JP2021042360A - ペンダント光吸収体を有するポリアミド及び関連する方法 - Google Patents
ペンダント光吸収体を有するポリアミド及び関連する方法 Download PDFInfo
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- JP2021042360A JP2021042360A JP2020144509A JP2020144509A JP2021042360A JP 2021042360 A JP2021042360 A JP 2021042360A JP 2020144509 A JP2020144509 A JP 2020144509A JP 2020144509 A JP2020144509 A JP 2020144509A JP 2021042360 A JP2021042360 A JP 2021042360A
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- Prior art keywords
- polyamide
- acid
- nylon
- halogen
- particles
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 229920002647 polyamide Polymers 0.000 title claims abstract description 244
- 239000004952 Polyamide Substances 0.000 title claims abstract description 243
- 238000000034 method Methods 0.000 title claims abstract description 149
- 239000006096 absorbing agent Substances 0.000 title claims abstract description 124
- 230000003287 optical effect Effects 0.000 title abstract description 11
- 239000002253 acid Substances 0.000 claims abstract description 43
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 35
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical group C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims abstract description 17
- -1 6-carboxyfluoresene Chemical compound 0.000 claims description 183
- 239000000203 mixture Substances 0.000 claims description 120
- 229920001778 nylon Polymers 0.000 claims description 100
- 239000004677 Nylon Substances 0.000 claims description 96
- 101100350063 Drosophila melanogaster Oamb gene Proteins 0.000 claims description 83
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 229920001577 copolymer Polymers 0.000 claims description 26
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical group C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 230000032050 esterification Effects 0.000 claims description 16
- 238000005886 esterification reaction Methods 0.000 claims description 16
- 229920002302 Nylon 6,6 Polymers 0.000 claims description 15
- WPWWKBNOXTZDQJ-UHFFFAOYSA-N xanthopurpurin Chemical compound C1=CC=C2C(=O)C3=CC(O)=CC(O)=C3C(=O)C2=C1 WPWWKBNOXTZDQJ-UHFFFAOYSA-N 0.000 claims description 14
- 229920000305 Nylon 6,10 Polymers 0.000 claims description 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 13
