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WO2025159134A1 - Composition de résine durcissable par rayonnement d'énergie active - Google Patents

Composition de résine durcissable par rayonnement d'énergie active

Info

Publication number
WO2025159134A1
WO2025159134A1 PCT/JP2025/001961 JP2025001961W WO2025159134A1 WO 2025159134 A1 WO2025159134 A1 WO 2025159134A1 JP 2025001961 W JP2025001961 W JP 2025001961W WO 2025159134 A1 WO2025159134 A1 WO 2025159134A1
Authority
WO
WIPO (PCT)
Prior art keywords
curable resin
active energy
energy ray
resin composition
component
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/JP2025/001961
Other languages
English (en)
Japanese (ja)
Inventor
晴彦 西田
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sekisui Fuller Co Ltd
Original Assignee
Sekisui Fuller Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sekisui Fuller Co Ltd filed Critical Sekisui Fuller Co Ltd
Publication of WO2025159134A1 publication Critical patent/WO2025159134A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G

Definitions

  • the present invention relates to an active energy ray-curable resin composition.
  • active energy ray-curable resin compositions have been widely used in applications such as coatings, adhesives, and cast-in-place liquid gaskets (CIPGs), due to their ability to cure in a short time.
  • CIPGs cast-in-place liquid gaskets
  • active energy ray-curable resin compositions used in the applications described above if the cured surface is exposed to air (oxygen) during photocuring, oxygen inhibition can occur, resulting in insufficient curing of the cured surface and the development of tackiness.
  • active energy ray-curable resin compositions used in coating and CIPG applications are required to have a tack-free cured surface to prevent dirt from adhering to the cured surface and to prevent substrates from sticking to each other.
  • Being tack-free plays a major role in reworkability, as it allows for easy peeling in the event of a defect in components where CIPG is applied to a housing containing a device and then bonded to a cover case.
  • the CIPG thickness needs to be increased depending on the shape and design of the component, and good deep curing properties are required.
  • a photocurable composition containing specific components such as an elastomer (A), a monomer (B) having a (meth)acryloyl group, and a photopolymerization initiator (C) has been proposed (see, for example, Patent Document 1).
  • the photocurable composition described in Patent Document 1 uses a specific elastomer (A) and a monomer (B) having a (meth)acryloyl group. Because the Tg of the monomer having a (meth)acryloyl group is high, the composition is expected to have high hardness. Active energy ray-curable resin compositions used in CIPG applications, etc., are required to have low hardness in the cured product. Furthermore, to improve the tack-free properties and reworkability of the cured surface, measures to increase crosslink density by using multifunctional acrylates or low-molecular-weight urethane acrylates are commonly used. However, using these measures raises the problem of high hardness in the cured product. When such cured products are used in housings made of resins such as ABS and polycarbonate, they can experience creep deformation.
  • a thiol compound into the active energy ray-curable resin composition or by selecting an oligomer skeleton, it is possible to form a soft cured product with low hardness, but this results in problems such as lower strength and reduced resistance to tearing under moist heat. Furthermore, the cured product is prone to developing surface tack, which reduces reworkability.
  • the photocurable composition described in Patent Document 1 has not been fully investigated in terms of exhibiting properties suitable for CIPG applications, such as dischargeability and a high aspect ratio.
  • Active energy ray-curable resin compositions used in CIPG applications are required to be able to be applied to the desired CIPG shape when applied to the desired location at a certain discharge pressure and application speed, in other words, to have excellent dischargeability.
  • the discharge volume at a certain discharge pressure is low, the composition cannot be used for CIPG applications.
  • the above-mentioned active energy ray-curable resin composition is required to be able to form the desired shape, and the resulting cured product must exhibit a high aspect ratio.
  • the present invention aims to provide an active energy ray-curable resin composition that has excellent dischargeability and deep curing properties, and that can produce a cured product with low hardness and a high aspect ratio, as well as good reworkability and moist heat tear resistance.
