TW201336895A - Resin composition - Google Patents

Resin composition Download PDF

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TW201336895A
TW201336895A TW102107219A TW102107219A TW201336895A TW 201336895 A TW201336895 A TW 201336895A TW 102107219 A TW102107219 A TW 102107219A TW 102107219 A TW102107219 A TW 102107219A TW 201336895 A TW201336895 A TW 201336895A
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group
resin composition
meth
carbon
present
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TW102107219A
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Chinese (zh)
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Takako Hoshino
Yoshitsugu Goto
Jun Watanabe
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Denki Kagaku Kogyo Kk
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/045—Polysiloxanes containing less than 25 silicon atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/541—Silicon-containing compounds containing oxygen
    • C08K5/5435—Silicon-containing compounds containing oxygen containing oxygen in a ring
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
    • C09J183/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/005—Stabilisers against oxidation, heat, light, ozone
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B6/00—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings
    • G02B6/10—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings of the optical waveguide type
    • G02B6/12—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings of the optical waveguide type of the integrated circuit kind
    • G02B6/122—Basic optical elements, e.g. light-guiding paths
    • G02B6/1221—Basic optical elements, e.g. light-guiding paths made from organic materials

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Silicon Polymers (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)

Abstract

Provided is a polyene-polythiol resin composition with outstanding heat resistance. A resin composition containing: (A) a silsesquioxane derivative represented by formula [1] below, having a random structure, and having two or more carbon-carbon unsaturated bonds per molecule; (B) a polythiol; and (C) a photoradical polymerization initiator. General formula [1] (R0-SiO3/2)m (in the formula, R0 has one or more functional groups selected from a (meth)acryloyl groups, a vinyl group, a vinyl ether group, an allyl group and an allyl ether group. R0 may be the same or different. Part of the (meth) acryloyl group, vinyl group, vinyl ether group, allyl group and allyl ether group may be substituted with a C1-6 alkyl group, a C1-6 alkoxy group, a C1-6 halogenated alkyl group, a phenyl group, or a halogen. m represents the degree of polymerisation.)

Description

樹脂組成物 Resin composition

本發明涉及例如由多烯(polyene)-多硫醇(polythiol)類樹脂組成物構成的膠黏劑。本發明涉及使用該膠黏劑膠黏的膠黏體、固化物、光學部件。在此，“多”表示二官能性以上的多官能性。 The present invention relates to an adhesive composed of, for example, a polyene-polythiol type resin composition. The present invention relates to an adhesive body, a cured product, and an optical member which are adhered using the adhesive. Here, "multiple" means a difunctional or higher polyfunctionality.

近年來，通過照射紫外線等活性光線或受熱而固化的樹脂組成物在膠黏劑、塗布劑等各種領域中使用。作為這樣的樹脂組成物之一，已知有以多烯和多硫醇作為主成分的樹脂組成物(專利文獻1)。 In recent years, a resin composition which is cured by irradiation with active light such as ultraviolet rays or by heat is used in various fields such as an adhesive and a coating agent. As one of such a resin composition, a resin composition containing a polyene and a polythiol as a main component is known (Patent Document 1).

多烯-多硫醇類樹脂組成物具有在可見光範圍(380~780nm)內的優良的透明性、膠黏性、在空氣下的表面的固化性(以下，稱為表面固化性)，因此，作為玻璃以及透明塑膠用的膠黏劑或成形材料，在光學部件和電子部件等各種領域中使用。 The polyene-polythiol-based resin composition has excellent transparency, adhesiveness, and surface curability (hereinafter referred to as surface curability) in the visible light range (380 to 780 nm). Adhesives or molding materials for glass and transparent plastics are used in various fields such as optical parts and electronic parts.

但是，以往的多烯-多硫醇類樹脂存在在回流焊等超過200℃的高溫暴露等中樹脂組成物發生黃變、透明性降低的課題。因此，期望滿足優良的耐熱性的樹脂組成物。 However, the conventional polyene-polythiol-based resin has a problem that the resin composition is yellowed and the transparency is lowered in high-temperature exposure such as reflow soldering at a temperature higher than 200 °C. Therefore, a resin composition that satisfies excellent heat resistance is desired.

半矽氧烷(silsesquioxane)衍生物作為具有優良的耐熱性和耐光性的樹脂組成物，是近年來備受矚目的材料之一。專利文獻2中公開了通過光或熱進行反應的 自由基反應型或付加反應型的半矽氧烷衍生物、共聚物、樹脂及其製造方法。專利文獻3中公開了利用上述特性的樹脂組成物、清漆、成形體、膠黏劑、膠黏片、密封材料、納米壓印用組成物等。 As a resin composition having excellent heat resistance and light resistance, a silsesquioxane derivative is one of the materials attracting attention in recent years. Patent Document 2 discloses that the reaction is carried out by light or heat. A radically reactive or superadded reaction type hemidecane derivative, copolymer, resin, and a method for producing the same. Patent Document 3 discloses a resin composition, a varnish, a molded body, an adhesive, an adhesive sheet, a sealing material, a composition for nanoimprinting, and the like which utilize the above characteristics.

專利文獻3公開了使用半矽氧烷衍生物的多烯-多硫醇類樹脂組成物具有透明性、膠黏性、耐熱性。並且，還公開了利用上述特性的膠黏劑、液晶密封用的密封劑和固化膜等。 Patent Document 3 discloses that a polyene-polythiol resin composition using a hemidecane derivative has transparency, adhesiveness, and heat resistance. Further, an adhesive using the above characteristics, a sealant for liquid crystal sealing, a cured film, and the like are also disclosed.

【現有技術文獻】 [Prior Art Literature] 【專利文獻】 [Patent Literature]

【專利文獻1】日本特開平03-243626號公報 [Patent Document 1] Japanese Patent Laid-Open No. 03-243626

【專利文獻2】日本特開2004-143449號公報 [Patent Document 2] Japanese Patent Laid-Open Publication No. 2004-143449

【專利文獻3】日本特開2010-168452號公報 [Patent Document 3] Japanese Patent Laid-Open Publication No. 2010-168452

但是，專利文獻2中並未記載有作為膠黏劑的用途。另外，專利文獻2以及專利文獻3的半矽氧烷衍生物為籠型。籠型的半矽氧烷衍生物的樹脂組成物具有不溶解於多烯-多硫醇類樹脂組成物的問題。 However, Patent Document 2 does not describe the use as an adhesive. Further, the semi-aluminoxane derivatives of Patent Document 2 and Patent Document 3 are cage type. The resin composition of the cage-type hemidecane derivative has a problem that it does not dissolve in the polyene-polythiol resin composition.

本發明提供一種樹脂組成物，其含有：(A)每1分子中具有2個以上碳-碳不飽和鍵、並且具有隨機(Random type)結構的由下述通式[1]表示的半矽氧烷衍生物、(B)多硫醇、和(C)光自由基聚合引發劑， The present invention provides a resin composition comprising: (A) a semiquinone represented by the following formula [1] having two or more carbon-carbon unsaturated bonds per molecule and having a random type structure Oxylkane derivative, (B) polythiol, and (C) photoradical polymerization initiator,

通式[1]【化2】 (R 0 -SiO 3/2 ) m General formula [1] [Chemical 2] (R 0 -SiO 3/2 ) m

(式中，R0具有選自(甲基)丙烯醯基(methacryloyl)、乙烯基(vinyl)、乙烯基醚基(vinyl ether group)、烯丙基(allyl)以及烯丙基醚基(allyl ether group)中的一種以上官能團，R0可以相同也可以不同，(甲基)丙烯醯基、乙烯基、乙烯基醚基、烯丙基以及烯丙基醚基的一部分可以由碳原子數1~6的烷基、碳原子數1~6的烷氧基、碳原子數1~6的鹵化烷基、苯基、鹵素取代，m表示聚合度)。 (wherein R 0 has a selected from the group consisting of (meth) methacryloyl, vinyl, vinyl ether group, allyl, and allyl ether (allyl) More than one functional group in the ether group), R 0 may be the same or different, and a part of the (meth)acryloyl group, the vinyl group, the vinyl ether group, the allyl group, and the allyl ether group may be one by one carbon atom An alkyl group of ~6, an alkoxy group having 1 to 6 carbon atoms, a halogenated alkyl group having 1 to 6 carbon atoms, a phenyl group or a halogen group, and m represents a degree of polymerization).

