JP6358930B2 - ジチオレン金属錯体の無色ｉｒ吸収剤 - Google Patents

ジチオレン金属錯体の無色ｉｒ吸収剤 Download PDF

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JP6358930B2
JP6358930B2 JP2014224288A JP2014224288A JP6358930B2 JP 6358930 B2 JP6358930 B2 JP 6358930B2 JP 2014224288 A JP2014224288 A JP 2014224288A JP 2014224288 A JP2014224288 A JP 2014224288A JP 6358930 B2 JP6358930 B2 JP 6358930B2
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unsubstituted
colorless
absorber
parts
alkyl
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JP2015057492A (ja
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レーマン，ウルス
ハイツラー，ダニエル
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BASF SE
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BASF SE
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    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/04—Nickel compounds
    • C07F15/045—Nickel compounds without a metal-carbon linkage
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    • B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
    • B29B13/00—Conditioning or physical treatment of the material to be shaped
    • B29B13/02—Conditioning or physical treatment of the material to be shaped by heating
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    • B29B13/024—Hollow bodies, e.g. tubes or profiles
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
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    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07—ORGANIC CHEMISTRY
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    • B29C35/02—Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mould
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    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
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    • B29K2067/00—Use of polyesters or derivatives thereof, as moulding material
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2067/00—Use of polyesters or derivatives thereof, as moulding material
    • B29K2067/003—PET, i.e. poylethylene terephthalate
