Ethylene-alpha-olefin copolymers and adhesive compositions comprising the same

By controlling parameters such as density, viscosity, and full width at half maximum (FWHM) of the crystallization peak of the ethylene-α-olefin copolymer, a copolymer with excellent processability and adhesion properties was prepared, solving the problem of processability and non-uniform physical properties of linear low-density polyethylene in film applications and improving the performance of the film.

CN122277786APending Publication Date: 2026-06-26LG CHEM LTD
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
LG CHEM LTD
Filing Date
2025-12-18
Publication Date
2026-06-26

AI Technical Summary

Technical Problem

In the existing technology, the processability and physical properties of linear low-density polyethylene are not uniform. In particular, when using 1-butene or 1-hexene as comonomers, the productivity is low and the processability is poor, making it difficult to meet the requirements of high-performance films.

Method used

By controlling parameters such as density, viscosity, full width at half maximum (FWHM) of the crystallization peak, and melt index of the ethylene-α-olefin copolymer, and combining nuclear magnetic resonance analysis and cross-fractional chromatography techniques, ethylene-α-olefin copolymers with densities ranging from 0.867 g/cc to 0.889 g/cc, viscosities ranging from 16,000 cP to 20,000 cP, and full WHMs of the crystallization peak ranging from 22 to 50 were prepared and combined with tackifiers to form adhesive compositions.

Benefits of technology

Excellent processability and adhesion properties of ethylene-α-olefin copolymers in adhesives have been achieved, improving their application performance in films and other fields.

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Abstract

This invention relates to an ethylene-α-olefin copolymer exhibiting excellent processability and adhesive properties, and adhesive compositions comprising the same.
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Description

[0001] Cross-references to related applications This application claims priority based on Korean Patent Application No. 10-2024-0195270 filed on December 24, 2024 and Korean Patent Application No. 10-2025-0202023 filed on December 17, 2025, the entire contents of which are incorporated herein by reference. Technical Field

[0002] This invention relates to an ethylene-α-olefin copolymer exhibiting excellent processability and adhesive properties, and adhesive compositions comprising the same. Background Technology

[0003] Olefin polymerization catalyst systems can be divided into Ziegler-Natta catalyst systems and metallocene catalyst systems. These two types of highly active catalyst systems have been developed based on their respective characteristics. Since its invention in the 1950s, the Ziegler-Natta catalyst has been widely used in existing commercial processes. However, as a multi-site catalyst with multiple active sites, it is characterized by a wide molecular weight distribution of the polymer and an uneven distribution of comonomer composition, making it difficult to obtain the desired physical properties.

[0004] On the other hand, metallocene catalysts consist of a main catalyst primarily composed of transition metal compounds and a cocatalyst primarily composed of aluminum organometallic compounds. Such catalysts, as homogeneous complex catalysts, are single-site catalysts. Due to the characteristics of a single active site, the resulting polymer has a narrow molecular weight distribution and a uniform composition of comonomers. Furthermore, by changing the ligand structure and polymerization conditions, the stereoregularity, copolymerization properties, molecular weight, and crystallinity of the polymer can be altered.

[0005] On the other hand, linear low-density polyethylene (LLDPE) is manufactured by copolymerizing ethylene with α-olefins under low pressure using a polymerization catalyst. It is a resin with a narrow molecular weight distribution and short branches of a certain length, without long branches. In addition to the properties of general polyethylene, LLDPE films also exhibit high tensile strength and elongation, as well as excellent tear strength and drop hammer impact strength. Therefore, its use is increasingly increasing in fields where traditional LLDPE or HLDPE stretch films and overlap films are difficult to apply.

[0006] However, when using 1-butene or 1-hexene as comonomers to produce linear low-density polyethylene, the productivity is higher compared to the process using 1-octene comonomers. However, due to limitations in the catalyst and process technologies used, the physical properties of this product are still significantly inferior to those of copolymers using 1-octene, and it also suffers from poor processability due to a narrower molecular weight distribution.

[0007] Furthermore, even with improved processability, the uneven dispersion of different molecular weights within a unit particle results in a rough extruded appearance and unstable physical properties, even under relatively good extrusion conditions.

[0008] Against this backdrop, there is a continued need to manufacture superior products that balance physical properties and processability, particularly with the increasing demand for polyethylene copolymers that offer excellent processability.

[0009] Existing technical documents Patent documents (Patent Document 1) U.S. Patent No. 5,064,802 Summary of the Invention

[0010] Technical issues The object of the present invention is to provide an ethylene-α-olefin copolymer that exhibits excellent processability and adhesive properties by controlling density, viscosity and melt index, as well as an adhesive composition utilizing the thereof.

[0011] Technical solution (1) The present invention provides an ethylene-α-olefin copolymer that satisfies the following conditions (a) to (c): (a) Density: 0.867 g / cc to 0.889 g / cc; (b) Viscosity: 16,000 cP to 20,000 cP at 177°C; (c) The full width at half maximum (FWHM) of the crystallization peaks, as measured by cross-fractionation chromatography (CFC), ranges from 22 to 50.

[0012] (2) The present invention provides an ethylene-α-olefin copolymer as described in (1) above, wherein the density is from 0.868 g / cc to 0.888 g / cc.

[0013] (3) The present invention provides an ethylene-α-olefin copolymer as described in (1) or (2) above, wherein the full width at half maximum (FWHM) of the crystallization peak shown when the crystallization temperature is measured by the cross-fractionation chromatography (CFC) is 22.2 to 49.0.

[0014] (4) The present invention provides an ethylene-α-olefin copolymer as described in any one of (1) to (3) above, wherein the melt index (190°C, 2.16 kg load conditions) is 400 dg / min to 1,600 dg / min.

[0015] (5) The present invention provides an ethylene-α-olefin copolymer as described in any one of (1) to (4) above, wherein the number of vinyl functional groups in each 1,000 carbon atoms of the ethylene-α-olefin copolymer as measured by nuclear magnetic resonance analysis is 0.01 to 2.0.

[0016] (6) The present invention provides an ethylene-α-olefin copolymer as described in any one of (1) to (5) above, wherein the number of ethylene-α-olefin copolymers per 1,000 carbon atoms as measured by nuclear magnetic resonance analysis is 0.01 to 0.9.

[0017] (7) The present invention provides an ethylene-α-olefin copolymer as described in any one of (1) to (6) above, wherein the number of vinylene functional groups per 1,000 carbon atoms as measured by nuclear magnetic resonance analysis is 0.1 to 1.9.

[0018] (8) The present invention provides an ethylene-α-olefin copolymer as described in any one of (1) to (7) above, wherein the number of trisubstituted vinyl functional groups per 1,000 carbon atoms in the ethylene-α-olefin copolymer, as measured by nuclear magnetic resonance analysis, is 0.01 to 0.8.

