KR101672794B1 - Novel silicone compound and its preparation method, and surfactant and cosmetics comprising the same - Google Patents
Novel silicone compound and its preparation method, and surfactant and cosmetics comprising the same Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 38
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 36
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 22
- 239000002537 cosmetic Substances 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims abstract description 8
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 7
- 229920000570 polyether Polymers 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- -1 dimethylsiloxane compound Chemical class 0.000 claims description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 claims description 3
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- PQPVPZTVJLXQAS-UHFFFAOYSA-N hydroxy-methyl-phenylsilicon Chemical class C[Si](O)C1=CC=CC=C1 PQPVPZTVJLXQAS-UHFFFAOYSA-N 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 7
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 abstract description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 7
- 239000002994 raw material Substances 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 230000001804 emulsifying effect Effects 0.000 description 4
- 150000003377 silicon compounds Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241000234435 Lilium Species 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 229940008099 dimethicone Drugs 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920001843 polymethylhydrosiloxane Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
- C08G77/08—Preparatory processes characterised by the catalysts used
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- Life Sciences & Earth Sciences (AREA)
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- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
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Abstract
본 발명은 신규한 실리콘 화합물 및 그 제조방법, 및 그를 포함하는 계면활성제 및 화장품에 관한 것으로, 더욱 상세하게는 실록산 주쇄에 폴리에테르기, 폴리알킬기 및 페닐기를 포함함으로써 우수한 상용성과 유화력을 가지는 신규한 실리콘 화합물 및 그 제조방법, 및 그를 포함하는 계면활성제 및 화장품에 관한 것이다.The present invention relates to a novel silicone compound, a method for producing the same, a surfactant and a cosmetic product containing the same, and more particularly to a novel silicone compound containing a polyether group, a polyalkyl group and a phenyl group in a siloxane main chain, A silicone compound, a process for producing the same, and a surfactant and a cosmetic product containing the same.
Description
본 발명은 신규한 실리콘 화합물 및 그 제조방법, 및 그를 포함하는 계면활성제 및 화장품에 관한 것으로, 더욱 상세하게는 실록산 주쇄에 폴리에테르기, 폴리알킬기 및 페닐기를 포함함으로써 우수한 상용성과 유화력을 가지는 신규한 실리콘 화합물 및 그 제조방법, 및 그를 포함하는 계면활성제 및 화장품에 관한 것이다.The present invention relates to a novel silicone compound, a method for producing the same, a surfactant and a cosmetic product containing the same, and more particularly to a novel silicone compound containing a polyether group, a polyalkyl group and a phenyl group in a siloxane main chain, A silicone compound, a process for producing the same, and a surfactant and a cosmetic product containing the same.
화장품 제형에 계면 활성제로서 사용되는 실리콘 화합물은 하기와 같은 구조식을 가지는 것이 대부분이다.
Most of the silicone compounds used as surfactants in cosmetic formulations have the following structural formula.
이러한 구조의 계면 활성제용 실리콘 화합물의 제조는 미국특허 제3,979,419호, 제3,979,420호, 제3,980,688호, 제4,016,000호, 제4,018,723호, 제4,147,847호, 제4,885,379호 외의 많은 특허에서 다루고 있다. 이들 특허에서는 상기의 구조에서 x, y, m, n의 비율을 달리 함으로써 다양한 목적을 가진 다양한 구조의 계면 활성제용 실리콘 화합물을 제조하였다. The preparation of silicone compounds for surfactants of this structure is described in many patents other than U.S. Patent Nos. 3,979,419, 3,979,420, 3,980,688, 4,016,000, 4,018,723, 4,147,847, 4,885,379. In these patents, silicon compounds for various surfactants having various purposes are prepared by varying the ratio of x, y, m and n in the above structure.
그러나 이러한 종래의 실리콘 화합물들은 그 유화력 및 상용성에 있어서 개선의 여지를 지니고 있으며, 따라서 보다 개선된 유화력 및 상용성을 가지는 새로운 구조의 계면 활성제용 실리콘 화합물의 개발이 요청되고 있다.However, such conventional silicone compounds have room for improvement in their emulsifying power and compatibility, and therefore, there is a demand for the development of a silicone compound for a surfactant having a new structure having improved emulsifying power and compatibility.
