JPH0649366A - Sulfur-containing resin composition and optical article made thereof - Google Patents
Sulfur-containing resin composition and optical article made thereofInfo
- Publication number
- JPH0649366A JPH0649366A JP20234992A JP20234992A JPH0649366A JP H0649366 A JPH0649366 A JP H0649366A JP 20234992 A JP20234992 A JP 20234992A JP 20234992 A JP20234992 A JP 20234992A JP H0649366 A JPH0649366 A JP H0649366A
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- Prior art keywords
- sulfur
- oil
- containing resin
- resin composition
- weight
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Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、臭気の少ない含硫黄樹
脂組成物およびそれを用いた光学物品に関するものであ
る。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a sulfur-containing resin composition having little odor and an optical article using the same.
【０００２】[0002]
【従来の技術】オレフィン系熱硬化性樹脂は一般的に耐
熱性・耐薬品性に優れている。2. Description of the Related Art Olefin-based thermosetting resins are generally excellent in heat resistance and chemical resistance.
【０００３】眼鏡レンズ等の光学用途には、ジエチレン
グリコールビスアリルカーボネートが幅広く用いられて
いるものの、レンズを薄型・軽量化する上で、低い屈折
率が問題となっている。Although diethylene glycol bisallyl carbonate is widely used for optical applications such as eyeglass lenses, a low refractive index is a problem in making the lens thin and lightweight.
【０００４】そこで、硫黄原子の導入による高屈折率樹
脂が提案され、例えば、チオールエステルを主成分とす
る樹脂が、特開昭63-316766 号公報や特開昭63-162671
号公報や特開昭63-188660 号公報等で、また、硫黄を含
有する屈折率１．６２〜１．６４の樹脂が、特開平2-15
8612号公報で提案されている。Therefore, a resin having a high refractive index by introducing a sulfur atom has been proposed. For example, a resin containing a thiol ester as a main component is disclosed in JP-A-63-316766 and JP-A-63-162671.
Japanese Patent Laid-Open No. 63-188660 and the like, and a resin having a refractive index of 1.62 to 1.64 containing sulfur is disclosed in
Proposed in 8612.
【０００５】[0005]
【発明が解決しようとする課題】ところが、硫黄原子を
導入した場合、導入率が高くなるにつれて、得られた樹
脂を加工する場合の臭気が強くなり、市場で受け入れら
れなくなる。However, when a sulfur atom is introduced, as the introduction rate increases, the odor of processing the obtained resin becomes stronger and it becomes unacceptable in the market.
【０００６】特に、架橋構造を持つ樹脂は耐熱性に優れ
るため、高温の加工が行われることが多く、加工時の臭
気が問題になることが多い。[0006] In particular, since a resin having a crosslinked structure is excellent in heat resistance, it is often subjected to high temperature processing, and odor during processing is often a problem.
【０００７】本発明は、かかる従来技術の欠点を解消し
ようとするものであり、表面処理の際の加熱処理や切削
加工時の臭気の少ない含硫黄樹脂組成物およびそれを用
いた光学物品を提供することを目的とする。The present invention is intended to solve the above-mentioned drawbacks of the prior art, and provides a sulfur-containing resin composition having less odor during heat treatment during surface treatment and during cutting and an optical article using the same. The purpose is to do.
【０００８】[0008]
【課題を解決するための手段】本発明は、上記目的を達
成するために下記の構成を有する。The present invention has the following constitution in order to achieve the above object.
【０００９】「(1) 含硫黄樹脂を主成分とし、植物油を
含有することを特徴とする含硫黄樹脂組成物。"(1) A sulfur-containing resin composition comprising a sulfur-containing resin as a main component and a vegetable oil.
