KR101298275B1 - Improved polyamide compound and its method of manufacture - Google Patents
Improved polyamide compound and its method of manufacture Download PDFInfo
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- KR101298275B1 KR101298275B1 KR1020110109043A KR20110109043A KR101298275B1 KR 101298275 B1 KR101298275 B1 KR 101298275B1 KR 1020110109043 A KR1020110109043 A KR 1020110109043A KR 20110109043 A KR20110109043 A KR 20110109043A KR 101298275 B1 KR101298275 B1 KR 101298275B1
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
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- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
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Abstract
본 발명은 개선된 폴리아마이드 화합물과 그의 제조방법에 관한 것으로 본 발명에 따른 개선된 폴리아마이드 화합물은 아미노산의 한 종류인 아스탐산의 중합체인 생분해성 고분자 폴리숙신이미드에 유기계 자외선 차단 화합물을 도입한 화합물로 신규한 자외선 차단제로 사용될 수 있다. The present invention relates to an improved polyamide compound and a method for preparing the same, wherein the improved polyamide compound according to the present invention is obtained by introducing an organic sunscreen compound into a biodegradable polymer polysuccinimide which is a polymer of asamic acid, which is a kind of amino acid. It can be used as a novel sunscreen as a compound.
Description
본 발명은 개선된 폴리아마이드와 그의 제조방법으로, 보다 상세하게는 자외선 차단제로 사용될 수 있는 개선된 폴리아마이드 와 그의 제조방법에 관한 것이다.The present invention relates to an improved polyamide and a method for producing the same, and more particularly, to an improved polyamide and a method for producing the same, which can be used as a sunscreen.
피부의 생리적인 자연노화와 햇빛에 의한 자외선의 노출 등 환경적인 요인들로 인해 우리 몸의 피부는 노화를 일으킨다. 피부의 노화는 주름의 증가, 처짐 및 이완 등과 밀접하게 관련되어 있는데, 특히, 화장품과 관련된 피부노화의 원인 중 대부분은 자외선에 대한 지속적인 노출이라고 할 수 있다. 이로 인해서 깊은 주름이 생기고, 피부가 처지며, 균일한 반점(기미)들이 생성되어 외관을 해치게 된다.Due to environmental factors such as physiological natural aging of the skin and exposure to ultraviolet rays by sunlight, the skin of our body causes aging. Aging of the skin is closely related to wrinkles, sagging and relaxation. In particular, most of the causes of skin aging associated with cosmetics are continuous exposure to ultraviolet rays. This results in deep wrinkles, sagging skin, and even spots that can spoil the appearance.
시간이 갈수록 증가하는 유해한 태양광선에 노출되는 집단에서 자외선 차단제에 대한 수요가 지속적으로 증가하고 있는 가운데, 반복적인 일광 노출은 광노화된(photoaged) 피부로 피부 변화를 야기할 수 있다. 광노화된 피부에서 보여지는 임상적 변화는 신체의 태양광선 차단 부위에서 통상적으로 노화된 피부의 변화와는 상이한데 이는 주름의 증가, 탄력섬유증, 색소 변화, 전암성 및 암성 피부 병변이 포함된다.As the demand for sunscreens continues to grow in populations exposed to harmful sunlight, which is increasing over time, repeated sun exposure can cause skin changes to photoaged skin. The clinical changes seen in photoaged skin differ from the changes in skin that are normally aged at the sun block of the body, including increased wrinkles, elastic fibrosis, pigmented changes, precancerous and cancerous skin lesions.
이러한 현상을 조직학적으로 살펴보면, 피부의 지속적인 자외선 노출로 표피가 얇아지고, 진피의 두께도 감소하며, 피부에 존재하는 탄력섬유의 주성분인 엘라스틴이 변형되어 진피의 상층과 중간층에 거대분자를 형성한 "엘라스토틱 (Elastotic)"이라는 물질이 축적되게 된다. 이는 탄력섬유의 정상적인 기능을 저해함으로써, MMPs(matrixmetalloproteinases)의 활성에 의한 콜라겐의 손실과 더불어 탄력성이 결여된 주름진 피부유형을 유발하게 된다. Histologically, the skin is thinned due to the continuous UV exposure, the thickness of the dermis is reduced, and elastin, the main component of the elastic fibers present in the skin, is deformed to form macromolecules in the upper and middle layers of the dermis. A substance called "Elastotic" accumulates. This inhibits the normal function of the elastic fibers, causing collagen loss due to the activity of matrix metalloproteinases (MMPs) and wrinkled skin type lacking elasticity.
