KR20080006242A - Stabilization of vitamin c derivatives using oligo-polysaccharides - Google Patents

Stabilization of vitamin c derivatives using oligo-polysaccharides Download PDF

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KR20080006242A
KR20080006242A KR1020060065133A KR20060065133A KR20080006242A KR 20080006242 A KR20080006242 A KR 20080006242A KR 1020060065133 A KR1020060065133 A KR 1020060065133A KR 20060065133 A KR20060065133 A KR 20060065133A KR 20080006242 A KR20080006242 A KR 20080006242A
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vitamin
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조계민
심진기
이상봉
박성용
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한국생산기술연구원
(주)코스몰
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    • A—HUMAN NECESSITIES
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    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
    • A61K47/61—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule the organic macromolecular compound being a polysaccharide or a derivative thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
    • A61K47/6921—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a particulate, a powder, an adsorbate, a bead or a sphere

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Abstract

A method for stabilizing a vitamin C derivative is provided to improve the oxidation stability of the vitamin C derivative, which has shortcomings of being easily decomposed by light and heat, by forming a complex of the vitamin C and an ionic oligo natural saccharide. A method for stabilizing a vitamin C derivative comprises the steps of: (a) mixing an aqueous solution of chitosan oligomer having a molecular weight of 1,000-2,000 Da with an aqueous solution of the vitamin C derivative; (b) adjusting the pH of the mixture solution to form a complex of a hydroxy and a carbonyl of vitamin C derivative and amino acid group of chitosan; and (c) distilling the complex under reduced pressure and drying it to obtain a powdery state product.

Description

올리고 다당체를 이용한 비타민Ｃ 유도체의 안정화 방법{Stabilization of vitamin C derivatives using oligo-polysaccharides}Stabilization of vitamin C derivatives using oligo-polysaccharides}

본 발명은 비타민 C 유도체를 항산화성이 우수한 이온성 올리고 천연다당류를 혼합하여 복합체를 형성한 후 산화안정성를 개선하는 방법에 관한 것으로, 보다 구체적으로는 키토산의 아민기와 비타민 C 유도체의 하이드록실기 및 카르복실기와의 복합체 형성을 통한 안정화 방법에 관한 것이다.The present invention relates to a method of improving the oxidative stability after forming a complex by mixing a vitamin C derivative with an ionic oligopolysaccharide having excellent antioxidant properties, and more specifically, the amine group of chitosan and the hydroxyl group and carboxyl group of the vitamin C derivative. It relates to a stabilization method through the formation of a complex with.

비타민 C는 피부에 유용한 생물학적 효과인 피부 진피층내에서 콜라겐합성을 촉진하여 피부탄력성을 증대하고, 자외선 등에서 발생되는 유해산소를 제거하는 피부미백효과 등의 우수성으로 인하여 화장품 및 피부 병리학 분야에서 각종 생약 형태로 제조하기 위하여 오랫동안 노력하였다. 좀 더 구체적으로 비타민 C는 결합조직을 자극하고, 자외선 및 공해 같은 환경요인으로부터 피부조직 방어를 향상하며, 피부의 색소를 제거시키며, 항-유리 라디칼 기능을 갖는다. Vitamin C promotes collagen synthesis in the dermal layer of skin, which is useful for skin, to increase skin elasticity, and the skin whitening effect that removes harmful oxygen generated from ultraviolet rays. Efforts have long been made to manufacture. More specifically, vitamin C stimulates connective tissue, improves skin defenses against environmental factors such as ultraviolet light and pollution, removes pigments from the skin, and has anti-free radical function.

일반적으로 화장품이나 의약품에 사용되는 비타민C는 빛이나 열에 의해 매우 약하고 분해되기 쉬운 단점을 가지고 있다. 특히, 화장품에 배합하면 쉽게 변색되 고 냄새가 변하는 등 안정성에 문제가 많아 업계에서는 비타민 C의 안정화 기술에 많은 연구 집중하고 있으나 큰 연구 성과를 이루지 못하고 있는 실정이다. 따라서, 순수 비타민 C를 사용하지 못하고 비타민 C 유도체를 사용하거나 순수 비타민 C를 오일류에 분산시키거나 폴리올에 녹여서 사용함으로써 사용성의 한계를 지니고 있다. In general, vitamin C, which is used in cosmetics and medicines, is very weak and easily decomposed by light or heat. In particular, the cosmetics are easily discolored and the smell is changed, so there are many problems in stability, the industry is focused on the stabilization technology of vitamin C, but the situation is not achieved. Therefore, the use of pure vitamin C has a limit of usability by using a vitamin C derivative or by dispersing pure vitamin C in oils or dissolving it in a polyol.

