpenes or terpenoids will rapidly evaporate to air when applied onto paper products.
  • the present invention overcomes this obstacle by adding a cannahinoid which effectively acts as "a fixative agent" that affords stability and enhances retention of the terpene/terpenoid within the paper product.
  • compositions that comprise, in addition to terpenes and terpenoids, a cannahinoid which acts as a fixative agent and/or an antioxidant agent, and/or that were infused with terpenes and terpenoids while applying pressure, present an improved retention and/or stability of the terpenes and/or terpenoids within the paper.
  • CBD cannabidiol
  • terpenoids cannabidiol
  • the CBD stabilizes the terpenes and terpenoids and inhibits their immediate evaporation by mediating a chemical interaction with the cellulose of the paper products. It is hypothesized that the CBD binds cellulose and also terpenes and terpenoids, thereby creating a chemical interaction that prolongs the retention time of the terpenes and terpenoids on paper products, such as hydrogen bonding, electrostatic interactions, and van der Waals dispersion forces.
  • Cannabidiol is known as an antioxidant agent comparable to BHT and tocopherol and therefore can additionally act as such when applied onto the paper products.
  • the aroma and/or flavor compounds are substantially stably maintained within the product, even following exposure to the environment or while smoking (i.e., upon burning the paper).
  • the herein disclosed products provide an improved smell, and/or flavor and/or increase or even modulate the smoking experience effect due to the combination of active compounds, i.e., terpenes and/or terpenoids and cannahinoids.
  • the paper products are optionally incorporated with terpene and/or terpenoid profile which is substantially similar (in the types of molecules and/or the ratio between the molecules) to terpene and/or terpenoid profile present naturally in a cannabis plant.
  • terpene and/or terpenoid profile mimics the flavor and/or aroma of natural cannabis plant.
  • Cannahinoids represent a group of C19 or C21 terpeno-phenolic compounds found in Cannabis sativa L. Geranyl pyrophosphate is a parent compound to both phytocannabinoids and terpenoids. After coupling with either olivetolic acid or divarinic acid, pentyl or propyl cannabinoid acids are produced, respectively, via enzymes that accept either substrate, a manifestation of Mechoulam’s postulated ‘Nature’s Law of Stinginess’. Although having important biochemical properties, acidic forms of phytocannabinoids are most commonly decarboxylated via heat to produce the more familiar neutral phytocannabinoids.
  • Cannabinoids bind to human cannabinoid receptors CB-l and CB-2, thus causing a range of physiological effects in, for example, the nervous system, the immune and bone cells.
  • the physiological effects of cannabinoids are facilitated by terpenes/terpenoids through the so called“entourage effect” or synergism between the cannabinoids and terpene/terpenoids.
  • the herein disclosed invention provides paper products which may also afford physiological effects facilitated by the combination of cannabinoids and terpenes and/or terpenoids on the papers.
  • the cannabinoids are further effective in stabilizing the terpenes and/or terpenoids, preventing oxidation and stabilizing those molecules within the papers.
  • terpene and/or terpenoid profile refers to an assembly of at least two types of terpene and/or terpenoid molecules being substantially similar to the types of terpene and/or terpenoid molecules present naturally in a cannabis plant.
  • the term refers to several types of terpene and/or terpenoid molecules in the profile. For example, 3 or more, 4 or more, 5 or more, or 10 or more, or 15 or more, or 20 or more terpene and/or terpenoid molecules.
  • the term relates to the ratio between terpenes and/or terpenoids molecules (i.e., molar or weight ratio).
  • the ratio between molecules in the terpene and/or terpenoid profile is substantially similar to the ratio between terpene and/or terpenoid molecules present naturally in a cannabis plant.
  • the term "stability" refers to terpenes and/or terpenoids maintained substantially stable in the paper product.
  • the herein disclosed paper products present significantly higher stability of the terpenes and/or terpenoids for longer time periods as compared to comparable paper products without an antioxidant and/or a fixative agent, and/or that did’t infused with the terpenes and/or terpenoids while applying pressure.
  • the terpenes/terpenoids exhibit substantial stability for at least about 3 minutes, 5 minutes, at least about 10 minutes or at least about 15 minutes, at least about 20 minutes, at least about 30 minutes, or any value in between.
  • the terpenes/terpenoids exhibit stability for at least about 5 minutes, and up to about 90 minutes. For example, at least about 5 minutes and up to about 80 minutes, or at least about 10 minutes and up to about 70 minutes, or at least about 10 minutes and up to about 60 minutes, at least about 5 minutes and up to about 50 minutes, or at least about 5 minutes and up to about 40 minutes, or at least about 5 minutes and up to about 30 minutes, or any time periods in between.
  • each possibility presents a separate embodiment of the invention.
  • At least about 50% of the terpenes/terpenoids molecule types (irrespective of the overall terpenes/terpenoids quantity), and/or overall quantity remain in the paper product, following exposure to ambient air, for at least about 3 minutes, 5 minutes, 10 minutes, 15 minutes, 20 minutes, 25 minutes, 30 minutes, 35 minutes, 40 minutes, 45 minutes, 50 minutes, 55 minutes, 60 minutes, 65 minutes, 70 minutes, 75 minutes, 80 minutes, 85 minutes, or about 90 minutes, or any value in between.
  • Each possibility presents a separate embodiment of the invention.
  • terpenes/terpenoids remain in the paper product, following exposure to ambient air, for at least about 3 minutes, 5 minutes, 10 minutes, 15 minutes, 20 minutes, 25 minutes, 30 minutes, 35 minutes, 40 minutes, 45 minutes, 50 minutes, 55 minutes, 60 minutes, 65 minutes, 70 minutes, 75 minutes, 80 minutes, 85 minutes, or about 90 minutes.
  • Each possibility presents a separate embodiment of the invention.
  • the enhanced stability is due to the addition of one or more cannabinoids and optionally additional fixating agent and/or antioxidant and/or due to applying pressure when manufacturing the paper product.
  • the term "comparable paper product” refers to a paper product comprising similar amounts of aroma and/or flavor compounds and without a fixating agent and/or without an antioxidant and/or, that wasn't manufactured while applying pressure on the paper following spreading the terpene/terpenoid composition.
  • the herein disclosed products present enhanced maintenance/retention of the aroma and/or flavor compounds in the paper which is significantly higher than a corresponding product containing a similar amount of flavor and/or aroma compounds but does not contain an antioxidant and/or a fixating agent.
  • the term "significantly higher” encompasses at least about 1.2, 1.5 folds, or at least 2 folds more. Each possibility presents a separate embodiment of the invention.
  • retention refers to the overall amount of aroma and/or flavor compounds that remains in the paper product as compared to comparable paper product without an antioxidant and/or a fixative agent, and/or that wasn't infused with terpene and/or terpenoid while applying pressure.
