JP4187295B2 - Dye dispersant - Google Patents
Dye dispersant Download PDFInfo
- Publication number
- JP4187295B2 JP4187295B2 JP36702097A JP36702097A JP4187295B2 JP 4187295 B2 JP4187295 B2 JP 4187295B2 JP 36702097 A JP36702097 A JP 36702097A JP 36702097 A JP36702097 A JP 36702097A JP 4187295 B2 JP4187295 B2 JP 4187295B2
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- Prior art keywords
- condensate
- formaldehyde
- synthesis example
- acid
- dye
- 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.)
- Expired - Fee Related
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- 239000002270 dispersing agent Substances 0.000 title claims description 18
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 97
- 239000000203 mixture Substances 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 20
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 10
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 6
- PXEDJBXQKAGXNJ-QTNFYWBSSA-L disodium L-glutamate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](N)CCC([O-])=O PXEDJBXQKAGXNJ-QTNFYWBSSA-L 0.000 claims description 6
- 235000013923 monosodium glutamate Nutrition 0.000 claims description 6
- 229940073490 sodium glutamate Drugs 0.000 claims description 6
- 239000006185 dispersion Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 36
- 238000003786 synthesis reaction Methods 0.000 description 36
- 239000000975 dye Substances 0.000 description 17
- 238000003756 stirring Methods 0.000 description 16
- 239000004744 fabric Substances 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- 238000005562 fading Methods 0.000 description 14
- 239000007788 liquid Substances 0.000 description 14
- 238000004043 dyeing Methods 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- 238000001694 spray drying Methods 0.000 description 13
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 11
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 238000011109 contamination Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 229930185605 Bisphenol Natural products 0.000 description 8
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000008098 formaldehyde solution Substances 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 229920005610 lignin Polymers 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 4
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 4
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 4
- 235000010265 sodium sulphite Nutrition 0.000 description 4
- 239000000986 disperse dye Substances 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 3
- 229940001607 sodium bisulfite Drugs 0.000 description 3
- -1 4'-dihydroxybiphenyl Chemical compound 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- IDCBOTIENDVCBQ-UHFFFAOYSA-N TEPP Chemical compound CCOP(=O)(OCC)OP(=O)(OCC)OCC IDCBOTIENDVCBQ-UHFFFAOYSA-N 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 239000013068 control sample Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 229940001482 sodium sulfite Drugs 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 2
