JPH01266287A - Coloring method for saponified product of ethylene/ vinylacetate copolymer and colored product - Google Patents
Coloring method for saponified product of ethylene/ vinylacetate copolymer and colored productInfo
- Publication number
- JPH01266287A JPH01266287A JP63093799A JP9379988A JPH01266287A JP H01266287 A JPH01266287 A JP H01266287A JP 63093799 A JP63093799 A JP 63093799A JP 9379988 A JP9379988 A JP 9379988A JP H01266287 A JPH01266287 A JP H01266287A
- Authority
- JP
- Japan
- Prior art keywords
- coloring
- ethylene
- colored
- product
- organic solvent
- 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.)
- Pending
Links
- 238000004040 coloring Methods 0.000 title claims abstract description 31
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 239000005977 Ethylene Substances 0.000 title claims abstract description 13
- 229920001577 copolymer Polymers 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 title claims description 18
- 229940117958 vinyl acetate Drugs 0.000 title abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000000986 disperse dye Substances 0.000 claims abstract description 18
- 239000003960 organic solvent Substances 0.000 claims abstract description 15
- 239000002736 nonionic surfactant Substances 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 239000000975 dye Substances 0.000 abstract description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 11
- 150000001298 alcohols Chemical class 0.000 abstract description 2
- 239000007788 liquid Substances 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 1
- 229920000219 Ethylene vinyl alcohol Polymers 0.000 description 23
- UFRKOOWSQGXVKV-UHFFFAOYSA-N ethene;ethenol Chemical compound C=C.OC=C UFRKOOWSQGXVKV-UHFFFAOYSA-N 0.000 description 23
- 239000004715 ethylene vinyl alcohol Substances 0.000 description 23
- 239000000843 powder Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 8
- 239000008187 granular material Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000004043 dyeing Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- CZNYJWQJSGRKRA-UHFFFAOYSA-N 2-[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]aniline Chemical compound NC1=CC=CC=C1C1=NN=C(C=2C=CC(Cl)=CC=2)O1 CZNYJWQJSGRKRA-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- VGKYEIFFSOPYEW-UHFFFAOYSA-N 2-methyl-4-[(4-phenyldiazenylphenyl)diazenyl]phenol Chemical compound Cc1cc(ccc1O)N=Nc1ccc(cc1)N=Nc1ccccc1 VGKYEIFFSOPYEW-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- BHOOSPBGGKYHCM-UHFFFAOYSA-N 3-[4-[(2-chloro-4-nitrophenyl)diazenyl]-n-ethyl-3-methylanilino]propanenitrile Chemical compound CC1=CC(N(CCC#N)CC)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1Cl BHOOSPBGGKYHCM-UHFFFAOYSA-N 0.000 description 1
- FOQABOMYTOFLPZ-ISLYRVAYSA-N Disperse Red 1 Chemical compound C1=CC(N(CCO)CC)=CC=C1\N=N\C1=CC=C([N+]([O-])=O)C=C1 FOQABOMYTOFLPZ-ISLYRVAYSA-N 0.000 description 1
- 239000004831 Hot glue Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000000981 basic dye Substances 0.000 description 1
- 239000001752 chlorophylls and chlorophyllins Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- 238000004044 disperse dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- OMRDZQXXMYCHBU-UHFFFAOYSA-N ethanol;propan-1-ol Chemical compound CCO.CCCO OMRDZQXXMYCHBU-UHFFFAOYSA-N 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000005340 laminated glass Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- -1 octatool Chemical compound 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Landscapes
- Coloring (AREA)
Abstract
Description
【発明の詳細な説明】
イ、産業上の利用分野
本発明はエチレン／ビニルアセテート共重合体のケン化
物（以下ＥＶＯＨという）、さらに詳しくは粒状、粉状
のＥＶＯＨの着色に関し、また分散染料を用いて着色し
たＥＶＯＨを提供する事に関する。該着色物はホットメ
ルト接着用、破瓶防止用、合わせ硝子用、着色フィルム
用、特殊加工紙用、粉体塗料用、その他ＥＶＯＨの接着
性、バリヤー性、耐久性、耐薬品性を応用した産業分野
に有用な素材を提供するものである。Detailed Description of the Invention A. Field of Industrial Application The present invention relates to the coloring of saponified ethylene/vinyl acetate copolymers (hereinafter referred to as EVOH), more specifically to the coloring of granular and powdered EVOH, and also to the coloring of granular and powdered EVOH. It relates to providing colored EVOH using The colored products are used for hot melt adhesives, bottle breakage prevention, laminated glass, colored films, specially processed paper, powder coatings, and other applications that utilize EVOH's adhesive properties, barrier properties, durability, and chemical resistance. It provides useful materials for industrial fields.
