JPH11255892A - Highly soluble acylated polylysine and method for producing the same - Google Patents
Highly soluble acylated polylysine and method for producing the sameInfo
- Publication number
- JPH11255892A JPH11255892A JP10061212A JP6121298A JPH11255892A JP H11255892 A JPH11255892 A JP H11255892A JP 10061212 A JP10061212 A JP 10061212A JP 6121298 A JP6121298 A JP 6121298A JP H11255892 A JPH11255892 A JP H11255892A
- Authority
- JP
- Japan
- Prior art keywords
- polylysine
- acylated
- acid
- fatty acid
- water
- 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.)
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Landscapes
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Detergent Compositions (AREA)
- Polyamides (AREA)
- Biological Depolymerization Polymers (AREA)
Abstract
(57)【要約】
【課題】 安全性や生分解性の高い界面活性剤として、
水及び各種の有機溶媒に溶解するアシル化ポリリジンを
提供すること。
【解決手段】 ポリリジンを脂肪酸無水物でアシル化し
て得られる下記の一般式（１）
【化１】
（式中、Ｒ及びＲ’は水素原子又はアシル基を表わし、
ｎは２以上を表わす。）で表わされる易溶性アシル化ポ
リリジンを提供する。脂肪酸無水物でアシル化すること
によって、水及び各種の有機溶媒に溶解するアシル化ポ
リリジンを得ることができる。(57) [Abstract] [Problem] As a surfactant with high safety and biodegradability,
To provide an acylated polylysine that is soluble in water and various organic solvents. SOLUTION: The following general formula (1) obtained by acylating polylysine with a fatty acid anhydride: (Wherein R and R ′ represent a hydrogen atom or an acyl group,
n represents 2 or more. The present invention provides a readily soluble acylated polylysine represented by the formula: By acylating with a fatty acid anhydride, an acylated polylysine that is soluble in water and various organic solvents can be obtained.
Description
【０００１】[0001]
【発明の属する技術分野】本発明は界面活性剤として有
用な、易溶性アシル化ポリリジン及びその製造方法に関
する。The present invention relates to a readily soluble acylated polylysine useful as a surfactant and a method for producing the same.
【０００２】[0002]
【従来の技術】近年、地球規模の環境保全や人体に対す
る安全性への関心が高まり、「人や地球に優しい」製品
は注目されている。界面活性剤としても、人体に対する
刺激が少なく、安全性の高い製品や、環境に対する負荷
の少ない生分解性の高い製品が望まれており、トイレタ
リー製品を中心に安全性や生分解性の高い界面活性剤の
開発が進められている。安全性が高い界面活性剤の原料
として、アミノ酸がある。アミノ酸は蛋白質の構造単位
であり、生体組織を構成するための重要な物質である。
このようなアミノ酸を原料とするアミノ酸誘導体型界面
活性剤は、安全で高い機能を有することが期待されてい
る。従来知られているアミノ酸誘導体型界面活性剤とし
ては、アシル化ペプチド、アシル化グルタミン酸等が挙
げられる。アシル化ペプチドは、動植物の蛋白質を加水
分解したポリペプチドをアシル化したもので、シャンプ
ー等のトイレタリー製品に配合されている。また、単一
アミノ酸の縮合物であるポリグルタミン酸、ポリアスパ
ラギン酸等は、合成皮革、表面処理剤、繊維原料、繊維
加工、紙加工、フィルム、塗料、電気部品等に利用され
ていることが知られている。又、同様のポリリジンは食
品保存剤、頭髪用化粧料、吸水ポリマー等として利用さ
れている。2. Description of the Related Art In recent years, interest in global environmental protection and safety for the human body has been increasing, and products that are "friendly to humans and the earth" are attracting attention. As surfactants, products with low irritation to the human body and high safety, and products with low environmental impact and high biodegradability are demanded. Activators are being developed. Amino acids are a raw material for highly safe surfactants. Amino acids are structural units of proteins and are important substances for constituting living tissues.
Such an amino acid derivative-type surfactant using an amino acid as a raw material is expected to have a safe and high function. Conventionally known amino acid derivative-type surfactants include acylated peptides and acylated glutamic acids. The acylated peptide is obtained by acylating a polypeptide obtained by hydrolyzing proteins of animals and plants and is used in toiletries such as shampoos. In addition, polyglutamic acid, polyaspartic acid, etc., which are condensates of a single amino acid, are known to be used in synthetic leather, surface treatment agents, fiber raw materials, fiber processing, paper processing, films, paints, electric parts, and the like. Have been. In addition, the same polylysine is used as a food preservative, a hair cosmetic, a water-absorbing polymer, and the like.
