JPH0420957B2 - - Google Patents
Info
- Publication number
- JPH0420957B2 JPH0420957B2 JP21628283A JP21628283A JPH0420957B2 JP H0420957 B2 JPH0420957 B2 JP H0420957B2 JP 21628283 A JP21628283 A JP 21628283A JP 21628283 A JP21628283 A JP 21628283A JP H0420957 B2 JPH0420957 B2 JP H0420957B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- compound
- hydrazine
- paper
- boric acid
- 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
- -1 hydrazine compound Chemical class 0.000 claims description 24
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 12
- 239000003063 flame retardant Substances 0.000 claims description 11
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
- 239000004327 boric acid Substances 0.000 claims description 9
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 7
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
- 235000019253 formic acid Nutrition 0.000 claims description 5
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 5
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 5
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 description 9
- 235000021317 phosphate Nutrition 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000010452 phosphate Substances 0.000 description 7
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- FUSNOPLQVRUIIM-UHFFFAOYSA-N 4-amino-2-(4,4-dimethyl-2-oxoimidazolidin-1-yl)-n-[3-(trifluoromethyl)phenyl]pyrimidine-5-carboxamide Chemical compound O=C1NC(C)(C)CN1C(N=C1N)=NC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 FUSNOPLQVRUIIM-UHFFFAOYSA-N 0.000 description 2
- LNEUSAPFBRDCPM-UHFFFAOYSA-N carbamimidoylazanium;sulfamate Chemical compound NC(N)=N.NS(O)(=O)=O LNEUSAPFBRDCPM-UHFFFAOYSA-N 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 239000012493 hydrazine sulfate Substances 0.000 description 2
- 229910000377 hydrazine sulfate Inorganic materials 0.000 description 2
- 150000002429 hydrazines Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- YFHNDHXQDJQEEE-UHFFFAOYSA-N acetic acid;hydrazine Chemical compound NN.CC(O)=O YFHNDHXQDJQEEE-UHFFFAOYSA-N 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- ZSFDBVJMDCMTBM-UHFFFAOYSA-N ethane-1,2-diamine;phosphoric acid Chemical compound NCCN.OP(O)(O)=O ZSFDBVJMDCMTBM-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/63—Inorganic compounds
- D21H17/65—Acid compounds
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
Description
本発明は主として紙用に使用する難燃化剤に関
するものである。
従来紙用の難燃化剤としては、スルフアミン酸
グアニジン等が用いられる。しかしながらこれら
難燃剤は多量に添加しなければその効果を発揮せ
ず、又難燃化処理した紙を加熱すると着色すると
言う問題がある。
一方、特公昭49−32754号公報に記載のあるポ
リエチレンポリアミン又はエチレンジアミンのリ
ン酸塩は優れた難燃性を示すが、該アミンのリン
酸塩を付着させた紙を加熱処理すると、その着色
が著しい事が欠点であつた。
本発明者らはアミンのリン酸塩の上記欠点を解
決すべく種々検討を重ねた結果、アミンのリン酸
塩にヒドラジン化合物及び／又はホウ酸化合物あ
るいはさらにギ酸、亜リン酸、次亜リン酸又はそ
の塩の一種以上を混合せしめる事により難燃性を
低下する事なしに、加熱処理時の着色をほとん
ど、あるいはごくわずかで実用上問題がない程度
に抑えられる事を見出し本発明の完成に至つた。
本発明におけるアミンのリン酸塩とはエチレン
ジアミン又はその縮合物であつて、たとえば
H2N−（CH2CH2NH）o−Ｈ（難燃性の点でｎ＝
１〜５が良い。）
HN−（C2H4）2NH，HN（C2H4）2NC2H4NH2
で表わされる一種以上のアミンとリン酸を反応さ