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
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    • B29K2067/00—Use of polyesters or derivatives thereof, as moulding material
    • B29K2067/006—PBT, i.e. polybutylene terephthalate
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    • B29K2069/00—Use of PC, i.e. polycarbonates or derivatives thereof, as moulding material
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
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    • B29K2077/00—Use of PA, i.e. polyamides, e.g. polyesteramides or derivatives thereof, as moulding material
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
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    • B29K2081/00—Use of polymers having sulfur, with or without nitrogen, oxygen or carbon only, in the main chain, as moulding material
    • B29K2081/04—Polysulfides, e.g. PPS, i.e. polyphenylene sulfide or derivatives thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
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    • B29K2081/00—Use of polymers having sulfur, with or without nitrogen, oxygen or carbon only, in the main chain, as moulding material
    • B29K2081/06—PSU, i.e. polysulfones; PES, i.e. polyethersulfones or derivatives thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
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    • B29K2105/00—Condition, form or state of moulded material or of the material to be shaped
    • B29K2105/0085—Copolymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
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    • B29K2105/00—Condition, form or state of moulded material or of the material to be shaped
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    • B29K2995/00—Properties of moulding materials, reinforcements, fillers, preformed parts or moulds
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    • B29K2995/00—Properties of moulding materials, reinforcements, fillers, preformed parts or moulds
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    • B29K2995/002—Coloured
