Compounds

Abstract

The present application can provide a compound, a release composition, a release layer, a release film, and a pressure-sensitive adhesive film. The present application can provide a compound which can form a release layer capable of exhibiting an appropriate level of release peeling force, and having excellent binding force to a base film and excellent solvent resistance. Furthermore, the present application can provide a compound which, when a release layer has been formed, exhibits a stable residual tack even in a case where it is repeatedly applied to a pressure-sensitive adhesive layer or the like. The present application can also provide a release composition and a release layer containing the compound, and a release film and a pressure-sensitive adhesive film including the release layer.

Description

Technical Field

[0001] Cross-reference to related applications

[0002] This application claims priority to Korean Patent Application No. 10-2022-0028888, filed on March 7, 2022, the disclosure of which is incorporated herein by reference in its entirety. Technical Field

[0004] This application relates to compounds, release compositions, release layers, release films, and pressure-sensitive adhesive films. Background Technology

[0005] Release films are used for various purposes, including protecting the surface of pressure-sensitive adhesives or adhesive surfaces, serving as carriers, and coating base materials. For example, so-called light-peel or medium-peel release films can be applied to protect optically clear adhesives (OCA). Furthermore, release films can be used as carriers for tapes, or as coating base materials for multilayer ceramic capacitors (MLCCs).

[0006] The release layer of a release film is typically formed from a silicone-based compound, wherein a composition containing a silicone-based compound, such as a silicone resin, can be coated onto a base film to form a release layer containing a silicone resin on the base film.

[0007] Release layers have low surface energy and flexibility. For example, Patent Document 1 discloses a release film having a release layer formed from an organosilicon-based compound.

[0008] In release films, the adhesion between the base film and the release layer must be ensured. If the adhesion between the base film and the release layer is reduced, it cannot function as a release film.

[0009] However, release layers formed using silicone-based compounds typically do not have high adhesion to the base film, and show a trend of further decrease in adhesion over time.

[0010] In addition, during the process of forming the release layer or using the release film, the release layer is frequently exposed to solvents. If the solvent resistance of the release layer decreases, the adhesion may decrease or the release layer may be easily damaged. Therefore, ensuring solvent resistance is also an important goal of the release layer.

[0011] (Patent Document 0001) Korean Patent Publication No. 10-2021-0115256 Summary of the Invention

[0012] Technical issues

[0013] This application provides compounds, release compositions, release layers, release films, and pressure-sensitive adhesive films.

[0014] This application aims to provide compounds capable of forming release layers that exhibit appropriate levels of release peel strength, excellent adhesion to a base film, and excellent solvent resistance. Furthermore, this application aims to provide compounds that, when formed, exhibit a stable residual adhesion rate even when repeatedly applied to pressure-sensitive adhesive layers, etc.

[0015] This application also aims to provide release compositions and release layers comprising the said compound, as well as release films and pressure-sensitive adhesive films comprising the said release layer.

[0016] Technical solution

[0017] In this specification, when the measurement temperature affects the relevant physical properties, unless otherwise stated, the physical properties are those measured at room temperature. In this specification, the term room temperature means the natural temperature without artificial heating or cooling, which may mean, for example, any temperature in the range of about 10°C to 30°C, or about 15°C or higher, 18°C ​​or higher, 20°C or higher, or about 23°C or higher while simultaneously about 27°C or lower, or about 23°C, about 25°C, or about 27°C.

[0018] Unless otherwise stated, the unit of temperature mentioned in this specification is °C.

[0019] In this specification, when the measurement pressure affects the relevant physical properties, unless otherwise stated, the physical properties are those measured at atmospheric pressure. In this specification, the term atmospheric pressure means natural pressure without artificial pressurization or depressurization, which may refer to pressure at the level of standard atmospheric pressure, for example, pressure around 740 mmHg to 780 mmHg.

[0020] As used herein, relative humidity is expressed as a percentage (%) of the amount of water vapor contained in a unit volume of current air to the maximum saturated vapor pressure that the unit volume of air can contain, and may be expressed as RH%. When relative humidity affects physical properties mentioned herein, unless otherwise stated, the relevant physical properties are those measured in a humid environment (approximately 30% to 70% RH).

[0021] As used in this application, the term "a to b" means "within the range of a to b, including both a and b". For example, the fact that it includes a parts by weight to b parts by weight has the same meaning as including the range of a parts by weight to b parts by weight.

[0022] 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, wherein there is no particular limitation on the position to be substituted, as long as it is the position where the hydrogen atom is substituted (i.e., the position where the substituent can be substituted), and when two or more substituents are substituted, the substituents may be the same as or different from each other.

[0023] Unless otherwise specified, the alkyl or alkoxy group referred to in this specification may be a linear or branched alkyl or alkoxy group having 1 to 20 carbon atoms, or 1 to 16 carbon atoms, or 1 to 12 carbon atoms, or 1 to 8 carbon atoms, or 1 to 6 carbon atoms, or a cyclic alkyl or alkoxy group having 3 to 20 carbon atoms, or 3 to 16 carbon atoms, or 3 to 12 carbon atoms, or 3 to 8 carbon atoms, or 3 to 6 carbon atoms. Here, cyclic alkyl or alkoxy groups also include alkyl or alkoxy groups having only a cyclic structure and alkyl or alkoxy groups containing a cyclic structure. For example, cyclohexyl and methylcyclohexyl both correspond to cyclic alkyl groups.

[0024] In this application, alkylene refers to a divalent residue formed by removing two hydrogen atoms from an alkane. In the case of alkylene, it is a structure in which two hydrogen atoms are removed from different carbon atoms of the alkane one by one, and alkylidene is a structure in which two hydrogen atoms are removed from one carbon atom of the alkane. Unless otherwise stated, alkylidene as mentioned in this specification can be a linear or branched alkylidene having 1 to 20 carbon atoms, or 1 to 16 carbon atoms, or 1 to 12 carbon atoms, or 1 to 8 carbon atoms, or 1 to 6 carbon atoms, or can be a cyclic alkylidene 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. Cyclic alkylidene also includes alkylidene having only a ring structure and alkylidene containing a ring structure. Unless otherwise specified, the alkylene groups mentioned in this specification may be linear or branched acyclic alkylene groups having 2 to 20 carbon atoms, or 2 to 16 carbon atoms, or 2 to 12 carbon atoms, or 2 to 8 carbon atoms, or 2 to 6 carbon atoms, or cyclic alkylene groups 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. Herein, cyclic alkylene groups include alkylene groups having only a cyclic structure and alkylene groups containing a cyclic structure.

[0025] Unless otherwise specified, the alkenyl or alkenyl groups mentioned in this specification can be linear or branched acyclic alkenyl or alkenyl groups having 2 to 20 carbon atoms, or 2 to 16 carbon atoms, or 2 to 12 carbon atoms, or 2 to 8 carbon atoms, or 2 to 6 carbon atoms, or can be cyclic alkenyl or alkenyl groups 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. Cyclic alkenyl or alkenyl groups also include alkenyl or alkenyl groups having only a ring structure and alkenyl or alkenyl groups containing a ring structure.

[0026] Unless otherwise specified, the ynyl or ynylene group mentioned in this specification can be a linear or branched acyclic ynyl or ynylene group having 2 to 20 carbon atoms, or 2 to 16 carbon atoms, or 2 to 12 carbon atoms, or 2 to 8 carbon atoms, or 2 to 6 carbon atoms, or a cyclic ynyl or ynylene 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. Here, if an ynyl or ynylene group with a cyclic structure is included, it corresponds to a cyclic ynyl or ynylene group.

[0027] Alkyl, alkoxy, alkylidene, alkylene, alkenyl, alkenylene, ynyl, and ynylene groups may also be substituted by any one or more substituents. In this case, the substituents may be selected from, but are not limited to, one or more of halogens (chlorine (Cl), iodine (I), bromine (Br), fluorine (F)), aryl, heteroaryl, epoxy, alkoxy, cyano, carboxyl, acryloyl, methacryloyl, acryloyloxy, methacryloyloxy, carbonyl, and hydroxyl groups.

[0028] In this specification, the term aryl means a substituent formed by removing a hydrogen atom from an aromatic cyclic compound, which may be a monocyclic or polycyclic compound. There is no particular limitation on the number of carbon atoms in an aryl group, but unless otherwise stated, an aryl group may have 6 to 20 carbon atoms, 6 to 18 carbon atoms, or 2 to 15 carbon atoms.

[0029] The term arylene as used in this specification refers to a divalent functional group in which an additional hydrogen atom has been removed from an aryl group. The description of aryl groups as described above can be applied in the same manner, except that these groups are each divalent. Aryl groups can be exemplified as phenyl, phenylethyl, phenylpropyl, benzyl, tolyl, xylyl, or naphthyl, but are not limited thereto.

[0030] In this application, the term heteroaryl refers to a functional group having a structure in which one or more carbon atoms constituting the aryl aromatic ring are replaced by heteroatoms other than carbon atoms. Here, heteroatoms may be exemplified as nitrogen (N), oxygen (O), sulfur (S), selenium (Se), or tellurium (Te). The atoms constituting the ring structure of the heteroaryl may be referred to as ring atoms. Furthermore, heteroaryl may comprise monocyclic or polycyclic compounds. There is no particular limitation on the number of carbon atoms or ring atoms in a heteroaryl, but it can be in the range of 2 to 30, 2 to 26, 2 to 22, 2 to 20, 2 to 18, or 2 to 15. In another example, there is no particular limitation on the number of ring atoms in a heteroaryl, but for example, a heteroaryl may be a heteroaryl having 5 to 30, 5 to 25, 5 to 20, 5 to 15, 5 to 10, or 5 to 8 ring atoms. Heteroaryl groups can be exemplified as, for example, thienyl, furanyl, pyrroleyl, imidazolyl, thiazolyl, etc. azole group, Diazolyl, Triazolyl, Pyridyl, Bipyridyl, Pyrimidinyl, Triazinyl, Acridineyl, Pyridazinyl, Quinolinyl, Quinazolinyl, Quinoxalinyl, Phtharazineyl, Pyridopyrimidinyl, Pyridopyrazinyl, Pyrazenopyrazinyl, Isoquinolinyl, Indoleyl, Carbazoleyl, Benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, dibenzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, dibenzofuranyl, benzothiopyrrolyl, dibenzothiopyrrolyl, phenanthrolinel, iso azole group, thiadiazole group, phenthiazin group, phen Zine groups, as well as the aforementioned fused structures, etc., but not limited to these.