本發明提供在上述樹脂組成物中還含有(D)半矽氧烷衍生物以外的、具有碳-碳不飽和鍵的化合物的樹脂組成物。另外，本發明提供在上述樹脂組成物中還含有(E)抗氧化劑的樹脂組成物。另外，本發明提供在上述樹脂組成物中還含有(F)密合性賦予劑的樹脂組成物。另外，本發明提供由上述樹脂組成物構成的膠黏劑。另外，本發明提供使用上述膠黏劑膠黏的膠黏體。另外，本發明提供由上述樹脂組成物構成的固化物。另外，本發明提供將由上述固化物構成的層、和具有比該層高的折射率的層進行層壓而成的光波導。另外，本發明提供含有上述樹脂組成物的光學部件。 The present invention provides a resin composition further containing a compound having a carbon-carbon unsaturated bond other than the (D) hemidecane derivative in the resin composition. Further, the present invention provides a resin composition further containing (E) an antioxidant in the above resin composition. Moreover, the present invention provides a resin composition further containing (F) an adhesion imparting agent in the resin composition. Further, the present invention provides an adhesive composed of the above resin composition. Further, the present invention provides an adhesive body which is adhered using the above adhesive. Further, the present invention provides a cured product composed of the above resin composition. Further, the present invention provides an optical waveguide in which a layer composed of the above-mentioned cured product and a layer having a refractive index higher than that of the layer are laminated. Further, the present invention provides an optical member containing the above resin composition.

本發明具有例如耐熱性、耐光性、透明性、速固化性或膠黏性。 The present invention has, for example, heat resistance, light resistance, transparency, rapid curability or adhesiveness.

以下，對本發明的實施方式詳細地進行說明。需要說明的是，本說明書中A~B是指A以上且B以下。 Hereinafter, embodiments of the present invention will be described in detail. In the present specification, A to B mean A or more and B or less.

關於(A)多烯 About (A) polyene

本實施方式的(A)多烯為(A)每1分子中具有2個以上碳-碳不飽和鍵、並且具有隨機結構的由下述通式[1]表示的半矽氧烷衍生物。本實施方式的(A)多烯與后述的多硫醇均作為主成分使用。 The (A) polyene of the present embodiment is a semiquinoxane derivative represented by the following general formula [1] which has (A) two or more carbon-carbon unsaturated bonds per molecule and has a random structure. The (A) polyene of the present embodiment and the polythiol described later are used as a main component.

通式[1]【化3】(R 0 -SiO 3/2 ) m General formula [1] [Chemical 3] (R 0 -SiO 3/2 ) m

(式中，R0具有選自(甲基)丙烯醯基、乙烯基、乙烯基醚基、烯丙基以及烯丙基醚基中的一種以上官能團，R0可以相同也可以不同，(甲基)丙烯醯基、乙烯基、乙烯基醚基、烯丙基以及烯丙基醚基的一部分可以由碳原子數1~6的烷基、碳原子數1~6的烷氧基、碳原子數1~6的鹵化烷基、苯基、鹵素取代，m表示聚合度)。 (wherein R 0 has one or more functional groups selected from the group consisting of a (meth) acrylonitrile group, a vinyl group, a vinyl ether group, an allyl group, and an allyl ether group, and R 0 may be the same or different, (A) A part of the acrylonitrile group, the vinyl group, the vinyl ether group, the allyl group and the allyl ether group may be an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a carbon atom. A halogenated alkyl group of 1 to 6 is substituted with a phenyl group or a halogen, and m represents a degree of polymerization).

本實施方式中，優選使用的半矽氧烷衍生物是在分子內具有(甲基)丙烯醯基、乙烯基、乙烯基醚基、烯丙基以及烯丙基醚基這樣的、具有碳-碳不飽和鍵的官能團的半矽氧烷化合物。1分子內的官能團的平均數優選為2~50，更優選為3~10。需要說明的是，1分子內的官能團的平均數可以為2、3、4、5、6、7、8、9、10、15、20、25、30、35、40、45、50中的任意1個值或任意2個值的範圍內。 In the present embodiment, the semiquinoxane derivative preferably used has a carbon (meth) acryl fluorenyl group, a vinyl group, a vinyl ether group, an allyl group, and an allyl ether group in the molecule, and has a carbon- A semi-oxane compound having a functional group of a carbon unsaturated bond. The average number of functional groups in one molecule is preferably 2 to 50, and more preferably 3 to 10. It should be noted that the average number of functional groups in one molecule may be 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 20, 25, 30, 35, 40, 45, 50 Any range of values or any two values.

已知本實施方式的半矽氧烷衍生物可以根據烷氧基矽烷(alkoxysilane)的共水解、共縮合的條件得到梯形或隨機結構，作為梯形結構的半矽氧烷衍生物，例如，可具有下述通式[2]所示的結構。 It is known that the hemidecane derivative of the present embodiment can obtain a trapezoidal or random structure according to the conditions of co-hydrolysis and co-condensation of alkoxysilane, and as a ladder-structured hemidecane derivative, for example, The structure represented by the following general formula [2].

通式[2]【化4】 General formula [2] [化4]

(式中，R0具有選自(甲基)丙烯醯基、乙烯基、乙烯基醚基、烯丙基以及烯丙基醚基中的一種以上官能團，R0可以相同也可以不同，(甲基)丙烯醯基、乙烯基、乙烯基醚基、烯丙基以及烯丙基醚基的一部分可以由碳原子數1~6的烷基、碳原子數1~6的烷氧基、碳原子數1~6的鹵化烷基、苯基、鹵素取代)。 (wherein R 0 has one or more functional groups selected from the group consisting of a (meth) acrylonitrile group, a vinyl group, a vinyl ether group, an allyl group, and an allyl ether group, and R 0 may be the same or different, (A) A part of the acrylonitrile group, the vinyl group, the vinyl ether group, the allyl group and the allyl ether group may be an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a carbon atom. A halogenated alkyl group of 1 to 6 is substituted with a phenyl group or a halogen.

本實施方式的半矽氧烷衍生物以隨機結構的半矽氧烷衍生物作為主成分，但在不阻礙本實施方式的目的的範圍內，也可以含有籠型結構(cage type)的半矽氧烷衍生物或梯形結構的半矽氧烷衍生物。具體而言，本實施方式的半矽氧烷衍生物優選以數平均計含有隨機結構10%以上，特別優選含有20%以上。該隨機結構如果為10%以上，則膠黏性優良。從其他觀點出發如果表現，則本實施方式的半矽氧烷衍生物優選以數平均計含有籠型結構或梯形結構僅90%以下，如果僅為80%以下，則進一步優選。作為本實施方式的半矽氧烷衍生物的隨機結構、籠型結構或梯形結構的含有率的測定方法，例如，可以列舉：將GPC的測定結果與液相色譜法分離後的質譜(LC-MS)的測定結果與1H-NMR的測定結果進行比較 並計算的方法。需要說明的是，本實施方式的半矽氧烷衍生物的隨機結構的含有率以數平均計可以為10%、20%、30%、40%、50%、60%、70%、80%、90%、100%中的任意1個值以上，也可以在任意2個值的範圍內。 The hemidecane derivative of the present embodiment contains a hemidecane derivative having a random structure as a main component, but may contain a cage type of hemi-half in a range not inhibiting the object of the present embodiment. An oxane derivative or a ladder-structured hemidecane derivative. Specifically, the hemidecane derivative of the present embodiment preferably contains a random structure of 10% or more, and particularly preferably 20% or more in terms of a number average. If the random structure is 10% or more, the adhesiveness is excellent. From the other viewpoints, the hemidecane derivative of the present embodiment preferably contains a cage structure or a trapezoidal structure of only 90% or less in terms of number average, and is more preferably 80% or less. The method for measuring the content of the random structure, the cage structure or the trapezoidal structure of the hemidecane derivative of the present embodiment is, for example, a mass spectrum obtained by separating the measurement result of GPC from liquid chromatography (LC- A method in which the measurement result of MS) is compared with the measurement result of 1 H-NMR and calculated. It should be noted that the content of the random structure of the hemidecane derivative of the present embodiment may be 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80% on a numerical average. Any one of 90% or 100% may be in the range of any two values.