【００１０】(2) 上記(1) 項の含硫黄樹脂組成物からな
る光学物品。」 植物油とは、植物中から抽出される化合物である。ま
た、抽出によって得られる化合物の他に、植物精製油の
中で、構造が既知で合成によって得られる化合物につい
ては、合成された化合物を用いても同様の効果を得るこ
とができ、本発明では、植物からの抽出・精製操作によ
って得られた植物精製油以外にも、これらと同じ構造を
有する合成化合物も植物油と総称する。(2) An optical article comprising the sulfur-containing resin composition according to the above item (1). A vegetable oil is a compound extracted from plants. Further, in addition to the compound obtained by extraction, among the plant refined oils, for the compound obtained by synthesis with a known structure, the same effect can be obtained by using the synthesized compound. In addition to plant refined oils obtained by plant extraction / refining operations, synthetic compounds having the same structure as these are also collectively referred to as vegetable oils.
【００１１】この植物油の具体例としては、レモン油、
プチグレン油、ネロリ油、オレンジ油、ペルガモット
油、バラ油、レモングラス油、ジンジャーグラス油、シ
トロネラ油、パルマローザ油、ベチバー油、白檀油、リ
ナロエ油、オポパナックス油、ローズマリー油、サイム
油、ペパーミント油、ラベンダー油、クラリセイジ油、
シソ油、スパイク油、パチュリー油、ゼラニウム油、ア
ジョワン油、アニス油、カラウェー油、コリアンデル
油、フェンネル油、ジャスミン油、ポアドロース油、シ
ンナモン油、カシア油、ベイ油、クローブ油、カヤブテ
油、イランイラン油、カナンガ油、シダーウッド油、ア
ビエス油、スターアニス油、チョーベローズ油、オリス
油、オークモス油、ショウノウ油、テレビン油、クロモ
ジ油、スペアミント油、ユーカリ油などがある。これら
の中で、好ましい植物油としては、スペアミント油、ペ
パーミント油、ユーカリ油が挙げられ、特に硫黄臭を無
臭化する効果が大きい。Specific examples of this vegetable oil include lemon oil,
Petit Glen Oil, Neroli Oil, Orange Oil, Pergamot Oil, Rose Oil, Lemongrass Oil, Gingergrass Oil, Citronella Oil, Palmarosa Oil, Vetiver Oil, Sandalwood Oil, Linaloe Oil, Opopanax Oil, Rosemary Oil, Sim Oil, Peppermint Oil , Lavender oil, clary sage oil,
Perilla oil, spike oil, patchouli oil, geranium oil, ajowan oil, anise oil, caraway oil, coriandel oil, fennel oil, jasmine oil, poadrose oil, cinnamon oil, cassia oil, bay oil, clove oil, kayak oil, Iran oil Iran oil, cananga oil, cedarwood oil, abies oil, star anise oil, chobelose oil, orris oil, oak moss oil, camphor oil, turpentine oil, chromodi oil, spearmint oil, eucalyptus oil and the like. Among these, preferred vegetable oils include spearmint oil, peppermint oil, and eucalyptus oil, and they are particularly effective in deodorizing the sulfur odor.
【００１２】また、これらの植物油の主成分である化合
物は、その化合物も減臭効果を持つ。たとえば、スペア
ミント油の主成分であるカルボン、ペパーミント油の主
成分であるメントール、ユーカリ油の主成分であるテル
ペンアルコール等は、これら主成分を添加することによ
っても、減臭効果が発揮され、これら植物油の主成分で
ある化合物についても、本発明でいう植物油に含まれ
る。The compounds which are the main components of these vegetable oils also have a deodorizing effect. For example, carvone, which is the main component of spearmint oil, menthol, which is the main component of peppermint oil, and terpene alcohol, which is the main component of eucalyptus oil, also exhibit a deodorizing effect by adding these main components. The compound which is the main component of vegetable oil is also included in the vegetable oil in the present invention.