본 발명은 상기한 바와 같은 종래 기술의 문제점을 해결하고자 한 것으로서, 기존의 실리콘 계면 활성제의 역할을 충실히 수행하면서도 추가적으로 우수한 상용성과 유화력을 가지는 실리콘 화합물 및 그 제조방법, 및 그를 포함하는 계면활성제 및 화장품을 제공하는 것을 기술적 과제로 한다.Disclosure of Invention Technical Problem [8] Accordingly, the present invention has been made in an effort to solve the problems of the prior art as described above, and an object of the present invention is to provide a silicone compound having excellent compatibility and emulsifying power while faithfully performing the role of a conventional silicone surfactant, And to provide a method of manufacturing the same.
상기한 기술적 과제를 해결하고자 본 발명은, 하기의 화학식 1을 가지는 신규한 실리콘 화합물을 제공한다:In order to solve the above-mentioned technical problems, the present invention provides a novel silicone compound having the following Formula 1:
[화학식 1][Chemical Formula 1]
상기 화학식 1에서 In Formula 1,
x는 10 ~ 300의 정수이고;x is an integer from 10 to 300;
R1은 CH3 또는 C6H5이고, y는 1 ~ 10의 정수이며;R 1 is CH 3 or C 6 H 5 and y is an integer from 1 to 10;
R2는
R3는 C2H4-(CH2)o-CH3 (여기서 o는 1 ~ 27의 정수임)이고, w는 1 ~ 20의 정수이며;R 3 is C 2 H 4 - (CH 2 ) o -CH 3 (where o is an integer from 1 to 27) and w is an integer from 1 to 20;
x/(z+w)는 1 ~ 10 이다.x / (z + w) is 1 to 10.
상기한 본 발명의 화학식 1의 실리콘 화합물은, 바람직하게는 이하에서 설명하는 바와 같은 방법에 의해 제조될 수 있다. 따라서, 본 발명의 다른 측면에 따르면, 본 발명의 화학식 1의 실리콘 화합물 제조방법이 또한 제공된다.The silicone compound of the formula (1) of the present invention described above can be preferably produced by a method as described below. Therefore, according to another aspect of the present invention, there is also provided a process for preparing a silicon compound of formula (1) of the present invention.
본 발명에 따른 화학식 1의 실리콘 화합물 제조방법은, 1) 하기 화학식 2의 메틸-페닐-하이드로 폴리실록산과 하기 화학식 3의 불포화 폴리에테르를 하이드로실릴화 반응시키는 단계, 및 2) 상기 1) 단계의 반응결과물과 하기 화학식 4의 불포화 화합물을 반응시키는 단계를 포함한다:The method for producing a silicone compound of Chemical Formula 1 according to the present invention comprises the steps of 1) hydrosilylating a methyl-phenyl-hydrogen polysiloxane of Chemical Formula 2 and an unsaturated polyether of Chemical Formula 3, and 2) And reacting the resultant with an unsaturated compound of the following formula (4): < EMI ID =
[화학식 2](2)
(여기서 R은 CH3 또는 C6H5이고, x는 10 ~ 300의 정수이고, y는 1 ~ 10의 정수이며, z+w는 2 ~ 30의 정수이고, x/(z+w)는 1 ~ 10이다)(Wherein R is CH 3 or C 6 H 5 , x is an integer of 10 to 300, y is an integer of 1 to 10, z + w is an integer of 2 to 30, and x / (z + w) 1 to 10)
[화학식 3](3)
(여기서 R4는 H, CH3 또는 C(=O)CH3 이고, m은 5 ~ 30의 정수이며, n은 0 ~ 30의 정수이다)(Wherein R 4 is H, CH 3 or C (= O) CH 3 , m is an integer of 5 to 30, and n is an integer of 0 to 30)
[화학식 4][Chemical Formula 4]
(여기서 o는 1 ~ 27의 정수이다)(Where o is an integer from 1 to 27)
본 발명의 일 구체예에 따르면, 상기 화학식 2의 메틸-페닐-하이드로 폴리실록산은 디메틸실록산 화합물, 예컨대, 디메틸사이클로실록산; 페닐-메틸실록산 또는 디페닐실록산 화합물, 예컨대 페닐-메틸사이클로실록산 또는 디페닐사이클로실록산; 메틸-하이드로실록산 화합물, 예컨대 폴리메틸하이드로실록산; 및 말단제로서 헥사메틸다이실록산을 상기 화학식 2에 나타난 비율에 맞게 혼합하고, 산 또는 염기 촉매의 존재하에 10 ~ 80℃에서 중합시켜 제조될 수 있다.According to one embodiment of the present invention, the methyl-phenyl-hydropolysiloxane of Formula 2 is a dimethylsiloxane compound such as dimethylcyclosiloxane; Phenyl-methylsiloxane or diphenylsiloxane compounds such as phenyl-methylcyclosiloxane or diphenylcyclosiloxane; Methyl-hydrosiloxane compounds such as polymethylhydroxylsiloxane; And hexamethyldisiloxane as a terminal agent in the proportions shown in Formula 2 and polymerizing at 10 to 80 캜 in the presence of an acid or base catalyst.
