JPS6214673B2 - - Google Patents
Info
- Publication number
- JPS6214673B2 JPS6214673B2 JP53106400A JP10640078A JPS6214673B2 JP S6214673 B2 JPS6214673 B2 JP S6214673B2 JP 53106400 A JP53106400 A JP 53106400A JP 10640078 A JP10640078 A JP 10640078A JP S6214673 B2 JPS6214673 B2 JP S6214673B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- group represented
- synthetic polyamide
- represented
- 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
Links
- 238000000034 method Methods 0.000 claims description 25
- 239000000463 material Substances 0.000 claims description 19
- 239000004952 Polyamide Substances 0.000 claims description 18
- 229920002647 polyamide Polymers 0.000 claims description 18
- 238000010023 transfer printing Methods 0.000 claims description 14
- 239000000986 disperse dye Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000000049 pigment Substances 0.000 claims description 5
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 4
- 150000004056 anthraquinones Chemical class 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 239000011159 matrix material Substances 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 16
- 239000004744 fabric Substances 0.000 description 6
- -1 monofluoro-1,3,5-triazinyl groups Chemical group 0.000 description 6
- 238000007639 printing Methods 0.000 description 6
- 229920002302 Nylon 6,6 Polymers 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 229920000298 Cellophane Polymers 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 229920000571 Nylon 11 Polymers 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Printing Methods (AREA)
- Coloring (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
Description
本発明はジ又はモノフルオロ−１・３・５−ト
リアジニル基を有する反応型分散染料を用いて合
成ポリアミド含有材料を熱転写捺染する方法に関
するものである。
ナイロン等の合成ポリアミド含有材料を熱転写
捺染する方法としては、紙等の仮の支持体に昇華
性の分散染料を含む印刷インキで図柄を印刷し、
これを転写シートとして被転写体である合成ポリ
アミド含有材料と重ね合せ、加熱加圧して転写印
捺する方法が採用され、実施されている。
しかしながらこの方法には、得られる捺染物の
湿潤堅牢度が極めて低いこと、またこの方法に使
用されている分散染料には耐光堅牢度の低いもの
が多いこと等の実用面で不満な点がある。
本発明者らは、これらの問題点を解決する方法
として、昇華性の反応型分散染料を使用する合成
ポリアミド含有材料の熱転写捺染法に着目し検討
した。反応型分散染料を使用する合成ポリアミド
含有材料の熱転写捺染法により良好な捺染物、特
にすぐれた湿潤堅牢度を有する捺染物を得るため
には、使用される反応型分散染料が、(1)紙等の仮
の支持体上で安定であること、(2)合成ポリアミド
含有材料の風合を損なわない転写条件下で安定で
効率よく昇華すること、(3)昇華した染料が定量的
に合成ポリアミド含有材料と反応して共有結合を
形成することにより染着することなどの性質を有
することが不可欠である。本発明者らは種々の反
応基を有する反応型分散染料についてこれらの性
質をみたすものを探索した結果、ジ又はモノフル
オロトリアジニル基を有する反応型分散染料が最
もこれらの性質をみたし、熱転写捺染に最適であ
ることを見出して本発明を完成した。
すなわち本発明の目的は合成ポリアミド含有材
料の熱転写捺染法において、合成ポリアミド含有
材料の風合を損なうことなく、すぐれた耐光堅牢
度、とりわけすぐれた湿潤堅牢度を有する捺染物
を得る方法を提供することにあり、この目的は、
合成ポリアミド含有材料を一般式〔〕
〔式中、Ｄはスルホン酸基及びカルボキシル基を
含有しないアゾ系又はアントラキノン系の色素母
体を表わし、Ｘは弗素原子、式−R1で表わされ
る基、式−OR1で表わされる基、式−SR1で表わ
される基または式
The present invention relates to a method for thermal transfer printing of synthetic polyamide-containing materials using reactive disperse dyes having di- or monofluoro-1,3,5-triazinyl groups. As a method for thermal transfer printing of synthetic polyamide-containing materials such as nylon, a pattern is printed on a temporary support such as paper with a printing ink containing a sublimable disperse dye.