ロ、従来の技術
ＥＶＯＨの着色方法としては、ＥＶＯＨを溶融させ、こ
れに顔料などの色素を加え、練り合わせたのち、目的に
応じた形態に成形するのが一般である。この方法による
とＥ Ｖ ＯＨは一旦溶融操作を経過するため、操作が
煩雑で熱エネルギー的にも経済的でない。B. Conventional technology The general method for coloring EVOH is to melt the EVOH, add a dye such as a pigment to it, knead it, and then mold it into a shape according to the purpose. According to this method, EV OH undergoes a melting operation once, so the operation is complicated and it is not economical in terms of thermal energy.
ＥＶＯＨを溶融することなく粒状または粉状等の固形状
のままその内部まで均一に着色する方法はこれまで見当
らない。Until now, no method has been found to uniformly color the inside of EVOH in a solid form such as granules or powder without melting it.
ハ１発明が解決しようとする課題
本発明の目的は特定着色肘で固形物の内部まで濃色かつ
均一に着色した。Ｅ Ｖ ＯＨを提供することである。C1 Problems to be Solved by the Invention The object of the present invention is to color a solid material deeply and uniformly to the inside using a specific coloring method. It is to provide EV OH.
第二の目的は第一の目的をうるためにＥＶＯＨを粒状ま
たは粉状等の固形状のままで着色する方法を確立するこ
とである。The second objective is to establish a method for coloring EVOH in a solid form such as granules or powder in order to achieve the first objective.
二０課題を解決するための手段
本発明者らは粒状または粉状等のＥＶＯＨを溶解または
溶融等の変形を伴わずかつ濃色に均一着色するために、
カラーインデックス（ソサエティオブ ダイヤーズカラ
リスト発行）の分類方式に基ずく、直接染料、酸性染料
、塩基性染料、反応性染料、分散染料を用い水系で染色
を行った。20 Means for Solving the Problems The present inventors have developed a method for uniformly coloring granular or powdered EVOH into a dark color without involving deformation such as melting or melting.
Dyeing was done in water using direct dyes, acid dyes, basic dyes, reactive dyes, and disperse dyes based on the classification system of Color Index (published by Society of Dyers Colorists).
これらの染料のうち、分散染料の一部は水溶媒中でＥＶ
ＯＨを不充分ながら着色することを見出したが、濃色で
かつ均一な着色物をうる事は出来なかった。Among these dyes, some of the disperse dyes have EV in water solvent.
Although it was found that coloring could be achieved with insufficient OH, it was not possible to obtain a dark and uniformly colored product.
本発明者らは、分散染料による粒状または粉状等のＥＶ
ＯＨの、濃色かつ均一な着色方法について、鋭意検討し
たところ、水溶媒中の着色方法に代え、水と親水性有機
溶媒との混合溶媒中で、好ましくはノニオン系界面活性
剤の共存下で着色操作を実施する事により、はとんどの
分散染料について再現性よく、いちぢるしく濃色にかつ
均一に固体の内部まで着色することを見出し、本発明を
完成させるにいたった。すなわち、本発明は
（１）水と親水性有機溶剤との混合液中で分散染料によ
って着色処理を行うことを特徴とするエチレン／ビニル
アセテート共重合体のケン化物の着色方法。The present inventors have developed EVs in granular or powder form using disperse dyes.
After extensive research into a method for coloring OH in a deep and uniform color, we found that instead of coloring in an aqueous solvent, we could use a method for coloring OH in a mixed solvent of water and a hydrophilic organic solvent, preferably in the coexistence of a nonionic surfactant. By carrying out the coloring operation, it was discovered that most disperse dyes can be reproducibly colored in a strikingly deep color and uniformly to the inside of a solid, leading to the completion of the present invention. That is, the present invention provides (1) a method for coloring a saponified product of ethylene/vinyl acetate copolymer, which is characterized by carrying out coloring treatment with a disperse dye in a mixture of water and a hydrophilic organic solvent.
（２）水と親水性有機溶剤及びノニオン系界面活性剤と
の混合液中で分散染料によって着色処理を行うことを特
徴とするエチレン／ビニルアセテート共重合体のケン化
物の着色方法。(2) A method for coloring a saponified product of an ethylene/vinyl acetate copolymer, which is characterized by carrying out a coloring treatment using a disperse dye in a mixture of water, a hydrophilic organic solvent, and a nonionic surfactant.
