Compound

Abstract

The present application can provide a compound, a release composition, a release layer, a release film, and an adhesive film. The present application can provide a compound that can form a release layer that exhibits an appropriate level of release force, has excellent bonding strength with a base film, and has excellent solvent resistance. In addition, the present application can provide a compound that, when the release layer is formed, exhibits a stable residual adhesion rate even when the release layer is repeatedly applied to an adhesive layer, etc. In addition, the present application can provide a release composition and a release layer containing the compound, and a release film and an adhesive film containing the release layer.

Description

[Technical field]

[0001] Cross-reference to related applications

[0002] This application claims the benefit of priority based on Korean Patent Application No. 10-2022-0028888, filed on March 7, 2022, and all contents disclosed in the documents of the Korean Patent Application are incorporated as part of this specification.

[0003] Technical Field

[0004] The present application relates to a compound, a release composition, a release layer, a release film and an adhesive film. [Background technology]

[0005] Release films are used to protect adhesive or bonding surfaces, as carriers, and as coating substrates. For example, so-called light or heavy release films can be used to protect optically clear adhesives (OCA). Release films can also be used as carriers for tapes, or as coating substrates for multi-layer ceramic capacitors (MLCCs).

[0006] The release layer of a release film is generally formed of a silicone-based compound, and a composition containing a silicone-based compound, such as a silicone resin, may be coated onto a substrate film to form a release layer containing the silicone resin on the substrate film.

[0007] The release layer has low surface energy and flexibility. For example, Patent Document 1 discloses a release film having a release layer formed of a silicone compound.

[0008] In a release film, the bonding strength between the base film and the release layer must be secured. If the bonding strength between the base film and the release layer is weakened, the release film cannot function.

[0009] However, a release layer formed using a silicone-based compound generally does not have a high bonding strength with a substrate film, and the bonding strength tends to decrease over time.

[0010] In addition, the release layer often comes into contact with a solvent during the process of forming the release layer or during the process of using the release film. If the solvent resistance of the release layer is poor at this time, the bonding strength decreases or the release layer can be easily damaged, so ensuring the solvent resistance of the release layer is also an important issue. [Prior art documents] [Patent documents]

[0011] [Patent Document 1] Republic of Korea Patent Publication No. 10-2021-0115256 Summary of the Invention [Problem to be solved by the invention]

[0012] The present application provides a compound, a release composition, a release layer, a release film and an adhesive film.

[0013] The present application aims to provide a compound capable of forming a release layer having an appropriate level of release force, excellent bonding strength with a base film, and excellent solvent resistance. The present application also aims to provide a compound that, when the release layer is formed, exhibits a stable residual adhesion rate even when the release layer is repeatedly applied to a pressure-sensitive adhesive layer or the like.

[0014] Another object of the present application is to provide a release composition and a release layer containing the compound, and a release film and an adhesive film containing the release layer. [Means for solving the problem]

[0015] In the present specification, when the measurement temperature affects a physical property, the physical property is measured at room temperature unless otherwise specified. In the present specification, the term "room temperature" refers to a natural temperature without artificial heating or cooling, and may refer to, for example, any one temperature within a range of 10°C to 30°C, or a temperature of about 15°C or more, 18°C ​​or more, 20°C or more, or about 23°C or more and about 27°C or less, or a temperature of about 23°C, about 25°C, or about 27°C.

[0016] Unless otherwise specified, temperatures referred to herein are in °C.

[0017] In the present application, when the measurement pressure affects a physical property, the physical property is measured at normal pressure unless otherwise specified. In the present specification, the term "normal pressure" refers to a natural pressure without artificial pressure or pressure reduction, and generally refers to a pressure at atmospheric pressure, for example, about 740 mmHg to 780 mmHg.

[0018] The term "relative humidity" used in this application means the ratio of the amount of water vapor contained in a unit volume of air to the maximum saturated water vapor pressure that the unit volume of air can contain, expressed as a percentage (%), and can be expressed as RH%. When the relative humidity affects any physical property mentioned in this application, the relevant physical property is measured in a normal humidity environment (approximately 30RH% to 70RH%) unless otherwise specified.

[0019] The term "a to b" used in this application means within the range between a and b, including a and b. For example, "containing a to b parts by weight" is the same as meaning contained within the range of a to b parts by weight.

[0020] The term "substituted" as used in the present application means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position of the substitution is not particularly limited as long as it is a position at which a hydrogen atom is substituted, i.e., a position at which a substituent can be substituted, and when two or more substituents are substituted, the substituents may be the same or different from each other.

[0021] The alkyl or alkoxy group referred to in this specification, unless otherwise specified, may be a straight or branched alkyl or alkoxy group having 1 to 20 carbon atoms, or 1 to 16 carbon atoms, or 1 to 12 carbon atoms, or 1 to 8 carbon atoms, or 1 to 6 carbon atoms, or a cyclic alkyl or alkoxy group having 3 to 20 carbon atoms, or 3 to 16 carbon atoms, or 3 to 12 carbon atoms, or 3 to 8 carbon atoms, or 3 to 6 carbon atoms. The cyclic alkyl or alkoxy group includes an alkyl or alkoxy group that is only a ring structure, and an alkyl or alkoxy group that includes a ring structure. For example, a cyclohexyl group and a methylcyclohexyl group are both cyclic alkyl groups.

[0022] In the present application, the alkylene group and the alkylene group refer to a divalent residue formed by removing two hydrogen atoms from an alkane. In the case of the alkylene group, the two hydrogen atoms are removed from different carbon atoms of the alkane, one each, and the alkylidene group is a structure in which the two hydrogen atoms are removed from one carbon atom of the alkane. In the present specification, unless otherwise specified, the alkylidene group may be a linear or branched alkylidene group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 6 carbon atoms, or a cyclic alkylidene group having 3 to 20 carbon atoms, 3 to 16 carbon atoms, 3 to 12 carbon atoms, 3 to 8 carbon atoms, or 3 to 6 carbon atoms. The cyclic alkylidene group also includes an alkylidene group that is only a ring structure and an alkylidene group that includes a ring structure. In this specification, unless otherwise specified, the alkylene group may be a straight-chain or branched-chain non-cyclic alkylene group having 2 to 20 carbon atoms, or 2 to 16 carbon atoms, or 2 to 12 carbon atoms, or 2 to 8 carbon atoms, or 2 to 6 carbon atoms, or a cyclic alkylene group having 3 to 20 carbon atoms, or 3 to 16 carbon atoms, or 3 to 12 carbon atoms, or 3 to 8 carbon atoms, or 3 to 6 carbon atoms. The cyclic alkylene group also includes an alkylene group which is only a ring structure and an alkylene group which contains a ring structure.

[0023] Unless otherwise specified, the alkenyl or alkenylene group referred to in this specification may be a straight-chain or branched non-cyclic alkenyl or alkenylene group having 2 to 20, 2 to 16, 2 to 12, 2 to 8, or 2 to 6 carbon atoms, or may be a cyclic alkenyl or alkenylene group having 3 to 20, 3 to 16, 3 to 12, 3 to 8, or 3 to 6 carbon atoms. The cyclic alkenyl or alkenylene group includes an alkenyl or alkenylene group which is only a ring structure and an alkenyl or alkenylene group which contains a ring structure.

[0024] Unless otherwise specified, the alkynyl or alkynylene group referred to in this specification may be a straight-chain or branched non-cyclic alkynyl or alkynylene group having 2 to 20, 2 to 16, 2 to 12, 2 to 8, or 2 to 6 carbon atoms, or a cyclic alkynyl or alkynylene group having 3 to 20, 3 to 16, 3 to 12, 3 to 8, or 3 to 6 carbon atoms. Here, if an alkynyl or alkynylene group having a ring structure is included, it corresponds to a cyclic alkynyl or alkynylene group.

[0025] The alkyl group, alkoxy group, alkylidene group, alkylene group, alkenyl group, alkenylene group, alkynyl group and alkynylene group may be substituted with any one or more substituents, in which case the substituents may be one or more selected from the group consisting of halogen (chlorine (Cl), iodine (I), bromine (Br), fluorine (F)), aryl group, heteroaryl group, epoxy group, alkoxy group, cyano group, carboxyl group, acryloyl group, methacryloyl group, acryloxy group, methacryloyloxy group, carbonyl group and hydroxy group, but are not limited thereto.

[0026] The term "aryl group" as used herein means a substituent formed by removing one hydrogen from an aromatic hydrocarbon ring compound, and the aromatic hydrocarbon ring compound may be a monocyclic or polycyclic ring compound. The number of carbon atoms in the aryl group is not particularly limited, but unless otherwise specified, the aryl group may be an aryl group having 6 to 20 carbon atoms, 6 to 18 carbon atoms, or 2 to 15 carbon atoms.

[0027] In the present specification, the term "arylene group" refers to a divalent functional group in which one hydrogen is removed from the aryl group. The above description of the aryl group may be applied to these groups except that they are divalent groups. Examples of the aryl group include, but are not limited to, a phenyl group, a phenylethyl group, a phenylpropyl group, a benzyl group, a tolyl group, a xylyl group, and a naphthyl group.

[0028] In the present application, the term "heteroaryl group" refers to a functional group having a structure in which one or more of the carbon atoms constituting the aromatic ring of an aryl group are replaced with a heteroatom other than a carbon atom. Examples of the heteroatom include nitrogen (N), oxygen (O), sulfur (S), selenium (Se) and tellurium (Te). The atoms constituting the ring structure of the heteroaryl group can be referred to as ring atoms. In addition, the heteroaryl group can include a monocyclic or polycyclic ring. The number of carbon atoms or ring atoms of the heteroaryl group is not particularly limited, and may be within the range of 2 to 30, or 2 to 26, or 2 to 22, or 2 to 20, or 2 to 18, or 2 to 15, unless otherwise specified. In other examples, the heteroaryl group is not particularly limited in the number of ring atoms, and may be, for example, a heteroaryl group having 5 to 30, 5 to 25, 5 to 20, 5 to 15, 5 to 10, or 5 to 8 ring atoms. Examples of the heteroaryl group include a thiophene group, a furan group, a pyrrole group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazinyl group, an acridyl group, a pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolinyl group, an indole group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a benzothiophene group, a dibenzothiophene group, a benzofuran group, a dibenzofuran group, a benzosilole group, a dibenzosilole group, a phenanthrolinyl group, group), an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, a phenoxazinyl group, and condensed structures thereof can be exemplified, but are not limited to these.

[0029] In addition, the term "heteroarylene group" used in this application means a divalent group obtained by removing one additional hydrogen atom from the heteroaryl group. The above description of the heteroaryl group can be applied to these groups, except that they are divalent groups.

[0030] The aryl group or heteroaryl group may be optionally substituted with one or more substituents, which may be one or more selected from the group consisting of halogen (chlorine (Cl), iodine (I), bromine (Br), fluorine (F)), aryl group, heteroaryl group, epoxy group, alkoxy group, cyano group, carboxyl group, acryloyl group, methacryloyl group, acryloxy group, methacryloyloxy group, carbonyl group, and hydroxy group, but are not limited thereto.

