JP6351189B2 - マーキングされた塗料組成物およびその認証法 - Google Patents
マーキングされた塗料組成物およびその認証法 Download PDFInfo
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- JP6351189B2 JP6351189B2 JP2016253073A JP2016253073A JP6351189B2 JP 6351189 B2 JP6351189 B2 JP 6351189B2 JP 2016253073 A JP2016253073 A JP 2016253073A JP 2016253073 A JP2016253073 A JP 2016253073A JP 6351189 B2 JP6351189 B2 JP 6351189B2
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- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- CCEFMUBVSUDRLG-UHFFFAOYSA-N limonene-1,2-epoxide Chemical compound C1C(C(=C)C)CCC2(C)OC21 CCEFMUBVSUDRLG-UHFFFAOYSA-N 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- KOARAHKGQSHYGJ-UHFFFAOYSA-N methyl 2-methylprop-2-enoate;oxiran-2-ylmethyl prop-2-enoate Chemical compound COC(=O)C(C)=C.C=CC(=O)OCC1CO1 KOARAHKGQSHYGJ-UHFFFAOYSA-N 0.000 description 1
- 239000004200 microcrystalline wax Substances 0.000 description 1
- 235000019808 microcrystalline wax Nutrition 0.000 description 1
- 235000021243 milk fat Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002086 nanomaterial Substances 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000002921 oxetanes Chemical class 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- YPNZYYWORCABPU-UHFFFAOYSA-N oxiran-2-ylmethyl 2-methylprop-2-enoate;styrene Chemical compound C=CC1=CC=CC=C1.CC(=C)C(=O)OCC1CO1 YPNZYYWORCABPU-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-O oxonium Chemical compound [OH3+] XLYOFNOQVPJJNP-UHFFFAOYSA-O 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000003847 radiation curing Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000550 scanning electron microscopy energy dispersive X-ray spectroscopy Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 239000010698 whale oil Substances 0.000 description 1
- INRGAWUQFOBNKL-UHFFFAOYSA-N {4-[(Vinyloxy)methyl]cyclohexyl}methanol Chemical compound OCC1CCC(COC=C)CC1 INRGAWUQFOBNKL-UHFFFAOYSA-N 0.000 description 1
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Description