- 239000011734 sodium Substances 0.000 claims description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- BZTDTCNHAFUJOG-UHFFFAOYSA-N 6-carboxyfluorescein Chemical compound C12=CC=C(O)C=C2OC2=CC(O)=CC=C2C11OC(=O)C2=CC=C(C(=O)O)C=C21 BZTDTCNHAFUJOG-UHFFFAOYSA-N 0.000 claims description 12
- 229920006012 semi-aromatic polyamide Polymers 0.000 claims description 12
- 229910052708 sodium Inorganic materials 0.000 claims description 12
- GVNWZKBFMFUVNX-UHFFFAOYSA-N Adipamide Chemical compound NC(=O)CCCCC(N)=O GVNWZKBFMFUVNX-UHFFFAOYSA-N 0.000 claims description 11
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 11
- 229920003189 Nylon 4,6 Polymers 0.000 claims description 11
- 125000001246 bromo group Chemical group Br* 0.000 claims description 11
- DEGAKNSWVGKMLS-UHFFFAOYSA-N calcein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC(CN(CC(O)=O)CC(O)=O)=C(O)C=C1OC1=C2C=C(CN(CC(O)=O)CC(=O)O)C(O)=C1 DEGAKNSWVGKMLS-UHFFFAOYSA-N 0.000 claims description 11
- 229960002378 oftasceine Drugs 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- JGZVUTYDEVUNMK-UHFFFAOYSA-N 5-carboxy-2',7'-dichlorofluorescein Chemical compound C12=CC(Cl)=C(O)C=C2OC2=CC(O)=C(Cl)C=C2C21OC(=O)C1=CC(C(=O)O)=CC=C21 JGZVUTYDEVUNMK-UHFFFAOYSA-N 0.000 claims description 9
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 claims description 9
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 claims description 9
- BATFHSIVMJJJAF-UHFFFAOYSA-N Morindone Chemical compound OC1=CC=C2C(=O)C3=C(O)C(C)=CC=C3C(=O)C2=C1O BATFHSIVMJJJAF-UHFFFAOYSA-N 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- MHXFWEJMQVIWDH-UHFFFAOYSA-N 1-amino-4-hydroxy-2-phenoxyanthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OC1=CC=CC=C1 MHXFWEJMQVIWDH-UHFFFAOYSA-N 0.000 claims description 7
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 claims description 7
- 229940077386 sodium benzenesulfonate Drugs 0.000 claims description 7
- MZSDGDXXBZSFTG-UHFFFAOYSA-M sodium;benzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC=C1 MZSDGDXXBZSFTG-UHFFFAOYSA-M 0.000 claims description 7
- VFNKZQNIXUFLBC-UHFFFAOYSA-N 2',7'-dichlorofluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC(Cl)=C(O)C=C1OC1=C2C=C(Cl)C(O)=C1 VFNKZQNIXUFLBC-UHFFFAOYSA-N 0.000 claims description 6
