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CN-117700582-B - Organosilicon modified hyaluronic acid, modified liquid organosilicon elastomer, and preparation methods and applications thereof

CN117700582BCN 117700582 BCN117700582 BCN 117700582BCN-117700582-B

Abstract

The invention provides an organosilicon modified hyaluronic acid, a modified liquid organosilicon elastomer, and a preparation method and application thereof; the organic silicon modified hyaluronic acid comprises the following preparation raw materials of hyaluronic acid and vinyl single-end socket, wherein the preparation raw materials of the modified liquid organic silicon elastomer comprise the following components of (A) hyaluronic acid with ethylenic unsaturated groups, (B) organic polysilane with at least two ethylenic unsaturated groups, (C) organopolysiloxane containing at least two SiH groups, (D) carrier fluid and (E) hydrosilylation catalyst, wherein the component (A) is the organic silicon modified hyaluronic acid. According to the invention, the organosilicon modified hyaluronic acid is introduced into the organosilicon elastomer chain segment, so that the organosilicon elastomer with excellent spreadability, smoothness, no sticky and wet feeling and excellent transparency is obtained. In addition, the modified organosilicon elastomer gel obtained by the invention is in a liquid state, and can be directly applied to various daily chemical products.

Inventors

  • YANG JIANKUN
  • SUN DONGMING

Assignees

  • 湖南斯洛柯有机硅有限公司

Dates

Publication Date
20260505
Application Date
20231222

Claims (14)

  1. 1. The organic silicon modified hyaluronic acid is characterized by comprising the following preparation raw materials of hyaluronic acid, dimethylvinylethoxysilane and an organic titanium catalyst; The preparation method of the organosilicon modified hyaluronic acid comprises the following steps of reacting hyaluronic acid, dimethylvinylethoxysilane and an organic titanium catalyst at the temperature of 150-190 ℃ and the pressure of 0.2-0.4 mpa to prepare the organosilicon modified hyaluronic acid; The mass ratio of the hyaluronic acid to the dimethylvinylethoxysilane is 100 (2-25).
  2. 2. A modified liquid organosilicon elastomer is characterized in that, the preparation raw materials of the modified liquid organic silicon elastomer comprise the following components: (A) Hyaluronic acid with ethylenically unsaturated groups; (B) An organopolysiloxane having at least two ethylenically unsaturated groups; (C) An organohydrogen polysiloxane containing at least two SiH groups; (D) A carrier fluid; (E) A hydrosilylation catalyst; the component (a) is the silicone-modified hyaluronic acid of claim 1; the component (A), the component (B) and the component (C) undergo hydrosilylation in the component (D).
  3. 3. The modified liquid silicone elastomer according to claim 2, wherein the molar ratio between the ethylenically unsaturated groups and the hydrosilylation groups in the preparation raw material is 1:0.01-0.2.
  4. 4. The modified liquid silicone elastomer according to claim 2, wherein the molecular weight of component (A) is less than or equal to 5000Da.
  5. 5. The modified liquid silicone elastomer according to claim 2, wherein the component (a) accounts for 0.1 to 5wt% of the total weight of the modified liquid silicone elastomer.
  6. 6. The modified liquid silicone elastomer according to claim 2, wherein the molecular weight of the component (B) is 10 to 130 ten thousand.
  7. 7. The modified liquid silicone elastomer according to claim 2, wherein the molecular weight of the component (B) is 90 to 130 ten thousand.
  8. 8. The modified liquid silicone elastomer according to claim 2, wherein the ethylenically unsaturated group content of the component (B) is 1 to 6wt%.
  9. 9. The modified liquid silicone elastomer according to claim 2, wherein the hydrogen content of the component (C) is 0.01 to 0.5wt%.
  10. 10. The modified liquid silicone elastomer of claim 2, wherein the carrier fluid comprises 75% -95% of the total weight of the liquid silicone elastomer.
  11. 11. A method for producing the modified liquid silicone elastomer according to any one of claims 2 to 10, characterized in that the method for producing the modified liquid silicone elastomer comprises the steps of: Mixing the (A) hyaluronic acid with ethylenic unsaturation, (B) an organopolysiloxane with at least two ethylenic unsaturation, (C) an organohydrogen polysiloxane with at least two SiH groups, and (E) a hydrosilylation catalyst, and reacting in (D) a carrier fluid to obtain the modified liquid silicone elastomer.
  12. 12. The method according to claim 11, wherein the reaction temperature is 70-120 ℃ and the reaction time is 2-10 hours.
  13. 13. The method of claim 11, wherein the hydrosilylation catalyst is one or more of Pt or Pd catalyst or its complex, karstedt catalyst or Speier' S catalyst.
  14. 14. Use of the modified liquid silicone elastomer according to any one of claims 2 to 10 or the modified liquid silicone elastomer produced by the production method according to claims 11 to 13 in daily chemical products.

