JPH08269814A - Flame retardant acrylic synthetic fiber excellent in weather resistance - Google Patents
Flame retardant acrylic synthetic fiber excellent in weather resistanceInfo
- Publication number
- JPH08269814A JPH08269814A JP10303995A JP10303995A JPH08269814A JP H08269814 A JPH08269814 A JP H08269814A JP 10303995 A JP10303995 A JP 10303995A JP 10303995 A JP10303995 A JP 10303995A JP H08269814 A JPH08269814 A JP H08269814A
- Authority
- JP
- Japan
- Prior art keywords
- acrylic synthetic
- weather resistance
- synthetic fiber
- retardant acrylic
- flame retardant
- 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
- Compositions Of Macromolecular Compounds (AREA)
- Artificial Filaments (AREA)
Abstract
Description
【0001】[0001]
【産業上の利用分野】本発明は耐候性に優れ、黄変、特
に高温時の黄変着色が改善された難燃アクリル系合成繊
維に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a flame-retardant acrylic synthetic fiber having excellent weather resistance and having improved yellowing, especially yellowing coloring at high temperature.
【0002】[0002]
【従来の技術】アクリル系合成繊維は、風合や染色性が
優れるため衣料用,寝装用に幅広く使われている。しか
しながら、光や熱によって繊維が黄変しやすく実用上種
々な制約を受けているのが現状である。特に塩素を共重
合成分に含むモダクリル繊維は光や熱によって黄変しや
すいという問題がある。2. Description of the Related Art Acrylic synthetic fibers are widely used for clothing and bedding because of their excellent texture and dyeability. However, under the present circumstances, the fibers are easily yellowed by light or heat and are practically restricted. In particular, modacrylic fibers containing chlorine as a copolymerization component have a problem that they are easily yellowed by light or heat.
【0003】かかる問題点を改良するために、例えばヒ
ンダートフェノール系の酸化防止剤,硫黄系酸化防止剤
を用いることが検討されてきたが、これらの方法はオレ
フィン系合成繊維には有効であるが、アクリル系合成繊
維に対しては効果が少ないという問題がある。また、例
えば特公平2−15642号公報にはベンゾトリアゾー
ル系化合物である紫外線吸収剤を添加したモダクリル繊
維や、特開平2−33315号公報には有機錫を添加し
たモダクリル繊維が提案されているが、湿式紡糸の場合
には凝固浴への紫外線吸収剤、有機錫の溶出のため歩留
りが不良であり、さらに染色性に悪影響及ぼす問題があ
る。また耐候性を向上せしめるためにルチル型の二酸化
チタンを用いることは塗料分野では行われているが、繊
維へ適用した場合、その硬度及び紡糸操業性に問題があ
り、繊維分野ではルチル型の二酸化チタンが用いられて
いないのが現状である。In order to improve such problems, it has been studied to use, for example, hindered phenol type antioxidants and sulfur type antioxidants, but these methods are effective for olefin type synthetic fibers. However, there is a problem that it is less effective for acrylic synthetic fibers. In addition, for example, Japanese Patent Publication No. 2-15642 proposes modacrylic fiber added with an ultraviolet absorber which is a benzotriazole compound, and Japanese Patent Application Laid-Open No. 2-33315 proposes modacrylic fiber added with organic tin. In the case of wet spinning, the yield is poor due to the elution of the ultraviolet absorber and organic tin into the coagulation bath, and there is a problem that the dyeability is adversely affected. Further, the use of rutile type titanium dioxide in order to improve weather resistance has been performed in the paint field, but when applied to fibers, there is a problem in hardness and spinning operability, and in the fiber field, rutile type titanium dioxide is used. The current situation is that titanium is not used.
【0004】[0004]
【発明が解決しようとする課題】上記したように難燃ア
クリル系合成繊維に対して耐候性、高温時の黄変着色を
改善せしめる手段は種々提案されているものの、染色
性,操業性が良好で耐候性に優れ、高温時の黄変着色が
改良された難燃アクリル系合成繊維は得られていない。
本発明は上述の問題点に鑑みてなされたものであって、
その目的は染色性,操業性が良好で、耐候性に優れ、高
温時の黄変着色が改良された難燃アクリル系合成繊維を
提供することにある。As described above, although various means have been proposed for improving the weather resistance and yellowing discoloration at high temperatures of flame-retardant acrylic synthetic fibers, they have good dyeability and operability. No flame-retardant acrylic synthetic fibers with excellent weather resistance and improved yellowing coloring at high temperature have been obtained.