A method has been adopted and practiced in which this is used as a transfer sheet and is superimposed on a synthetic polyamide-containing material to be transferred, and then heated and pressed for transfer printing. However, this method has practical disadvantages, such as the extremely low wet fastness of the prints obtained and the fact that many of the disperse dyes used in this method have low light fastness. . As a method for solving these problems, the present inventors focused on and studied a thermal transfer printing method for a synthetic polyamide-containing material using a sublimable reactive disperse dye. In order to obtain good prints, especially prints with good wet fastness, by the thermal transfer printing process of synthetic polyamide-containing materials using reactive disperse dyes, the reactive disperse dyes used are (1) (2) Stable and efficient sublimation under transfer conditions that do not impair the texture of the synthetic polyamide-containing material; (3) The sublimated dye quantitatively transfers to the synthetic polyamide-containing material. It is essential that the dye has properties such as dyeing by reacting with the contained material to form a covalent bond. The present inventors searched for reactive disperse dyes having various reactive groups that satisfied these properties, and found that reactive disperse dyes having di- or monofluorotriazinyl groups best met these properties. The present invention was completed by discovering that it is optimal for thermal transfer printing. That is, an object of the present invention is to provide a method for obtaining a print having excellent light fastness, especially excellent wet fastness, without impairing the texture of the synthetic polyamide-containing material, in a thermal transfer printing method for synthetic polyamide-containing materials. In particular, this purpose is to
General formula for synthetic polyamide-containing materials [] [In the formula, D represents an azo or anthraquinone pigment matrix that does not contain a sulfonic acid group or a carboxyl group, and X is a fluorine atom, a group represented by the formula -R 1 , a group represented by the formula -OR 1, or a group represented by the formula -OR 1 . - Group or formula represented by SR 1
【式】で表わされる基（式
中R1は置換基を有していてもよい炭素数１〜５
のアルキル基、R2は水素原子または置換基を有
していてもよい炭素数１〜５のアルキル基を表わ
す。ただしR1、R2がいずれもアルキル基を表わ
すときは、R1及びR2に含まれる炭素数の総和は
５以下でなければならない。）を表わす。〕で示さ
れる反応型分散染料を用いて熱転写捺染すること
により容易に達成される。
以下、本発明を詳細に説明する。本発明におけ
る合成ポリアミド含有材料としては、ナイロン
６、ナイロン6.6、ナイロン6.10、ナイロン11等
の繊維及びこれらの織編物、不織布、フイルム等
が挙げられる。
本発明の熱転写捺染法においては、染料として
前記一般式〔〕で示されるジ又はモノフルオロ
−１・３・５−トリアジニル基を有する分子量
800以下の昇華性分散染料が使用される。
前記一般式〔〕においてＸは弗素原子、式−
R1で表わされる基、式−OR1で表わされる基、式
−SR1で表わされる基または式A group represented by [Formula] (in the formula, R 1 has 1 to 5 carbon atoms, which may have a substituent)
The alkyl group represented by R 2 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms which may have a substituent. However, when both R 1 and R 2 represent an alkyl group, the total number of carbon atoms contained in R 1 and R 2 must be 5 or less. ). This can be easily achieved by thermal transfer printing using a reactive disperse dye shown in ]. The present invention will be explained in detail below. Examples of the synthetic polyamide-containing material in the present invention include fibers such as nylon 6, nylon 6.6, nylon 6.10, and nylon 11, as well as woven and knitted fabrics, nonwoven fabrics, and films thereof. In the thermal transfer printing method of the present invention, the molecular weight dye having a di- or monofluoro-1,3,5-triazinyl group represented by the general formula []
A sublimable disperse dye of up to 800 is used. In the above general formula [], X is a fluorine atom, and the formula -
Group represented by R 1 , group represented by formula-OR 1 , group or formula represented by formula-SR 1
【式】で表わ
される基であるが、Ｘが弗素原子の場合とくに良
好な結果が得られる。式−R1で表わされる基と
してはメチル基、エチル基、プロピル基等が挙げ
られ、式−OR1で表わされる基としてはメトキシ
基、エトキシ基、エトキシエトキシ基、メトキシ
エトキシエトキシ基等が挙げられる。また、式−
SR1で表わされる基としてはメチルチオ基、エチ
ルチオ基等が挙げられ、式In the group represented by the formula, particularly good results can be obtained when X is a fluorine atom. Examples of the group represented by the formula -R 1 include a methyl group, ethyl group, propyl group, etc., and examples of the group represented by the formula -OR 1 include a methoxy group, an ethoxy group, an ethoxyethoxy group, a methoxyethoxyethoxy group, etc. It will be done. Also, the formula −
Groups represented by SR 1 include methylthio group, ethylthio group, etc.