【００１３】植物油を添加する量は、好ましくは、樹脂
に対して０．０１〜３．０重量％の範囲であり、さらに
好ましくは、樹脂に対して０．０１〜２．０重量％の範
囲である。２．０重量％を越えると、樹脂の機械的特性
の低下を生じる傾向がある。樹脂中に植物油を添加する
方法は、樹脂の原料となる単量体中に植物油を添加した
後に、加熱やエネルギー線の照射によって、樹脂を硬化
する方法が好ましい。また、植物油を溶解した溶剤中に
樹脂を浸漬して樹脂中に含浸させる方法、あるいは、樹
脂と植物油を混合した後に成型することによっても可能
である。The amount of vegetable oil added is preferably in the range of 0.01 to 3.0% by weight with respect to the resin, and more preferably in the range of 0.01 to 2.0% by weight with respect to the resin. Is. If it exceeds 2.0% by weight, the mechanical properties of the resin tend to be deteriorated. The method of adding the vegetable oil to the resin is preferably a method of curing the resin by heating or irradiating energy rays after adding the vegetable oil to the monomer that is the raw material of the resin. It is also possible to immerse the resin in a solvent in which the vegetable oil is dissolved to impregnate the resin, or to mix the resin and the vegetable oil and then mold the resin.
【００１４】本発明において、含硫黄樹脂としては、硫
黄を含む樹脂であれば特に限定されることなく用いら
れ、ラジカル重合可能な官能基を有する単量体を重合す
ることによって得られる樹脂、−ＳＨ基を持つ化合物と
イソシアネート基を持つ化合物を反応させて得られるウ
レタン樹脂、−ＳＨ基を持つ化合物とエポキシ基を持つ
化合物を反応させて得られる樹脂、−Ｓ−の構造を樹脂
中に有する樹脂などがある。中でも特に、熱によって溶
解せず、分解が生じる架橋構造を有する樹脂である場合
に特に有効である。さらに、架橋構造を有し、かつ、屈
折率１．５５以上である樹脂である場合には、高屈折率
で薄型化可能な樹脂が期待できるため効果的である。In the present invention, the sulfur-containing resin is not particularly limited as long as it is a resin containing sulfur, and it is a resin obtained by polymerizing a monomer having a radically polymerizable functional group, Urethane resin obtained by reacting a compound having an SH group with a compound having an isocyanate group, a resin obtained by reacting a compound having an -SH group with a compound having an epoxy group, and having a -S- structure in the resin Resin etc. Above all, it is particularly effective in the case of a resin having a crosslinked structure which is not dissolved by heat and decomposes. Further, a resin having a crosslinked structure and a refractive index of 1.55 or more is effective because a resin having a high refractive index and capable of being thinned can be expected.
【００１５】また、含硫黄樹脂として、芳香環を有する
ラジカル重合可能な単量体を含む単量体組成物を重合し
てなる樹脂が好ましく用いられる。芳香環を有するラジ
カル重合可能な単量体とは、分子内に１個以上のラジカ
ル重合可能な官能基を有し、なおかつ、ベンゼン環を有
する化合物であれば特に限定はないが、好ましくは、得
られる樹脂において硫黄臭を低減させる効果が特に期待
できる点で、下記の一般式（Ａ）で示される構造を有す
る化合物が用いられる。As the sulfur-containing resin, a resin obtained by polymerizing a monomer composition containing a radically polymerizable monomer having an aromatic ring is preferably used. The radically polymerizable monomer having an aromatic ring is not particularly limited as long as it has at least one radically polymerizable functional group in the molecule and has a benzene ring, but preferably, In the obtained resin, a compound having a structure represented by the following general formula (A) is used because the effect of reducing the sulfur odor can be expected.
【００１６】[0016]
【化２】 （式（Ａ）中、Ｒ1 は、水素あるいはメチル基を示す。
Ｒ2 は、水素あるいは炭素数１〜６の飽和炭化水素を示
す。） 式（Ａ）中、Ｒ2 は水素あるいは炭素数１〜６の飽和炭
化水素を示し、飽和炭化水素の具体例としては、メチル
基、エチル基、イソプロピル基、ｎ−プロピル基、ｔ−
ブチル基、ｎ−ブチル基、イソブチル基、ネオペンチル
基、ｎ−ヘキシル基、シクロヘキシル基などが挙げられ
る。[Chemical 2] (In the formula (A), R 1 represents hydrogen or a methyl group.