【０００３】[0003]
【発明が解決しようとする課題】ところで、このような
ポリリジン縮合物をアシル化したアシル化ポリリジンが
知られている。例えば、特開平５−２４６９６３号公報
には、アシル化ポリリジンを利用した乳化剤、抗菌剤、
食品添加剤等が開示されている。しかし、特開平５−２
４６９６３号公報記載のアシル化ポリリジンは水や有機
溶媒に溶解しないため、界面活性剤としての利用が制限
されていた。これはアシル化剤として酸クロライドを使
用していることが原因であると考えられる。このような
現状に鑑み、安全性や生物分解性の高い界面活性剤とし
て、アシル化ポリリジンの水や各種の有機溶媒への溶解
性の向上が求められていた。そこで本発明者らは、アシ
ル化ポリリジンを製造する場合において、アシル化剤と
して脂肪酸無水物を使用した場合、酸クロライドを使用
した場合とは明らかに物性が異なる化合物が得られるこ
とを発見した。従って本発明の目的は、アシル化剤とし
て脂肪酸無水物を使用した易溶性アシル化ポリリジンを
提供することにある。An acylated polylysine obtained by acylating such a polylysine condensate is known. For example, JP-A-5-246983 discloses an emulsifier using an acylated polylysine, an antibacterial agent,
Food additives and the like are disclosed. However, Japanese Patent Laid-Open No. 5-2
Since the acylated polylysine described in No. 46963 does not dissolve in water or an organic solvent, its use as a surfactant has been limited. This is thought to be due to the use of acid chloride as the acylating agent. In view of such a current situation, improvement in the solubility of acylated polylysine in water and various organic solvents has been demanded as a surfactant having high safety and high biodegradability. Thus, the present inventors have found that, when producing an acylated polylysine, when a fatty acid anhydride is used as an acylating agent, a compound whose physical properties are clearly different from those obtained when an acid chloride is used is obtained. Accordingly, an object of the present invention is to provide a readily soluble acylated polylysine using a fatty acid anhydride as an acylating agent.
【０００４】[0004]
【課題を解決する手段】即ち本発明は、ポリリジンを脂
肪酸無水物でアシル化して得られる下記の一般式（１）That is, the present invention provides a compound represented by the following general formula (1) obtained by acylating polylysine with a fatty acid anhydride.
【０００５】[0005]
【化２】 Embedded image
【０００６】（式中、Ｒ及びＲ’は水素原子又はアシル
基を表わし、ｎは２以上を表わす。）で表わされる易溶
性アシル化ポリリジン及びその製造方法である。(Wherein, R and R ′ each represent a hydrogen atom or an acyl group, and n represents 2 or more) and a process for producing the same.
【０００７】[0007]
【発明の実施の形態】本発明の易溶性アシル化ポリリジ
ンの原料として使用することができるポリリジンとして
は例えば、Ｄ−リジン又はＬ−リジンから通常のペプチ
ド合成で得られるポリリジンや、微生物が産出するε−
ポリリジン又はそれを酸、アルカリ又は酵素等で適当な
分子量に分解したε−ポリリジン等が挙げられる。本発
明に使用するポリリジンの好ましい分子量は１，０００
〜５，０００である。又、アシル化剤である脂肪酸無水
物としては例えば、酢酸、プロピオン酸、酪酸、吉草
酸、イソ吉草酸、カプロン酸、カプリル酸、カプリン
酸、ウンデシレン酸、ラウリン酸、ミリスチン酸、パル
ミチン酸、ステアリン酸、イソステアリン酸、アラキン
酸、ベヘン酸、リグノセリン酸、ゾーマリン酸、オレイ
ン酸、リノール酸、リノレン酸、ガドレン酸、エルカ
酸、セラコレイン酸等の脂肪酸の無水物が挙げられる。
これらの中でも、炭素数８〜２２の脂肪酸の無水物が好
ましい。ここで使用した脂肪酸無水物に対応するアシル
基がＲ又はＲ’に対応する。BEST MODE FOR CARRYING OUT THE INVENTION As polylysine which can be used as a raw material of the easily soluble acylated polylysine of the present invention, for example, polylysine obtained by ordinary peptide synthesis from D-lysine or L-lysine, and microorganisms are produced. ε-
Polylysine or ε-polylysine obtained by decomposing the same to an appropriate molecular weight with an acid, alkali, enzyme or the like can be used. The preferred molecular weight of the polylysine used in the present invention is 1,000.
