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 PDF

Info

Publication number
KR101672794B1
KR101672794B1 KR1020100039885A KR20100039885A KR101672794B1 KR 101672794 B1 KR101672794 B1 KR 101672794B1 KR 1020100039885 A KR1020100039885 A KR 1020100039885A KR 20100039885 A KR20100039885 A KR 20100039885A KR 101672794 B1 KR101672794 B1 KR 101672794B1
Authority
KR
South Korea
Prior art keywords
integer
formula
silicone compound
surfactant
compound
Prior art date
Application number
KR1020100039885A
Other languages
Korean (ko)
Other versions
KR20110120462A (en
Inventor
김상임
정유석
김성열
박지윤
Original Assignee
주식회사 케이씨씨
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 주식회사 케이씨씨 filed Critical 주식회사 케이씨씨
Priority to KR1020100039885A priority Critical patent/KR101672794B1/en
Publication of KR20110120462A publication Critical patent/KR20110120462A/en
Application granted granted Critical
Publication of KR101672794B1 publication Critical patent/KR101672794B1/en

Links

Classifications

    • 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
    • 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 System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • 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

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

신규한 실리콘 화합물 및 그 제조방법, 및 그를 포함하는 계면활성제 및 화장품{Novel silicone compound and its preparation method, and surfactant and cosmetics comprising the same}TECHNICAL FIELD [0001] The present invention relates to a novel silicone compound, a method for preparing the same, a surfactant and a cosmetic comprising the same,

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.

Figure 112010027766632-pat00001
Figure 112010027766632-pat00001

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.

미국특허 제3,979,419호U.S. Patent No. 3,979,419 미국특허 제3,979,420호U.S. Patent No. 3,979,420 미국특허 제3,980,688호U.S. Patent No. 3,980,688 미국특허 제4,016,000호U.S. Pat. No. 4,016,000 미국특허 제4,018,723호U.S. Patent No. 4,018,723 미국특허 제4,147,847호U.S. Patent No. 4,147,847 미국특허 제4,885,379호U.S. Patent No. 4,885,379

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]

Figure 112010027766632-pat00002
Figure 112010027766632-pat00002

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

Figure 112010027766632-pat00003
(여기서 R4는 H, CH3 또는 C(=O)CH3 이고, m은 5 ~ 30의 정수이며, n은 0 ~ 30의 정수임)이고, z는 1 ~ 10의 정수이며;R 2 is
Figure 112010027766632-pat00003
(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), and z is an integer of 1 to 10;

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)

Figure 112010027766632-pat00004
Figure 112010027766632-pat00004

(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)

Figure 112010027766632-pat00005
Figure 112010027766632-pat00005

(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]

Figure 112010027766632-pat00006
Figure 112010027766632-pat00006

(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]

Figure 112010027766632-pat00007
Figure 112010027766632-pat00007

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]

Figure 112010027766632-pat00008
Figure 112010027766632-pat00008

실시예Example 4 ~ 6 및  4 to 6 and 비교예Comparative Example 3 ~ 4  3 to 4

< 화장품 조성물의 제조 및 테스트 >&Lt; 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]

Figure 112010027766632-pat00009
Figure 112010027766632-pat00009

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)

하기의 화학식 1을 가지는 실리콘 화합물:
[화학식 1]
Figure 112010027766632-pat00010

상기 화학식 1에서
x는 10~300의 정수이고;
R1은 CH3 또는 C6H5 이고, y는 1~10의 정수이며;
R2는
Figure 112010027766632-pat00011
(여기서
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]
Figure 112010027766632-pat00010

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
Figure 112010027766632-pat00011
(here
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. 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 포함하는, 제1항에 따른 화학식 1의 실리콘 화합물 제조방법:
[화학식 2]
Figure 112010027766632-pat00012

(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]
Figure 112010027766632-pat00013

(여기서 R4는 H, CH3 또는 C(=O)CH3 이고, m은 5 ~ 30의 정수이며, n은 0 ~ 30의 정수이다)
[화학식 4]
Figure 112010027766632-pat00014

(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)
Figure 112010027766632-pat00012

(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)
Figure 112010027766632-pat00013

(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]
Figure 112010027766632-pat00014

(Where o is an integer from 1 to 27). 제2항에 있어서, 화학식 2의 메틸-페닐-하이드로 폴리실록산은 디메틸실록산 화합물, 페닐-메틸실록산 또는 디페닐실록산 화합물, 메틸-하이드로실록산 화합물, 및 말단제로서 헥사메틸다이실록산을 중합시켜 제조된 것임을 특징으로 하는 방법. 3. The process of claim 2, wherein the methyl-phenyl-hydropolysiloxane of formula (2) is prepared by polymerizing a dimethylsiloxane compound, a phenyl-methylsiloxane or diphenylsiloxane compound, a methyl-hydrosiloxane compound, and a hexamethyldisiloxane Lt; / RTI &gt; 제2항에 있어서, 1)단계의 하이드로실릴화 반응이 백금촉매의 존재 하에서 수행되는 것을 특징으로 하는 방법.The process according to claim 2, wherein the hydrosilylation reaction of step 1) is carried out in the presence of a platinum catalyst. 제1항에 따른 화학식 1의 실리콘 화합물을 포함하는 것을 특징으로 하는 계면 활성제 조성물.A surfactant composition comprising a silicone compound of formula (1) according to claim 1. 제1항에 따른 화학식 1의 실리콘 화합물을 계면 활성 성분으로 포함하는 것을 특징으로 하는 화장품 조성물.
A cosmetic composition comprising a silicone compound of formula (1) according to claim 1 as a surfactant component.
KR1020100039885A 2010-04-29 2010-04-29 Novel silicone compound and its preparation method, and surfactant and cosmetics comprising the same KR101672794B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1020100039885A KR101672794B1 (en) 2010-04-29 2010-04-29 Novel silicone compound and its preparation method, and surfactant and cosmetics comprising the same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR1020100039885A KR101672794B1 (en) 2010-04-29 2010-04-29 Novel silicone compound and its preparation method, and surfactant and cosmetics comprising the same