本発明は、ワニス、インクおよびペンキなどの塗料組成物の認証分野に関し、銀行券または他の貴重な文書などの基板に塗布される場合のこのような塗料組成物の認証分野で特に有用である。本発明は特に、認証を可能にするようなマーカー(タガント)でマーキングされる、マーキングされた塗料組成物、例えば、インク、およびこのようなマーキングされた塗料組成物を認証する方法に関する。
製品の認証、すなわち、製品の出所の識別および/または検証は、全ての範囲の異なる産業および用途で重要な役割を果たす。製品の識別および認証を可能にするために、いわゆるタガント、すなわち、特異的マーカーなどの認証可能な化学成分を製品に添加することが当技術分野で知られている。
第1に、本発明は、
(i)オリゴマーまたはポリマー部分(2a)と、共有結合性の連結基(4)を通して前記部分(2a)に結合した少なくとも1つのマーカー部分(3a)とを含むマーキングされた非抽出性成分(marked non−extractable component)(5);または
(ii)オリゴマーまたはポリマー成分(2)ならびにマーカー部分(3a)および連結基(4)を形成して組成物(1)を硬化すると前記成分(5)を得ることができる基を含む少なくとも1つのマーカー(3)
を含むマーキングされた塗料組成物(1)であって、
前記組成物(1)に基づくマーカー部分(3a)の量は0.001〜1重量%である、組成物(1)を提供する。
(S100)基板から組成物(1)の試料を回収して回収試料を得るステップと;
(S200)回収試料を熱誘導化学断片化条件に供して少なくとも1つのマーカー部分(3a)とオリゴマーまたはポリマー部分(2a)に共有結合した共有結合性の連結基(4)とで形成される単位に由来する化学断片化生成物を得るステップと;
(S300)化学試料断片化の化学生成物を分析するステップと;
(S400)これらの化学生成物を1つまたは複数の基準物質と比較することにより、組成物(1)を認証するステップと
を含む方法を提供する。
以下では、本発明の種々の実施形態が記載され、ここでは代表的に、塗料組成物がインクとなるよう選択される。しかしながら、これは、これらの実施形態の開示をインクまたはその認証にのみ限定することを決して意図していない。むしろ、第1の態様に係る任意の他のマーキングされた塗料組成物も、以下に記載される全ての実施形態を含めて、代わりにおよび制限なく使用され得る。
(式中、
Rはそれぞれ独立に、H、D(重水素)、T(トリチウム)、C1〜18−アルキル、C1〜18−アルケニル、C1〜18−アルキニル、C3〜12−シクロアルキル、C3〜12−シクロアルケニル、C1〜12−ヘテロシクロアルキル、C7〜12−アラルキル、Hal、CH2Hal、CHHal2、CHal3、CN、CXXR2、OR2、SR2、NR2R3、−N=N−Ar、=N−NR2Ar、SiR4R5R6、X−P(X)(XR2)(XR3)、P(X)(XR2)(XR3)、SOR2、SO2R2、Hとは異なる1〜3個の基R2で置換されたフェニル、または環内にO、S、N、NHおよびN(C1〜18−アルキル)の少なくとも1つを有する5〜8員複素芳香族基から選択される;
または2個もしくは3個の炭素原子により分離されている2個の隣接する基Rは
から選択される部分を一緒に形成し;
R1はそれぞれ独立に、H、D(重水素)、T(トリチウム)、C1〜18−アルキル、Hal、CH2Hal、CHHal2、CHal3、CN、CXXR2、OR2、SR2、NR2R3、SiR4R5R6、P(X)(XR2)(XR3)、X−P(X)(XR2)(XR3)、SOR2、SO2R2から選択される;
または式(VIa)〜(VId)中、2個のジェミナル基R1は、それらが結合している炭素原子と共に、それぞれ独立に、C=O、C=NR2またはC=Sであり;
R2、R3はそれぞれ独立に、H、D(重水素)、C1〜18−アルキル、C1〜18−アルケニル、C1〜18−アルキニル、C3〜12−シクロアルキル、C3〜12−シクロアルケニル、C1〜12−ヘテロシクロアルキル、C7〜12−アラルキル、CH2Hal、CHHal2、CHal3、SiR4R5R6、フェニルならびに環内にO、S、N、NHおよびN(C1〜18−アルキル)の少なくとも1つを有する5〜8員複素芳香族基から選択され;
R4、R5およびR6はそれぞれ独立に、C1〜18−アルキル、O(C1〜18−アルキル)およびN(C1〜18−アルキル)から選択され;
HalはF、Cl、BrまたはIであり;
Arは芳香族基であり;
XはO、NH、N(C1〜18−アルキル)またはSであり;
m、n、pはそれぞれ、0〜20の範囲の数であり;
