Wallpaper composition and wallpaper that releases fragrance components by heating

Abstract

The present invention relates to a wallpaper composition and wallpaper that releases fragrance components by heating, and more particularly, to a wallpaper composition and wallpaper comprising a novel compound, wherein the compound includes a portion derived from a sugar compound and a portion derived from a fragrance compound in a basic skeleton, and the compound decomposes into a lactone compound, a sugar compound and a fragrance compound when thermally decomposed.

Description

Technical Field

[0001] The present invention relates to a wallpaper composition capable of releasing fragrance components upon heating and the wallpaper. Background Art

[0002] Currently, there are numerous fire detection devices (e.g., fire alarms) on the market that detect fires within facilities or buildings and provide warnings. These devices are widely used in daily life. Generally, fire alarms sound an alarm to mitigate damage. However, if fire alarms are not installed or are malfunctioning, the only way to identify a fire is through the spread of combustion products, such as smoke, burning odors, and soot, produced by the high temperatures of flames on interior furnishings like furniture and wallpaper. This can delay fire detection for people far from the source of the fire (e.g., the flames), resulting in insufficient evacuation time in large buildings and high-rise apartments, potentially causing property and personal damage.

[0003] Therefore, the present invention provides a novel fire detection system or material, in which, when the heat generated by the fire is transferred, the volatile aroma components (e.g., lactone and / or menthol) decomposed by the heat quickly diffuse from the area close to the flames in the burning building to the entire building, so that people far away from the fire location can also quickly identify the fire through the unique aroma components (e.g., lactone and / or menthol). Summary of the Invention

[0004] Problems to be solved by the invention

[0005] Existing compounds that function as fragrance agents have poor chemical structure stability at or near room temperature (rt), resulting in structural transformation or decomposition, leading to the volatilization of fragrance components. This results in the fragrance released not being sufficient to identify a fire in the event of a fire, or failing to perform the corresponding function. To address this problem, the present invention provides a wallpaper composition comprising a novel compound that has a stable chemical structure at or near room temperature (rt) and can release volatile and / or fragrance components through thermal decomposition when heated. These volatile and / or fragrance components can be used to quickly identify a fire.

[0006] The present invention provides a wallpaper made of the wallpaper composition of the present invention, which releases volatile and / or fragrant components through thermal decomposition when heated, thereby enabling rapid identification of fire.

[0007] The present invention provides a wallpaper, which is made from the wallpaper composition of the present invention.

[0008] The present invention provides a coating composition comprising the wallpaper composition of the present invention or the novel compound represented by Chemical Formula 1 of the present invention.

[0009] However, the technical problems to be solved by the present invention are not limited to the above-mentioned technical problems, and a person skilled in the art can easily understand other technical problems not mentioned through the following description.

[0010] Means used to solve problems

[0011] The present invention relates to a wallpaper composition comprising: a substrate; and a compound represented by the following Chemical Formula 1:

[0012] [Chemical Formula 1]

[0013]

[0014] In the chemical formula 1,

[0015] n is an integer of 1 or 2,

[0016] R is a straight or branched chain alkyl group having 1 to 30 carbon atoms,

[0017] The moiety A' is a moiety derived from a fragrance compound containing at least one of an aromatic ring, an aliphatic ring, and an aliphatic chain having a hydroxyl group (-OH) participating in a carbonate bond. Moiety A' corresponds to the fragrance compound except for the hydroxyl group,

[0018] The moiety G' is a moiety derived from a sugar compound, at least one of the hydroxyl groups (-OH) bonded to the ring of the sugar compound participates in an ester bond. G' is a sugar compound other than the hydroxyl group involved in the ester bond, and m is a moiety bonded to G' via the ester bond. The number of m is an integer from 1 to 8.

[0019] The present invention relates to a wallpaper or a paint produced from the composition of the present invention.

[0020] Effects of the Invention

[0021] According to one embodiment of the present invention, the wallpaper composition can be formed into wallpaper itself or readily applied to wallpaper base paper, building structures, interior decoration products, etc. When directly heated and / or subjected to ignition temperatures, it releases highly volatile lactones and / or fragrance components through thermal decomposition. These thermally decomposed components diffuse throughout a building, allowing people near or far from the fire to quickly identify the fire. BRIEF DESCRIPTION OF THE DRAWINGS

[0022] Figure 1This is the NMR analysis result of ethyl 4-hydroxyheptanoate (2a) prepared in Example according to one embodiment of the present invention.

[0023] Figure 2 This is the NMR analysis result of ethyl 4-(menthylcarbonyloxy)heptanoate (3a) prepared in Example according to one embodiment of the present invention.

[0024] Figure 3 These are the results of NMR analysis of 4-(menthylcarbonyloxy)heptanoic acid (4a).

[0025] Figure 4 1 is the NMR analysis result of glucosyl-(4-menthylcarbonyloxy)heptanoate (5a) prepared in Example according to one embodiment of the present invention.

[0026] Figure 5 1 is the NMR analysis result of glucosyl-(4-menthylcarbonyloxy)heptanoate (5a) prepared in Example according to one embodiment of the present invention.

[0027] Figure 6 1 is the NMR analysis result of 4-(menthylcarbonyloxy)nonanoic acid (4b) prepared in Example according to one embodiment of the present invention.

[0028] Figure 7 1 is the NMR analysis result of glucosyl-(4-menthylcarbonyloxy)nonanoate (5b) prepared in Example according to one embodiment of the present invention.

[0029] Figure 8 1 is the NMR analysis result of glucosyl-(4-menthylcarbonyloxy)nonanoate (5b) prepared in Example according to one embodiment of the present invention.

[0030] Figure 9 This is the NMR analysis result of ethyl 5-(menthylcarbonyloxy)decanoate (3c) prepared in Example according to one embodiment of the present invention.

[0031] Figure 10 This is the NMR analysis result of ethyl 5-(menthylcarbonyloxy)decanoate (3c) prepared in Example according to one embodiment of the present invention.

[0032] Figure 11 1 is the NMR analysis result of 5-(menthylcarbonyloxy)decanoic acid (4c) prepared in Example according to one embodiment of the present invention.

[0033] Figure 12 1 is the NMR analysis result of 5-(menthylcarbonyloxy)decanoic acid (4c) prepared in Example according to one embodiment of the present invention.

[0034] Figure 13 This is the NMR analysis result of 5-isopropyl-2-methylcyclohexyl-(1-oxo-1-(2-thioxothiazolidin-3-yl)decane-5-yl) carbonate (5c) prepared in Example according to one embodiment of the present invention.

[0035] Figure 14 1 is the NMR analysis result of glucosyl-(5-menthylcarbonyloxy)decanoate (6c) prepared in Example according to one embodiment of the present invention.

[0036] Figure 15 1 is the NMR analysis result of glucosyl-(5-menthylcarbonyloxy)decanoate (6c) prepared in Example according to one embodiment of the present invention.

[0037] Figure 16 This is the NMR analysis result of ethyl 4-hydroxyundecanoate (2d) prepared in Example according to one embodiment of the present invention.

[0038] Figure 17 This is the NMR analysis result of ethyl 4-hydroxyundecanoate (2d) prepared in Example according to one embodiment of the present invention.

[0039] Figure 18 1 is the NMR analysis result of ethyl 4-(menthylcarbonyloxy)undecanoate (3d) prepared in Example according to one embodiment of the present invention.

[0040] Figure 19 1 is the NMR analysis result of 4-(menthylcarbonyloxy)undecanoic acid (4d) prepared in Example according to one embodiment of the present invention.

[0041] Figure 20 1 is the NMR analysis result of 4-(menthylcarbonyloxy)undecanoic acid (4d) prepared in Example according to one embodiment of the present invention.

[0042] Figure 21 1 is the NMR analysis result of glucosyl-(4-menthylcarbonyloxy)undecanoate (6d) prepared in Example according to one embodiment of the present invention.

[0043] Figure 22 1 is the NMR analysis result of glucosyl-(4-menthylcarbonyloxy)undecanoate (6d) prepared in Example according to one embodiment of the present invention.

[0044] Figure 23 1 is the NMR analysis result of ethyl 4-(benzyloxycarbonyloxy)undecanoate (3e) prepared in Example according to one embodiment of the present invention.

[0045] Figure 241 is the NMR analysis result of glucosyl-(4-benzyloxycarbonyloxy)nonanoate (5e) prepared in Example according to one embodiment of the present invention.

[0046] Figure 25 1 is a thermal analysis result of a compound prepared in an example according to one example of the present invention.