[0031] The present application provides a compound of a specific structure. In one embodiment, the compound may be a compound that includes a silicon atom to which a radical-generating functional group is bonded.

[0032] For example, the compound may be a compound that includes a chain formed of silicon atoms connected by a linker and a radical-generating functional group linked to the silicon atoms present in the chain.

[0033] Such compounds can be represented, for example, by the average unit of Formula 1 below.

[0034] [Chemical formula 1]

[0035] R 1 m R 2 n Six (4-m-n) / 2

[0036] In formula 1, R 1 may be a radical-generating functional group, R 2may be hydrogen, an isocyanatoalkyl group, a hydroxyalkyloxy group, an alkoxy group, or a monovalent hydrocarbon group, and X may be a linker connecting the silicon atoms of the compound to each other.

[0037] In Chemical Formula 1, m may be a number in the range of 1 to 3, n may be a number in the range of 0 to 2, and the sum of m and n (m+n) may be a number in the range of 1 to 3.

[0038] The term "average unit" as used herein refers to a formula in which the number of moles of silicon atoms contained in the compound is taken as 1 mole, and the number of moles of functional groups (functional groups directly linked to silicon atoms) and linkers (linkers linking silicon atoms to silicon atoms) contained in the compound are converted based on this. Such an average unit may be for one molecule of a compound or for a mixture of two or more molecules of a compound. When the average unit is for a mixture of two or more molecules of a compound, the proportion of other functional groups or linkers is calculated assuming that the number of all silicon atoms contained in the mixture is 1.

[0039] R shown to the left of the silicon atom (Si) in chemical formula 1 1 and R 2 represents a functional group directly linked to the silicon atom, and the X on the right represents a linker connecting the silicon atoms.

[0040] In Chemical Formula 1, m is the functional group R 1 n is the number of moles of the functional group R 2 is the number of moles.

[0041] In addition, in Chemical Formula 1, (4-mn) is the number of moles of the linker X, calculated assuming that the number of moles of silicon atoms contained in the compound is 1 mole. In the case of the linker X, since two silicon atoms are bonded, the number of moles is divided by 2.

[0042] This method of expression is similar to the method of expressing the average unit of a so-called polyorganosiloxane.

[0043] In Formula 1, the linker X may be an oxygen atom or a bivalent linker of Formula 2 below:

[0044] [Chemical formula 2]

[0045] [ka]

[0046] In Formula 2, L1 may be an alkylene group or an alkylidene group.

[0047] Specific examples of the alkylene group or alkylidene group in the above formula 2 are as exemplified at the beginning of this specification.

[0048] In Chemical Formula 2, the oxygen atoms on both sides of L1 are each directly linked to a silicon atom of the compound.

[0049] As described below, the compound is a compound having a desired functional group (R 1 The compound is prepared by reacting an alkoxysilane having an alkoxy group introduced therein with a diol compound forming a linker of the formula 2. In this case, the alkoxy group of the alkoxysilane reacts with the hydroxy group of the diol compound to produce a structure in which the silicon atom of the alkoxysilane is linked by the linker of the formula 2. In this reaction process, a siloxane bond in which silicon atoms are bonded via an oxygen atom may be produced by a condensation reaction between the alkoxy groups of the alkoxysilane. Therefore, in the formula 1, X may be an oxygen atom or a divalent linker of the formula 2.

[0050] In one example, a certain level or more of the total linker X contained in the compound having an average unit of Chemical Formula 1 may be the linker of Chemical Formula 2. For example, the lower limit of the ratio of the number of moles of the linker of Chemical Formula 2 based on the total number of moles of the linker X contained in the compound may be about 70 mol%, 75 mol%, 80 mol%, 85 mol%, 90 mol%, 95 mol%, or 97 mol%, and the upper limit may be about 100. The ratio may be equal to or greater than any one of the lower limits described above, or may be equal to or greater than any one of the lower limits described above and less than or equal to the upper limit described above.

[0051] In formula 1, R 1 is a radical-generating functional group. The term "radical-generating functional group" refers to a functional group that includes a moiety that can generate a radical upon application of energy such as irradiation with light or application of heat, and the type of such functional group is not limited as long as it can generate a radical.

[0052] In formula 1, R 2 may be hydrogen, an isocyanatoalkyl group, a hydroxyalkyloxy group, an alkoxy group, or a monovalent hydrocarbon group.

[0053] R in Chemical Formula 1 2 Specific types of the isocyanatoalkyl group and the alkyl group contained in the hydroxyalkyloxy group and specific types of the alkoxy group are as described at the beginning of this specification.

[0054] The term "monovalent hydrocarbon group" as used above refers to a monovalent residue derived from a substituted or unsubstituted hydrocarbon (an organic compound consisting of carbon and hydrogen), examples of which include an alkyl group, an alkenyl group, an alkynyl group, or an aryl group. Specific examples of the alkyl group, the alkenyl group, the alkynyl group, or the aryl group are as described at the beginning of this specification.

[0055] As described below, the compound has the radical-generating functional group (R 1The alkoxysilane having the isocyanatoalkyl group introduced therein can be reacted in the presence of a diol compound, and the radical-generating functional group can be introduced by a urethane reaction using an alkoxysilane compound having an isocyanatoalkyl group. In this case, theoretically, all of the isocyanatoalkyl groups contained in the alkoxysilane compound are converted to the radical-generating functional group, and all of the alkoxy groups of the alkoxysilane compound are converted to a linker (oxygen atom or the linker of the above formula 2). However, in the final compound, isocyanatoalkyl groups that did not participate in the urethane reaction may remain, and alkoxy groups that did not form the linker and / or alkoxy groups that reacted with the diol compound but did not form the linker (these alkoxy groups exist in the form of hydroxyalkyloxy groups) may remain. In addition, hydrogen or monovalent hydrocarbon groups that do not participate in the urethane reaction and the linker-forming reaction may be present in the alkoxysilane compound.

[0056] Therefore, R in formula 1 2 may be hydrogen, an isocyanatoalkyl group, a hydroxyalkyloxy group, an alkoxy group, or a monovalent hydrocarbon group.

[0057] In Chemical Formula 1, m is a number within the range of 1 to 3, a number within the range of 1 to 2.5, a number within the range of 1 to 2, or a number within the range of 1 to 1.5, or may be approximately 1.

[0058] In Chemical Formula 1, n may be a number in the range of 0 to 2, a number in the range of 0 to 1.5, or a number in the range of 0 to 1.

[0059] The sum of m and n (m+n) in Chemical Formula 1 may be a number in the range of 1 to 3, a number in the range of 1.5 to 3, a number in the range of 2 to 3, or a number in the range of 2.5 to 3.

[0060] In one example, the radical-forming functional group R 1 may be a functional group represented by the following chemical formula 3:

[0061] [Chemical formula 3]

[0062] [ka]

[0063] In Formula 3, L2 and L3 may each independently be an alkylene group or an alkylidene group, and R3 may be an aryl group or a heteroaryl group.

[0064] Specific examples of the alkylene group and alkylidene group of L2 and L3 in Chemical Formula 3 are as described at the beginning of this specification. Specific examples of the aryl group or heteroaryl group of R3 are also as described at the beginning of this specification.

[0065] L2 in Formula 3 is directly linked to the silicon atom of the compound.

[0066] In one example, in Formula 3, L2 and L3 may each independently be the alkylene group, and R3 may be the aryl group.

[0067] The functional group of Chemical Formula 3 has an oxygen atom on both sides of L3. Due to the high electronegativity of the oxygen atom, the carbon-carbon bond or carbon-oxygen bond in the -O-L3-C(=0)- structure has a relatively weak bond strength, and therefore, when external energy such as light irradiation or heat is applied, the bond can be broken to generate a radical.

[0068] The compound can have a branched structure, a cage structure or a partial cage structure. The branched structure, the cage structure or the partial cage structure is substantially the same as the branched structure, the cage structure or the partial cage structure referred to for so-called polyorganosiloxane. The difference is that in the case of polyorganosiloxane, the linker connecting silicon atoms in the structure is an oxygen atom, while in the case of the compound, the linker (X in formula 1) is an oxygen atom or the linker in formula 2.

[0069] The compound may be a polymer compound. Therefore, the compound may have a molecular weight of a certain level or more. For example, the lower limit of the weight average molecular weight of the compound may be 5,000 g / mol, 6,000 g / mol, 7,000 g / mol, 8,000 g / mol, 9,000 g / mol, 10,000 g / mol, 15,000 g / mol, 20,000 g / mol, 25,000 g / mol, 30,000 g / mol, 35,000 g / mol, 40,000 g / mol, 45,000 g / mol, or 50,000 g / mol. The weight average molecular weight of the compound may be about 200,000 g / mol, 150,000 g / mol, 100,000 g / mol, 95,000 g / mol, 90,000 g / mol, 85,000 g / mol, 80,000 g / mol, 75,000 g / mol, 70,000 g / mol, 65,000 g / mol, 60,000 g / mol, 55,000 g / mol, or 50,000 g / mol. The weight average molecular weight of the compound may be less than or equal to any one of the upper limits described above, or greater than or equal to any one of the lower limits described above, or may be less than or equal to any one of the upper limits described above and greater than or equal to any one of the lower limits described above.

[0070] The compound may have a certain level of polydispersity index. The polydispersity index is the weight average molecular weight (Mw) of the compound divided by the number average molecular weight (Mn) (Mw / Mn). The lower limit of the polydispersity index may be about 1, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2 or 2.1, and the upper limit may be about 10, 9, 8, 7, 6, 5, 4.5, 4, 3.5, 3 or 2.5. The polydispersity index of the compound may be less than or equal to any of the upper limits described above, or may be greater than or equal to any of the lower limits described above, or may be less than or equal to any of the upper limits described above and greater than or equal to any of the lower limits described above.

[0071] The above-mentioned compounds are contained in the release layer to form a specific crosslinked structure, thereby providing the release layer of the present application.

[0072] The above compounds can be synthesized by utilizing known methods, for example, known methods for producing polyorganosiloxanes.

[0073] Among the methods for synthesizing polyorganosiloxane, a method is known in which an alkoxysilane is used as a monomer and the alkoxysilane is subjected to a condensation reaction to form the polyorganosiloxane. In the present application, the condensation reaction of the polyorganosiloxane is carried out in the presence of a diol compound. In this case, the linker of the formula 2 can be formed through a reaction between the hydroxy group of the diol compound and the alkoxy group of the alkoxysilane. In addition, the R 1 and / or R 2 A compound having an average unit of the above formula 1 can be synthesized by applying a compound having the above formula:

[0074] In the process, the alkoxysilane is 1 and / or R 2 In particular, the functional group R 1 The method for introducing the functional group R is not particularly limited. For example, a commercially available alkoxysilane may be used which contains the alkoxy group and the functional group R 1 and / or R 2 Alternatively, the functional group may be introduced into the alkoxysilane through a separate reaction. For example, when an alkoxysilane having an isocyanate group is used as the alkoxysilane and is reacted with a radical generating compound having a hydroxyl group, the radical generating site of the radical generating compound can be introduced into the alkoxysilane through a urethane reaction or the like.