(i)少なくとも1個、好ましくは1〜4個、より好ましくは1または2個の基Rは、マーカー部分(3a)をオリゴマーまたはポリマー部分(2a)と結合する共有結合性の連結基(4)であり、それぞれ独立に結合、(3a)−COO−(2a)、(3a)−CONR2−(2a)、(3a)−O−CO−O−(2a)、(3a)−O−CO−NR2−(2a)、(3a)−NH−CO−NR2−(2a)、(3a)−O−(2a)、(3a)−S−(2a)または(3a)−NR2−(2a)から選択され、(3a)および(2a)はそれぞれ、マーカー部分(3a)およびオリゴマーまたはポリマー部分(2a)の位置を示し;
(ii)共有結合性の連結基(4)ではない少なくとも1つのRまたはR2はHではない)。
Rはそれぞれ独立に、H、D(重水素)、T(トリチウム)、C1〜18−アルキル、C3〜12−シクロアルキル、C3〜12−シクロアルケニル、C1〜12−ヘテロシクロアルキル、Hal、CHHal2、CHal3、CXX−R2、OR2、SR2、NR2R3、−N=N−Ar、=N−NR2Ar、SiR4R5R6、X−P(X)(XR2)(XR3)、P(X)(XR2)(XR3)、SOR2およびSO2R2から選択され;R2はC4〜18−アルキルである;
または2個もしくは3個の炭素原子により分離されている2個の隣接する基Rは式[IV]、[Va]、[Vc]、[VIa]または[VIc]から選択される部分を一緒に形成し、
R1はそれぞれ独立に、H、C1〜18−アルキル、Hal、CH2Hal、CHHal2、CHal3、CXXR2、OR2、SR2、NR2R3、SOR2およびSO2R2から選択され;R2はC4〜18−アルキルであり;
式(VIa)中、2個のジェミナル基R1は、結合している炭素原子と共に、それぞれ独立に、さらにC=O、C=NR2またはC=Sであってもよく;
共有結合性の連結基(4)は、結合、(3a)−COO−(2a)、(3a)−CONR2−(2a)、(3a)−O−CO−NR2−(2a)、(3a)−NH−CO−NR2−(2a)、(3a)−O−(2a)、(3a)−S−(2a)および(3a)−NR2−(2a)から選択される。
Rはそれぞれ独立に、H、D(重水素)、C1〜18−アルキル、C3〜12−シクロアルキル、C1〜12−ヘテロシクロアルキル、Hal、CHHal2、CHal3、CXX−R2、OR2、SR2、NR2R3、P(X)(XR2)(XR3)、SOR2およびSO2R2から選択され;R2はC4〜18−アルキルである;
または2個もしくは3個の炭素原子により分離されている2個の隣接する基Rは式[IV]、[Va]、[Vc]、[VIa]または[VIc]から選択される部分を一緒に形成し、
R1はそれぞれ独立に、H、C1〜18−アルキル、CHal3、CXXR2、OR2、SR2、NR2R3、SOR2およびSO2R2から選択され;R2はC4〜18−アルキルであり;
式(VIa)中、2個のジェミナル基R1は、結合している炭素原子と共に、それぞれ独立に、さらにC=O、C=NR2またはC=Sであってもよく;
共有結合性の連結基(4)は、結合、(3a)−COO−(2a)、(3a)−CONR2−(2a)、(3a)−O−CO−NR2−(2a)、(3a)−NH−CO−NR2−(2a)、(3a)−O−(2a)、(3a)−S−(2a)および(3a)−NR2−(2a)から選択される。
(A1)水、メタノール、エタノール、酢酸エチル、アセトンおよびトルエンの各々、より好ましくは
(A2)水、メタノール、エタノール、酢酸エチル、ジメチルホルムアミド、アセトン、クロロホルム、トリクロロエチレン、テレピン、キシレン、トルエンおよびホワイトスピリット(米国で「ミネラルスピリット」としても知られている石油蒸留物)の各々、
さらにより好ましくは
(A3)以下の溶媒:
水、
水性(1mol/l)次亜塩素酸ナトリウム溶液、
メタノール、
エタノール、
酢酸エチル、
ジメチルホルムアミド、
アセトン、
クロロホルム、
トリクロロエチレン、
パークロロエチレン、
テレピン、
キシレン、
トルエン、
ホワイトスピリット(米国で「ミネラルスピリット」としても知られている石油蒸留物)、
ポリエチレングリコール、
水性(1mol/l)酢酸、
水性(1mol/l)塩酸、
水性(1mol/l)硫酸、
水性(1mol/l)水酸化ナトリウムおよび
水性(1mol/l)アンモニア
の各々に非抽出性である。
(S100)基板から組成物(1)の試料を回収して回収試料を得るステップと;
(S200)回収試料を熱誘導化学断片化条件に供して少なくとも1つのマーカー部分(3a)とオリゴマーまたはポリマー部分(2a)に共有結合した共有結合性の連結基(4)とで形成される単位に由来する化学断片化生成物を得るステップと;
(S300)化学試料断片化の化学生成物を分析するステップと;
(S400)これらの化学生成物を1つまたは複数の基準物質と比較することにより、組成物(1)を認証するステップと
を含む方法を提供する。
