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JP4812006B2 - Paper density adjuster - Google Patents

Paper density adjuster Download PDF

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JP4812006B2
JP4812006B2 JP2006055275A JP2006055275A JP4812006B2 JP 4812006 B2 JP4812006 B2 JP 4812006B2 JP 2006055275 A JP2006055275 A JP 2006055275A JP 2006055275 A JP2006055275 A JP 2006055275A JP 4812006 B2 JP4812006 B2 JP 4812006B2
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paper
pulp
alkylene oxide
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adjusting agent
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JP2007254900A (en
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厚 新井
朝海 田中
潔 平
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Miyoshi Oil and Fat Co Ltd
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Description

本発明は、紙類の嵩高を向上させてボリューム感を付与することのできる紙密度調整剤に関する。   The present invention relates to a paper density adjusting agent capable of improving the bulk of paper and imparting a volume feeling.

近年紙類にはコスト低減化、印刷適正向上、高級なボリューム感の付与、ならびに森林資源保護の観点から原料パルプや薬剤の使用量低減化、古紙利用率の上昇等が求められている。しかし古紙利用率の上昇は、古紙パルプ繊維がヴァージンパルプ繊維に比べ短繊維化している為、嵩高性が低下する等の問題が生じ、結果としてパルプ使用量の増大を引き起こしていた。また古紙再生に使用される水酸化ナトリウムや珪酸ナトリウム等のアルカリ剤や過酸化水素、次亜塩素酸塩などの漂白剤等の薬剤が抄紙工程へ流入するようになり、紙密度調整剤やサイズ剤といった機能性を付与する薬剤の効果が弱まり、使用量増加をもたらす結果となっている。紙類の嵩を高める方法として、架橋剤と反応させた架橋パルプや熱融着性繊維をパルプに混合して抄紙する方法(特許文献1)、芯鞘型やサイドバイサイド型のポリエステル繊維をパルプに混合する方法(特許文献2)や紙密度調整剤を用いる方法が知られており、紙密度調整剤としては脂肪酸多価アルコールエステルやそのアルキレンオキシド付加物(特許文献3)、油脂系非イオン界面活性剤、糖アルコール系非イオン界面活性剤、糖系非イオン界面活性剤の少なくとも1種を含むもの(特許文献4)、カチオン性化合物、アミン、アミンの酸塩、両性化合物の少なくとも1種からなるもの(特許文献5)等が知られている。   In recent years, papers have been required to reduce costs, improve printing suitability, give a high-class volume, and reduce the amount of raw pulp and chemicals used, and increase the utilization rate of used paper from the viewpoint of protecting forest resources. However, the increase in the waste paper utilization rate has caused problems such as a decrease in bulkiness because waste paper pulp fibers are shorter than virgin pulp fibers, resulting in an increase in the amount of pulp used. In addition, alkali agents such as sodium hydroxide and sodium silicate used for waste paper recycling, and chemicals such as hydrogen peroxide and bleaching agents such as hypochlorite flow into the papermaking process. The effect of a drug imparting functionality such as a drug is weakened, resulting in an increase in the amount used. As a method for increasing the bulk of paper, a method of making paper by mixing a cross-linked pulp or heat-fusible fiber reacted with a cross-linking agent (Patent Document 1), a core-sheath type or side-by-side type polyester fiber into a pulp A method of mixing (Patent Document 2) and a method using a paper density adjuster are known, and examples of the paper density adjuster include fatty acid polyhydric alcohol esters and alkylene oxide adducts thereof (Patent Document 3), oil-based nonionic interfaces. From at least one of an activator, a sugar alcohol-based nonionic surfactant, a sugar-containing nonionic surfactant (Patent Document 4), a cationic compound, an amine, an amine acid salt, and an amphoteric compound (Patent Document 5) and the like are known.