R 2 represents hydrogen or a saturated hydrocarbon having 1 to 6 carbon atoms. In the formula (A), R 2 represents hydrogen or a saturated hydrocarbon having 1 to 6 carbon atoms, and specific examples of the saturated hydrocarbon include methyl group, ethyl group, isopropyl group, n-propyl group, t-
Examples thereof include a butyl group, an n-butyl group, an isobutyl group, a neopentyl group, an n-hexyl group and a cyclohexyl group.
【００１７】式（Ａ）で示される化合物の好ましい具体
例としては、スチレン、α−メチルスチレン、核置換ス
チレン、核置換α−メチルスチレンなどが挙げられる。Preferred specific examples of the compound represented by the formula (A) include styrene, α-methylstyrene, nucleus-substituted styrene and nucleus-substituted α-methylstyrene.
【００１８】これら芳香環を有するラジカル重合可能な
単量体は、硫黄臭気を低減させる効果が特に大きく、ま
た、低比重でかつ、高屈折率の樹脂が期待できる点で
０．５〜７０重量％の含有率で単量体組成物中に含有さ
せることが好ましい。さらに、芳香環を有するラジカル
重合可能な単量体を０．５〜７０重量％含有する場合に
は、植物油を単量体組成物中に０．０５〜３．０重量％
の範囲で含有することが好ましい。The radical-polymerizable monomer having an aromatic ring has a particularly large effect of reducing sulfur odor, and has a low specific gravity and is expected to be a resin having a high refractive index. It is preferable that the content thereof be contained in the monomer composition at a content rate of%. Furthermore, when the radical polymerizable monomer having an aromatic ring is contained in an amount of 0.5 to 70% by weight, vegetable oil is contained in the monomer composition in an amount of 0.05 to 3.0% by weight.
It is preferable to contain in the range of.
【００１９】また、これら含硫黄樹脂のうち、硫黄原子
を９重量％以上、中でも１２重量％以上含有する樹脂は
加工時の臭気対策を必要とする場合が多く、この場合に
本発明は特に有効である。Of these sulfur-containing resins, those containing 9% by weight or more, and especially 12% by weight or more of sulfur atoms, often require countermeasures against odor during processing. In this case, the present invention is particularly effective. Is.
【００２０】本発明で得られた樹脂組成物の表面に、ハ
ードコート膜や反射防止膜をもうけることによって、表
面特性に優れた光学物品を製造することができる。By providing a hard coat film or an antireflection film on the surface of the resin composition obtained in the present invention, an optical article having excellent surface characteristics can be manufactured.
【００２１】また、本発明で添加する植物油だけでな
く、各種の紫外線吸収剤・酸化防止剤を樹脂に添加する
ことによって、耐久性に優れた樹脂が得られる。By adding not only the vegetable oil added in the present invention but also various ultraviolet absorbers and antioxidants to the resin, a resin having excellent durability can be obtained.
【００２２】本発明により得られた樹脂組成物は、光学
レンズ、メガネレンズ、塗料、光学機器用物品などとし
て好適に用いられる。The resin composition obtained by the present invention is suitably used as an optical lens, a spectacle lens, a coating material, an article for optical equipment and the like.
【００２３】[0023]
【実施例】以下実施例により、本発明を具体的に説明す
る。The present invention will be specifically described with reference to the following examples.