[0031] Furthermore, as used in this application, the term heteroaryl means a divalent group in which a hydrogen atom is further removed from a heteroaryl group. The description of heteroaryl groups as described above can be applied, except that these are divalent groups.

[0032] The aryl or heteroaryl group may also optionally be substituted with one or more substituents. In this case, the substituent may be selected from, but is not limited to, one or more of halogens (chlorine (Cl), iodine (I), bromine (Br), fluorine (F)), aryl, heteroaryl, epoxy, alkoxy, cyano, carboxyl, acryloyl, methacryloyl, acryloyloxy, methacryloyloxy, carbonyl, and hydroxyl.

[0033] This application provides compounds having specific structures. In one example, the compound may be a compound containing silicon atoms therein bonded with radical-generating functional groups.

[0034] For example, the compound may be a compound comprising a chain consisting of silicon atoms linked by linking groups and functional groups generated by free radicals linked to silicon atoms present in the chain.

[0035] Such compounds can be represented, for example, by the average unit of Formula 1.

[0036] [Formula 1]

[0037] R 1 m R 2 n SiX (4-m-n) / 2

[0038] In Equation 1, R 1 It can generate functional groups for free radicals, R 2 It can be hydrogen, isocyanate alkyl, hydroxyalkoxy, alkoxy, or monovalent hydrocarbon group, and X can be a linking group that connects the silicon atoms of the compound to each other.

[0039] In Equation 1, m can be a number in the range of 1 to 3, n can be a number in the range of 0 to 2, and the sum of m and n (m+n) can be a number in the range of 1 to 3.

[0040] In this specification, the term "average unit" refers to a formula expressed by converting the molar number of functional groups (functional groups directly bonded to silicon atoms) and linking groups (linking groups that connect silicon atoms to silicon atoms) in a compound, based on the fact that the molar number of silicon atoms contained in the compound is considered as 1 mole. Such an average unit can be applied to a monomolecular compound or a mixture of bimolecular or higher-order compounds. When the average unit is applied to a mixture of bimolecular or higher-order compounds, the ratio of other functional groups or linking groups is calculated by assuming that the total molar number of silicon atoms contained in the mixture is 1.

[0041] In Equation 1, R to the left of the silicon atom (Si) 1 and R 2 The symbol represents a functional group that is directly connected to a silicon atom, and the X on the right represents a linking group that connects silicon atoms to silicon atoms.

[0042] In Equation 1, m is the functional group R transformed by assuming that the number of silicon atoms contained in the compound is 1 mole. 1 The number of moles, and n is the functional group R converted by assuming that the number of silicon atoms contained in the compound is 1 mole. 2 The number of moles.

[0043] Furthermore, in Formula 1, (4-mn) represents the number of moles of the linking group X, converted by assuming that the compound contains 1 mole of silicon atoms. In the case of the linking group X, two silicon atoms are bonded to it, so the number of moles is represented by dividing the number of moles by 2.

[0044] This representation is similar to the method used to represent the average unit of a so-called polyorganosiloxane.

[0045] In Formula 1, the linking group X can be an oxygen atom or a divalent linking group of Formula 2 below.

[0046] [Equation 2]

[0047] -O-L1-O-

[0048] In Formula 2, L1 can be an alkylene group or an alkylidene group.

[0049] The specific types of alkylene or alkylidene groups in Formula 2 are illustrated at the beginning of this specification.

[0050] In Equation 2, the oxygen atoms on both sides of L1 are directly connected to the silicon atoms of the compound.

[0051] As described below, the compound is obtained by introducing a desired functional group (R) into it. 1 The alkoxysilane (e.g., alkoxysilane) is produced by reacting it with a diol compound that forms the linking group of Formula 2 above. In this case, the alkoxy group of the alkoxysilane reacts with the hydroxyl group of the diol compound, thereby yielding a structure in which the silicon atom of the alkoxysilane is linked by the linking group of Formula 2 above. In such a reaction, a siloxane bond in which the silicon atom is bonded to the silicon atom via an oxygen atom can also be generated through a condensation reaction between the alkoxy groups of the alkoxysilane. Therefore, in Formula 1, X can be an oxygen atom or a divalent linking group from Formula 2 above.

[0052] In one example, all or more of the linking groups X contained in a compound having an average unit of Formula 1 can be linking groups of Formula 2. For example, based on the total number of moles of linking groups X contained in the compound, the lower limit of the ratio of the number of moles of linking groups of Formula 2 above can be approximately 70 mol%, 75 mol%, 80 mol%, 85 mol%, 90 mol%, 95 mol%, or 97 mol%, and its upper limit can be approximately 100 mol%. This ratio can be greater than or equal to or greater than any of the aforementioned lower limits, or it can be less than or equal to or less than any of the aforementioned upper limits while being greater than or equal to or greater than any of the aforementioned lower limits.

[0053] In Equation 1, R 1Free radical generating functional groups. The term free radical generating functional group refers to a functional group that contains a portion capable of generating free radicals by applying energy, such as light or heat, and there is no restriction on the type of such functional group, as long as it can generate free radicals.

[0054] In Equation 1, R 2 It can be hydrogen, isocyanate alkyl, hydroxyalkoxy, alkoxy, or a monovalent hydrocarbon group.

[0055] R in Equation 1 2 The specific types of alkyl groups and alkoxy groups contained in the isocyanate alkyl and hydroxyalkoxy groups are as described at the beginning of this specification.

[0056] Furthermore, the term "monovalent hydrocarbon" is used herein to refer 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, alkenyl, ynyl, or aryl groups. Specific examples of such alkyl, alkenyl, ynyl, or aryl groups are described at the beginning of this specification.

[0057] As described below, the compound can be introduced into a radical-generating functional group (R) in the presence of a diol compound. 1 The product is produced by the reaction of alkoxysilanes (e.g., alkyl groups), and the introduction of radical-generating functional groups can be carried out by the urethane reaction of alkoxysilane compounds having isocyanate alkyl groups. In this case, theoretically, all isocyanate alkyl groups contained in the alkoxysilane compound are converted into radical-generating functional groups, and all alkoxy groups in the alkoxysilane compound are converted into linking groups (oxygen atoms or linking groups of formula 2). However, isocyanate alkyl groups that do not participate in the urethane reaction may remain in the final compound, as well as alkoxy groups that fail to form linking groups and / or alkoxy groups that react with diol compounds but do not form linking groups (these alkoxy groups exist in the form of hydroxyalkoxy groups) may be retained. Furthermore, hydrogen or monovalent hydrocarbon groups that do not participate in the urethane reaction and linking group formation reaction may be present in the alkoxysilane compound.

[0058] Therefore, R in Equation 1 2 It can be hydrogen, isocyanate alkyl, hydroxyalkoxy, alkoxy, or a monovalent hydrocarbon group.

[0059] In Equation 1, m can be a number in the range of 1 to 3, 1 to 2.5, 1 to 2, 1 to 1.5, or approximately 1.

[0060] In Equation 1, n can be a number in the range of 0 to 2, 0 to 1.5, or 0 to 1.

[0061] The sum of m and n in Formula 1 (m+n) can be a number in the range of 1 to 3, 1.5 to 3, 2 to 3, or 2.5 to 3.

[0062] In one instance, the free radical of Equation 1 generates the functional group R. 1 It can be a functional group represented by the following formula 3.

[0063] [Formula 3]

[0064]

[0065] In Formula 3, L2 and L3 can each be alkylene or alkylidene groups independently, and R3 can be aryl or heteroaryl.

[0066] Specific examples of the alkylene and alkylidene groups of L2 and L3 in Formula 3 are as described at the beginning of this specification, as are specific examples of the aryl or heteroaryl groups of R3.

[0067] In Formula 3, L2 is directly connected to the silicon atoms of the compound.

[0068] In one instance, L2 and L3 in Formula 3 can each be an alkylene group independently, and R3 can be an aryl group.

[0069] The functional group of Formula 3 has a structure in which oxygen atoms are located on both sides of L3. Due to the high electronegativity of oxygen atoms, the carbon-carbon bonds or carbon-oxygen bonds in the -O-L3-C(=O)- structure have relatively weak bond strength. Therefore, when the bonds are broken by external energy, such as light irradiation or heat, free radicals can be generated.

[0070] The compound can have a branched structure, a cage structure, or a partially cage structure. This branched structure, cage structure, or partially cage structure is essentially the same as the branched structure, cage structure, or partially cage structure mentioned for so-called polyorganosiloxanes. The difference lies in the fact that, in the case of polyorganosiloxanes, the linking group connecting silicon atoms in the above structure is an oxygen atom, but in the case of the above compound, the linking group (X in Formula 1) is an oxygen atom or the linking group in Formula 2.

