WO2023055087A1 - 경화성 조성물 - Google Patents
경화성 조성물 Download PDFInfo
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- WO2023055087A1 WO2023055087A1 PCT/KR2022/014589 KR2022014589W WO2023055087A1 WO 2023055087 A1 WO2023055087 A1 WO 2023055087A1 KR 2022014589 W KR2022014589 W KR 2022014589W WO 2023055087 A1 WO2023055087 A1 WO 2023055087A1
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
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- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000012796 inorganic flame retardant Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- ZQKXQUJXLSSJCH-UHFFFAOYSA-N melamine cyanurate Chemical compound NC1=NC(N)=NC(N)=N1.O=C1NC(=O)NC(=O)N1 ZQKXQUJXLSSJCH-UHFFFAOYSA-N 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 229910052574 oxide ceramic Inorganic materials 0.000 description 1
- 239000011224 oxide ceramic Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
Definitions
- a silicone resin, a polyolefin resin, an acrylic resin, an epoxy resin, or the like is usually used as a resin binder.
- the heat dissipation material when it is necessary to replace a part in contact with a heat dissipation material in a product or to change a location of a heat dissipation material in a process, the heat dissipation material needs to exhibit low adhesive strength.
- materials showing low adhesive strength include materials to which a silicone resin is applied as a resin binder.
- silicone resins are relatively expensive.
- silicone resins contain components that cause contact failure and the like when applied to electronic/electrical products, their uses are limited.
- the present application aims to provide a curable composition.
- One object of the present application is to make the curable composition or its cured product exhibit high thermal conductivity and low adhesive strength to a predetermined adherend.
- an object of the present application includes achieving the low adhesive force without using an adhesive force adjusting component such as a plasticizer or in a state where the use ratio is minimized.
- the lower limit of the adhesive strength for the polyester is 0 gf/10mm, 5 gf/10mm, 10 gf/10mm, 15 gf/10mm, 20 gf/10mm, 25 gf/10mm, 30 gf/10mm, 35 gf/10mm, 40 gf/10mm, 45 gf/10mm, 50 gf/10mm, 55 gf/10mm, 60 gf/10mm, 65 gf/10mm, 70 gf/10mm, 75 gf/10mm, 80 gf/10mm, 85 It may be gf/10mm, 90 gf/10mm or 95 gf/10mm.
- the resin composition or a cured product thereof may exhibit appropriate hardness. For example, if the hardness of the resin composition or its cured product is too high, problems may occur due to excessive brittleness. In addition, through the adjustment of the hardness of the resin composition or its cured product, it is possible to secure impact resistance and vibration resistance, and to secure the durability of the product according to the application purpose.
- the resin composition or a cured product thereof can exhibit appropriate flexibility.
- applications can be greatly expanded by adjusting the flexibility of the resin composition or its cured product to a desired level.
- the lower limit of the radius of curvature of the resin composition or its cured body may be about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12, and the upper limit may be 20, 19 , 18, 17, 16, 15, 14, 13, 12, 11, 10, 9, 8, 7, 6, 5 or 4.
- the radius of curvature is less than or equal to or less than any one of the upper limits described above, is greater than or exceeds any one of the lower limits described above, or is greater than or exceeds any one of the lower limits described above, It may be within a range of less than or equal to any one of the upper limits described.
- the radius of curvature of this resin composition or its cured body can be measured by the method disclosed in Examples below.
- the unit of curvature radius in this specification is mm.
- Examples of the compound having a hydroxy group forming the hydroxy functional component include oil-modified polyol compounds, general polyol compounds, and oil-modified alcohol compounds, but are not limited thereto.
- the hydroxy functional component may include a polyol compound.
- polyol compound means a compound containing two or more hydroxyl groups. Such a polyol compound may also be referred to as a polyfunctional polyol compound. These polyol compounds may be monomolecular, oligomeric or macromolecular compounds.
- the lower limit of the number of hydroxy groups included in the polyol compound may be 2 or 3, and the upper limit thereof is 10, 9, 8, 7, 6, 5, 4, 3 or There may be as many as two.
- the number of hydroxy groups in the polyol compound is equal to or less than any one of the upper limits described above, is equal to or more than any one of the lower limits described above, or exceeds any one of the lower limits described above. or greater, but may be within a range of less than or equal to any one of the upper limits described above.
- the hydrocarbon group that is the oil group, an alkyl group, an alkenyl group, or an alkynyl group can be exemplified.
- the hydrocarbon group may be connected to the polyol compound via a carbonyl group or a carbonyloxy group, and in this case, the oil group hydrocarbon group is an alkylcarbonyl group, an alkenylcarbonyl group, an alkynylcarbonyl group, an alkylcarbonyloxy group, It may be an alkenylcarbonyloxy group or an alkynylcarbonyloxy group.
- the number of hydrocarbon groups included in the polyol compound is not particularly limited, but in one example, the polyol compound may include one or more or two or more hydrocarbon groups per molecule. There is no particular limitation on the upper limit of the number of hydrocarbon groups included in the polyol compound. For example, the number of hydrocarbon groups per molecule of the polyol compound is 10 or less, 9 or less, 8 or less, 7 or less, 6 or less. It may be about 1 or less, 5 or less, 4 or less, 3 or less, or 2 or less.
- the polyol compound may have various forms as long as it includes the hydroxyl group and the hydrocarbon group.
- the polyol compound may be a compound having a polyester skeleton or a polyether skeleton.
- the polyol compound may be an oligomeric compound or a polymeric compound.
- the polyol compound having a polyester skeleton is a so-called polyester polyol, and may be a polyol having a structure in which the hydrocarbon group is connected to the polyester polyol.
- the polyester skeleton may be a so-called polycaprolactone skeleton
- the polyether skeleton may be a so-called polyalkylene skeleton
- X 1 and X 2 are each independently a single bond or an oxygen atom, L 1 may be an alkylene group, and n is an arbitrary number.
- single bond means a case where no atom exists at the corresponding site.
- the alkylene group may be, in one example, an alkylene group having 1 to 20 carbon atoms, 4 to 20 carbon atoms, 4 to 16 carbon atoms, 4 to 12 carbon atoms, or 4 to 8 carbon atoms, which may be linear or branched. .
- alkylene group refers to a divalent substituent formed by leaving two hydrogen atoms from an alkane. It can also break away from the carbon atom.
- the polyester skeleton may be a polycaprolactone skeleton.