【式】で表わされ
る基としてはジメチルアミノ基、ジエチルアミノ
基等が挙げられる。
Ｄで表わされるスルホン酸基及びカルボキシル
基を含有しないアゾ系又はアントラキノン系の色
素母体としては、Examples of the group represented by the formula include a dimethylamino group and a diethylamino group. The azo or anthraquinone pigment base containing no sulfonic acid group or carboxyl group represented by D is as follows:
【式】
等のアゾ系色素母体、
或は
等のアントラキノン系色素母体が挙げられる。
本発明において用いられる染料は、大気圧下で
140〜240℃の温度条件で10秒間〜４分間、好まし
くは15〜60秒間で昇華又は蒸発するものが特に好
適である。本発明において用いられる転写シート
は公知の方法で製造することができる。すなわち
前記染料を含むインキにより紙、セロハン、金属
箔、プラスチツクフイルム等の支持体上にオフセ
ツト印刷、フレキソ印刷、グラビア印刷或はスク
リーンプロセス等の任意の印刷方式で図柄、文
字、数字等を印刷することにより作成される。
転写シートを作成するために使用されるインキ
は、公知の方法によつて製造することができる。
すなわち前記染料を水および（または）溶媒また
は溶媒混合物中に有利には結合剤の存在下で溶解
または分散することにより製造される。溶剤、結
合剤等のインキを構成するビヒクル及び助剤は、
採用する印刷方式により異なるので、印刷方式に
適したものが使用される。
本発明により合成ポリアミド含有材料の転写捺
染を行なうには、先に説明した転写シートと合成
ポリアミド含有材料とを転写シートの印刷面を接
して重ね合わせ、所望ならば機械的に圧着させて
140〜240℃、好ましくは170〜210℃で、10秒間〜
４分間、好ましくは15〜60秒間加熱処理すれば良
い。
転写を行なう際は常圧下で行つてもよく、また
減圧下例えば15〜150mmHg程度の圧力下で行なつ
ても良好な結果が得られる。
以上詳述したように本発明方法は従来の方法に
比し
１ 熱転写捺染時に合成ポリアミド含有材料とジ
又はモノフルオロ−１・３・５−トリアジニル
基との共有結合がほぼ定量的に生成されるた
め、本発明方法により得られる捺染物は従来既
知の方法により得られる捺染物に比較して極め
てすぐれた湿潤堅牢度を示す。
２ 本発明方法に使用される前記一般式〔〕で
表わされる染料は、合成ポリアミド含有材料の
風合を損なわない熱転写条件下で熱分解するこ
となく極めて効率よく昇華し、かつ合成ポリア
ミド含有材料との反応性が非常に高いので本発
明方法により極めて高い固着率で鮮明な捺染物
が得られる。
等の優位性を示し、その工業的価値は極めて大き
いものである。
以下、本発明を実施例によつて更に詳細に説明
するが、本発明をその要旨を超えない限り、以下
の実施例に限定されるものではない。
尚、実施例中「部」とあるのは「重量部」を示
す。
実施例 １
下記染料６部、
エチルセルロース８部及びイソプロピルアルコー
ル86部をペイントコンデイシヨナーで摩砕してイ
ンキを調製し、このインキをグラビア用コート紙
上にバーコーター（0.5mm）を用いて印刷し転写
シートを作成した。
この転写シート上にナイロン６、６の織物を重
ね合わせ、平圧プレス機を用いて200℃、１Kg／
cm2Ｇで60秒間加熱加圧して転写固着した。その結
果、表１の昇華率、染着率で示すごとく、転写シ
ート上の染料のほぼ全部が上記ナイロン６、６織
物に染着した。得られた染色物は鮮明な赤味の黄
色であつた。このものを２ｇ／のノニオン界面
活性剤（花王石鹸(株)製、商標；スコアロール
#900）を用いて浴比１：50で95℃で20分間ソー
ピングをしたところ染料の脱落は全く認められな
かつた。更に引きつづいてジメチルホルムアミド
を用いて100℃10分間抽出したところ、染料の脱
落は全く認められなかつた。すなわちナイロン
６、６織物に染着した染料は表１の反応率で示す
ように全てナイロン６、６織物と反応し、共有結
合を形成して染着していた。そして本染料を使用
した捺染布の湿潤堅牢度は表１に示すように極め
てすぐれていた。
比較のために表１に示す種類の染料を用いた以
外は前記実施例と同様にして転写捺染を行なつ
た。その結果を表−１に示した。Azo pigment matrix such as [Formula], or Examples include anthraquinone pigment matrices such as The dye used in the present invention is
Particularly suitable are those that sublime or evaporate in 10 seconds to 4 minutes, preferably 15 to 60 seconds at a temperature of 140 to 240°C. The transfer sheet used in the present invention can be manufactured by a known method. That is, designs, letters, numbers, etc. are printed using ink containing the dye on a support such as paper, cellophane, metal foil, plastic film, etc. by any printing method such as offset printing, flexo printing, gravure printing, or screen process. Created by The ink used to create the transfer sheet can be manufactured by a known method.
