KR20180132645A - Active energy ray-curable resin composition for optical articles, cured article and optical sheet - Google Patents
Active energy ray-curable resin composition for optical articles, cured article and optical sheet Download PDFInfo
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- KR20180132645A KR20180132645A KR1020187027336A KR20187027336A KR20180132645A KR 20180132645 A KR20180132645 A KR 20180132645A KR 1020187027336 A KR1020187027336 A KR 1020187027336A KR 20187027336 A KR20187027336 A KR 20187027336A KR 20180132645 A KR20180132645 A KR 20180132645A
- Authority
- KR
- South Korea
- Prior art keywords
- active energy
- meth
- acrylate
- energy ray
- ethylene oxide
- Prior art date
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- 230000003287 optical effect Effects 0.000 title claims abstract description 52
- 239000011342 resin composition Substances 0.000 title abstract description 39
- 150000001875 compounds Chemical class 0.000 claims abstract description 67
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- 239000000203 mixture Substances 0.000 claims abstract description 21
- 239000003999 initiator Substances 0.000 claims abstract description 11
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- 238000000034 method Methods 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 11
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 103
- -1 ethylene oxide modified urethane Chemical class 0.000 description 36
- 238000001723 curing Methods 0.000 description 20
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 12
- 239000000178 monomer Substances 0.000 description 12
- 239000004593 Epoxy Substances 0.000 description 11
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- 239000003963 antioxidant agent Substances 0.000 description 6
- 230000003078 antioxidant effect Effects 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
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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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F20/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
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- C—CHEMISTRY; METALLURGY
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Abstract
[과제] 틀 재현성, 내(耐)스크래치성, 또한 치수 안정성이나 컬성이 우수한 광학 물품용 활성 에너지선 경화형 수지 조성물, 경화물, 및 광학 시트를 제공하는 것에 있다.
[해결 수단] 활성 에너지선 중합성 화합물 및 광중합개시제를 함유하고, (1) 활성 에너지선 중합성기를 2개 이상 가지며 또한 에틸렌옥사이드기를 갖는 중합성 화합물을 함유하고, 당해 에틸렌옥사이드기의 중량 농도가 상기 활성 에너지선 중합성 화합물 전량에 대하여 6.0∼15.0중량％이며, (2) 활성 에너지선 중합성기를 2개 이상 갖는 중합성 화합물을 상기 활성 에너지선 중합성 화합물 전량에 대하여 30∼70중량％ 함유하는 광학 물품용 활성 에너지선 경화성 조성물, 당해 광학 물품용 활성 에너지선 경화성 조성물을 활성 에너지선으로 경화시킨 경화물, 및 광학 시트.[PROBLEMS] To provide an active energy ray-curable resin composition for optical articles, a cured product, and an optical sheet excellent in mold reproducibility, scratch resistance, dimensional stability and curling property.
[MEANS FOR SOLVING PROBLEMS] An image forming apparatus comprising an active energy ray-polymerizable compound and a photopolymerization initiator, wherein (1) contains a polymerizable compound having two or more active energy linear polymerizable groups and having an ethylene oxide group, (2) a polymerizable compound having at least two active energy linear polymerizable groups in an amount of 30 to 70% by weight based on the total amount of the active energy linear polymerizable compounds; An active energy ray curable composition for an optical article, a cured product obtained by curing the active energy ray curable composition for an optical article with an active energy ray, and an optical sheet.
Description
본 발명은 활성 에너지선 조사에 의한 경화 반응을 응용한 주형(注型) 중합에 사용되는 광학 물품용 활성 에너지선 경화형 수지 조성물, 및 당해 조성물을 경화시켜 얻은 광학 시트에 관한 것이다.The present invention relates to an active energy ray-curable resin composition for optical articles used in casting polymerization applying a curing reaction by active energy ray irradiation, and an optical sheet obtained by curing the composition.
활성 에너지선 조사에 의한 경화 반응을 응용한 기술은, 도료, 레지스트 재료, 인쇄 잉크, 접착제 등에 폭넓게 응용되고 있다. 이전에는 두께 수 ㎛ 정도의 막두께에 의한 응용 기술이 일반적이었지만, 근래에는 활성 에너지선 경화형 수지 조성물이 무용제 도공 가능한 이점이나, 조사에 의해 순시(瞬時)에 경화 반응이 일어나는 이점을 살려, 수십 ㎛ 이상의 막두께로 특정의 형상을 만들어 내는 가공·도공 기술도 주목을 받고 있고, 광조형법이나 광주형(光注型) 중합법 등이 실용화되고 있다. Techniques using a curing reaction by irradiation with active energy rays are widely applied to paints, resist materials, printing inks, and adhesives. In the past, application techniques using a film thickness of about several micrometers in thickness were common, but in recent years, taking advantage of the fact that the active energy ray-curable resin composition can be applied without a solvent, the curing reaction occurs instantaneously by irradiation, Processing technique for producing a specific shape with a film thickness equal to or more than the above is also attracting attention, and an optical shaping method, a light casting polymerization method, and the like are put into practical use.
이 중, 광주형 중합법은, 예를 들면, 미세한 형상을 부과한 모형(母型)에 활성 에너지선 경화형 수지 조성물을 충전(일괄 주입)하고, 모형에 개재(介在)시켜, 자외선 등에 의해 당해 수지 조성물을 경화시키는 방법이며, 모형의 복제를 정밀하게 대량으로 제조할 수 있다.Of these, in the photoluminescent polymerization method, for example, an active energy ray-curable resin composition is charged (injected in a batch) into a mold to which a fine shape is imposed and interposed in the mold, The resin composition is cured, and the replica of the model can be precisely mass-produced.
상기 광주형 중합법은, 기기의 소형화, 경량화에 수반하여, 플라스틱 기재상에 수지 경화물로 이루어지는 미세하고 복잡한 요철 표면 형상을 갖는 형상 부착 광학 시트(예를 들면, 프리즘 렌즈 시트나 프레넬 렌즈 시트 등), 렌즈, 프리즘 등의 플라스틱 물품이나 광학 물품의 제조에 적합한 방법이다. 이 광주형 중합법에 의한 플라스틱 물품이나 광학 물품을 제조할 때에 사용하는 활성 에너지선 경화형 수지 조성물에는 우수한 경화성이 요구되는 것에 더하여, 제조하는 경화물에는, 틀 재현성(경화물을 모형으로부터 벗길 때에, 틀로부터 찍어 낸 미세 형상이 깨지거나 변형하지 않는 성질)이나 내(耐)스크래치성이 요구된다. 또한 얻어진 경화물이 광학 시트일 경우, 확산 필름 등 다른 필름과 적층시키는 것이 종종 행해지고, 그때에는 치수 안정성이나 컬성 저감도 요구된다. 그러나 광주형 중합법 등의 광에 의한 중합은 중합시의 경화 수축이 커, 치수 안정성이나 내컬성이 떨어지는 것과 같은 경우가 있었다.[0005] The above-described photomultiplier polymerization method has been widely used in the field of optical equipment such as a shape-fitted optical sheet (for example, a prism lens sheet or a fresnel lens sheet) having a fine and complicated uneven surface shape, Etc.), lenses, prisms, and other plastic articles and optical articles. In addition to being required to have excellent curability, the active energy ray-curable resin composition for use in producing a plastic article or an optical article by this photopolymerization method is required to have excellent reproducibility of the mold (when the cured product is peeled from the mold, It is required that the fine shape drawn from the frame is not broken or deformed) and scratch resistance. When the obtained cured product is an optical sheet, lamination with another film such as a diffusion film is often carried out. At the same time, dimensional stability and curling property are also required. However, the polymerization by light such as the photopolymerization method has a problem that the curing shrinkage during polymerization is large and the dimensional stability and inner curl are inferior.
경화성이 우수하고, 얻어지는 경화물의 틀 재현성도 우수한 광학 물품용 활성 에너지선 경화형 수지 조성물로서, 예를 들면, 에폭시(메타)아크릴레이트나 우레탄(메타)아크릴레이트를 함유하는 활성 에너지선 경화형 수지 조성물이 많이 보고되고 있다. 구체적으로는, 예를 들면, 비스페놀A형 에폭시(메타)아크릴레이트와, 단관능 (메타)아크릴레이트와, 2관능 (메타)아크릴레이트와, 중량 평균 분자량이 9.5만인 아크릴 수지 등의 폴리머 성분을 함유하고, 경화 후의 굴절율이 1.55 이상인 프레넬 렌즈용 전리 방사선 경화형 수지 조성물이나(예를 들면, 특허문헌 1참조), 식 (1)로 표시되는 화합물을 함유하는 중합성 불포화 이중 결합을 갖는 단량체와, 중합성 불포화 단량체를 중합하여 얻어지고 중량 평균 분자량이 2,000∼100,000이며 중합체 구조 중에 중합성 불포화 이중 결합을 함유하는 중합체와, 광중합개시제를 함유하며, 또한, 상기 단량체와 중합체를 특정의 비율로 포함하는 광학 물품용 활성 에너지선 경화형 수지 조성물이 알려져 있다(예를 들면, 특허문헌 2 참조).An active energy ray curable resin composition excellent in curability and excellent in mold reproducibility of an obtained cured product, for example, an active energy ray curable resin composition containing epoxy (meth) acrylate or urethane (meth) Many are reported. Specifically, for example, a polymer component such as bisphenol A type epoxy (meth) acrylate, monofunctional (meth) acrylate, bifunctional (meth) acrylate, and acrylic resin having a weight average molecular weight of 9, (For example, see Patent Document 1), a monomer having a polymerizable unsaturated double bond containing a compound represented by Formula (1) and a compound having a refractive index after curing of 1.55 or more , A polymer obtained by polymerizing a polymerizable unsaturated monomer and having a weight average molecular weight of 2,000 to 100,000 and containing a polymerizable unsaturated double bond in the polymer structure and a photopolymerization initiator and further containing the monomer and the polymer in a specific ratio An active energy ray-curable resin composition for an optical article is known (see, for example, Patent Document 2).
그러나, 상기 특허문헌 1에 기재된 프레넬 렌즈용 전리 방사선 경화형 수지 조성물에 있어서, 상기 폴리머 성분은 경화 반응에 의해 생기는 가교 구조에 결합되지 않는다. 그 때문에, 폴리머 성분의 함유량이 많을 경우에는 경화성이 나빠지는 경향이 있었다. 또한 특허문헌 2에 기재된 광학 물품용 활성 에너지선 경화형 수지 조성물은, 틀 재현성이 우수하지만 치수 안정성이나 컬성이 떨어질 경우가 있었다.However, in the ionizing radiation curable resin composition for a Fresnel lens described in Patent Document 1, the polymer component is not bonded to the crosslinking structure caused by the curing reaction. Therefore, when the content of the polymer component is large, the curability tends to deteriorate. In addition, the active energy ray-curable resin composition for an optical article described in Patent Document 2 is excellent in frame reproducibility but sometimes has poor dimensional stability and curl.
본 발명의 과제는, 틀 재현성, 내스크래치성, 또한 치수 안정성이나 컬성이 우수한 광학 물품용 활성 에너지선 경화형 수지 조성물, 경화물, 및 광학 물품용 활성 에너지선 경화형 수지 조성물을 경화시켜 얻은 광학 시트를 제공하는 것에 있다.An object of the present invention is to provide an active energy ray-curable resin composition for optical articles excellent in mold reproducibility, scratch resistance, dimensional stability and curling property, a cured product, and an optical sheet obtained by curing an active energy ray- .
