KR20180128926A - CURING COMPOSITION, METHOD FOR PRODUCING CURED PRODUCT, AND CURED PRODUCT - Google Patents
CURING COMPOSITION, METHOD FOR PRODUCING CURED PRODUCT, AND CURED PRODUCT Download PDFInfo
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- KR20180128926A KR20180128926A KR1020187028910A KR20187028910A KR20180128926A KR 20180128926 A KR20180128926 A KR 20180128926A KR 1020187028910 A KR1020187028910 A KR 1020187028910A KR 20187028910 A KR20187028910 A KR 20187028910A KR 20180128926 A KR20180128926 A KR 20180128926A
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
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Classifications
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- 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
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Abstract
경화물의 유리 전이 온도가 높고, 밀착성이 우수한 경화성 조성물, 경화물의 제조 방법, 및 그 경화물을 제공한다. 양이온 중합성 성분(A) 45∼90 질량부, 양이온 중합 개시제(B) 0.001∼15 질량부, 라디칼 중합성 성분(C) 1∼15 질량부, 라디칼 중합 개시제(D) 1∼10 질량부, 및 하기 식(I)
(식 중, X는, 탄소 원자수 1∼7의 알킬기 등)으로 표시되는 단량체로부터 얻어지는 폴리머, 하기 식(II)
(식 중, R1은 수소 원자 등을 나타내고, X'는 탄소 원자수 1∼7의 알킬기 등)으로 표시되는 단량체로부터 얻어지는 폴리머 등(E) 1∼20 질량부를, (A) 성분과 (C) 성분의 합계가 100질량부가 되도록 함유하고, (A) 성분이, 다가 알코올의 글리시딜화물 등(A1)과, 옥세탄 화합물(A2)을 필수 성분으로 하고, (C) 성분이, 에폭시기 및 에틸렌성 불포화기를 가지는 화합물(C1) 등을 필수 성분으로 한다.A curable composition having a high glass transition temperature of a cured product and excellent adhesiveness, a process for producing a cured product, and a cured product thereof. (C), 1 to 15 parts by mass of a radical polymerization initiator (D), 1 to 10 parts by mass of a radical polymerization initiator (D), and 5 to 50 parts by mass of a cationic polymerizable component (A) And (I)
(Wherein X is an alkyl group having 1 to 7 carbon atoms, etc.), a polymer obtained from a monomer represented by the following formula (II)
(E) 1 to 20 parts by mass of a polymer obtained from a monomer represented by the following formula ( 1 ): wherein R 1 represents a hydrogen atom or the like and X 'represents an alkyl group having 1 to 7 carbon atoms, Wherein the component (A) is at least one compound selected from the group consisting of a glycidyl compound of a polyhydric alcohol (A1) and an oxetane compound (A2) as essential components, and the component (C) And a compound (C1) having an ethylenic unsaturated group as essential components.
Description
본 발명은, 경화성 조성물, 경화물의 제조 방법, 및 그 경화물에 관한 것이며, 상세하게는, 경화물의 유리 전이 온도가 높고, 밀착성이 우수한 경화성 조성물, 경화물의 제조 방법, 및 그 경화물에 관한 것이다.TECHNICAL FIELD The present invention relates to a curable composition, a method for producing a cured product, and a cured product thereof, and more particularly, to a curable composition having a high glass transition temperature and excellent adhesiveness, a method for producing the cured product, and a cured product thereof .
경화성 조성물은, 잉크, 도료, 각종 코팅제, 접착제, 광학 부재 등의 분야에 있어서 사용되고 있다. 이와 같은, 경화성 조성물의 개량에 관하여, 다양한 보고가 이루어지고 있다.Curable compositions are used in the fields of inks, paints, various coatings, adhesives, optical members and the like. Various reports have been made on the improvement of the curable composition.
예를 들면, 하기 특허문헌 1∼3에는, 양이온 중합성 성분 및 라디칼 중합성 성분을 함유하는 에너지선 경화성 조성물 또는 그 경화물이 제안되어 있다. 구체적으로는, 특허문헌 1에서는, 초기 경화성 및 접착성이 우수한 편광판용 접착제 조성물이 제안되어 있다. 또한, 특허문헌 2에서는, 투습도가 낮은 수지 필름을 보호막으로 하는 경우라도, 광조사 후 신속하게 접착력을 발현하고, 일정 시간 경과 후의 접착력이 다양한 힘에 대하여 양호하며, 내구 시험 후에도 문제를 일으키지 않으며, 내습열 시험 종료 후의 접착력도 양호한, 저점도의 광경화성 접착제가 제안되어 있다. 또한, 특허문헌 3에서는, 불포화지환식 에폭시에스테르 화합물을 포함하는 고내열성이나 고굴절율화와 투명성을 양립할 수 있는 활성 에너지선 중합성 수지 조성물이 제안되어 있다.For example, Patent Documents 1 to 3 below disclose an energy ray-curable composition containing a cationic polymerizable component and a radically polymerizable component or a cured product thereof. Specifically, Patent Document 1 proposes an adhesive composition for a polarizing plate that is excellent in initial curability and adhesiveness. In Patent Document 2, even when a resin film having a low moisture permeability is used as a protective film, an adhesive force is developed rapidly after light irradiation, an adhesive force after a lapse of a predetermined time is satisfactory for various forces, There has been proposed a photo-curable adhesive having a low viscosity and good adhesive strength after completion of the anti-wet heat test. Further, Patent Document 3 proposes an active energy ray polymerizable resin composition including both an unsaturated alicyclic epoxy ester compound and high transparency and high heat resistance.
그러나, 특허문헌 1∼3에서 제안되어 있는 경화성 조성물이라도, 경화성 및 밀착성에 대해서는, 반드시 만족할 수 있는 것은 아닌 경우가 있고, 경화성 및 밀착성을 고도로 양립시킬 수 있는, 새로운 경화성 조성물이 요구되고 있는 것이 현재 실정이다. However, even in the curable compositions proposed in Patent Documents 1 to 3, there are cases in which the curability and the adhesiveness are not necessarily satisfactory, and a new curable composition capable of highly matching the curability and the adhesion property is required It is true.
이에, 본 발명의 목적은, 경화물의 유리 전이 온도가 높고, 밀착성이 우수한 경화성 조성물, 경화물의 제조 방법, 및 그 경화물을 제공하는 것에 있다.Accordingly, an object of the present invention is to provide a curable composition having a high glass transition temperature of the cured product and excellent adhesiveness, a process for producing the cured product, and a cured product thereof.
본 발명자들은, 상기 과제를 해결하기 위해 예의(銳意) 검토한 결과, 특정한 조성을 가지는 경화성 조성물이라면, 상기 과제를 해소할 수 있는 일을 발견하여, 본 발명을 완성하기에 이르렀다.DISCLOSURE OF THE INVENTION The inventors of the present invention have conducted intensive studies to solve the above-mentioned problems, and as a result, discovered that a curable composition having a specific composition can solve the above problems, and have completed the present invention.
즉, 본 발명의 경화성 조성물은, 양이온 중합성 성분(A) 45∼90 질량부와, 양이온 중합 개시제(B) 0.001∼15 질량부와, 라디칼 중합성 성분(C) 1∼15 질량부와, 라디칼 중합 개시제(D) 1∼10 질량부와,That is, the curable composition of the present invention comprises 45 to 90 parts by mass of the cationic polymerizable component (A), 0.001 to 15 parts by mass of the cationic polymerization initiator (B), 1 to 15 parts by mass of the radical polymerizable component (C) 1 to 10 parts by mass of a radical polymerization initiator (D)
하기 식(I)(I)
(식중, X는, 탄소 원자수 1∼7의 알킬기, 탄소 원자수 1∼7의 알콕시기, 탄소 원자수 6∼12의 아릴기, 탄소 원자수 6∼12의 아릴옥시기 혹은 탄소 원자수 6∼10의 지환식 탄화수소기, 또는 이들 기 중의 수소 원자가, 에폭시기, 옥세탄기, 수산기 및 카르복실기로 이루어지는 군으로부터 선택되는 1종 이상의 기로 치환된 것임)으로 표시되는 단량체로부터 얻어지는 폴리머, 하기 식(II)(Wherein X represents an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aryloxy group having 6 to 12 carbon atoms, Or an alicyclic hydrocarbon group having 1 to 10 carbon atoms, or hydrogen atoms in these groups are substituted with at least one group selected from the group consisting of an epoxy group, an oxetane group, a hydroxyl group and a carboxyl group), a polymer obtained from a monomer represented by the following formula )
(식중, R1은, 수소 원자, 메틸기 또는 할로겐 원자를 나타내고, X'는, 탄소 원자수 1∼7의 알킬기, 탄소 원자수 6∼12의 아릴기 혹은 탄소 원자수 6∼10의 지환식 탄화수소기, 또는 이들 기 중의 수소 원자가, 에폭시기, 옥세탄기, 수산기 및 카르복실기로 이루어지는 군으로부터 선택되는 1종 이상의 기로 치환된 것임)으로 표시되는 단량체로부터 얻어지는 폴리머, 상기 식(I)으로 표시되는 단량체로부터 선택되는 2종 이상의 단량체로부터 얻어지는 폴리머, 상기 식(II)으로 표시되는 단량체로부터 선택되는 2종 이상의 단량체로부터 얻어지는 폴리머, 및 상기 식(I)으로 표시되는 단량체 및 상기 식(II)으로 표시되는 단량체로부터 얻어지는 폴리머로 이루어지는 군으로부터 선택되는 중량 평균 분자량 1,000∼30,000인 폴리머(E) 1∼20 질량부를, 상기 양이온 중합성 성분(A), 상기 라디칼 중합성 성분(C) 및 상기 폴리머(E)의 합계가 100질량부가 되도록 함유하고,(Wherein R 1 represents a hydrogen atom, a methyl group or a halogen atom, and X 'represents an alkyl group having 1 to 7 carbon atoms, an aryl group having 6 to 12 carbon atoms or an alicyclic hydrocarbon having 6 to 10 carbon atoms Or a hydrogen atom in these groups is substituted with at least one group selected from the group consisting of an epoxy group, an oxetane group, a hydroxyl group and a carboxyl group), a polymer obtained from a monomer represented by the formula (I) A polymer obtained from two or more selected monomers, a polymer obtained from two or more kinds of monomers selected from the monomers represented by the formula (II), and a monomer represented by the formula (I) and a monomer represented by the formula (II) 1 to 20 parts by mass of a polymer (E) having a weight average molecular weight of 1,000 to 30,000 selected from the group consisting of the polymers obtained from the cationic polymerization The sum of components (A), the radical polymerizable component (C) and the polymer (E) contains 100 parts by mass to add,
상기 양이온 중합성 성분(A)이, 다가 알코올의 글리시딜화물 또는 다가 알코올 알킬렌옥사이드 부가물의 글리시딜화물(A1)과, 옥세탄 화합물(A2)을 필수 성분으로 하고,Wherein the cationic polymerizable component (A) is a glycidylated product of a polyhydric alcohol or a glycidylated product of a polyhydric alcohol alkylene oxide adduct (A1) and an oxetane compound (A2)
상기 라디칼 중합성 성분(C)이, 에폭시기 및 에틸렌성 불포화기를 가지는 화합물(C1), 또는 탄소 원자수 2∼20인 다가 알코올의 아크릴산 에스테르 혹은 탄소 원자수 2∼20인 다가 알코올의 메타크릴산 에스테르(C2)를 필수 성분으로 하는 것을 특징으로 하는 것이다. 여기서, 중량 평균 분자량이란, 테트라하이드로퓨란(THF) 용매중, GPC에 의해 측정하고, 스티렌 환산으로 구한 중량 평균 분자량을 일컫는다.Wherein the radical polymerizing component (C) is a compound (C1) having an epoxy group and an ethylenically unsaturated group, or a methacrylate ester (C2) as an essential component. Here, the weight average molecular weight refers to a weight average molecular weight determined by GPC in a tetrahydrofuran (THF) solvent and calculated in terms of styrene.
본 발명의 경화성 조성물에 있어서는, 상기 양이온 중합성 성분(A)으로서, 방향족 에폭시 화합물(A3)을 더욱 함유하는 것이 바람직하다. 또한, 본 발명의 경화성 조성물에 있어서는, 상기 방향족 에폭시 화합물(A3)은, 다관능 방향족 에폭시 화합물인 것이 바람직하다. 또한, 본 발명의 경화성 조성물에 있어서는, 상기 폴리머(E)가, 상기 식(I)으로 표시되는 단량체 및 상기 식(II)으로 표시되는 단량체로부터 얻어지는 폴리머이며, 상기 식(I) 중의 X가, 탄소 원자수 6∼12의 아릴기이며, 상기 식(II) 중의 X'가, 탄소 원자수 1∼7의 알킬기이며, 상기 알킬기가 에폭시기로 치환되어 있는 것이 바람직하다. In the curable composition of the present invention, it is preferable to further contain an aromatic epoxy compound (A3) as the cationic polymerizable component (A). Further, in the curable composition of the present invention, the aromatic epoxy compound (A3) is preferably a polyfunctional aromatic epoxy compound. In the curable composition of the present invention, the polymer (E) is a polymer obtained from the monomer represented by the formula (I) and the monomer represented by the formula (II) Is an aryl group having 6 to 12 carbon atoms, and X 'in the formula (II) is an alkyl group having 1 to 7 carbon atoms, and the alkyl group is preferably substituted with an epoxy group.
본 발명의 경화물의 제조 방법은, 본 발명의 경화성 조성물에, 활성 에너지선을 조사하는 것, 또는, 가열하는 것을 특징으로 하는 것이다. The method for producing a cured product of the present invention is characterized in that the curable composition of the present invention is irradiated with an active energy ray or heated.
본 발명의 경화물은, 본 발명의 경화성 조성물의 경화물인 것을 특징으로 하는 것이다. The cured product of the present invention is a cured product of the curable composition of the present invention.
본 발명에 의하면, 경화물의 유리 전이 온도가 높고, 밀착성이 우수한 경화성 조성물, 경화물의 제조 방법, 및 그 경화물을 제공할 수 있다. 본 발명의 경화성 조성물은, 특히 접착제에 유용하다.According to the present invention, it is possible to provide a curable composition having a high glass transition temperature of the cured product and excellent adhesiveness, a process for producing the cured product, and a cured product thereof. The curable composition of the present invention is particularly useful for adhesives.
이하, 본 발명의 경화성 조성물에 대하여 상세하게 설명한다.Hereinafter, the curable composition of the present invention will be described in detail.
본 발명의 경화성 조성물은, 양이온 중합성 성분(A) 45∼90 질량부와, 양이온 중합 개시제(B) 0.001∼15 질량부와, 라디칼 중합성 성분(C) 1∼15 질량부와, 라디칼 중합 개시제(D) 1∼10 질량부와, 하기 식(I)으로 표시되는 단량체로부터 얻어지는 폴리머, 하기 식(II)으로 표시되는 단량체로부터 얻어지는 폴리머, 하기 식(I)으로 표시되는 단량체로부터 선택되는 2종 이상의 단량체로부터 얻어지는 폴리머, 하기 식(II)으로 표시되는 단량체로부터 선택되는 2종 이상의 단량체로부터 얻어지는 폴리머, 및 하기 식(I)으로 표시되는 단량체 및 하기 식(II)으로 표시되는 단량체로부터 얻어지는 폴리머로 이루어지는 군으로부터 선택되는 중량 평균 분자량 1,000∼30,000인 폴리머(E) 1∼20 질량부를 함유한다. 본 발명의 경화성 조성물에 있어서는, 양이온 중합성 성분(A)은, 다가 알코올의 글리시딜화물 또는 다가 알코올 알킬렌옥사이드 부가물의 글리시딜화물(A1)과, 옥세탄 화합물(A2)을 필수 성분으로 하고, 라디칼 중합성 성분(C)은, 에폭시기 및 에틸렌성 불포화기를 가지는 화합물(C1), 또는 탄소 원자수 2∼20인 다가 알코올의 아크릴산 에스테르 혹은 탄소 원자수 2∼20인 다가 알코올의 메타크릴산 에스테르(C2)를 필수 성분으로 한다.The curable composition of the present invention comprises 45 to 90 parts by mass of the cationic polymerizable component (A), 0.001 to 15 parts by mass of the cationic polymerization initiator (B), 1 to 15 parts by mass of the radical polymerizable component (C) 1 to 10 parts by mass of an initiator (D), a polymer obtained from a monomer represented by the following formula (I), a polymer obtained from a monomer represented by the following formula (II), a polymer obtained from a monomer represented by the following formula A polymer obtained from two or more kinds of monomers selected from monomers represented by the following formula (II), a polymer obtained from the monomers represented by the following formula (I) and a monomer represented by the following formula (II) And 1 to 20 parts by mass of a polymer (E) having a weight average molecular weight of 1,000 to 30,000. In the curable composition of the present invention, the cationic polymerizable component (A) is obtained by reacting a glycidylated product of a polyhydric alcohol or a glycidylated product of a polyhydric alcohol alkylene oxide adduct (A1) with an oxetane compound (A2) (C) having an epoxy group and an ethylenic unsaturated group, or an acrylate ester of a polyhydric alcohol having 2 to 20 carbon atoms or a methacrylic ester of a polyhydric alcohol having 2 to 20 carbon atoms An acid ester (C2) as an essential component.