  • retention refers to the entire terpene/terpenoid molecules maintained for longer period in a paper product (i.e., presents a reduced evaporation) as compared to a comparable paper without an antioxidant and/or a fixative agent, and/or that wasn't infused with terpene and/or terpenoid while applying pressure.
  • the terpenes/terpenoids exhibits substantial enhanced retention for at least about 5 minutes, at least about 10 minutes, at least about 15 minutes, at least about 20 minutes, at least about 25 minutes, or at least about 30 minutes, or at least about 40 minutes, or at least about 50 minutes, or at least about 60 minutes, or any value in between.
  • the overall quantity of the terpenes/terpenoids exhibits retention of at least about 20% for 90 minutes or above at ambient air.
  • at least about 50%, or 60%, or 70%, or 80% of the overall terpenes/terpenoids is still infused following about 5 minutes or above, or 10 minutes or above exposure to ambient air.
  • At least about 50% of the overall terpenes/terpenoids is still infused following about 5, 10 or 20 minutes or above, or at least about 40% of the overall terpenes/terpenoids is still infused following about 20, or 30 minutes or above, or at least about 15% of overall terpenes/terpenoids is still infused following about 60 minutes or above, or at least about 10% of the overall terpenes/terpenoids is still infused following about 90 minutes or above, exposure to ambient air.
  • the term "paper products” encompasses various types of products made of paper.
  • the paper product may present various colors and sizes.
  • the paper product is a smoking paper product.
  • the term “smoking product” encompasses any optional product used for smoking and made of paper.
  • the smoking product is made of a paper for which the addition of an aroma and/flavor compound may be applicable.
  • the paper product is a smoking product. Suitable smoking products include, without limitation, a rolling paper, a tip, and a filter (e.g., a straw filter).
  • the paper product is not a tobacco paper product. Any smoking rolling papers, filters and tips are contemplated.
  • Exemplary filters include those filters used in pipes or hookahs.
  • the term includes sanitary and/or toiletries paper products, such as wet wipes, wiping papers, paper hand towels, tissues, toilet paper, and pads. In one or more embodiments, the term does not include sanitary and/or toiletries paper products, such as toilet paper and pads.
  • the paper product has a thickness of at least about 15 pm.
  • the thickness may be no more than about 35 pm, 30 pm, 25 pm or 20 pm, or within the range of about 15 pm to about 35 pm, between about 15 pm to about 30 pm, or between about 18 pm to about 22 pm, or between about 20 pm to about 22 pm, or any value in between.
  • Each possibility presents a separate embodiment of the invention.
  • the paper product has a grammage (i.e., mass per unit of area) of at least about 10 g/m 2 .
  • the grammage may be no more than about 20 g/m 2 , 18 g/m 2 , 17 g/m 2 , 16 g/m 2 or 15 g/m 2 , or within the range of about 10 g/m 2 to about 20 g/m 2 , between about 10 g/m 2 to about 16 g/m 2 , or between about 11 g/m 2 to 15 g/m 2 , or any value in between.
  • a grammage i.e., mass per unit of area
  • the grammage may be no more than about 20 g/m 2 , 18 g/m 2 , 17 g/m 2 , 16 g/m 2 or 15 g/m 2 , or within the range of about 10 g/m 2 to about 20 g/m 2 , between about 10 g/m 2 to about 16 g/m
  • the paper product has a density of at least about 350 kg/m 3 .
  • the density may be no more than about 750 kg/m 3 , 700 kg/m 3 , 680 kg/m 3 , or 670 kg/m 3 , or within the range of about 400 kg/m 3 to about 700 kg/m 3 , between about 630 kg/m 3 to about 670 kg/m 3 , between 649 kg/m 3 and 651 kg/m 3 , or any value in between.
  • the density may be no more than about 750 kg/m 3 , 700 kg/m 3 , 680 kg/m 3 , or 670 kg/m 3 , or within the range of about 400 kg/m 3 to about 700 kg/m 3 , between about 630 kg/m 3 to about 670 kg/m 3 , between 649 kg/m 3 and 651 kg/m 3 , or any value in between.
  • Each possibility presents a separate embodiment of the invention.
  • the smoking paper may be porous, presenting pores with a diameter in the range of between about lxlO 3 pm to about 2xl0 3 pm. For example, about 1.4x10 3 pm to about l.6xl0 3 pm, or about 0.54 to about 2.54 pm.
  • the smoking paper may have porosity (herein referred to as percentage of the bulk volume of air) in the range of between about 50% to about 70%. For example, about 50% to about 65%, or about 54% to about 58%, or about 55.6% to about 57.6%.
  • the smoking paper may have smoothness (according to Bekk method) in the range of between about lOs to about 20s. For example, about 13 to about 20 Bekk seconds, or about 15 to 17 Bekk seconds.
  • the paper product is a rolling paper having a size of between 5 cm (width) and 11 cm (length).
  • the term "aroma compound” encompasses any compound that may add an aroma or odor to paper products.
  • the aroma compound should be suitable such that it can be incorporated within a paper.
  • flavor compound encompasses any compound that may add flavor or taste to paper products.
  • the flavor compound should be suitable such that it can be incorporated within a paper.
  • the aroma and/or flavor compound is purified from a plant (e.g., from a plant extract). In one or more embodiment, the aroma and/or flavor compound is provided within a plant extract. In one or more embodiment, the aroma and/or flavor compound is a synthetic compound. In one or more embodiment, the aroma and/or flavor compound is a terpene. In one or more embodiment, the aroma and/or flavor compound is a terpenoid.
  • composition comprising at least one terpene and/or terpenoid.
  • the composition may further comprise a fixative agent.
  • the composition may further comprise an antioxidant agent.
  • terpenes encompasses a large and diverse class of organic compounds, produced by a variety of plants or animals. Terpenes confer a strong odor. Terpenes are also major constituents of cannabis plants (such as Cannabis sativa ), which contain at least 120 identified compounds. The difference between terpenes and terpenoids is that terpenes are hydrocarbons, whereas terpenoids are considered as modified terpenes that contain additional functional groups, or in which methyl groups have been moved or removed, or oxygen atoms added. For example, myrcene (a hydrocarbon) is a terpene, and linalool (an alcohol) is a terpenoid.
  • Terpenoids are also known as isoprenoids. Cannabis essential oils contain mostly mono- and sesquiterpenes/terpenoids. Monoterpenes (e.g. limonene) contain 10 carbon atoms, and sesquiterpenes (e.g. caryophyllene) contain 15 carbon atoms.
  • Monoterpenes e.g. limonene
  • sesquiterpenes e.g. caryophyllene
  • Major terpenes/terpenoids are referred to herein as those compounds present in Cannabis sativa L strain in relatively high concentration. Depending on the cannabis strain, their amount usually varies from a few percent to about 50% of the total weight of the cannabis essential oil.
  • Minor terpenes/terpenoids are referred to herein as those compounds present in Cannabis sativa L strain in relatively low concentration. Their amount in cannabis essential oils may vary from below detection limit, to fractions of a percent, to (seldom) a few weight percent in some strains. In an embodiment of the invention, the present invention is not limited in scope to the particular type of terpene/ terpenoid.