That is, they are prepared by dissolving or dispersing the dyes in water and/or a solvent or solvent mixture, preferably in the presence of a binder. Vehicles and auxiliaries that make up the ink, such as solvents and binders, are
Since it differs depending on the printing method employed, the one suitable for the printing method is used. In order to carry out transfer printing of a synthetic polyamide-containing material according to the present invention, the above-described transfer sheet and the synthetic polyamide-containing material are overlapped with the printing surfaces of the transfer sheets in contact and, if desired, are mechanically pressed together.
140~240℃, preferably 170~210℃ for 10 seconds~
The heat treatment may be performed for 4 minutes, preferably for 15 to 60 seconds. The transfer may be carried out under normal pressure, or good results can be obtained even if it is carried out under reduced pressure, for example, at a pressure of about 15 to 150 mmHg. As detailed above, the method of the present invention has the following advantages over conventional methods: 1. Covalent bonds between the synthetic polyamide-containing material and the di- or monofluoro-1,3,5-triazinyl group are almost quantitatively generated during thermal transfer printing. Therefore, the prints obtained by the method of the present invention exhibit extremely superior wet fastness compared to prints obtained by conventionally known methods. 2 The dye represented by the general formula [] used in the method of the present invention sublimates extremely efficiently without thermal decomposition under thermal transfer conditions that do not impair the feel of the synthetic polyamide-containing material, and is compatible with the synthetic polyamide-containing material. Since the reactivity of the dye is very high, the method of the present invention allows obtaining clear prints with an extremely high fixation rate. The industrial value is extremely large. EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to examples, but the present invention is not limited to the following examples unless it exceeds the gist thereof. In addition, "parts" in the examples indicate "parts by weight." Example 1 6 parts of the following dye, An ink was prepared by grinding 8 parts of ethyl cellulose and 86 parts of isopropyl alcohol with a paint conditioner, and this ink was printed on gravure coated paper using a bar coater (0.5 mm) to prepare a transfer sheet. A nylon 6,6 fabric was layered on top of this transfer sheet, and a 1kg/1kg/200cm press was applied at 200°C using a flat press machine.