半矽氧烷衍生物的分子量優選為100~100000，更優選為500~60000。分子量如果為100以上，則能夠得到優良的耐熱性，如果為100000以下，則膠黏劑的黏度不會變得過高，或者不會損害作業性和成形性，或者在保存穩定性上不會發生問題。需要說明的是，半矽氧烷衍生物的分子量可以為100、200、300、400、500、600、700、800、900、1000、2000、3000、4000、5000、6000、7000、8000、9000、10000、20000、30000、40000、50000、60000、70000、80000、90000、100000中的任意1個值或任意2個值的範圍內。 The molecular weight of the hemidecane derivative is preferably from 100 to 100,000, more preferably from 500 to 60,000. When the molecular weight is 100 or more, excellent heat resistance can be obtained, and if it is 100,000 or less, the viscosity of the adhesive does not become too high, or workability and formability are not impaired, or storage stability is not improved. A problem has occurred. It should be noted that the molecular weight of the hemidecane derivative may be 100, 200, 300, 400, 500, 600, 700, 800, 900, 1000, 2000, 3000, 4000, 5000, 6000, 7000, 8000, 9000. Any one of 10000, 20000, 30000, 40000, 50000, 60000, 70000, 80000, 90000, 100000 or any two values.

低聚物(oligomer)的分子量是指作為每1個分子的平均分子量計算出的重量平均分子量。本實施方式的實施例中，使用通過GPC(凝膠滲透色譜法)測定的聚苯乙烯換算的重量平均分子量。 The molecular weight of the oligomer (oligomer) means the weight average molecular weight calculated as the average molecular weight per molecule. In the examples of the present embodiment, the weight average molecular weight in terms of polystyrene measured by GPC (gel permeation chromatography) was used.

本實施方式的半矽氧烷衍生物中，烯屬不飽和基團每1當量的半矽氧烷衍生物的克數(例如，烯屬不飽和基團為(甲基)丙烯醯基的情況下，相當於(甲基)丙烯醯基當量)，優選為50~300g/eq，更優選為100~200g/eq。烯屬不飽和基團是指選自(甲基)丙烯醯基、乙烯基、乙烯基醚基、烯丙基以及烯丙基醚基中的一種以上的官能團。需要說明的是，烯屬不飽和基團每1當量的半矽氧烷衍生物的克數可以為50、60、70、80、90、100、110、120、130、140、150、160、170、180、190、200、210、220、230、240、250、260、270、280、290、300g/eq中的任意1個值或任意2個值的範圍內。 In the semi-oxane derivative of the present embodiment, the number of grams of the ethylenically unsaturated group per one equivalent of the hemidecane derivative (for example, the case where the ethylenically unsaturated group is a (meth) acrylonitrile group) The ratio is equivalent to (meth)acrylonitrile equivalent, preferably from 50 to 300 g/eq, and more preferably from 100 to 200 g/eq. The ethylenically unsaturated group means one or more functional groups selected from the group consisting of a (meth)acryl fluorenyl group, a vinyl group, a vinyl ether group, an allyl group, and an allyl ether group. It should be noted that the number of grams of the ethylenically unsaturated group per one equivalent of the hemidecane derivative may be 50, 60, 70, 80, 90, 100, 110, 120, 130, 140, 150, 160, Any one of 170, 180, 190, 200, 210, 220, 230, 240, 250, 260, 270, 280, 290, 300 g/eq or any two values.

關於(B)多硫醇 About (B) polythiol

本實施方式的(B)多硫醇在每1分子中具有2個以上巰基。本實施方式的多硫醇的平均分子量優選為50~15000。本實施方式的多硫醇與上述多烯一起作為主成 分使用。作為優選的多硫醇，可以列舉：二巰基丁烷(dimercaptobutane)或三巰基己烷(trimercaptohexane)等巰基取代烷基化合物、二巰基苯等巰基取代烯丙基化合物、巰基乙酸(thioglycolic acid)或巰基丙酸(thiopropionic acid)等多元醇酯以及多元醇的環氧烷烴加成物與硫化氫的反應產物等。 The (B) polythiol of the present embodiment has two or more mercapto groups per molecule. The average molecular weight of the polythiol of the present embodiment is preferably from 50 to 15,000. The polythiol of the present embodiment is combined with the above polyene as a main component Use separately. Preferred examples of the polythiol include a mercapto-substituted alkyl compound such as dimercaptobutane or trimercaptohexane, a mercapto-substituted allyl compound such as dimercaptobenzene, thioglycolic acid or A polyol ester such as thiopropionic acid and a reaction product of an alkylene oxide adduct of a polyhydric alcohol and hydrogen sulfide.

作為本實施方式的多硫醇，可以列舉：三[(3-巰基丙醯氧基)-乙基]異氰脲酸酯、三羥甲基丙烷-三(β-硫代丙酸酯)、三2-羥乙基-異氰脲酸酯、三β-巰基丙酸酯、季戊四醇四(β-硫代丙酸酯)、1,8-二巰基-3,6-二氧雜辛烷、1,8-二巰基-3,6-二硫醚辛烷、三嗪硫醇、以及半矽氧烷衍生物的多硫醇等。本實施方式的多硫醇沒有特別限定，可以單獨使用，也可以為2種以上的混合物。 Examples of the polythiol of the present embodiment include tris[(3-mercaptopropyloxy)-ethyl]isocyanurate, trimethylolpropane-tris(β-thiopropionate), and Tris 2-hydroxyethyl-isocyanurate, tri-β-mercaptopropionate, pentaerythritol tetrakis(β-thiopropionate), 1,8-dimercapto-3,6-dioxaoctane, 1,8-Dimercapto-3,6-dithioether octane, triazine thiol, and a polythiol of a hemidecane derivative. The polythiol of the present embodiment is not particularly limited, and may be used singly or in combination of two or more.

關於本實施方式的(A)半矽氧烷衍生物與(B)多硫醇的質量比，在將(A)與(B)的合計設為100的情況下，優選為5~95：95~5，更優選為15~90：85~10，最優選為35~85：65~15。需要說明的是，該質量比可以為5：95、10：90、15：85、20：80、25：75、30：70、35：65、40：60、45：55、50：50、55：45、60：40、65：35、70：30、75：25、80：20、85：15、90：10、95：5中的任意1個值或任意2個值的範圍內。 In the mass ratio of the (A) hemidecane derivative and (B) polythiol in the present embodiment, when the total of (A) and (B) is 100, it is preferably 5 to 95:95. ~5, more preferably 15~90:85~10, most preferably 35~85:65~15. It should be noted that the mass ratio may be 5:95, 10:90, 15:85, 20:80, 25:75, 30:70, 35:65, 40:60, 45:55, 50:50, Any one of 55:45, 60:40, 65:35, 70:30, 75:25, 80:20, 85:15, 90:10, 95:5 or any two values.

關於(C)光自由基聚合引發劑 About (C) photoradical polymerization initiator

另外，本實施方式的樹脂組成物優選含有(C)光自由基聚合引發劑。 Further, the resin composition of the present embodiment preferably contains (C) a photoradical polymerization initiator.

作為本實施方式的(C)光自由基聚合引發劑，只要是吸收光、產生具有聚合引發能的自由基的化合物，則沒有特別限制。作為本實施方式的光自由基聚合引發劑，可以列舉：苯偶醯(benzil)、苯偶姻(benzoin)、苯偶姻苯甲酸、苯偶姻乙基醚、苯偶姻異丙基醚、苯偶姻異丁基醚等苯偶姻衍生物、二苯甲酮(benzoph enone)、4-苯基二苯甲酮等二苯甲酮衍生物、2,2-二甲氧基-1,2-二苯基乙烷-1-酮、2,2-二乙氧基苯乙酮、苄基二甲基縮酮等烷基苯乙酮衍生物、1-羥基環已基苯基酮、1-(4-異丙基苯基)-2-羥基-2-甲基丙烷-1-酮、1-(4-(2-羥基乙氧基)-苯基)-2-羥基 -2-甲基-1-丙烷-1-酮、2-羥基-2-甲基-1-苯基丙烷-1-酮等α-羥基苯乙酮衍生物、雙二乙基氨基二苯甲酮、2-甲基-1-(4-(甲基硫代)苯基)-2-嗎啉代丙烷-1-酮、2-苄基-2-二甲基氨基-1-(4-嗎啉代苯基)-1-丁酮-1-酮等α-氨基烷基苯乙酮衍生物、2,4,6-三甲基苯甲醯二苯基氧化膦、雙(2,4,6-三甲基苯甲醯)-苯基氧化膦、雙(2,6-二甲氧基苯甲醯)-2,4,4-三甲基-戊基氧化膦等醯基氧化膦衍生物。本實施方式的光自由基聚合引發劑沒有特別限定，可以單獨使用，也可以為2種以上的混合物。 The (C) photoradical polymerization initiator of the present embodiment is not particularly limited as long as it absorbs light and generates a radical having a polymerization initiation energy. Examples of the photoradical polymerization initiator of the present embodiment include benzil, benzoin, benzoin benzoic acid, benzoin ethyl ether, and benzoin isopropyl ether. Benzoin derivatives such as benzoin isobutyl ether, benzophenone, benzophenone derivatives such as 4-phenylbenzophenone, 2,2-dimethoxy-1, An alkylacetophenone derivative such as 2-diphenylethane-1-one, 2,2-diethoxyacetophenone or benzyldimethylketal, 1-hydroxycyclohexyl ketone, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 1-(4-(2-hydroxyethoxy)-phenyl)-2-hydroxyl Α-hydroxyacetophenone derivatives such as 2-methyl-1-propan-1-one and 2-hydroxy-2-methyl-1-phenylpropan-1-one, bisdiethylaminobiphenyl Ketone, 2-methyl-1-(4-(methylthio)phenyl)-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4- α-Aminoalkylacetophenone derivatives such as morpholinophenyl)-1-butanone-1-one, 2,4,6-trimethylbenzimidium diphenylphosphine oxide, double (2,4 , 6-trimethylbenzhydrazide)-phenylphosphine oxide, bis(2,6-dimethoxybenzhydrazide)-2,4,4-trimethyl-pentylphosphine oxide derivative. The photoradical polymerization initiator of the present embodiment is not particularly limited, and may be used singly or in combination of two or more.