비타민 C의 안정화를 위한 제재로서 대한민국특허 공고번호 92-10272호에서는 다상유화형 유액상 화장료를 이용하였고, 대한민국특허출원 제 98-53973호에서는 2-히드록시 프로필 싸이클로덱스트린을 이용한 유중수형 타입을 이용하였다. 대한민국특허출원 제 10-2004-0069856호에서는 예덕나무 추출물을 유효성분으로 포함하는 제재를 사용하였고, 미국특허 제610267호는 L-아스코르빈산과 함께 수용성 고분자가 용해된 수용액과 계면활성제를 혼합한 수용액의 혼합물을 오일에 투입하여 유화한 후 냉각함으로써 수용성 고분자와 L-아스코르빈산을 입자형태로 고형하하여 오일에 분산되도록 하는 방법을 제시하고 있다. As a preparation for stabilizing vitamin C, Korean Patent Publication No. 92-10272 used a multiphase emulsified emulsion cosmetic, and Korean Patent Application No. 98-53973 used a water-in-oil type using 2-hydroxypropyl cyclodextrin. It was. In Korean Patent Application No. 10-2004-0069856, a preparation including Yeok-Duk extract as an active ingredient was used, and US Patent No. 616267 was prepared by mixing surfactant with an aqueous solution in which a water-soluble polymer was dissolved together with L-ascorbic acid. A method of adding an aqueous solution to an oil to emulsify and then cooling to provide a method of solidifying a water-soluble polymer and L-ascorbic acid into particles to disperse it in oil.

본 발명에서 사용되는 비타민 C 유도체(ethyl ascorbyl ether)는 비타민 C의 3위치 수산기(水酸基)를 Ethoxy기로 치환한 화합물이다. 이러한 비타민 C 유도체의 안정성의 경우 비타민 C 자체에 비해서 다소 개선되었지만 현재까지 불만스러운 문제가 있다. The vitamin C derivative (ethyl ascorbyl ether) used in the present invention is a compound in which the 3-position hydroxyl group of the vitamin C is substituted with an Ethoxy group. The stability of these vitamin C derivatives is somewhat improved compared to vitamin C itself, but there are currently unsatisfactory problems.

비타민 C 유도체의 안정성 향상을 위해 사용되는 키토산은 게, 새우, 가재 등의 갑각류로부터 얻어지는 키틴을 탈아세틸화시켜 얻은 D-글루코사민의 단당류 또는 이당류가 모노머로 중합되어 있는 폴리사카라이드계 생체고분자 물질이다. 키 토산은 항균성 및 항산화성이 우수한 것으로 알려져 있으며, 그 외에도 면역효과, 생리활성효과, 항산화작용, 세포활성화 작용, 출혈방지 등의 효능이 우수한 것으로 알려져 있다.Chitosan, which is used to improve the stability of vitamin C derivatives, is a polysaccharide-based biopolymer material in which monosaccharides or disaccharides of D-glucosamine obtained by deacetylation of chitin obtained from shellfish such as crabs, shrimps, and crayfish are polymerized with monomers. . Chitosan is known to be excellent in antimicrobial and antioxidant properties, in addition to the effects of immune, physiological activity, antioxidant activity, cell activation, bleeding prevention is known to be excellent.

이에 본 발명자들은, 비타민 C 유도체를 안정화하기 위하여 항산화성이 우수한 키토산 올리고당을 사용하여 유도체와의 복합체를 형성하게 하고 외부의 자극에 대해 비타민 C 유도체의 안정성을 확인하고 본 발명을 완성하게 되었다. Accordingly, the present inventors used chitosan oligosaccharides having excellent antioxidant properties to stabilize the vitamin C derivatives, thereby forming a complex with the derivatives, confirming the stability of the vitamin C derivatives against external stimuli, and completing the present invention.

본 발명은 상기와 같은 점을 감안하여 안출된 것으로서, 본 발명은 이온성 올리고 천연다당류를 비타민 C 유도체에 첨가하여 복합체를 형성시킴으로써, 빛이나 열에 의해 매우 약하고 분해되기 쉬운 단점을 가지는 비타민 C 유도체의 산화안정성을 개선시키는 올리고 다당체를 이용한 비타민 C 유도체의 안정화 방법을 제공하는데 그 목적이 있다.The present invention has been made in view of the above, the present invention by adding an ionic oligopolysaccharide to the vitamin C derivatives to form a complex, the vitamin C derivative having the disadvantage of very weak and easy to decompose by light or heat It is an object of the present invention to provide a method for stabilizing vitamin C derivatives using oligopolysaccharides that improve oxidative stability.

