CN111685361A - Latent fragrant cigarette paper containing-hydroxy acid alcohol ester as well as preparation method and application of latent fragrant cigarette paper - Google Patents
Latent fragrant cigarette paper containing-hydroxy acid alcohol ester as well as preparation method and application of latent fragrant cigarette paper Download PDFInfo
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- CN111685361A CN111685361A CN201910183922.3A CN201910183922A CN111685361A CN 111685361 A CN111685361 A CN 111685361A CN 201910183922 A CN201910183922 A CN 201910183922A CN 111685361 A CN111685361 A CN 111685361A
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- alcohol ester
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- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B3/00—Preparing tobacco in the factory
- A24B3/12—Steaming, curing, or flavouring tobacco
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- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
- A24B15/301—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances by aromatic compounds
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- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
- A24B15/34—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a carbocyclic ring other than a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
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- 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
- D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
- D21H17/14—Carboxylic acids; Derivatives thereof
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- 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
- D21H19/00—Coated paper; Coating material
- D21H19/10—Coatings without pigments
- D21H19/14—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Manufacture Of Tobacco Products (AREA)
- Paper (AREA)
- Cigarettes, Filters, And Manufacturing Of Filters (AREA)
Abstract
The invention belongs to the technical field of cigarette flavoring, and particularly provides a hydroxy acid alcohol ester latent fragrant cigarette paper, and a preparation method and application thereof. The invention innovatively applies the hydroxy-acid alcohol ester latent aroma to the technical route of perfuming cigarette paper. The cigarette paper provided by the invention can release alcohol perfume and another lactone by self-cracking of the hydroxy acid alcohol ester potential perfume during combustion. The cigarette paper prepared by the invention can effectively provide the compound aroma of alcohol spices and another lactone during the combustion of the cigarette, and can improve the smoking quality of the cigarette.
Description
Technical Field
The invention belongs to the technical field of cigarette paper and flavors and fragrances, and particularly relates to a preparation method of cigarette paper containing hydroxy-acid alcohol ester.
Background
The cigarette paper is an essential auxiliary material in the cigarette manufacturing process, and burns together with tobacco shreds in the cigarette smoking process, so that the cigarette paper has a burnt paper taste and the smoking quality of the cigarette is influenced. The cigarette paper is added with fragrance, so that the positive influence of the combustion process of the cigarette paper on the cigarette smoking can be improved.
The prior cigarette paper flavoring method mainly comprises the following technical means: 1) adding the spice directly to the cigarette paper in the form of coating liquid; 2) performing cyclodextrin molecule encapsulation or embedding on the spice to prepare a paste, and then adding the paste into the cigarette paper in a coating liquid manner; 3) performing cyclodextrin molecule encapsulation or embedding on the spice, performing powder spraying and drying to obtain powder, and adding the powder into the cigarette paper in a filling manner; 4) the perfume is loaded on the inorganic porous material, the surface of the porous material is coated with the water-insoluble high polymer material to form a film for sealing the perfume, and the film is added to the cigarette paper in a filling mode.
Alcohol spices are important fragrant raw materials in cigarettes, but the application of the alcohol spices to the perfuming of the cigarettes often has two problems: the volatility causes the fragrance to be difficult to store for a long time, and in addition, the smoked taste is inconsistent.
For example, leaf alcohol naturally exists in various plants, is a representative spice of green aroma, has fresh green leaf aroma, has special herb aroma and leaf odor after being diluted, and is widely usedIs applied to blending of essence with natural fresh flavor[1]. To increase the processing and storage resistance of folyl alcohol, the following studies have been mainly made: minjie (Chinese character)[2]And the leaf alcohol microcapsule is prepared by taking chitosan oligosaccharide as a wall material, and the particle size and the embedding rate of the leaf alcohol microcapsule are examined. Zhao Ming Qin etc[3]The leaf alcohol is derived into 3-picolinic acid leaf alcohol ester, the thermal cracking behavior of the 3-picolinic acid leaf alcohol ester at different temperatures is discussed, a small amount of free leaf alcohol can be generated in a cracking state, and the cigarette flavoring effect of the 3-picolinic acid leaf alcohol ester is investigated. Poplar and stannum root for flood and deluxe[4]The leaf alcohol is derived to prepare leaf alcohol glycoside (namely cis-3-hexenyl- β -D-glucopyranoside), the thermal degradation behavior and the products of the leaf alcohol glycoside are examined by de-Wangcui and the like, the optimal temperature for the leaf alcohol glycoside to release the leaf alcohol is 350 ℃, the characteristic product of thermal cracking is the leaf alcohol, and the main cracking reaction is the breakage of oxygen glycosidic bond[5]。
In the prior art, a technical route for applying the-hydroxy acid alcohol ester latent aromatic to perfuming cigarette paper is not available.
