Curable composition and product

A technology for curable compositions and cured products, applied in the field of curable compositions and products, can solve the problems of time-consuming, brittle, and hardened products, and achieve the effect of ensuring design freedom

Inactive Publication Date: 2019-03-01
CEMEDAINE CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, in the photocurable adhesive composition described in Patent Document 1, when light is irradiated, it is necessary to shield the photocurable adhesive composition from the outside air by a PET film or the like. Objects that can be coated with a photocurable adhesive composition, and it takes time to obtain a cured product with adhesive properties
[0008] In addition, in the "(a) method of physically shielding oxygen" described in Non-Patent Document 1, the curable composition cannot be treated in air, and in the "(b) method of selecting an initiator system", although in a certain Oxygen-inhibited polymerization is inhibited to a certain extent, but its effect is not sufficient
In addition, in "(c) Method of selecting a monomer", in the case of using a multifunctional monomer, since the multifunctional monomer contains many crosslinking points, there is a possibility that the cured product of the curable composition becomes hard and brittle. The problem
However, in the case of using a monomer having a hydroxyl group, although oxygen-inhibited polymerization is suppressed to a certain extent, the effect is not sufficient
Furthermore, in the case of using N-vinylamide monomer, due to the high polarity of the compound, the compatibility with other compounding substances is poor, and there is a problem that the cured product obtained by curing is also hard. In the method, there is a problem that the effect of inhibiting polymerization inhibition is small
In addition, in the method of using a phosphorus-based secondary antioxidant deterioration agent, there is a problem that the effect lasts only for about 24 hours after the antioxidant is added.
Then, in "(d) Method of photocuring using thiol / ene", there is a problem of poor storage stability due to the presence of mercapto groups
Furthermore, since a polyfunctional vinyl compound and a polyfunctional thiol are combined for photocuring, there is a problem that the cured product of the curable composition becomes hard and brittle.

Method used

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  • Curable composition and product
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  • Curable composition and product

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0180] Hereinafter, an Example is given and it demonstrates more concretely. It should be noted that these Examples are illustrative and should not be construed as limiting, which is self-evident.

Synthetic example 1

[0181] (Synthesis example 1) GMA decanoic acid

[0182] Add 4.00 g (28.1 mmol) of glycidyl methacrylate (product name "LIGHTESTER G", manufactured by Kyoeisha Science Co., Ltd.), 4.85 g (28.1 mmol) of capric acid, and 0.074 g (0.28 mmol) of triphenylphosphine as a catalyst. , and allowed to react for 24 hours at 60°C. A light brown compound (GMADAc) mainly composed of 2-hydroxy-3-decanoyloxypropyl methacrylate was obtained. From the results of the IR spectrum measurement of the compound, it was confirmed that the -OH stretching (broad peak, 3300 to 2500 cm- 1 ) absorption disappears. In addition, it was confirmed that -OH stretching (broad peak, 3300 to 3600 cm- 1 )peak.

[0183] It should be noted that, in the above synthesis reaction, the epoxy group of glycidyl methacrylate is ring-opened, and is bonded with an unsaturated carboxylic acid to form an ester bond. The ring-opening occurs at both the α-position and the β-position, and the α-adduct formed at the α-position ...

Synthetic example 2

[0184] (Synthesis Example 2) GMA 2-ethylhexanoic acid

[0185] Add 5.00 g (35.2 mmol) of glycidyl methacrylate, 5.07 g (35.2 mmol) of 2-ethylhexanoic acid, and 0.092 g (0.35 mmol) of triphenylphosphine as a catalyst, and react at 60°C for 24 hours . A dark brown compound (GMA2EHAc) mainly composed of 2-hydroxy-3-(2-ethylhexanoyloxy)propyl methacrylate was obtained. From the results of the IR spectrum measurement of the compound, it was confirmed that the -OH stretching (broad peak, 3300 to 2500 cm- 1 ) absorption disappears. In addition, it was confirmed that -OH stretching (broad peak, 3300 to 3600 cm- 1 )peak.

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Abstract

Provided are: a curable composition which is able to undergo an adequate polymerization reaction by considerably suppressing polymerization inhibition by oxygen even if used in air, while being capable of ensuring a degree of freedom of design of the composition; and a product. This curable composition contains (A) a monoacrylate compound that is represented by general formula (1), general formula(2) or general formula (3) and at least one initiator selected from the group consisting of (B1) a photoinitiator, (B2) a thermal initiator and (B3) a redox initiator. (In general formula (1), general formula (2) and general formula (3), R1 represents -H or -CH3. In general formula (1), R2 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a heterocyclic ring structure-containing group, a group having a plurality of rings or -(CmH2mO)nR5 (wherein m represents an integer of 2-4, n represents an integer of 1-30, and R5 represents -H, a substitutedor unsubstituted alkyl group or a substituted or unsubstituted phenyl group). In general formula (2), each of R3 and R4 represents -H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a heterocyclic ring structure-containing group, -(CmH2mO)nR5 (wherein m represents an integer of 2-4, n represents an integer of 1-30, and R5 represents -H, a substituted or unsubstituted alkyl group or a substituted or unsubstituted phenyl group), or a group having a plurality of rings; or alternatively, R3 and R4 may combine with each other and form a cyclic structure or aheterocyclic structure together with carbon atoms to which R3 and R4 are bonded. In general formula (3), each of R' and R'' represents an organic group or a hydrogen atom.)

Description

technical field [0001] The invention relates to a curable composition and a product. In particular, the present invention relates to a curable composition and product containing a compound that inhibits oxygen-inhibited polymerization. Background technique [0002] Conventionally, there is known a photocurable adhesive composition comprising: a (meth)acrylate oligomer having polyisoprene in its skeleton, and a hydrogenated terpene phenolic tackifier (for example, Refer to Patent Document 1). In Patent Document 1, the photocurable adhesive composition of Patent Document 1 is coated on a PET film, the PET film after double-sided peeling treatment is covered from the coated surface, and UV light is irradiated to obtain Adhesive cured product. According to the photocurable adhesive composition of Patent Document 1, it is possible to provide a photocurable adhesive combination that provides a cured product that is excellent in workability during dissolution preparation and coa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F20/10
CPCC08F20/10
Inventor 冈村直实河村尚孝角矢敦史阿部宽生
Owner CEMEDAINE CO LTD
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