[0071] This compound can be a high molecular weight compound. Therefore, it can have a molecular weight higher than a certain level. For example, the lower limit of the weight-average molecular weight of the above compounds can be 5,000 g / mol, 6,000 g / mol, 7,000 g / mol, 8,000 g / mol, 9,000 g / mol, 10,000 g / mol, 15,000 g / mol, 20,000 g / mol, 25,000 g / mol, 30,000 g / mol, 35,000 g / mol, 40,000 g / mol, 45,000 g / mol, or 50,000 g / mol. The weight-average molecular weight of the compound can 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 approximately 50,000 g / mol. The weight-average molecular weight of the compound can be less than or equal to or less than any of the above upper limits, or greater than or equal to or greater than any of the above lower limits, or can have a range greater than or equal to or greater than any of the above lower limits while being less than or equal to or less than any of the above upper limits.

[0072] The compound may possess a certain level of polydispersity index. The polydispersity index is the value obtained by dividing the compound's weight-average molecular weight (Mw) by its number-average molecular weight (Mn) (Mw / Mn). The lower limit of the polydispersity index can be approximately 1, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2, or 2.1, and its upper limit can be approximately 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 or less than any of the above upper limits, or may be greater than or equal to or greater than any of the above lower limits, or may have a range greater than or equal to or greater than any of the above lower limits while being less than or equal to or less than any of the above upper limits.

[0073] Since such compounds are contained in the release layer to form a unique cross-linked structure, the desired release layer can be provided in this application.

[0074] Such compounds can be synthesized using known methods, such as those used to produce polyorganosiloxanes.

[0075] In methods for synthesizing polyorganosiloxanes, it is known to form polyorganosiloxanes by using alkoxysilanes as monomers and performing a condensation reaction of the alkoxysilanes. In this application, the condensation reaction of the polyorganosiloxane is carried out in the presence of a diol compound. In this case, the linking group of Formula 2 can be formed by the reaction between the hydroxyl group of the diol compound and the alkoxy group of the alkoxysilane. Furthermore, compounds having the average unit of Formula 1 above can be formed by applying the above R... 1 and / or R 2 The compound was synthesized as an alkoxysilane used in condensation reactions.

[0076] In the above process, the above R 1 and / or R 2 Functional groups, especially the above R 1 There are no particular limitations on the method of introducing functional groups into alkoxysilanes. For example, in commercially available alkoxysilanes, those having the above R... 1 and / or R 2 The functional group and the alkoxy group are alkoxysilanes. Alternatively, the functional group can be introduced into the alkoxysilane by a separate reaction. For example, when an alkoxysilane having an isocyanate group is used as an alkoxysilane and it reacts with a radical-generating compound having a hydroxyl group, the radical-generating portion of the radical-generating compound can be introduced into the alkoxysilane by a carbamate reaction or the like.

[0077] An example of such a method for synthesizing the above compounds is described in Preparation Example 1 of this specification.

[0078] In Preparation Example 1, an isocyanate compound having an alkoxysilyl group (an alkoxysilane having an isocyanate group) is first reacted with a radical-generating compound having a hydroxyl group to obtain an alkoxysilane (intermediate product) in which a radical-generating moiety of the radical-generating compound is introduced. Here, commercially available compounds can be used as the isocyanate compound having an alkoxysilyl group, and commercially available compounds (e.g., compounds having a hydroxyl group among compounds called radical initiators) can be used as the radical-generating compound.

[0079] If desired, the reaction to obtain the intermediate product can be carried out by adding a catalyst, at a predetermined temperature, and for a predetermined time. Subsequently, the intermediate product can be further reacted in the presence of a polyol (diol compound) to obtain the target compound. Additional reactions can also be carried out at a predetermined temperature and for a predetermined time. The temperature and time can be adjusted considering factors such as the yield of the reacting compound and the target compound. For example, the predetermined temperature can be in the range of 60°C to 150°C, and the predetermined time can be in the range of 1 hour to 7 hours, but is not limited to these.

[0080] As described above, as a free radical generating compound used in the above reactions, for example, a compound containing a hydroxyl group can be used, which is known to generate free radicals. An example of such a compound is a free radical initiator having both a hydroxyl and a ketone group. As such a free radical initiator, one or more selected from 2-hydroxy-2-methyl-1-phenyl-1-propanone, 1-hydroxycyclohexylphenyl ketone, 4-(2-hydroxyethoxy)phenyl-2-(hydroxy-2-propyl) ketone, and oligomeric [2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]propanone] can be used, but are not particularly limited thereto. Furthermore, the free radical generating compound may contain one or more functional groups selected from aryl and heteroaryl groups. When the free radical generating compound contains aryl and / or heteroaryl groups, polymerization is initiated without decomposition, thereby forming a compound capable of post-curing and reducing unreacted products.

[0081] There are no particular restrictions on the type of isocyanate compound containing an alkoxysilyl group, as long as it is a compound containing both an alkoxysilyl group and an isocyanate group at the end. For example, an alkylene group having 1 to 20 carbon atoms may be bonded between the silicon atom (Si) of the alkoxysilyl group and the nitrogen atom (N) of the isocyanate. In another example, the upper limit for the number of carbon atoms can be approximately 19, 18, 17, 16, 15, 14, 13, 12, 11, 10, 9, 8, 7, 6, 5, 4, or 3. The number of carbon atoms may be less than or equal to, or less than any of the above upper limits, but is not limited thereto.

[0082] Furthermore, isocyanate compounds having an alkoxysilyl group may have at least one or more alkoxysilyl groups, and the alkoxy group bonded to the silicon atom (Si) in the alkoxysilyl group may be an alkoxy group having 1 to 20 carbon atoms. The upper limit for the number of carbon atoms may be approximately 19, 18, 17, 16, 15, 14, 13, 12, 11, 10, 9, 8, 7, 6, 5, 4, or 3. The number of carbon atoms may be less than or equal to, or less than any of the above upper limits, and for example, 3-(triethoxysilyl)propyl isocyanate, 3-(trimethoxysilyl)propyl isocyanate, 3-(triethoxysilyl)ethyl isocyanate, 3-(triethoxysilyl)butyl isocyanate, or 3-(triethoxysilyl)methyl isocyanate, etc., may be used as isocyanate compounds having an alkoxysilyl group.

[0083] The intermediate used to synthesize this compound can be obtained by reacting a composition comprising an isocyanate compound having an alkoxysilyl group as described above and a radical-generating compound. In this case, the ratio of each reactive compound in the composition can be adjusted with consideration of the desired compound structure.

[0084] For example, relative to the total weight of the composition, the lower limit of the content of the free radical generating compound in the composition can be approximately 10 wt%, 12.5 wt%, 15 wt%, 17.5 wt%, 20 wt%, 22.5 wt%, 25 wt%, 27.5 wt%, 30 wt%, 32.5 wt%, or 35 wt%, and the upper limit can be approximately 50 wt%, 48 wt%, 46 wt%, 44 wt%, 42 wt%, or 40 wt%. This ratio can be less than or equal to or less than any of the above upper limits, or greater than or equal to or greater than any of the above lower limits, or can have a range greater than or equal to or greater than any of the above lower limits while being less than or equal to or less than any of the above upper limits. When the composition forming the intermediate product contains the above compounds in the above amounts, a compound capable of forming a release layer can be provided, the release layer having excellent film-forming properties, an appropriate level of release peel strength and excellent residual adhesion, and minimal variation in release peel strength caused by external factors such as heat and ultraviolet radiation.

[0085] In this composition, the lower limit of the weight parts of the isocyanate compound having an alkoxysilyl group relative to 100 parts by weight of the radical-generating compound can 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 can 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. This ratio can be less than or equal to or less than any of the above upper limits, or it can be greater than or equal to or greater than any of the above lower limits, or it can have a range greater than or equal to or greater than any of the above lower limits while being less than or equal to or less than any of the above upper limits. When the composition forming the intermediate product contains an isocyanate compound having an alkoxysilyl group within the above range, a compound capable of forming a release layer can be formed, which facilitates the formation of a coating film by exhibiting excellent cohesiveness, has an appropriate level of release peel force and excellent residual adhesion by exhibiting appropriate elasticity and hydrophilicity, and has minimized variations in release peel force caused by external factors such as heat and ultraviolet radiation.

[0086] The reaction that forms the intermediate product can be carried out in the presence of a suitable catalyst, such as a carbamate catalyst. Such catalysts can be exemplified by, for example, tertiary amine compounds, aprotic salts, or organometallic compounds, and specifically, organotin-based catalysts such as dibutyltin dilaurate (DBTDL) can be used, but are not limited thereto.

[0087] The lower limit of the catalyst content relative to 100 parts by weight of the composition for forming the intermediate product can be 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. Approximately 18 parts by weight, 0.2 parts by weight, 0.22 parts by weight, or 0.24 parts by weight, with an upper limit of approximately 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 or less than any of the above upper limits, or may be greater than or equal to or greater than any of the above lower limits, or may be greater than or equal to or greater than any of the above lower limits while being less than or equal to or less than any of the above upper limits.

[0088] The intermediate obtained by reacting the composition can be condensed in the presence of a polyol (diol compound) to prepare a compound represented by the average unit of Formula 1 above.

[0089] Polyols are compounds that have two or more hydroxyl groups in their molecules. Furthermore, the type of polyol is not particularly limited as long as it has two or more hydroxyl groups in its molecule, and for example, (poly)ethylene glycol, diethylene glycol, (poly)propylene glycol, 1,2-butanediol, 2,3-butanediol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 1,6-hexanediol, neopentyl glycol, 1,2-ethylhexyl glycol, 1,5-pentanediol, 1,9-nonanediol, 1,10-decanediol, 1,3-cyclohexanediol and 1,4-cyclohexanediol, (poly)ethylenetriol, diethylenetriol, (poly)propylenetriol, glycerol, 1,2,3-butanetriol, 1,2,4-butanetriol, 1,3,4-hexanetriol, 1,3,6-hexanetriol, trimethylolpropane and 2,2-dimethyl-1,3-propanediol, etc., but not particularly limited thereto, can be used.