Reference to the literature
[1] The research progress of folyl alcohol is progress [ J ] Chinese food additives, 2004(6):34-37.
[2] Minjie, Wang Shun Xian, Zhuquan, etc. research on the shell forming process of the leaf alcohol microcapsules [ J ] printing and dyeing auxiliary agents, 2009,26(12):24-26.
[3] Zhao Mingzhou, Baozhu, Jixiaoming, etc. the synthesis of 3-pyridinecarboxylic acid leaf alcohol ester and its application in perfuming cigarette [ J ] modern food science and technology, 2013(11): 2669-2674).
[4] Poplar stannum flood, Wancui, Wanweimin, and the like, synthesis, purification and characterization of cis-3-hexenyl-beta-D-glucopyranoside [ J ] proceedings of Jiangsu university (Nature science edition), 2007,28(5): 438-.
[5] TGA/SDTA, DSC and Py-GC-MS analyze the thermal degradation property of the phytol glucoside (J), the university report of Jiangsu (natural science edition), 2006,27(6):475-479.
Disclosure of Invention
In view of the problems of the prior art, the invention provides a cigarette paper with latent fragrance of hydroxy acid alcohol ester (the cigarette paper is also called cigarette paper containing the latent fragrance of hydroxy acid alcohol ester, or simply called cigarette paper), and aims to provide a brand-new cigarette paper capable of releasing alcohol fragrance and lactone fragrance in a smoking process.
The second purpose of the invention is to provide a preparation method of the hydroxy acid alcohol ester latent fragrant cigarette paper.
The third purpose of the invention is to provide the application of the hydroxy acid alcohol ester latent fragrant cigarette paper.
The fourth purpose of the invention is to provide a cigarette with the function of simultaneously slowly releasing the alcohol spices and the lactone.
The hydroxy acid alcohol ester latent aroma cigarette paper is characterized in that the hydroxy acid alcohol ester latent aroma (also called 5-hydroxy acid alcohol ester latent aroma) is at least one compound with a structural formula 1;
the-hydroxy acid alcohol ester latent aromatic substance can be cracked into R at the temperature of not less than 120 DEG C1OH and a-lactone of the structure of formula 2;
R1OH and-lactones have an acceptable odor on cigarettes.
The invention innovatively applies the hydroxy-acid alcohol ester latent aroma to the technical route of perfuming cigarette paper. The alcohol ester latent aromatic substance contained in the cigarette paper provided by the invention can be cracked to release alcohol perfume and another lactone during combustion. The technology of the invention can effectively solve the problem of burst release of low-boiling-point alcohol spices, reduce the fragrance difference between the first few mouths and the last few mouths and obviously improve the smoking taste.
The invention provides a new idea of adding various mixed aromas into cigarettes, namely, the various aromas are released by utilizing the self dissociation of innovative materials. Based on the innovative inventive concept of the invention, the invention utilizes the hydroxy-acid alcohol ester as the additive of the cigarette paper, and utilizes the compound to generate intramolecular cracking in the smoking process and release two types of aroma substances, thereby realizing the controlled-release flavoring effect of the two types of aroma substances. Compared with the method of directly applying the two types of incense raw materials in the cigarette, the hydroxy acid alcohol ester latent incense in the cigarette paper can release alcohol perfume and lactone in the burning and smoking process of the cigarette. The technology can reduce or avoid the volatile loss of the two spices in the processing and storage stages, and can realize the uniform and stable release of the two spices in the cigarette smoking.