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Description

本発明は、無色ＩＲ吸収剤としての特異的なジチオレン金属錯体の使用に関する。本発明は、また、新規なジチオレン金属錯体にも関する。
無色、または少なくともほとんど無色のＩＲ吸収剤は、広範囲の適用、例えば、セキュリティー印刷（銀行通帳、クレジットカード、ＩＤカード、パスポートなど）、目に見えないがＩＲ読取が可能なバーコード、プラスチックのレーザ溶接、ＩＲラジエータを用いた表面コーティングの硬化、プリントの乾燥および硬化、紙表面のトナー固定、ＰＤＰ（プラズマディスプレイパネル）用の光学フィルタ、レーザマーキング、プラスチック製プレフォームの加熱などでの重要な技術的要件を満たす。
ＩＲ吸収剤の複数の分類、例えば、キノン−ジインモニウムまたはアミニウム塩、ポリメチン（例えば、シアニン、スクアラン、クロコナイン）、フタロシアニンおよびナフタロシニン、ジチオレン、ならびに他の金属錯体が知られている。より新しい構造、例えばクオテリレンジイミドも、近年になり知られるようになった。
それらの有機物質の他にも、例えば、六ホウ化ランタン、酸化インジウムスズ（ＩＴＯ）、ナノ粒子形態の酸化アンチモンスズ（ＡＴＯ）およびコーティングされたマイカ材（Merkの「Lazerflair」）も、知られている。
その多数の公知の化合物類および構造にもかかわらず、技術的観点を満たすＩＲ吸収剤は、いまだに知られていない。特に「無色」、即ち本来の色が最小のものに関しては、他の技術的な安定性の要件（熱安定性および／または光安定性）を同時に満たす真に満足のいく解決は知られていない。例えばセキュリティー印刷用のＩＲ吸収剤は、例えば、「American Dye Source」から入手できるが、それらは事実上全てが、可視（ＶＩＳ）範囲のスペクトル（４００〜７００nm）に吸収を有する。
意外にも、それ自体が公知の複素環式ジチオレン金属錯体類が、それらの要件を満たし得ることがここに見出された。特に無色に関しては、これらの化合物は、公知のＩＲ吸収剤よりもかなり優れており、他の技術的要件、例えば、プラスチック材料（プラスチックのレーザ溶接物）に組込まれた場合の良好な光堅牢度（例えば、セキュリティー印刷）または良好な熱安定性を同時に満たす。
したがって本発明は、無色ＩＲ吸収剤としての式Ｉおよび／または式II：
Figure 0006358930
（式中、
Ｍは、Ｎｉ、Ｐｄ、Ｐｔ、Ａｕ、Ｉｒ、Ｆｅ、Ｚｎ、Ｗ、Ｃｕ、Ｍｏ、Ｉｎ、Ｍｎ、Ｃｏ、Ｍｇ、Ｖ、ＣｒまたはＴｉであり、
Ｘ１、Ｘ２およびＸ３は、それぞれ他から独立して、硫黄または酸素であり、
Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５およびＲ６は、それぞれ他から独立して、水素、ＮＲ７Ｒ８、非置換もしくは置換Ｃ１〜Ｃ１８アルキル、アルキレン鎖が酸素で中断されたＣ１〜Ｃ１８アルキル、非置換もしくは置換Ｃ１〜Ｃ１８アルケニル、非置換もしくは置換アリール、非置換もしくは置換アリールアルキル、または非置換もしくは置換へテロアリールアルキルであり、Ｒ７およびＲ８は、それぞれ他から独立して、非置換もしくは置換Ｃ１〜Ｃ１８アルキル、非置換もしくは置換アリール、非置換もしくは置換アリールアルキル、または非置換もしくは置換へテロアリールアルキルである）で示される化合物の使用、式ＩおよびIIで示される化合物に場合により添加される更なるＩＲ吸収剤に関する。
好ましいのは、金属：Ｍが、Ｎｉ、ＰｄまたはＰｔである、式Ｉで示される化合物である。（請求項２）
置換基：Ｒ１〜Ｒ６またはＲ１〜Ｒ４が、Ｃ１〜Ｃ１８アルキル基である場合、それらは、好ましくは非置換Ｃ１〜Ｃ１８アルキル基、より好ましくはＣ１〜Ｃ８アルキル基であり、直鎖および分枝鎖ならびに環状のアルキル基を含む。以下のもの、例えばプロピル、イソプロピル、ｎ−ブチル、sec−ブチル、tert−ブチル、ｎ−ヘキシル、２−エチルヘキシル、ｎ−オクチル、シクロペンチル、シクロヘキシルが挙げられる。
置換基：Ｒ１〜Ｒ６またはＲ１〜Ｒ４が、アルキレン鎖が酸素で中断されたＣ１〜Ｃ１８アルキル基である場合、それらは、好ましくは−（ＣＨ２）ｎ−［Ｏ−（ＣＨ２）ｍ］ｋ−ＯＣＨ３（ｎ＝２〜６、ｍ＝２または３、ｋ＝１〜６）である。
置換基：Ｒ１〜Ｒ６またはＲ１〜Ｒ４が、Ｃ１〜Ｃ１８アルケニル基である場合、それらは、好ましくは非置換Ｃ１〜Ｃ１８アルケニル基、より好ましくはＣ１〜Ｃ６アルケニル基である。例えば、ビニルまたはアリルであってもよい。
置換基：Ｒ１〜Ｒ６またはＲ１〜Ｒ４が、アリール基である場合、それらは、好ましくは非置換アリール基、例えば、フェニル、ナフチル、アントリルまたはフェナントリル基である。
