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] Mutual citation with related applications

[0002] This application claims priority under Republic of Korea Patent Application No. 10-2022-0028888, filed on 7 March 2022, and all content disclosed in the literature of the said Republic of Korea Patent Application is incorporated herein by reference.

[0003] Technical field

[0004] This application relates to compounds, release compositions, release layers, release films, and adhesive films. [Background technology]

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

[0006] The release layer of a release film is generally formed from a silicone-based compound, but a release layer containing the silicone resin can be formed on the base film by coating the base film with a composition containing a silicone-based compound, such as a silicone resin.

[0007] The aforementioned 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 ensured. If the bonding strength between the base film and the release layer decreases, the release film cannot perform its function.

[0009] However, a release layer formed using a silicone-based compound usually does not have a high bonding strength with the base film and shows a tendency for the bonding strength to further decrease over time.

[0010] In addition, during the process of forming the release layer or using the release film, the release layer often comes into contact with a solvent. At this time, if the solvent resistance of the release layer is poor, the bonding strength may decrease or the release layer may be easily damaged. Therefore, ensuring the solvent resistance of the release layer is also an important issue.

Prior Art Documents

Patent Documents

[0011]

Patent Document 1

Summary of the Invention

Problems 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] An object of the present application is to provide a compound that can exhibit an appropriate level of release peel strength, has excellent bonding strength with a base film, and can form a release layer with excellent solvent resistance. Another object of the present application is to provide a compound that shows a stable residual adhesion rate even when the release layer is repeatedly applied to an adhesive layer or the like when the release layer is formed.

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

[0015] In this specification, if the measurement temperature affects any physical property mentioned herein, unless otherwise specified, the physical property is the one measured at room temperature. In this specification, the term "room temperature" means the natural temperature without artificial heating or deheating, and can mean, for example, any single temperature within the range of 10°C to 30°C, or a temperature of approximately 15°C or higher, 18°C ​​or higher, 20°C or higher, or approximately 23°C or higher, and approximately 27°C or lower, or a temperature of approximately 23°C, approximately 25°C, or 27°C.

[0016] Unless otherwise specified, the unit of temperature referred to herein is °C.

[0017] In this application, if the measurement pressure affects any physical property, unless otherwise specified, the physical property is measured at atmospheric pressure. In this specification, the term "atmospheric pressure" refers to the natural pressure without artificial pressurization or depressurization, and generally means atmospheric pressure, for example, a pressure of approximately 740 mmHg to 780 mmHg.

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

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

[0020] As used in this application, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent. The position of substitution is not particularly limited as long as it is a position where a hydrogen atom can be substituted, i.e., a position where a substituent can be substituted. If two or more substituents are substituted, the substituents may be identical or different from each other.

[0021] In this specification, an alkyl group or alkoxy group is, unless otherwise specified, a linear or branched alkyl group or alkoxy 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 alkyl group or alkoxy 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 alkyl group or alkoxy group mentioned above includes alkyl groups or alkoxy groups that consist only of a ring structure and alkyl groups or alkoxy groups that include a ring structure. For example, both cyclohexyl groups and methylcyclohexyl groups are cyclic alkyl groups.

[0022] In this application, alkylene group and alkyldene group refer to a divalent residue formed by the removal of two hydrogen atoms from an alkane. In the case of an alkylene group, the two hydrogen atoms are formed by the removal of one hydrogen atom each from different carbon atoms of the alkane, while in the case of an alkylidene group, the two hydrogen atoms are formed by the removal of one carbon atom of the alkane. In this specification, unless otherwise stated, the alkylidene group may be a linear or branched alkylidene group having 1 to 20 carbon atoms, or 1 to 16 carbon atoms, or a cyclic alkylidene 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 atom cyclic alkylidene groups. The cyclic alkylidene group includes alkylidene groups having only a ring structure and alkylidene groups containing a ring structure. In this specification, unless otherwise stated, an alkylene group may be a linear or branched acyclic alkylene group having 2 to 20 carbon atoms, 2 to 16 carbon atoms, 2 to 12 carbon atoms, 2 to 8 carbon atoms, or 2 to 6 carbon atoms, or a cyclic alkylene 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 alkylene group includes alkylene groups having only a ring structure and alkylene groups having a ring structure.

[0023] In this specification, an alkenyl group or alkenylene group is, unless otherwise specified, a linear or branched acyclic alkenyl group or alkenylene 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 a cyclic alkenyl group or alkenylene 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 alkenyl group or alkenylene group mentioned above includes both alkenyl groups or alkenylene groups having only a ring structure and alkenyl groups or alkenylene groups having a ring structure.

[0024] In this specification, an alkynyl group or alkynylene group is, unless otherwise specified, a linear or branched acyclic alkynyl or alkynylene group having 2 to 20 carbon atoms, 2 to 16 carbon atoms, 2 to 12 carbon atoms, 2 to 8 carbon atoms, or 2 to 6 carbon atoms, or a cyclic alkynyl or alkynylene 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. Here, including a cyclic alkynyl or alkynylene group, it falls under the category of 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 one or more substituents. In this case, the substituent may be one or more selected from the group consisting of halogens (chlorine (Cl), iodine (I), bromine (Br), fluorine (F)), aryl group, heteroaryl group, epoxy group, alkoxy group, cyano group, carboxyl group, acryloyl group, methacryloyl group, acryloyloxy group, methacryloyloxy group, carbonyl group, and hydroxyl group, but is not limited thereto.

[0026] In this specification, the term "aryl group" means a substituent formed by removing one hydrogen atom from an aromatic hydrocarbon ring compound, and the aromatic hydrocarbon ring compound may be a monocyclic or polycyclic compound. The aryl group is not particularly limited in terms of the number of carbon atoms, but unless otherwise stated, 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 this specification, "arylene group" means a divalent functional group obtained by removing an additional hydrogen atom from the aryl group. Except for the fact that each is a divalent group, the above-described explanation for aryl groups applies equally to these. Examples of the aryl group include, but are not limited to, phenyl, phenylethyl, phenylpropyl, benzyl, tolyl, xylyl group, or naphthyl group.

[0028] In this application, the term "heteroaryl group" refers to a functional group having an aryl group in which one or more carbon atoms constituting the aromatic ring of the aryl group are replaced by heteroatoms other than carbon atoms. Examples of heteroatoms include nitrogen (N), oxygen (O), sulfur (S), selenium (Se), and tellurium (Te). The atoms constituting the ring structure of the heteroaryl group can be called ring atoms. Furthermore, the heteroaryl group may include monocyclic or polycyclic rings. The number of carbon atoms or ring atoms of the heteroaryl group is not particularly limited, but unless otherwise stated, it may be in 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. In other examples, the heteroaryl group is not particularly limited in the number of ring atoms, but for example, the heteroaryl group may be 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. The heteroaryl group is, for example, 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 pyridadinyl group, a pyrazinyl group, a quinolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyramidinyl group, a pyrazinopyramidinyl group, a 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 benzosilol group, a dibenzosilol group, or a phenanthrolinyl group. Examples include, but are not limited to, isoxazolyl groups, thiadiazolyl groups, phenothiazinyl groups, phenoxyazazine groups, and condensed structures thereof.