- MHMNJMPURVTYEJ-UHFFFAOYSA-N fluorescein-5-isothiocyanate Chemical compound O1C(=O)C2=CC(N=C=S)=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 MHMNJMPURVTYEJ-UHFFFAOYSA-N 0.000 claims description 6
- KQSBZNJFKWOQQK-UHFFFAOYSA-N hystazarin Natural products O=C1C2=CC=CC=C2C(=O)C2=C1C=C(O)C(O)=C2 KQSBZNJFKWOQQK-UHFFFAOYSA-N 0.000 claims description 6
- LJFWQNJLLOFIJK-UHFFFAOYSA-N solvent violet 13 Chemical compound C1=CC(C)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O LJFWQNJLLOFIJK-UHFFFAOYSA-N 0.000 claims description 6
- RJPSHDMGSVVHFA-UHFFFAOYSA-N 2-[carboxymethyl-[(7-hydroxy-4-methyl-2-oxochromen-8-yl)methyl]amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)CC1=C(O)C=CC2=C1OC(=O)C=C2C RJPSHDMGSVVHFA-UHFFFAOYSA-N 0.000 claims description 5
- VDABVNMGKGUPEY-UHFFFAOYSA-N 6-carboxyfluorescein succinimidyl ester Chemical compound C=1C(O)=CC=C2C=1OC1=CC(O)=CC=C1C2(C1=C2)OC(=O)C1=CC=C2C(=O)ON1C(=O)CCC1=O VDABVNMGKGUPEY-UHFFFAOYSA-N 0.000 claims description 5
- RZRJYURCNBXIST-UHFFFAOYSA-N 2-anthroic acid Chemical compound C1=CC=CC2=CC3=CC(C(=O)O)=CC=C3C=C21 RZRJYURCNBXIST-UHFFFAOYSA-N 0.000 claims description 4
- YVTPVJDECOUTJW-UHFFFAOYSA-N 3-(2,5-dioxopyrrolidin-1-yl)oxycarbonyl-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoic acid;4-(2,5-dioxopyrrolidin-1-yl)oxycarbonyl-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoic acid Chemical compound C1=C(C2=C3C=CC(=O)C=C3OC3=CC(O)=CC=C32)C(C(=O)O)=CC=C1C(=O)ON1C(=O)CCC1=O.C12=CC=C(O)C=C2OC2=CC(=O)C=CC2=C1C=1C(C(=O)O)=CC=CC=1C(=O)ON1C(=O)CCC1=O YVTPVJDECOUTJW-UHFFFAOYSA-N 0.000 claims description 4
- DHXNZYCXMFBMHE-UHFFFAOYSA-N 3-bromopropanoic acid Chemical compound OC(=O)CCBr DHXNZYCXMFBMHE-UHFFFAOYSA-N 0.000 claims description 4
- QEYMMOKECZBKAC-UHFFFAOYSA-N 3-chloropropanoic acid Chemical compound OC(=O)CCCl QEYMMOKECZBKAC-UHFFFAOYSA-N 0.000 claims description 4
- GRHQDJDRGZFIPO-UHFFFAOYSA-N 4-bromobutanoic acid Chemical compound OC(=O)CCCBr GRHQDJDRGZFIPO-UHFFFAOYSA-N 0.000 claims description 4
- IPLKGJHGWCVSOG-UHFFFAOYSA-N 4-chlorobutanoic acid Chemical compound OC(=O)CCCCl IPLKGJHGWCVSOG-UHFFFAOYSA-N 0.000 claims description 4
- WNXNUPJZWYOKMW-UHFFFAOYSA-N 5-bromopentanoic acid Chemical compound OC(=O)CCCCBr WNXNUPJZWYOKMW-UHFFFAOYSA-N 0.000 claims description 4