중합이 종결되면 예컨대 소듐 카보네이트와 같은 중화제를 투입하여 촉매를 중화하고, 중화완료 후 여과한 뒤 및 진공감압을 통하여 환상구조의 휘발분을 제거하여 메틸-페닐-하이드로 폴리실록산을 수득한다. When the polymerization is completed, a neutralizing agent such as sodium carbonate is added to neutralize the catalyst. After completion of neutralization, the catalyst is filtrated and the volatile components in the cyclic structure are removed through vacuum depressurization to obtain methyl-phenyl-hydropolysiloxane.
본 발명에 따른 화학식 1의 실리콘 화합물 제조방법의 상기 1)단계에서는, 상기 설명한 바와 같이 하여 제조된 메틸-페닐-하이드로 폴리실록산과 과량의 화학식 3의 불포화 폴리에테르를 하이드로실릴화 반응시킨다. 이 하이드로실릴화 반응은 미국특허 제 4,031,044호에 개시된 절차에 따라 백금촉매의 존재 하에서 수행될 수 있으나, 이에 반드시 제한되는 것은 아니다. 이 반응은 통상 25 내지 100 ℃의 온도에서 5 내지 10 시간 동안 수행된다.In the above step 1) of the method for producing a silicone compound of formula (1) according to the present invention, the methyl-phenyl-hydropolysiloxane prepared as described above is excessively hydrosilylated with an unsaturated polyether of formula (3). This hydrosilylation reaction can be carried out in the presence of a platinum catalyst according to the procedure disclosed in U.S. Patent No. 4,031,044, but is not necessarily limited thereto. This reaction is usually carried out at a temperature of 25 to 100 DEG C for 5 to 10 hours.
본 발명에 따른 화학식 1의 실리콘 화합물 제조방법의 상기 2)단계에서는, 1) 단계에서 얻어진 반응결과물과 화학식 4의 불포화 화합물을 반응시켜 화학식 1의 실리콘 화합물을 제조한다. 이 단계의 반응은 통상 백금촉매와 같은 촉매의 존재 하에 25 내지 100 ℃의 온도에서 5 내지 10 시간 동안 수행되나, 이에 반드시 제한되는 것은 아니다.In the step 2) of the method for producing a silicon compound of formula (1) according to the present invention, the reaction product obtained in step (1) is reacted with an unsaturated compound of formula (4) to prepare a silicone compound of formula (1). The reaction of this step is usually carried out in the presence of a catalyst such as a platinum catalyst at a temperature of 25 to 100 DEG C for 5 to 10 hours, but this is not essential.
상기한 바와 같은 본 발명의 화학식 1의 실리콘 화합물은, 계면 활성제용으로 기존에 사용되어온 실리콘 화합물과 달리 측쇄에 폴리에테르기, 폴리알킬기 및 페닐기를 함께 가짐으로써 조성물 다른 유기원료와 우수한 상용성 및 유화력을 나타낼 수 있고, 이에 따라 계면 활성 성분으로서, 특히 화장품용 계면 활성 성분으로서 적합하게 사용될 수 있다.As described above, the silicone compound of the formula (1) of the present invention has polyether groups, polyalkyl groups and phenyl groups in the side chains unlike the silicone compounds conventionally used for surfactants, and thus has excellent compatibility with emulsifiers And thus can be suitably used as a surfactant component, particularly as a surfactant component for cosmetics.