[0029] Furthermore, the term "heteroarylene group" as used in this application refers to a divalent group obtained by removing one additional hydrogen atom from the heteroaryl group. Aside from being a divalent group, the above-described explanation of the heteroaryl group can be applied to these groups.

[0030] The aryl group or heteroaryl group may be optionally substituted with one or more substituents. In this case, the substituent may be one or more selected from the group consisting of halogens (chlorine (Cl), iodine (I), bromine (Br), fluorine (F)), aryl groups, heteroaryl groups, epoxy groups, alkoxy groups, cyano groups, carboxyl groups, acryloyl groups, methacryloyl groups, acryloyloxy groups, methacryloyloxy groups, carbonyl groups, and hydroxyl groups, but is not limited thereto.

[0031] This application provides a compound having a specific structure. For example, the compound may be a compound containing a silicon atom to which a radical-generating functional group is bonded.

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

[0033] Such compounds can be expressed, for example, in the average units of the chemical formula 1 shown below.

[0034] [Chemical formula 1]

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

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

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

[0038] As used herein, the term "average unit" means an expression obtained by converting the number of moles of functional groups (functional groups directly linked to silicon atoms) and linkers (linkers connecting silicon atoms to each other) contained in the compound based on the assumption that the number of moles of silicon atoms contained in the compound is 1 mole. Such an average unit may be for one molecule of the compound or for a mixture of two or more molecules of the compound. When the average unit is for a mixture of two or more molecules of the compound, the ratio of other functional groups or linkers is calculated assuming that the total number of silicon atoms contained in the mixture is 1.

[0039] R shown on the left side of the silicon atom (Si) in Chemical Formula 1 1 and R 2 represent functional groups directly linked to the silicon atom, and X on the right represents a linker that connects silicon atoms to each other.

[0040] In Chemical Formula 1, m is the number of moles of the functional group R 1 converted assuming that the number of moles of silicon atoms contained in the compound is 1 mole, and n is the number of moles of the functional group R 2 converted assuming that the number of moles of silicon atoms contained in the compound is 1 mole.

[0041] Also, in Chemical Formula 1, (4 - m - n) is the number of moles of the linker X converted 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 for display.

[0042] This method of display is similar to the method used to display the average unit of so-called polyorganosiloxanes.

[0043] In chemical formula 1, linker X may be an oxygen atom or a divalent linker of the following chemical formula 2.

[0044] [Chemical formula 2]

[0045] [ka]

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

[0047] The specific types of alkylene or alkylidene groups of chemical 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 directly bonded to the silicon atoms of the compound.

[0049] As described later, the compound has the desired functional group (R 1 It is produced by reacting an alkoxysilane (such as) into which a linker of the chemical formula 2 is introduced with a diol compound that forms the linker of the chemical formula 2. In such a case, the alkoxy group of the alkoxysilane reacts with the hydroxyl group of the diol compound to derive a structure in which the silicon atoms of the alkoxysilane are linked by the linker of the chemical formula 2. In this reaction process, a siloxane bond may be formed in which silicon atoms are linked to each other via an oxygen atom through a condensation reaction between the alkoxy groups of the alkoxysilane. Therefore, in chemical formula 1, X can be an oxygen atom or the divalent linker of the chemical formula 2.

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

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

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

[0053] R in chemical formula 1 2 The specific types of alkyl groups contained in the isocyanate alkyl group and hydroxyalkyloxy group, and the specific types of alkoxy groups, are as described at the beginning of this specification.

[0054] Furthermore, 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), and examples of such residues include alkyl groups, alkenyl groups, alkynyl groups, or aryl groups. Specific examples of the alkyl groups, alkenyl groups, alkynyl groups, or aryl groups are as described at the beginning of this specification.

[0055] As described later, the compound has the radical-generating functional group (R 1Alkoxysilanes to which radical-generating functional groups (such as) have been introduced can be produced by reacting them in the presence of a diol compound, and the introduction of the radical-generating functional group can be carried out by a urethane reaction using an alkoxysilane compound having an isocyanate alkyl group. In such a case, theoretically, all of the isocyanate alkyl groups contained in the alkoxysilane compound are converted to the radical-generating functional group, and all of the alkoxy groups in the alkoxysilane compound are converted to linkers (oxygen atoms or the linker of chemical formula 2). However, the final compound may contain isocyanate alkyl groups that did not participate in the urethane reaction, and may contain alkoxy groups that did not form a linker and / or alkoxy groups that reacted with the diol compound but did not form a linker (these alkoxy groups exist in the form of hydroxyalkyloxy groups). Furthermore, the alkoxysilane compound may contain hydrogen or monovalent hydrocarbon groups that do not participate in the urethane reaction and the linker formation reaction.

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

[0057] In chemical formula 1, m can be a number in the range of 1 to 3, a number in the range of 1 to 2.5, a number in the range of 1 to 2, or a number in the range of 1 to 1.5, or it 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 in chemical formula 1 (m+n) may be a number within the range of 1 to 3, a number within the range of 1.5 to 3, a number within the range of 2 to 3, or a number within the range of 2.5 to 3.

[0060] As one example, the radical-generating functional group R of chemical formula 1. 1 This may be a functional group represented by the following chemical formula 3.

[0061] [Chemical formula 3]

[0062] [ka]

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

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

[0065] L2 in chemical formula 3 is directly bonded to the silicon atom of the compound.

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

[0067] The functional group of chemical formula 3 has a structure in which oxygen atoms are present on both sides of L3. Due to the high electronegativity of the oxygen atoms, the carbon-carbon bond or carbon-oxygen bond within the -O-L3-C(=0)- structure has a relatively weak bond strength, and therefore, the bond can break and generate radicals when external energy is applied, such as by irradiation with light or application of heat.

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

[0069] The compound may be a polymer. Therefore, the compound can have a molecular weight above a certain level. For example, the lower limit of the weight-average molecular weight of the compound is 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. It may be to a certain extent, and the upper limit may be approximately 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 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 one of the lower limits described above.

[0070] The compound may have a certain level of polydispersity index. The polydispersity index is the value obtained by dividing the weight-average molecular weight (Mw) of the compound by the number-average molecular weight (Mn) (Mw / Mn). The lower limit of the polydispersity index may be around 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 around 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 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 one of the lower limits described above.

