CN111518278A - Natural oil modified organic silicon elastomer and preparation method thereof - Google Patents

Natural oil modified organic silicon elastomer and preparation method thereof Download PDF

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Publication number
CN111518278A
CN111518278A CN202010446768.7A CN202010446768A CN111518278A CN 111518278 A CN111518278 A CN 111518278A CN 202010446768 A CN202010446768 A CN 202010446768A CN 111518278 A CN111518278 A CN 111518278A
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natural oil
oil
organic silicon
fat
natural
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李信成
孙东明
许丹静
杨建坤
吴寒
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Hunan Sloco Silicone Co ltd
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Hunan Sloco Silicone Co ltd
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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
    • C08G77/38—Polysiloxanes modified by chemical after-treatment
    • 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
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A61K8/893—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by an alkoxy or aryloxy group, e.g. behenoxy dimethicone or stearoxy dimethicone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/10—General cosmetic use
    • 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
    • C08G77/12—Polysiloxanes containing silicon bound to hydrogen

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  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Dermatology (AREA)
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  • Cosmetics (AREA)

Abstract

The invention relates to the field of high polymer materials, in particular to a natural oil modified organic silicon elastomer and a preparation method thereof. The natural oil modified organic silicon elastomer is

Description

Natural oil modified organic silicon elastomer and preparation method thereof
Technical Field
The invention relates to the field of high polymer materials, in particular to a natural oil modified organic silicon elastomer and a preparation method thereof.
Technical Field
Silicone elastomers are a class of materials prepared with the relatively small particle structure inherent to silicone powder particles and their elastic properties (the ability to deform but return to their original shape after removal of the deforming force), which have a unique silky and powdery feel and are widely used in personal care products.
Silicone elastomers have limited compatibility with various personal care ingredients, personal care actives and healthcare actives. The thickening, gelling efficiency, and even sensory benefits of silicone elastomers in the presence of personal care ingredients, personal care actives and healthcare actives are lost, and therefore, there is a need to further improve the compatibility of silicone elastomers with various personal care ingredients and actives.
Disclosure of Invention
Technical problem to be solved
The invention aims to provide a natural oil modified organic silicon elastomer which is compatible with most active ingredients (such as spice, sunscreen cream, vitamins and vitamin derivatives), is easy to add and can be used as a thickening agent for water-in-oil and anhydrous formulas on the basis of absorbing the previous research experience, and also aims to provide a preparation method of the organic silicon elastomer, which is convenient for industrial production.
(II) technical scheme
The invention provides a natural grease modified organic silicon elastomer which has the following structure:
Figure BDA0002506128860000011
wherein R is a natural oil or an acrylated natural oil containing an unsaturated bond, and m and n are 3-8.
The natural oil is natural oil with high unsaturated fatty acid content or natural oil which is subjected to acrylic acid treatment.
The natural oil with high unsaturated fatty acid content is one of sunflower seed oil, olive oil, soybean oil, peanut oil and corn oil.
The natural oil subjected to the acrylation is acrylated epoxidized soybean oil.
The natural oil modified organic silicon elastomer is
Figure BDA0002506128860000021
m、n＝3～8。
The natural oil modified organic silicon elastomer
Figure BDA0002506128860000022
m、n＝3～8。
The natural grease modified organic silicon elastomer is prepared by the following method: in N2Under protection, hydrogen-containing silicone oil with an H value of 1-20 percent is stirred and reacted with natural oil with high unsaturated fatty acid content or acrylated natural oil and a catalyst to generate the natural oil modified organic silicon elastomer.
The natural oil modified organic silicon elastomer is used as an additive for skin care products, cosmetics, antiperspirants or deodorants.
The method provides a novel natural grease modified organic silicon elastomer, and the organic silicon elastomer is modified by natural grease, so that the organic silicon elastomer has higher stability and does not react with solvents and other substances. Meanwhile, the organic silicon elastomer prepared by the method has better compatibility with natural grease, and has the characteristics of high glossiness, refreshing property and no greasiness; at the same time, the silicone elastomers prepared in accordance with the present invention may be mixed with personal care or health care actives; and can promote the rapid absorption of active ingredients, reduce the sticky feeling of the formula and have long-lasting skin texture.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the description is intended to be exemplary only, and is not intended to limit the scope of the present invention. Moreover, in the following description, descriptions of well-known structures and techniques are omitted so as to not unnecessarily obscure the concepts of the present invention.