여기서, 식(I) 중, X는, 탄소 원자수 1∼7의 알킬기, 탄소 원자수 1∼7의 알콕시기, 탄소 원자수 6∼12의 아릴기, 탄소 원자수 6∼12의 아릴옥시기 혹은 탄소 원자수 6∼10의 지환식 탄화수소기, 또는 이들 기 중의 수소 원자가, 에폭시기, 옥세탄기, 수산기 및 카르복실기로 이루어지는 군으로부터 선택되는 1종 이상의 기로 치환된 것이다.In the formula (I), X represents an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aryloxy group having 6 to 12 carbon atoms Or an alicyclic hydrocarbon group having 6 to 10 carbon atoms, or hydrogen atoms in these groups are substituted with at least one group selected from the group consisting of an epoxy group, oxetane group, hydroxyl group and carboxyl group.
여기서, 식(II) 중, R1은, 수소 원자, 메틸기 또는 할로겐 원자를 나타내고, X'는, 탄소 원자수 1∼7의 알킬기, 탄소 원자수 6∼12의 아릴기 혹은 탄소 원자수 6∼10의 지환식 탄화수소기, 또는 이들 기 중의 수소 원자가, 에폭시기, 옥세탄기, 수산기 및 카르복실기로 이루어지는 군으로부터 선택되는 1종 이상의 기로 치환된 것이다.X 'represents an alkyl group having 1 to 7 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an aryl group having 6 to 12 carbon atoms. In the formula (II), R 1 represents a hydrogen atom, a methyl group or a halogen atom, Or an alicyclic hydrocarbon group having 1 to 10 carbon atoms or hydrogen atoms in these groups is substituted with at least one group selected from the group consisting of an epoxy group, oxetane group, hydroxyl group and carboxyl group.
본 발명의 경화성 조성물에 관한 양이온 중합성 성분(A)은, 에너지선 조사 또는 가열에 의해 활성화한 양이온 중합 개시제에 의해, 고분자화 또는 가교 반응을 일으키는 화합물이다. 에폭시 화합물, 옥세탄 화합물, 비닐 에테르 화합물 등을 예로 들 수 있다.The cationic polymerizable component (A) related to the curable composition of the present invention is a compound which causes polymerisation or crosslinking reaction by a cationic polymerization initiator activated by energy ray irradiation or heating. An epoxy compound, an oxetane compound, and a vinyl ether compound.
본 발명의 경화성 조성물에 관한 양이온 중합성 성분(A)은, 다가 알코올의 글리시딜화물 또는 다가 알코올 알킬렌옥사이드 부가물의 글리시딜화물(A1)과, 옥세탄 화합물(A2)을 필수 성분으로 하지만, 그 외의 에폭시 화합물로서, 방향족 에폭시 화합물(A3) 및 지환식 에폭시 화합물(A4) 등을 사용할 수도 있다.The cationic polymerizable component (A) relating to the curable composition of the present invention is a composition comprising a glycidylated product of a polyhydric alcohol or a glycidylated product of a polyhydric alcohol alkylene oxide adduct and an oxetane compound (A2) as essential components However, as the other epoxy compounds, an aromatic epoxy compound (A3) and an alicyclic epoxy compound (A4) may also be used.
상기 다가 알코올의 글리시딜화물 또는 다가 알코올 알킬렌옥사이드 부가물의 글리시딜화물(A1)로서는, 다가 알코올 또는 다가 알코올 알킬렌옥사이드 부가물을 글리시딜화한 것을 예로 들 수 있고, 글리시딜화물의 분자량이 250 이상인 것이 바람직하다.Examples of glycidylates of polyhydric alcohols or glycidylates (A1) of polyhydric alcohol alkylene oxide adducts include glycidylated polyhydric alcohols or polyhydric alcohol alkylene oxide adducts. Examples of the glycidyl Is preferably 250 or more.
상기 다가 알코올의 글리시딜화물, 또는 다가 알코올알킬렌옥사이드 부가물의 글리시딜화물(A1)로서는, 1,4-부탄디올디글리시딜에테르, 1,6-헥산디올디글리시딜에테르, 네오펜틸글리콜디글리시딜에테르, 글리세린의 트리글리시딜에테르, 트리메틸올프로판의 트리글리시딜에테르, 소르비톨의 테트라글리시딜에테르, 디펜타에리트리톨의 헥사글리시딜에테르, 폴리에틸렌글리콜의 디글리시딜에테르, 폴리프로필렌글리콜의 디글리시딜에테르, 디시클로펜타디엔디메탄올디글리시딜에테르 등의 다가 알코올의 글리시딜에테르, 또한 프로필렌글리콜, 트리메틸올프로판, 글리세린 등의 지방족 다가 알코올에 1종 또는 2종 이상의 알킬렌옥사이드를 부가함으로써 얻어지는 폴리에테르폴리올의 폴리글리시딜에테르화물, 지방족 장쇄(長鎖) 이염기산의 디글리시딜에스테르를 예로 들 수 있다.Examples of the glycidylate of the polyhydric alcohol or the glycidylate (A1) of the polyhydric alcohol alkylene oxide adduct include 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, neo Pentyl glycol diglycidyl ether, triglycidyl ether of glycerin, triglycidyl ether of trimethylol propane, tetraglycidyl ether of sorbitol, hexaglycidyl ether of dipentaerythritol, diglycidyl of polyethylene glycol Glycidyl ether of a polyhydric alcohol such as ether, diglycidyl ether of polypropylene glycol, and dicyclopentadiene dimethanol diglycidyl ether, and aliphatic polyhydric alcohol such as propylene glycol, trimethylol propane, and glycerin, A polyglycidyl ether compound of a polyether polyol obtained by adding two or more alkylene oxides, a polyglycidyl ether compound of an aliphatic long chain dibasic acid There may be mentioned the esters sidil example.
다가 알코올의 글리시딜화물 또는 다가 알코올알킬렌옥사이드 부가물의 글리시딜화물(A1)로서는, 지방족 고급 알코올의 모노글리시딜에테르나 고급 지방산의 글리시딜에스테르, 에폭시화 대두유, 에폭시스테아르산 옥틸, 에폭시스테아르산 부틸, 에폭시화 대두유, 에폭시화 폴리부타디엔 등을 예로 들 수 있다.Examples of glycidylates of polyhydric alcohols or polyhydric alcohol alkylene oxide adducts include monoglycidyl ethers of aliphatic higher alcohols, glycidyl esters of higher fatty acids, epoxidized soybean oil, octyl stearate , Butyl epoxystearate, epoxidized soybean oil, and epoxidized polybutadiene.
다가 알코올의 글리시딜화물 또는 다가 알코올 알킬렌옥사이드 부가물의 글리시딜화물(A1)로서는, 포화 축합환을 가지는 것이, 경화물의 경화성 및 밀착성이 향상되므로 바람직하다.As the glycidylate of the polyhydric alcohol or the glycidylate (A1) of the polyhydric alcohol alkylene oxide adduct, it is preferable to have a saturated condensed ring since the curing property and adhesion of the cured product are improved.
상기 다가 알코올의 글리시딜화물, 또는 다가 알코올알킬렌옥사이드 부가물의 글리시딜화물(A1)로서는, 시판품을 사용할 수 있으며, 예를 들면, 데나콜 EX-121, 데나콜 EX-171, 데나콜 EX-192, 데나콜 EX-211, 데나콜 EX-212, 데나콜 EX-313, 데나콜 EX-314, 데나콜 EX-321, 데나콜 EX-411, 데나콜 EX-421, 데나콜 EX-512, 데나콜 EX-521, 데나콜 EX-611, 데나콜 EX-612, 데나콜 EX-614, 데나콜 EX-622, 데나콜 EX-810, 데나콜 EX-811, 데나콜 EX-850, 데나콜 EX-851, 데나콜 EX-821, 데나콜 EX-830, 데나콜 EX-832, 데나콜 EX-841, 데나콜 EX-861, 데나콜 EX-911, 데나콜 EX-941, 데나콜 EX-920, 데나콜 EX-931(나가세켐텍스(주)사 제조); 에포라이트 M-1230, 에포라이트 40E, 에포라이트 100E, 에포라이트 200E, 에포라이트 400E, 에포라이트 70P, 에포라이트 200P, 에포라이트 400P, 에포라이트 1500NP, 에포라이트 1600, 에포라이트 80MF, 에포라이트 100MF(교에이샤화학(共榮社化學)(주)사 제조), 아데카글리시롤 ED-503, 아데카글리시롤 ED-503G, 아데카글리시롤 ED-506, 아데카글리시롤 ED-523T, 아데카레진 EP-4088S, 아데카레진 EP-4080E((주)ADEKA사 제조) 등이 있다.As the glycidylated product of the polyhydric alcohol or the glycidylated product (A1) of the polyhydric alcohol alkylene oxide adduct, commercially available products can be used. Examples of the glycidylated product include Denacol EX-121, Denacol EX-171, Denacol EX-421, Denacol EX-421, Denacol EX-311, Denacol EX-321, Denacol EX-421, Denacol EX-421, Denacol EX- Denacol EX-810, Denacol EX-811, Denacol EX-850, Denacol EX-810, Denacol EX- Denacol EX-911, Denacol EX-941, Denacol EX-821, Denacol EX-821, Denacol EX-832, Denacol EX-841, Denacol EX-861, EX-920, Denacol EX-931 (manufactured by Nagase ChemteX Corporation); Epolite M-1230, Epolite 40E, Epolite 100E, Epolite 200E, Epolite 400E, Epolite 70P, Epolite 200P, Epolite 400P, Epolite 1500NP, Epolite 1600, Epolite 80MF, Epolite 100MF ( (Manufactured by Kyoeisha Chemical Co., Ltd.), adekaglycylol ED-503, adekaglycylol ED-503G, adekaglycollol ED-506, adekaglycollol ED -523T, ADEKA RESIN EP-4088S, ADEKA RESIN EP-4080E (manufactured by ADEKA Corporation), and the like.
상기 옥세탄 화합물(A2)로서는, 3,7-비스(3-옥세타닐)-5-옥사-노난, 1,4-비스[(3-에틸-3-옥세타닐메톡시)메틸]벤젠, 1,2-비스[(3-에틸-3-옥세타닐메톡시)메틸]에탄, 1,3-비스[(3-에틸-3-옥세타닐메톡시)메틸]프로판, 에틸렌글리콜비스(3-에틸-3-옥세타닐메틸)에테르, 트리에틸렌글리콜비스(3-에틸-3-옥세타닐메틸)에테르, 테트라에틸렌글리콜비스(3-에틸-3-옥세타닐메틸)에테르, 1,4-비스(3-에틸-3-옥세타닐메톡시)부탄, 1,6-비스(3-에틸-3-옥세타닐메톡시)헥산 등의 2관능 지방족 옥세탄 화합물, 3-에틸-3-[(페녹시)메틸]옥세탄, 3-에틸-3-(헥실옥시메틸)옥세탄, 3-에틸-3-(2-에틸헥실옥시메틸)옥세탄, 3-에틸-3-(하이드록시메틸)옥세탄, 3-에틸-3-(클로로메틸)옥세탄 등의 1관능 옥세탄 화합물 등을 예로 들 수 있다. 그 중에서도 2관능 지방족 옥세탄 화합물이, 밀착성이 향상되므로 바람직하다. 이들은 1종 단독 혹은 2종 이상을 조합하여 사용할 수 있다.Examples of the oxetane compound (A2) include 3,7-bis (3-oxetanyl) -5-oxa- nonane, 1,4-bis [3-ethyl-3- oxetanylmethoxy) (3-ethyl-3-oxetanylmethoxy) methyl] propane, ethylene glycol bis (3- Ethyl-3-oxetanylmethyl) ether, triethylene glycol bis (3-ethyl-3-oxetanylmethyl) ether, tetraethylene glycol bis Bifunctional aliphatic oxetane compounds such as bis (3-ethyl-3-oxetanylmethoxy) butane and 1,6-bis (3-ethyl-3-oxetanylmethoxy) Ethyl-3- (2-ethylhexyloxymethyl) oxetane, 3-ethyl-3- (hydroxymethyl) ) Oxetane, and 3-ethyl-3- (chloromethyl) oxetane; and the like. Among them, a bifunctional aliphatic oxetane compound is preferable because adhesion is improved. These may be used singly or in combination of two or more.
상기 옥세탄 화합물(A2)로서는, 시판품을 사용할 수 있으며, 예를 들면, 2-하이드록시에틸비닐에테르, 디에틸렌글리콜모노비닐에테르, 4-하이드록시부틸비닐에테르(마루젠석유화학(丸善石油化學)(주)사 제조); 아론옥세탄 OXT-121, OXT-221, EXOH, POX, OXA, OXT-101, OXT-211, OXT-212(도아합성(주)사 제조), 에타나콜 OXBP, OXTP(우베흥산(宇部興産)(주)사 제조) 등이 있다.As the oxetane compound (A2), commercially available products can be used, and examples thereof include 2-hydroxyethyl vinyl ether, diethylene glycol monovinyl ether, 4-hydroxybutyl vinyl ether (Maruzen Petrochemical Co., )); OXT-121, OXT-221, EXOH, POX, OXA, OXT-101, OXT-211 and OXT-212 (manufactured by Toa Gosei Co., Ltd.), Ethanacol OXBP, OXTP (manufactured by Ube Industries, (Manufactured by Nippon Steel Chemical Co., Ltd.).
상기 방향족 에폭시 화합물(A3)은, 방향환을 포함하는 에폭시 화합물을 나타내고, 방향족 에폭시 화합물(A3)의 구체예로서는, 페놀, 크레졸, 부틸페놀 등, 적어도 1개의 방향족환을 가지는 다가 페놀 또는, 그 알킬렌옥사이드 부가물의 모노/폴리글리시딜에테르화물, 예를 들면, 비스페놀 A, 비스페놀 F, 또는 이들에 알킬렌옥사이드를 더 부가한 화합물의 글리시딜에테르화물이나 에폭시 노볼락 수지; 레조르시놀이나 하이드로퀴논, 카테콜 등의 2개 이상의 페놀성 수산기를 가지는 방향족 화합물의 모노/폴리글리시딜에테르화물; 페닐디메탄올이나 페닐디에탄올, 페닐디부탄올 등의 알코올성 수산기를 2개 이상 가지는 방향족 화합물의 글리시딜에테르화물; 프탈산, 테레프탈산, 트리멜리트산 등의 2개 이상의 카르복시산을 가지는 다염기산 방향족 화합물의 글리시틸에스테르, 벤조산의 글리시틸에스테르, 스티렌옥사이드 또는 디비닐벤젠의 에폭시화물 등이 있다.Specific examples of the aromatic epoxy compound (A3) include a polyhydric phenol having at least one aromatic ring, such as phenol, cresol, and butylphenol, or a polyhydric phenol having at least one aromatic ring Mono- / polyglycidyl ether compounds of phenol, phenol, bisphenol A, bisphenol F, or alkylene oxide added thereto, or epoxy novolac resins; Mono / polyglycidyl ether compounds of aromatic compounds having two or more phenolic hydroxyl groups such as resorcinol, hydroquinone, and catechol; Glycidyl ether compounds of aromatic compounds having two or more alcoholic hydroxyl groups such as phenyl dimethanol, phenyl diethanol and phenyl dibutanol; Glycidyl esters of polybasic acid aromatic compounds having two or more carboxylic acids such as phthalic acid, terephthalic acid and trimellitic acid, glycityl esters of benzoic acid, styrene oxide or epoxides of divinylbenzene.