~ 5,000. Examples of the fatty acid anhydride as an acylating agent include acetic acid, propionic acid, butyric acid, valeric acid, isovaleric acid, caproic acid, caprylic acid, capric acid, undecylenic acid, lauric acid, myristic acid, palmitic acid, and stearic acid. Acids, anhydrides of fatty acids such as isostearic acid, arachinic acid, behenic acid, lignoceric acid, zomaric acid, oleic acid, linoleic acid, linolenic acid, gadrenic acid, erucic acid, and seracoleic acid.
Among them, anhydrides of fatty acids having 8 to 22 carbon atoms are preferable. The acyl group corresponding to the fatty acid anhydride used here corresponds to R or R '.
【０００８】本発明の易溶性アシル化ポリリジンは、上
記のポリリジンと脂肪酸無水物を溶媒中で反応させて得
られるものである。アシル化度は、ポリリジンに対する
脂肪酸無水物の仕込み比で制御することができる。例え
ば、アシル化度が４０ｍｏｌ％以下であると本発明の易
溶性アシル化ポリリジンは水溶性を示す。反応に使用す
る溶媒は、ポリリジン及び脂肪酸無水物が共に溶解する
溶媒であれば特に限定されないが、例えば、水−メタノ
ール混合溶媒、水−エタノール混合溶媒、水−アセトン
混合溶媒、水−ジメチルホルムアミド混合溶媒、水−酢
酸混合溶媒等が挙げられる。反応温度は好ましくは室温
〜１００℃程度であり、特に高温であることは要求され
ない。反応時間は好ましくは２〜４８時間程度である。
本発明の易溶性アシル化ポリリジンは、水又は様々な有
機溶媒に溶解可能である。これは、アシル化剤として脂
肪酸無水物を使用した本発明特有の効果である。先行技
術である特開平５−２４６９６３号公報にもアシル化ポ
リリジンが開示されており見かけ上は同一の化学式で表
現されるが、本発明の易溶性アシル化ポリリジンはポリ
リジンと脂肪酸無水物との反応によって得られる種々の
混合物であるため、このような製法の相違によって前記
のアシル化ポリリジンとは異なった性質のものとなると
考えられる。[0008] The easily soluble acylated polylysine of the present invention is obtained by reacting the above polylysine with a fatty acid anhydride in a solvent. The degree of acylation can be controlled by the charge ratio of fatty acid anhydride to polylysine. For example, when the degree of acylation is 40 mol% or less, the easily soluble acylated polylysine of the present invention shows water solubility. The solvent used in the reaction is not particularly limited as long as it is a solvent in which both polylysine and the fatty acid anhydride are dissolved.For example, a water-methanol mixed solvent, a water-ethanol mixed solvent, a water-acetone mixed solvent, a water-dimethylformamide mixed solvent are used. And a mixed solvent of water and acetic acid. The reaction temperature is preferably from room temperature to about 100 ° C., and is not particularly required to be high. The reaction time is preferably about 2 to 48 hours.
The easily soluble acylated polylysine of the present invention can be dissolved in water or various organic solvents. This is an effect unique to the present invention in which a fatty acid anhydride is used as the acylating agent. An acylated polylysine is also disclosed in the prior art, Japanese Patent Application Laid-Open No. Hei 5-246963, and is apparently represented by the same chemical formula. It is presumed that the above-mentioned various methods give different properties from the above-mentioned acylated polylysine.
【０００９】本発明のアシル化ポリリジンは易溶性であ
るため、界面活性剤としての性質を示し、その性質を利
用し今まで困難であったアシル化ポリリジンの種々の用
途への利用が可能となった。具体的な用途としては例え
ば、洗浄剤、乳化剤、消泡剤、分散剤、繊維処理剤、帯
電防止剤、抗菌剤等が挙げられる。Since the acylated polylysine of the present invention is easily soluble, it exhibits properties as a surfactant, and its properties make it possible to use acylated polylysine for various uses which has been difficult so far. Was. Specific applications include, for example, detergents, emulsifiers, defoamers, dispersants, fiber treatment agents, antistatic agents, antibacterial agents and the like.