[0075] One exemplary synthesis scheme for such compounds is described in Preparation 1 herein.

[0076] In Production Example 1, first, an isocyanate compound having an alkoxysilyl group (alkoxysilane having an isocyanate group) is reacted with a radical generating compound having a hydroxyl group to obtain an alkoxysilane (intermediate product) having a radical generating site introduced therein. A commercially available compound can be used as the isocyanate compound having an alkoxysilyl group, and a commercially available compound (for example, a compound having a hydroxyl group among compounds known as radical initiators) can also be used as the radical generating compound.

[0077] The reaction to obtain the intermediate product can be carried out at a predetermined temperature for a predetermined time by adding a catalyst if necessary. Then, the intermediate product can be further reacted in the presence of a polyol (diol compound) to obtain a target compound. The further reaction can also be carried out at a predetermined temperature for a predetermined time. The temperature and time can be adjusted in consideration of the reacting compounds and the yield of the target compound, and for example, the predetermined temperature can be in the range of 60°C to 150°C, and the predetermined time can be in the range of 1 hour to 7 hours, but are not limited thereto.

[0078] As described above, the radical generating compound applied to the reaction may be, for example, a compound having a hydroxy group among compounds known to be capable of generating radicals. One example of such a compound is a radical initiator having a hydroxy group and a ketone group. As such a radical initiator, one or more selected from the group consisting of 2-hydroxy-2-methyl-1-phenyl-1-propanone, 1-hydroxycyclohexyl phenyl ketone, 4-(2-hydroxyethoxy)phenyl-2-(hydroxy-2-propyl)ketone, and oligo[2-hydroxy-2-methyl-1[4-(1-methylvinyl)phenyl]propanone] may be used, but is not particularly limited thereto. In addition, the radical generating compound may contain one or more functional groups selected from the group consisting of an aryl group and a heteroaryl group. When the radical generating compound contains an aryl group and / or a heteroaryl group, it is possible to form a compound that can be post-cured by initiating polymerization without decomposition and that can reduce unreacted materials.

[0079] The type of the isocyanate compound having an alkoxysilyl group is not particularly limited as long as it is a compound containing an alkoxysilyl group and an isocyanate group at the end. For example, the silicon atom (Si) of the alkoxysilyl group and the nitrogen atom (N) of the isocyanate may be bonded with an alkylene group having 1 to 20 carbon atoms. In another example, the upper limit of the carbon number may be about 19, 18, 17, 16, 15, 14, 13, 12, 11, 10, 9, 8, 7, 6, 5, 4, or 3. The carbon number may be equal to or less than any of the upper limits described above, but is not limited thereto.

[0080] The isocyanate compound having an alkoxysilyl group may have at least one or more alkoxysilyl groups, and the alkoxy group bonded to the silicon atom (Si) in the alkoxysilyl group may be an alkoxy group having 1 to 20 carbon atoms. The upper limit of the carbon number may be about 19, 18, 17, 16, 15, 14, 13, 12, 11, 10, 9, 8, 7, 6, 5, 4, or 3. The carbon number may be equal to or less than any of the upper limits described above, and for example, the isocyanate compound having an alkoxysilyl group may be 3-(triepoxysilyl)propyl isocyanate, 3-(trimethoxysilyl)propyl isocyanate, 3-(triepoxysilyl)ethyl isocyanate, 3-(triethoxysilyl)butyl isocyanate, or 3-(triethoxysilyl)methyl isocyanate.

[0081] The intermediate product for synthesizing the compound can be obtained by reacting a composition containing an isocyanate compound having an alkoxysilyl group and a radical generating compound as described above. At this time, the ratio of each reacting compound in the composition can be adjusted in consideration of the structure of the target compound.

[0082] For example, the lower limit of the content of the radical generating compound in the composition may be about 10 wt%, 12.5 wt%, 15 wt%, 17.5 wt%, 20 wt%, 22.5 wt%, 25 wt%, 27.5 wt%, 30 wt%, 32.5 wt%, or 35 wt%, and the upper limit may be about 50 wt%, 48 wt%, 46 wt%, 44 wt%, 42 wt%, or 40 wt%. The ratio may be less than or equal to any of the upper limits described above, or greater than or equal to any of the lower limits described above, or less than or equal to any of the upper limits described above and greater than or equal to any of the lower limits described above. When the composition forming the intermediate product contains the compound in the above content, it is possible to provide a compound that can form a release layer having excellent film-forming properties, an appropriate level of release force, and excellent residual adhesion rate, and in which changes in release force due to external factors such as heat and ultraviolet rays are minimized.

[0083] The lower limit of the weight of the isocyanate compound having an alkoxysilyl group in the composition relative to 100 parts by weight of the radical generating compound may be about 100 parts by weight, 105 parts by weight, 110 parts by weight, 115 parts by weight, 120 parts by weight, 125 parts by weight, 130 parts by weight, 135 parts by weight, 140 parts by weight, 145 parts by weight, or 150 parts by weight, and the upper limit may be about 300 parts by weight, 280 parts by weight, 260 parts by weight, 240 parts by weight, 220 parts by weight, 200 parts by weight, 180 parts by weight, or 160 parts by weight. The ratio may be less than or equal to any one of the upper limits described above, or greater than or equal to any one of the lower limits described above, or less than or equal to any one of the upper limits described above, and greater than or equal to any one of the lower limits described above. When the composition forming the intermediate product contains an isocyanate compound having an alkoxysilyl group within the above range, it is possible to form a compound that exhibits excellent cohesive strength, which is advantageous for forming a coating film, exhibits appropriate elasticity and hydrophilicity, has an appropriate level of release force, has an excellent residual adhesion rate, and can form a release layer in which changes in release force due to external factors such as heat and ultraviolet rays are minimized.

[0084] The reaction to form the intermediate product may be carried out in the presence of a suitable catalyst, for example, a catalyst known as a urethane catalyst. Examples of such catalysts include tertiary amine compounds, aprotic salts, and organometallic compounds, and specifically, organotin catalysts such as dibutyltin dilaurate (DBTDL) may be used, but are not limited thereto.

[0085] The lower limit of the content of the catalyst relative to 100 parts by weight of the composition for forming the intermediate product is 0.001 parts by weight, 0.005 parts by weight, 0.01 parts by weight, 0.015 parts by weight, 0.02 parts by weight, 0.025 parts by weight, 0.03 parts by weight, 0.035 parts by weight, 0.04 parts by weight, 0.045 parts by weight, 0.05 parts by weight, 0.055 parts by weight, 0.06 parts by weight, 0.065 parts by weight, 0.07 parts by weight, 0.075 parts by weight, 0.08 parts by weight, 0.085 parts by weight, 0.09 parts by weight, 0.095 parts by weight, 0.1 parts by weight, 0.12 parts by weight, 0.14 parts by weight, 0.16 parts by weight, 0.18 parts by weight, 0.20 parts by weight, 0.25 parts by weight, 0.26 parts by weight, 0.28 parts by weight, 0.29 parts by weight, 0.30 parts by weight, 0.31 parts by weight, 0.32 parts by weight, 0.33 parts by weight, 0.34 parts by weight, 0.35 parts by weight, 0.36 parts by weight, 0.37 parts by weight, 0.38 parts by weight, 0.39 parts by weight, 0.40 parts by weight, 0.41 parts by weight, 0.42 parts by weight, 0.43 parts by weight, 0.44 parts by weight, 0.45 parts by weight, 0.46 parts by weight, 0.47 parts by weight, 0.48 parts by weight, 0.49 parts by weight, 0.50 parts by weight, 0.51 parts by weight, 0.52 parts parts by weight, 0.2 parts by weight, 0.22 parts by weight, or 0.24 parts by weight, and the upper limit may be about 0.5 parts by weight, 0.49 parts by weight, 0.48 parts by weight, 0.47 parts by weight, 0.46 parts by weight, 0.45 parts by weight, 0.44 parts by weight, 0.43 parts by weight, 0.42 parts by weight, 0.41 parts by weight, 0.4 parts by weight, 0.39 parts by weight, 0.38 parts by weight, 0.37 parts by weight, 0.36 parts by weight, 0.35 parts by weight, 0.34 parts by weight, 0.32 parts by weight, 0.31 parts by weight, 0.3 parts by weight, 0.29 parts by weight, 0.28 parts by weight, 0.27 parts by weight, 0.26 parts by weight, or 0.25 parts by weight. The catalyst content may be below or below any of the upper limits described above, or above or above any of the lower limits described above, or below or below any of the upper limits described above and above or above any of the lower limits described above.

[0086] The intermediate product obtained by reacting the composition can be condensed in the presence of a polyol (diol compound) to produce a compound represented by the average unit of Formula 1.

[0087] The polyol means a compound having two or more hydroxyl groups in the molecule. The polyol is sufficient as long as it has two or more hydroxyl groups in the molecule, and the type is not particularly limited. Examples of the polyol include (poly)ethylene glycol, diethylene glycol, (poly)propylene glycol, 1,2-butylene glycol, 2,3-butylene glycol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 1,6-hexanediol, neopentyl glycol, 1,2-ethylhexyldiol, 1,5-pentanediol, 1,9-nonanediol, and the like. Examples of the polyolefin copolymer that can be used include, but are not limited to, 1,10-decanediol, 1,3-cyclohexanedimethanol and 1,4-cyclohexanedimethanol, (poly)ethylenetriol, diethylenetriol, (poly)propylenetriol, glycerin, 1,2,3-butanetriol, 1,2,4-butanetriol, 1,3,4-hexanetriol, 1,3,6-hexanetriol unit, trimethylolpropane, and 2,2-dimethyl-1,3-propanediol.

[0088] The amount of the polyol used may also be adjusted in consideration of the structure of the target compound. For example, the lower limit of the weight part of the polyol relative to 100 parts by weight of the intermediate product may be 0.1 parts by weight, 0.2 parts by weight, 0.3 parts by weight, 0.4 parts by weight, 0.5 parts by weight, 0.6 parts by weight, 0.7 parts by weight, 0.8 parts by weight or more, or 0.9 parts by weight, and the upper limit may be 5 parts by weight, 4.5 parts by weight, 4 parts by weight or less, 3.5 parts by weight, 3 parts by weight, 2.5 parts by weight, 2 parts by weight, 1.5 parts by weight or 1 part by weight. The polyol may be less than or equal to any of the upper limits described above, greater than or equal to any of the lower limits described above, or less than or equal to any of the upper limits described above and greater than or equal to any of the lower limits described above.

[0089] The method for carrying out the condensation reaction is not particularly limited, and may be carried out in a known manner.

[0090] The present application also relates to a release composition comprising said compound. The term "release composition" means a composition capable of forming a release layer, where the meaning of release layer is as known in the art.

[0091] The release composition may be a curable composition, in which case the composition can form the release layer before or after curing.