The epoxidized soybean oil acrylate is prepared according to the method of Chinese invention patent CN103013682B or by adopting the commercially available epoxidized soybean oil, and comprises the following specific steps:
Figure BDA0002506128860000031
a. placing a mixture of 50g of refined soybean oil, 12.5g of formic acid and 25g of petroleum ether in a three-opening reaction bottle with an electric stirrer, a dropping funnel and a condensing tube, placing the mixture in a constant-temperature water bath, uniformly mixing, stirring, raising the temperature to 45 ℃, and dropwise adding a mixture of hydrogen peroxide and phosphoric acid in a mass ratio of 1.3: 0.005;
b. after the mixture of the hydrogen peroxide and the phosphoric acid is dripped and the temperature is stable, adjusting the temperature of the system to 55 ℃ and reacting for 3 hours;
c. after the reaction is finished, transferring the reaction mixture into a separating funnel, standing for layering, removing a water layer, washing an oil layer to be neutral by using water, and distilling under reduced pressure to obtain epoxidized soybean oil, wherein the epoxy value is 5.3, the iodine value is 1.3, the acid value is 0.3, and the yield is 91%;
d. adding calcium oxide with the mass percent of 5% of the raw material into the residual formic acid aqueous solution after the reaction to obtain calcium formate, and recovering;
e. adding epoxidized soybean oil, acrylic acid, p-toluenesulfonic acid and hydroquinone in a mass ratio of 1:0.3:0.01:0.008 into a reaction kettle, vacuumizing at the temperature of 60 ℃ (the pressure is 0.03MPa), and reacting for 3 hours;
f. after the reaction, the unreacted mixed fatty acid is evaporated out under reduced pressure, and the light yellow transparent oily matter epoxy soybean oil acrylate is obtained, wherein the iodine value is 32.8 percent.
Example 1
The preparation method comprises the following steps: in a 500mL four-necked flask equipped with a stirrer, a thermometer, a reflux condenser and an electric heating jacket, 10g of hydrogen-containing silicone oil having an H value of 5% and a polymerization degree of 45 and epoxy soybean oil acrylate were charged into the flask in a mass ratio of 24: 5, and the mixture was stirred in a nitrogen atmosphere2Stirring under protection, heating to 70 deg.CAdding activated platinum catalyst, wherein the addition amount (based on the mass of Pt) is 4 × 10 of the total mass of the raw materials-4And percent, continuously heating to 90 ℃, observing that the materials in the reactor are changed from milk white to transparent to judge that the reaction reaches the end point, continuously stirring for 8 hours at constant temperature, cooling and discharging, and removing the solvent in vacuum to obtain the natural oil modified organic silicon elastomer A1.
Figure BDA0002506128860000041
The IR chart of the reaction product revealed that Si-H (2280 cm) as a raw material was not observed-1～2080cm-1) and-CH ═ CH2(1640cm-1～1630cm-1) Characteristic absorption peaks indicating that the starting material has been converted to the product. The characteristic absorption peaks of the product natural oil modified organic silicon elastomer A1 are as follows: 1385cm-1～1375cm-1Is- (CH)3)2C-；1108cm-1Is Si-O-Si; 2967cm-1、1297cm-1Is Si-CH3。
Example 2
100g of polysiloxane with an H value of 15% and a polymerization degree of 56, 20g of epoxy soybean oil acrylate and 0.05g of activated platinum catalyst are added into a reaction kettle, stirred and reacted for 8 hours at the temperature of 60 ℃, and the solvent is removed in vacuum at the temperature of 90 ℃ to obtain the natural grease modified organic silicon elastomer A2.
Figure BDA0002506128860000051
The IR chart of the reaction product revealed that Si-H (2280 cm) as a raw material was not observed-1～2080cm-1) and-CH ═ CH2(1640cm-1～1630cm-1) Characteristic absorption peaks indicating that the starting material has been converted to the product. The characteristic absorption peaks of the product natural oil modified organic silicon elastomer A2 are as follows: 1490cm-1～1350cm-1is-CH-; 2925cm-1、2985cm-1is-CH2-；1108cm-1Is Si-O-Si; 2967cm-1、1297cm-1Is Si-CH3。
Test example 1 compatibility with common cosmetic ingredients
Table 1: the silicone elastomer (content 50%) obtained by the invention is compatible with common cosmetic ingredients
Figure BDA0002506128860000052
Figure BDA0002506128860000061
Remarking: c is compatible I is incompatible
As can be seen from the above table, the silicone elastomer of the present invention has better compatibility than commercial silicone elastomers.
Test example 2 Long-lasting Foundation
Table 2A formulation:
Figure BDA0002506128860000062
Figure BDA0002506128860000071
the elastomers are respectively: examples 1 to 2.
The preparation method comprises the following steps:
1) completely and uniformly dispersing magnesium aluminum silicate in water, and adding the rest phase A;
2) uniformly mixing the phase B, and paying attention to the dispersion condition of the toner;
3) heating the A and B phases to 75 deg.C respectively. Adding the phase A into the phase B under the condition of stirring. And cooling to room temperature. So far, the emulsion is also a common foundation, and if the C/D phase is added, the emulsion is a long-acting lasting foundation;
4) adding the phase C into the mixture of the phases A and B, and homogenizing. Then adding phase D until mixing evenly;
5) adding antiseptic, and stirring for 5 min.
Evaluation of sensory Properties C
Sensory properties can be defined by the ease of product selection, spreadability, and after-use feel, although such sensory evaluation methods can vary from person to person. To examine the changes that elastomers impart to the formulation, comparative experiments were conducted and evaluated by l8 experienced evaluation subjects, the results of which are shown in Table 3.
Figure BDA0002506128860000072
Figure BDA0002506128860000081
Table 3 shows that the elastomers prepared by the invention have long-lasting, silky, smooth, soft and powdery skin feel.

