JPH0375670B2 - - Google Patents
Info
- Publication number
- JPH0375670B2 JPH0375670B2 JP62280548A JP28054887A JPH0375670B2 JP H0375670 B2 JPH0375670 B2 JP H0375670B2 JP 62280548 A JP62280548 A JP 62280548A JP 28054887 A JP28054887 A JP 28054887A JP H0375670 B2 JPH0375670 B2 JP H0375670B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- heat resistance
- light
- light resistance
- resistance
- 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 - Lifetime
Links
- 239000000835 fiber Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- 229920002647 polyamide Polymers 0.000 claims description 12
- 239000004952 Polyamide Substances 0.000 claims description 9
- 239000007983 Tris buffer Substances 0.000 claims description 3
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 3
- -1 biuret compound Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 claims 1
- 239000004611 light stabiliser Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000004043 dyeing Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000003017 thermal stabilizer Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000006641 stabilisation Effects 0.000 description 3
- 238000011105 stabilization Methods 0.000 description 3
- RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000007730 finishing process Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- BVNWQSXXRMNYKH-UHFFFAOYSA-N 4-phenyl-2h-benzotriazole Chemical compound C1=CC=CC=C1C1=CC=CC2=C1NN=N2 BVNWQSXXRMNYKH-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
Description
（産業上の利用分野）
ポリアミド系剛性繊維はスポーツ衣料、産業資
材等の材料として現在広く使用されている。特に
自動車内装材として、シート表皮フアブリツク、
天井張りフアブリツク、トリム表皮フアブリツ
ク、フロアカーペツト等に、また最近ではコンソ
ール、トリム、ピラー、天井張り等の基材表面に
フロツク加工したものが使用されているが、これ
ら素材は長時間日光の照射と高温下に曝されるた
め、とりわけ耐熱性および耐光性が強く要求され
ている。
本発明は、かかるポリアミド系剛性繊維又はそ
の染色物の耐熱・耐光性向上法に関するものであ
る。
（従来の技術）
ポリアミド系繊維又はその染色物の耐光性は従
来、染色工程において耐光性に優れた金属錯塩酸
性染料で染色し、更に銅、ニツケル等の錯塩を染
浴に併用し染色する方法を行うことにより得ら
れ、これによつてある程度の効果を達成してい
る。
しかしながら、近年、前述した各種用途への拡
がりと共により優れた耐光性のみならず耐熱性が
要求されるに及んで、前記従来方法では必らずし
も満足すべき高性能を得ることができず、そのた
めこの点に関し改善が強く望まれている状況であ
る。
（発明が解決しようとする問題点）
本発明は上述の如き実状に対処し、特に安定化
材処理に着目し、一層高性能の耐光性、耐熱性を
達成するための、ポリアミド繊維又はその染色物
の耐熱・耐光性向上を図ることを目的とするもの
である。
（問題点を解決するための手段）
即ち、上記目的を適合する本発明のポリアミド
繊維又はその染色物の耐熱・耐光性向上法の特徴
とするところは、下記構造式を有するヒドラジノ
アミド基含有ビウレツト化合物（）単独又は化
合物（）と下記構造式を有するベンドトリアゾ
ール誘導体（）との組み合わせを含む光、熱安
定化材で処理し、付着させることにある。
（但し式中Ｒ，R′は同じか相異なるＣ原子数１
〜５のアルキル基、ｎは１〜６の整数、ｍは１〜
８の整数、Ｘはハロゲン原子を表わす。）
以下、更にこれを詳述すれば、上記光・熱安定
化剤における化合物（）の具体例として特に好
ましいものはＲ，R′＝メチル基、ｎ＝６の場合
のＮ，N′，N″−トリス（イソシアナトヘキサメ
チレン）ビウレツトとＮ，Ｎ−ジメチルヒドラジ
ンとの反応生成物であるＮ，N′，N″−トリス
（Ｎ，Ｎ−ジメチルヒドラジノアミドヘキサメチ
レン）ビウレツト(1)であり、また化合物（）の
うち特に具体的に好ましいのはＸ＝Cl、ｍ＝１の
場合の、２−（２−ヒドロキシ−クロロ−５−ヒ
ドロキシカルボニルエチル）フエニル−ベンゾト
リアゾール(2)である。
そして、上記化合物（）又は化合物（）＋
（）は適当な有機溶剤の溶液或いは水性乳化分
散液の形で、光・熱安定化剤処理液として調製さ
れる。
そして、このように調製された本発明の光・熱
安定化処理液はその一態様によればポリアミド繊
維又はその染色物の仕上加工工程において、パジ
ング・ドライ法又はスプレー・ドライ法により適
用され、付着されて繊維表面に薄膜を形成して、
それが光や熱に対する遮蔽効果を発揮する。
なお、上記とは別の他の態様によれば、本発明
の光・熱安定化処理液はポリアミド繊維カーマツ
ト、カーシート、フロツキー等のバツキング、コ
ーテイング、接着工程等の応用加工工程において
バツキング剤、コーテイング剤、バインダー等に
添加混合されて適用され、繊維表面に付着され
る。
また、本発明の光・熱安定化処理液は前記仕上
加工工程および応用加工工程の両工程でも適用す
ることができ、その結果、更に良好な耐熱・耐光
性を得ることが可能である。
実施例 １
次に前記本発明向上法の好ましい実施態様なら
びにその効果を実施例により更に説明する。
ナイロン６カーシート用起毛トリコツトを第１
表Ａ，Ｂに示す各染色条件で染色した。得られた
各試料Ａ，Ｂの耐光性、耐熱性の評価は併記した
通りであつた。
そして、その後、上記得られた試料Ｂについて