特開平4−185791号公報Japanese Patent Laid-Open No. 4-185791 特開平3−269199号公報JP-A-3-269199 特開平11−350380号公報JP 11-350380 A 特開平11−200283号公報JP-A-11-200263 特開平11−269799号公報JP-A-11-269799

しかしながら、特許文献1、2の方法は、パルプとは異なる素材を用いるため紙本来の特性が損なわれる虞があるとともに、嵩を高める効果も十分ではなかった。また特許文献3、4に記載の非イオン系の紙密度調整剤は、十分な嵩高効果が得られる量を添加すると、紙力低下、サイズ度低下という問題を生じ易く、特に古紙パルプの使用量の増加や抄紙工程のクローズド化によりアニオントラッシュが増加している近年、紙力低下の問題は更に大きくなってきている。特許文献5に記載の紙密度調整剤は嵩高性と紙力強度を両立させる観点の薬剤であり、(1)カチオン性薬剤では、古紙再生に使用されるアルカリ剤や漂白剤等の薬剤が抄紙工程へ流入する事により、カチオン性薬剤の性能が不十分となる。(2)アミン薬剤類では、腐食性や安全性に問題があり、またアニオントラッシュとなり装置汚染やピッチトラブルの原因となり、更にサイズ性が低下するとともに、アルカリ抄紙傾向となる為、印刷インク特性に影響を生じる。(3)アミンの酸塩として実施例記載薬剤では、対イオンとなるCl、Brや酢酸での欠点として、対イオンを形成させる原料の安全性(腐食性、臭気の問題)、少量でのpH変動が大きく薬剤調製、安定性や、抄紙マシンやポンプを腐食させ操業に支障をきたす虞があり、更に紙製品を焼却した際に、薬剤に起因したダイオキシン類等の汚染物質による大気汚染の虞がある。(4)両性薬剤類では、嵩高効果が元々不十分であるのに加え、アニオントラッシュと反応し装置汚染やピッチトラブル、更にサイズ性の低下などが生じる。特許文献5に記載の紙密度調整剤は、上記(1)〜(4)に挙げたようなサイズ性の問題や、古紙使用率の上昇、クローズド化、薬剤の増加及び安全性、トラッシュ増加、紙質の安定性、操業性、ダイオキシン類生成の問題等、使用環境特性(抄紙工程の諸問題)・環境保全への配慮が成されていない等の点で不十分なものであった。   However, since the methods of Patent Documents 1 and 2 use a material different from pulp, the original properties of paper may be impaired, and the effect of increasing the bulk is not sufficient. In addition, the nonionic paper density adjusting agents described in Patent Documents 3 and 4 are prone to cause problems such as a reduction in paper strength and a reduction in size when added in an amount that provides a sufficient bulky effect. In recent years, the anion trash has increased due to the increase in the paper making process and the closed paper making process, and the problem of paper strength reduction has become even greater. The paper density adjusting agent described in Patent Document 5 is a drug from the viewpoint of achieving both bulkiness and paper strength. (1) With cationic drugs, chemicals such as alkaline agents and bleaching agents used for recycling recycled paper are used for papermaking. By flowing into the process, the performance of the cationic drug becomes insufficient. (2) Amine chemicals have problems with corrosiveness and safety, cause anion trash, cause device contamination and pitch trouble, further reduce size, and tend to produce alkaline paper, resulting in improved printing ink characteristics. Produces an impact. (3) In the drugs described in the examples as amine acid salts, the disadvantages of Cl, Br, and acetic acid as counterions are the safety of raw materials that form counterions (corrosion and odor problems), pH in small amounts Fluctuation is large and there is a risk that the preparation and stability of the chemicals may corrode the paper machine and pump, which may hinder the operation. Further, when paper products are incinerated, there is a risk of air pollution caused by chemicals and other pollutants such as dioxins. There is. (4) In amphoteric drugs, the bulky effect is originally insufficient, and it reacts with anion trash to cause device contamination, pitch trouble, and further decrease in size. The paper density adjusting agent described in Patent Document 5 is a problem of size as listed in the above (1) to (4), an increase in used paper usage rate, closed, increased drug and safety, increased trash, It was inadequate in terms of stability of the paper quality, operability, problems of dioxin generation, environmental characteristics of use (problems in the papermaking process), and consideration for environmental conservation.

本発明は上記従来技術の問題を解決するためになされたもので、抄紙工程において古紙パルプ使用量が増加したり、抄紙工程のクローズド化によってアニオントラッシュが増加した場合でも、紙力やサイズ度の低下を抑制し、嵩高で低密度の紙類を得ることのできる紙密度調整剤を提供することを目的とする。   The present invention was made to solve the above-mentioned problems of the prior art, and even when the amount of used paper pulp increases in the paper making process, or when anion trash increases due to the closed paper making process, the paper strength and sizing degree are increased. An object of the present invention is to provide a paper density adjusting agent capable of suppressing the decrease and obtaining a bulky and low density paper.