- L 1 of Chemical Formula 2 may be a straight-chain alkylene group having 5 carbon atoms.
- the skeleton of Formula 2 is a polyester polyol skeleton, and may be a so-called carboxylic acid polyol skeleton or a caprolactone polyol skeleton.
- a backbone may be formed in a known manner, and for example, the backbone of the carboxylic acid polyol may be formed by reacting a component including a carboxylic acid and a polyol (eg, diol or triol), and capro
- the skeleton of the lactone polyol can be formed by reacting components including caprolactone and polyol (eg, diol or triol).
- the carboxylic acid may be a dicarboxylic acid.
- the hydroxyl group or the aforementioned hydrocarbon group may be present at the end of the skeleton of Chemical Formula 2.
- the skeleton of Formula 2 may be represented by Formula 3 below.
- the lower limit of the number of skeletons represented by Formula 2 or 3 included in the polyol compound may be one or two, and the upper limit may be 10, 9, 8, 7, 6, 5, or 4. It can be as many as 1, 3 or 2.
- the number of backbones is less than or less than any one of the upper limits described above, is greater than or exceeds any one of the lower limits described above, or is greater than or more than any one of the lower limits described above, It may be within a range of less than or equal to any one of the upper limits described above.
- the polyol compound having a polyester backbone may have a straight chain or branched chain structure.
- the straight chain structure is a structure in which a main chain including a skeleton of Formula 2 or 3 is present and no other polymer chain is connected to the main chain
- a branched chain structure is a structure in which a main chain including a skeleton of Formula 2 or 3 is present.
- a side chain a chain including a backbone of Formula 2 or 3 may be bonded.
- the number of chains comprising the backbone of Formula 2 or 3 connected as side chains in the branched chain structure above is, for example, 1 to 5, 1 to 4, 1 to 3, 1 to 2 or one.
- the polyol compound having a polyester skeleton may be a compound in which at least some hydrogen atoms of a hydrocarbon compound such as an alkane, alkene or alkyne are substituted with the hydroxyl group and/or the skeleton of Chemical Formula 3.
- the number of carbon atoms in the hydrocarbon compound such as the alkane, alkene or alkyne may be, for example, 1 to 20, 1 to 16, 1 to 8, or 4 to 6.
- Hydrocarbon compounds such as alkanes, alkenes or alkynes may be straight chain, branched chain or cyclic.
- the hydroxyl group and/or the skeleton of Formula 3 may be substituted on the same carbon atom in the alkane, alkene or alkyne, or may be substituted on a different carbon atom.
- the polyether skeleton may be a skeleton having a repeating unit represented by Formula 5 below.
- X 4 and X 5 are each independently a single bond or an oxygen atom, L 2 may be an alkylene group, and m is an arbitrary number.
- the alkylene group may be, in one example, an alkylene group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms, which may be linear or branched. there is.
- m is an arbitrary number representing the number of repeating units, and may be, for example, a number within the range of 1 to 25.
- the lower limit of m in Formula 5 may be 1, 3, 5, 7, 9, 11, 13, 15, 17, 19, 21 or 23, and the upper limit may be 25, 23, 21, 19, 17, 15, 13 , 11, 9, 7, 5 or 3 or so.
- m is less than or less than any one of the upper limits described above, is greater than or exceeds any one of the lower limits described above, or is greater than or exceeds any one of the lower limits described above, It may be within a range of less than or equal to any one of the upper limits described.
- the hydroxyl group or the aforementioned hydrocarbon group may be present at the end of the skeleton of Chemical Formula 5.
- the skeleton of Formula 5 may be represented by Formula 6 below.
- X 4 , X 5 , L 2 and m are as defined in Formula 5, and R 2 may be a hydroxy group or a substituent represented by Formula 7 below.
- X 6 is a single bond or an oxygen atom, and R is the same as R in Formula 1 above.
- the lower limit of the number of skeletons represented by Formula 5 or 6 included in the polyol compound may be 1 or 2, and the upper limit may be 10, 9, 8, 7, 6, 5, or 4. It can be as many as 1, 3 or 2.
- the number of backbones is less than or equal to or less than any one of the upper limits described above, is greater than or exceeds any one of the lower limits described above, or is greater than or exceeds any one of the lower limits described above , It may be within a range that is less than or equal to any one of the upper limits described above.
- the polyol compound having a polyether backbone may have a straight chain or branched chain structure.
- the straight chain structure is a structure in which a main chain including a skeleton of Formula 5 or 6 is present and no other polymer chain is connected to the main chain
- a branched chain structure is a structure in which a main chain including a skeleton of Formula 5 or 6 is present.
- a side chain a chain including a backbone of Formula 5 or 6 may be bonded.
- the number of chains containing the backbone of Formula 5 or 6 connected as side chains in the branched chain structure above is, for example, 1 to 5, 1 to 4, 1 to 3, 1 to 2 or one.
- the polyol compound having a polyether skeleton may be a compound in which at least a portion of hydrogen atoms of a hydrocarbon compound such as an alkane, alkene or alkyne is substituted with a hydroxyl group and/or a skeleton of Chemical Formula 5.
- the number of carbon atoms in the hydrocarbon compound such as the alkane, alkene or alkyne may be, for example, 1 to 20, 1 to 16, 1 to 8, or 4 to 6.
- Hydrocarbon compounds such as alkanes, alkenes or alkynes may be straight chain, branched chain or cyclic.
- the hydroxy group and/or the skeleton of Formula 5 may be substituted on the same carbon atom in the alkane, alkene or alkyne, or may be substituted on a different carbon atom.
- the compound described above is an oligomeric or polymeric compound
- the compound may have an appropriate level of molecular weight.
- the lower limit of the weight average molecular weight of the oligomeric or polymeric polyol compound is 100 g/mol, 200 g/mol, 300 g/mol, 400 g/mol, 500 g/mol, 600 g/mol, 700 It may be about g/mol, 800 g/mol or 900 g/mol, and the upper limit is 5000 g/mol, 4500 g/mol, 4000 g/mol, 3500 g/mol, 3000 g/mol, 2500 g/mol. , 2000 g/mol, 1500 g/mol, 1000 g/mol or 800 g/mol.
- the weight average molecular weight is less than or less than any one of the upper limits described above, is greater than or exceeds any one of the lower limits described above, or is greater than or greater than any one of the lower limits described above, It may be within a range of less than or equal to any one of the upper limits described above.
- oil-modified polyol compound as described above, desired physical properties can be more effectively secured.