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 1
- GEQWCUVIQMRCAZ-UHFFFAOYSA-N 2-(4-hydroxyphenyl)butanoic acid Chemical compound CCC(C(O)=O)C1=CC=C(O)C=C1 GEQWCUVIQMRCAZ-UHFFFAOYSA-N 0.000 description 1
- FEVVTKCAZXCXEQ-UHFFFAOYSA-N 2-(4-hydroxyphenyl)pentanoic acid Chemical compound CCCC(C(O)=O)C1=CC=C(O)C=C1 FEVVTKCAZXCXEQ-UHFFFAOYSA-N 0.000 description 1
- RXNYJUSEXLAVNQ-UHFFFAOYSA-N 4,4'-Dihydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1 RXNYJUSEXLAVNQ-UHFFFAOYSA-N 0.000 description 1
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 1
- NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 1
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 108010024636 Glutathione Proteins 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
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- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
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- 238000007605 air drying Methods 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229940124277 aminobutyric acid Drugs 0.000 description 1
- 229960002684 aminocaproic acid Drugs 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 229960003180 glutathione Drugs 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000007965 phenolic acids Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
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- 150000003839 salts Chemical class 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
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- Coloring (AREA)
Description
【０００１】
【発明の属する技術分野】
本発明は、染料分散剤に関するものであり、特に高温染色性に優れ、しかもスプレードライ適性、汚染性、還元退色性に優れた分散剤に関する。
【０００２】
【従来の技術】
従来からポリエステル繊維等の染色を目的として分散染料が使用されている。これは分散染料の染料自身は、水に不溶、あるいは難溶であるため、分散剤を用いて水に安定に分散できるようにしたものである。この場合の分散剤として、主として部分脱スルホンリグニンスルホン酸やナフタレンスルホン酸ホルムアルデヒド縮合物が使用されてきた。
【０００３】
【発明が解決しようとする課題】
部分脱スルホンリグニンスルホン酸は、ポリエステル繊維等の染色のような高温染色時において良好な染色性（高温染色性）を示し、染料分散物としたときに良好なスプレードライ適性を示す。しかしながら、布を汚染する傾向があり、またアゾ系の染料に対しては、リグニンスルホン酸の構成成分中に染料を還元してしまうものが存在し、色の退色が起きる場合がある。
【０００４】
また、ナフタレンスルホン酸ホルムアルデヒド縮合物は、布への汚染性は少なく還元退色も起こさないが、高温染色性及びスプレードライ適性に著しく劣るという問題がある。
【０００５】
近年、スプレードライ適性、汚染性、還元退色性がいずれも良好な分散剤として、ビスフェノール類と亜硫酸塩のホルムアルデヒド縮合物が提案されている（特公平６−７４３８７号公報）。しかしながら上記の縮合物は、汚染性、還元退色性がいずれも良好であり、スプレードライ適性もナフタレンスルホン酸ホルムアルデヒド縮合物と比べ改善されているが、高温染色性が部分脱スルホンリグニンスルホン酸と比べると未だ不十分であるという欠点を有していた。
【０００６】
従って、本発明の目的は、汚染性、還元退色性、スプレードライ適性、高温染色性がいずれも優れた染料分散剤を提供することにある。
【０００７】
【課題を解決するための手段】
そこで、本発明者らは、種々検討の結果、（ａ）ビスフェノール類、（ｂ）亜硫酸塩及びアミノカルボン酸の混合物、（ｃ）ホルムアルデヒドを反応モル比（ａ：ｂ：ｃ）１．０：０．４〜２．０：１．０〜４．０で水性下反応させて得られる縮合物の中で、その重量平均分子量が５００〜１００００であることを特徴とする染料分散剤により、汚染性、還元退色性、スプレードライ適性はいずれも良好なまま、高温染色性を大幅に改善できることを見出した。
【０００８】
本発明の上記の目的は、以下に示す縮合物からなる染料分散剤によって達成された。
【０００９】
【発明の実施の形態】
本発明に用いるビスフェノール類としては、２，２’−ビス（４−ヒドロキシフェニル）プロパン、４，４’−ジヒドロキシジフェニルメタン、４，４’−ジヒドロキシベンゾフェノン、４，４’−ジヒドロキシジフェニルスルホン、４，４’−ジヒドロキシビフェニル、４，４’−ジヒドロキシジフェニルエーテル、４，４’−ジヒドロキシジフェニルサルファイド、４，４’−エチリデン−ビスフェノール、４，４’−ビス（４−ヒドロキシフェニル）吉草酸、４，４’−ビス（４−ヒドロキシフェニル）酪酸及びそれらの異性体が好んで用いられ、これらを組み合わせて用いることもできるが、２，２’−ビス（４−ヒドロキシフェニル）プロパンが性能面に優れ、安価であることから最も好ましい。また、ビスフェノール類については、ビスフェノール類の単独使用のみならずフェノール類、例えばフェノール、フェノールスルホン酸、フェノールカルボン酸等との併用も可能である。