[0071] The aforementioned compounds can provide the release layer targeted in this application by being included in the release layer and forming a unique cross-linking structure.

[0072] The aforementioned compounds can be synthesized using known methods, such as known methods for producing polyorganosiloxanes.

[0073] Among the methods for synthesizing polyorganosiloxanes, 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 this application, the condensation reaction of the polyorganosiloxane is carried out in the presence of a diol compound. In such a case, the linker of chemical formula 2 can be formed through the reaction between the hydroxyl group of the diol compound and the alkoxy group of the alkoxysilane. Furthermore, the alkoxysilane applied to the condensation reaction is R. 1 and / or R 2 By applying compounds containing the aforementioned chemical formula, it is possible to synthesize compounds having the average unit of the chemical formula 1.

[0074] In the above process, the alkoxysilane is R 1 and / or R 2 The functional group of, in particular the R 1 The method for introducing the functional group is not particularly limited. For example, among commercially available alkoxysilanes, the alkoxy group together with the R 1 and / or R 2 Alkoxysilanes having the functional group can be used. Alternatively, the functional group may be introduced into the alkoxysilane through a separate reaction. For example, when using an alkoxysilane having an isocyanate group as the alkoxysilane and reacting it 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 example of a synthesis method for such a compound is described in Production Example 1 of this specification.

[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) into which the radical-generating site of the radical-generating compound has been introduced. As the isocyanate compound having an alkoxysilyl group, a commercially available compound can be used, and as the radical-generating compound, a commercially available compound (for example, a compound having a hydroxyl group among compounds known as radical initiators) can be applied.

[0077] The reaction to obtain the intermediate product can be carried out at a predetermined temperature for a predetermined time, with the addition of a catalyst if necessary. The intermediate product can then be reacted further in the presence of a polyol (diol compound) to obtain the target compound. This additional reaction can also be carried out at a predetermined temperature for a predetermined time. The temperature and time can be adjusted considering the yields of the reacting compounds and the target compound. For example, the predetermined temperature may be in the range of 60°C to 150°C, and the predetermined time may be in the range of 1 hour to 7 hours, but is not limited thereto.

[0078] As described above, the radical-generating compound applied to the reaction may be, for example, a compound having a hydroxyl group among compounds known to generate radicals. One example of such a compound is a radical initiator having a hydroxyl 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-hydroxycyclohexylphenyl 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. Furthermore, the radical-generating compound may contain one or more active groups selected from the group consisting of aryl groups and heteroaryl groups. When the radical-generating compound contains an aryl group and / or a heteroaryl group, post-curing is possible by initiating polymerization without decomposition, and a compound that can reduce unreacted products can be formed.

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

[0080] Furthermore, the isocyanate compound having an alkoxysilyl group may have at least one alkoxysilyl group, and the alkoxy group bonded to the silicon atom (Si) by the alkoxysilyl group may be an alkoxy group having 1 to 20 carbon atoms. The upper limit of the carbon number may be approximately 19, 18, 17, 16, 15, 14, 13, 12, 11, 10, 9, 8, 7, 6, 5, 4, or 3. The carbon number may be less than or equal to any of the upper limits described above. 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 aforementioned compound can be obtained by reacting a composition containing an isocyanate compound having an alkoxysilyl group and a radical-generating compound, as described above. In this case, the proportion of each reaction compound in the composition can be adjusted considering 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 approximately 10% by weight, 12.5% ​​by weight, 15% by weight, 17.5% by weight, 20% by weight, 22.5% by weight, 25% by weight, 27.5% by weight, 30% by weight, 32.5% by weight, or 35% by weight, relative to the total weight of the composition, and the upper limit may be approximately 50% by weight, 48% by weight, 46% by weight, 44% by weight, 42% by weight, or 40% by weight. The percentage 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 one of the lower limits described above. When the composition forming the intermediate product contains the compound in the aforementioned content, it is possible to provide a compound that has excellent film-forming properties, an appropriate level of release force and excellent residual adhesion, and can form a release layer in which changes in release force due to external factors such as heat and ultraviolet light are minimized.

[0083] The lower limit of the amount of the isocyanate compound having the alkoxysilyl group in the composition relative to 100 parts by weight of the radical generating compound may be approximately 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 approximately 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 proportion 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 one of the lower limits described above. When the composition forming the intermediate product contains an isocyanate compound having an alkoxysilyl group within the range, it is possible to form a compound that exhibits excellent cohesive force, is advantageous for coating film formation, has appropriate elasticity and hydrophilicity, possesses an appropriate level of release force and excellent residual adhesion, 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 that forms the aforementioned intermediate product can be carried out in the presence of a suitable catalyst, such as a catalyst known as a urethane catalyst. Examples of such catalysts include tertiary amine compounds, aprotic salts, or organometallic compounds. Specifically, organotin catalysts such as dibutyltin dilaurate (DBTDL) may be used, but are not limited to these.

[0085] The lower limit of the content of the catalyst per 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. It may be about parts, 0.2 parts by weight, 0.22 parts by weight, or 0.24 parts by weight, and its 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 content of the catalyst 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.

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

[0087] The term "polyol" refers to a compound having two or more hydroxyl groups in its molecule. Furthermore, it is sufficient that the polyol has two or more hydroxyl groups in its molecule; there are no particular restrictions on its type. Examples 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, and 1,9-nonol. These may include, but are not limited to, diethylenetriol, 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 units, trimethylolpropane and 2,2-dimethyl-1,3-propanediol.

[0088] The amount of polyol used can also be adjusted in consideration of the structure of the target compound. For example, the lower limit of the amount of polyol per 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 about 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 about 1 part by weight. The amount of 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 by which the condensation reaction proceeds is not particularly limited and can be carried out by known methods.

[0090] Furthermore, this application relates to a release composition containing the aforementioned compound. The term "release composition" means a composition capable of forming a release layer, and the meaning of the release layer is as is well known in the industry.

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

[0092] If the release composition is curable, it may be an active energy ray (e.g., ultraviolet) curing type, a moisture curing type, a thermosetting type, or a room-temperature curing type, and in some cases, it may be a hybrid form in which two or more of the above are combined. If the release composition is an active energy ray curing type, curing of the release composition is carried out by irradiation with active energy rays such as ultraviolet rays; if it is a moisture curing type, curing of the release composition is carried out by maintaining it under appropriate humidity; if it is a thermosetting type, curing of the release composition is carried out by applying appropriate heat; or if it is a room-temperature curing type, curing of the release composition may be carried out by maintaining the release composition at room temperature.