The present invention has been made in view of the above problems,
It is an object of the present invention to provide a flame-retardant acrylic synthetic fiber having good dyeability and operability, excellent weather resistance, and improved yellowing coloring at high temperatures.
【0005】[0005]
【課題を解決するための手段】上述の目的は、塩化ビニ
ル及び/又は塩化ビニリデンを含有するアクリロニトリ
ル系重合体に対して、9−10−ジヒドロ−9−オキサ
−10−フォスファフェナンスレン−10−オキサイド
を0.05〜2重量%及び2−ヒドロキシ−4−(メタ
クリロイルオキシエトキシ)ベンゾフェノン/メタクリ
ル酸メチル共重合体を0.1〜5重量%含有してなるこ
とを特徴とする耐候性に優れた難燃アクリル系合成繊維
により達成される。SUMMARY OF THE INVENTION The above-mentioned object is to provide an acrylonitrile polymer containing vinyl chloride and / or vinylidene chloride with 9-10-dihydro-9-oxa-10-phosphaphenanthrene- Weather resistance characterized by containing 0.05 to 2% by weight of 10-oxide and 0.1 to 5% by weight of 2-hydroxy-4- (methacryloyloxyethoxy) benzophenone / methyl methacrylate copolymer. It is achieved by excellent flame-retardant acrylic synthetic fiber.
【0006】以下、本発明を詳細に説明する。The present invention will be described in detail below.
【0007】本発明に使用する塩化ビニル及び/又は塩
化ビニリデンを含有するアクリロニトリル系重合体とし
ては、アクリロニトリル40〜70重量%、塩化ビニル
及び/又は塩化ビニリデン30〜60重量%、他の不飽
和単量体及びアニオン性モノマーより達成されるものが
挙げられる。前記不飽和単量体としては、アクリル酸メ
チル,メタクリル酸メチル等のアクリル酸エステル類,
メタクリル酸エステル類、スチレン,酢酸ビニル等の中
性単量体、アクリル酸,メタクリル酸等の酸性単量体が
挙げられる。また前記アニオン性モノマーとしては、ア
リルスルフォン酸,メタリルスルフォン酸,ブチレンス
ルフォン酸,2−アクリルアミド−2−メチルプロパン
スルフォン酸等のアルカリ金属塩が挙げられる。As the acrylonitrile-based polymer containing vinyl chloride and / or vinylidene chloride used in the present invention, acrylonitrile 40 to 70% by weight, vinyl chloride and / or vinylidene chloride 30 to 60% by weight, and other unsaturated monomer are used. Examples include those achieved from a monomer and an anionic monomer. Examples of the unsaturated monomer include acrylic acid esters such as methyl acrylate and methyl methacrylate,
Examples thereof include methacrylic acid esters, neutral monomers such as styrene and vinyl acetate, and acidic monomers such as acrylic acid and methacrylic acid. Examples of the anionic monomer include alkali metal salts such as allyl sulfonic acid, methallyl sulfonic acid, butylene sulfonic acid and 2-acrylamido-2-methylpropane sulfonic acid.
【0008】本発明に使用される重合体は、水系懸濁重
合,乳化重合,溶液重合などの公知の重合方法によって
作られ、特に限定されるものではない。The polymer used in the present invention is produced by a known polymerization method such as aqueous suspension polymerization, emulsion polymerization and solution polymerization, and is not particularly limited.
【0009】本発明に使用する9−10−ジヒドロ−9
−オキサ−10−フォスファフェナンスレン−10−オ
キサイド(以下、DOPOと略称する)は、下記構造式
(1)で示される物である。9-10-dihydro-9 used in the present invention
-Oxa-10-phosphaphenanthrene-10-oxide (hereinafter abbreviated as DOPO) is a compound represented by the following structural formula (1).
【0010】[0010]
【化1】 Embedded image
【0011】かかるDOPOはアクリロニトリル系重合
体に対して0.05〜2重量%、好ましくは0.05〜
1重量%含有させることが必要である。0.05重量%
未満では着色防止効果が得られず、一方2重量%を超え
るとDOPOによる着色が増し好ましくない。Such DOPO is contained in an amount of 0.05 to 2% by weight, preferably 0.05 to 2% by weight, based on the acrylonitrile polymer.
It is necessary to contain 1% by weight. 0.05% by weight
If it is less than the above range, the effect of preventing coloration cannot be obtained.