【００１０】
本発明で用いる亜硫酸塩としては、亜硫酸ナトリウム、亜硫酸水素ナトリウム、ピロ亜硫酸ナトリウム等が挙げられる。
【００１１】
本発明で用いられるアミノカルボン酸は、低分子量のアミノ酸であり、例えばグルタミン酸、グリシン、イミノ二酢酸、アラニン、アスパラギン酸、セリン、アミノ酪酸、グルタチオン、アミノカプロン酸、バリン、フェニルアラニン、メチオニン、ロイシン等又はそれらの塩が挙げられ、これらを組み合わせて用いることもできるが、グルタミン酸ソーダが性能面に優れ、安価であることから最も好ましい。
【００１２】
亜硫酸塩及びアミノカルボン酸の混合物については、亜硫酸塩とアミノカルボン酸の混合比（モル比）は、９：１〜２：８の範囲が好ましい。この範囲より亜硫酸塩の混合割合が大きくなると、アミノカルボン酸の混合効果がなくなり好ましくない。逆にアミノカルボン酸の混合割合が大きくなっても高温分散性は悪化する。
【００１３】
亜硫酸塩及びアミノカルボン酸の混合物における亜硫酸塩とアミノカルボン酸の組み合わせについては、上記した化合物を任意に組み合わせられる。組み合わせ例としては、亜硫酸水素ナトリウムとグルタミン酸ナトリウム、亜硫酸ナトリウムとグルタミン酸ナトリウム、亜硫酸水素ナトリウムとイミノ二酢酸、亜硫酸ナトリウムとイミノ二酢酸などが挙げられるが、亜硫酸水素ナトリウムとグルタミン酸ナトリウム、亜硫酸ナトリウムとグルタミン酸ナトリウムの組み合わせが最も性能面に優れることから好ましい。
【００１４】
本発明において、（ａ）ビスフェノール類、（ｂ）亜硫酸塩及びアミノカルボン酸の混合物、（ｃ）ホルムアルデヒドとの反応モル比（ａ：ｂ：ｃ）は、 １．０：０．４〜２．０：１．０〜４．０、より好ましくは１．０：０．６〜 １．０：１．４〜２．０である。本発明指定のモル比を外して反応を行った場合、高温分散性が悪化する。
【００１５】
さらに、本発明の（ａ）ビスフェノール類、（ｂ）亜硫酸塩及びアミノカルボン酸の混合物、（ｃ）ホルムアルデヒドとの縮合物の重量平均分子量は５００〜１００００、より好ましくは１０００〜５０００に調製することが必要である。この重量平均分子量の調製は必要に応じ膜処理等を施して行うことができる。本発明の重量分子量範囲を外れると、高温分散性が悪化する。
【００１６】
重量平均分子量の測定は、ＧＰＣを用いて以下の条件で行う。
本発明の縮合物は、通常ナトリウム等のアルカリ金属塩をも包含する。
更に、縮合物合成時における条件を挙げておくと、合成は水性条件下（固形分濃度２０〜５０ｗｔ％）、常圧ないしは加圧下、温度３０℃〜１４０℃で通常４〜５０時間で行われる。また、合成時のｐＨは、６〜１１（必要に応じてアルカリを添加し、ｐＨを調整する）、ホルムアルデヒドの滴下は１〜２時間で行うことが望ましい。
【００１８】
【作用】
本発明の縮合物を用いると、汚染性、還元退色性、スプレードライ適性、高温染色性いずれも良好な染料分散剤を得ることができる。
特公平６−７４３８７号公報記載の従来のビスフェノール類と亜硫酸塩のホルムアルデヒド縮合物に比べて、高温染色性を改善できた理由については、アミノカルボン酸導入による縮合物の化学構造の変化にあると推測している。
【００１９】
【実施例】
以下、本発明を実施例にしたがって更に詳述するが、本発明はこれによって限定されるものではない。なお、縮合物の合成例中、配合量を示す「部」は重量部を示す。重量平均分子量はＭｗと略した。
【００２０】
（縮合物の合成実施例）
合成例１
撹拌装置、還流装置、ホルムアルデヒド水溶液滴下装置及び温度コントローラーのついた反応器に下記の物質を所定量仕込んだ。
この固液混合物を攪拌下、９０℃に加温後、ホルムアルデヒド１．５０モル（３７％ホルムアルデヒド水溶液１２１．６部）を１時間で滴下し、その後９０℃で１９時間反応させて合成例１の縮合物（Ｍｗ＝１０００）を得た。
【００２２】
合成例２
合成例１の縮合物調製と同様に下記の物質を所定量仕込んだ。
この固液混合物を攪拌下、９０℃に加温後、ホルムアルデヒド１．９０モル（３７％ホルムアルデヒド水溶液１５４．１部）を１時間で滴下し、その後９５℃で４０時間反応させて合成例２の縮合物（Ｍｗ＝７０００）を得た。
【００２４】
合成例３
合成例１の縮合物調製と同様に下記の物質を所定量仕込んだ。
この固液混合物を攪拌下、９０℃に加温後、ホルムアルデヒド２．４０モル（３７％ホルムアルデヒド水溶液１９４．６部）を１時間で滴下し、その後９５℃で３５時間反応させて合成例３の縮合物（Ｍｗ＝９０００）を得た。
【００２６】
合成例４
合成例１の縮合物調製と同様に下記の物質を所定量仕込んだ。
この固液混合物を攪拌下、９０℃に加温後、ホルムアルデヒド２．５０モル（３７％ホルムアルデヒド水溶液２０２．７部）を１時間で滴下し、その後１００℃で１６時間反応させて合成例４の縮合物（Ｍｗ＝１００００）を得た。
【００２８】
合成例５
合成例１の縮合物調製と同様に下記の物質を所定量仕込んだ。
この固液混合物を攪拌下、９０℃に加温後、ホルムアルデヒド２．３０モル（３７％ホルムアルデヒド水溶液１８６．５部）を１時間で滴下し、その後９０℃で１９時間反応させて合成例５の縮合物（Ｍｗ＝９０００）を得た。
【００３０】
合成例６
合成例１の縮合物調製と同様に下記の物質を所定量仕込んだ。
この固液混合物を攪拌下、８０℃に加温後、ホルムアルデヒド１．２０モル（３７％ホルムアルデヒド水溶液１１０．３部）を１時間で滴下し、その後８０℃で１５時間反応させて合成例６の縮合物（Ｍｗ＝８００）を得た。
【００３２】
合成例７
合成例１の縮合物調製と同様に下記の物質を所定量仕込んだ。
この固液混合物を攪拌下、９０℃に加温後、ホルムアルデヒド２．２０モル（３７％ホルムアルデヒド水溶液１７８．４部）を１時間で滴下し、その後８５℃で３０時間反応させて合成例７の縮合物（Ｍｗ＝８０００）を得た。
【００３４】
合成例８
合成例１の縮合物調製と同様に下記の物質を所定量仕込んだ。
この固液混合物を攪拌下、９０℃に加温後、ホルムアルデヒド１．７０モル（３７％ホルムアルデヒド水溶液１３７．８部）を１時間で滴下し、その後９０℃で２５時間反応させて合成例８の縮合物（Ｍｗ＝４０００）を得た。
【００３６】
（縮合物の合成比較例）
合成例９
合成例１の縮合物調製と同様に下記の物質を所定量仕込んだ。
この固液混合物を攪拌下、９０℃に加温後、ホルムアルデヒド３．００モル（３７％ホルムアルデヒド水溶液２４３．３部）を１時間で滴下し、その後１００℃で１０時間反応させて合成例９の縮合物（Ｍｗ＝１６０００）を得た。
【００３８】
合成例１０
合成例１の縮合物調製と同様に下記の物質を所定量仕込んだ。
この固液混合物を攪拌下、９０℃に加温後、ホルムアルデヒド３．００モル（３７％ホルムアルデヒド水溶液２４３．３部）を１時間で滴下し、その後１００℃で１０時間反応させて合成例１０の縮合物（Ｍｗ＝１５０００）を得た。
【００４０】
合成例１１
合成例１の縮合物調製と同様に下記の物質を所定量仕込んだ。