[0092] When the release composition is curable, the composition may be of an active energy ray (e.g., ultraviolet ray) curable type, a moisture curable type, a heat curable type, or a room temperature curable type, and in some cases, may be a hybrid type in which two or more of the above are combined. When the release composition is of an active energy ray curable type, the release composition is cured by irradiation of an active energy ray such as ultraviolet ray, when the release composition is of a moisture curable type, the release composition is cured by maintaining the release composition under appropriate humidity, when the release composition is of a heat curable type, the release composition is cured by applying appropriate heat, or when the release composition is of a room temperature curable type, the release composition is cured by maintaining the release composition at room temperature.

[0093] In the release composition, the lower limit of the content of the compound having an average unit of Chemical Formula 1 may be about 0.01 wt%, 0.05 wt%, 0.1 wt%, 0.5 wt%, 1 wt%, 5 wt%, 7 wt%, 9 wt%, 10 wt%, 11 wt%, 13 wt%, or 14 wt%, and the upper limit thereof may be about 40 wt%, 39 wt%, 38 wt%, 36 wt%, 34 wt%, 32 wt%, 30 wt%, 28 wt%, 26 wt%, 24 wt%, 22 wt%, 20 wt%, 18 wt%, 16 wt%, 14 wt%, 12 wt%, 10 wt%, 8 wt%, 6 wt%, 4 wt%, 2 wt%, or 1 wt%. The ratio may be less than or equal to any one of the upper limits described above, or may be greater than or equal to any one of the lower limits described above, or may be greater than or equal to any one of the lower limits described above and less than or equal to any one of the upper limits described above. Within the above range, a release composition that can ensure appropriate coating film forming ability, release peel strength, and excellent residual adhesion rate can be provided. The ratio is based on the solid content, and therefore, when the release composition contains a solvent, it is the ratio relative to the total weight of the release composition excluding the weight of the solvent. The ratio may be the ratio of the compound or its reactant in the release layer described below.

[0094] The release composition may be a solvent-based, water-based or solventless release composition.

[0095] The mold release composition includes the compound and may further include a curable silicone resin component. As used herein, the term "silicone resin component" refers to a component that is either a polyorganosiloxane or a mixture of two or more polyorganosiloxanes.

[0096] In one example, the silicone resin component of the mold release composition may be a so-called addition curing type component. Such a resin component may include, for example, a polyorganosiloxane containing a siloxane unit having an alkenyl group bonded to a silicon atom (hereinafter, may be referred to as a first polyorganosiloxane or a first polyorganosiloxane component).

[0097] The first polyorganosiloxane or the first polyorganosiloxane component may have, for example, an average unit of the following chemical formula 4. Such an average unit may be for one molecule of polyorganosiloxane or for a mixture of two or more molecules of polyorganosiloxane. When the average unit is for a mixture of two or more molecules of polyorganosiloxane, the ratio of other functional groups or atoms is calculated assuming that the number of all silicon atoms contained in the mixture is 1.

[0098] [Chemical formula 4]

[0099] P a Q b SiO (4-a-b) / 2

[0100] In Chemical Formula 4, P may be an alkenyl group, Q may be an alkoxy group, a hydroxy group, or a monovalent hydrocarbon group, a may be a number in the range of 0.0001 to 0.1, and b may be a number in the range of 1 to 4.

[0101] In Chemical Formula 4, the specific types of the alkenyl group and alkoxy group are as described at the beginning of this specification, and the specific type of the monovalent hydrocarbon group is the same as the monovalent hydrocarbon group in Chemical Formula 1.

[0102] In chemical formula 4, the lower limit of a is 0.0002, 0.0003, 0.0004, 0.0005, 0.0006, 0.0007, 0.0008, 0.0009, 0.001, 0.002, 0.003, 0.004, 0.005, 0.006, 0.007, 0.008, 0.009, 0.01, 0.012, 0.01 4, 0.016, 0.018, 0.02 or 0.022, and the upper limit may be about 0.09, 0.08, 0.07, 0.06, 0.05, 0.04, 0.03, 0.02, 0.01, 0.009, 0.008, 0.007, 0.006, 0.005, 0.004 or 0.003. The a may be less than or less than any one of the upper limits described above, or greater than or exceeding any one of the lower limits described above, or less than or less than any one of the upper limits described above, and may be greater than or exceeding any one of the lower limits described above.

[0103] In the formula 4, the lower limit of b may be about 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8 or 1.9, and the upper limit of b may be about 3.5, 3, 2.9, 2.8, 2.7, 2.6, 2.5, 2.4, 2.2, 2.1 or 2. The b may be less than or equal to any one of the upper limits described above, greater than or equal to any one of the lower limits described above, or less than or equal to any one of the upper limits described above, and greater than or equal to any one of the lower limits described above.

[0104] The polyorganosiloxane having the average unit of the chemical formula 4 may contain alkenyl groups in the range of 0.01 mol% to 1.5 mol% of the total organic groups. For example, the lower limit of the molar number of the alkenyl groups based on the molar number of the total organic groups contained in the organic group polyorganosiloxane having the average unit of the chemical formula 4 is 0.01 mol%, 0.02 mol%, 0.03 mol%, 0.04 mol%, 0.05 mol%, 0.06 mol%, 0.07 mol%, 0.08 mol%, 0.09 mol%, 0.1 mol%, 0.11 mol%, 0.12 mol%, 0.13 mol%, 0.14 mol%, 0.15 mol%, 0.16 mol%, 0.17 mol%, 0.18 mol%, 0. The ratio may be about 19 mol%, 0.2 mol%, 0.3 mol%, 0.4 mol%, 0.5 mol%, 0.6 mol%, 0.7 mol%, 0.8 mol%, 0.9 mol%, or 1 mol%, and the upper limit may be about 1.5 mol%, 1.4 mol%, 1.3 mol%, 1.2 mol%, 1.1 mol%, 1 mol%, 0.9 mol%, 0.8 mol%, 0.7 mol%, 0.6 mol%, 0.5 mol%, 0.4 mol%, 0.3 mol%, 0.2 mol%, 0.1 mol%, 0.19 mol%, or 0.18 mol%. The ratio may be less than or equal to any one of the upper limits described above, or greater than or equal to any one of the lower limits described above, or less than or equal to any one of the upper limits described above and greater than or equal to any one of the lower limits described above.

[0105] The polyorganosiloxane having an average unit of the formula 4 may include one or more siloxane units selected from the group consisting of a siloxane unit of the following formula 6 and a siloxane unit of the following formula 7.

[0106] [Chemical formula 6]

[0107] ViR 6 2SiO 1 / 2

[0108] [Chemical formula 7]

[0109] ViR 6 SiO2 / 2

[0110] In formulas 6 and 7, Vi is an alkenyl group and R 6 is a hydroxy group, an alkoxy group, or a monovalent hydrocarbon group. Specific types of the alkenyl group, the alkoxy group, and the monovalent hydrocarbon group are as described in Chemical Formula 4.

[0111] When included, the lower limit of the ratio of the siloxane units of the chemical formula 6 based on the total siloxane units in the first polyorganosiloxane component may be about 0.001 mol%, 0.005 mol%, 0.01 mol%, 0.02 mol%, 0.03 mol%, 0.04 mol%, 0.05 mol%, 0.06 mol%, 0.07 mol%, 0.08 mol%, 0.09 mol%, or 0.095 mol%, and the upper limit may be about 0.5 mol%, 0.4 mol%, 0.3 mol%, 0.2 mol%, 0.1 mol%, 0.09 mol%, 0.08 mol%, or 0.07 mol%. The ratio may be less than or equal to any one of the upper limits described above, or greater than or equal to any one of the lower limits described above, or greater than or equal to or greater than any one of the lower limits described above and within a range of less than or equal to any one of the upper limits described above.

[0112] When included, the lower limit of the ratio of the siloxane units of the formula 7 based on the total siloxane units in the first polyorganosiloxane component may be about 0.01 mol%, 0.05 mol%, 0.1 mol%, 0.15 mol%, 0.2 mol%, 0.3 mol%, 0.4 mol%, 0.5 mol%, 0.6 mol%, 0.7 mol%, 0.8 mol%, or 0.9 mol%, and the upper limit may be about 10 mol%, 9 mol%, 8 mol%, 7 mol%, 6 mol%, 5 mol%, 4 mol%, 3 mol%, 2 mol%, or 1 mol%. The ratio may be less than or equal to any one of the upper limits described above, or greater than or equal to any one of the lower limits described above, or greater than or equal to any one of the lower limits described above and less than or equal to any one of the upper limits described above.

[0113] The first organosiloxane component may include all of the siloxane units of Formula 6 and Formula 7. In this case, the lower limit of the molar ratio of the siloxane units of Formula 7 to the siloxane units of Formula 6 may be about 0.1, 0.5, 1, 1.5, 2, 2.5, 3, 4, 5, 6, 7, 8, 9, or 9.5, and the upper limit may be about 20, 18, 16, 14, 12, 11, 10, 9, 8, 7, 6, 5, 4, or 3. The ratio may be less than or equal to any one of the upper limits described above, or greater than or equal to any one of the lower limits described above, or greater than or equal to any one of the lower limits described above and less than or equal to any one of the upper limits described above.

[0114] The lower limit of the number of silicon atoms contained in the first polyorganosiloxane component may be about 500, 1,500, 2,000, 2,500 or 3,000, and the upper limit may be about 10,000, 5,000, 4,000, 3,500, 3,000, 2,500 or 2,100. The number of silicon atoms may be equal to or greater than any one of the lower limits described above, equal to or less than any one of the upper limits described above, or equal to or greater than any one of the lower limits described above and equal to or less than any one of the upper limits described above.

[0115] The first polyorganosiloxane component can have a substantially linear structure.In this case, the polyorganosiloxane can have a structure that is substantially composed of M units (monofunctional siloxane units) and D units (difunctional siloxane units), or includes T units (trifunctional siloxane units) and / or Q units (tetrafunctional siloxane units) together with M units (monofunctional siloxane units) and D units (difunctional siloxane units), but the proportion of T units (trifunctional siloxane units) and / or Q units (tetrafunctional siloxane units) is below a certain level.

[0116] For example, in the first polyorganosiloxane component, the upper limit of the ratio of the total moles of the T and Q units to the total moles of the siloxane units contained in the polyorganosiloxane (100 × (moles of T units + moles of Q units) / total moles of siloxane units) may be about 10 mol%, 9 mol%, 8 mol%, 7 mol%, 6 mol%, 5 mol%, 4 mol%, 3 mol%, 2 mol%, 1 mol% or 0.5 mol%, and the lower limit may be 0 mol%. The ratio may be less than or equal to any one of the upper limits described above, or may be greater than or equal to any one of the lower limits described above and less than or equal to any one of the upper limits described above.

[0117] The lower limit of the weight average molecular weight of the polyorganosiloxane having the average unit of the chemical formula 4 may be about 100,000 g / mol, 125,000 g / mol, 150,000 g / mol, 175,000 g / mol, 200,000 g / mol, 225,000 g / mol, 250,000 g / mol, 275,000 g / mol, or 300,000 g / mol, and the upper limit may be about 1,00 The weight average molecular weight may be about 0,000 g / mol, 950,000 g / mol, 900,000 g / mol, 850,000 g / mol, 800,000 g / mol, 750,000 g / mol, 700,000 g / mol, 650,000 g / mol, 600,000 g / mol, 550,000 g / mol, 500,000 g / mol, 450,000 g / mol, or 400,000 g / mol. The weight average molecular weight may be less than or equal to any one of the upper limits described above, or greater than or equal to any one of the lower limits described above, or greater than or equal to any one of the lower limits described above and less than or equal to any one of the upper limits described above. The polyorganosiloxane having the 4-average unit of the formula has a weight average molecular weight within the above range, thereby ensuring an appropriate viscosity and exhibiting excellent coating properties.