[0093] In the release composition, the lower limit of the content of the compound having the average unit of chemical formula 1 may be approximately 0.01% by weight, 0.05% by weight, 0.1% by weight, 0.5% by weight, 1% by weight, 5% by weight, 7% by weight, 9% by weight, 10% by weight, 11% by weight, 13% by weight, or 14% by weight, and the upper limit may be approximately 40% by weight, 39% by weight, 38% by weight, 36% by weight, 34% by weight, 32% by weight, 30% by weight, 28% by weight, 26% by weight, 24% by weight, 22% by weight, 20% by weight, 18% by weight, 16% by weight, 14% by weight, 12% by weight, 10% by weight, 8% by weight, 6% by weight, 4% by weight, 2% by weight, or 1% by weight. The aforementioned 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 may also be within the range of less than or equal to any one of the upper limits described above. Within this range, a release composition can be provided that can ensure appropriate film-forming ability, release force, and excellent residual adhesion. The aforementioned ratio is a ratio based on solid content, and therefore, if the release composition contains a solvent, it is a ratio to the total weight of the release composition excluding the weight of the solvent. The aforementioned ratio may also be the ratio of the compound or its reactants in the release layer described later.

[0094] The aforementioned release composition may be a solvent-based, aqueous, or solvent-free release composition.

[0095] The release composition comprises the compound and may further contain a curable silicone resin component. In this specification, the term "silicone resin component" means a component consisting of one polyorganosiloxane or a mixture of two or more polyorganosiloxanes.

[0096] As one example, the silicone resin component of the release agent composition may be a so-called addition-curing component. Such a resin component may include, for example, a polyorganosiloxane (hereinafter referred to as a first polyorganosiloxane or first polyorganosiloxane component) containing siloxane units having alkenyl groups bonded to silicon atoms.

[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. If the average unit is for a mixture of two or more molecules of polyorganosiloxane, the proportion of other functional groups or atoms is calculated by assuming that the total number of silicon atoms 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 is an alkenyl group, Q is an alkoxy group, a hydroxyl group, or a monovalent hydrocarbon group, a is 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 alkenyl and alkoxy groups are as described at the beginning of this specification, and the specific type of monovalent hydrocarbon group is the same as that of 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 may be approximately, and its upper limit may be approximately 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 above a 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 one of the lower limits described above.

[0103] In the aforementioned chemical formula 4, the lower limit of b may be approximately 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 approximately 3.5, 3, 2.9, 2.8, 2.7, 2.6, 2.5, 2.4, 2.2, 2.1, or 2. The aforementioned b 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 one of the lower limits described above.

[0104] A polyorganosiloxane having the average unit of chemical formula 4 may contain alkenyl groups in a range of 0.01 mol% to 1.5 mol% of the total organic groups. For example, the lower limit of the number of moles of alkenyl groups, based on the total number of moles of organic groups in the polyorganosiloxane having the average unit of 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 percentage may be approximately 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 its upper limit may be approximately 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 percentage 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 one of the lower limits described above.

[0105] Such polyorganosiloxanes having the average unit of chemical formula 4 may contain one or more siloxane units selected from the group consisting of the siloxane units of chemical formula 6 and the siloxane units of chemical formula 7.

[0106] [Chemical formula 6]

[0107] ViR 6 2SiO 1 / 2

[0108] [Chemical formula 7]

[0109] ViR 6 SiO2 / 2

[0110] In chemical formulas 6 and 7, Vi is an alkenyl group, and R 6 This group is a hydroxyl group, an alkoxy group, or a monovalent hydrocarbon group. The specific types of alkenyl groups, alkoxy groups, and monovalent hydrocarbon groups are as described in Chemical Formula 4.

[0111] If present, the lower limit of the proportion of siloxane units of chemical formula 6, based on the total siloxane units in the first polyorganosiloxane component, may be approximately 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 approximately 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 aforementioned 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 may also be within the range of less than or equal to any one of the upper limits described above.

[0112] If included, the lower limit of the proportion of siloxane units of chemical formula 7, based on the total siloxane units in the first polyorganosiloxane component, may be approximately 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 approximately 10 mol%, 9 mol%, 8 mol%, 7 mol%, 6 mol%, 5 mol%, 4 mol%, 3 mol%, 2 mol%, or 1 mol%. The proportion 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 contain all of the siloxane units of chemical formulas 6 and 7. In such cases, the lower limit of the molar ratio of siloxane units of chemical formula 7 to siloxane units of chemical formula 6 may be approximately 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 approximately 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 approximately 500, 1,500, 2,000, 2,500, or 3,000, and the upper limit may be approximately 10,000, 5,000, 4,000, 3,500, 3,000, 2,500, or 2,100. The number of silicon atoms may be greater than or greater than 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 greater than any one of the lower limits described above, and less than or equal to any one of the upper limits described above.

[0115] The first polyorganosiloxane component may have a substantially linear structure. In such cases, the polyorganosiloxane may consist substantially only of M units (monofunctional siloxane units) and D units (difunctional siloxane units), or it may contain T units (trifunctional siloxane units) and / or Q units (tetrafunctional siloxane units) along 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) may be below a certain level.

[0116] For example, in the first polyorganosiloxane component, the upper limit of the ratio of the total number of moles of T and Q units to the total number of moles of siloxane units contained in the polyorganosiloxane (100 × (number of moles of T units + number of moles of Q units) / total number of moles of siloxane units) may be approximately 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 greater than or equal to any one of the lower limits described above, and within the range of 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 approximately 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 is 100 The weight-average molecular weight may be approximately 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, 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 aforementioned chemical formula 4 average units can ensure appropriate viscosity and exhibit excellent coating properties by having a weight-average molecular weight within the range described above.

[0118] The lower limit of the polyvariance index of the polyorganosiloxane having the average unit of chemical formula 4 may be approximately 1, 1.25, or 1.5, and the upper limit may be approximately 5, 3.5, or 2.5. The polyvariance index 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 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 include a polyorganosiloxane having the average unit of chemical formula 4 described above, as well as a polyorganosiloxane having the average unit of chemical formula 5 (hereinafter referred to as a second polyorganosiloxane or second polyorganosiloxane component). Such an average unit may be for one molecule of polyorganosiloxane or for a mixture of two or more polyorganosiloxane molecules. If the average unit is for a mixture of two or more polyorganosiloxane molecules, the proportion of other functional groups or atoms is calculated by assuming that the total number of silicon atoms 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 is a hydrogen atom, Q is an alkoxy group, a hydroxyl group, or a monovalent hydrocarbon group, c is a number in the range of 0.01 to 0.9, and d may be a number in the range of 1 to 4. Specific examples of the alkoxy group or monovalent hydrocarbon group in chemical formula 5 are the same as in the case of chemical formula 4.

[0123] In the aforementioned chemical formula 5, the lower limit of c may be approximately 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 its upper limit may be approximately 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 value of c 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 one of the lower limits described above.