この固液混合物を攪拌下、９０℃に加温後、ホルムアルデヒド３．２０モル（３７％ホルムアルデヒド水溶液２５９．５部）を１時間で滴下し、その後１００℃で２０時間反応させて合成例１１の縮合物（Ｍｗ＝１８０００）を得た。
【００４２】
合成例１２
合成例１の縮合物調製と同様に下記の物質を所定量仕込んだ。
この固液混合物を攪拌下、９０℃に加温後、ホルムアルデヒド１．７０モル（３７％ホルムアルデヒド水溶液１３７．８部）を１時間で滴下し、その後１００℃で２０時間反応させて合成例１２の縮合物（Ｍｗ＝７０００）を得た。
【００４４】
合成例１３
合成例１の縮合物調製と同様に下記の物質を所定量仕込んだ。
この固液混合物を攪拌下、９０℃に加温後、ホルムアルデヒド４．５０モル（３７％ホルムアルデヒド水溶液３６４．９部）を１時間で滴下し、その後９０℃で２０時間反応させて合成例１３の縮合物（Ｍｗ＝１２０００）を得た。
【００４６】
合成例１４
合成例１の縮合物調製と同様に下記の物質を所定量仕込んだ。
この固液混合物を攪拌下、９０℃に加温後、ホルムアルデヒド１．５０モル（３７％ホルムアルデヒド水溶液１２１．６部）を１時間で滴下し、その後７０℃で１６時間反応させて合成例１４の縮合物（Ｍｗ＝４００）を得た。
【００４８】
実施例１（高温染色性試験）
ナフタレンスルホン酸ホルムアルデヒド縮合物と染料原体(C.I.Disperse Red 60）とが、固形分重量比で１：３の混合物に水を加え、攪拌後、ジューサーミキサー及びサンドミル（ガラスビーズ使用）で染料原体を微粒化し、染料破砕溶液（固形分２０％程度）を得る。次に各種分散剤溶液（固形分換算０．５ｇ）に、この染料破砕溶液（固形分換算０．８ｇ）及び水を加え、酢酸でｐＨ５．０に調整後、２５０mlにメスアップし、染色ポットに仕込む。次にポリエステルジャージ布１０ｇを内筒に巻き付けセットした染色用ホルダーを染色ポットに投入し、カラーペット染色機（日本染色機械（株）製）で染色を行った（１３０℃、１０分）。染色後急速に冷却し、直ちにポリエステルジャージ布を取り出して水洗し、風乾する。風乾後、ポリエステルジャージ布を取り出し、繊維上に付着した染料凝集物の多少を目視で以下のように１０段階評価した。結果を表１に示す。表中、ランク１０は最良の評価で凝集物の付着性が見られないもの、ランク１は最悪の評価で凝集物が著しく付着しているものを示す。
なお、試験に用いた分散剤は、合成例１〜１４の縮合物と、対照例としての部分脱スルホンリグニンスルホン酸（日本製紙（株）バニレックスＲＮを使用、以下ＬＩＧと略）、ナフタレンスルホン酸ホルムアルデヒド縮合物（日本製紙（株）バニオールＨＤ−２００を使用、以下ＮＳＦと略）である。
【００４９】
実施例２（スプレードライ適性）
合成例１〜１４の縮合物水溶液をスプレードライヤーで粉末化したもの、及び対照サンプルとしてＬＩＧ、ＮＳＦのスプレードライ適性の試験を行った。試験法は以下の通りである。
【００５０】
染料原体(C.I.Disperse Red 60）と分散剤とが固形分重量比で１：１の混合物に水を加え、撹拌後、ジューサーミキサーおよびサンドミル（ガラスビーズ使用）で染料原体を微粒化し、染料破砕溶液（固形分３０％程度）を得る。次にこれを濾布（テトロン／コットン混紡布（色洗社（株））で濾過して凝集物を取り除いた後に、スプレードライで乾燥し粉末とした（入口温度１０５〜１５０℃、出口温度５０〜５５℃）。その後スペック試験を行った。スペック試験は、スプレードライ適性を示す指標である。具体的には、上記スプレードライ粉末１０ｇを５００mlの温水（４０℃）に撹拌下溶解し、得られた水溶液を濾布（テトロン／コットン混紡布）で濾過し、凝集物付着の有無を黙視で判定した。凝集物の布への付着が少ないほどスプレードライ適性は良好となる。結果を表１に示した。
【００５１】
実施例３（汚染性試験）
合成例１〜１４の縮合物水溶液をスプレードライヤーで粉末化し、粉末化した試料を用いて布への汚染性の試験を行った。また、対照サンプルとして、ＬＩＧ、ＮＳＦの汚染性試験を同時に行った。汚染性の試験は、以下のとおりである。
【００５２】
分散剤６６０mg（固形分換算）を水に溶解し、酢酸を用いてｐＨ５．０に調整した後、全量を２５０mlとする。８ｇの試験布と共にカラーペット染色機に仕込み１３０℃にて１時間染色を行った後、試験布を乾燥し、白色度を測定する。得られた結果を表１に示した。
【００５３】
実施例４（還元退色性試験）
合成例１〜１４の縮合物水溶液をスプレードライヤーで粉末化したもの、及び対照サンプルとして、ＬＩＧ、ＮＳＦの還元退色性試験を行った。還元退色性試験は以下の通りである。
【００５４】
アゾ系分散染料原体と、分散剤（染料原体に対し４００％）に水を加え酢酸を用いてｐＨ５．０に調整した後、全量を２５０mlにする。８ｇのポリエステルジャージ布と共にカラーペット染色機に仕込み１３０℃で１時間染色した後、試験布を乾燥し還元退色性の比較を行った。結果を表１に示した。
【００５５】
【表１】
表１の結果より、本発明の染料分散剤が、汚染性、還元退色性、スプレードライ適性に加え、高温染色性も優れていることがわかる。
【００５７】
【発明の効果】
本発明の縮合物を用いると、汚染性、還元退色性、スプレードライ適性、高温染色性いずれも良好な染料分散剤を得ることができる。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a dye dispersant, and particularly relates to a dispersant excellent in high-temperature dyeability and excellent in spray drying suitability, stain resistance, and reduction fading.
[0002]
[Prior art]
Conventionally, disperse dyes have been used for the purpose of dyeing polyester fibers and the like. This is because the disperse dye itself is insoluble or hardly soluble in water, so that it can be stably dispersed in water using a dispersant. As the dispersant in this case, mainly partially desulfonated lignin sulfonic acid or naphthalene sulfonic acid formaldehyde condensate has been used.
[0003]
[Problems to be solved by the invention]