The transfer was fixed by heating and pressing at cm 2 G for 60 seconds. As a result, as shown in the sublimation rate and dyeing rate in Table 1, almost all of the dye on the transfer sheet was dyed onto the nylon 6,6 fabric. The dyed product obtained was a bright reddish yellow. 2 g of this nonionic surfactant (manufactured by Kao Soap Co., Ltd., trademark: Score Roll)
#900) at a bath ratio of 1:50 at 95°C for 20 minutes, no loss of dye was observed. Further, when the mixture was extracted with dimethylformamide at 100°C for 10 minutes, no loss of dye was observed. That is, all the dyes dyed on the nylon 6,6 fabric reacted with the nylon 6,6 fabric as shown in the reaction rates in Table 1, forming covalent bonds and dyeing. The wet fastness of the printed fabric using this dye was extremely excellent as shown in Table 1. For comparison, transfer printing was carried out in the same manner as in the previous example except that dyes of the types shown in Table 1 were used. The results are shown in Table-1.
【表】
実施例 ２〜22
実施例１の方法において表２に示す染料を使用
する以外は実施例１に記載の通り実施した。その
結果、各実施例毎に表−２の右欄に示す鮮明な色
相の湿潤堅牢度の極めてすぐれた捺染物が得られ
た。[Table] Examples 2 to 22 The procedure was as described in Example 1 except that the dyes shown in Table 2 were used in the method of Example 1. As a result, prints with clear hues and extremely excellent wet fastness as shown in the right column of Table 2 were obtained for each example.
【表】【table】
【表】【table】
【表】【table】
Claims (1)
含有しないアゾ系又はアントラキノン系の色素母
体を表わし、Ｘは弗素原子、式−R1で表わされ
る基、式−OR1で表わされる基、式−SR1で表わ
される基または式【式】で表わされる基（式 中R1は置換基を有していてもよい炭素数１〜５
のアルキル基、R2は水素原子または置換基を有
していてもよい炭素数１〜５のアルキル基を表わ
す。ただしR1、R2がいずれもアルキル基を表わ
すときは、R1及びR2に含まれる炭素数の総和は
５以下でなければならない。）を表わす。〕で示さ
れる反応型分散染料を用いて熱転写捺染すること
を特徴とする合成ポリアミド含有材料の熱転写捺
染法。[Claims] 1. A synthetic polyamide-containing material represented by the general formula [] [In the formula, D represents an azo or anthraquinone pigment matrix that does not contain a sulfonic acid group or a carboxyl group, and X is a fluorine atom, a group represented by the formula -R 1 , a group represented by the formula -OR 1, or a group represented by the formula -OR 1 . - A group represented by SR 1 or a group represented by the formula
The alkyl group represented by R 2 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms which may have a substituent. However, when both R 1 and R 2 represent an alkyl group, the total number of carbon atoms contained in R 1 and R 2 must be 5 or less. ). A method for thermal transfer printing of synthetic polyamide-containing materials, characterized by thermal transfer printing using a reactive disperse dye shown in ].
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10640078A JPS5532638A (en) | 1978-08-31 | 1978-08-31 | Thermal copy printing process of material containing synthetic polyamide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10640078A JPS5532638A (en) | 1978-08-31 | 1978-08-31 | Thermal copy printing process of material containing synthetic polyamide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5532638A JPS5532638A (en) | 1980-03-07 |
| JPS6214673B2 true JPS6214673B2 (en) | 1987-04-03 |
Family
ID=14432629
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10640078A Granted JPS5532638A (en) | 1978-08-31 | 1978-08-31 | Thermal copy printing process of material containing synthetic polyamide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5532638A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59109384A (en) * | 1982-12-15 | 1984-06-25 | Hida Seisakusho:Kk | Surface decorating method of plastic |
-
1978
- 1978-08-31 JP JP10640078A patent/JPS5532638A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5532638A (en) | 1980-03-07 |
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