【0012】本発明に使用する2−ヒドロキシ−4−
(メタクリロイルオキシエトキシ)ベンゾフェノン(以
下、HMBと略称する)/メタクリル酸メチル共重合体
は、下記構造式(2)で示される物である。2-hydroxy-4-used in the present invention
The (methacryloyloxyethoxy) benzophenone (hereinafter abbreviated as HMB) / methyl methacrylate copolymer is represented by the following structural formula (2).
【0013】[0013]
【化2】 Embedded image
【0014】該共重合体中のHMBの含有率は20〜6
0重量%、好ましくは30〜50重量%である。20重
量%未満では耐候性向上の効果が不十分であり、またH
MBが20重量%未満の含有量の共重合体を大量に添加
すると、難燃アクリル系合成繊維の難燃性の低下や耐熱
性の低下等繊維物性に悪影響がでる。一方60重量%を
越えると共重合体の着色や耐熱性の低下が起き好ましく
ない。共重合体の分子量はゲルパーミエーションクロマ
トグラフ(以下、GPCと略称する)におけるポリスチ
レン換算分子量で2000〜50000が好ましい。分
子量が2000未満では、湿式紡糸の際に凝固浴中に溶
出して歩留りが不良となるので好ましくない。一方分子
量が50000を超えると、ポリマーの溶液粘度が高く
なり紡糸原液への添加混合が困難となるので好ましくな
い。The content of HMB in the copolymer is 20 to 6
It is 0% by weight, preferably 30 to 50% by weight. If it is less than 20% by weight, the effect of improving weather resistance is insufficient, and H
When a large amount of a copolymer having a content of MB less than 20% by weight is added, the physical properties of the fiber such as the flame retardance and heat resistance of the flame-retardant acrylic synthetic fiber are adversely affected. On the other hand, when it exceeds 60% by weight, the copolymer is colored and heat resistance is deteriorated, which is not preferable. The molecular weight of the copolymer is preferably 2,000 to 50,000 in terms of polystyrene equivalent in a gel permeation chromatograph (hereinafter abbreviated as GPC). When the molecular weight is less than 2000, it is not preferable because it is eluted in the coagulation bath during wet spinning and the yield becomes poor. On the other hand, if the molecular weight exceeds 50,000, the solution viscosity of the polymer becomes high, which makes it difficult to add and mix it in the spinning dope, which is not preferable.
【0015】かかるHMB/メタクリル酸メチル共重合
体はアクリロニトリル系重合体に対して0.1〜5重量
%、好ましくは0.3〜3重量%含有させることが必要
である。0.1重量%未満では耐候性向上の効果が得ら
れず、一方5重量%を超えると繊維の製造時に膠着が生
じるとともに耐候性向上効果も飽和となるので好ましく
ない。The HMB / methyl methacrylate copolymer should be contained in an amount of 0.1 to 5% by weight, preferably 0.3 to 3% by weight, based on the acrylonitrile polymer. If it is less than 0.1% by weight, the effect of improving the weather resistance cannot be obtained. On the other hand, if it exceeds 5% by weight, sticking occurs during the production of the fiber and the effect of improving the weather resistance is saturated, which is not preferable.
【0016】次に、本発明の耐候性に優れた難燃アクリ
ル系合成繊維の製造方法の一例について説明する。本発
明の難燃性アクリル系合成繊維は、塩化ビニル及び/又
は塩化ビニリデンを含有するアクリロニトリル系重合体
の有機溶剤溶液にDOPO及びHMB/メタクリル酸メ
チル共重合体を添加し紡糸することによって、繊維中に
DOPO及びHMB/メタクリル酸メチル共重合体を均
一に含有せしめる。紡糸方法は通常の湿式,乾式,乾・
湿式いずれもが可能である。そして例えば湿式紡糸の場
合には通常の難燃アクリル系合成繊維と同様の条件で行
えば良く、数段の浴槽を通し、順次延伸,水洗,乾燥,
後処理を行う。Next, an example of the method for producing the flame-retardant acrylic synthetic fiber having excellent weather resistance of the present invention will be described. The flame-retardant acrylic synthetic fiber of the present invention is obtained by adding DOPO and HMB / methyl methacrylate copolymer to an organic solvent solution of an acrylonitrile polymer containing vinyl chloride and / or vinylidene chloride, and spinning the resulting fiber. DOPO and HMB / methyl methacrylate copolymer are uniformly contained therein. Spinning method is normal wet, dry, dry
Both wet methods are possible. Then, for example, in the case of wet spinning, it may be carried out under the same conditions as for ordinary flame-retardant acrylic synthetic fibers.
Post-process.