i)マーキングされた塗料組成物、例えば、染色インクを保有する基板の試験試料を室温(25℃)で24時間、選択された溶媒に浸漬(および放置)する。使用する溶媒の量は、塗料に含有されるマーキングされた塗料組成物成分(5)100μg当たり1mlとする。次いで、試験試料を、試験に使用したのと同じ量の有機溶媒または同じ量の水で洗浄し、水または希釈水溶液を使用した場合には、引き続いて乾燥させる。
(B1)水、メタノール、エタノール、酢酸エチル、アセトンおよびトルエンの各々、より好ましくは
(B2)水、メタノール、エタノール、酢酸エチル、ジメチルホルムアミド、アセトン、クロロホルム、トリクロロエチレン、テレピン、キシレン、トルエンおよびホワイトスピリット(米国で「ミネラルスピリット」としても知られている石油蒸留物)の各々、
さらにより好ましくは
(B3)以下の溶媒:
水、
水性(1mol/l)次亜塩素酸ナトリウム溶液、
メタノール、
エタノール、
酢酸エチル、
ジメチルホルムアミド、
アセトン、
クロロホルム、
トリクロロエチレン、
パークロロエチレン、
テレピン、
キシレン、
トルエン、
ホワイトスピリット(米国で「ミネラルスピリット」としても知られている石油蒸留物)、
ポリエチレングリコール、
水性(1mol/l)酢酸、
水性(1mol/l)塩酸、
水性(1mol/l)硫酸、
水性(1mol/l)水酸化ナトリウムおよび
水性(1mol/l)アンモニア
の各々に非抽出性である。
全ての分析を、GC−MS装置の下限検出限界が許す最小量のマーキングされたインクで行った。
例えば、芸術的または考古学的試料の分析に使用されるようなミクロ破壊(micro−destructive)技術を使用した。小型外科用メス刃を用いた穏やかなマイクロサンプリングが、切除領域が肉眼で識別可能でないようにインク試料を切除することを可能にした。この技術により得られたインク断片のサイズを、タガントの検出に必要な量に相当する約100μg範囲の物質に含めた。試料をさらなる処理なしにPY−GC−MS装置の熱分解装置に直接入れた。
インク試料の分析のために使用する装置は、熱分解モジュール、オートサンプラAS−1020Eを有するFrontier Lab製のDouble−Shot Pyrolyser PY−2020iDを備え、MS分光計Agilent5973と連結したEA−CG−02、GC Agilent 6890シリーズとした。熱分解装置は、Frontier Lab製のDouble−Shot PyrolyserシステムPY−2020iDとした。
タガントと混合した凹版ワニスの調製(タガントは混合しているが、共有結合はしていない)
タガントの共有結合を証明するために、タガントが混合しているが、他のワニス成分と反応はしていない比較例を調製した。
1.脂肪酸(63部)、グリセリン(12部)、ポリオール(11部)および無水フタル酸(13.6部)の混合物を不活性雰囲気下で加熱して5時間還流した。混合物を真空下で蒸発させて水を除去し、透明なワニスV−1を得た。
2.ジ−イソシアネート(9部)を透明なワニスV−1のN−ウンデカン中混合物(48部)に添加した。ジルコニウム触媒(0.1部)を添加し、混合物を125℃で2時間加熱して淡黄色油(V−1A)を得た。
4−フルオロ無水フタル酸(FPA)(タガント)による凹版ワニスV−4のタグ付け
タグ付きインク成分の合成:
1.脂肪酸(63部)(V1と同じ脂肪酸)、グリセリン(12部)、ポリオール(11部)(V1と同じポリオール)、無水フタル酸(13部)および4−フルオロ無水フタル酸FPA(0.6部)の混合物を不活性雰囲気下で加熱して5時間還流した。混合物を真空下で蒸発させて水を除去し、透明なワニスV−3を得た。
2.ジ−イソシアネート(9部)(V1と同じジ−イソシアネート)をN−ウンデカン中の透明なワニスV−3(48部)に添加した。ジルコニウム触媒(0.1部)を添加し、混合物を125℃で2時間加熱して淡黄色ワニスV−4を得た(V−4はタグ付きインク成分であり、タガントが共有結合している)。
ワニスV−2およびV−4をGPCにより分析した。各ワニスを2つの分画、F1およびF2に分割した。GPCポリスチレン標準を使用した通常の方法に基づいて、分画の平均分子量を計算した。
分割ワニスV2およびV−4をPY−GC−MSで分析した。各ワニスV−2およびV−4の分画F1およびF2を熱分解し、GC−MSで分析した。タガントFPAの特徴的ピークの存在を種々の分画のMSスペクトログラムで確認した。
インクI−1およびI−2を当技術分野で既知の凹版印刷により基板(銀行券)に印刷した。
各印刷インクI−1およびI−2の試料を外科用メスで掻きむしり、PY−GC−MSにより分析した。タガントFPAの特徴的ピークの存在をMS−スペクトログラムで確認した。タガントの特徴的ピークは、インク試料I−1に見られたが、インクI−2には見られなかった。