【００１０】[0010]
【実施例】以下、実施例により本発明を更に具体的に説
明する。尚、以下の実施例中、部及び％は特に記載がな
い限り重量基準である。EXAMPLES The present invention will be described more specifically with reference to the following examples. In the following examples, parts and percentages are by weight unless otherwise specified.
【００１１】（製造例１）ε−ポリリジン２．９７ｇ
（１ｍｍｏｌ）を２０％酢酸水溶液とメタノールの１：
５混合溶媒に溶解し、室温でラウリン酸無水物４．４０
ｇ（１１．５ｍｍｏｌ）と２４時間反応させた。生成物
をアセトンによって３回再結晶を行い、目的物を得た。
該化合物の1Ｈ−ＮＭＲスペクトルにおいて、０．９ｐ
ｐｍ付近に脂肪酸残基のメチルプロトン由来のピーク
ａ、３．３ｐｐｍ付近にリジンのメチレン基由来のｂ、
ｃのピークが検出された。目的物のアシル化度（アシル
化されたアミノ基／全アミノ基）は９．８ｍｏｌ％であ
った。(Production Example 1) 2.97 g of ε-polylysine
(1 mmol) in 20% acetic acid aqueous solution and methanol:
5 in a mixed solvent and lauric anhydride 4.40 at room temperature.
g (11.5 mmol) for 24 hours. The product was recrystallized three times with acetone to obtain the desired product.
In the 1 H-NMR spectrum of the compound, 0.9 p
A peak a derived from the methyl proton of the fatty acid residue near pm, a b derived from the methylene group of lysine near 3.3 ppm,
c peak was detected. The degree of acylation of the desired product (acylated amino groups / total amino groups) was 9.8 mol%.
【００１２】[0012]
【化３】 Embedded image
【００１３】以下、脂肪酸無水物の種類及び使用量を変
えて同様にして反応を行い、ラウロイル化ε−ポリリジ
ン（アシル化度１６．４ｍｏｌ％）、デシロイル化ε−
ポリリジン（アシル化度１０．０ｍｏｌ％）、デシロイ
ル化ε−ポリリジン（アシル化度２１．９ｍｏｌ％）、
オクチロイル化ε−ポリリジン（アシル化度１０．０ｍ
ｏｌ％）を得た。The reaction was carried out in the same manner as above except that the type and amount of the fatty acid anhydride were changed to obtain lauroylated ε-polylysine (degree of acylation: 16.4 mol%) and desiroylated ε-polylysine.
Polylysine (degree of acylation 10.0 mol%), desiroylated ε-polylysine (degree of acylation 21.9 mol%),
Octyloylated ε-polylysine (degree of acylation 10.0 m
ol%).
【００１４】（評価）製造例１で得られた種々のアシル
化ε−ポリリジンは何れも水及びメタノール及びエタノ
ールに対して良好な溶解性を示した。又、これらのアシ
ル化ε−ポリリジンについて、以下に示す方法により表
面張力、起泡力及び生分解性を評価した。(Evaluation) The various acylated ε-polylysines obtained in Production Example 1 all showed good solubility in water, methanol and ethanol. The surface tension, foaming power and biodegradability of these acylated ε-polylysine were evaluated by the following methods.
【００１５】「表面張力」製造例１で合成したアシル化
ポリリジンの種々の濃度の水溶液について、その２５℃
の表面張力をウイルヘルミ法によって測定した。その結
果を表１に示す。いずれのアシル化ポリリジンも十分な
表面活性能を示す。"Surface tension" The aqueous solutions of the acylated polylysine synthesized in Production Example 1 at various concentrations were measured at 25 ° C.
Was measured by the Wilhelmy method. Table 1 shows the results. All acylated polylysines show sufficient surface activity.
【００１６】[0016]
【表１】 [Table 1]
【００１７】「起泡力及び泡安定性」同様に、製造例１
で合成した下記のアシル化ポリリジン及び典型的な非イ
オン性界面活性剤であるポリオキシエチレンモノラウリ
ルエーテルについて、起泡力及び泡安定性を測定した。
測定は、各試料の臨海ミセル濃度の水溶液を調製し、２
５℃にて起泡力計を用いて半微量ＴＫ法により起泡力を
求め、その５分後泡の容積より泡安定性を求めた。その
結果を表２に示す。本発明の易溶性アシル化ポリリジン
は、起泡力ではポリオキシエチレンモノラウリルエーテ
ルのような起泡力はなく、低泡性の界面活性剤である。Production Example 1 as in "foaming power and foam stability"
The foaming power and foam stability of the following acylated polylysine synthesized in the above and polyoxyethylene monolauryl ether, which is a typical nonionic surfactant, were measured.