  • an active energy ray-curable resin composition containing specific components (A) to (D), where component (C) includes a compound having a benzoyl group, and wherein the active energy ray-curable resin composition is irradiated with ultraviolet light using a high-pressure mercury lamp at an illuminance of 300 mW/ cm2 and an integrated light dose of 3,000 mJ/ cm2 , and the resulting cured product has a thickness of 2 mm, and the cured product has a storage modulus G' at 25°C of 700,000 Pa or less, a Tan ⁇ peak temperature of 15°C or less, and a Tan ⁇ peak height of 1.7 or less, as measured using a dynamic viscoelasticity apparatus in a rotational shear mode with an oscillation frequency of 1 Hz, a heating rate of 5°C/min, and a temperature range of -60°C to 70°C, and thereby completed the present
  • An active energy ray-curable resin composition containing the following components (A), (B), (C), and (D): (A) a urethane acrylate oligomer having a weight average molecular weight of 10,000 or more and less than 40,000, which is composed of a urethane skeleton having an ether bond; (B) a monofunctional acrylate monomer, (C) a photopolymerization initiator, (D) fumed silica, The component (C) contains a compound having a benzoyl group, The active energy ray-curable resin composition is irradiated with ultraviolet light using a high-pressure mercury lamp at an illuminance of 300 mW/ cm2 and an integrated light dose of 3000 mJ/ cm2 to obtain a cured product having a thickness of 2 mm.
  • An active energy ray-curable resin composition comprising: 2. The active energy ray-curable resin composition according to Item 1, wherein the component (C) includes (i) methylbenzoyl formate and (ii) a benzophenone compound or an ⁇ -hydroxyacetophenone compound. 3.
  • the component (B) contains the following components (B1) and (B2): (B1) phenoxyethyl acrylate; (B2) C8 or C12 alkyl acrylate, or C9 to C10 alkyl acrylate having an iso structure; and the content of the component (B2) is 30% by mass or less, where the total content of the components (B1) and (B2) is 100% by mass.
  • the active energy ray-curable resin composition of the present invention has excellent dischargeability and deep curing properties, and the cured product has low hardness and a high aspect ratio, and the cured product exhibits good reworkability and moist heat tear resistance.
  • the active energy ray-curable resin composition of the present invention is an active energy ray-curable resin composition containing the following components (A), (B), (C), and (D): (A) a urethane acrylate oligomer having a urethane skeleton having an ether bond and a weight average molecular weight of 10,000 or more but less than 40,000, (B) a monofunctional acrylic acid ester monomer, (C) a photopolymerization initiator, and (D) fumed silica; the component (C) contains a compound having a benzoyl group; and the active energy ray-curable resin composition is photoirradiated with a high-pressure mercury lamp at an illuminance of 300 mW/ cm2 and an integrated light dose of 3,000 mJ/cm.
  • the cured product having a thickness of 2 mm obtained by UV irradiation under the conditions of 2 is an active energy ray-curable resin composition having a storage modulus G' at 25°C of 700,000 Pa or less, a Tan ⁇ peak temperature of 15°C or less, and a Tan ⁇ peak height of 1.7 or less, as measured using a dynamic viscoelasticity device in a rotational shear mode with an oscillation frequency of 1 Hz, a heating rate of 5°C/min, and a temperature range of -60°C to 70°C.
  • the active energy ray-curable resin composition having the above characteristics contains the specific components (A) to (D) described above, and component (C) contains a compound having a benzoyl group. Furthermore, when cured under specific conditions, the cured product exhibits the above-mentioned properties, resulting in excellent dischargeability of the active energy ray-curable resin composition.
  • dischargeability refers to the ability to apply a CIPG or other cured product to the desired shape (bead shape) when applied at a certain discharge pressure and application speed to the desired location. It means that application can be performed under a wide range of conditions, specifically, that a wide range of bead widths can be achieved within a specified discharge pressure range, and that a wide range of bead heights can be achieved, but does not mean that a wide range of bead widths and bead heights can be applied.
  • the active energy ray-curable resin composition of the present invention has the above-mentioned configuration, it has excellent deep curing properties, the cured product has low hardness and excellent flexibility, and the cured product can exhibit a high aspect ratio, and the cured product can exhibit good reworkability and moist heat tear resistance.