  • the terpenes/terpenoids is Generally Regarded As Safe (GRAS), i.e., an FDA designation that a chemical or substance added to food is considered safe.
  • the terpene/terpenoid is regarded as a cannabis essential oil. In one or more embodiments, the terpene/terpenoid is other than those terpenes/terpenoids known to exhibit toxicity.
  • the terpene/terpenoid is selected from a monoterpene, a bicyclic terpene, a sesquiterpene, a diterpene, a triterpene, a tetraterpene, or from a terpene alcohol, terpene aldehyde or terpene ketone.
  • the terpene/terpenoid is selected from the group consisting of fenchol, b-caryophyllene, epoxy-ocimene, nerolidol, l-epi-cubenol, l,8-cineole, allo- aromadendrene, aromadendrene, bicyclogermacrene, bisabolene, borneol, camphene, camphor, caryophyllene oxide, coachelnsol, curcumene, delta-3-carene, elemene, geraniol, germacrene, guaiene, guaiol, gurjunene, humulene epoxide II, ipsdienol, isoborneol, limonene, dipentene, linalool, menthol, muurolene, myrcene, nerol, p-cymen-8-ol, p-cymene
  • the terpene/terpenoid is a major terpene/terpenoid.
  • the major terpene/terpenoid is selected from the group consisting of: limonene, linalool, myrcene, humulene, a-pinene, b-caryophyllene, b-pinene, and any combination thereof.
  • the terpene/terpenoid is a minor terpene/terpenoid.
  • the minor terpene/terpenoid is selected from the group consisting of: fenchol, epoxy-ocimene, nerolidol, l-epi-cubenol, 7-epi-sesqui thujene, 1,8- cineole, allo-aromadendrene, aromadendrene, bicyclogermacrene, bisabolene, borneol, camphene, camphor, caryophyllene oxide, ocimene, coachelnsol, curcumene, delta-3-carene, elemene, geraniol, germacrene, guaiene, guaiol, gurjunene, humulene epoxide II, ipsdienol, isoborneol, menthol, muurolene, nerol, p-cymen-8-ol, p-cymene, sabinene,
  • the terpene/terpenoid is selected from the group consisting of: linalool, terpinolene, humulene, g-terpinene, D-limonene, a-pinene, myrcene, b- caryophyllene, a derivative thereof, and any combination thereof.
  • the terpene and/or terpenoid is purified from a cannabis plant.
  • the terpene and/or terpenoid is a synthetic compound.
  • the aroma and/or flavor compound is a derivative or a homologue of a terpene or a terpenoid, or a compound mimicking terpene or terpenoid.
  • the terpene/terpenoid is in an isolated form. In one or more embodiment, the terpene/terpenoid is isolated from a cannabis plant or from any other plant or animal.
  • the term“isolated” refers to the terpene and/or terpenoid which is separated from at least some of the components with which it is usually associated in nature or in in vitro conditions, and/or prepared or purified by a process that involves the hand of a man.
  • the terpene/terpenoid is substantially free of any natural or synthetic compounds. In one or more embodiment, the terpene/terpenoid is essentially free of any natural or synthetic compounds. In one or more embodiment, the terpene/terpenoid is free of any natural or synthetic compounds.
  • the term“substantially free” refers to a compound or composition comprising less than about 0.5%, or less than about 0.4%, or less than about 0.3%, or less than about 0.2%, or less than about 0.1%, or any percentage in between of a particular compound.
  • the term“essentially free” refers to a compound or composition comprising less than about 0.05%, or less than about 0.04%, or less than about 0.03%, or less than about 0.02%, or less than about 0.01%, or less than about 0.005%, or any percentage in between, or having only trace amounts of a particular compound or of other compounds.
  • the purified or isolated terpene and/or terpenoid refers to the compound being substantially or essentially pure of any other naturally occurring or non-naturally occurring substances, including cannabinoids that occur naturally in cannabis plants.
  • substantially pure can be taken to mean that no substantial amounts of cannabinoids other than terpenes and/or terpenoids are detectable by HPLC.
  • the purified terpene and/or terpenoid comprises up to about 1 % of non-terpene or terpenoid compound.
  • the herein disclosed paper products are produced by application of a composition comprising terpenes and/or terpenoids.
  • the herein disclosed terpenes and/or terpenoids composition or rolling paper comprising same includes a mixture of pure and synthetic terpene and/or terpenoid compounds.
  • the herein disclosed terpene/terpenoid composition or rolling paper comprising same includes a profile of terpenes and/or terpenoids compounds that is substantially similar to a cannabis plant.
  • the terpene(s) and/or terpenoid(s) is present in the terpene and/or terpenoid composition at about 15% to about 70% by weight of the composition. In some embodiments, the terpene(s) and/or terpenoid(s) is present in the terpene and/or terpenoid composition at about 20% to about 65%, at about 20% to about 60%, or at about 40% to about 60%, or at about 45% to about 55% by weight. For example, the terpene(s) and/or terpenoid(s) is present at about 49% to about 51% by weight.
  • the herein disclosed terpene(s) and/or terpenoid(s) composition comprises at least about 15%, at least about 20%, at least about 25%, at least about 30%, at least about 35%, at least about 40%, or at least about 45% of terpenes and/or terpenoids.
  • Each possibility represents a separate embodiment of the invention.
  • one terpene/terpenoid may reach up to about 59% of the terpene and/or terpenoid composition.
  • one terpene/terpenoid may be present in an amount of between 10% and 59%.
  • a combination of two terpenes and/or terpenoids may reach up to 50% of the composition.
  • two terpenes and/or terpenoids may be present in an amount of between 20% and 50%.
  • a combination of three terpenes and/or terpenoids may reach up to 50% of the composition.
  • three terpenes and/or terpenoids may be present in an amount of between 30% and 50%.
  • a combination of four and more terpenes and/or terpenoids may reach up to 50% of the composition.
  • four terpenes and/or terpenoids may be present in an amount of between 40% and 50%.
  • the terpene(s) and/or terpenoid(s) weight per paper area is below about 1 mg/cm 2 . In some embodiments, the terpene(s) and/or terpenoid(s) weight per paper area is at least about 0.2 mg/cm 2 , at least about 0.4 mg/cm 2 , or at least about 0.5 mg/cm 2 .
  • the terpene(s) and/or terpenoid(s) weight per paper area is within the range of about 0.2 mg/cm 2 to about 0.8 mg/cm 2 , or about 0.2 mg/cm 2 to about 0.7 mg/cm 2 , or about 0.2 mg/cm 2 to about 0.5 mg/cm 2 .
  • the terpene(s) and/or terpenoid(s) weight per paper area is about 0.37 mg/cm 2 .
  • the aroma and/or flavor compound presents a chemical profile or composition that is substantially similar to the chemical composition of those compounds present naturally within a cannabis plant.
  • Said similarity can be of a full profile or a partial profile consisting of at least two terpenes and/or at least two terpenoids.
  • the weight or molar ratio between the at least two terpenes and/or the at least two terpenoids is substantially similar to the actual ratio between those compounds present in the natural cannabis plant.
  • the smoking product of the invention includes at least one terpene or terpenoid.