- the oil-modified polyol compound may be present in an appropriate ratio in the resin composition.
- the lower limit of the content of the oil-modified polyol compound in the resin composition is 5% by weight, 10% by weight, 15% by weight, 20% by weight, 25% by weight, 30% by weight, 35% by weight, 40% by weight.
- 45% by weight, 50% by weight, 55% by weight, 60% by weight, 65% by weight, 70% by weight, 75% by weight, 80% by weight, 85% by weight, 90% by weight or 95% by weight may be about, the upper limit thereof Silver 100 wt%, 95 wt%, 90 wt%, 85 wt%, 80 wt%, 75 wt%, 70 wt%, 65 wt%, 60 wt%, 55 wt%, 50 wt%, 45 wt%, 40 It may be as much as 35%, 30%, 25% or 20% by weight.
- the content is less than or less than any one of the upper limits described above, is greater than or exceeds any one of the lower limits described above, or is greater than or exceeds any one of the lower limits described above, and It may be within a range of less than or equal to any one of the upper limits.
- the content of the oil-modified polyol compound is the content in the one-component resin composition when the resin composition is a one-component type, and the content in the part where the oil-modified polyol compound is present when the resin composition is a two-component type.
- the content of the oil-modified polyol is based on the total weight of the main part. It may be a content of .
- the resin composition includes a solvent and/or a filler
- the content is based on weight excluding the solvent and filler.
- the lower limit of the content of the oil-modified polyol compound relative to 100 parts by weight of the filler component is 1 part by weight, 3 parts by weight, 5 parts by weight, 7 parts by weight, 9 parts by weight It may be about 11 parts by weight or 13 parts by weight, and the upper limit thereof is 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, 8 parts by weight, It may be about 6 parts by weight, 4 parts by weight or 3 parts by weight.
- the content is less than or equal to or less than any one of the upper limits described above, is greater than or exceeds any one of the lower limits described above, or is greater than or exceeds any one of the lower limits described above, It may be within a range of less than or equal to any one of the upper limits described.
- the ratio to the filler component is the ratio to 100 parts by weight of the total filler components included in the resin composition when the resin composition is a one-component type, and in the case of a two-component type, the part containing the oil-modified polyol (the subject part or the curing agent) Part) relative to 100 parts by weight of all filler components present in the composition.
- the hydroxy functional component may also optionally include an alcohol compound.
- alcohol compound means a compound containing one hydroxyl group per molecule. These alcohol compounds may be monomolecular, oligomeric or macromolecular compounds.
- an oil denatured alcohol compound can also be used as the alcohol compound.
- the term oil denatured alcohol compound refers to a compound that includes one hydroxyl group per molecule and at the same time includes at least one straight-chain or branched-chain hydrocarbon group having 3 or more carbon atoms, which is the oil group, at the terminal.
- the method for confirming the number of hydroxyl groups and the number of hydrocarbon groups is the same as that of the polyol compound.
- These alcohol compounds may be monomolecular, oligomeric or macromolecular compounds.
- the oil-denatured alcohol compound may have a form similar to that of the oil-denatured polyol compound, except that it contains one hydroxyl group per molecule. Therefore, the description of the oil-modified polyol compound can be equally applied to the oil-modified alcohol compound, except for the number of hydroxyl groups.
- the lower limit of the number of carbon atoms of the straight-chain or branched-chain hydrocarbon group present in the oil-denatured alcohol compound is 4, 5, 6, 7, 8, 9, 10 , 11, 12, 13, 14, 15, 16, or 17, and the upper limit is 50, 49, 48, 47, 46, 45, 44, 43, 42, 41, 40, 39, 38, 37, 36, 35, 34, 33, 32, 31, 30, 29, 28, 27 , 26, 25, 24, 23, 22, 21, 20, 19, 18, 17, 16, 15, 14, 13, 12, 11 or 10 It might even be a dog.
- the number of carbon atoms is less than or less than any one of the upper limits described above, is greater than or exceeds any one of the lower limits described above, or is greater than or exceeds any one of the lower limits described above. While, it may be within a range of less than or less than any one of the upper limits described above.
- the straight-chain or branched-chain hydrocarbon group may or may not contain a double bond.
- the double bond may be a conjugated double bond or a cis double bond.
- the hydrocarbon group may be linked to an alcohol compound via a carbonyl group or a carbonyloxy group, in which case the hydrocarbon group may be an alkylcarbonyl group, an alkenylcarbonyl group, an alkynylcarbonyl group, an alkylcarbonyloxy group, an alkenyl group. It may be a carbonyloxy group or an alkynylcarbonyloxy group.
- the lower limit of the number of carbon atoms in the alkyl group, alkenyl group or alkynyl group is 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 It may be about 15, 16, or 17, and the upper limit is 50, 49, 48, 47, 46, 45, 44, 43, 42, 41, 40 , 39, 38, 37, 36, 35, 34, 33, 32, 31, 30, 29, 28, 27, 26, 25, 24, 23 22, 21, 20, 19, 18, 17, 16, 15, 14, 13, 12, 11 or 10.
- the number of carbon atoms is less than or less than any one of the upper limits described above, is greater than or exceeds any one of the lower limits described above, or is greater than or exceeds any one of the lower limits described above. While, it may be within a range of less than or less than any one of the upper limits described above.
- the alkyl group, alkenyl group or alkynyl group may be straight-chain or branched-chain, and may be optionally substituted with one or more substituents.
- substituents there is no particular limitation on the type of the substituent, and for example, a halogen atom such as fluorine may be exemplified as the substituent.
- the hydrocarbon of the oil-denatured alcohol compound may also be included in the substituent of Formula 1 above.
- the details of the substituent of Formula 1 are also the same as in the case of the oil-modified polyol compound.
- the number of hydrocarbon groups included in the alcohol compound is not particularly limited, but in one example, the lower limit of the number of hydrocarbon groups included in the alcohol compound may be about 1 or 2 per molecule, and the upper limit is , It may be about 10, 9, 8, 7, 6, 5, 4, 3 or 2 per molecule.
- the number of carbon atoms is less than or less than any one of the upper limits described above, is greater than or exceeds any one of the lower limits described above, or is more than or more than any one of the lower limits described above , It may be within a range that is less than or equal to any one of the upper limits described above.
- the alcohol compound may have various forms as long as it includes the hydroxyl group and the hydrocarbon group.