【００２４】臭気については、玉摺研磨機で研磨した場
合の研磨機周辺の臭気を評価した。尚、臭気の評価は３
人の人間が行い、２人以上の人間が悪臭を感じる場合を
×、１人の人間が悪臭を感じる場合を△、悪臭を感じる
人がいない場合を○とした。Regarding the odor, the odor around the polishing machine was evaluated when the polishing was performed with a ball-scraping machine. In addition, odor evaluation is 3
A case where one person feels a bad odor is evaluated as Δ, and a case where one person feels a bad odor is evaluated as Δ, and a case where no one feels a bad odor is evaluated as ◯.
【００２５】実施例１ 次の構造式で表される化合物（Ｂ）９９．７重量部に、
アゾビスイソブチロニトリル０．１重量部、スペアミン
ト油を０．２重量部添加した単量体組成物をガラスモー
ルドと塩化ビニル製のガスケットからなるモールド型に
注入して、４０〜１００℃の温度で１５時間加熱し重合
を行った。Example 1 To 99.7 parts by weight of the compound (B) represented by the following structural formula,
A monomer composition containing 0.1 part by weight of azobisisobutyronitrile and 0.2 part by weight of spearmint oil was poured into a mold made of a glass mold and a gasket made of vinyl chloride, and the mixture was heated at 40 to 100 ° C. Polymerization was carried out by heating at temperature for 15 hours.
【００２６】得られた樹脂を玉摺研磨機で研磨し、臭気
を評価した。結果を表１に示す。The resin thus obtained was polished by a ball-sliding machine to evaluate odor. The results are shown in Table 1.
【００２７】[0027]
【化３】 実施例２〜６、比較例１〜３ 樹脂原料の組成を表１に示すとおりに変更した以外は、
実施例１と同様の方法で樹脂を得て臭気の評価を行っ
た。結果を表１に示す。[Chemical 3] Examples 2 to 6, Comparative Examples 1 to 3, except that the composition of the resin raw material was changed as shown in Table 1.
A resin was obtained in the same manner as in Example 1 and the odor was evaluated. The results are shown in Table 1.
【００２８】[0028]
【表１】 実施例７ 次の構造式で表される化合物（Ｃ）９２．０重量部、α
−メチルスチレン７．６重量部にアゾビスイソブチロニ
トリル０．２重量部、スペアミント油を０．２重量部添
加した単量体組成物をガラスモールドと塩化ビニル製の
ガスケットからなるモールド型に注入して、４０〜１０
０℃の温度で１５時間加熱し重合を行った。[Table 1] Example 7 92.0 parts by weight of compound (C) represented by the following structural formula, α
-A monomer composition obtained by adding 0.2 parts by weight of azobisisobutyronitrile and 0.2 parts by weight of spearmint oil to 7.6 parts by weight of methyl styrene is used as a mold type comprising a glass mold and a vinyl chloride gasket. Inject, 40-10
Polymerization was carried out by heating at a temperature of 0 ° C. for 15 hours.
【００２９】得られた樹脂を玉摺研磨機で研磨し、臭気
を評価した。結果を表２に示す。The resin thus obtained was ground with a ball-sliding grinder to evaluate odor. The results are shown in Table 2.
【００３０】[0030]
【化４】 実施例８〜９、比較例４〜５ 樹脂原料の組成を表に示すとおりに変更した以外は、実
施例４と同様の方法で樹脂を得て臭気の評価を行った。
結果を表２に示す。[Chemical 4] Examples 8 to 9 and Comparative Examples 4 to 5 Resins were obtained and odors were evaluated in the same manner as in Example 4, except that the composition of the resin raw material was changed as shown in the table.
The results are shown in Table 2.
【００３１】[0031]
【表２】 [Table 2]
【００３２】[0032]
【発明の効果】本発明により、臭気の少ない含硫黄樹脂
組成物を提供することができる。According to the present invention, it is possible to provide a sulfur-containing resin composition having a low odor.