일반적으로, 조성물 중의 활성 에너지선 중합성기 농도를 낮게 하면, 가교 밀도가 저하하므로 경화 수축이 저감되어 컬성은 억제할 수 있다. 그러나 반면, 내스크래치성 등의 기계 물성도 저하해 버린다. 그러나 본 발명자들은 예의 검토한 결과, 조성물 중의 에틸렌옥사이드 농도, 및 활성 에너지선 중합성기를 2개 이상 갖는 중합성 화합물의 양을 특정의 범위로 함으로써, 상기 과제를 해결할 수 있음을 찾아냈다.Generally, when the concentration of the active energy pre-polymerizable group in the composition is lowered, the crosslinking density is lowered, so that the curing shrinkage is reduced and curling can be suppressed. However, on the other hand, mechanical properties such as scratch resistance are deteriorated. However, as a result of intensive studies, the inventors of the present invention have found that the above problems can be solved by setting the ethylene oxide concentration in the composition and the amount of the polymerizable compound having two or more active energy linear polymerizable groups within a specific range.
에틸렌옥사이드 골격을 구조로 갖는 활성 에너지선 중합성기를 2개 이상 갖는 중합성 화합물을 사용함으로써, 경화물의 주쇄(主鎖)에 유연한 에틸렌옥사이드기를 효과적으로 도입하여, 경화시에 발생하는 내부 응력 즉 경화 수축을 저감할 수 있었던 결과, 내스크래치성을 유지하는데다 컬성이 억제된 경화물을 얻을 수 있음을 찾아냈다.By using a polymerizable compound having two or more active energy pre-polymerizable groups having an ethylene oxide skeleton as a structure, a flexible ethylene oxide group is effectively introduced into the main chain (main chain) of the cured product and the internal stress generated upon curing, As a result, it has been found that a cured product having suppressed multifunctionality can be obtained in order to maintain scratch resistance.
즉, 본 발명은 활성 에너지선 중합성 화합물 및 광중합개시제를 함유하는 광학 물품용 활성 에너지선 경화성 조성물로서,That is, the present invention provides an active energy ray curable composition for an optical article containing an active energy ray polymerizable compound and a photopolymerization initiator,
(1) 활성 에너지선 중합성기를 2개 이상 가지며 또한 에틸렌옥사이드기를 갖는 중합성 화합물을 함유하고, 당해 에틸렌옥사이드기의 중량 농도가 상기 활성 에너지선 중합성 화합물 전량에 대하여 6.0∼15.0중량％이며,(1) A composition comprising (1) a polymerizable compound having two or more active energy linear polymerizable groups and having an ethylene oxide group, the weight concentration of the ethylene oxide group being 6.0 to 15.0% by weight based on the total amount of the active energy linear polymerizable compound,
(2) 활성 에너지선 중합성기를 2개 이상 갖는 중합성 화합물을 상기 활성 에너지선 중합성 화합물 전량에 대하여 30∼70중량％ 함유하는 광학 물품용 활성 에너지선 경화성 조성물을 제공한다.(2) an active energy ray-curable composition for an optical article containing a polymerizable compound having at least two active energy pre-polymerizable groups in an amount of 30 to 70% by weight based on the total amount of the active energy ray-polymerizable compound.
또한 본 발명은, 상기 기재한 광학 물품용 활성 에너지선 경화성 조성물을 활성 에너지선으로 경화시킨 경화물을 제공한다.The present invention also provides a cured product obtained by curing the active energy ray curable composition for an optical article described above with an active energy ray.
또한 본 발명은, 상기 기재한 광학 물품용 활성 에너지선 경화성 조성물을 활성 에너지선으로 경화시킨 광학 시트를 제공한다.The present invention also provides an optical sheet obtained by curing the aforementioned active energy ray curable composition for an optical article with an active energy ray.
본 발명에 의해, 틀 재현성, 내스크래치성, 또한 치수 안정성이나 내컬성이 우수하고, 프리즘 렌즈 시트나 프레넬 렌즈 시트 등의 미세한 표면 형상을 갖는 광학 시트를 얻을 수 있다.According to the present invention, it is possible to obtain an optical sheet having a fine surface shape such as a prism lens sheet or a Fresnel lens sheet, which is excellent in frame reproducibility, scratch resistance, dimensional stability and lubrication resistance.
(활성 에너지선 중합성 화합물)(Active energy ray polymerizable compound)
본 발명에서 사용하는 활성 에너지선 중합성 화합물은, (1) 활성 에너지선 중합성기를 2개 이상 가지며 또한 에틸렌옥사이드기를 갖는 중합성 화합물을 필수 성분으로서 함유하며, 또한 (2) 활성 에너지선 중합성기를 2개 이상 갖는 중합성 화합물을 상기 활성 에너지선 중합성 화합물 전량에 대하여 30∼70중량％ 함유한다.The active energy ray polymerizable compound used in the present invention is a compound having (1) a polymerizable compound having two or more active energy linear polymerizable groups and having an ethylene oxide group as essential components, and (2) In an amount of 30 to 70% by weight based on the total amount of the active energy ray-polymerizable compound.
(1) 활성 에너지선 중합성기를 2개 이상 가지며 또한 에틸렌옥사이드기를 갖는 중합성 화합물(1) a polymerizable compound having two or more active energy linear polymerizable groups and having an ethylene oxide group
본 발명에서 사용하는 활성 에너지선 중합성기를 2개 이상 가지며 또한 에틸렌옥사이드기를 갖는 중합성 화합물로서는, 특별히 한정 없이 공지의 것을 사용할 수 있다.As the polymerizable compound having two or more active energy-polymerizable groups and having an ethylene oxide group used in the present invention, known ones can be used without particular limitation.
(또한 본 발명에 있어서, 디(메타)아크릴레이트는 (메타)아크릴로일기를 2개 갖는 화합물을 나타내고, 트리(메타)아크릴레이트는 (메타)아크릴로일기를 3개 갖는 화합물을 나타내고, 폴리(메타)아크릴레이트는 (메타)아크릴로일기를 2개 이상 갖는 화합물을 나타내고, (메타)아크릴레이트는 아크릴레이트 및 메타크릴레이트의 총칭을 나타내고, (메타)아크릴로일기는 아크릴로일기 및 메타크릴로일기의 총칭을 나타낸다. 또한 에틸렌옥사이드는 EO라고 약칭할 경우가 있다)(In the present invention, the di (meth) acrylate represents a compound having two (meth) acryloyl groups, the tri (meth) acrylate represents a compound having three (meth) acryloyl groups, (Meth) acrylate is a compound having two or more (meth) acryloyl groups, (meth) acrylate is a generic term of acrylate and methacrylate, and the (meth) acryloyl group is acryloyl group and metha (Ethylene oxide) may be abbreviated as " EO "
예를 들면, 에틸렌글리콜디(메타)아크릴레이트, 디에틸렌글리콜디(메타)아크릴레이트, 트리에틸렌글리콜디(메타)아크릴레이트, 테트라에틸렌글리콜디(메타)아크릴레이트, 헵타에틸렌글리콜디(메타)아크릴레이트 등의 에틸렌옥사이드기를 갖는 디올에 (메타)아크릴산을 반응시킨 에틸렌옥사이드기 변성 디(메타)아크릴레이트나,(Meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, heptaethylene glycol di (Meth) acrylate obtained by reacting a diol having an ethylene oxide group such as acrylate with a (meth) acrylic acid,
트리메틸올프로판의 에틸렌옥사이드 변성 폴리(메타)아크릴레이트, 디트리메틸올프로판의 에틸렌옥사이드 변성 폴리(메타)아크릴레이트, 펜타에리트리톨의 에틸렌옥사이드 변성 폴리(메타)아크릴레이트, 디펜타에리트리톨의 에틸렌옥사이드 변성 폴리(메타)아크릴레이트, 테트라메틸올메탄의 에틸렌옥사이드 변성 폴리(메타)아크릴레이트 등의, 에틸렌옥사이드기를 갖는 폴리올에 (메타)아크릴산을 반응시킨 에틸렌옥사이드기 변성 폴리(메타)아크릴레이트나,(Meth) acrylate of trimethylolpropane, ethylene oxide-modified poly (meth) acrylate of ditrimethylolpropane, ethylene oxide-modified poly (meth) acrylate of pentaerythritol, ethylene oxide of dipentaerythritol (Meth) acrylate obtained by reacting a (meth) acrylic acid with a polyol having an ethylene oxide group, such as a poly (meth) acrylate modified with a poly (meth) acrylate and an ethylene oxide modified poly
에틸렌옥사이드기 변성 에폭시폴리(메타)아크릴레이트, 에틸렌옥사이드기 변성 우레탄폴리(메타)아크릴레이트, 에틸렌옥사이드기 변성 폴리에스테르폴리(메타)아크릴레이트 등의, 에틸렌옥사이드 변성 폴리(메타)아크릴레이트 올리고머 등을 들 수 있다.Ethylene oxide modified poly (meth) acrylate oligomers such as ethylene oxide modified epoxy poly (meth) acrylate, ethylene oxide modified urethane poly (meth) acrylate and ethylene oxide modified polyester poly (meth) .
상기 에틸렌옥사이드기의 중량 농도는, 상기 활성 에너지선 중합성 화합물 전량에 대하여 6.0∼15.0중량％이다. 당해 중량 농도를 이 범위로 함으로써, 컬성과 내스크래치성 등의 기계 물성과의 양립이 가능해진다. 상기 에틸렌옥사이드기의 중량 농도는 그 중에서도 6.5∼10.0중량％인 것이 바람직하고, 7.0∼9.0중량％인 것이 가장 바람직하다.The weight concentration of the ethylene oxide group is 6.0 to 15.0% by weight based on the total amount of the active energy ray polymerizable compound. By setting the weight concentration within this range, compatibility with mechanical properties such as curl and scratch resistance can be achieved. The weight concentration of the ethylene oxide group is preferably 6.5-10.0 wt%, and most preferably 7.0-10.0 wt%.
상기 활성 에너지선 중합성기를 2개 이상 가지며 또한 에틸렌옥사이드기를 갖는 중합성 화합물 중에서도, 트리메틸올프로판의 에틸렌옥사이드 변성 폴리(메타)아크릴레이트, 디트리메틸올프로판의 에틸렌옥사이드 변성 폴리(메타)아크릴레이트, 펜타에리트리톨의 에틸렌옥사이드 변성 폴리(메타)아크릴레이트, 디펜타에리트리톨의 에틸렌옥사이드 변성 폴리(메타)아크릴레이트, 테트라메틸올메탄의 에틸렌옥사이드 변성 폴리(메타)아크릴레이트 등의, 에틸렌옥사이드기를 갖는 폴리올에 (메타)아크릴산을 반응시킨 에틸렌옥사이드기 변성 폴리(메타)아크릴레이트를 사용하는 것이 바람직하고, 디펜타에리트리톨의 에틸렌옥사이드 변성 폴리(메타)아크릴레이트를 사용하는 것이 가장 바람직하다.Of the polymerizable compounds having two or more active energy linear polymerizable groups and having an ethylene oxide group, ethylene oxide-modified poly (meth) acrylates of trimethylolpropane, ethylene oxide-modified poly (meth) acrylates of ditrimethylolpropane, (Meth) acrylate of pentaerythritol such as ethylene oxide modified poly (meth) acrylate, dipentaerythritol ethylene oxide modified poly (meth) acrylate, and tetramethylol methane ethylene oxide modified poly It is preferable to use an ethylene oxide-modified poly (meth) acrylate obtained by reacting a polyol with (meth) acrylic acid, and it is most preferable to use ethylene oxide-modified poly (meth) acrylate of dipentaerythritol.
(2) 활성 에너지선 중합성기를 2개 이상 갖는 중합성 화합물(2) Polymerizable compound having two or more active energy-polymerizable groups
본 발명에서 사용하는 활성 에너지선 중합성기를 2개 이상 갖는 중합성 화합물로서는, 특별히 한정되지 않고 공지의 화합물을 사용할 수 있다.The polymerizable compound having two or more active energy-polymerizable groups used in the present invention is not particularly limited and known compounds can be used.