- the alcohol compound may be a compound in which at least a portion of hydrogen atoms of a hydrocarbon compound such as an alkane, alkene or alkyne is substituted with one hydroxyl group and/or the hydrocarbon group.
- a hydrocarbon compound such as an alkane, alkene or alkyne
- the number of carbon atoms in the hydrocarbon compound such as the alkane, alkene or alkyne may be, for example, 1 to 20, 1 to 16, 1 to 8, or 4 to 6.
- Hydrocarbon compounds such as alkanes, alkenes or alkynes may be straight chain, branched chain or cyclic.
- the hydroxyl group and/or hydrocarbon group may be substituted on the same carbon atom in the alkane, alkene or alkyne, or may be substituted on a different carbon atom.
- the alcohol compound may be a compound having a polyester skeleton or a polyether skeleton.
- the alcohol compound may be an oligomeric compound or a polymeric compound.
- the polyester backbone may be a so-called polycaprolactone backbone
- the polyether backbone may be a so-called polyalkylene backbone
- the polyester skeleton may be a skeleton having a repeating unit represented by Chemical Formula 2.
- Chemical Formula 2 the specific details of the repeating unit of Chemical Formula 2 are the same as those of the polyol compound.
- the hydroxyl group or the aforementioned hydrocarbon group in the alcohol compound having the skeleton of Formula 2 may be present at the terminal of the skeleton of Formula 2, and in this case, the skeleton of Formula 2 is can be displayed as In this case, the specific details of the skeleton of Chemical Formula 3 are the same as those of the polyol compound.
- the lower limit of the number of skeletons of Formula 2 or 3 of the alcohol compound may be 1 or 2 on the premise that the compound contains one hydroxyl group per molecule, and the upper limit is 10, 9, 8 It can be as many as 1, 7, 6, 5, 4, 3 or 2.
- the number of backbones is less than or equal to or less than any one of the upper limits described above, is greater than or exceeds any one of the lower limits described above, or is greater than or exceeds any one of the lower limits described above , It may be within a range that is less than or equal to any one of the upper limits described above.
- the alcohol compound having the polyester skeleton may also have a linear or branched chain structure.
- the straight chain structure is a structure in which a main chain including a skeleton of Formula 2 or 3 is present and no other polymer chain is connected to the main chain
- a branched chain structure is a structure in which a main chain including a skeleton of Formula 2 or 3 is present.
- a side chain a chain including a backbone of Formula 2 or 3 may be bonded.
- the number of chains comprising the backbone of Formula 2 or 3 connected as side chains in the branched chain structure above is, for example, 1 to 5, 1 to 4, 1 to 3, 1 to 2 or one.
- the alcohol compound having the polyester skeleton may also be a compound in which at least some of the hydrogen atoms of a hydrocarbon compound such as an alkane, alkene or alkyne are substituted with the hydroxyl group and/or the skeleton of Formula 3.
- the number of carbon atoms in the hydrocarbon compound such as the alkane, alkene or alkyne may be, for example, 1 to 20, 1 to 16, 1 to 8, or 4 to 6.
- Hydrocarbon compounds such as alkanes, alkenes or alkynes may be straight chain, branched chain or cyclic.
- the hydroxyl group and/or the skeleton of Formula 3 may be substituted on the same carbon atom in the alkane, alkene or alkyne, or may be substituted on a different carbon atom.
- the polyether skeleton of the alcohol compound may also be a skeleton having a repeating unit represented by Chemical Formula 5 in one example. At this time, the specific details of Formula 5 are the same as those of the polyol compound.
- the lower limit of the number of skeletons of Formula 5 or 6 included in the alcohol compound may be about 1 or 2, and the upper limit is 10, It can be as many as 9, 8, 7, 6, 5, 4, 3 or 2.
- the number of backbones is less than or equal to or less than any one of the upper limits described above, is greater than or exceeds any one of the lower limits described above, or is greater than or exceeds any one of the lower limits described above , It may be within a range that is less than or equal to any one of the upper limits described above.
- the alcohol compound having a polyether backbone may have a linear or branched chain structure.
- the straight chain structure is a structure in which a main chain including a skeleton of Formula 5 or 6 is present and no other polymer chain is connected to the main chain
- a branched chain structure is a structure in which a main chain including a skeleton of Formula 5 or 6 is present.
- a side chain a chain including a backbone of Formula 5 or 6 may be bonded.
- the number of chains containing the backbone of Formula 5 or 6 connected as side chains in the branched chain structure above is, for example, 1 to 5, 1 to 4, 1 to 3, 1 to 2 or one.
- the alcohol compound having a polyether skeleton may be a compound in which at least some of the hydrogen atoms of a hydrocarbon compound such as an alkane, alkene or alkyne are substituted with a hydroxyl group and/or a skeleton of Formula 5.
- the number of carbon atoms in the hydrocarbon compound such as the alkane, alkene or alkyne may be, for example, 1 to 20, 1 to 16, 1 to 8, or 4 to 6.
- Hydrocarbon compounds such as alkanes, alkenes or alkynes may be straight chain, branched chain or cyclic.
- the hydroxy group and/or the skeleton of Formula 5 may be substituted on the same carbon atom in the alkane, alkene or alkyne, or may be substituted on a different carbon atom.
- the compound described above is an oligomeric or polymeric compound
- the compound may have an appropriate level of molecular weight.
- the lower limit of the weight average molecular weight of the oligomeric or polymeric polyol compound is 100 g/mol, 200 g/mol, 300 g/mol, 400 g/mol, 500 g/mol, 600 g/mol, 700 It may be about g/mol, 800 g/mol or 900 g/mol, and the upper limit is 5000 g/mol, 4500 g/mol, 4000 g/mol, 3500 g/mol, 3000 g/mol, 2500 g/mol. , 2000 g/mol, 1500 g/mol, 1000 g/mol or 800 g/mol.
- the weight average molecular weight is less than or less than any one of the upper limits described above, is greater than or exceeds any one of the lower limits described above, or is greater than or greater than any one of the lower limits described above, It may be within a range of less than or equal to any one of the upper limits described above.
- the desired physical properties can be more effectively secured.
