JP5693586B2 - ポリマーの着色のための非移染性の着色共重縮合物 - Google Patents
ポリマーの着色のための非移染性の着色共重縮合物 Download PDFInfo
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- JP5693586B2 JP5693586B2 JP2012530215A JP2012530215A JP5693586B2 JP 5693586 B2 JP5693586 B2 JP 5693586B2 JP 2012530215 A JP2012530215 A JP 2012530215A JP 2012530215 A JP2012530215 A JP 2012530215A JP 5693586 B2 JP5693586 B2 JP 5693586B2
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- cycloalkane
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/08—Naphthalimide dyes; Phthalimide dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/101—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an anthracene dye
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/101—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an anthracene dye
- C09B69/102—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an anthracene dye containing a perylene dye
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/103—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing a diaryl- or triarylmethane dye
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/109—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing other specific dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/0004—General aspects of dyeing
- D06P1/0012—Effecting dyeing to obtain luminescent or phosphorescent dyeings
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/0052—Dyeing with polymeric dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/006—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated using polymeric dyes
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Description
・ 少なくとも1つの1,2−C4〜C8シクロアルカンジカルボン酸、1,3−C4〜C8シクロアルカンジカルボン酸、または1,4−C4〜C8シクロアルカンジカルボン酸、あるいはそれらのエステル、無水物、または酸塩化物と、
・ 1モルのC4〜C8シクロアルカンジカルボン酸に対して、0.3〜0.8モル、好ましくは0.4〜0.8モル、より好ましくは0.5〜0.7モルの、少なくとも1種の1,2−C6〜C12シクロアルカンジアミン、1,3−C6〜C12シクロアルカンジアミン、または1,4−C6〜C12シクロアルカンジアミン、あるいはそれらの潜在型と、
・ 1モルのC4〜C8シクロアルカンジカルボン酸に対して、0.2〜0.6モル、好ましくは0.3〜0.5モルの、1,2−C2〜C6アルカンジオール、1,3−C2〜C6アルカンジオール、または1,4−C2〜C6アルカンジオールの少なくとも1種(これらの1つのヒドロキシル基の0〜0.05モルは、モノカルボン酸によってエステル化されていてもよく、C2〜C6アルカンジオールは、割りこまれていなくても、または−O−で割り込まれていてもよく、ただし、C2〜C6アルカンジオールの炭素原子で、1つより多くの酸素原子に結合しているものはない)と、
・ 任意により、1モルのC4〜C8シクロアルカンジカルボン酸に対して、0〜0.1モル、好ましくは0または0.01〜0.05モルの1種以上のアミノ酸と、
・ 任意により、1モルのC4〜C8シクロアルカンジカルボン酸に対して、0〜0.1モル、好ましくは0〜0.05モル、より好ましくは0〜0.02モルの、それぞれ1〜18個の炭素原子を有するモノアルコール、第一級モノアミン、および一塩基酸からなる群より選択される1種以上の単官能性成分と、