In order to better exert the fragrance release effect of the 5-hydroxy acid alcohol ester and improve the self-dissociation behavior in the smoking process, the research of the invention finds that the release behavior in the smoking process can be improved and the mixed perfuming effect can be improved by regulating and controlling the substituent groups in the compound shown in the formula 1 and through the intramolecular interaction between the groups.
Preferably, R2、R3Is a hydrocarbon group of H, C1 to C10; further preferably, R is2Is H; r3Is C1-C7 alkyl. Even more preferably, R is3Is straight chain alkyl.
Or, R2、R3Cyclizing to form a saturated cyclic group, a partially unsaturated cyclic group, or an aromatic group; preferably, R is1、R2And cyclizing to synthesize saturated cycloalkyl or aryl.
Further preferably, the alcohol ester of a hydroxy acid has the structure of formula 1-a or formula 1-B:
said R4Is a hydrocarbon group of H, C1 to C4.
The lactone comprises at least one of caprolactone, heptalactone, octalactone, nonalactone, decalactone, undecalactone, dihydrocoumarin and octahydrocoumarin.
Further preferably, R is1OH is selected from the group consisting of geraniol, isoamyl alcohol, phenethyl alcohol, geraniol, citronellol, anisyl alcohol, cinnamyl alcohol, menthol,At least one of isopulegol, most preferably leaf alcohol or geraniol.
Preferably, the-hydroxy acid alcohol ester latent fragrance comprises 5-hydroxy hexanoic acid leaf alcohol ester, 5-hydroxy heptanoic acid leaf alcohol ester, 5-hydroxy octanoic acid leaf alcohol ester, 5-hydroxy nonanoic acid leaf alcohol ester, 5-hydroxy decanoic acid leaf alcohol ester, 5-hydroxy undecanoic acid leaf alcohol ester, 5-hydroxy dodecanoic acid leaf alcohol ester, 3- (2-hydroxycyclohexyl) propionic acid leaf alcohol ester, 3- (2-hydroxyphenyl) propionic acid geraniol ester and the like, and comprises but is not limited to at least one of the above 5-hydroxy acid leaf alcohol esters.
Preferably, the alcohol ester of a hydroxy acid is cleaved during smoking of the cigarette.
Further preferably, the hydroxy acid alcohol ester is cracked at the temperature of 120-260 ℃.
Preferably, the-hydroxy acid alcohol ester latent fragrance is coated on the surface of the cigarette paper or is uniformly dispersed in the cigarette paper.
Preferably, the weight of the-hydroxy acid alcohol ester latent aroma accounts for 0.0001-0.5% of the weight of the cigarette paper; more preferably 0.001 to 0.01%.
The hydroxy acid alcohol ester cigarette latent aromatic substance can pass R1OH and-lactone are subjected to ester exchange reaction under the catalysis of acid or alkali as a catalyst.
The transesterification reaction scheme of the present invention is shown in equation 1:
the invention also provides a preparation method of the-hydroxy acid alcohol ester latent fragrant cigarette paper, which is characterized in that the-hydroxy acid alcohol ester latent fragrant substance is dissolved by a solvent to obtain a coating liquid, and the coating liquid is coated on the cigarette paper, or the cigarette paper is soaked in the coating liquid and then dried to obtain the-hydroxy acid alcohol ester latent fragrant cigarette paper.
The off-line coating method of the present invention may be gravure coating. Wherein the speed of the coating machine is preferably controlled at 50-100m/min, and the temperature of the oven is preferably controlled at 70-110 ℃.
Preferably, the solvent is an alcohol-water mixed solution, and the alcohol is ethanol and/or propylene glycol.
The invention also provides application of the cigarette paper, which is used for preparing a combustible cigarette or a heating non-combustible cigarette.
The invention also provides a combustible cigarette with the function of simultaneously slowly releasing the alcohol spices and the lactone, and the tobacco shred rod is coated with the cigarette paper.