- the lower limit of the content of the oil-modified alcohol compound relative to 100 parts by weight of the oil-modified polyol compound is 10 parts by weight, 20 parts by weight, 30 parts by weight, 40 parts by weight, 50 parts by weight, 60 parts by weight, 70 parts by weight, 80 parts by weight 90 parts by weight, 100 parts by weight, 110 parts by weight, 120 parts by weight, 130 parts by weight, 140 parts by weight, 150 parts by weight, 160 parts by weight, 170 parts by weight, 180 parts by weight, 190 parts by weight, 200 parts by weight, 210 parts by weight, 220 parts by weight, 230 parts by weight, 240 parts by weight, 250 parts by weight, 260 parts by weight, 270 parts by weight, 280 parts by weight, 290 parts by weight or 300 parts by weight may be about, and the upper limit is 1,000 parts by weight , 950 parts by weight, 900 parts by weight, 850 parts by weight, 800 parts by weight, 750 parts by weight, 700 parts by weight, 650 parts by weight, 600 parts by weight, 550 parts by weight
- the ratio is less than or equal to or less than any one of the upper limits described above, is greater than or exceeds any one of the lower limits described above, or is greater than or exceeds any one of the lower limits described above, and It may be within a range of less than or equal to any one of the upper limits.
- the ratio may be changed in consideration of the overall composition or desired physical properties of the resin composition.
- the oil-modified polyol compound or alcohol compound may be synthesized through a known synthesis method. That is, the compounds may be prepared by reacting a compound capable of introducing the hydrocarbon group corresponding to the oil-modified portion with a known polyol compound.
- a compound capable of introducing the hydrocarbon group saturated or unsaturated fatty acids may be exemplified, and specifically, butyric acid, caproic acid, 2-ethyl hexanoic acid ), caprylic acid, isononanoic acid, capric acid, lauric acid, myristic acid, palmitic acid, Stearic acid, linoleic acid, or oleic acid may be exemplified, but is not limited thereto.
- polyol compound reacting with the saturated or unsaturated fatty acid there is no particular limitation on the type of polyol compound reacting with the saturated or unsaturated fatty acid, and for example, an appropriate type of general polyol compound described later may be applied, but is not limited thereto.
- the hydroxy functional component may further include a polyol compound different from the oil-modified polyol compound.
- the polyol compound does not include the aforementioned oil hydrocarbon group, that is, a straight-chain or branched-chain hydrocarbon group having 3 or more carbon atoms.
- these polyol compounds may be referred to herein as general polyol compounds.
- the lower limit of the number of carbon atoms of the hydrocarbon group not included in the general polyol compound is 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 It may be about 15, 16, or 17, and the upper limit is 50, 49, 48, 47, 46, 45, 44, 43, 42, 41, 40 , 39, 38, 37, 36, 35, 34, 33, 32, 31, 30, 29, 28, 27, 26, 25, 24, 23 22, 21, 20, 19, 18, 17, 16, 15, 14, 13, 12, 11 or 10.
- the number of carbon atoms is less than or less than any one of the upper limits described above, is greater than or exceeds any one of the lower limits described above, or is greater than or exceeds any one of the lower limits described above. While, it may be within a range of less than or less than any one of the upper limits described above.
- the hydrocarbon group may be an alkyl group, an alkenyl group, or an alkynyl group having the number of carbon atoms.
- the general polyol compound may include two or more hydroxyl groups per molecule, and the polyol compound may be a monomolecular, oligomeric or polymeric compound.
- the number of hydroxy groups included in the general polyol compound is not particularly limited, but in one example, the lower limit of the number of hydroxy groups included in the general polyol compound may be about 2 or 3 per molecule, and the lower limit is 1 molecule It could be 10, 9, 8, 7, 6, 5, 4, 3 or 2 per.
- the number of hydroxy groups is less than or equal to or less than any one of the upper limits described above, is greater than or exceeds any one of the lower limits described above, or is greater than or greater than any one of the lower limits described above , It may be within a range that is less than or equal to any one of the upper limits described above.
- Common polyol compounds can take many forms.
- the general polyol compound may be a polyester polyol.
- polyester polyols so-called carboxylic acid polyols or caprolactone polyols can be used, for example.
- the polyester polyol may be a skeleton having a repeating unit represented by Formula 8 below.
- X 7 and X 8 are each independently a single bond or an oxygen atom, L 3 may be an alkylene group, and p is an arbitrary number.
- the alkylene group may be, in one example, an alkylene group having 1 to 20 carbon atoms, 4 to 20 carbon atoms, 4 to 16 carbon atoms, 4 to 12 carbon atoms, or 4 to 8 carbon atoms, which may be linear or branched. there is.
- L 3 in Chemical Formula 8 may be a straight-chain alkylene group having 5 carbon atoms.
- p is an arbitrary number representing the number of repeating units, and may be, for example, a number within the range of 1 to 25.
- the polyester polyol having the skeleton of Formula 8 may be a so-called carboxylic acid polyol or caprolactone polyol.
- a polyol compound can be formed by a known method.
- the carboxylic acid polyol can be formed by reacting a component including a carboxylic acid and a polyol (eg, diol or triol), and caprolactone Polyols can be formed by reacting components including caprolactone and polyols (eg, diols or triols).
- the carboxylic acid may be a dicarboxylic acid.
- the hydroxyl group may be present at the end of the skeleton of Chemical Formula 8 or at another site of the polyester polyol.
- the lower limit of the number of skeletons of Formula 8 included in the general polyol compound may be 1 or 2, and the upper limit thereof is 10, 9, 8, 7, 6, 5, 4, It could be 3, 2 or 1.
- the number of backbones is less than or equal to or less than any one of the upper limits described above, is greater than or exceeds any one of the lower limits described above, or is greater than or exceeds any one of the lower limits described above , It may be within a range that is less than or equal to any one of the upper limits described above.
- the polyol compound having a polyester backbone may have a straight chain or branched chain structure.
- Polyol compounds of this kind are, for example, Kuraray's P-510, P-1010, P-2010, P-3010, P-4010, P-5010, P-6010, F-510, F-1010, F- 2010, F-3010, P-2011, P-520, P-2020, P-1012, P-2012, P-630, P-2030, P-2050 or N-2010.
- polyisocyanate compound examples include aliphatic polyisocyanates such as hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, lysine diisocyanate, norbornane diisocyanate methyl, ethylene diisocyanate, propylene diisocyanate or tetramethylene diisocyanate; alicyclic polyisocyanates such as transcyclohexane-1,4-diisocyanate, isophorone diisocyanate, bis(isocyanatemethyl)cyclohexane diisocyanate, or dicyclohexylmethane diisocyanate; Alternatively, one or more of the above carbodiimide-modified polyisocyanates or isocyanurate-modified polyisocyanates may be used.
