JP2002088368A - Agent for flame-retarding treatment - Google Patents
Agent for flame-retarding treatmentInfo
- Publication number
- JP2002088368A JP2002088368A JP2000279916A JP2000279916A JP2002088368A JP 2002088368 A JP2002088368 A JP 2002088368A JP 2000279916 A JP2000279916 A JP 2000279916A JP 2000279916 A JP2000279916 A JP 2000279916A JP 2002088368 A JP2002088368 A JP 2002088368A
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- flame
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- general formula
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- weight
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- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Fireproofing Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、難燃加工薬剤に関
する。さらに詳しくは、本発明は、耐久性に優れた難燃
性をポリエステル繊維に付与し、安定な難燃加工を可能
とする難燃加工薬剤に関する。[0001] The present invention relates to a flame retardant chemical. More specifically, the present invention relates to a flame-retardant agent that imparts excellent flame retardancy to polyester fibers and enables stable flame-retardant processing.
【０００２】[0002]
【従来の技術】従来より、ポリエステル繊維の耐久難燃
加工は、ヘキサブロモシクロドデカンに代表される脂環
式ハロゲン化合物を染色浴中又はサーモゾル法にて繊維
の内部に浸透させることにより行われていた。しかし、
ハロゲン化合物により難燃加工されたポリエステル繊維
は、燃焼時に人体に有害なガスが発生したり、自然環境
への有害性が危惧されるなどの問題を有していた。ハロ
ゲン化合物に変わる難燃成分として、リン系化合物が各
種検討され、一般式［１］で表される縮合リン酸エステ
ルが良好な難燃性を有し、ハロゲン化合物に代わり得る
化合物として見いだされている。ただし、式中、ｐは１
又は２である。2. Description of the Related Art Durable flame-retardant processing of polyester fiber has been conventionally performed by infiltrating an alicyclic halogen compound represented by hexabromocyclododecane into a fiber in a dye bath or by a thermosol method. Was. But,
Polyester fibers that have been flame-retarded with halogen compounds have had problems such as the generation of harmful gases to the human body during combustion and the fear of harm to the natural environment. Various phosphorus-based compounds have been studied as flame-retardant components replacing halogen compounds, and condensed phosphoric esters represented by the general formula [1] have been found to have good flame retardancy and can be substituted for halogen compounds. I have. Where p is 1
Or 2.
【化４】 この縮合リン酸エステルをポリエステル繊維に付与する
には、溶剤などに溶解するか、あるいはエマルジョンに
して、染色浴中又はパディング処理にて付与する必要が
有る。溶剤に溶解した場合、溶剤が排液や大気中に放出
されるために、環境へ与える負荷が大きい。エマルジョ
ンとするには、一般に各種の界面活性剤が使用される
が、この縮合リン酸エステルのエマルジョンは、経時的
にエマルジョンが破壊し分離するなど、安定にエマルジ
ョン化することが困難であった。また、この縮合リン酸
エステルのエマルジョンは、染浴同浴で付与する際に、
染料の分散性を阻害するなどの欠点を有し、実用に耐え
ないという問題があった。Embedded image In order to apply this condensed phosphoric acid ester to polyester fibers, it is necessary to dissolve it in a solvent or the like or to make it into an emulsion and apply it in a dyeing bath or by padding. When dissolved in a solvent, the solvent is released into the drainage and the atmosphere, and thus has a large impact on the environment. Generally, various surfactants are used to form an emulsion. However, it has been difficult to stably form an emulsion of this condensed phosphate ester, for example, the emulsion is broken and separated over time. Also, when the emulsion of the condensed phosphate ester is applied in the same bath as the dyeing bath,
It has disadvantages such as impairing the dispersibility of the dye, and has a problem that it is not practical.
【０００３】[0003]
【発明が解決しようとする課題】本発明は、耐久性に優
れた難燃性をポリエステル繊維に付与し、安定な難燃加
工を可能とする難燃加工薬剤を提供することを目的とし
てなされたものである。SUMMARY OF THE INVENTION An object of the present invention is to provide a flame-retardant agent capable of imparting flame resistance excellent in durability to polyester fiber and enabling stable flame-retardant processing. Things.
【０００４】[0004]
【課題を解決するための手段】本発明者らは、上記の課
題を解決すべく鋭意研究を重ねた結果、スチレン化フェ
ノールのエチレンオキサイド付加物又はその硫酸エステ
ル塩を界面活性剤として用いることにより、従来は安定
かつ実用的なエマルジョン化が困難であった縮合リン酸
エステルを乳化分散し、ポリエステル繊維の耐久難燃加
工を可能とする優れた非ハロゲン系の難燃加工薬剤が得
られることを見いだし、この知見に基づいて本発明を完
成するに至った。すなわち、本発明は、（１）一般式
［１］で表される縮合リン酸エステルが、一般式［２］
で表される界面活性剤及び／又は一般式［３］で表され
る界面活性剤を用いて、水中に乳化分散されてなること
を特徴とする難燃加工薬剤、Means for Solving the Problems The inventors of the present invention have conducted intensive studies to solve the above-mentioned problems, and as a result, they have found that an ethylene oxide adduct of styrenated phenol or a sulfate thereof is used as a surfactant. By emulsifying and dispersing the condensed phosphoric acid ester, which was conventionally difficult to emulsify stably and practically, it is possible to obtain an excellent non-halogen flame retardant agent that enables durable flame retardant processing of polyester fiber. The present inventors have completed the present invention based on this finding. That is, in the present invention, (1) the condensed phosphoric acid ester represented by the general formula [1]
A flame-retardant processing agent characterized by being emulsified and dispersed in water using a surfactant represented by the formula and / or a surfactant represented by the general formula [3].