상기 목적을 달성하기 위한 본 발명에 따른 올리고 다당체를 이용한 비타민C 유도체의 안정화 방법은, (a)키토산 올리고머 수용액에 비타민 C 유도체 수용액을 혼합하는 단계, (b)상기 혼합용액의 pH를 조절하여 키토산 아미노산기와 비타민 C 유도체의 히드록시기 및 카르보닐기와의 복합체를 형성시키는 단계 및, (c)상기 복합체를 감압 증류 및 건조하여 분말 상태로 만드는 단계를 포함하는 것을 특징으로 한다.The stabilizing method of the vitamin C derivative using the oligopolysaccharide according to the present invention for achieving the above object, (a) mixing the aqueous solution of the vitamin C derivative with chitosan oligomer aqueous solution, (b) by adjusting the pH of the mixed solution chitosan Forming a complex with an amino group and a hydroxyl group and a carbonyl group of the vitamin C derivative, and (c) distilling the complex under reduced pressure to dry the powder.

또한, 상기 (a)단계에서 키토산 올리고머의 분자량은 1,000Da 내지 2,000 Da인 것이 바람직하다.In addition, the molecular weight of the chitosan oligomer in the step (a) is preferably 1,000 Da to 2,000 Da.

나아가, 상기 (b)단계에서 혼합용액의 pH는 3.5 내지 4인 것이 바람직하다. Further, the pH of the mixed solution in step (b) is preferably 3.5 to 4.

이하, 실시예를 통하여 본 발명을 더욱 상세히 설명하고자 한다. 이들 실시예는 오로지 본 발명을 예시하기 위한 것으로서, 본 발명의 범위가 이들 실시예에 의해 제한되는 것으로 해석되어서는 아니된다.Hereinafter, the present invention will be described in more detail with reference to Examples. These examples are only for illustrating the present invention, and the scope of the present invention should not be construed as being limited by these examples.

실시예Example 1 :  One : 올리고머Oligomer -비타민C 유도체 복합에의 제조Preparation to -vitamin C derivative complex

비타민 C 유도체(0.6g)를 증류수(15ml)에 넣어 교반하여 상온에서 용해시켰다. 키토산 올리고당(분자량 1,600Da)을 15ml의 증류수에 0.6부터 3 g까지 다양한 중량분율로 녹인다. 상기 비타민 C 유도체 수용액과 키토산 올리고당 수용액을 부피비율 1:1로 혼합한 후 상온에서 10분간 교반하였다. 교반된 혼합용액의 pH를 HCl 및 NaOH 희석용액으로 4.0으로 고정시킨 후 30분간 상온에서 교반하였다. 교반후 냉장고에서 동결시킨 후 건조기를 이용하여 냉동 건조시켰다(비교예1 내지 비교예5).Vitamin C derivative (0.6 g) was added to distilled water (15 ml) and stirred to dissolve at room temperature. Chitosan oligosaccharides (molecular weight 1600 Da) are dissolved in 15 ml of distilled water at various weight fractions from 0.6 to 3 g. The aqueous solution of the vitamin C derivative and the aqueous chitosan oligosaccharide solution were mixed at a volume ratio of 1: 1, and then stirred at room temperature for 10 minutes. The pH of the stirred mixed solution was fixed to 4.0 with dilute HCl and NaOH and stirred at room temperature for 30 minutes. After stirring, the mixture was frozen in a refrigerator and freeze-dried using a dryer (Comparative Examples 1 to 5).

또한, 상기의 과정을 혼합 용액의 pH조건을 달리하여 제조하였다(비교예6 내지 비교예9).In addition, the above process was prepared by varying the pH conditions of the mixed solution (Comparative Examples 6 to 9).

비타민 C 유도체와 키토산 올리고머 성분 혼합비율          Mixing ratio of vitamin C derivatives and chitosan oligomer components 비타민 C 유도체 중량(g)Vitamin C Derivative Weight (g) 키토산 올리고당중량(g)Chitosan oligosaccharide weight (g) 혼합용액 pHMixed solution pH 비교예 1Comparative Example 1 0.60.6 0.60.6 4.04.0 비교예 2Comparative Example 2 0.60.6 1.21.2 4.04.0 비교예 3Comparative Example 3 0.60.6 1.81.8 4.04.0 비교예 4Comparative Example 4 0.60.6 2.42.4 4.04.0 비교예 5Comparative Example 5 0.60.6 3.03.0 4.04.0 비교예 6Comparative Example 6 0.60.6 1.81.8 2.02.0 비교예 7Comparative Example 7 0.60.6 1.81.8 5.05.0 비교예 8Comparative Example 8 0.60.6 1.81.8 6.06.0 비교예 9Comparative Example 9 0.60.6 1.81.8 7.07.0

또한, 상기 실시예에서 혼합된 비타민 C 유도체 및 키토산 올리고당의 구조식은 다음과 같다.In addition, the structural formula of the vitamin C derivative and chitosan oligosaccharide mixed in the above embodiment is as follows.