[0090] The amount of polyol used can also be adjusted considering the structure of the target compound. For example, relative to 100 parts by weight of the intermediate product, the lower limit of the polyol by weight can be approximately 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, or 0.9 parts by weight, and its upper limit can be approximately 5, 4.5, 4 or less, 3.5, 3, 2.5, 2, 1.5, or 1 part by weight. The polyol can be less than or equal to or less than any of the above upper limits, or greater than or equal to or greater than any of the above lower limits, or greater than or equal to or greater than any of the above lower limits while being less than or equal to or less than any of the above upper limits.

[0091] There are no particular restrictions on the methods for carrying out condensation reactions; they can be carried out in a known manner.

[0092] This application also relates to release compositions comprising the above-mentioned compounds. The term release composition means a composition capable of forming a release layer, and in this case, the meaning of release layer is known in the industry.

[0093] The release composition can be a curable composition, and in this case, the composition can form a release layer before or after curing.

[0094] When the release composition is curable, it can be an active energy ray (e.g., ultraviolet) curable, moisture-curable, thermosetting, or room temperature curable composition, and in some cases, it can be a mixture of two or more of the foregoing. When the release composition is an active energy ray curable composition, curing can be carried out by irradiation with an active energy ray such as ultraviolet light; when the release composition is a moisture-curable composition, curing can be carried out by maintaining it at a suitable humidity; in the case of a thermosetting composition, curing can be carried out by applying appropriate heat thereto; or in the case of a room temperature curable composition, curing can be carried out by maintaining the release composition at room temperature.

[0095] The lower limit of the content of the compound having the average unit of Formula 1 above in the release composition may be about 0.01 wt%, 0.05 wt%, 0.1 wt%, 0.5 wt%, 1 wt%, 5 wt%, 7 wt%, 9 wt%, 10 wt%, 11 wt%, 13 wt%, or 14 wt%, and the upper limit may be about 40 wt%, 39 wt%, 38 wt%, 36 wt%, 34 wt%, 32 wt%, 30 wt%, 28 wt%, 26 wt%, 24 wt%, 22 wt%, 20 wt%, 18 wt%, 16 wt%, 14 wt%, 12 wt%, 10 wt%, 8 wt%, 6 wt%, 4 wt%, 2 wt%, or 1 wt%. This ratio can be less than or equal to any of the upper limits mentioned above, or it can be greater than or equal to any of the lower limits mentioned above, or it can be within a range where it is less than or equal to or less than any of the upper limits mentioned above while being greater than or equal to or greater than any of the lower limits mentioned above. Within the above range, release compositions that can ensure appropriate film-forming ability and release peel strength, excellent residual adhesion, etc., can be provided. This ratio is based on solid content; therefore, when the release composition contains a solvent, it is a ratio to the total weight of the release composition excluding the weight of the solvent. This ratio can also be a ratio of compounds or reactants thereof in the release layer to be described below.

[0096] Release compositions can be solvent-based, water-based, or solvent-free release compositions.

[0097] The release composition may contain the above-mentioned compounds and may also 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.

[0098] In one example, the silicone resin component of the release composition can be a so-called addition-curing component. Such a resin component may contain, for example, a polyorganosiloxane (hereinafter referred to as a first polyorganosiloxane or first polyorganosiloxane component) having an alkenyl group bonded to a silicon atom.

[0099] The first polyorganosiloxane or the first polyorganosiloxane component may have, for example, an average unit of Formula 4 below. Such an average unit may be for a monomolecular polyorganosiloxane or a mixture of bimolecular or higher-order polyorganosiloxanes. When the average unit is for a mixture of bimolecular or higher-order polyorganosiloxanes, the ratio of other functional groups or atoms is calculated by assuming that the total number of moles of silicon atoms contained in the mixture is 1.

[0100] [Formula 4]

[0101] P a Q b SiO (4-a-b) / 2

[0102] In Formula 4, P can be an alkenyl group, Q can be an alkoxy group, a hydroxyl group, or a monovalent hydrocarbon group, a can be a number in the range of 0.0001 to 0.1, and b can be a number in the range of 1 to 4.

[0103] In Formula 4, the specific types of alkenyl and alkoxy groups are as described at the beginning of this specification, and the specific types of monovalent hydrocarbon groups are the same as those of monovalent hydrocarbon groups in Formula 1.

[0104] The lower limit of 'a' in Equation 4 can be 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, or 0.012. The range is approximately 0.014, 0.016, 0.018, 0.02, or 0.022, with an upper limit of 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. 'a' can be less than or equal to any of the upper limits mentioned above, or greater than or equal to any of the lower limits mentioned above, or can have a range greater than or equal to any of the lower limits mentioned above while being less than or equal to any of the upper limits mentioned above.

[0105] In Equation 4, the lower limit of b can 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 can be approximately 3.5, 3, 2.9, 2.8, 2.7, 2.6, 2.5, 2.4, 2.2, 2.1, or 2. b can be less than or equal to any of the above upper limits, or greater than or equal to any of the above lower limits, or have a range that is greater than or equal to any of the above lower limits while being less than or equal to any of the above upper limits.

[0106] Polyorganosiloxanes having the average unit of Formula 4 may contain alkenyl groups in the range of 0.01 mol% to 1.5 mol% of all organic groups. For example, based on the molar number of all organic groups in a polyorganosiloxane having the average unit of Formula 4, the lower limit of the molar number of alkenyl groups may be 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%, 0.19 mol%, 0. The percentages are approximately 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%, with upper limits of 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%. This percentage can be less than or equal to any of the upper limits mentioned above, or it can be greater than or equal to any of the lower limits mentioned above, or it can have a range greater than or equal to any of the lower limits mentioned above while being less than or equal to any of the upper limits mentioned above.

[0107] Such a polyorganosiloxane having an average unit of Formula 4 above may contain one or more siloxane units selected from siloxane units of Formula 6 and Formula 7 below.

[0108] [Formula 6]

[0109] ViR 6 2SiO 1 / 2

[0110] [Formula 7]

[0111] ViR 6 SiO 2 / 2

[0112] In formulas 6 and 7, Vi is an alkenyl group, and R... 6 It can be a hydroxyl, alkoxy, or monovalent hydrocarbon group. Here, the specific types of alkenyl, alkoxy, and monovalent hydrocarbon groups are as described in Formula 4.

[0113] When included, based on all siloxane units in the first polyorganosiloxane component, the lower limit of the ratio of siloxane units in Formula 6 above can 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 its upper limit can 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%. This ratio can be less than or equal to, or less than any of the above upper limits, or greater than, or equal to, or greater than any of the above lower limits, or can be within a range where it is less than or equal to, or less than any of the above upper limits and simultaneously greater than, or equal to, or greater than any of the above lower limits.

[0114] When included, based on all siloxane units in the first polyorganosiloxane component, the lower limit of the ratio of siloxane units in Formula 7 above can 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 its upper limit can be approximately 10 mol%, 9 mol%, 8 mol%, 7 mol%, 6 mol%, 5 mol%, 4 mol%, 3 mol%, 2 mol%, or 1 mol%. This ratio can be less than or equal to, or less than any of the above upper limits, or greater than or equal to, or greater than any of the above lower limits, or within a range where it is less than or equal to, or less than any of the above upper limits and simultaneously greater than or equal to, or greater than any of the above lower limits.

[0115] The first polyorganosiloxane component may comprise both the siloxane unit of Formula 6 and the siloxane unit of Formula 7. In this case, the lower limit of the molar ratio of the siloxane unit of Formula 7 to the siloxane unit of 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. This ratio may be less than or equal to, or less than any of the above upper limits, or may be greater than or equal to, or greater than any of the above lower limits, or may be within a range where it is less than or equal to, or less than any of the above upper limits and simultaneously greater than or equal to, or greater than any of the above lower limits.

[0116] The lower limit of the number of silicon atoms in the first polyorganosiloxane component can be approximately 500, 1,500, 2,000, 2,500, or 3,000, and the upper limit can be approximately 10,000, 5,000, 4,000, 3,500, 3,000, 2,500, or 2,100. The number of silicon atoms can be greater than or equal to, or greater than any of the above lower limits, or less than or equal to, or less than any of the above upper limits, or can be within a range where it is less than or equal to, or less than any of the above upper limits while being greater than or equal to, or greater than any of the above lower limits.

[0117] The first polyorganosiloxane component can have a substantially linear structure. In this case, the polyorganosiloxane can consist essentially only of M units (monofunctional siloxane units) and D units (bifunctional siloxane units), or it can contain T units (trifunctional siloxane units) and / or Q units (tetrafunctional siloxane units) as well as M units (monofunctional siloxane units) and D units (bifunctional siloxane units), but can have a structure in which the ratio of T units (trifunctional siloxane units) and / or Q units (tetrafunctional siloxane units) is below a certain level.

[0118] For example, in the first polyorganosiloxane component, the upper limit of the ratio of the total number of moles of T units and Q units contained in the polyorganosiloxane to the total number of moles of all siloxane units (100 × (moles of T units + moles of Q units) / total number of moles of all siloxane units) can 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 its lower limit can be 0 mol%. This ratio can be less than or equal to, or less than any of the above upper limits, or can be within the range of being less than or equal to, or less than any of the above upper limits while being greater than or equal to, or greater than any of the above lower limits.

[0119] The lower limit of the weight-average molecular weight of polyorganosiloxanes having average units of Formula 4 above can 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 can be approximately 1,000,000 g / mol. The weight-average molecular weight can be less than or equal to any of the upper limits mentioned above, or greater than or equal to any of the lower limits mentioned above, or within a range where it is less than or equal to any of the upper limits mentioned above and simultaneously greater than or equal to any of the lower limits mentioned above. Because the polyorganosiloxanes having the average units of Formula 4 above have weight-average molecular weights within the above ranges, appropriate viscosity can be ensured to exhibit excellent coating properties.