前記化合物化合物（）として前記具体例で示し
た化合物（）を、また「化合物（）として前
記具体例で示した化合物(2)を第２表に表記する割
合で含む本発明の光・熱安定化処理液によりパジ
ング・ドライ法（100℃×５分間）を適用し仕上
加工を施し、フエド・オ・メーター（F.O.M）で
83℃、200時間、300時間、400時間（10mmウレタ
ンフオーム添付）の各条件下での耐光性及び耐熱
性を測定した。結果を第２表に併せて示す。
(Industrial Application Fields) Polyamide-based rigid fibers are currently widely used as materials for sports clothing, industrial materials, etc. In particular, seat fabrics are used as automobile interior materials,
Flocked materials have been used for ceiling fabrics, trim skin fabrics, floor carpets, etc., and recently for the surfaces of consoles, trims, pillars, ceiling coverings, etc., but these materials cannot be exposed to sunlight for long periods of time. Because it is exposed to high temperatures, heat resistance and light resistance are particularly required. The present invention relates to a method for improving the heat resistance and light resistance of such polyamide-based rigid fibers or dyed products thereof. (Prior art) The light resistance of polyamide fibers or dyed products thereof has traditionally been determined by dyeing with a metal complex acid dye with excellent light resistance in the dyeing process, and then using complex salts such as copper or nickel in the dye bath. This has been achieved by doing this, and has achieved some degree of effectiveness. However, in recent years, with the expansion of the various uses mentioned above, not only superior light resistance but also heat resistance has been required, and it has not always been possible to obtain satisfactory high performance with the conventional methods. Therefore, there is a strong need for improvement in this regard. (Problems to be Solved by the Invention) The present invention deals with the above-mentioned actual situation, and focuses particularly on the stabilizing material treatment, and provides polyamide fibers or their dyeing in order to achieve even higher performance light resistance and heat resistance. The purpose is to improve the heat resistance and light resistance of objects. (Means for Solving the Problems) That is, the method for improving the heat resistance and light resistance of polyamide fibers or dyed products thereof according to the present invention, which satisfies the above objectives, is characterized by the fact that polyamide fibers containing hydrazinoamide groups having the following structural formula: The method is to treat and adhere a biuret compound () alone or a combination of the compound () and a bendtriazole derivative () having the following structural formula with a light and heat stabilizer. (However, in the formula, R and R′ are the same or different C atoms, 1
~5 alkyl group, n is an integer of 1 to 6, m is 1 to
An integer of 8, X represents a halogen atom. ) Hereinafter, to further explain this in detail, particularly preferable examples of the compound () in the above light/thermal stabilizer are R, R'=methyl group, N, N', N when n=6 N,N′,N″-tris(N,N-dimethylhydrazinoamidohexamethylene)biuret (1), which is a reaction product of ″-tris(isocyanatohexamethylene)biuret and N,N-dimethylhydrazine. Among the compounds (), particularly preferred is 2-(2-hydroxy-chloro-5-hydroxycarbonylethyl)phenyl-benzotriazole (2) when X = Cl and m = 1. . And the above compound () or compound () +