せたものである。アミンとリン酸の反応割合は特
に限定するものではないが、紙に与える影響の少
なさ及び水に対する溶解度の高い点においてPH７
前後に調整したものが好ましい。
本発明に用いられるヒドラジン化合物として
は、例えば抱水ヒドラジン、硫酸ヒドラジン、ヒ
ドラジン酢酸塩などが挙げられる。これらは単独
でもあるいは二種以上併用しても良い。これらヒ
ドラジン化合物の混合量は、アミンのリン酸塩１
重量部に対して0.1重量部以上が好ましい。
又ホウ酸化合物としては、例えばホウ酸、ホウ
酸ナトリウム等が挙げられ、単独あるいは二種以
上併用して用いられる。該ホウ酸化合物の混合量
は、アミンのリン酸塩１重量部に対して0.2重量
部以上が好ましいが、0.8重量部をこえて混合す
ると紙が硬化し風合がおちる。
ギ酸、亜リン酸、次亜リン酸又はその塩の添加
は、ヒドラジン化合物の混合量を削減できる効果
を有し、又ホウ酸化合物と共に用いると一層着色
を抑える事ができる。塩としてはナトリウム塩等
水に対する溶解度の高いものがよく、又その混合
量としては、アミンのリン酸塩１重量部に対して
0.1重量部以上が好ましい。
上記難燃化剤の付着率は、従来のスルフアミン
酸グアニジンの18％以上に比べて10％でも十分そ
の効果を発揮する。
本難燃化剤は次の如く製造する事ができる。
即ち、その一方法はアミンのリン酸水溶液また
はスラリーにヒドラジン化合物及び／又はホウ酸
化合物を溶解し又は混合してスラリーとし、ある
いは該溶解液又は該スラリーにギ酸、亜リン酸、
次亜リン酸又はその塩を添加し、液状あるいはス
ラリー状とするものであり、他の方法は水又はア
ルコール等の溶媒から析出したアミンのリン酸塩
の結晶を別、乾燥した後硫酸ヒドラジン等の固
体のヒドラジン化合物及び／又はホウ酸化合物を
混合せしめ、あるいはさらにギ酸、亜リン酸、次
亜リン酸の塩を混合せしめて粉状とするもので、
これら液状、スラリー状、あるいは粉状の三者の
難燃化剤においてその効果に差異は認められな
い。
以下実施例により本発明を具体的に説明する。
実施例 １
500mlフラスコに水134ml、75wt％リン酸を53
ｇ仕込み撹拌しながら濃度50wt％エチレンジア
ミン水溶液49ｇを徐々に滴下した。液温は60℃を
越えない様に冷却しながら約20分で反応を終了さ
せた。これに和光純薬工業株式会社製抱水ヒドラ
ジン（NH2NH2・H2O）を13ｇ及び関東化学株
式会社製ホウ酸（H3BO3）39ｇを加えた。得ら
れた透明の液体を25ｇ分取し、さらに水60mlを加
えて希釈しこれに東洋紙株式会社製5Aの紙
を浸漬した後、70℃に保たれた乾燥器で30分間乾
燥させた。該紙を180℃及び200℃において各３
分間加熱しその着色性を観察した。さらにその難
燃効果についても調べた。その結果を表−３に示
す。
実施例 ２〜６
実施例１において表−１の如く難燃化剤を調整
した以外は同一にして処理して、実施例１と同様
に着色性および難燃効果を試験した。その結果を
表−３に示す。尚アミンはいずれも50wt％水溶
液を使用した。
The present invention relates primarily to flame retardants for use in paper. Conventional flame retardants for paper include guanidine sulfamate. However, these flame retardants do not exhibit their effects unless added in large amounts, and there is a problem in that flame retardant-treated paper becomes colored when heated. On the other hand, the polyethylene polyamine or ethylene diamine phosphate described in Japanese Patent Publication No. 49-32754 exhibits excellent flame retardancy, but when paper coated with the amine phosphate is heat-treated, its coloration is reduced. There were some notable drawbacks. The present inventors have conducted various studies in order to solve the above-mentioned drawbacks of amine phosphates, and have found that amine phosphates contain hydrazine compounds and/or boric acid compounds, or even formic acid, phosphorous acid, and hypophosphorous acid. The present invention has been completed by discovering that by mixing one or more of these salts, the coloration during heat treatment can be suppressed to a level that is minimal or minimal and poses no problem in practical use, without reducing flame retardancy. I've reached it. The amine phosphate in the present invention is ethylenediamine or its condensate, for example, H 2 N-(CH 2 CH 2 NH) o -H (in terms of flame retardancy, n=
1-5 is good. ) HN-(C 2 H 4 ) 2 NH, HN(C 2 H 4 ) 2 NC 2 H 4 NH 2 and one or more amines are reacted with phosphoric acid. The reaction ratio of amine and phosphoric acid is not particularly limited, but PH7 is recommended because it has little effect on paper and has high solubility in water.