[0047] Figure 26 1 is the component distribution of the compound prepared in the embodiment according to one embodiment of the present invention as the thermal decomposition temperature changes.

[0048] Figure 27 1 is the component distribution of the compound prepared in the embodiment according to one embodiment of the present invention as the thermal decomposition temperature changes. DETAILED DESCRIPTION

[0049] The embodiments of the present invention will be described in detail below with reference to the accompanying drawings. When describing the present invention, if it is considered that a detailed description of related well-known functions or structures would unnecessarily obscure the main points of the present invention, the detailed description will be omitted. In addition, the terms in this specification are used to accurately describe the embodiments and may vary depending on the intention of the user or operator or the conventions in the technical field to which the present invention belongs. Therefore, the definition of terms should be based on the content of the entire specification. The same reference numerals in each figure represent the same components.

[0050] Throughout the specification, when it is stated that a member is located “on” another member, this includes not only a case where one member is in contact with another member but also a case where another member is present between the two members.

[0051] Throughout the specification, when a part “includes” a certain component, it means that other components may be further included, rather than excluding other components.

[0052] The composition comprising the compound of the present invention and the method of using the composition of the present invention will be described in detail below with reference to the examples and the accompanying drawings, but the present invention is not limited to the examples and the accompanying drawings.

[0053] The present invention relates to a composition comprising the compound of the present invention. According to one embodiment of the present invention, the composition comprises a compound represented by the following Chemical Formula 1, which is a fragrance compound that releases fragrance or fragrance components upon thermal decomposition.

[0054] According to one embodiment of the present invention, the composition may include at least one of a base material (or matrix), a solvent, and an additive; and the compound represented by Chemical Formula 1. As an example of the present invention, the composition may be a wallpaper composition and / or a coating composition.

[0055] According to one embodiment of the present invention, the composition can be applied to wallpaper or paint. When a fire occurs, the heat brought by the combustion will cause the composition to undergo thermal decomposition, and the flavor components (e.g., lactones or menthol) released thereby will rapidly diffuse within a building (e.g., a residence, an apartment, a factory, etc.), thereby providing a scent signal that can identify a fire. Under normal circumstances, only when wallpaper and furniture, etc., burn at high temperatures due to a fire, will soot and combustion products diffuse with the smoke. However, under conditions with thermal decomposition components, it is possible to identify the fire earlier and escape quickly. For example, when exposed to or close to an ignition point (heat source), the closer the part using the composition of the present invention is to the ignition point, the higher the temperature it is subjected to. When heated, the thermally decomposed synthetic compound decomposes, and the lactone compound released thereby rapidly diffuses to the entire building space. Such volatile lactone compounds can enable people in a space away from the flame to quickly identify a fire.

[0056] According to one embodiment of the present invention, the compound represented by the following chemical formula 1 releases volatile fragrance components by thermal decomposition when heated:

[0057] [Chemical Formula 1]

[0058]

[0059] As an example of the present invention, the chemical formula 1 includes a portion (G') derived from a sugar compound and a portion (A') derived from a flavor compound. In the chemical formula 1, the flavor compound is covalently bonded via a carbonate bond, and the sugar compound is covalently bonded via an ester bond. Bonding. The compound of Chemical Formula 1 is thermally decomposed into sugar compounds, flavor compounds, and flavor components of lactone compounds when heated and emits flavor components. For example, the compound of Chemical Formula 1 is synthesized in the following manner: the lactone compound reacts with the hydroxyl group (-OH) of the sugar compound through an ester bond through a ring-opening mechanism, and reacts with the hydroxyl group of the flavor compound through a carbonate bond. That is, the compound of Chemical Formula 1 is structurally stable and has low volatility at approximately room temperature or a similar temperature. When heated, the carbonate and ester bonds break through a ring closure mechanism, thereby decomposing into a sugar compound (G), a lactone compound, and a fragrance compound (A), releasing a fragrance. Furthermore, harmless carbon dioxide is produced during the decomposition process. Specifically, during the heating process, the carbonate bonds break and decompose into the fragrance compound, generating carbon dioxide. The ester bonds then break through the ring closure mechanism, decomposing into the sugar compound and the lactone compound, thereby releasing the fragrance.

[0060] According to one embodiment of the present invention, the moiety A' in the chemical formula 1 may be a moiety derived from a fragrance compound comprising at least one of an aromatic ring having a hydroxyl group, an aliphatic ring having a hydroxyl group, and an aliphatic chain having a hydroxyl group. The hydroxyl group may include at least one of a ring, a chain, or both (e.g., one or two), which may correspond to a substituent, a basic skeleton, and / or a moiety having a hydroxyl group. The hydroxyl group may participate in the covalent bonding of a carbonate bond in the chemical formula 1, and the moiety A' may correspond to a fragrance compound other than the hydroxyl group. That is, the hydroxyl group of the fragrance compound in the moiety A' is protected by a carbonate bond, which can prevent a decomposition reaction based on a closed ring from occurring at room temperature.

[0061] According to one embodiment of the present invention, the fragrance compound can be selected from cyclic monoterpenoid compounds having a hydroxyl group, acyclic monoterpenoid compounds having a hydroxyl group, aromatic compounds having 6 to 10 carbon atoms having a hydroxyl group, or non-aromatic rings having 5 to 6 carbon atoms and their isomers. For example, the fragrance compound can be selected from the following compounds, which are compounds produced by cleavage of carbonate bonds during thermal decomposition of Chemical Formula 1:

[0062] as well as

[0063] According to one embodiment of the present invention, the moiety A' can be selected from the following chemical formulas.

[0064] Where * is the oxygen site within the carbonate bond:

[0065]

[0066]

[0067] as well as

[0068] According to one embodiment of the present invention, the moiety G' is a moiety derived from a sugar compound, wherein the hydroxyl group bonded to the ring of the sugar compound participates in an ester bond. The generated moiety G' can be equivalent to a sugar compound other than the hydroxyl group. The compound of Chemical Formula 1 can reduce volatility at room temperature through the bonding of sugar compounds, thereby maintaining structural stability and improving solubility in organic solvents. This can improve compatibility and / or processability in various substrates (or matrices) of the compound of Chemical Formula 1, expanding its application range as food, smoking products, wallpaper, coatings, etc.

[0069] According to one embodiment of the present invention, the sugar compound includes a six-membered ring, a five-membered ring, or both, and at least one, at least two, at least three, or all of the hydroxyl groups bonded to the ring of the sugar compound can participate in the ester bond of the chemical formula 1. For example, by forming an ester bond based on a single or multiple hydroxyl groups, a single or multiple "[]" part (i.e., ) may be bonded to a moiety G'.

[0070] According to one embodiment of the present invention, the m refers to a [ ] portion bonded to the moiety G' via the ester bond (ie, ), said m can be an integer from 1 to 8; 1 to 7; 1 to 6; 1 to 5; 1 to 4; 1 to 3; or 1 to 2.

[0071] According to one embodiment of the present invention, the sugar compound can be selected from tagatose, trehalose, galactose, rhamnose, cyclodextrin, maltodextrin, dextran, sucrose, glucose, ribulose, fructose, threose, arabinose, xylose, lyxose, allose, altrose, mannose, idose, lactose, maltose, invert sugar, isotrehalose, neotrehalose, palatinose or isomaltulose, erythrose, deoxyribose, glucose, idose, ... ribulose, fructose, threose, arabinose, xylose, lyxose, allose, altrose, mannose, idose, lactose, maltose, invert sugar, isotrehalose, neotrehalose, palatinose or isomaltulose, erythrose, deoxyribose, glucose, idose, The present invention also includes sugars, erythrulose, xylulose, psicose, turanose, cellobiose, amylopectin, glucosamine, mannosamine, fucose, glucuronic acid, gluconic acid, gluconolactone, abequose, galactosamine, isomaltooligosaccharides, xylo-oligosaccharides, gentio-oligosaccharides, sorbose, niger oligosaccharides, palatinose, fructooligosaccharides, maltotetraol, maltotriol, malto-oligosaccharides, lactulose, melibiose, raffinose, rhamnose and ribose. Preferably, the ... glucuronic acid, gluconic acid, gluconolactone, abequose, galactosamine, isomaltooligosaccharides, xylo-oligosaccharides, gentio-oligosaccharides, sorbose, niger oligosaccharides, palatinose,

[0072] In one embodiment of the present invention, the flavoring agent may be selected from the following chemical formulas 1-1 to 1-9:

[0073] [Chemical Formula 1-1]

[0074]

[0075] [Chemical formula 1-2]

[0076]

[0077] [Chemical formula 1-3]

[0078]

[0079] [Chemical formula 1-4]

[0080]

[0081] [Chemical Formula 1-5]

[0082]

[0083] In one example of the present invention, R 1 to R 5 It can be obtained from hydroxyl (-OH) and (n, R and A' are as defined in the chemical formula 1).