예를 들면, 1,3-부틸렌글리콜디(메타)아크릴레이트, 1,4-부탄디올디(메타)아크릴레이트, 1,5-펜탄디올디(메타)아크릴레이트, 3-메틸-1,5-펜탄디올디(메타)아크릴레이트, 1,6-헥산디올디(메타)아크릴레이트, 네오펜틸글리콜디(메타)아크릴레이트, 1,8-옥탄디올디(메타)아크릴레이트, 1,9-노난디올디(메타)아크릴레이트, 트리시클로데칸디메탄올디(메타)아크릴레이트, 에틸렌글리콜디(메타)아크릴레이트나,(Meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,5-pentanediol di (meth) acrylate, 3-methyl- Octanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, (Meth) acrylate, tricyclodecane dimethanol di (meth) acrylate, ethylene glycol di (meth) acrylate,
활성 에너지선 중합성기를 2개 이상 가지며 또한 에틸렌옥사이드기를 갖는 중합성 화합물, 에틸렌옥사이드기 이외의 알킬렌옥사이드기를 갖는 중합성 화합물, 예를 들면 프로필렌글리콜디(메타)아크릴레이트, 디프로필렌글리콜디(메타)아크릴레이트, 트리프로필렌글리콜디(메타)아크릴레이트, 테트라프로필렌글리콜디(메타)아크릴레이트, 폴리프로필렌글리콜디(메타)아크릴레이트, 1,3-부틸렌글리콜디(메타)아크릴레이트, 1,4-부틸렌글리콜디(메타)아크릴레이트, 1,6-헥사메틸렌글리콜디(메타)아크릴레이트, 1,9-노난디올디(메타)아크릴레이트, 네오펜틸글리콜디(메타)아크릴레이트, 히드록시피발산네오펜틸글리콜디(메타)아크릴레이트, 히드록시피발산네오펜틸글리콜에 카프로락톤을 부가한 화합물의 디(메타)아크릴레이트, 네오펜틸글리콜아디페이트디(메타)아크릴레이트나,A polymerizable compound having two or more active energy linear polymerizable groups and having an ethylene oxide group and a polymerizable compound having an alkylene oxide group other than an ethylene oxide group such as propylene glycol di (meth) acrylate, dipropylene glycol di (Meth) acrylate, tripropylene glycol di (meth) acrylate, tetrapropylene glycol di (meth) acrylate, polypropylene glycol di Acrylate, 1,6-hexanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, Di (meth) acrylate of a compound obtained by adding caprolactone to hydroxypivalic acid neopentyl glycol, di (meth) acrylate of neopentyl glycol di Di (meth) acrylate, or
트리메틸올프로판트리(메타)아크릴레이트, 펜타에리트리톨트리(메타)아크릴레이트, 디펜타에리트리톨의 폴리(메타)아크릴레이트, 트리메틸올프로판, 디트리메틸올프로판, 펜타에리트리톨, 디펜타에리트리톨, 테트라메틸올메탄에 1∼20몰의 에틸렌옥사이드 이외의 알킬렌옥사이드를 부가시킨 수산기 함유 화합물 등의 수산기를 3개 이상 갖는 화합물에 (메타)아크릴산이 3분자 이상 에스테르 결합한 화합물 등이나,Trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol poly (meth) acrylate, trimethylol propane, ditrimethylol propane, pentaerythritol, dipentaerythritol, A compound having three or more molecules of (meth) acrylic acid ester-bonded to a compound having three or more hydroxyl groups such as a hydroxyl group-containing compound in which alkylene oxide other than ethylene oxide is added to tetramethylolmethane,
비스페놀A형 에폭시 수지, 비스페놀F형 에폭시 수지, 일부 할로겐 치환된 비스페놀A형 에폭시 수지, 일부 할로겐 치환된 비스페놀F형 에폭시 수지, 수첨(水添) 비스페놀A형 에폭시 수지, 및 그것들의 혼합물로 이루어지는 군에서 선택되는 1종 이상의 에폭시 수지와 복수 몰의 (메타)아크릴산과의 반응에서 얻어지는 비스페놀형의 에폭시(메타)아크릴레이트나 페놀노볼락형의 에폭시(메타)아크릴레이트, 크레졸노볼락형의 에폭시(메타)아크릴레이트, 나프탈렌 골격의 에폭시(메타)아크릴레이트 또는 이들의 혼합물이나,A bisphenol A type epoxy resin, a bisphenol F type epoxy resin, a halogen-substituted bisphenol A type epoxy resin, a halogen-substituted bisphenol F type epoxy resin, a hydrogenated bisphenol A type epoxy resin, (Meth) acrylate, phenol novolak type epoxy (meth) acrylate, and cresol novolak type epoxy (meth) acrylate obtained by the reaction of one or more epoxy resins selected from (Meth) acrylate, epoxy (meth) acrylate of naphthalene skeleton or a mixture thereof,
폴리올과 환상(環狀) 구조를 갖는 유기 폴리이소시아네이트와 복수 몰의 수산기 함유 (메타)아크릴레이트의 반응에 의해 얻어지는 우레탄(메타)아크릴레이트, 환상 구조를 갖는 디올과 유기 폴리이소시아네이트와 복수 몰의 수산기 함유 (메타)아크릴레이트의 반응에 의해 얻어지는 우레탄(메타)아크릴레이트, 환상 구조를 갖는 유기 폴리이소시아네이트와 복수 몰의 수산기 함유 (메타)아크릴레이트의 반응에 의해 얻어지는 우레탄(메타)아크릴레이트 등을 들 수 있다.(Meth) acrylate obtained by reacting an organic polyisocyanate having a cyclic structure with a polyol and a hydroxyl group-containing (meth) acrylate having a plurality of moles, a diol having a cyclic structure, an organic polyisocyanate having a cyclic structure, Urethane (meth) acrylate obtained by the reaction of a polyfunctional (meth) acrylate having a cyclic structure and urethane (meth) acrylate obtained by the reaction of an organic polyisocyanate having a cyclic structure with a hydroxyl group .
상기 활성 에너지선 중합성기를 2개 이상 갖는 중합성 화합물은, 1종을 사용해도 되고 복수종을 혼합하여 사용해도 된다.The polymerizable compound having two or more active energy pre-polymerizable groups may be used either singly or in combination.
상술한 바와 같이, 본 발명에 있어서는, 상기 활성 에너지선 중합성기를 2개 이상 갖는 중합성 화합물은 상기 활성 에너지선 중합성 화합물 전량에 대하여 30∼70중량％인 것이 필수이다. 이 범위에 있어서, 특히 내컬성·내스크래치성 등의 기계 특성의 밸런스가 우수한 경화물을 얻을 수 있다. 활성 에너지선 중합성기를 2개 이상 갖는 중합성 화합물은 그 중에서도 40∼60중량％인 것이 바람직하다.As described above, in the present invention, it is essential that the polymerizable compound having two or more active energy linear polymerizable groups is contained in an amount of 30 to 70% by weight based on the total amount of the active energy linear polymerizable compounds. Within this range, it is possible to obtain a cured product having excellent balance of mechanical properties such as lubrication property and scratch resistance. The polymerizable compound having two or more active energy-polymerizable groups is preferably 40 to 60% by weight.
(방향족기를 갖는 중합성 화합물)(Polymerizable compound having an aromatic group)
본 발명에 있어서는, 방향족기를 갖는 중합성 화합물, 환상 지방족 구조를 갖는 중합성 화합물, 복소환 구조를 갖는 중합성 화합물, 스티렌계 화합물, 직쇄상 지방족 구조를 갖는 중합성 화합물 등을 사용하는 것은, 내스크래치성이나, 광학 시트에 필수 성능인 고굴절율을 얻을 수 있어 바람직하다. 예를 들면, 상기 방향족기를 갖는 중합성 화합물의 함유량은, 방향족기의 중량 농도가 상기 활성 에너지선 중합성 화합물 전량에 대하여 30∼60중량％가 되도록 하는 것이 바람직하고, 그 중에서도 30∼50중량％가 바람직하다.In the present invention, the use of a polymerizable compound having an aromatic group, a polymerizable compound having a cyclic aliphatic structure, a polymerizable compound having a heterocyclic structure, a styrene compound, a polymerizable compound having a linear aliphatic structure, Scratching property, and high refractive index, essential for optical sheets, can be obtained. For example, the content of the polymerizable compound having an aromatic group is preferably such that the weight concentration of the aromatic group is 30 to 60% by weight, more preferably 30 to 50% by weight, .
상기 방향족기를 갖는 중합성 화합물로서는, 예를 들면, 방향환을 갖는 (메타)아크릴산에스테르류 등을 들 수 있다. 방향환을 갖는 (메타)아크릴산에스테르류로서는, 예를 들면, 벤조일옥시에틸(메타)아크릴레이트, 벤질(메타)아크릴레이트, 페닐에틸(메타)아크릴레이트, 페녹시에틸(메타)아크릴레이트, 페녹시디에틸렌글리콜(메타)아크릴레이트, 2-히드록시-3-페녹시프로필(메타)아크릴레이트, 2-페닐-2-(4-아크릴로일옥시페닐)프로판, 2-페닐-2-(4-아크릴로일옥시알콕시페닐)프로판, 2,4,6-트리클로로페닐(메타)아크릴레이트, 2,4,6-트리브로모페닐(메타)아크릴레이트, 2,4,6-트리클로로벤질(메타)아크릴레이트, 2,4,6-트리브로모벤질(메타)아크릴레이트, 2,4,6-트리클로로페녹시에틸(메타)아크릴레이트, 2,4,6-트리브로모페녹시에틸(메타)아크릴레이트, o-페닐페놀(폴리)에톡시(메타)아크릴레이트, p-페닐페놀(폴리)에톡시(메타)아크릴레이트 등을 들 수 있다.Examples of the polymerizable compound having an aromatic group include (meth) acrylic acid esters having an aromatic ring and the like. Examples of the (meth) acrylic esters having an aromatic ring include benzoyloxyethyl (meth) acrylate, benzyl (meth) acrylate, phenylethyl (meth) acrylate, phenoxyethyl (meth) (Meth) acrylate, 2-phenyl-2- (4-acryloyloxyphenyl) propane, 2-phenyl- Acryloyloxyalkoxyphenyl) propane, 2,4,6-trichlorophenyl (meth) acrylate, 2,4,6-tribromophenyl (meth) acrylate, 2,4,6-trichlorobenzyl (Meth) acrylate, 2,4,6-tribromobenzyl (meth) acrylate, 2,4,6-trichlorophenoxyethyl (meth) acrylate, 2,4,6-tribromophenoxy Ethyl (meth) acrylate, o-phenylphenol (poly) ethoxy (meth) acrylate and p-phenylphenol (poly) ethoxy (meth) acrylate.
상기 환상 지방족 구조를 갖는 중합성 화합물로서는, 예를 들면, 환상 지방족을 갖는 (메타)아크릴산에스테르류 등을 들 수 있다. 환상 지방족을 갖는 (메타)아크릴산에스테르류로서는, 예를 들면, 시클로헥실(메타)아크릴레이트, 이소보로닐(메타)아크릴레이트, 디시클로펜타닐(메타)아크릴레이트, 디시클로펜테닐옥시에틸(메타)아크릴레이트, 테트라히드로푸르푸릴(메타)아크릴레이트, 글리시딜시클로카보네이트(메타)아크릴레이트, 트리시클로데칸디메틸올디(메타)아크릴레이트 등을 들 수 있다.Examples of the polymerizable compound having a cyclic aliphatic structure include (meth) acrylic acid esters having a cyclic aliphatic group. Examples of the (meth) acrylic esters having a cyclic aliphatic group include cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyloxyethyl (Meth) acrylate, tetrahydrofurfuryl (meth) acrylate, glycidylcyclocarbonate (meth) acrylate, and tricyclodecane dimethylol (meth) acrylate.