[0120] The lower limit of the polydispersity index of polyorganosiloxanes with average units of Equation 4 above can be approximately 1, 1.25, or 1.5, and the upper limit can be approximately 5, 3.5, or 2.5. The polydispersity index can be less than or equal to, or less than any of the above upper limits, or greater than or equal to, or greater than any of the above lower limits, or can be within the range of being less than or equal to, or less than any of the above upper limits while being greater than or equal to, or greater than any of the above lower limits.

[0121] The curable silicone resin component may comprise a polyorganosiloxane having an average unit of Formula 5 (hereinafter referred to as a second polyorganosiloxane or second polyorganosiloxane component) and a polyorganosiloxane having an average unit of Formula 4 as described above. Such an average unit may be used for monomolecular polyorganosiloxanes or mixtures of bimolecular or higher-order polyorganosiloxanes. When the average unit is for a mixture of bimolecular or higher-order polyorganosiloxanes, the ratio of other functional groups or atoms is calculated by assuming that the total number of moles of silicon atoms contained in the mixture is 1.

[0122] [Formula 5]

[0123] H c Q d SiO (4-c-d)2

[0124] In Formula 5, H can be a hydrogen atom, Q can be an alkoxy, hydroxyl, or monovalent hydrocarbon group, c can be a number in the range of 0.01 to 0.9, and d can be a number in the range of 1 to 4. Specific examples of alkoxy or monovalent hydrocarbon groups in Formula 5 are the same as those in Formula 4.

[0125] In Equation 5 above, the lower limit of c can 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 can 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. c can be less than or equal to, or less than any of the above upper limits, or greater than or equal to, or greater than any of the above lower limits, or have a range that is greater than or equal to, or greater than any of the above lower limits while being less than or equal to, or less than any of the above upper limits.

[0126] In Equation 5 above, the lower limit of d can be approximately 0.5, 1, 1.1, 1.2, 1.3, 1.4, 1.5, or 1.6, and its upper limit can be approximately 4, 3.5, 3, 2.5, 2, 1.9, 1.8, 1.7, 1.6, or 1.5. d can be less than or equal to, or less than any of the above upper limits, or greater than or equal to, or greater than any of the above lower limits, or can have a range greater than or equal to, or greater than any of the above lower limits while being less than or equal to, or less than any of the above upper limits.

[0127] Based on the molar number of all organic groups bonded to silicon atoms contained in the average unit of Formula 5, the lower limit of the ratio of the molar number of all hydrogen atoms bonded to silicon atoms contained in the average unit of Formula 5 can be approximately 1 mol%, 5 mol%, 10 mol%, 15 mol%, 20 mol%, 25 mol%, or 30 mol%, and its upper limit can 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%. This ratio can be less than or equal to, or less than, any of the above upper limits, or greater than or equal to, or greater than any of the above lower limits, or within a range where it is less than or equal to, or less than, any of the above upper limits and simultaneously greater than or equal to, or greater than any of the above lower limits. At such ratios, appropriate curability can be ensured, and a release layer with desired peel properties can be formed.

[0128] According to one example of this application, a polyorganosiloxane having an average unit of Formula 5 may contain a siloxane unit of Formula 9.

[0129] [Formula 9]

[0130] HR 6 SiO 2 / 2

[0131] In Equation 9, R 6 It can be a hydroxyl, alkoxy, or monovalent hydrocarbon group. Specific examples of alkoxy or monovalent hydrocarbon groups in Formula 9 are the same as those in Formula 5.

[0132] Based on the total number of moles of siloxane units containing hydrogen atoms bonded to silicon atoms in all siloxane units of the second polyorganosiloxane component, the lower limit of the molar ratio of siloxane units in Formula 9 above can be approximately 85 mol%, 90 mol%, 95 mol%, 96 mol%, 97 mol%, 98 mol%, 99 mol%, or 99.5 mol%, and its upper limit can be approximately 100 mol%. This ratio can be less than or equal to, or less than any of the above upper limits, or greater than or equal to, or greater than any of the above lower limits, or can be within the range of being less than or equal to, or less than any of the above upper limits while being greater than or equal to, or greater than any of the above lower limits.

[0133] Based on all the siloxane units in the second polyorganosiloxane component, the lower limit of the ratio of siloxane units in Formula 9 above can 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 its upper limit can be approximately 85 mol%, 80 mol%, 75 mol%, 70 mol%, 65 mol%, 60 mol%, 55 mol%, or 50 mol%. This ratio can be less than or equal to, or less than any of the above upper limits, or greater than or equal to, or greater than any of the above lower limits, or within a range where it is less than or equal to, or less than any of the above upper limits while simultaneously greater than or equal to, or greater than any of the above lower limits.

[0134] The lower limit of the number of silicon atoms in the second polyorganosiloxane component can be approximately 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, or 90, and the upper limit can 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 can be greater than or equal to, or greater than any of the lower limits mentioned above, or less than, or less than any of the upper limits mentioned above, or within a range where it is less than or equal to, or less than any of the upper limits mentioned above while being greater than or equal to, or greater than any of the lower limits mentioned above.

[0135] The second polyorganosiloxane component can have a substantially linear structure. In this case, the polyorganosiloxane can consist essentially of only M and D units, or it can contain T and / or Q units as well as M and D units, but can have a structure in which the ratio of T and / or Q units is below a certain level.

[0136] For example, in the second polyorganosiloxane component, the upper limit of the ratio of the total number of moles of T units and Q units in the polyorganosiloxane to the total number of moles of all siloxane units (100 × (moles of T units + moles of Q units) / total number of moles of all siloxane units) can 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 its lower limit can be approximately 0 mol%. This ratio can be less than or equal to, or less than any of the above upper limits, or can be within a range that is less than or equal to, or less than any of the above upper limits while being greater than or equal to, or greater than any of the above lower limits.

[0137] The lower limit of the weight-average molecular weight of polyorganosiloxanes having the average unit of Formula 5 above can 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 can be approximately 100,000 g / mol, 90,000 g / mol, etc. 80,000g / mol, 70,000g / mol, 60,000g / mol, 50,000g / mol, 45,000g / mol, 40,000g / mol, 30,000g / mol, 20,000g / mol, 15,000g / mol, 10,000g / mol, 50,000g / mol, 45,000g / mol, 40,000g / mol, 35,000g / mol, 30,000g / mol, 25,000g / mol, 20,000g / mol, 15,000g / mol, or around 12,000g / mol. The weight-average molecular weight can be greater than or equal to, or greater than any of the lower limits mentioned above, or it can be less than or equal to, or less than any of the upper limits mentioned above, or it can be within the range of being less than or equal to, or less than any of the upper limits mentioned above while being greater than or equal to, or greater than any of the lower limits mentioned above. Since the polyorganosiloxanes having the average units of Formula 5 above have a weight-average molecular weight within the above range, excellent curability can be ensured.

[0138] In polyorganosiloxanes having average units as defined in Formula 5 above, the lower limit of the polydispersity index can be approximately 1, 1.25, or 1.5, and the upper limit can be approximately 5, 3.5, or 2.5. The polydispersity index can be greater than or equal to, or greater than any of the aforementioned lower limits, or it can be less than or equal to, or less than any of the aforementioned upper limits, or it can be within a range where it is less than or equal to, or less than any of the aforementioned upper limits while being greater than or equal to, or greater than any of the aforementioned lower limits.

[0139] The lower limit of the content of polyorganosiloxane having the average unit of Formula 4 above in the curable silicone resin component or release composition may be approximately 50 wt%, 52 wt%, 54 wt%, 56 wt%, 58 wt%, 60 wt%, 62 wt%, 64 wt%, 66 wt%, 68 wt%, 70 wt%, 75 wt%, 80 wt%, 85 wt%, or 90 wt%, and the upper limit may be approximately 98 wt%, 95 wt%, 94 wt%, 93 wt%, 92 wt%, 90 wt%, 85 wt%, or 80 wt%. The ratio may be greater than or equal to, or greater than any of the above lower limits, or may be less than or equal to, or less than any of the above upper limits, or may be within a range where it is less than or equal to, or less than any of the above upper limits while being greater than or equal to, or greater than any of the above lower limits. This ratio is based on the solids content; therefore, when the release composition contains a solvent, this ratio is relative to the total weight of the release composition excluding the solvent. By including a polyorganosiloxane having average units of Formula 4 within the above-described range, an appropriate level of release peel strength and excellent residual adhesion of the release layer, as described below, can be ensured.

[0140] Relative to 100 parts by weight of the polyorganosiloxane having the average unit of Formula 4 above, the lower limit of the weight of the polyorganosiloxane having the average unit of Formula 5 above in the curable silicone resin component or release composition can 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 can be approximately 10 parts by weight, 8 parts by weight, 6 parts by weight, 4 parts by weight, or 3 parts by weight. The ratio can be greater than or equal to, or greater than any of the lower limits above, or less than or equal to, or less than any of the upper limits above, or within a range where it is less than or equal to, or less than any of the upper limits above, and simultaneously greater than or equal to, or greater than any of the lower limits above. When the polyorganosiloxane having the average unit of Formula 5 above is included within the above range, the crosslinking density can be improved to ensure a cured product with excellent durability.

[0141] Relative to 100 parts by weight of a polyorganosiloxane having an average unit of Formula 4 above, the lower limit of the weight of the compound having an average unit of Formula 1 above in the release composition can 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 can 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 ratio can be greater than or equal to, or greater than any of the lower limits mentioned above, or it can be less than or equal to, or less than any of the upper limits mentioned above, or it can be within a range where it is less than or equal to, or less than any of the upper limits mentioned above while being greater than or equal to, or greater than any of the lower limits mentioned above. By adjusting the ratio of compounds having the average unit of Formula 1 above, the desired release layer can be formed more effectively.