（３）分散染料によって着色されたエチレン／ビニルア
セテート共重合体のケン化物。(3) A saponified product of ethylene/vinyl acetate copolymer colored with a disperse dye.
である。It is.
発明に使用されるＥＶＯＨはエチレン含有量２０〜９０
モル％、ケン化率５０〜１００％の通常市場に用いられ
るＥＶＯＨが適する。The EVOH used in the invention has an ethylene content of 20 to 90
EVOH which is commonly used in the market and has a saponification rate of 50 to 100% by mole is suitable.
本発明で用い得る分散染軌はカラーインデックスの分散
染料の項に記載゛されているような染料であり、要望す
る色相と堅牢度に適する染料を選択し単一または複数の
染料を混合し採用することができる。好適には Ｄｉｓ
ｐｅｒｓｅ Ｙｅｌｌｏｗ ８２、Ｙｅｌｌｏｗ５、Ｙ
ｅｌｌｏｗ ６４、Ｙｅｌｌｏｗ ７６、 Ｄｉｓｐｅ
ｒｓｅ Ｒｅｄ ６５、Ｒｅｄ １４６、Ｒｅｄ ３４
８’％Ｒｅｄ ９２、Ｄｉｓｐｅｒｓｅ Ｂｌｕｅ ５
６゜Ｂｌｕｅ ８７：１等が挙げられる。Disperse dyeing patterns that can be used in the present invention are those listed in the disperse dye section of the Color Index, and dyes suitable for the desired hue and fastness are selected and a single or multiple dyes are mixed and employed. can do. Preferably Dis
perse Yellow 82, Yellow5, Y
yellow 64, yellow 76, Dispe
rse Red 65, Red 146, Red 34
8'% Red 92, Disperse Blue 5
Examples include 6°Blue 87:1.
本発明で用い得る親水性有機溶媒は水に溶解する有機溶
媒であり、好ましい例としては０１〜Ｃ１のアルコール
、Ｃ２〜Ｃ８のケトンおよびそれらの誘導体であり、具
体的には例えばメタノール、エタノールプロパノール、
ブタノール、オクタツールやアセトン、メチルエチルケ
トン、メチルイソブチルケトンであり、又エチレングリ
コール、プロピレングリコール、低重合ポリエチレング
リコール、低重合ポリプロピレングリコール、メチルセ
ロソルブ、エチルセロソルブ等が挙げられ、単一または
併用することができる。The hydrophilic organic solvent that can be used in the present invention is an organic solvent that dissolves in water, and preferable examples include alcohols of 01 to C1, ketones of C2 to C8, and derivatives thereof, and specific examples include methanol, ethanol propanol, etc. ,
These include butanol, octatool, acetone, methyl ethyl ketone, methyl isobutyl ketone, and ethylene glycol, propylene glycol, low polymerization polyethylene glycol, low polymerization polypropylene glycol, methyl cellosolve, ethyl cellosolve, etc., which can be used alone or in combination. .
またノニオン系界面活性剤としては例えば、スコアロー
ル１００．スコアロール４００．レベノールＣ−２００
、レバノールＮ−コンク、エマルケン１０４９．エマル
ゲン１４７（以上花王石鹸社製）、エバン４５０、ノイ
ゲンＥ＾１２０、ノイゲンＥ１４０（以上第一工業製薬
社製）、イオネットＬＤ−７（三洋化成社製）である。Examples of nonionic surfactants include Score Roll 100. Score roll 400. Lebenol C-200
, Levanol N-Conc, Emarken 1049. These are Emulgen 147 (manufactured by Kao Soap Co., Ltd.), Evan 450, Neugen E^120, Neugen E140 (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.), and Ionet LD-7 (manufactured by Sanyo Chemical Co., Ltd.).
本発明の着色方法に関して、水と親水性有機溶媒の混合
割合は任意でよいが、混合したときに、水層と有機溶媒
層が分離しない範囲であるような混合割合であることが
好ましい、ノニオン系界面活性剤の添加量は特に限定し
ないが、好ましくは着色しようとすＥＶＯＨの０．０５
〜０．５重量％である。また分散染料の使用量は目的と
する着色物の要望する濃度によって定まるところである
が、本発明の方法によれば、着色しようとするＥＶＯＨ
の０．３〜２．０％を用いることにより、充分なる濃色
の着色物をうる。Regarding the coloring method of the present invention, the mixing ratio of water and the hydrophilic organic solvent may be arbitrary, but it is preferable that the mixing ratio is such that the water layer and the organic solvent layer do not separate when mixed. The amount of the surfactant added is not particularly limited, but is preferably 0.05 of the EVOH to be colored.