상기 방향족 에폭시 화합물(A3)로서는, 시판품을 사용할 수 있으며, 예를 들면, 데나콜 EX-146, 데나콜 EX-147, 데나콜 EX-201, 데나콜 EX-203, 데나콜 EX-711, 데나콜 EX-721, 온코트 EX-1020, 온코트 EX-1030, 온코트 EX-1040, 온코트 EX-1050, 온코트 EX-1051, 온코트 EX-1010, 온코트 EX-1011, 온코트 1012(나가세켐텍스(주)사 제조); 오그솔 PG-100, 오그솔 EG-200, 오그솔 EG-210, 오그솔 EG-250(오사카가스케미컬(주)사 제조); HP4032, HP4032D, HP4700(DIC(주)사 제조); ESN-475V(신닛테츠스미킨(新日鐵住金)화학(주)사 제조); 에피코트 YX8800(미쓰비시화학(주)사 제조); 마프루프 G-0105SA, 마프루프 G-0130SP(니치유(日油)(주)사 제조); 에피클론 N-665, 에피클론 HP-7200(DIC(주) 사 제조); EOCN-1020, EOCN-102S, EOCN-103S, EOCN-104S, XD-1000, NC-3000, EPPN-501H, EPPN-501HY, EPPN-502H, NC-7000L(닛폰카야쿠(日本化藥)(주)사 제조); 아데카레진 EP-4000, 아데카레진 EP-4005, 아데카레진 EP-4100, 아데카레진 EP-4901((주)ADEKA사 제조); TECHMORE VG-3101L((주)프린텍사 제조) 등을 들 수 있다. 상기 방향족 에폭시 화합물(A3)로서는, 다관능인 것이, 경화성이 우수하므로 바람직하다.Examples of the aromatic epoxy compound (A3) include commercially available products such as Denacol EX-146, Denacol EX-147, Denacol EX-201, Denacol EX-203, Denacol EX- OnCoat EX-1010, OnCoat EX-1011, Oncoat EX-1010, Oncoat EX-1051, Oncoat EX-1010, Oncoat EX-1011, Oncoat EX- (Manufactured by Nagase ChemteX Corporation); Ogrosol PG-100, Oggol EG-200, Oggol EG-210, Oggol EG-250 (manufactured by Osaka Gas Chemical Co., Ltd.); HP4032, HP4032D, HP4700 (manufactured by DIC Corporation); ESN-475V (manufactured by Shin-Nitetsu Sumitomo Chemical Co., Ltd.); Epikote YX8800 (manufactured by Mitsubishi Chemical Corporation); Mahurup G-0105SA, Mahuruf G-0130SP (manufactured by Nihon Oil Co., Ltd.); Epiclon N-665, Epiclon HP-7200 (manufactured by DIC Corporation); EOCN-1020, EOCN-102S, EOCN-103S, EOCN-104S, XD-1000, NC-3000, EPPN-501H, EPPN-501HY, EPPN-502H, NC-7000L (Nippon Kayaku )); ADEKA RESIN EP-4000, ADEKA RESIN EP-4005, ADEKA RESIN EP-4100, ADEKA RESIN EP-4901 (manufactured by ADEKA Corporation); TECHMORE VG-3101L (manufactured by PRINTEC Co., Ltd.), and the like. The aromatic epoxy compound (A3) is preferably polyfunctional because it is excellent in curability.
상기 지환식 에폭시 화합물(A4)이란, 포화환에 결합기를 통하지 않고 직접 옥시란환이 결합하고 있는 것을 일컫는다. 지환식 에폭시 화합물(A4)의 구체예로서는, 적어도 1개의 지환식환을 가지는 다가 알코올의 폴리글리시딜에테르화물 또는 시클로헥센이나 시클로펜텐환 함유 화합물을 산화제로 에폭시화함으로써 얻어지는 시클로헥센옥사이드나 시클로펜텐옥사이드 함유 화합물을 들 수 있다. 예를 들면, 3,4-에폭시시클로헥실에틸-3,4-에폭시시클로헥산카르복실레이트, 3,4-에폭시-1-메틸시클로헥실-3,4-에폭시-1-메틸헥산카르복실레이트, 6-메틸-3,4-에폭시시클로헥실에틸-6-메틸-3,4-에폭시시클로헥산카르복실레이트, 3,4-에폭시-3-메틸시클로헥실메틸-3,4-에폭시-3-메틸시클로헥산카르복실레이트, 3,4-에폭시-5-메틸시클로헥실메틸-3,4-에폭시-5-메틸시클로헥산카르복실레이트, 비스(3,4-에폭시시클로헥실에틸)아디페이트, 3,4-에폭시-6-메틸시클로헥산카르복실레이트, 메틸렌비스(3,4-에폭시시클로헥산), 프로판-2,2-디일-비스(3,4-에폭시시클로헥산), 2,2-비스(3,4-에폭시시클로헥실)프로판, 디시클로펜타디엔디에폭사이드, 에틸렌비스(3,4-에폭시시클로헥산카르복실레이트), 에폭시헥사하이드로프탈산 디옥틸, 에폭시헥사하이드로프탈산 디-2-에틸헥실, 1-에폭시에틸-3,4-에폭시시클로헥산, 1,2-에폭시-2-에폭시에틸시클로헥산, α-피넨옥사이드, 리모넨디옥사이드 등이 있다. 지환식 에폭시 화합물(A4)로서는, 3,4-에폭시시클로헥실에틸-3,4-에폭시시클로헥산카르복실레이트 또는 3,4-에폭시-1-메틸시클로헥실-3,4-에폭시-1-메틸헥산카르복실레이트가, 밀착성 향상의 관점에서 바람직하다.The alicyclic epoxy compound (A4) means that the oxirane ring is directly bonded to the prepolymer without passing through a bonding group. Specific examples of the alicyclic epoxy compound (A4) include polyglycidyl ether compounds of polyhydric alcohols having at least one alicyclic ring or cyclohexene or cyclopentene oxide obtained by epoxidizing cyclohexene or cyclopentane ring- Containing compound. For example, 3,4-epoxycyclohexylethyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-1-methylcyclohexyl-3,4-epoxy-1-methylhexanecarboxylate, Epoxycyclohexylethyl-6-methyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-3-methylcyclohexylmethyl-3,4- (3,4-epoxycyclohexylethyl) adipate, 3, 4-epoxy-5-methylcyclohexylmethyl-3,4-epoxy-5-methylcyclohexanecarboxylate, (3,4-epoxycyclohexane), propane-2,2-diyl-bis (3,4-epoxycyclohexane), 2,2-bis Epoxycyclohexyl) propane, dicyclopentadiene diepoxide, ethylenebis (3,4-epoxycyclohexanecarboxylate), epoxyhexahydrophthalate dioctyl, epoxyhexahydrophthalic acid di-2-ethylhexyl , 1- Epoxy-3, 4-epoxycyclohexane, 1,2-epoxy-2-epoxyethylcyclohexane, alpha -pinene oxide, limonene dioxide and the like. As the alicyclic epoxy compound (A4), 3,4-epoxycyclohexylethyl-3,4-epoxycyclohexanecarboxylate or 3,4-epoxy-1-methylcyclohexyl-3,4-epoxy- Hexanecarboxylate is preferable from the viewpoint of improving the adhesion.
상기 지환식 에폭시 화합물(A4)로서는, 시판품을 사용할 수 있고, 예를 들면, 셀록사이드 2021P, 셀록사이드 2081, 셀록사이드 2000, 셀록사이드 3000((주)다이셀사 제조) 등이 있다. As the alicyclic epoxy compound (A4), a commercially available product can be used. Examples of the alicyclic epoxy compound (A4) include Celloxide 2021P, Celloxide 2081, Celloxide 2000, and Celloxide 3000 (manufactured by Daicel Chemical Industries, Ltd.).
상기 비닐에테르 화합물로서는, 예를 들면, 디에틸렌글리콜모노비닐에테르, 트리에틸렌글리콜디비닐에테르, n-도데실비닐에테르, 시클로헥실비닐에테르, 2-에틸헥실비닐에테르, 2-클로로에틸비닐에테르, 에틸비닐에테르, 이소부틸비닐에테르, 트리에틸렌글리콜비닐에테르, 2-하이드록시에틸비닐에테르, 4-하이드록시부틸비닐에테르, 1,6-시클로헥산디메탄올모노비닐에테르, 에틸렌글리콜디비닐에테르, 1,4-부탄디올디비닐에테르, 1,6-시클로헥산디메탄올디비닐에테르 등이 있다.Examples of the vinyl ether compound include diethylene glycol monovinyl ether, triethylene glycol divinyl ether, n-dodecyl vinyl ether, cyclohexyl vinyl ether, 2-ethylhexyl vinyl ether, 2-chloroethyl vinyl ether, Ethyl vinyl ether, isobutyl vinyl ether, triethylene glycol vinyl ether, 2-hydroxyethyl vinyl ether, 4-hydroxybutyl vinyl ether, 1,6-cyclohexanedimethanol monovinyl ether, ethylene glycol divinyl ether, , 4-butanediol divinyl ether, 1,6-cyclohexanedimethanol divinyl ether, and the like.
상기 양이온 중합성 성분(A)에 있어서, 상기 다가 알코올의 글리시딜화물 또는 다가 알코올알킬렌옥사이드 부가물의 글리시딜화물(A1), 옥세탄 화합물(A2), 방향족 에폭시 화합물(A3), 지환식 에폭시 화합물(A4) 및 비닐에테르 화합물의 사용 비율은, 양이온 중합성 성분(A) 100질량부에 대하여, 다가 알코올의 글리시딜화물 또는 다가 알코올알킬렌옥사이드 부가물의 글리시딜화물(A1) 50∼80 질량부, 옥세탄 화합물(A2) 20∼50 질량부, 방향족 에폭시 화합물(A3) 0∼50 질량부, 지환식 에폭시 화합물(A4) 0∼30 질량부, 비닐에테르 화합물 0∼20질량부인 것이, 점도, 도포성, 반응성 및 경화성이 향상되므로 바람직하다.In the cationic polymerizable component (A), the glycidylate of the polyhydric alcohol or the glycidylate of the polyhydric alcohol alkylene oxide adduct (A1), the oxetane compound (A2), the aromatic epoxy compound (A3) The ratio of the epoxy compound (A4) and the vinyl ether compound to the glycidylated product of the polyhydric alcohol or the polyhydric alcohol alkylene oxide adduct (A1) relative to 100 parts by mass of the cationic polymerizable component (A) (A3), 0 to 50 parts by mass of an aromatic epoxy compound (A3), 0 to 30 parts by mass of an alicyclic epoxy compound (A4), 0 to 20 parts by mass of a vinyl ether compound Is preferred because it improves viscosity, coatability, reactivity and curability.
본 발명의 경화성 조성물에 관한 양이온 중합 개시제(B)란, 에너지선 조사 또는 가열에 의해 양이온 중합을 개시시키는 물질을 방출시키는 것이 가능한 화합물이라면 어떤 것이라도 구애받지 않지만, 바람직하게는, 에너지선의 조사에 의해 루이스산을 방출하는 오늄염인 복염, 또는 그의 유도체이다. 이러한 화합물의 대표적인 것으로서는, 하기 일반식The cationic polymerization initiator (B) related to the curable composition of the present invention is not particularly limited as long as it is a compound capable of releasing a substance that initiates cationic polymerization by energy ray irradiation or heating, Onium salt, or a derivative thereof, which releases Lewis acid. Representative examples of such compounds include compounds represented by the following general formula
[A]r+[B]r- [A] r + [B] r-
로 표시되는 양이온과 음이온의 염을 예로 들 수 있다.For example, salts of anions and cations represented by the following formulas.
여기서 양이온 [A]r+는 오늄인 것이 바람직하고, 그 구조는, 예를 들면, 하기 일반식Here, the cation [A] r + is preferably onium, and its structure is, for example,
[(R2)aQ]r+ [(R 2 ) a Q] r +
으로 표시할 수 있다.As shown in FIG.
또한 여기서, R2는 탄소 원자수가 1∼60이며, 탄소 원자 이외의 원자를 몇 개 포함하고 있어도 되는 유기의 기이다. a는 1∼5가 되는 정수이다. a개의 R2는 각각 독립적이며, 동일할 수도 있고 상이할 수도 있다. 또한, 적어도 1개는, 방향환를 가지는 상기와 같은 유기의 기인 것이 바람직하다. Q는 S, N, Se, Te, P, As, Sb, Bi, O, I, Br, Cl, F, N=N으로 이루어지는 군으로부터 선택되는 원자 혹은 원자단이다. 또한, 양이온 [A]r+ 중의 Q의 원자가를 q로 했을 때, r=a-q가 되는 관계가 성립하는 것이 필요하다(다만, N=N은 원자가 0으로서 취급함).Here, R 2 is an organic group having 1 to 60 carbon atoms, which may contain several atoms other than carbon atoms. and a is an integer of 1 to 5. a > R < 2 > are each independent, and may be the same or different. It is also preferred that at least one is an organic group as described above having an aromatic ring. Q is an atom or atomic group selected from the group consisting of S, N, Se, Te, P, As, Sb, Bi, O, I, Br, Cl, When the valence of Q in the cation [A] r + is q, it is necessary that the relation r = aq is satisfied (note that N = N is treated as 0).
또한, 음이온 [B]r-은, 할로겐화물 착체인 것이 바람직하고, 그 구조는, 예를 들면, 하기 일반식The anion [B] r- is preferably a halide complex, and its structure may be, for example,
[LYb]r-로[LY b ] r-
표시할 수 있다.Can be displayed.
또한 여기서, L은 할로겐화물 착체의 중심 원자인 금속 또는 반금속(Metalloid)이며, B, P, As, Sb, Fe, Sn, Bi, Al, Ca, In, Ti, Zn, Sc, V, Cr, Mn, Co 등이다. Y는 할로겐 원자이다. b는 3∼7이 되는 정수이다. 또한, 음이온 [B]r- 중의 L의 원자가를 p로 했을 때, r=b-p가 되는 관계가 성립하는 것이 필요하다.In addition, L is a metal or a metalloid, which is a central atom of a halide complex, and B, P, As, Sb, Fe, Sn, Bi, Al, Ca, In, Ti, Zn, Sc, , Mn, Co, and the like. Y is a halogen atom. and b is an integer of 3 to 7. Further, when the valence of L in the anion [B] r- is p, it is necessary that the relation r = bp is established.
상기 일반식의 음이온 [LYb]r-의 구체예로서는, 테트라키스(펜타플루오로페닐)보레이트, 테트라(3,5-디플루오로-4-메톡시페닐)보레이트, 테트라플루오로보레이트(BF4)-, 헥사플루오로포스페이트(PF6)-, 헥사플루오로안티모네이트(SbF6)-, 헥사플루오로아르세네이트(AsF6)-, 헥사클로로안티모네이트(SbCl6)- 등을 들 수 있다.Anions of the formula [b LY] Specific examples of the r-, tetrakis (pentafluorophenyl) borate, tetra (3,5-difluoro-4-methoxyphenyl) borate, and borate (BF 4 tetrafluoro ) - or the like -, phosphate (PF 6) hexafluoro -, hexafluoroantimonate (SbF 6), hexafluorophosphate are Senate (AsF 6), hexachloro antimonate (SbCl 6) .