The invention has the beneficial effects that:
1. the cigarette paper prepared by the invention can uniformly release R in the burning process of the cigarette1the-OH and the-lactone generate composite aroma provided by two spices simultaneously, and the use value of the cigarette paper and the smoking quality of the cigarette are improved;
2. and two monomer raw material spices R are directly applied to cigarettes1Application of the-hydroxy acid leaf alcohol esters to cigarette paper can reduce the volatile loss of both flavors during processing and in-stock compared to-lactones; solves the problem that the low-boiling point spice leaf alcohol has inconsistent front and back mouthfeel in cigarette smoking.
Drawings
FIG. 1: MS (EI) spectrum of 3- (2-hydroxyphenyl) menthyl propionate;
FIG. 2: GC spectrum of a thermal cracking product of 3- (2-hydroxyphenyl) menthyl propionate at 200 ℃;
FIG. 3: TG-DSC curve of menthyl 3- (2-hydroxyphenyl) propionate.
Detailed Description
The following examples are intended to illustrate the invention without further limiting it.
Example 1
6.00g of leaf alcohol, 3.42g of caprolactone and 50mg of citric acid were mixed in a 50mL single-neck flask and reacted at 70 ℃ with stirring for 3 hours. GC-MS detects the progress of the reaction. After the reaction, 3.63g of 5-hydroxycaproic acid leaf alcohol ester is obtained by column chromatography separation and purification. The yield was 56%.
Dissolving 3g of 5-hydroxyhexanoate leaf alcohol ester in 997g of absolute ethyl alcohol to prepare a 0.3% solution, and diluting the ethanol solution with 9000g of water to prepare a 0.03% solution in percentage by mass, wherein the solution is the coating liquid.
Coating the coating liquid on the cigarette paper in an off-line gravure coating mode, controlling the speed of a coating machine at 60m/min, controlling the temperature of an oven at 90 ℃, and drying to obtain the cigarette paper containing 5-hydroxycaproic acid leaf alcohol ester, wherein the addition amount of the 5-hydroxycaproic acid leaf alcohol ester is about 0.005% of the cigarette paper.
Taking cut tobacco with certain low tar specification, rolling the cigarette paper into cigarettes, and rolling the cigarettes with the same cut tobacco and the cigarette paper without the 5-hydroxy caproic acid phyllyl ester.
Tests show that in the smoking process of the cigarette loaded with the cigarette paper, 5-hydroxy caproic acid leaf alcohol ester is subjected to intramolecular cracking, and two fragrances, namely caprolactone and leaf alcohol, can be uniformly released. Compared with the result of the control sample, the cigarette paper cigarette of the case has more obvious fresh and fragrant characteristics, increased thick sense of fragrance and good consistency of the smoking taste.
Example 2
Geraniol 3- (2-hydroxyphenyl) propionate was prepared by transesterification of geraniol and dihydrocoumarin under acidic conditions in a similar manner to that in example 1.
3g of geraniol 3- (2-hydroxyphenyl) propionate is dissolved in 997g of absolute ethanol to prepare a 0.3% solution, and 9000g of water is added to the ethanol solution to dilute the solution to prepare a coating solution with the mass percent of 0.03%. Adding the mixture to cigarette paper in an off-line gravure coating mode, controlling the speed of a coating machine at 60m/min, controlling the temperature of an oven at 100 ℃, and drying to obtain the cigarette paper containing 3- (2-hydroxyphenyl) geraniol propionate, wherein the adding amount of the 3- (2-hydroxyphenyl) geraniol propionate accounts for about 0.005% of the cigarette paper.
And (3) taking cut tobacco with a certain low tar specification, rolling the cut tobacco into cigarettes by using the cigarette paper, and rolling the cigarettes by using the same cut tobacco and the cigarette paper without adding the 3- (2-hydroxyphenyl) geraniol propionate.
Tests show that the 3- (2-hydroxyphenyl) geraniol propionate generates intramolecular cracking during the smoking process of the cigarette loaded with the cigarette paper of the invention, and can uniformly release two fragrances of dihydrocoumarin and geraniol. Compared with the control sample, the cigarette of the case has more obvious faint scent characteristic, obviously increased bean scent characteristic and good consistency of the smoking taste.