- YSXDKDWNIPOSMF-UHFFFAOYSA-N 5-chloropentanoic acid Chemical compound OC(=O)CCCCCl YSXDKDWNIPOSMF-UHFFFAOYSA-N 0.000 claims description 4
- XWWKSLXUVZVGSP-UHFFFAOYSA-N 6-chlorohexanoic acid Chemical compound OC(=O)CCCCCCl XWWKSLXUVZVGSP-UHFFFAOYSA-N 0.000 claims description 4
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 4
- 229940106681 chloroacetic acid Drugs 0.000 claims description 4
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 4
- GTKIEPUIFBBXJQ-UHFFFAOYSA-M sodium;2-[(4-hydroxy-9,10-dioxoanthracen-1-yl)amino]-5-methylbenzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(C)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O GTKIEPUIFBBXJQ-UHFFFAOYSA-M 0.000 claims description 4
- JOQSWWMMXQAPQU-UHFFFAOYSA-N 1,3-dioxo-4h-anthracene-2-sulfonic acid Chemical compound C1=CC=C2C=C(C(C(S(=O)(=O)O)C(=O)C3)=O)C3=CC2=C1 JOQSWWMMXQAPQU-UHFFFAOYSA-N 0.000 claims description 3
- CAWJMKHIWZGFOS-UHFFFAOYSA-N 3-pyren-2-ylpropanoic acid Chemical compound C1=CC=C2C=CC3=CC(CCC(=O)O)=CC4=CC=C1C2=C43 CAWJMKHIWZGFOS-UHFFFAOYSA-N 0.000 claims description 3
- FGMCKNLTEOTVMP-UHFFFAOYSA-N C1=C(C=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)CCC(=O)O Chemical compound C1=C(C=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)CCC(=O)O FGMCKNLTEOTVMP-UHFFFAOYSA-N 0.000 claims description 3
- ISQRJFLLIDGZEP-CMWLGVBASA-N Sophoricoside Chemical group O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C(C=2C(C3=C(O)C=C(O)C=C3OC=2)=O)C=C1 ISQRJFLLIDGZEP-CMWLGVBASA-N 0.000 claims description 3
- LVZIWKFQFKNSMO-UHFFFAOYSA-N 1-chlorobutan-1-ol Chemical compound CCCC(O)Cl LVZIWKFQFKNSMO-UHFFFAOYSA-N 0.000 claims description 2
- HZTPKMIMXLTOSK-UHFFFAOYSA-N 2-bromohexanoic acid Chemical compound CCCCC(Br)C(O)=O HZTPKMIMXLTOSK-UHFFFAOYSA-N 0.000 claims description 2
- IIZGWPQZWKLJOI-UHFFFAOYSA-N perylene-3-carboxylic acid Chemical compound C=12C3=CC=CC2=CC=CC=1C1=CC=CC2=C1C3=CC=C2C(=O)O IIZGWPQZWKLJOI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- CZXGXYBOQYQXQD-UHFFFAOYSA-N methyl benzenesulfonate Chemical compound COS(=O)(=O)C1=CC=CC=C1 CZXGXYBOQYQXQD-UHFFFAOYSA-N 0.000 claims 1
- 239000002245 particle Substances 0.000 description 215
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- 239000000839 emulsion Substances 0.000 description 115