상기 스티렌계 화합물로서는, 예를 들면, 스티렌, α-메틸스티렌, 클로로스티렌 등을 들 수 있다.Examples of the styrene compound include styrene,? -Methylstyrene, chlorostyrene, and the like.
상기 복소환계 화합물로서는, 예를 들면, N-비닐피롤리돈, N-비닐카프로락톤, 아크릴로일포르몰린, 트리스(2-히드록시에틸)이소시아누레이트, 트리스(히드록시프로필)이소시아누레이트, 및 그것들에 1∼20몰의 알킬렌옥사이드 혹은 ε카프로락톤을 개환(開環) 부가시킨 수산기 함유 화합물 등의 수산기를 갖는 화합물에 (메타)아크릴산이 에스테르 결합한 이소시아누르산 구조를 갖는 화합물 등을 들 수 있다.Examples of the heterocyclic compound include N-vinylpyrrolidone, N-vinylcaprolactone, acryloylmorpholine, tris (2-hydroxyethyl) isocyanurate, tris (hydroxypropyl) iso Cyanurate, and an isocyanuric acid structure in which (meth) acrylic acid is ester-bonded to a compound having a hydroxyl group such as a hydroxyl group-containing compound in which 1 to 20 moles of alkylene oxide or 竜 caprolactone is ring- And the like.
(활성 에너지선 중합성기를 2개 이상 갖고 또한 에틸렌옥사이드기를 가지며, 또한 방향족기를 갖는 중합성 화합물)(A polymerizable compound having two or more active energy linear polymerizable groups and also having an ethylene oxide group and having an aromatic group)
또한, 상기 활성 에너지선 중합성기를 2개 이상 갖고 또한 에틸렌옥사이드기를 가지며, 또한 방향족기를 갖는 중합성 화합물을 사용하는 것도 물론 바람직하다. 이러한 중합성 화합물로서는, 에틸렌옥사이드기 변성 에폭시폴리(메타)아크릴레이트인, 에틸렌옥사이드 변성 비스페놀A 에폭시폴리(메타)아크릴레이트, 에틸렌옥사이드 변성 비스페놀F 에폭시폴리(메타)아크릴레이트, 에틸렌옥사이드 변성 비스페놀S 에폭시폴리(메타)아크릴레이트 등을 들 수 있다. 이들의 에틸렌옥사이드기 변성 에폭시폴리(메타)아크릴레이트가 갖는 에틸렌옥사이드기는, 1분자 중 평균치로 1∼30개의 반복 단위수를 갖는 것이 바람직하다.It is also preferable to use a polymerizable compound having two or more of the above-mentioned active energy linear polymerizable groups and having an ethylene oxide group and also having an aromatic group. Examples of such a polymerizable compound include ethylene oxide modified epoxy (meth) acrylate, ethylene oxide modified epoxy (meth) acrylate, ethylene oxide modified bisphenol F epoxy poly (meth) acrylate, ethylene oxide modified bisphenol S Epoxy poly (meth) acrylate, and the like. The ethylene oxide group of the ethylene oxide-modified epoxy poly (meth) acrylate is preferably an ethylene oxide group having an average of 1 to 30 repeating units in one molecule.
상기 에틸렌옥사이드기 및 활성 에너지선 중합성기를 2개 이상 갖는 중합성 화합물은, 1종을 사용해도 되고 복수종을 혼합하여 사용해도 된다. 복수종을 혼합하여 사용할 경우에는, 예를 들면, 비스페놀A의 에틸렌옥사이드 부가의 디아크릴레이트와 디펜타에리트리톨의 에틸렌옥사이드 부가물의 아크릴레이트와의 조합이나, 비스페놀A의 에틸렌옥사이드 부가의 디아크릴레이트와 트리메틸올프로판의 에틸렌옥사이드 부가물의 아크릴레이트와의 조합이 매우 바람직하다.The polymerizable compound having two or more ethylene oxide groups and active energy linear polymerizable groups may be used either singly or in combination. When a mixture of plural species is used, for example, a combination of diacrylate of ethylene oxide addition of bisphenol A and acrylate of ethylene oxide adduct of dipentaerythritol, diacrylate of ethylene oxide addition of bisphenol A And an acrylate of an ethylene oxide adduct of trimethylol propane is very preferable.
본 발명의 경화성 조성물은, 가교 구조 중에 에틸렌옥사이드쇄가 도입됨으로써 컬성이 우수하며, 또한 기계 물성(내스크래치성 등)도 겸비한 경화물이 얻어지는 것으로 추정하고 있다. 가교 구조 중에 에틸렌옥사이드쇄가 도입되지 않고, 측쇄에 펜던트되는 에틸렌옥사이드 골격을 갖는 단관능의 중합성 화합물을 사용했을 경우, 가교 밀도는 저하하기 때문에, 컬성은 억제되지만 기계 물성을 겸비한 경화물이 얻어지지 않을 가능성이 있다. The curable composition of the present invention is presumed to be capable of obtaining a cured product having excellent curl and mechanical properties (scratch resistance, etc.) by introducing ethylene oxide chain into the crosslinked structure. When a monofunctional polymerizable compound having an ethylene oxide skeleton pendant to the side chain is used without introducing ethylene oxide chain into the cross-linking structure, the cross-linking density is lowered, so that curl is suppressed, but a cured product having mechanical properties is obtained There is a possibility of not supporting.
이 점에서, 활성 에너지선 중합성기를 2개 이상 갖고 또한 에틸렌옥사이드기를 갖는 중합성 화합물은, 복수의 활성 에너지선 중합성기 사이에 에틸렌옥사이드쇄가 존재하는 구조인 것이 바람직하다.From this point of view, it is preferable that the polymerizable compound having two or more active energy linear polymerizable groups and also having an ethylene oxide group has a structure in which ethylene oxide chains exist between a plurality of active energy linear polymerizable groups.
(그 밖의 중합성 화합물)(Other polymerizable compound)
본 발명에 있어서는, 활성 에너지선 중합성기를 1개 갖는 중합성 화합물(단관능 모노머라고 할 경우가 있음)을 병용해도 매우 바람직하다. 단관능 모노머로서는 특별히 한정 없이 공지의 모노머를 사용할 수 있다.In the present invention, a polymerizable compound having one active energy linear polymerizable group (sometimes referred to as a monofunctional monomer) is also preferably used in combination. As the monofunctional monomer, a known monomer can be used without particular limitation.
예를 들면, (메타)아크릴산메틸, (메타)아크릴산에틸, (메타)아크릴산프로필, (메타)아크릴산부틸, (메타)아크릴산헥실, (메타)아크릴산헵실, (메타)아크릴산옥틸, (메타)아크릴산노닐, (메타)아크릴산데실, (메타)아크릴산도데실, (메타)아크릴산테트라데실, (메타)아크릴산헥사데실, (메타)아크릴산스테아릴, (메타)아크릴산옥타데실, (메타)아크릴산도데실 등의 탄소수 1∼22의 알킬기를 가지는 (메타)아크릴산에스테르류; (메타)아크릴산히드록시에틸, (메타)아크릴산히드록시프로필, (메타)아크릴산글리세롤, 락톤 변성 (메타)아크릴산히드록시에틸, (메타)아크릴산폴리에틸렌글리콜, (메타)아크릴산폴리프로필렌글리콜 등의 히드록시알킬기를 갖는 아크릴산에스테르류 등의 알킬기를 갖는 (메타)아크릴산에스테르류나,Examples of the (meth) acrylic acid include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, hexyl (Meth) acrylate, decyl (meth) acrylate, dodecyl (meth) acrylate, tetradecyl (meth) acrylate, hexadecyl (Meth) acrylic acid esters having an alkyl group having 1 to 22 carbon atoms; (Meth) acrylate such as hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, glycerol (meth) acrylate, lactone modified (meth) acrylate, polyethylene glycol (Meth) acrylic acid esters having an alkyl group such as an acrylate having an alkyl group,
(메타)아크릴산글리시딜, α-에틸(메타)아크릴산글리시딜, α-n-프로필(메타)아크릴산글리시딜, α-n-부틸(메타)아크릴산글리시딜, (메타)아크릴산-3,4-에폭시부틸, (메타)아크릴산-4,5-에폭시펜틸, (메타)아크릴산-6,7-에폭시펜틸, α-에틸(메타)아크릴산-6,7-에폭시펜틸, β-메틸글리시딜(메타)아크릴레이트, (메타)아크릴산-3,4-에폭시시클로헥실, 락톤 변성 (메타)아크릴산-3,4-에폭시시클로헥실, 비닐시클로헥센옥사이드 등의 중합성 불포화 이중 결합 및 에폭시기를 갖는 중합성 화합물,(Meth) acrylic acid glycidyl,? -Ethyl (meth) acrylate, glycidyl? -Propyl (meth) acrylate, glycidyl? (Meth) acrylic acid-6,7-epoxypentyl,? -Ethyl (meth) acrylate-6,7-epoxypentyl,? -Methylglycidyl (Meth) acrylate, a polymerizable unsaturated double bond such as (meth) acrylic acid-3,4-epoxycyclohexyl, lactone-modified (meth) acrylate- Containing polymerizable compound,
(메타)아크릴산, β-카르복시에틸(메타)아크릴레이트, 2-아크릴로일옥시에틸숙신산, 2-아크릴로일옥시에틸프탈산, 2-아크릴로일옥시에틸헥사히드로프탈산 및 이들의 락톤 변성물 등 에스테르 결합을 갖는 불포화 모노 카르복시산, 말레산 등의 중합성 불포화 이중 결합 및 카르복시기를 갖는 중합성 단량체,(Meth) acrylic acid,? -Carboxyethyl (meth) acrylate, 2-acryloyloxyethylsuccinic acid, 2-acryloyloxyethylphthalic acid, 2-acryloyloxyethylhexahydrophthalic acid and their lactone- Unsaturated monocarboxylic acids having an ester bond, polymerizable unsaturated double bonds such as maleic acid and polymerizable monomers having a carboxyl group,
푸마르산디메틸, 푸마르산디에틸, 푸마르산디부틸, 이타콘산디메틸, 이타콘산디부틸, 푸마르산메틸에틸, 푸마르산메틸부틸, 이타콘산메틸에틸 등의 불포화 디카르복시산에스테르류,Unsaturated dicarboxylic acid esters such as dimethyl fumarate, diethyl fumarate, dibutyl fumarate, dimethyl itaconate, dibutyl itaconate, methyl ethyl fumarate, methyl butyl fumarate and methyl ethyl itaconate,
스티렌, α-메틸스티렌, 클로로스티렌 등의 스티렌 유도체류; 부타디엔, 이소프렌, 피페릴렌, 디메틸부타디엔 등의 디엔계 화합물류; 염화 비닐, 브롬화 비닐 등의 할로겐화 비닐이나 할로겐화 비닐리덴류; 메틸비닐케톤, 부틸비닐케톤 등의 불포화 케톤류; 아세트산비닐, 부티르산비닐 등의 비닐에스테르류; 메틸비닐에테르, 부틸비닐에테르 등의 비닐에테르류; 아크릴로니트릴, 메타크릴로니트릴, 시안화 비닐리덴 등의 시안화 비닐류; 아크릴아미드나 그 알키드 치환 아미드류; N-페닐말레이미드, N-시클로헥실말레이미드 등의 N-치환 말레이미드류;Styrene derivatives such as styrene,? -Methyl styrene and chlorostyrene; Diene-based compounds such as butadiene, isoprene, piperylene and dimethylbutadiene; Vinyl halides such as vinyl chloride and vinyl bromide; halogenated vinylidene halides; Unsaturated ketones such as methyl vinyl ketone and butyl vinyl ketone; Vinyl esters such as vinyl acetate and vinyl butyrate; Vinyl ethers such as methyl vinyl ether and butyl vinyl ether; Vinyl cyanide such as acrylonitrile, methacrylonitrile, and vinylidene cyanide; Acrylamide or its alkyd substituted amides; N-substituted maleimides such as N-phenylmaleimide and N-cyclohexylmaleimide;