따라서, 가장 중요한 UV-A 및 UV-B 및 단파장(UVC)의 조사량 증가가 동반될 것으로 예상되는 지구 오존층의 추가 고갈의 견지에서, 훨씬 더 강력한 자외선차단 화학물질 및 이들을 함유하는 제제, 및 그의 보다 용이하고 경제적으로 보다 유리한 화학 합성법의 개발에 대한 요구가 존재한다. Thus, in view of the further depletion of the global ozone layer, which is expected to be accompanied by the most significant increase in the dose of UV-A and UV-B and short wavelength (UVC), much stronger sunscreen chemicals and formulations containing them, and their more There is a need for the development of chemical synthesis methods that are easier and economically more advantageous.
이를 해결하기 위한 일차적인 방법으로 자외선(특히 UV-A, B)으로부터 피부를 보호하기 위하여 자외선 차단 화합물에 관한 연구가 많이 진행되어 왔으며, 특히 p-아미노벤조산(aminobenzoic acid) 유도체, 벤질리데네캠포(benzylidenecamphor) 유도체, 시남산(cinnamic acid) 유도체, 벤조트리아졸(benzotriazole) 유도체와 같은 많은 유기계 자외선차단제가 개발되어 사용되고 있다. In order to solve this problem, many studies have been conducted on sunscreen compounds to protect the skin from ultraviolet rays (especially UV-A and B), and especially p-aminobenzoic acid derivatives and benzylidenecampo. Many organic sunscreen agents, such as (benzylidenecamphor) derivatives, cinnamic acid derivatives, benzotriazole derivatives have been developed and used.
하지만 이러한 유기계 자외선차단제들은 화장료로 사용했을 때 광안정도에서 문제가 발견되고 있으며, 또한 피부에 흡수되어 자체가 자극을 일으키거나 광반응에 의한 생성물, 또는 피부나 눈을 자극하고 접촉성 피부염, 피부의 광과민성 반응을 유발하는 등의 문제점이 등으로 인하여 안전성에 심각한 문제를 야기하기도 하므로 대부분의 유기계 자외선차단제는 사용에 있어서 많은 제약을 가지고 있다.However, these organic sunscreens have been found to have problems in light stability when used as cosmetics, and they are also absorbed by the skin, causing irritation or photoreaction, or irritating the skin or eyes, causing contact dermatitis, Most of the organic sunscreens have many restrictions in use because they may cause serious problems in safety due to such problems as causing photosensitive reactions.
상기와 같은 유기계 자외선차단제의 문제점을 해결하기 위하여 한국공개특허공보 2010-0060476에 개시된 것과 같이 실리콘 분자를 치환한 자외선차단제의 개발이 보고되었는데, 이는 주로 저분자의 실리콘 물질을 유기계 자외선차단제에 도입함으로써 유기용매에 대한 용해도를 증진시키고 광안정도를 증가시킬 목적에서 수행되었으나 피부투과에 의한 안전성 문제를 만족스럽게 해결하지는 못하였다.In order to solve the problems of the organic sunscreen as described above has been reported the development of a sunscreen substituted with silicon molecules as disclosed in Korea Patent Publication No. 2010-0060476, which is mainly by introducing a low molecular weight silicone material into the organic sunscreen Although it was performed to improve solubility in solvents and to increase light stability, it did not satisfactorily solve the safety problem due to skin penetration.
따라서 본 발명자들은 종래의 유기계 자외선 차단제의 단점을 극복하기 위해 생분해성 고분자에 불안정한 유기계 자외선차단제를 도입함으로써 유기계 자외선차단제가 피부로 흡수되는 것을 방지하며, 자외선 차단제의 부작용을 없애는 새로운 자외선차단제를 개발할 수 있음에 착안하여 본 발명을 완성하였다. Therefore, the present inventors can introduce an organic sunscreen agent that is unstable to a biodegradable polymer to overcome the shortcomings of the conventional organic sunscreen, thereby preventing the organic sunscreen from being absorbed into the skin and developing a new sunscreen that eliminates the side effects of the sunscreen. With this in mind, the present invention has been completed.
본 발명은 생분해성 고분자인 폴리숙신이미드에 아릴아미노화합물을 도입하여 화학적 특성을 개선시킨 폴리아마이드 화합물 및 이의 제조방법을 제공한다.The present invention provides a polyamide compound having improved chemical properties by introducing an arylamino compound into a polysuccinimide, a biodegradable polymer, and a method for preparing the same.