フロントページの続き (51)Int.Cl.5 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｃ０８Ｌ 25:04 9166−4Ｊ 91:00） 7415−4Ｊ Continuation of the front page (51) Int.Cl. 5 Identification code Office reference number FI technical display area C08L 25:04 9166-4J 91:00) 7415-4J
Claims (8)
ることを特徴とする含硫黄樹脂組成物。1. A sulfur-containing resin composition comprising a sulfur-containing resin as a main component and a vegetable oil.
合可能な単量体を含む単量体組成物を重合して得られる
ことを特徴とする請求項１記載の含硫黄樹脂組成物。2. The sulfur-containing resin composition according to claim 1, wherein the sulfur-containing resin is obtained by polymerizing a monomer composition containing a radically polymerizable monomer having an aromatic ring.
単量体を０．５重量％以上、７０重量％以下の範囲で含
有し、かつ、植物精製油を０．０５重量％以上、３．０
重量％以下の範囲で含有する単量体組成物を重合するこ
とにより得られることを特徴とする請求項１または２記
載の含硫黄樹脂。 【化１】 （式中、Ｒ1 は、水素あるいはメチル基を示す。Ｒ
2 は、水素あるいは炭素数１〜６の飽和炭化水素を示
す。）3. A monomer having a structure represented by the following general formula (A) is contained in an amount of 0.5% by weight or more and 70% by weight or less, and a plant refined oil is 0.05% by weight or more. , 3.0
The sulfur-containing resin according to claim 1 or 2, which is obtained by polymerizing a monomer composition that is contained in an amount of not more than 5% by weight. [Chemical 1] (In the formula, R 1 represents hydrogen or a methyl group.
2 represents hydrogen or a saturated hydrocarbon having 1 to 6 carbon atoms. )
橋構造を有する樹脂であることを特徴とする請求項１、
２または３記載の含硫黄樹脂組成物。4. The sulfur-containing resin is a resin having a cross-linking structure and a refractive index of 1.55 or more.
The sulfur-containing resin composition according to 2 or 3.
黄原子を含有することを特徴とする請求項１、２、３ま
たは４記載の含硫黄樹脂組成物。5. The sulfur-containing resin composition according to claim 1, 2, 3 or 4, wherein the sulfur-containing resin contains a sulfur atom in a content of 9% by weight or more.
よびスペアミント油から選ばれることを特徴とする請求
項１、２、３、４または５記載の含硫黄樹脂組成物。6. A sulfur-containing resin composition according to claim 1, wherein the vegetable oil is selected from eucalyptus oil, peppermint oil and spearmint oil.
ルペンアルコールから選ばれる１つの化合物を０．００
５重量％以上含有することを特徴とする請求項１、２、
３、４、５または６記載の含硫黄樹脂組成物。7. The vegetable oil contains 0.001 of one compound selected from carvone, menthol and terpene alcohol.
The content of 5% by weight or more,
The sulfur-containing resin composition according to 3, 4, 5 or 6.
ことを特徴とする光学物品。8. An optical article comprising the sulfur-containing resin composition according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20234992A JPH0649366A (en) | 1992-07-29 | 1992-07-29 | Sulfur-containing resin composition and optical article made thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20234992A JPH0649366A (en) | 1992-07-29 | 1992-07-29 | Sulfur-containing resin composition and optical article made thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0649366A true JPH0649366A (en) | 1994-02-22 |
Family
ID=16456064
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20234992A Pending JPH0649366A (en) | 1992-07-29 | 1992-07-29 | Sulfur-containing resin composition and optical article made thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0649366A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7618141B2 (en) | 2004-06-21 | 2009-11-17 | Essilor International (Compagnie Generale D'optique) | Polymerizable composition containing an odor masking agent and a perfume, an optical lens and a production method |
-
1992
- 1992-07-29 JP JP20234992A patent/JPH0649366A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7618141B2 (en) | 2004-06-21 | 2009-11-17 | Essilor International (Compagnie Generale D'optique) | Polymerizable composition containing an odor masking agent and a perfume, an optical lens and a production method |
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