또한, 음이온 [B]r-는, 하기 일반식The anion [B] r- can be represented by the following general formula
[LYb-1(OH)]r- [LY b-1 (OH)] r-
로 표시되는 구조의 것도 바람직하게 사용할 수 있다. L, Y, b는 상기와 동일하다. 또, 그 외 사용할 수 있는 음이온으로서는, 과염소산 이온(ClO4)-, 트리플루오로메틸아황산 이온(CF3SO3)-, 플루오로술폰산 이온(FSO3)-, 톨루엔술폰산 음이온, 트리니트로벤젠술폰산 음이온, 캠퍼 술포네이트, 노나플루오로부탄술포네이트, 헥사데카플루오로옥탄술포네이트, 테트라아릴보레이트, 테트라키스(펜타플루오로페닐)보레이트 등을 예로 들 수 있다.Can also be preferably used. L, Y, and b are the same as described above. Examples of other anions that can be used include perchlorate ion (ClO 4 ) - , trifluoromethyl sulfite ion (CF 3 SO 3 ) -, fluorosulfonate ion (FSO 3 ) - , toluenesulfonate anion, trinitrobenzenesulfonate anion , Camphorsulfonate, nonafluorobutanesulfonate, hexadecafluorooctanesulfonate, tetraarylborate, tetrakis (pentafluorophenyl) borate, and the like.
본 발명의 경화성 조성물에서는, 이와 같은 오늄염 중에서도, 하기 (ㄱ)∼ (ㄷ)의 방향족오늄염을 사용하는 것이 특히 유효하다. 이들 중으로부터, 그 1종을 단독으로, 또는 2종 이상을 혼합하여 사용할 수 있다.In the curable composition of the present invention, among these onium salts, it is particularly effective to use the following (a) to (c) aromatic onium salts. Of these, one type may be used alone, or two or more types may be used in combination.
(ㄱ) 페닐디아조늄헥사플루오로포스페이트, 4-메톡시페닐디아조늄헥사플루오로안티모네이트, 4-메틸페닐디아조늄헥사플루오로포스페이트 등의 아릴디아조늄염(A) aryldiazonium salts such as phenyldiazonium hexafluorophosphate, 4-methoxyphenyldiazonium hexafluoroantimonate, and 4-methylphenyldiazonium hexafluorophosphate;
(ㄴ) 디페닐요오드늄헥사플루오로안티모네이트, 디(4-메틸페닐)요오드늄헥사플루오로포스페이트, 디(4-tert-부틸페닐)요오드늄헥사플루오로포스페이트, 톨릴쿠밀요오드늄테트라키스(펜타플루오로페닐)보레이트 등의 디아릴요오드늄염(B) diphenyliodonium hexafluoroantimonate, di (4-methylphenyl) iodonium hexafluorophosphate, di (4-tert-butylphenyl) iodonium hexafluorophosphate, tolyl cumyl iodonium tetrakis Diaryl iodonium salts such as pentafluorophenylborate
(ㄷ) 하기 군 I 또는 군 II로 표시되는 술포늄 양이온과 헥사플루오로안티몬 이온, 헥사플루오로포스페이트 이온, 테트라키스(펜타플루오로페닐)보레이트 이온 등의 술포늄염(C) Sulfonium cations represented by the following Group I or Group II: sulfonium cations such as hexafluoroantimony ion, hexafluorophosphate ion and tetrakis (pentafluorophenyl)
<군 I><Group I>
<군 II><Group II>
또한, 그 외 바람직한 것으로서는, (η5-2,4-시클로펜타디엔-1-일)[(1,2,3,4,5,6-η)-(1-메틸에틸)벤젠]-아이언-헥사플루오로포스페이트 등의 철-아렌 착체나, 트리스(아세틸아세토네이트)알루미늄, 트리스(에틸아세토네이트아세테이트)알루미늄, 트리스(살리실알데히데이트)알루미늄 등의 알루미늄 착체와 트리페닐실라놀 등의 실라놀류와의 혼합물; 티오페늄염, 티오라늄염, 벤질암모늄, 피리디늄염, 히드라지늄염 등의 염; 디에틸렌트리아민, 트리에틸렌트리아민, 테트라에틸렌펜타민 등의 폴리알킬폴리아민류; 1,2-디아미노시클로헥산, 1,4-디아미노-3,6-디에틸시클로헥산, 이소포론디아민 등의 지환식 폴리아민류; m-크실릴렌디아민, 디아미노디페닐메탄, 디아미노디페닐술폰 등의 방향족 폴리아민류; 상기 폴리아민류와, 페닐글리시딜에테르, 부틸글리시딜에테르, 비스페놀 A-디글리시딜에테르, 비스페놀 F-디글리시딜에테르 등의 글리시딜에테르류 또는 카르복시산의 글리시딜에스테르류 등의 각종 에폭시 수지를 통상적인 방법에 의해 반응시킴으로써 제조되는 폴리에폭시 부가 변성물; 상기 유기 폴리아민류와, 프탈산, 이소프탈산, 다이머산 등의 카르복시산류를 통상적인 방법에 의해 반응시킴으로써 제조되는 아미드화 변성물; 상기 폴리아민류와 포름알데히드 등의 알데히드류 및 페놀, 크레졸, 크실레놀, tert-부틸페놀, 레조르신 등의 핵에 적어도 1개의 알데히드화 반응성 장소를 가지는 페놀류를 통상적인 방법에 의해 반응시킴으로써 제조되는 만니히화 변성물; 다가 카르복시산(옥살산, 말론산, 숙신산, 글루타르산, 아디프산, 피멜산, 수베르산, 아젤라산, 세바스산, 도데칸이산, 2-메틸숙신산, 2-메틸아디프산, 3-메틸아디프산, 3-메틸펜탄이산, 2-메틸옥탄이산, 3,8-디메틸데칸이산, 3,7-디메틸데칸이산, 수첨(水添) 다이머산, 다이머산 등의 지방족 디카르복시산류; 프탈산, 테레프탈산, 이소프탈산, 나프탈렌디카르복시산 등의 방향족 디카르복시산류; 시클로헥산디카르복시산 등의 지환식 디카르복시산류; 트리멜리트산, 트리메스산, 피마자유 지방산의 3량체 등의 트리카르복시산류; 피로멜리트산 등의 테트라카르복시산류 등)의 산무수물; 디시안디아미드, 이미다졸류, 카르복시산 에스테르, 술폰산 에스테르, 아민이미드 등을 예로 들 수 있다.In addition, as other preferable examples, (侶5 -2,4-cyclopentadien-1-yl) [(1,2,3,4,5,6-η) - (1-methylethyl) benzene] (Acetylacetonate) aluminum, tris (ethyl acetonate acetate) aluminum, tris (salicyl aldehyde) aluminum and the like, and triphenylsilanol, such as triphenylsilanol Of silanol; Thiophenium salts, thioronium salts, benzylammonium salts, pyridinium salts, hydrazinium salts and the like; Polyalkylpolyamines such as diethylenetriamine, triethylenetriamine, and tetraethylenepentamine; Alicyclic polyamines such as 1,2-diaminocyclohexane, 1,4-diamino-3,6-diethylcyclohexane and isophoronediamine; aromatic polyamines such as m-xylylenediamine, diaminodiphenylmethane and diaminodiphenylsulfone; Glycidyl ethers such as phenyl glycidyl ether, butyl glycidyl ether, bisphenol A-diglycidyl ether, and bisphenol F-diglycidyl ether, glycidyl esters of carboxylic acid, etc. A polyepoxy addendum modified product prepared by reacting various epoxy resins by the conventional method; An amidated modified product prepared by reacting the above organic polyamines with carboxylic acids such as phthalic acid, isophthalic acid and dimeric acid by a conventional method; Aldehydes such as polyamines and formaldehyde, and phenols having at least one aldehyde-reactive site in nuclei such as phenol, cresol, xylenol, tert-butylphenol, resorcin and the like by a conventional method Mannichite Modified Water; Examples of the polyvalent carboxylic acid include polyvalent carboxylic acids such as oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, dodecanedioic acid, Aliphatic dicarboxylic acids such as adipic acid, 3-methylpentanedioic acid, 2-methyloctanedioic acid, 3,8-dimethyldecanedioic acid, 3,7-dimethyldecanedioic acid, hydrogenated dimer acid and dimeric acid; , Aromatic dicarboxylic acids such as terephthalic acid, isophthalic acid and naphthalene dicarboxylic acid, alicyclic dicarboxylic acids such as cyclohexanedicarboxylic acid, tricarboxylic acids such as trimellitic acid, trimesic acid and trimer of castor oil fatty acid, Tetracarboxylic acids such as acetic acid and the like); Dicyandiamide, imidazoles, carboxylic acid esters, sulfonic acid esters, amine imides and the like.
이들 중에서도, 실용면과 광감도 향상의 관점에서, 방향족 요오드알루미늄염, 방향족 술포늄염, 철-아렌 착체를 사용하는 것이 바람직하고, 하기 구조를 가지는 방향족 술포늄염을, 양이온 중합 개시제(B) 100질량%에 대하여, 적어도 0.1질량% 이상 함유하는 것이 더욱 바람직하다.Of these, aromatic iodoaluminum salts, aromatic sulfonium salts and iron-arene complexes are preferably used from the viewpoints of practical use and improvement of photosensitivity, and an aromatic sulfonium salt having the following structure is mixed with 100% by mass of the cationic polymerization initiator (B) By mass, more preferably at least 0.1% by mass or more.
여기서, 식 중, R11, R12, R13, R14, R15, R16, R17, R18, R19 및 R20은, 각각 독립적으로, 수소 원자, 할로겐 원자, 탄소 원자수 1∼10의 알킬기, 탄소 원자수 1∼10의 알콕시기 또는 탄소 원자수 2∼10의 에스테르 기를 나타내고, R21, R22, R23 및 R24는, 각각 독립적으로, 수소 원자, 할로겐 원자 또는 탄소 원자수 1∼10의 알킬기를 나타내고, R25는, 수소 원자, 할로겐 원자, 탄소 원자수 1∼10의 알킬기 또는 하기 화학식(A)∼화학식(C)으로부터 선택되는 어느 하나의 치환기를 나타내고, Anq -는 q가의 음이온을 나타내고, p는 전하를 중성으로 하는 계수를 나타낸다.In the formula, R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 and R 20 each independently represent a hydrogen atom, a halogen atom, An alkoxy group having 1 to 10 carbon atoms or an ester group having 2 to 10 carbon atoms; and R 21 , R 22 , R 23 and R 24 each independently represent a hydrogen atom, a halogen atom or a carbon And R 25 represents any one substituent selected from a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms or the following formulas (A) to (C), and An q - represents an anion of q, and p represents a coefficient for neutralizing the charge.
여기서, 식 중, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21, R22, R23, R24, R26, R27, R28, R29, R35, R36, R37, R38 및 R39는, 각각 독립적으로, 수소 원자, 할로겐 원자, 탄소 원자수 1∼10의 알킬기, 탄소 원자수 1∼10의 알콕시기 또는 탄소 원자수 2∼10의 에스테르기를 나타내고, R30, R31, R32, R33 및 R34는, 각각 독립적으로, 수소 원자, 할로겐 원자 또는 탄소 원자수 1∼10의 알킬기를 나타낸다.Wherein R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 26 , Each of R 27 , R 28 , R 29 , R 35 , R 36 , R 37 , R 38 and R 39 independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, And R 30 , R 31 , R 32 , R 33, and R 34 each independently represent a hydrogen atom, a halogen atom, or an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 2 to 10 carbon atoms, .
상기 일반식(1)으로 표시되는 화합물에 있어서, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21, R22, R23, R24, R25, R26, R27, R28, R29, R30, R31, R32, R33, R34, R35, R36, R37, R38 및 R39로 표시되는 할로겐 원자로서는, 불소, 염소, 브롬, 요오드 등을 예로 들 수 있다.In the compound represented by the general formula (1), R 11, R 12, R 13, R 14, R 15, R 16, R 17, R 18, R 19, R 20, R 21, R 22, R 23, with R 24, R 25, R 26 , R 27, R 28, R 29, R 30, R 31, R 32, R 33, R 34, R 35, R 36, R 37, R 38 and R 39 Examples of the halogen atom to be displayed include fluorine, chlorine, bromine, and iodine.
R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21, R22, R23, R24, R25, R26, R27, R28, R29, R30, R31, R32, R33, R34, R35, R36, R37, R38 및 R39로 표시되는 탄소 원자수 1∼10의 알킬기로서는, 메틸, 에틸, 프로필, 이소프로필, 부틸, sec-부틸, tert-부틸, 이소부틸, 아밀, 이소아밀, tert-아밀, 헥실, 시클로헥실, 헵틸, 옥틸, 노닐, 에틸 옥틸, 2-메톡시에틸, 3-메톡시프로필, 4-메톡시부틸, 2-부톡시에틸, 메톡시에톡시에틸, 메톡시에톡시에톡시에틸, 3-메톡시부틸, 2-메틸티오에틸, 플루오로메틸, 디플루오로메틸, 트리플루오로메틸, 클로로메틸, 디클로로메틸, 트리클로로메틸, 브로모메틸, 디브로모메틸, 트리브로모메틸, 디플루오로에틸, 트리클로로에틸, 디클로로디플루오로에틸, 펜타플루오로에틸, 헵타플루오로프로필, 노나플루오로부틸, 데카플루오로펜틸, 트리데카플루오로헥실, 펜타데카플루오로헵틸, 헵타데카플루오로옥틸, 메톡시메틸, 1,2-에폭시에틸, 메톡시에틸, 메톡시에톡시메틸, 메틸티오메틸, 에톡시에틸, 부톡시메틸, tert-부틸티오메틸, 4-펜테닐옥시메틸, 트리클로로에톡시메틸, 비스(2-클로로에톡시)메틸, 메톡시시클로헥실, 1-(2-클로로에톡시)에틸, 1-메틸-1-메톡시에틸, 에틸디티오에틸, 트리메틸실릴에틸, tert-부틸디메틸실릴옥시메틸, 2-(트리메틸실릴)에톡시메틸, tert-부톡시카르보닐메틸, 에틸옥시카르보닐메틸, 에틸카르보닐메틸, tert-부톡시카르보닐메틸, 아크릴로일옥시에틸, 메타크릴로일옥시에틸, 2-메틸-2-아다만틸옥시카르보닐메틸, 아세틸에틸, 2-메톡시-1-프로페닐, 하이드록시메틸, 2-하이드록시에틸, 1-하이드록시에틸, 2-하이드록시프로필, 3-하이드록시프로필, 3-하이드록시부틸, 4-하이드록시부틸, 1,2-디하이드록시에틸 등을 예로 들 수 있다. R 11, R 12, R 13 , R 14, R 15, R 16, R 17, R 18, R 19, R 20, R 21, R 22, R 23, R 24, R 25, R 26, R 27 Examples of the alkyl group having 1 to 10 carbon atoms represented by R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 and R 39 include methyl Butyl, isobutyl, amyl, isoamyl, tert-amyl, hexyl, cyclohexyl, heptyl, octyl, nonyl, ethyloctyl, 2-methoxyethyl, Methoxypropyl, 3-methoxybutyl, 2-butoxyethyl, methoxyethoxyethyl, methoxyethoxyethoxyethyl, 3-methoxybutyl, 2- methylthioethyl, fluoromethyl, difluoro And examples thereof include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, isobutyl, sec-butyl, Ethyl, heptafluoropropyl, nonafluorobutyl, decaf Methoxymethyl, 1,2-epoxyethyl, methoxyethyl, methoxyethoxymethyl, methylthiomethyl, ethoxyethyl, methoxyethoxyethyl, methoxyethoxy, ethoxyethyl, (2-chloroethoxy) ethyl, 1 (2-chloroethoxy) ethyl, 1-pentyloxymethyl, trichloroethoxymethyl, bis Butyldimethylsilyloxymethyl, 2- (trimethylsilyl) ethoxymethyl, tert-butoxycarbonylmethyl, ethyloxycarbonylmethyl, tert-butyldimethylsilyloxymethyl, Methoxycarbonylmethyl, tert-butoxycarbonylmethyl, acryloyloxyethyl, methacryloyloxyethyl, 2-methyl-2-adamantyloxycarbonylmethyl, acetylethyl, 2- Propyl, hydroxymethyl, 2-hydroxyethyl, 1-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, The like are exemplified bitter butyl, 4-hydroxybutyl, 1,2-dihydroxy-ethyl.