本實施方式的光自由基聚合引發劑也可以預先在多烯或多硫醇中混合。 The photoradical polymerization initiator of the present embodiment may be mixed in advance in a polyene or a polythiol.

本實施方式的(C)光自由基聚合引發劑的使用量，相對於成分(A)、成分(B)以及需要根據使用的成分(D)的合計100質量部(parts)，優選為0.01~10質量部，更優選為0.05~5質量部。如果為0.01質量部以上，則能夠得到充分的固化性，如果為10質量部以下，則也不會損害可見光透明性。需要說明的是，該使用量可以為0.01、0.02、0.03、0.04、0.05、0.06、0.07、0.08、0.09、0.1、0.2、0.3、0.4、0.5、0.6、0.7、0.8、0.9、1、2、3、4、5、6、7、8、9、10質量部中的任意1個值或任意2個值的範圍內。 The amount of the (C) photoradical polymerization initiator used in the present embodiment is preferably 0.01% with respect to the total of 100 parts by mass of the component (A), the component (B), and the component (D) to be used. 10 parts by mass, more preferably 0.05 to 5 parts by mass. When it is 0.01 mass part or more, sufficient curability can be obtained, and if it is 10 mass parts or less, the visible light transparency will not be impaired. It should be noted that the usage amount may be 0.01, 0.02, 0.03, 0.04, 0.05, 0.06, 0.07, 0.08, 0.09, 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1, 2, Any one of the 3, 4, 5, 6, 7, 8, 9, and 10 mass parts or any two of the values.

關於(D)具有其他碳-碳不飽和鍵的化合物 About (D) compounds having other carbon-carbon unsaturated bonds

本實施方式的樹脂組成物還可以含有(D)半矽氧烷衍生物以外的、具有碳-碳不飽和鍵的化合物。 The resin composition of the present embodiment may further contain a compound having a carbon-carbon unsaturated bond other than the (D) hemidecane derivative.

作為(D)半矽氧烷衍生物以外的、具有碳-碳不飽和鍵的化合物，沒有特別限定，可以為具有1個碳-碳不飽和鍵的單官能化合物，也可以為具有2個以上碳-碳不飽和鍵的2官能以上的化合物。 The compound having a carbon-carbon unsaturated bond other than the (D) hemi-oxyalkylene derivative is not particularly limited, and may be a monofunctional compound having one carbon-carbon unsaturated bond, or may have two or more. A bifunctional or higher compound of a carbon-carbon unsaturated bond.

關於本實施方式的(D)半矽氧烷衍生物以外的、具有碳-碳不飽和鍵的化合物的黏度，從組成物的黏度調節的觀點出發，優選為1000mPa．s以下，更優選為50 0mPa．s以下，最優選為100mPa．s以下。 The viscosity of the compound having a carbon-carbon unsaturated bond other than the (D) hemi-oxyalkylene derivative of the present embodiment is preferably 1000 mPa from the viewpoint of viscosity adjustment of the composition. s or less, more preferably 50 0mPa. Below s, most preferably 100mPa. s below.

關於本實施方式的(D)半矽氧烷衍生物以外的、具有碳-碳不飽和鍵的化合物的分子量，從組成物的黏度調節的觀點出發，優選為1000以下，更優選為100~800，最優選為100~500。碳-碳不飽和鍵特別是指碳-碳雙鍵。 The molecular weight of the compound having a carbon-carbon unsaturated bond other than the (D) hemi-oxyalkylene derivative of the present embodiment is preferably 1,000 or less, and more preferably 100 to 800, from the viewpoint of viscosity adjustment of the composition. Most preferably, it is 100 to 500. The carbon-carbon unsaturated bond refers in particular to a carbon-carbon double bond.

作為本實施方式的(D)半矽氧烷衍生物以外的、具有碳-碳不飽和鍵的化合物，沒有特別限定，可以列舉：2-乙基已基(甲基)丙烯酸酯、2-乙基已基卡必醇(甲基)丙烯酸酯、2-羥丁基(甲基)丙烯酸酯、2-羥乙基(甲基)丙烯酸酯、2-羥丙基(甲基)丙烯酸酯、4-羥丁基(甲基)丙烯酸酯、苄基(甲基)丙烯酸酯、丁二醇單(甲基)丙烯酸酯、丁基(甲基)丙烯酸酯、環氧乙烷改性(以下稱為“EO”)甲酚(甲基)丙烯酸酯、二丙二醇(甲基)丙烯酸酯、乙氧基化苯基(甲基)丙烯酸酯、乙基(甲基)丙烯酸酯、異丁基(甲基)丙烯酸酯、異辛基(甲基)丙烯酸酯、環已基(甲基)丙烯酸酯、異冰片基(甲基)丙烯酸酯、二環戊基(甲基)丙烯酸酯、二環戊氧基乙基(甲基)丙烯酸酯、十二烷基(甲基)丙烯酸酯、壬基苯氧基聚乙二醇(甲基)丙烯酸酯、壬基苯氧基聚丙二醇(甲基)丙烯酸酯、辛基(甲基)丙烯酸酯、苯氧基乙基(甲基)丙烯酸酯、1,9-壬二醇二(甲基)丙烯酸酯、環氧丙烷(以下稱為“PO”)新戊二醇二(甲基)丙烯酸酯、三羥甲基丙烷三(甲基)丙烯酸酯、PO改性三羥甲基丙烷三(甲基)丙烯酸酯、三((甲基)丙烯醯氧乙基)異氰脲酸酯、二季戊四醇六(甲基)丙烯酸酯、二季戊四醇羥基五(甲基)丙烯酸酯、二三羥甲基丙烷四(甲基)丙烯酸酯、季戊四醇乙氧基四(甲基)丙烯酸酯、季戊四醇四(甲基)丙烯酸酯、三羥甲基乙烷三乙烯基醚、己二醇二乙烯基醚、四乙二醇二乙烯基醚、季戊四醇二乙烯基醚、三乙二醇二亞乙基乙烯基醚、乙二醇二亞丙基乙烯基醚、三乙二醇二亞乙基乙烯基醚、二烯丙基鄰苯二甲酸酯、二烯丙基馬來酸酯、三烯丙基氰脲酸酯、三烯丙基異氰脲酸酯、三烯丙基偏苯三酸酯、四烯丙氧基乙烷、三羥甲基丙烷二烯丙基醚、三羥甲基丙烷三烯丙基醚等。這些中，優選為烯丙基化合物。作為烯丙基化合物，可以列舉：二烯丙基鄰苯二甲酸酯、二烯丙基馬來酸酯、三烯丙基 氰脲酸酯、三烯丙基異氰脲酸酯、三烯丙基偏苯三酸酯、四烯丙氧基乙烷、三羥甲基丙烷二烯丙基醚、三羥甲基丙烷三烯丙基醚等。 The compound having a carbon-carbon unsaturated bond other than the (D) hemi-oxyalkylene derivative of the present embodiment is not particularly limited, and examples thereof include 2-ethylhexyl (meth) acrylate and 2-B. Base carbitol (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4 -Hydroxybutyl (meth) acrylate, benzyl (meth) acrylate, butane diol mono (meth) acrylate, butyl (meth) acrylate, ethylene oxide modification (hereinafter referred to as "EO") cresol (meth) acrylate, dipropylene glycol (meth) acrylate, ethoxylated phenyl (meth) acrylate, ethyl (meth) acrylate, isobutyl (methyl) Acrylate, isooctyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, dicyclopentyl (meth) acrylate, dicyclopentyloxy Ethyl (meth) acrylate, dodecyl (meth) acrylate, nonyl phenoxy polyethylene glycol (meth) acrylate, nonyl phenoxy polypropylene glycol (meth) acrylate, Octyl (meth) acrylate, benzene Ethyl ethyl (meth) acrylate, 1,9-nonanediol di(meth) acrylate, propylene oxide (hereinafter referred to as "PO") neopentyl glycol di(meth) acrylate, trihydroxyl Methylpropane tri(meth)acrylate, PO modified trimethylolpropane tri(meth)acrylate, tris((meth)acryloyloxyethyl)isocyanurate, dipentaerythritol Acrylate, dipentaerythritol hydroxy penta (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, pentaerythritol ethoxy tetra (meth) acrylate, pentaerythritol tetra (meth) acrylate , trimethylolethane trivinyl ether, hexanediol divinyl ether, tetraethylene glycol divinyl ether, pentaerythritol divinyl ether, triethylene glycol diethylene vinyl ether, ethylene glycol Dipropylene vinyl ether, triethylene glycol diethylene vinyl ether, diallyl phthalate, diallyl maleate, triallyl cyanurate, three Allyl isocyanurate, triallyl trimellitate, tetraallyloxyethane, trimethylolpropane diallyl ether, trimethylolpropane triallyl ether, and the like. Among these, an allyl compound is preferable. Examples of the allyl compound include diallyl phthalate, diallyl maleate, and triallyl. Cyanurate, triallyl isocyanurate, triallyl trimellitate, tetraallyloxyethane, trimethylolpropane diallyl ether, trimethylolpropane tri Allyl ether and the like.