Figure 112006049631913-PAT00001
+
Figure 112006049631913-PAT00002
Figure 112006049631913-PAT00001
+
Figure 112006049631913-PAT00002

Ethyl ascorbyl ether Chitosan          Ethyl ascorbyl ether chitosan

실시예Example 2 2 : 온도변화에 따른 안정성 시험: Stability test according to temperature change

본 발명의 실시예에 따라 제조된 복합체의 열적 안정성을 시험하기 위하여, 상기 실시예 1에서 제조된 용액을 25℃, 45℃의 항온조에서 불투명 초자 용기에 담아 2주 동안 보관하고, 보관 후 잔존하는 비타민 C 유도체의 양을 고성능 액체 크로마트그래피(HPLC)를 사용하여 측정하였다. 각각의 잔존율은 아래의 식에 의해 결정하였다. In order to test the thermal stability of the composite prepared according to the embodiment of the present invention, the solution prepared in Example 1 was stored in an opaque glass container in a thermostatic bath at 25 ℃, 45 ℃ for 2 weeks, and stored after The amount of vitamin C derivative was measured using high performance liquid chromatography (HPLC). Each residual rate was determined by the following formula.

Figure 112006049631913-PAT00003
Figure 112006049631913-PAT00003

상기 실험결과에 따른 잔존율은 다음 표2와 같다.The remaining rate according to the test result is shown in Table 2 below.

온도변화에 따른 안정성 시험  Stability test according to temperature change 샘플Sample 잔존율(%)Survival rate (%) 1주1 week 2주2 weeks 25℃25 ℃ 45℃45 ℃ 25℃25 ℃ 45℃45 ℃ 비교예 1Comparative Example 1 97.497.4 93.193.1 91.291.2 88.488.4 비교예 2Comparative Example 2 98.498.4 94.594.5 91.591.5 89.289.2 비교예 3Comparative Example 3 98.598.5 95.495.4 92.492.4 89.589.5 비교예 4Comparative Example 4 98.398.3 95.195.1 91.491.4 89.689.6 비교예 5Comparative Example 5 98.698.6 96.496.4 91.691.6 89.489.4 비교예 6Comparative Example 6 92.392.3 90.190.1 85.485.4 80.580.5 비교예 7Comparative Example 7 93.493.4 90.590.5 86.186.1 81.481.4 비교예 8Comparative Example 8 90.190.1 88.188.1 85.485.4 80.680.6 비교예 9Comparative Example 9 89.289.2 85.685.6 80.180.1 77.577.5

실시예Example 3 :  3: 자유라디칼Free radical 소거능력 Elimination ability

본 발명의 실시예예 따라 제조된 복합체의 자유라디칼 소거능력을 다음과 같이 측정하였다. 구체적으로는 1,1-디페닐-2-피크릴-히드라진(DPPH)의 방법을 사용하여 측정하였다. DPPH는 비교적 안정한 라디칼로서 517nm에서 최대 흡광을 보이며, 라디칼 소멸시 흡광성을 잃는다. The free radical scavenging ability of the composite prepared according to the embodiment of the present invention was measured as follows. Specifically, it measured using the method of 1, 1- diphenyl- 2-picryl- hydrazine (DPPH). DPPH is a relatively stable radical, exhibiting maximum absorption at 517 nm and losing absorbance upon radical disappearance.

상기 비교예 3용액을 96웰 플레이트의 각 웰에 100μl씩 넣었다. 여기에 DPPH용액을 10μl씩 첨가한 다음 상온에서 30분간 방치한 후 마이크로 플레이트 리이더를 사용하여 517nm에서의 흡광도를 측정하였다. 이때 대조군으로는 비교예 3용액과 같은 농도의 키토산 올리고머 용액 및 비타민 C 유도체 각각의 용액 100μl를 넣은 것을 사용하였다. 상기와 같은 실험결과 자유라디칼 소거 능력은 표3과 같다.100 μl of the Comparative Example 3 solution was added to each well of a 96 well plate. 10 μl of DPPH solution was added thereto, followed by standing at room temperature for 30 minutes, and then the absorbance at 517 nm was measured using a microplate reader. At this time, as a control, 100 μl of a solution of a chitosan oligomer and a vitamin C derivative having the same concentration as in Comparative Example 3 was used. As a result of the above experiment, free radical scavenging ability is shown in Table 3.