R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21, R22, R23, R24, R26, R27, R28, R29, R35, R36, R37, R38 및 R39로 표시되는 탄소 원자수 1∼10의 알콕시기로서는, 메톡시, 에톡시, 프로필옥시, 이소프로필옥시, 부틸옥시, sec-부틸옥시, tert-부틸옥시, 이소부틸옥시, 펜틸옥시, 이소아밀옥시, tert-아밀옥시, 헥실옥시, 시클로헥실옥시, 시클로헥실메틸옥시, 테트라하이드로퓨라닐옥시, 테트라하이드로피라닐옥시, 2-메톡시에틸옥시, 3-메톡시프로필옥시, 4-메톡시부틸옥시, 2-부톡시에틸옥시, 메톡시에톡시에틸옥시, 메톡시에톡시에톡시에틸옥시, 3-메톡시부틸옥시, 2-메틸티오에틸옥시, 트리플루오로메틸옥시 등을 예로 들 수 있다. R 11, R 12, R 13 , R 14, R 15, R 16, R 17, R 18, R 19, R 20, R 21, R 22, R 23, R 24, R 26, R 27, R 28 Examples of the alkoxy group having 1 to 10 carbon atoms represented by R 29 , R 35 , R 36 , R 37 , R 38 and R 39 include methoxy, ethoxy, propyloxy, isopropyloxy, butyloxy, sec- Butyloxy, tert-butyloxy, isobutyloxy, pentyloxy, isoamyloxy, tert-amyloxy, hexyloxy, cyclohexyloxy, cyclohexylmethyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, Methoxyethyloxy, 3-methoxypropyloxy, 4-methoxybutyloxy, 2-butoxyethyloxy, methoxyethoxyethyloxy, methoxyethoxyethoxyethyloxy, 3-methoxybutyloxy , 2-methylthioethyloxy, trifluoromethyloxy, and the like.
R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21, R22, R23, R24, R26, R27, R28, R29, R35, R36, R37, R38 및 R39로 표시되는 탄소 원자수 2∼10의 에스테르기로서는, 메톡시카르보닐, 에톡시카르보닐, 이소프로필옥시카르보닐, 페녹시카르보닐, 아세톡시, 프로피오닐옥시, 부티릴옥시, 클로로아세틸옥시, 디클로로아세틸옥시, 트리클로로아세틸옥시, 트리플루오로아세틸옥시, tert-부틸카르보닐옥시, 메톡시아세틸옥시, 벤조일옥시 등을 예로 들 수 있다. R 11, R 12, R 13 , R 14, R 15, R 16, R 17, R 18, R 19, R 20, R 21, R 22, R 23, R 24, R 26, R 27, R 28 , R 29 , R 35 , R 36 , R 37 , R 38 and R 39 include an ester group having 2 to 10 carbon atoms such as methoxycarbonyl, ethoxycarbonyl, isopropyloxycarbonyl, phenoxycar Such as, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, isobutyl, sec-butyl, tert-butyl, .
(A) 성분과 (B) 성분과 (C) 성분의 합계 100질량부에 대한 양이온 중합 개시제(B)의 사용 비율은, 양이온 중합 개시제(B) 0.001∼15 질량부, 바람직하게는 0.1∼10 질량부이다. 지나치게 적으면 경화가 불충분하게 되기 쉽고, 지나치게 많으면 경화물의 흡수율이나 경화물 강도 등의 여러가지 물성에 악영향을 미치는 경우가 있다.The ratio of the cationic polymerization initiator (B) to the total 100 parts by mass of the component (A), the component (B) and the component (C) is 0.001 to 15 parts by mass, preferably 0.1 to 10 parts by mass, Mass part. If it is too small, the curing tends to be insufficient, while if it is too much, it may adversely affect various physical properties such as the water absorption of the cured product and the cured product strength.
본 발명의 경화성 조성물에 관한 라디칼 중합성 성분(C)은, 에폭시기 및 에틸렌성 불포화기를 가지는 화합물(C1) 또는 탄소 원자수 2∼20인 알코올의 아크릴산 에스테르 혹은 탄소 원자수 2∼20인 알코올의 메타크릴산 에스테르(C2)를 필수 성분으로 한다.The radically polymerizable component (C) relating to the curable composition of the present invention is a compound (C1) having an epoxy group and an ethylenically unsaturated group or an acrylate ester of an alcohol having 2 to 20 carbon atoms or an alcohol having 2 to 20 carbon atoms (C2) as an essential component.
상기 에폭시기 및 에틸렌성 불포화기를 가지는 화합물(C1)로서는, 예로서, 에폭시아크릴레이트 또는 에폭시메타크릴레이트를 들 수 있고, 구체적으로는, 종래 공지의 방향족 에폭시 수지, 지환식 에폭시 수지, 지방족 에폭시 수지 등과, 아크릴산 또는 메타크릴산을 반응시켜 얻어지는 아크릴레이트이다. 이들 에폭시아크릴레이트 또는 에폭시메타크릴레이트 중, 특히 바람직한 것은, 알코올류의 글리시딜에테르의 아크릴레이트 또는 메타크릴레이트이다.Examples of the compound (C1) having an epoxy group and an ethylenic unsaturated group include an epoxy acrylate or an epoxy methacrylate, and specific examples thereof include conventionally known aromatic epoxy resins, alicyclic epoxy resins, aliphatic epoxy resins and the like , Acrylic acid or methacrylic acid. Of these epoxy acrylates or epoxy methacrylates, particularly preferred are acrylates or methacrylates of glycidyl ethers of alcohols.
상기 탄소 원자수 2∼20인 알코올의 아크릴레이트 혹은 탄소 원자수 2∼20인 알코올의 메타크릴레이트(C2)로서는, 분자 중에 적어도 1개의 수산기를 가지는 방향족 또는 지방족 알코올, 및 그 알킬렌옥사이드 부가체와 아크릴산 또는 메타크릴산을 반응시켜 얻어지는 아크릴레이트 또는 메타크릴레이트를 예로 들 수 있다. 구체적으로는, 2-에틸헥실아크릴레이트, 2-하이드록시에틸아크릴레이트, 2-하이드록시프로필아크릴레이트, 이소아밀아크릴레이트, 라우릴아크릴레이트, 스테아릴아크릴레이트, 이소옥틸아크릴레이트, 테트라하이드로푸르푸릴아크릴레이트, 이소보닐아크릴레이트, 벤질아크릴레이트, 1,3-부탄디올디아크릴레이트, 1,4-부탄디올디아크릴레이트, 1,6-헥산디올디아크릴레이트, 디에틸렌글리콜디아크릴레이트, 트리에틸렌글리콜디아크릴레이트, 네오펜틸글리콜디아크릴레이트, 폴리에틸렌글리콜디아크릴레이트, 폴리프로필렌글리콜디아크릴레이트, 트리메틸올프로판트리아크릴레이트, 펜타에리트리톨테트라아크릴레이트, 디펜타에리트리톨헥사아크릴레이트, ε-카프로락톤 변성 디펜타에리트리톨헥사아크릴레이트, 2-에틸헥실메타크릴레이트, 2-하이드록시에틸메타크릴레이트, 2-하이드록시프로필메타크릴레이트, 이소아밀메타크릴레이트, 라우릴메타크릴레이트, 스테아릴메타크릴레이트, 이소옥틸메타크릴레이트, 테트라하이드로푸르푸릴메타크릴레이트, 이소보닐메타크릴레이트, 벤질메타크릴레이트, 1,3-부탄디올디메타크릴레이트, 1,4-부탄디올디메타크릴레이트, 1,6-헥산디올디메타크릴레이트, 디에틸렌글리콜디메타크릴레이트, 트리에틸렌글리콜디메타크릴레이트, 네오펜틸글리콜디메타크릴레이트, 폴리에틸렌글리콜디메타크릴레이트, 폴리프로필렌글리콜디메타크릴레이트, 트리메틸올프로판트리메타크릴레이트, 펜타에리트리톨테트라메타크릴레이트, 디펜타에리트리톨헥사메타크릴레이트, ε-카프로락톤 변성 디펜타에리트리톨헥사메타크릴레이트 등을 예로 들 수 있다. 그리고, 이들 아크릴레이트 또는 메타크릴레이트 중에서, 다가 알코올의 폴리아크릴레이트류 또는 다가 알코올의 폴리메타크릴레이트류가 특히 바람직하다.The methacrylate (C2) of the alcohol having 2 to 20 carbon atoms or the alcohol having 2 to 20 carbon atoms is preferably an aromatic or aliphatic alcohol having at least one hydroxyl group in the molecule and an alkylene oxide adduct And acrylic acid or methacrylic acid are reacted with each other. Specific examples thereof include acrylic acid esters such as 2-ethylhexyl acrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, isoamyl acrylate, lauryl acrylate, stearyl acrylate, isooctyl acrylate, Butanediol diacrylate, 1,6-hexanediol diacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, triethylene glycol diacrylate, triethylene glycol diacrylate, But are not limited to, glycol diacrylate, neopentyl glycol diacrylate, polyethylene glycol diacrylate, polypropylene glycol diacrylate, trimethylolpropane triacrylate, pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate, Lactone-modified dipentaerythritol hexaacrylate, 2-ethylhexyl methacrylate, 2- Hydroxyethyl methacrylate, hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, isoamyl methacrylate, lauryl methacrylate, stearyl methacrylate, isooctyl methacrylate, tetrahydrofurfuryl methacrylate, isobornyl methacrylate Butylene glycol dimethacrylate, 1,6-hexanediol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, triethylene glycol dimethacrylate, But are not limited to, dimethacrylate, dimethacrylate, neopentyl glycol dimethacrylate, polyethylene glycol dimethacrylate, polypropylene glycol dimethacrylate, trimethylolpropane trimethacrylate, pentaerythritol tetramethacrylate, dipentaerythritol hexamethacrylate Acrylate, 竜 -caprolactone-modified dipentaerythritol hexamethacrylate, and the like. Of these acrylates or methacrylates, polyacrylates of polyhydric alcohols or polyacrylates of polyhydric alcohols are particularly preferred.
상기 라디칼 중합성 성분(C)으로서는, (C1) 또는 (C2) 이외의 에너지선 조사 또는 가열에 의해 활성화한 라디칼 중합 개시제에 의해 고분자화 또는 가교 반응하는 화합물을 사용할 수도 있고, 예를 들면, 알릴우레탄 화합물, 불포화 폴리에스테르 화합물, 스티렌계 화합물 등이 있다. 라디칼 중합성 성분(C)에서의, 상기 (C1) 성분 및 (C2) 성분의 비율은, 50질량% 이상이 바람직하다.As the radically polymerizable component (C), a compound capable of polymerizing or cross-linking with a radical polymerization initiator activated by energy ray irradiation or heating other than (C1) or (C2) may be used. Urethane compounds, unsaturated polyester compounds, styrene compounds, and the like. The proportion of the component (C1) and the component (C2) in the radical polymerizable component (C) is preferably 50% by mass or more.
본 발명의 경화성 조성물에 관한 라디칼 개시제(D)로서는 특별히 제한은 없고, 공지의 것을 사용할 수 있다. 예를 들면, 아세토페논계 화합물, 벤질계 화합물, 벤조페논계 화합물, 디옥산톤계 화합물 등의 케톤계 화합물, 옥심계 화합물 등을 사용할 수 있다.The radical initiator (D) for the curable composition of the present invention is not particularly limited, and any known radical initiator may be used. For example, ketone-based compounds such as acetophenone-based compounds, benzyl-based compounds, benzophenone-based compounds, and dioxantane-based compounds, oxime-based compounds, and the like can be used.
본 발명의 경화성 조성물에 관한 폴리머(E)는, 상기 식(I)으로 표시되는 단량체로부터 얻어지는 폴리머, 상기 식(II)으로 표시되는 단량체로부터 얻어지는 폴리머, 상기 식(I)으로 표시되는 단량체로부터 선택되는 2종 이상의 단량체로부터 얻어지는 폴리머, 상기 식(II)으로 표시되는 단량체로부터 선택되는 2종 이상의 단량체로부터 얻어지는 폴리머, 및 상기 식(I)으로 표시되는 단량체 및 상기 식(II)으로 표시되는 단량체로부터 얻어지는 폴리머로 이루어지는 군으로부터 선택되고, 중량 평균 분자량이, 폴리스티렌 환산으로 1,000∼30,000이다.The polymer (E) relating to the curable composition of the present invention is a polymer obtained from the monomer represented by the formula (I), the polymer obtained from the monomer represented by the formula (II), the monomer selected from the monomer represented by the formula (I) , A polymer obtained from two or more monomers selected from the monomers represented by the formula (II), and a polymer obtained from the monomers represented by the formula (I) and the monomer represented by the formula (II) And a weight average molecular weight of 1,000 to 30,000 in terms of polystyrene.
상기 식(I) 중의 X로 표시되는 탄소 원자수 1∼7의 알킬기로서는, 메틸, 에틸, 프로필, iso-프로필, 부틸, sec-부틸, tert-부틸, iso-부틸, 아밀, iso-아밀, tert-아밀, 헥실, 2-헥실, 3-헥실, 시클로헥실, 4-메틸시클로헥실, 헵틸, 2-헵틸, 3-헵틸, iso-헵틸, tert-헵틸 등을 예로 들 수 있다. 이들 중에서도, 탄소 원자수 1∼4의 알킬기, 또는, 에폭시기, 옥세탄기, 수산기 및 카르복실기로 이루어지는 군으로부터 선택되는 1종 이상의 기로 부분적으로 치환된 탄소 원자수 1∼4의 알킬기가, 경화성의 점에서 바람직하다.Examples of the alkyl group having 1 to 7 carbon atoms represented by X in the above formula (I) include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert- butyl, isobutyl, cyclohexyl, 4-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, iso-heptyl, tert-heptyl and the like. Among them, an alkyl group having 1 to 4 carbon atoms or an alkyl group having 1 to 4 carbon atoms partially substituted with at least one group selected from the group consisting of an epoxy group, an oxetane group, a hydroxyl group and a carboxyl group, .
상기 식(I) 중의 X로 표시되는 탄소 원자수 1∼7의 알콕시기로서는, 메톡시, 에톡시, 프로필 옥시, iso-프로필 옥시, 부틸옥시, sec-부틸옥시, tert-부틸옥시, iso-부틸옥시, 아밀 옥시, iso-아밀 옥시, tert-아밀 옥시, 헥실옥시, 2-헥실옥시, 3-헥실옥시, 시클로헥실옥시, 4-메틸시클로헥실옥시, 헵틸옥시, 2-헵틸옥시, 3-헵틸옥시, iso-헵틸옥시, tert-헵틸옥시 등을 예로 들 수 있다. 이들 중에서도, 탄소 원자수 1∼4의 알콕시기, 또는, 에폭시기, 옥세탄기, 수산기 및 카르복실기로 이루어지는 군으로부터 선택되는 1종 이상의 기로 부분적으로 치환된 탄소 원자수 1∼4의 알콕시기가, 경화성의 점에서 바람직하다.Examples of the alkoxy group having 1 to 7 carbon atoms represented by X in the formula (I) include methoxy, ethoxy, propyloxy, isopropyloxy, butyloxy, sec-butyloxy, tert- Butyloxy, amyloxy, iso-amyloxy, tert-amyloxy, hexyloxy, 2-hexyloxy, 3-hexyloxy, cyclohexyloxy, 4-methylcyclohexyloxy, heptyloxy, 2- Heptyloxy, 3-heptyloxy, iso-heptyloxy, tert-heptyloxy and the like. Among them, an alkoxy group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms which is partially substituted with at least one group selected from the group consisting of an epoxy group, an oxetane group, a hydroxyl group and a carboxyl group, .
상기 식(I) 중의 X로 표시되는 탄소 원자수 6∼12의 아릴기로서는, 페닐, 메틸페닐, 나프틸 등을 예로 들 수 있다.Examples of the aryl group having 6 to 12 carbon atoms represented by X in the formula (I) include phenyl, methylphenyl, naphthyl and the like.