【化５】 （ただし、式中、ｐは１又は２である。）Embedded image (Where p is 1 or 2)
【化６】 （ただし、式中、ｍは１〜３であり、ｎは５〜３０であ
る。）Embedded image (Where m is 1 to 3 and n is 5 to 30)
【化７】 （ただし、式中、ｍは１〜３であり、ｎは５〜３０であ
り、Ｍ+はＮａ+、Ｋ+又はＮＨ4 +である。）、を提供す
るものである。さらに、本発明の好ましい態様として、
（２）一般式［１］で表される縮合リン酸エステルの含
有量が、２０〜７０重量％である第１項記載の難燃加工
薬剤、及び、（３）一般式［２］及び／又は一般式
［３］で表される界面活性剤の使用量が、一般式［１］
で表される縮合リン酸エステル１００重量部に対して、
５〜４０重量部である第１項記載の難燃加工薬剤、を挙
げることができる。Embedded image (Wherein, m is 1 to 3, n is 5 to 30, M + is Na +, K + or NH 4 is +.), There is provided a. Further, as a preferred embodiment of the present invention,
(2) The flame-retardant processing agent according to (1), wherein the content of the condensed phosphoric ester represented by the general formula [1] is 20 to 70% by weight, and (3) the general formula [2] and / or Alternatively, the amount of the surfactant represented by the general formula [3] is less than that of the general formula [1].
With respect to 100 parts by weight of the condensed phosphoric ester represented by
The flame-retardant processing agent according to item 1, which is 5 to 40 parts by weight.
【０００５】[0005]
【発明の実施の形態】本発明の難燃加工薬剤は、一般式
［１］で表される縮合リン酸エステルが、一般式［２］
で表される界面活性剤及び／又は一般式［３］で表され
る界面活性剤を用いて、水中に乳化分散されてなる薬剤
である。BEST MODE FOR CARRYING OUT THE INVENTION The flame-retardant processing agent of the present invention is obtained by converting the condensed phosphate represented by the general formula [1] to the general formula [2]
And / or a surfactant represented by the general formula [3] and emulsified and dispersed in water.
【化８】 ただし、式中、ｐは１又は２であり、ｍは１〜３であ
り、ｎは５〜３０であり、Ｍ+はＮａ+、Ｋ+又はＮＨ4 +
である。本発明に用いる一般式［１］で表される縮合リ
ン酸エステルは、例えば、アクゾ ノーベル社などから
ファイロールフレックスＲＤＰなどの商品名で販売され
ているので、市販品を購入して使用することができる。Embedded image However, in the formula, p is 1 or 2, m is 1 to 3, n is 5 to 30, and M + is Na + , K +, or NH 4 +
It is. The condensed phosphoric acid ester represented by the general formula [1] used in the present invention is, for example, sold by Akzo Nobel under the trade name of Filolflex RDP or the like. Can be.
【０００６】本発明に用いる一般式［２］で表される界
面活性剤は、フェノール１モルにスチレンを１〜３モル
付加して得られるスチレン化フェノール１モルに対し
て、エチレンオキサイド３〜５０モルを付加することに
より得ることができる。エチレンオキサイドの平均付加
モル数が５未満であっても、３０を超えても、一般式
［１］で表される縮合リン酸エステルのエマルジョン安
定性が不良になるおそれがある。本発明に用いる一般式
［３］で表される界面活性剤は、一般式［２］で表され
る界面活性剤を硫酸エステル化し、水酸化ナトリウム、
水酸化カリウム、アンモニアなどを用いて中和すること
により得ることができる。一般式［３］で表される界面
活性剤のエチレンオキサイドの平均付加モル数が５未満
であっても、３０を超えても、一般式［１］で表される
縮合リン酸エステルのエマルジョン安定性が不良になる
おそれがある。本発明の難燃加工薬剤は、一般式［１］
で表される縮合リン酸エステルの含有量が、２０〜８０
重量％であることが好ましく、３０〜７０重量％である
ことがより好ましい。一般式［１］で表される縮合リン
酸エステルの含有量が２０重量％未満であると、多量の
薬剤を取り扱うことになり、製造、輸送、貯蔵などの段
階で、経済性が損なわれるおそれがある。一般式［１］
で表される縮合リン酸エステルの含有量が８０重量％を
超えると、液状物を得るのは困難となり、難燃加工薬剤
として使用できない。The surfactant represented by the general formula [2] used in the present invention is obtained by adding 1 to 3 moles of styrene to 1 mole of phenol, and adding 3 to 50 moles of ethylene oxide to 1 mole of styrenated phenol. It can be obtained by adding a mole. If the average number of added moles of ethylene oxide is less than 5 or more than 30, emulsion stability of the condensed phosphate represented by the general formula [1] may be poor. The surfactant represented by the general formula [3] used in the present invention is obtained by subjecting the surfactant represented by the general formula [2] to sulfate esterification, and adding sodium hydroxide,
It can be obtained by neutralizing with potassium hydroxide, ammonia or the like. Even if the average number of moles of ethylene oxide added to the surfactant represented by the general formula [3] is less than 5 or more than 30, the emulsion stability of the condensed phosphate ester represented by the general formula [1] May be poor. The flame-retardant processing agent of the present invention has the general formula [1]
Is from 20 to 80.