[0118] The polydispersity index of the polyorganosiloxane having the average unit of the chemical formula 4 may have a lower limit of about 1, 1.25 or 1.5, and the upper limit may be about 5, 3.5 or 2.5. The polydispersity index may be less than or equal to any one of the upper limits described above, or greater than or equal to any one of the lower limits described above, or greater than or equal to any one of the lower limits described above and less than or equal to any one of the upper limits described above.

[0119] The curable silicone resin component may contain a polyorganosiloxane having an average unit of the following chemical formula 5 together with the polyorganosiloxane having an average unit of the above-mentioned chemical formula 4 (hereinafter, it may be referred to as the second polyorganosiloxane or the second polyorganosiloxane component). Such an average unit may be for one molecule of polyorganosiloxane or for a mixture of two or more molecules of polyorganosiloxane. When the average unit is for a mixture of two or more molecules of polyorganosiloxane, the ratio of other functional groups or atoms is calculated assuming that the number of all silicon atoms contained in the mixture is 1.

[0120] [Chemical formula 5]

[0121] H c Q d SiO (4-c-d) / 2

[0122] In Chemical Formula 5, H may be a hydrogen atom, Q may be an alkoxy group, a hydroxy group, or a monovalent hydrocarbon group, c may be a number within the range of 0.01 to 0.9, and d may be a number within the range of 1 to 4. Specific examples of the alkoxy group or monovalent hydrocarbon group in Chemical Formula 5 are the same as those in Chemical Formula 4.

[0123] In the formula 5, the lower limit of c may be about 0.05, 0.1, 0.15, 0.2, 0.25, 0.3, 0.31, 0.32, 0.33, 0.34, 0.35, 0.4, 0.5, or 0.6, and the upper limit may be about 2, 1.5, 1, 0.9, 0.8, 0.7, 0.65, 0.6, 0.5, 0.4, 0.39, 0.38, 0.37, 0.36, or 0.35. The c may be less than or equal to any one of the upper limits described above, or greater than or equal to any one of the lower limits described above, or less than or equal to any one of the upper limits described above and greater than or equal to any one of the lower limits described above.

[0124] In the formula 5, the lower limit of d may be about 0.5, 1, 1.1, 1.2, 1.3, 1.4, 1.5, or 1.6, and the upper limit may be 4, 3.5, 3, 2.5, 2, 1.9, 1.8, 1.7, 1.6, or 1.5. The d may be less than or equal to any one of the upper limits described above, or greater than or equal to any one of the lower limits described above, or less than or equal to any one of the upper limits described above and greater than or equal to any one of the lower limits described above.

[0125] The lower limit of the ratio of the number of moles of all silicon-bonded hydrogen atoms contained in the average unit of the chemical formula 5 based on the number of moles of all silicon-bonded organic groups contained in the average unit of the chemical formula 5 may be about 1 mol%, 5 mol%, 10 mol%, 15 mol%, 20 mol%, 25 mol%, or 30 mol%, and the upper limit may be about 85 mol%, 80 mol%, 75 mol%, 70 mol%, 65 mol%, 60 mol%, 55 mol%, 50 mol%, 45 mol%, 40 mol%, 35 mol%, 30 mol%, 25 mol%, or 20 mol%. The ratio may be less than or equal to any one of the upper limits described above, or greater than or equal to any one of the lower limits described above, or greater than or equal to any one of the lower limits described above and less than or equal to any one of the upper limits described above. Under such a ratio, it is possible to secure appropriate curability and form a release layer having the desired release properties.

[0126] According to one embodiment of the present application, the organic group polyorganosiloxane having an average unit of formula 5 may include siloxane units of formula 9 below.

[0127] [Chemical formula 9]

[0128] HR 6 SiO 2 / 2

[0129] In formula 9, R 6may be a hydroxy group, an alkoxy group, or a monovalent hydrocarbon group. Specific examples of the alkoxy group and the monovalent hydrocarbon group in Chemical Formula 9 are the same as those in Chemical Formula 5.

[0130] The lower limit of the ratio of the number of moles of the siloxane units of the silicon chemical formula 9 based on the total number of moles of the siloxane units containing silicon-bonded hydrogen atoms among all the siloxane units contained in the second polyorganosiloxane component may be about 85 mol%, 90 mol%, 95 mol%, 96 mol%, 97 mol%, 98 mol%, 99 mol% or 99.5 mol%, and the upper limit may be about 100 mol%. The ratio may be less than or equal to any one of the upper limits described above, or greater than or equal to any one of the lower limits described above, or greater than or equal to any one of the lower limits described above and less than or equal to any one of the upper limits described above.

[0131] The lower limit of the ratio of the siloxane units of the formula 9 based on the total siloxane units in the second polyorganosiloxane component may be about 10 mol%, 15 mol%, 20 mol%, 25 mol%, 30 mol%, 35 mol%, 40 mol%, 45 mol%, 50 mol%, 55 mol% or 60 mol%, and the upper limit may be about 85 mol%, 80 mol%, 75 mol%, 70 mol%, 65 mol%, 60 mol%, 55 mol% or 50 mol%. The ratio may be less than or equal to any one of the upper limits described above, or greater than or equal to any one of the lower limits described above, or greater than or equal to any one of the lower limits described above and less than or equal to any one of the upper limits described above.

[0132] The lower limit of the number of silicon atoms contained in the second polyorganosiloxane component may be about 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85 or 90, and the upper limit may be about 1,000, 950, 900, 850, 800, 750, 700, 650, 600, 550, 500, 450, 400, 350, 300, 250, 200, 150, 100, 95, 90, 85, 80, 75, 70, 65, 60, 55 or 50. The number of silicon atoms may be greater than or equal to any one of the lower limits described above, or less than or equal to any one of the upper limits described above, or may be within a range of greater than or equal to any one of the lower limits described above and less than or equal to any one of the upper limits described above.

[0133] The second polyorganosiloxane component may have a substantially linear structure. In such a case, the polyorganosiloxane may have a structure that is substantially composed of only M and D units, or that contains T and / or Q units in addition to M and D units, but the proportion of the T and / or Q units is below a certain level.

[0134] For example, in the second polyorganosiloxane component, the upper limit of the ratio of the total moles of the T and Q units to the total moles of the siloxane units contained in the polyorganosiloxane (100 × (moles of T units + moles of Q units) / total moles of siloxane units) may be about 10 mol%, 9 mol%, 8 mol%, 7 mol%, 6 mol%, 5 mol%, 4 mol%, 3 mol%, 2 mol%, 1 mol% or 0.5 mol%, and the lower limit may be 0 mol%. The ratio may be less than or equal to any one of the upper limits described above, or may be greater than or equal to any one of the lower limits described above and less than or equal to any one of the upper limits described above.

[0135] The lower limit of the weight average molecular weight of the polyorganosiloxane having the average unit of the chemical formula 5 may be about 1,000 g / mol, 1,500 g / mol, 2,000 g / mol, 2,500 g / mol, 3,000 g / mol, 3,500 g / mol, 4,000 g / mol, 4,500 g / mol, 5,000 g / mol, 5,500 g / mol, 6,000 g / mol, 6,500 g / mol, 7,000 g / mol, 7,500 g / mol, or 8,000 g / mol, and the upper limit may be about 100,000 g / mol, 90,000 g / mol, mol, 80,000 g / mol, 70,000 g / mol, 60,000 g / mol, 50,000 g / mol, 45,000 g / mol, 40,000 g / mol, 30,000 g / mol, 20,000 g / mol, 15,000 g / mol, 10,000 g / mol, 50,000 g / mol, 45,000 g / mol, 40,000 g / mol, 35,000 g / mol, 30,000 g / mol, 25,000 g / mol, 20,000 g / mol, 15,000 g / mol or 12,000 g / mol. The weight average molecular weight may be greater than or exceeding any one of the lower limits described above, less than or equal to any one of the upper limits described above, or greater than or exceeding any one of the lower limits and less than or equal to any one of the upper limits described above. The polyorganosiloxane having an average unit of the formula 5 has a weight average molecular weight within the above range, thereby ensuring excellent curability.

[0136] The polyorganosiloxane having an average unit of the chemical formula 5 may have a polydispersity index of about 1, 1.25 or 1.5, and an upper limit of about 5, 3.5 or 2.5. The polydispersity index may be greater than or exceed any one of the lower limits described above, less than or equal to any one of the upper limits described above, or greater than or exceed any one of the lower limits described above and less than or equal to any one of the upper limits described above.

[0137] The lower limit of the content of the polyorganosiloxane having an average unit of the chemical formula 4 in the curable silicone resin component or the mold release composition may be about 50% by weight, 52% by weight, 54% by weight, 56% by weight, 58% by weight, 60% by weight, 62% by weight, 64% by weight, 66% by weight, 68% by weight, 70% by weight, 75% by weight, 80% by weight, 85% by weight, or 90% by weight, and the upper limit may be about 98% by weight, 95% by weight, 94% by weight, 93% by weight, 92% by weight, 90% by weight, 85% by weight, or 80% by weight. The ratio may be equal to or greater than any one of the lower limits described above, equal to or less than any one of the upper limits described above, or equal to or greater than any one of the lower limits described above and equal to or less than any one of the upper limits described above. The ratio is based on the solid content, and therefore, when the release composition contains a solvent, it is the ratio to the total weight of the release composition excluding the weight of the solvent. By including polyorganosiloxane having an average unit of Formula 4 within the above range, it is possible to ensure an appropriate level of release force and excellent residual adhesion rate of the release layer described later.

[0138] The lower limit of the weight of the polyorganosiloxane having the average unit of the chemical formula 5 in the curable silicone resin component or the mold release composition relative to 100 parts by weight of the polyorganosiloxane having the average unit of the chemical formula 4 may be about 0.1 parts by weight, 0.25 parts by weight, 0.5 parts by weight, 0.75 parts by weight, 1 part by weight, 1.25 parts by weight, 1.5 parts by weight, 1.75 parts by weight or 2 parts by weight, and the upper limit may be about 10 parts by weight, 8 parts by weight, 6 parts by weight, 4 parts by weight or 3 parts by weight. The ratio may be equal to or greater than any one of the lower limits described above, equal to or less than any one of the upper limits described above, or equal to or greater than any one of the lower limits described above and equal to or less than any one of the upper limits described above. When the polyorganosiloxane having the average unit of the chemical formula 5 is contained within the above range, the crosslink density can be improved to ensure a cured product with excellent durability.