Claims (14)
- マーキングされた非抽出性成分(5)を含む組成物(1)が塗布された基材を含む物品中に存在する組成物(1)を認証する方法であって、
前記マーキングされた非抽出性成分(5)は、オリゴマーまたはポリマー部分(2a)と、共有結合性の連結基又は共有結合(4)を介して前記部分(2a)に結合した少なくとも1つのマーカー部分(3a)とを含み、
前記組成物(1)に基づく前記マーカー部分(3a)の量は0.001〜1重量%であり、
前記方法は、
(a)前記基材から前記組成物(1)の試料を物理的に回収して回収試料を得るステップと;
(b)前記回収試料を熱分解処理に供して前記少なくとも1つのマーカー部分(3a)と前記オリゴマーまたはポリマー部分(2a)に共有結合した前記共有結合性の連結基(4)とで形成される単位に由来する熱分解断片化生成物を得るステップと;
(c)熱分解断片化生成物を質量分析計により分析するステップと;
(d)これらの熱分解断片化生成物の分析結果を1つまたは複数の基準物質と比較することにより、前記組成物(1)を認証するステップと
を含む方法。 - 前記マーカー部分(3a)および前記共有結合性の連結基(4)を含む部分が
(式中、
Rはそれぞれ独立に、H、D(重水素)、T(トリチウム)、C1〜18−アルキル、C1〜18−アルケニル、C1〜18−アルキニル、C3〜12−シクロアルキル、C3〜12−シクロアルケニル、C1〜12−ヘテロシクロアルキル、C7〜12−アラルキル、Hal、CH2Hal、CHHal2、CHal3、CN、CXXR2、OR2、SR2、NR2R3、−N=N−Ar、=N−NR2Ar、SiR4R5R6、X−P(X)(XR2)(XR3)、P(X)(XR2)(XR3)、SOR2、SO2R2、Hとは異なる1〜3個の基R2で置換されたフェニル、または環内にO、S、N、NHおよびN(C1〜18−アルキル)の少なくとも1つを有する5〜8員複素芳香族基から選択される;
または2個もしくは3個の炭素原子により分離されている2個の基Rは
から選択される部分を一緒に形成し;
R1はそれぞれ独立に、H、D(重水素)、T(トリチウム)、C1〜18−アルキル、Hal、CH2Hal、CHHal2、CHal3、CN、CXXR2、OR2、SR2、NR2R3、SiR4R5R6、P(X)(XR2)(XR3)、X−P(X)(XR2)(XR3)、SOR2、SO2R2から選択される;
または式(VIa)〜(VId)中、2個のジェミナル基R1は、それらが結合している炭素原子と共に、それぞれ独立に、C=O、C=NR2またはC=Sであり;
R2、R3はそれぞれ独立に、H、D(重水素)、C1〜18−アルキル、C1〜18−アルケニル、C1〜18−アルキニル、C3〜12−シクロアルキル、C3〜12−シクロアルケニル、C1〜12−ヘテロシクロアルキル、C7〜12−アラルキル、CH2Hal、CHHal2、CHal3、SiR4R5R6、フェニルならびに環内にO、S、N、NHおよびN(C1〜18−アルキル)の少なくとも1つを有する5〜8員複素芳香族基から選択され;
R4、R5およびR6はそれぞれ独立に、C1〜18−アルキル、O(C1〜18−アルキル)およびN(C1〜18−アルキル)から選択され;
HalはF、Cl、BrまたはIであり;
Arは芳香族基であり;
XはO、NH、N(C1〜18−アルキル)またはSであり;
m、n、pはそれぞれ、0〜20の範囲の数であり;
(i)少なくとも1個の基Rは、前記マーカー部分(3a)を前記オリゴマーまたはポリマー部分(2a)と結合する共有結合性の連結基又は共有結合(4)であり、それぞれ独立に共有結合、(3a)−COO−(2a)、(3a)−CONR2−(2a)、(3a)−O−CO−O−(2a)、(3a)−O−CO−NR2−(2a)、(3a)−NH−CO−NR2−(2a)、(3a)−O−(2a)、(3a)−S−(2a)または(3a)−NR2−(2a)から選択され、(3a)および(2a)はそれぞれ、前記マーカー部分(3a)および前記オリゴマーまたはポリマー部分(2a)の位置を示し;
(ii)共有結合性の連結基(4)ではない少なくとも1つのRまたはR2はHではない)
から選択される、請求項1に記載の方法。 - 前記組成物(1)が、
不飽和脂肪酸残基、飽和脂肪酸残基もしくはこれらの組合せを含むオリゴマーもしくはポリマー、または、アルキド樹脂、ビニルポリマー、ポリウレタン樹脂、高分岐樹脂、ロジン変性マレイン酸樹脂、テルペン樹脂、ニトロセルロース樹脂、ポリオレフィン、ポリアミド、アクリル樹脂およびこれらの混合物から選択される樹脂、及び酸化乾燥剤を含む酸化乾燥組成物、