關於本實施方式的(D)半矽氧烷衍生物以外的、具有碳-碳不飽和鍵的化合物的使用量，從低黏度時作業性良好、膠黏性提高的觀點出發，在成分(A)、成分(B)以及成分(D)的合計100質量部中，優選為2~50質量部，更優選為5~30質量部，最優選為7~15質量部。 The amount of the compound having a carbon-carbon unsaturated bond other than the (D) hemi-oxyalkylene derivative of the present embodiment is a component (A) from the viewpoint of good workability at low viscosity and improvement of adhesiveness. The total mass portion of the component (B) and the component (D) is preferably 2 to 50 parts by mass, more preferably 5 to 30 parts by mass, and most preferably 7 to 15 parts by mass.

關於(E)抗氧化劑 About (E) Antioxidants

從得到優良的耐熱性、保存穩定性的觀點出發，優選本實施方式的樹脂組成物還含有(E)抗氧化劑。 From the viewpoint of obtaining excellent heat resistance and storage stability, the resin composition of the present embodiment preferably further contains (E) an antioxidant.

(E)抗氧化劑是用於抑制製品中的成分的氧化而添加的抗氧化物質。作為抗氧化劑，沒有特別限定，可以列舉：三乙二醇-雙[3-(3-叔丁基-5-甲基-4-羥基苯基)丙酸酯]、1,6-己二醇-雙[3-(3,5-二叔丁基-4-羥基苯基)丙酸酯]、季戊四醇.四[3-(3,5-二叔丁基-4-羥基苯基)丙酸酯]、2,2’-亞甲基雙(6-叔丁基-對甲酚)、異辛基-3-(3,5-二叔丁基-4-羥基苯基)丙酸酯、2,2’-亞甲基雙(4-甲基-6-叔丁基苯酚)等酚類、2,2,4,4-四甲基-21-氧代-7-氧雜-3.20-二氮雜環雙螺[5.1.11.2]-二十一烷-20-丙酸十二烷基酯以及2,2,4,4-四甲基-21-氧代-7-氧雜-3.20-二氮雜環雙螺[5.1.11.2]-二十一烷-20-丙酸十四烷基酯的混合物、2-[2-羥基-3,5-雙(α,α-二甲基苄基)苯基]-2H-苯並***、雙(2,2,6,6-四甲基-4-呱啶基)癸二酸酯等受阻胺類、6-[3-(3-叔丁基-4-羥基-5-甲基苯基)丙氧基]-2,4,8,10-四-叔丁基二苯並[d、f][1,3,2]二氧雜膦等磷類化合物、二月桂基3,3′-硫代二丙酸酯、二肉豆蔻基3,3′-硫代二丙酸酯、二硬脂基3,3’-硫代二丙酸酯、季戊四醇四(3-十二烷基硫代丙酸酯)、2-巰基苯並咪唑等硫類化合物。這些中，優選為酚類化合物和/或受阻胺化合物，更優選為酚類化合物。 (E) The antioxidant is an antioxidant substance added for suppressing oxidation of components in the product. The antioxidant is not particularly limited, and examples thereof include triethylene glycol-bis[3-(3-tert-butyl-5-methyl-4-hydroxyphenyl)propionate] and 1,6-hexanediol. - bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], pentaerythritol. Tetra[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propanoic acid Ester], 2,2'-methylenebis(6-tert-butyl-p-cresol), isooctyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, Phenols such as 2,2'-methylenebis(4-methyl-6-tert-butylphenol), 2,2,4,4-tetramethyl-21-oxo-7-oxa-3.20- Diazohetero[5.1.11.2]-docosane-20-propionic acid lauryl ester and 2,2,4,4-tetramethyl-21-oxo-7-oxa-3.20 - Mixture of diazabicyclosuccinyl [5.1.11.2]-docosane-20-tetradecyl propionate, 2-[2-hydroxy-3,5-bis(α,α-dimethyl Hindered amines such as benzyl)phenyl]-2H-benzotriazole, bis(2,2,6,6-tetramethyl-4-acridinyl) sebacate, 6-[3-(3 -tert-Butyl-4-hydroxy-5-methylphenyl)propoxy]-2,4,8,10-tetra-tert-butyldibenzo[d,f][1,3,2] Phosphorus compounds such as oxaphosphine, dilauryl 3,3'-thiodipropionate, dimyristyl 3,3'-thiodipropionate Distearyl 3,3'-thiodipropionate, pentaerythritol tetrakis (3-lauryl thiopropionate), 2-mercaptobenzimidazole and other sulfur compounds. Among these, a phenol compound and/or a hindered amine compound is preferable, and a phenol compound is more preferable.

關於本實施方式的(E)抗氧化劑的使用量，相對於成分(A)、成分(B)以及根據 需要使用的成分(D)的合計100質量部，優選為0.001~3質量部，更優選為0.01~2質量部。如果為0.001質量部以上，則耐久性以及貯藏穩定性充分，如果為3質量部以下，則得到確實的膠黏性，沒有未固化的可能。 The amount of (E) antioxidant used in the present embodiment is based on the component (A), the component (B), and The total amount of the component (D) to be used is 100 parts by mass, preferably 0.001 to 3 parts by mass, and more preferably 0.01 to 2 parts by mass. When it is 0.001 part by mass or more, durability and storage stability are sufficient, and if it is 3 parts by mass or less, reliable adhesiveness is obtained, and there is no possibility of uncured.

關於本實施方式的多烯與多硫醇的質量比，在得到良好的耐熱性、膠黏性的方面，優選為49：1~1：49，更優選為45：5~5：45。特別是多烯中的雙鍵與多硫醇中的巰基為化學當量時最優選。在此所謂的化學當量是指(多烯的摩爾數/多烯分子具有的雙鍵的數)與(多硫醇的摩爾數/多硫醇分子具有的SH基的數)相等。在此，多烯是指成分(A)和成分(D)，多硫醇是指成分(B)。 The mass ratio of the polyene to the polythiol in the present embodiment is preferably 49:1 to 1:49, and more preferably 45:5 to 5:45, in terms of obtaining good heat resistance and adhesiveness. In particular, it is most preferred when the double bond in the polyene and the thiol group in the polythiol are stoichiometric. The chemical equivalent here means that (the number of moles of polyene/the number of double bonds of the polyene molecule) is equal to (the number of moles of polythiol/the number of SH groups of the polythiol molecule). Here, polyene means component (A) and component (D), and polythiol means component (B).