Example 3
In a similar manner to example 1, 3- (2-hydroxyphenyl) propanoic acid leaf alcohol ester was prepared.
0.1g of 3- (2-hydroxyphenyl) propionic acid leaf alcohol ester is taken and dissolved in 50g of absolute ethyl alcohol, and 950g of water is added for dilution to prepare 0.01 percent solution. Soaking the cigarette paper in the solution for 10 minutes, airing the paper at room temperature after soaking, and drying to obtain the cigarette paper containing 3- (2-hydroxyphenyl) propionic acid leaf alcohol ester, wherein the addition amount of the 3- (2-hydroxyphenyl) propionic acid leaf alcohol ester is about 0.15 percent of the cigarette paper.
Taking cut tobacco with certain low tar specification, rolling the cigarette paper into cigarettes, and rolling the cigarettes with the same cut tobacco and the cigarette paper without adding 3- (2-hydroxyphenyl) propionic acid phyllo alcohol ester as a contrast. Tests show that in the smoking process of the cigarette loaded with the cigarette paper, the 3- (2-hydroxyphenyl) propionic acid leaf alcohol ester is subjected to intramolecular cracking, and two fragrances of dihydrocoumarin and leaf alcohol can be uniformly released. The result of the smoking evaluation compared with the control sample shows that the fragrance and bean fragrance of the cigarette of the invention are too obvious, and the original fragrance of the tobacco is obviously suppressed. The consistency of the smoking mouthfeel is better.
Example 4
The method similar to the embodiment 1 is adopted, and the ester exchange reaction is carried out on the L-menthol and the dihydrocoumarin under the acidic condition to prepare the 3- (2-hydroxyphenyl) menthyl propionate; the melting point is 83-84 ℃, and the mass spectrum of the mass spectrum is shown in figure 1.
Thermal cracking analysis is carried out on menthyl 3- (2-hydroxyphenyl) propionate, and at 200 deg.C, the cracked product is menthol and dihydrocoumarin, as shown in figure 2.
Thermogravimetric analysis is carried out on the 3- (2-hydroxyphenyl) menthyl propionate, the latent aroma starts to crack at about 120 ℃, the weight loss rate is gradually increased along with the gradual gasification of the temperature, and the latent aroma is completely gasified when the temperature reaches about 260 ℃. Its TG-DSC spectrum is shown in figure 3.
1g of menthol 3- (2-hydroxyphenyl) propionate is dissolved in 999g of absolute ethyl alcohol to prepare a 0.1 percent solution, and 9000g of water is added into the ethanol solution to dilute the solution to prepare a coating solution with the mass percent of 0.01 percent. Adding the cigarette paper into the cigarette paper in an off-line gravure coating mode, controlling the speed of a coating machine at 60m/min, controlling the temperature of an oven at 100 ℃, and drying to obtain the cigarette paper containing 3- (2-hydroxyphenyl) menthyl propionate, wherein the adding amount of the 3- (o-hydroxyphenyl) menthyl propionate accounts for about 0.0017% of the cigarette paper.
Taking cut tobacco with certain low tar specification, rolling the cigarette paper into cigarettes, and rolling the cigarettes with the same cut tobacco and the cigarette paper without 3- (2-hydroxyphenyl) menthyl propionate. Tests show that in the smoking process of the cigarette loaded with the cigarette paper, the 3- (2-hydroxyphenyl) menthyl propionate is subjected to intramolecular cracking, and two fragrances, namely dihydrocoumarin and L-menthol, can be uniformly released.
Example 5
The 3- (2-hydroxyphenyl) phenylpropanoic acid phenethyl alcohol ester is prepared by the similar method of the embodiment 1 through ester exchange reaction of phenethyl alcohol and dihydrocoumarin under the acidic condition.