Description

Organosilicon modified hyaluronic acid, modified liquid organosilicon elastomer, and preparation methods and applications thereof Technical Field The invention belongs to the technical field of organic silicon, and particularly relates to an organic silicon modified hyaluronic acid, a modified liquid organic silicon elastomer, and a preparation method and application thereof. Background Hyaluronic acid is an acidic mucopolysaccharide, has excellent moisturizing effect, is called ideal natural moisturizing factor, can play an excellent role in protecting skin, can keep skin moist and smooth, and has the functions of preventing wrinkles, resisting wrinkles, beautifying and protecting health and recovering physiological functions of the skin when applied to cosmetics. It has been widely used in personal care products at present, but it has problems of poor film forming property, sticky and wet feeling, and poor skin feel. In addition, the moisturizing property of the silicone elastomer can be improved by combining the hyaluronic acid with the silicone elastomer, but at present, the physical blending of the hyaluronic acid and the silicone elastomer is usually carried out, so that the film forming property and the spreadability of the hyaluronic acid are poor, and a better moisturizing effect cannot be obtained. CN115232316a discloses a silicone elastomer comprising the polymerization reaction product of polymer a and polymer b, wherein polymer a is sodium hyaluronate modified polysiloxane with a polymerization degree of 100-150, polymer b is vinyl polysiloxane with a polymerization degree of 50-80, and the molar ratio of polymer b to polymer a is 1:2-1:0.5. The obtained organosilicon elastomer has the effects of moisturizing and nourishing by grafting the moisturizing raw material sodium hyaluronate onto polysiloxane, and has good compatibility with skin when being applied to cosmetic products. However, the silicone elastomer is a solid elastomer, which can be used only after the silicone elastomer is crushed after the reaction is completed, and which cannot achieve better sensory properties. Accordingly, it is a technical problem in the art to provide a modified liquid silicone elastomer having a good moisturizing effect. Disclosure of Invention Aiming at the defects of the prior art, the invention provides an organosilicon modified hyaluronic acid, a modified liquid organosilicon elastomer, and a preparation method and application thereof. In a first aspect, the invention provides an organosilicon modified hyaluronic acid, which comprises the following preparation raw materials of hyaluronic acid and vinyl single-end socket. Preferably, the mass ratio between the hyaluronic acid and the dimethylvinylethoxysilane is 100 (2-25). Preferably, the vinyl single seal head is dimethyl vinyl ethoxy silane and/or dimethyl vinyl methoxy silane. Preferably, the preparation raw material further comprises an organic titanium catalyst. In a second aspect, the present invention provides a method for preparing the organosilicon modified hyaluronic acid according to the first aspect, which comprises the step of reacting hyaluronic acid with a vinyl single end socket under certain conditions to obtain the organosilicon modified hyaluronic acid. Preferably, the reaction conditions are that the reaction temperature is 150-190 ℃ and the reaction pressure is 0.2-0.3 mpa. According to the invention, the carboxyl of the hyaluronic acid reacts with the alkoxy of the vinyl single-end socket to obtain the organosilicon modified hyaluronic acid with double bonds. In a third aspect, the present invention provides a modified liquid silicone elastomer, wherein the preparation raw materials of the liquid silicone elastomer include the following components: (A) Hyaluronic acid with ethylenically unsaturated groups; (B) An organopolysiloxane having at least two ethylenically unsaturated groups; (C) An organohydrogen polysiloxane containing at least two SiH groups; (D) A carrier fluid; (E) A hydrosilylation catalyst; the component (A) is the organic silicon modified hyaluronic acid or the organic silicon modified hyaluronic acid obtained by the preparation method. Preferably, the molar ratio of the ethylenically unsaturated groups to the hydrosilylation groups in the preparation raw material is 1:0.01-0.2. Preferably, the molar ratio of the ethylenically unsaturated groups to the hydrosilylation groups in the preparation raw material is 1:0.01-0.1. Preferably, the molecular weight of component (A) is less than or equal to 5000Da. Preferably, the component (A) accounts for 0.1-5wt% of the total weight of the liquid organic silicon elastomer. Preferably, the molecular weight of the component (B) is 10-130 ten thousand. Preferably, the molecular weight of the component (B) is 90-130 ten thousand. Preferably, the component (B) has an ethylenically unsaturated group content of 1 to 6wt%. Preferably, the hydrogen content of the component (C) is 0.01