【0017】尚、DOPO及びHMB/メタクリル酸メ
チル共重合体の添加方法は、紡糸原液に直接添加しても
よく、有機溶剤に分散又は溶解し原液に添加してもよ
く、特に制限されるものではない。また、場合によって
は紡糸後ゲル膨潤状態の繊維に乳化剤を用いたエマルジ
ョン状態で付与し、乾熱及び緻密化を行う方法で添加し
ても良い。The DOPO and HMB / methyl methacrylate copolymer may be added directly to the spinning dope, or may be dispersed or dissolved in an organic solvent and added to the dope, which is not particularly limited. is not. In some cases, the fibers may be added in a gel swollen state after spinning in an emulsion state using an emulsifier, followed by dry heat and densification.
【0018】[0018]
【実施例】次に実施例を示し本発明を具体的に説明す
る。実施例中の部、%は特に断わらない限り重量部、重
量%を示す。耐熱黄変性の測定評価は、得られたアクリ
ル系繊維を常法により紡績して30番単糸となした後丸
編したものを、150℃で30分、乾熱熱処理機におい
て処理し、処理前後の比較を変退色(グレースケール)
で評価を行った。耐候性の測定評価は、上記と同様に丸
編したものを、カーボンフェードメーターでブラックパ
ネル温度63℃×200時間の条件下で照射し、処理前
後の比較を変退色(グレースケール)で評価を行なっ
た。EXAMPLES Next, the present invention will be specifically described by showing examples. Parts and% in the examples are parts by weight and% by weight, unless otherwise specified. The heat-resistant yellowing was measured and evaluated by spinning the obtained acrylic fiber into a number 30 single yarn and then circularly knitting the same, which was treated at 150 ° C. for 30 minutes in a dry heat treatment machine and treated. Discolored before and after comparison (gray scale)
It was evaluated by. For the measurement and evaluation of the weather resistance, circular knitting as in the above was irradiated with a carbon fade meter under the condition of a black panel temperature of 63 ° C. for 200 hours, and the comparison before and after the treatment was evaluated by discoloration (gray scale). I did.
【0019】実施例1〜8、比較例1〜5 アクリロニトリル(AN)/塩化ビニリデン(VC
l2 )/2−アクリルアミド−2−メチルプロパンスル
ホン酸ソーダ(SAM)=53/44/3からなるアク
リロニトリル系重合体のジメチルホルムアミド(以下、
DMFと略称する)溶液を準備し、紡糸原液とした。一
方、DOPO15重量%をDMFに均一分散し、またH
MB/メタクリル酸メチル共重合体をDMFに溶解して
15重量%のDMF溶液とした。そして、上記DOPO
のDMF分散液とHMB/メタクリル酸メチル共重合体
のDMF溶液を所定量紡糸原液に添加混合した後に、こ
の紡糸原液を20℃、60%DMF水溶液中に紡出し、
脱溶媒させながら延伸、水洗工程を経た後、繊維油剤を
付与し、次にローラー式乾燥機を用い150℃で乾燥緻
密化を行った。ついで機械クリンプを付与し湿熱115
℃でクリンプのセットを行った。得られた繊維をカット
し、次いで紡績をした後丸編布を作製した。この繊維を
さきに述べた方法により評価した。結果を表1に示す。Examples 1 to 8 and Comparative Examples 1 to 5 Acrylonitrile (AN) / vinylidene chloride (VC)
l 2 ) / 2-acrylamido-2-methylpropanesulfonic acid sodium (SAM) = 53/44/3, an acrylonitrile polymer dimethylformamide (hereinafter,
A solution (abbreviated as DMF) was prepared and used as a spinning dope. Meanwhile, 15% by weight of DOPO was uniformly dispersed in DMF, and H
The MB / methyl methacrylate copolymer was dissolved in DMF to give a 15 wt% DMF solution. And the above DOPO
After adding and mixing a predetermined amount of the DMF dispersion liquid and the DMF solution of the HMB / methyl methacrylate copolymer to the spinning stock solution, the spinning stock solution was spun into a 60% DMF aqueous solution at 20 ° C.
A fiber oil was applied after stretching and washing with water while removing the solvent, and then densification was performed at 150 ° C. using a roller dryer. Next, a mechanical crimp is applied to wet heat 115
The crimp was set at ° C. The obtained fiber was cut and then spun to make a circular knit fabric. The fiber was evaluated by the method previously described. The results are shown in Table 1.