%, More preferably 30 to 70% by weight. If the content of the condensed phosphoric ester represented by the general formula [1] is less than 20% by weight, a large amount of the drug will be handled, and the economy may be impaired at the stage of production, transportation, storage and the like. There is. General formula [1]
When the content of the condensed phosphoric ester represented by the formula (1) exceeds 80% by weight, it becomes difficult to obtain a liquid material and cannot be used as a flame retardant.
【０００７】本発明の難燃加工薬剤において、一般式
［２］及び／又は一般式［３］で表される界面活性剤の
使用量に特に制限はないが、一般式［１］で表される縮
合リン酸エステル１００重量部に対して、一般式［２］
及び／又は一般式［３］で表される界面活性剤が５〜４
０重量部であることが好ましく、１０〜３０重量部であ
ることがより好ましい。一般式［２］及び／又は一般式
［３］で表される界面活性剤の使用量が一般式［１］で
表される縮合リン酸エステル１００重量部に対して５重
量部未満であると、難燃加工薬剤のエマルジョン安定性
が不良になるおそれがある。一般式［２］及び／又は一
般式［３］で表される界面活性剤の使用量が一般式
［１］で表される縮合リン酸エステル１００重量部に対
して４０重量部を超えると、吸尽率の低下を招くおそれ
がある。本発明の難燃加工薬剤の製造方法に特に制限は
なく、例えば、一般式［１］で表される縮合リン酸エス
テルと一般式［２］で表される界面活性剤及び／又は一
般式［３］で表される界面活性剤の混合物を撹拌しなが
ら、徐々に水を加えていくことにより、縮合リン酸エス
テルを水中に乳化分散させることができ、あるいは、一
般式［１］で表される縮合リン酸エステルと一般式
［２］で表される界面活性剤及び／又は一般式［３］で
表される界面活性剤と水の混合物をホモジナイザーなど
を用いて乳化し、縮合リン酸エステルを水中に乳化分散
させることもできる。本発明の難燃加工薬剤は、縮合リ
ン酸エステルが粒径の小さい微粒子状になっているの
で、安定性に優れ長期間保存してもエマルジョンが分離
するおそれがない。また、縮合リン酸エステルが微粒子
状になっているために、ポリエステル繊維の内部に浸透
し、水洗い洗濯やドライクリーニングにより脱落しにく
くなり、本発明の難燃加工薬剤で処理したポリエステル
繊維の難燃性は、洗濯によってもほとんど低下しない。
さらに、本発明の難燃加工薬剤は、染浴に添加しても染
料の分散性を阻害しないので、染浴同浴で処理すること
ができる。The amount of the surfactant represented by the general formula [2] and / or the general formula [3] in the flame retardant agent of the present invention is not particularly limited, but is represented by the general formula [1]. [2] with respect to 100 parts by weight of the condensed phosphate ester
And / or the surfactant represented by the general formula [3] is 5 to 4
It is preferably 0 parts by weight, more preferably 10 to 30 parts by weight. When the amount of the surfactant represented by the general formula [2] and / or the general formula [3] is less than 5 parts by weight based on 100 parts by weight of the condensed phosphoric ester represented by the general formula [1]. The emulsion stability of the flame-retardant processing agent may be poor. When the amount of the surfactant represented by the general formula [2] and / or the general formula [3] exceeds 40 parts by weight based on 100 parts by weight of the condensed phosphate ester represented by the general formula [1], The exhaustion rate may be reduced. There is no particular limitation on the method for producing the flame-retardant processing agent of the present invention. For example, a condensed phosphate represented by the general formula [1] and a surfactant represented by the general formula [2] and / or a general formula [2] 3] The condensed phosphate ester can be emulsified and dispersed in water by gradually adding water while stirring the surfactant mixture represented by the formula [1], or represented by the general formula [1]. A mixture of the condensed phosphate ester and the surfactant represented by the general formula [2] and / or the surfactant represented by the general formula [3] and water is emulsified using a homogenizer or the like, and the condensed phosphate ester Can be emulsified and dispersed in water. Since the condensed phosphoric acid ester is in the form of fine particles having a small particle diameter, the flame retardant processing agent of the present invention has excellent stability and does not have the possibility of separating the emulsion even when stored for a long period of time. In addition, since the condensed phosphate ester is in the form of fine particles, it penetrates into the interior of the polyester fiber and is hard to fall off by washing with water or dry cleaning, and the flame retardancy of the polyester fiber treated with the flame retardant of the present invention. Sex is hardly reduced by washing.
Furthermore, since the flame retardant processing agent of the present invention does not inhibit the dispersibility of the dye even when it is added to the dye bath, it can be treated in the dye bath.
【０００８】[0008]
【実施例】以下に、実施例を挙げて本発明をさらに詳細
に説明するが、本発明はこれらの実施例によりなんら限
定されるものではない。なお、実施例及び比較例におい
て、評価は下記の方法で行った。 （１）乳化物の平均粒径 レーザ回折式粒度分布測定装置［(株)島津製作所、ＳＡ
ＬＤ−１１００］を用いて測定する。 （２）燃焼性 洗濯なしの試料、水洗い洗濯後の試料及びドライクリー
ニング後の試料について、ＪＩＳ Ｌ １０９１ Ａ−１
法にしたがって残炎時間と炭化面積を測定し、ＪＩＳ
Ｌ １０９１ Ｄ法にしたがって接炎回数を測定する。 実施例１ 縮合リン酸エステル［アクゾ ノーベル社、ファイロー
ルフレックスＲＤＰ、一般式［１］においてｐ＝１の化
合物とｐ＝２の化合物の混合物］５０重量部とトリスチ
レン化フェノールのエチレンオキサイド１０モル付加物
８重量部の混合物に、水４２重量部を撹拌しながら少し
ずつ加えて乳化分散し、難燃加工薬剤を得た。この難燃
加工薬剤中の乳化物の平均粒径は、０.２μｍであっ
た。目付１３０ｇ／ｍ2のポリエステル未染色布を、ミ
ニカラー染色機［テクサム社］を使用し、分散染料
［Ｃ.Ｉ.Ｄｉｓｐｅｒｓｅ Ｂｌｕｅ ５６］１％ｏ.ｗ.