[0142] The release composition may contain the above components, and may optionally contain additional components if necessary.

[0143] For example, the release composition may also contain a compound of formula 10.

[0144] [Formula 10]

[0145]

[0146] In Formula 10, R1 can be a group containing a double bond, and R2 to R4 can each be an alkyl group independently.

[0147] By applying the compound of Formula 10, a release composition with excellent film-forming properties can be formed, and such a release composition can form a release layer with excellent bonding properties to the base material, an appropriate level of release peel force and excellent residual adhesion, and minimized variation in release peel force caused by external factors such as heat and ultraviolet radiation.

[0148] Specific examples of the alkyl groups R2 to R4 in Formula 10 are described at the beginning of this specification.

[0149] Furthermore, there is no particular limitation on the specific type of the double-bonded group in Formula 10. For example, the double-bonded group can be exemplified as alkenyl or (meth)acryloyloxyalkyl. Here, the specific type of alkyl group in alkenyl and (meth)acryloyloxyalkyl is as described at the beginning of this specification.

[0150] When included, the lower limit of the content of the compound of Formula 10 relative to 100 parts by weight of the compound having the average unit of Formula 1 above can 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 can 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 ratio can be greater than or equal to, or greater than any of the lower limits mentioned above, or it can be less than or equal to, or less than any of the upper limits mentioned above, or it can be within a range where it is less than or equal to, or less than any of the upper limits mentioned above while being greater than or equal to, or greater than any of the lower limits mentioned above. By adjusting the ratio of the compound as described above, the desired release layer can be formed more effectively.

[0151] In another example, when included, the lower limit of the weight parts of the compound of formula 10 relative to 100 parts by weight of the polyorganosiloxane having the average unit of formula 4 above can 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 can be approximately 10 parts by weight, 8 parts by weight, 6 parts by weight, 4 parts by weight, or 3 parts by weight. The ratio can be greater than or equal to, or greater than any of the lower limits mentioned above, or less than or equal to, or less than any of the upper limits mentioned above, or within a range where it is less than or equal to, or less than any of the upper limits mentioned above while being greater than or equal to, or greater than any of the lower limits mentioned above. By adjusting the ratio of the compound as described above, the desired release layer can be formed more effectively.

[0152] Considering curability, the release composition of this application may further contain a metal catalyst if necessary. The metal catalyst may include one or more of the following as the central metal element: aluminum, bismuth, lead, mercury, tin, zinc, platinum, silver, and zirconium. For example, bis[1,3-bis(2-vinyl)-1,1,3,3-tetramethyldisiloxane]platinum (CAS No. 81032-58-8), dibutyltin dilaurate, or dimethyltin diacetate can be used as the metal catalyst, but are not particularly limited thereto. For example, catalysts industrially known as so-called addition-curing catalysts can be used.

[0153] Relative to 100 parts by weight of a polyorganosiloxane having an average unit of Formula 4 above, the lower limit of the weight of the metal catalyst can 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 can 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 ratio can be greater than or equal to, or greater than any of the above lower limits, or less than or equal to, or less than any of the above upper limits, or within a range where it is less than or equal to, or less than any of the above upper limits while simultaneously greater than or equal to, or greater than any of the above lower limits. By using a catalyst within the above range, side reactions can be reduced while effectively promoting the formation of the cured product.

[0154] Furthermore, the release composition according to one example of this application may also contain a solvent.

[0155] Considering the composition of the release composition, the solvent can be a suitable organic solvent. There are no particular limitations on the organic solvent, as long as it is commonly used in industry, and solvents such as tetrahydrofuran, methyl ethyl ketone, toluene, and heptane, or mixtures thereof, can be used. Furthermore, there are no particular limitations on their mixing ratios, and they can be appropriately formulated as needed.

[0156] The amount of solvent can be adjusted as needed, and there are no particular limitations.

[0157] This application also relates to release layers. Release layers may contain the above-described release composition or its cured product.

[0158] Therefore, the release layer may contain a compound having an average unit of Formula 1 above, or a reactant thereof, and if necessary, may contain a curable silicone resin component as described above, a reactant of the curable silicone resin component, and / or a compound of Formula 10 or a reactant of a compound of Formula 10 above. Furthermore, the release layer can be formed by curing the release composition according to one example of this application described above. As described above, curing can be carried out appropriately according to various methods. Additionally, the release layer may contain the components remaining after curing the release composition according to one example of this application described above.

[0159] The release layer can satisfy at least one of the following physical properties by containing a release composition or its cured product.

[0160] For example, the release layer may have a peel force variation rate AR within a predetermined range according to the following Equation 1. For example, the upper limit of AR may be approximately 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 approximately 0%, 5%, or 10%. AR may be less than or equal to, or less than any of the above upper limits, or may be within a range that is less than or equal to, or less than any of the above upper limits, while being greater than or equal to, or greater than any of the above lower limits.

[0161] [Equation 1]

[0162] AR = 100 × |A2 - A1| / A1

[0163] In Equation 1, A1 is the release peel force measured at 25°C with a peel angle of 180 degrees and a peel speed of 0.3 m / min after the release layer is held at 25°C and attached to the pressure-sensitive adhesive layer for 24 hours, and A2 is the release peel force measured at 25°C with a peel angle of 180 degrees and a peel speed of 0.3 m / min after the release layer is attached to the pressure-sensitive adhesive layer, subjected to ultraviolet irradiation and held at 60°C for 24 hours, and then at 25°C with a peel angle of 180 degrees and a peel speed of 0.3 m / min.

[0164] The release peel force A2 can be the release peel force measured after the sample is first irradiated with ultraviolet light and then kept at 60°C for 24 hours (A21), or it can be the release peel force measured by irradiating with ultraviolet light after the sample is kept at 60°C for 24 hours (A22).

[0165] In Equation 1, |A2-A1| represents the absolute value of the difference between A2 and A1.

[0166] The specific measurement method for the rate of change of peel force AR in Equation 1 (the measurement method for release peel forces A1 and A2) is described in the Examples section.

[0167] The release layer may also have a residual adhesion rate Ad within a predetermined range according to Equation 2 below. For example, the lower limit of the residual adhesion rate 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%. Ad may be greater than or equal to, or greater than, any of the aforementioned lower limits, or may be within a range that is less than or equal to, or less than, any of the aforementioned upper limits, while simultaneously being greater than or equal to, or greater than, any of the aforementioned lower limits. When a release layer according to an embodiment of this application has a residual adhesion rate (Ad) that satisfies the above range, it may be said to have an excellent (or appropriate) residual adhesion rate.

[0168] [Equation 2]

[0169] Ad = 100 × Af / Ai

[0170] In Equation 2, Ai is the release peel force measured while the pressure-sensitive adhesive tape is attached to the release layer and peeled off at 25°C with a peel angle of 180 degrees and a peel rate of 0.3 m / min, and Af is the release peel force measured while the pressure-sensitive adhesive tape is attached to the release layer for which the peel force Ai is measured in the same manner as when the peel force Ai is measured and peeled off at 25°C with a peel angle of 180 degrees and a peel rate of 0.3 m / min.

[0171] The specific method for measuring the residual adhesion rate Ad according to Equation 2 above is described in the Examples section of this specification.

[0172] In a release layer according to one embodiment of this application, the release peel force, measured at room temperature (approximately 25°C) with a peel angle of 180 degrees and a peel rate of 0.3 m / min after being attached to a pressure-sensitive adhesive tape and left at room temperature (approximately 25°C) for 24 hours, is within a predetermined range. For example, the lower limit of the release peel force may be approximately 5 gf / inch, and its 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 peel force may be less than or equal to, or less than any of the above upper limits, or may be within the range of being less than or equal to, or less than any of the above upper limits while being greater than or equal to, or greater than any of the above lower limits. When a release layer according to one embodiment of this application has a release peel force (placed at room temperature) that satisfies the above range, it can be said to have excellent (or appropriate) residual adhesion.

[0173] Furthermore, in the release layer of one example according to this application, it is attached to a pressure-sensitive adhesive tape and then exposed to ultraviolet light with a wavelength of about 150 nm at 3 J / m. 2After irradiation with light for approximately 60 seconds and subsequent maintenance at 60°C for 24 hours, the release peel force, measured at room temperature (approximately 25°C) with a peel angle of 180 degrees and a peel rate of 0.3 m / min, is within a predetermined range. For example, the lower limit of the release peel force can be approximately 5 gf / inch, and its upper limit can 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 peel force can be less than or equal to, or less than any of the above upper limits, or can be within a range that is less than or equal to, or less than any of the above upper limits while being greater than or equal to, or greater than any of the above lower limits. When the release layer according to an example of this application has a release peel force (after UV irradiation and high-temperature placement) that satisfies the above range, it can be said to have excellent (or appropriate) residual adhesion. Furthermore, in this case, the release peel force is independent of the order of UV irradiation and high-temperature placement.

[0174] This application also relates to release films.

[0175] Release film may include a base film and release layers attached to one or both sides of the base film.

[0176] The release layer of the release film according to one example of this application is as described above.

[0177] The type of base film for the release film according to one example of this application is not particularly limited. Any base film that is commonly used to form a release film can be used as the base film.

[0178] For example, as a base membrane, PET (poly(ethylene terephthalate)) membrane, PTFE (poly(tetrafluoroethylene)) membrane, PP (polypropylene) membrane, PE (polyethylene) membrane, polyimide membrane, polyamide membrane, COP (cyclic olefin polymer) membrane, polybutene membrane, polybutadiene membrane, vinyl chloride copolymer membrane, polyurethane membrane, ethylene-vinyl acetate membrane, ethylene-propylene copolymer membrane, ethylene-ethyl acrylate copolymer membrane, ethylene-methyl acrylate copolymer membrane and / or polyimide membrane, etc., but not limited to these, can be used.