  • the smoking product includes a mixture (or a profile) comprising at least 2 terpenes, or at least 3, 4, 6, 8, 10, 12, 14, 16, 18, 20, 22, 24, 26, 28 or 30 of terpenes, or any value in between.
  • the smoking paper product may include even higher amounts of terpenes or terpenoids. For example, more than 40, 60, 80, 100, 150, 200, 250 or above. Each possibility presents a separate embodiment of the invention.
  • the smoking product of the invention includes at least one terpenoid.
  • the smoking product includes a mixture (of a profile) comprising at least 2 of terpenoids, or at least 4, 6, 8, 10, 12, 14, 16, 18, 20, 22, 24, 26, 28 or 30 of terpenoids.
  • a mixture of a profile
  • the smoking product includes a mixture (of a profile) comprising at least 2 of terpenoids, or at least 4, 6, 8, 10, 12, 14, 16, 18, 20, 22, 24, 26, 28 or 30 of terpenoids.
  • the aroma and/or flavor compound(s) is incorporated within the paper, infused within the paper, bound within the paper, and/or coated onto the paper.
  • composition or products comprising same further contain a cannabinoid as a fixating agent (interchangeable with the term "fixative agent").
  • the herein disclosed composition or products comprising same further contain a fixating agent other than a cannabinoid.
  • Terpenes and terpenoids are known in their relatively high volatile characteristics. Accordingly, in typical cases, providing paper products with terpenes or terpenoids will result in fast evaporation of the terpenes/terpenoids from the paper.
  • the present invention overcomes this obstacle by adding a cannabinoid(s) and optionally an additional agent other than cannabinoid(s) (hereinafter referred to as "a fixative agent”) that affords stability and enhances retention of the terpene/terpenoid within the paper product. Further advantageously, the terpenes and/or terpenoids are maintained within the paper even in an opened environment (i.e., ambient air) and even when the product is being smoked.
  • an opened environment i.e., ambient air
  • the "fixative agent” may be any agent capable of incorporating and/or binding and/or maintaining, and/or stabilizing, and/or enhance retention, and/or reduce evaporation of the flavor and/or aroma compound within the paper.
  • the fixative agent is capable of binding to oils.
  • the fixative agent is soluble in oil (i.e., it is oil soluble).
  • the fixative agent is not water soluble, or in other words is water insoluble.
  • the fixative agent is amphiphilic.
  • the fixative agent is low volatile with vapor pressure less than 0.1 mm Hg at 20°C. In one or more embodiments, the fixative agent is hydrophobic.
  • the fixative agent is miscible with the terpene profile. In one or more embodiments, the fixative agent is capable of binding to cellulose without dissolving its components (Hansen parameters 5P and dH below 19.9 MPa 172 and 22.5 MPa 172 , resp.). In one or more embodiments, the fixative agent is odorless and safe for use in smoking products.
  • fixatives are used as substances capable to impart increased stability to the scent molecules and to slow the evaporation of those scent components such that the scent character during evaporation remains substantially constant.
  • the substances typically used as fixatives are mostly low volatile, having high-boiling temperature and may themselves be scented or unscented.
  • oil soluble refers to a compound which is soluble in nonpolar substances, such as ether, chloroform, and oils. Oil-soluble compounds are often insoluble in water.
  • the fixative agent is capable of binding to volatile oils. In one or more embodiments, the fixative agent is capable of binding to aroma oil, or essential oil. In one or more embodiments, the fixative agent is dissolved in aroma oil, or essential oil. In one or more embodiments, the fixative agent is capable of binding to a terpene and/or terpenoid.
  • the fixative agent may thus have binding affinity to terpene and/or terpenoid.
  • the fixative agent may bind to a terpene and/or terpenoid via intramolecular hydrogen bonding and van der Waals dispersion forces.
  • the fixative agent is capable of binding (to a paper, or to one or more substances within a paper (e.g., cellulose).
  • the fixative agent may thus have binding affinity to cellulose.
  • the fixative agent may bind to cellulose via intramolecular hydrogen bonding, van der Waals forces, and electrostatic interactions.
  • Each possibility presents a separate embodiment of the invention. For example, it can interact with terpene and/or terpenoid via van der Waals forces.
  • the fixative agent is capable of binding concomitantly to a terpene and/or terpenoid and to cellulose.
  • the fixative agent is a fragrance fixative. In one or more embodiments, the fixative agent is not a fragrance fixative.
  • fragrance fixatives are liquid or waxy, natural or synthetic compounds with low to no volatility that can dissolve or be dissolved in fragrant compounds (e.g., terpenes/terpenoids).
  • the fixative agent is used herein and is capable of substantially reducing the evaporation of one or more terpene/terpenoid from the paper product.
  • the fixatives are non-toxic or possess a very low toxicity and, when burned, produce low/insignificant amounts of irritating/toxic/obnoxious decomposition products.
  • the fixatives have a very weak to no smell. In an embodiment of the invention, the fixatives do not affect substantially the smell of the terpene composition.
  • the fixative agent is flavorless. In one or more embodiments, the fixative agent is odorless. In an embodiment of the invention, the fixative agent is a cannabinoid or a derivative thereof. In an embodiment of the invention, the cannabinoid is selected from cannabidiol (CBD), A 9 -tetrahydrocannabinol (THC), cannabigerol (CBG), cannabinol (CBN), cannabichromene (CBC), cannabichromevarin (CBCV), cannabivarin (CBV), cannabidivarin (CBDV), tetrahydrocannabivarin (THCV), cannabigerovarin (CBGV), cannabicyclol (CBL), cannabielsoin (CBE), and any combination thereof.
  • CBD cannabidiol
  • THC cannabigerol
  • CBN cannabinol
  • CBCV cannabichromene
  • CBCV cann
  • cannabinoid acids include, without limitation, cannabidiolic acid (CBD A), A 9 -tetrahydrocannabinolic acid (THCA), cannabigerolic acid (CBGA), cannabichromenenic acid (CBCA), cannabichromevarinic acid (CBCV A), tetrahydrocanabivarinic acid (THCV A), cannabigerovarinic acid (CBGV A), cannabidivarinic acid (CBDV A), cannabicyclolic acid (CBLA), a derivative thereof, and a combination thereof.
  • CBD A cannabidiolic acid
  • THCA cannabidiolic acid
  • CBDA cannabigerolic acid
  • CBCA cannabichromenenic acid
  • CBCV A cannabichromevarinic acid
  • THCV A cannabigerovarinic acid
  • CBDV A cannabidivarinic acid
  • CBDLA cannabicyclolic acid
  • the fixative agent is cannabidiol (CBD).
  • CBD cannabidiol
  • the fixative agent is a polymer (e.g., a polypropylene glycol-based polymer).
  • the polypropylene glycol is having a M.W. (Molecular Weight) of 160 Dalton to 10000 Dalton.
  • the molecular weight should be within the ranges of 160-400 Da, or of 4000 to 10,000 Da. Such compounds with these molecular weights have the lowest toxicity.
  • the fixative agent is PPG-20 methyl glucose ether (a.k.a, Glucam P-20).
  • the fixative agent is triethyl citrate. In a further exemplary embodiment, the fixative agent is diprolylene glycol. In a further exemplary embodiment, the fixative agent is PEG-400.
  • the fixative agent is present in the terpene/terpenoid composition at about 30% to about 80% by weight.