[0019] (9) The present invention provides an ethylene-α-olefin copolymer as described in any one of (1) to (8) above, wherein the melting temperature of the ethylene-α-olefin copolymer is 50°C to 90°C.

[0020] (10) The present invention provides an ethylene-α-olefin copolymer as described in any one of (1) to (9) above, wherein the crystallization temperature of the ethylene-α-olefin copolymer is 30°C to 70°C.

[0021] (11) The present invention provides an adhesive composition comprising an ethylene-α-olefin copolymer as described in any one of (1) to (10) above and a tackifier.

[0022] (12) The present invention provides an adhesive composition as described in (11) above, wherein the tackifier is selected from one or more of modified C5 hydrocarbon resins, styrene-modified terpene resins, fully hydrogenated or partially hydrogenated C9 hydrocarbon resins, hydrogenated alicyclic hydrocarbon resins, hydrogenated aromatic modified alicyclic hydrocarbon resins, and mixtures thereof.

[0023] (13) The present invention provides an adhesive composition as described in (11) or (12) above, wherein the adhesive composition has a viscosity of 450 cP to 1,400 cP at 177°C.

[0024] Invention Effects The ethylene-α-olefin copolymer of the present invention exhibits excellent processability and adhesion properties. Detailed Implementation

[0025] The present invention will now be described in more detail to aid in understanding it.

[0026] The terms or words used in this specification and claims should not be construed as limited to their ordinary or dictionary meanings, but should be interpreted as meanings and concepts consistent with the technical concept of this invention. The principle is that the inventor is able to properly define the concepts of the terms to best interpret his invention.

[0027] ethylene-α-olefin copolymer The ethylene-α-olefin copolymer of the present invention satisfies the following conditions (a) to (c): (a) Density: 0.867 g / cc to 0.889 g / cc; (b) Viscosity: 16,000 cP to 20,000 cP at 177°C; (c) The full width at half maximum (FWHM) of the crystallization peaks, as measured by cross-fractionation chromatography (CFC), ranges from 22 to 50.

[0028] The inventors completed this invention by controlling the density, viscosity, and full width at half maximum (FWHM) of the crystallization peaks at the crystallization temperature measured by cross-fractional chromatography within a specific range, thus confirming that the ethylene-α-olefin copolymer exhibits excellent processability and adhesive properties during the adhesive manufacturing process.

[0029] The ethylene-α-olefin copolymer of the present invention has a density of 0.867 g / cc to 0.889 g / cc as measured according to ASTM D-792. The density can be above 0.868 g / cc, above 0.869 g / cc, or above 0.870 g / cc, and can be below 0.888 g / cc, below 0.886 g / cc, or below 0.885 g / cc, for example, from 0.868 to 0.888 g / cc.

[0030] The ethylene-α-olefin copolymer has a density within the aforementioned range, thus exhibiting excellent processability and adhesion. If the density is below 0.867 g / cc, the set time increases, leading to increased adhesive application time and reduced productivity; if it is above 0.889 g / cc, there is a problem of excessively increasing the melt temperature of the adhesive.

[0031] The ethylene-α-olefin copolymer of the present invention has a viscosity of 16,000 cP to 20,000 cP at 177°C. The ethylene-α-olefin copolymer having a viscosity within this range exhibits excellent processability and adhesive strength. If the viscosity is below 16,000 cP, the adhesive strength is poor; if it is above 20,000 cP, the flowability decreases, resulting in reduced processability.

[0032] The ethylene-α-olefin copolymer of the present invention exhibits a full width at half maximum (FWHM) of 22 to 50 when the crystallization temperature is measured by cross-fractionation chromatography (CFC). Specifically, the FWHM can be 22.2 or higher, 22.5 or higher, 22.7 or higher, or 23.0 or higher, and can be 49.0 or lower, 48.0 or lower, 47.0 or lower, 46.0 or lower, or 45.0 or lower, for example, 22.2 to 49.0.

[0033] Ethylene-α-olefin copolymers have a full width at half maximum (FWHM) within the aforementioned range, thus exhibiting excellent processability and adhesion. If the FWHM is below 22, the processability or adhesion is poor.

[0034] In this invention, the melt index (at 190°C and a 2.16 kg load) of the ethylene-α-olefin copolymer is between 400 dg / min and 1,600 dg / min. Specifically, the melt index can be 420 dg / min or higher, 440 dg / min or higher, 460 dg / min or higher, or 470 dg / min or higher, and can be 1,500 dg / min or lower, 1,400 dg / min or lower, 1,300 dg / min or lower, or 1,250 dg / min or lower.

[0035] When the melt flow index is met, it exhibits excellent processability and adhesion.

[0036] In this invention, the elution temperature (T) of the ethylene-α-olefin copolymer e The temperature can be between 20°C and 35°C. Specifically, it can be above 21°C, above 22°C, or above 23°C, and it can be below 34°C, below 33°C, below 32°C, or below 31°C.

[0037] When the elution temperature is within the above range, it exhibits excellent processability and adhesion.

[0038] In this invention, the melting temperature (T0) of the ethylene-α-olefin copolymer is... m The temperature can be between 50°C and 90°C. Specifically, it can be above 51°C, above 52°C, above 53°C, above 54°C, above 55°C, or above 56°C, and can be below 89°C, below 88°C, below 87°C, below 86°C, below 85°C, below 84°C, below 83°C, below 82°C, below 81°C, below 80°C, below 79°C, below 78°C, or below 77°C.

[0039] In this invention, the crystallization temperature (T) of the ethylene-α-olefin copolymer is... c The temperature can be between 30°C and 70°C. Specifically, it can be above 31°C, above 32°C, above 33°C, above 34°C, above 35°C, above 36°C, or above 37°C, and can be below 69°C, below 68°C, below 67°C, below 66°C, below 65°C, below 64°C, below 63°C, below 62°C, below 61°C, below 60°C, or below 59°C.

[0040] When the melting and crystallization temperatures within the above range are met, the low-temperature adhesion is excellent and the processability is improved.

[0041] The melting and crystallization temperatures can be measured using a differential scanning calorimeter (DSC). Specifically, the copolymer is heated to 150°C and held for 5 minutes, then cooled to 20°C, and then heated again. The heating and cooling rates are controlled at 10°C / min, and the result measured during the second heating phase is taken as the melting temperature, while the result measured during the cooling phase is taken as the crystallization temperature.

[0042] In this invention, the number of vinyl functional groups per 1,000 carbon atoms in the ethylene-α-olefin copolymer, as measured by nuclear magnetic resonance analysis, can be from 0.01 to 2.0. Specifically, it can be more than 0.02 or more than 0.03, and can be less than 1.9, less than 1.8, less than 1.7, less than 1.6, less than 1.5, less than 1.4, or less than 1.3.