[0179] Furthermore, the base film can be composed of a single layer or two or more layers laminated together, and in some cases, it may also include functional layers, such as antifouling layers or antistatic layers. Additionally, from the perspective of improving the adhesion of the base material, further surface treatments, such as primer treatments, can be applied to one or both sides of the base material.

[0180] The thickness of the base membrane is selected appropriately according to the application, and there are no particular restrictions. It can typically be formed in thicknesses of 5 μm to 500 μm, 5 μm to 250 μm, or 5 μm to 100 μm.

[0181] The release film of this application can be manufactured in known ways. In one example, the release film of this application can be manufactured by applying a release composition according to an example of this application to one or both sides of a base material and then curing it to form a release layer. Here, the method of applying the release composition is not particularly limited, as long as it is commonly used in industry, including, for example, blade coating, roller coating, or reverse coating. Furthermore, the release layer can be formed after sufficiently removing components that cause bubbles, such as volatile components of the release composition or reaction residues. Moreover, the method of curing the release composition is not particularly limited, and it can be cured by a suitable aging process, or by curing in a suitable high-temperature environment or under light irradiation, as described above.

[0182] There is no particular limitation on the thickness of the release layer contained in the release film, which can be, for example, 10 nm to 10 μm, 10 nm to 1 μm, or 10 nm to 100 nm.

[0183] In addition, this application relates to pressure-sensitive adhesive films.

[0184] According to one embodiment of this application, the pressure-sensitive adhesive film may include the aforementioned release layer and a pressure-sensitive adhesive layer to which the release layer is attached. By including the release layer, the pressure-sensitive adhesive layer can be protected until it is used.

[0185] The release layer of the pressure-sensitive adhesive film according to one example of this application is as described above.

[0186] There are no particular limitations on the pressure-sensitive adhesive that forms the pressure-sensitive adhesive layer of the pressure-sensitive adhesive film according to one example of this application.

[0187] For example, as a pressure-sensitive adhesive forming a pressure-sensitive adhesive layer, pressure-sensitive adhesives using acrylic polymers, silicone-based polymers, polyesters, polyurethanes, polyamides, polyethers, or fluorine-based or rubber-based polymers as base polymers can be appropriately selected and used.

[0188] Beneficial effects

[0189] This application provides compounds, release compositions, release layers, release films, and pressure-sensitive adhesive films. This application provides compounds capable of forming release layers that exhibit appropriate levels of release peel strength and possess excellent adhesion to a base film and excellent solvent resistance. Furthermore, this application provides compounds that, when formed, exhibit a stable residual adhesion rate even when repeatedly applied to pressure-sensitive adhesive layers, etc. This application may also provide release compositions and release layers comprising the aforementioned compounds, as well as release films and pressure-sensitive adhesive films comprising the aforementioned release layers. Attached Figure Description

[0190] Figure 1 The steps for preparing the compound according to one example of this application are briefly illustrated. Detailed Implementation

[0191] The contents of this application will be described in detail below with reference to embodiments and comparative examples, but the contents of this application are not limited to the following embodiments.

[0192] 1. Release peel force

[0193] Samples were prepared by laminating a pressure-sensitive adhesive tape (TESA7475 PV2, TESA) used to measure the peel force of the release layer of each release film of the examples or comparative examples. Attachment was performed by placing the pressure-sensitive adhesive tape on the release layer and then reciprocating the roller three times under a load of 2.5 kg. The samples were held at room temperature (approximately 25°C) or 60°C for 24 hours, and then the release peel force was measured using a physical property measuring device (Cheminstruments, AR-1000) while peeling the pressure-sensitive adhesive tape used to measure the peel force at a peel angle of 180 degrees and a peel rate of 0.3 m / min at room temperature (approximately 25°C).

[0194] 2. Rate of change of release force (AR)

[0195] The rate of change of release peel force AR of each release layer in the embodiments or comparative examples is determined by the following Equation 1.

[0196] [Equation 1]

[0197] AR = 100 × |A2 - A1| / A1

[0198] In Equation 1, A1 is the release peel force measured using a physical property measuring device (Cheminstruments, AR-1000) at room temperature (approximately 25°C) at a peel angle of 180 degrees and a peel rate of 0.3 m / min after the sample, which was manufactured by laminating a pressure-sensitive adhesive tape (TESA7475 PV2, TESA) used for measuring peel force in the same manner as in the release peel force measurement, was kept at room temperature (approximately 25°C) for 24 hours.

[0199] In Equation 1, A2 represents the release peel force measured using a physical property measuring device (Cheminstruments, AR-1000) at room temperature (approximately 25°C) at a peel angle of 180 degrees and a peel rate of 0.3 m / min after a sample prepared by laminating a pressure-sensitive adhesive tape (TESA7475 PV2, TESA) used for peel force measurement in the same manner as in the release peel force measurement, was irradiated with ultraviolet light and held at 60°C for 24 hours. The ultraviolet light used was approximately 150 nm wavelength at a rate of 3 J / m. 2 The light intensity was applied for approximately 60 seconds.

[0200] The release peel force A2 can be the release peel force measured after the sample is first irradiated with ultraviolet light and then kept at 60°C for 24 hours (A21), or it can be the release peel force measured by irradiating with ultraviolet light after the sample is kept at 60°C for 24 hours (A22).

[0201] 3. Residual Adhesion Rate (Ad)

[0202] The residual adhesion rate Ad of the release layer of each release film in the examples or comparative examples is determined according to the following Equation 2.

[0203] [Equation 2]

[0204] Ad = 100 × Af / Ai

[0205] In Equation 2, Ai is the release peel force measured after the sample prepared according to the method for evaluating release peel force is held at room temperature (approximately 25°C) for 24 hours.

[0206] In Equation 2, Af is the release peel force measured after the standard tape (TESA7475, TESA) is reattached to the release layer of the release film after the release force Ai has been measured, in the same manner as when the release force Ai was measured, to prepare the sample, and then the sample is kept at room temperature (about 25°C) for about 24 hours.

[0207] While peeling pressure-sensitive adhesive tape (TESA7475) at room temperature (approximately 25°C) with a peel angle of 180 degrees and a peel rate of 0.3 m / min, the release peel forces Ai and Af were measured using a physical property measuring device (AR-1000, Cheminstruments) in the same manner as in the release peel force measurement method.

[0208] 4. Solvent resistance assessment method

[0209] The release layer of each release film of the examples or comparative examples is irradiated with ultraviolet light, and kept at 60°C for 24 hours. The ultraviolet irradiation is performed in the same manner as that for measuring the release peeling force A2 of the above Equation 1. Subsequently, using a No. 542-AB device (Yasauda), a cloth soaked in toluene is reciprocated until the release layer falls off. At this time, the number of reciprocating motions before the release layer is about to fall off is measured, to evaluate the solvent resistance according to the following solvent resistance evaluation criteria.

[0210] [Solvent Resistance Evaluation Criteria]

[0211] PASS: more than 10 times

[0212] NG: less than 10 times

[0213] 5. Evaluation of weight average molecular weight

[0214] GPC (gel permeation chromatography) is used to measure the weight average molecular weight (Mw) and the polydispersity index (PDI). The unit of the weight average molecular weight (Mw) and number average molecular weight (Mn) mentioned in the present specification is g / mol.

[0215] A sample (sample to be analyzed) is placed in a 20 mL vial, diluted with THF (tetrahydrofuran) to a concentration of about 20 mg / mL. Both the standard sample for calibration and the sample to be analyzed are filtered through a syringe filter (pore size: 0.2 μm), then the molecular weight characteristics are measured. As the analysis program, ChemStation from Agilent Technologies is used, and the elution time of the sample is compared with a calibration curve to obtain the number average molecular weight (Mn) and weight average molecular weight (Mw), then the value obtained by dividing the weight average molecular weight (Mw) by the number average molecular weight (Mn) (Mw / Mn) is taken as the polydispersity index.

[0216] <GPC Measurement Conditions>

[0217] Instrument: 1200 Series from Agilent Technologies

[0218] Column: TL Mix. A&B from Agilent Technologies is used

[0219] Solvent: THF

[0220] Column temperature: 40°C

[0221] Sample concentration: 20 mg / mL, injection volume 10 μl

[0222] MP: 364000, 91450, 17970, 4910, 1300 are used as standard samples

[0223] Preparation Example 1.

[0224] According to the compound Figure 1 The reaction scheme shown is used for synthesis. First, 2-hydroxy-2-methylphenylacetone (S1) and 3-(triethoxysilyl)propyl isocyanate (S2) are mixed in a weight ratio of 16.42:24.7 (S1:S2) and reacted at about 80°C in the presence of a catalyst (DBTDL; dibutyltin dilaurate), thereby reacting the hydroxyl group of 2-hydroxy-2-methylphenylacetone (S1) with the isocyanate group of 3-(triethoxysilyl)propyl isocyanate (S2) to produce intermediate (A). The catalyst is used in an amount of about 0.292 parts by weight relative to the total amount of 100 parts by weight of 2-hydroxy-2-methylphenylacetone (S1) and 3-(triethoxysilyl)propyl isocyanate (S2).

[0225] Subsequently, intermediate (A) and 2,2-dimethyl-1,3-propanediol (B) were mixed at a weight ratio of approximately 100:0.948 (A:B) and subjected to a condensation reaction at approximately 100°C for approximately 3 to 5 hours to produce the target compound. Figure 1 The compound shown in the figure was purified in a known manner.

[0226] The target compound has a weight-average molecular weight of approximately 50,000 g / mol and a polydispersity index (PDI) of approximately 2.1851.

