KR20180035623A - New semi interpenetrated polymer network in powder form working as a thickening and stabilizing agent - Google Patents
New semi interpenetrated polymer network in powder form working as a thickening and stabilizing agent Download PDFInfo
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- KR20180035623A KR20180035623A KR1020160125947A KR20160125947A KR20180035623A KR 20180035623 A KR20180035623 A KR 20180035623A KR 1020160125947 A KR1020160125947 A KR 1020160125947A KR 20160125947 A KR20160125947 A KR 20160125947A KR 20180035623 A KR20180035623 A KR 20180035623A
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- South Korea
- Prior art keywords
- polymer
- mol
- semi
- anionic copolymer
- water
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- FWFUWXVFYKCSQA-UHFFFAOYSA-M sodium;2-methyl-2-(prop-2-enoylamino)propane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(C)(C)NC(=O)C=C FWFUWXVFYKCSQA-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229960005078 sorbitan sesquioleate Drugs 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
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- C08F20/52—Amides or imides
- C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F20/56—Acrylamide; Methacrylamide
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- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
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- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers
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- A—HUMAN NECESSITIES
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- C08J3/00—Processes of treating or compounding macromolecular substances
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- C08J3/122—Pulverisation by spraying
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08K5/00—Use of organic ingredients
- C08K5/01—Hydrocarbons
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/04—Polymer mixtures characterised by other features containing interpenetrating networks
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Abstract
Description
본 발명은 화장품 및 제약 산업에서 수용성 제형의 점증제 및 안정화제로 사용 가능한 분말 형태의 새로운 반 상호 침투성 격자형 중합체(SIPN) 및 이를 포함하는 수상의 화장품, 약제 또는 피부약제의 조성물에 관한 것이다.The present invention relates to a novel semi-interpenetrating lattice polymer (SIPN) in the form of a powder, which can be used as thickeners and stabilizers in water-soluble formulations in the cosmetics and pharmaceutical industry, and compositions of aqueous cosmetic, pharmaceutical or dermatological preparations comprising them.
화장품 및 제약 산업에서 크림(creams), 유화액(emulsions), 로션(lotions) 및 기타 외용액(topical solutions)의 점도를 유용하게 증가시키기 위해 액상 형태 또는 분말 형태의 합성 고분자 점증제를 사용한다.In the cosmetic and pharmaceutical industries, synthetic polymer thickeners in liquid or powder form are used to usefully increase the viscosity of creams, emulsions, lotions and other topical solutions.
액상 형태의 점증제는 역상 라텍스(inverse latex)라고도 하는 유중 수형 고분자 에멀젼(water in oil polymeric emulsion) 형태로서, 이러한 액상 형태의 점증제는 물에서 해리(dissolution) 시간이 매우 짧기 때문에 다루고 사용하기에 편리하다. Liquid form thickeners are in the form of water in oil polymeric emulsions, also called inverse latexes. These liquid form thickeners have very short dissolution times in water, It is convenient.
그러나 유중 수형 고분자 에멀젼은 시간이 지나면 수상과 유상의 분리(sedimentations/separations)가 일어나는 문제점이 있다. 또한 민감한 사용자에 대한 피부 알레르기 반응을 일으킬 수 있는 오일을 포함하며, 오일은 투명 젤(clear gels)을 제조하는데 방해가 된다. However, the water-in-oil type polymer emulsion has a problem that sedimentations / separations occur over time. It also contains oils that can cause skin allergic reactions to sensitive users, and oils can interfere with the production of clear gels.
따라서 상기와 같은 문제점 때문에 분말 형태의 점증제가 널리 이용되고, 몇 가지 분말 형태의 점증제들이 화장품 및 제약 산업분야에 사용된다. Therefore, due to the above problems, powder-type thickeners are widely used, and some powder-type thickeners are used in the cosmetic and pharmaceutical industries.
가장 잘 알려진 분말 형태의 점증제들은 아크릴산을 기본으로 한 중합체 또는 아크릴산 및 아크릴산 에스테르를 기본으로 한 공중합체이다. 예를 들면 Noveon/Lubrizol 사에 의해 판매되고 있는 Carbopol (아크릴 산의 중합체) 제품 또는 Pemulen (아크릴 산 및 아크릴 에스테르의 공중합체) 제품 등을 언급할 수 있다.The most well known thickeners in powder form are polymers based on acrylic acid or copolymers based on acrylic acid and acrylic acid esters. For example, Carbopol (a polymer of acrylic acid) or Pemulen (a copolymer of acrylic acid and acrylic ester) sold by Noveon / Lubrizol.
상기 제품들은 미국특허 5,373,044, 미국특허 2,798,053, 유럽특허 EP 301,532에 그 제조방법이 개시되어 있다. 하지만 상기 제품들은 낮은 pH에서 점증 효과가 없는 점, 물에 점증제를 분산하고 용해시키기 위하여 시간이 오래 소요되는 점, 산성(아크릴 산) 물질의 중화가 필요한 단점이 있다. These products are disclosed in U.S. Patent No. 5,373,044, U.S. Patent No. 2,798,053, and European Patent EP 301,532. However, these products are disadvantageous in that they do not have a gradual effect at low pH, take a long time to disperse and dissolve the thickener in water, and neutralize the acid (acrylic acid) material.
또 다른 분말 형태의 점증제로서 암모늄염으로 염화된 2-acrylamido-2-methylpropanesulfonic acid (AMPS)을 기본으로 한 중합체이다. 예를 들면 Aristoflex 제품 등을 언급할 수 있다.Another powder-form thickener is a polymer based on 2-acrylamido-2-methylpropanesulfonic acid (AMPS) that is chlorinated with an ammonium salt. For example, Aristoflex products.
Aristoflex 제품은 유럽 특허 EP 816403, EP 1116733, EP 1069142에 그 제조방법이 개시되어 있으며, 미국특허 US2012/0172457에는 Sepimax로서 개시되어 있다. 하지만 이 제품의 경우 AMPS를 중화하는데 사용된 암모니아를 포함하고, 단량체로서 일부의 에스테르와 일부의 아크릴아미드 유도체를 포함하는 단점이 있다. Aristoflex products are disclosed in European Patent EP 816403, EP 1116733, EP 1069142, and Sepimax in US Patent No. US2012 / 0172457. However, this product has the disadvantage that it contains ammonia used to neutralize AMPS and contains some esters and some acrylamide derivatives as monomers.
암모니아는 휘발성이며, 디하이드록시아세톤(dihydroxy acetone)과 같은 화장품 배합 성분과 반응하여 악취를 줄 수 있어 많은 사용자들이 암모니아를 포함하는 제품을 사용하는 것을 매우 꺼려하고, 높은 pH에서 이러한 점증제의 사용이 어렵다. Ammonia is volatile and can react with cosmetic ingredients such as dihydroxy acetone to give offensive odors, making it very difficult for many users to use products containing ammonia, and the use of such thickeners at high pH This is difficult.
또한 코모노머(comonomer)로 사용되는 에스테르는 40℃ 이상의 온도에서 특히 높거나 낮은 pH에서 안정하지 않다. 중합 시 수반되는 가수분해 반응은 폴리머 백본의 변형 및 증점력, 안정화와 관련된 물성의 변화를 유발할 수 있으며 또한 독성성향이 잘 알려져 있지 않은 일부 불순물을 생성시킬 수 있다. Also, esters used as comonomers are not stable at temperatures above 40 DEG C, especially at high or low pH. The hydrolysis reaction that accompanies the polymerization can lead to changes in physical properties associated with the deformation, boiling point, and stabilization of the polymer backbone, and can also result in some impurities that are not well known for their toxicity.
미국특허 US2012/0172457에 사용되는 디메틸아크릴아미드는 아크릴아미드 유도체로서 최종 소비자가 아크릴아미드로 인식하고, 아크릴아미드는 매우 유독한 것으로 알려져 있기 때문에 많이 사용하지 않는다. The dimethylacrylamide used in U.S. Patent No. US2012 / 0172457 is an acrylamide derivative and is not widely used because it is known to the end consumer as acrylamide and because acrylamide is known to be very toxic.