  • the active energy ray-curable resin composition of the present invention as described above can be used for CIPG applications in a variety of products, and can be suitably used in, for example, control devices such as sensors, devices for home appliances, digital cameras, and automotive electrical components.
  • the active energy ray-curable resin composition of the present invention is irradiated with ultraviolet light using a high-pressure mercury lamp at an illuminance of 300 mW/ cm2 and an integrated light dose of 3,000 mJ/ cm2 to obtain a cured product having a thickness of 2 mm.
  • the cured product has a storage modulus G' of 700,000 Pa or less at 25°C, as measured using a dynamic viscoelasticity analyzer in a rotational shear mode with a vibration frequency of 1 Hz, a heating rate of 5°C/min, and a temperature range of -60°C to 70°C. If the storage modulus G' of the cured product exceeds 700,000 Pa, the hardness increases.
  • the storage modulus G' is preferably 650,000 Pa or less, more preferably 650,000 Pa or less, and even more preferably 600,000 Pa or less.
  • the lower limit of the storage modulus G' is not particularly limited and may be, for example, 100,000 Pa, 200,000 Pa, 300,000 Pa, or 400,000 Pa.
  • the active energy ray-curable resin composition of the present invention is irradiated with ultraviolet light using a high-pressure mercury lamp at an illuminance of 300 mW/ cm2 and an integrated light dose of 3,000 mJ/ cm2 to obtain a cured product having a thickness of 2 mm.
  • the cured product has a Tan ⁇ peak temperature of 15°C or less, measured using a dynamic viscoelasticity apparatus in a rotational shear mode with an oscillation frequency of 1 Hz, at a temperature rise rate of 5°C/min, and in a temperature range of -60°C to 70°C.
  • the Tan ⁇ peak temperature is preferably 10°C or less.
  • the lower limit of the Tan ⁇ peak temperature is not particularly limited and may be -25°C, -20°C, etc.
  • the active energy ray-curable resin composition of the present invention is irradiated with ultraviolet light using a high-pressure mercury lamp at an illuminance of 300 mW/ cm2 and an integrated light dose of 3,000 mJ/ cm2 , resulting in a 2 mm-thick cured product.
  • a dynamic viscoelasticity analyzer in a rotational shear mode with a vibration frequency of 1 Hz, at a temperature increase rate of 5°C/min, and in a temperature range of -60°C to 70°C, the peak height of Tan ⁇ is 1.7 or less. If the Tan ⁇ peak height exceeds 1.7, reworkability is reduced.
  • the Tan ⁇ peak height is preferably 1.5 or less, more preferably 1.3 or less.
  • the lower limit of the Tan ⁇ peak height is not particularly limited and may be 0.8 or 0.85.
  • the storage modulus G', Tan ⁇ peak temperature, and Tan ⁇ peak height are specifically measured by the following measurement method.
  • Measurement method for dynamic viscoelasticity (storage modulus G', Tan ⁇ peak temperature, and Tan ⁇ peak height): A 2 mm thick silicone rubber sheet formed into a rectangular frame was prepared as a spacer. The spacer was then placed on a release-treated aluminum plate, and an active energy ray-curable resin composition was dripped into the spacer frame. Quartz glass was prepared, placed on top of the active energy ray-curable resin composition, and compressed. In this state, ultraviolet light was irradiated using a high-pressure mercury lamp at an illuminance of 300 mW/ cm2 and an integrated light dose of 3000 mJ/ cm2 . The quartz glass was then peeled off to prepare a sample for dynamic viscoelasticity measurement.
  • dynamic viscoelasticity measurements (heating process) were performed using a dynamic viscoelasticity measuring device (TA Instruments, Model HR-10) in rotational shear mode at a frequency of 1 Hz, over a temperature range of -60°C to 70°C, and at a heating rate of 5°C/min.
  • the peak temperature, peak height, and storage modulus G' at 25°C of Tan ⁇ obtained by the measurement are taken as the measured values.
  • Component (A) is a urethane acrylate oligomer having a weight average molecular weight of 10,000 or more and less than 40,000, which is composed of a urethane skeleton having an ether bond.
  • the weight-average molecular weight (Mw) of component (A) is 10,000 or more and less than 40,000. If the weight-average molecular weight is less than 10,000, the hardness of the cured product of the active energy ray-curable resin composition will be too high, making it unsuitable for applications such as CIPG.
  • the weight-average molecular weight is preferably 11,000 to 38,000, and more preferably 13,000 to 33,000.
  • the weight-average molecular weight (Mw) is a measured value obtained by converting it to standard polystyrene using a gel permeation chromatograph (GPC) measuring device.