[0084] Preferably, It can be R 1 to R 5 At least one; at least two; at least three; at least four; or all, more preferably, may be R 1 and R 5 At least one of R 1 and R 4 At least one of; and / or R 3 and R 4 At least one of them.

[0085] [Chemical formula 1-6]

[0086]

[0087] In one example of the present invention, R in the chemical formula 1-6 1 to R 4 It can be obtained from hydroxyl (-OH) and (n, R and A' are as defined in the chemical formula 1).

[0088] Preferably, It can be R 1 to R 4 At least one; at least two; at least three; or all, more preferably, may be R 1 and R 4 At least one of R 2 and R 3中 At least one of; and / or R 1 and R3中 at least one of them.

[0089] [Chemical Formula 1-7]

[0090]

[0091] [Chemical Formula 1-8]

[0092]

[0093] [Chemical Formula 1-9]

[0094]

[0095] In one example of the present invention, R in the chemical formulas 1-7 to 1-9 1 to R 8 It can be obtained from hydroxyl (-OH) and (n, R and A' are as defined in the chemical formula 1).

[0096] Preferably, It can be R 1 to R 8 At least one; at least two; at least three; at least four; or all, more preferably, may be R 1 to R 3 At least one of; and / or R 5 and R 8 At least one of; most preferably, it can be R 1 to R 2 At least one of R 1 and R 3 At least one of R 6 and R 8 At least one of; and / or R 7 and R 5 At least one of .

[0097] According to one embodiment of the present invention, the flavoring agent may be selected from the following chemical formulas 1-1-a to 1-9-a:

[0098] [Chemical formula 1-1-a]

[0099]

[0100] [Chemical formula 1-2-a]

[0101]

[0102] [Chemical formula 1-3-a]

[0103]

[0104] [Chemical formula 1-4-a]

[0105]

[0106] [Chemical formula 1-5-a]

[0107]

[0108] [Chemical formula 1-6-a]

[0109]

[0110] [Chemical formula 1-7-a]

[0111]

[0112] [Chemical formula 1-8-a]

[0113]

[0114] [Chemical formula 1-9-a]

[0115]

[0116] wherein n, R, and A' are as defined in Chemical Formula 1.

[0117] According to one embodiment of the present invention, n in Chemical Formula 1 is an integer of 1 or 2. R may be a linear or branched alkyl group having 1 to 30 carbon atoms; preferably, a linear or branched alkyl group having 2 to 10 carbon atoms.

[0118] According to an embodiment of the present invention, the lactone compound may be a γ-lactone of the following Chemical Formula 2 or a δ-lactone of the following Chemical Formula 3.

[0119] [Chemical Formula 2]

[0120]

[0121] [Chemical Formula 3]

[0122]

[0123] In one example of the present invention, R in Chemical Formula 1 and Chemical Formula 2 may be a linear or branched alkyl group having 1 to 30 carbon atoms, preferably a linear or branched alkyl group having 2 to 10 carbon atoms.

[0124] For example, the lactone compound can be selected from the following chemical formula:

[0125]

[0126] as well as

[0127] According to one embodiment of the present invention, the thermal decomposition temperature of the compound may be above 70° C., above 80° C., above 90° C., or above 100° C., preferably, above 120° C., above 150° C., above 200° C., or more preferably, between 200° C. and 300° C. Furthermore, the thermal decomposition may be performed in an environment containing oxygen and / or moisture.

[0128] According to one embodiment of the present invention, the compound may be present in an amount of 0.0001% by weight or more of the composition; 0.001% by weight or more; 0.01% by weight or more; 0.1% to 100% by weight (or less); 0.1% to 80% by weight; 0.0001% to 60% by weight; 0.001% to 50% by weight; 0.1% to 30% by weight; 1% to 20% by weight; 5% to 20% by weight; or 5% to 10% by weight. Preferably, the compound may be present in an amount of 0.0001 to 1% by weight. When included within the above ranges, a fragrance may be released based on the thermal decomposition of the fragrance agent. When the compound is exposed to a temperature condition that allows thermal decomposition to occur at and / or near an ignition point, or when a substrate is directly burned and / or ignited, a function of enabling people to recognize a fire may be provided by releasing a fragrance (e.g., volatile lactones and / or fragrance compounds produced by the thermal decomposition of the compound of Chemical Formula 1).

[0129] According to one embodiment of the present invention, the substrate (or matrix) can be 1% to 100% by weight (less than) 30% to 99% by weight; 50% to 99% by weight; 60% to 90% by weight; 80% to 90% by weight; 30% to 60% by weight; or 30% to 50% by weight of the composition. The substrate can be provided as a matrix to provide or control mechanical, physical and / or chemical properties according to the purpose of the composition. For example, when two or more substrates are included, the mass ratio of the first component to the remaining components can be 1:0.01 to 100; 1:0.1 to 20; 1:0.1 to 10; or 1:0.1 to 5.

[0130] According to one embodiment of the present invention, the substrate (or matrix) can be appropriately selected based on the intended use of the composition. For example, the substrate (or matrix) can be a material that can be used for wallpaper and / or coatings. Non-limiting examples of the substrate (or matrix) include fiber, paper, pulp, wood powder, polymer resin, wood, starch powder, alginic acid, oil, wax, fatty acid, organic and / or inorganic matter, or ceramic powder. For example, the substrate (or matrix) can be in the form of fiber, powder, etc.

[0131] According to one embodiment of the present invention, the organic and / or inorganic or ceramic powder can be chalk, perlite, vermiculite, diatomaceous earth, colloidal silica, magnesium oxide, magnesium sulfate, magnesium carbonate, diatomaceous earth powder, loess powder, clay powder, rice husk powder, charcoal, shell powder, medical stone, activated carbon powder, zeolite powder, activated clay powder, silicon dioxide, titanium dioxide, etc., and can be used as a substrate or functional filler according to its content.

[0132] According to one embodiment of the present invention, the oil can be vegetable oil, petroleum-derived oil (e.g., paraffin oil, mineral oil), animal oil, fatty acid (e.g., animal fat having 1 to 50 carbon atoms, vegetable fat having 1 to 50 carbon atoms, saturated fatty acid having 1 to 50 carbon atoms, unsaturated fatty acid having 1 to 50 carbon atoms (e.g., monounsaturated fatty acid or polyunsaturated fatty acid)), etc., but is not limited thereto. The wax can be a wax prepared from a higher fat phase and a higher alcohol, such as animal wax, vegetable wax, synthetic wax, petroleum wax, or for example, paraffin wax, lanolin wax, carnauba wax, beeswax, beeswax, PE wax, PP wax, etc., but is not limited thereto.

[0133] According to one embodiment of the present invention, the starch may be plant starch, modified starch, etc. For example, the plant starch includes corn starch, potato starch, sweet potato starch, tapioca starch, and cassava starch; modified starch, etc. For example, the modified starch may be oxidized starch, acetylated distarch adipate, acetylated distarch phosphate, starch sodium octenyl succinate, distarch phosphate, monostarch phosphate, phosphated distarch phosphate, starch acetate, hydroxypropyl distarch phosphate, and hydroxypropyl starch, but is not limited thereto.

[0134] According to one embodiment of the present invention, the polymer resin may be a cellulose resin, polylactic acid (PLA), polyhydroxyalkanoate (PHA), polyvinyl acetate resin, PVC, TPU, EVA, PP, PE (low density, high density), PET, polyvinyl chloride (PVC), etc., or may be a liquid resin. For example, the polymer resin may have the function of an adhesive. For example, the cellulose resin may provide a polymer matrix, non-limiting examples of which include methyl cellulose, ethyl cellulose, carboxymethyl cellulose, carboxyethyl cellulose, hydroxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methyl cellulose, hydroxyethyl methyl cellulose, agar, sodium carboxymethyl cellulose (CMC), etc. For example, the cellulose resin may be microfibrillated cellulose (e.g., having a thickness of 20 μm to 300 μm).