關於(F)密合性賦予劑 About (F) adhesion imparting agent

本實施方式為了提高膠黏性，可以使用(F)密合性賦予劑。作為密合性賦予劑，可以列舉：3-環氧丙氧丙基三甲氧基矽烷、γ-氯丙基三甲氧基矽烷、乙烯基三甲氧基矽烷、乙烯基三氯矽烷、乙烯基三乙氧基矽烷、乙烯基-三(β-甲氧基乙氧基)矽烷、γ-(甲基)丙烯醯氧丙基三甲氧基矽烷、β-(3,4-環氧環已基)乙基三甲氧基矽烷、γ-環氧丙氧丙基三甲氧基矽烷、γ-巰基丙基三甲氧基矽烷、γ-氨基丙基三乙氧基矽烷、N-β-(氨基乙基)-γ-氨基丙基三甲氧基矽烷、N-β-(氨基乙基)-γ-氨基丙基甲基二甲氧基矽烷、γ-脲基丙基三乙氧基矽烷、羥乙基(甲基)丙烯酸酯磷酸酯、(2-羥乙基)(甲基)丙烯酸磷酸酯、2-甲基-2-丙烯酸-2-羥乙基酯磷酸酯(methacryloyloxyethyl acid phosphate)、2-甲基-2-丙烯酸-2-羥乙基酯磷酸酯單乙基胺半鹽(half salt)等。 In the present embodiment, in order to improve the adhesiveness, (F) an adhesion imparting agent can be used. Examples of the adhesion imparting agent include 3-glycidoxypropyltrimethoxydecane, γ-chloropropyltrimethoxydecane, vinyltrimethoxydecane, vinyltrichlorodecane, and vinyltriethyl. Oxydecane, vinyl-tris(β-methoxyethoxy)decane, γ-(meth)acryloxypropyltrimethoxydecane, β-(3,4-epoxycyclohexyl)B Trimethoxy decane, γ-glycidoxypropyltrimethoxy decane, γ-mercaptopropyltrimethoxydecane, γ-aminopropyltriethoxydecane, N-β-(aminoethyl)- γ-Aminopropyltrimethoxydecane, N-β-(aminoethyl)-γ-aminopropylmethyldimethoxydecane, γ-ureidopropyltriethoxydecane, hydroxyethyl (A) Acrylate phosphate, (2-hydroxyethyl) (meth) acrylate, methacryloyloxyethyl acid phosphate, 2-methyl- 2-Hydroxy-2-hydroxyethyl ester phosphate monoethylamine half salt or the like.

關於(F)密合性賦予劑的使用量，相對於成分(A)、成分(B)以及根據需要使用的成分(D)的合計100質量部，優選為0.001~10質量部，更優選為0.01~5質量部。如果為0.001質量部以上，則膠黏性充分，如果為10質量部以下，則得到確實的膠黏性。 The amount of use of the (F) adhesion-imparting agent is preferably 0.001 to 10 parts by mass, more preferably 0.001 to 10 parts by mass, based on 100 parts by mass of the total of the component (A), the component (B), and the component (D) to be used. 0.01~5 mass parts. When it is 0.001 part by mass or more, the adhesiveness is sufficient, and if it is 10 mass parts or less, a reliable adhesiveness is obtained.

本實施方式的樹脂組成物，在不損害目標效果的範圍內，根據需要，可以添加熱自由基聚合引發劑、固化促進劑、填充劑、著色劑、觸變性賦予劑、增塑劑、表面活性劑、潤滑劑、抗靜電劑等添加劑。 In the resin composition of the present embodiment, a thermal radical polymerization initiator, a curing accelerator, a filler, a colorant, a thixotropic agent, a plasticizer, and a surface active agent may be added as needed within a range that does not impair the intended effect. Additives such as agents, lubricants, and antistatic agents.

本實施方式的樹脂組成物可以作為膠黏劑使用。作為通過本實施方式的膠黏劑膠黏的基材或通過本發明的膠黏劑形成成形體的基材，可以列舉：石英、石英玻璃、硼矽酸玻璃、鈉鈣玻璃等玻璃材料、溴化鉀、氟化鈣等鹵化礦物、藍寶石等單晶陶瓷、丙烯酸樹脂、聚碳酸酯樹脂、聚苯乙烯樹脂、聚酯樹脂、聚乙烯樹脂、聚丙烯樹脂、含氟樹脂、纖維素樹脂、苯乙烯-丁二烯共聚物、甲基丙烯酸酸甲酯-苯乙烯共聚物、矽樹脂、聚環烯烴樹脂、丙烯腈-丁二烯-苯乙烯共聚物樹脂、聚苯硫醚樹脂、液晶聚合物、環氧樹脂、用玻璃纖維或碳纖維強化後的樹脂等樹脂材料、矽、鍺、鎵、銦、氧化鋅、氧化鈦等半導體材料、金屬層、樹脂層、陶瓷層被蒸鍍、鍍覆、濺射後的上述半導體材料、以及鐵、不銹鋼、鋁、鋅、鎂、銅、黃銅、磷青銅、銀、金、鉑等金屬材料等。 The resin composition of the present embodiment can be used as an adhesive. Examples of the substrate to which the molded article is adhered by the adhesive of the present embodiment or the adhesive formed by the adhesive of the present invention include glass materials such as quartz, quartz glass, borosilicate glass, and soda lime glass, and bromine. Halogenated minerals such as potassium and calcium fluoride, single crystal ceramics such as sapphire, acrylic resin, polycarbonate resin, polystyrene resin, polyester resin, polyethylene resin, polypropylene resin, fluorine resin, cellulose resin, benzene Ethylene-butadiene copolymer, methyl methacrylate-styrene copolymer, oxime resin, polycycloolefin resin, acrylonitrile-butadiene-styrene copolymer resin, polyphenylene sulfide resin, liquid crystal polymer A resin material such as an epoxy resin or a resin reinforced with glass fiber or carbon fiber, a semiconductor material such as lanthanum, cerium, gallium, indium, zinc oxide or titanium oxide, a metal layer, a resin layer or a ceramic layer is vapor-deposited or plated. The semiconductor material after sputtering, and a metal material such as iron, stainless steel, aluminum, zinc, magnesium, copper, brass, phosphor bronze, silver, gold, or platinum.

本實施方式的樹脂組成物可以通過光或紫外線等活性能量射線固化。使用由本實施方式的樹脂組成物構成的膠黏劑的光學構件也可以通過活性能量射線膠黏。 The resin composition of the present embodiment can be cured by active energy rays such as light or ultraviolet rays. The optical member using the adhesive composed of the resin composition of the present embodiment can also be adhered by active energy rays.

利用活性能量射線的固化或膠黏中，可以應用以鹵素燈、金屬鹵化物燈、高功率金屬鹵化物燈(含有銦等)、低壓水銀燈、高壓水銀燈、超高壓水銀燈、氙燈、氙氣激勵燈(xenon excimer lamp)、氙氣閃光燈(xenon flash lamp)等作為光源的照射裝置，另外，也可以應用鐳射和電子射線(EUV)等。 In the curing or adhesion of active energy rays, halogen lamps, metal halide lamps, high-power metal halide lamps (including indium, etc.), low-pressure mercury lamps, high-pressure mercury lamps, ultra-high pressure mercury lamps, xenon lamps, xenon excitation lamps can be used ( An xenon excimer lamp), a xenon flash lamp, or the like is used as a light source illumination device, and laser and electron beam (EUV) may be applied.

上述裝置可以進行直接照射、通過反射鏡等的集光照射、利用纖維等的集光照射，也可以使用低波長截止濾光片、熱線截止濾光片、冷光鏡等。 The above device may be subjected to direct irradiation, light collection by a mirror or the like, or light collection by fibers or the like, or a low wavelength cut filter, a heat cut filter, a cold mirror or the like may be used.

本實施方式通過使用例如含有作為半矽氧烷衍生物的多烯和多硫醇為主成分的多烯-多硫醇樹脂組成物，具有耐熱性、耐光性、透明性、速固化性、膠黏性、保存穩定性優良的效果。本發明能夠提供膠黏體、固化物、成形體、光學部件、光波導。 In the present embodiment, by using, for example, a polyene-polythiol resin composition containing a polyene and a polythiol as a hemidecane derivative, heat resistance, light resistance, transparency, rapid curability, and gelation are obtained. Excellent viscosity and storage stability. The present invention can provide an adhesive body, a cured product, a molded body, an optical member, and an optical waveguide.