3g of 3- (2-hydroxyphenyl) phenethyl alcohol propionate is dissolved in 997g of absolute ethyl alcohol to prepare a 0.3 percent solution, and 9000g of water is added into the ethanol solution to dilute the solution to prepare a coating solution with the mass percent of 0.03 percent. Adding the obtained product to cigarette paper in an off-line gravure coating mode, controlling the speed of a coating machine at 60m/min, controlling the temperature of an oven at 100 ℃, and drying to obtain the cigarette paper containing 3- (2-hydroxyphenyl) phenethyl alcohol propionate, wherein the addition amount of the 3- (o-hydroxyphenyl) phenethyl alcohol propionate accounts for about 0.005% of the cigarette paper.
Taking tobacco shreds with certain low tar specification, rolling into cigarette with the above cigarette paper, and rolling into cigarette with the same tobacco shreds and cigarette paper without 3- (2-hydroxyphenyl) phenylpropionate. Tests show that in the smoking process of the cigarette loaded with the cigarette paper, the 3- (2-hydroxyphenyl) phenethyl alcohol propionate is subjected to intramolecular cracking, and two fragrances of dihydrocoumarin and phenethyl alcohol can be uniformly released.
Example 6
31.25g of menthol, 11.41g of caprolactone, 14.82g of dihydrocoumarin and 0.4g of citric acid are mixed in a 100mL single-neck bottle and heated at 70 ℃ for 5 hours to prepare the mixed latent aroma containing 5-hydroxyhexanoate menthol ester and 3- (2-hydroxyphenyl) propionate menthol ester (in this case, the mixed latent aroma is also called as-hydroxy acid menthol ester collectively).
Cigarette paper was prepared in a similar manner to example 1. And a comment experiment was performed thereon.
Claims (16)
1. The hydroxy acid alcohol ester latent aromatic cigarette paper is characterized in that the hydroxy acid alcohol ester latent aromatic substance is at least one compound with a structural formula 1;
the-hydroxy acid alcohol ester latent aromatic substance can be cracked into R at the temperature of not less than 120 DEG C1OH and a-lactone of the structure of formula 2;
R1OH and-lactones have an acceptable odor on cigarettes.
2. The hydroxy acid alcohol ester pro-fragrance cigarette paper of claim 1, wherein R is R2、R3Is a hydrocarbon group of H, C1 to C10; or R2、R3Cyclizing to form a saturated cyclic group, a partially unsaturated cyclic group, or an aromatic group.
3. The hydroxy acid alcohol ester pro-fragrance cigarette paper of claim 1, wherein R is R2Is H; r3Is C1-C7 alkyl.
4. The hydroxy acid alcohol ester pro-fragrance cigarette paper of claim 3, wherein R is R3Is straight chain alkyl.
5. The hydroxy acid alcohol ester pro-fragrance cigarette paper of claim 1, wherein R is R2、R3And cyclizing to synthesize saturated cycloalkyl or aryl.
6. The hydroxy acid alcohol ester pro-fragrance cigarette paper of claim 5, wherein the hydroxy acid alcohol ester pro-fragrance has the structure of formula 1-A or formula 1-B:
said R4Is a hydrocarbon group of H, C1 to C4.
7. The hydroxy acid alcohol ester latent aromatic cigarette paper according to any one of claims 1 to 6, wherein R is R1-OH is at least one of leaf alcohol, isoamyl alcohol, phenethyl alcohol, geraniol, citronellol, anisyl alcohol, cinnamyl alcohol, menthol and isopulegol.
8. The hydroxy acid alcohol ester pro-fragrance cigarette paper according to claim 1, wherein the hydroxy acid alcohol ester pro-fragrance comprises 5-hydroxyhexanoate, 5-hydroxyheptanoate, 5-hydroxyoctanoate, 5-hydroxynonanoate, 5-hydroxydecanoate, 5-hydroxyundecanoate, 5-hydroxydodecanoate, 3- (2-hydroxycyclohexyl) propionate, 3- (2-hydroxyphenyl) propionate, isoamyl 3- (2-hydroxyphenyl) propionate, geranyl 3- (2-hydroxyphenyl) propionate, and the like, and includes, but is not limited to, at least one of the above 5-hydroxy acid folates.
9. The hydroxy acid alcohol ester pro-fragrance cigarette paper of claim 1, wherein the hydroxy acid alcohol ester pro-fragrance is cracked during smoking of the cigarette.