상기 식(I) 중의 X로 표시되는 탄소 원자수 6∼12의 아릴옥시기로서는, 페닐옥시, 메틸페닐옥시, 나프틸옥시 등을 예로 들 수 있다.Examples of the aryloxy group having 6 to 12 carbon atoms represented by X in the formula (I) include phenyloxy, methylphenyloxy, naphthyloxy and the like.
상기 식(I) 중의 X로 표시되는 탄소 원자수 6∼10의 지환식 탄화수소기로서는, 시클로헥실, 메틸시클로헥실, 노르보르닐, 비시클로펜틸, 비시클로옥틸, 트리메틸비시클로헵틸, 트리시클로옥틸, 트리시클로데카닐, 스피로옥틸, 스피로비시클로펜틸, 아다만틸, 이소보르닐 등을 예로 들 수 있다.Examples of the alicyclic hydrocarbon group having 6 to 10 carbon atoms represented by X in the formula (I) include cyclohexyl, methylcyclohexyl, norbornyl, bicyclopentyl, bicyclooctyl, trimethylbicycloheptyl, tricyclooctyl , Tricyclodecanyl, spirooctyl, spirobicyclo pentyl, adamantyl, isobornyl, and the like.
이들 알킬기, 알콕시기, 아릴기, 아릴옥시기 및 지환식 탄화수소기는, 이들 기 중의 수소 원자가, 에폭시기, 옥세탄기, 수산기 및 카르복실기로 이루어지는 군으로부터 선택되는 1종 이상의 기로 치환되어 있어도 된다.These alkyl groups, alkoxy groups, aryl groups, aryloxy groups and alicyclic hydrocarbon groups may be substituted with at least one group selected from the group consisting of epoxy groups, oxetane groups, hydroxyl groups and carboxyl groups in these groups.
상기 식(I)에 있어서, X의 일부가 에폭시기 또는 옥세탄기로 치환되어 있는 경우에서의, 식(I)으로 표시되는 단량체로서는, 예를 들면, 하기 식(1)∼식(3)으로 표시되는 단량체가 있다.Examples of the monomer represented by the formula (I) in the case where a part of X in the formula (I) is substituted with an epoxy group or an oxetane group include those represented by the following formulas (1) to (3) ≪ / RTI >
여기서, 식(1) 중, R3는, 수소 원자 또는 탄소 원자수 1∼6의 알킬기를 나타내고, m은, 1∼6의 정수이다.Here, in the formula (1), R 3 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and m is an integer of 1 to 6.
여기서, 식(2) 중, R4는, 수소 원자 또는 탄소 원자수 1∼6의 알킬기를 나타내고, n은, 1∼6의 정수이다.In the formula (2), R 4 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and n is an integer of 1 to 6.
여기서, 식(3) 중, R5는, 수소 원자 또는 탄소 원자수 1∼6의 알킬기를 나타내고, s는, 1∼6의 정수이다.Here, in the formula (3), R 5 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and s is an integer of 1 to 6.
상기 식(II)에 있어서, R1으로 표시되는 할로겐 원자로서는, 불소, 염소, 브롬, 요오드 등을 예로 들 수 있다.In the above formula (II), examples of the halogen atom represented by R 1 include fluorine, chlorine, bromine, iodine and the like.
상기 식(II)에 있어서, X'의 탄소 원자수 1∼7의 알킬기, 탄소 원자수 6∼12의 아릴기 또는 탄소 원자수 6∼10의 지환식 탄화수소기로서는, 상기 식(I)과 동일한 것을 예로 들 수 있다.In the formula (II), examples of the alkyl group having 1 to 7 carbon atoms, the aryl group having 6 to 12 carbon atoms, or the alicyclic hydrocarbon group having 6 to 10 carbon atoms in X ' For example.
상기 식(II)에 있어서, X'의 일부가 에폭시기 또는 옥세탄기로 치환되어 있는 경우에서의, 식(II)으로 표시되는 단량체로서는, 하기 식(4)∼식(6)으로 표시되는 것을 예로 들 수 있다.Examples of the monomer represented by the formula (II) in the case where a part of X 'in the formula (II) is substituted with an epoxy group or an oxetane group include those represented by the following formulas (4) to (6) .
여기서, 식(4) 중, R1은, 상기 식(II)과 동일하며, R6는, 수소 원자 또는 탄소 원자수 1∼6의 알킬기를 나타내고, t는, 1∼6의 정수이다.Here, in the formula (4), R 1 is the same as in the formula (II), R 6 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and t is an integer of 1 to 6.
여기서, 식(5) 중, R1은, 상기 식(II)과 동일하며, R7은, 수소 원자 또는 탄소 원자수 1∼6의 알킬기를 나타내고, q는, 1∼6의 정수이다.Here, R 1 in the formula (5) is the same as in the formula (II), R 7 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and q is an integer of 1 to 6.
여기서, 식(6) 중, R1은, 상기 식(II)과 동일하며, R8은, 수소 원자 또는 탄소 원자수 1∼6의 알킬기를 나타내고, y는, 1∼6의 정수이다.Here, R 1 in the formula (6) is the same as in the formula (II), R 8 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and y is an integer of 1 to 6.
상기 폴리머(E)에 있어서, 폴리머를 구성하는 단량체의 사용 비율은, 상기 X가, 에폭시기, 옥세탄기, 수산기 및 카르복실기로 이루어지는 군으로부터 선택되는 1종 이상의 기로 치환된 탄소 원자수 1∼7의 알킬기, 탄소 원자수 6∼12의 아릴기 혹은 탄소 원자수 6∼10의 지환식 탄화수소기인 경우에서의, 상기 (I) 또는 (II)로 표시되는 단량체가 10∼100 질량%가 되도록 사용하는 것이, 접착성이 향상되므로 바람직하다.In the polymer (E), the ratio of the monomers constituting the polymer is such that X is an alkyl group having 1 to 7 carbon atoms substituted with at least one group selected from the group consisting of an epoxy group, an oxetane group, a hydroxyl group and a carboxyl group (I) or (II) in an amount of 10 to 100% by mass in the case of an alkyl group, an aryl group having 6 to 12 carbon atoms or an alicyclic hydrocarbon group having 6 to 10 carbon atoms , And adhesion is improved.
본 발명의 경화성 조성물에 있어서는, 양이온 중합성 성분(A)과 라디칼 중합성 성분(C)과 폴리머(E)의 합계 100질량부에 대하여, 상기 양이온 중합성 성분(A)은 45∼90 질량부, 상기 양이온 중합 개시제(B)가 0.001∼15 질량부, 상기 라디칼 중합성 성분(C)이 1∼15 질량부, 상기 라디칼 중합 개시제(D)가 1∼10 질량부, 상기 폴리머(E)가 1∼20 질량부이다. 상기한 배합 비율 이외이면, 경화물의 경화성 및 밀착성이 좋지 못하게 될 우려가 있다.In the curable composition of the present invention, the amount of the cationic polymerizable component (A) is preferably 45 to 90 parts by mass based on 100 parts by mass of the total of 100 parts by mass of the cationic polymerizable component (A), the radical polymerizable component (C) (C) is 1 to 15 parts by mass, the radical polymerization initiator (D) is 1 to 10 parts by mass, the polymer (E) is a polymer 1 to 20 parts by mass. If the compounding ratio is outside the above range, the curing property and adhesion of the cured product may be poor.
본 발명의 경화성 조성물에는, 필요에 따라, 증감제 및/또는 증감 조제를 더 사용할 수 있다. 증감제는, 양이온 중합 개시제(B)가 나타내는 극대 흡수 파장보다 긴 파장에 극대 흡수를 나타내고, 양이온 중합 개시제(B)에 의한 중합 개시 반응을 촉진시키는 화합물이다. 또한 증감 조제는, 증감제의 작용을 한층 촉진시키는 화합물이다.In the curable composition of the present invention, a sensitizer and / or a sensitizer may be further used if necessary. The sensitizer is a compound which exhibits maximum absorption at a wavelength longer than the maximum absorption wavelength exhibited by the cationic polymerization initiator (B) and promotes the polymerization initiation reaction by the cationic polymerization initiator (B). In addition, the sensitization assistant is a compound that further promotes the action of the sensitizer.
증감제 및 증감 조제로서는, 안트라센계 화합물, 나프탈렌계 화합물 등을 예로 들 수 있다.Examples of the sensitizer and sensitizer include anthracene compounds and naphthalene compounds.
안트라센계 화합물로서는, 예를 들면, 하기 식(7)으로 표시되는 것이 있다.As the anthracene compound, for example, there is one represented by the following formula (7).
여기서, 식(7) 중, R50 및 R51은, 각각 독립적으로 수소 원자, 탄소 원자수 1∼6의 알킬기 또는 탄소 원자수 2∼12의 알콕시 알킬기를 나타내고, R52는 수소 원자 또는 탄소 원자수 1∼6의 알킬기를 나타낸다.In the formula (7), R 50 and R 51 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or an alkoxyalkyl group having 2 to 12 carbon atoms, R 52 is a hydrogen atom or a carbon atom Represents an alkyl group having a number of 1 to 6.
상기 식(7)으로 표시되는 안트라센계 화합물의 구체예를 들면, 다음과 같은 화합물이 있다.Specific examples of the anthracene compound represented by the formula (7) include the following compounds.
예를 들면, 9,10-디메톡시안트라센, 9,10-디에톡시 안트라센, 9,10-디프로폭시안트라센, 9,10-디이소프로폭시안트라센, 9,10-디부톡시안트라센, 9,10-디펜틸옥시안트라센, 9,10-디헥실옥시안트라센, 9,10-비스(2-메톡시에톡시)안트라센, 9,10-비스(2-에톡시에톡시)안트라센, 9,10-비스(2-부톡시에톡시)안트라센, 9,10-비스(3-부톡시프로폭시)안트라센, 2-메틸- 또는 2-에틸-9,10-디메톡시안트라센, 2-메틸- 또는 2-에틸-9,10-디에톡시안트라센, 2-메틸- 또는 2-에틸-9,10-디프로폭시안트라센, 2-메틸- 또는 2-에틸-9,10-디이소프로폭시안트라센, 2-메틸- 또는 2-에틸-9,10-디부톡시안트라센, 2-메틸- 또는 2-에틸-9,10-디펜틸옥시안트라센, 2-메틸- 또는 2-에틸-9,10-디헥실옥시안트라센 등이 있다.For example, 9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 9,10-dipropoxyanthracene, 9,10-diisopropoxyanthracene, 9,10-dibutoxyanthracene, 9,10 Bis (2-methoxyethoxy) anthracene, 9,10-bis (2-ethoxyethoxy) anthracene, 9,10-bis (3-butoxypropoxy) anthracene, 2-methyl- or 2-ethyl-9,10-dimethoxyanthracene, 2- methyl- or 2- ethyl Diethoxy anthracene, 2-methyl- or 2-ethyl-9,10-dipropoxyanthracene, 2-methyl- or 2-ethyl-9,10-diisopropoxyanthracene, Or 2-ethyl-9,10-dibutoxyanthracene, 2-methyl- or 2-ethyl-9,10-dipentyloxyanthracene, 2- have.
나프탈렌계 화합물로서는, 예를 들면, 하기 식(8)으로 표시되는 것이 있다.Examples of the naphthalene-based compound include those represented by the following formula (8).
여기서, 식(8) 중, R53 및 R54는 각각 독립적으로 탄소 원자수 1∼6의 알킬기를 나타낸다.Here, in formula (8), R 53 and R 54 each independently represent an alkyl group having 1 to 6 carbon atoms.
상기 식(8)으로 표시되는 나프탈렌계 화합물의 구체예를 들면, 다음과 같은 화합물이 있다.Specific examples of the naphthalene-based compound represented by the formula (8) include the following compounds.
예를 들면, 4-메톡시-1-나프톨, 4-에톡시-1-나프톨, 4-프로폭시-1-나프톨, 4-부톡시-1-나프톨, 4-헥실옥시-1-나프톨, 1,4-디메톡시나프탈렌, 1-에톡시-4-메톡시나프탈렌, 1,4-디에톡시나프탈렌, 1,4-디프로폭시나프탈렌, 1,4-디부톡시나프탈렌 등이 있다.Naphthol, 4-ethoxy-1-naphthol, 4-propoxy-1-naphthol, 4-butoxy-1-naphthol, 4-hexyloxy- 1,4-dimethoxynaphthalene, 1,4-dimethoxynaphthalene, 1-ethoxy-4-methoxynaphthalene, 1,4-diethoxynaphthalene, 1,4-dipropoxynaphthalene and 1,4-dibutoxynaphthalene.
상기 양이온 중합성 성분(A)에 대한 증감제 및 증감 조제의 사용 비율은 특별히 한정되지 않으며, 본 발명의 목적을 저해하지 않는 범위 내에서 대체로 통상의 사용 비율로 사용하면 바람직하지만, 예를 들면, 상기 양이온 중합성 성분(A)의 100질량부에 대하여, 증감제 및 증감 조제 각각 0.1∼3 질량부인 것이, 경화성 향상의 관점에서 바람직하다.The ratio of the sensitizer and the sensitizer to the cationic polymerizable component (A) is not particularly limited, and it is generally preferred to use the sensitizer in a usual ratio within the range not hindering the object of the present invention. For example, From the viewpoint of improving the curability, it is preferable that each of the sensitizer and the sensitizer is added in an amount of 0.1 to 3 parts by mass based on 100 parts by mass of the cationic polymerizable component (A).
본 발명의 경화성 조성물에는, 필요에 따라 실란 커플링제를 사용할 수 있다. 실란 커플링제로서는, 예를 들면, 디메틸디메톡시실란, 디메틸디에톡시실란, 메틸에틸디메톡시실란, 메틸에틸디에톡시실란, 메틸트리메톡시실란, 메틸트리에톡시실란, 에틸트리메톡시실란, 에틸트리메톡시실란 등의 알킬 관능성 알콕시실란, 비닐트리클로로실란, 비닐트리메톡시실란, 비닐트리에톡시실란, 알릴트리메톡시실란 등의 알케닐 관능성 알콕시실란, 3-메타크릴옥시프로필트리에톡시실란, 3-메타크릴옥시프로필트리메톡시실란, 3-메타크릴옥시프로필메틸디에톡시실란, 3-메타크릴옥시프로필메틸디메톡시실란, 2-메타크릴옥시프로필트리메톡시실란, γ-글리시독시프로필트리메톡시실란, γ-글리시독시프로필메틸디에톡시실란, β-(3,4-에폭시시클로헥실)에틸트리메톡시실란 등의 에폭시 관능성 알콕시실란, N-β(아미노에틸)-γ-아미노프로필트리메톡시실란, γ-아미노프로필트리에톡시실란, N-페닐-γ-아미노프로필트리메톡시실란 등의 아미노 관능성 알콕시실란, γ-머캅토프로필트리메톡시실란 등의 머캅토 관능성 알콕시실란, 티탄테트라이소프로폭시드, 티탄테트라노르말부톡시드 등의 티탄알콕시드류, 티탄디옥틸옥시비스(옥틸렌글리콜레이트), 티탄디이소프로폭시비스(에틸아세토아세테이트) 등의 티탄 킬레이트류, 지르코늄테트라아세틸아세토네이트, 지르코늄트리부톡시모노아세틸아세토네이트 등의 지르코늄 킬레이트류, 지르코늄트리부톡시모노스테아레이트 등의 지르코늄아실레이트류, 메틸트리이소시아네이트실란 등의 이소시아네이트실란류 등을 사용할 수 있다.In the curable composition of the present invention, a silane coupling agent may be used if necessary. As the silane coupling agent, there may be mentioned, for example, dimethyldimethoxysilane, dimethyldiethoxysilane, methylethyldimethoxysilane, methylethyldiethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyl Alkenyl functional alkoxysilanes such as vinyl trichlorosilane, vinyltrimethoxysilane, vinyltriethoxysilane, and allyltrimethoxysilane, alkoxy functional alkoxysilanes such as trimethoxysilane, and 3-methacryloxypropyl tri Methacryloxypropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 2-methacryloxypropyltrimethoxysilane, Epoxyfunctional alkoxysilanes such as glycidoxypropyltrimethoxysilane,? -Glycidoxypropylmethyldiethoxysilane and? - (3,4-epoxycyclohexyl) ethyltrimethoxysilane, N-β (aminoethyl ) -γ-aminopropyl Amino functional alkoxy silanes such as trimethoxy silane, dimethoxy silane, γ-aminopropyl triethoxy silane and N-phenyl-γ-aminopropyl trimethoxy silane, mercapto functional alkoxysilanes such as γ-mercaptopropyl trimethoxy silane , Titanium alkoxides such as titanium tetraisopropoxide and titanium tetra-n-butoxide, titanium chelates such as titanium dioctyloxybis (octylene glycolate) and titanium diisopropoxybis (ethylacetoacetate), zirconium tetra Zirconium chelates such as acetylacetonate and zirconium tributoxymonoacetylacetonate; zirconium acylates such as zirconium tributoxymonostearate; and isocyanate silanes such as methyltriisocyanate silane.