即ち本発明は、一級あるいは二級アミンの窒素に、一級あるいは二級アミン1モル当たり、総炭素数10〜22のアルキレンオキシドが1モル付加したヒドロキシアミン誘導体に、総炭素数2〜4のアルキレンオキシドを付加し、アルキレンオキシドがヒドロキシアミン誘導体の水酸基にも付加した一般式(a)で示される化合物のリンゴ酸塩及び/又は乳酸塩よりなることを特徴とする紙密度調整剤を要旨とするものであるThat is, the present invention relates to nitrogen one primary or secondary amine, per primary or secondary amine 1 mol of the total carbon number of 10 to 22 to the hydroxylamine derivative alkylene oxide is 1 mol adduct, a total carbon number of 2 to 4 A paper density adjusting agent comprising a malate and / or a lactate of a compound represented by the general formula (a) in which an alkylene oxide is added and the alkylene oxide is also added to a hydroxyl group of a hydroxyamine derivative. To do .

Figure 0004812006
Figure 0004812006

本発明の紙密度調整剤は、古紙パルプ使用量の多い抄紙工程や、クローズド化された抄紙工程において使用しても、抄紙マシンやポンプ等の装置の腐食性および汚染を低減し、紙力やサイズ度の低下を抑制し、嵩高性に優れた紙類を得ることができる。また本発明の紙密度調整剤は少ない使用量で優れた嵩高性を付与できるため、使用量を削減することができ、しかも本発明の紙密度調整剤で処理した紙類は焼却した際に有害な物質を排出する虞がないため、環境汚染問題を生じることもない等の効果を有する。   The paper density adjusting agent of the present invention reduces the corrosiveness and contamination of equipment such as a paper machine and a pump even when used in a paper making process with a large amount of used paper pulp or a closed paper making process. Papers excellent in bulkiness can be obtained by suppressing the decrease in size. Further, since the paper density adjusting agent of the present invention can impart excellent bulkiness with a small amount of use, the amount of use can be reduced, and papers treated with the paper density adjusting agent of the present invention are harmful when incinerated. Since there is no possibility of discharging a nuisance substance, it has the effect of not causing environmental pollution problems.

本発明の紙密度調整剤を構成させる一級アミンとしては、モノメタノールアミン、モノエタノールアミン、3−アミノ−1−プロパノール、1−アミノ−2−プロパノール、4−アミノ−1−ブタノール、4−アミノ−2−ブタノール、5−アミノ−1−ペンタノール、6−アミノ−1−ヘキサノール等のモノアルカノールアミン等が挙げられ、なかでも嵩高効果に優れるため、モノメタノールアミン、モノエタノールアミンが好ましい。二級アミンとしてはジメタノールアミン、ジエタノールアミン、ジプロパノールアミン、ジイソプロパノールアミン等のジアルカノールアミンが挙げられ、なかでも嵩高効果に優れるため、ジメタノールアミン、ジエタノールアミンがより好ましい。 The primary amine which constitutes the paper density modifier of the present invention, mono methanol, monoethanolamine, 3-amino-1-propanol, 1-amino-2-propanol, 4-amino-1-butanol, 4- Examples thereof include monoalkanolamines such as amino-2-butanol, 5-amino-1-pentanol, and 6-amino-1-hexanol. Among them, monomethanolamine and monoethanolamine are preferable because they are excellent in bulking effect. Examples of secondary amines include dialkanolamines such as dimethanolamine, diethanolamine, dipropanolamine, and diisopropanolamine. Among them, dimethylethanolamine and diethanolamine are more preferable because they are excellent in bulkiness.

上記一級あるいは二級アミンの窒素に反応する総炭素数10〜22のアルキレンオキシドとしては例えば、1,2−エポキシデカン、1,2−エポキシドデカン、1,2−エポキシテトラデカン、1,2−エポキシヘキサデカン、1,2−エポキシエイコサン、1,2−エポキシドコサン等が挙げられる。   Examples of alkylene oxides having 10 to 22 carbon atoms that react with nitrogen of the primary or secondary amine include 1,2-epoxydecane, 1,2-epoxydodecane, 1,2-epoxytetradecane, and 1,2-epoxy. Hexadecane, 1,2-epoxyeicosane, 1,2-epoxydocosane and the like can be mentioned.