[0124] In the aforementioned chemical formula 5, the lower limit of d may be approximately 0.5, 1, 1.1, 1.2, 1.3, 1.4, 1.5, or 1.6, and its upper limit may be 4, 3.5, 3, 2.5, 2, 1.9, 1.8, 1.7, 1.6, or 1.5. d 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 one of the lower limits described above.

[0125] The lower limit of the ratio of moles of silicon-bonded hydrogen atoms in the average unit of chemical formula 5, based on the total number of moles of silicon-bonded organic groups in the average unit of chemical formula 5, may be approximately 1 mol%, 5 mol%, 10 mol%, 15 mol%, 20 mol%, 25 mol%, or 30 mol%, and the upper limit may be approximately 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, 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 ratios, appropriate curability can be ensured, and a release layer with the desired release properties can be formed.

[0126] The average unit of chemical formula 5 in this application, which is an organic group polyorganosiloxane, may contain the siloxane unit of the following chemical formula 9.

[0127] [Chemical formula 9]

[0128] HR 6 SiO 2 / 2

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

[0130] The lower limit of the percentage of moles of the silicon siloxane unit of chemical formula 9, based on the total number of moles of siloxane units containing silicon-bonded hydrogen atoms among the total siloxane units contained in the second polyorganosiloxane component, may be approximately 85 mol%, 90 mol%, 95 mol%, 96 mol%, 97 mol%, 98 mol%, 99 mol%, or 99.5 mol%, and the upper limit may be approximately 100 mol%. The percentage 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 proportion of siloxane units of chemical formula 9, based on the total siloxane units in the second polyorganosiloxane component, may be approximately 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 approximately 85 mol%, 80 mol%, 75 mol%, 70 mol%, 65 mol%, 60 mol%, 55 mol%, or 50 mol%. The proportion 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 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 approximately 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, or 90, and the upper limit may be approximately 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 greater than 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 greater than 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 cases, the polyorganosiloxane may consist substantially only of M units and D units, or it may contain T and / or Q units along with M and D units, but the proportion of T and / or Q units may be below a certain level.

[0134] For example, in the second polyorganosiloxane component, the upper limit of the ratio of the total number of moles of T and Q units to the total number of moles of siloxane units contained in the polyorganosiloxane (100 × (number of moles of T units + number of moles of Q units) / total number of moles of siloxane units) may be approximately 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 greater than or equal to any one of the lower limits described above, and within the range of 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 chemical formula 5 may be approximately 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 100,000 g / mol, 90,000 g / mol. It may be 1 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 approximately 12,000 g / mol. The weight-average molecular weight may be greater than or greater than 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 greater than any one of the lower limits described above, and less than or equal to any one of the upper limits described above. Excellent curability can be ensured by having a weight-average molecular weight within the above range for the polyorganosiloxane having the average unit of chemical formula 5.

[0136] The polyorganosiloxane having the average unit of chemical formula 5 may have a lower limit of polyvariance index of approximately 1, 1.25, or 1.5, and an upper limit of approximately 5, 3.5, or 2.5. The polyvariance index may be greater than or greater than 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 greater than 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 the average unit of chemical formula 4 in the curable silicone resin component or the release composition may be approximately 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 approximately 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 percentage may be greater than or greater than 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 greater than any one of the lower limits described above, and less than or equal to any one of the upper limits described above. The aforementioned ratio is based on the solid content and, therefore, is the ratio to the total weight of the release product excluding the weight of the solvent when the release composition contains a solvent. By including a polyorganosiloxane having the average unit of chemical formula 4 within the range described above, it is possible to ensure an appropriate level of release strength and excellent residual adhesion of the release layer described later.

[0138] The lower limit of the amount of polyorganosiloxane having the average unit of chemical formula 5 in the curable silicone resin component or the release composition relative to 100 parts by weight of polyorganosiloxane having the average unit of chemical formula 4 may be approximately 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 approximately 10 parts by weight, 8 parts by weight, 6 parts by weight, 4 parts by weight, or 3 parts by weight. The proportion may be greater than or greater than 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 greater 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 polyorganosiloxane having the average unit of chemical formula 5 is included within the above range, the crosslinking density can be improved to ensure a cured product with excellent durability.

[0139] The lower limit of the amount by weight of the compound having the average unit of chemical formula 1 in the release composition relative to 100 parts by weight of the polyorganosiloxane having the average unit of chemical formula 4 may be approximately 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 approximately 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 aforementioned ratio may be greater than or greater than 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 greater than any one of the lower limits described above, and less than or equal to any one of the upper limits described above. By adjusting the ratio of compounds having the average unit of chemical formula 1, the desired release layer can be formed more effectively.

[0140] The release composition comprises the aforementioned components and may optionally include additional components as needed.

[0141] For example, the release composition may additionally contain the compound of the following chemical 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 be an alkyl group independently.

[0145] By applying the compound of chemical formula 10, a release composition having excellent film-forming properties can be formed. Such a release composition has excellent bonding properties to the substrate, possesses appropriate level release force and excellent residual adhesion, 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] Specific examples of the alkyl groups R2 to R4 in chemical formula 10 are as described at the beginning of this specification.

[0147] Furthermore, there are no particular restrictions on the specific type of double bond-containing group in chemical formula 10. For example, the double bond-containing group may be an alkenyl group or a (meth)acryloyloxyalkyl group. The specific types of the alkyl group in the alkenyl group and (meth)acryloyloxyalkyl group are as described at the beginning of this specification.

[0148] If included, the lower limit of the content of the compound of chemical formula 10 relative to 100 parts by weight of the compound having the average unit of chemical formula 1 may be approximately 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 approximately 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 aforementioned ratio may be greater than or greater than 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 greater than any one of the lower limits described above, and less than or equal to 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.

[0149] In other examples, the lower limit of parts by weight of the compound of chemical formula 10 relative to 100 parts by weight of polyorganosiloxane having the average unit of chemical formula 4, if included, may be approximately 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 approximately 10 parts by weight, 8 parts by weight, 6 parts by weight, 4 parts by weight, or 3 parts by weight. The proportion may be greater than or greater than 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 greater than any one of the lower limits described above, and less than or equal to any one of the upper limits described above. By adjusting the proportion of the compound as described above, the desired release layer can be formed more effectively.

[0150] The release composition of this application may, if necessary, contain an additional metal catalyst, taking into consideration curability. The metal catalyst may contain one or more elements selected from the group consisting of aluminum, bismuth, lead, mercury, tin, zinc, platinum, silver, and zirconium as a central metal element. Examples of the metal catalyst include, but are not particularly limited to, Bis[1,3-bis(2-ethenyl)-1,1,3,3-tetramethyldisiloxane]platinum (CAS No. 81032-58-8), dibutylthin dilaurate, or dimethylthin diacetate. For example, a catalyst known in the industry as a so-called addition-curing catalyst can be used as the catalyst.