또한 분말 형태의 다른 제품으로서 Sepinov EMT 10 제품 등이 사용되며, 이 제품에 대하여 미국특허 7,771,710에 제조방법이 개시되어 있다. 상기 제품의 코모노머(comonomer)로서 사용되는 중성 단량체(neutral monomer)는 아크릴아미드(acrylamide), 메타크릴아미드(methacrylamide), 디메틸아크릴아미드(dimethyl acrylamide), 히드록시에틸아크릴레이트(hydroxy ethyl acrylate), 히드록시에틸메타크릴레이트(hydroxy ethyl methacrylate), 기타 다른 아크릴레이트 또는 메타크릴레이트 등이 선택된다. 따라서 상기 제품은 아크릴아미드 또는 이의 유도체의 존재 및 가수분해에 따른 안정성 문제 등의 단점이 있다. 제품의 점증 특성과 관련하여, 코모노머로서 아크릴아미드를 포함하는 제품만이 넓은 범위의 pH에서 사용할 수 있는 것으로 미국특허 7,771,710에 기재되어 있다. Sepinov EMT 10 products and the like are also used as other products in powder form, and the production method is disclosed in U.S. Patent 7,771,710. The neutral monomer used as a comonomer of the product may be one or more selected from the group consisting of acrylamide, methacrylamide, dimethyl acrylamide, hydroxy ethyl acrylate, Hydroxyethyl methacrylate, other acrylates or methacrylates, and the like are selected. Therefore, the above products have disadvantages such as the presence of acrylamide or derivatives thereof and stability problems due to hydrolysis. With respect to the increasing character of the product, it is described in U.S. Patent 7,771,710 that only products containing acrylamide as comonomer can be used at a wide range of pH.
분말 형태의 다른 점증제는 일본특허 JP200114642(시세이도)에 기술되어 있다. 이 제품은 솔루션 중합, 벌크 중합 또는 서스펜션 중합에 의해 제조된 sodium 2-acrylamido-2-methylpropane sulfonate / acryloyl morpholine 의 공중합체이다. 그러나 이 제품의 경우 중합과정의 결과로서 분말의 습윤성(wet ability) 부족으로 인한 용해시간이 매우 긴 문제점이 있다. Other thickeners in powder form are described in Japanese Patent JP200114642 (Shiseido). This product is a copolymer of sodium 2-acrylamido-2-methylpropane sulfonate / acryloyl morpholine prepared by solution polymerization, bulk polymerization or suspension polymerization. However, in the case of this product, as a result of the polymerization process, there is a problem that the dissolution time is very long due to lack of wet ability of the powder.
따라서 본 발명을 통하여 해당 기술분야에서 점증제 및 안정화제로 사용 가능한 충분한 점증 특성을 갖는 점증제로서, 상기 문제점을 해결 가능한 분말 형태의 신규한 증점제를 제공하고자 한다. Accordingly, it is an object of the present invention to provide a novel thickener capable of solving the above-mentioned problems as a thickening agent having a sufficient gradual property to be used as a thickener and a stabilizer in the technical field of the present invention.
본 발명은 상기와 같은 문제점을 해결하기 위한 것으로 가교된 음이온 공중합체(폴리머 네트워크)와 폴리글리세릴 에스테르(선형 폴리머)로 구성되는 분말 형태의 새로운 반 상호 침투성 격자형 중합체를 제공하는 것이다. Disclosure of Invention Technical Problem [8] The present invention provides a new semi-interpenetrating lattice polymer in the form of a powder composed of a crosslinked anionic copolymer (polymer network) and a polyglyceryl ester (linear polymer).
그러나 본 발명의 목적들은 상기에 언급된 목적으로 제한되지 않으며, 언급되지 않은 또 다른 목적들은 아래의 기재로부터 당업자에게 명확하게 이해될 수 있을 것이다.However, the objects of the present invention are not limited to the above-mentioned objects, and other objects not mentioned can be clearly understood by those skilled in the art from the following description.
본 발명은 적어도 하나의 가교된 음이온 공중합체 및 적어도 하나의 폴리글리세릴 지방산 에스테르(polyglyceryl fatty ester)를 포함하고, 유중 수형 에멀젼 중합 후 스프레이 건조하여 제조되는 분말 형태의 반 상호 침투성 격자형 중합체를 제공함으로써, 수상(water phase)을 포함하는 화장품, 약제 또는 피부약제 조성물에 포함되어 증점 또는 안정화 효과를 제공한다.The present invention provides a semi-interpenetrating lattice polymer in the form of a powder comprising at least one crosslinked anionic copolymer and at least one polyglyceryl fatty ester and spray dried after water-in-oil emulsion polymerization Thereby providing a thickening or stabilizing effect by being contained in a cosmetic, pharmaceutical or skin care composition containing a water phase.
상기 가교된 음이온 공중합체는 2-아크릴아미도-2-메틸프로판-솔폰산 나트륨(sodium salt of 2-acrylamido-2-methylpropane-sulfonic acid)을 35 내지 85 mol%, 아크릴로일 모르폴린(acryloyl morpholine)을 10 내지 50 mol%, 전부 또는 일부 나트륨에 의해 염화된 아크릴산(sodium salt of acrylic acid)을 2 내지 25 mol% 및 가교제로서 적어도 하나 이상의 폴리에틸레닉 단량체(polyethylenic monomer)를 0.005 내지 1 mol% 포함하여 중합된 공중합체인 것을 특징으로 한다. The crosslinked anionic copolymer may contain 35 to 85 mol% of 2-acrylamido-2-methylpropane-sulfonic acid, acryloylmorpholine, morpholine in an amount of 10 to 50 mol%, 2 to 25 mol% of sodium salt of acrylic acid with all or a part of sodium, and 0.005 to 1 mol of at least one polyethylenic monomer as a crosslinking agent %. ≪ / RTI >
또한 상기 폴리에틸레닉 단량체(polyethylenic monomer)는 메틸렌비스아크릴아미드(methylene bis acrylamide), 에틸렌글리콜디메타크릴레이트(ethylene glycol dimethacrylate), 디에틸렌글리콜 디메타크릴레이트(diethylene glycol dimethacrylate), 트리알릴아민(triallylamine), 트리메틸올프로판 트리(메타)아크릴레이트(trimethylolpropane tri(meth)acrylate), 디알릴우레아(diallyl urea), 테트라알릴옥시에탄(tetra allyl oxy ethane), 디알릴옥시아세트산(diallyl oxy acetic acid), 알릴펜타에리트리톨(allyl penta erythritol), 알릴슈크로오스(allyl sucrose) 및 트리메틸올프로판 디알릴에테르(trimethylolpropane diallyl ether)로 구성되는 군에서 선택되는 적어도 하나 이상을 포함하는 것을 특징으로 한다.The polyethylenic monomer may be selected from the group consisting of methylene bis acrylamide, ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triallylamine, triallylamine, trimethylolpropane tri (meth) acrylate, diallyl urea, tetraallyl oxy ethane, diallyl oxyacetic acid, At least one selected from the group consisting of allyl pentaerythritol, allyl sucrose, and trimethylolpropane diallyl ether.
또한 상기 반 상호 침투성 격자형 중합체는 상기 폴리글리세릴 지방산 에스테르를 상기 가교된 음이온 공중합체를 중합한 유중 수형 에멀젼에 첨가한 후 스프레이 건조하여 제조되거나, 상기 폴리글리세릴 지방산 에스테르 및 상기 가교된 음이온 공중합체를 중합한 유중 수형 에멀젼을 동시에 스프레이 건조하여 제조되는 것을 특징으로 한다.The semi-interpenetrating lattice polymer may be prepared by adding the polyglyceryl fatty acid ester to a water-in-oil emulsion obtained by polymerizing the crosslinked anionic copolymer, followed by spray drying, or the polyglyceryl fatty acid ester and the crosslinked anionic copolymer And a water-in-oil type emulsion obtained by polymerizing the coalescent material is spray-dried at the same time.
또한 상기 반 상호 침투성 격자형 중합체는 상기 적어도 하나의 가교된 음이온 공중합체를 70 내지 90%, 상기 적어도 하나의 폴리글리세릴 지방산 에스테르를 4 내지 20% 및 물, 계면활성제, 오일 및 무기물 입자를 포함하는 공정상 요구되는 기술적 첨가제를 10% 이하로 포함하는 것을 특징으로 한다. The semi-interpenetrating lattice polymer also comprises 70 to 90% of the at least one crosslinked anionic copolymer, 4 to 20% of the at least one polyglyceryl fatty acid ester, and water, surfactant, oil and mineral particles Of the technical additives required in the process of the present invention.