  • the fixative agent is present in the terpene/terpenoid composition at about 40% to about 75%, 40% to about 70%, or at about 45% to about 60%, or at about 45% to about 55%, or at about 49% to about 51% by weight.
  • the terpene/terpenoid composition includes at least about 40%, at least about 50%, at least about 60%, or at least about 65% of a fixative agent.
  • the fixative agent is a cannabinoid (e.g., cannabidiol) and is present in the terpene/terpenoid composition at about 1% to about 80% by weight.
  • the cannabinoid is present in the terpene/terpenoid composition at about 1% to about 75%, 1% to about 70%, or at about 1% to about 60%, or at about 1% to about 55%, or at about 1% to about 50% by weight.
  • the terpene/terpenoid composition includes at least about 1%, at least about 2%, at least about 3%, at least about 5%, at least about 10%, at least about 20%, or at least about 30% of a cannabinoid.
  • a combination of fixative agents is included in the terpene/terpenoid composition.
  • a combination of a cannabinoid and another fixative agent is applicable and contemplated.
  • the weight ratio between the fixative agent and the terpene and/or terpenoid is about 5: 1 to about 1 :5, or about 4: 1 to about 1 :4, or about 3: 1 to about 1:3, or about 1 : 1.
  • the weight ratio between the fixative agent and the terpene and/or terpenoid is 1: 1 to 1 :5, or 1 : 1 to 1 :4, or about 1: 1 to about 1:3, or about 1: 1.
  • the fixative agent weight per paper area is below about 1 mg/cm 2 . In some embodiments, the fixative agent weight per paper area is at least about 0.2 mg/cm 2 , 0.4 mg/cm 2 , or 0.5 mg/cm 2 , or 1 mg/cm 2 . For example, the fixative agent weight per paper area is within the range of about 0.2 mg/cm 2 to about 0.8 mg/cm 2 , or about 0.2 mg/cm 2 to about 0.7 mg/cm 2 , or about 0.2 mg/cm 2 to about 0.5 mg/cm 2 . In an exemplary embodiment, the fixative agent weight per paper area is about 0.37 mg/cm 2 . In one or more embodiments, the fixative agent is Glucam P-20 or a derivative thereof. In one or more embodiments, the fixative agent is cannabidiol or a derivative thereof.
  • the fixative agent does not dissolve or solubilize the main paper compound cellulose. Accordingly, the fixative agent may possess 5P and dH below the dR and dH of cellulose. A fixative agent may further possess dR and dH above the dR and dH of terpenes and terpenoids applied onto the paper product, in order to allow solubilizing the terpenes and terpenoids. The fixative agent may possess d ⁇ below the d ⁇ of cellulose. Thus, in one or more embodiments, the fixative agent/cannabinoid has dR value of below about 19.9 MPa 1 ⁇ 2 .
  • the fixative agent/cannabinoid possesses a dR value of below 19, or below 18, or below 17 MPa 1 ⁇ 2 .
  • the fixative agent/cannabinoid possesses a dR value of above about 1, or above 2, or above 3, or above 4, or above 5 and below 19.9 MPa 1 ⁇ 2 .
  • the fixative agent/cannabinoid has dH value of below about 22.5 MPa 1 ⁇ 2 .
  • the fixative agent/cannabinoid possesses a dH value of below 22, or below 21, or below 20 MPa 1 ⁇ 2 .
  • the fixative agent/cannabinoid possesses a dH value of above 2, or above 3, or above 4, or above 5, or above 6, or above 7 and below about 22.5 MPa 1 ⁇ 2 .
  • the fixative agent/cannabinoid has d ⁇ value of below about 24.3 MPa 1 ⁇ 2 .
  • the fixative agent/cannabinoid possesses a dH value of below 23, or below 21, or below 20 MPa 1 ⁇ 2 .
  • the fixative agent/cannabinoid possesses a d ⁇ value of above 2, or above 3, or above 4, or above 5, or above 6, or above 7 and below about 24.3 MPa 1 ⁇ 2 .
  • the paper product comprises a cannabinoid and a mixture of terpenes and/or terpenoids in a ratio of between about 4: 1 to about 1:4, or between about 3: 1 to about 1 :3. For example, between about 2: 1 to about 1:2, or about 1: 1.
  • the paper product comprises a cannabidiol and a mixture of the following terpenes in a ratio of 1 : 1 : a-pinene, camphene, b-pinene, myrcene, pseudolimonene, limonene, a- terpinolene, l,2-epoxylinalool, linalool, camphor, 3-allyl-2-methoxyphenol, a-cubebene, clovene, a-copaene, b-c/.v-caryophyllene, -trans-caxyo >ay ⁇ e,ne,, humulene-(vl), humulene, b- cadinene, b-sebnene, a-selinene, L-calamenene, caryophyllene oxide, and cembrene.
  • the terpene/terpenoid composition or paper product comprising same further comprise an antioxidant.
  • the antioxidant prevents oxidation of the terpenes and terpenoids, allowing an enhanced stability and/retention of the paper product.
  • the antioxidant in the presently described compositions and/or products can include any known acceptable compound that functions by inhibiting oxidation.
  • antioxidant agent refers to compounds being either natural or synthetic that possess the capacity to slow down or prevent the oxidation/decomposition of an extremely wide range of products (e.g., foods, fragrances to plastics). Some antioxidants are better soluble in water; other antioxidants are better soluble in oils. In an exemplary embodiment of the invention, the antioxidant is oil soluble. In one or more embodiments, the antioxidant dissolves in the herein disclosed composition of terpene/terpenoid.
  • the antioxidant is not water soluble, or in other words is water insoluble. Alternatively, or additionally, the antioxidant is amphiphilic. In one or more embodiments, the antioxidant is capable of binding to volatile oils. In one or more embodiments, the antioxidant is capable of binding to aroma oil, or essential oil. In one or more embodiments, the antioxidant is capable of binding to a terpene and/or terpenoid. The antioxidant may thus have binding affinity to terpene and/or terpenoid. The antioxidant may bind to a terpene and/or terpenoid via a chemical bond such as via an ionic bond, via a polar bond, a covalent bond, and/or a hydrogen bond.
  • the antioxidant can interact with terpene and/or terpenoid via van der Waals forces.
  • the antioxidant is a fragrance antioxidant.
  • the antioxidant is capable of binding to a paper, or to one or more substances within a paper (e.g., cellulose). The antioxidant may thus have binding affinity to cellulose.
  • fragment antioxidant can dissolve fragrant compounds (e.g., terpenes/terpenoids).
  • the antioxidant is used herein and is capable of substantially preventing oxidation of one or more terpene/terpenoid, thereby contributing in enhancing the stability and/or retention of the terpenes and terpenoids in the paper product.
  • the antioxidant is non-toxic or possesses a very low toxicity and, when burned, produces low/insignificant amounts of irritating/toxic/obnoxious decomposition products.
  • the antioxidant has a very weak to no smell.
  • the antioxidant does not affect substantially the smell of the terpene and/or terpenoid composition.
  • the antioxidant is flavorless.
  • the antioxidant is odorless.
  • the antioxidant is selected from butylated hydroxyanisole (BHA, E320), butylated hydroxytoluene (BHT, E321), cannabinoid, cannabidiol (CBD), propyl gallate (PG, E310), tertiary butylhydroquinone (TBHQ, E319), tocopherols (e.g., vitamin E, E306-E309), vitamin C (E300), a derivative thereof and any combination thereof.
  • BHA butylated hydroxyanisole
  • BHT butylated hydroxytoluene
  • CBD cannabidiol
  • PG propyl gallate
  • TBHQ tertiary butylhydroquinone
  • tocopherols e.g., vitamin E, E306-E309
  • vitamin C E300