[0043] Furthermore, the number of vinylidene functional groups per 1,000 carbon atoms in the ethylene-α-olefin copolymer of the present invention can be from 0.01 to 0.9. Specifically, it can be more than 0.02, and can be less than 0.8, less than 0.7, or less than 0.6.

[0044] Furthermore, the number of vinylene functional groups per 1,000 carbon atoms in the ethylene-α-olefin copolymer of the present invention, as measured by nuclear magnetic resonance analysis, can be from 0.1 to 1.9. Specifically, it can be more than 0.11, more than 0.12, more than 0.13, or more than 0.14, and can be less than 1.8, less than 1.7, less than 1.6, or less than 1.5.

[0045] Furthermore, the number of trisubstituted vinyl functional groups per 1,000 carbon atoms in the ethylene-α-olefin copolymer of the present invention can be from 0.01 to 0.8. Specifically, it can be more than 0.02 or more than 0.03, and less than 0.7 or less than 0.6.

[0046] Furthermore, the total number of unsaturated functional groups per 1,000 carbon atoms in the ethylene-α-olefin copolymer of the present invention, as measured by nuclear magnetic resonance analysis, can be from 0.2 to 5.5. More specifically, it can be more than 0.21, more than 0.22, more than 0.23, more than 0.24, more than 0.25, more than 0.26, or more than 0.27, and can be less than 5.0, less than 4.9, less than 4.8, less than 4.7, less than 4.6, less than 4.5, less than 4.4, less than 4.3, less than 4.2, less than 4.1, less than 4.0, less than 3.9, less than 3.8, or less than 3.7.

[0047] The ethylene-α-olefin copolymer of the present invention has the number of unsaturated functional groups within the above-mentioned range, thereby improving the adhesion at low and room temperatures, exhibiting excellent processability, and demonstrating excellent long-term physical properties.

[0048] The vinyl group has an R-CH=CH2 structure, the trisubstituted vinyl group has an RCH=CR'R" structure, the ethylene propylene (also known as "1,2-vinylene") has an RCH=CHR'(E-form) or Z-RCH=CHR'(Z-form) structure, and the ethylene propylene (also known as "1,1-vinylene") has an RR'C=CH2 structure. R, R', and R" can each independently be a polymer chain or a branch formed from α-olefin comonomers.

[0049] In this invention, the contents of vinyl groups, ethylene ions, ethylene propylene, and trisubstituted vinyl groups in the copolymer can be calculated based on NMR analysis results. Specifically, the copolymer is dissolved in 1,1,2,2-deuterated tetrachloroethane (TCE-d2) solvent, and the measurements are performed at 393 K using a Bruker AVANCE III 500MHz NMR instrument. 1 In the 1H NMR spectrum, the TCE-d2 peak was corrected to 6.0 ppm, and the content ratio of comonomers was calculated using the integral values ​​in the 1.4 ppm and 0.96 ppm regions. The contents of vinyl, ethylene ide, ethylene ethylene, and trisubstituted vinyl groups observed in the range of 4.7 ppm to 5.6 ppm were calculated (analytical method: AMT-3863). Peak assignment is referenced in [Macromolecules 2014, 47, 3282-3790].

[0050] Furthermore, the molecular weight distribution (MWD) of the ethylene-α-olefin copolymer of the present invention can be from 1.5 to 3.5. Specifically, it can be 1.6 or more, 1.7 or more, 1.8 or more, 1.9 or more, 2.0 or more, 2.1 or more, 2.2 or more, 2.3 or more, or 2.4 or more, and can be 3.4 or less, 3.3 or less, 3.2 or less, 3.1 or less, 3.0 or less, 2.9 or less, or 2.8 or less.

[0051] The weight-average molecular weight (Mw) of the ethylene-α-olefin copolymer described in one embodiment of the present invention can be from 16,000 g / mol to 30,000 g / mol. Specifically, it can be 17,000 g / mol or more, 18,000 g / mol or more, 19,000 g / mol or more, or 20,000 g / mol or more, and can be 29,000 g / mol or less or 28,000 g / mol or less.

[0052] When the weight-average molecular weight meets the above-mentioned range, it is associated with the viscosity of the binder composition containing it, thereby expecting a significant improvement in processability. That is, the mechanical properties, impact strength, and viscosity of ethylene-α-olefin copolymers can be controlled by adjusting the type and amount of catalyst used in the polymerization process, and while meeting the above conditions, excellent mechanical properties can be maintained and improved processability can be exhibited.

[0053] On the other hand, in this invention, the weight-average molecular weight (Mw) and number-average molecular weight (Mn) are the equivalent molecular weights of polystyrene analyzed by gel permeation chromatography (GPC), and the molecular weight distribution can be calculated by the ratio of Mw / Mn.

[0054] The ethylene-α-olefin copolymer of the present invention is manufactured by copolymerizing ethylene with α-olefin monomers. Here, α-olefin refers to the portion of the copolymer derived from α-olefin monomers, including C4 to C20 α-olefins. Specifically, examples include propylene, 1-butene, 1-pentene, 4-methyl-1-pentene, 1-hexene, 1-heptene, 1-octene, 1-decene, 1-undecene, 1-dodecene, 1-tetradecene, 1-hexadecene, 1-eicosene, etc., and may be a single α-olefin or a mixture of two or more α-olefins.

[0055] The α-olefin may be 1-butene, 1-hexene, or 1-octene, preferably 1-butene, 1-hexene, or a combination thereof.

[0056] Furthermore, in the ethylene-α-olefin copolymer, the content of α-olefin can be appropriately selected within the range that meets the above-mentioned physical property requirements. Specifically, it can be greater than 0 and less than 99 mol%, or 10 to 50 mol%.

[0057] The ethylene-α-olefin copolymer of the present invention can be manufactured by thermally decomposing an existing ethylene-α-olefin copolymer at a suitable temperature and time. The existing ethylene-α-olefin copolymer is independent of commercially available ethylene-α-olefin copolymers or ethylene-α-olefin copolymers manufactured by known methods, as long as it is readily available to those skilled in the art. More specifically, ethylene-α-olefin copolymers with a melt index (MI; 190°C, 2.16 kg load) of 5.0 g / 10 min to 15.0 g / 10 min and a density of 0.850 g / cc to 0.890 g / cc can be used, but are not limited thereto.

[0058] The thermal decomposition can specifically involve heating at 350°C to 470°C, or at temperatures above 360°C, 370°C, 380°C, 390°C, or 400°C, and can be below 460°C, 450°C, 440°C, 430°C, or 420°C.

[0059] Furthermore, under the temperature conditions described above, thermal decomposition can be performed for 1 to 7 hours, specifically, for more than 1 hour, more than 2 hours, or more than 3 hours, and for less than 6 hours or less than 5 hours.

[0060] Furthermore, the ethylene-α-olefin copolymer of the present invention can be manufactured by a method of simultaneously polymerizing ethylene and butene by adding hydrogen to a catalyst composition containing metallocene compounds.

