JPH06228816A - Production of polyurethane fiber excellent in light-fastness - Google Patents
Production of polyurethane fiber excellent in light-fastnessInfo
- Publication number
- JPH06228816A JPH06228816A JP1539793A JP1539793A JPH06228816A JP H06228816 A JPH06228816 A JP H06228816A JP 1539793 A JP1539793 A JP 1539793A JP 1539793 A JP1539793 A JP 1539793A JP H06228816 A JPH06228816 A JP H06228816A
- Authority
- JP
- Japan
- Prior art keywords
- polyurethane
- spinning
- polyurethane fiber
- ultraviolet absorber
- fiber
- 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
Landscapes
- Chemical Treatment Of Fibers During Manufacturing Processes (AREA)
- Artificial Filaments (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、耐光性に優れたポリウ
レタン繊維の製法に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing a polyurethane fiber having excellent light resistance.
【０００２】[0002]
【従来の技術】一般に、ポリウレタン樹脂は光による黄
変や劣化などの耐光性に劣るため、ポリウレタン弾性繊
維を一般の繊維と混用する場合には耐光性の改良が必要
とされている。ポリウレタン繊維の耐光性を改良する方
法として、繊維中に酸化チタンなどの微粒子を高濃度で
添加し、遮光効果により耐光性を改良したり、酸化防止
剤や紫外線吸収剤を用いることが行われている。例え
ば、本発明者らは特開平４−１５３３１６号公報にヒン
ダードフェノール系またはヒンダードアミン系酸化防止
剤及びベンゾトリアゾール系紫外線吸収剤を含有する熱
可塑性エラストマーからなる弾性繊維を提案している。
また、本発明者らは、特願平４−３０８７５０号で染色
時にベンゾトリアゾール系耐光性向上剤を併用すること
により耐光性に優れた織編物の製法を提案している。2. Description of the Related Art Generally, polyurethane resins are inferior in light resistance such as yellowing and deterioration due to light. Therefore, when polyurethane elastic fibers are mixed with general fibers, it is necessary to improve light resistance. As a method for improving the light resistance of polyurethane fibers, fine particles such as titanium oxide are added to the fibers at a high concentration to improve the light resistance by a light-shielding effect, or an antioxidant or an ultraviolet absorber is used. There is. For example, the present inventors have proposed in JP-A-4-153316 an elastic fiber made of a thermoplastic elastomer containing a hindered phenol-based or hindered amine-based antioxidant and a benzotriazole-based UV absorber.
In addition, the present inventors have proposed in Japanese Patent Application No. 4-308750 a method for producing a woven or knitted fabric excellent in light resistance by using a benzotriazole-based light resistance improver together with the dyeing.
【０００３】[0003]
【発明が解決しようとする課題】繊維中に酸化チタンな
どの微粒子を高濃度に添加すると、ポリウレタン繊維の
透明性が低下し白っぽくなるため、伸縮性布帛に用いた
場合、特に濃色に染色した場合にはいわゆる目剥きの状
態となり白く目立ち、品位の低いものとなってしまう。When a high concentration of fine particles such as titanium oxide is added to the fiber, the transparency of the polyurethane fiber is lowered and it becomes whitish. Therefore, when it is used for a stretchable fabric, it is dyed particularly deeply. In such a case, a so-called blinding state is produced, which is conspicuous white and becomes of low quality.
【０００４】酸化防止剤や紫外線吸収剤をポリウレタン
に添加して紡糸することは、溶融紡糸においては添加剤
の耐熱性や、比較的少量の添加剤を均一に混合する上で
工業的な安定性が得られにくく、湿式紡糸においては紡
糸原液に対する添加剤の溶解性の面で難点がある。ま
た、添加した紫外線吸収剤などは表層部から内部まで分
布するため、表面部での濃度が低く効果が不十分となり
やすい。さらに、染色時に併用する方法では、交編織し
た繊維に吸収されたり、浴比が大きいと使用する紫外線
吸収剤などの量が多くなり、無駄がでやすく、コストア
ップとなりやすい。また、染色時に蛍光増白剤などを併
用するとき、増白効果が阻害されるなど染色条件が一部
制限されることがある。Spinning by adding an antioxidant and an ultraviolet absorber to polyurethane is industrially stable in melt spinning, in view of heat resistance of additives, and in uniformly mixing a relatively small amount of additives. Is difficult to obtain and there is a problem in the wet spinning in terms of the solubility of the additive in the spinning dope. In addition, since the added ultraviolet absorber and the like are distributed from the surface layer portion to the inside, the concentration at the surface portion is low and the effect tends to be insufficient. Further, in the method used in combination at the time of dyeing, when the fibers are mixed and woven, the amount of the ultraviolet absorber or the like used is increased when the bath ratio is large, and it is easy to waste and increase the cost. Further, when a fluorescent whitening agent or the like is used at the time of dyeing, the dyeing conditions may be partially limited such that the whitening effect is hindered.