・ 1モルのC4〜C8シクロアルカンジカルボン酸に対して、0.001〜0.15モル、好ましくは0.001〜0.01モル、より好ましくは0.002〜0.05モル、最も好ましくは0.01〜0.03モルの、−X、−NH2、−COX、−SO2X、−CO−O−CO−、および−SO2−O−SO2−からなる群より選択される少なくとも2つの置換基を有する少なくとも1種の着色剤(ここで、Xは、ヒドロキシル、または反応性の塩素、臭素、フッ素原子、ヨウ素、またはニトロであり、ただし、これらの置換基の少なくとも2つは、互いと縮合して10員環未満の分子内環を形成したりしない程度に、互いに離れていなければならない)と、
の共重縮合によって得ることができる共重縮合物であって、
ただし、すべてのヒドロキシル基および第一級アミノ基あるいはそれらの潜在型の総量と、すべてのカルボキシル基およびスルホ基の総量とのモル比は、5:4〜4:5、好ましくは9:8〜8:9である、
共重縮合物に関する。
・ 少なくとも1つの1,2−C4〜C8シクロアルカンジカルボン酸、1,3−C4〜C8シクロアルカンジカルボン酸、または1,4−C4〜C8シクロアルカンジカルボン酸、あるいはそれらのエステル、無水物、または酸塩化物と、
・ 1モルのC4〜C8シクロアルカンジカルボン酸に対して、0.3〜0.8モルの少なくとも1種の1,2−C6〜C12シクロアルカンジアミン、1,3−C6〜C12シクロアルカンジアミン、または1,4−C6〜C12シクロアルカンジアミン、あるいはそれらの潜在型と、
・ 1モルのC4〜C8シクロアルカンジカルボン酸に対して、0.2〜0.6モルの少なくとも1種の1,2−C2〜C6アルカンジオール、1,3−C2〜C6アルカンジオール、または1,4−C2〜C6アルカンジオール(これらの1つのヒドロキシル基の0〜0.05モルは、モノカルボン酸によってエステル化されていてもよく、C2〜C6アルカンジオールは、割りこまれていなくても、または−O−で割り込まれていてもよく、ただし、C2〜C6アルカンジオールの炭素原子で、1つより多くの酸素原子に結合しているものはない)と、
・ 任意により、1モルのC4〜C8シクロアルカンジカルボン酸に対して、0〜0.1モルの1種以上のアミノ酸と、
・ 任意により、1モルのC4〜C8シクロアルカンジカルボン酸に対して、0〜0.1モルのそれぞれ1〜18個の炭素原子を含有するモノアルコール、第一級モノアミン、および一塩基酸からなる群より選択される1種以上の単官能性成分と、
・ 1モルのC4〜C8シクロアルカンジカルボン酸に対して、0.001〜0.15モルの、−X、−NH2、−COX、−SO2X、−CO−O−CO−、および−SO2−O−SO2−からなる群より選択される少なくとも2つの置換基を有する少なくとも1種の着色剤(ここで、Xは、ヒドロキシル、または反応性の塩素、臭素、フッ素原子、ヨウ素、またはニトロであり、ただし、これらの置換基の少なくとも2つは、互いと縮合して10員環未満の分子内環を形成したりしない程度に、互いに離れていなければならない)と
の共重縮合によって得ることができる共重縮合物であって、
ただし、すべてのヒドロキシル基および第一級アミノ基あるいはそれらの潜在型の総量と、すべてのカルボキシル基およびスルホ基の総量とのモル比は、5:4〜4:5である、
共重縮合物である。
・ 少なくとも1つの1,2−C4〜C8シクロアルカンジカルボン酸、1,3−C4〜C8シクロアルカンジカルボン酸、または1,4−C4〜C8シクロアルカンジカルボン酸、あるいはそれらのエステル、無水物、または酸塩化物と、
・ 1モルのC4〜C8シクロアルカンジカルボン酸に対して、0.5〜0.7モルの少なくとも1種の1,2−C6〜C12シクロアルカンジアミン、1,3−C6〜C12シクロアルカンジアミン、または1,4−C6〜C12シクロアルカンジアミン、あるいはそれらの潜在型と、
・ 1モルのC4〜C8シクロアルカンジカルボン酸に対して、0.3〜0.5モルの少なくとも1種の1,2−C2〜C6アルカンジオール、1,3−C2〜C6アルカンジオール、または1,4−C2〜C6アルカンジオール(これらの1つのヒドロキシル基の0〜0.05モルは、モノカルボン酸によってエステル化されていてもよく、C2〜C6アルカンジオールは、割りこまれていなくても、または−O−で割り込まれていてもよく、ただし、C2〜C6アルカンジオールの炭素原子で、1つより多くの酸素原子に結合しているものはない)と、
・ 任意により、1モルのC4〜C8シクロアルカンジカルボン酸に対して、0〜0.05モルの1種以上のアミノ酸と、
・ 任意により、1モルのC4〜C8シクロアルカンジカルボン酸に対して、0〜0.02モルの、それぞれ1〜18個の炭素原子を含有するモノアルコール、第一級モノアミン、および一塩基酸からなる群より選択される1種以上の単官能性成分と、
・ 1モルのC4〜C8シクロアルカンジカルボン酸に対して、0.01〜0.03モルの、−X、−NH2、−COX、−SO2X、−CO−O−CO−、および−SO2−O−SO2−からなる群より選択される少なくとも2つの置換基を有する少なくとも1種の着色剤(ここで、Xは、ヒドロキシル、または反応性の塩素、臭素、フッ素原子、ヨウ素、またはニトロであり、ただし、これらの置換基の少なくとも2つは、互いと縮合して10員環未満の分子内環を形成したりしない程度に、互いに離れていなければならない)と、
の共重縮合によって得ることができる共重縮合物であって、
ただし、すべてのヒドロキシル基および第一級アミノ基あるいはそれらの潜在型の総量と、すべてのカルボキシル基およびスルホ基の総量とのモル比は、9:8〜8:9である、
共重縮合物である。
Y1およびY2は、それぞれ独立して、OまたはN−であり、ならびにY3およびY4は、それぞれ独立して、O、N−、またはSである]を有し、