【0020】[0020]
【表1】 [Table 1]
【0021】表1から明らかなように、実施例品は比較
例品に比べて優れた耐熱黄変性,耐候性を有しているこ
とがわかる。また、染色試験を行った所、染色性に悪影
響は見られず、得られた製品は通常の難燃アクリル系合
成繊維を染色したものと大きな差はなかった。As can be seen from Table 1, the product of the example has excellent heat yellowing resistance and weather resistance as compared with the product of the comparative example. In addition, when a dyeing test was conducted, no adverse effect was observed on the dyeability, and the obtained product was not significantly different from that obtained by dyeing ordinary flame-retardant acrylic synthetic fibers.
【0022】[0022]
【発明の効果】本発明の難燃アクリル系合成繊維は、耐
候性に優れ、高温時の黄変着色が改良されており、また
通常の染色性,操業性等を有しており頗る有用である。
また、本発明によって得られた繊維は、通常のアクリル
系合成繊維,ポリエステル,ナイロン,木綿,レーヨ
ン,羊毛等他の繊維と混用して使用することも可能であ
り、耐候性を必要とするカーペット,カーテン等の用途
に使用することが出来るため、産業上極めて有意義なも
のである。The flame-retardant acrylic synthetic fiber of the present invention is excellent in weather resistance, has improved yellowing and coloring at high temperatures, and has ordinary dyeability, operability, etc. is there.
Further, the fiber obtained by the present invention can also be used by mixing with other fibers such as ordinary acrylic synthetic fiber, polyester, nylon, cotton, rayon, wool, etc., and a carpet which requires weather resistance. Since it can be used for applications such as curtains, it is extremely meaningful industrially.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 FI 技術表示箇所 C08L 27/06 KHW C08L 27/06 KHW 27/08 LFU 27/08 LFU 33/20 LJL 33/20 LJL ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 6 Identification code Internal reference number FI Technical display location C08L 27/06 KHW C08L 27/06 KHW 27/08 LFU 27/08 LFU 33/20 LJL 33/20 LJL
Claims (1)
含有するアクリロニトリル系重合体に対して、9−10
−ジヒドロ−9−オキサ−10−フォスファフェナンス
レン−10−オキサイドを0.05〜2重量%及び2−
ヒドロキシ−4−(メタクリロイルオキシエトキシ)ベ
ンゾフェノン/メタクリル酸メチル共重合体を0.1〜
5重量%含有してなることを特徴とする耐候性に優れた
難燃アクリル系合成繊維。1. Acrylonitrile-based polymer containing vinyl chloride and / or vinylidene chloride, 9-10
-Dihydro-9-oxa-10-phosphaphenanthrene-10-oxide 0.05-2% by weight and 2-
Hydroxy-4- (methacryloyloxyethoxy) benzophenone / methyl methacrylate copolymer is added to 0.1 to
A flame-retardant acrylic synthetic fiber having excellent weather resistance, which is characterized by containing 5% by weight.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10303995A JPH08269814A (en) | 1995-04-03 | 1995-04-03 | Flame retardant acrylic synthetic fiber excellent in weather resistance |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10303995A JPH08269814A (en) | 1995-04-03 | 1995-04-03 | Flame retardant acrylic synthetic fiber excellent in weather resistance |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH08269814A true JPH08269814A (en) | 1996-10-15 |
Family
ID=14343532
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP10303995A Pending JPH08269814A (en) | 1995-04-03 | 1995-04-03 | Flame retardant acrylic synthetic fiber excellent in weather resistance |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH08269814A (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001122977A (en) * | 1999-10-27 | 2001-05-08 | Sanko Chem Co Ltd | Flame-retardant polyacrylonitrile-based resin molded product |
CN102759593A (en) * | 2012-07-20 | 2012-10-31 | 青岛普仁仪器有限公司 | Chromatograph detection method for inorganic anions and cations in DOPO |
CN103897104A (en) * | 2014-03-04 | 2014-07-02 | 河北联合大学 | Polymeric phosphorus-silicon flame retardant containing DOPO side group and preparation method thereof |
CN107250449A (en) * | 2015-02-16 | 2017-10-13 | 株式会社钟化 | The manufacture method of acrylic fibers |
CN110670351A (en) * | 2019-10-09 | 2020-01-10 | 湖南工程学院 | Synthesis and application of novel triazine derivative flame retardant |
-
1995
- 1995-04-03 JP JP10303995A patent/JPH08269814A/en active Pending
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001122977A (en) * | 1999-10-27 | 2001-05-08 | Sanko Chem Co Ltd | Flame-retardant polyacrylonitrile-based resin molded product |
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