Preferably, it is adjusted back and forth. Examples of the hydrazine compound used in the present invention include hydrazine hydrate, hydrazine sulfate, and hydrazine acetate. These may be used alone or in combination of two or more. The mixing amount of these hydrazine compounds is 1
It is preferably 0.1 part by weight or more. Examples of boric acid compounds include boric acid and sodium borate, which may be used alone or in combination of two or more. The amount of the boric acid compound to be mixed is preferably 0.2 parts by weight or more per 1 part by weight of the amine phosphate, but if more than 0.8 parts by weight is mixed, the paper will harden and its texture will deteriorate. Addition of formic acid, phosphorous acid, hypophosphorous acid, or a salt thereof has the effect of reducing the amount of hydrazine compound mixed, and when used together with a boric acid compound, coloring can be further suppressed. Salts with high solubility in water, such as sodium salts, are preferred, and the mixing amount is approximately 1 part by weight of the amine phosphate.
It is preferably 0.1 part by weight or more. The adhesion rate of the above flame retardant is sufficiently effective even at 10%, compared to 18% or more for conventional guanidine sulfamate. This flame retardant can be produced as follows. That is, one method is to dissolve or mix a hydrazine compound and/or a boric acid compound in an aqueous phosphoric acid solution or slurry of an amine to form a slurry, or to add formic acid, phosphorous acid,
Hypophosphorous acid or a salt thereof is added to form a liquid or slurry.Another method is to separate the amine phosphate crystals precipitated from a solvent such as water or alcohol, and then dry the crystals, which are then mixed with hydrazine sulfate, etc. A solid hydrazine compound and/or a boric acid compound, or a salt of formic acid, phosphorous acid, or hypophosphorous acid is mixed to form a powder.
There is no discernible difference in the effectiveness of these three types of flame retardants: liquid, slurry, and powder. The present invention will be specifically explained below using Examples. Example 1 134 ml of water and 75 wt% phosphoric acid in a 500 ml flask
While stirring, 49 g of an aqueous solution of ethylenediamine with a concentration of 50 wt% was gradually added dropwise. The reaction was completed in about 20 minutes while cooling the solution so that the temperature did not exceed 60°C. To this were added 13 g of hydrazine hydrate (NH 2 NH 2 .H 2 O) manufactured by Wako Pure Chemical Industries, Ltd. and 39 g of boric acid (H 3 BO 3 ) manufactured by Kanto Chemical Co., Ltd. 25 g of the resulting transparent liquid was taken, diluted with 60 ml of water, and 5A paper manufactured by Toyo Shi Co., Ltd. was immersed in the liquid, followed by drying in a dryer kept at 70° C. for 30 minutes. The paper was heated at 180℃ and 200℃ for 3 times each.
The mixture was heated for a minute and its colorability was observed. Furthermore, its flame retardant effect was also investigated. The results are shown in Table-3. Examples 2 to 6 Coloring properties and flame retardant effects were tested in the same manner as in Example 1, except that the flame retardant was adjusted as shown in Table 1. The results are shown in Table-3. In each case, a 50 wt% aqueous solution of the amine was used.