Partially desulfurized lignin sulfonic acid exhibits good dyeability (high temperature dyeability) at the time of high-temperature dyeing such as dyeing of polyester fibers and the like, and good spray-drying suitability when formed into a dye dispersion. However, there is a tendency to contaminate the cloth, and for azo dyes, some components of lignin sulfonic acid reduce the dye, and color fading may occur.
[0004]
Further, naphthalene sulfonic acid formaldehyde condensate has a problem that it has a low stainability to cloth and does not cause reductive fading, but has a problem that it is extremely inferior in high-temperature dyeability and spray-drying suitability.
[0005]
In recent years, formaldehyde condensates of bisphenols and sulfites have been proposed as dispersants having good spray-drying suitability, contamination properties, and reduction fading properties (Japanese Patent Publication No. 6-74387). However, the above-mentioned condensate has good contamination and reduction fading properties, and spray dryability is improved as compared with naphthalene sulfonic acid formaldehyde condensate, but high-temperature dyeing property is compared with partially desulfonated lignin sulfonic acid. And still have the disadvantage of being insufficient.
[0006]
Accordingly, an object of the present invention is to provide a dye dispersant which is excellent in all of stain resistance, reduction fading property, spray drying suitability and high temperature dyeability.
[0007]
[Means for Solving the Problems]
Therefore, as a result of various studies, the present inventors have investigated (a) bisphenols, (b) a mixture of sulfite and aminocarboxylic acid, (c) formaldehyde with a reaction molar ratio (a: b: c) of 1.0: 0.4-2.0: Among condensates obtained by reacting in an aqueous solution at 1.0-4.0, contamination is caused by a dye dispersant having a weight average molecular weight of 500-10000. It has been found that the high-temperature dyeability can be greatly improved while all of the colorability, the reduction fading property, and the spray drying suitability are good.
[0008]
The above object of the present invention has been achieved by a dye dispersant comprising the condensate shown below.
[0009]
DETAILED DESCRIPTION OF THE INVENTION
Examples of bisphenols used in the present invention include 2,2′-bis (4-hydroxyphenyl) propane, 4,4′-dihydroxydiphenylmethane, 4,4′-dihydroxybenzophenone, 4,4′-dihydroxydiphenyl sulfone, 4'-dihydroxybiphenyl, 4,4'-dihydroxydiphenyl ether, 4,4'-dihydroxydiphenyl sulfide, 4,4'-ethylidene-bisphenol, 4,4'-bis (4-hydroxyphenyl) valeric acid, 4,4 '-Bis (4-hydroxyphenyl) butyric acid and isomers thereof are preferably used, and these may be used in combination, but 2,2'-bis (4-hydroxyphenyl) propane is excellent in performance, Most preferable because it is inexpensive. As for bisphenols, not only bisphenols can be used alone, but also phenols such as phenol, phenolsulfonic acid, phenolcarboxylic acid and the like can be used in combination.
[0010]
Examples of the sulfite used in the present invention include sodium sulfite, sodium hydrogen sulfite, and sodium pyrosulfite.