- aliphatic polyisocyanates such as hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, lysine diisocyanate
- the upper limit of the proportion of the filler component in the resin composition is 99% by weight, 98% by weight, 97% by weight, 96% by weight, 95% by weight, 94.5% by weight, 94% by weight, 93.5% by weight, 93% by weight, 92.5% by weight, 92% by weight, 91.5% by weight, 91% by weight, 90.5% by weight, 90.0% by weight, 89.5% by weight, 89.0% by weight, 88.5% by weight or 88.0% by weight, and the lower limit is about 70% by weight.
- the ratio is less than or equal to or less than any one of the upper limits described above, is greater than or exceeds any one of the lower limits described above, or is greater than or exceeds any one of the lower limits described above, It may be within a range of less than or equal to any one of the upper limits described.
- the resin composition may be a one-component composition or a two-component composition.
- each of the above-described components of the resin composition may be separately included in a physically separated main part and a curing agent part.
- the main part may include at least an oil-modified polyol compound among the hydroxy functional components
- the curing agent part may include at least the polyisocyanate.
- the filler component may be included in any one of the subject and curing agent parts, or may be included in both of the subject and curing agent parts. When the filler component is included in both the main agent and the curing agent part, the same amount of the filler component may be included in the main agent and the curing agent part.
- a volume ratio (P/N) of the volume (P) of the main part to the volume (N) of the curing agent part may be in the range of about 0.8 to 1.2.
- the present application it is possible to provide a resin composition or a cured product thereof that exhibits low adhesive strength to a predetermined adherend while exhibiting high thermal conductivity.
- the low adhesive strength may be achieved without using an adhesive force adjusting component such as a plasticizer or by minimizing the use ratio thereof.
- the present application may also provide a product including the curable composition or a cured product thereof.
- the thermal conductivity of the resin composition (curable composition) or its cured product was measured by a hot-disk method according to ISO 22007-2 standards. Specifically, a mixture of a volume ratio of 1:1 of the subject part and the curing agent part of Examples or Comparative Examples composed of a two-component type was placed in a mold having a thickness of about 7 mm, and thermal conductivity was measured in the through plane direction using a hot disk device. was measured.
- Hot Disk equipment is a device that can check thermal conductivity by measuring temperature change (electrical resistance change) while the sensor in which the nickel wire has a double spiral structure is heated. Thermal conductivity was measured according to.
- a resin composition (a mixture of a subject part and a curing agent part in a volume ratio of 1:1) is applied to the aluminum plate to have a thickness of about 2 mm after curing, and then the PET film is adhered to the layer of the resin composition. and maintained at room temperature (about 25° C.) for about 24 hours to cure the resin composition.
- the peeling was performed at a peeling speed of about 0.5 mm/min and a peeling angle of 180 degrees until the PET film was completely peeled off.
- An uncured resin composition (a mixture of a main part and a curing agent part) is coated on the center of an aluminum substrate having a width of 2 cm and a length of 7 cm, respectively, to a size of about 2 cm in width and 2 cm in length, and then on the coating layer again.
- the two aluminum substrates were attached to form an angle of 90 degrees to each other.
- the lower aluminum substrate was pressed at a speed of 0.5 mm/min to measure the force while the lower aluminum substrate was separated, and the maximum force measured in the process was expressed as the area of the specimen.
- the adhesive strength to aluminum was obtained by dividing.
- the radius of curvature of the cured body was evaluated using a cured body having a width, length, and thickness of 1 cm, 10 cm, and 2 mm, respectively.
- the radius of curvature is the minimum radius of a cylinder at which cracks do not occur in the hardened body when the hardened body is attached to cylinders having various radii and bent along the longitudinal direction.
- the weight average molecular weight (Mw) was measured using GPC (Gel permeation chromatography). Specifically, for the weight average molecular weight (Mw), put the sample to be analyzed in a 5 mL vial, dilute with a THF (tetrahydrofuran) solvent to a concentration of about 1 mg/mL, and then prepare a standard sample for calibration and an analysis sample. It can be filtered and measured through a syringe filter (pore size: 0.45 ⁇ m). ChemStation of Agilent technologies was used as an analysis program, and the weight average molecular weight (Mw) can be obtained by comparing the elution time of the sample with the calibration curve.
- GPC Gel permeation chromatography
- Standard samples using polystyrene (MP: 3900000, 723000, 316500, 52200, 31400, 7200, 3940, 485)
- a hydroxyl functional component (A) consisting of an oil-modified polyol compound of the following formula (A) was prepared in the following manner.
- n and m are each greater than 0, and their sum is about 4.8.
- Polycaprolactone polyol Perstorp Capa 3031
- isononanoic acid a saturated fatty acid
- Capa 3031: isononanoic acid a catalyst
- Ti(II) 2-ethylhexanoate Sigma-Aldrich
- a hydroxyl functional component (B) comprising an oil-modified polyol compound represented by the following formula (B) was prepared in the following manner.
- each n is about 4
- R 4 is a substituent represented by Formula B-1 below
- R 3 is a substituent represented by Formula B-2 below.
- n is about 4.
- a compound of formula C (PPG, manufacturer: Perstorp, product name: Polyol3380) and isononanoic acid, a saturated fatty acid, were mixed in a flask at a weight ratio of 1:0.38 (compound of formula C: isononanoic acid).
- each n is about 4, and R 4 is a substituent represented by Formula C-1 below.
- n is about 4.
- a catalyst Te(II) 2-ethylhexanoate (Sigma-Aldrich) was added to the mixture in an amount of 0.3 parts by weight based on 100 parts by weight of the total mixture, and stirred at 150 ° C. for 30 minutes under an inert gas purge condition. Subsequently, a small amount of xylene, an azeotropic solution, was added, the temperature was raised to 190° C., and the reaction was performed for 10 hours or more, and the pressure was reduced to 40 Torr or less for 1 hour or more to remove xylene and unreacted substances. The reactant was cooled and filtered through a filter to obtain the target product.
- the weight average molecular weight was about 800 g/mol.
- 2 is a diagram showing the results of GPC analysis performed on the target object.
- a main part was prepared by mixing the hydroxyl functional component (B) of Preparation Example 2, the filler component and the plasticizer (diisononyl adipate) in a weight ratio of 10:89:1 (component (B):filler component:plasticizer).