~0.5% by weight. Furthermore, the amount of disperse dye to be used is determined depending on the desired concentration of the intended colored product, but according to the method of the present invention, the amount of disperse dye to be colored is
By using 0.3 to 2.0% of the amount, a sufficiently deep colored product can be obtained.
水と親水性有機溶媒との混合液または水と親水性有機溶
媒及びノニオン系界面活性剤との混合液に分散染料を分
散または溶解した染浴に粒状または粉状のＥＶＯＨを浸
漬し着色するが、染浴は被着色物と同量乃至５倍比とす
るのが好ましく、着色処理温度はＥＶＯＨの物性や形態
を損わない程度に高温が好ましいが、さらに好適に４０
〜６０℃の範囲である。ＥＶＯＨをか−る条件で着色処
理すれば約２０〜３０分間で染料のほとんど大部分がＥ
ＶＯＨ側に吸尽され目的を達することができる。かくし
て得られた着色物はこれを取出し、必要に応じて水洗し
たのち乾燥する。Granular or powdered EVOH is immersed in a dye bath in which a disperse dye is dispersed or dissolved in a mixture of water and a hydrophilic organic solvent or a mixture of water, a hydrophilic organic solvent, and a nonionic surfactant, and colored. The dye bath is preferably used in the same amount to 5 times the ratio of the material to be colored, and the coloring treatment temperature is preferably high enough not to impair the physical properties and form of EVOH, but more preferably 40%
It is in the range of ~60°C. If EVOH is colored under these conditions, most of the dye will be converted to E in about 20 to 30 minutes.
The goal can be achieved by being exhausted by the VOH side. The colored material thus obtained is taken out, washed with water if necessary, and then dried.
ホ０発明の効果
本発明によれば、得られたＥＶＯＨの着色物は粒状また
は粉状の内部まで均一に着色していて、通常の水溶媒に
よる室温〜１３０℃の染色ではとうてい果たし得なかっ
た欠点を克服することができた。また１本発明の方法は
着色温度が４０〜６０℃でよく、通常分散染料で着色す
る場合の温度よりいちぢるしく低温でかつ２０乃至３０
分という短時間で染料が吸尽するという大きな特徴を有
していて、省エネルギー、着色操作時間の短縮という工
業的にも経済的にも極めて有意義な染色方法を提供した
。Effects of the Invention According to the present invention, the EVOH colored product obtained is uniformly colored even inside the granules or powder, which cannot be achieved by dyeing with a normal water solvent at room temperature to 130°C. I was able to overcome my shortcomings. In addition, in the method of the present invention, the coloring temperature may be 40 to 60°C, which is much lower than the temperature normally used when coloring with disperse dyes, and the coloring temperature is 20 to 30°C.
It has the great feature that the dye is exhausted in a short time of minutes, and it provides a dyeing method that is extremely meaningful both industrially and economically, saving energy and shortening the coloring operation time.
本発明によってえられる染着物は原料Ｅ Ｖ ＯＨの物
理的な性状を損うことなく鮮明でかつ均一に固形物の内
部まで着色しているためこれを用いてフィルムその他の
成形加工をする場合には容易かっ安定な操作で実施する
ことが出来、得られた成形物も従来にみられない視覚的
な付加価値をもち産業上極めて有用な素材を提供する。The dyed product obtained by the present invention is vividly and uniformly colored to the inside of the solid material without impairing the physical properties of the raw material EV OH, so it can be used to form films or other products. The method can be carried out easily and stably, and the molded product obtained has visual added value that has not been seen before, and provides an extremely useful material industrially.
へ、実施例
次に実施例を示すが本発明は実施例に限定されるもので
はない。EXAMPLES Next, examples will be shown, but the present invention is not limited to these examples.
実施例１
水３００ｍ１及びアセトン１００ｍ１の混合液にＣ，Ｉ
。Example 1 Add C and I to a mixture of 300 ml of water and 100 ml of acetone.
.