[0061] The amount of hydrogen added can be from 100cc / min to 700cc / min, and can be above 150cc / min, above 170cc / min, above 200cc / min or above 250cc / min, and can be below 600cc / min, below 500cc / min, below 400cc / min or below 380cc / min, but is not limited thereto.

[0062] Adhesive composition The present invention provides an adhesive composition comprising the ethylene-α-olefin copolymer and a tackifier.

[0063] In this invention, the viscosity of the adhesive composition at 177°C can be from 450 cP to 1,400 cP. Specifically, the viscosity can be 460 cP or more, 470 cP or more, 480 cP or more, 490 cP or more, 500 cP or more, 510 cP or more, 520 cP or more, or 530 cP or more, and can be 1,390 cP or less, 1,380 cP or less, 1,370 cP or less, 1,360 cP or less, 1,350 cP or less, 1,340 cP or less, 1,330 cP or less, 1,320 cP or less, or 1,310 cP or less.

[0064] The tackifier may be an aliphatic hydrocarbon resin, for example selected from modified C5 hydrocarbon resins (C5 / C9 resins), styrene-modified terpene resins, fully hydrogenated or partially hydrogenated C9 hydrocarbon resins, hydrogenated alicyclic hydrocarbon resins, hydrogenated aromatic modified alicyclic hydrocarbon resins, and mixtures thereof.

[0065] The tackifier is not particularly limited, and its content can be from 5 to 70 parts by weight, specifically 20 to 70 parts by weight, relative to 100 parts by weight of the adhesive composition. If the tackifier content is less than 5 parts by weight, the viscosity of the adhesive composition may increase, resulting in decreased processability; if the content is greater than 70 parts by weight, it may lead to decreased heat resistance.

[0066] The ethylene-α-olefin copolymer may be 10 to 50 parts by weight, specifically 15 to 30 parts by weight, relative to 100 parts by weight of the adhesive composition. Excellent adhesive properties are maintained when the above numerical range is met.

[0067] In addition, the adhesive composition may also contain a plasticizer. The plasticizer is not particularly limited and may be, for example, a paraffinic or naphthenic plasticizing oil. Specifically, it may be a low molecular weight polymer such as olefin oligomers, liquid polybutene, polyisoprene copolymers, liquid styrene-isoprene copolymers, or liquid hydrogenated styrene-conjugated diene copolymers, vegetable oils and their derivatives, or microcrystalline waxes.

[0068] The plasticizer is not particularly limited, and its content may be from 10 to 50 parts by weight, specifically from 20 to 40 parts by weight, relative to 100 parts by weight of the adhesive composition. If the plasticizer content is less than 10 parts by weight, the viscosity of the adhesive composition may increase, resulting in decreased processability; if the content is greater than 50 parts by weight, it may lead to decreased adhesive properties.

[0069] In addition, the adhesive composition may also contain antioxidants to improve heat resistance and color, etc.

[0070] At this time, the antioxidant is not particularly limited and can be a conventionally known one in the art. With respect to 100 parts by weight of the binder composition, its content can be 0.01 to 5 parts by weight, or 0.01 to 1 part by weight, or 0.05 to 0.75 parts by weight.

[0071] In addition, the binder composition may further contain one or more additives selected from UV stabilizers, colorants or pigments, fillers, flow aids, coupling agents, crosslinking agents, surfactants, solvents, and combinations thereof.

[0072] The filler can be selected from sand, talc, dolomite, calcium carbonate, clay, silica, mica, wollastonite, feldspar, aluminum silicate, alumina, hydrated alumina, glass beads, glass microspheres, ceramic microspheres, thermoplastic microspheres, barite, wood powder, or combinations thereof, and the filler can be present in an amount of 80% by weight or less of the total composition.

[0073] In the present invention, the binder composition can be a hot-melt binder composition.

[0074] The present invention provides a product comprising a substrate coated with the binder composition. The product can be selected from tapes, labels, transfer papers, boxes, cardboard, pallets, medical devices, bandages, and hygiene products, but is not limited thereto.

[0075] Examples The present invention will be further described in detail below by way of examples. However, the following examples are only for illustrating the present invention and do not limit the scope of the present invention.

[0076] Production Example 1 (1) Production of ligand compound (Synthesis of N-tert-butyl-1-(1,2-dimethyl-3H-benzo[b]cyclopenta[d]thiophen-3-yl)-1,1-dimethylsilanamine) In a 100 mL Schlenk flask, 4.65 g (15.88 mmol) of chloro(1,2-dimethyl-6,7-dihydro-3H-benzo[b]cyclopenta[d]thiophen-3-yl)dimethylsilane compound was weighed and added, and then 80 mL of THF was added. t-BuNH2 (4 eq, 6.68 mL) was added at room temperature, and then the reaction was carried out for 3 days at room temperature. After the reaction, THF was removed, and then filtered with hexane. After drying the solvent, 4.50 g of a yellow liquid was obtained with a yield of at 86%.

[0077] 1 H-NMR (in CDCl3, 500 MHz): 7.99 (d, 1H), 7.83 (d, 1H), 7.35 (dd, 1H), 7.24 (dd, 1H), 3.49 (s, 1H), 2.37 (s, 3H), 2.17 (s, 3H), 1.27 (s, 9H), 0.19 (s, 3H), -0.17 (s, 3H).

[0078] (2) Preparation of transition metal compound In a 50 mL Schlenk flask, add the ligand compound (1.06 g, 3.22 mmol / 1.0 eq) and 16.0 mL (0.2 M) of MTBE, and stir first. Add n-BuLi (2.64 mL, 6.60 mmol / 2.05 eq, 2.5 M in THF) at -40 °C, and then react overnight at room temperature. Subsequently, slowly add MeMgBr (2.68 mL, 8.05 mmol / 2.5 eq, 3.0 M in diethyl ether) dropwise at -40 °C, and then add TiCl4 (2.68 mL, 3.22 mmol / 1.0 eq, 1.0 M in toluene) successively, and react overnight at room temperature. Then, filter the reaction mixture through Celite with hexane. After drying the solvent, 1.07 g of brown solid is obtained with a yield of 82%.

[0079] 1 H-NMR (in CDCl3, 500 MHz): 7.99 (d, 1H), 7.68 (d, 1H), 7.40 (dd, 1H), 7.30 (dd, 1H), 3.22 (s, 1H), 2.67 (s, 3H), 2.05 (s, 3H), 1.54 (s, 9H), 0.58 (s, 3H), 0.57 (s, 3H), 0.40 (s, 3H), -0.45 (s, 3H).