[0011]
The aminocarboxylic acid used in the present invention is a low molecular weight amino acid, such as glutamic acid, glycine, iminodiacetic acid, alanine, aspartic acid, serine, aminobutyric acid, glutathione, aminocaproic acid, valine, phenylalanine, methionine, leucine, etc. These salts can be mentioned, and these can be used in combination, but sodium glutamate is most preferable because of its excellent performance and low cost.
[0012]
Regarding the mixture of sulfite and aminocarboxylic acid, the mixing ratio (molar ratio) of sulfite and aminocarboxylic acid is preferably in the range of 9: 1 to 2: 8. When the mixing ratio of sulfite is larger than this range, the mixing effect of aminocarboxylic acid is lost, which is not preferable. Conversely, even if the mixing ratio of the aminocarboxylic acid is increased, the high temperature dispersibility is deteriorated.
[0013]
Regarding the combination of sulfite and aminocarboxylic acid in the mixture of sulfite and aminocarboxylic acid, the above-mentioned compounds can be arbitrarily combined. Examples of combinations include sodium bisulfite and sodium glutamate, sodium sulfite and sodium glutamate, sodium bisulfite and iminodiacetic acid, sodium sulfite and iminodiacetic acid, but sodium bisulfite and sodium glutamate, sodium sulfite and sodium glutamate This combination is preferable because it is most excellent in performance.
[0014]
In the present invention, the reaction molar ratio (a: b: c) with (a) bisphenols, (b) a mixture of sulfite and aminocarboxylic acid, and (c) formaldehyde is 1.0: 0.4-2. 0: 1.0 to 4.0, more preferably 1.0: 0.6 to 1.0: 1.4 to 2.0. When the reaction is carried out at a molar ratio specified by the present invention, the high-temperature dispersibility deteriorates.
[0015]
Furthermore, the weight average molecular weight of (a) bisphenols, (b) a mixture of sulfite and aminocarboxylic acid, and (c) a condensate with formaldehyde of the present invention is adjusted to 500 to 10,000, more preferably 1000 to 5,000. is required. The weight average molecular weight can be adjusted by performing a membrane treatment or the like as necessary. When the weight molecular weight range of the present invention is not satisfied, the high-temperature dispersibility deteriorates.
[0016]
The weight average molecular weight is measured using GPC under the following conditions.
The condensate of the present invention usually includes an alkali metal salt such as sodium.
Furthermore, the conditions at the time of synthesizing the condensate will be mentioned. The synthesis is carried out under aqueous conditions (solid content concentration: 20 to 50 wt%), at normal pressure or under pressure, at a temperature of 30 ° C. to 140 ° C., usually for 4 to 50 hours. . The pH during synthesis is preferably 6 to 11 (adding alkali as necessary to adjust the pH), and formaldehyde is preferably added dropwise for 1 to 2 hours.
[0018]
[Action]
When the condensate of the present invention is used, a dye dispersant having good contamination, reduction fading, spray drying suitability, and high-temperature dyeability can be obtained.
Compared to the conventional formaldehyde condensates of bisphenols and sulfites described in Japanese Patent Publication No. 6-74387, the reason why the high-temperature dyeability can be improved is that the chemical structure of the condensates is changed by the introduction of aminocarboxylic acid. I guess.
[0019]
【Example】
EXAMPLES Hereinafter, although this invention is explained in full detail according to an Example, this invention is not limited by this. In addition, in the synthesis examples of the condensate, “part” indicating the blending amount indicates part by weight. The weight average molecular weight was abbreviated as Mw.
[0020]
(Synthesis Example of Condensate)
Synthesis example 1
A predetermined amount of the following substances was charged into a reactor equipped with a stirrer, a reflux device, a formaldehyde aqueous solution dropping device, and a temperature controller.
The solid-liquid mixture was heated to 90 ° C. with stirring, and 1.50 mol of formaldehyde (121.6 parts of 37% formaldehyde aqueous solution) was added dropwise over 1 hour, followed by reaction at 90 ° C. for 19 hours. A condensate (Mw = 1000) was obtained.
[0022]
Synthesis example 2
In the same manner as in the preparation of the condensate of Synthesis Example 1, the following substances were charged in predetermined amounts.
The solid-liquid mixture was heated to 90 ° C. with stirring, and 1.90 mol of formaldehyde (154.1 parts of 37% formaldehyde aqueous solution) was added dropwise over 1 hour, followed by reaction at 95 ° C. for 40 hours to A condensate (Mw = 7000) was obtained.
[0024]
Synthesis example 3
In the same manner as in the preparation of the condensate of Synthesis Example 1, the following substances were charged in predetermined amounts.
The solid-liquid mixture was heated to 90 ° C. with stirring, and 2.40 mol of formaldehyde (194.6 parts of 37% formaldehyde aqueous solution) was added dropwise over 1 hour, followed by reaction at 95 ° C. for 35 hours to A condensate (Mw = 9000) was obtained.