【０００５】本発明は、上記のごとき問題のない、耐光
性に優れたポリウレタン繊維をきわめて容易に製造する
方法を提供しようとするものである。すなわち、本発明
者らの検討によれば、従来、染色工程などにおいて脱落
し永続的な効果が期待できないと考えられていた油剤に
紫外線吸収剤を添加しポリウレタン繊維に付与すること
によりきわめて容易に永続的な耐光性をポリウレタン繊
維に付与し得ることを見いだし、本発明を完成するにい
たった。The present invention is intended to provide a method for extremely easily producing a polyurethane fiber having excellent light resistance, which is free from the above problems. That is, according to the study by the present inventors, it is extremely easy to add a UV absorber to an oil agent, which has been conventionally considered to be lost in a dyeing step or the like, and a permanent effect cannot be expected, and imparted to a polyurethane fiber. They have found that durable light resistance can be imparted to polyurethane fibers and have completed the present invention.
【０００６】[0006]
【課題を解決するための手段】本発明は、紡糸したポリ
ウレタン繊維に紫外線吸収剤を添加した紡糸油剤を付与
することを特徴とする耐光性に優れたポリウレタン繊維
の製法である。DISCLOSURE OF THE INVENTION The present invention is a process for producing polyurethane fibers having excellent light resistance, which is characterized in that a spinning oil containing an ultraviolet absorber is added to spun polyurethane fibers.
【０００７】本発明で紫外線吸収剤を付与するポリウレ
タン繊維は、溶融紡糸したポリウレタン繊維、乾式法あ
るいは湿式法によって得られたポリウレタン繊維のいず
れであってもよい。ポリウレタンの紡糸時には紫外線吸
収剤を添加せずに紡糸し、紫外線吸収剤を添加した紡糸
油剤を付与する。このような方法をとることにより、比
較的少量の紫外線吸収剤をポリウレタン繊維の表面に均
一に付与することができる。The polyurethane fiber to which the ultraviolet absorbent is applied in the present invention may be either melt spun polyurethane fiber or polyurethane fiber obtained by a dry method or a wet method. At the time of spinning of polyurethane, it is spun without adding an ultraviolet absorber, and a spinning oil containing an ultraviolet absorber is applied. By using such a method, a relatively small amount of the ultraviolet absorber can be uniformly applied to the surface of the polyurethane fiber.
【０００８】本発明で使用することのできる紫外線吸収
剤は、従来公知のベンゾトリアゾール系あるいはベンゾ
フェノン系のもので、使用する紡糸油剤に溶解するある
いは安定に懸濁するものが使用される。また、染色工程
や家庭での洗濯により脱落しにくいものを選択する。ベ
ンゾトリアゾール系の紫外線吸収剤としては、例えば、
２−ヒドロキシ−３−ドデシル−５−メチルフェニルベ
ンゾトリアゾールなどのヒドロキシフェニルベンゾトリ
アゾール誘導体、２−［２−ヒドロキシ−３，５−ビス
（α，α−ジメチルベンジル）フェニル］−２Ｈ−ベン
ゾトリアゾールなどが挙げられ、また、ベンゾフェノン
系紫外線吸収剤としては、例えば、２−ヒドロキシ−４
−メトキシベンゾフェノン、２−ヒドロキシ−４−オク
チロキシ−ベンゾフェノンなどが挙げられる。The ultraviolet absorber which can be used in the present invention is a conventionally known benzotriazole type or benzophenone type, which is dissolved or stably suspended in the spinning oil used. Also, select a material that does not easily come off during the dyeing process or at home. Examples of the benzotriazole-based ultraviolet absorber include, for example:
Hydroxyphenylbenzotriazole derivative such as 2-hydroxy-3-dodecyl-5-methylphenylbenzotriazole, 2- [2-hydroxy-3,5-bis (α, α-dimethylbenzyl) phenyl] -2H-benzotriazole, etc. Examples of the benzophenone-based ultraviolet absorber include 2-hydroxy-4.