불화 비닐, 불화 비닐리덴, 트리플루오로에틸렌, 클로로트리플루오로에틸렌, 브로모트리플루오로에틸렌, 펜타플루오로프로필렌 혹은 헥사플루오로프로필렌과 같은 불소 함유 α-올레핀류; 또는 트리플루오로메틸트리플루오로비닐에테르, 펜타플루오로에틸트리플루오로비닐에테르 혹은 헵타플루오로프로필트리플루오로비닐에테르와 같은 (퍼)플루오로알킬기의 탄소수가 1 내지 18이 되는 (퍼)플루오로알킬·퍼플루오로비닐에테르류; 2,2,2-트리플루오로에틸(메타)아크릴레이트, 2,2,3,3-테트라플루오로프로필(메타)아크릴레이트, 1H,1H,5H-옥타플루오로펜틸(메타)아크릴레이트, 1H,1H,2H,2H-헵타데카플루오로데실(메타)아크릴레이트 혹은 퍼플루오로에틸옥시에틸(메타)아크릴레이트와 같은 (퍼)플루오로알킬기의 탄소수가 1 내지 18이 되는 (퍼)플루오로알킬(메타)아크릴레이트류 등의 불소 함유 에틸렌성 불포화 단량체류;Fluorine-containing? -Olefins such as vinyl fluoride, vinylidene fluoride, trifluoroethylene, chlorotrifluoroethylene, bromotrifluoroethylene, pentafluoropropylene or hexafluoropropylene; (Per) fluoroalkyl group having 1 to 18 carbon atoms in the (per) fluoroalkyl group such as trifluoromethyltrifluorovinyl ether, pentafluoroethyltrifluorovinyl ether or heptafluoropropyltrifluorovinyl ether, Cycloalkyl perfluorovinyl ethers; 2,2,2-trifluoroethyl (meth) acrylate, 2,2,3,3-tetrafluoropropyl (meth) acrylate, 1H, 1H, 5H-octafluoropentyl (meth) (Per) fluoroalkyl group having 1 to 18 carbon atoms in the (per) fluoroalkyl group such as 1H, 1H, 2H, 2H-heptadecafluorodecyl (meth) acrylate or perfluoroethyloxyethyl Fluorine-containing ethylenically unsaturated monomers such as cyclohexyl (meth) acrylate;
(16) γ-메타크릴옥시프로필트리메톡시실란 등의 실릴기 함유 (메타)아크릴레이트류; N,N-디메틸아미노에틸(메타)아크릴레이트, N,N-디에틸아미노에틸(메타)아크릴레이트 혹은 N,N-디에틸아미노프로필(메타)아크릴레이트 등의 N,N-디알킬아미노알킬(메타)아크릴레이트;(16) silyl group-containing (meth) acrylates such as? -Methacryloxypropyltrimethoxysilane; N, N-dialkylaminoalkyl (meth) acrylates such as N, N-dimethylaminoethyl (meth) acrylate, N, N-diethylaminoethyl (Meth) acrylate;
(메타)아크릴산포스포에틸, N,N-디메틸아미노에틸(메타)아크릴레이트, N,N-디에틸아미노에틸(메타)아크릴레이트 혹은 N,N-디에틸아미노프로필(메타)아크릴레이트, 디[(메타)아크릴로일옥시에틸]포스페이트, 트리[(메타)아크릴로일옥시에틸]포스페이트 등을 사용할 수 있다.(Meth) acrylate, N, N-diethylaminopropyl (meth) acrylate, N, N-dimethylaminoethyl (meth) [(Meth) acryloyloxyethyl] phosphate, tri [(meth) acryloyloxyethyl] phosphate, and the like.
그 중에서도, 바람직한 단관능 모노머로서는, 예를 들면 식 (1)로 표시되는 1관능 (메타)아크릴레이트를 들 수 있다.Among them, preferred monofunctional monomers include monofunctional (meth) acrylates represented by the formula (1).
(식 (1) 중, R1은 수소 원자이며, R2은 수소 원자 또는 메틸기이며, n의 평균치는 1∼5의 수임)(In the formula (1), R 1 is a hydrogen atom, R 2 is a hydrogen atom or a methyl group, and the average value of n is a number of 1 to 5)
식 (1)로 표시되는 화합물은, 예를 들면 p-페닐페놀 혹은, o-페닐페놀과 에틸렌옥사이드 혹은, 프로필렌옥사이드와의 반응물과 (메타)아크릴산을 반응시킴으로써 얻을 수 있다. p-페닐페놀 혹은 o-페닐페놀과 에틸렌옥사이드 혹은, 프로필렌옥사이드의 반응물은, 시장에서 용이하게 입수할 수 있다. 예를 들면, 산요가세이(주)제, 뉴폴 OPE-20(o-페닐페놀 1몰에 에틸렌옥사이드 2몰을 반응시킨 것), 뉴폴 OPE-40(o-페닐페놀 1몰에 에틸렌옥사이드 4몰을 반응시킨 것) 등을 사용할 수 있다.The compound represented by the formula (1) can be obtained, for example, by reacting p-phenylphenol or a reaction product of o-phenylphenol and ethylene oxide or propylene oxide with (meth) acrylic acid. Reaction products of p-phenylphenol or o-phenylphenol with ethylene oxide or propylene oxide are readily available on the market. For example, Newpol OPE-20 (1 mole of o-phenylphenol reacted with 2 moles of ethylene oxide) manufactured by Sanyo Chemical Industries, Ltd., Newpol OPE-40 (4 mole of o-phenylphenol and 1 mole of ethylene oxide ) Or the like can be used.
상기 단관능 모노머로서는, 1종을 사용해도 되고 복수종을 혼합하여 사용해도 된다. 복수종을 혼합하여 사용할 경우에는, 예를 들면, o-페닐페놀(폴리)에톡시(메타)아크릴레이트와 페녹시(폴리)에톡시(메타)아크릴레이트와의 조합이, 고굴절율과 기재 필름과의 밀착성을 확보하는데 있어서 바람직하다. 또한, o-페닐페놀(폴리)에톡시(메타)아크릴레이트와 페녹시벤질아크릴레이트와의 조합은 고굴절율과 저점도와 복원성(프리즘) 부여의 면에서 바람직하다.As the monofunctional monomer, one type may be used, or a plurality of types may be used in combination. (Meth) acrylate and phenoxy (poly) ethoxy (meth) acrylate are used in combination with a plurality of species, for example, a combination of o-phenylphenol It is preferable to secure the adhesion with. Also, the combination of o-phenylphenol (poly) ethoxy (meth) acrylate and phenoxybenzyl acrylate is preferable in terms of high refractive index, low viscosity, and stability (prism).
본 발명에 있어서는, 상기 단관능 모노머는, 본 발명의 효과를 훼손하지 않는 범위 내에서 사용하는 것이 바람직하다. 구체적으로는 상기 활성 에너지선 중합성 화합물 전량에 대하여 30∼70중량％의 범위 내가 바람직하다. 단관능 모노머는 그 중에서도 40∼60중량％인 것이, 작업성(저점도화)과 기계 물성의 양립을 도모하는데 있어서 바람직하다.In the present invention, the monofunctional monomer is preferably used within a range that does not impair the effect of the present invention. Specifically, it is preferably in the range of 30 to 70% by weight based on the total amount of the active energy ray polymerizable compound. Among them, the monofunctional monomer is preferably 40 to 60% by weight in order to achieve compatibility between workability (low viscosity) and mechanical properties.
(광중합개시제)(Photopolymerization initiator)
본 발명에서 사용하는 광중합개시제로서는, 예를 들면, 벤조페논, 3,3'-디메틸-4-메톡시벤조페논, 4,4'-비스디메틸아미노벤조페논, 4,4'-비스디에틸아미노벤조페논, 4,4'-디클로로벤조페논, 미힐러케톤, 3,3',4,4'-테트라(t-부틸퍼옥시카르보닐)벤조페논 등의 벤조페논류;Examples of the photopolymerization initiator used in the present invention include benzophenone, 3,3'-dimethyl-4-methoxybenzophenone, 4,4'-bisdimethylaminobenzophenone, 4,4'-bisdiethylamino Benzophenones such as benzophenone, 4,4'-dichlorobenzophenone, Michler's ketone, 3,3 ', 4,4'-tetra (t-butylperoxycarbonyl) benzophenone;
잔톤, 티오잔톤, 2-메틸티오잔톤, 2-클로로티오잔톤, 2,4-디에틸티오잔톤 등의 잔톤, 티오잔톤류; 벤조인, 벤조인메틸에테르, 벤조인에틸에테르, 벤조인이소프로필에테르 등의 아실로인에테르류;Xanthone such as xanthone, thioxanthone, 2-methylthioxanthone, 2-chlorothioxanthone and 2,4-diethylthioxanthone, thioxanthones; Acyloin ethers such as benzoin, benzoin methyl ether, benzoin ethyl ether, and benzoin isopropyl ether;
벤질, 디아세틸 등의 α-디케톤류; 테트라메틸티우람디설피드, p-톨릴디설피드 등의 설피드류; 4-디메틸아미노벤조산, 4-디메틸아미노벤조산에틸 등의 벤조산류;? -Diketones such as benzyl and diacetyl; Sulfhydrides such as tetramethylthiuram disulfide and p-tolyl disulfide; Benzoic acids such as 4-dimethylaminobenzoic acid and ethyl 4-dimethylaminobenzoate;
3,3'-카르보닐-비스(7-디에틸아미노)쿠마린, 1-히드록시시클로헥실페닐케톤, 2,2'-디메톡시-1,2-디페닐에탄-1-온, 2-메틸-1-〔4-(메틸티오)페닐〕-2-모르폴리노프로판-1-온, 2-벤질-2-디메틸아미노-1-(4-모르폴리노페닐)-부탄-1-온, 2-히드록시-2-메틸-1-페닐프로판-1-온, 2,4,6-트리메틸벤조일디페닐포스핀옥사이드, 비스(2,4,6-트리메틸벤조일)페닐포스핀옥사이드, 1-〔4-(2-히드록시에톡시)페닐〕-2-히드록시-2-메틸-1-프로판-1-온, 1-(4-이소프로필페닐)-2-히드록시-2-메틸프로판-1-온, 1-(4-도데실페닐)-2-히드록시-2-메틸프로판-1-온, 4-벤조일-4'-메틸디메틸설피드, 2,2'-디에톡시아세토페논, 벤질디메틸케탈, 벤질-β-메톡시에틸아세탈, o-벤조일벤조산메틸, 비스(4-디메틸아미노페닐)케톤, p-디메틸아미노아세토페논, α,α-디클로로-4-페녹시아세토페논, 펜틸-4-디메틸아미노벤조에이트, 2-(o-클로로페닐)-4,5-디페닐이미다졸릴 이량체, 2,4-비스-트리클로로메틸-6-[디-(에톡시카르보닐메틸)아미노]페닐-S-트리아진, 2,4-비스-트리클로로메틸-6-(4-에톡시)페닐-S-트리아진, 2,4-비스-트리클로로메틸-6-(3-브로모-4-에톡시)페닐-S-트리아진안트라퀴논, 2-t-부틸안트라퀴논, 2-아밀안트라퀴논, β-클로로안트라퀴논 등을 들 수 있다.2-methyl-2-methyl-2-methyl-2-methylpropane, 3,3'-carbonyl-bis (7-diethylamino) coumarin, 1-hydroxycyclohexyl phenyl ketone, 2,2'- 2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, 2- 2-methyl-1-phenylpropane-1-one, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide, 1- Methyl-1-propan-1-one, 1- (4-isopropylphenyl) -2-hydroxy- 1-one, 1- (4-dodecylphenyl) -2-hydroxy-2-methylpropan-1-one, 4-benzoyl-4'-methyldimethylsulfide, 2,2'-diethoxyacetophenone Benzyl dimethyl ketal, benzyl-beta-methoxy ethyl acetal, methyl o-benzoyl benzoate, bis (4-dimethylaminophenyl) ketone, p- dimethylaminoacetophenone,?,? -Dichloro- Pentyl-4-dimethylaminobenzo Di (ethoxycarbonylmethyl) amino] phenyl-S (2-hydroxyphenyl) imidazolyl dimer, 2,4-bis-trichloromethyl-6- -Triazine, 2,4-bis-trichloromethyl-6- (4-ethoxy) phenyl-S-triazine, 2,4-bis- trichloromethyl-6- (3- 2-t-butyl anthraquinone, 2-amylanthraquinone, and? -Chloroanthraquinone.