[0151] The lower limit of the amount of the metal catalyst in parts by weight relative to 100 parts by weight of polyorganosiloxane having the average unit of chemical formula 4 may be approximately 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 approximately 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 proportion may be greater than or greater than 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 greater than any one of the lower limits described above, and less than or equal to any one of the upper limits described above. By including the catalyst within the above range, side reactions can be reduced and the cured product formation reaction can be effectively carried out.

[0152] Furthermore, the release composition according to one example of this application may additionally contain a solvent.

[0153] The solvent may be an organic solvent, considering the composition of the release composition. The organic solvent is not particularly limited as long as it is commonly used in the industry, and solvents such as tetrahydrofuran, methyl ethyl ketone, toluene, and heptane, or mixtures thereof, can be used. Furthermore, the mixing ratio of these solvents is not particularly limited and can be appropriately blended as needed.

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

[0155] This 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 contain a compound having the average unit of chemical formula 1 or a reactant thereof, and may, if necessary, include the curable silicone resin component described above, 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. Furthermore, the release layer may be formed by curing the release composition according to the example of this application described above. The curing can be appropriately carried out by a variety of methods as described above. Furthermore, the release layer may contain components remaining after curing the release composition according to the example of this application described above.

[0157] The release layer can satisfy at least one of the physical properties described below by including the release composition or its cured product.

[0158] For example, the release layer may have a peeling force change rate AR calculated using the following formula 1 within a predetermined range. For example, the upper limit of AR may be around 30%, 29%, 28%, 27%, 26%, 25%, 24%, 23%, 22%, 21%, 20%, 19%, 18%, 17%, 16%, 15%, 14%, 13%, or 12%, and its lower limit may be around 0%, 5%, or 10%. The AR 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, and within the range of less than or equal to 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 with a peel angle of 180 degrees and a peel speed of 0.3 m / min after maintaining the release layer in contact with the adhesive layer at 25°C for 24 hours, and A2 is the release force measured at 25°C with a peel angle of 180 degrees and a peel speed of 0.3 m / min after irradiating the release layer with the adhesive layer and maintaining it at 60°C for 24 hours.

[0162] The release force A2 may be either the release force (A21) measured after first irradiating the test piece with ultraviolet light and then maintaining it at 60°C for 24 hours, or the release 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| represents the absolute value of the difference between A2 and A1.

[0164] The specific measurement method for the rate of change of release force AR in Equation 1 (measurement method for release forces A1 and A2) will be described in the Examples section.

[0165] Furthermore, the release layer may have a residual adhesion ratio Ad calculated using the following formula 2 within a predetermined range. For example, the lower limit of the residual adhesion ratio Ad may be approximately 80%, 81%, 82%, 83%, 84%, 85%, 86%, 87%, 88%, 89%, 90%, or 91%, and its upper limit may be approximately 100% or 95%. The Ad may be greater than or greater than any one of the lower limits described above, or greater than 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. The residual adhesion ratio (A) of the release layer according to an example of this application that satisfies the above range is d When it has ), it can be said to have excellent (or appropriate) residual adhesion.

[0166] [Formula 2]

[0167] Ad = 100 × Af / Ai

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

[0169] The specific method for measuring the residual adhesion ratio Ad using the above formula 2 is described in the Examples section of this specification.

[0170] The release layer according to one example of this application may have a release force within a predetermined range when attached to an adhesive tape and maintained at room temperature (approximately 25°C) for 24 hours, and then measured at room temperature (approximately 25°C) with a peeling angle of 180 degrees and a peeling speed of 0.3 m / min. 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 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, and also within the range of less than or equal to any one of the upper limits described above. When the release layer according to one example of this 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] Furthermore, the release layer according to one example of this application adheres to the adhesive tape and is exposed to ultraviolet light with a wavelength of approximately 150 nm at 3 J / m². 2The release force measured at room temperature (approximately 25°C) with a peeling angle of 180 degrees and a peeling speed of 0.3 m / min after irradiating with a light intensity of 0.3 m / min for approximately 60 seconds and maintaining at 60°C for 24 hours may be within a predetermined range. For example, the lower limit of the release force may be approximately 5 gf / inch, and the upper limit may be approximately 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 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, and within the range of less than or equal to any one of the upper limits described above. When a release layer according to an example of this application has a release force (under ultraviolet light and high-temperature storage) that satisfies the above range, it can be said to have an excellent (or appropriate) residual adhesion rate. Furthermore, the release force at this time does not depend on the order of ultraviolet irradiation and high-temperature exposure.

[0172] Furthermore, this application 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 an example of this application is as described above.

[0175] The type of base film for the release film according to this application is not particularly limited. The base film can be any base film that is commonly applicable to the formation of a release film.

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

[0177] Furthermore, the base film may consist of a single layer or two or more layers laminated together, and may also include additional functional layers such as an anti-fouling layer or an antistatic layer. In addition, from the viewpoint of improving adhesion to the base material, surface treatment such as primer treatment may be applied to one or both sides of the base material.

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

[0179] The release film of this application may be manufactured by known methods. For example, the release film of this application may be manufactured by forming a release layer by applying a release composition according to an example of this application to one or both sides of a substrate and then curing it. The method of applying the release composition is not particularly limited as long as it is commonly used in the industry, for example, knife coating, roll coating or reverse coating. Furthermore, when forming the release layer, it may be done after thoroughly 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 may be cured by a suitable maturation process or in a suitable high-temperature environment or light irradiation environment as described above.

[0180] The thickness of the release layer 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] Furthermore, this application relates to adhesive films.

[0182] An example of an adhesive film according to this application may include the above-described release layer and an adhesive layer to which the release layer is attached. The inclusion of the release layer provides protection until the adhesive layer is used.

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

[0184] The adhesive used to form the adhesive layer of the adhesive film according to an example of this application is not particularly limited.

[0185] For example, as the adhesive forming the adhesive layer, an appropriate selection of an adhesive based on an acrylic polymer, silicone polymer, polyester, polyurethane, polyamide, polyether, or a polymer such as a fluorine-based or rubber-based polymer can be used. [Effects of the Invention]

[0186] This application can provide compounds, release compositions, release layers, release films, and adhesive films. This application can provide compounds that can form a release layer that exhibits appropriate Renel release strength, has excellent bonding strength to a base film, and has outstanding solvent resistance. This application can also provide compounds that, when the release layer is formed, exhibit a stable residual adhesion rate even when the release layer is repeatedly applied to an adhesive layer or the like. This application can also provide release compositions and release layers containing the compound, and release films and adhesive films containing the release layer. [Brief explanation of the drawing]

[0187] [Figure 1] This figure shows a simplified step in producing a compound using an example method described in this application. [Modes for carrying out the invention]

[0188] The contents of this application will be described in detail below with reference to the examples and comparative examples, but the contents of this application are not limited to the examples described below.