따라서, 본 발명의 또 다른 측면에 따르면, 본 발명의 화학식 1의 실리콘 화합물을 특징적인 성분으로 포함하는 계면 활성제 조성물 및 화장품 조성물이 제공된다.Thus, according to another aspect of the present invention, there is provided a surfactant composition and a cosmetic composition comprising the silicone compound of the present invention as a characteristic component.
본 발명에 따른 실리콘 화합물을 계면활성제 성분으로 화장품 등에 사용하면 기존의 실리콘계 계면활성제에 비하여 우수한 상용성 및 유화력을 나타낼 수 있다.When the silicone compound according to the present invention is used as a surfactant component in cosmetics and the like, excellent compatibility and emulsifying power can be exhibited as compared with the conventional silicone surfactants.
이하, 본 발명을 실시예에 의해 상세히 설명한다. 단, 하기 실시예는 본 발명을 예시하는 것일 뿐, 본 발명의 내용이 하기 실시예에 의해 한정되는 것은 아니다. Hereinafter, the present invention will be described in detail with reference to examples. However, the following examples are illustrative of the present invention, and the contents of the present invention are not limited by the following examples.
실시예Example 1 One
질소가스관 및 에어 컨덴서, 교반기, 온도계, 히터가 설치되어 있는 4구 플라스크에 디메틸사이클로실록산 2960g, 디페닐사이클로폴리실록산 200g, 폴리메틸하이드로실록산 1200g 그리고 헥사메틸다이실록산 82g을 사입하여 혼합한 후 25℃로 승온하였다. 여기에 촉매로 황산 1.5g을 투입하고 60℃에서 6시간의 유지반응을 통하여 중합을 진행한 뒤, 소듐카보네이트 40g을 투입하고 2시간동안 교반하여 촉매를 중화하고 결과물을 여과한 다음, 결과물을 150℃에서 2시간 동안 10 토르(torr) 이하에서 진공 감압하여 휘발분을 제거하고, 메틸-페닐-하이드로 폴리실록산을 수득하였다.In a four-necked flask equipped with a nitrogen gas pipe, an air condenser, a stirrer, a thermometer and a heater, 2960 g of dimethylcyclosiloxane, 200 g of diphenylcyclopolysiloxane, 1200 g of polymethylhydrosiloxane and 82 g of hexamethyldisiloxane were mixed and mixed at 25 ° C Lt; / RTI > 1.5 g of sulfuric acid was added as a catalyst and polymerization was carried out at 60 ° C for 6 hours. After the polymerization was carried out, 40 g of sodium carbonate was added and stirred for 2 hours to neutralize the catalyst. The resulting product was filtered, Deg. C < / RTI > for 2 hours to remove the volatiles and obtain methyl-phenyl-hydropolysiloxane.
제조된 메틸-페닐-하이드로 폴리실록산 120g과 불포화폴리에테르 PKA-5003(에틸렌옥사이드 9몰, 일본유지사 제품) 240g, 이소프로필알코올(IPA) 300g을 투입하여 혼합한 후, 클로로플라틴산 1g을 투입하고 70℃로 승온하여 6시간 동안 하이드로실릴화 반응을 수행하였다. NMR 또는 IR 분석기기를 통하여 반응이 종결된 것을 확인한 후, 100℃로 승온하여 IPA를 제거하였다.120 g of the prepared methyl-phenyl-hydropolysiloxane, 240 g of unsaturated polyether PKA-5003 (9 mol of ethylene oxide, manufactured by Nippon Oil and Fats Co., Ltd.) and 300 g of isopropyl alcohol (IPA) were added thereto and mixed with 1 g of chloroplatinic acid And the temperature was raised to 70 DEG C to carry out hydrosilylation reaction for 6 hours. After confirming that the reaction was terminated through NMR or IR analyzer, the temperature was raised to 100 ° C to remove IPA.