The measurement was performed by preparing an aqueous solution of the seaside micelle concentration of each sample,
The foaming power was determined by the semi-trace TK method using a foaming force meter at 5 ° C., and 5 minutes later, the foam stability was determined from the foam volume. Table 2 shows the results. The easily soluble acylated polylysine of the present invention does not have the foaming power of polyoxyethylene monolauryl ether as the foaming power, and is a low-foaming surfactant.
【００１８】[0018]
【表２】 [Table 2]
【００１９】「生分解性」同様に合成したアシル化ポリ
リジンおよび原料のε−ポリリジンの生分解性を測定し
た。測定は、活性汚泥を使用したＯＥＣＤ−３０１Ｄ法
によって行った。その結果を表３に示す。本発明の易溶
性アシル化ポリリジンは、良好な生分解性を示した。"Biodegradability" The biodegradability of the acylated polylysine synthesized in the same manner as above and the raw material ε-polylysine were measured. The measurement was performed by the OECD-301D method using activated sludge. Table 3 shows the results. The easily soluble acylated polylysine of the present invention showed good biodegradability.
【００２０】[0020]
【表３】 [Table 3]
【００２１】（比較製造例１）ε−ポリリジン２．９７
ｇ（１ｍｍｏｌ）水溶液に、室温でラウリン酸クロライ
ド５．０３ｇ（２３ｍｍｏｌ）と水酸化ナトリウム０．
９６ｇ（２３ｍｍｏｌ）水溶液を徐々に添加した。１時
間反応後、生じた結晶をろ別し、エタノール及び水で洗
浄後、凍結乾燥により目的物を得た。この精製物は、
水、メタノール、エタノール、アセトン及びトルエンに
は全く溶解しなかった。(Comparative Production Example 1) ε-polylysine 2.97
g (1 mmol) aqueous solution at room temperature, 5.03 g (23 mmol) of lauric acid chloride and 0.1 g of sodium hydroxide.
A 96 g (23 mmol) aqueous solution was slowly added. After reacting for 1 hour, the resulting crystals were separated by filtration, washed with ethanol and water, and lyophilized to obtain the desired product. This purified product
It did not dissolve at all in water, methanol, ethanol, acetone and toluene.
【００２２】[0022]
【発明の効果】本発明の効果は、水及び様々な溶媒に溶
解するアシル化ポリリジン及びその製造方法を提供した
ことにある。これにより、安全性と生物分解性の高いア
シル化ポリリジンの界面活性剤としての利用が可能とな
った。The effect of the present invention is to provide an acylated polylysine which is soluble in water and various solvents and a method for producing the same. This has made it possible to use acylated polylysine having high safety and high biodegradability as a surfactant.
Claims (3)
て得られる下記の一般式（１） 【化１】 （式中、Ｒ及びＲ’は水素原子又はアシル基を表わし、
ｎは２以上を表わす。）で表わされる易溶性アシル化ポ
リリジン。1. The following general formula (1) obtained by acylating polylysine with a fatty acid anhydride: (Wherein R and R ′ represent a hydrogen atom or an acyl group,
n represents 2 or more. A) a readily soluble acylated polylysine represented by the formula:
ンからなる界面活性剤。2. A surfactant comprising the easily soluble acylated polylysine according to claim 1.