[0135] According to one embodiment of the present invention, described fiber can comprise the crushed thing, nonwoven fabric, felt (felt) etc. of staple fiber, long fiber, fabric or fabric, and it can be made into synthetic yarn and / or natural yarn.For example, it can be the natural fiber of hemp, flax, ramie, kenaf, jute, cotton, banana, fiber, banana fiber, pulp fiber, bamboo fiber etc.For example, described long fiber can comprise PLA long fiber, aliphatic polyester copolymer long fiber.The non-limitative example of described aliphatic polyester copolymer has polyethylene succinate, polyethylene adipate, poly ethylene azelaic acid, poly oxalate, poly butylene succinate, poly butylene adipate, poly succinic acid-butylene adipate and poly butylene sebacate etc.

[0136] According to one embodiment of the present invention, the solvent may be 1 to 99 weight %; 10 to 90 weight %; 10 to 80 weight %; 10 to 60 weight %; or 10 to 30 weight % in the balance or composition. Furthermore, the solvent may be water, a water-soluble organic solvent, or a fat-soluble organic solvent. The solvent may be appropriately selected according to the intended use. Preferably, any solvent suitable for use in wallpaper or paint may be used without restriction. For example, non-limiting examples of the solvent include alcohols having 1 to 5 carbon atoms, water, glycol solvents, and the like. For example, the glycol solvent may be ethylene glycol butyl ether, ethylene glycol, ethylene glycol monoacetate, diethylene glycol, diethylene glycol acetate, tetraethylene glycol, propylene glycol, propylene glycol monomethyl ether, trimethylene glycol, and the like.

[0137] According to one embodiment of the present invention, the composition may further include additives according to the purpose. Examples of the additives include solvents, adhesives, binders, rubber (natural rubber, epoxy-modified natural rubber and synthetic rubber), surfactants, diluents, disintegrants, lubricants, flavoring agents, colorants, preservatives, antioxidants, emulsifiers, stabilizers, flavoring agents, foaming agents, fillers, antibacterial agents, plasticizers, wetting agents (for example, glycerol or propylene glycol) and acetate compounds, etc. Additives known in the art can be selected and will not be described in detail here.

[0138] According to one embodiment of the present invention, the composition can be prepared into various phases, for example, a solid (e.g., powder, crystal, flake, crushed material), slurry, suspension, paste, gel, liquid, emulsion, or aerosol. For example, the composition can be formed or mixed with a desired product, or used by coating (painting), printing, dipping, spraying, and / or applying methods known in the art, which are not specifically described here.

[0139] According to one embodiment of the present invention, the composition can be formed into a film, sheet, or other shape, or applied to a substrate by coating, impregnation, printing, or application. The substrate is not particularly limited, as long as it is suitable for use with the composition. For example, when used as a building structure or interior material, the substrate can be concrete, reinforced concrete, cement moldings, bricks, plywood, wood, gypsum board, ceramic tile, stone, sinks, furniture, wallpaper, etc. The composition can also be applied to electronic products, mechanical equipment, and devices.

[0140] According to one embodiment of the present invention, the composition can be used as a coating finishing material composition for buildings and interior decorations, such as sofas, windows, doors, furniture, wallpaper (e.g., decorative panels), etc. In addition, for example, the composition can be coated on wallpaper base paper.

[0141] According to one embodiment of the present invention, the decorative products or accessories may be interior and exterior decorative materials for buildings, homes, automobiles, aviation, ships, trains, and other industrial fields. For example, they may be decorative materials for automobiles, airplanes, trains, and the like.

[0142] According to one embodiment of the present invention, the composition can be used as wallpaper and / or paint. For example, the wallpaper can be a wallpaper sheet or film formed from the composition. For example, the wallpaper can be in a form obtained by applying liquid wallpaper (e.g., paint wallpaper) and then drying it.

[0143] According to one embodiment of the present invention, the coating may be a water-soluble / lipid-soluble coating, which may be applied to a substrate to provide a wallpaper effect, for example.

[0144] According to one embodiment of the present invention, the wallpaper and / or paint includes the compound represented by Chemical Formula 1 of the present invention. The compound represented by Chemical Formula 1 can be pre-added to the wallpaper as an additive during wallpaper manufacturing, or pre-added to the paint before applying the paint to walls, trees, or furniture, thereby allowing the compound represented by Chemical Formula 1 to be applied together. When heat generated by a fire is transferred, the aroma components (e.g., lactones and menthol) of the compound represented by Chemical Formula 1 are released through thermal decomposition at a certain high temperature (e.g., approximately 200-300°C). At this point, the volatile aroma components rapidly diffuse from the area near the flames of the burning building to the entire building, allowing people away from the fire to quickly identify the fire by the unique lactone / menthol smell. Under normal circumstances, soot and combustion products only diffuse with the smoke when wallpaper and furniture burn at high temperatures. However, the presence of thermally decomposed components allows for earlier fire identification.

[0145] As an example of the present invention, the coating can be used in building structures, interior decoration products, accessories, electronic products, automobiles, aviation, trains, etc. The interior decoration products can be used in the above-mentioned household and industrial components.

[0146] As an example of the present invention, the thickness of the wallpaper may be greater than 0.1 mm; 0.1 mm to 5 mm; 0.1 mm to 3 mm; 0.1 mm to 2 mm; 0.1 mm to 1 mm; or 1 mm to 2 mm.

[0147] As an example of the present invention, the wallpaper can be composed of a single layer or multiple layers and can include, for example, a base sheet, a resin layer, and a printing layer, but is not limited thereto. In addition, the composition of the present invention can be sprayed, printed, and / or coated on the base paper of the wallpaper.

[0148] The present invention will be described in more detail below through examples and comparative examples. However, the following examples are only used to illustrate the present invention, and the content of the present invention is not limited to the following examples.

[0149] Example 1

[0150] [Scheme 1]

[0151]

[0152] (1-1) Synthesis of Ethyl 4-hydroxyheptanoate (2a)

[0153] 20 g of γ-heptalactone (0.15 mol) was dissolved in 100 mL of methanol, and 11.17 g of KOH (0.16 mol, 1.05 eq.) was slowly added while stirring, followed by reaction at room temperature for 12 hours. After the reaction solution was concentrated under reduced pressure, 80 mL of DMF was added, and 17 g of bromoethane (0.15 mol, 1 eq.) was added while stirring and allowed to react for 12 hours. 100 mL of water was added to the reaction solution, and the product was extracted with ethyl acetate, followed by washing with water and brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain 18.1 g of the desired product 2a (66.7%, two steps).

[0154] 1 H NMR (CDCl3, 400.13 MHz); δ 8.01 (s, 1H, -OH), 4.12 (q, 2H, J = 8 Hz, COO-CH2-), 3.63 (m, 1H, CH-O), 2.42 (m, 2H, CO-CH2), 1.81-0.92 (m, 12H, alkyl).

[0155] (1-2) Synthesis of ethyl 4-(mentylcarbonyloxy)heptanoate [Ethyl 4-(mentylcarbonyloxy)heptanoate, 3a]

[0156] 18 g of ethyl 4-hydroxyheptanoate (2a, 0.1 mol) was dissolved in 120 mL of THF. Then, 16 g of pyridine (0.2 mol, 2 eq.) was added and the mixture was cooled with ice water while stirring. Meanwhile, a solution of 23 g of mentyl chloroformate (0.1 mol, 1 eq.) dissolved in 20 mL of THF was slowly added dropwise. After one hour, the reaction solution was warmed to room temperature and allowed to react overnight. Water was then added and the mixture was extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid, a saturated sodium bicarbonate solution, and brine, respectively, then dried over MgSO4 and concentrated under reduced pressure to obtain 30 g (81% yield) of the desired product 3a as a yellow liquid.

[0157] 1 H NMR (CDCl3, 400.13 MHz); δ 4.74 (7tet, 1H, J = 4 Hz, -COOCH-), 4.51 (td, 1H, J = 9, 4 Hz, COO-CH-), 4.12 (q, 2H, J = 8 Hz, COO-CH2-), 2.36 (m, 2H, CO-CH2-), 1.93-0.79 (m, 30H, alkyl).

[0158] (1-3) Synthesis of 4-(mentylcarbonyloxy)heptanoic acid [4a]

[0159] 25 g of ethyl 4-(mentylcarbonyloxy)heptanoate (3a, 68.5 mmol) was dissolved in 100 mL of THF and 30 mL of distilled water. 4.2 g of lithium hydroxide monohydrate (102.4 mmol, 1.5 eq.) was added and allowed to react at room temperature for 12 hours. 50 mL of distilled water was added and the mixture was extracted with ether. The aqueous layer was adjusted to pH 3 with concentrated hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO, and concentrated under reduced pressure to obtain 21.8 g (81% yield) of the desired product 4a as a yellow liquid.