상기의 방법으로 제조된 실리콘 화합물에 대한 NMR 분석 결과, 수득된 실리콘 화합물은 폴리알킬이 도입된 화학식 1의 구조를 가짐이 확인되었다 (화학식 1에서 R1은 페닐, R4는 CH3, x = 40, y = 1, z = 10, w=5, m = 9, n = 0, o = 13).As a result of NMR analysis of the silicon compound prepared by the above method, it was confirmed that the obtained silicone compound had the structure of the formula (1) wherein the polyalkyl was introduced (R 1 in the formula ( 1) is phenyl, R 4 is CH 3 , x = 40, y = 1, z = 10, w = 5, m = 9, n = 0, o = 13).
실시예Example 2 ~ 3 2 to 3
상기 실시예 1과 동일한 방법으로 각 원료의 투입량을 조절하여 z 및 w 값을 달리하는 실리콘 화합물들을 각각 제조하였다. NMR 분석을 통해, 수득된 실리콘 화합물들이 화학식 1의 구조를 가짐을 확인하였으며, 그 결과를 아래 표 1에 정리하였다.The amounts of each raw material were controlled in the same manner as in Example 1 to prepare silicone compounds having different z and w values. Through NMR analysis, it was confirmed that the obtained silicone compounds had the structure of Chemical Formula 1, and the results are summarized in Table 1 below.
[표 1][Table 1]
비교예Comparative Example 1 ~ 2 1-2
상기 실시예 1과 동일한 방법으로 제조하되 디페닐사이클로폴리실록산을 사용하지 않고, 각 원료의 투입량을 조절하여 z 및 w 값을 달리하는 화합물들을 각각 제조하였다. 이들 비교예 1 및 2는 각각 기존 상용품 계면활성제인 Abil EM 90(Deggusa 사 제품) 및 KF-6028(Shin-etsu 사 제품)에서 사용되는 물질들에 대응하는 것들이다. NMR 분석을 통해, 수득된 실리콘 화합물들이 페닐 부위를 제외한 화학식 1의 구조를 가짐을 확인하였으며, 그 결과를 아래 표 2에 정리하였다. Except that diphenyl cyclopolysiloxane was not used and the amounts of each raw material were controlled to prepare compounds having different z and w values. These Comparative Examples 1 and 2 correspond to materials used in Abil EM 90 (manufactured by Deggusa) and KF-6028 (manufactured by Shin-etsu) which are conventional commercial surfactants, respectively. NMR analysis confirmed that the obtained silicone compounds had the structure of Formula 1 except for the phenyl moiety. The results are summarized in Table 2 below.
[표 2][Table 2]
실시예Example 4 ~ 6 및 4 to 6 and 비교예Comparative Example 3 ~ 4 3 to 4
< 화장품 조성물의 제조 및 테스트 >≪ Preparation and Test of Cosmetic Composition >
상기 실시예 1~3 및 비교예 1~2에서 제조된 실리콘 화합물들을 O/W 유화제용 계면활성성분으로 사용하여 화장품 조성물을 각각 제조하고, 그 유화안정성을 실험하였다. Each of the silicone compounds prepared in Examples 1 to 3 and Comparative Examples 1 and 2 was used as a surfactant component for an O / W emulsifier to prepare cosmetic compositions, and their emulsion stability was tested.
사이클로디메티콘(D5) 10 중량부, 디메티콘(6cst) 5 중량부, 장쇄알킬원료(Lily 70) 5 중량부 그리고 상기 실시예 1~3 및 비교예 1~2에서 각각 제조된 실리콘 화합물 1 중량부를 혼합한 오일상에 증류수 73.5, NaCl 1.5 중량부, 장쇄알콜(1,3-BG) 4 중량부를 혼합한 수상을 드롭핑하면서 유화시켜 화장품 조성물을 각각 제조하고, 그 유화안정성을 확인하였다. 결과를 아래 표 3에 정리하였다. 10 parts by weight of cyclodiimethicone (D5), 5 parts by weight of dimethicone (6cst), 5 parts by weight of a long chain alkyl raw material (Lily 70), and 1 part by weight of the silicone compound 1 prepared in Examples 1 to 3 and Comparative Examples 1 and 2 Weight portion, 73.5 parts of distilled water, 1.5 parts of NaCl and 4 parts of long-chain alcohol (1,3-BG) was emulsified while dropping to prepare each of the cosmetic compositions, and their emulsion stability was confirmed. The results are summarized in Table 3 below.