[0189] 1. Release force

[0190] Test specimens were prepared by laminating the adhesive layer of a release force measuring adhesive tape (TESA7475 PV2, TESA) onto the release layer of a linear film of an example or comparative example. The adhesion was performed by positioning the adhesive tape on the release layer and then passing a roller with a 2.5 kg load back and forth three times. After maintaining the test specimens at room temperature (approximately 25°C) or 60°C for 24 hours, the release force was measured using a physical property measuring device (Cheminstruments, AR-1000) while peeling off the release force measuring adhesive tape at room temperature (approximately 25°C) at a peeling angle of 180 degrees and a peeling speed of 0.3 m / min.

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

[0192] The rate of change AR of the release force of the release layer in the examples or comparative examples was confirmed by 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 (approximately 25°C) using a physical property measuring device (Cheminstruments, AR-1000) at a peeling angle of 180 degrees and a peeling speed of 0.3 m / min. This test specimen was manufactured by laminating a release force measuring adhesive tape (TESA7475 PV2, TESA) using the same method as the release force measurement described above, and maintained at room temperature (approximately 25°C) for 24 hours.

[0196] In Equation 1, A2 is the release force measured at room temperature (approximately 25°C) using a physical property measuring device (Cheminstruments, AR-1000) at a peel angle of 180 degrees and a peel speed of 0.3 m / min. This test specimen was prepared by laminating a release force measuring adhesive tape (TESA7475 PV2, TESA) using the same method as the release force measurement described above, irradiated with ultraviolet light, maintained at 60°C for 24 hours, and then measured at room temperature (approximately 25°C). The ultraviolet light used was ultraviolet light with a wavelength of approximately 150 nm at a rate of 3 J / m 2 The light was shone at this intensity for approximately 60 seconds.

[0197] The release force A2 may be either the release force (A21) measured after first irradiating the test piece with ultraviolet light and then maintaining it at 60°C for 24 hours, or the release 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 in the examples or comparative examples was confirmed by the following formula 2.

[0200] [Formula 2]

[0201] Ad = 100 × Af / Ai

[0202] In Equation 2, Ai is the release force measured after maintaining a test specimen manufactured according to the method described above for evaluating release force at room temperature (approximately 25°C) for 24 hours.

[0203] In Equation 2, Af is the release force measured after a test specimen is manufactured by further attaching a standard tape (TESA7475, TESA) to the release layer of the release film after measuring the release force Ai, using the same method as the method used to measure the release force Ai, and then maintaining the test specimen at room temperature (approximately 25°C) for approximately 24 hours.

[0204] The aforementioned release forces Ai and Af were measured using the same method as for measuring the release force, with a physical property measuring device (AR-1000, Chemininstruments) while peeling the adhesive tape (TESA7475) at room temperature (approximately 25°C) at a peeling angle of 180 degrees and a peeling speed of 0.3 m / min.

[0205] 4. Method for evaluating solvent resistance

[0206] The release layer of the release film of the example or comparative example was irradiated with ultraviolet light and maintained at 60°C for 24 hours. The ultraviolet irradiation was performed in the same manner as when measuring the release force A2 in Formula 1. Subsequently, a cloth soaked in toluene (toluene) was moved back and forth using equipment No. 542-AB (Yasauda) until the release layer was removed. The number of back-and-forth movements until just before the release layer was removed was measured, and the solvent resistance was evaluated according to the following solvent resistance evaluation criteria.

[0207] <Evaluation criteria for solvent resistance>

[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 approximately 20 mg / mL, and after filtering the calibration standard sample and the sample to be analyzed with 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 used 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 equation 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 approximately 80°C in the presence of a catalyst (DBTDL; Dibutyltin dilaurate) to produce intermediate product (A) by reacting the hydroxyl group of 2-hydroxy-2-methylpropiophenone (S1) with the isocyanate group of 3-(triethoxysilyl)propyl isocyanate (S2). The catalyst was used in an amount of approximately 0.292 parts by weight per 100 parts by weight of the total of 2-hydroxy-2-methylpropiophenone (S1) and 3-(triethoxysilyl)propyl isocyanate (S2).

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

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

[0224] Through the aforementioned synthesis process, it can be seen that the target compound is a compound having the average unit of the following chemical formula A.

[0225] [Chemical formula A]

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

[0227] In chemical formula A, R1 R is a functional group of the chemical formula B shown below, 2 is an isocyanatetopropyl 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 in the range of 0 to 2.

[0228] [Chemical formula B]

[0229] [ka]

[0230] In chemical formula B, the leftmost carbon atom is directly bonded to the silicon atom in chemical formula A.

[0231] [Chemical formula C]

[0232] [ka]

[0233] In chemical formula C, the rightmost oxygen atom is directly bonded to the silicon atom in chemical formula A.

[0234] [Chemical formula D]

[0235] [ka]

[0236] In chemical formula D, the oxygen atoms on both sides are directly bonded to the silicon atoms in chemical formula A.

[0237] <Example 1>

[0238] A polyorganosiloxane of chemical formula E (KS-847H, ShinetsuSilicone) (weight-average molecular weight approximately 350,000 g / mol), a polyorganosiloxane of chemical formula F (X-92-122, Shinetsu Silicone) (weight-average molecular weight approximately 10,000 g / mol), a platinum catalyst (PL-50L, Shinetsu Silicone) (C), the compound from Production Example 1, and an 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:Production Example 1:G) and dispersed in a solvent to produce a release composition. The solvent (S) used was 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).

[0239] [Chemical formula E]

[0240] [ka]

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

[0242] [Chemical formula F]

[0243] [ka]

[0244] In chemical formula F, a and b are each approximately 34 to 36 in number.

[0245] <Example 2>

[0246] A polyorganosiloxane of chemical formula E (KS-847H, Shinetsu Silicone) (weight-average molecular weight approximately 350,000 g / mol), a polyorganosiloxane of chemical formula F (X-92-122, Shinetsu Silicone) (weight-average molecular weight approximately 10,000 g / mol), a platinum catalyst (PL-50L, Shinetsu Silicone) (C), the compound from Production 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:Production Example 1:G) and dispersed in a solvent to produce 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 approximately 350,000 g / mol), a polyorganosiloxane of chemical formula F (X-92-122, Shinetsu Silicone) (weight-average molecular weight approximately 10,000 g / mol), a platinum catalyst (PL-50L, Shinetsu Silicone) (C), the compound from Production 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:Production Example 1:G) and dispersed in a solvent to produce a release composition. The same solvent as in Example 1 was used.