자유라디칼 소거 능력Free radical scavenging ability 샘플명Sample name 자유라디칼 소거도(%)Free radical scavenging degree (%) 비교예 3Comparative Example 3 9595 올리고 키토산Oligo chitosan 8080 비타민 C 유도체Vitamin C derivatives 9797

이상에서 본 발명의 바람직한 실시예에 대하여 설명하였으나 본 발명은 상술한 특정의 실시예에 한정되지 아니한다. 즉, 본 발명이 속하는 기술분야에서 통상의 지식을 가지는 자라면 첨부된 특허청구범위의 사상 및 범주를 일탈함이 없이 본 발명에 대한 다수의 변경 및 수정이 가능하며, 그러한 모든 적절한 변경 및 수정의 균등물들도 본 발명의 범위에 속하는 것으로 간주되어야 할 것이다.Although preferred embodiments of the present invention have been described above, the present invention is not limited to the above-described specific embodiments. That is, those skilled in the art to which the present invention pertains can make many changes and modifications to the present invention without departing from the spirit and scope of the appended claims, and all such appropriate changes and modifications are possible. Equivalents should be considered to be within the scope of the present invention.

이상에서 살펴본 바와 같이 본 발명에 따른 올리고 다당체를 이용한 비타민C 유도체의 안정화 방법에 의하면, 이온성 올리고 천연다당류를 비타민 C 유도체에 첨가하여 복합체를 형성시킴으로써, 빛이나 열에 의해 매우 약하고 분해되기 쉬운 단점을 가지는 비타민 C 유도체의 산화안정성을 개선하는 효과가 있다. 또한, 본 발명에 따른 키토산올리고머-비타민 C 유도체 복합체는 미백화장품 원료로 유용하게 사용될 수 있다.As described above, according to the stabilization method of the vitamin C derivative using the oligopolysaccharide according to the present invention, by adding an ionic oligopolysaccharide to the vitamin C derivative to form a complex, it is very weak and easily decomposed by light or heat. Eggplant has the effect of improving the oxidative stability of the vitamin C derivative. In addition, the chitosan oligomer-vitamin C derivative complex according to the present invention can be usefully used as a raw material for whitening cosmetics.

Claims (3)

(a) 키토산 올리고머 수용액에 비타민 C 유도체 수용액을 혼합하는 단계; (a) mixing an aqueous vitamin C derivative with an aqueous chitosan oligomer solution; (b) 상기 혼합용액의 pH를 조절하여 키토산 아미노산기와 비타민 C 유도체의 히드록시기 및 카르보닐기와의 복합체를 형성시키는 단계; 및,(b) adjusting the pH of the mixed solution to form a complex of a chitosan amino acid group with a hydroxy group and a carbonyl group of a vitamin C derivative; And, (c) 상기 복합체를 감압 증류 및 건조하여 분말 상태로 만드는 단계;를 포함하는 것을 특징으로 하는 올리고 다당체를 이용한 비타민C 유도체의 안정화 방법.(c) distilling and drying the complex under reduced pressure to a powder state; stabilizing a vitamin C derivative using an oligopolysaccharide, characterized in that it comprises a. 제1항에 있어서, 상기 키토산 올리고머의 분자량은 1,000Da 내지 2,000 Da인 것을 특징으로 하는 비타민C 유도체의 안정화 방법.The method of claim 1, wherein the chitosan oligomer has a molecular weight of 1,000 Da to 2,000 Da. 제1항에 있어서, 상기 혼합용액의 pH는 3.5 내지 4인 것을 특징으로 하는 비타민C 유도체의 안정화 방법.According to claim 1, wherein the pH of the mixed solution is a stabilizing method of vitamin C derivatives, characterized in that 3.5 to 4.
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US8119780B2 (en) 2006-06-02 2012-02-21 Synedgen, Inc. Chitosan-derivative compounds and methods of controlling microbial populations
US8658775B2 (en) 2006-06-02 2014-02-25 Shenda Baker Chitosan-derivative compounds and methods of controlling microbial populations
US9029351B2 (en) 2006-06-02 2015-05-12 Synedgen, Inc. Chitosan-derivative compounds and methods of controlling microbial populations
US9732164B2 (en) 2006-06-02 2017-08-15 Synedgen, Inc. Chitosan-derivative compounds and methods of controlling microbial populations
US10494451B2 (en) 2006-06-02 2019-12-03 Synedgen, Inc. Chitosan-derivative compounds and methods of controlling microbial populations

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