[0080] Production Example 2 (1) Preparation of ligand compound <Synthesis of N-tert-butyl-1-(1,2-dimethyl-3H-benzo[b]cyclopenta[d]thiophen-3-yl)-1,1-(methyl)(2-methylphenyl)silanamine> (i) Preparation of chloro-1-(1,2-dimethyl-3H-benzo[b]cyclopenta[d]thiophen-3-yl)-1,1-(methyl)(2-methylphenyl)silan In a 250 mL Schlenk flask, 2.0 g (1.0 eq, 9.985 mmol) of 1,2-dimethyl-3H-benzo[b]cyclopentadieno[d]thiophene and 50 mL of THF were added. 4.2 mL (1.05 eq, 10.484 mmol, 2.5 M hexane) of n-BuLi was added dropwise at -30 °C, followed by stirring overnight at room temperature. The stirred Li-complex THF solution was transferred through a sleeve at -78 °C to a Schlenk flask containing 2.46 g (1.2 eq, 11.982 mmol) of dichloro(o-tolylmethyl)silane and 30 mL of THF, followed by stirring overnight at room temperature. After stirring, the solution was dried under vacuum and then extracted with 100 mL of hexane.

[0081] (ii) Preparation of N-tert-butyl-1-(1,2-dimethyl-3H-benzo[b]cyclopentadien[d]thiophen-3-yl)-1,1-(methyl)(2-methylphenyl)silaneamine 4.0 g (1.0 eq, 10.0 mmol) of extracted chloro-1-(1,2-dimethyl-3H-benzo[b]cyclopentadieno[d]thiophen-3-yl)-1,1-(methyl)(2-methylphenyl)silane was stirred in 10 mL of hexane, and then 4.2 mL (4.0 eq, 40.0 mmol) of t-BuNH2 was added at room temperature, followed by stirring overnight at room temperature. After stirring, the mixture was dried under vacuum and then extracted with 150 mL of hexane. After solvent drying, 4.26 g (99%, dr = 1:0.83) of a viscous liquid was obtained.

[0082] 1 H-NMR (CDCl3, 500MHz): δ 7.95(t, 2H), 7.70(d, 1H), 7.52(d, 1H), 7.47-7.44(m, 2H), 7.24-7.02(m, 9H), 6.97(t, 1H), 3.59(s, 1H), 3.58(s, 1H), 2.50(s,3H), 2.44(s, 3H), 2.25(s, 3H), 2.16(s, 3H), 2.06(s, 3H), 1.56(s, 3H), 1.02(s,9H), 0.95(s, 9H), -0.03(s, 3H), -0.11(s, 3H).

[0083] (2) Manufacturing of transition metal compounds In a 250 mL round-bottom flask, the ligand compound (4.26 g, 10.501 mmol) was added to 53 mL (0.2 M) of MTBE and stirred. n-BuLi (8.6 mL, 21.52 mmol, 2.05 eq, 2.5 M hexane) was added at -40 °C, and the mixture was stirred overnight at room temperature.

[0084] Subsequently, MeMgBr (8.8 mL, 26.25 mmol, 2.5 eq, 3.0 M diethyl ether) was slowly added dropwise at -40 °C, followed by TiCl4 (10.50 mL, 10.50 mmol), and the mixture was stirred overnight at room temperature. The reaction mixture was then filtered through hexane. DME (3.3 mL, 31.50 mmol) was added to the filtrate, and the solution was filtered through hexane and concentrated to give 3.42 g (68%, dr = 1:0.68) of a yellow solid.

[0085] 1 H NMR (CDCl3, 500MHz): δ 7.83(d, 1H), 7.80(d, 1H), 7.74(d, 1H), 7.71(d,1H), 7.68(d, 1H), 7.37(d, 1H), 7.31-6.90(m, 9H), 6.84(t, 1H), 2.54(s, 3H),2.47(s, 3H), 2.31(s, 3H), 2.20(s, 3H), 1.65(s, 9H), 1.63(s, 9H), 1.34(s, 3H),1.00(s, 3H), 0.98(s, 3H), 0.81(s, 3H), 0.79(s, 3H), 0.68(s, 3H), 0.14(s, 3H), -0.03(s, 3H).

[0086] Example 1 Weigh 1 kg of ethylene-octene copolymer (LG Chem LC670, MI: 5 g / 10 min, density: 0.871 g / cc) and place it in a 5 L batch reactor. Maintain a vacuum and remove moisture and oxygen. After removal, argon (Ar) gas is introduced into the beaker to create an inert environment. Connect the beaker containing the ethylene-butene copolymer to a mechanical stirrer and impeller, stir at 300 rpm, and heat at 400 °C for 5 hours for thermal decomposition. After fully cooling the thermally decomposed copolymer under an argon (Ar) atmosphere, open the beaker to obtain the product.

[0087] Example 2 Weigh 1 kg of ethylene-butene copolymer (LG Chem LC575, MI: 5 g / 10 min, density: 0.875 g / cc) and place it in a 5 L batch reactor. Maintain a vacuum and remove moisture and oxygen. After removal, argon (Ar) gas is introduced into the beaker to create an inert environment. Connect the beaker containing the ethylene-butene copolymer to a mechanical stirrer and impeller, stir at 400 rpm, and heat at 400 °C for 5 hours for thermal decomposition. After fully cooling the thermally decomposed copolymer under an argon (Ar) atmosphere, open the beaker to obtain the product.

[0088] Example 3 In a 1.5L continuous process reactor, hexane solvent was added at a rate of 5.0 kg / h, and 1-butene was added at a rate of 0.7 kg / h, with preheating at 150°C. Simultaneously, triisobutylaluminum compound (0.045 mmol / min), a metallocene catalyst (a mixture of Preparation Example 1 and Preparation Example 2 in a 5:5 molar ratio, 0.240 μmol / min), and dimethylphenylammonium tetra(pentafluorophenyl)borate co-catalyst (2.288 μmol / min) were added to the reactor. Subsequently, ethylene (0.87 kg / h) and hydrogen (280 cc / min) were added to the reactor, and the copolymerization reaction was carried out at 150°C for at least 60 minutes in a continuous process at a pressure of 89 bar to obtain an ethylene-butene copolymer. The copolymer was then dried in a vacuum oven for at least 12 hours before its physical properties were measured.

[0089] Example 4 In a 1.5L continuous process reactor, hexane solvent was added at a rate of 5.0 kg / h, and 1-butene was added at a rate of 0.85 kg / h, with preheating at 150°C. Simultaneously, triisobutylaluminum compound (0.045 mmol / min), a metallocene catalyst (a mixture of Preparation Example 1 and Preparation Example 2 in a 5:5 molar ratio, 0.240 μmol / min), and dimethylphenylammonium tetra(pentafluorophenyl)borate co-catalyst (2.288 μmol / min) were added to the reactor. Subsequently, ethylene (0.87 kg / h) and hydrogen (250 cc / min) were added to the reactor, and the copolymerization reaction was carried out at 150°C for at least 60 minutes in a continuous process at a pressure of 89 bar to obtain an ethylene-butene copolymer. The copolymer was then dried in a vacuum oven for at least 12 hours before its physical properties were measured.