  • the antioxidant is selected from cannabidiol (CBD), D 9 - tetrahydrocannabinol (THC), cannabigerol (CBG), cannabinol (CBN), cannabichromene (CBC), cannabichromevarin (CBCV), cannabivarin (CBV), cannabidivarin (CBDV), tetrahydrocannabivarin (THCV), cannabigerovarin (CBGV), cannabicyclol (CBL), cannabielsoin
  • CBDA cannabidiolic acid
  • THCA cannabidiolic acid
  • CBDG cannabigerolic acid
  • CBCV cannabichromenenic acid
  • THCV cannabigerovarinic acid
  • CBDV A cannabidivarinic acid
  • CBDLA cannabicyclolic acid
  • the antioxidant may be used in various concentrations and the optimal concentration depends on the type of the antioxidant used.
  • the choice of antioxidant, its concentration, or the use of mixes of more than one antioxidant should comply with the respective regulations.
  • BHA is used to preserve essential oils in concentrations of up to 0.5%.
  • Natural cannabidiol is as good as synthetic BHT and can be used in concentrations of less than 0.5%.
  • the antioxidant is present in the terpene/terpenoid composition at about 0.1% to about 5% by weight.
  • the antioxidant is present at about 0.1% to about 2%, or at about 0.5% to about 2% by weight.
  • the antioxidant is present at about 0.9% to about 1%, or at about 0.93% to about 0.95% by weight of the terpene/terpenoid composition.
  • the antioxidant is tocopherol or a derivative thereof. In a further embodiment of the invention, the antioxidant is vitamin E, or a derivative thereof.
  • the amount of vitamin E in a paper product is less than about 0.5 mg.
  • vitamin E is present in the composition at about 0.5% to about 2.5% by weight of the composition.
  • vitamin E is present at about 0.5% to about 2% by weight, or at about 0.75% to about 1.5%.
  • vitamin E is present at about 1 % by weight.
  • antioxidant weight per paper area is below about 0.1 mg/cm 2 , or below about 0.01 mg/cm 2 .
  • the antioxidant weight per paper area is about 7xl0 3 mg/cm 2
  • a terpene/terpenoid composition provided herein is substantially water free. In some embodiments, a terpene/terpenoid composition provided herein is essentially water free. In some embodiments, a terpene/terpenoid composition provided herein is water free.
  • a terpene/terpenoid composition provided herein is substantially wax free. In some embodiments, a terpene/terpenoid composition provided herein is essentially wax free. In some embodiments, a terpene/terpenoid composition provided herein is wax free.
  • a terpene/terpenoid composition provided herein is substantially free of solids. In some embodiments, a terpene/terpenoid composition provided herein is essentially free of solids. In some embodiments, a terpene/terpenoid composition provided herein is solids free.
  • a terpene/terpenoid composition provided herein is substantially free of an alcohol. In some embodiments, a terpene/terpenoid composition provided herein is essentially free of an alcohol. In some embodiments, a terpene/terpenoid composition provided herein is alcohol free.
  • a terpene/terpenoid composition provided herein is substantially free of ethylene-vinyl acetate copolymer. In some embodiments, a terpene/terpenoid composition provided herein is essentially free of ethylene-vinyl acetate copolymer. In some embodiments, a terpene/terpenoid composition provided herein is ethylene-vinyl acetate copolymer free.
  • the term“substantially free” refers to a compound or composition comprising less than about 0.5%, or less than about 0.4%, or less than about 0.3%, or less than about 0.2%, or less than about 0.1%, or any percentage in between of a particular compound.
  • the term“essentially free” refers to a compound or composition comprising less than about 0.05%, or less than about 0.04%, or less than about 0.03%, or less than about 0.02%, or less than about 0.01%, or less than about 0.005%, or any percentage in between, or having only trace amounts of a particular compound or of other compounds.
  • the invention overcomes the obstacle associated with evaporation of many flavor and/or aroma compounds by incorporation of one or more fixative agent and/or one or more antioxidant agent, and/or by applying pressure when manufacturing the paper product.
  • the herein disclosed paper product does not include aroma and/or favor compound other than terpene and/or terpenoid. In one or more embodiments, the herein disclosed paper product consists of at least one compound selected from the list of: terpene(s), terpenoid(s), fixative agent(s), and antioxidant(s).
  • the phrase“effective amount” describes an amount of the aroma and/or flavor compound that is sufficient to provide an added aroma and/or flavor to the paper product.
  • an exemplary terpene/terpenoid composition for application to paper products may include:
  • a further exemplary terpene/terpenoid composition for application to paper products may include:
  • terpene profile e.g., 17% g-terpinene, 17% terpinolene, 5% b-cfv-ocimene, 1% D-limonene, 1% P-rra/r.v-caryophyllene, 1% l,8-cineole, 1% P-fra/rv-ocimene
  • a terpene profile e.g., 17% g-terpinene, 17% terpinolene, 5% b-cfv-ocimene, 1% D-limonene, 1% P-rra/r.v-caryophyllene, 1% l,8-cineole, 1% P-fra/rv-ocimene
  • a fixative agent e.g., Glucam P-20
  • a further exemplary terpene/terpenoid composition for application to paper products may include:
  • composition of a terpene profile e.g., 20% -trans- caryophyllene, 10% humulene, 9% D-limonene, 5% linalool;
  • a fixative agent e.g., Glucam P-20
  • an antioxidant e.g., vitamin E acetate.
  • a further exemplary terpene/terpenoid composition for application to paper products may include:
  • a terpene profile (20% terpinolene, 7,0% P-fra/rv-caryophyllene, 5% D-limonene, 5% P-rra/r.v-ocimene, 3% myrcene, 2% b-pinene, 1% g-terpinene, 1% a-pinene); about 40% or above of a fixative agent (e.g., Glucam P-20); and
  • an antioxidant e.g., vitamin E acetate.
  • a further exemplary terpene/terpenoid composition for application to paper products may include:
  • composition of a terpene and/or terpenoid profile about 20% or above by weigh of the composition of a terpene and/or terpenoid profile; and about 20% or above by weigh of the composition of a cannabinoid (e.g., CBD).
  • CBD cannabinoid
  • a further exemplary terpene/terpenoid composition for application to paper products may include:
  • terpene and/or terpenoid profile e.g., 18% g-terpinene, 18% terpinolene, 5% b- .n-ocimene, 2% D-limonene, 2% P-rra/r.v-ocimene, 2% fi-trans-c aryophyllene, 1% l,8-cineole
  • a terpene and/or terpenoid profile e.g., 18% g-terpinene, 18% terpinolene, 5% b- .n-ocimene, 2% D-limonene, 2% P-rra/r.v-ocimene, 2% fi-trans-c aryophyllene, 1% l,8-cineole
  • CBD cannabinoid
  • a further exemplary terpene/terpenoid composition for application to paper products may include:
  • terpene and/or terpenoid profile e.g., 31% P-/ran.Y-caryophyllene, 15% humulene, 14% D-limonene, 8% linalool, 1% caryophyllene oxide, 1% b-pinene, 1% a-terpineol
  • a terpene and/or terpenoid profile e.g., 31% P-/ran.Y-caryophyllene, 15% humulene, 14% D-limonene, 8% linalool, 1% caryophyllene oxide, 1% b-pinene, 1% a-terpineol
  • CBD cannabinoid
  • a further exemplary terpene/terpenoid composition for application to paper products may include:
  • composition of a cannabinoid e.g., CBD
  • a fixative agent other than a cannabinoid e.g., PEG-400
  • the present invention provides a method of manufacturing an aromatized and/or flavored paper product.
  • the herein disclosed paper products are manufactured by preparing a composition comprising certain amounts of an aroma and/or a flavor compound.