[0139] The lower limit of the weight of the compound having an average unit of the chemical formula 1 in the mold release composition relative to 100 parts by weight of the polyorganosiloxane having an average unit of the chemical formula 4 may be about 0.1 parts by weight, 0.25 parts by weight, 0.5 parts by weight, 0.75 parts by weight, 1 part by weight, 1.25 parts by weight, 1.5 parts by weight, 1.75 parts by weight, 2 parts by weight, 5 parts by weight, 10 parts by weight, 15 parts by weight, or 20 parts by weight, and the upper limit may be about 100 parts by weight, 95 parts by weight, 90 parts by weight, 85 parts by weight, 80 parts by weight, 75 parts by weight, 70 parts by weight, 65 parts by weight, 60 parts by weight, 55 parts by weight, 50 parts by weight, 45 parts by weight, 40 parts by weight, 35 parts by weight, 30 parts by weight, 25 parts by weight, 20 parts by weight, 15 parts by weight, 10 parts by weight, or 5 parts by weight. The ratio may be equal to or greater than any one of the lower limits described above, equal to or less than any one of the upper limits described above, or equal to or greater than any one of the lower limits and equal to or less than any one of the upper limits described above. By adjusting the ratio of the compound having the average unit of Chemical Formula 1, the desired release layer can be more effectively formed.

[0140] The release composition includes the components described above and can optionally include additional components, if desired.

[0141] For example, the release composition may further include a compound represented by the following Formula 10:

[0142] [Chemical formula 10]

[0143] [ka]

[0144] In Chemical Formula 10, R1 is a double bond-containing group, and R2 to R4 may each independently be an alkyl group.

[0145] By using the compound of Formula 10, a release composition having excellent film-forming properties can be formed. Such a release composition has excellent bonding properties to a substrate, an appropriate level of release force, and an excellent residual adhesion rate, and can form a release layer in which changes in release force due to external factors such as heat and ultraviolet rays are minimized.

[0146] In Chemical Formula 10, specific examples of the alkyl groups R2 to R4 are as described at the beginning of this specification.

[0147] In addition, the specific type of the double bond-containing group in Chemical Formula 10 is not particularly limited, and for example, the double bond-containing group may be an alkenyl group or a (meth)acryloyloxyalkyl group, etc. Specific types of the alkyl group of the alkenyl group and the (meth)acryloyloxyalkyl group are as described at the beginning of this specification.

[0148] When included, the lower limit of the content of the compound of Chemical Formula 10 relative to 100 parts by weight of the compound having an average unit of Chemical Formula 1 may be about 0.1 parts by weight, 0.5 parts by weight, 1 part by weight, 5 parts by weight, 10 parts by weight, 15 parts by weight, 20 parts by weight, 35 parts by weight, 40 parts by weight, 50 parts by weight, 100 parts by weight, 150 parts by weight, or 200 parts by weight, and the upper limit may be about 1000 parts by weight, 800 parts by weight, 600 parts by weight, 400 parts by weight, 200 parts by weight, 150 parts by weight, 100 parts by weight, 90 parts by weight, 80 parts by weight, 70 parts by weight, 60 parts by weight, 50 parts by weight, 40 parts by weight, 30 parts by weight, 20 parts by weight, or 10 parts by weight. The ratio may be equal to or greater than any one of the lower limits described above, equal to or less than any one of the upper limits described above, or equal to or greater than any one of the lower limits described above and equal to or less than any one of the upper limits described above. By adjusting the ratio of the compounds as described above, the desired release layer can be formed more effectively.

[0149] In another example, the lower limit of the weight of the compound of formula 10 relative to 100 parts by weight of the polyorganosiloxane having an average unit of formula 4 when included may be about 0.1 parts by weight, 0.25 parts by weight, 0.5 parts by weight, 0.75 parts by weight, 1 part by weight, 1.25 parts by weight, 1.5 parts by weight, 1.75 parts by weight, or 2 parts by weight, and the upper limit may be about 10 parts by weight, 8 parts by weight, 6 parts by weight, 4 parts by weight, or 3 parts by weight. The ratio may be equal to or greater than any one of the lower limits described above, equal to or less than any one of the upper limits described above, or equal to or greater than any one of the lower limits described above and equal to or less than any one of the upper limits described above. By adjusting the ratio of the compound as described above, the desired release layer can be formed more effectively.

[0150] The release composition of the present application may further include a metal catalyst, if necessary, in consideration of curability. The metal catalyst may include at least one central metal element selected from the group consisting of aluminum, bismuth, lead, mercury, tin, zinc, platinum, silver, and zirconium. Examples of the metal catalyst include, but are not limited to, Bis[1,3-bis(2-ethenyl)-1,1,3,3-tetramethyldisiloxane]platinum (CAS No. 81032-58-8), dibutyltin dilaurate, and dimethyltin diacetate. For example, the catalyst may be a catalyst known in the art as an addition curing catalyst.

[0151] The lower limit of the weight of the metal catalyst relative to 100 parts by weight of the polyorganosiloxane having an average unit of the chemical formula 4 may be about 0.1 parts by weight, 0.5 parts by weight, 1 part by weight, 1.5 parts by weight, 2 parts by weight, 2.5 parts by weight, or 3 parts by weight, and the upper limit may be about 10 parts by weight, 9 parts by weight, 8 parts by weight, 7 parts by weight, 6 parts by weight, 5 parts by weight, or 4 parts by weight. The ratio may be equal to or greater than any one of the lower limits described above, equal to or less than any one of the upper limits described above, or equal to or greater than any one of the lower limits described above and equal to or less than any one of the upper limits described above. By including the catalyst within the above range, side reactions can be reduced and the reaction to form a cured product can be effectively promoted.

[0152] The release composition according to one embodiment of the present application may further include a solvent.

[0153] Considering the composition of the release composition, the solvent may be an organic solvent. The organic solvent is not particularly limited as long as it is one generally used in the industry, and tetrahydrofuran, methyl ethyl ketone, toluene, heptane, etc., or a mixture thereof can be used. The mixing ratio of these is not particularly limited, and they can be appropriately mixed as necessary.

[0154] The amount of the solvent can be adjusted as necessary and is not particularly limited.

[0155] The present application also relates to a release layer. The release layer may include the release composition described above or a cured product thereof.

[0156] Therefore, the release layer may include a compound having an average unit of Chemical Formula 1 or a reactant thereof, and may include the above-described curable silicone resin component, a reactant of the curable silicone resin component, and / or a compound of Chemical Formula 10 or a reactant of the compound of Chemical Formula 10, if necessary. The release layer may be formed by curing the release composition according to the above-described example of the present application. The curing may be appropriately performed by various methods as described above. The release layer may include a component remaining after curing the release composition according to the above-described example of the present application.

[0157] The release layer may contain the release composition or a cured product thereof, and may therefore satisfy at least one of the following physical properties.

[0158] For example, the release layer may have a peel force change rate AR according to the following formula 1 within a predetermined range. For example, the upper limit of the AR may be about 30%, 29%, 28%, 27%, 26%, 25%, 24%, 23%, 22%, 21%, 20%, 19%, 18%, 17%, 16%, 15%, 14%, 13%, or 12%, and the lower limit may be about 0%, 5%, or 10%. The AR may be equal to or less than any one of the upper limits described above, or may be equal to or greater than any one of the lower limits described above and within a range of equal to or less than any one of the upper limits described above.

[0159] [Formula 1]

[0160] AR=100×|A2-A1| / A1

[0161] In Equation 1, A1 is the release force measured at 25°C at a peel angle of 180° and a peel speed of 0.3 m / min after maintaining the release layer attached to the pressure-sensitive adhesive layer at 25°C for 24 hours, and A2 is the release force measured at 25°C at a peel angle of 180° and a peel speed of 0.3 m / min after irradiating the release layer attached to the pressure-sensitive adhesive layer with ultraviolet light and maintaining it at 60°C for 24 hours.

[0162] The release peel force A2 may be a release peel force (A21) measured after first irradiating the test piece with ultraviolet light and then maintaining it at 60°C for 24 hours, or a release peel force (A22) measured after first maintaining the test piece at 60°C for 24 hours and then irradiating it with ultraviolet light.

[0163] In Equation 1, |A2-A1| means the absolute value of the difference between A2 and A1.

[0164] A specific method for measuring the peel force change rate AR in formula 1 (method for measuring release peel forces A1 and A2) will be described in the Examples section.

[0165] The release layer may have a residual adhesion ratio Ad according to the following formula 2 within a predetermined range. For example, the lower limit of the residual adhesion ratio Ad may be about 80%, 81%, 82%, 83%, 84%, 85%, 86%, 87%, 88%, 89%, 90% or 91%, and the upper limit may be about 100% or 95%. The Ad may be equal to or greater than any one of the lower limits described above, or may be equal to or greater than any one of the lower limits described above and less than or equal to any one of the upper limits described above. A release layer according to one example of the present application has a residual adhesion ratio (A d ) is said to have excellent (or adequate) residual adhesion.

[0166] [Formula 2]

[0167] Ad=100×Af / Ai

[0168] In Equation 2, Ai is the release force measured by attaching an adhesive tape to the release layer and peeling the adhesive tape at a peel angle of 180° at 25° C. and a peel speed of 0.3 m / min, and Af is the release force measured by attaching an adhesive tape to the release layer on which the release force Ai was measured in the same manner as when the release force Ai was measured and peeling the adhesive tape at a peel angle of 180° at 25° C. and a peel speed of 0.3 m / min.

[0169] A specific method for measuring the residual adhesion rate Ad according to the above formula 2 will be described in the Examples section of this specification.

[0170] The release layer according to one embodiment of the present application may have a release force within a predetermined range when attached to an adhesive tape and maintained at room temperature (about 25° C.) for 24 hours, and then measured at a peel angle of 180° and a peel speed of 0.3 m / min at room temperature (about 25° C.). For example, the lower limit of the release force may be about 5 gf / inch, and the upper limit may be about 500 gf / inch, 400 gf / inch, 300 gf / inch, 200 gf / inch, 100 gf / inch, 50 gf / inch, or 25 gf / inch. The release force may be equal to or less than any one of the upper limits described above, or may be equal to or more than any one of the lower limits described above and less than or equal to any one of the upper limits described above. When the release layer according to one embodiment of the present application has a release force (left at room temperature) that satisfies the above range, it can be said to have an excellent (or appropriate) residual adhesion rate.

[0171] In addition, the release layer according to one example of the present application is attached to an adhesive tape and irradiates ultraviolet rays having a wavelength of about 150 nm at 3 J / m 2After performing a process of irradiating the film with a light amount of 10000 for about 60 seconds and maintaining the film at 60° C. for 24 hours, the release force measured at room temperature (about 25° C.) at a peel angle of 180° and a peel speed of 0.3 m / min may be within a predetermined range. For example, the lower limit of the release force may be about 5 gf / inch, and the upper limit may be about 500 gf / inch, 400 gf / inch, 300 gf / inch, 200 gf / inch, 100 gf / inch, 50 gf / inch, or 25 gf / inch. The release force may be equal to or less than any one of the upper limits described above, or may be equal to or more than any one of the lower limits described above and equal to or less than any one of the upper limits described above. When the release layer according to one embodiment of the present application has a release force (ultraviolet light and high temperature exposure) that satisfies the above range, it can be said to have an excellent (or appropriate) residual adhesion rate. Moreover, the release force at this time does not depend on the order of irradiation with ultraviolet light and leaving at high temperature.