또한 본 발명은 유기 자외선 차단제의 단점인 피부 흡수와 광불안전성을 개선한 본 발명에 따른 개선된 폴리아마이드 화합물을 포함하는 자외선 차단제 조성물을 제공한다.The present invention also provides a sunscreen composition comprising the improved polyamide compound according to the invention which improves skin absorption and photosafety which is a disadvantage of organic sunscreens.
또한 본 발명에 따른 폴리아마이드 화합물을 자외선 차단제로 함유하는 화장료 조성물을 제공한다.It also provides a cosmetic composition containing the polyamide compound according to the invention as a sunscreen.
본 발명은 개선된 폴리아마이드 화합물 및 이의 제조방법에 관한 것으로, 상세하게는 본 발명에 따른 개선된 폴리아마이드 화합물은 하기 화학식 1로 표시된다.The present invention relates to an improved polyamide compound and a method for preparing the same, in detail, the improved polyamide compound according to the present invention is represented by the following Chemical Formula 1.
[화학식 1][Formula 1]
[상기 화학식 1에서,[In Formula 1,
R1 은 독립적으로 수소이며, R은 수소, 할로겐, C1-C7알킬, C6-C12의 아릴이며, p는 0-4의 정수이며, p가 2이상인 경우 R은 동일하거나 상이할 수 있으며, l 은 500-800의 정수이다.R 1 is independently hydrogen, R is hydrogen, halogen, C 1 -C 7 alkyl, C 6 -C 12 aryl, p is an integer of 0-4, and when p is 2 or more R is the same or different. Where l is an integer from 500 to 800.
또한 본 발명은 폴리숙신이미드를 하기 화학식 3으로 표시되는 아릴아미노화합물을 반응시켜 상기 화학식 1을 얻는 단계를 포함하는 개선된 폴리아마이드 화합물의 제조방법을 제공한다.In another aspect, the present invention provides a method for preparing an improved polyamide compound comprising the step of reacting a polysuccinimide with an arylamino compound represented by the following formula (3).
[화학식 2][Formula 2]
상기 화학식 3에서,In Formula 3,
R1은 서로 독립적으로 수소이며 R은 수소, 할로겐, C1-C7알킬, C6-C12의 아릴이며, p는 0-4의 정수이다.R 1 is independently of each other hydrogen, R is hydrogen, halogen, C 1 -C 7 alkyl, C 6 -C 12 aryl, p is an integer from 0-4.
상기 화학식 2으로 표시되는 아릴아미노 화합물은 아미노벤조익산인 것이 바람직하다. The arylamino compound represented by Formula 2 is preferably aminobenzoic acid.
상기 중합 반응의 온도는 중합 중 반응의 안정성과 중합도를 높이고 부생성물의 생성을 최소화하기 위한 측면에서 30 내지 100℃이며 바람직하게는 30~70℃이다. The temperature of the polymerization reaction is 30 to 100 ℃ and preferably 30 to 70 ℃ in terms of increasing the stability and polymerization degree of the reaction during polymerization and minimizing the formation of by-products.
또한 반응의 용매로는 알코올류, 에테르류, 케톤류, 할로겐화 탄화수소류, 지방족 유기산류 또는 이들의 혼합용매로 선택되며, 바람직하게는 메탄올, 에탄올, 프로판올, 아세토나이트릴, 디옥산, 에틸아세테이트, 테트라하이드로퓨란, 디에틸에테르, 디클로로메탄, 디메틸술폭사이드, 디메틸포름아미드, 디메틸아세트아미드 및 메틸피롤리돈으로부터 선택되는 1종 이상을 사용하고, 더욱 바람직하게는 메탄올, 에탄올, 프로판올, 아세토니트릴, 디옥산, 에틸아세테이트, 테트라하이드로퓨란, 디에틸에테르 또는 디클로로메탄 등의 끊는점이 낮은 단일 또는 두 가지 이상의 혼합용매를 사용한다.The reaction solvent may be selected from alcohols, ethers, ketones, halogenated hydrocarbons, aliphatic organic acids or mixed solvents thereof, preferably methanol, ethanol, propanol, acetonitrile, dioxane, ethyl acetate, tetra Hydrofuran, diethyl ether, dichloromethane, dimethyl sulfoxide, dimethylformamide, dimethylacetamide and methylpyrrolidone are used, and more preferably methanol, ethanol, propanol, acetonitrile, di Single or two or more mixed solvents having a low breaking point such as oxane, ethyl acetate, tetrahydrofuran, diethyl ether or dichloromethane are used.