[0249] <Example 4>

[0250] A polyorganosiloxane of chemical formula E (KS-847H, ShinetsuSilicone) (weight-average molecular weight approximately 350,000 g / mol), a polyorganosiloxane of chemical formula F (X-92-122, Shinetsu Silicone) (weight-average molecular weight approximately 10,000 g / mol), a platinum catalyst (PL-50L, Shinetsu Silicone) (C), the compound from Production 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:Production Example 1:G) and dispersed in a solvent to produce a release composition. The same solvent as in Example 1 was used.

[0251] <Comparative Example 1>

[0252] A release composition was prepared by mixing a polyorganosiloxane of chemical formula E (KS-847H, ShinetsuSilicone) (weight-average molecular weight approximately 350,000 g / mol), a polyorganosiloxane of chemical formula F (X-92-122, Shinetsu Silicone) (weight-average molecular weight approximately 10,000 g / mol), and a platinum catalyst (PL-50L, Shinetsu Silicone) (C) in a weight ratio of 5:0.1:0.25 (E:F:C), and dispersing the mixture in a solvent. The same solvent used in Example 1 was employed.

[0253] <Evaluation of physical properties>

[0254] The release composition of the example or comparative example was applied to a base film, and a release layer was formed on the base film by maintaining a temperature of approximately 150°C for about 3 minutes. The thickness of the release layer was approximately 50 nm to 80 nm. A PET (polyethylene terephthalate) film with a thickness of approximately 50 μm was used as the base film.

[0255] The results of 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 of release force, with units of gf / inch, and A21 is the release force A21 mentioned in the evaluation method for the rate of change of release force (AR), which is the release force measured after first irradiating the test piece with ultraviolet light and then maintaining it at 60°C for 24 hours, with units of gf / inch.

[0258] Furthermore, in Table 1, AR1 is the value obtained by substituting A21 as A2 into 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 release force A22 mentioned in the evaluation method for the rate of change (AR) of release force, which is the release force measured after maintaining the test specimen at 60°C for 24 hours and irradiating it with ultraviolet light, and the unit is gf / inch.

[0260] In Table 1, AR2 is the value obtained by substituting A22 into formula A of the method for evaluating the rate of change (AR) of release force, and the unit is %.

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

[0262] The solvent resistance shown in Table 1 is the result of measurement using the solvent resistance evaluation method described above, and the number of cycles is the number of times the fabric was immersed in toluene until just before the release layer detached during the solvent resistance evaluation.

Claims

1. Compounds expressed in the average units of the following chemical formula 1: [Chemical formula 1] R １ ｍ R ２ ｎ SiX （４－ｍ－ｎ）／２ In chemical formula 1, R １ It is represented by the following chemical formula 3, R ２ is hydrogen, isocyanate alkyl group, hydroxyalkyloxy group, alkoxy group, or monovalent hydrocarbon group, X is a linker that connects silicon atoms of the compound to each other, and is 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, and the oxygen atoms on both sides of L １ are each directly linked to the silicon atom of the said compound: [Chemical formula 3] 【Chemistry 2】 In chemical formula 3, L2 and L3 are independently alkylene groups or alkylidene groups, R3 is an aryl group or a heteroaryl group, and L2 in chemical formula 3 is directly bonded to the silicon atom of the compound.

2. The compound according to claim 1, wherein in chemical formula 1, m is 1 and n is a number in the range of 0 to 2.

3. The compound according to claim 1, having a branched structure, a cage structure, or a partial cage structure.

4. The compound according to claim 1, wherein the weight-average molecular weight is in the range of 5,000 g / mol to 200,000 g / mol.

5. The compound according to claim 1, wherein the polydispersity index is in the range of 1 to 10.

6. A release composition comprising the compound described in any one of claims 1 to 5.

7. The release composition according to claim 6, further comprising a curable silicone resin component.

8. The mold release composition according to claim 7 comprises a polyorganosiloxane having the average unit of the following chemical formula 4 and a polyorganosiloxane having the 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 hydroxyl 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 hydroxyl 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.

9. The release composition according to claim 8, wherein the polyorganosiloxane of chemical formula 4 comprises one or more siloxane units selected from the group consisting of the siloxane units of chemical formula 6 and the siloxane units of chemical formula 7: [Chemical formula 6] Viｲ ６ ２ SiO １／２ [Chemical formula 7] Viｲ ６ SiO ２／２ In chemical formulas 6 and 7, Vi is an alkenyl group, and R ６ This is a hydroxyl group, an alkoxy group, or a monovalent hydrocarbon group.

10. The release composition according to claim 8, wherein the polyorganosiloxane of chemical formula 5 contains the siloxane unit of chemical formula 9 below: [Chemical formula 9] HR ６ SiO ２／２ In chemical formula 9, R ６ This is a hydroxyl group, an alkoxy group, or a monovalent hydrocarbon group.

11. The release composition according to claim 8, wherein the polyorganosiloxane having the average unit of chemical formula 4 has a weight-average molecular weight in the range of 100,000 g / mol to 1,000,000 g / mol.

12. The release composition according to claim 8, wherein the polyorganosiloxane having the average unit of chemical formula 5 has a weight-average molecular weight in the range of 1,000 g / mol to 50,000 g / mol.

13. The release composition according to claim 7, further comprising the compound of the following chemical formula 10: [Chemical formula 10] 【Transformation 3】 In chemical formula 10, R １ R is a double bond-containing group, ２ ~R ４ These are each an alkyl group, independently of each other.

14. A release layer comprising the release composition described in claim 6 or a cured product thereof.

15. The release layer according to claim 14, wherein the rate of change of release force AR calculated by 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 with a peel angle of 180 degrees and a peel speed of 0.3 m / min after maintaining the release layer in contact with the adhesive layer at 25°C for 24 hours, and A2 is the release force measured at 25°C with a peel angle of 180 degrees and a peel speed of 0.3 m / min after irradiating the release layer with the adhesive layer and maintaining it at 60°C for 24 hours.

16. The release layer according to claim 14, wherein the residual adhesion rate Ad calculated by formula 2 below is 80% or more: [Formula 2] Ad=100×Af / Ai In Equation 2, Ai is the release force measured by attaching adhesive tape to the release layer and peeling the adhesive tape at a peel angle of 180 degrees and a peel speed of 0.3 m / min at 25°C, and Af is the release force measured by attaching adhesive tape to the release layer in the same manner as when the release force Ai was measured and peeling the adhesive tape at a peel angle of 180 degrees and a peel speed of 0.3 m / min at 25°C.

17. A release film comprising a base film and a release layer according to claim 14 attached to one or both sides of the base film.

18. An adhesive film comprising a release layer according to claim 14, and an adhesive layer attached to the release layer.

Images