ｆ.、分散均染剤［日華化学(株)、ニッカサンソルトＲ
Ｍ−３４０］０.５ｇ／Ｌ、９０重量％酢酸０.３mL／Ｌ
及び難燃加工薬剤２０％ｏ.ｗ.ｆ.を含む染浴で、浴比
１：１５、温度１３０℃の条件で、３０分処理した。次
いで、ソーピング剤［日華化学(株)、エスクードＦＲ］
２ｇ／Ｌ、ソーダ灰２ｇ／Ｌ及びハイドロサルファイト
２ｇ／Ｌを含む水溶液を用いて、８０℃で２０分還元洗
浄を行ない、１１０℃で２分乾燥し、試料を得た。得ら
れた試料について、ＪＩＳ Ｌ １０９１の洗濯方法(１)
(ａ)にしたがう水洗い洗濯と、洗濯方法(２)にしたがう
ドライクリーニングを行い、洗濯なしの試料、水洗い洗
濯後の試料及びドライクリーニング後の試料について、
燃焼性試験を行った。残炎時間は、すべての試料が０秒
であり、炭化面積は、洗濯なしの試料が１７cm2、水洗
い洗濯後の試料とドライクリーニング後の試料がともに
１８cm2であり、接炎回数は、すべての試料が４回であ
った。目付２００ｇ／ｍ2のポリエステル未染色布を、
カラーペット染色機を使用し、分散染料［Ｃ.Ｉ.Ｄｉｓ
ｐｅｒｓｅ Ｂｌｕｅ ６０］と分散染料［Ｃ.Ｉ.Ｄｉｓ
ｐｅｒｓｅ Ｒｅｄ １６７］それぞれ１.５％ｏ.ｗ.
ｆ.、分散均染剤［日華化学(株)、ニッカサンソルトＲ
Ｍ−３４０］０.５ｇ／Ｌ、９０重量％酢酸０.３mL／Ｌ
及び難燃加工薬剤３０％ｏ.ｗ.ｆ.を含む染浴で、浴比
１：３０、温度１３０℃の条件で、３０分処理し、処理
布を水洗した。処理布への染料の斑付きはなく、染料分
散性は良好であった。難燃加工薬剤３００mLをガラスび
んに入れて密栓し、４５℃の送風恒温乾燥機に保管し
て、１日後、７日後及び３０日後の状態を観察した。３
０日後も分離はなく、エマルジョンは安定であった。EXAMPLES The present invention will be described in more detail with reference to the following Examples, which should not be construed as limiting the present invention. In the examples and comparative examples, evaluation was performed by the following method. (1) Average particle size of emulsified product Laser diffraction particle size distribution analyzer [Shimadzu Corporation, SA
LD-1100]. (2) Combustibility Regarding the sample without washing, the sample after washing with water, and the sample after dry cleaning, JIS L 1091 A-1 was used.
After-flame time and carbonized area were measured according to the
The number of times of flame contact is measured according to the L1091 D method. Example 1 50 parts by weight of a condensed phosphoric acid ester [Akzo Nobel, Filol Flex RDP, a mixture of a compound of p = 1 and a compound of p = 2 in the general formula [1]] and 10 mol of ethylene oxide of tristyrenated phenol To a mixture of 8 parts by weight of the adduct, 42 parts by weight of water was added little by little while stirring, and the mixture was emulsified and dispersed to obtain a flame retardant. The average particle size of the emulsion in the flame retardant was 0.2 μm. An undyed polyester fabric having a basis weight of 130 g / m 2 was dispersed in a disperse dye [CI Disperse Blue 56] 1% ow using a mini color dyeing machine [Texam].
f., Dispersion leveling agent [Nikka Chemical Co., Ltd., Nikka Sun Salt R
M-340] 0.5 g / L, 90% by weight acetic acid 0.3 mL / L
And a dyeing bath containing a flame-retardant processing agent 20% owf at a bath ratio of 1:15 and a temperature of 130 ° C. for 30 minutes. Next, a soaping agent [Nichika Chemical Co., Ltd., Escudo FR]
Using an aqueous solution containing 2 g / L, 2 g / L of soda ash and 2 g / L of hydrosulfite, reduction washing was performed at 80 ° C. for 20 minutes, and drying was performed at 110 ° C. for 2 minutes to obtain a sample. About the obtained sample, the washing method of JIS L1091 (1)
(a) Washing with water according to (a) and dry cleaning according to the washing method (2) are performed, and for a sample without washing, a sample after washing with water and a sample after dry cleaning,
A flammability test was performed. The residual flame time was 0 seconds for all samples, the carbonized area was 17 cm 2 for the sample without washing, the sample after washing with water and the sample after dry cleaning were 18 cm 2 , and the number of times of flame contact was all Sample was 4 times. A polyester undyed cloth having a basis weight of 200 g / m 2
Using a color pet dyeing machine, disperse dye [C.I.
perse Blue 60] and a disperse dye [C.I.
perse Red 167] 1.5% ow each.
f., Dispersion leveling agent [Nikka Chemical Co., Ltd., Nikka Sun Salt R
M-340] 0.5 g / L, 90% by weight acetic acid 0.3 mL / L
And a dyeing bath containing a flame-retardant processing agent 30% owf at a bath ratio of 1:30 and a temperature of 130 ° C. for 30 minutes, and the treated cloth was washed with water. There was no spotting of the dye on the treated cloth, and the dye dispersibility was good. 300 mL of the flame retardant was placed in a glass bottle, sealed tightly, stored in a 45 ° C. constant-temperature oven, and the state after 1, 7, and 30 days was observed. 3
There was no separation after 0 days and the emulsion was stable.