[0160] 1 H NMR (CDCl3, 400.13 MHz); δ 4.76 (m, 1H, -COOCH-), 4.52 (td, 1H, J = 9, 4 Hz, COO-CH-), 4.11 (q, 2H, J = 8 Hz, COO-CH2-), 2.42 (m, 2H, CO-CH2-), 1.99-0.82 (m, 27H, alkyl)

[0161] (1-4) Synthesis of Glucosyl-(4-mentylcarbonyloxy)heptanoate, 5a

[0162] 3 g of 4-(menthylcarbonyloxy)heptanoic acid (4a, 9.1 mmol) was dissolved in 20 mL of DMF, followed by the addition of 3.7 g of glucose (20.5 mmol, 2.2 eq.). While stirring at room temperature, 1.7 g of diisopropylcarbodiimide (13.4 mmol, 1.5 eq.) and 0.05 g of DMAP (cat.) were added sequentially, and the mixture was allowed to react at room temperature for 12 hours. Distilled water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid, saturated sodium bicarbonate solution, and brine, dried over MgSO₄, and then concentrated under reduced pressure. The mixture was subjected to silica gel column chromatography using a 6:1 mixture of methylene chloride and methanol to obtain 0.6 g (13% yield) of the desired product 5a.

[0163] 1 H NMR (CDCl3, 400.13 MHz); δ 5.30-3.54 (m, 13H, glucose, -COOCH, -COOCH), 2.45 (m, 2H, CO-CH2-), 2.03-0.78 (m, 27H, alkyl).

[0164] 2. Synthesis of Glucosyl-(4-mentylcarbonyloxy)nonanoate (5b)

[0165] [Scheme 2]

[0166]

[0167] (2-1) Synthesis of ethyl 4-hydroxynonanoate [Ethyl 4-hydroxynonanoate, 2b]

[0168] 20g of γ-nonalactone (0.13mol) was dissolved in 100mL of methanol, and 9.18g of KOH (0.14mol, 1.05eq.) was slowly added while stirring, and the reaction was continued at room temperature for 12 hours. After the reaction solution was concentrated under reduced pressure, 80mL of DMF was added and stirred, and 14g of bromoethane (0.13mol, 1eq.) was added while stirring and the reaction was continued for 12 hours. 100mL of water was added to the reaction solution and extracted with ethyl acetate, followed by washing with water and salt water. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain 24g (93%, two steps) of the target product 2b.

[0169] (2-2) Synthesis of ethyl 4-(mentylcarbonyloxy)nonanoate [Ethyl 4-(mentylcarbonyloxy)nonanoate, 3b]

[0170] 24 g of ethyl 4-hydroxynonanoate (2, 0.12 mol) was dissolved in 120 mL of THF, and 18 g of pyridine (0.42 mol, 2 eq.) was added, followed by ice-cold cooling. A 30 mL THF solution containing 26 g of menthyl chloroformate (0.12 mol, 1 eq.) was slowly added dropwise while stirring. After one hour, the reaction solution was warmed to room temperature, reacted overnight, and then water was added and extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid, a saturated sodium bicarbonate solution, and brine, respectively, and then dried over MgSO4. The mixture was then concentrated under reduced pressure to obtain 34 g (yield 74.5%) of the desired product 3 as a yellow liquid.

[0171] 1 H NMR (CDCl3, 400.13MHz); δ4.74 (7tet, 1H, J=4Hz, -COOCH-), 4.51 (td, 1H, J=9, 4Hz, CO O-CH-), 4.12 (q, 2H, J=8Hz, COO-CH2-), 2.36 (m, 2H, CO-CH2-), 1.93~0.79 (m, 23H, alkyl).

[0172] (2-3) Synthesis of 4-(mentylcarbonyloxy)nonanoic acid [4b]

[0173] 11.5 g of ethyl 4-(menthylcarbonyloxy)nonanoate (3, 29.9 mmol) was dissolved in 50 mL of THF and 20 mL of distilled water. 2 g of lithium hydroxide monohydrate (48.7 mmol, 1.6 eq.) was added and allowed to react at room temperature for 12 hours. 50 mL of distilled water was added and the mixture was extracted with ether. Concentrated hydrochloric acid was added to adjust the aqueous layer to pH 3, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over MgSO, and concentrated under reduced pressure to obtain 8.6 g (80% yield) of the desired product 4b as a yellow liquid.

[0174] 1 H NMR (CDCl3, 400.13 MHz); δ 4.75 (m, 1H, -COOCH-), 4.49 (m, 1H, COO-CH-), 2.04 (m, 2H, CO-CH2-), 1.93-0.79 (m, 31H, alkyl).

[0175] (2-4) Synthesis of Glucosyl-(4-mentylcarbonyloxy)nonanoate, 5b

[0176] 6.6 g of 4-(menthylcarbonyloxy)nonanoic acid (4b, 24.1 mmol) was dissolved in 30 mL of DMF, followed by the addition of 13 g of glucose (72.1 mmol, 3 eq.). While stirring at room temperature, 3.4 g of diisopropylcarbodiimide (26.9 mmol, 1.2 eq.) and 0.05 g of DMAP (cat.) were added sequentially, followed by reaction at room temperature for 12 hours. Distilled water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid, a saturated sodium bicarbonate solution, and brine, dried over MgSO4, and then concentrated under reduced pressure. The mixture was subjected to silica gel column chromatography using a mixed solvent of dichloromethane and methanol (8:1) to obtain 2 g (yield 16%) of the target product 5b.

[0177] 1 H NMR (CDCl3, 400.13 MHz); δ 5.57-3.35 (m, 13H, glucose, -COOCH, -COOCH), 2.43 (m, 2H, CO-CH2-), 2.03-0.78 (m, 31H, alkyl).

[0178] 3. Synthesis of Glucosyl-(5-mentylcarbonyloxy)decanoate

[0179] [Scheme 3]

[0180]

[0181] (3-1) Synthesis of 5-hydroxydecanoate (2c)

[0182] 10 g of butyl-decanoic acid (δ-Decalactone, 58.7 mmol) was dissolved in 50 mL of methanol, and 4.2 g of KOH (64.7 mmol, 1.05 eq.) was slowly added while stirring. The mixture was allowed to react at room temperature for 12 hours. The reaction solution was concentrated under reduced pressure, and 40 mL of DMF was added. 6.4 g of bromoethane (58.7 mmol, 1 eq) was added while stirring and the reaction was continued for 12 hours.

[0183] 100 mL of water was added to the reaction solution and the mixture was extracted with ethyl acetate, followed by washing with water and brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain 7.6 g (60%, 2 steps) of the target product 2c.

[0184] (3-2) Synthesis of 5-(mentylcarbonyloxy)decanoate [Ethyl5-(mentylcarbonyloxy)decanoate, 3c]

[0185] 7.5 g of ethyl 4-hydroxynonanoate (3c, 34.6 mmol) was dissolved in 50 mL of THF, 5.3 g of pyridine (69.2 mmol, 2 eq.) was added, and the mixture was cooled with ice water. Then, while stirring, a solution of 8.3 g of menthyl chloroformate (37.9 mmol, 1.1 eq.) dissolved in 20 mL of THF was slowly added dropwise. After one hour, the reaction solution was warmed to room temperature and allowed to react overnight. Water was then added and the mixture was extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid, a saturated sodium bicarbonate solution, and brine, dried over MgSO4, and concentrated under reduced pressure. The mixture was subjected to silica gel column chromatography using a mixed solvent of n-hexane and ethyl acetate (7:1) to obtain 4.5 g (yield 32.6%) of the desired product 3c.

[0186] 1 H NMR (CDCl3, 400.13MHz); δ4.72 (m, 1H, -COOCH-), 4.52 (m, 1H, COO-CH-), 4.12 (q, 2H, J=8Hz, COO-CH2-), 2.31 (t, 2H, J=8Hz, CO-CH2-), 2.08~0.86 (m, 27H, alkyl), 0.79 (d, 6H, J=8Hz, -CH3).

[0187] (3-3) Synthesis of 5-(mentylcarbonyloxy)decanoic acid [4c]

[0188] 2.7 g of ethyl 4-(menthylcarbonyloxy)nonanoate (3, 6.8 mmol) was dissolved in 20 mL of THF and 10 mL of distilled water, and 0.42 g of lithium hydroxide monohydrate (10.2 mmol, 1.5 eq.) was added. The mixture was allowed to react at room temperature for 12 hours. 10 mL of distilled water was added and the mixture was extracted with ether. Concentrated hydrochloric acid was added to adjust the aqueous layer to pH 3, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over MgSO, and then concentrated under reduced pressure to obtain 2.1 g (78% yield) of the desired product 4b as a yellow liquid.