[0090] Example 5 In a 1.5L continuous process reactor, hexane solvent was added at a rate of 5.0 kg / h, and 1-octene was added at a rate of 1.2 kg / h, with preheating at 150°C. Simultaneously, triisobutylaluminum compound (0.045 mmol / min), a metallocene catalyst (a mixture of Preparation Example 1 and Preparation Example 2 in a 5:5 molar ratio, 0.240 μmol / min), and dimethylphenylammonium tetra(pentafluorophenyl)borate co-catalyst (2.288 μmol / min) were added to the reactor. Subsequently, ethylene (0.87 kg / h) and hydrogen (280 cc / min) were added to the reactor, and the copolymerization reaction was carried out at 150°C for at least 60 minutes in a continuous process at a pressure of 89 bar to obtain an ethylene-octene copolymer. The copolymer was then dried in a vacuum oven for at least 12 hours before its physical properties were measured.

[0091] Comparative Example 1 Weigh 1 kg of ethylene-butene copolymer (LG Chem LC675, MI: 14 g / 10 min, density: 0.877 g / cc) and place it in a 5 L batch reactor. Maintain a vacuum and remove moisture and oxygen. After removal, argon (Ar) gas is introduced into the beaker to create an inert environment. Connect the beaker containing the ethylene-butene copolymer to a mechanical stirrer and impeller, stir at 300 rpm, and heat at 380 °C for 2 hours for thermal decomposition. After fully cooling the thermally decomposed copolymer under an argon (Ar) atmosphere, open the beaker to obtain the product.

[0092] Comparative Example 2 Weigh 1 kg of ethylene-butene copolymer (LG Chem LC675, MI: 14 g / 10 min, density: 0.877 g / cc) and place it in a 5 L batch reactor. Maintain a vacuum and remove moisture and oxygen. After removal, argon (Ar) gas is introduced into the beaker to create an inert environment. Connect the beaker containing the ethylene-butene copolymer to a mechanical stirrer and impeller, stir at 300 rpm, and heat at 430 °C for 2 hours for thermal decomposition. After fully cooling the thermally decomposed copolymer under an argon (Ar) atmosphere, open the beaker to obtain the product.

[0093] Comparative Example 3 In a 1.5L continuous process reactor, hexane solvent was added at a rate of 5.0 kg / h, and 1-butene was added at a rate of 0.6 kg / h, with preheating at 150°C. Simultaneously, triisobutylaluminum compound (0.045 mmol / min), a metallocene catalyst (a mixture of Preparation Example 1 and Preparation Example 2 in a 5:5 molar ratio, 0.240 μmol / min), and dimethylphenylammonium tetra(pentafluorophenyl)borate co-catalyst (2.288 μmol / min) were added to the reactor. Subsequently, ethylene (0.87 kg / h) and hydrogen (300 cc / min) were added to the reactor, and the copolymerization reaction was carried out in a continuous process at 150°C for at least 60 minutes at a pressure of 89 bar to obtain an ethylene-butene copolymer. The copolymer was then dried in a vacuum oven for at least 12 hours before its physical properties were measured.

[0094] Comparative Example 4 In a 1.5L continuous process reactor, hexane solvent was added at a rate of 5.0 kg / h, and 1-butene was added at a rate of 0.9 kg / h, with preheating at 150°C. Simultaneously, triisobutylaluminum compound (0.045 mmol / min), a metallocene catalyst (a mixture of Preparation Example 1 and Preparation Example 2 in a 5:5 molar ratio, 0.240 μmol / min), and dimethylphenylammonium tetra(pentafluorophenyl)borate co-catalyst (2.288 μmol / min) were added to the reactor. Subsequently, ethylene (0.87 kg / h) and hydrogen (310 cc / min) were added to the reactor, and the copolymerization reaction was carried out in a continuous process at 150°C for at least 60 minutes at a pressure of 89 bar to obtain an ethylene-butene copolymer. The copolymer was then dried in a vacuum oven for at least 12 hours before its physical properties were measured.

[0095] Comparative Example 5 In a 1.5L continuous process reactor, hexane solvent was added at a rate of 5.0 kg / h, and 1-butene was added at a rate of 0.8 kg / h, with preheating at 150°C. Simultaneously, triisobutylaluminum compound (0.045 mmol / min), a metallocene catalyst (Preparation Example 1, 0.240 μmol / min), and dimethylphenylammonium tetra(pentafluorophenyl)borate co-catalyst (2.288 μmol / min) were added to the reactor. Subsequently, ethylene (0.87 kg / h) and hydrogen (330 cc / min) were added to the reactor, and the copolymerization reaction was carried out at 150°C for at least 60 minutes in a continuous process at a pressure of 89 bar to obtain an ethylene-butene copolymer. The copolymer was then dried in a vacuum oven for at least 12 hours before its physical properties were measured.

[0096] Comparative Example 6 In a 1.5L continuous process reactor, hexane solvent was added at a rate of 5.0 kg / h, and 1-octene was added at a rate of 1.4 kg / h, with preheating at 150 °C. Simultaneously, triisobutylaluminum compound (0.045 mmol / min), a metallocene catalyst (Preparation Example 1, 0.240 μmol / min), and dimethylphenylammonium tetra(pentafluorophenyl)borate co-catalyst (2.288 μmol / min) were added to the reactor. Subsequently, ethylene (0.87 kg / h) and hydrogen (230 cc / min) were added to the reactor, and the copolymerization reaction was carried out at 150 °C for at least 60 minutes in a continuous process at a pressure of 89 bar to obtain an ethylene-octene copolymer. The copolymer was then dried in a vacuum oven for at least 12 hours before its physical properties were measured.

[0097] Comparative Example 7 1 kg of ethylene-butene copolymer (LG Chem LC675, MI: 14 g / 10 min, density: 0.877 g / cc) was weighed and placed in a 5 L batch reactor. Vacuum was maintained to remove moisture and oxygen. After removal, argon (Ar) gas was introduced into the beaker to create an inert environment. The beaker containing the ethylene-butene copolymer was connected to a mechanical stirrer and impeller, stirred at 300 rpm, and heated at 420 °C for 3 hours for thermal decomposition. After the copolymer was fully cooled under an argon (Ar) atmosphere, the beaker was opened to obtain the product.