光波導為如下電子部件，即，在基板的表面或基板表面正下方製作折射率比周圍略高的部分並封入光，控制光的傳播、分支、反射、折射、放大、衰減等，並進行光的合波/分波和開關。本發明通過將由本發明的樹脂組成物的固化物構成的層與具有比該層高的折射率的層進行層壓而可以提供光波導。 The optical waveguide is an electronic component in which a portion having a refractive index slightly higher than that of the periphery is formed directly on the surface of the substrate or the surface of the substrate, and light is enclosed, and light propagation, branching, reflection, refraction, amplification, attenuation, and the like are controlled, and light is performed. Combine/divide and switch. The present invention can provide an optical waveguide by laminating a layer composed of a cured product of the resin composition of the present invention and a layer having a refractive index higher than that of the layer.

作為光波導的具體的部件的通常例，可以列舉：在通信和光資訊處理的領域中使用的光合波電路、頻率濾波器、光開關、光互連部件等。 Typical examples of the specific components of the optical waveguide include an optical multiplexer circuit, a frequency filter, an optical switch, an optical interconnection member, and the like used in the field of communication and optical information processing.

以上，參照附圖對本發明的實施方式進行了說明，但這些為本發明的例示，也可以採用上述以外的各種構成。 The embodiments of the present invention have been described above with reference to the drawings, but these are examples of the present invention, and various configurations other than the above may be employed.

【實施例】 [Examples]

以下，使用實施例以及比較例，更詳細地說明本發明，但本發明沒有被這些實施例限定。 Hereinafter, the present invention will be described in more detail by way of examples and comparative examples, but the invention is not limited thereto.

〈實施例1~20以及比較例1~3〉 <Examples 1 to 20 and Comparative Examples 1 to 3>

將表1~3所示種類的各成分以表中所示的組成進行混合，製備樹脂組成物。表1~3中記載的各成分，選擇以下的化合物。 Each component of the type shown in Tables 1 to 3 was mixed in the composition shown in the table to prepare a resin composition. The following compounds were selected for each component described in Tables 1-3.

(A)：每1分子中具有2個以上碳-碳不飽和鍵、並且隨機結構的半矽氧烷衍生物 (A): a semiquinoxane derivative having 2 or more carbon-carbon unsaturated bonds per molecule and having a random structure

(a-1)：東亞合成公司製：聚丙烯醯氧丙基聚有機半矽氧烷(AC-SQ TA-100)(利用GPC的聚苯乙烯換算的重量平均分子量1200~4000、丙烯醯基當量165g/eq (a-2)：東亞合成公司製：聚甲基丙烯醯氧丙基聚有機半矽氧烷(MAC-SQ TM-100)(利用GPC的聚苯乙烯換算的重量平均分子量1000~2500、甲基丙烯醯基當量179g/eq (a-1): manufactured by Toagosei Co., Ltd.: Polypropylene oxiranyl polyorgano-halfoxane (AC-SQ TA-100) (weight-average molecular weight of 1200-4000 in terms of polystyrene by GPC, acrylonitrile Equivalent 165g/eq (a-2): manufactured by Toagosei Co., Ltd.: polymethacrylic oxirane polyorgano-halfoxane (MAC-SQ TM-100) (weight-average molecular weight of 1000 to 2500 in terms of polystyrene by GPC, A Acryl hydrazide equivalent 179g/eq

(B)：多硫醇 (B): polythiol

(b-1)：澱化學公司製：三羥甲基丙烷-三(β-硫代丙酸酯)(TP) (b-1): manufactured by Dian Chemical Co., Ltd.: Trimethylolpropane-tris(β-thiopropionate) (TP)

(b-2)：SC有機化學公司：三[(3-巰基丙醯氧基)-乙基]異氰脲酸酯(TEMPIC) (b-2): SC Organic Chemicals: Tris[(3-decylpropenyloxy)-ethyl]isocyanurate (TEMPIC)

(D)：半矽氧烷衍生物以外的、具有碳-碳不飽和鍵的化合物 (D): a compound having a carbon-carbon unsaturated bond other than a heptane derivative

(d-1)：日本化成公司製：三烯丙基異氰脲酸酯(TAIC) (d-1): manufactured by Nippon Kasei Co., Ltd.: triallyl isocyanurate (TAIC)

(d-2)：黑金化成公司製：二烯丙基馬來酸酯(DAM) (d-2): manufactured by Heijin Chemical Co., Ltd.: diallyl maleate (DAM)

(C)：光自由基聚合引發劑 (C): Photoradical polymerization initiator

(c-1)：BASF公司製：2,2-二甲氧基-1,2-二苯基乙烷-1-酮(IRGACURE651) (c-1): manufactured by BASF Corporation: 2,2-dimethoxy-1,2-diphenylethane-1-one (IRGACURE651)

(c-2)：BASF公司製：2-羥基-2-甲基-1-苯基-丙烷-1-酮(DAROCUR1173) (c-2): manufactured by BASF: 2-hydroxy-2-methyl-1-phenyl-propan-1-one (DAROCUR1173)

(E)：抗氧化劑 (E): Antioxidants

(e-1)：BASF公司製：異辛基-3-(3,5-二叔丁基-4-羥基苯基)丙酸酯(IRGANOX1135) (e-1): manufactured by BASF Corporation: isooctyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate (IRGANOX 1135)

(e-2)：住友化學公司製：2,2’-亞甲基雙(4-甲基-6-叔丁基苯酚)(Sumilizer MDP-S) (e-2): Sumitomo Chemical Co., Ltd.: 2,2'-methylenebis(4-methyl-6-tert-butylphenol) (Sumilizer MDP-S)

(F)：密合性賦予劑 (F): adhesion imparting agent

(f-1)：momentive公司製：γ-甲基丙烯酰氧丙基三甲氧基硅烷(A-174) (f-1): manufactured by Momentive: γ-methacryloxypropyltrimethoxysilane (A-174)

(f-2)：信越化學公司製：3-環氧丙氧丙基三甲氧基矽烷(KBM-403) (f-2): Shin-Etsu Chemical Co., Ltd.: 3-glycidoxypropyltrimethoxydecane (KBM-403)

(G)：籠型結構的半矽氧烷衍生物多烯 (G): cage-structured hemioxane derivative polyene

(g-1)：東亞合成公司製：八[(3-甲基丙烯醯氧丙基)二甲基甲矽烷氧基]半矽氧烷](Q-8)(分子量2027) (g-1): manufactured by Toagosei Co., Ltd.: octa [(3-methacryloxypropyl) dimethylformaloxy] hemidecane] (Q-8) (molecular weight 2027)

基於上述實施例以及比較例中得到的組成物，進行下述的性能評價，將其結果示於表1~3。 Based on the compositions obtained in the above examples and comparative examples, the following performance evaluations were carried out, and the results are shown in Tables 1 to 3.

(膠黏劑的固化條件) (curing conditions of the adhesive)

進行評價時，根據如下所述的順序製作膠黏試驗體。 At the time of evaluation, a tacky test body was produced in the order described below.

固化方法 Curing method

通過使用超高壓水銀燈的HOYA公司製固化裝置，在365nm的波長的累積光量3000mJ/cm2的條件下使其固化。 The curing apparatus was cured under the conditions of a cumulative light amount of 3,000 nm at a wavelength of 3,000 mJ/cm 2 by using a curing apparatus manufactured by HOYA Co., Ltd. using an ultrahigh pressure mercury lamp.

(1)黏度 (1) Viscosity

使用E型黏度計，在溫度25℃、轉速20rpm的條件下測定組成物的黏度。 The viscosity of the composition was measured using an E-type viscometer at a temperature of 25 ° C and a rotation speed of 20 rpm.

(2)透光率(透明性評價、UV固化後) (2) Light transmittance (after transparency evaluation, after UV curing)

作為試驗片，製作在BK7玻璃(硼矽酸玻璃、30mm φ×3mmt)基板上將形狀20mm φ×200μmt的樹脂組成物在如上所述的固化條件下固化而成的試驗片。透光率使用分光光度計(島津製作所株式會社制、UV-2550)，測定波長400nm和600nm的透過率，將90%以上評價為良好。將評價結果示於表1~3。 As a test piece, a test piece obtained by curing a resin composition having a shape of 20 mm φ × 200 μmt on a BK7 glass (boron silicate glass, 30 mm φ × 3 mmt) substrate under the curing conditions as described above was prepared. The light transmittance was measured using a spectrophotometer (UV-2550, manufactured by Shimadzu Corporation), and the transmittances at wavelengths of 400 nm and 600 nm were measured, and 90% or more was evaluated as good. The evaluation results are shown in Tables 1 to 3.