ＤＬｓｐｅｒｓｅ Ｒｅｄ １４６（スミカロン ブリ
リアントレッドＳＦ！−ＢＬ、住人化学工業製）０．５
ｇを分散した。DLsperse Red 146 (Sumikaron Brilliant Red SF!-BL, manufactured by Sumika Chemical Industry) 0.5
g was dispersed.
粉状スミリンクＤＲ−１５０（住友化学工業ＩＩＩＥＶ
ＯＨ）１００ｇを浸漬し、５０〜５５℃に３０分間ゆっ
くりかきまぜたところ染料は略完全に粉状物の染着に消
費された。ろ過、水洗、乾燥して鮮明な均一赤色粉状物
１００ｇが得られた。この着色物を１５０〜１６０℃に
溶融し、厚さ０ 、５ｍｍの美麗な赤色フィルムとした
が均一に着色されており耐熱性耐光性が優れていた。Powdered Sumilink DR-150 (Sumitomo Chemical IIIEV
When 100 g of OH) was immersed and slowly stirred at 50 to 55°C for 30 minutes, the dye was almost completely consumed for dyeing the powder. After filtering, washing with water, and drying, 100 g of a clear uniform red powder was obtained. This colored product was melted at 150 to 160°C to form a beautiful red film with a thickness of 0.5 mm, which was uniformly colored and had excellent heat resistance and light resistance.
比較例１゜
実施例１においてアセトン１００ｍ１の代りに水１００
票１を加え同様に着色処理を５５〜６０℃に１時間行っ
たが殆ど着色できなかった。Comparative Example 1゜In Example 1, 100ml of water was replaced with 100ml of acetone.
Addition of No. 1 was carried out in the same manner for coloring at 55 to 60° C. for 1 hour, but almost no coloring could be achieved.
実施例２
水３００ｍ１とイソブタノール１００ｍ１の混合液を静
置して水層を分離した。水層にＣ，１，Ｄｉｓｐｅｒｓ
ｅＹｅｌｌｏｗ ６４（スミカロンエロー５Ｒ−３ＧＬ
、住友化学工業！’ｌ）Ｏ，職を分散し粒状ＥＶＯＨ（
スミテートにＥ−１０住友化学工業製エチレン／ビニル
アセテートをアルカリでその９５％をケン化したもの）
１００ｇを浸漬し、５０〜５５℃に３０分間ゆっくりか
きまぜたのちろ過、水洗、乾燥した。鮮明な黄色透明粒
状物的１００ｇが得られた。Example 2 A mixed solution of 300 ml of water and 100 ml of isobutanol was left standing to separate the aqueous layer. C,1,Dispers in the water layer
eYellow 64 (Sumikaron Yellow 5R-3GL
, Sumitomo Chemical! 'l) O, dispersing the job and granular EVOH (
95% of Sumitate and E-10 Sumitomo Chemical ethylene/vinyl acetate saponified with alkali)
100 g was immersed, stirred slowly at 50 to 55°C for 30 minutes, filtered, washed with water, and dried. 100 g of bright yellow transparent granules were obtained.
実施例３〜１２
表１に示す水、親水性有機溶剤及び分散染料を使い、実
施例１の方法に準拠してＥＶＯＨを着色した。但し、ス
ミリンク０Ｒ−５５は住人化学工業製ＥＶＯＨである。Examples 3 to 12 EVOH was colored according to the method of Example 1 using water, a hydrophilic organic solvent, and a disperse dye shown in Table 1. However, Sumilink 0R-55 is EVOH manufactured by Sumitomo Chemical Industry.
実施例はいずれも鮮明均一濃色着色物を得た。In all of the examples, bright, uniform, deep colored products were obtained.
実施例１３
水３５０閣１及びアセトン３０ｍ１の混合液に Ｃ，Ｉ
。Example 13 C, I in a mixed solution of 350 ml of water and 30 ml of acetone
.
Ｄｉｓｐｅｒｓｅ Ｙｅｌｌｏｗ ６４（スミカロン
エロー５Ｅ−３ＧＬ住友化学工業製）０．５ｇを分散し
た。イオネットＬＤ−７（ノニオン系界面活性剤、三洋
化成社製）０．２ｇを添加し、５０〜５５℃で粉状スミ
リンクＤＲ−５５（住人化学工業製ＥＶＯＨ）１００ｇ
を浸漬し、３０分間ゆっくりかきまぜたところ染料は略
完全に粉状の着色に消費された。ろ過、水洗、乾燥して
鮮明な均一黄色粉状物１００ｇが得られた。Disperse Yellow 64 (Sumikaron)
0.5 g of Yellow 5E-3GL (manufactured by Sumitomo Chemical Industries) was dispersed. Add 0.2 g of Ionet LD-7 (nonionic surfactant, manufactured by Sanyo Chemical Co., Ltd.) and heat at 50 to 55°C to 100 g of powdered Sumilink DR-55 (EVOH manufactured by Sumima Chemical Industry Co., Ltd.).