[0189] 1 H NMR (CDCl3, 400.13 MHz); δ 4.72 (m, 1H, -COOCH-), 4.51 (td, 1H, J = 8, 4 Hz, COO-CH-), 4.11 (q, 2H, J = 8 Hz, COO-CH2-), 2.38 (m, 2H, CO-CH2-), 2.06-0.78 (m, 33H, alkyl).

[0190] (3-4) Synthesis of 5-Isopropyl-2-methylcyclohexyl(1-oxo-1-(2-thioxothiazolidin-3-yl)decan-5-yl)carbonate

[0191] 1.9 g of 5-(Menthylcarbonyloxy)decanoic acid (4c, 5.1 mmol) was dissolved in 20 mL of dried dichloromethane. 0.73 g of 2-mercaptothiazoline (6.1 mmol, 1.2 eq.) was added, followed by ice-cold cooling. Then, 1.2 g of EDC-HCl (6.1 mmol, 1.2 eq.) and 50 mg of DMAP were slowly added while stirring. After one hour, the reaction solution was warmed to room temperature and allowed to react overnight. Water was then added and the mixture was extracted with dichloromethane. The organic layer was washed with dilute hydrochloric acid, saturated sodium bicarbonate solution, and brine, dried over MgSO4, and concentrated under reduced pressure. The mixture was subjected to silica gel column chromatography using a 3:1 mixture of n-hexane and ethyl acetate to obtain 2.1 g (87.5% yield) of the desired product 5c.

[0192] 1 H NMR (CDCl3, 400.13MHz); δ4.71 (m, 1H, -COOCH-), 4.57 (t, 2H, J=8Hz, N-CH2), 4.51 (m, 1H, COO-CH-), 4. 11 (q, 2H, J=8Hz, COO-CH2-), 3.28 (t, 2H, J=8Hz, S-CH2), 3.21 (m, 2H, CO-CH2-), 2.04~0.79 (m, 33H, alkyl).

[0193] (3-5) Synthesis of Glucosyl-(5-mentylcarbonyloxy)decanoate, 6c

[0194] 2.2 g of 5-isopropyl-2-methylcyclohexyl (1-oxo-1-(2-thiothiazolidin-3-yl)decan-5-yl) carbonate (5c, 4.7 mmol) was dissolved in 20 mL of pyridine, followed by the addition of 2.5 g of glucose (14.1 mmol, 3 eq.). While stirring at room temperature, 93 mg of sodium hydride (60%, 2.4 mmol, 0.5 eq.) and 0.03 g of DMAP (cat.) were added sequentially, and the mixture was allowed to react at room temperature for 12 hours. 0.5 mL of acetic acid was added to the reaction mixture, followed by saturated brine and extraction with ethyl acetate. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The mixture was subjected to silica gel column chromatography using a mixture of dichloromethane and methanol (8:1) to obtain 0.55 g (22% yield) of the desired product 6c.

[0195] 1 H NMR (CDCl3, 400.13 MHz); δ 5.57-3.15 (m, 13H, glucose, -COOCH, -COOCH), 2.36 (m, 2H, CO-CH2-), 2.05-0.80 (m, 33H, alkyl).

[0196] 4. Synthesis of Glucosyl-(4-mentylcarbonyloxy)undecanoate (6d)

[0197] [Scheme 4]

[0198]

[0199] (4-1) Synthesis of Ethyl 4-hydroxyundecanoate (2d)

[0200] 10 g of γ-undecalactone (54.2 mmol) was dissolved in 50 mL of methanol. 3.9 g of KOH (56.9 mmol, 1.05 eq.) was slowly added while stirring, and the mixture was allowed to react at room temperature for 12 hours. The reaction solution was concentrated under reduced pressure, 50 mL of DMF was added, and 5.9 g of bromoethane (54.2 mmol, 1 eq.) was added while stirring, and the reaction was continued for 12 hours.

[0201] 80 mL of water was added to the reaction solution, and the mixture was extracted with ethyl acetate, washed with water and brine, and the organic layer was dried over MgSO 4 and concentrated under reduced pressure to obtain 10.7 g (85.6%, 2 steps) of the target product 2d.

[0202] 1 H NMR (CDCl3, 400.13 MHz); δ 4.12 (q, 2H, J = 8 Hz, COO-CH2-), 3.59 (m, 1H, CH-O), 2.43 (m, 2H, CO-CH2), 1.81-0.92 (m, 20H, alkyl).

[0203] (4-2) Synthesis of ethyl 4-(mentylcarbonyloxy)undecanoate

[0204] 11 g of ethyl 4-hydroxyundecanoate (2d, 47.7 mmol) was dissolved in 60 mL of THF. 6.8 g of pyridine (95.5 mmol, 2 eq.) was added and the mixture was cooled with ice water. Then, while stirring, a solution of 10.5 g of menthyl chloroformate (47.7 mmol, 1 eq.) dissolved in 20 mL of THF was slowly added dropwise. After one hour, the reaction solution was warmed to room temperature and allowed to react overnight. Water was then added and the mixture was extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid, a saturated sodium bicarbonate solution, and brine, respectively, then dried over MgSO4 and concentrated under reduced pressure to obtain 8.3 g (42.1% yield) of the desired product 3d as a yellow liquid.

[0205] 1 H NMR (CDCl3, 400.13MHz); δ4.74 (7tet, 1H, J=4Hz, -COOCH-), 4.51 (td, 1H, J=9, 4Hz, CO O-CH-), 4.12 (q, 2H, J=8Hz, COO-CH2-), 2.36 (m, 2H, CO-CH2-), 1.93~0.79 (m, 23H, alkyl).

[0206] (4-3) Synthesis of 4-(mentylcarbonyloxy)undecanoic acid [4d]

[0207] 8.3 g of ethyl 4-(menthylcarbonyloxy)undecanoate (3d, 19.4 mmol) was dissolved in 30 mL of THF and 20 mL of distilled water, 1.2 g of lithium hydroxide monohydrate (29.1 mmol, 1.5 eq.) was added, and the mixture was reacted for 12 hours at room temperature. 20 mL of distilled water was added and extracted with ether. Concentrated hydrochloric acid was added to adjust the aqueous layer to pH 3 and then extracted with ethyl acetate. The organic layer was washed with brine and dried over MgSO4, then concentrated under reduced pressure. The mixture was subjected to silica gel column chromatography using a mixed solvent of n-hexane and ethyl acetate (8:1) to obtain 6.8 g (yield 91.8%) of the target product 4d.

[0208] 1 H NMR (CDCl3, 400.13 MHz); δ 4.75 (m, 1H, -COOCH-), 4.51 (m, 1H, COO-CH-), 2.43 (m, 2H, CO-CH2-), 2.17-0.78 (m, 35H, alkyl).

[0209] (4-4) Synthesis of 5-Isopropyl-2-methylcyclohexyl(1-oxo-1-(2-thioxothiazolidin-3-yl)dodecan-5-yl)carbonate

[0210] 9.1 g of 5-(menthylcarbonyloxy)undecanoic acid (4d, 23.6 mmol) was dissolved in 50 mL of dried dichloromethane. 3 g of 2-mercaptothiazoline (24.8 mmol, 1.05 eq.) was added and the mixture was cooled with ice water. Then, 5 g of EDC-HCl (25.9 mmol, 1.1 eq.) and 20 mg of DMAP were slowly added while stirring. After one hour, the reaction solution was warmed to room temperature and allowed to react overnight. Water was then added and the mixture was extracted with dichloromethane. The organic layer was washed with dilute hydrochloric acid, saturated sodium bicarbonate solution, and brine, dried over MgSO4, and concentrated under reduced pressure to obtain 10.9 g (92% yield) of the desired product 5d.

[0211] 1H NMR (CDCl3, 400.13MHz); δ4.71 (m, 1H, -COOCH-), 4.57 (t, 2H, J=8Hz, N-CH2), 4.51 (m, 1H, COO-CH-), 4. 11 (q, 2H, J=8Hz, COO-CH2-), 3.28 (t, 2H, J=8Hz, S-CH2), 3.21 (m, 2H, CO-CH2-), 2.04~0.79 (m, 33H, alkyl).