또한 본 발명은 상기 분말 형태의 반 상호 침투성 격자형 중합체를 0.1 내지 5% 포함하여, 밀크(milk), 로션(lotion), 크림(cream), 비누(soap), 목욕폼(foam bath), 밤(balm), 샴푸(shampoo), 컨디셔너(conditioner) 또는 스프레이(spray) 형태를 포함하는 제형의 화장품, 약제 또는 피부약제 조성물을 제공한다.The present invention also relates to a process for the preparation of a composition comprising from 0.1 to 5% of a powder of the semi-interpenetrating lattice polymer in the form of a milk, a lotion, a cream, a soap, a foam bath, the present invention provides a cosmetic, pharmaceutical or dermatological composition in the form of a composition comprising the form of a balm, a shampoo, a conditioner or a spray.
본 발명에 따른 증점제는 사용하기 전에 중화할 필요가 없고, 수상 용액에서 분산/용해 시간이 매우 짧은 효과를 제공한다. The thickener according to the present invention does not need to be neutralized before use and provides a very short dispersion / dissolution time in the aqueous solution.
또한 본 발명에 따른 증점제는 아크릴아미드, 아크릴아미드의 유도체 또는 에스테르 그룹을 가지는 모노머를 포함하지 않아 장시간에 매우 안정하고, 시간 및 온도, 특히 낮거나 높은 pH에서도 화학적 변화(chemical modification)를 유발하지 않는 효과를 제공한다.Further, the thickener according to the present invention does not contain acrylamide, derivatives of acrylamide or monomers having an ester group, and is very stable over a long period of time and does not cause chemical modification even at a time and temperature, especially at low or high pH Effect.
또한 본 발명에 따른 증점제는 화학적으로 불활성(inert)이면서도, 디하이드록시아세톤(DHA) 또는 과산화수소를 포함하는 수상 용액에서도 증점이 가능하다. 또한 염을 포함한 수상 용액에서도 증점이 가능하며, 넓은 범위의 pH에서도 증점이 가능하다. Also, the thickener according to the present invention is chemically inert and can be thickened in aqueous solutions containing dihydroxyacetone (DHA) or hydrogen peroxide. It can also be thickened in aqueous solutions containing salts and can be thickened over a wide range of pH.
이하에 본 발명을 상세하게 설명하기에 앞서, 본 명세서에 사용된 용어는 특정의 실시예를 기술하기 위한 것일 뿐 첨부하는 특허청구의 범위에 의해서만 한정되는 본 발명의 범위를 한정하려는 것은 아님을 이해하여야 한다. 본 명세서에 사용되는 모든 기술용어 및 과학용어는 다른 언급이 없는 한은 기술적으로 통상의 기술을 가진 자에게 일반적으로 이해되는 것과 동일한 의미를 가진다.Before describing the present invention in detail, it is to be understood that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to limit the scope of the invention, which is defined solely by the appended claims. shall. All technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art unless otherwise stated.
본 명세서 및 청구범위의 전반에 걸쳐, 다른 언급이 없는 한 포함(comprise, comprises, comprising)이라는 용어는 언급된 물건, 단계 또는 일군의 물건, 및 단계를 포함하는 것을 의미하고, 임의의 어떤 다른 물건, 단계 또는 일군의 물건 또는 일군의 단계를 배제하는 의미로 사용된 것은 아니다.Throughout this specification and claims, the word "comprise", "comprises", "comprising" means including a stated article, step or group of articles, and steps, , Step, or group of objects, or a group of steps.
한편, 본 발명의 여러 가지 실시예들은 명확한 반대의 지적이 없는 한 그 외의 어떤 다른 실시예들과 결합될 수 있다. 특히 바람직하거나 유리하다고 지시하는 어떤 특징도 바람직하거나 유리하다고 지시한 그 외의 어떤 특징 및 특징들과 결합될 수 있다. 이하, 첨부된 도면을 참조하여 본 발명의 실시예 및 이에 따른 효과를 설명하기로 한다.On the contrary, the various embodiments of the present invention can be combined with any other embodiments as long as there is no clear counterpoint. Any feature that is specifically or advantageously indicated as being advantageous may be combined with any other feature or feature that is indicated as being preferred or advantageous. Hereinafter, embodiments of the present invention and effects thereof will be described with reference to the accompanying drawings.
본 발명의 일 실시예에 따른 반 상호 침투성 격자형 중합체(Semi Interpenetrated Polymer Network, SIPN)는 적어도 하나의 가교된 음이온 공중합체 및 적어도 하나의 폴리글리세릴 지방산 에스테르(Polyglyceryl fatty ester)를 포함하며, 유중 수형 에멀젼 중합 후 분무 건조하는 단계를 포함하여 제조된다. Semi Interpenetrated Polymer Network (SIPN) according to one embodiment of the present invention comprises at least one crosslinked anionic copolymer and at least one polyglyceryl fatty ester, Spray-drying after the emulsion polymerization of the male emulsion.
반 상호 침투성 격자형 중합체(Semi Interpenetrated Polymer Network, SIPN)는 하나 이상의 네트워크(망상) 중합체 및 하나 이상의 선형 또는 분기된 중합체를 포함하는 폴리머 블렌드(polymer blends)로서, 적어도 하나의 네트워크 중합체에 적어도 몇 개의 선형 또는 분기된 고분자가 분자 단위로 침투된 것을 특징으로 한다. Semi Interpenetrated Polymer Network (SIPN) is a polymer blend comprising one or more network (network) polymers and one or more linear or branched polymers, wherein at least one network polymer Linear or branched polymer is permeated in a molecular unit.
반 상호 침투성 격자형 중합체는 폴리머 블렌드(polymer blends)로서, 원칙적으로 선형 또는 분기된 고분자가 네트워크 중합체로부터 화학 결합이 깨지지 않은 상태로 분리될 수 있는 점에서 침투성 격자형 중합체(interpenetrating polymer network)와 구별된다. Semi-interpenetrating lattice polymers are polymer blends which, in principle, are distinguished from interpenetrating polymer networks in that linear or branched polymers can be separated from the network polymer into unbreakable chemical bonds. do.
본 발명에 따른 가교된 음이온 공중합체는 2-아크릴아미도-2-메틸프로판-솔폰산 나트륨(sodium salt of 2-acrylamido-2-methylpropane-sulfonic acid, AMPS-Na)을 35 내지 85 mol%, 아크릴로일 모르폴린(acryloyl morpholine, ACMO)을 10 내지 50 mol%, 전부 또는 일부 나트륨에 의해 염화된 아크릴산(sodium salt of acrylic acid, AA-Na)을 2 내지 25 mol% 및 가교제로서 적어도 하나 이상의 폴리에틸레닉 단량체(polyethylenic monomer)를 0.005 내지 1 mol% 포함하여 중합된 중합체이다. The crosslinked anionic copolymer according to the present invention may contain 35 to 85 mol% of 2-acrylamido-2-methylpropane-sulfonic acid (AMPS-Na) Acryloyl morpholine (ACMO) in an amount of 10 to 50 mol%, 2 to 25 mol% of sodium salt of acrylic acid (AA-Na) in whole or part of sodium, and at least one And polymerized by incorporating 0.005 to 1 mol% of a polyethylenic monomer.
바람직하게는 2-아크릴아미도-2-메틸프로판-솔폰산 나트륨(sodium salt of 2-acrylamido-2-methylpropane-sulfonic acid)을 40 내지 80 mol%, 아크릴로일 모르폴린(acryloyl morpholine)을 15 내지 45 mol%, 전부 또는 일부 나트륨에 의해 염화된 아크릴산(sodium salt of acrylic acid)을 2 내지 15 mol% 및 가교제로서 적어도 하나 이상의 폴리에틸레닉 단량체를 0.005 내지 1 mol% 포함하여 중합된 중합체인 것이 좋다. Preferably 40 to 80 mol% of 2-acrylamido-2-methylpropane-sulfonic acid, 2 to 15 mol% of acryloyl morpholine, To 45 mol%, a polymer polymerized with 2 to 15 mol% of sodium salt of acrylic acid by all or part of sodium and 0.005 to 1 mol% of at least one polyethylenic monomer as a crosslinking agent good.