[표 3][Table 3]
상기 표에서 볼 수 있듯이 실시예 1~3의 실리콘 화합물이 비교예 1(기존 상용품 계면활성제인 Abil EM 90에 대응) 및 비교예 2(기존 상용품 계면활성제인 KF-6028에 대응)보다 유화안정성이 우수한 것으로 나타났다.As can be seen from the above table, the silicone compounds of Examples 1 to 3 were superior to those of Comparative Example 1 (corresponding to Abil EM 90, a conventional commercial surfactant) and Comparative Example 2 (corresponding to KF-6028, And stability.
이와 같이, 본 발명의 실리콘 화합물은 기존 상용품 계면활성제에 비하여 유화안정성이 뛰어나며, 또한 페닐 그룹의 도입으로 인해 광택성 및 화장품 원료로 사용하는 다른 페닐원료와의 상용성 또한 우수하다.As described above, the silicone compound of the present invention is superior in emulsification stability to conventional surfactants, and is also excellent in gloss and compatibility with other phenyl raw materials used as cosmetic raw materials due to the introduction of phenyl groups.
Claims (6)
[화학식 1]
상기 화학식 1에서
x는 10~300의 정수이고;
R1은 CH3 또는 C6H5 이고, y는 1~10의 정수이며;
R2는
R4는 H, CH3 또는 C(=O)CH3 이고, m은 5~30의 정수이며, n은 0~30의 정수임)이고, z는 1~10의 정수이며;
R3는 C2H4-(CH2)o-CH3 (여기서 o는 1~27의 정수임)이고, w는 1~20의 정수이며;
x/(z+w)는 1~10 이다.A silicone compound having the following formula:
[Chemical Formula 1]
In Formula 1,
x is an integer from 10 to 300;
R 1 is CH 3 or C 6 H 5 and y is an integer from 1 to 10;
R 2 is
R 4 is H, CH 3 or C (= O) CH 3 , m is an integer of 5 to 30 and n is an integer of 0 to 30, and z is an integer of 1 to 10;
R 3 is C 2 H 4 - (CH 2 ) o -CH 3 (where o is an integer from 1 to 27) and w is an integer from 1 to 20;
x / (z + w) is 1 to 10.
2) 상기 1) 단계의 반응결과물과 하기 화학식 4의 불포화 화합물을 반응시키는 단계를 포함하는, 제1항에 따른 화학식 1의 실리콘 화합물 제조방법:
[화학식 2]
(여기서 R은 CH3 또는 C6H5이고, x는 10 ~ 300의 정수이고, y는 1 ~ 10의 정수이며, z+w는 2 ~ 30의 정수이고, x/(z+w)는 1 ~ 10이다)
[화학식 3]
(여기서 R4는 H, CH3 또는 C(=O)CH3 이고, m은 5 ~ 30의 정수이며, n은 0 ~ 30의 정수이다)
[화학식 4]
(여기서 o는 1 ~ 27의 정수이다).1) hydrosilylating a methyl-phenyl-hydropolysiloxane of Formula 2 and an unsaturated polyether of Formula 3, and
2) A process for producing a silicone compound represented by formula (1) according to claim 1, comprising reacting the reaction product of step 1) with an unsaturated compound represented by formula (4)
(2)
(Wherein R is CH 3 or C 6 H 5 , x is an integer of 10 to 300, y is an integer of 1 to 10, z + w is an integer of 2 to 30, and x / (z + w) 1 to 10)
(3)
(Wherein R 4 is H, CH 3 or C (= O) CH 3 , m is an integer of 5 to 30, and n is an integer of 0 to 30)
[Chemical Formula 4]
(Where o is an integer from 1 to 27).
A cosmetic composition comprising a silicone compound of formula (1) according to claim 1 as a surfactant component.
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