또한 본 발명은 본 발명에 따른 개선된 폴리아마이드 화합물을 포함하는 자외선 차단제를 제공한다.The present invention also provides a sunscreen comprising an improved polyamide compound according to the invention.
본 발명의 개선된 폴리아마이드 화합물은 아미노산의 한 종류인 아스탐산의 중합체인 생분해성 고분자 폴리숙신이미드에 유기계 자외선 차단 물질인 아릴아미노 화합물을 도입하여 제조하였다.The improved polyamide compound of the present invention was prepared by introducing an organic sunscreen material, an arylamino compound, into a biodegradable polymer polysuccinimide, which is a polymer of asamic acid, a type of amino acid.
따라서 본 발명의 개선된 폴리아마이드 화합물은 생분해성 고분자인 폴리숙신이미드를 사용하여, 나노 계열의 자외선 차단제의 단점인 피부 내로의 침투율을 낮추고, 아릴아미노 화합물인 자외선 차단물질의 안전성을 향상시켜, 새로운 유기 자외선 차단 물질로 사용되어 질 수 있다.Therefore, the improved polyamide compound of the present invention uses a biodegradable polymer polysuccinimide to lower the penetration rate into the skin, which is a disadvantage of the nano-based sunscreen agent, and to improve the safety of the sunscreen material, an arylamino compound, It can be used as a new organic sunscreen.
또한 본 발명은 본 발명에 따른 개선된 폴리아마이드 화합물을 포함하는 화장료 조성물을 제공한다.The invention also provides a cosmetic composition comprising the improved polyamide compound according to the invention.
화장료 조성물에 포함되는 본 발명에 따른 개선된 폴리아마이드 화합물은 화장료 전체 조성물 총 중량에 대하여 0.1 ~ 20중량%의 양 보다 바람직하게는 1 ~ 10중량%의 양으로 포함될 수 있다. 본 발명에 따른 개선된 폴리아마이드 화합물의 함량이 0.1중량%미만일 경우에는 자외선 차단효과가 미미하고 20중량%초과일 경우에는 제형상 어려움이 발생할 수 있기 때문이다.The improved polyamide compound according to the present invention contained in the cosmetic composition may be included in an amount of preferably 1 to 10% by weight rather than an amount of 0.1 to 20% by weight based on the total weight of the cosmetic composition. If the content of the improved polyamide compound according to the present invention is less than 0.1% by weight because the sunscreen effect is insignificant and when the content of more than 20% by weight may cause difficulties in formulation.
본 발명은 생분해성 고분자인 폴리숙신이미드에 유기계 자외선 차단 화합물인 p-aminobenzoic acid를 도입하여 폴리아마이드 화합물의 특성을 개선한 것이다. The present invention improves the properties of polyamide compounds by introducing p-aminobenzoic acid, an organic UV blocking compound, into polysuccinimide, a biodegradable polymer.
본 발명에 따른 개선된 폴리아마이드 화합물을 포함하는 자외선 차단제와 화장료 조성물은 광과 피부에 대한 안정성이 우수하며 유기용매에 대한 용해도도 향상되는 장점을 가진다. The sunscreen and the cosmetic composition including the improved polyamide compound according to the present invention have excellent stability to light and skin and have solubility in organic solvents.
도 1은 실시예에서 제조된 화합물의 IR 스펙트럼이다.1 is an IR spectrum of the compound prepared in the Examples.
이하, 하기의 실시예를 통하여 본 발명을 상세하게 설명하지만, 본 발명이 이 예들에 의하여 한정되는 것은 아니다. Hereinafter, the present invention will be described in detail by way of the following examples, but the present invention is not limited to these examples.
[실시예] 개선된 폴리아마이드 화합물(PA)의 제조EXAMPLES Preparation of Improved Polyamide Compounds (PA)
Polysuccinimide 2g을 Dimethylformaldehyde(DMF) 30mL, para-aminobenzoic acid 2.1 g을 20mL에 용해시킨다. PSI solution의 온도를 30~70℃로 맞추고 dropping fennel을 이용하여 PABA/DMF solution을 PSI solution에 2시간에 걸쳐 서서히 드랍핑 후 24시간 동안 교반시켰다. 반응 종료 후 MeOH나 Ether 혹은 mixing solvent에 침전 및 washing 후 여과하여 얻어진 파우더를 실온에서 24시간동안 건조 후 PA 2.3g을 하얀색 고체로 수득하였다.Dissolve 2 g of Polysuccinimide in 30 mL of Dimethylformaldehyde (DMF) and 2.1 g of para-aminobenzoic acid in 20 mL. The temperature of the PSI solution was adjusted to 30-70 ° C., and the dropping fennel was used to drop the PABA / DMF solution into the PSI solution over 2 hours and then stirred for 24 hours. After the completion of the reaction, precipitated and washed with MeOH or Ether or mixing solvent, and the powder obtained by filtration was dried for 24 hours at room temperature to give 2.3g of PA as a white solid.