置換基：Ｒ１〜Ｒ６またはＲ１〜Ｒ４が、アリールアルキル基である場合、それらは、好ましくは非置換アリールアルキル基、例えば、−（ＣＨ２）ｑ−フェニル（ｑ＝１〜６）、特にベンジル、エチルフェニル、プロピルフェニルである。
置換基：Ｒ１〜Ｒ６またはＲ１〜Ｒ４が、ヘテロアリールアルキル基である場合、それらは、好ましくは非置換へテロアリールアルキル基であり、それは複素芳香族環が、アルキル基に直接結合していることを示す。複素芳香族環は、例えば、イミダゾリル、ピリジル、チエニル、フリル、チアゾリル、インドリル、キノリニル、ピラゾリル、ピラジル、ピリダジルまたはピリミジニルである。
置換基：Ｒ１〜Ｒ６またはＲ１〜Ｒ４は、好ましくは非置換Ｃ１〜Ｃ１８アルキル、−（ＣＨ２）ｎ−［Ｏ−（ＣＨ２）ｍ］ｋ−ＯＣＨ３（ｎ＝２〜６、ｍ＝２または３、ｋ＝１〜６）、非置換Ｃ１〜Ｃ１８アルケニル、非置換アリールアルキルまたは−Ｎ（Ｃ１〜Ｃ６アルキル）２である。
置換基：Ｒ７およびＲ８は、好ましくはＣ１〜Ｃ６アルキル基である。
好ましい実施形態において、
Ｍが、Ｎｉ、Ｐｄ、Ｐｔであり、
Ｘ１、Ｘ２およびＸ３が、それぞれ他から独立して、硫黄または酸素であり、
Ｒ１、Ｒ２、Ｒ３、Ｒ４が、それぞれ他から独立して、−Ｎ（Ｃ１〜Ｃ６アルキル）２、非置換Ｃ１〜Ｃ８アルキル、−（ＣＨ２）ｎ−［Ｏ−（ＣＨ２）ｍ］ｋ−ＯＣＨ３（ｎ＝２〜６、ｍ＝２または３、ｋ＝１〜６）、ビニルまたはアリル、−（ＣＨ２）ｑ−フェニル（ｑ＝１〜６）である、
式Ｉで示される化合物が、無色ＩＲ吸収剤として用いられる。（請求項３）
特に該当するのは、構造：Ｉａ〜Ｉｈである。
Figure 0006358930
（請求項４）
無色ＩＲ吸収剤は、ＩＲ吸収剤に残存する不可視性により、全ての適用分野で用いることができる。以下の使用、例えば：セキュリティー印刷（銀行通帳、クレジットカード、ＩＤカード、パスポートなど）、目に見えないがＩＲ読取が可能なバーコード、プラスチックのレーザ溶接、ＩＲラジエータを用いた表面コーティングの硬化、プリントの乾燥および硬化、紙表面のトナー固定、レーザマーキング（プラスチック材料、紙、木など）およびプラスチック製プレフォームの加熱などが挙げられる。（請求項５）
特に適した適用分野は、セキュリティー印刷およびプラスチック材料のレーザ溶接における式Ｉおよび／またはIIで示される化合物の使用である。（請求項６）
別の実施形態において、式ＩおよびIIで示される化合物は、セキュリティー印刷およびバーコードの印刷で用いられる。（請求項７）
式ＩおよびIIで示されるＩＲ吸収剤は、更なる公知のＩＲ吸収剤との混合物、特にポリメチン（シアニン、スクアランおよびクロコナイン）との混合物の形態であってもよい。そのようなＩＲ吸収剤混合物は、特にセキュリティー印刷に適している。（請求項８）
好ましいポリメチンの例を、以下の表に列挙する：
Figure 0006358930
Figure 0006358930
ＩＲ吸収剤は、選択された適用に応じて、１０ppm〜１０％、好ましくは１００ppm〜２％の濃度で用いられる。
レーザ溶接は、好ましくは１０６４nmのＮＤ：ＹＡＧレーザを用いて、または９８０nmもしくは９４０nmのダイオードレーザを用いて実施され、ＩＲ吸収剤の濃度は、例えば５〜５００ppm、好ましくは１０〜１００ppmである。
レーザ溶接では、プラスチック成分が、互いに溶接される。本発明のジチオレンは、特に透明プラスチック材料、例えば、ポリプロピレン、ポリビニルブチラール、ポリアミド、ポリカーボナート、ポリカーボナート−ポリエチレンテレフタレート混合物、ポリカーボナート−ポリブチレンテレフタレート混合物、ポリカーボナート−アクリロニトリル−スチレン−アクリロニトリル共重合体混合物、ポリカーボナート−アクリロニトリル−ブタジエン−スチレン共重合体混合物、ポリメチルメタクリレート−アクリロニトリル−ブタジエン−スチレン共重合体混合物（ＭＡＢＳ）、ポリエチレンテレフタレート、ポリブチレンテレフタレート、ポリメチルメタクリレート、ポリブチルアクリレート、ポリメチルメタクリレート−ポリ二フッ化ビニリデン混合物、アクリロニトリル−ブタジエン−スチレン共重合体（ＡＢＳ）、スチレン−アクリロニトリル共重合体（ＳＡＮ）およびポリフェニレンスルホンならびにそれらの混合物を溶接するのに適している。
溶接に特に有利なのは、２種の同様に透明のプラスチック加工物、例えば、無色−透明／無色−透明または有色−透明／有色−透明の使用である。
セキュリティー印刷において、ＩＲ吸収剤は、印刷インクに添加される。適切な印刷インクは、インクジェット印刷、フレキソ印刷、スクリーン印刷、凹版印刷、オフセット印刷、レーザ印刷または凸版印刷用および電子写真に使用される顔料または染色を基にした水性、油性または溶媒性の印刷インクである。
本発明は、