[0212] (4-5) Synthesis of Glucosyl-(4-mentylcarbonyloxy)undecanoate, 6d

[0213] 4.9 g of 4-(menthylcarbonyloxy)undecanoic acid (12.7 mmol) was dissolved in 30 mL of dichloromethane, followed by the addition of 3 g of thionyl chloride (25.2 mmol, 2 eq) and reflux for two hours. In a separate flask, 6.9 g of glucose (3 eq) and 4.9 g of pyridine (5 eq) were added to DMF solvent and stirred at room temperature while slowly adding the reaction solution dropwise. The reaction mixture was allowed to react for 12 hours. Water was added to the reaction solution, and the mixture was extracted with dichloromethane. The organic layer was washed with dilute hydrochloric acid, saturated sodium bicarbonate solution, and brine, dried over MgSO4, and concentrated under reduced pressure. The product was purified by silica gel column chromatography (MC / MeOH, 10:1) to obtain 2.6 g of the desired product (6d, 37.7% yield).

[0214] 1 H NMR (CDCl3, 400.13 MHz); δ 5.23-3.35 (m, 13H, glucose, -COOCH, -COOCH), 2.43 (m, 2H, CO-CH2-), 2.03-0.78 (m, 35H, alkyl).

[0215] 5. Synthesis of Glucosyl-(4-benzyloxycarbonyloxy)undecanoate (5e)

[0216] [Scheme 5]

[0217]

[0218] (5-1) Synthesis of ethyl 4-hydroxyundecanoate (2d)

[0219] 10 g of γ-undecalactone (54.2 mmol) was dissolved in 50 mL of methanol. 3.9 g of KOH (56.9 mmol, 1.05 eq.) was slowly added while stirring, and the mixture was allowed to react at room temperature for 12 hours. The reaction solution was concentrated under reduced pressure, 50 mL of DMF was added, and 5.9 g of bromoethane (54.2 mmol, 1 eq.) was added while stirring, and the reaction was continued for 12 hours.

[0220] 80 mL of water was added to the reaction solution, and the mixture was extracted with ethyl acetate, washed with water and brine, and the organic layer was dried over MgSO 4 and concentrated under reduced pressure to obtain 10.7 g (85.6%, 2 steps) of the target product 2d.

[0221] 1 H NMR (CDCl3, 400.13 MHz); δ 4.12 (q, 2H, J = 8 Hz, COO-CH2-), 3.59 (m, 1H, CH-O), 2.43 (m, 2H, CO-CH2), 1.81-0.92 (m, 20H, alkyl).

[0222] (5-2) Synthesis of ethyl 4-(benzyloxycarbonyloxy)undecanoate

[0223] 8.3 g of ethyl 4-hydroxyundecanoate (2d, 36 mmol) was dissolved in 50 mL of THF. 5.5 g of pyridine (72.3 mmol, 2 eq.) was added and the mixture was cooled with ice water. A solution of 6.1 g of benzylchloroformate (35.3 mmol, 1 eq.) dissolved in 20 mL of THF was then slowly added dropwise while stirring. After one hour, the reaction solution was warmed to room temperature and allowed to react overnight. Water was then added and the mixture was extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid, a saturated sodium bicarbonate solution, and brine, dried over MgSO, and concentrated under reduced pressure to obtain 9.9 g (yield 75.6%) of the desired product 3e as a yellow liquid.

[0224] 1 H NMR (CDCl3, 400.13 MHz); δ 7.37-7.34 (m, 5H, ph), 5.14 (m, 2H, O-CH2-Ph), 4.12 (brs, 1H, O-CH-), 2.42 (m, 2H, CO-CH2-), 1.90-0.79 (m, 21H, alkyl) ( Figure 24 ).

[0225] (5-3) Synthesis of 4-(benzyloxycarbonyloxy)undecanoic acid [4e]

[0226] 10 g of ethyl 4-(benzyloxycarbonyloxy)undecanoate (3e, 27.5 mmol) was dissolved in 30 mL of THF and 20 mL of distilled water, and 1.7 g of lithium hydroxide monohydrate (41.4 mmol, 1.5 eq.) was added. The mixture was reacted at room temperature for 12 hours. 20 mL of distilled water was added and the mixture was extracted with ether. Concentrated hydrochloric acid was added to adjust the aqueous layer to pH 3, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO, and concentrated under reduced pressure to obtain 8.2 g (89% yield) of the desired product 4e.

[0227] 1 H NMR (CDCl3, 400.13 MHz); δ 7.37-7.35 (m, 5H, ph), 5.14 (m, 2H, O-CH2-Ph), 4.48 (m, 1H, O-CH-), 2.47 (m, 2H, CO-CH2-), 1.90-0.79 (m, 21H, alkyl).

[0228] (5-4) Synthesis of Glucosyl-(4-benzyloxycarbonyloxy)nonanoate [5e]

[0229] 8 g of 4-(Benzyloxycarbonyloxy)undecanoic acid (4e, 23.8 mmol) was dissolved in 30 mL of DMF, followed by the addition of 13 g of glucose (72.1 mmol, 3 eq.). While stirring at room temperature, 3.4 g of diisopropylcarbodiimide (26.9 mmol, 1.1 eq.) and 0.05 g of DMAP (cat.) were added sequentially, and the mixture was allowed to react at room temperature for 12 hours. Distilled water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid, saturated sodium bicarbonate solution, and brine, dried over MgSO4, and then concentrated under reduced pressure. The mixture was subjected to silica gel column chromatography using a mixed solvent of dichloromethane and methanol (8:1) to obtain 0.3 g (yield 2.5%) of the desired product 5e.

[0230] 1 H NMR (CDCl3, 400.13 MHz); δ 7.37-7.34 (m, 5H, ph), 5.30-3.37 (m, 13H, glucose, -COOCH, -COOCH), 2.39 (m, 2H, CO-CH2-), 1.92-0.84 (m, 17H, alkyl).

[0231] Experimental example

[0232] Pyrolysis testing was performed to determine the thermal properties (pyrolytic behavior) of compound 6d (2C) upon exposure to heat. This testing utilized the well-known pyrolysis-gas chromatography / mass spectrometry (Py-GC / MS) method. Pyrolysis was performed using a Double-Shot Pyrolyzer 2020iD (Frontier Lab, Japan) system coupled to a GC / MS system (Agilent 6890gC, USA / Agilent 7890MSD, USA). 2C was diluted to a 2.5% concentration in ethanol, and 10 μl of the solution was placed in a pyrolyzer sample cup for pyrolysis.

[0233] The pyrolysis temperature experienced by the sample was controlled by specifying the furnace temperature of the Double-Shot Pyrolyzer. The initial pyrolysis temperature was 80°C. The sample cup containing the sample was exposed to the furnace for 30 seconds, causing the target compound (2C) in the sample cup to pyrolyze. The components generated by heat or volatilized by heat were immediately injected into the GC / MS injection port and separated. During the GC / MS analysis after pyrolysis, the sample cup was removed from the furnace to avoid being affected by the pyrolysis temperature. After the GC / MS analysis of the first pyrolysis was completed, the sample cup used initially was pyrolyzed again without the injection of new compounds. The pyrolysis temperature was then increased by 10°C to 90°C for 30 seconds. Similarly, the sample cup was removed from the furnace after the pyrolysis was completed to avoid being affected by the pyrolysis temperature. In this way, after the initial sample is placed in the sample cup, the thermal decomposition experiment is performed by raising the thermal decomposition temperature to 80°C, 90°C, 100°C, and finally to 320°C. In this way, the thermal decomposition characteristics of the compound that change with the increase in thermal decomposition temperature can be observed at different temperatures. The results are as follows Figures 25 to 27 shown.

[0234] [Decomposition mechanism]

[0235]

[0236] Reference Figures 25 to 27,The results of thermal decomposition experiments show that compound 2B ,decomposes into menthol and γ-undecalactone at a temperature of about 120 ,℃.

[0237] That is, in the decomposition mechanism, the lactone [1C, gamma-undecalactone] is ring-opened, the hydroxyl group is bonded to L-menthol (L-Menthol) via a carbonate linkage, and then ester-bonded to sugar (glucose) to produce the [2C] compound. After the [2C] compound is applied to the product substrate, L-menthol ([3C]) and CO2 are generated by heating, and the [4C] compound with the exposed hydroxyl group is formed. The [4C] compound is also ring-closed (intramolecular esterification) by heat, thereby producing γ-undecalactone [5C]. In the [2C] state, the hydroxyl group is protected by the menthyl carbonate group, thereby suppressing the ring closure (intramolecular esterification) at room temperature. In addition, as a result of the thermal decomposition experiment, it was confirmed that the lactone ring was generated while the menthol was thermally decomposed.