[0026]
Synthesis example 4
In the same manner as in the preparation of the condensate of Synthesis Example 1, the following substances were charged in predetermined amounts.
The solid-liquid mixture was heated to 90 ° C. with stirring, and then 2.50 mol of formaldehyde (202.7 parts of 37% aqueous formaldehyde solution) was added dropwise over 1 hour, followed by reaction at 100 ° C. for 16 hours to A condensate (Mw = 10000) was obtained.
[0028]
Synthesis example 5
In the same manner as in the preparation of the condensate of Synthesis Example 1, the following substances were charged in predetermined amounts.
The solid-liquid mixture was heated to 90 ° C. with stirring, and then 2.30 mol of formaldehyde (186.5 parts of 37% aqueous formaldehyde solution) was added dropwise over 1 hour, followed by reaction at 90 ° C. for 19 hours to A condensate (Mw = 9000) was obtained.
[0030]
Synthesis Example 6
In the same manner as in the preparation of the condensate of Synthesis Example 1, the following substances were charged in predetermined amounts.
The solid-liquid mixture was heated to 80 ° C. with stirring, and then 1.20 mol of formaldehyde (110.3 parts of 37% aqueous formaldehyde solution) was added dropwise over 1 hour, followed by reaction at 80 ° C. for 15 hours. A condensate (Mw = 800) was obtained.
[0032]
Synthesis example 7
In the same manner as in the preparation of the condensate of Synthesis Example 1, the following substances were charged in predetermined amounts.
The solid-liquid mixture was heated to 90 ° C. with stirring, and 2.20 mol of formaldehyde (178.4 parts of 37% formaldehyde aqueous solution) was added dropwise over 1 hour, followed by reaction at 85 ° C. for 30 hours. A condensate (Mw = 8000) was obtained.
[0034]
Synthesis Example 8
In the same manner as in the preparation of the condensate of Synthesis Example 1, the following substances were charged in predetermined amounts.
The solid-liquid mixture was heated to 90 ° C. with stirring, and 1.70 mol of formaldehyde (137.8 parts of a 37% formaldehyde aqueous solution) was added dropwise over 1 hour, followed by reaction at 90 ° C. for 25 hours. A condensate (Mw = 4000) was obtained.
[0036]
(Synthesis comparison example of condensate)
Synthesis Example 9
In the same manner as in the preparation of the condensate of Synthesis Example 1, the following substances were charged in predetermined amounts.
The solid-liquid mixture was heated to 90 ° C. with stirring, and then 3.00 mol of formaldehyde (243.3 parts of 37% aqueous formaldehyde solution) was added dropwise over 1 hour, followed by reaction at 100 ° C. for 10 hours to A condensate (Mw = 16000) was obtained.
[0038]
Synthesis Example 10
In the same manner as in the preparation of the condensate of Synthesis Example 1, the following substances were charged in predetermined amounts.
This solid-liquid mixture was heated to 90 ° C. with stirring, and then 3.00 mol of formaldehyde (243.3 parts of 37% aqueous formaldehyde solution) was added dropwise over 1 hour, followed by reaction at 100 ° C. for 10 hours to A condensate (Mw = 15000) was obtained.
[0040]
Synthesis Example 11
In the same manner as in the preparation of the condensate of Synthesis Example 1, the following substances were charged in predetermined amounts.
The solid-liquid mixture was heated to 90 ° C. with stirring, and then 3.20 mol of formaldehyde (259.5 parts of 37% aqueous formaldehyde solution) was added dropwise over 1 hour, and then reacted at 100 ° C. for 20 hours to A condensate (Mw = 18000) was obtained.
[0042]
Synthesis Example 12
In the same manner as in the preparation of the condensate of Synthesis Example 1, the following substances were charged in predetermined amounts.
The solid-liquid mixture was heated to 90 ° C. with stirring, and 1.70 mol of formaldehyde (137.8 parts of 37% formaldehyde aqueous solution) was added dropwise over 1 hour, followed by reaction at 100 ° C. for 20 hours to A condensate (Mw = 7000) was obtained.
[0044]
Synthesis Example 13
In the same manner as in the preparation of the condensate of Synthesis Example 1, the following substances were charged in predetermined amounts.
The solid-liquid mixture was heated to 90 ° C. with stirring, and then 4.50 mol of formaldehyde (364.9 parts of a 37% aqueous formaldehyde solution) was added dropwise over 1 hour, followed by reaction at 90 ° C. for 20 hours. A condensate (Mw = 12000) was obtained.
[0046]
Synthesis Example 14
In the same manner as in the preparation of the condensate of Synthesis Example 1, the following substances were charged in predetermined amounts.
The solid-liquid mixture was heated to 90 ° C. with stirring, and 1.50 mol of formaldehyde (121.6 parts of 37% formaldehyde aqueous solution) was added dropwise over 1 hour, followed by reaction at 70 ° C. for 16 hours to A condensate (Mw = 400) was obtained.