- 239000003381 stabilizer Substances 0.000 description 99
- 229920000642 polymer Polymers 0.000 description 78
- 239000002612 dispersion medium Substances 0.000 description 55
- 239000002105 nanoparticle Substances 0.000 description 55
- 239000000975 dye Substances 0.000 description 35
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 27
- 239000005977 Ethylene Substances 0.000 description 27
- 238000000576 coating method Methods 0.000 description 26
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- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 14
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Abstract
Description
本明細書で使用するとき、用語「不混和性」は、組み合わされたときに、周囲気圧にて室温で、又は室温で固体である場合は構成成分の融点で、互いに5重量%未満の溶融度を有する2つ以上の相を形成する構成成分の混合物を指す。例えば、10,000g/モルの分子量を有するポリエチレンオキシドは、室温で固体であり、65℃の融点を有する。したがって、室温で液体である材料及び当該ポリエチレンオキシドが65℃で5重量%未満の溶融度を有する場合、当該ポリエチレンオキシドは当該材料と不混和性である。
本開示はポリアミドの骨格から垂下する光吸収体を有するポリアミド及び関連する方法に関する。
本明細書に記載のOAMBポリアミドは、様々な物体(又は物品)を製造するために使用され得る。本明細書に記載のOAMBポリアミドは、単独で、又は他の熱可塑性ポリマー(例えば、光吸収体及び/又は他の熱可塑性ポリマーを含まないポリアミド)と組み合わせて使用され得る。本開示の1種以上のOAMBポリアミドと共に使用され得る熱可塑性ポリマーの例としては、限定するものではないが、ポリアミド、ポリウレタン、ポリエチレン、ポリプロピレン、ポリアセタール、ポリカーボネート、ポリブチレンテレフタレート(PBT)、ポリエチレンテレフタレート(PET)、ポリエチレンナフタレート(PEN)、ポリトリメチレンテレフタレート(PTT)、ポリヘキサメチレンテレフタレート、ポリスチレン、ポリ塩化ビニル、ポリテトラフルオロエテン、ポリエステル(例えば、ポリ乳酸)、ポリエーテル、ポリエーテルスルホン、ポリエーテルエーテルケトン、ポリアクリレート、ポリメタクリレート、ポリイミド、アクリロニトリルブタジエンスチレン(ABS)、ポリフェニレンスルフィド、ビニルポリマー、ポリアリーレンエーテル、ポリアリーレンスルフィド、ポリスルホン、ポリエーテルケトン、ポリアミドイミド、ポリエーテルイミド、ポリエーテルエステル、ポリエーテルブロック及びポリアミドブロック(PEBA又はポリエーテルブロックアミド)を含むコポリマー、グラフト化又は非グラフト化熱可塑性ポリオレフィン、官能化又は非官能化エチレン/ビニルモノマーポリマー、官能化又は非官能化エチレン/アルキル(メタ)アクリレート、官能化又は非官能化(メタ)アクリル酸ポリマー、官能化又は非官能化エチレン/ビニルモノマー/アルキル(メタ)アクリレートターポリマー、エチレン/ビニルモノマー/カルボニルターポリマー、エチレン/アルキル(メタ)アクリレート/カルボニルターポリマー、メチルメタクリレート−ブタジエン−スチレン(MBS)型コアシェルポリマー、ポリスチレン−ブロック−ポリブタジエン−ブロック−ポリ(メチルメタクリレート)(SBM)ブロックターポリマー、塩素化又はクロロスルホン化ポリエチレン、ポリフッ化ビニリデン(PVDF)、フェノール樹脂、ポリ(エチレン/酢酸ビニル)、ポリブタジエン、ポリイソプレン、スチレンブロックコポリマー、ポリアクリロニトリル、シリコーンなど、及びこれらの任意の組み合わせが挙げられる。前述の1つ以上を含むコポリマーはまた、本明細書に記載の方法及びシステムにおいて使用され得る。
図は、本開示の非限定的な例示的方法100のフローチャートである。熱可塑性ポリマー102(1種以上のOAMBポリアミド及び任意選択的に1種以上の他の熱可塑性ポリマーを含む)、分散媒104、及び任意選択的に乳化安定剤106を組み合わせて(108)、混合物110を生成する。構成成分102、104、及び106は、任意の順序で添加され、構成成分102、104、及び106を組み合わせるプロセス108中の混合及び/又は加熱を含み得る。