【０００９】実施例２ トリスチレン化フェノールエチレンオキサイド１０モル
付加物８重量部の代わりに、トリスチレン化フェノール
エチレンオキサイド１０モル付加物の硫酸エステル化物
のナトリウム塩８重量部を用いた以外は、実施例１と同
様にして、難燃加工薬剤を調製し、評価を行った。難燃
加工薬剤中の乳化物の平均粒径は、０.３μｍであっ
た。燃焼性試験において、残炎時間は、すべての試料が
０秒であり、炭化面積は、洗濯なしの試料が１９cm2、
水洗い洗濯後の試料が１５cm2、ドライクリーニング後
の試料が１７cm 2であり、接炎回数は、すべての試料が
４回であった。染料分散試験において、処理布への染料
の斑付きはなく、染料分散性は良好であった。難燃加工
薬剤は、３０日後も分離はなく、エマルジョンは安定で
あった。 実施例３ トリスチレン化フェノールエチレンオキサイド１０モル
付加物８重量部の代わりに、トリスチレン化フェノール
エチレンオキサイド１０モル付加物４重量部及びトリス
チレン化フェノールエチレンオキサイド１０モル付加物
の硫酸エステル化物のアンモニウム塩４重量部を用いた
以外は、実施例１と同様にして、難燃加工薬剤を調製
し、評価を行った。難燃加工薬剤中の乳化物の平均粒径
は、０.２μｍであった。燃焼性試験において、残炎時
間は、すべての試料が０秒であり、炭化面積は、洗濯な
しの試料が１８cm2、水洗い洗濯後の試料が１６cm2、ド
ライクリーニング後の試料が１９cm 2であり、接炎回数
は、すべての試料が４回であった。染料分散試験におい
て、処理布への染料の斑付きはなく、染料分散性は良好
であった。難燃加工薬剤は、３０日後も分離はなく、エ
マルジョンは安定であった。 実施例４ トリスチレン化フェノールエチレンオキサイド１０モル
付加物８重量部の代わりに、ジスチレン化フェノールエ
チレンオキサイド１０モル付加物８重量部を用いた以外
は、実施例１と同様にして、難燃加工薬剤を調製し、評
価を行った。難燃加工薬剤中の乳化物の平均粒径は、
０.２μｍであった。燃焼性試験において、残炎時間
は、すべての試料が０秒であり、炭化面積は、洗濯なし
の試料が１７cm2、水洗い洗濯後の試料とドライクリー
ニング後の試料がともに１９cm2であり、接炎回数は、
すべての試料が４回であった。染料分散試験において、
処理布への染料の斑付きはなく、染料分散性は良好であ
った。難燃加工薬剤は、３０日後も分離はなく、エマル
ジョンは安定であった。Example 2 Tristyrenated phenol ethylene oxide 10 mol
Instead of 8 parts by weight of adduct, tristyrenated phenol
Sulfate of ethylene oxide 10 mol adduct
Example 1 was repeated except that 8 parts by weight of the sodium salt was used.
In this way, a flame-retardant processing chemical was prepared and evaluated. Flame retardant
The average particle size of the emulsion in the processing chemical was 0.3 μm.
Was. In the flammability test, the afterflame time was determined for all samples.
0 seconds, carbonized area was 19 cm for the sample without washingTwo,
15cm after washing with waterTwoAfter dry cleaning
Sample is 17cm TwoAnd the flame contact frequency is
It was four times. In the dye dispersion test, the dye on the treated cloth
Was not observed and the dye dispersibility was good. Flame retardant processing
The drug is not separated after 30 days and the emulsion is stable
there were. Example 3 10 mol of tristyrenated phenol ethylene oxide
Instead of 8 parts by weight of adduct, tristyrenated phenol
4 parts by weight of ethylene oxide 10 mol adduct and tris
10 mol of adrenalized phenol ethylene oxide
4 parts by weight of ammonium salt of a sulfated product of
Except for the above, a flame retardant chemical was prepared in the same manner as in Example 1.
And evaluated. Average particle size of emulsion in flame retardant chemicals
Was 0.2 μm. In the flammability test, after flame
In the meantime, all samples were 0 seconds, and the carbonized area was
The sample is 18cmTwo16cm after washing and washingTwo,
Sample after lye cleaning is 19cm TwoAnd the number of flame contact
Was 4 times for all samples. In dye dispersion test
The dye is not spotted on the treated cloth and the dye dispersibility is good.
Met. The flame retardant does not separate after 30 days.