Publications (2)

Publication Number Publication Date
KR20110120462A KR20110120462A (en) 2011-11-04
KR101672794B1 true KR101672794B1 (en) 2016-11-07

Family

ID=45391576

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020100039885A KR101672794B1 (en) 2010-04-29 2010-04-29 Novel silicone compound and its preparation method, and surfactant and cosmetics comprising the same

Country Status (1)

Country Link
KR (1) KR101672794B1 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105367802A (en) * 2015-11-20 2016-03-02 陕西科技大学 Polyether modified phenyl hydrogen-containing silicone oil and preparation method thereof
CN105778107A (en) * 2016-03-15 2016-07-20 陕西科技大学 Oil-soluble demulsifier and preparation method thereof

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005537364A (en) 2002-08-27 2005-12-08 ダウ・コーニング・コーポレイション Silicone elastomer composition

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4147847A (en) 1973-11-14 1979-04-03 Dow Corning Corporation Method of preparing flexible flame retardant polyether based one-shot polyurethane foams and compositions therefore
US4016000A (en) 1973-11-29 1977-04-05 Union Carbide Corporation Organosilicone polymer solutions
US3980688A (en) 1974-09-20 1976-09-14 Union Carbide Corporation Polysiloxane-polyoxyalkylene block copolymers
US3979420A (en) 1974-12-27 1976-09-07 Union Carbide Corporation Cyano-ether polysiloxane-polyoxyalkylene copolymers
US3979419A (en) 1974-12-27 1976-09-07 Union Carbide Corporation Cyano-ether polysiloxane-polyoxyalkylene copolymers
US4018723A (en) 1975-02-25 1977-04-19 Union Carbide Corporation Morpholino-modified polysiloxane-polyoxyalkylene copolymers and their use as foam stabilizers in polyurethanes
US4885379A (en) 1988-04-12 1989-12-05 Henkel Corporation Neutralized alkyl ether sulfuric acid half-ester compositions containing polyhydroxy oligomers
JPH0619028B2 (en) * 1989-01-17 1994-03-16 信越化学工業株式会社 Organopolysiloxane composition for release coating

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005537364A (en) 2002-08-27 2005-12-08 ダウ・コーニング・コーポレイション Silicone elastomer composition

Also Published As

Publication number Publication date
KR20110120462A (en) 2011-11-04

Similar Documents

Publication Publication Date Title
CA2785475C (en) Process for producing polysiloxanes with nitrogen-containing groups
JP2012007124A (en) Polyether-modified polysiloxane containing perfluoropolyether group and its production method
JPH1046473A (en) Production of linear polyorganosiloxane capable of being used for softening finish of woven fabric without yellowing
JP5745652B2 (en) Amphiphilic high refractive index organopolysiloxane
JPH03170530A (en) Organopolysiloxane having one branched molecular terminal and blocked by aminoalkyl group, and its preparation
JPH1067786A (en) Alkyl-substituted siloxane and alkyl-substituted polyether fluid
EP0797612A1 (en) Method for preparing essentially cyclene-free polyorganosiloxanes and organofunctional siloxanes
KR100864269B1 (en) Process for the preparation of organosilicon compounds having urethane groups
KR101672794B1 (en) Novel silicone compound and its preparation method, and surfactant and cosmetics comprising the same
JP2007063348A (en) Surfactant comprising highly volatile polyether-modified silicone
CN105061769A (en) Polysiloxane diol and preparation method thereof
JP3962898B2 (en) Method for producing linear organosiloxane polymer
EP2551291B1 (en) Dihydroxypropylamide-modified polysiloxane compound
JP4178266B2 (en) Alkyl polyether siloxane
CA2352912C (en) Linear polydialkylorganosiloxanes having polyoxyalkylene and amino-functional groups which additionally have terminal alkoxy groups
US6573355B2 (en) Method for preparation of organopolysilixame having branched molecular structure
US9499671B2 (en) Hydrophilic polysiloxane compositions containing carbinol groups
KR20080087741A (en) Novel silicon compound, material thereof and method for producing the same
JP2841268B2 (en) Amidobetaine-modified organo (poly) siloxane and method for producing the same
CN113631638A (en) Both-terminal lactylsilyl-modified organopolysiloxane and method for producing same
RU2783679C1 (en) Method for producing polyorganosiloxane molecular brushes
JPH10182827A (en) Production of amino-containing organopolysiloxane
EP4339225A1 (en) Fluorine-including organohydrosilane compound
WO2001032750A1 (en) Fluoroelastomers for a wide temperature range of applications
EP0978526A1 (en) Process for the preparation of fluorosilicone compounds having hydrolyzable groups

Legal Events

Date Code Title Description
A201 Request for examination
E701 Decision to grant or registration of patent right
FPAY Annual fee payment

Payment date: 20190926

Year of fee payment: 4