- component (B):filler component:plasticizer a weight ratio of 10:89:1
- the weight ratio during the mixing was about 6:2:2 (first alumina filler:second alumina filler:third alumina filler).
- Polyisocyanate (Tolonate HDT-LV2, manufactured by Vencorex) was used as a curing agent.
- a curing agent part was prepared by mixing the polyisocyanate, filler component, and plasticizer (diisononyl adipate) in a weight ratio of 5:5:90 (polyisocyanate:filler component:plasticizer).
- plasticizer diisononyl adipate
- the filler component in the above the same filler component as the filler component of the main part was used.
- a resin composition (curable composition) was prepared by preparing the subject part and the curing agent part, respectively, and the subject and the curing agent part were mixed and maintained at room temperature to form a cured body.
- the equivalent ratio (OH/NCO) of the hydroxyl group (OH) present in the main part and the isocyanate group (NCO) present in the curing agent part was about 100.
- a resin composition (curable composition) was prepared by preparing the main part and the curing agent part in the same manner as in Example 1, and after mixing the main part and the curing agent part, a cured body was formed by maintaining the main part and the curing agent part at room temperature, but the mixing was performed in the main part.
- the equivalence ratio (OH/NCO) of the hydroxy group (OH) present and the isocyanate group (NCO) present in the curing agent part was set to about 170.
- Polyisocyanate (Vencorex, Tolonate HDT-LV2) was used as a curing agent.
- a curing agent part was prepared by mixing the polyisocyanate, filler component, and plasticizer (diisononyl adipate) in a weight ratio of 5:5:90 (polyisocyanate:filler component:plasticizer).
- plasticizer diisononyl adipate
- the filler component in the above the same filler component as in Example 1 was used.
- a resin composition (curable composition) was prepared by preparing the subject part and the curing agent part, respectively, and the subject and the curing agent part were mixed and maintained at room temperature to form a cured body.
- the equivalent ratio (OH/NCO) of the hydroxyl group (OH) present in the main part and the isocyanate group (NCO) present in the curing agent part was about 100.
- a resin composition (curable composition) was prepared by preparing the main part and the curing agent part in the same manner as in Example 3, and after mixing the main part and the curing agent part, a cured body was formed by maintaining the main part and the curing agent part at room temperature, but the mixing was carried out in the main part.
- the equivalence ratio (OH/NCO) of the hydroxy group (OH) present and the isocyanate group (NCO) present in the curing agent part was set to about 170.
- the hydroxyl functional component (A) of Preparation Example 1 a general polyol compound (Kuraray, F-2010), a filler component and a plasticizer (diisononyl adipate) in a weight ratio of 11.4: 1.1: 87: 0.5
- component (A): general A main part was prepared by mixing polyol compound:filler component:plasticizer).
- the same filler component as in Example 1 was used.
- Polyisocyanate (Vencorex, Tolonate HDT-LV2) was used as a curing agent.
- a curing agent part was prepared by mixing the polyisocyanate, filler component, and plasticizer (diisononyl adipate) in a weight ratio of 5:5:90 (polyisocyanate:filler component:plasticizer).
- plasticizer diisononyl adipate
- the filler component in the above the same filler component as in Example 1 was used.
- a resin composition (curable composition) was prepared by preparing the subject part and the curing agent part, respectively, and the subject and the curing agent part were mixed and maintained at room temperature to form a cured body.
- the equivalent ratio (OH/NCO) of the hydroxyl group (OH) present in the main part and the isocyanate group (NCO) present in the curing agent part was about 179.
- a resin composition (curable composition) was prepared by preparing the main part and the curing agent part in the same manner as in Example 5, and after mixing the main part and the curing agent part, a cured body was formed by maintaining the main part and the curing agent part at room temperature, but the mixing was performed in the main part.
- the equivalence ratio (OH/NCO) of the hydroxy group (OH) present and the isocyanate group (NCO) present in the curing agent part was set to about 157.
- a resin composition (curable composition) was prepared by preparing the subject part and the curing agent part in the same manner as in Example 5, and after mixing the subject and the curing agent part, a cured body was formed by maintaining the subject part and the curing agent part at room temperature.
- the equivalent ratio (OH/NCO) of the hydroxyl group (OH) present in the curing agent part and the isocyanate group (NCO) present in the curing agent part was set to about 140.
- the hydroxyl functional component (A) of Preparation Example 1 a general polyol compound (Kuraray Co., F-2010), a filler component and a plasticizer (diisononyl adipate) in a weight ratio of 7.4: 3.2: 87: 2.4 (component (A): general polyol:filler component:plasticizer) to prepare the main part.
- Polyisocyanate (Vencorex, Tolonate HDT-LV2) was used as a curing agent.
- a curing agent part was prepared by mixing the polyisocyanate, filler component, and plasticizer (diisononyl adipate) in a weight ratio of 5:5:90 (polyisocyanate:filler component:plasticizer).
- plasticizer diisononyl adipate
- the filler component in the above the same filler component as in Example 1 was used.
- a resin composition (curable composition) was prepared by preparing the subject part and the curing agent part, respectively, and the subject and the curing agent part were mixed and maintained at room temperature to form a cured body.
- the equivalent ratio (OH/NCO) of the hydroxyl group (OH) present in the main part and the isocyanate group (NCO) present in the curing agent part was about 170.
- a resin composition (curable composition) was prepared by preparing the main part and the curing agent part in the same manner as in Example 8, and after mixing the main part and the curing agent part, a cured body was formed by maintaining the main part and the curing agent part at room temperature, but the mixing was performed in the main part.
- the equivalence ratio (OH/NCO) of the hydroxy group (OH) present and the isocyanate group (NCO) present in the curing agent part was set to about 140.