【表】【table】
【表】
実施例 ７
500mlフラスコに水100ml、75wt％リン酸を106
ｇ仕込み撹拌しながら濃度50wt％エチレンジア
ミン水溶液98ｇを徐々に滴下した。液温は60℃を
越えない様に冷却しながら約30分で反応を終了さ
せた。析出するアミンのリン酸塩結晶を過した
後、100℃に保たれた乾燥器において２時間乾燥
した。得られる白色結晶10ｇ及びホウ酸６ｇを水
90mlに溶解した後、実施例１と同様に紙を処理
し試験を行つた。その結果を表−３に示す。
実施例８〜９，比較例１
実施例７において乾燥したアミンのリン酸塩10
ｇと表−２に示す割合でヒドラジン化合物、ホウ
酸化合物とを水に溶解した以外は実施例７と同一
にして処理した。その後、実施例１と同様に紙
を処理し試験を行つた。その結果を表−３に示
す。[Table] Example 7 100ml of water and 75wt% phosphoric acid in a 500ml flask
While stirring, 98 g of an aqueous solution of ethylenediamine with a concentration of 50 wt% was gradually added dropwise. The reaction was completed in about 30 minutes while cooling the solution so that the temperature did not exceed 60°C. After filtering out the precipitated amine phosphate crystals, the mixture was dried for 2 hours in a dryer kept at 100°C. Add 10 g of the obtained white crystals and 6 g of boric acid to water.
After dissolving in 90 ml, the paper was treated and tested in the same manner as in Example 1. The results are shown in Table-3. Examples 8-9, Comparative Example 1 Amine phosphate 10 dried in Example 7
The treatment was carried out in the same manner as in Example 7, except that the hydrazine compound and the boric acid compound were dissolved in water in the proportions shown in Table 2. Thereafter, the paper was treated and tested in the same manner as in Example 1. The results are shown in Table-3.
【表】
製試薬特級
[Table] Special grade reagents
Claims (1)
種以上とリン酸との反応生成物と、 (イ) ヒドラジン化合物及び／もしくはホウ酸化合
物 または (ロ) ヒドラジン化合物及び／もしくはホウ酸化合
物ならびに一種以上のギ酸、亜リン酸、次亜リ
ン酸もしくはその塩 とからなる難燃化剤。[Scope of Claims] 1. A reaction product of ethylenediamine and/or one or more of its condensates and phosphoric acid, and (a) a hydrazine compound and/or a boric acid compound, or (b) a hydrazine compound and/or a boric acid compound. and a flame retardant comprising one or more of formic acid, phosphorous acid, hypophosphorous acid, or a salt thereof.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21628283A JPS60108491A (en) | 1983-11-18 | 1983-11-18 | Flame-retardant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21628283A JPS60108491A (en) | 1983-11-18 | 1983-11-18 | Flame-retardant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60108491A JPS60108491A (en) | 1985-06-13 |
| JPH0420957B2 true JPH0420957B2 (en) | 1992-04-07 |
Family
ID=16686088
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21628283A Granted JPS60108491A (en) | 1983-11-18 | 1983-11-18 | Flame-retardant |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60108491A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012090671A1 (en) * | 2010-12-28 | 2012-07-05 | 株式会社ダイセル | Method for manufacturing composite molded body |
| WO2014156989A1 (en) | 2013-03-26 | 2014-10-02 | ダイセルポリマー株式会社 | Composite molded body production method |
| WO2015008771A1 (en) | 2013-07-18 | 2015-01-22 | ダイセルポリマー株式会社 | Composite moulded body |
-
1983
- 1983-11-18 JP JP21628283A patent/JPS60108491A/en active Granted
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012090671A1 (en) * | 2010-12-28 | 2012-07-05 | 株式会社ダイセル | Method for manufacturing composite molded body |
| WO2014156989A1 (en) | 2013-03-26 | 2014-10-02 | ダイセルポリマー株式会社 | Composite molded body production method |
| EP3248750A1 (en) | 2013-03-26 | 2017-11-29 | Daicel Polymer Ltd. | Composite molded body production method |
| WO2015008771A1 (en) | 2013-07-18 | 2015-01-22 | ダイセルポリマー株式会社 | Composite moulded body |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60108491A (en) | 1985-06-13 |
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