When the dye was soaked and slowly stirred for 30 minutes, the dye was almost completely consumed into colored powder. After filtering, washing with water, and drying, 100 g of a clear uniform yellow powder was obtained.
この着色物を１６０〜１７０℃に溶融し、厚さ０．５ｍ
ｍの美麗な黄色フィルムを得た。耐熱性耐光性が優れて
いた。This colored material was melted at 160-170°C, and the thickness was 0.5 m.
A beautiful yellow film of m was obtained. It had excellent heat resistance and light resistance.
実施例１４
実施例１３でＣ，１，Ｄｉｓｐｅｒｓｅ Ｙｅｌｌｏｗ
６４の代りにＣ，１，Ｄｉｓｐｅｒｓｅ Ｒｅｄ １
４６（スミカロン ブリリアント レッド５Ｅ−Ｂ’Ｌ
、住人化学工業製）を使用しスミリンクＤＲ−５５の代
りに粒状ＥＶＯＨ（スミテートにＣ−１０をアルカリで
その９０％をケン化したもの）を着色した。鮮明な透明
赤色粒状物的１００ｇが得られた。Example 14 In Example 13, C, 1, Disperse Yellow
C, 1, Disperse Red 1 instead of 64
46 (Sumikaron Brilliant Red 5E-B'L
Particulate EVOH (90% of Sumitate C-10 saponified with an alkali) was colored instead of Sumilink DR-55. 100 g of bright transparent red granules were obtained.
実施例１５〜２１
以下同様にして表２に実施例を示すが何れも均一鮮明な
黄色、赤色、青色に至る粉状ＥＶＯＨ着色物が得られた
。Examples 15 to 21 The following Examples are shown in Table 2 in the same manner, and in all of them, powdered EVOH colored products with uniform and vivid yellow, red, and blue colors were obtained.
Claims (3)
って着色処理を行うことを特徴とするエチレン／ビニル
アセテート共重合体のケン化物の着色方法。(1) A method for coloring a saponified product of ethylene/vinyl acetate copolymer, which is characterized by coloring a saponified product of ethylene/vinyl acetate copolymer, which is colored with a disperse dye in a mixture of water and a hydrophilic organic solvent.
の混合液中で分散染料によって着色処理を行うことを特
徴とするエチレン／ビニルアセテート共重合体のケン化
物の着色方法。(2) A method for coloring a saponified product of an ethylene/vinyl acetate copolymer, which is characterized by carrying out a coloring treatment using a disperse dye in a mixture of water, a hydrophilic organic solvent, and a nonionic surfactant.
セテート共重合体のケン化物。(3) A saponified product of ethylene/vinyl acetate copolymer colored with a disperse dye.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63093799A JPH01266287A (en) | 1988-04-15 | 1988-04-15 | Coloring method for saponified product of ethylene/ vinylacetate copolymer and colored product |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63093799A JPH01266287A (en) | 1988-04-15 | 1988-04-15 | Coloring method for saponified product of ethylene/ vinylacetate copolymer and colored product |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01266287A true JPH01266287A (en) | 1989-10-24 |
Family
ID=14092466
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63093799A Pending JPH01266287A (en) | 1988-04-15 | 1988-04-15 | Coloring method for saponified product of ethylene/ vinylacetate copolymer and colored product |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01266287A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102558909A (en) * | 2011-12-15 | 2012-07-11 | 合肥工业大学 | Hydroxy-terminated polyether type macromolecular fluorescent dye and synthesis method thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6285085A (en) * | 1985-10-03 | 1987-04-18 | 三井東圧化学株式会社 | Dyeing of high refractive index plastic lens |
-
1988
- 1988-04-15 JP JP63093799A patent/JPH01266287A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6285085A (en) * | 1985-10-03 | 1987-04-18 | 三井東圧化学株式会社 | Dyeing of high refractive index plastic lens |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102558909A (en) * | 2011-12-15 | 2012-07-11 | 合肥工业大学 | Hydroxy-terminated polyether type macromolecular fluorescent dye and synthesis method thereof |
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