1H-NMR (500 MHz, DMSO-d6): δ 8.11 (s, 1H, Benzene), 7.26 (s, 1H, Benzene), 6.48 (s, 1H, Benzene), 5.12 ~ 5.34 (m, 1H, succinimide), 2.90(m, 1H, succinimide), 3.1 ~ 3.4 (m, 2H, succinimide), 2.69 ~ 73(m, 2H, succinimide) 1 H-NMR (500 MHz, DMSO-d 6 ): δ 8.11 (s, 1H, Benzene), 7.26 (s, 1H, Benzene), 6.48 (s, 1H, Benzene), 5.12 to 5.34 (m, 1H, succinimide), 2.90 (m, 1H, succinimide), 3.1 to 3.4 (m, 2H, succinimide), 2.69 to 73 (m, 2H, succinimide)
Claims (7)
[화학식 1]
상기 화학식 1에서,
R1은 수소이며, R은 할로겐, C1-C7알킬, C6-C12의 아릴이며, p는 0-4의 정수이며, p가 2이상인 경우 R은 동일하거나 상이할 수 있으며, l은 500-800의 정수이다.Polyamide compound represented by the following formula (1).
[Formula 1]
In Chemical Formula 1,
R 1 is hydrogen, R is halogen, C 1 -C 7 alkyl, C 6 -C 12 aryl, p is an integer of 0-4, and when p is 2 or more, R may be the same or different, l Is an integer from 500 to 800.
R1 이 수소인 폴리아마이드 화합물.The method of claim 1,
A polyamide compound wherein R 1 is hydrogen.
[화학식 1]
[화학식 2]
상기 화학식 1 및 화학식 2에서,
R1은 수소, C1-C7알킬이며 R은 할로겐, C1-C7알킬, C6-C12의 아릴이며, p는 0-4의 정수이며, l은 500-800의 정수이다.A method for producing a polyamide compound, comprising the step of reacting a polysuccinimide with an arylamino compound represented by the following formula (2) to obtain the following formula (1).
[Formula 1]
(2)
In the above formulas (1) and (2)
R 1 is hydrogen, C 1 -C 7 alkyl, R is halogen, C 1 -C 7 alkyl, C 6 -C 12 aryl, p is an integer of 0-4, and l is an integer of 500-800.
상기 아릴아미노 화합물은 아미노벤조익산인 폴리아마이드 화합물의 제조방법.The method of claim 3,
The arylamino compound is a method for producing a polyamide compound is aminobenzoic acid.
상기 반응의 온도는 30 내지 100℃에서 수행되는 폴리아마이드 화합물의 제조방법.The method of claim 3,
The temperature of the reaction is a method for producing a polyamide compound is carried out at 30 to 100 ℃.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11240949A (en) * | 1997-01-30 | 1999-09-07 | Mitsui Chem Inc | Crosslinked polymer and its production |
| JP2002069184A (en) | 2000-06-12 | 2002-03-08 | Mitsui Chemicals Inc | Polymer and method of producing the same |
| JP2002194078A (en) | 2000-12-27 | 2002-07-10 | Mitsui Chemicals Inc | Polymer and its production method |
| JP2007191643A (en) | 2006-01-20 | 2007-08-02 | Mitsui Chemicals Inc | Polyamino acid derivative imparted with fixability to living body |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11240949A (en) * | 1997-01-30 | 1999-09-07 | Mitsui Chem Inc | Crosslinked polymer and its production |
| JP2002069184A (en) | 2000-06-12 | 2002-03-08 | Mitsui Chemicals Inc | Polymer and method of producing the same |
| JP2002194078A (en) | 2000-12-27 | 2002-07-10 | Mitsui Chemicals Inc | Polymer and its production method |
| JP2007191643A (en) | 2006-01-20 | 2007-08-02 | Mitsui Chemicals Inc | Polyamino acid derivative imparted with fixability to living body |
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