本発明の紙密度調整剤は、一級あるいは二級アミンの窒素に、総炭素数10〜22のアルキレンオキシドが1モル付加したヒドロキシアミン誘導体に、更に総炭素数2〜4のアルキレンオキシドが付加した化合物のリンゴ酸塩、乳酸塩であり、一般式(b)で示されるヒドロキシアミン誘導体に総炭素数2〜4のアルキレンオキシドが付加した構造を有する、一般式(a)で示される化合物のリンゴ酸塩や乳酸塩が挙げられ、リンゴ酸塩と乳酸塩の混合物であっても良い。総炭素数2〜4のアルキレンオキシドとしては、エチレンオキシド(EO)、プロピレンオキシド(PO)、ブチレンオキシド(BO)等が挙げられ、2種以上が付加したものでも良い。異なる2種以上のアルキレンオキシドが付加している場合、ランダムに付加したものでも、ブロック状に付加したものでも良い。総炭素数2〜4のアルキレンオキシドの付加モル数は1〜100モルが好ましい。 In the paper density adjusting agent of the present invention, an alkylene oxide having 2 to 4 carbon atoms is further added to a hydroxyamine derivative in which 1 mole of alkylene oxide having 10 to 22 carbon atoms is added to nitrogen of a primary or secondary amine. An apple of a compound represented by the general formula (a), which is a malate or lactate of the compound and has a structure in which an alkylene oxide having 2 to 4 carbon atoms is added to the hydroxyamine derivative represented by the general formula (b) Examples thereof include acid salts and lactate, and may be a mixture of malate and lactate. Examples of the alkylene oxide having 2 to 4 carbon atoms include ethylene oxide (EO), propylene oxide (PO), butylene oxide (BO), etc., and those having two or more added may be used. When two or more different alkylene oxides are added, they may be added randomly or in a block form. Number of moles of added alkylene oxide having a total carbon number of 2 to 4 from 1 to 100 mol is not preferable.

Figure 0004812006
Figure 0004812006

Figure 0004812006
Figure 0004812006

級あるいは二級アミンの窒素に、総炭素数10〜22のアルキレンオキシドが付加したヒドロキシアミン誘導体に、更に総炭素数2〜4のアルキレンオキシドが付加した化合物のリンゴ酸及び/又は乳酸塩がより嵩高効果、紙力強度に優れ好ましく、特に一般式(a)で示されるヒドロキシアミン誘導体の水酸基にもアルキレンオキシドが付加した構造を有する化合物のリンゴ酸塩、乳酸塩が、アニオントラッシュ分散効果に優れるので、濾水性が向上し工程時間が短縮すると共に、色差(明度、白度、黄色度)の低下、ムラを抑制し紙質が均一となりピッチトラブルが低減でき好ましい To the nitrogen of a primary or secondary amine, the total hydroxylamine derivative alkylene oxide is added with a carbon number of 10 to 22, further malic acid and / or lactate salt of the compound of alkylene oxide is added in the total carbon number of 2 to 4 bulkier effect, preferably superior paper strength, particularly malate of general formula (a) compound shown alkylene oxide to the hydroxyl group of Ruhi Dorokishiamin derivative has a structure added, the lactate salts, anionic trash dispersion effect Therefore, the drainage is improved, the process time is shortened, and the color difference (brightness, whiteness, yellowness) is reduced, unevenness is suppressed, the paper quality becomes uniform, and pitch trouble can be reduced .