  • the composition includes at least one antioxidant and/or at least one fixative agent.
  • an amount of the overall compounds in the composition over the paper is between about 0.4 mg/cm 2 to about 2 mg/cm 2 . Applying an amount of the composition on one side of the paper.
  • the method includes preparing a first composition of a cannabinoid and applying same onto the paper product and preparing a second composition that includes terpenes and/or terpenoids and applying same following the application of the first composition.
  • the first and/or second compositions include an antioxidant.
  • the first composition includes a fixative agent other than cannabinoid. Spreading the composition, optionally with using one or more rollers. Alternatively, or additionally the paper product may be immersed within a bath containing the terpene and/or terpenoid composition.
  • the pressure is between about 16 g/cm 2 and about 775 g/cm 2 .
  • the pressure is between about 16 g/cm 2 and about 620 g/cm 2 , between about 16 g/cm 2 and about 465 g/cm 2 , between about 16 g/cm 2 and about 310 g/cm 2 , between about 16 g/cm 2 and about 155 g/cm 2 , between about 16 g/cm 2 and about 775 g/cm 2 , between about 62 g/cm 2 and about 775 g/cm 2 , between about 124 g/cm 2 and about 775 g/cm 2 , between about 155 g/cm 2 and about 775 g/cm 2 , between about 310 g/cm 2 and about 775 g/cm 2 , between about 465 g/cm 2 and about 775 g/cm 2 , or between about 620 g/cm
  • the method may optionally include cutting the paper to any desired dimensions and packing the paper with the aroma and flavor compounds inserted therein the paper.
  • the method further comprises a step of sealing the package.
  • the paper is inserted within the package immediately thereafter the paper is prepared.
  • the method may optionally include a step of incubating the paper product with the composition for at least about 10 minutes.
  • Reference to the term“about” has its usual meaning in context to the herein invention of a reasonable variation from a stated amount that retains the ability to achieve one or more functional effect to substantially the same extent as the stated amount.
  • the term may also refer herein to a value of plus or minus 15% of the stated value; plus or minus 10% of the stated value; or plus or minus 5%, or plus or minus 1%, or plus or minus 0.5%, or plus or minus 0.1%, or any percentage in between.
  • "about 20" may mean or include amounts from 18 up to and including 22, to the extent those amounts achieve one or more functional effect to substantially the same extent as an amount of 20 would.
  • a molecule is said to be a "chemical derivative" of another molecule when it contains additional chemical moieties not normally a part of the molecule. Such moieties can improve the molecule's solubility, absorption, biological half-life, and the like. The moieties can alternatively decrease the toxicity of the molecule, eliminate or attenuate any undesirable side effect of the molecule, and the like. Moieties capable of mediating such effects are disclosed in Remington's Pharmaceutical Sciences (1980). Procedures for coupling such moieties to a molecule are well known in the art.
  • the term "chemical derivative” includes a functional activity of a molecule that possesses an activity that is substantially similar to a chemical activity of the molecule stated.
  • Example 1- Application on the papers of CBD (100 mg), dissolved in 100 m ⁇ diethyl ether, which after the solvent evaporation provided papers infused with CBD (45 mg) and it was followed by the infusion of pure terpenoids (45 mg).
  • the final weight ratio between CBD and the terpenoids was 1 : 1.
  • the mixture (mg) retained on the papers during 10 min interval in open environment is presented in FIG. 1.
  • the terpene weight (mg) remaining on the papers during the 10 minutes period in open environment is presented in FIG 2.
  • Example 2- Application of various amounts (10 to 240 m ⁇ ) of a mixture containing CBD and terpenoids in ratio 1: 1 (Tables 1 and 2, FIG. 3). As can be seen from FIG. 3 application of a mixture of CBD and terpenoids in ratio 1: 1 ensures more than 90% retention in the paper of the overall mixture and in particular of the terpenoids, resp.
  • Table 1 retention of various amounts of a mixture of CBD and terpenoids (1: 1) during 10 minutes at ambient temperature.
  • Table 2 - Weight (%) of a mixture of CBD and terpenoids in a ratio of 1: 1, retained on papers infused with various amounts (m ⁇ ) of the mixture during 10 minutes period at ambient conditions.
  • Example 3 The following are exemplary compositions of terpenes and/or terpenoids, an antioxidant (vitamin E acetate) and a fixative agent (Glucam P-20).
  • Formulation #1 The formulation composition includes 49.5% terpene profile (17% g- terpinene, 17% terpinolene, 5% b-cfv-ocimene, 1% D-limonene, 1% P-fra/rv-caryophyllene, 1% l,8-cineole, 1% P-fra/rv-ocimene), 49.5% Glucam P-20, and 1.0% vitamin E acetate.
  • Formulation #2 The formulation composition includes 49,5% terpene profile (20% b- /ran.v-caryophyllene, 10% humulene, 9% D-limonene, 5% linalool), 49,5% Glucam P-20, and 1,0% vitamin E acetate.
  • Formulation #3 The formulation composition includes 49,5% terpene profile (20% terpinolene, 7,0% fi-trans-c aryophyllene, 5% D-limonene, 5% b-rra/i.v-ocimene, 3% myrcene, 2% b-pinene, 1% g-terpinene, 1% a-pinene), 49,5% Glucam P-20, and 1,0% vitamin E acetate.
  • Example 4 The following are exemplary compositions of terpenes and/or terpenoids, and a cannabidiol.
  • Formulation #4 The formulation composition includes 50.0% terpene profile (18% g- terpinene, 18% terpinolene, 5% b-cfv-ocimene, 2% D-limonene, 2% P-rra/r.v-ocimene, 2% b- /ran.v-caryophyllene, 1% l,8-cineole) and 50.0% CBD.
  • Formulation #5 The formulation composition includes 78,3% terpene profile (31% b- /ran.v-caryophyllene, 15% humulene, 14% D-limonene, 8% linalool, 1% caryophyllene oxide, 1% b-pinene, 1% a-terpineol) and 21,7% CBD.
  • Example 5 The following is an exemplary composition of terpenes and/or terpenoids, and a combination of cannabidiol and PEG-400 as fixatives.
  • Formulation #6 The formulation composition includes 26,4% terpene profile (11% terpinolene, 4% b-/t£//7.n- c ⁇ Gg r ⁇ g1 ⁇ 6h6, 2% D-limonene, 2% b-rra/i.v-ocimene, 1% myrcene, 1% b-pinene), 7,0% CBD, and 66.0% PEG-400.
  • Example 6 The following table 3 illustrates the Hansen Solubility Parameters (HSP) of cellulose, fixatives, selected cannabinoids, and major cannabis fragrance terpenes. Table 3 - the Hansen Solubility Parameters (HSP) of cellulose, fixatives, selected cannabinoids, and major cannabis fragrance terpenes.
  • CBD solubility parameters of cannabinoids and terpene(s)/terpenoid(s) were calculated using the Hansen HSPiP software.
  • the minimal quantity of CBD that improves the retention of b-caryophyllene is about 1% (b- caryophyllene: CBD in a ratio of 100: 1 or b-caryophyllene: CBD in a ratio of 1 :0.0l).
  • Example 6- A mixture of CBD and a relatively unstable terpenoid, such as linalool (flash point 78 °C, Sigma-Aldrich) were incorporated onto a paper product.
  • linalool flash point 78 °C, Sigma-Aldrich
  • 50% CBD by weight (linalool: CBD 1: 1) improves significantly the linalool retention on the paper at ambient conditions for the first 15 minutes after the infusion.
  • the minimal amount of CBD able to fixate linalool is about 20% (linalool: CBD in a ratio of 4: 1 or linalool: CBD 1 :0.25).