-Methoxybenzophenone, 2-hydroxy-4-octyloxy-benzophenone and the like.
【０００９】紫外線吸収剤の付与量は、ポリウレタン繊
維に対して３００〜１００００ｐｐｍ、好ましくは、１
０００〜６０００ｐｐｍの範囲である。付与量が少ない
と十分な効果を上げることができず、また、多いと交編
織した他の繊維に移行したりして蛍光増白効果を阻害し
たり、コストアップとなる。紫外線吸収剤は、所要量を
紡糸油剤に溶解あるいは懸濁してポリウレタン繊維に付
与する。ポリウレタン繊維の油剤は一般に紡糸時に付与
され、追油されることは希であるが、必要であれば、追
油するときに追油する油剤に溶解あるいは懸濁して追油
することもできる。The amount of the ultraviolet absorber applied is 300 to 10000 ppm, preferably 1
It is in the range of 000 to 6000 ppm. If the applied amount is small, the sufficient effect cannot be achieved, and if the applied amount is large, the fibers are transferred to other fibers that have been interwoven, and the fluorescent whitening effect is hindered, or the cost is increased. The ultraviolet absorber is applied to the polyurethane fiber by dissolving or suspending a required amount in a spinning oil agent. The oil agent of the polyurethane fiber is generally applied during spinning and is rarely added, but if necessary, it can be dissolved or suspended in the oil agent to be added at the time of additional oil to add oil.
【００１０】本発明においてはポリウレタン繊維には紫
外線吸収剤のみではなく、耐光安定剤や酸化防止剤を併
用することが好ましい。これらは単独で紫外線吸収剤と
組み合わせてもよいが、併用して紫外線吸収剤と組み合
わせることによりそれらの相乗効果により効果がより高
くなるため好ましい。本発明で好ましい耐光安定剤とし
てはヒンダードアミン系光安定剤が挙げられ、酸化防止
剤としてはヒンダードフェノール系酸化防止剤が挙げら
れる。In the present invention, it is preferable to use not only an ultraviolet absorber but also a light resistance stabilizer and an antioxidant together with the polyurethane fiber. These may be used alone in combination with an ultraviolet absorber, but by combining them together with an ultraviolet absorber, the effects are further enhanced by their synergistic effect, which is preferable. In the present invention, preferred light resistance stabilizers include hindered amine-based light stabilizers, and antioxidants include hindered phenol-based antioxidants.
【００１１】本発明に用いられるヒンダードアミン系光
安定剤は、種々の物が用い得るがポリウレタン繊維の紡
糸や編織、染色等の工程中にブリードアウトや昇華分解
を生じない出来るだけ分子量の大きいものあるいはポリ
ウレタン繊維を形成するポリウレタンの分子中に組み込
まれるものが好ましく、特に後者のタイプが好ましく用
いられる。本発明に於いて用いられるヒンダードアミン
系光安定剤のポリウレタン繊維への添加時期は、用いる
ポリウレタンの合成からポリウレタン繊維としての製糸
時迄のどの時点でも良いが、酸化劣化による効果の低下
を考慮すると、製糸直前の添加が最も好ましい。しか
し、ポリウレタンに組み込まれるタイプの光安定剤の場
合には、ポリウレタンの合成時に添加するのが好まし
い。As the hindered amine light stabilizer used in the present invention, various kinds of substances can be used, but those having a molecular weight as large as possible without causing bleed-out or sublimation decomposition during the steps of spinning, knitting, dyeing, etc. of polyurethane fibers, or Those incorporated in the molecule of polyurethane forming the polyurethane fiber are preferred, and the latter type is particularly preferably used. The hindered amine light stabilizer used in the present invention may be added to the polyurethane fiber at any time from the synthesis of the polyurethane used to the spinning of the polyurethane fiber, but in consideration of the decrease in the effect due to oxidative deterioration, Most preferred is the addition just before spinning. However, in the case of a light stabilizer of the type incorporated in polyurethane, it is preferably added during the synthesis of the polyurethane.