더욱 바람직하게는 2-아크릴아미도-2-메틸프로판-솔폰산 나트륨(sodium salt of 2-acrylamido-2-methylpropane-sulfonic acid)을 50 내지 70 mol%, 아크릴로일 모르폴린(acryloyl morpholine)을 20 내지 40 mol%, 전부 또는 일부 나트륨에 의해 염화된 아크릴산(sodium salt of acrylic acid)을 2 내지 10 mol% 및 가교제로서 적어도 하나 이상의 폴리에틸레닉 단량체를 0.005 내지 1 mol% 포함하여 중합된 중합체인 것이 좋다. More preferably 50 to 70 mol% of 2-acrylamido-2-methylpropane-sulfonic acid, 2 to 20 mol% of acryloyl morpholine, 20 to 40 mol%, 2 to 10 mol% of sodium salt of acrylic acid by whole or part of sodium, and 0.005 to 1 mol% of at least one polyethylenic monomer as a crosslinking agent It is good.
가교된 공중합체라 함은 비선형의 공중합체를 의미하는 것으로서, 이는 물에 녹지 않고 팽윤되는(swellable) 삼차원 상태로 존재하므로 화학적인 젤(gel)의 수득을 유도할 수 있다. Crosslinked copolymer refers to a non-linear copolymer, which is soluble in water and is present in a swellable three-dimensional state, which can lead to the production of a chemical gel.
가교된 음이온 공중합체는 반 상호 침투성 격자형 중합체의 격자(network) 부분에 해당한다. The crosslinked anionic copolymer corresponds to the network portion of the semi-interpenetrating lattice polymer.
가교제로서 포함되는 폴리에틸레닉 단량체는 메틸렌비스아크릴아미드(methylene bis acrylamide), 에틸렌글리콜디메타크릴레이트(ethylene glycol dimethacrylate), 디에틸렌글리콜 디메타크릴레이트(diethylene glycol dimethacrylate), 트리알릴아민(triallylamine), 트리메틸올프로판 트리(메타)아크릴레이트(trimethylolpropane tri(meth)acrylate), 디알릴우레아(diallyl urea), 테트라알릴옥시에탄(tetra allyl oxy ethane), 디알릴옥시아세트산(diallyl oxy acetic acid), 알릴펜타에리트리톨(allyl penta erythritol), 알릴슈크로오스(allyl sucrose) 및 트리메틸올프로판 디알릴에테르(trimethylolpropane diallyl ether)로 구성되는 군에서 선택되는 어느 하나 또는 두 개 이상을 포함한다. The polyethylenic monomer included as the crosslinking agent includes methylene bis acrylamide, ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triallylamine, Trimethylolpropane tri (meth) acrylate, diallyl urea, tetra allyl oxy ethane, diallyl oxyacetic acid, allyl (meth) acrylate, And one or more selected from the group consisting of allyl penta erythritol, allyl sucrose, and trimethylolpropane diallyl ether.
바람직하게는 메틸렌비스아크릴아미드(methylene bis acrylamide), 트리알릴아민(triallylamine) 또는 이들의 혼합물을 포함하는 것이 좋다. Preferably, it includes methylene bis acrylamide, triallylamine, or a mixture thereof.
폴리에틸레닉 단량체는 0.005 내지 1mol%로 포함되며, 바람직하게는 0.01 내지 0.6 mol%, 더욱 바람직하게는 0.01 내지 0.4 mol%로 포함되는 것이 좋다. 폴리에틸레닉 단량체가 0.005mol%보다 적으면 정상적인 격자형태가 형성되지 않으며 1mol%보다 많으면 물에 팽윤되지 않아 화학적인 젤의 형성이 어렵다.The polyethylenic monomer is contained in an amount of 0.005 to 1 mol%, preferably 0.01 to 0.6 mol%, and more preferably 0.01 to 0.4 mol%. When the amount of the polyethylenic monomer is less than 0.005 mol%, a normal lattice form is not formed. When the amount of the polyethylenic monomer is more than 1 mol%, it is not swollen in water, thereby making it difficult to form a chemical gel.
폴리글리세릴 지방산 에스테르는 예를 들어 데카글리세릴 모노올레이트(decaglyceryl monooleate), 데카글리세릴 디올레이트(decaglyceryl dioleate), 데카글리세릴 모노라우레이트(decaglyceryl monolaurate) 또는 데카글리세릴 디라우레이트(decaglyceryl dilaurate)를 포함하며, 반 상호 침투성 격자형 중합체의 선형 구성요소에 해당한다.The polyglyceryl fatty acid esters include, for example, decaglyceryl monooleate, decaglyceryl dioleate, decaglyceryl monolaurate or decaglyceryl dilaurate, ) And corresponds to a linear component of the semi-interpenetrating lattice polymer.
바람직하게는 데카글리세릴 모노라우레이트(decaglyceryl monolaurate) 또는 데카글리세릴 디라우레이트(decaglyceryl dilaurate)를 포함하는 것이 좋다.It is preferable to include decaglyceryl monolaurate or decaglyceryl dilaurate.
유중 수형 고분자 중합(water in oil polymerization)은 수상(water phase)에서 용해되는 2-acrylamido-2-methylpropane-sulfonic acid (AMPS), acryloyl morpholine (ACMO) 및 acrylic acid (AA)의 모노머의 고분자 중합을 의미하고, 여기서 수상(water phase)은 오일 상(oil phase)에서 계면활성제나 고분자 계면활성제에 의해 유화된다. Water in oil polymerization is a method of polymerizing monomers of 2-acrylamido-2-methylpropane-sulfonic acid (AMPS), acryloyl morpholine (ACMO) and acrylic acid (AA) dissolved in the water phase. Wherein the water phase is emulsified in the oil phase by a surfactant or a polymer surfactant.
최종적으로 가교된 음이온 공중합체는 중합반응의 마지막 단계에서 유상 또는 유기상에 분산된다.Finally, the crosslinked anionic copolymer is dispersed in the oil phase or the organic phase at the final stage of the polymerization reaction.
상기 중합방법은 Hunkeler et al, Adv. Polym.Sci. 123:115-133 (1994) 등 다양하게 개시되어 있으며 또한 다수의 특허에 기술되어 있다. 유럽특허 EP1047716, EP161038, EP503853 등에 유중 수형 고분자 에멀젼을 얻기 위한 유중 수형(또는 역상) 에멀젼 고분자 중합 방법을 개시하고 있다.The polymerization method is described in Hunkeler et al, Adv. Polym.Sci. 123: 115-133 (1994), and are also described in numerous patents. (Or reverse phase) emulsion polymeric polymerization method for obtaining a water-in-oil type polymer emulsion in EP1047716, EP161038, EP503853 and the like.
유중 수형 고분자 에멀젼은 스프레이 건조(spray-drying) 방법에 의해 용이하게 건조된다. 상기 스프레이 건조 방법은 뜨거운 공기의 흐름 속으로 고분자 에멀젼의 미세한 방울을 도입하는 것으로 구성된다. The water-in-oil type polymer emulsion is easily dried by the spray-drying method. The spray drying process consists of introducing fine droplets of the polymer emulsion into the flow of hot air.
스프레이 건조 장비는 “Spray drying Handbook by K.Master, 5th Ed, Longman Scientific 1991 에 자세하게 기술되어 있다.Spray drying equipment is described in detail in "Spray drying Handbook by K. Master, 5th Ed, Longman Scientific 1991".
폴리글리세릴 지방산 에스테르는 라디칼 고분자 중합 반응의 마지막에 음이온 가교 공중합체에 도입되어 혼합될 수 있다. 또는 스프레이 건조 장비에 유중 수형 에멀젼의 도입과 동시에 병렬로 직접적으로 도입할 수도 있다.The polyglyceryl fatty acid ester may be introduced into the anionic crosslinking copolymer and mixed at the end of the radical polymer polymerization reaction. Or may be introduced directly in parallel with the introduction of a water-in-oil emulsion into a spray drying equipment.
즉 본 발명에 따른 반 상호 침투성 격자형 중합체는 폴리글리세릴 지방산 에스테르를 가교된 음이온 공중합체를 중합한 유중 수형 에멀젼에 첨가한 후 스프레이 건조하여 제조되거나, 폴리글리세릴 지방산 에스테르 및 가교된 음이온 공중합체를 중합한 유중 수형 에멀젼을 동시에 스프레이 건조하여 제조될 수 있다. That is, the semi-interpenetrating lattice polymer according to the present invention may be prepared by adding a polyglyceryl fatty acid ester to a water-in-oil type emulsion obtained by polymerizing a crosslinked anionic copolymer and then spray-drying the polyglyceryl fatty acid ester or a polyglyceryl fatty acid ester and a crosslinked anionic copolymer Water-in-oil type emulsion polymerized by spray drying at the same time.