상기 실란 커플링제의 사용량은, 특별히 한정되지 않지만, 통상, 경화성 조성물 중의 고형물의 전량 100질량부에 대하여, 0.01∼20 질량부의 범위이다.The amount of the silane coupling agent to be used is not particularly limited, but is usually in the range of 0.01 to 20 parts by mass based on 100 parts by mass of the total amount of the solid matter in the curable composition.
본 발명의 경화성 조성물에는, 필요에 따라 열가소성 유기 중합체를 사용함으로써, 경화물의 특성을 개선할 수도 있다. 열가소성 유기 중합체로서는, 예를 들면, 폴리스티렌, 폴리메틸메타크릴레이트, 메틸메타크릴레이트에틸아크릴레이트 공중합체, 메틸메타크릴레이트글리시딜메타크릴레이트 공중합체, 폴리(메타)아크릴산, 스티렌-(메타)아크릴산 공중합체, (메타)아크릴산-메틸메타크릴레이트 공중합체, 글리시딜(메타)아크릴레이트-폴리메틸(메타)아크릴레이트 공중합체, 폴리비닐부티랄, 셀룰로오스 에스테르, 폴리아크릴아미드, 포화 폴리에스테르 등이 있다.The properties of the cured product may be improved by using a thermoplastic organic polymer, if necessary, in the curable composition of the present invention. Examples of the thermoplastic organic polymer include polystyrene, polymethyl methacrylate, methyl methacrylate ethyl acrylate copolymer, methyl methacrylate glycidyl methacrylate copolymer, poly (meth) acrylic acid, styrene- ) Acrylic acid copolymers, (meth) acrylic acid-methyl methacrylate copolymers, glycidyl (meth) acrylate-polymethyl (meth) acrylate copolymers, polyvinylbutyral, cellulose esters, polyacrylamides, saturated poly Esters and the like.
본 발명의 경화성 조성물에는, 필요에 따라, 자외선 흡수제나, 상온(常溫)에서는 불활성이며 소정의 온도로의 가열·광조사·산 등에 의해 보호기가 탈리(脫離)하고, 활성화되어 자외선 홉수능이 발현되는 화합물을 더 사용할 수도 있다.In the curable composition of the present invention, the ultraviolet absorber may be added to the curable composition of the present invention, the ultraviolet absorber may be inactivated at room temperature, the protective group may be desorbed by heating to a predetermined temperature, May be further used.
또한, 본 발명의 효과를 손상시키지 않는 한, 필요에 따라, 폴리올, 무기 필러, 유기 필러, 안료, 염료 등의 착색제, 소포제(消泡劑), 증점제(增粘劑), 계면 활성제, 레벨링제, 난연제, 틱소제, 희석제, 가소제, 안정제, 중합 금지제, 자외선 흡수제, 산화 방지제, 정전 방지제, 유동(流動) 조정제, 접착 촉진제 등의 각종 수지 첨가물 등을 첨가할 수 있다.As long as it does not impair the effect of the present invention, it is possible to add a colorant such as a polyol, an inorganic filler, an organic filler, a pigment and a dye, a defoaming agent, a thickening agent, a surfactant, , Various additives such as a flame retardant, a thickener, a diluent, a plasticizer, a stabilizer, a polymerization inhibitor, an ultraviolet absorber, an antioxidant, an antistatic agent, a flow control agent and an adhesion promoter.
본 발명의 경화성 조성물에는, 특별히 제한되지 않고 통상 사용되는 상기 (A), (B), (C), (D) 및 (E)의 각 성분을 용해 또는 분산할 수 있는 용매를 사용할 수 있다. 용매로서는, 예를 들면, 메틸에틸케톤, 메틸아밀케톤, 디에틸케톤, 아세톤, 메틸이소프로필케톤, 메틸이소부틸케톤, 시클로헥사논, 2-헵타논 등의 케톤류; 에틸에테르, 디옥산, 테트라하이드로퓨란, 1,2-디메톡시에탄, 1,2-디에톡시에탄, 프로필렌글리콜모노메틸에테르, 디프로필렌글리콜디메틸에테르 등의 에테르계 용매; 아세트산 메틸, 아세트산 에틸, 아세트산-n-프로필, 아세트산 이소프로필, 아세트산 n-부틸, 아세트산 시클로헥실, 락트산 에틸, 숙신산 디메틸, 텍사놀 등의 에스테르계 용매; 에틸렌글리콜모노메틸에테르, 에틸렌글리콜모노에틸에테르 등의 셀로솔브계 용매; 메탄올, 에탄올, 이소- 또는 n-프로판올, 이소- 또는 n-부탄올, 아밀알코올 등의 알코올계 용매; 에틸렌글리콜모노메틸아세테이트, 에틸렌글리콜모노에틸아세테이트, 프로필렌글리콜-1-모노메틸에테르-2-아세테이트(PGMEA), 디프로필렌글리콜모노메틸에테르아세테이트, 3-메톡시부틸아세테이트, 에톡시에틸프로피오네이트 등의 에테르에스테르계 용매; 벤젠, 톨루엔, 크실렌 등의 BTX계 용매; 헥산, 헵탄, 옥탄, 시클로헥산 등의 지방족 탄화수소계 용매; 테르핀유, D-리모넨, 피넨 등의 테르펜계 탄화수소유; 미네랄 스피릿, 스와졸 #310(코스모 마쓰야마(松山)석유(주)사 제조), 소르벳소 #100(엑손(Exxon) 화학사) 등의 파라핀계 용매; 사염화탄소, 클로로포름, 트리클로로에틸렌, 염화메틸렌, 1,2-디클로로에탄 등의 할로겐화 지방족 탄화수소계 용매; 클로로벤젠 등의 할로겐화 방향족 탄화수소계 용매; 프로필렌카보네이트, 카르비톨계 용매, 아닐린, 트리에틸아민, 피리딘, 아세트산, 아세토니트릴, 이황화 탄소, N,N-디메틸포름아미드, N,N-디메틸아세트아미드, N-메틸피롤리돈, 디메틸술폭시드, 물 등이 있다. 이들 용매는, 1종 또는 2종 이상의 혼합 용매로서 사용할 수 있다.The curable composition of the present invention is not particularly limited and a solvent capable of dissolving or dispersing the components (A), (B), (C), (D) and (E) Examples of the solvent include ketones such as methyl ethyl ketone, methyl amyl ketone, diethyl ketone, acetone, methyl isopropyl ketone, methyl isobutyl ketone, cyclohexanone and 2-heptanone; Ether solvents such as ethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, propylene glycol monomethyl ether and dipropylene glycol dimethyl ether; Esters such as methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, cyclohexyl acetate, ethyl lactate, dimethyl succinate, and texanol; Cellosolve solvents such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; Alcohol-based solvents such as methanol, ethanol, iso-or n-propanol, iso- or n-butanol, and amyl alcohol; Propylene glycol monomethyl ether-2-acetate (PGMEA), dipropylene glycol monomethyl ether acetate, 3-methoxybutyl acetate, ethoxyethyl propionate, etc. Ether-based solvent; BTX type solvents such as benzene, toluene and xylene; Aliphatic hydrocarbon solvents such as hexane, heptane, octane and cyclohexane; Terpene-based hydrocarbon oils such as terpine oil, D-limonene, and pinene; Paraffin type solvents such as mineral spirits, Swazol # 310 (manufactured by Cosmo Matsuyama Petroleum Co., Ltd.) and sorboxo # 100 (manufactured by Exxon Chemical); Halogenated aliphatic hydrocarbon solvents such as carbon tetrachloride, chloroform, trichlorethylene, methylene chloride, and 1,2-dichloroethane; Halogenated aromatic hydrocarbon solvents such as chlorobenzene; Propylene carbonate, carbitol-based solvent, aniline, triethylamine, pyridine, acetic acid, acetonitrile, carbon disulfide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, dimethylsulfoxide , And water. These solvents may be used singly or as a mixed solvent of two or more kinds.
본 발명의 경화성 조성물은, 경화성, 접착성, 액저장 안정성이 향상되므로, 수분량이 5질량부 이하인 것이 바람직하고, 3질량부 이하인 것이 더욱 바람직하다. 수분이 지나치게 많으면, 백탁하거나 성분이 석출할 우려가 있으므로, 바람직하지 않다.The curable composition of the present invention preferably has a water content of 5 parts by mass or less, more preferably 3 parts by mass or less, because curing properties, adhesiveness, and liquid storage stability are improved. If the water content is excessively high, it may be cloudy or the component may precipitate, which is undesirable.
본 발명의 경화성 조성물은, 롤 코터, 커튼 코터, 각종 인쇄, 침지 등의 공지의 수단에 의해, 지지 기체(基體) 상에 적용된다. 또한, 일단 필름 등의 지지 기체 상에 실시한 후, 다른 지지 기체 상에 전사할 수도 있고, 그 적용 방법에 제한은 없다.The curable composition of the present invention is applied on a supporting base by a known means such as a roll coater, a curtain coater, various printing, immersion and the like. Further, after being applied onto a supporting substrate such as a film, it may be transferred onto another supporting substrate.
상기 지지 기체의 재료로서는, 특별히 제한되지 않고 통상 사용되는 것을 사용할 수 있고, 예를 들면, 유리 등의 무기 재료로 된 것; 디아세틸셀룰로오스, 트리아세틸셀룰로오스(TAC), 프로피오닐셀룰로오스, 부티릴셀룰로오스, 아세틸프로피오닐셀룰로오스, 니트로셀룰로오스 등의 셀룰로오스에스테르; 폴리아미드; 폴리이미드; 폴리우레탄; 에폭시 수지; 폴리카보네이트; 폴리에틸렌테레프탈레이트, 폴리에틸렌나프탈레이트, 폴리부틸렌테레프탈레이트, 폴리-1,4-시클로헥산디메틸렌테레프탈레이트, 폴리에틸렌-1,2-디페녹시에탄-4,4'-지카르복실레이트, 폴리부틸렌테레프탈레이트 등의 폴리에스테르; 폴리스티렌; 폴리에틸렌, 폴리프로필렌, 폴리메틸펜텐 등의 폴리올레핀; 폴리아세트산 비닐, 폴리 염화 비닐, 폴리 불화 비닐 등의 비닐 화합물; 폴리메틸메타크릴레이트, 폴리아크릴레이트 등의 아크릴계 수지; 폴리카보네이트; 폴리술폰; 폴리에테르술폰; 폴리에테르케톤; 폴리에테르이미드; 폴리옥시에틸렌, 노르보르넨 수지, 시클로올레핀 폴리머(COP) 등의 고분자 재료가 있다. 그리고, 상기 지지 기체에, 코로나 방전 처리, 화염 처리, 자외선 처리, 고주파 처리, 글로우 방전 처리, 활성 플라스마 처리, 레이저 처리 등의 표면 활성화 처리를 행할 수도 있다.The material of the support base is not particularly limited and may be a commonly used one, for example, an inorganic material such as glass; Cellulose esters such as diacetylcellulose, triacetylcellulose (TAC), propionylcellulose, butyrylcellulose, acetylpropionylcellulose, and nitrocellulose; Polyamide; Polyimide; Polyurethane; Epoxy resin; Polycarbonate; Polyethylene terephthalate, polyethylene naphthalate, polybutylene terephthalate, poly-1,4-cyclohexanedimethylene terephthalate, polyethylene-1,2-diphenoxyethane-4,4'-dicarboxylate, polybutyl Polyesters such as rheneterephthalate; polystyrene; Polyolefins such as polyethylene, polypropylene and polymethylpentene; Vinyl compounds such as polyvinyl acetate, polyvinyl chloride and polyvinyl fluoride; Acrylic resins such as polymethyl methacrylate and polyacrylate; Polycarbonate; Polysulfone; Polyethersulfone; Polyether ketones; Polyetherimide; There are polymer materials such as polyoxyethylene, norbornene resin and cycloolefin polymer (COP). Then, the supporting substrate may be subjected to surface activation treatment such as corona discharge treatment, flame treatment, ultraviolet treatment, high frequency treatment, glow discharge treatment, active plasma treatment, laser treatment and the like.
본 발명의 경화성 조성물을 에너지선의 조사에 의해 경화시키는 방법에 있어서, 에너지선으로서는, 자외선, 전자선, X선, 방사선, 고주파 등을 예로 들 수 있고, 자외선이 경제적으로 가장 바람직하다. 자외선의 광원으로서는, 자외선 레이저, 수은 램프, 크세논 레이저, 메탈할라이드 램프 등을 예로 들 수 있다.In the method of curing the curable composition of the present invention by irradiation with energy rays, examples of the energy ray include ultraviolet rays, electron rays, X rays, radiation, high frequency waves and the like, and ultraviolet rays are most economically preferable. Examples of ultraviolet light sources include ultraviolet lasers, mercury lamps, xenon lasers, and metal halide lamps.
본 발명의 경화성 조성물을 가열에 의해 경화시키는 방법에서의 조건은, 70∼250 ℃에서 1∼100 분이다. 프리베이크(PAB; Pre applied bake)한 후, 가압하고, 포스트베이크(PEB; Post exposure bake)해도 되고, 상이한 몇 단계의 온도에서 베이크해도 된다. 가열 조건은 각 성분의 종류 및 배합 비율에 따라 상이하지만, 예를 들면, 70∼180 ℃에서, 오븐이라면 5∼15 분간, 핫 플레이트라면 1∼5 분간이다. 그 후, 도막(塗膜)을 경화시키기 위해 180∼250 ℃, 바람직하게는 200∼250 ℃에서, 오븐이라면 30∼90 분간, 핫 플레이트라면 5∼30 분간 가열 처리함으로써 경화막을 얻을 수 있다.The conditions for the method of curing the curable composition of the present invention by heating are 1 to 100 minutes at 70 to 250 캜. After pre-applied bake (PAB), it may be pressurized, post-bake (PEB), or baked at several different temperatures. The heating conditions vary depending on the kind of the respective components and the mixing ratio. For example, the heating conditions are from 70 to 180 DEG C for 5 to 15 minutes in an oven, and from 1 to 5 minutes in a hot plate. Thereafter, in order to cure the coating film (coating film), the cured film can be obtained by heating at 180 to 250 캜, preferably 200 to 250 캜, for 30 to 90 minutes for an oven and for 5 to 30 minutes for a hot plate.