  • the urethane acrylate oligomer of component (A) has a urethane backbone with an ether bond, and is not particularly limited as long as its weight-average molecular weight is within the above range.
  • examples of such urethane acrylate oligomers include urethane acrylates having a polytetramethylene ether glycol derivative backbone, a polypropylene glycol backbone, a polyethylene glycol backbone, or modified structures of these.
  • the urethane acrylate oligomer of component (A) can be obtained by reacting a polyol having the above-mentioned polytetramethylene ether glycol derivative skeleton, polyether polycarbonate skeleton, polypropylene glycol skeleton, polyethylene glycol skeleton, polypropylene triol skeleton, or modified structures thereof with at least one isocyanate compound selected from the group consisting of alicyclic diisocyanate compounds, aliphatic diisocyanate compounds, and aromatic diisocyanate compounds, followed by an addition reaction (also known as a urethanization reaction) between the isocyanate group and the hydroxyl group of an acrylate having a hydroxyl group.
  • an addition reaction also known as a urethanization reaction
  • the above diisocyanate compound is preferably an alicyclic diisocyanate, such as 4,4'-methylenebis(cyclohexyl isocyanate), 1,3-(isocyanatomethyl)cyclohexane, or isophorone diisocyanate.
  • urethane acrylate oligomer (A) Commercially available products can be used as the urethane acrylate oligomer (A). Examples of such commercially available products include UV-3300B (manufactured by Mitsubishi Chemical Corporation) and UV-3700B (manufactured by Mitsubishi Chemical Corporation).
  • the content of component (A) is preferably 4 to 45% by mass, more preferably 7 to 40% by mass, and even more preferably 9 to 30% by mass, based on 100% by mass of the active energy ray-curable resin composition.
  • the content of component (A) is preferably 4 to 45% by mass, more preferably 7 to 40% by mass, and even more preferably 9 to 30% by mass, based on 100% by mass of the active energy ray-curable resin composition.
  • the content of component (A) relative to the total of component (A) and component (B), which will be described later, is preferably 5 to 45% by mass, more preferably 8 to 40% by mass, and even more preferably 10 to 30% by mass.
  • the dischargeability of the active energy ray-curable resin composition is further improved, and the cured product can have lower hardness and a higher aspect ratio, and can exhibit better reworkability and moist heat tear resistance.
  • Component (B) is a monofunctional acrylic acid ester monomer.
  • the hardness of the cured product of the active energy ray-curable resin composition is reduced, making it suitable for use in CIPG applications, etc.
  • the active energy ray-curable resin composition of the present invention can exhibit excellent reworkability and moist heat tear resistance.
  • Component (B) is not particularly limited as long as it is a monofunctional acrylic acid ester monomer.
  • monofunctional acrylic acid ester monomers include monofunctional (meth)acrylic acid ester monomers having one unsaturated bond in the molecule.
  • benzophenone compounds include benzophenone, 4-methylbenzophenone, 4-phenylbenzophenone, and benzophenone derivatives.
  • the benzophenone compound contained in component (C) may be a commercially available product.
  • Examples of such commercially available products include those manufactured by iGM Resins under the product names "Ommiad BP Flakes,” “Omnirad 4MBZ Flakes,” “Omnirad BMS,” “Omnirad EMK,” “Omnirad OMBB,” and “Omnirad 4PBZ.”
  • benzyl ketal compounds examples include 2,2-dimethoxy-2-phenylacetophenone.
  • Commercially available products of the above benzyl ketal compounds include "Omnirad 651.”
  • Component (D) Component (D) is fumed silica.
  • the Shore A hardness of the cured product is measured using the method described in the Examples.
  • A Component (A1): Urethane acrylate (polyether skeleton), Mw 13000, product name Art Resin UN-6304 (manufactured by Negami Chemical Industrial Co., Ltd.)
  • the active energy ray-curable resin composition was applied to a 5cm x 15cm stainless steel plate to a width of 1000 ⁇ 150 ⁇ m, a height of 750 ⁇ m ⁇ 50 ⁇ m, and a length of 11cm.
  • the active energy ray-curable resin composition was applied in two parallel bead-like strips spaced 2cm apart.
  • the cured product was then cured using the same UV irradiation device and light source as in the hardness measurement described above, with an illuminance of 300mW/ cm2 and an integrated light dose of 3000mJ/ cm2 . 5mm of each end of the bead-like cured product was then cut to a length of 10cm.