Marjon was stable. Example 4 10 mol of tristyrenated phenol ethylene oxide
Instead of 8 parts by weight of the adduct, distyrenated phenol
Except for using 8 parts by weight of a 10 mol adduct of Tylene oxide
Prepared a flame-retardant processing chemical in the same manner as in Example 1,
Value. The average particle size of the emulsion in the flame retardant is
0.2 μm. Afterflame time in flammability test
Indicates that all samples are 0 seconds and the carbonized area is without washing
Sample is 17cmTwo, Sample and dry cream after washing with water
19cm for both samplesTwoAnd the number of flame contacts is
All samples were four times. In the dye dispersion test,
There is no spotting of the dye on the treated cloth, and the dye dispersibility is good.
Was. Flame-retardant processing chemicals are not separated after 30 days
John was stable.
【００１０】比較例１ トリスチレン化フェノールエチレンオキサイド１０モル
付加物８重量部の代わりに、ノニルフェノールエチレン
オキサイド１０モル付加物８重量部を用いた以外は、実
施例１と同様にして、難燃加工薬剤を調製し、評価を行
った。難燃加工薬剤中の乳化物の平均粒径は、１.５μ
ｍであった。燃焼性試験において、残炎時間は、洗濯な
しの試料が０秒、水洗い洗濯後の試料が１０秒、ドライ
クリーニング後の試料が８秒であり、炭化面積は、洗濯
なしの試料が２０cm2、水洗い洗濯後の試料が５４cm2、
ドライクリーニング後の試料が４２cm2であり、接炎回
数は、洗濯なしの試料が４回、水洗い洗濯後の試料とド
ライクリーニング後の試料がともに１回であった。染料
分散試験において、処理布への染料の斑付きがあり、染
料分散性は不良であった。難燃加工薬剤は、１日後には
分離していた。 比較例２ トリスチレン化フェノールエチレンオキサイド１０モル
付加物８重量部の代わりに、ラウリルアルコールエチレ
ンオキサイド１０モル付加物８重量部を用いた以外は、
実施例１と同様にして、難燃加工薬剤を調製し、評価を
行った。難燃加工薬剤中の乳化物の平均粒径は、１.５
μｍであった。燃焼性試験において、残炎時間は、洗濯
なしの試料が３秒、水洗い洗濯後の試料が８秒、ドライ
クリーニング後の試料が１２秒であり、炭化面積は、洗
濯なしの試料が２８cm2、水洗い洗濯後の試料が４８c
m2、ドライクリーニング後の試料が６０cm2であり、接
炎回数は、洗濯なしの試料が４回、水洗い洗濯後の試料
とドライクリーニング後の試料がともに１回であった。
染料分散試験において、処理布への染料の斑付きがあ
り、染料分散性は不良であった。難燃加工薬剤は、１日
後には分離していた。 比較例３ トリスチレン化フェノールエチレンオキサイド１０モル
付加物８重量部の代わりに、ラウリルアルコールエチレ
ンオキサイド１０モル付加物の硫酸エステル化物のナト
リウム塩８重量部を用いた以外は、実施例１と同様にし
て、難燃加工薬剤を調製し、評価を行った。難燃加工薬
剤中の乳化物の平均粒径は、１.５μｍであった。燃焼
性試験において、残炎時間は、洗濯なしの試料が１秒、
水洗い洗濯後の試料が８秒、ドライクリーニング後の試
料が５秒であり、炭化面積は、洗濯なしの試料が２２cm
2、水洗い洗濯後の試料が４５cm2、ドライクリーニング
後の試料が３８cm2であり、接炎回数は、洗濯なしの試
料が４回、水洗い洗濯後の試料とドライクリーニング後
の試料がともに１回であった。染料分散試験において、
処理布への染料の斑付きがあり、染料分散性は不良であ
った。難燃加工薬剤は、１日後には分離していた。実施
例１〜４及び比較例１〜３の結果を、第１表に示す。Comparative Example 1 Flame retardant processing was performed in the same manner as in Example 1 except that 8 parts by weight of nonylphenol ethylene oxide 10 mols was used instead of 8 parts by weight of tristyrenated phenol ethylene oxide 10 mols. Drugs were prepared and evaluated. The average particle size of the emulsion in the flame retardant is 1.5μ
m. In the flammability test, the afterflame time was 0 seconds for the sample without washing, the sample after washing with water was 10 seconds, the sample after dry cleaning was 8 seconds, and the carbonized area was 20 cm 2 for the sample without washing. The sample after washing with water is 54cm 2 ,
The sample after dry cleaning was 42 cm 2 , and the number of times of flame contact was 4 for the sample without washing, and 1 for both the sample after washing with water and the sample after dry cleaning. In the dye dispersion test, the treated cloth had spots of the dye, and the dye dispersibility was poor. The flame retardant was separated after one day. Comparative Example 2 Instead of 8 parts by weight of tristyrenated phenol ethylene oxide 10 moles adduct, 8 parts by weight of lauryl alcohol ethylene oxide 10 moles adduct was used.
In the same manner as in Example 1, a flame-retardant processing agent was prepared and evaluated. The average particle size of the emulsion in the flame retardant is 1.5
μm. In the flammability test, the afterflame time was 3 seconds for the sample without washing, 8 seconds for the sample after washing with water, 12 seconds for the sample after dry cleaning, and the carbonization area was 28 cm 2 for the sample without washing. 48c after washing with water
m 2 , the sample after dry cleaning was 60 cm 2 , and the number of times of flame contact was 4 for the sample without washing, and once for the sample after washing with water and the sample after dry cleaning.