(3)耐熱試驗(透光率、耐熱試驗後) (3) Heat resistance test (light transmittance, heat resistance test)

作為試驗片，製作在BK7玻璃(30mm φ×3mmt)基板上將形狀20mm φ×200μmt的樹脂組成物在如上所述的固化條件下固化而成的試驗片。將該試驗片在260℃的氣氛中暴露40秒。關於暴露後的試驗片的透光率，使用分光光度計(島津製作所株式會社制、UV-2550)，測定波長400nm和600nm的透過率，將90%以上評價為良好。將評價結果示於表1~3。 As a test piece, a test piece obtained by curing a resin composition having a shape of 20 mm φ × 200 μmt on a BK7 glass (30 mm φ × 3 mmt) substrate under the curing conditions as described above was prepared. The test piece was exposed to an atmosphere of 260 ° C for 40 seconds. The light transmittance of the test piece after the exposure was measured using a spectrophotometer (UV-2550, manufactured by Shimadzu Corporation), and the transmittances at wavelengths of 400 nm and 600 nm were measured, and 90% or more was evaluated as good. The evaluation results are shown in Tables 1 to 3.

(4)耐光試驗(透光率、耐光試驗後) (4) Light resistance test (light transmittance, light resistance test)

作為試驗片，製作在BK7玻璃(30mm φ×3mmt)基板上將形狀20mm φ×200μmt的樹脂組成物在如上所述的固化條件下固化而成的試驗片。使用高壓水銀燈(東芝公司製、一400 HC-0411型)，在365nm光的照度7mW/cm2的光下， 將該試驗片暴露80小時。關於暴露後的試驗片的透光率，使用分光光度計(島津製作所株式會社制、UV-2550)，測定波長400nm和600nm的透過率，將90%以上評價為良好。將評價結果示於表1~3。 As a test piece, a test piece obtained by curing a resin composition having a shape of 20 mm φ × 200 μmt on a BK7 glass (30 mm φ × 3 mmt) substrate under the curing conditions as described above was prepared. Use high pressure mercury lamp (made by Toshiba Corporation, A 400 HC-0411 type), the test piece was exposed to light at illuminance of 365 nm light of 7 mW/cm 2 for 80 hours. The light transmittance of the test piece after the exposure was measured using a spectrophotometer (UV-2550, manufactured by Shimadzu Corporation), and the transmittances at wavelengths of 400 nm and 600 nm were measured, and 90% or more was evaluated as good. The evaluation results are shown in Tables 1 to 3.

(5)拉伸膠黏剪切強度(膠黏性) (5) Tensile adhesive shear strength (adhesiveness)

基於JIS K 6850測定。具體而言，使用作為被黏材料的(商標)TEMPAX玻璃(25mm×25mm×2.0mm)，將膠黏部位設為直徑8mm，用所製作的樹脂組成物黏合2片TEMPAX玻璃，使上述膠黏劑在如上所述的固化條件下固化，製作拉伸剪切膠黏強度試驗片。關於製作的試驗片，使用拉伸試驗機，在溫度23℃、濕度50%的環境下以拉伸速度10mm/分鐘測定拉伸剪切膠黏強度。將評價結果示於表1~3。 It is measured based on JIS K 6850. Specifically, using (trademark) TEMPAX glass (25 mm × 25 mm × 2.0 mm) as a material to be adhered, the adhesive portion was set to have a diameter of 8 mm, and two TEMPAX glasses were bonded with the prepared resin composition to make the above-mentioned adhesive The agent was cured under the curing conditions as described above to prepare a tensile shear adhesive strength test piece. With respect to the produced test piece, the tensile shear adhesive strength was measured at a tensile speed of 10 mm/min in a temperature of 23 ° C and a humidity of 50% using a tensile tester. The evaluation results are shown in Tables 1 to 3.

由表1~3可以確認到以下事項：本實施例的樹脂組成物的耐熱性、耐光性、透明性、膠黏性優良。在沒有使用本實施例的(A)半矽氧烷衍生物的情況下，未得到耐熱性、耐光性、膠黏性(比較例1)。在使用籠型結構的半矽氧烷衍生物的情況下，在樹脂組成物中不溶解，未得到本實施例的效果(比較例2)。在沒有使用本實施例的(B)多硫醇的情況下，未得到耐熱性、膠黏性(比較例3)。 From Tables 1 to 3, it was confirmed that the resin composition of the present example is excellent in heat resistance, light resistance, transparency, and adhesiveness. When the (A) semi-oxane derivative of the present Example was not used, heat resistance, light resistance, and adhesiveness were not obtained (Comparative Example 1). In the case of using a semiquinoxane derivative having a cage structure, it was not dissolved in the resin composition, and the effect of the present example was not obtained (Comparative Example 2). When the (B) polythiol of the present Example was not used, heat resistance and adhesiveness were not obtained (Comparative Example 3).

【產業上的可利用性】 [Industrial availability]

本發明提供耐熱性、耐光性、透明性、速固化性、膠黏性、保存穩定性優良的多烯-多硫醇類樹脂組成物。本發明的膠黏劑在光波導的層、光學部件、電子部件等各種領域中顯示出顯著的效果。 The present invention provides a polyene-polythiol resin composition excellent in heat resistance, light resistance, transparency, rapid curability, adhesiveness, and storage stability. The adhesive of the present invention exhibits remarkable effects in various fields such as layers of optical waveguides, optical members, and electronic components.

Claims (9)

一種樹脂組成物，其中，含有：(A)每1分子中具有2個以上碳-碳不飽和鍵，並且具有隨機結構的由下述通式[1]表示的半矽氧烷衍生物；(B)多硫醇；(C)光自由基聚合引發劑，通式[1]【化1】(R 0 -SiO 3/2 ) m (式中，R0具有選自(甲基)丙烯醯基、乙烯基、乙烯基醚基、烯丙基以及烯丙基醚基中的一種以上官能團，R0可以相同也可以不同，(甲基)丙烯醯基、乙烯基、乙烯基醚基、烯丙基以及烯丙基醚基的一部分可以由碳原子數1~6的烷基、碳原子數1~6的烷氧基、碳原子數1~6的鹵化烷基、苯基、鹵素取代，m表示聚合度)。 A resin composition comprising: (A) a hemidecane derivative represented by the following formula [1] having two or more carbon-carbon unsaturated bonds per molecule and having a random structure; B) polythiol; (C) photoradical polymerization initiator, general formula [1] [Chemical Formula 1] (R 0 - SiO 3/2 ) m (wherein R 0 has a selected from (meth) propylene oxime More than one functional group in the group, vinyl group, vinyl ether group, allyl group and allyl ether group, R 0 may be the same or different, (meth) acryl fluorenyl group, vinyl group, vinyl ether group, olefin A part of the propyl group and the allyl ether group may be substituted by an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a halogenated alkyl group having 1 to 6 carbon atoms, a phenyl group or a halogen. m represents the degree of polymerization). 如申請專利範圍第1項所述的樹脂組成物，還含有(D)半矽氧烷衍生物以外的、具有碳-碳不飽和鍵的化合物。 The resin composition according to claim 1, further comprising (D) a compound having a carbon-carbon unsaturated bond other than the hemidecane derivative. 如申請專利範圍第1項所述的樹脂組成物，還含有(E)抗氧化劑。 The resin composition according to claim 1, further comprising (E) an antioxidant. 如申請專利範圍第1項所述的樹脂組成物，還含有(F)密合性賦予劑。 The resin composition according to claim 1, further comprising (F) an adhesion imparting agent. 一種膠黏劑，是由如申請專利範圍第1項~4中任一項所述的樹脂組成物構成。 An adhesive composition comprising the resin composition according to any one of claims 1 to 4. 一種膠黏體，是使用如申請專利範圍第5項所述的膠黏劑進行膠黏而成。 An adhesive body obtained by gluing using an adhesive as described in claim 5 of the patent application. 一種固化物，是由如申請專利範圍第1項~4中任一項所述的樹脂組成物構成。 A cured product is composed of a resin composition as described in any one of claims 1 to 4. 一種光波導，是將由如申請專利範圍第7項所述的固化物構成的層與具有比該層高的折射率的層進行層壓而成。 An optical waveguide obtained by laminating a layer composed of a cured product as described in claim 7 and a layer having a refractive index higher than that of the layer. 一種光學部件，其含有如申請專利範圍第1項~4中任一項所述的樹脂組成物。 An optical component comprising the resin composition according to any one of claims 1 to 4.
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