본 발명의 바람직한 관점에서 반 상호 침투성 격자형 중합체의 구성은 가교된 음이온 공중합체를 70 내지 90%, 폴리글리세릴 지방산 에스테르를 4 내지 20%, 물, 계면활성제, 오일, 무기물 입자 등 공정을 진행하는데 필요한 기술적 첨가제를 최대 10%까지 포함한다. 상기 첨가제들은 공정을 바람직하게 하기 위하여 요구될 수 있다. In a preferred aspect of the present invention, the structure of the semi-interpenetrating lattice polymer comprises 70 to 90% of the crosslinked anionic copolymer, 4 to 20% of the polyglyceryl fatty acid ester, and the water, surfactant, oil, Up to 10%. Such additives may be required to favor the process.
더욱 바람직한 반 상호 침투성 격자형 중합체의 구성은 가교된 음이온 공중합체를 75 내지 90%, 폴리글리세릴 지방산 에스테르를 5 내지 10%, 물, 계면활성제, 오일, 무기물 입자 등 공정을 진행하는데 필요한 기술적 첨가제를 최대 10%까지 포함한다.More preferably, the composition of the semi-interpenetrating lattice polymer comprises 75 to 90% of the crosslinked anionic copolymer, 5 to 10% of the polyglyceryl fatty acid ester, the technical additive necessary for proceeding the process such as water, surfactant, oil, Up to 10%.
본 발명에 따른 신규한 반 상호 침투성 격자형 중합체는 수상을 포함하는 화장품, 약제 또는 피부 약제 조성물에 포함되어 증점제 또는 안정화제로 사용될 수 있다. The novel semi-interpenetrating lattice polymers according to the invention can be used as thickeners or stabilizers in cosmetic, pharmaceutical or dermatological compositions comprising water-based polymers.
또한 본 발명에 따른 신규한 반 상호 침투성 격자형 중합체를 포함하는 화장품, 약제 또는 피부약제의 조성물을 제공할 수 있다. 분말 형태의 반 상호 침투성 격자형 중합체는 상기 화장품, 약제 또는 피부약제 조성물에 0.1 내지 5% 로 포함된다.Also provided is a cosmetic, pharmaceutical or dermatological composition comprising the novel semi-interpenetrating lattice polymer according to the present invention. The semi-interpenetrating lattice polymer in powder form is included in the cosmetic, pharmaceutical or dermatological composition in an amount of 0.1 to 5%.
상기 화장품, 약제 또는 피부약제 조성물은 밀크(milk), 로션(lotion), 크림(cream), 비누(soap), 목욕폼(foam bath), 밤(balm), 샴푸(shampoo), 컨디셔너(conditioner) 또는 스프레이(spray) 형태를 포함한다. The cosmetic, pharmaceutical or dermatological composition may be in the form of a milk, a lotion, a cream, a soap, a foam bath, a balm, a shampoo, a conditioner, Or a spray form.
실시예Example
실시예 1Example 1
(1) 수상 용액의 제조(1) Preparation of aqueous solution
① 1000ml 비이커에 이온교환수 183.5g을 넣고 교반한다. ① Add 183.5 g of ion-exchanged water to a 1000 ml beaker and stir.
② 50% NaOH 수용액 105.6g을 넣고 혼합한다. ② Add 105.6 g of 50% NaOH solution and mix.
③ 2-Acrylamido-2-methylpropanesulfonic acid(AMPS) 273.3g을 투입하여 용해한다. 3) Add 273.3 g of 2-acrylamido-2-methylpropanesulfonic acid (AMPS) to dissolve.
④ Sodium diethylenetriaminepentaacetate 0.2g을 투입한다. ④ Add 0.2 g of sodium diethylenetriaminepentaacetate.
⑤ Acryloyl morpholine(ACMO) 77.6g, Acrylic acid(AA) 23.8g을 투입하고 혼합한다. ⑤ Add 77.6 g of Acryloyl morpholine (ACMO) and 23.8 g of Acrylic acid (AA) and mix.
⑥ Triallyl amine 1.0g을 투입하고 50% NaOH 수용액 15g으로 중화한다. ⑥ Add 1.0 g of triallyl amine and neutralize with 15 g of 50% aqueous NaOH solution.
⑦ 이온교환수를 추가하여 680g으로 만든다.⑦ Ion exchange water is added to make 680g.
(2) 유상 용액의 제조(2) Preparation of an oil solution
① 1000ml 비이커에 Isopar M 235g을 넣고 교반한다. ① Add 235 g of Isopar M to a 1000 ml beaker and stir.
② Hypermer 1083(water in oil emulsifier, CRODA사) 25g을 넣고 혼합한다. ② Add 25 g of Hypermer 1083 (water in oil emulsifier, CRODA) and mix.
③ Azobisisobutyronitrile 0.2g을 투입하여 용해한다.③ Add 0.2 g of Azobisisobutyronitrile to dissolve.
(3) 에멀젼 용액(유화액)의 제조(3) Preparation of Emulsion Solution (Emulsion)
① 제조된 유상 용액에 수상 용액을 투입하면서 호모지나이저 (Homogenizer)로 7000rpm의 회전 속도로 강하게 교반한다. ① Stir strongly with a homogenizer at a rotation speed of 7000 rpm while putting the aqueous solution into the prepared oily solution.
② 7000rpm의 회전속도로 20분 정도 교반하여 균질한 유중 수형 에멀젼 용액(유화액)을 제조한다.(2) The mixture is stirred for about 20 minutes at a rotation speed of 7000 rpm to prepare a homogeneous water-in-oil type emulsion solution (emulsion).
(4) 반응(4) Reaction
① 제조된 유중 수형 에멀젼 용액(유화액)을 1000ml 반응용 플라스크로 이송하고 교반기, 온도계, 질소도입구 및 촉매 투입구를 설치한다. ① The prepared water-in-oil type emulsion solution (emulsion) is transferred to a 1000 ml reaction flask, and a stirrer, a thermometer, a nitrogen inlet and a catalyst inlet are installed.
② 200rpm의 회전속도로 교반하면서 질소를 액 중으로 1시간 정도 투입하여 산소를 제거한다. (2) While stirring at 200 rpm, nitrogen is poured into the solution for about 1 hour to remove oxygen.
③ 유중 수형 에멀젼(유화액)의 온도를 15℃로 맞추고 cumene hydroperoxide 0.023g을 Isopar M 4g에 혼합하여 투입한다. ③ Set the temperature of the water-in-oil type emulsion (emulsion) to 15 ℃ and add 0.023g of cumene hydroperoxide to 4g of Isopar M.
④ 5분 교반 한 후 Sodium metabisulfite 수용액(0.375g in 100g H2O)을 분당 0.3ml의 속도로 반응기로 투입한다. ④ After stirring for 5 minutes, add sodium metabisulfite aqueous solution (0.375 g in 100 g H 2 O) to the reactor at a rate of 0.3 ml per minute.
⑤ Sodium metabisulfite 수용액 투입 10분 후 발열이 시작되며 75℃로 도달한다. ⑤ Sodium metabisulfite starts to heat up after 10 minutes of water injection and reaches 75 ℃.
⑥ 이후 20분간 메타중아황산나트륨(Sodium metabisulfite) 수용액을 연속하여 투입하고 1시간 동안 온도를 75℃로 유지한다. (6) Continue to add aqueous sodium metabisulfite solution for 20 minutes and keep the temperature at 75 ℃ for 1 hour.
⑦ 40℃로 냉각한 후 Polyglyceryl-10 dilaurate (KCI PGLLA210KC) 25g을 투입하고 혼합한다. ⑦ After cooling to 40 ℃, add 25 g of Polyglyceryl-10 dilaurate (KCI PGLLA210KC) and mix.
⑧ 최종 수득된 제품은 에멀젼 형태의 점증제이다.(8) The final product obtained is an emulsion-type thickener.
(5) 건조(5) Drying
상기 반응의 완료에 의해 수득된 유중 수형 고분자 에멀젼은 정량펌프로 스프레이 드라이어에 도입되었다. 이 스프레이 드라이어는 스위스의 Buchi사의 미니스프레이 드라이어로 B-290모델이다The water-in-oil type polymer emulsion obtained by completing the above reaction was introduced into a spray dryer by a metering pump. This spray dryer is a B-290 miniature spray dryer from Buchi, Switzerland.