상기 광중합개시제는, 1종을 사용해도 되고 복수종을 혼합하여 사용해도 된다. 그 사용량은 특별히 제한은 없지만, 감도를 양호하게 유지하고, 결정(結晶)의 석출, 도막 물성의 열화(劣化) 등 방지하기 위해, 본 발명의 광학 물품용 활성 에너지선 경화형 수지 조성물 100중량부에 대하여 0.05∼20중량부 사용하는 것이 바람직하고, 그 중에서도 0.1∼10중량부가 특히 바람직하다.The photopolymerization initiator may be used either singly or in combination. The amount of the active energy ray-curable resin composition for optical articles of the present invention is not particularly limited, but it is preferable that 100 parts by weight of the active energy ray-curable resin composition for an optical article of the present invention is used in order to keep the sensitivity well and prevent precipitation of crystal (crystal) Is preferably 0.05 to 20 parts by weight, and particularly preferably 0.1 to 10 parts by weight.
그 중에서도, 1-히드록시시클로헥실페닐케톤, 2-히드록시-2-메틸-1-페닐프로판-1-온, 1-〔4-(2-히드록시에톡시)페닐〕-2-히드록시-2-메틸-1-프로판-1-온, 티오잔톤 및 티오잔톤 유도체, 2,2'-디메톡시-1,2-디페닐에탄-1-온, 2,4,6-트리메틸벤조일디페닐포스핀옥사이드, 비스(2,4,6-트리메틸벤조일)페닐포스핀옥사이드, 2-메틸-1-[4-(메틸티오)페닐]-2-모르폴리노-1-프로판온, 2-벤질-2-디메틸아미노-1-(4-모르폴리노페닐)-부탄-1-온의 군에서 선택되는 1종 또는 2종류 이상의 혼합계가, 경화성이 높은 광학 물품용 활성 에너지선 경화형 수지 조성물이 얻어지기 때문에 특히 바람직하다.Among them, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- [4- (2- hydroxyethoxy) Methyl-1-propan-1-one, thioxanthone and thioxanthone derivatives, 2,2'-dimethoxy-1,2-diphenylethan-1-one, 2,4,6-trimethylbenzoyldiphenyl (2-methyl-1- [4- (methylthio) phenyl] -2-morpholino-1-propanone, 2-benzyl 2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, a curable highly active energy ray radiation curable resin composition for an optical article is obtained Which is particularly preferable.
또한, 본 발명의 광학 물품용 활성 에너지선 경화형 수지 조성물에서는, 상기 광중합개시제에 각종 광증감제를 병용할 수 있다. 광증감제로서는, 예를 들면, 아민류, 요소류, 함(含)황 화합물, 함인 화합물, 함염소 화합물 또는 니트릴류 혹은 그 밖의 함질소 화합물 등을 들 수 있다.In the active energy ray-curable resin composition for an optical article of the present invention, various photo-sensitizers may be used in combination with the photopolymerization initiator. Examples of the photosensitizer include amines, ureas, sulfur compounds, phosphorus compounds, chlorine compounds or nitriles or other nitrogen-containing compounds.
본 발명의 광학 물품용 활성 에너지선 경화형 수지 조성물을 사용한 물품의 제조에서는, 자외선 등의 활성 에너지선은, 지지체가 되는 투명 기재면을 통해 조사될 경우가 많다. 그 때문에, 광중합개시제는, 장파장 영역에 흡광 능력을 갖는 개시제가 바람직하고, 예를 들면, 자외선이 360∼450㎚의 범위에 있어서 광개시 능력을 발휘하는 광중합개시제가 바람직하다.In the production of an article using the active energy ray-curable resin composition for an optical article of the present invention, active energy rays such as ultraviolet rays are often irradiated through a transparent substrate surface to be a support. Therefore, as the photopolymerization initiator, an initiator having a light absorbing ability in a long wavelength region is preferable, and for example, a photopolymerization initiator that exhibits photoinitiation ability in the range of 360 to 450 nm of ultraviolet light is preferable.
본 발명의 광학 물품용 활성 에너지선 경화형 수지 조성물은, 점도나 투명 기판에의 접착성 개량 등을 목적으로 하여 수지 등을 병용할 수도 있다. 예를 들면, 메틸메타크릴레이트 수지, 메틸메타크릴레이트계 공중합물 등의 아크릴 수지; 폴리스티렌, 메틸메타크릴레이트-스티렌계 공중합물; 폴리에스테르 수지; 폴리우레탄 수지; 폴리부타디엔이나 부타디엔-아크릴로니트릴계 공중합물 등의 폴리부타디엔 수지; 비스페놀형 에폭시 수지, 페녹시 수지나 노볼락형 에폭시 수지 등의 에폭시 수지 등을 들 수 있다.The active energy ray-curable resin composition for an optical article of the present invention may be used in combination with a resin for the purpose of improving viscosity or improving adhesion to a transparent substrate. For example, acrylic resins such as methyl methacrylate resin and methyl methacrylate type copolymer; Polystyrene, methyl methacrylate-styrene copolymer; Polyester resin; Polyurethane resin; Polybutadiene resins such as polybutadiene and butadiene-acrylonitrile copolymers; Epoxy resins such as bisphenol type epoxy resin, phenoxy resin and novolak type epoxy resin, and the like.
본 발명의 광학 물품용 활성 에너지선 경화형 수지 조성물의 점도는, 모형에 균일하게 도포을 할 수 있고, 추가로 미세 구조를 갖는 모형의 복제가 가능하도록 하기 위해, 25℃에서 100∼30000mPa·s의 범위에 있는 것이 바람직하고, 그 중에서도 150∼20000mPa·s인 것이 특히 바람직하다. 상기 범위 이외의 점도여도, 수지 조성물의 온도를 컨트롤해서 점도를 조절하는 등의 방법을 취하면, 사용할 수 있다.The viscosity of the active energy ray-curable resin composition for an optical article of the present invention is preferably in the range of 100 to 30000 mPa 占 퐏 at 25 占 폚 in order to uniformly coat the model and enable the replica of the model further having a microstructure. , And particularly preferably 150 to 20,000 mPa · s. Even if the viscosity is outside the above range, the viscosity of the resin composition can be controlled by controlling the temperature of the resin composition.
본 발명의 광학 물품용 활성 에너지선 경화형 수지 조성물의 산가(시료 1g 중에 존재하는 산 만큼을 규정하는 방법에 의거하여, 중화하는데 필요한 수산화칼륨의 밀리그램수)는, 5.0㎎KOH／g 이하인 것이 환경 안정성이 우수한 경화물이 얻어지는 광학 물품용 활성 에너지선 경화형 수지 조성물이 되므로 바람직하고, 0㎎KOH／g∼3.0㎎KOH／g이 특히 바람직하다.The acid value of the active energy ray-curable resin composition for an optical article of the present invention (the number of milligrams of potassium hydroxide necessary for neutralization based on the method of specifying the acid present in 1 g of the sample) is 5.0 mgKOH / g or less, Particularly preferably 0 mgKOH / g to 3.0 mgKOH / g, in order to obtain an active energy ray-curable resin composition for an optical article from which an excellent cured product can be obtained.
본 발명의 광학 물품용 활성 에너지선 경화형 수지 조성물은, 기재상에 형성된 경화 수지 성형층에 추가적인 내광성이 요구될 경우 등, 필요에 따라, 자외선 흡수제를 첨가할 수 있다. 또한, 도막의 개질이나 도장(塗裝) 적성, 모형으로부터의 이형성(離型性)을 개선시킬 경우에는, 산화 방지제, 실리콘계 첨가제, 불소계 첨가제, 레올로지 컨트롤제, 탈포제, 이형제, 실란커플링제, 대전 방지제, 방담제(防曇劑), 착색제 등을 첨가하는 것도 가능하다.The ultraviolet absorber may be added to the active energy ray-curable resin composition for an optical article of the present invention, if necessary, such as when additional light resistance is required for the cured resin molding layer formed on the substrate. In order to improve the coating film modulus, coating suitability, and releasability from the model, it is preferable to add an antioxidant, a silicon additive, a fluorine additive, a rheology control agent, a defoaming agent, a releasing agent, , An antistatic agent, an antifogging agent, a coloring agent and the like may be added.
자외선 흡수제로서는, 예를 들면, 2-[4-{(2-히드록시-3-도데실옥시프로필)옥시}-2-히드록시페닐]-4,6-비스(2,4-디메틸페닐)-1,3,5-트리아진, 2-[4-{(2-히드록시-3-트리데실옥시프로필)옥시}-2-히드록시페닐]-4,6-비스(2,4-디메틸페닐)-1,3,5-트리아진 등의 트리아진 유도체, 2-(2'-잔텐카르복시-5'-메틸페닐)벤조트리아졸, 2-(2'-o-니트로벤질옥시-5'-메틸페닐)벤조트리아졸, 2-잔텐카르복시-4-도데실옥시벤조페논, 2-o-니트로벤질옥시-4-도데실옥시벤조페논 등을 들 수 있다.Examples of the ultraviolet absorber include 2- [4 - {(2-hydroxy-3-dodecyloxypropyl) oxy} -2-hydroxyphenyl] -4,6-bis (2,4- Hydroxyphenyl] -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2- [4 - {(2-hydroxy-3-tridecyloxypropyl) oxy} (2'-o-nitrobenzyloxy-5'-methylphenyl) -1,3,5-triazine, 2- Methylphenyl) benzotriazole, 2-xanthene carboxy-4-dodecyloxybenzophenone, and 2-o-nitrobenzyloxy-4-dodecyloxybenzophenone.
산화 방지제로서는, 예를 들면, 힌더드페놀계 산화 방지제, 힌더드아민계 산화 방지제, 유기 황계 산화 방지제, 인산에스테르계 산화 방지제 등을 들 수 있다.Examples of the antioxidant include a hindered phenol-based antioxidant, a hindered amine-based antioxidant, an organic sulfur-based antioxidant, and a phosphoric acid ester-based antioxidant.