【００１２】本発明に用いられるヒンダードフェノール
系酸化防止剤としては、ポリウレタン繊維の紡糸や編
織、染色等の工程中にブリードアウトや昇華分解の生じ
ない出来るだけ分子量の大きいものが好ましく用いられ
る。ヒンダードのタイプとしては、片ヒンダードでも両
ヒンダードでも良いが、フェノール基がイソシアネート
基と反応しないタイプの物が良く、この反応に触媒作用
を有する金属類の存在に十分な注意が必要である。例え
ば、ヒンダードアミン系光安定剤やヒンダードフェノー
ル系酸化防止剤の合成に用いられるリチウム等の存在に
留意する必要がある。本発明に於いて用いられるヒンダ
ードフェノール系酸化防止剤のポリウレタン繊維への添
加時期は、耐光性の観点から言えば、ポリウレタン繊維
としての製糸時に添加するのが最も良いが、その工程上
の最適な時点を選択することが可能である。As the hindered phenol-based antioxidant used in the present invention, those having a molecular weight as large as possible without causing bleed-out and sublimation decomposition during the processes such as spinning, knitting and dyeing of polyurethane fibers are preferably used. The hindered type may be one-sided hindered type or both-sided hindered type, but a type in which a phenol group does not react with an isocyanate group is preferable, and it is necessary to pay sufficient attention to the presence of a metal having a catalytic action for this reaction. For example, it is necessary to pay attention to the presence of lithium and the like used in the synthesis of hindered amine light stabilizers and hindered phenol antioxidants. From the viewpoint of light resistance, it is best to add the hindered phenolic antioxidant used in the present invention to the polyurethane fiber at the time of spinning as the polyurethane fiber, but the optimum process It is possible to select any time point.
【００１３】[0013]
【実施例】以下、実施例により説明する。なお、本発明
における耐光性評価方法は、ＪＩＳ Ｌ０８４２−１９
７１に従い、カーボンア−ク灯法（６３℃）により実施
した。EXAMPLES Examples will be described below. The light resistance evaluation method in the present invention is based on JIS L0842-19.
No. 71, the carbon arc lamp method (63 ° C.).
【００１４】実施例１、比較例１ 分子量１５００のポリ−３−メチルペンタンアゼレート
をソフトセグメントとするポリウレタンを溶融紡糸し、
紡糸時に紫外線吸収剤として２−ヒドロキシ−３−ドデ
シル−５−メチルフェニルベンゾトリアゾールを５％濃
度に溶解した紡糸油剤を油剤付着量が４％となるように
給油して４０デニールのポリウレタン繊維を得た（紫外
線吸収剤は２０００ｐｐｍ）。一方、比較のために紫外
線吸収剤を添加しない油剤を給油して同様に４０デニー
ルのポリウレタン繊維を得た。これらのポリウレタン繊
維と、５０デニール／３６フィラメントのポリエステル
繊維よりなるツーウェイトリコットを、Ｓｍｉｋａｌｏ
ｎ Ｒｅｄ Ｅ−ＲＰＤ ０．１％ｏｗｆにて１２５℃
で染色した。染め上がった布を１６０℃でファイナルセ
ットし、耐光性を評価したところ、紫外線吸収剤を添加
したものは４−５級であるのに対し、添加しなかったも
のは３級以下であった。Example 1 and Comparative Example 1 Polyurethane having poly-3-methylpentane azelate having a molecular weight of 1500 as a soft segment was melt-spun,
A 40-denier polyurethane fiber was obtained by lubricating a spinning oil solution containing 2-hydroxy-3-dodecyl-5-methylphenylbenzotriazole dissolved in a 5% concentration as an ultraviolet absorber at the time of spinning so that the amount of oil adhered was 4%. (UV absorber is 2000 ppm). On the other hand, for comparison, a 40 denier polyurethane fiber was similarly obtained by supplying an oil agent containing no ultraviolet absorber. A two-weight ricott made of these polyurethane fibers and a polyester fiber of 50 denier / 36 filaments is used in Smikalo.
n Red E-RPD 0.1% owf at 125 ° C
Stained with. When the dyed fabric was final set at 160 ° C. and evaluated for light resistance, it was grade 4-5 when the ultraviolet absorber was added, whereas grade 3 or lower was not added.