- 입구 온도: 150℃- Inlet temperature: 150 ° C
- 출구 온도: 105 - 110℃- Outlet temperature: 105 - 110 ° C
- 정량펌프 속도: 10 ml / minute- Dosing pump speed: 10 ml / minute
최종 제품은 분말 형태의 가교된 공중합체이다.The final product is a crosslinked copolymer in powder form.
입자 크기 분포는 1 내지 100 μm으로 구성된다.The particle size distribution is comprised between 1 and 100 mu m.
최종으로 SIPN(반 상호 침투성 격자형 중합체)를 제조하였다.Finally, SIPN (semi-interpenetrating lattice polymer) was prepared.
실시예Example 2 내지 4 2 to 4
하기 표 1에 나타낸 것과 같이 수상 용액 상의 아크릴계 단량체의 함량 및 기타 조성물의 함량을 변경한 것 이외에는 실시예 1과 동일하게 반 상호 침투성 격자형 중합체를 제조하였다. A semi-interpenetrating lattice polymer was prepared in the same manner as in Example 1 except that the content of the acrylic monomer and the content of the other composition in the aqueous solution were changed as shown in Table 1 below.
실시예 5Example 5
(1) 수상 용액의 제조(1) Preparation of aqueous solution
Triallyl amine 1.0g을 투입하는 대신 Methylene-bis-acrylamide 0.1g투입한 점을 제외하고는 실시예 2 와 동일한 방법으로 수상 용액을 제조하였다.Aqueous solution was prepared in the same manner as in Example 2, except that 0.1 g of Methylene-bis-acrylamide was added instead of 1.0 g of triallyl amine.
(2) 유상 용액의 제조(2) Preparation of an oil solution
Azobisisobutyronitrile 0.2g을 투입하지 않는 점을 제외하고는 실시예 1 과 동일한 방법으로 유상 용액을 제조하였다.An oily solution was prepared in the same manner as in Example 1, except that 0.2 g of Azobisisobutyronitrile was not added.
(3) 유중 수형 에멀젼(유화액)의 제조(3) Preparation of water-in-oil emulsion (emulsion)
실시예 1과 동일한 방법으로 균질한 유중 수형 에멀젼을 제조하였다. A homogeneous water-in-oil type emulsion was prepared in the same manner as in Example 1.
(4) 중합 반응 (4) Polymerization
유중 수형 에멀젼(유화액)의 온도를 15℃로 맞추고 ammonium persulfate 0.3g을 물 4g에 녹여 투입한 후 5분 후 cumene hydroperoxide 0.023g을 Isopar M 4g에 혼합하여 투입한 것을 제외하고 실시예 1과 동일한 방법으로 유중 수형 에멀젼 중합 조성물을 제조하였다.The temperature of the water-in-oil type emulsion (emulsion) was adjusted to 15 ° C. 0.3 g of ammonium persulfate was dissolved in 4 g of water, and 5 minutes later, 0.023 g of cumene hydroperoxide was mixed with 4 g of Isopar M, To prepare a water-in-oil emulsion polymerization composition.
(5) 건조(5) Drying
실시예 1과 동일 방법으로 SIPN(반 상호 침투성 격자형 중합체)를 제조하였다.SIPN (semi-interpenetrating lattice polymer) was prepared in the same manner as in Example 1.
실시예 6Example 6
Polyglyceryl-10 dilaurate (KCI PGLLA210KC)를 투입한 것을 제외하고 실시예 1과 동일한 방법으로 유중 수형 에멀젼 중합 조성물을 제조하였다.A water-in-oil type emulsion polymerization composition was prepared in the same manner as in Example 1, except that Polyglyceryl-10 dilaurate (KCI PGLLA210KC) was added.
수득된 유중 수형 에멀젼 중합 조성물과 Polyglyceryl-10 dilaurate 를 각각 별도의 정량펌프로 동시에 스프레이 드라이어에 도입하였다.The resulting water-in-oil type emulsion polymerization composition and Polyglyceryl-10 dilaurate were simultaneously introduced into the spray drier by separate dosing pumps.
스프레이 드라이어의 건조 조건은 실시예 1과 동일하게 진행하여 SIPN(반 상호 침투성 격자형 중합체)를 제조하였다.The drying conditions of the spray dryer were the same as in Example 1 to prepare SIPN (semi-interpenetrating lattice polymer).
실험예Experimental Example
(1) 성분 및 점도 특성(1) Components and viscosity characteristics
실시예 1 내지 6에 의하여 제조된 최종 SIPN(반 상호 침투성 격자형 중합체)에 대한 성분 및 점도 특성을 하기 표 2에 나타내었다.Component and viscosity characteristics for the final SIPN (semi-interpenetrating lattice polymer) prepared according to Examples 1 to 6 are shown in Table 2 below.
+ 0.1% NaCl 점도 (mPa·s)1.5% solution
+ 0.1% NaCl viscosity (mPa · s)
- 점도(mPa·s) 측정: Brookfield RVT, spindle no 6, 5rpm, 25℃- viscosity (mPa s) measurement: Brookfield RVT, spindle no 6, 5 rpm, 25 캜
(2) pH별 점도 측정(2) Measurement of viscosity by pH
실시예에 의해 얻은 최종 SIPN(반 상호 침투성 격자형 중합체)의 1.5% 수용액의 pH별 점도를 브룩필드 알브이티(Brookfield RVT) 점도계로 온도 25℃에서 측정(spindle no 6, 5rpm)하였으며, 그 결과를 하기 표 3에 나타내었다. The viscosity of a 1.5% aqueous solution of the final SIPN (semi-interpenetrating lattice polymer) obtained according to the example was measured (spindle no 6, 5 rpm) at 25 ° C. with a Brookfield RVT viscometer, The results are shown in Table 3 below.
(Brookfield RVT점도계로 spindle no 6, 5rpm, 25℃에서 측정)Viscosity of 1.5% aqueous solution by pH
(Measured with a Brookfield RVT viscometer at spindle no 6, 5 rpm, at 25 ° C)
(3) 과산화물에 대한 점도 및 디하이드록시아세톤에 대한 색상 안정성(3) viscosity for peroxide and color stability for dihydroxyacetone
과산화물(Hydrogen peroxide)에 대한 점도 안정성은 각각의 실시예로 제조된 최종 SIPN(반 상호 침투성 격자형 중합체)을 1% 수용액으로 제조하고 Hydrogen peroxide 2%를 추가하여 혼합한 후 40℃에서 1 개월 보관 후 점도 변화를 확인하였다. 점도변화율[ (초기점도-1개월 후 점도) x 100 / 초기점도]이 5% 이내면 안정으로 판단하였다. The viscosity stability for the hydrogen peroxide was determined by preparing the final SIPN (semi-interpenetrating lattice polymer) prepared in each Example in 1% aqueous solution, adding 2% of hydrogen peroxide and then storing at 40 ° C for 1 month The change in viscosity was confirmed. The viscosity change rate [(initial viscosity - viscosity after 1 month) x 100 / initial viscosity] was judged to be stable within 5%.
디하이드록시아세톤(Dihydroxy acetone)에 대한 색상 안정성은 각각의 실시예로 제조된 최종 SIPN(반 상호 침투성 격자형 중합체)을 1g, Dihydroxy acetone 5g, 물 94g과 혼합하여 40℃에서 1 개월 보관 후 색상변화를 확인하여 노란색은 양호한 것으로, 진한 노란색은 중간으로, 갈색은 나쁨으로 판단하였다.The color stability to dihydroxyacetone was determined by mixing 1 g of the final SIPN (semi-interpenetrating lattice polymer) prepared in each Example, 5 g of dihydroxy acetone and 94 g of water, storing at 40 ° C for 1 month, Change was judged to be good, yellow to medium, and brown to poor.
그 결과를 하기 표 4에 나타내었다.The results are shown in Table 4 below.
(단위 mPa·s)Initial viscosity
(Unit: mPa · s)
점도(단위 mPa·s)1 month after 40 ℃
Viscosity (unit: mPa · s)
상기 표 2 내지 표 4 에서 나타나는 것과 같이 본 발명에 따른 SIPN(반 상호 침투성 격자형 중합체)는 물에 용해 시 pH는 6 정도로서 사용 전에 중화할 필요가 없으며, pH 3내지 11의 넓은 범위에서 안정적으로 증점력을 보이며 과산화물 및 디하이드록시아세톤에서 안정한 효과가 있다. As shown in Tables 2 to 4, the SIPN (semi-interpenetrating lattice polymer) according to the present invention has a pH of about 6 when dissolved in water and does not need to be neutralized before use and is stable in a wide range of pH 3 to 11 It has a booster point and stable effect on peroxide and dihydroxyacetone.