本明細書に記載のOAMBポリアミド粒子は、様々な物体(又は物品)を製造するために使用され得る。本明細書に記載のOAMBポリアミドは、単独で、又は他の熱可塑性ポリマー(例えば、光吸収体及び/又は他の熱可塑性ポリマーを含まないポリアミド)を含む他の粒子と組み合わせて使用され得る。このような他の粒子で使用され得る熱可塑性ポリマーの例としては、限定するものではないが、ポリアミド、ポリウレタン、ポリエチレン、ポリプロピレン、ポリアセタール、ポリカーボネート、ポリブチレンテレフタレート(PBT)、ポリエチレンテレフタレート(PET)、ポリエチレンナフタレート(PEN)、ポリトリメチレンテレフタレート(PTT)、ポリヘキサメチレンテレフタレート、ポリスチレン、ポリ塩化ビニル、ポリテトラフルオロエテン、ポリエステル(例えば、ポリ乳酸)、ポリエーテル、ポリエーテルスルホン、ポリエーテルエーテルケトン、ポリアクリレート、ポリメタクリレート、ポリイミド、アクリロニトリルブタジエンスチレン(ABS)、ポリフェニレンスルフィド、ビニルポリマー、ポリアリーレンエーテル、ポリアリーレンスルフィド、ポリスルホン、ポリエーテルケトン、ポリアミドイミド、ポリエーテルイミド、ポリエーテルエステル、ポリエーテルブロック及びポリアミドブロック(PEBA又はポリエーテルブロックアミド)を含むコポリマー、グラフト化又は非グラフト化熱可塑性ポリオレフィン、官能化又は非官能化エチレン/ビニルモノマーポリマー、官能化又は非官能化エチレン/アルキル(メタ)アクリレート、官能化又は非官能化(メタ)アクリル酸ポリマー、官能化又は非官能化エチレン/ビニルモノマー/アルキル(メタ)アクリレートターポリマー、エチレン/ビニルモノマー/カルボニルターポリマー、エチレン/アルキル(メタ)アクリレート/カルボニルターポリマー、メチルメタクリレート−ブタジエン−スチレン(MBS)型コアシェルポリマー、ポリスチレン−ブロック−ポリブタジエン−ブロック−ポリ(メチルメタクリレート)(SBM)ブロックターポリマー、塩素化又はクロロスルホン化ポリエチレン、ポリフッ化ビニリデン(PVDF)、フェノール樹脂、ポリ(エチレン/酢酸ビニル)、ポリブタジエン、ポリイソプレン、スチレンブロックコポリマー、ポリアクリロニトリル、シリコーンなど、及びこれらの任意の組み合わせが挙げられる。前述の1つ以上を含むコポリマーはまた、本明細書に記載の方法及びシステムにおいて使用され得る。
第1の非限定的な例示的実施形態は、ハロゲン末端脂肪族酸でヒドロキシルペンダント光吸収体をエステル化してハロゲン末端アルキル光吸収体を生成することと、ハロゲン末端アルキル光吸収体でポリアミドをNアルキル化して、ポリアミドの骨格から垂下する光吸収体を有するポリアミド(OAMBポリアミド)を生成することと、を含む方法である。第1の非限定的な例示的実施形態は、ハロゲン末端脂肪族酸がクロロ脂肪族酸又はブロモ脂肪族酸である、要素1、ハロゲン末端脂肪族酸がC2〜C18ハロゲン末端脂肪族酸である、要素2、ヒドロキシルペンダント光吸収体が、1,2−ジヒドロキシアントラキノン、カルミン酸、1,3−ジヒドロキシアントラキノン、1,4−ジヒドロキシアントラキノン、1−ヒドロキシ−4−(p−トリルアミノ)アントラキノン、1,8−ジヒドロキシ−3−メトキシ−6−メチルアントラキノン、1,2,5−トリヒドロキシ−6−メチルアントラセン−9,10−ジオン、カルセイン、6−カルボキシフルオレセインスクシンイミジルエステル、6−カルボキシフルオレセイン、2’,7’−ジクロロ−3’,6’−ジヒドロキシ−3H−スピロ[2−ベンゾフラン−1,9’−キサンテン]−3−オン、フルオレセインイソチオシアネート、4’,5’−ジブロモフルオレセイン、5(6)−カルボキシ−2’7’−ジクロロフルオレセイン、4−クロロ−3−[(2Z)−2−[1−[5−クロロ−4−[[(2Z)−2−[[2−クロロ−5−[N−[2−(4−クロロフェノキシ)−5−(トリフルオロメチル)フェニル]−C−ヒドロキシカルボンイミドイル]フェニル]ヒドラジニリデン]−3−オキソブタノイル]アミノ]−2−メチルアニリノ]−1,3−ジオキソブタン−2−イリデン]ヒドラジニル]−N−[2−(4−クロロフェノキシ)−5−(トリフルオロメチル)フェニル]ベンゼンカルボキシミド酸、2−[(3−カルボキシ−2−オキシドナフタレン−1−イル)ジアゼニル]−4−クロロ−5−メチルベンゼンスルホン酸二ナトリウム、フェノール染料、3,3−ビス(4−ヒドロキシフェニル)−2−ベンゾフラン−1−オン、4,8−ジアミノ−1,5−ジヒドロキシ−9,10−ジオキソアントラセン−2−スルホン酸ナトリウム、1−アミノ−4−ヒドロキシ−2−フェノキシアントラセン−9,10−ジオン、5−オキソ−1−(4−スルホナートフェニル)−4−[(4−スルホナートフェニル)ジアゼニル]−4H−ピラゾール−3−カルボン酸三ナトリウム、5−クロロ−2−ヒドロキシ−3−[(3−メチル−5−オキソ−1−フェニル−4H−ピラゾール−4−イル)ジアゼニル]ベンゼンスルホン酸ナトリウム、2−[(4−ヒドロキシ−9,10−ジオキソアントラセン−1−イル)アミノ]−5−メチルベンゼンスルホン酸ナトリウム、3,5,6,8テトラヒドロキシ−1−メチル−9,10−ジオキソ−7−[3,4,5−トリヒドロキシ−6−(ヒドロキシメチル)