- Example 1 Adhesion to polyester (gf/cm) Al adhesion (N/mm 2 ) Shore OO hardness Thermal conductivity (W/mK) radius of curvature
- Example 1 182 0.15 91 2.546 8
- Example 2 90 0.13 64 2.626 0
- Example 3 333 0.15 98 2.755 >12
- Example 4 125 0.039 92 2.631 8
- Example 5 96 0.064 74 2.481 4
- Example 6 133 0.048 88 2.556 6
- Example 7 116 0.07 93 2.434 7
- Example 8 255 0.045 86 2.558 3
- Example 9 222 0.032 95 2.627 8
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Abstract
Description
폴리에스테르에 대한 접착력(gf/cm) | Al 접착력(N/mm2) | Shore OO 경도 | 열전도도(W/mK) | 곡률 반경 | |
실시예1 | 182 | 0.15 | 91 | 2.546 | 8 |
실시예2 | 90 | 0.13 | 64 | 2.626 | 0 |
실시예3 | 333 | 0.15 | 98 | 2.755 | >12 |
실시예4 | 125 | 0.039 | 92 | 2.631 | 8 |
실시예5 | 96 | 0.064 | 74 | 2.481 | 4 |
실시예6 | 133 | 0.048 | 88 | 2.556 | 6 |
실시예7 | 116 | 0.07 | 93 | 2.434 | 7 |
실시예8 | 255 | 0.045 | 86 | 2.558 | 3 |
실시예9 | 222 | 0.032 | 95 | 2.627 | 8 |
Claims (16)
- 탄소 원자수가 5개 이상인 분지쇄형 탄화수소 사슬을 말단에 적어도 하나 포함하는 폴리올 화합물 및 필러를 포함하는 경화성 조성물.
- 제 1 항에 있어서, 알루미늄에 대한 접착력이 0.1 N/mm2 이하인 경화체를 형성하는 경화성 조성물.
- 제 1 항 또는 제 2 항에 있어서, 폴리에스테르 표면에 대한 접착력이 100 gf/cm 이하인 경화체를 형성하는 경화성 조성물.
- 제 1 항 내지 제 3 항 중 어느 한 항에 있어서, 쇼어 OO 경도가 95 이하인 경화체를 형성하는 경화성 조성물.
- 제 1 항 내지 제 4 항 중 어느 한 항에 있어서, 탄화수소기는 알킬기, 알케닐기 또는 알키닐기인 경화성 조성물.
- 제 1 항 내지 제 6 항 중 어느 한 항에 있어서, 폴리올 화합물은, 폴리에스테르 골격 또는 폴리에테르 골격을 가지는 경화성 조성물.
- 제 1 항 내지 제 7 항 중 어느 한 항에 있어서, 폴리올 화합물은, 폴리카프로락톤 골격 또는 폴리알킬렌 골격을 가지는 경화성 조성물.
- 제 1 항 내지 제 8 항 중 어느 한 항에 있어서, 폴리올 화합물은 중량평균분자량이 100 g/mol 내지 3000 g/mol 의 범위 내에 있는 폴리올 화합물을 포함하는 경화성 조성물.
- 제 1 항 내지 제 9 항 중 어느 한 항에 있어서, 탄소 원자수가 5개 이상인 분지형 탄화수소기를 가지지 않는 폴리올 화합물을 추가로 포함하는 경화성 조성물.
- 제 10 항에 있어서, 탄소 원자수가 5개 이상인 분지형 탄화수소기를 가지지 않는 폴리올 화합물은 폴리카프로락톤 폴리올 또는 알칸디올 단위, 폴리올 단위 및 디카복실산 단위를 가지는 폴리올인 경화성 조성물.
- 제 1 항 내지 제 11 항 중 어느 한 항에 있어서, 폴리이소시아네이트를 추가로 포함하는 경화성 조성물.
- 제 1 항 내지 제 12 항 중 어느 한 항에 있어서, 가소제를 추가로 포함하는 경화성 조성물.
- 제 1 항 내지 제 13 항 중 어느 한 항에 있어서, 필러는, 수산화 알루미늄, 수산화 마그네슘, 수산화 칼슘, 하이드로마그네사이트, 마그네시아, 알루미나, 질화 알루미늄, 질화 붕소, 질화 규소, 탄화 규소, 산화 아연 또는 산화 베릴륨인 경화성 조성물.
- 탄소 원자수가 5개 이상인 분지쇄형 탄화수소 사슬을 말단에 적어도 하나 포함하는 폴리올 화합물 폴리올 화합물 및 필러를 포함하는 주제 파트; 및경화제 성분 및 필러를 포함하는 경화제 파트를 포함하는 2액형 조성물.
- 발열 부품 및 상기 발열 부품과 인접하여 존재하는, 제 1 항 내지 제 14 항 중 어느 한 항의 경화성 조성물 또는 제 15 항의 2액형 조성물의 경화체를 포함하는 제품.
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KR20100037058A (ko) * | 2007-06-06 | 2010-04-08 | 바스프코팅즈재팬 가부시키가이샤 | 높은 oh 가를 갖는 결합제, 및 상기 결합제를 포함하고 양호한 광학 특성 및 양호한 내스크래치성 및 내화학성을 갖는 클리어 페인트 조성물 |
US20130071340A1 (en) * | 2010-05-31 | 2013-03-21 | Evonik Goldschmidt Gmbh | Polyol partial esters for use in cosmetics |
KR20160105354A (ko) | 2015-02-27 | 2016-09-06 | 주식회사 엘지화학 | 배터리 모듈 |
US20170204310A1 (en) * | 2016-01-19 | 2017-07-20 | H.B. Fuller Company | One-part polyurethane adhesive composition, method of making a laminate, and laminate |
KR20190136646A (ko) * | 2018-05-31 | 2019-12-10 | 주식회사 엘지화학 | 수지 조성물 |
KR20210071564A (ko) * | 2019-12-06 | 2021-06-16 | 주식회사 엘지화학 | 이액형 수지 조성물 및 이를 포함하는 배터리 모듈의 제조방법 |
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KR20100037058A (ko) * | 2007-06-06 | 2010-04-08 | 바스프코팅즈재팬 가부시키가이샤 | 높은 oh 가를 갖는 결합제, 및 상기 결합제를 포함하고 양호한 광학 특성 및 양호한 내스크래치성 및 내화학성을 갖는 클리어 페인트 조성물 |
US20130071340A1 (en) * | 2010-05-31 | 2013-03-21 | Evonik Goldschmidt Gmbh | Polyol partial esters for use in cosmetics |
KR20160105354A (ko) | 2015-02-27 | 2016-09-06 | 주식회사 엘지화학 | 배터리 모듈 |
US20170204310A1 (en) * | 2016-01-19 | 2017-07-20 | H.B. Fuller Company | One-part polyurethane adhesive composition, method of making a laminate, and laminate |
KR20190136646A (ko) * | 2018-05-31 | 2019-12-10 | 주식회사 엘지화학 | 수지 조성물 |
KR20210071564A (ko) * | 2019-12-06 | 2021-06-16 | 주식회사 엘지화학 | 이액형 수지 조성물 및 이를 포함하는 배터리 모듈의 제조방법 |
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