실리콘계 첨가제로서는, 예를 들면, 디메틸폴리실록산, 메틸페닐폴리실록산, 환상 디메틸폴리실록산, 메틸하이드로겐폴리실록산, 폴리에테르 변성 디메틸폴리실록산 공중합체, 폴리에스테르 변성 디메틸폴리실록산 공중합체, 불소 변성 디메틸폴리실록산 공중합체, 아미노 변성 디메틸폴리실록산 공중합체 등과 같이 알킬기나 페닐기를 갖는 폴리오르가노실록산류를 들 수 있다.Examples of the silicone additive include dimethylpolysiloxane, methylphenylpolysiloxane, cyclic dimethylpolysiloxane, methylhydrogenpolysiloxane, polyether-modified dimethylpolysiloxane copolymer, polyester-modified dimethylpolysiloxane copolymer, fluorine-modified dimethylpolysiloxane copolymer, amino-modified dimethylpolysiloxane And polyorganosiloxanes having an alkyl group or a phenyl group such as a copolymer.
상기한 바와 같이 각종 첨가제의 사용량으로서는, 그 효과를 충분히 발휘하고, 또한 자외선 경화를 저해하지 않는 범위이므로, 당해 광학 물품용 활성 에너지선 경화형 수지 조성물 100중량부에 대하여, 각각 0.01∼10중량부의 범위인 것이 바람직하다.As described above, the amount of the various additives to be used is within a range that sufficiently exhibits its effect and does not inhibit ultraviolet curing. Therefore, the amount of each additive is preferably in the range of 0.01 to 10 parts by weight per 100 parts by weight of the active energy ray- .
본 발명의 광학 물품용 활성 에너지선 경화형 수지 조성물에는 필요에 따라 용제를 함유시켜도 되지만, 용제의 함유율은 적은 쪽이 작업 환경을 오염시키기 어려운 광학 물품용 활성 에너지선 경화형 수지 조성물이 얻어지므로 바람직하다. 구체적으로는, 본 발명의 광학 물품용 활성 에너지선 경화형 수지 조성물 중의 용제 함유율은 1중량％ 이하가 바람직하다.The active energy ray-curable resin composition for an optical article of the present invention may contain a solvent if necessary, but it is preferable that an active energy ray-curable resin composition for an optical article which is less likely to contaminate the working environment is obtained if the content of the solvent is small. Specifically, the content of the solvent in the active energy ray-curable resin composition for an optical article of the present invention is preferably 1% by weight or less.
본 발명의 광학 물품용 활성 에너지선 경화형 수지 조성물은, 필름상, 시트상, 판상의 투명 기재상의 수지 경화물로 이루어지는 성형 수지층을 마련한 구조의 각종 물품에 적합한 재료이다. 그 중에서도, 렌즈 등의 투명성을 필요로 하는 물품의 제조에 사용할 경우에는, 두께 200±25㎛의 경화물에 있어서 400∼900㎚의 파장 영역의 광선 투과율이 80％ 이상, 바람직하게는 85％ 이상이 되도록 각 수지 조성물 성분을 조합시켜 사용하는 것이 바람직하다.The active energy ray-curable resin composition for an optical article of the present invention is a material suitable for various articles having a structure in which a molded resin layer composed of a resin cured product on a film, sheet, or plate-like transparent substrate is provided. Among them, when used in the production of an article requiring transparency such as a lens, it is preferable that the light transmittance in a wavelength range of 400 to 900 nm is 80% or more, preferably 85% or more It is preferable to use the resin composition components in combination.
(경화물)(Hard goods)
본 발명의 경화물은 본 발명의 광학 물품용 활성 에너지선 경화형 수지 조성물을 경화시켜 이루어지는 것이다. 당해 경화물은, 미세 형상을 부과한 수지 경화층에 가해지는 압력이 작을 경우에는 변형하지 않을 정도의 단단함을 갖고, 또한 일시적으로 강한 압력이 가해졌을 경우에도 형상이 무너지지 않기 위해서는(경취(硬脆) 상태가 아니기 위해서는), 25℃에 있어서의 동적 점탄성에 의한 탄성율이 2500∼3000MPa인 것이 바람직하고, 2700∼2900MPa이 보다 바람직하다.The cured product of the present invention is obtained by curing the active energy ray curable resin composition for an optical article of the present invention. The cured product has such a rigidity as not to be deformed when the pressure applied to the resin cured layer to which the fine shape is applied is small and in order to prevent the shape from breaking even when a strong pressure is temporarily applied ) State), the elastic modulus by dynamic viscoelasticity at 25 DEG C is preferably 2500 to 3000 MPa, more preferably 2700 to 2900 MPa.
마찬가지로 컬에 관해서도, 탄성율이 높을수록 경화 수축에 의한 영향이 발현되기 쉬우므로, 물성 밸런스를 생각해서 상기 범위 내에서 설계하는 것이 바람직하다.Likewise, as for the curl, the higher the modulus of elasticity is, the easier the effect of the curing shrinkage tends to appear, so that it is preferable to design within the above-mentioned range in consideration of the balance of physical properties.
컬성을 제어하는 인자(因子)로서는, 동적 점탄성에 있어서의 tanδmax도 들 수 있다. Tanδmax의 피크치는, 가교 구조에 있어서의 가교점간 분자량의 분포를 나타내고 있으며, 피크치가 낮고 브로드일 경우에는, 가교점간 분자량의 분포가 넓고, 경화 수축이 분산되기 위해 컬성은 양호해지고, 피크치가 높아서 샤프할 경우에는, 가교점간 분자량의 분포가 균일하기 때문에, 경화시에 단번에 수축이 일어나기 때문에, 컬성은 악화되기 때문에, 바람직하지 못하다. 이 점, 내스크래치성에 관해서도, 가교점간 분자량의 분포를 넓힘으로써, 수지 경화물의 인성(靭性)을 높일 수 있으므로, 강도·탄성율과의 밸런스를 유지하는 범위 내에서 Tanδmax의 피크치를 낮게 설계하는 것이 보다 바람직하다.As a factor controlling the curl, there is also tan? Max in dynamic viscoelasticity. The peak value of tan delta max indicates the distribution of the molecular weight between the crosslinking points in the crosslinking structure. When the peak value is low and broad, the distribution of the molecular weight between the crosslinking points is wide, the curing shrinkage is dispersed and the curling property becomes good, , Since the distribution of the molecular weight between the crosslinking points is uniform, shrinkage occurs at a time at the time of curing, and curling is deteriorated, which is not preferable. With respect to this point and scratch resistance, it is also possible to increase the toughness of the resin cured product by widening the distribution of the molecular weight between the crosslinking points, so that it is preferable to design the peak value of Tanδmax to be low within a range in which the balance with strength / desirable.
또한 본 발명에 있어서, 동적 점탄성은, 점탄성 측정 장치로서 Rheometoric Scientific사제의 「RSAII」를 사용하고, 측정 조건으로서, 승온 스피드 3℃／Min, 주파수는 3.5Hz의 조건으로 측정한 값으로 한다.In the present invention, the dynamic viscoelasticity is a value measured by using RSAII manufactured by Rheometoric Scientific as a viscoelasticity measuring apparatus under the conditions of a temperature rise speed of 3 캜 / min and a frequency of 3.5 Hz as a measurement condition.
(경화 방법)(Curing method)
본 발명의 광학 물품용 활성 에너지선 경화형 수지 조성물을 경화시키는 활성 에너지선은, 전자파 또는 하전 입자선 중, 분자를 중합, 가교할 수 있는 에너지 양자(量子)를 갖는 것을 의미하고, 예를 들면, 가시광선, 자외선, X선 등의 전자파, 또는 전자선 등의 하전 입자선을 들 수 있다. 이들 중에서 실용상 자주 사용되는 것은, 가시광선, 자외선이다. 자외선의 경우에는, 초고압 수은등, 고압 수은등, 저압 수은등, 카본 아크, 블랙라이트 램프, 메탈할라이드 램프 등의 광원을 사용할 수 있다.The active energy ray for curing the active energy ray-curable resin composition for an optical article of the present invention means having an energy quantum capable of polymerizing and crosslinking a molecule in an electromagnetic wave or a charged particle beam. For example, Electron beams such as visible light, ultraviolet rays, and X-rays, and charged particle beams such as electron beams. Of these, visible light and ultraviolet light are frequently used in practice. In the case of ultraviolet rays, light sources such as ultrahigh pressure mercury lamps, high pressure mercury lamps, low pressure mercury lamps, carbon arc lamps, black light lamps, and metal halide lamps can be used.
(광학 시트)(Optical sheet)
본 발명의 광학 시트를 제조하는 방법으로서는, 본 발명의 광학 물품용 활성 에너지선 경화형 수지 조성물을, 필요로 하는 미세 형상을 갖는 모형상에 충전한 후, 충전된 당해 수지 조성물상에 플라스틱 기재를 공기가 혼입하지 않도록 가압 적층하여 밀착시키고, 플라스틱 기재측으로부터 자외선 등의 활성 에너지선을 조사하여 당해 수지 조성물을 경화시킨 후, 모형으로부터 이형하는 방법 등을 들 수 있다. 또한 예를 들면, 롤상의 모형에 당해 수지 조성물을 연속적으로 충전한 후, 충전된 당해 수지 조성물상에 플라스틱 기재를 공기가 혼입하지 않도록 연속적으로 밀착시켜, 플라스틱 기재측으로부터 자외선 등의 활성 에너지선을 조사하여 당해 수지 조성물을 경화시킨 후, 롤상의 모형으로부터 이형하는 연속 제조 방법 등을 들 수 있다.As a method of producing the optical sheet of the present invention, the active energy ray-curable resin composition for an optical article of the present invention is filled in a mold having a required fine shape, and then the plastic substrate is filled with air A method in which the resin composition is hardened by irradiating an active energy ray such as ultraviolet rays from the plastic substrate side and releasing from the model. For example, after the resin composition is continuously charged into a mold on a roll, the plastic substrate is continuously brought into close contact with the plastic substrate so that air is not mixed with the plastic substrate, and an active energy ray such as ultraviolet rays And then curing the resin composition, and thereafter releasing the resin composition from the mold on the roll.
이것에 사용할 수 있는 필름상, 시트상, 판상의 투명 기재로서는, 예를 들면, 폴리에틸렌테레프탈레이트(PET), 폴리에틸렌나프탈레이트(PEN) 등의 폴리에스테르 수지, 트리아세틸셀룰로오스, 폴리카보네이트 수지, 메틸메타크릴레이트계 공중합물 등의 아크릴 수지, 스티렌 수지, 폴리설폰 수지, 폴리에테르설폰 수지, 폴리카보네이트 수지, 염화 비닐 수지, 폴리메타크릴이미드 수지 등을 들 수 있다. 또한, 플라스틱 기재는 아니지만, 유리 기재 등의 무기 기재도 마찬가지로 사용하는 것이 가능하다.Examples of the film-like, sheet-like, and plate-like transparent substrates which can be used for this purpose include polyester resins such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), triacetylcellulose, polycarbonate resin, Acrylate resins such as acrylate resins, acrylate resins, polyether sulfone resins, polycarbonate resins, vinyl chloride resins and polymethacrylimide resins. Further, although not a plastic substrate, an inorganic substrate such as a glass substrate can be used as well.
[실시예][Example]
이하에 실시예 및 비교예를 들어, 본 발명을 보다 구체적으로 설명한다. 예 중의 부 및 ％는, 특별히 기재가 없는 한, 전부 중량 기준이다.Hereinafter, the present invention will be described in more detail by way of examples and comparative examples. All parts and percentages are by weight unless otherwise specified.