[0172] The present application also relates to a release film.

[0173] The release film may include a base film and a release layer attached to one or both sides of the base film.

[0174] The release layer of the release film according to one example of the present application is as described above.

[0175] The type of the base film of the release film according to the embodiment of the present application is not particularly limited. As the base film, a base film that can be generally used for forming a release film may be used.

[0176] For example, the substrate film may be, but is not limited to, a PET (poly(ethyleneterephthalate)) film, a PTFE (poly(tetrafluoroethylene)) film, a PP (polypropylene) film, a PE (polyethylene) film, a polyimide film, a polyamide film, a COP (cyclic olefin polymer) film, a polybutene film, a polybutadiene film, a vinyl chloride copolymer film, a polyurethane film, an ethylene-vinyl acetate film, an ethylene-propylene copolymer film, an ethylene-ethyl acrylate copolymer film, an ethylene-ethyl acrylate copolymer film, and / or a polyimide film.

[0177] The substrate film may be composed of a single layer or may be composed of two or more layers, and may further include a functional layer such as an antifouling layer or an antistatic layer, etc. From the viewpoint of improving the adhesion to the substrate, a surface treatment such as a primer treatment may be additionally performed on one or both sides of the substrate.

[0178] The thickness of the substrate film is appropriately selected depending on the application and is not particularly limited, and can usually be formed to a thickness of 5 μm to 500 μm, 5 μm to 250 μm, or 5 μm to 100 μm.

[0179] The release film of the present application may be manufactured by a known method. In one example, the release film of the present application may be manufactured by applying a release composition according to one example of the present application to one or both sides of a substrate, and then curing the composition to form a release layer. Here, the application method of the release composition is not particularly limited as long as it is a method commonly used in the art, and may be, for example, knife coating, roll coating, or reverse coating. In addition, when forming a release layer, it may be performed after sufficiently removing bubble-inducing components such as volatile components and reaction residues of the release composition. In addition, the method of curing the release composition is not particularly limited, and the release composition may be cured through a suitable aging process or in a suitable high temperature environment or light irradiation environment as described above.

[0180] The thickness of the release layer contained in the release film is not particularly limited and may be, for example, 10 nm to 10 μm, 10 nm to 1 μm, or 10 nm to 100 nm.

[0181] The present application also relates to an adhesive film.

[0182] The adhesive film according to an embodiment of the present application may include the above-mentioned release layer and the adhesive layer to which the release layer is attached. By including the release layer, the adhesive layer can be protected before use.

[0183] The release layer of the adhesive film according to one example of the present application is as described above.

[0184] The adhesive that forms the adhesive layer of the adhesive film according to one example of the present application is not particularly limited.

[0185] For example, the adhesive for forming the adhesive layer can be appropriately selected from those having a base polymer such as an acrylic polymer, a silicone polymer, a polyester, a polyurethane, a polyamide, a polyether, or a fluorine-based or rubber-based polymer. Effect of the Invention

[0186] The present application can provide a compound, a release composition, a release layer, a release film, and an adhesive film. The present application can provide a compound that can form a release layer that exhibits an appropriate release force, has excellent bonding strength with a base film, and has excellent solvent resistance. In addition, the present application can provide a compound that, when the release layer is formed, exhibits a stable residual adhesion rate even when the release layer is repeatedly applied to an adhesive layer, etc. In addition, the present application can provide a release composition and a release layer containing the compound, and a release film and an adhesive film containing the release layer. [Brief description of the drawings]

[0187] [Figure 1] FIG. 1 is a simplified diagram illustrating steps for preparing a compound in a manner according to one example of the present application. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0188] The present application will be described in detail below with reference to examples and comparative examples, but the present application is not limited to the following examples.

[0189] 1. Release strength

[0190] A test specimen was prepared by laminating the adhesive layer of an adhesive tape for measuring release force (TESA7475 PV2, TESA) to the release layer of the linear film of the Examples or Comparative Examples. The adhesion was performed by placing the adhesive tape on the release layer and then moving a roller with a load of 2.5 kg back and forth three times. The test specimen was kept at room temperature (about 25°C) or 60°C for 24 hours, and then the release force was measured by peeling the adhesive tape for measuring release force at room temperature (about 25°C) at a peel angle of 180° and a peel speed of 0.3 m / min using a physical property measuring device (Cheminstruments, AR-1000).

[0191] 2. Rate of change of release force (AR)

[0192] The rate of change AR of the release force of the release layer of each of the Examples and Comparative Examples was determined according to the following formula 1.

[0193] [Formula 1]

[0194] AR=100×|A2-A1| / A1

[0195] In Equation 1, A1 is the release force measured at room temperature (about 25°C) using a physical property measuring device (Cheminstruments, AR-1000) at a peel angle of 180° and a peel speed of 0.3 m / min after maintaining a test piece prepared by laminating an adhesive tape for release force measurement (TESA7475 PV2, TESA) in the same manner as in the above release force measurement at room temperature (about 25°C) for 24 hours.

[0196] In Equation 1, A2 is the release force measured at room temperature (about 25°C) using a physical property measuring device (Cheminstruments, AR-1000) at a peel angle of 180° and a peel speed of 0.3m / min, after irradiating a test piece prepared by laminating an adhesive tape for release force measurement (TESA7475 PV2, TESA) in the same manner as in the above release force measurement with ultraviolet light and maintaining it at 60°C for 24 hours. The ultraviolet light was about 150nm in wavelength and 3J / m 2 The sample was irradiated with a light intensity of 1000 for approximately 60 seconds.

[0197] The demolding peel force A2 may be a demolding peel force (A21) measured after first irradiating the test piece with ultraviolet light and then maintaining it at 60°C for 24 hours, or a demolding peel force (A22) measured after first maintaining the test piece at 60°C for 24 hours and then irradiating it with ultraviolet light.

[0198] 3.Residual adhesion rate (Ad)

[0199] The residual adhesion rate Ad of the release layer of the release film of each of the Examples and Comparative Examples was determined by the following formula 2.

[0200] [Formula 2]

[0201] Ad=100×Af / Ai

[0202] In Equation 2, Ai is the release force measured after the test piece prepared according to the method for evaluating the release force was kept at room temperature (about 25° C.) for 24 hours.

[0203] In Equation 2, Af is the release force measured after a standard tape (TESA7475, TESA) is attached to the release layer of the release film after measuring the release force Ai in the same manner as for measuring the release force Ai to prepare a test specimen, and the test specimen is kept at room temperature (about 25° C.) for about 24 hours.

[0204] The release peel strengths Ai and Af were measured by peeling an adhesive tape (TESA7475) at a peel angle of 180 degrees and a peel speed of 0.3 m / min at room temperature (about 25° C.) using a physical property measuring device (AR-1000, Cheminstruments) in the same manner as in the measurement of the release peel strength.

[0205] 4. Method for evaluating solvent resistance

[0206] The release layer of the release film of the Examples or Comparative Examples was irradiated with ultraviolet light and maintained at 60° C. for 24 hours. The ultraviolet light irradiation was performed in the same manner as in the measurement of the release force A2 in Equation 1. Then, using No. 542-AB equipment (Yasauda), the fabric soaked in toluene was moved back and forth until the release layer fell off, and the number of times the fabric was moved back and forth until the release layer fell off was measured, and the solvent resistance was evaluated according to the following solvent resistance evaluation criteria.

[0207] <Solvent resistance evaluation criteria>

[0208] PASS: Exceeded 10 times

[0209] NG: Less than 10 times

[0210] 5. Evaluation of weight-average molecular weight

[0211] The weight-average molecular weight (Mw) and polydispersity index (PDI) were measured using GPC (Gel permeation chromatography). The units of the weight-average molecular weight (Mw) and number-average molecular weight (Mn) referred to in this specification are g / mol.

[0212] The sample (the sample to be analyzed) was placed in a 20 mL vial, diluted with THF (tetrahydrofuran) to a concentration of about 20 mg / mL, and after filtering the calibration standard sample and the sample to be analyzed through a syringe filter (pore size: 0.2 μm), the molecular weight characteristics were measured. As the analysis program, ChemStation of Agilent technologies was used. After comparing the elution time of the sample with the calibration curve to obtain the number-average molecular weight (Mn) and weight-average molecular weight (Mw), the value obtained by dividing the weight-average molecular weight (Mw) by the number-average molecular weight (Mn) (Mw / Mn) was taken as the polydispersity index.

[0213] <GPC measurement conditions>

[0214] Instrument: 1200 series of Agilent technologies

[0215] Column: TL Mix.A&B of Agilent technologies was used

[0216] Solvent: THF

[0217] Column temperature: 40 °C

[0218] Sample concentration: 20 mg / mL, 10 μL injection

[0219] Standard samples with MP: 364000, 91450, 17970, 4910, 1300 were used

[0220] <Production Example 1>

[0221] The compound was synthesized according to the reaction scheme shown in Figure 1. First, 2-hydroxy-2-methylpropiophenone (S1) and 3-(triethoxysilyl)propyl isocyanate (S2) were mixed in a weight ratio of 16.42:24.7 (S1:S2) and reacted at about 80°C in the presence of a catalyst (DBTDL; dibutyltin dilaurate), and the hydroxyl group of 2-hydroxy-2-methylpropiophenone (S1) reacted with the isocyanate group of 3-(triethoxysilyl)propyl isocyanate (S2) to produce intermediate product (A). The catalyst was used in an amount of about 0.292 parts by weight per 100 parts by weight of the total of the 2-hydroxy-2-methylpropiophenone (S1) and 3-(triethoxysilyl)propyl isocyanate (S2).

[0222] Then, the intermediate product (A) and 2,2-dimethyl-1,3-propanediol (B) were mixed in a weight ratio (A:B) of about 100:0.948, and subjected to a condensation reaction at about 100° C. for about 3 to 5 hours to produce the target compound (the compound shown in FIG. 1), which was then purified by a known method.

[0223] The weight average molecular weight of the target compound was about 50,000 g / mol, and the polydispersity index (PDI) was about 2.1851.

[0224] Through the above synthesis process, it is found that the target compound is a compound having an average unit of the following chemical formula A.

[0225] [Chemical formula A]

[0226] R 1 R 2 n Six (3-n) / 2

[0227] In the chemical formula A, R1 is a functional group of the following chemical formula B, R 2 is an isocyanatopropyl group, a functional group of the following chemical formula C, or an ethoxy group; X is a linker that connects silicon atoms of the target compound to each other, and is an oxygen atom or a divalent linker of the following chemical formula D; and n is a number within the range of 0 to 2.

[0228] [Chemical formula B]

[0229] [ka]

[0230] In formula B, the left-most carbon atom is directly linked to the silicon atom of formula A.

[0231] [Chemical formula C]

[0232] [ka]

[0233] In formula C, the right-most oxygen atom is directly linked to the silicon atom of formula A.

[0234] [Chemical formula D]

[0235] [ka]

[0236] In formula D, the oxygens on either side are each directly linked to a silicon atom in formula A.