【００１５】実施例２ 実施例１のツーウェイトリコットを蛍光染料Ｕｖｉｔｅ
ｘ−ＥＲＮ １％ｏｗｆで染色したところ、蛍光染料の
効果により良好な白色となった。この布帛の耐光性は３
−４級であった。Example 2 The two-weight ricott of Example 1 was replaced with the fluorescent dye Uvit.
When dyed with x-ERN 1% owf, a good white color was obtained due to the effect of the fluorescent dye. The light resistance of this fabric is 3
It was grade -4.
【００１６】比較例２ 比較例１のツーウェイトリコットを、実施例１の紫外線
吸収剤、Ｓｕｍｉｐｏｎ−ＵＬ １％ｏｗｆ蛍光染料Ｕ
ｖｉｔｅｘ−ＥＲＮ １％ｏｗｆで染色したところ、紫
外線吸収剤により蛍光染料の効果が損なわれ、蛍光増白
効果が得られなかった。COMPARATIVE EXAMPLE 2 The two-weight cotton of Comparative Example 1 was replaced with the ultraviolet absorber of Example 1, Sumipon-UL 1% owf fluorescent dye U.
When dyed with vitex-ERN 1% owf, the effect of the fluorescent dye was impaired by the ultraviolet absorber, and the fluorescent whitening effect was not obtained.
【００１７】実施例３ ヒンダードアミン系光安定剤としてコハク酸ジメチル−
１−（２−ヒドロキシエチル）−４−ヒドロキシ−２，
２，６，６，−テトラメチルピペリジン重縮合物（分子
量３０００以上）を５０００ｐｐｍ添加して分子量２０
００のポリ−３−メチル−ペンタンアゼレートをソフト
セグメントとするポリウレタンを合成し、これを２１０
デニール／６フィラメントのポリウレタン繊維に紡糸す
る際に、実施例１と同様に紫外線吸収剤を添加した紡糸
油剤を付与した。得られたポリウレタン繊維と５０デニ
ール／４８フィラメントのポリエステル糸でラッセル生
地を編成し実施例１と同様に染色し耐光性を評価したと
ころ４−５級であった。Example 3 Dimethyl succinate as a hindered amine light stabilizer
1- (2-hydroxyethyl) -4-hydroxy-2,
A molecular weight of 2,6,6-tetramethylpiperidine polycondensate (molecular weight of 3000 or more) was added at 5000 ppm to obtain a molecular weight of 20.
Polyurethane having poly-3-methyl-pentaneazelate of 00 as a soft segment was synthesized and
When spinning a denier / 6 filament polyurethane fiber, a spinning oil containing an ultraviolet absorber was applied in the same manner as in Example 1. When the Russell fabric was knitted with the obtained polyurethane fiber and polyester yarn of 50 denier / 48 filament and dyed in the same manner as in Example 1 to evaluate the light resistance, it was 4-5 grade.
【００１８】実施例４ 実施例３において、紡糸時にヒンダードフェノール系酸
化防止剤として、３，９−ビス［２−｛３−（３−ｔ−
ブチル−４−ヒドロキシ−５−メチルフェニル）プロピ
オニルオキシ｝−１，１−ジメチルエチル］−２，４，
８、１０−テトラオキサスピロ［５，５］ウンデカンを
４０００ｐｐｍ添加し、他は同様にしてラッセル生地に
編成し、染色し、耐光性を評価したところ、５級と良好
な耐光性を示した。Example 4 In Example 3, 3,9-bis [2- {3- (3-t- was used as a hindered phenolic antioxidant during spinning.
Butyl-4-hydroxy-5-methylphenyl) propionyloxy} -1,1-dimethylethyl] -2,4
When 4000 ppm of 8,10-tetraoxaspiro [5,5] undecane was added and the others were similarly knitted into a Russell fabric, dyed, and evaluated for light resistance, light resistance was evaluated to be Grade 5, and good light resistance was exhibited.