화장품 제형의 제조예Manufacturing Example of Cosmetic Formulation
제조예 1: AHA 크림Production Example 1: AHA cream
제조예 1에 따른 AHA 크림 조성을 하기 표 5에 나타내었다. 하기 표 5의 A, B를 다른 용기에서 혼합하고 70℃로 승온하고, B를 A에 투입한 후 호모믹서 4000rpm으로 5분간 유화하고, C를 투입 후 호모믹서 4000rpm으로 3분간 유화하고, 45℃로 냉각 후 D를 투입하여 AHA 크림을 제조하였으며, 제조된 AHA 크림은 32,000 mPa·s (brookfield RVT, No 6, 5 rpm) pH 3.60였다.The composition of the AHA cream according to Preparation Example 1 is shown in Table 5 below. A and B shown in Table 5 were mixed in different containers and heated to 70 DEG C and B was introduced into A, followed by emulsification at 4000 rpm for 5 minutes. C was added, followed by emulsification for 3 minutes at 4000 rpm in a homomixer, And D was added to prepare an AHA cream. The prepared AHA cream had a pH of 3.60 at 32,000 mPa · s (brookfield RVT, No. 6, 5 rpm).
제조예 2 : 마스크시트 침적액Production Example 2: Mask sheet Deposition liquid
제조예 2에 따른 마스크시트 침적액의 조성을 하기 표 6에 나타내었다. 하기 표 6의 A, B를 다른 용기에서 혼합하고 70℃로 승온하고, B를 A에 투입한 후 호모믹서 4000rpm으로 5분간 유화하고, C를 투입 후 호모믹서 4000rpm으로 3분간 유화하고, 45℃로 냉각 후 D를 투입하여 마스크시트 침적액을 제조하였으며, 제조된 마스크시트 침적액은 1,000 mPa·s (brookfield RVT, No 6, 5 rpm ) pH 6.5였다.The composition of the mask sheet immersion liquid according to Production Example 2 is shown in Table 6 below. A and B shown in Table 6 were mixed in different containers and heated to 70 DEG C, B was introduced into A, emulsified for 5 minutes at 4000 rpm in a homomixer, C was introduced and emulsified for 3 minutes at 4000 rpm in a homomixer, And D was added to prepare a mask sheet immersion liquid. The prepared mask sheet immersion liquid was 1,000 mPa.s (brookfield RVT, No. 6, 5 rpm) at a pH of 6.5.
제조예 3 : 보습 크림Production Example 3: Moisturizing cream
제조예 3에 따른 보습 크림의 조성을 하기 표 7에 나타내었다. 하기 표 7의 A, B를 다른 용기에서 혼합하고 70℃로 승온하고, B를 A에 투입한 후 호모믹서 4000rpm으로 5분간 유화하고, C를 투입 후 호모믹서 4000rpm으로 3분간 유화하고, 45℃로 냉각 후 D를 투입하여 보습 크림을 제조하였으며, 제조된 보습 크림은 60,000 mPa·s (brookfield RVT, No 6, 5 rpm) pH 5.5였다. The composition of the moisturizing cream according to Preparation Example 3 is shown in Table 7 below. A and B shown in Table 7 were mixed in different containers and heated to 70 DEG C, B was introduced into A, emulsified for 5 minutes at 4000 rpm in a homomixer, C was introduced and emulsified for 3 minutes at 4000 rpm in a homomixer, , And D was added thereto to prepare a moisturizing cream. The moisturizing cream prepared was 60,000 mPa · s (brookfield RVT, No. 6, 5 rpm) at a pH of 5.5.
제조예 4 : 겔 크림Preparation Example 4: Gel cream
제조예 4에 따른 겔 크림의 조성을 하기 표 8에 나타내었다. 하기 표 8의 A 를 혼합하고 70℃로 승온하고, B를 A에 투입한 후 호모믹서 4000rpm으로 5분간 유화하고, C를 투입 후 호모믹서 4000rpm으로 3분간 유화하여 겔 크림을 제조하였으며, 제조된 겔 크림은 백색의 크림 형태로, 점도 20000mPa.s, pH 5.50였다. The composition of the gel cream according to Production Example 4 is shown in Table 8 below. A of the following Table 8 was mixed and the temperature was raised to 70 DEG C and B was added to A, followed by emulsification for 5 minutes at 4000 rpm for a homomixer. C was injected and emulsified at 4000 rpm for 3 minutes to prepare a gel cream. The gel cream had a white creamy form, having a viscosity of 20,000 mPa.s and a pH of 5.50.
전술한 각 실시예에서 예시된 특징, 구조, 효과 등은 실시예들이 속하는 분야의 통상의 지식을 가지는 자에 의하여 다른 실시예들에 대해서도 조합 또는 변형되어 실시 가능하다. 따라서 이러한 조합과 변형에 관계된 내용들은 본 발명의 범위에 포함되는 것으로 해석되어야 할 것이다.The features, structures, effects, and the like illustrated in the above-described embodiments can be combined and modified in other embodiments by those skilled in the art to which the embodiments belong. Therefore, it should be understood that the present invention is not limited to these combinations and modifications.
Claims (14)
아크릴로일 모르폴린(acryloyl morpholine)을 10 내지 50 mol%,
전부 또는 일부 나트륨에 의해 염화된 아크릴산(sodium salt of acrylic acid)을 2 내지 25 mol% 및
가교제로서 적어도 하나 이상의 폴리에틸레닉 단량체(polyethylenic monomer)를 0.005 내지 1 mol% 포함하여 중합된 적어도 하나의 가교된 음이온 공중합체; 및
적어도 하나의 폴리글리세릴 지방산 에스테르(polyglyceryl fatty ester);를 포함하고,
유중 수형 에멀젼 중합 후 스프레이 건조하여 제조되는 분말 형태의 반 상호 침투성 격자형 중합체.
35 to 85 mol% of 2-acrylamido-2-methylpropane-sulfonic acid as a sodium salt of 2-acrylamido-2-
10 to 50 mol% of acryloyl morpholine,
2 to 25 mol% of sodium salt of acrylic acid, all or part of which is chlorinated by sodium,
At least one crosslinked anionic copolymer polymerized in the presence of 0.005 to 1 mol% of at least one polyethylenic monomer as a crosslinking agent; And
At least one polyglyceryl fatty ester,
A semi-interpenetrating lattice polymer in powder form prepared by spray-drying after polymerization in water-in-oil emulsion.
상기 가교된 음이온 공중합체는
상기 2-아크릴아미도-2-메틸프로판-솔폰산 나트륨(sodium salt of 2-acrylamido-2-methylpropane-sulfonic acid)을 40 내지 80 mol%,
상기 아크릴로일 모르폴린(acryloyl morpholine)을 15 내지 45 mol%,
상기 전부 또는 일부 나트륨에 의해 염화된 아크릴산(sodium salt of acrylic acid)을 2 내지 15 mol% 및
상기 가교제로서 적어도 하나 이상의 폴리에틸레닉 단량체를 0.005 내지 1 mol% 포함하여 중합된 중합체인 것을 특징으로 하는 분말 형태의 반 상호 침투성 격자형 중합체.
The method according to claim 1,
The crosslinked anionic copolymer
Acrylamido-2-methylpropane-sulfonic acid in an amount of 40 to 80 mol%, the amount of the 2-acrylamido-2-methylpropane-
15 to 45 mol% of the acryloyl morpholine,
2 to 15 mol% of sodium salt of acrylic acid, all or part of which is sodium chloride,
Wherein the cross-linking agent is a polymer polymerized with 0.005 to 1 mol% of at least one polyethylenic monomer as the cross-linking agent.
상기 가교된 음이온 공중합체는
상기 2-아크릴아미도-2-메틸프로판-솔폰산 나트륨(sodium salt of 2-acrylamido-2-methylpropane-sulfonic acid)을 50 내지 70 mol%,
상기 아크릴로일 모르폴린(acryloyl morpholine)을 20 내지 40 mol%,
상기 전부 또는 일부 나트륨에 의해 염화된 아크릴산(sodium salt of acrylic acid)을 2 내지 10 mol% 및
상기 가교제로서 적어도 하나 이상의 폴리에틸레닉 단량체를 0.005 내지 1 mol% 포함하여 중합된 중합체인 것을 특징으로 하는 분말 형태의 반 상호 침투성 격자형 중합체.