() is prepared as a light/thermal stabilizer treatment solution in the form of a solution in a suitable organic solvent or an aqueous emulsion dispersion. According to one embodiment, the light/thermal stabilization treatment liquid of the present invention thus prepared is applied in the finishing process of polyamide fibers or dyed products thereof by a padding drying method or a spray drying method, It is attached and forms a thin film on the fiber surface,
It exerts a shielding effect against light and heat. In addition, according to another aspect different from the above, the light/thermal stabilization treatment liquid of the present invention can be used as a backing agent, It is applied by being mixed with a coating agent, binder, etc., and attached to the fiber surface. Furthermore, the light/thermal stabilization treatment liquid of the present invention can be applied to both the finishing process and the applied processing process, and as a result, it is possible to obtain even better heat resistance and light resistance. Example 1 Next, preferred embodiments of the improvement method of the present invention and their effects will be further explained with reference to Examples. First brushed tricot for nylon 6 car seats
Staining was carried out under each staining condition shown in Tables A and B. The evaluation of the light resistance and heat resistance of each of the obtained samples A and B was as described below. Then, for the sample B obtained above, the compound () shown in the above specific example is written as the compound compound (), and the compound (2) shown in the above specific example is written as "compound ()" in Table 2. Finishing was performed by applying the padding dry method (100°C x 5 minutes) using the photo-thermal stabilizing treatment liquid of the present invention containing a proportion of
Light resistance and heat resistance were measured at 83°C for 200 hours, 300 hours, and 400 hours (10 mm urethane foam attached). The results are also shown in Table 2.
【表】【table】
【表】
上記各表において耐光性の評価はJIS変褪色用
グレースケールに拠つた。
又、耐熱性の評価は次のような基準による。
○：良好（熱処理前と同じ強度を有するも）
△：やや不良（熱処理により若干強度低下が認め
られるもの）
×：不良（熱処理による強度低下が大きいもの）
なお、オーブン乾燥機を用いて150℃×５時間
熱処理した試験布を引張試験機を用いて引裂強度
を測定した。
実施例 ２
前記実施例１における試料Ｂを用いて、第２表
試験No.２により仕上加工処理し、その後、第３表
に示すバツキング剤に本発明の光・熱安定化剤を
40％の割合で添加混合した混合物を適用し、処理
加工した。
得られた各試料の耐光性、耐熱性は併記の通り
であつた。[Table] In each of the above tables, the evaluation of light resistance was based on the JIS fading gray scale. In addition, the evaluation of heat resistance is based on the following criteria. ○: Good (same strength as before heat treatment) △: Slightly poor (slight decrease in strength due to heat treatment) ×: Poor (same strength decrease due to heat treatment) The tear strength of the test fabric heat-treated for 5 hours was measured using a tensile tester. Example 2 Sample B in Example 1 was subjected to finishing treatment according to Test No. 2 in Table 2, and then the light/thermal stabilizer of the present invention was added to the backing agent shown in Table 3.
A 40% additive mixture was applied and processed. The light resistance and heat resistance of each sample obtained were as indicated.