オキサン−2−イル]アントラセン−2−カルボン酸など、及びこれらの任意の組み合わせからなる群から選択される、要素3、ポリアミドが、ポリカプロアミド、ポリ(ヘキサメチレンスクシンアミド)、ポリヘキサメチレンアジパミド、ポリペンタメチレンアジパミド、ポリヘキサメチレンセバカミド、ポリウンデカアミド、ポリドデカアミド、ポリヘキサメチレンテレフタルアミド、ナイロン10,10、ナイロン10,12、ナイロン10,14、ナイロン10,18、ナイロン6,18、ナイロン6,12、ナイロン6,14、ナイロン12,12、半芳香族ポリアミド、芳香族ポリアミド、これらの任意のコポリマー、及びこれらの任意の組み合わせからなる群から選択される、要素4、ハロゲン末端脂肪族酸がX−(CH2)n−COOHであり、式中、Xがブロモ又はクロロであり、nが1〜17である、要素5、ハロゲン末端脂肪族酸が、ブロモ酢酸、クロロ酢酸、3−ブロモプロピオン酸、3−クロロプロピオン酸、4−ブロモ酪酸、4−クロロ酪酸、5−ブロモ吉草酸、5−クロロ吉草酸、6−ブロモヘキサン酸、6−クロロヘキサン酸、及びこれらの任意の組み合わせからなる群から選択される、要素6、エステル化が約0℃〜約70℃にて行われる、要素7、エステル化が約10分〜約24時間行われる、要素8、ヒドロキシルペンダント光吸収体対ハロゲン末端脂肪族酸のモル比が約5:1〜約1:5である、要素9、Nアルキル化が約100℃〜約200℃にて行われる、要素10(lement 10)、Nアルキル化が約10分〜約48時間行われる、要素11、並びにハロゲン末端アルキル光吸収体対ポリアミドのモル比が好ましくは約500:1〜約10:1である、要素12のうちの1つ以上を含んでよい。組み合わせの例としては、限定するものではないが、要素2〜12のうちの1つ以上と組み合わせた要素1、要素3〜12のうちの1つ以上と組み合わせた要素2、要素4〜12のうちの1つ以上と組み合わせた要素3、要素5〜12のうちの1つ以上と組み合わせた要素4、要素6〜12のうちの1つ以上と組み合わせた要素5、要素7〜12のうちの1つ以上と組み合わせた要素6、要素8〜12のうちの1つ以上と組み合わせた要素7、要素9〜12のうちの1つ以上と組み合わせた要素8、要素10〜12のうちの1つ以上と組み合わせた要素9、要素11〜12のうちの1つ以上と組み合わせた要素10、及び要素11と要素12との組み合わせが挙げられる。
第1節.ハロゲン末端脂肪族酸でヒドロキシルペンダント光吸収体をエステル化してハロゲン末端アルキル光吸収体を生成することと、ハロゲン末端アルキル光吸収体でポリアミドをNアルキル化して、ポリアミドの骨格から垂下する光吸収体を有するポリアミド(OAMBポリアミド)を生成することと、を含む方法。
Claims (20)
- ハロゲン末端脂肪族酸でヒドロキシルペンダント光吸収体をエステル化してハロゲン末端アルキル光吸収体を生成することと、
前記ハロゲン末端アルキル光吸収体でポリアミドをNアルキル化して、ポリアミドの骨格から垂下する光吸収体を有するポリアミド(OAMBポリアミド)を生成することと、を含む方法。 - 前記ハロゲン末端脂肪族酸はクロロ脂肪族酸又はブロモ脂肪族酸である、請求項1に記載の方法。
- 前記ハロゲン末端脂肪族酸はC2〜C18ハロゲン末端脂肪族酸である、請求項1に記載の方法。
- 前記ヒドロキシルペンダント光吸収体は、1,2−ジヒドロキシアントラキノン、カルミン酸、1,3−ジヒドロキシアントラキノン、1,4−ジヒドロキシアントラキノン、1−ヒドロキシ−4−(p−トリルアミノ)アントラキノン、1,8−ジヒドロキシ−3−メトキシ−6−メチルアントラキノン、1,2,5−トリヒドロキシ−6−メチルアントラセン−9,10−ジオン、カルセイン、6−カルボキシフルオレセインスクシンイミジルエステル、6−カルボキシフルオレセイン、2’,7’−ジクロロ−3’,6’−ジヒドロキシ−3H−スピロ[2−ベンゾフラン−1,9’−キサンテン]−3−オン、フルオレセインイソチオシアネート、4’,5’−ジブロモフルオレセイン、5(6)−カルボキシ−2’7’−ジクロロフルオレセイン、4−クロロ−3−[(2Z)−2−[1−[5−クロロ−4−[[(2Z)−2−[[2−クロロ−5−[N−[2−(4−クロロフェノキシ)−5−(トリフルオロメチル)フェニル]−C−ヒドロキシカルボンイミドイル]フェニル]ヒドラジニリデン]−3−オキソブタノイル]アミノ]−2−メチルアニリノ]−1,3−ジオキソブタン−2−イリデン]ヒドラジニル]−N−[2−(4−クロロフェノキシ)−5−(トリフルオロメチル)フェニル]ベンゼンカルボキシミド酸、2−[(3−カルボキシ−2−オキシドナフタレン−1−イル)ジアゼニル]−4−クロロ−5−メチルベンゼンスルホン酸二ナトリウム、フェノール染料、3,3−ビス(4−ヒドロキシフェニル)−2−ベンゾフラン−1−オン、4,8−ジアミノ−1,5−ジヒドロキシ−9,10−ジオキソアントラセン−2−スルホン酸ナトリウム、1−アミノ−4−ヒドロキシ−2−フェノキシアントラセン−9,10−ジオン、5−オキソ−1−(4−スルホナートフェニル)−4−[(4−スルホナートフェニル)ジアゼニル]−4H−ピラゾール−3−カルボン酸三ナトリウム、5−クロロ−2−ヒドロキシ−3−[(3−メチル−5−オキソ−1−フェニル−4H−ピラゾール−4−イル)ジアゼニル]ベンゼンスルホン酸ナトリウム、2−[(4−ヒドロキシ−9,10−ジオキソアントラセン−1−イル)アミノ]−5−メチルベンゼンスルホン酸ナトリウム、3,5,6,8テトラヒドロキシ−1−メチル−9,10−ジオキソ−7−[3,4,5−トリヒドロキシ−6−(ヒドロキシメチル)オキサン−2−イル]アントラセン−2−カルボン酸など、及びこれらの任意の組み合わせからなる群から選択される、請求項1に記載の方法。