The method according to claim 1,
The crosslinked anionic copolymer
Acrylate, 2-acrylamido-2-methylpropane-sulfonic acid, 50 to 70 mol% of sodium salt of 2-acrylamido-
The acryloyl morpholine may be used in an amount of 20 to 40 mol%
2 to 10 mol% of sodium salt of acrylic acid by all or part of the sodium salt, and
Wherein the cross-linking agent is a polymer polymerized with 0.005 to 1 mol% of at least one polyethylenic monomer as the cross-linking agent.
상기 가교된 음이온 공중합체는
상기 가교제로서 적어도 하나 이상의 폴리에틸레닉 단량체(polyethylenic monomer)를 0.005 내지 1 mol% 포함하여 중합된 중합체인 것을 특징으로 하는 분말 형태의 반 상호 침투성 격자형 중합체.
The method according to claim 1,
The crosslinked anionic copolymer
Wherein the cross-linking agent is a polymer that is polymerized with 0.005 to 1 mol% of at least one polyethylenic monomer.
상기 가교된 음이온 공중합체는
상기 가교제로서 적어도 하나 이상의 폴리에틸레닉 단량체(polyethylenic monomer)를 0.01 내지 0.4 mol% 포함하여 중합된 중합체인 것을 특징으로 하는 분말 형태의 반 상호 침투성 격자형 중합체.
The method according to claim 1,
The crosslinked anionic copolymer
Wherein the cross-linking agent is a polymer polymer comprising 0.01 to 0.4 mol% of at least one polyethylenic monomer as the cross-linking agent.
상기 폴리에틸레닉 단량체(polyethylenic monomer)는
메틸렌비스아크릴아미드(methylene bis acrylamide), 에틸렌글리콜디메타크릴레이트(ethylene glycol dimethacrylate), 디에틸렌글리콜 디메타크릴레이트(diethylene glycol dimethacrylate), 트리알릴아민(triallylamine), 트리메틸올프로판 트리(메타)아크릴레이트(trimethylolpropane tri(meth)acrylate), 디알릴우레아(diallyl urea), 테트라알릴옥시에탄(tetra allyl oxy ethane), 디알릴옥시아세트산(diallyl oxy acetic acid), 알릴펜타에리트리톨(allyl penta erythritol), 알릴슈크로오스(allyl sucrose) 및 트리메틸올프로판 디알릴에테르(trimethylolpropane diallyl ether)로 구성되는 군에서 선택되는 적어도 하나 이상을 포함하는 것을 특징으로 하는 분말 형태의 반 상호 침투성 격자형 중합체.
The method according to claim 1,
The polyethylenic monomer may be selected from the group consisting of
(Meth) acrylate, methylene bis acrylamide, ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triallylamine, trimethylolpropane tri (meth) acrylate, Trimethylolpropane tri (meth) acrylate, diallyl urea, tetra allyl oxy ethane, diallyl oxyacetic acid, allyl penta erythritol, Wherein the polymer comprises at least one member selected from the group consisting of allyl sucrose and trimethylolpropane diallyl ether.
상기 폴리에틸레닉 단량체(polyethylenic monomer)는
메틸렌비스아크릴아미드(methylene bis acrylamide), 트리알릴아민(triallylamine) 또는 이들의 혼합물을 포함하는 것을 특징으로 하는 분말 형태의 반 상호 침투성 격자형 중합체.
The method according to claim 1,
The polyethylenic monomer may be selected from the group consisting of
A semi-interpenetrating lattice polymer in the form of a powder, characterized in that it comprises methylene bis acrylamide, triallylamine or mixtures thereof.
상기 반 상호 침투성 격자형 중합체는
상기 폴리글리세릴 지방산 에스테르를 상기 가교된 음이온 공중합체를 중합한 유중 수형 에멀젼에 첨가한 후 스프레이 건조하여 제조되는 것을 특징으로 하는 분말 형태의 반 상호 침투성 격자형 중합체.
The method according to claim 1,
The semi-interpenetrating lattice polymer
Wherein the polyglyceryl fatty acid ester is added to a water-in-oil type emulsion obtained by polymerizing the cross-linked anionic copolymer, followed by spray drying, thereby producing a semi-interpenetrating lattice polymer in powder form.
상기 반 상호 침투성 격자형 중합체는
상기 폴리글리세릴 지방산 에스테르 및 상기 가교된 음이온 공중합체를 중합한 유중 수형 에멀젼을 동시에 스프레이 건조하여 제조되는 것을 특징으로 하는 분말 형태의 반 상호 침투성 격자형 중합체.
The method according to claim 1,
The semi-interpenetrating lattice polymer
Wherein the polyglyceryl fatty acid ester and the cross-linked anionic copolymer are prepared by simultaneously spray-drying a water-in-oil type emulsion obtained by polymerizing the polyglyceryl fatty acid ester and the crosslinked anionic copolymer.
상기 반 상호 침투성 격자형 중합체는
상기 적어도 하나의 가교된 음이온 공중합체를 70 내지 90%,
상기 적어도 하나의 폴리글리세릴 지방산 에스테르를 4 내지 20% 및
물, 계면활성제, 오일 및 무기물 입자를 포함하는 공정상 요구되는 기술적 첨가제를 10% 이하로 포함하는 것을 특징으로 하는 분말 형태의 반 상호 침투성 격자형 중합체.
The method according to claim 1,
The semi-interpenetrating lattice polymer
70 to 90% of said at least one crosslinked anionic copolymer,
4 to 20% of said at least one polyglyceryl fatty acid ester and
Characterized in that it comprises less than 10% of the technical additive required in the process, including water, surfactants, oils and mineral particles.
상기 반 상호 침투성 격자형 중합체는
상기 적어도 하나의 가교된 음이온 공중합체를 75 내지 90%,
상기 적어도 하나의 폴리글리세릴 지방산 에스테르를 5 내지 10% 및
물, 계면활성제, 오일 및 무기물 입자를 포함하는 공정상 요구되는 기술적 첨가제를 10% 이하로 포함하는 것을 특징으로 하는 분말 형태의 반 상호 침투성 격자형 중합체.
The method according to claim 1,
The semi-interpenetrating lattice polymer
75 to 90% of said at least one crosslinked anionic copolymer,
5 to 10% of said at least one polyglyceryl fatty acid ester and
Characterized in that it comprises less than 10% of the technical additive required in the process, including water, surfactants, oils and mineral particles.
상기 반 상호 침투성 격자형 중합체는
수상(water phase)을 포함하는 화장품, 약제 또는 피부약제 조성물에 포함되어 증점 또는 안정화를 위하여 사용되는 것을 특징으로 하는 분말 형태의 반 상호 침투성 격자형 중합체.
The method according to claim 1,
The semi-interpenetrating lattice polymer
Characterized in that it is contained in a cosmetic, pharmaceutical or dermopharmaceutical composition comprising a water phase and is used for thickening or stabilizing the semi-interpenetrating lattice polymer in powder form.
12. A cosmetic, pharmaceutical or dermatological composition comprising from 0.1 to 5% of a semi-interpenetrating lattice polymer in powder form according to any one of claims 1 to 11.
상기 조성물은 밀크(milk), 로션(lotion), 크림(cream), 비누(soap), 목욕폼(foam bath), 밤(balm), 샴푸(shampoo), 컨디셔너(conditioner) 또는 스프레이(spray) 형태를 포함하는 것을 특징으로 하는 조성물.
14. The method of claim 13,
The composition may be in the form of a milk, a lotion, a cream, a soap, a foam bath, a balm, a shampoo, a conditioner or a spray ≪ / RTI >
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| WO2021060869A1 (en) * | 2019-09-24 | 2021-04-01 | 주식회사 엘지생활건강 | Microparticle-structured thickener having improved sensation of use |
| CN114423403A (en) * | 2019-09-24 | 2022-04-29 | 株式会社Lg生活健康 | Thickener having fine particle structure with improved feeling in use |
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| WO2021060869A1 (en) * | 2019-09-24 | 2021-04-01 | 주식회사 엘지생활건강 | Microparticle-structured thickener having improved sensation of use |
| CN114423403A (en) * | 2019-09-24 | 2022-04-29 | 株式会社Lg生活健康 | Thickener having fine particle structure with improved feeling in use |
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