본 발명의 경화성 조성물 또는 그 경화물이 구체적인 용도로서는, 접착제, 안경, 촬상용 렌즈로 대표되는 광학 재료, 도료, 코팅제, 라이닝제, 잉크, 레지스트, 액상(液狀) 레지스트, 인쇄판, 컬러 TV, PC 모니터, 휴대정보 단말기, 디지털카메라, 유기 EL, 터치패널 등의 표시 소자, 절연 바니스, 절연 시트, 적층판, 프린트 기판, 반도체 장치용·LED 패키지용·액정 주입구용·유기 EL용·광소자용·전기 절연용·전자 부품용·분리막용 등의 봉지제, 성형 재료, 퍼티, 유리 섬유 함침제, 실링제, 반도체용·태양 전지용 등의 패시베이션막, 층간 절연막, 보호막, 액정 표시 장치의 백라이트에 사용되는 프리즘 렌즈 시트, 프로젝션 TV 등의 스크린에 사용되는 프레넬 렌즈 시트, 렌티큘러 렌즈 시트 등의 렌즈 시트의 렌즈부, 또는 이와 같은 시트를 사용한 백라이트 등, 마이크로 렌즈 등의 광학 렌즈, 광학 소자, 광 커넥터, 광도파로, 광학적 조형용 주형제 등을 예로 들 수 있다.Specific examples of the use of the curable composition or the cured product of the present invention include an optical material, a coating material, a coating material, a lining material, an ink, a resist, a liquid resist, a printing plate, a color TV, Display devices such as a PC monitor, a portable information terminal, a digital camera, an organic EL, a touch panel, an insulating varnish, an insulating sheet, a laminated board, a printed board, a semiconductor device, an LED package, a liquid crystal injection hole, Used in backlighting of passivation films, interlayer insulating films, protective films, liquid crystal display devices such as encapsulants, molding materials, putties, glass fiber impregnants, sealants, semiconductors and solar cells for electrical insulation, electronic components and separation membranes. A lens portion of a lens sheet such as a lenticular lens sheet or a backlight using such a sheet, An optical lens such as a microlens, an optical element, an optical connector, an optical waveguide, a mold for optical molding, and the like.
표시 장치로서는, 투명 지지체에, 필요에 따라 언더코트층, 반사 방지층, 편광 소자층, 위상차층, 복굴절율층, 광산란층, 하드 코트층, 윤활층, 보호층 등의 각 층을 설치한 것을 예로 들 수 있고, 각 층에 본 발명의 경화물로 이루어지는 필름을 사용할 수 있다.Examples of the display device include those in which respective layers such as an undercoat layer, an antireflection layer, a polarizing element layer, a retardation layer, a birefringent layer, a light scattering layer, a hard coat layer, a lubricating layer, And a film made of the cured product of the present invention can be used for each layer.
[실시예][Example]
이하, 실시예 등을 예로 들어 본 발명을 더욱 상세하게 설명하지만, 본 발명은 이들 실시예로 한정되는 것은 아니다.Hereinafter, the present invention will be described in more detail by way of examples and the like, but the present invention is not limited to these examples.
[실시예 1∼20, 비교예 1∼7][Examples 1 to 20, Comparative Examples 1 to 7]
하기 [표 1]∼[표 5]에 나타낸 배합으로 각 성분을 충분히 혼합하여, 각각 실시예 1∼20의 경화성 조성물 및 비교예 1∼7의 경화성 조성물을 얻었다. 그리고, 실시예 및 비교예의 단위는 질량부이다.The components shown in [Table 1] to [Table 5] were sufficiently mixed to obtain the curable compositions of Examples 1 to 20 and Comparative Examples 1 to 7, respectively. The units of Examples and Comparative Examples are parts by mass.
양이온 중합성 성분(A)으로서는 하기 화합물을 사용했다.As the cationic polymerizable component (A), the following compounds were used.
화합물(A1-1): 네오펜틸글리콜디글리시딜에테르Compound (A1-1): Neopentyl glycol diglycidyl ether
화합물(A1-2): 1,4-부탄디올디글리시딜에테르Compound (A1-2): 1,4-butanediol diglycidyl ether
화합물(A2-1): 아론옥세탄 OXT-221(도아합성(주)사 제조)Compound (A2-1): Aronoxetane OXT-221 (manufactured by Toa Gosei Co., Ltd.)
화합물(A3-1): 비스페놀형 디글리시딜에테르Compound (A3-1): Bisphenol-type diglycidyl ether
화합물(A3-2): TECHMORE VG3101(방향족 3관능 에폭시: (주)프린텍사 제조)Compound (A3-2): TECHMORE VG3101 (aromatic trifunctional epoxy: manufactured by PRINTEC Co., Ltd.)
양이온 중합 개시제(B)로서는 하기 화합물(B-1)을 사용했다.As the cationic polymerization initiator (B), the following compound (B-1) was used.
화합물(B-1): 하기 식(9)으로 표시되는 화합물 및 하기 식(10)으로 표시되는 화합물의 혼합물의 프로필렌카보네이트 50% 용액Compound (B-1): A 50% solution of propylene carbonate in a mixture of the compound represented by the following formula (9) and the compound represented by the following formula (10)
라디칼 중합성 성분(C)으로서는, 하기 화합물을 사용했다.As the radical polymerizable component (C), the following compounds were used.
화합물(C1-1): 에폭시에스테르 M-600A(교에이샤화학(주)사 제조)Compound (C1-1): Epoxy ester M-600A (manufactured by Kyoeisha Chemical Co., Ltd.)
화합물(C1-2): 에폭시에스테르 70PA(교에이샤화학(주)사 제조)Compound (C1-2): Epoxy ester 70PA (manufactured by Kyoeisha Chemical Co., Ltd.)
화합물(C2-1): 1,6-헥산디올디아크릴레이트Compound (C2-1): 1,6-hexanediol diacrylate
라디칼 중합 개시제(D)로서는, 하기 화합물(D-1)을 사용했다.As the radical polymerization initiator (D), the following compound (D-1) was used.
화합물(D-1): 이르가큐어 184(BASF사 제조)Compound (D-1): Irgacure 184 (manufactured by BASF)
폴리머(E)로서는, 하기 화합물(E-1)을 사용했다.As the polymer (E), the following compound (E-1) was used.
폴리머(E-1): 메틸메타크릴레이트 75질량부와 글리시딜메타크릴레이트 25의 공중합체(중량 평균 분자량 7,000)Polymer (E-1): A copolymer of 75 parts by mass of methyl methacrylate and glycidyl methacrylate 25 (weight average molecular weight: 7,000)
폴리머(E')로서는, 하기 화합물(E'-1) 및 하기(E'-2)을 사용했다.As the polymer (E '), the following compounds (E'-1) and (E'-2) were used.
화합물(E'-1): 메틸메타크릴레이트 75질량부와 글리시딜메타크릴레이트 25의 공중합체(중량 평균 분자량 800)Compound (E'-1): A copolymer of 75 parts by mass of methyl methacrylate and glycidyl methacrylate 25 (weight average molecular weight of 800)
화합물(E'-2): 메틸메타크릴레이트 75질량부와 글리시딜메타크릴레이트 25의 공중합체(중량 평균 분자량 35,000)Compound (E'-2): 75 parts by mass of methyl methacrylate and 25 parts by mass of a copolymer of glycidyl methacrylate (weight average molecular weight: 35,000)
얻어진 실시예 1∼20 및 비교예 1∼7의 각 경화성 조성물에 대하여, 하기 수순에 따라, 유리 전이 온도(Tg), 탄성율, 점성 및 밀착성의 평가를 행하였다.Each of the obtained curable compositions of Examples 1 to 20 and Comparative Examples 1 to 7 was evaluated for glass transition temperature (Tg), elastic modulus, viscosity and adhesion according to the following procedure.
결과를 [표 1]∼[표 5]에 병기한다.The results are shown in [Table 1] to [Table 5].
(유리 전이 온도 및 탄성율)(Glass transition temperature and elastic modulus)
얻어진 실시예 1∼20 및 비교예 1∼7의 각 경화성 조성물을, 각각을 폴리에틸렌테레프탈레이트(PET) 필름 상에, 바 코터로 30㎛의 두께로 도포하고, 메탈할라이드 램프를 사용하여 3000mJ/cm2의 에너지를 조사했다. 24시간 후에 필름으로부터 접착제 경화물을 꺼내고, (주)히타치하이테크사이언스에서 제조한 점탄성 측정 장치(DMA7100)를 사용하여 Tg 및 80℃에서의 탄성율을 측정했다.Each of the obtained curable compositions of Examples 1 to 20 and Comparative Examples 1 to 7 was coated on a polyethylene terephthalate (PET) film in a thickness of 30 탆 using a bar coater, and the curable composition was coated with a metal halide lamp at 3000 mJ / cm 2 energy. After 24 hours, the adhesive cured product was taken out from the film, and the modulus of elasticity at Tg and 80 ° C was measured using a viscoelasticity measuring apparatus (DMA7100) manufactured by Hitachi High-Tech Science Co.,
얻어진 실시예 1∼20 및 비교예 1∼7의 각 경화성 조성물 각각에 대하여, 25℃에서의 점도를 E형 점도계로 측정했다. 결과를 [표 1]∼[표 5]에 병기한다.With respect to each of the obtained respective curable compositions of Examples 1 to 20 and Comparative Examples 1 to 7, the viscosity at 25 캜 was measured by an E-type viscometer. The results are shown in [Table 1] to [Table 5].
(밀착성)(Adhesion)
상기에서 얻어진 실시예 1∼20 및 비교예 1∼7의 조성물을, 1장의 코로나 처리 PMMA 필름(스미토모화학(주)사 제조: 데크노로이 125S001)으로 각각 도포한 후, 또 1장의 코로나 방전 처리를 실시한 COP(시클로올레핀 폴리머, 니혼제온 제조: 품번 제오노아 필름 14-060) 필름과 라미네이터를 사용하여 접합하고, 무전극 자외광 램프를 사용하여 1000mJ/cm2에 상당하는 광을 COP 필름 너머로 조사하여 접착하여 시험편을 얻었다. 얻어진 시험편에 대하여, 90도 필(peel) 시험을 행하였다.The compositions of Examples 1 to 20 and Comparative Examples 1 to 7 obtained above were coated with a single corona-treated PMMA film (Deckleoi 125S001, manufactured by Sumitomo Chemical Co., Ltd.), and then subjected to one corona discharge treatment A COP (cycloolefin polymer, manufactured by Nippon Zeon Co., Ltd., part no. Zeonoafilm 14-060) film was laminated with a laminator, and light corresponding to 1000 mJ / cm 2 was irradiated onto the COP film using an electrodeless ultraviolet lamp To obtain a test piece. The obtained test pieces were subjected to a 90-degree peel test.
[표 1][Table 1]
[표 2][Table 2]
[표 3][Table 3]
[표 4][Table 4]
[표 5][Table 5]
[표 1]∼[표 5]에 의해, 본 발명의 경화성 조성물은, 경화물의 경화성 및 밀착성이 우수한 것을 명백하게 알 수 있다.The curable compositions of the present invention clearly show that the cured products are excellent in curability and adhesiveness from [Table 1] to [Table 5].
Claims (7)
하기 식(I)으로 표시되는 단량체로부터 얻어지는 폴리머:
(상기 식(I) 중에서, X는 탄소 원자수 1∼7의 알킬기, 탄소 원자수 1∼7의 알콕시기, 탄소 원자수 6∼12의 아릴기, 탄소 원자수 6∼12의 아릴옥시기 혹은 탄소 원자수 6∼10의 지환식 탄화수소기, 또는 이들 기 중의 수소 원자가 에폭시기, 옥세탄기, 수산기 및 카르복실기로 이루어지는 군으로부터 선택되는 1종 이상의 기로 치환된 것임),
하기 식(II)으로 표시되는 단량체로부터 얻어지는 폴리머:
(상기 식(II) 중에서, R1은 수소 원자, 메틸기 또는 할로겐 원자를 나타내고, X'는 탄소 원자수 1∼7의 알킬기, 탄소 원자수 6∼12의 아릴기 혹은 탄소 원자수 6∼10의 지환식 탄화수소기, 또는 이들 기 중의 수소 원자가 에폭시기, 옥세탄기, 수산기 및 카르복실기로 이루어지는 군으로부터 선택되는 1종 이상의 기로 치환된 것임), 상기 식(I)으로 표시되는 단량체로부터 선택되는 2종 이상의 단량체로부터 얻어지는 폴리머, 상기 식(II)으로 표시되는 단량체로부터 선택되는 2종 이상의 단량체로부터 얻어지는 폴리머, 및 상기 식(I)으로 표시되는 단량체 및 상기 식(II)으로 표시되는 단량체로부터 얻어지는 폴리머로 이루어지는 군으로부터 선택되는 중량 평균 분자량 1,000∼30,000인 폴리머(E) 1∼20 질량부를, 상기 양이온 중합성 성분(A), 상기 라디칼 중합성 성분(C) 및 상기 폴리머(E)의 합계가 100질량부가 되도록 함유하고,
상기 양이온 중합성 성분(A)이, 다가 알코올의 글리시딜화물 또는 다가 알코올 알킬렌옥사이드 부가물의 글리시딜화물(A1)과, 옥세탄 화합물(A2)을 필수 성분으로 하고,
상기 라디칼 중합성 성분(C)이, 에폭시기 및 에틸렌성 불포화기를 가지는 화합물(C1), 또는 탄소 원자수 2∼20인 다가 알코올의 아크릴산 에스테르 혹은 탄소 원자수 2∼20인 다가 알코올의 메타크릴산 에스테르(C2)를 필수 성분으로 하는, 경화성 조성물.(C), 1 to 15 parts by mass of a radical polymerization initiator (D), 1 to 10 parts by mass of a radical polymerization initiator (D), and 5 to 50 parts by mass of a cationic polymerizable component (A) And
A polymer obtained from a monomer represented by the following formula (I):
(Wherein X represents an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aryloxy group having 6 to 12 carbon atoms, An alicyclic hydrocarbon group having 6 to 10 carbon atoms or hydrogen atoms in these groups is substituted with at least one group selected from the group consisting of an epoxy group, oxetane group, hydroxyl group and carboxyl group)
A polymer obtained from a monomer represented by the following formula (II):
(In the formula (II), R 1 represents a hydrogen atom, a methyl group or a halogen atom, X 'represents an alkyl group having 1 to 7 carbon atoms, an aryl group having 6 to 12 carbon atoms, An alicyclic hydrocarbon group, or a group in which hydrogen atoms in these groups are substituted with at least one group selected from the group consisting of an epoxy group, oxetane group, hydroxyl group and carboxyl group), at least two kinds selected from the monomers represented by the formula (I) A polymer obtained from a monomer, a polymer obtained from two or more monomers selected from the monomers represented by the formula (II), and a polymer obtained from a monomer represented by the formula (I) and a monomer represented by the formula (II) 1 to 20 parts by weight of a polymer (E) having a weight average molecular weight of 1,000 to 30,000 selected from the group consisting of the cationic polymerizable component (A) (C) and the polymer (E) is 100 parts by mass,
Wherein the cationic polymerizable component (A) is a glycidylated product of a polyhydric alcohol or a glycidylated product of a polyhydric alcohol alkylene oxide adduct (A1) and an oxetane compound (A2)
Wherein the radical polymerizing component (C) is a compound (C1) having an epoxy group and an ethylenically unsaturated group, or a methacrylate ester (C2) as an essential component.
상기 양이온 중합성 성분(A)으로서, 방향족 에폭시 화합물(A3)을 더 함유하는, 경화성 조성물. The method according to claim 1,
The curable composition further contains an aromatic epoxy compound (A3) as the cationic polymerizable component (A).
상기 방향족 에폭시 화합물(A3)이 다관능 방향족 에폭시 화합물인, 경화성 조성물.3. The method of claim 2,
Wherein the aromatic epoxy compound (A3) is a polyfunctional aromatic epoxy compound.
상기 폴리머(E)가 상기 식(I)으로 표시되는 단량체 및 상기 식(II)으로 표시되는 단량체로부터 얻어지는 폴리머이며, 상기 식(I) 중의 X가 탄소 원자수 6∼12의 아릴기이며, 상기 식(II) 중의 X'가 탄소 원자수 1∼7의 알킬기이며, 상기 알킬기가 에폭시기로 치환되어 있는, 경화성 조성물.The method according to claim 1,
Wherein the polymer (E) is a polymer obtained from the monomer represented by the formula (I) and the monomer represented by the formula (II), X in the formula (I) is an aryl group having 6 to 12 carbon atoms, Wherein X 'in the formula (II) is an alkyl group having 1 to 7 carbon atoms, and the alkyl group is substituted with an epoxy group.
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WO2017170882A1 (en) | 2017-10-05 |
JP2017179162A (en) | 2017-10-05 |
KR102272147B1 (en) | 2021-07-01 |
JP7216470B2 (en) | 2023-02-01 |
CN108884298A (en) | 2018-11-23 |
TW201809021A (en) | 2018-03-16 |
TWI797078B (en) | 2023-04-01 |
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