[0237] <Example 1>

[0238] Polyorganosiloxane of the following formula E (KS-847H, Shinetsu Silicone) (weight average molecular weight about 350,000 g / mol), polyorganosiloxane of the following formula F (X-92-122, Shinetsu Silicone) (weight average molecular weight about 10,000 g / mol), platinum catalyst (PL-50L, Shinetsu Silicone) (C), the compound of Preparation Example 1, and alkoxysilane (G) (3-(trimethoxysilyl)propyl acrylate) were mixed in a weight ratio of 5:0.1:0.25:0.5:0.1 (E:F:C: Preparation Example 1:G) and dispersed in a solvent to prepare a release composition. As the solvent (S), a mixture of THF (tetrahydrofuran), MEK (methylethyl ketone), toluene (T) and n-heptane (H) in a weight ratio of 50:30:10:10 (THF:MEK:T:H) was used.

[0239] [Chemical formula E]

[0240] [ka]

[0241] In chemical formula E, m is a number of about 1,500, and n is a number of about 12 to 13.

[0242] [Chemical formula F]

[0243] [ka]

[0244] In chemical formula F, a and b are each a number between about 34 and 36.

[0245] <Example 2>

[0246] A polyorganosiloxane of chemical formula E (KS-847H, Shinetsu Silicone) (weight average molecular weight about 350,000 g / mol), a polyorganosiloxane of chemical formula F (X-92-122, Shinetsu Silicone) (weight average molecular weight about 10,000 g / mol), a platinum catalyst (PL-50L, Shinetsu Silicone) (C), the compound of Preparation Example 1, and an alkoxysilane of chemical formula G (Gelest, DMS-R11, 3-(trimethoxysilyl)propyl acrylate) were mixed in a weight ratio of 5:0.1:0.25:0.05:0.1 (E:F:C: Preparation Example 1:G) and dispersed in a solvent to prepare a release composition. The same solvent as in Example 1 was used.

[0247] <Example 3>

[0248] A polyorganosiloxane of chemical formula E (KS-847H, Shinetsu Silicone) (weight average molecular weight about 350,000 g / mol), a polyorganosiloxane of chemical formula F (X-92-122, Shinetsu Silicone) (weight average molecular weight about 10,000 g / mol), a platinum catalyst (PL-50L, Shinetsu Silicone) (C), the compound of Preparation Example 1, and an alkoxysilane of chemical formula G (Gelest, DMS-R11, 3-(trimethoxysilyl)propyl acrylate) were mixed in a weight ratio of 5:0.1:0.25:0.25:0.1 (E:F:C: Preparation Example 1:G) and dispersed in a solvent to prepare a release composition. The same solvent as in Example 1 was used.

[0249] <Example 4>

[0250] A polyorganosiloxane of chemical formula E (KS-847H, Shinetsu Silicone) (weight average molecular weight about 350,000 g / mol), a polyorganosiloxane of chemical formula F (X-92-122, Shinetsu Silicone) (weight average molecular weight about 10,000 g / mol), a platinum catalyst (PL-50L, Shinetsu Silicone) (C), the compound of Preparation Example 1, and an alkoxysilane of chemical formula G (Gelest, DMS-R11, 3-(trimethoxysilyl)propyl acrylate) were mixed in a weight ratio of 5:0.1:0.25:1:0.1 (E:F:C: Preparation Example 1:G) and dispersed in a solvent to prepare a release composition. The same solvent as in Example 1 was used.

[0251] <Comparative Example 1>

[0252] A polyorganosiloxane of chemical formula E (KS-847H, Shinetsu Silicone) (weight average molecular weight about 350,000 g / mol), a polyorganosiloxane of chemical formula F (X-92-122, Shinetsu Silicone) (weight average molecular weight about 10,000 g / mol), and a platinum catalyst (PL-50L, Shinetsu Silicone) (C) were mixed in a weight ratio of 5:0.1:0.25 (E:F:C) and dispersed in a solvent to prepare a release composition. The same solvent as in Example 1 was used.

[0253] <Physical property evaluation>

[0254] The release composition of the Example or Comparative Example was applied to a base film and maintained at a temperature of about 150° C. for about 3 minutes to form a release layer on the base film. The thickness of the release layer was about 50 nm to 80 nm. A PET (polyethylene terephthalate) film with a thickness of about 50 μm was used as the base film.

[0255] The test data measured in the above examples and comparative examples are summarized in Table 1 below.

[0256] [Table 1]

[0257] In Table 1, A1 is the release force A1 in Equation 1 for evaluating the rate of change in release force, and its unit is gf / inch. A21 is the release force A21 mentioned in the method for evaluating the rate of change in release force (AR), which is a release force measured after first irradiating a test specimen with ultraviolet light and then maintaining it at 60°C for 24 hours, and its unit is gf / inch.

[0258] In Table 1, AR1 is a value calculated by substituting the above-mentioned A21 for A2 in Equation 1 of the method for evaluating the rate of change (AR) of release force, and the unit is %.

[0259] In Table 1, A22 is the peel force A22 mentioned in the evaluation method for the rate of change (AR) of release force, which is the release force measured after the test piece was kept at 60°C for 24 hours and irradiated with ultraviolet light, and its unit is gf / inch.

[0260] In Table 1, AR2 is a value obtained by substituting the above-mentioned A22 as A2 into formula A in the evaluation method for the rate of change (AR) of release force, and the unit is %.

[0261] In Table 1, Ad is the value calculated by Equation 2 in the item of the residual adhesion rate Ad measurement method, and the unit is %.

[0262] The solvent resistance in Table 1 is the result of measurement by the solvent resistance evaluation method, and the number of times is the number of times the fabric was immersed back and forth in toluene just before the release layer fell off during the solvent resistance evaluation.

Claims

1. A compound represented by average units of the following formula 1: [Chemical formula 1] R １ ｍ R ２ ｎ SiX （４－ｍ－ｎ）／２ In Formula 1, R １ is a radical-generating functional group, R ２ is a hydrogen atom, an isocyanatoalkyl group, a hydroxyalkyloxy group, an alkoxy group, or a monovalent hydrocarbon group; X is a linker connecting silicon atoms of the compound to each other, and is an oxygen atom or a divalent linker of the following chemical formula 2; m is a number in the range of 1 to 3; n is a number in the range of 0 to 2; and m+n is a number in the range of 1 to 3: [Chemical formula 2] 【Chemistry 1】 In Chemical Formula 2, L １ is an alkylene group or an alkylidene group, L １ The oxygen atoms on either side of each are directly linked to the silicon atom of the compound.

2. R １ is a compound according to claim 1, represented by the following chemical formula 3: [Chemical formula 3] 【Chemistry 2】 In Chemical Formula 3, L ２ and L ３ are each independently an alkylene group or an alkylidene group; R ３ is an aryl group or a heteroaryl group, and L in Chemical Formula 3 ２ is directly linked to the silicon atom of said compound.

3. 2. The compound according to claim 1, wherein in formula 1, m is 1 and n is a number ranging from 0 to 2.

4. The compound of claim 1 having a branched structure, a cage structure or a partial cage structure.

5. The compound according to claim 1, having a weight average molecular weight in the range of 5,000 g / mol to 200,000 g / mol.

6. The compound of claim 1, having a polydispersity index in the range of 1 to 10.

7. A mold release composition comprising the compound according to any one of claims 1 to 6.

8. 8. The mold release composition of claim 7, additionally comprising a curable silicone resin component.

9. The mold release composition of claim 8, wherein the curable silicone resin component comprises a polyorganosiloxane having an average unit of the following chemical formula 4 and a polyorganosiloxane having an average unit of the following chemical formula 5: [Chemical formula 4] P ａ Q ｂ Yes （４－ａ－ｂ）／２ In Chemical Formula 4, P is an alkenyl group, Q is an alkoxy group, a hydroxy group, or a monovalent hydrocarbon group, a is a number in the range of 0.0001 to 0.1, and b is a number in the range of 1 to 4: [Chemical formula 5] H ｃ Q ｄ Yes （４－ｃ－ｄ）／２ In Chemical Formula 5, Q is an alkoxy group, a hydroxy group, or a monovalent hydrocarbon group; c is a number in the range of 0.01 to 0.9; and d is a number in the range of 1 to 4.

10. The mold release composition according to claim 9, wherein the polyorganosiloxane of the formula 4 comprises one or more siloxane units selected from the group consisting of a siloxane unit of the following formula 6 and a siloxane unit of the following formula 7: [Chemical formula 6] Viｲ ６ ２ SiO １／２ [Chemical formula 7] Viｲ ６ SiO ２／２ In formulas 6 and 7, Vi is an alkenyl group, R ６ is a hydroxy group, an alkoxy group, or a monovalent hydrocarbon group.

11. The mold release composition of claim 9, wherein the polyorganosiloxane of formula 5 comprises a siloxane unit of formula 9: [Chemical formula 9] HR ６ SiO ２／２ In Chemical Formula 9, R ６ is a hydroxy group, an alkoxy group, or a monovalent hydrocarbon group.

12. 10. The mold release composition of claim 9, wherein the polyorganosiloxane having an average unit of formula 4 has a weight average molecular weight in the range of 100,000 g / mol to 1,000,000 g / mol.

13. 10. The mold release composition of claim 9, wherein the polyorganosiloxane having an average unit of formula 5 has a weight average molecular weight in the range of 1,000 g / mol to 50,000 g / mol.

14. The mold release composition according to claim 8, further comprising a compound of the following formula 10: [Chemical formula 10] 【Chemistry 3】 In formula 10, R １ is a double bond-containing group, R ２ ~R ４ are each independently an alkyl group.

15. A release layer comprising the release composition according to claim 7 or a cured product thereof.

16. The release layer according to claim 15, wherein the peel force change rate AR according to the following formula 1 is 30% or less: [Formula 1] AR=100×|A2-A1| / A1 In Equation 1, A1 is the release force measured at 25° C. at a peel angle of 180° and a peel speed of 0.3 m / min after maintaining the release layer attached to the pressure-sensitive adhesive layer at 25° C. for 24 hours, and A2 is the release force measured at 25° C. at a peel angle of 180° and a peel speed of 0.3 m / min after irradiating the release layer attached to the pressure-sensitive adhesive layer with ultraviolet light and maintaining the temperature at 60° C. for 24 hours.

17. The release layer according to claim 15, having a residual adhesion rate Ad of 80% or more according to the following formula 2: [Formula 2] Ad=100×Af / Ai In Equation 2, Ai is the release force measured by attaching an adhesive tape to the release layer and peeling the adhesive tape at a peel angle of 180° at 25° C. and a peel speed of 0.3 m / min, and Af is the release force measured by attaching an adhesive tape to the release layer on which the release force Ai was measured in the same manner as when the release force Ai was measured and peeling the adhesive tape at a peel angle of 180° at 25° C. and a peel speed of 0.3 m / min.

18. A release film comprising a base film and the release layer according to claim 15 attached to one or both sides of the base film.

19. 16. An adhesive film comprising: the release layer according to claim 15; and an adhesive layer attached to the release layer.

Images