Ｍが、Ｎｉ、Ｐｄ、Ｐｔ、Ａｕ、Ｉｒ、Ｆｅ、Ｚｎ、Ｗ、Ｃｕ、Ｍｏ、Ｉｎ、Ｍｎ、Ｃｏ、Ｍｇ、Ｖ、ＣｒまたはＴｉであり、
Ｘ１が、酸素であり、Ｘ２およびＸ３が、酸素または硫黄であり、
Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５およびＲ６が、それぞれ他から独立して、水素、ＮＲ７Ｒ８、非置換もしくは置換Ｃ１〜Ｃ１８アルキル、アルキレン鎖が酸素で中断されたＣ１〜Ｃ１８アルキル、非置換もしくは置換Ｃ１〜Ｃ１８アルケニル、非置換もしくは置換アリール、非置換もしくは置換アリールアルキル、または非置換もしくは置換へテロアリールアルキルであり、Ｒ７およびＲ８が、それぞれ他から独立して、非置換もしくは置換Ｃ１〜Ｃ１８アルキル、非置換もしくは置換アリール、非置換もしくは置換アリールアルキル、または非置換もしくは置換へテロアリールアルキルである、
式ＩおよびIIで示される新規なジチオレン化合物にも関する。（請求項９）
それらの化合物は、対応する硫黄成分（Ｘ１、Ｘ２、Ｘ３＝Ｓ）から、適切な溶媒での酸化により、または例に記載されたとおり、得られる。
以下の化合物が、例として挙げられる。
Figure 0006358930
本発明は、
Ｍが、Ｎｉ、Ｐｄ、Ｐｔ、Ａｕ、Ｉｒ、Ｆｅ、Ｚｎ、Ｗ、Ｃｕ、Ｍｏ、Ｉｎ、Ｍｎ、Ｃｏ、Ｍｇ、Ｖ、ＣｒまたはＴｉであり、
Ｘ１、Ｘ２およびＸ３が、それぞれ他から独立して、硫黄または酸素であり、
Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５およびＲ６が、ＮＲ７Ｒ８（式中、Ｒ７およびＲ８は、それぞれ他から独立して、非置換もしくは置換Ｃ１〜Ｃ１８アルキル、非置換もしくは置換アリール、非置換もしくは置換アリールアルキル、または非置換もしくは置換へテロアリールアルキルである）である、
式ＩおよびIIで示される新規なジチオレン化合物にも関する。（請求項１０）
好ましい−ＮＲ７Ｒ８は、−Ｎ（Ｃ１〜Ｃ６アルキル）２である。
以下の化合物：ＩｃおよびＩｄが、例として挙げられる。
Figure 0006358930
新規なジチオレン化合物は、既知のジチオレン化合物のように、セキュリティー印刷（銀行通帳、クレジットカード、ＩＤカード、パスポートなど）、目に見えないがＩＲ読取が可能なバーコード、プラスチックのレーザ溶接、ＩＲラジエータを用いた表面コーティングの硬化、プリントの硬化および乾燥、紙表面のトナー固定、レーザマーキング（プラスチック、紙、木など）およびプラスチック製プレフォームの加熱などでの使用に適している。
加えて、式ＩおよびIIで示される新規なジチオレン化合物は、プラズマディスプレイパネル（ＰＤＰ）用の光学フィルタとしての使用に適している。この適用では、１０００nm未満、特に約９００nmの吸収が、特に該当する。
実施例
実施例１
Figure 0006358930
の製造
その化合物は、J. Chem. Soc., Dalton Trans 1998, 3731-3736から公知であり、その製造は、そこに記載されている。
１，３−ジイソプロピル−４，５−ジオキソイミダゾリン−２−チオンを、還流条件下、クロロベンゼン中で金属ニッケルおよびLawesson試薬：
Figure 0006358930
と反応させた。
吸収最大（クロロホルム）：１００１nm（７９０００）
実施例２
Figure 0006358930
の製造
二塩化白金およびLawesson試薬を用いて、実施例１と同様に反応を実施した。
吸収最大（クロロホルム）：１０００nm（１１３０００）
実施例３ａ
Figure 0006358930
の製造
Ｎ，Ｎ−ジメチルヒドラジン１２．２６部を、撹拌しながら、ジクロロエタン２５０部中の二硫化炭素７．６５部の溶液に室温で添加した。その後、温度を４０℃に上昇させ、その温度で１６時間撹拌を実施して、反応を完了させた。続いて１時間の間、温度を８０℃に上昇させた。その後、更にジクロロエタン７５０部を添加して、塩化オキサリル１３．８８部（少量のジクロロエタンに溶解）を、９０分間かけて滴下した。その後、反応混合物を加熱還流して２時間還流を持続し、その後それを濃縮して黄色結晶をろ別し、少量のジクロロエタンで洗浄した。乾燥後、先に示した構造を有する生成物１４部を得た。
実施例３ｂ
Figure 0006358930
の製造
二塩化白金０．３３３部を、トルエン５０部中の実施例３ａの生成物０．５４１部およびLawesson試薬１．０８５部の溶液に添加した。反応混合物を１１０℃で９０分間保持して高温のままろ過し、ｎ−ヘキサン５００部を添加して冷却後にろ過した。得られた沈殿をろ別して乾燥させ、生成物０．５部を得た（吸収最大９９４nm）。
実施例４
手順は、用いた金属がモリブデンであること以外はこれまでの実施例と同様であり、こうして対応する１：３モリブデン錯体：