本発明の紙密度調整剤は、抄紙工程においてパルプスラリーに添加することにより、得られる紙類の嵩を高めることができる。本発明の紙密度調整剤をパルプスラリー中に添加する量は、パルプ原料乾燥重量の0.01〜2重量%が好ましい。パルプ原料としては、針葉樹系パルプ、広葉樹系パルプ、化学パルプ化法パルプ、セミケミカルパルプ、機械パルプ、古紙パルプ等のいずれも使用することができる。本発明の紙密度調整剤はヴァージンパルプ、古紙パルプのいずれに対しても優れた嵩高効果を発揮し、またクローズド化された抄紙工程において用いても、オープンな抄紙工程において用いても、優れた嵩高効果が発揮されるが、従来の紙密度調整剤により嵩高性が付与され難い古紙パルプを含むクローズド化された抄紙工程においても、優れた嵩高性付与効果が発揮される。本発明の紙密度調整剤とともに、サイズ剤、紙力増強剤、スケール防止剤、消泡剤等、一般的に使用される抄紙工程用薬剤を併用することができる。   By adding the paper density adjusting agent of the present invention to the pulp slurry in the paper making process, the bulk of the resulting paper can be increased. The amount of the paper density adjusting agent of the present invention added to the pulp slurry is preferably 0.01 to 2% by weight of the pulp raw material dry weight. As the pulp raw material, any of softwood pulp, hardwood pulp, chemical pulping pulp, semi-chemical pulp, mechanical pulp, waste paper pulp and the like can be used. The paper density adjusting agent of the present invention exerts an excellent bulky effect on both virgin pulp and waste paper pulp, and is excellent in both the closed paper making process and the open paper making process. Although a bulky effect is exhibited, an excellent bulkiness imparting effect is also exhibited in a closed papermaking process including waste paper pulp, which is difficult to impart bulkiness with a conventional paper density adjusting agent. The paper density adjusting agent of the present invention can be used in combination with commonly used paper making process agents such as a sizing agent, a paper strength enhancer, a scale inhibitor, and an antifoaming agent.

以下、実施例を挙げて本発明を更に詳細に説明する。
実施例、比較例1〜8
パルプ原料として、クローズド化抄紙工程採用の製紙メーカーより提供された工程薬剤の含まれる約3%の古紙パルプスラリーを用いて、坪量60g/m2の紙シートが得られるように調整した。このパルプスラリーを攪拌しながらパルプスラリー中のパルプ原料乾燥重量に対して紙密度調整剤を0.6重量%、サイズ剤(アルキルケテンダイマー系)を1.0重量%添加し、120メッシュワイヤーを備えた角型タッピ抄紙機で試験紙を作成し圧搾後、100メッシュの濾布で挟み、鏡面ドライヤーを用い、105℃で3分間乾燥した。使用した紙密度調整剤の種類を表1に示した。乾燥した紙シートを25℃、湿度40%の条件下で24時間調湿した後、紙密度(嵩高性)、紙力残存率(紙力強度)、サイズ度、アニオントラッシュ分散性の確認を以下の方法で測定した。嵩高性、紙力残存率の測定値は10回の測定、アニオントラッシュ分散性の確認は5回の測定の平均値評価である。これらの結果を紙密度調整剤とサイズ剤を使用していない参考例1とサイズ剤のみを使用した参考例2とともに表2に示す。
Hereinafter, the present invention will be described in more detail with reference to examples.
Example 1 and Comparative Examples 1-8
As a pulp raw material, a paper sheet having a basis weight of 60 g / m 2 was prepared by using about 3% waste paper pulp slurry containing a process chemical provided by a paper manufacturer using a closed paper making process. While stirring the pulp slurry, 0.6% by weight of a paper density adjusting agent and 1.0% by weight of a sizing agent (alkyl ketene dimer system) are added to the dry weight of the pulp raw material in the pulp slurry, and a 120 mesh wire is added. A test paper was prepared and squeezed with the square tapi paper machine provided, sandwiched between 100 mesh filter cloths, and dried at 105 ° C. for 3 minutes using a mirror dryer. Table 1 shows the types of paper density adjusting agents used. After conditioning the dried paper sheet for 24 hours under conditions of 25 ° C. and 40% humidity, confirmation of paper density (bulkness), paper strength remaining rate (paper strength), sizing degree, and anion trash dispersibility is as follows: It measured by the method of. The measured value of bulkiness and paper residual ratio is 10 measurements, and the confirmation of anion trash dispersibility is an average evaluation of 5 measurements. These results are shown in Table 2 together with Reference Example 1 in which the paper density adjusting agent and the sizing agent are not used and Reference Example 2 in which only the sizing agent is used.