10. The hydroxy acid alcohol ester latent aromatic cigarette paper according to claim 9, wherein the hydroxy acid alcohol ester latent aromatic substance is cracked at a temperature of 120-260 ℃.
11. The hydroxy acid alcohol ester pro-fragrance cigarette paper according to claim 1, wherein the hydroxy acid alcohol ester pro-fragrance is coated on the surface of the cigarette paper or is uniformly dispersed in the cigarette paper.
12. The hydroxy acid alcohol ester latent aroma cigarette paper according to claim 1, wherein the weight of the single hydroxy acid alcohol ester latent aroma is 0.0001-0.5% of the weight of the cigarette paper.
13. The preparation method of the hydroxy acid alcohol ester latent aromatic cigarette paper as claimed in any one of claims 1 to 12, characterized by dissolving the hydroxy acid alcohol ester latent aromatic substance with a solvent to obtain a coating liquid, coating the coating liquid on the cigarette paper, or soaking the cigarette paper in the coating liquid, and then drying to obtain the hydroxy acid alcohol ester latent aromatic cigarette paper.
14. The method according to claim 13, wherein the solvent is an alcohol-water mixed solution, and the alcohol is ethanol and/or propylene glycol.
15. The application of the cigarette paper according to any one of claims 1 to 12 or the cigarette paper prepared by the preparation method according to any one of claims 13 to 14 is characterized in that the cigarette paper is used for preparing a combustible cigarette or a non-combustible cigarette.
16. A combustible cigarette with a function of slowly releasing alcohol spices and lactone simultaneously is characterized in that a tobacco shred rod is coated with the cigarette paper of any one of claims 1 to 12 or the cigarette paper prepared by the preparation method of any one of claims 13 to 14.
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| CN113876022A (en) * | 2021-09-20 | 2022-01-04 | 河南中烟工业有限责任公司 | High-molecular latent-fragrance slow-release material and application thereof in heating cigarettes |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007063171A (en) * | 2005-08-30 | 2007-03-15 | Ube Ind Ltd | Manufacturing method of acrylic acid higher alcohol ester and methacrylic acid higher alcohol ester |
| CN102936535A (en) * | 2012-11-23 | 2013-02-20 | 中国烟草总公司郑州烟草研究院 | Preparation method and application of natural tobacco aroma enhancer |
| CN106916626A (en) * | 2017-03-31 | 2017-07-04 | 武汉黄鹤楼香精香料有限公司 | A kind of milk tea perfume mixing odor type essence wrapped up in for recombination tobacco leaf in clothing and preparation method thereof |
| CN108601958A (en) * | 2016-02-15 | 2018-09-28 | 爱客多有限公司 | Pro-perfume compositions |
-
2019
- 2019-03-12 CN CN201910183922.3A patent/CN111685361B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007063171A (en) * | 2005-08-30 | 2007-03-15 | Ube Ind Ltd | Manufacturing method of acrylic acid higher alcohol ester and methacrylic acid higher alcohol ester |
| CN102936535A (en) * | 2012-11-23 | 2013-02-20 | 中国烟草总公司郑州烟草研究院 | Preparation method and application of natural tobacco aroma enhancer |
| CN108601958A (en) * | 2016-02-15 | 2018-09-28 | 爱客多有限公司 | Pro-perfume compositions |
| CN106916626A (en) * | 2017-03-31 | 2017-07-04 | 武汉黄鹤楼香精香料有限公司 | A kind of milk tea perfume mixing odor type essence wrapped up in for recombination tobacco leaf in clothing and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| 刘善宇: "酯类烟用潜香物质的合成与加香效应研究", 《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》 * |
| 王明锋等: "《烟用香料控释释放技术及其应用》", 31 May 2016, 西南交通大学出版社 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113876022A (en) * | 2021-09-20 | 2022-01-04 | 河南中烟工业有限责任公司 | High-molecular latent-fragrance slow-release material and application thereof in heating cigarettes |
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| CN111685361B (en) | 2022-05-03 |
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