In the dye dispersion test, the treated cloth had spots of the dye, and the dye dispersibility was poor. The flame retardant was separated after one day. Comparative Example 3 In the same manner as in Example 1 except that 8 parts by weight of a 10 mol adduct of tristyrenated phenol ethylene oxide was replaced by 8 parts by weight of a sodium salt of a sulfated product of a 10 mol adduct of lauryl alcohol ethylene oxide. Thus, a flame retardant was prepared and evaluated. The average particle size of the emulsion in the flame retardant was 1.5 μm. In the flammability test, the afterflame time was 1 second for the sample without washing,
The sample after washing with water was 8 seconds, the sample after dry cleaning was 5 seconds, and the carbonized area was 22 cm for the sample without washing.
2. The sample after washing with water is 45 cm 2 , the sample after dry cleaning is 38 cm 2 , and the number of times of flame contact is 4 for the sample without washing, and once for the sample after washing with water and once for the sample after dry cleaning. Met. In the dye dispersion test,
Dye was spotted on the treated cloth, and the dye dispersibility was poor. The flame retardant was separated after one day. Table 1 shows the results of Examples 1 to 4 and Comparative Examples 1 to 3.
【００１１】[0011]
【表１】 [Table 1]
【００１２】第１表に見られるように、実施例１〜４の
本発明の難燃加工薬剤は、乳化物の平均粒径が小さく、
３０日後も分離することがなく、エマルジョンの安定性
に優れている。これに対して、従来から用いられている
界面活性剤を用いて製造した比較例１〜３の難燃加工薬
剤は、乳化物の平均粒径が大きく、１日後には分離を生
じ、エマルジョンの安定性に劣っている。実施例と比較
例について燃焼性試験の結果を比較すると、残炎時間と
炭化面積は実施例の方が小さく、接炎回数は実施例の方
が多く、本発明の難燃加工薬剤を用いて処理したポリエ
ステル布の方が、優れた難燃性を備えている。特に、洗
濯なしの試料と水洗い洗濯後の試料又はドライクリーニ
ング後の試料の結果を比較すると、比較例の試料は、洗
濯後には難燃性が著しく低下しているのに対して、本発
明の難燃加工薬剤を用いて処理した実施例の試料は、洗
濯の前後において難燃性がほとんど変化しないことか
ら、本発明の難燃加工薬剤により、ポリエステル繊維に
耐久性に優れた難燃性が付与されていることが分かる。
また、従来から用いられている界面活性剤を用いて製造
した難燃加工薬剤は、染浴に添加すると染料分散性が不
良になるが、本発明の難燃加工薬剤は、染浴に添加して
も染料は良好な分散性を保つ。As can be seen from Table 1, the flame-retardant processing agents of the present invention of Examples 1 to 4 have a small average particle size of the emulsion.
There is no separation even after 30 days, and the emulsion has excellent stability. On the other hand, the flame-retardant processing agents of Comparative Examples 1 to 3 manufactured using the conventionally used surfactants have a large average particle size of the emulsified substance, cause separation after one day, and Poor stability. Comparing the results of the flammability test for the Examples and Comparative Examples, the residual flame time and the carbonized area are smaller in the Examples, the number of times of flame contact is larger in the Examples, and the flame retardant processing agent of the present invention is used. The treated polyester fabric has better flame retardancy. In particular, comparing the results of the sample without washing and the sample after washing with water or the sample after dry cleaning, the sample of the comparative example has significantly reduced flame retardancy after washing, whereas the sample of the present invention has a significantly reduced flame retardancy. Since the samples of the examples treated with the flame retardant agent had almost no change in flame retardancy before and after washing, the flame retardant agent of the present invention provided the polyester fiber with excellent durability. It can be seen that it is provided.
In addition, the flame retardant agent produced using a conventionally used surfactant has poor dye dispersibility when added to a dye bath, but the flame retardant agent of the present invention is added to a dye bath. However, the dye maintains good dispersibility.
【００１３】[0013]
【発明の効果】本発明の難燃加工薬剤は、エマルジョン
の安定性に優れ、ポリエステル繊維に染浴同浴処理によ
り、良好かつ安全に難燃性を付与することができ、優れ
た耐久難燃性が付与される。EFFECT OF THE INVENTION The flame-retardant processing agent of the present invention has excellent emulsion stability, can impart good and safe flame retardancy to polyester fibers by dyeing and bathing, and has excellent durable flame retardancy. Is imparted.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 ＦＩ テーマコート゛(参考） Ｄ０６Ｍ 13/256 Ｄ０６Ｍ 13/256 13/292 13/292 (72)発明者 木下 裕貴 福井県福井市文京４丁目23番１号 日華化 学株式会社内 Ｆターム(参考） 4D077 AA05 AC03 BA03 BA13 BA15 DD02Y DD32Y DE04Y DE29Y 4H028 AA35 BA05 4J002 CH021 CH051 EW046 FD136 FD311 GK02 HA07 4L033 AC05 BA13 BA14 BA28 BA39 CA48 ──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. 7 Identification symbol FI Theme coat ゛ (Reference) D06M 13/256 D06M 13/256 13/292 13/292 (72) Inventor Yuki Kinoshita 4 Bunkyo, Fukui City, Fukui Prefecture No. 23-1, F-term in Nikka Kagaku Co., Ltd. (reference) 4D077 AA05 AC03 BA03 BA13 BA15 DD02Y DD32Y DE04Y DE29Y 4H028 AA35 BA05 4J002 CH021 CH051 EW046 FD136 FD311 GK02 HA07 4L033 AC05 BA13 BA14 BA28 BA39 CA48
Claims (1)
ルが、一般式［２］で表される界面活性剤及び／又は一
般式［３］で表される界面活性剤を用いて、水中に乳化
分散されてなることを特徴とする難燃加工薬剤。 【化１】 （ただし、式中、ｐは１又は２である。） 【化２】 （ただし、式中、ｍは１〜３であり、ｎは５〜３０であ
る。） 【化３】 （ただし、式中、ｍは１〜３であり、ｎは５〜３０であ
り、Ｍ+はＮａ+、Ｋ+又はＮＨ4 +である。）1. A method according to claim 1, wherein the condensed phosphoric ester represented by the general formula [1] is prepared by using a surfactant represented by the general formula [2] and / or a surfactant represented by the general formula [3]. A flame-retardant processing agent characterized by being emulsified and dispersed in water. Embedded image (Where p is 1 or 2) (Wherein, m is 1 to 3 and n is 5 to 30.) (Wherein, m is 1 to 3, n is 5 to 30, M + is Na +, K + or NH 4 +.)