ポリエステル樹脂、ポリエーテル樹脂、塩化ビニルポリマーおよび塩化ビニル系共重合体、ニトロセルロース樹脂、セルロールアセトブチレートまたはアセトプロピオネート樹脂、マレイン酸樹脂、ポリアミド、ポリオレフィン、ポリウレタン樹脂、官能化ポリウレタン樹脂、ポリウレタンアルキド樹脂、ポリウレタン−(メタ)アクリレート樹脂、ウレタン−(メタ)アクリル樹脂、スチレン(メタ)アクリレート樹脂あるいはこれらの混合物から選ばれる樹脂を含む熱乾燥組成物、
オリゴマー(メタ)アクリレート、ビニルエーテル、プロペニルエーテル、環状エーテル、ラクトン、環状チオエーテル、ビニルおよびプロペニルチオエーテル、ヒドロキシル含有化合物、ならびにこれらの混合物からなる群から選択される1種または複数の化合物から調製されるバインダーを含むUV−可視光硬化性組成物、あるいは
これらの組合せ
である、請求項1または2に記載の方法。 - 1つのマーカー部分(3a)が存在する、請求項1〜3のいずれか一項に記載の方法。
- 2つ以上の異なるマーカー部分(3a)が存在する、請求項1〜3のいずれか一項に記載の方法。
- 前記部分(2a)が樹脂成分またはワニス成分である、請求項1〜5のいずれか一項に記載の方法。
- 前記組成物が顔料、染料、発光化合物、油、樹脂、溶媒、反応性希釈剤、可塑剤、ワックス、充填剤、乾燥剤、抗酸化剤、界面活性剤、消泡剤、触媒、UV安定剤および光開始剤から選択される1種または複数の追加の成分(6)をさらに含む、請求項1〜6のいずれか一項に記載の方法。
- 前記組成物がマーキングされたインクである、請求項1〜7のいずれか一項に記載の方法。
- 前記組成物が染色インクである、請求項8に記載の方法。
- 前記組成物が2種以上の異なるマーキングされた非抽出性成分(5)を含む、請求項1〜9のいずれか一項に記載の方法。
- 前記基材が銀行券または価値文書であり、前記組成物(1)が前記基材に印刷されている、請求項1〜10のいずれか一項に記載の方法。
- 前記ステップ(b)が300〜600℃の温度での前記回収試料の熱分解を含む、請求項1〜11のいずれか一項に記載の方法。
- 前記ステップ(c)で、試料断片化の異なる生成物を分離するためにガスクロマトグラフィー(GC)が使用され、これらの生成物の1種または複数を識別するための質量分析(MS)が使用される、請求項1〜12のいずれか一項に記載の方法。
- 前記ステップ(b)および(c)を行うために複合型熱分解−ガスクロマトグラフィー−質量分析計が使用される、請求項13に記載の方法。
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AR089033A1 (es) | 2014-07-23 |
JP2017095724A (ja) | 2017-06-01 |
PT2785800T (pt) | 2017-02-27 |
HK1202887A1 (en) | 2015-10-09 |
AU2012343949A1 (en) | 2014-06-05 |
CA2856354A1 (en) | 2013-06-06 |
WO2013079521A1 (en) | 2013-06-06 |
PL2785800T3 (pl) | 2017-07-31 |
EP2785800A1 (en) | 2014-10-08 |
CN104093789A (zh) | 2014-10-08 |
US20150132543A1 (en) | 2015-05-14 |
CA2856354C (en) | 2020-06-09 |
HUE032645T2 (en) | 2017-10-30 |
BR112014012666A2 (pt) | 2017-06-13 |
RS55816B1 (sr) | 2017-08-31 |
TW201335295A (zh) | 2013-09-01 |
DK2785800T3 (en) | 2017-04-03 |
RU2614676C2 (ru) | 2017-03-28 |
KR20140098153A (ko) | 2014-08-07 |
ES2621391T3 (es) | 2017-07-03 |
AU2012343949B2 (en) | 2015-11-26 |
KR102020690B1 (ko) | 2019-09-10 |
RU2014126387A (ru) | 2016-01-27 |
BR112014012666A8 (pt) | 2017-06-20 |
JP2015507028A (ja) | 2015-03-05 |
EP2785800B1 (en) | 2017-01-04 |
CN104093789B (zh) | 2017-05-03 |
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