  • a test specimen was prepared by sandwiching the bead between two SUS plates of the same size using a 0.5mm thick aluminum spacer to achieve a compression ratio of approximately 30%.
  • the SUS plates were then clamped in place until they were tightly attached to the spacers.
  • the test piece was then exposed to an oven at 70°C for 5 hours, and then left in an environment at 25°C for 19 hours.
  • the clamp was removed and the test piece was evaluated according to the following evaluation criteria.
  • a rating of ⁇ indicates that there is no problem in actual use.
  • ⁇ The SUS plate can be easily peeled off by hand without resistance, and no residue remains on the peeled surface of the SUS plate.
  • ⁇ The adhesive was so strong that the SUS plate could not be peeled off even with manual force.
  • an active energy ray-curable resin composition was applied to a peelable PET film to form a bead height of 900 ⁇ m ⁇ 100 ⁇ m and a bead length of 10 cm.
  • the composition was then cured by irradiation with UV light at an illuminance of 300 mW/ cm2 and an integrated light dose of 3000 mJ/ cm2 to prepare a test specimen.
  • the test specimen was then left in a high-temperature, high-humidity chamber set at 40°C and 95% humidity for 168 hours, then removed and left at room temperature for another day.
  • the test specimen was used to measure the breaking strength at 23°C ⁇ 2°C using a universal tensile tester (Shimadzu Corporation, Autograph) and evaluated for wet heat tear resistance according to the following evaluation criteria. A rating of ⁇ or higher was deemed acceptable for practical use.
  • ⁇ Breaking force 1.5N or more
  • ⁇ Breaking force 0.8N to less than 1.5N
  • ⁇ Breaking force less than 0.8N
  • Dynamic viscoelasticity (storage modulus G', Tan ⁇ peak temperature, Tan ⁇ peak height)
  • a 2 mm-thick silicone rubber sheet formed into a rectangular frame was prepared as a spacer.
  • the spacer was then placed on a release-treated aluminum plate, and the active energy ray-curable resin composition was dripped into the spacer frame.
  • Quartz glass was prepared, placed on top of the active energy ray-curable resin composition, and compressed.
  • UV irradiation was performed using the same UV irradiation device and light source as used in the hardness measurement above , at an illuminance of 300 mW/cm2 and an integrated light dose of 3000 mJ/ cm2 .
  • the quartz glass was then peeled off to prepare a sample for dynamic viscoelasticity measurement.
  • dynamic viscoelasticity measurements (heating process) were performed using a dynamic viscoelasticity measuring device (TA Instruments, Model: HR-10) in rotational shear mode at a frequency of 1 Hz over a temperature range of -60°C to 70°C at a heating rate of 5°C/min.
  • the peak temperature and peak height of Tan ⁇ and the storage modulus G' at 25°C were recorded as measured values.
  • Dischargeability The same apparatus and SUS plate were prepared as in the aspect ratio measurement method described above. The temperature of the active energy ray-curable resin composition was adjusted to 25.0°C, and then the active energy ray-curable resin composition was applied to a length of 11 cm using an 18G nozzle at a coating pressure of 150 kPa and a coating speed of 30 mm/s, with the gap between the SUS plate and the nozzle tip adjusted to 6.0 mm. The weight of the applied active energy ray-curable resin composition was measured, and this was used as the discharge amount. Dischargeability was evaluated according to the following evaluation criteria. A rating of fair or better was deemed acceptable for practical use. ⁇ : Discharge amount 0.3g or more ⁇ : Discharge amount 0.15g or more but less than 0.3g ⁇ : Discharge amount 0.05g or more but less than 0.15g ⁇ : Discharge amount less than 0.05g
  • An active energy ray-curable resin composition was applied to a deep-curing release-treated aluminum plate to a thickness of 2.0 mm ⁇ 0.1 mm, and cured by UV irradiation using the same UV irradiation device and light source as used in the hardness measurement above, under conditions of an illuminance of 300 mW/ cm2 and an integrated light dose of 3000 mJ/ cm2 .
  • the cured product was then peeled from the aluminum plate, and the cured state of the back surface was visually observed, and deep curability was evaluated according to the following criteria.
  • a rating of ⁇ indicates that there is no problem in practical use. ⁇ : No liquid uncured material was observed. ⁇ : Liquid uncured material observed
  • Comparative Example 3 was rated as x for deep curability, and because it was difficult to obtain a cured product of the active energy ray-curable resin composition, the hardness (Shore A), storage modulus G', Tan ⁇ peak temperature, and Tan ⁇ peak height could not be measured, and were therefore marked as "measurable.”