[0227] Through the above synthesis process, it can be known that the target compound is a compound having an average unit of the following formula A.

[0228] [Formula A]

[0229] R 1 R 2 n SiX (3-n)2

[0230] In equation A, R 1 R is the functional group of formula B. 2 X is an isocyanate propyl group, a functional group of formula C below, or an ethoxy group, X is a linking group that connects the silicon atoms of the target compound to each other, which is an oxygen atom or a divalent linking group of formula D below, and n is a number in the range of 0 to 2.

[0231] [Formula B]

[0232]

[0233] The leftmost carbon atom in formula B is directly connected to the silicon atom in formula A.

[0234] [Formula C]

[0235]

[0236] The rightmost oxygen atom in formula C is directly connected to the silicon atom in formula A.

[0237] [Form D]

[0238]

[0239] In formula D, the oxygen atoms on both sides are directly connected to the silicon atoms in formula A.

[0240] Example 1.

[0241] A release composition was prepared by mixing polyorganosiloxane of formula E (KS-847H, Shinetsu Silicone) (weight average molecular weight about 350,000 g / mol), polyorganosiloxane of formula F (X-92-122, Shinetsu Silicone) (weight average molecular weight about 10,000 g / mol), platinum catalyst (PL-50L, Shinetsu Silicone) (C), the compound of Preparation Example 1 above, and alkoxysilane (G) (3-(trimethoxysilyl)propyl acrylate) in a weight ratio of 5:0.1:0.25:0.5:0.1 (E:F:C:Preparation Example 1:G), and dispersing them in a solvent. As solvent (S), a solvent obtained by mixing THF (tetrahydrofuran), MEK (methyl ethyl ketone), toluene (T), and n-heptane (H) in a weight ratio of 50:30:10:10 (THF:MEK:T:H).

[0242] [Formula E]

[0243]

[0244] In E, m is a number of approximately 1,500, and n is a number of approximately 12 to 13.

[0245] [Formula F]

[0246]

[0247] In formula F, a and b are each a number of approximately 34 to 36.

[0248] Example 2.

[0249] A polyorganosiloxane of formula E (KS-847H, Shinetsu Silicone) (weight-average molecular weight about 350,000 g / mol), a polyorganosiloxane of formula F (X-92-122, Shinetsu Silicone) (weight-average molecular weight about 10,000 g / mol), a platinum catalyst (PL-50L, Shinetsu Silicone) (C), the compound of Preparation Example 1, and an alkoxysilane of formula G (Gelest, DMS-R11, 3-(trimethoxysilyl)propyl acrylate) were mixed in a weight ratio of 5:0.1:0.25:0.05:0.1 (E:F:C:Preparation Example 1:G) and dispersed in a solvent to prepare a release composition. The same solvent as in Example 1 was used as the solvent.

[0250] Example 3.

[0251] A polyorganosiloxane of formula E (KS-847H, Shinetsu Silicone) (weight-average molecular weight about 350,000 g / mol), a polyorganosiloxane of formula F (X-92-122, Shinetsu Silicone) (weight-average molecular weight about 10,000 g / mol), a platinum catalyst (PL-50L, Shinetsu Silicone) (C), the compound of Preparation Example 1, and an alkoxysilane of formula G (Gelest, DMS-R11, 3-(trimethoxysilyl)propyl acrylate) were mixed in a weight ratio of 5:0.1:0.25:0.25:0.1 (E:F:C:Preparation Example 1:G) and dispersed in a solvent to prepare a release composition. The same solvent as in Example 1 was used as the solvent.

[0252] Example 4.

[0253] A polyorganosiloxane of formula E (KS-847H, Shinetsu Silicone) (weight-average molecular weight about 350,000 g / mol), a polyorganosiloxane of formula F (X-92-122, Shinetsu Silicone) (weight-average molecular weight about 10,000 g / mol), a platinum catalyst (PL-50L, Shinetsu Silicone) (C), the compound of Preparation Example 1, and an alkoxysilane of formula G (Gelest, DMS-R11, 3-(trimethoxysilyl)propyl acrylate) were mixed in a weight ratio of 5:0.1:0.25:1:0.1 (E:F:C:Preparation Example 1:G) and dispersed in a solvent to prepare a release composition. The same solvent as in Example 1 was used as the solvent.

[0254] Comparative Example 1.

[0255] A release composition was prepared by mixing polyorganosiloxane of formula E (KS-847H, Shinetsu Silicone) (weight average molecular weight about 350,000 g / mol), polyorganosiloxane of formula F (X-92-122, Shinetsu Silicone) (weight average molecular weight about 10,000 g / mol), and platinum catalyst (PL-50L, Shinetsu Silicone) (C) in a weight ratio of 5:0.1:0.25 (E:F:C) and dispersing them in a solvent. The same solvent as in Example 1 was used as the solvent.

[0256] Physical property evaluation

[0257] The release compositions of the examples or comparative examples were each applied to a base film and held at a temperature of about 150°C for about 3 minutes to form a release layer on the base film. The thickness of the release layer was about 50 nm to 80 nm. As the base film, a PET (polyethylene terephthalate) film with a thickness of about 50 μm was used.

[0258] The results of the test data measured in the above embodiments and comparative examples are summarized in Table 1 below.

[0259] [Table 1]

[0260]

[0261] In Table 1, A1 is the peel force A1 in Equation 1 for evaluating the rate of change of release peel force, where the unit is gf / inch, and A21 is the peel force A21 mentioned in the evaluation method for the rate of change of release peel force (AR), which is the release peel force measured after the sample is first irradiated with ultraviolet light and then kept at 60°C for 24 hours, where the unit is gf / inch.

[0262] Furthermore, in Table 1, AR1 is the value obtained by substituting A21 as A2 into Equation 1 of the release force change rate (AR) evaluation method, where the unit is %.

[0263] In Table 1, A22 is the release force A22 mentioned in the release force change rate (AR) evaluation method. It is the release force measured after the sample is kept at 60°C for 24 hours and then irradiated with ultraviolet light, where the unit is gf / inch.

[0264] In Table 1, AR2 is the value obtained by substituting A22 above as A2 into Equation 1 of the release force change rate (AR) evaluation method, where the unit is %.

[0265] In Table 1, Ad is the value calculated according to Equation 2 in the Residual Adhesion Rate Measurement Method section, where the unit is %.

[0266] The solvent resistance in Table 1 is the result measured according to the solvent resistance evaluation method, and the number of times refers to the number of reciprocating movements of the fabric immersed in toluene before the release layer is about to fall off during the solvent resistance evaluation.

Claims

1. A compound represented by the average unit of Formula 1: [Formula 1] in, R 1 Equation 3 below represents R 2 X is a hydrogen, isocyanate alkyl, hydroxyalkoxy, alkoxy, or monovalent hydrocarbon group; X is a linking group that connects the silicon atoms of the compound to each other; X is a divalent linking group of formula 2 below; 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. [Equation 2] Wherein, L1 is an alkylene group or an alkylidene group, and the oxygen atoms on both sides of L1 are directly connected to the silicon atoms of the compound: [Formula 3] In this compound, L2 and L3 are each independently alkylene or alkylidene, R3 is aryl or heteroaryl, and L2 in Formula 3 is directly connected to the silicon atom of the compound.

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

3. The compound according to claim 1 has a branched structure, a cage structure, or a partially 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 according to any one of claims 1 to 5.

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

8. The release composition according to claim 7, wherein the curable silicone resin component comprises a polyorganosiloxane having an average unit of formula 4 and a polyorganosiloxane having an average unit of formula 5: [Formula 4] in, P is an alkenyl group, Q is an alkoxy, hydroxyl, or 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. [Formula 5] Where Q is an alkoxy, hydroxy, or 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 formula 4 comprises one or more siloxane units selected from formula 6 and formula 7: [Formula 6] [Formula 7] in, Vi is an alkenyl group, and R 6 It can be a hydroxyl, alkoxy, or monovalent hydrocarbon group.

10. The release composition according to claim 8, wherein the polyorganosiloxane of formula 5 comprises a siloxane unit of formula 9: [Formula 9] in, R 6 It can be a hydroxyl, alkoxy, or monovalent hydrocarbon group.

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

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

13. The release composition according to claim 7, further comprising a compound of formula 10: [Formula 10] in, R1 is a group containing a double bond, and R2 to R4 are each independently an alkyl group.

14. A release layer comprising the release composition according to claim 6 or a cured product thereof.

15. The release layer according to claim 14, wherein the peel force variation rate AR according to the following equation 1 is 30% or less: [Equation 1] in, A1 is the release peel force measured at 25°C with a peel angle of 180 degrees and a peel speed of 0.3 m / min after the release layer has been held at 25°C and attached to the pressure-sensitive adhesive layer for 24 hours. A2 is the release peel force measured at 25°C with a peel angle of 180 degrees and a peel speed of 0.3 m / min after the release layer has been irradiated with ultraviolet light and held at 60°C for 24 hours while attached to the pressure-sensitive adhesive layer.

16. The release layer according to claim 14, wherein the residual adhesion rate Ad according to the following equation 2 is 80% or greater: [Equation 2] in, Ai is the release peel force measured while the pressure-sensitive adhesive tape is attached to the release layer and peeled off at 25°C with a peel angle of 180 degrees and a peel rate of 0.3 m / min; and Af is the release peel force measured while the pressure-sensitive adhesive tape is attached to the release layer to which the peel force Ai has been measured in the same manner as when the peel force Ai is measured and peeled off at 25°C with a peel angle of 180 degrees and a peel rate of 0.3 m / min.

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. A pressure-sensitive adhesive film comprising a release layer according to claim 14; and a pressure-sensitive adhesive layer attached to the release layer.

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