Priority Applications (1)
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|---|---|---|---|
| JP2000279916A JP3559514B2 (en) | 2000-09-14 | 2000-09-14 | Flame retardant for textile |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000279916A JP3559514B2 (en) | 2000-09-14 | 2000-09-14 | Flame retardant for textile |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002088368A true JP2002088368A (en) | 2002-03-27 |
| JP3559514B2 JP3559514B2 (en) | 2004-09-02 |
Family
ID=18764848
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|---|---|---|---|
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| JP2005307396A (en) * | 2004-04-22 | 2005-11-04 | Daikyo Kagaku Kk | Flame-retardant finishing agent of polyester-based fiber product and flame-retardant finishing method |
| JP2006348443A (en) * | 2005-06-20 | 2006-12-28 | Nicca Chemical Co Ltd | Flame retardant for polyester fiber |
| JP2007092263A (en) * | 2005-09-30 | 2007-04-12 | Meisei Kagaku Kogyo Kk | Flame-retardant processing agent, and flame-retardant processing method of polyester-based fiber using the agent |
| JP2007197867A (en) * | 2006-01-26 | 2007-08-09 | Komatsu Seiren Co Ltd | Flame-retardant finishing agent and flame-retardant finishing method for polyester fiber product |
| JP2008189817A (en) * | 2007-02-05 | 2008-08-21 | Nicca Chemical Co Ltd | Flame-retardant processing agent for polyester-based fiber and flame-retardant processing method and flame-retardant polyester-based fiber |
| JP2009029889A (en) * | 2007-07-25 | 2009-02-12 | Komatsu Seiren Co Ltd | Flame-retarding agent and flame-retarding method for polyester-based fiber |
| WO2014163013A1 (en) | 2013-04-01 | 2014-10-09 | 株式会社Adeka | Flame-retardant agent composition, flame-retardant fiber treated with flame-retardant agent composition, and method for increasing amount of flame-retardant component adhered onto fibers using said composition |
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|---|---|---|---|---|
| JP2005307396A (en) * | 2004-04-22 | 2005-11-04 | Daikyo Kagaku Kk | Flame-retardant finishing agent of polyester-based fiber product and flame-retardant finishing method |
| JP2006348443A (en) * | 2005-06-20 | 2006-12-28 | Nicca Chemical Co Ltd | Flame retardant for polyester fiber |
| JP4721853B2 (en) * | 2005-09-30 | 2011-07-13 | 明成化学工業株式会社 | Flame retardant finishing agent and method for flame retardant processing of polyester fiber using the flame retardant finishing agent |
| JP2007092263A (en) * | 2005-09-30 | 2007-04-12 | Meisei Kagaku Kogyo Kk | Flame-retardant processing agent, and flame-retardant processing method of polyester-based fiber using the agent |
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| JP2008189817A (en) * | 2007-02-05 | 2008-08-21 | Nicca Chemical Co Ltd | Flame-retardant processing agent for polyester-based fiber and flame-retardant processing method and flame-retardant polyester-based fiber |
| JP2009029889A (en) * | 2007-07-25 | 2009-02-12 | Komatsu Seiren Co Ltd | Flame-retarding agent and flame-retarding method for polyester-based fiber |
| WO2014163013A1 (en) | 2013-04-01 | 2014-10-09 | 株式会社Adeka | Flame-retardant agent composition, flame-retardant fiber treated with flame-retardant agent composition, and method for increasing amount of flame-retardant component adhered onto fibers using said composition |
| KR20150138260A (en) | 2013-04-01 | 2015-12-09 | 가부시키가이샤 아데카 | Flame-retardant agent composition, flame-retardant fiber treated with flame-retardant agent composition, and method for increasing amount of flame-retardant component adhered onto fibers using said composition |
| JP6333239B2 (en) * | 2013-04-01 | 2018-05-30 | 株式会社Adeka | Flame retardant composition, flame retardant fiber treated with flame retardant composition, and method for increasing the amount of flame retardant component fixed to fiber using the composition |
| KR102129650B1 (en) | 2013-04-01 | 2020-07-02 | 가부시키가이샤 아데카 | Flame-retardant agent composition, flame-retardant fiber treated with flame-retardant agent composition, and method for increasing amount of flame-retardant component adhered onto fibers using said composition |
| US10190051B2 (en) | 2014-06-10 | 2019-01-29 | Alexium, Inc. | Emulsification of hydrophobic organophosphorous compounds |
| US10590345B2 (en) | 2014-06-10 | 2020-03-17 | Alexium, Inc. | Emulsification of hydrophobic organophosphorous compounds |
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