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Cigarettes, Filters, And Manufacturing Of Filters (AREA)

Abstract

La présente invention concerne des produits en papier, notamment des produits en papier à fumer, enrichis de manière stable avec des cannabinoïdes actifs et des composés d'arôme et/ou de parfum. Plus particulièrement, l'invention concerne des produits en papier enrichis avec un profil cannabinoïde et un profil terpène, imitant l'effet du cannabis.
PCT/IL2019/050965 2018-08-31 2019-08-28 Produits en papier aromatisés et parfumés comprenant des terpènes et des cannabinoïdes WO2020044343A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201862725350P 2018-08-31 2018-08-31
US62/725,350 2018-08-31

Publications (1)

Publication Number Publication Date
WO2020044343A1 true WO2020044343A1 (fr) 2020-03-05

Family

ID=69643559

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IL2019/050965 WO2020044343A1 (fr) 2018-08-31 2019-08-28 Produits en papier aromatisés et parfumés comprenant des terpènes et des cannabinoïdes

Country Status (1)

Country Link
WO (1) WO2020044343A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20230036051A1 (en) * 2021-07-21 2023-02-02 Resurgent Biosciences, Inc. Cannabinoid storage stability
WO2024044145A1 (fr) * 2022-08-23 2024-02-29 Tribu Hemp Llc Composition de cannabinoïde et de terpène à appliquer sur un matériau absorbant

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080011312A1 (en) * 2005-03-15 2008-01-17 Japan Tobacco Inc. Low flame-spreading cigarette paper
US20130209753A1 (en) * 2012-02-14 2013-08-15 Amer M. Idheileh Laminated rolling papers
US20150181925A1 (en) * 2013-12-26 2015-07-02 John Turner Herbal smoking blend
WO2017196840A1 (fr) * 2016-05-09 2017-11-16 Michael Beck Procédé et dispositif pour un papier à rouler des cigarettes infusé de résine

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080011312A1 (en) * 2005-03-15 2008-01-17 Japan Tobacco Inc. Low flame-spreading cigarette paper
US20130209753A1 (en) * 2012-02-14 2013-08-15 Amer M. Idheileh Laminated rolling papers
US20150181925A1 (en) * 2013-12-26 2015-07-02 John Turner Herbal smoking blend
WO2017196840A1 (fr) * 2016-05-09 2017-11-16 Michael Beck Procédé et dispositif pour un papier à rouler des cigarettes infusé de résine

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
BERNHARD EITZINGER ET AL.: "The Pore Size Distribution of Naturally Porous Cigarette Paper and its Relation to Permeability and Diffusion Capacity", BEITRÄGE ZUR TABAKFORSCHUNG INTERNATIONAL, CONTRIBUTIONS TO TOBACCO RESEARCH, vol. 26, no. 7, 1 September 2015 (2015-09-01), pages 312 - 319, XP055697287 *
SAMEER H. KAREEM ET AL.: "Porosity Measurements of Cellulose Acetate Filters for Some", AL- MUSTANSIRIYA J. SCI, vol. 21, no. 2, 1 January 2010 (2010-01-01), pages 57 - 66, XP055697285 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20230036051A1 (en) * 2021-07-21 2023-02-02 Resurgent Biosciences, Inc. Cannabinoid storage stability
WO2024044145A1 (fr) * 2022-08-23 2024-02-29 Tribu Hemp Llc Composition de cannabinoïde et de terpène à appliquer sur un matériau absorbant

Similar Documents

Publication Publication Date Title
US11346051B2 (en) Aromatized and flavored paper products
US10821147B2 (en) Printable cannabinoid and terpene compositions
Bilia et al. [Retracted] Essential Oils Loaded in Nanosystems: A Developing Strategy for a Successful Therapeutic Approach
US10835839B1 (en) Cannabis products modified by removing volatile organic compounds and adding volatile unsaturated hydrocarbons
CN110177543A (zh) 包含纯化***素的水溶性组合物
EP3589787A1 (fr) Produits en papier aromatisés et parfumés
US10561731B2 (en) Method and compositions for solubilizing non-polar constituents
US20220323403A1 (en) Cannabis tablet formulations and compositions and methods of making the same
WO2020044343A1 (fr) Produits en papier aromatisés et parfumés comprenant des terpènes et des cannabinoïdes
AU2018227544A1 (en) Compositions purposefully selected comprising purified cannabinoids and/or purified terpenes
US20210038666A1 (en) Printable cannabinoid and terpene compositions
WO2023028708A1 (fr) Compositions de cannabinoïdes solubles dans l&#39;eau, procédés de préparation et d&#39;utilisation
EP3261629A1 (fr) Compositions comprenant des combinaisons de cannabinoïdes purifiés, ayant au moins un flavonoïde, terpène ou minéral
Omar et al. Recent progress in eco-synthesis of essential oil-based nanoparticles and their possible mechanisms
US20220241199A1 (en) Cannabinoid emulsion composition and method of manufacture
EP3761821A1 (fr) Dispositif et procédé d&#39;administration de principes actifs
US20220266168A1 (en) Methods of modifying a naturally occurring cannabis raw plant material, a purified cannabis product from a naturally occurring cannabis raw plant material, and a modified cannabis product from a naturally occurring cannabis raw plant material
Recio-Cázares et al. Relationship Between the Chemical Composition and Transport Properties with the Antimicrobial Activity of Essential Oil from Leaves of Mexican Lippia (Aloysia citriodora) Extracted by Hydro-Distillation

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 19855469

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 19855469

Country of ref document: EP

Kind code of ref document: A1