[0098] Comparative Example 8 In a 1.5L continuous process reactor, hexane solvent was added at a rate of 5.0 kg / h, and 1-butene was added at a rate of 0.7 kg / h, with preheating at 150°C. Simultaneously, triisobutylaluminum compound (0.045 mmol / min), a metallocene catalyst (a mixture of Preparation Example 1 and Preparation Example 2 in a 5:5 molar ratio, 0.240 μmol / min), and dimethylphenylammonium tetra(pentafluorophenyl)borate co-catalyst (2.288 μmol / min) were added to the reactor. Subsequently, ethylene (0.87 kg / h) and hydrogen (380 cc / min) were added to the reactor, and the copolymerization reaction was carried out in a continuous process at 150°C for at least 60 minutes at a pressure of 89 bar to obtain an ethylene-butene copolymer. The copolymer was then dried in a vacuum oven for at least 12 hours before its physical properties were measured.

[0099] Comparative Example 9 Weigh 1 kg of ethylene-butene copolymer (LG Chem LC575, MI: 5 g / 10 min, density: 0.875 g / cc) and place it in a 5 L batch reactor. Maintain a vacuum and remove moisture and oxygen. After removal, argon (Ar) gas is introduced into the beaker to create an inert environment. Connect the beaker containing the ethylene-butene copolymer to a mechanical stirrer and impeller, stir at 420 rpm, and heat at 420 °C for 5 hours for thermal decomposition. After fully cooling the thermally decomposed copolymer under an argon (Ar) atmosphere, open the beaker to obtain the product.

[0100] Experimental Example 1 The physical properties of the copolymers manufactured in the above examples and comparative examples were compared and analyzed. The measurement conditions and methods are as follows: density According to ASTM D-792, the sample was pressed into a sheet with a thickness of 3 mm and a radius of 2 cm at 180°C, cooled at 10°C / min, and then measured using a Mettler balance.

[0101] Viscosity (cP) The following method was used to measure the viscosity using a Brookfield RVDV3T viscometer. Specifically, the sample was placed in a 13 mL sample chamber and heated to 177°C using a Brookfield Thermosel. After the sample was completely melted, the viscometer was lowered, and the rotor was fixed in the sample chamber. The rotation speed of the rotor (SC-29 high-temperature melting rotor) was fixed at 10 rpm. The readings were then taken for at least 20 minutes or until the values ​​stabilized, and the final values ​​were recorded.

[0102] Melt Index (MI) MI was measured according to ASTM D-1238. 2.16 (Condition E, 190℃, 2.16kg load).

[0103] Full width at half maximum (FWHM) of the crystallization peak The measurement equipment used was PolymerChar's CFC. First, using o-dichlorobenzene as a solvent, the copolymer solution was completely dissolved in an oven within the CFC analyzer at 130°C for 60 minutes. This solution was then poured into a TREF column adjusted to 135°C, cooled to 95°C, and stabilized at this temperature for 45 minutes. Subsequently, the TREF column temperature was lowered to -20°C at a rate of 0.5°C / min and maintained at -20°C for 10 minutes. The elution volume (mass %) was then measured using an infrared spectrophotometer. Next, the TREF column temperature was increased to a preset temperature at a rate of 20°C / min and maintained at that temperature for a preset time (approximately 27 minutes). This process was repeated until the TREF temperature reached 130°C, and the amount of eluted fraction (mass %) was measured within each temperature range. Furthermore, the eluted fractions at each temperature were fed to a GPC column, and the molecular weight (Mw) was measured using the same principle as GPC measurements, except that o-dichlorobenzene was used as the solvent. The FWHM value is calculated by fitting a Gaussian curve to the elution volume profile (dW / dT vs T) obtained through CFC in the program (Origin).

[0104] Elution temperature (T) e ) Elution temperature is determined by taking the highest point of the largest peak from the CFC elution curve expressed as elution volume (dC / dT) as T. e Exported.

[0105] Molecular weight distribution Under the following gel permeation chromatography (GPC) analytical conditions, the weight-average molecular weight (Mw) and number-average molecular weight (Mn) of the generated copolymer were measured: -Column: Agilent Olexis Solvent: Trichlorobenzene (TCB) - Flow rate: 1.0 mL / min - Sample concentration: 1.0 mg / mL -Injection volume: 200μL - Column temperature: 160℃ - Detector: Agilent High Temperature RI detector -Standard: Polystyrene (corrected using a cubic function) Data processing: Cirrus software The molecular weight distribution is calculated from the Mw / Mn ratio.

[0106] Melting temperature and crystallization temperature Melting temperature (T) m ) and crystallization temperature (T) c The results were obtained using a Differential Scanning Calorimeter (DSC 6000) manufactured by PerkinElmer. Specifically, the copolymer was heated to 200°C and held for 5 minutes under a nitrogen atmosphere using DSC, then cooled to 30°C, and then heated again while observing the DSC curve. The heating and cooling rates were 10°C / min.

[0107] In the measured DSC curve, the melting temperature is the maximum point of the endothermic peak during the second heating, and the crystallization temperature is the maximum point of the exothermic peak during cooling.

[0108] Table 1 Referring to Table 1, the ethylene-α-olefin copolymers of Examples 1 to 5 of the present invention were confirmed to have densities of 0.867 g / cc to 0.889 g / cc, viscosities of 16,000 cP to 20,000 cP at 177°C, and full width at half maximum (FWHM) of the crystallization peaks at the crystallization temperature measured by cross-fractionation chromatography (CFC) of 22 to 50.

[0109] On the other hand, it was confirmed that the viscosity of the ethylene-α-olefin copolymers of Comparative Examples 1, 2, 4 to 9 decreased from 16,000 cP to 20,000 cP, the density of Comparative Examples 3 and 4 decreased from 0.867 g / cc to 0.889 g / cc, and the full width at half maximum (FWHM) of the crystallization peak of Comparative Examples 5 and 6 decreased from 22 to 50.

[0110] Number of unsaturated functional groups In addition, the number of each functional group (ethylene ethylene, trisubstituted vinyl, vinyl, and vinylidene) per 1,000 carbon atoms in the copolymer was measured by nuclear magnetic resonance analysis, as follows: The copolymer was dissolved in 1,1,2,2-deuterated tetrachloroethane (TCE-d2) solvent and measured at 393 K using a Bruker AVANCE III 500MHz NMR instrument.

[0111] exist 1In the 1H NMR spectrum, the TCE-d2 peak was corrected to 6.0 ppm, and the content ratio of comonomers was calculated using the integral values ​​in the 1.4 ppm and 0.96 ppm regions. The contents of vinyl, ethylene ide, ethylene ethylene, and trisubstituted vinyl groups observed in the range of 4.7 ppm to 5.6 ppm were calculated (analytical method: AMT-3863). Peak assignments are referenced in [Macromolecules 2014, 47, 3282-3790].

[0112] Table 2 Experimental Example 2 200g of ethylene-α-olefin copolymer, 200g of Eastman's Regaltac H100W, 100g of Sasol's H1, and 2.5g of antioxidant, prepared in the above examples and comparative examples, were placed in a beaker, heated and melted using a heating mantle, and then thoroughly stirred and mixed with an impeller to produce an adhesive.