ることを特徴とする請求項１記載の易溶性アシル化ポリ
リジンの製造方法。3. The method for producing a readily soluble acylated polylysine according to claim 1, wherein the polylysine is acylated with a fatty acid anhydride.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP06121298A JP4089841B2 (en) | 1998-03-12 | 1998-03-12 | Detergent containing a surfactant comprising a readily soluble acylated polylysine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP06121298A JP4089841B2 (en) | 1998-03-12 | 1998-03-12 | Detergent containing a surfactant comprising a readily soluble acylated polylysine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH11255892A true JPH11255892A (en) | 1999-09-21 |
| JP4089841B2 JP4089841B2 (en) | 2008-05-28 |
Family
ID=13164679
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP06121298A Expired - Fee Related JP4089841B2 (en) | 1998-03-12 | 1998-03-12 | Detergent containing a surfactant comprising a readily soluble acylated polylysine |
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| JP (1) | JP4089841B2 (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002293719A (en) * | 2001-03-29 | 2002-10-09 | Asahi Denka Kogyo Kk | Hair treatment composition |
| JP2003003196A (en) * | 2001-06-25 | 2003-01-08 | Asahi Denka Kogyo Kk | Disinfectant cleaning agent |
| FR2889448A1 (en) * | 2005-08-05 | 2007-02-09 | Oreal | COSMETIC COMPOSITION COMPRISING FATTY CHAIN POLYLYSINS, FOR IMPROVING THE SURFACE CONDITION OF KERATIN FIBERS |
| JP2008056878A (en) * | 2006-09-04 | 2008-03-13 | Osaka Univ | Thermosensitive polylysine |
| EP2194063A3 (en) * | 2005-11-25 | 2010-09-08 | Basf Se | Production and use of modified polylysines |
| JP2013525261A (en) * | 2009-04-22 | 2013-06-20 | ディーエスエム アイピー アセッツ ビー．ブイ． | Novel composition |
| CN112480400A (en) * | 2020-11-25 | 2021-03-12 | 华南理工大学 | Poly-lysine graft modified mineralized crystal growth inhibitor and preparation method and application thereof |
| CN115551985A (en) * | 2020-05-12 | 2022-12-30 | 巴斯夫欧洲公司 | Use of carboxymethylated lysine polymers as dispersants and compositions containing the same |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7887838B2 (en) | 2002-01-18 | 2011-02-15 | Banner Pharmacaps, Inc. | Non-gelatin film and method and apparatus for producing same |
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1998
- 1998-03-12 JP JP06121298A patent/JP4089841B2/en not_active Expired - Fee Related
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002293719A (en) * | 2001-03-29 | 2002-10-09 | Asahi Denka Kogyo Kk | Hair treatment composition |
| JP2003003196A (en) * | 2001-06-25 | 2003-01-08 | Asahi Denka Kogyo Kk | Disinfectant cleaning agent |
| FR2889448A1 (en) * | 2005-08-05 | 2007-02-09 | Oreal | COSMETIC COMPOSITION COMPRISING FATTY CHAIN POLYLYSINS, FOR IMPROVING THE SURFACE CONDITION OF KERATIN FIBERS |
| WO2007017610A3 (en) * | 2005-08-05 | 2007-03-29 | Oreal | Cosmetic composition comprising at least one fatty-chain polylysine, which is intended to improve the surface state of keratin fibres |
| US8846842B2 (en) | 2005-11-25 | 2014-09-30 | Basf Aktiengesellschaft | Production and use of highly functional, highly branched or hyperbranched polylysines |
| EP2194063A3 (en) * | 2005-11-25 | 2010-09-08 | Basf Se | Production and use of modified polylysines |
| US20100249369A1 (en) * | 2005-11-25 | 2010-09-30 | Basf Se | Production and use of highly functional, highly branched or hyperbranched polylysines |
| EP2332969A3 (en) * | 2005-11-25 | 2011-11-02 | Basf Se | Production of highly functional, highly branched or hyperbranched polylysines |
| JP2012255169A (en) * | 2005-11-25 | 2012-12-27 | Basf Se | Production and use of highly functional highly-branched or hyperbranched polylysine |
| US8378049B2 (en) | 2005-11-25 | 2013-02-19 | Basf Aktiengesellschaft | Production and use of highly functional, highly branched or hyperbranched polylysines |
| WO2008029739A1 (en) * | 2006-09-04 | 2008-03-13 | Osaka University | Thermo-responsive polylysine |
| JP2008056878A (en) * | 2006-09-04 | 2008-03-13 | Osaka Univ | Thermosensitive polylysine |
| JP2013525261A (en) * | 2009-04-22 | 2013-06-20 | ディーエスエム アイピー アセッツ ビー．ブイ． | Novel composition |
| CN115551985A (en) * | 2020-05-12 | 2022-12-30 | 巴斯夫欧洲公司 | Use of carboxymethylated lysine polymers as dispersants and compositions containing the same |
| CN112480400A (en) * | 2020-11-25 | 2021-03-12 | 华南理工大学 | Poly-lysine graft modified mineralized crystal growth inhibitor and preparation method and application thereof |
| CN112480400B (en) * | 2020-11-25 | 2021-09-21 | 华南理工大学 | Poly-lysine graft modified mineralized crystal growth inhibitor and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JP4089841B2 (en) | 2008-05-28 |
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