[0238] The compounds of the present invention that release flavor components upon thermal decomposition are as follows. This pyrolytic behavior reveals the temperature range in which lactones are produced. Therefore, when used in heated cigarettes, the degree and rate of menthol and lactone release from compound 2C added to the medium can be adjusted by appropriately adjusting the heating temperature. This allows for a consistent taste and flavor even when puffed continuously at optimal temperature conditions.

[0239] Example 2

[0240] The target product of the preparation example (synthetic glucosyl-(4-menthylcarbonyloxy)heptanoate, 5a, 1 wt %), a matrix (natural long fiber, pulp, and carboxymethyl cellulose (CMC), 15:50:5 (w / w), 90 wt %), and the remainder of water were mixed, coated onto a substrate, and dried to produce a wallpaper sheet (approximately 2 mm thick). When the wallpaper sheet was smelled at room temperature, no odor of the fragrance composition used to synthesize the target product was detected. However, when the wallpaper sheet was burned, a fragrance (e.g., lactone and menthol aromas used to synthesize the target product) was released.

[0241] Example 3

[0242] The target product of the preparation example (synthetic glucosyl-(4-menthylcarbonyloxy)nonanoate, 5b, 1 wt %), a matrix (natural long fiber, pulp, and carboxymethyl cellulose (CMC), 15:50:5 (w / w), 90 wt %), and the remainder of water were mixed, then coated onto a substrate and dried to produce a wallpaper sheet (approximately 2 mm thick). When the sheet was smelled at room temperature, no odor of the fragrance composition used to synthesize the target product was detected. However, when the wallpaper sheet was burned, a fragrance (e.g., lactone and menthol aromas used to synthesize the target product) was released.

[0243] Example 4

[0244] The target product of the preparation example (synthetic glucosyl-(5-menthylcarbonyloxy)decanoate, 6c, 1 wt%), a matrix (natural long fibers, pulp, and carboxymethyl cellulose (CMC), 15:50:5 (w / w), 95 wt%), and the remainder of water were mixed, then coated onto a substrate and dried to produce a wallpaper sheet (approximately 2 mm thick). When the sheet was smelled at room temperature, no odor of the fragrance composition used to synthesize the target product was detected. However, when the wallpaper sheet was burned, a fragrance (e.g., lactone and menthol aromas used to synthesize the target product) was released.

[0245] Example 5

[0246] A liquid coating composition was prepared comprising the target product of the preparation example (synthetic glucosyl-(5-menthylcarbonyloxy)decanoate, 6c, 1 wt %), a matrix (natural long fibers, pulp, and carboxymethyl cellulose (CMC), 15:50-60:5 (w / w), 80 wt %), propylene glycol, turpentine, and the balance water. The liquid composition was applied to a concrete wall with a brush and dried to produce a wallpaper-like effect. When the decorated wall was smelled at room temperature, no odor of the fragrance composition used to synthesize the target product was detected. However, when the wall was heated by burning furniture near the wall, a fragrance (e.g., lactone and menthol aromas used to synthesize the target product) was released from the wall.

[0247] In summary, the embodiments are described with limited drawings, and those skilled in the art will be able to make various changes and modifications based on the description. Even if the described techniques are performed in a different order, and / or if the described components are combined or combined in different forms or replaced or substituted with other components or equivalents, appropriate results can be obtained. Therefore, other embodiments, other embodiments, and the scope of equivalents to the claims should be interpreted as included in the present invention.

Claims

1. A wallpaper composition, characterized in that: include: A compound represented by the following Chemical Formula 1; as well as substrate, [Chemical Formula 1] In the chemical formula 1, n is an integer of 1 or 2, R is a straight or branched chain alkyl group having 1 to 30 carbon atoms, The moiety A' is a moiety derived from a fragrance compound comprising at least one of an aromatic ring, an aliphatic ring, and an aliphatic chain having a hydroxyl group participating in a carbonate bond. The portion A' corresponds to the fragrance compound other than the hydroxyl groups participating in the carbonate bond, The moiety G' is a moiety derived from a sugar compound, at least one of the hydroxyl groups bonded to the ring of the sugar compound participates in an ester bond. The moiety G' corresponds to a sugar compound excluding the hydroxyl group participating in the ester bond, and m is bonded to the moiety G' via the ester bond. The number of m is an integer from 1 to 8.

2. The wallpaper composition according to claim 1, characterized in that The fragrance compound is selected from cyclic monoterpenoid compounds having a hydroxyl group, acyclic monoterpenoid compounds having a hydroxyl group, aromatic compounds having 6 to 10 carbon atoms and having a hydroxyl group, and non-aromatic ring compounds having 5 to 6 carbon atoms and having a hydroxyl group.

3. The wallpaper composition according to claim 1, characterized in that The fragrance compound is selected from the following chemical formulas: as well as 4. The wallpaper composition according to claim 1, characterized in that The part A' is selected from the following chemical formulas, Wherein, * is the oxygen bonding site within the carbonate bond in Chemical Formula 1: as well as 5. The wallpaper composition according to claim 1, characterized in that The sugar compound is selected from tagatose, trehalose, galactose, rhamnose, cyclodextrin, maltodextrin, dextran, sucrose, glucose, ribulose, fructose, threose, arabinose, xylose, lyxose, allose, altrose, mannose, idose, lactose, maltose, invert sugar, isotrehalose, neotrehalose, palatinose or isomaltulose, erythrose, deoxyribose, idose, talose, erythrulose, Xylulose, psicose, turanose, cellobiose, amylopectin, glucosamine, mannosamine, fucose, glucuronic acid, gluconic acid, gluconolactone, abequose, galactosamine, isomaltooligosaccharides, xylooligosaccharides, gentiooligosaccharides, sorbose, niger oligosaccharides, palatinose, fructooligosaccharides, maltotetraol, maltotriol, maltooligosaccharides, lactulose, melibiose, raffinose, rhamnose, and ribose.

6. The wallpaper composition according to claim 1, characterized in that The compound represented by Chemical Formula 1 is selected from the following Chemical Formulas 1-1 to 1-9: [Chemical Formula 1-1] [Chemical formula 1-2] [Chemical formula 1-3] [Chemical formula 1-4] [Chemical Formula 1-5] Wherein, R in the chemical formulas 1-1 to 1-5 1 to R 5 From hydroxyl and wherein n, R and A' are as defined in the chemical formula 1; [Chemical formula 1-6] Among them, R 1 to R 4 From hydroxyl and wherein n, R and A' are as defined in the chemical formula 1; [Chemical Formula 1-7] [Chemical Formula 1-8] [Chemical Formula 1-9] Wherein, R in the chemical formulas 1-7 to 1-9 1 to R 8 From hydroxyl and , n, R and A' are as defined in the chemical formula 1.

7. The wallpaper composition according to claim 1, characterized in that The compound is selected from the following chemical formulas 1-1-a to 1-9-a: [Chemical formula 1-1-a] [Chemical formula 1-2-a] [Chemical formula 1-3-a] [Chemical formula 1-4-a] [Chemical formula 1-5-a] [Chemical formula 1-6-a] [Chemical formula 1-7-a] [Chemical formula 1-8-a] [Chemical formula 1-9-a] 8. The wallpaper composition according to claim 1, characterized in that The composition generates fragrance upon thermal decomposition, During thermal decomposition, it decomposes into the sugar compound, the flavor compound, the lactone compound and carbon dioxide.

9. The wallpaper composition according to claim 1, characterized in that The compound thermally decomposes at temperatures above 80°C.

10. The wallpaper composition according to claim 8, characterized in that The lactone compound decomposes into the following γ-lactone of Chemical Formula 2 or δ-lactone of Chemical Formula 3: [Chemical Formula 2] [Chemical Formula 3] wherein R is a linear or branched alkyl group having 1 to 30 carbon atoms.

11. The wallpaper composition according to claim 8, characterized in that The lactone compound is selected from the following chemical formula: as well as 12. The wallpaper composition according to claim 1, characterized in that The substrate includes at least one selected from the group consisting of fiber, paper, pulp, cellulose resin, and liquid resin.

13. The wallpaper composition according to claim 1, characterized in that The composition includes at least one of water, a water-soluble organic solvent and a fat-soluble organic solvent.

14. The wallpaper composition according to claim 1, characterized in that The wallpaper composition is a solid, a slurry, a paste, a gel, a liquid, an emulsion or an aerosol.

15. A wallpaper made from the composition of claim 1.

16. The wallpaper according to claim 15, characterized in that The wallpaper is a paint wallpaper or a sheet-type wallpaper.

17. The wallpaper according to claim 16, characterized in that The wallpaper releases a fragrance when burned or exposed to fire temperatures.

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