[0113] Viscosity measurement The following method was used to measure the viscosity using a Brookfield RVDV3T viscometer. Specifically, the obtained adhesive was placed in an 8 mL sample chamber and heated to 150°C using a Brookfield Thermosel. After the sample was completely melted, the viscometer was lowered, the rotor was fixed in the sample chamber, and the rotation speed of the rotor (SC-21 high-temperature melting rotor) was fixed at 5 rpm. The readings were then taken for at least 20 minutes or until the values ​​stabilized, and the final values ​​were recorded.

[0114] Using the same method, the viscosity was measured when the heating temperature was set to 177°C. On the other hand, if the viscosity was less than 450 cp or greater than 1,400 cp, the fluidity was too high or too low, resulting in poor processability and uneven bonding surfaces.

[0115] Measurement of fiber tear The obtained adhesive is used to form a film of uniform thickness using a roller coater, which is then transferred onto kraft paper and bonded together. The paper is then stored in ovens at -30°C and 25°C. After a certain storage period, the film is peeled off, and the proportion of the bonded area is calculated to determine fiber tearing. Fiber tearing represents the area where the adhesive force is maintained; a larger area indicates better adhesion.

[0116] The results of the evaluation, based on the following criteria, are shown in Table 3.

[0117] ◎: Fiber tear rate greater than 75% ○: Fiber tearing greater than 50% △: Fiber tearing greater than 25% ×: Fiber tearing less than 25% Measurement of set time After the adhesive is fully melted in an oven at 180°C, it is applied to kraft paper to a certain thickness. The kraft paper is then quickly attached. The kraft paper is peeled off every second, and the time required for the bonded area to reach more than 50% is measured. A shorter curing time indicates less time for the adhesive to cure and gain adhesion, thus indicating excellent productivity.

[0118] The results of the evaluation, based on the following criteria, are shown in Table 3.

[0119] ◎: Curing time less than 5 seconds ○: Curing time less than 10 seconds △: Curing time less than 15 seconds ×: Curing time 15 seconds or more Shear-bonded failure temperature (SAFT, °C) After the adhesive was fully melted in a 180°C oven, it was coated onto kraft paper to a certain thickness, and then the kraft paper was quickly glued onto it to create test pieces. The shear bond failure temperature of each test piece was measured using a 500g weight in shear mode, according to ASTM D4498. The test started at room temperature (25°C), and the oven temperature was increased at an average rate of 0.5°C / min, with the temperature at which the test piece failed (detached) recorded. The shear bond failure temperature is the temperature at which the adhesive surface detaches due to shear load when the adhesive is exposed to high temperatures; therefore, a higher temperature indicates better high-temperature adhesion.

[0120] Table 3 Examples 1 to 5, as ethylene-α-olefin copolymers with density, viscosity, and FWHM within the appropriate range of the present invention, exhibit excellent low-temperature and room-temperature adhesion, excellent productivity due to short curing time, and excellent high-temperature adhesion confirmed by elevated shear bond failure temperature.

[0121] On the other hand, Comparative Example 1, as an adhesive containing a very high-viscosity ethylene-α-olefin copolymer, exhibits excellent adhesion due to its high viscosity. However, at 177°C, its viscosity exceeds 1,400 cp, resulting in very low flowability. This leads to difficulties in adhesive application, poor processability, and uneven bonding surfaces. Furthermore, the long curing time results in a prolonged time to achieve adhesion, leading to poor productivity. Conversely, Comparative Example 2 has a very low viscosity, resulting in very high flowability. This, in turn, makes adhesive application difficult, leads to poor processability, and reduces adhesion.

[0122] Furthermore, the low-temperature and room-temperature adhesion of Comparative Examples 3 to 6 were poor, or the adhesives cured slowly, resulting in poor productivity, and the high-temperature adhesion was also poor.

[0123] Furthermore, Comparative Examples 7 to 9 showed a lower shear bond failure temperature compared to the Examples, thus confirming poor high-temperature adhesion.

Claims

1. An ethylene-α-olefin copolymer that satisfies the following conditions (a) to (c): (a) Density: 0.867 g / cc to 0.889 g / cc; (b) Viscosity: 16,000 cP to 20,000 cP at 177°C; (c) The full width at half maximum (FWHM) of the crystallization peaks, as measured by cross-fractional chromatography, is 22 to 50.

2. The ethylene-α-olefin copolymer according to claim 1, wherein, The density is between 0.868 g / cc and 0.888 g / cc.

3. The ethylene-α-olefin copolymer according to claim 1, wherein, The full width at half maximum (FWHM) of the crystallization peaks, as measured by the cross-fractional chromatography, ranged from 22.2 to 49.0 when the crystallization temperature was measured.

4. The ethylene-α-olefin copolymer according to claim 1, wherein, The melt index of the ethylene-α-olefin copolymer is 400 dg / min to 1,600 dg / min at 190°C and 2.16 kg load.

5. The ethylene-α-olefin copolymer according to claim 1, wherein, The number of vinyl functional groups in the ethylene-α-olefin copolymer, as measured by nuclear magnetic resonance analysis, ranges from 0.01 to 2.0 per 1,000 carbon atoms.

6. The ethylene-α-olefin copolymer according to claim 1, wherein, The number of ethylene-α-olefin copolymers per 1,000 carbon atoms, as measured by nuclear magnetic resonance analysis, ranges from 0.01 to 0.

9.

7. The ethylene-α-olefin copolymer according to claim 1, wherein, The number of ethylene-α-olefin copolymers per 1,000 carbon atoms, as measured by nuclear magnetic resonance analysis, ranges from 0.1 to 1.

9.

8. The ethylene-α-olefin copolymer according to claim 1, wherein, The number of trisubstituted vinyl functional groups per 1,000 carbon atoms in the ethylene-α-olefin copolymer, as measured by nuclear magnetic resonance analysis, is between 0.01 and 0.

8.

9. The ethylene-α-olefin copolymer according to claim 1, wherein, The melting temperature of the ethylene-α-olefin copolymer is 50°C to 90°C.

10. The ethylene-α-olefin copolymer according to claim 1, wherein, The crystallization temperature of the ethylene-α-olefin copolymer is 30°C to 70°C.

11. An adhesive composition comprising: an ethylene-α-olefin copolymer as described in any one of claims 1 to 10; and a tackifier.

12. The adhesive composition according to claim 11, wherein, The tackifier is selected from one or more of the following: modified C5 hydrocarbon resin, styrene-modified terpene resin, fully hydrogenated or partially hydrogenated C9 hydrocarbon resin, hydrogenated alicyclic hydrocarbon resin, hydrogenated aromatic modified alicyclic hydrocarbon resin, and mixtures thereof.

13. The adhesive composition according to claim 11, wherein, The adhesive composition has a viscosity of 450 cP to 1,400 cP at 177°C.

Citation Information

Patent Citations

  • US5064802A