Figure 0006358930
を得た。
実施例５
Figure 0006358930
の製造
実施例２の化合部を、還流温度でジクロロメタン中の大気中の酸素で酸化して、対応するオキソ化合物を形成した。吸収最大は、９６８nmで見出された。
実施例６ａ
Figure 0006358930
の製造
１，３−ジ−ｎ−プロピル尿素２９．１４部を、４０℃のトルエン３００部に溶解した。その撹拌溶液に塩化オキサリル２７．１８部を、８０℃で４０分間かけて添加した。１００℃で更に１時間撹拌した後、溶液を６０℃で蒸発し、乾固して、生成物３６．８部を得た。
実施例６ｂ
Figure 0006358930
の製造
実施例６ａの生成物１．５９部、二塩化白金１．０６部およびLawesson試薬３．４７部を、トルエン１００部中、窒素下で１１０℃に加熱した。４５分の反応時間後に、暗色溶液を−１０℃に冷却し、沈殿をろ別して、エタノールおよび少量のアセトンで洗浄した。精製のために、粗生成物をジクロロメタンに溶解し、メタノールを添加して緩やかに沈殿させた。暗青色結晶をろ過により回収した。生成物の吸収最大は、９００nmで見出された（クロロホルム）。
実施例７
Figure 0006358930
の製造
実施例６ｂと同様に進行させ、塩化白金の代わりに塩化パラジウムを用いると、吸収最大９２１nmの対応するパラジウム錯体が得られた。
実施例８
Figure 0006358930
の製造
実施例６ｂと同様に進行させ、塩化白金の代わりに金属ニッケルを用いると、吸収最大８９１nmの対応するニッケル錯体が得られた。
実施例９〜２４
実施例９〜２４の化合物（下記の表に示す構造）を、実施例１〜８に記載されたものと同様の手順により得た。
Figure 0006358930
Figure 0006358930
適用例
実施例Ａ１（セキュリティー印刷）
塩化ビニル１１．９部、酢酸ビニル２．１部、エトキシプロパノール１０部、メチルエチルケトン７５．５部および実施例１の生成物０．５部を、ガラスビーズ１５０ｇと共にSkandexミキサーで３０分間振とうした。得られた印刷インクをドクターブレードを用いてコントラスト紙に塗布した（湿った時の膜厚：６μm）。プリントは、見た目には無色であるが、ＩＲ観察装置（IR-viewing device）（カットオフフィルター７１５nm）を用いると、ＩＲ範囲では明瞭に見ることができた。光堅牢度が、優れていた。
実施例Ａ２（セキュリティー印刷）
実施例Ａ１に示されたとおり進行させ、実施例２のＩＲ吸収剤を用いると、優れた光堅牢度を有し、ＩＲ観察装置を用いると赤外範囲では明瞭に見られる無色プリントが、同様に得られた。
実施例Ａ３（プラスチック材料のレーザ溶接）
射出成形機を用いて、実施例１のＩＲ吸収剤を、２mmの厚さ（濃度：１００ppm）を有するポリカーボナートディスクに組込んだ。Ｎｄ：ＹＡＧレーザを用いて、得られた事実上無色のディスクを、出力３０ワットおよび進行速度（a rate of advance）２０mm/分で、ＩＲ吸収剤を含まない純粋な第２の１mm厚ポリカーボナートディスクに溶接した。得られた溶接物は優れた結合、不変の透明性、溶融侵入（melt irruptions）がないことおよび気泡のないことを特徴とする。機械的負荷を重くした時に、ディスクの破壊が溶接シームに生じなかった。
実施例Ａ４（プラスチック材料のレーザ溶接）
実施例Ａ３に示されたとおり進行させ、実施例２のＩＲ吸収剤を用いると、優れた溶接性を有する事実上無色のポリカーボナートディスクが同様に得られた。得られた溶接物は、不変の透明性を有し、その溶接物は、溶融侵入または気泡が残存せず、溶接物の強度が優れていた。
実施例Ａ５およびＡ６
実施例Ａ３およびＡ４に示されたとおり進行させ、Ｎｄ：ＹＡＧレーザ（１０６４nm）を用いる代わりに発光波長９８０nmを有するダイオードレーザを用いると、実施例Ａ３およびＡ４に記載されたものと同様の良好な結果が得られた。
実施例Ａ７およびＡ８
実施例Ａ３およびＡ４に示されたとおり進行させ、Ｎｄ：ＹＡＧレーザ（１０６４nm）を用いる代わりに発光波長９４０nmを有するダイオードレーザを用いると、同等に良好な溶接物が、レーザ出力８０ワットで得られた。
実施例Ａ９
実施例Ａ３に示されたとおり進行させ、１．５mmの厚さを有するポリプロピレンディスクを用いると、得られた溶接物は、同様に非常に良好であった。

Claims (1)

  1. セキュリティー印刷またはプラスチックのレーザ溶接における、熱安定性および／または光安定性を有する無色のための無色ＩＲ吸収剤としての式Ｉａ：
    Figure 0006358930
     で示される化合物の使用。
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