Claims (8)

1. The invention provides a natural oil modified organic silicon elastomer which is characterized by having the following structure:
Figure FDA0002506128850000011
wherein R is a natural oil or an acrylated natural oil containing an unsaturated bond, and m and n are 3-8.
2. The natural oil-and-fat modified silicone elastomer according to claim 1, wherein the natural oil-and-fat is a natural oil-and-fat having a high unsaturated fatty acid content, or an acrylated natural oil-and-fat.
3. The natural oil-modified silicone elastomer of claim 1, wherein the natural oil having a high content of unsaturated fatty acids is one of sunflower oil, olive oil, soybean oil, peanut oil and corn oil.
4. The natural oil-and-fat-modified silicone elastomer according to claim 1, wherein the acrylated natural oil is acrylated epoxidized soybean oil.
5. The natural oil-and-fat-modified silicone elastomer according to claim 1, wherein the natural oil-and-fat-modified silicone elastomer is
Figure FDA0002506128850000012
m、n＝3～8。
6. The natural oil-and-fat-modified silicone elastomer according to claim 1, wherein the natural oil-and-fat-modified silicone elastomer is
Figure FDA0002506128850000021
m、n＝3～8。
7. A preparation method of a natural oil modified organic silicon elastomer is characterized by comprising the following steps:
in N2Under protection, hydrogen-containing silicone oil with an H value of 1-20 percent is stirred and reacted with natural oil with high unsaturated fatty acid content or acrylated natural oil and a catalyst to generate the natural oil modified organic silicon elastomer.
8. Use of the silicone elastomer according to claim 1 as an additive for skin care products, make-up, antiperspirants or deodorants.
CN202010446768.7A 2020-05-25 2020-05-25 Natural oil modified organic silicon elastomer and preparation method thereof Pending CN111518278A (en)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103013682A (en) * 2012-12-13 2013-04-03 中国科学院新疆理化技术研究所 Synthetic method for epoxy soybean oil acrylate
CN104372621A (en) * 2014-11-07 2015-02-25 东华大学 Vegetable-oil-based softening agent and preparation method thereof
CN108261350A (en) * 2018-02-01 2018-07-10 湖南斯洛柯有机硅有限公司 A kind of emulsifier and preparation method thereof and the cosmetics containing it
CN109384925A (en) * 2018-10-28 2019-02-26 湖南斯洛柯有机硅有限公司 A kind of natural oil modified organic silicon elastomer
CN111004662A (en) * 2019-12-19 2020-04-14 刘涛 Bio-based lubricating oil base oil and preparation method thereof

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103013682A (en) * 2012-12-13 2013-04-03 中国科学院新疆理化技术研究所 Synthetic method for epoxy soybean oil acrylate
CN104372621A (en) * 2014-11-07 2015-02-25 东华大学 Vegetable-oil-based softening agent and preparation method thereof
CN108261350A (en) * 2018-02-01 2018-07-10 湖南斯洛柯有机硅有限公司 A kind of emulsifier and preparation method thereof and the cosmetics containing it
CN109384925A (en) * 2018-10-28 2019-02-26 湖南斯洛柯有机硅有限公司 A kind of natural oil modified organic silicon elastomer
CN111004662A (en) * 2019-12-19 2020-04-14 刘涛 Bio-based lubricating oil base oil and preparation method thereof

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
ABDELKRIM EL KADIB,等: "Nanocomposites from natural templates based on fatty compound-functionalised siloxanes", 《JOURNAL OF MATERIALS CHEMISTRY》 *
兰中旭，等: "大豆油基柔软剂的合成及其应用性能研究", 《印染助剂》 *

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Application publication date: 20200811