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

La présente invention concerne une composition de résine durcissable par rayonnement d'énergie active qui présente d'excellentes propriétés d'éjection et d'aptitude au durcissement dans une partie profonde, et qui permet d'obtenir un produit durci qui présente une faible dureté, qui peut présenter un rapport d'aspect élevé, et qui peut présenter une bonne aptitude au refaçonnage et une bonne résistance à la déchirure à la chaleur humide.　L'invention concerne une composition de résine durcissable par rayonnement d'énergie active qui contient le composant (A), le composant (B), le composant (C) et le composant (D) suivants : (A) un oligomère d'acrylate d'uréthane qui présente un poids moléculaire moyen en poids supérieur ou égal à 10 000 mais inférieur à 40 000 et qui comprend un squelette uréthane comportant une liaison éther ; (B) un monomère d'ester d'acide acrylique monofonctionnel ; (C) un initiateur de photopolymérisation ; et (D) de la silice pyrogénée. La composition de résine durcissable par rayonnement d'énergie active est caractérisée en ce que : le composant (C) contient un composé qui a un groupe benzoyle ; un produit durci, qui présente une épaisseur de 2 mm et qui est obtenu par éclairage de la composition de résine durcissable par rayonnement d'énergie active avec une lumière ultraviolette à un éclairement de 300 mW/cm2 et une quantité de lumière accumulée de 3 000 mJ/cm2 à l'aide d'une lampe au mercure à haute pression, qui présente un module de conservation de l'élasticité G' égal ou inférieur à 700 000 Pa à 25 °C tel que déterminé dans un mode de cisaillement rotatif à une fréquence de vibration de 1 Hz à une vitesse de chauffage de 5 °C/min sur une plage de température de -60 °C à 70 °C à l'aide d'un dispositif de mesure de la viscoélasticité dynamique ; et par rapport au produit durci, le pic de température de Tanδ est égal ou inférieur à 15 °C et la hauteur de pic de Tanδ est égale ou inférieure à 1,7.
PCT/JP2025/001961 2024-01-23 2025-01-22 Composition de résine durcissable par rayonnement d'énergie active Pending WO2025159134A1 (fr)

Applications Claiming Priority (2)

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JP2024-008367 2024-01-23
JP2024008367 2024-01-23

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016194870A1 (fr) * 2015-06-05 2016-12-08 株式会社タイカ Composition de résine durcissable sous l'action d'un rayon d'énergie active, et matériau d'étanchéité et matériau tampon, chacun se composanr du produit durci de celle-ci
JP2019129280A (ja) * 2018-01-26 2019-08-01 協立化学産業株式会社 インプリント成型用光硬化性樹脂組成物
WO2022163443A1 (fr) * 2021-02-01 2022-08-04 ナガセケムテックス株式会社 Composition de résine photodurcissable et produit de stéréolithographie en trois dimensions
WO2023002973A1 (fr) * 2021-07-21 2023-01-26 株式会社スリーボンド Composition photodurcissable
JP2023147244A (ja) * 2022-03-29 2023-10-12 荒川化学工業株式会社 活性エネルギー線硬化型粘着剤組成物、硬化物及び粘着シート

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016194870A1 (fr) * 2015-06-05 2016-12-08 株式会社タイカ Composition de résine durcissable sous l'action d'un rayon d'énergie active, et matériau d'étanchéité et matériau tampon, chacun se composanr du produit durci de celle-ci
JP2019129280A (ja) * 2018-01-26 2019-08-01 協立化学産業株式会社 インプリント成型用光硬化性樹脂組成物
WO2022163443A1 (fr) * 2021-02-01 2022-08-04 ナガセケムテックス株式会社 Composition de résine photodurcissable et produit de stéréolithographie en trois dimensions
WO2023002973A1 (fr) * 2021-07-21 2023-01-26 株式会社スリーボンド Composition photodurcissable
JP2023147244A (ja) * 2022-03-29 2023-10-12 荒川化学工業株式会社 活性エネルギー線硬化型粘着剤組成物、硬化物及び粘着シート

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