【表】【table】
【表】
上記各実施例より本発明の安定化剤によつて仕
上加工および／又は応用加工することにより、ポ
リアミド繊維染色物の耐光性と耐熱性が著しく向
上することが分かる。特に両加工法を併用すれ
ば、抜群の高性能を達成することが首肯される。
また、本発明の光・熱安定化剤は化合物（）
単独よりも化合物（）と（）の併用の方が優
れた効果を達成し得ることがわかる。
（発明の効果）
以上のように、本発明によれば従来の耐光性、
耐熱性向上法に対し、より一層の性能向上が達成
され、長時間の日光の照射、高温下被曝において
も充分、耐えることができ、用途の拡大と共に
益々要求されるポリアミド系合成繊維またはその
染色物の耐熱、耐光性向上法として今後における
実効が大いに期待される。[Table] From the above examples, it can be seen that the light resistance and heat resistance of dyed polyamide fibers are significantly improved by finishing and/or applying the stabilizer of the present invention. In particular, if both processing methods are used together, it is confirmed that outstanding performance can be achieved. In addition, the light/thermal stabilizer of the present invention is a compound ()
It can be seen that a combination of compounds () and () can achieve better effects than when used alone. (Effect of the invention) As described above, according to the present invention, the conventional light resistance,
Compared to the heat resistance improvement method, polyamide-based synthetic fibers and their dyeing have achieved even greater performance and can withstand long-term sunlight irradiation and high-temperature exposure, and are increasingly required as their uses expand. It is highly anticipated that this method will be effective in the future as a method for improving the heat resistance and light resistance of objects.
Claims (1)
造式を有するヒドラジノアミド基含有ビウレツト
化合物（）単独又は該化合物（）と下記構造
式を有するベンゾトリアゾール誘導体（）との
組み合わせを含む安定化剤で処理し、付着させる
ことを特徴とするポリアミド系繊維又はその染色
物の耐熱・耐光性向上法。 （但し式中、Ｒ，R′は同じか相異なる炭素原子
数１〜５のアルキル基、ｎは１〜６の整数、ｍは
１〜８の整数、Ｘはハロゲン原子を表す。） ２ 化合物（）がＮ，N′，N″−トリス（Ｎ，
Ｎ−ジメチルヒドラジノアミドヘキサメチレン）
−ビウレツトである特許請求の範囲第１項記載の
ポリアミド系繊維又はその染色物の耐熱・耐光性
向上法。[Scope of Claims] 1 Polyamide fibers or dyed products thereof are prepared by using a hydrazinoamide group-containing biuret compound () having the following structural formula alone or in combination with the compound () and a benzotriazole derivative () having the following structural formula. A method for improving the heat resistance and light resistance of polyamide fibers or dyed products thereof, characterized by treating and adhering them with a stabilizer containing. (However, in the formula, R and R' are the same or different alkyl groups having 1 to 5 carbon atoms, n is an integer of 1 to 6, m is an integer of 1 to 8, and X represents a halogen atom.) 2 Compound () is N, N′, N″−tris(N,
N-dimethylhydrazinoamidohexamethylene)
- A method for improving heat resistance and light resistance of a polyamide fiber or a dyed product thereof according to claim 1, which is biuret.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62280548A JPH01124695A (en) | 1987-11-05 | 1987-11-05 | Method for enhancing heat resistance and light fastness of polyamide fiber or dyed article thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62280548A JPH01124695A (en) | 1987-11-05 | 1987-11-05 | Method for enhancing heat resistance and light fastness of polyamide fiber or dyed article thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01124695A JPH01124695A (en) | 1989-05-17 |
| JPH0375670B2 true JPH0375670B2 (en) | 1991-12-02 |
Family
ID=17626595
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62280548A Granted JPH01124695A (en) | 1987-11-05 | 1987-11-05 | Method for enhancing heat resistance and light fastness of polyamide fiber or dyed article thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01124695A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2969395A (en) * | 1994-07-26 | 1996-02-22 | Procter & Gamble Company, The | Rinse added fabric softener compositions containing sunscreens for sun-fade protection for fabrics |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6081370A (en) * | 1983-10-07 | 1985-05-09 | 日華化学株式会社 | Treatment of fiber product |
-
1987
- 1987-11-05 JP JP62280548A patent/JPH01124695A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6081370A (en) * | 1983-10-07 | 1985-05-09 | 日華化学株式会社 | Treatment of fiber product |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH01124695A (en) | 1989-05-17 |
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