- 前記ポリアミドは、ポリカプロアミド、ポリ(ヘキサメチレンスクシンアミド)、ポリヘキサメチレンアジパミド、ポリペンタメチレンアジパミド、ポリヘキサメチレンセバカミド、ポリウンデカアミド、ポリドデカアミド、ポリヘキサメチレンテレフタルアミド、ナイロン10,10、ナイロン10,12、ナイロン10,14、ナイロン10,18、ナイロン6,18、ナイロン6,12、ナイロン6,14、ナイロン12,12、半芳香族ポリアミド、芳香族ポリアミド、これらの任意のコポリマー、及びこれらの任意の組み合わせからなる群から選択される、請求項1に記載の方法。
- 前記ハロゲン末端脂肪族酸はX−(CH2)n−COOHであり、式中、Xはブロモ又はクロロであり、nは1〜17である、請求項1に記載の方法。
- 前記ハロゲン末端脂肪族酸は、ブロモ酢酸、クロロ酢酸、3−ブロモプロピオン酸、3−クロロプロピオン酸、4−ブロモ酪酸、4−クロロ酪酸、5−ブロモ吉草酸、5−クロロ吉草酸、6−ブロモヘキサン酸、6−クロロヘキサン酸、及びこれらの任意の組み合わせからなる群から選択される、請求項1に記載の方法。
- エステル化は約0℃〜約70℃にて行われる、請求項1に記載の方法。
- エステル化は約10分〜約24時間行われる、請求項1に記載の方法。
- 前記ヒドロキシルペンダント光吸収体対前記ハロゲン末端脂肪族酸のモル比が約5:1〜約1:5である、請求項1に記載の方法。
- 前記ハロゲン末端アルキル光吸収体対前記ポリアミドのモル比が、好ましくは約500:1〜約10:1である、請求項1に記載の方法。
- ハロゲン末端脂肪族アルコールでカルボキシルペンダント光吸収体をエステル化してハロゲン末端アルキル光吸収体を生成することと、
前記変性光吸収体でポリアミドをNアルキル化して、ポリアミドの骨格から垂下する光吸収体を有するポリアミド(OAMBポリアミド)を生成することと、を含む方法。 - 前記カルボキシルペンダント光吸収体は、カルセイン、5(6)−カルボキシフルオレセイン、6−カルボキシフルオレセイン、5(6)−カルボキシフルオレセイン−N−ヒドロキシスクシンイミドエステル、2−ピレンプロパン酸、2−ペリレンプロパン酸、3,9−ペリレンジカルボン酸、5(6)−カルボキシ−2’7’−ジクロロフルオレセイン、カルセインブルー、2−[(3−カルボキシ−2−オキシドナフタレン−1−イル)ジアゼニル]−4−クロロ−5−メチルベンゼンスルホン酸二ナトリウム、5−オキソ−1−(4−スルホナートフェニル)−4−[(4−スルホナートフェニル)ジアゼニル]−4H−ピラゾール−3−カルボン酸三ナトリウムなど、及びこれらの任意の組み合わせからなる群から選択される、請求項12に記載の方法。
- 前記ポリアミドは、ポリカプロアミド、ポリ(ヘキサメチレンスクシンアミド)、ポリヘキサメチレンアジパミド、ポリペンタメチレンアジパミド、ポリヘキサメチレンセバカミド、ポリウンデカアミド、ポリドデカアミド、ポリヘキサメチレンテレフタルアミド、ナイロン10,10、ナイロン10,12、ナイロン10,14、ナイロン10,18、ナイロン6,18、ナイロン6,12、ナイロン6,14、ナイロン12,12、半芳香族ポリアミド、芳香族ポリアミド、これらの任意のコポリマー、及びこれらの任意の組み合わせからなる群から選択される、請求項12に記載の方法。
- 前記ハロゲン末端脂肪族アルコールはX−(CH2)n−OHであり、式中、Xはブロモ又はクロロであり、nは2〜18である、請求項12に記載の方法。
- 前記ハロゲン末端脂肪族アルコールは、3−ブロモエタン−1−オール、3−クロロエタン−1−オール、4−ブロモプロパン−1−オール、4−クロロプロパン−1−オール、5−ブロモブタン−1−オール、5−クロロブタン−1−オール、6−ブロモペンタン−1−オール、6−クロロペンタン−1−オール、7−ブロモヘキサン−1−オール、7−クロロヘキサン−1−オール、及びこれらの任意の組み合わせからなる群から選択される、請求項12に記載の方法。
- エステル化は約0℃〜約70℃にて行われる、請求項12に記載の方法。
- 前記カルボキシルペンダント光吸収体対前記ハロゲン末端脂肪族アルコールのモル比が約5:1〜約1:5である、請求項14に記載の方法。
- 前記ハロゲン末端アルキル光吸収体対前記ポリアミドのモル比が、好ましくは約500:1〜約10:1である、請求項14に記載の方法。
- ポリアミドの骨格から垂下する光吸収体を有するポリアミドを含む組成物であって、前記ポリアミド及び前記光吸収体はアルキルリンカーによって連結されている、組成物。
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