好ましい着色剤は、部分構造:
(a)(a)および(b)の合計に対して、0.05〜70質量%の本発明の共重縮合物と、
(b)(a)および(b)の合計に対して、99.95〜30質量%の高分子量有機材料と
を含む、バルク着色された高分子量有機材料にも関する。
ガラス転移温度(Tg)は、ASTM規格D−3418に従って測定する。
PVC:150〜160℃において二本ロール機により、0.2質量%の共重縮合物を含有する厚さ約0.3mmのPVCフィルムを作製する。
PVC:実施例1〜31による共重縮合物を含有するPVCフィルムは、強い蛍光性および非移染性を示している。
Claims (11)
- ・少なくとも1種の1,2−C4〜C8シクロアルカンジカルボン酸、1,3−C4〜C8シクロアルカンジカルボン酸、または1,4−C4〜C8シクロアルカンジカルボン酸、あるいはそれらのエステル、無水物、または酸塩化物と、
・1モルのC4〜C8シクロアルカンジカルボン酸に対して、0.3〜0.8モルの少なくとも1種の1,2−C6〜C12シクロアルカンジアミン、1,3−C6〜C12シクロアルカンジアミン、または1,4−C6〜C12シクロアルカンジアミンと、
・1モルのC4〜C8シクロアルカンジカルボン酸に対して、0.2〜0.6モルの少なくとも1種の1,2−C2〜C6アルカンジオール、1,3−C2〜C6アルカンジオール、または1,4−C2〜C6アルカンジオール(これらの1つのヒドロキシル基の0〜0.05モルは、モノカルボン酸によってエステル化されていてもよく、C2〜C6アルカンジオールは、割りこまれていなくても、または−O−で割り込まれていてもよく、ただし、C2〜C6アルカンジオールの炭素原子で、1つより多くの酸素原子に結合しているものはない)と、
・任意により、1モルのC4〜C8シクロアルカンジカルボン酸に対して、0〜0.1モルの1種以上のアミノ酸と、
・任意により、1モルのC4〜C8シクロアルカンジカルボン酸に対して、0〜0.1モルの、それぞれ1〜18個の炭素原子を有するモノアルコール、第一級モノアミン、および一塩基酸からなる群より選択される1種以上の単官能性成分と、
・1モルのC4〜C8シクロアルカンジカルボン酸に対して、0.001〜0.15モルの、−X、−NH2、−COX、−SO2X、−CO−O−CO−、および−SO2−O−SO2−からなる群より選択される少なくとも2つの置換基を有する少なくとも1種の着色剤(ここで、Xは、ヒドロキシル、または、塩素、臭素、フッ素、またはヨウ素であり、ただし、これらの置換基の少なくとも2つは、互いと縮合して10員環未満の分子内環を形成しえない程度に、互いに離れていなければならない)又は着色剤である4−ニトロ−1,8−ナフトエ酸無水物と
の共重縮合によって得ることができる共重縮合物であって、
ただし、すべてのヒドロキシル基および第一級アミノ基の総量と、すべてのカルボキシル基およびスルホ基の総量とのモル比は、5:4〜4:5である、前記共重縮合物。 - 60〜200℃のガラス転移温度(Tg)を有することを特徴とする、請求項1または2に記載の共重縮合物。
- 前記C4〜C8シクロアルカンジカルボン酸、前記C6〜C12シクロアルカンジアミン、前記C2〜C6アルカンジオール、前記着色剤、ならびに任意により前記単官能性成分が、任意により酸性触媒の存在下において、1秒〜100時間にわたっておよそ50〜300℃に加熱される、請求項1、2または3に記載の共重縮合物の製造方法。
- 前記共重縮合物が、該共重縮合物の本発明による反応物質の総質量に対して0〜5000質量%の不活性媒体の存在下において製造される、請求項4に記載の方法。
- 前記共重縮合が、押出機中において行われる、請求項4または5に記載の方法。
- ポリマー性基材が、前記押出機に追加的に計量供給される、請求項6に記載の方法。
- ポリマーのバルク着色のための、請求項1、2、または3に記載の共重縮合物の使用。
- 塗料、印刷用インク、固体トナー、ワックス転写リボンまたはカラーフィルターを着色するための、請求項1、2、または3に記載の共重縮合物の使用。
- (a)(a)および(b)の合計に対して0.05〜70質量%の、請求項1、2または3に記載の共重縮合物と、
(b)(a)および(b)の合計に対して99.95〜30質量%の高分子量有機材料と
を含む、バルク着色された高分子量有機材料。 - 高分子量有機材料をバルク着色する方法であって、請求項1、2または3に記載の共重縮合物を、該高分子量有機材料中に導入することを特徴とする、前記方法。
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ATE390457T1 (de) | 2004-09-03 | 2008-04-15 | Ciba Sc Holding Ag | In-can stabilisatoren |
JP4291296B2 (ja) * | 2005-04-08 | 2009-07-08 | 株式会社メニコン | 新規重合性染料およびそれを含む眼用レンズ |
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US20120172529A1 (en) | 2012-07-05 |
CN102510882B (zh) | 2015-04-15 |
JP2013506020A (ja) | 2013-02-21 |
EP2480610A1 (en) | 2012-08-01 |
CN102510882A (zh) | 2012-06-20 |
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