Figure 0004812006
Figure 0004812006

Figure 0004812006
Figure 0004812006

※1:紙密度(嵩高性)(g/cm3):
調湿後の紙シートの坪量(g/m2)と厚み(mm)を測定し、下記(1)式により密度(g/cm3)を求めた。密度が小さい程、嵩高である。
紙密度=坪量÷厚み×0.001 (1)
* 1: Paper density (bulkyness) (g / cm 3 ):
The basis weight (g / m 2 ) and thickness (mm) of the paper sheet after humidity control were measured, and the density (g / cm 3 ) was determined by the following formula (1). The smaller the density, the higher the bulk.
Paper density = basis weight ÷ thickness × 0.001 (1)

※2:紙力残存率(%):
調湿後の紙シートから2.5cm×10cmの大きさの試験片10枚を切り出し、ユニトロン引張り試験機((株)上島製作所)により、紙力強度(引張強さ)を測定した。10枚の試料について平均した値を平均紙力強度として求め、ブランク(薬剤未使用で抄紙したもの)の紙力強度を100とし、下記式(2)より紙力残存率を算出した。
紙力残存率=試験片の平均紙力強度÷ブランクの平均紙力強度×100 (2)
* 2: Paper strength remaining rate (%):
Ten test pieces having a size of 2.5 cm × 10 cm were cut out from the paper sheet after humidity control, and the paper strength (tensile strength) was measured with a Unitron tensile tester (Ueshima Seisakusho Co., Ltd.). The average value for 10 samples was determined as the average paper strength, and the paper strength of blanks (made without using any chemicals) was set to 100, and the residual strength was calculated from the following formula (2).
Remaining paper strength = average paper strength of the test piece ÷ average paper strength of the blank × 100 (2)

※3:ステキヒト・サイズ度(s):
調湿後の紙シートを5cm×5cmに切り取った試験片の四隅を指定通りに折り、この試験片を2%チオシアン酸アンモニウム溶液上に浮かべると同時に1%塩化第二鉄溶液をピペットで一滴落とし、3個の赤色斑点が現れるまでの時間を測定し、その秒数をステキヒト・サイズ度とした。
* 3: Stekihito size (s):
Fold the paper sheet after humidity control to 5cm x 5cm and fold the four corners as specified. Float the test piece on 2% ammonium thiocyanate solution and drop 1% ferric chloride solution with a pipette. The time until the appearance of three red spots was measured, and the number of seconds was defined as a steecht size.

※4:アニオントラッシュ分散性:
アニオントラッシュ分散性が悪いと、紙シートの色差が低下するため、調湿後の紙シートから20cm×20cmの大きさの試験片を切り出し、5cm×5cmの大きさまで4回折りたたみ、色差計(日本電色工業株式会社製)にて明度、白度、黄色度を測定し、各5枚の平均値から以下のように総合的に評価した。
◎:明度74以上、白度45以上、黄色度28未満。
○:明度72以上74未満、白度43以上45未満、黄色度28以上30未満。
△:明度70以上72未満、白度41以上43未満、黄色度30以上32未満。
×:明度70未満、白度41未満、黄色度32以上。
* 4: Anion trash dispersibility:
If the anion trash dispersibility is poor, the color difference of the paper sheet decreases, so a test piece of 20 cm x 20 cm is cut out from the paper sheet after humidity control, and is folded four times to a size of 5 cm x 5 cm. Lightness, whiteness, and yellowness were measured by Denshoku Industries Co., Ltd., and were evaluated comprehensively from the average value of each 5 sheets as follows.
A: Brightness 74 or more, whiteness 45 or more, yellowness 28 or less.
○: Lightness 72 or more and less than 74, whiteness 43 or more and less than 45, yellowness 28 or more and less than 30
(Triangle | delta): Lightness 70-72, Whiteness 41-43, Yellowness 30-32.
X: Lightness less than 70, whiteness less than 41, yellowness of 32 or more.

Claims (1)

一級あるいは二級アミンの窒素に、一級あるいは二級アミン1モル当たり、総炭素数10〜22のアルキレンオキシドが1モル付加したヒドロキシアミン誘導体に、総炭素数2〜4のアルキレンオキシドを付加し、アルキレンオキシドがヒドロキシアミン誘導体の水酸基にも付加した一般式(a)で示される化合物のリンゴ酸塩及び/又は乳酸塩よりなることを特徴とする紙密度調整剤。
Figure 0004812006
Addition of alkylene oxide having 2 to 4 carbon atoms to hydroxyamine derivative in which 1 mole of alkylene oxide having 10 to 22 carbon atoms is added per mole of primary or secondary amine to nitrogen of primary or secondary amine , A paper density adjusting agent comprising a malate and / or a lactate of a compound represented by the general formula (a) in which an alkylene oxide is also added to a hydroxyl group of a hydroxyamine derivative .
Figure 0004812006
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