【００１９】[0019]
【発明の効果】本発明の方法によれば、従来のポリウレ
タンの紡糸時に酸化チタンや紫外線吸収剤を練り込んだ
り、染色時に紫外線吸収剤を併用する方法などに比べ、
下記の利点を有する。 ・溶融紡糸に適用することにより透明性の高いポリウレ
タン繊維が得られる。 ・紡糸時の溶融温度や溶剤との反応による紫外線吸収剤
の劣化がなく、適用できる紫外線吸収剤の選択範囲が広
くなる。 ・比較的少量の紫外線吸収剤を繊維表面に効率的に均一
に付与できる。 ・高価な紫外線吸収剤の無駄がない。 ・染色時の蛍光増白効果などを阻害しない。 ・酸化紡糸剤、耐光安定剤などの併用による相乗効果が
期待できる。 ・紡糸時に酸化紡糸剤、耐光安定剤などとの相互反応に
よる劣化がない。EFFECTS OF THE INVENTION According to the method of the present invention, as compared with the conventional method of kneading titanium oxide or an ultraviolet absorber during spinning of polyurethane or using the ultraviolet absorber together during dyeing,
It has the following advantages: -By applying it to melt spinning, highly transparent polyurethane fiber can be obtained. -There is no deterioration of the UV absorber due to the melting temperature during spinning or the reaction with the solvent, and the applicable range of UV absorbers is widened. -A relatively small amount of UV absorber can be efficiently and uniformly applied to the fiber surface.・ There is no waste of expensive UV absorbers. -Does not interfere with the fluorescent whitening effect during dyeing. -A synergistic effect can be expected due to the combined use of oxidative spinning agents and light resistance stabilizers. -No deterioration due to mutual reaction with oxidative spinning agents, light stabilizers, etc. during spinning.
Claims (1)
剤を添加した紡糸油剤を付与することを特徴とする耐光
性に優れたポリウレタン繊維の製法。1. A method for producing a polyurethane fiber having excellent light resistance, which comprises applying a spinning oil agent containing an ultraviolet absorber to the spun polyurethane fiber.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1539793A JPH06228816A (en) | 1993-02-02 | 1993-02-02 | Production of polyurethane fiber excellent in light-fastness |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1539793A JPH06228816A (en) | 1993-02-02 | 1993-02-02 | Production of polyurethane fiber excellent in light-fastness |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH06228816A true JPH06228816A (en) | 1994-08-16 |
Family
ID=11887602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1539793A Pending JPH06228816A (en) | 1993-02-02 | 1993-02-02 | Production of polyurethane fiber excellent in light-fastness |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH06228816A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2240498B (en) * | 1990-01-23 | 1993-10-06 | Akechi Ceramics Kk | Molten steel pouring nozzle |
| WO2008102822A1 (en) | 2007-02-20 | 2008-08-28 | Fujifilm Corporation | Polymer material containing ultraviolet absorbent |
| WO2008123504A1 (en) | 2007-03-30 | 2008-10-16 | Fujifilm Corporation | Ultraviolet ray absorber composition |
| WO2009022736A1 (en) | 2007-08-16 | 2009-02-19 | Fujifilm Corporation | Heterocyclic compound, ultraviolet ray absorbent, and composition comprising the ultraviolet ray absorbent |
| WO2009123142A1 (en) | 2008-03-31 | 2009-10-08 | 富士フイルム株式会社 | Ultraviolet absorbent compositions |
| WO2009123141A1 (en) | 2008-03-31 | 2009-10-08 | 富士フイルム株式会社 | Ultraviolet absorbent compositions |
| WO2009136624A1 (en) | 2008-05-09 | 2009-11-12 | 富士フイルム株式会社 | Ultraviolet absorbent composition |
-
1993
- 1993-02-02 JP JP1539793A patent/JPH06228816A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2240498B (en) * | 1990-01-23 | 1993-10-06 | Akechi Ceramics Kk | Molten steel pouring nozzle |
| WO2008102822A1 (en) | 2007-02-20 | 2008-08-28 | Fujifilm Corporation | Polymer material containing ultraviolet absorbent |
| WO2008123504A1 (en) | 2007-03-30 | 2008-10-16 | Fujifilm Corporation | Ultraviolet ray absorber composition |
| WO2009022736A1 (en) | 2007-08-16 | 2009-02-19 | Fujifilm Corporation | Heterocyclic compound, ultraviolet ray absorbent, and composition comprising the ultraviolet ray absorbent |
| WO2009123142A1 (en) | 2008-03-31 | 2009-10-08 | 富士フイルム株式会社 | Ultraviolet absorbent compositions |
| WO2009123141A1 (en) | 2008-03-31 | 2009-10-08 | 富士フイルム株式会社 | Ultraviolet absorbent compositions |
| WO2009136624A1 (en) | 2008-05-09 | 2009-11-12 | 富士フイルム株式会社 | Ultraviolet absorbent composition |
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