[0048]
Example 1 (High-temperature dyeability test)
Naphthalenesulfonic acid formaldehyde condensate and dye base (CIDisperse Red 60) are added to a 1: 3 solids weight ratio of water, stirred, and then mixed with a juicer mixer and sand mill (using glass beads). Atomized to obtain a dye crushing solution (solid content of about 20%). Next, this dye crushing solution (solid content conversion 0.8g) and water are added to various dispersant solutions (solid content conversion 0.5g), adjusted to pH 5.0 with acetic acid, made up to 250ml, and dyeing pot Prepare. Next, a dyeing holder in which 10 g of a polyester jersey cloth was wound around an inner cylinder was put into a dyeing pot and dyed with a color pet dyeing machine (manufactured by Nippon Dyeing Machinery Co., Ltd.) (130 ° C., 10 minutes). Cool quickly after dyeing, immediately remove the polyester jersey cloth, wash with water and air dry. After air-drying, the polyester jersey cloth was taken out, and the degree of dye agglomerates adhering to the fiber was visually evaluated in 10 stages as follows. The results are shown in Table 1. In the table, rank 10 indicates that no adhesion of the aggregate is observed in the best evaluation, and rank 1 indicates that the aggregation is remarkably adhered in the worst evaluation.
In addition, the dispersing agent used for the test was a condensate of Synthesis Examples 1 to 14, partially desulfonated lignin sulfonic acid (using Nippon Paper Industries Co., Ltd. Vanillex RN, hereinafter abbreviated as LIG), naphthalene sulfonic acid. It is a formaldehyde condensate (Nippon Paper Co., Ltd. Vaniol HD-200, hereinafter abbreviated as NSF).
[0049]
Example 2 (Spray dry suitability)
The condensate aqueous solutions of Synthesis Examples 1 to 14 were pulverized with a spray dryer, and LIG and NSF were tested for spray drying suitability as control samples. The test method is as follows.
[0050]
Water is added to a mixture of the dye base (CIDisperse Red 60) and the dispersant in a solid weight ratio of 1: 1. After stirring, the dye base is atomized with a juicer mixer and sand mill (using glass beads), and the dye is crushed. A solution (solid content of about 30%) is obtained. Next, this was filtered through a filter cloth (Tetron / Cotton blended cloth (Color Wash Co., Ltd.) to remove aggregates, and then dried by spray drying to obtain a powder (inlet temperature 105 to 150 ° C., outlet temperature 50). After that, a spec test was conducted, which is an indicator of spray drying suitability.Specifically, 10 g of the spray dry powder was dissolved in 500 ml of warm water (40 ° C.) with stirring. The resulting aqueous solution was filtered through a filter cloth (Tetron / cotton blended cloth), and the presence or absence of aggregates was determined with unaided eye.The less the aggregates adhered to the cloth, the better the spray drying suitability. It was shown to.
[0051]
Example 3 (Contamination test)
The aqueous condensate solutions of Synthesis Examples 1 to 14 were pulverized with a spray dryer, and the fabric contamination test was performed using the pulverized sample. Moreover, the contamination test of LIG and NSF was performed simultaneously as a control sample. Contamination tests are as follows.
[0052]
660 mg (in terms of solid content) of the dispersant is dissolved in water, adjusted to pH 5.0 with acetic acid, and the total amount is 250 ml. After charging into a color pet dyeing machine together with 8 g of test cloth and dyeing at 130 ° C. for 1 hour, the test cloth is dried and the whiteness is measured. The obtained results are shown in Table 1.
[0053]
Example 4 (Reduction Fading Test)
As a control sample prepared by pulverizing the aqueous condensate solutions of Synthesis Examples 1 to 14 with a spray dryer, LIG and NSF reduction fading tests were performed. The reduction fading test is as follows.
[0054]
Water is added to the azo-based disperse dye base and the dispersant (400% with respect to the dye base), and the pH is adjusted to 5.0 with acetic acid, and the total amount is adjusted to 250 ml. After being charged into a color pet dyeing machine together with 8 g of polyester jersey cloth and dyed at 130 ° C. for 1 hour, the test cloth was dried and compared for reduction fading. The results are shown in Table 1.
[0055]
[Table 1]
From the results shown in Table 1, it can be seen that the dye dispersant of the present invention is excellent in high-temperature dyeability in addition to stainability, reduction fading property, and spray drying suitability.
[0057]
【The invention's effect】
When the condensate of the present invention is used, a dye dispersant having good contamination, reduction fading, spray drying suitability, and high-temperature dyeability can be obtained.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP36702097A JP4187295B2 (en) | 1997-12-25 | 1997-12-25 | Dye dispersant |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP36702097A JP4187295B2 (en) | 1997-12-25 | 1997-12-25 | Dye dispersant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH11181316A JPH11181316A (en) | 1999-07-06 |
| JP4187295B2 true JP4187295B2 (en) | 2008-11-26 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP36702097A Expired - Fee Related JP4187295B2 (en) | 1997-12-25 | 1997-12-25 | Dye dispersant |
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| Country | Link |
|---|---|
| JP (1) | JP4187295B2 (en) |
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| JPH11181316A (en) | 1999-07-06 |
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