(광학 물품용 활성 에너지선 경화성 조성물의 조정)(Adjustment of active energy ray-curable composition for optical article)
하기 표 1에 나타내는 바와 같은 배합으로 조성물을 조정했다. 또한, 각 성분의 당해 에틸렌옥사이드기의 중량 농도나 방향족기의 중량 농도는, 각 구조 성분의 구조식으로부터 산출했다.The composition was adjusted as shown in Table 1 below. The weight concentration of the ethylene oxide group and the weight concentration of the aromatic group of each component were calculated from the structural formulas of the respective structural components.
[표 1][Table 1]
표 중, 약어는 이하와 같다.Abbreviations in the table are as follows.
유니딕크 V-5500(DIC사제, BPA형 에폭시아크릴레이트)Unidix V-5500 (manufactured by DIC, BPA type epoxy acrylate)
방향환량: 33.7％, EO쇄 함유량: 0％Directional volume: 33.7%, EO chain content: 0%
TMP3EO-3A: 트리메틸올프로판의 EO 변성(n＝3) 트리아크릴레이트TMP3EO-3A: EO-modified (n = 3) trimethylolpropane triacrylate
방향환량: 0％, EO쇄 함유량: 18％Directional volume: 0%, EO chain content: 18%
BPA4EO-2A: BPA의 EO 변성(n＝4) 디아크릴레이트BPA4EO-2A: EO-modified (n = 4) diacrylate of BPA
방향환량: 30.5％, EO쇄 함유량: 31.2％Directional volume: 30.5%, EO chain content: 31.2%
오르토 페녹시페닐에틸아크릴레이트Orthophenoxyphenyl ethyl acrylate
방향환량: 58.2％, EO쇄 함유량: 16.4％Directional volume: 58.2%, EO chain content: 16.4%
페녹시에틸아크릴레이트Phenoxy ethyl acrylate
방향환량: 40.6％, EO쇄 함유량: 20.8％Directional exchange rate: 40.6%, EO chain content: 20.8%
벤질아크릴레이트Benzyl acrylate
방향환량: 48.1％, EO쇄 함유량: 0％Directional volume: 48.1%, EO chain content: 0%
DP6A／DP5A＝6／4: 디펜타에리트리톨헥사아크릴레이트／디펜타에리트리톨펜타아크릴레이트＝6／4DP6A / DP5A = 6/4: dipentaerythritol hexaacrylate / dipentaerythritol pentaacrylate = 6/4
방향환량: 0％, EO쇄 함유량: 0％Directional volume: 0%, EO chain content: 0%
h) DP-EO-6A／DP-EO-5A＝6／4: 디펜타에리트리톨의 EO 변성 헥사아크릴레이트／디펜타에리트리톨의 EO 변성 펜타아크릴레이트＝6／4(EO 중합도: 0.85)EO-modified hexaacrylate of dipentaerythritol / EO-modified pentaacrylate of dipentaerythritol = 6/4 (EO degree of polymerization: 0.85) DP-EO-6A / DP-
방향환량: 0％, EO쇄 함유량: 26.7％Directional volume: 0%, EO chain content: 26.7%
i) I-184: 1-히드록시-시클로헥실페닐케톤(광개시제) 이르가큐어 184[BASF사제]i) I-184: 1-Hydroxy-cyclohexyl phenyl ketone (photoinitiator) Irgacure 184 [manufactured by BASF]
(경화물의 작성 방법, 및 평가 방법)(Method for preparing cured product and evaluation method)
경화물의 작성 방법, 및 평가 방법은 이하와 같이 행했다.The preparation method of the cured product and the evaluation method were carried out as follows.
<동적 점탄성 측정 Tg·저장 탄성률·tanδmax(피크 높이)의 측정>≪ Dynamic viscoelasticity measurement Tg, storage elastic modulus, tan delta max (peak height)
(경화물의 작성 방법)(Preparation method of cured product)
유리판에 실시예 또는 비교예의 수지 조성물을 적하하고, 스핀 코터로 막두께 100㎛가 되도록 도장한 후, 질소 분위기 하에서 UV 조사를 행하여 경화 도막을 작성했다. 조사 조건은, 아이그라픽스사제의 메탈할라이드 램프로 적산 광량 1000mJ／㎠로 행했다. 그 후, 유리판으로부터 경화물인 수지 필름을 벗기고, 3㎜×50㎜로 재단하여 시험편으로 했다.The resin composition of Example or Comparative Example was dropped on a glass plate, coated with a spin coater so as to have a film thickness of 100 mu m, and then subjected to UV irradiation in a nitrogen atmosphere to prepare a cured coating film. Irradiation was performed with a metal halide lamp manufactured by Igraphics Co., at an integrated light quantity of 1000 mJ / cm 2. Thereafter, the resin film as a cured product was peeled off from the glass plate and cut into 3 mm x 50 mm to obtain a test piece.
(동적 점탄성 측정)(Dynamic viscoelasticity measurement)
수지 필름의 Tg, 저장 탄성률, 및 tanδmax(피크 높이)의 측정에는, 점탄성 측정 장치로서 Rheometoric Scientific사제의 「RSAII」를 사용하고, 측정 조건은 승온 스피드: 3℃／Min, 주파수: 3.5Hz로 행했다.RSAII manufactured by Rheometoric Scientific Co., Ltd. was used as the viscoelasticity measuring apparatus, and the measurement conditions were a temperature rise speed of 3 占 폚 / min and a frequency of 3.5 Hz to measure the Tg, the storage elastic modulus and the tan? Max (peak height) .
<컬성 평가><Curriculum Evaluation>
75㎛의 PET 필름(도요보사제: 코스모샤인 A4300)을 기재로 하여, 실시예 또는 비교예의 수지 조성물을 도장하고, 질소 분위기 하에서 UV 조사를 행하고(조사 조건은, 아이그라픽스사제의 메탈할라이드 램프로 적산 광량 1000mJ／㎠), 프리즘 시트(피치 간격 20㎛)를 작성했다.The resin composition of Example or Comparative Example was coated on a 75 μm PET film (Toyobo Co., Ltd., Cosmo Shine A4300) as a base material, and UV irradiation was conducted in a nitrogen atmosphere (irradiation conditions were integrating with a metal halide lamp manufactured by Igraphics Co., Light quantity: 1000 mJ / cm 2) and a prism sheet (pitch interval: 20 탆).
작성한 프리즘 시트를 5㎝ 각으로 재단하고, 1일 실온에서 방치한 후, 4귀퉁이의 휘어짐(컬)의 정도를 메이저로 밀리미터 단위로 계측하고, 4귀퉁이의 합계치를 컬성의 지표로 했다. 값이 낮을수록, 컬하고 있지 않음을 나타낸다. 본 평가에 있어서는 10㎜ 이하이면 합격으로 했다.The prepared prism sheet was cut to a 5 cm square and allowed to stand at room temperature for 1 day. Then, the degree of warping (curl) of four corners was measured in units of millimeters as a major, and the total value of four corners was used as an index of curl. The lower the value, the less curl. In this evaluation, if the distance is 10 mm or less, the acceptance is made.
<내스크래치성><Scratch resistance>
상기와 마찬가지의 조건으로 작성한 프리즘 시트 위에, 편광 필름을 중첩시키고, 그 위에 추를 올렸다. 이 상태에서 프리즘 시트만을 당겨, 프리즘 시트 표면에 생긴 흠집의 정도를 육안으로 관찰했다.A polarizing film was superimposed on a prism sheet prepared under the same conditions as above, and a weight was placed on the polarizing film. In this state, only the prism sheet was pulled, and the degree of scratches formed on the prism sheet surface was visually observed.
추의 무게를 바꾸어 시험하고, 흠집이 나지 않은 최대의 중량(g)을 내스크래치성의 값으로 했다. 값이 높을수록, 내스크래치가 우수하다. 본 평가에 있어서는, 100g 이상이면 합격으로 했다.The weights of the weights were varied and tested, and the maximum weight (g) without scratches was taken as the scratch resistance value. The higher the value, the better the scratch resistance. In this evaluation, if it is 100 g or more, it was accepted.
실시예 및 비교예의 결과를 표 2에 나타낸다.The results of Examples and Comparative Examples are shown in Table 2.
[표 2][Table 2]
이 결과, 실시예 1∼3의 광학 물품용 활성 에너지선 경화성 조성물의 경화물은, 컬성 및 내스크래치성이 우수했다. 특히 디펜타에리트리톨의 에틸렌옥사이드 변성 폴리(메타)아크릴레이트를 사용한 실시예 1과 실시예 2는, 내스크래치성이 매우 우수했다. 한편 비교예 1∼3은 모두 에틸렌옥사이드기의 농도가 6중량％ 이하이기 때문에, 내스크래치성이 떨어졌다. 또한 비교예 3은 DMA 저장 탄성률(25℃)이 3000으로 매우 높고, 컬성이 떨어지는 것을 알 수 있었다.As a result, the cured products of the active energy ray curable compositions for optical articles of Examples 1 to 3 were excellent in curl and scratch resistance. In particular, Example 1 and Example 2 using ethylene oxide modified poly (meth) acrylate of dipentaerythritol were excellent in scratch resistance. On the other hand, in all of Comparative Examples 1 to 3, the concentration of ethylene oxide groups was less than 6% by weight, and thus scratch resistance was deteriorated. In Comparative Example 3, it was found that the DMA storage elastic modulus (25 ° C) was as high as 3000, and the curl was deteriorated.
Claims (5)
(1) 활성 에너지선 중합성기를 2개 이상 가지며 또한 에틸렌옥사이드기를 갖는 중합성 화합물을 함유하고, 당해 에틸렌옥사이드기의 중량 농도가 상기 활성 에너지선 중합성 화합물 전량에 대하여 6.0∼15.0중량％이며,
(2) 활성 에너지선 중합성기를 2개 이상 갖는 중합성 화합물을 상기 활성 에너지선 중합성 화합물 전량에 대하여 30∼70중량％ 함유하는 것을 특징으로 하는 광학 물품용 활성 에너지선 경화성 조성물.An active energy ray curable composition for an optical article comprising an active energy ray polymerizable compound and a photopolymerization initiator,
(1) A composition comprising (1) a polymerizable compound having two or more active energy linear polymerizable groups and having an ethylene oxide group, the weight concentration of the ethylene oxide group being 6.0 to 15.0% by weight based on the total amount of the active energy linear polymerizable compound,
(2) An active energy ray curable composition for an optical article, which contains 30 to 70% by weight of a polymerizable compound having two or more active energy pre-polymerizable groups based on the total amount of the active energy ray polymerizable compounds.
상기 활성 에너지선 중합성기를 2개 이상 가지며 또한 에틸렌옥사이드기를 갖는 중합성 화합물이 디펜타에리트리톨의 에틸렌옥사이드 변성 폴리(메타)아크릴레이트인 광학 물품용 활성 에너지선 경화성 조성물.The method according to claim 1,
Wherein the polymerizable compound having two or more active energy linear polymerizable groups and having an ethylene oxide group is an ethylene oxide modified poly (meth) acrylate of dipentaerythritol.
방향족기의 중량 농도가 상기 활성 에너지선 중합성 화합물 전량에 대하여 30∼60중량％인 광학 물품용 활성 에너지선 경화성 조성물.3. The method according to claim 1 or 2,
Wherein the weight concentration of the aromatic group is 30 to 60% by weight based on the total amount of the active energy ray polymerizable compound.
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| JP2016033206A (en) * | 2014-03-31 | 2016-03-10 | 株式会社日本触媒 | Active energy ray-curable aqueous resin composition |
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| Publication number | Publication date |
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| JP6390817B2 (en) | 2018-09-19 |
| KR102367697B1 (en) | 2022-02-28 |
| WO2017169838A1 (en) | 2017-10-05 |
| TW201802172A (en) | 2018-01-16 |
| TWI708808B (en) | 2020-11-01 |
| JPWO2017169838A1 (en) | 2018-06-28 |
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