PL442995A1 - New bifunctional and trifunctional polysiloxanes, method of preparation and use as a UV radiation absorbing agent and emulsifier in oil-water systems - Google Patents
New bifunctional and trifunctional polysiloxanes, method of preparation and use as a UV radiation absorbing agent and emulsifier in oil-water systemsInfo
- Publication number
- PL442995A1 PL442995A1 PL442995A PL44299522A PL442995A1 PL 442995 A1 PL442995 A1 PL 442995A1 PL 442995 A PL442995 A PL 442995A PL 44299522 A PL44299522 A PL 44299522A PL 442995 A1 PL442995 A1 PL 442995A1
- Authority
- PL
- Poland
- Prior art keywords
- sub
- group
- cinnamate
- polysiloxanes
- trifunctional
- Prior art date
Links
- -1 polysiloxanes Polymers 0.000 title abstract 9
- 229920001296 polysiloxane Polymers 0.000 title abstract 7
- 230000001588 bifunctional effect Effects 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 3
- 230000005855 radiation Effects 0.000 title abstract 3
- 239000006096 absorbing agent Substances 0.000 title abstract 2
- 239000003995 emulsifying agent Substances 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 150000001336 alkenes Chemical class 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 abstract 3
- GVZIBGFELWPEOC-UHFFFAOYSA-N (2-hydroxy-4-prop-2-enoxyphenyl)-phenylmethanone Chemical compound OC1=CC(OCC=C)=CC=C1C(=O)C1=CC=CC=C1 GVZIBGFELWPEOC-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 abstract 2
- 229940114081 cinnamate Drugs 0.000 abstract 2
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 abstract 2
- 125000000524 functional group Chemical group 0.000 abstract 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 2
- 239000000758 substrate Substances 0.000 abstract 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 abstract 1
- WULAHPYSGCVQHM-UHFFFAOYSA-N 2-(2-ethenoxyethoxy)ethanol Chemical compound OCCOCCOC=C WULAHPYSGCVQHM-UHFFFAOYSA-N 0.000 abstract 1
- KCMITHMNVLRGJU-CMDGGOBGSA-N Allyl cinnamate Chemical compound C=CCOC(=O)\C=C\C1=CC=CC=C1 KCMITHMNVLRGJU-CMDGGOBGSA-N 0.000 abstract 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 abstract 1
- 239000012965 benzophenone Substances 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract 1
- 230000008034 disappearance Effects 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
Classifications
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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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/12—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- General Chemical & Material Sciences (AREA)
- Silicon Polymers (AREA)
Abstract
Przedmiotem zgłoszenia są nowe dwufunkcyjne lub trójfunkcyjne polisiloksany, sposób otrzymywania oraz zastosowania jako czynnik absorbujący promieniowanie ultrafioletowe i emulgator w układach olej-woda. Wynalazek dotyczy dwufunkcyjnych lub trójfunkcyjnych pochodnych krzemoorganicznych - polisiloksanów (mających co najmniej jedną grupę funkcyjną absorbującą promieniowanie UV oraz co najmniej jedną grupę hydrofilową), które stanowią składnik emulsji w stężeniu 0,2 - 20 w.w.%, korzystnie 2 - 3 w.w.%. Nowe dwufunkcyjne lub trójfunkcyjne polisiloksany o budowie liniowej z grupami funkcyjnymi sililoetylową i benzofenonową o wzorze 1 lub cynamonianową o wzorze 2 albo eterową i cynamonianową o wzorze 3, gdzie R<sub>1</sub> oznacza grupę sililoetylową, R<sub>2</sub> oznacza grupę benzofenonową oraz R<sub>3</sub> grupę cynamonianową. Sposób ich otrzymywania polega na tym, że w kolbie pod chłodnicą zwrotną umieszcza się substraty: PS1: PWS991 oraz olefiny eter monowinylowy glikoli dietylenowego, winylotrimetoksysilanu oraz 4-alliloksy-2-hydroksybenzofenonu w proporcjach 1:1:2 w przeliczeniu na liczbę moli Si-H użytego polisiloksanu, PS2: PWS991 oraz olefiny okten, winylotrimetoksysilanu, cynamonianu allilu w proporcjach 1:1:2 w przeliczeniu na liczbę moli Si-H użytego polisiloksanu, PS3: PWS991 oraz olefiny eter monowinylowy glikolu dietylenowego oraz 4-alliloksy 2-hydroksybenzofenonu w proporcjach 2:1 w przeliczeniu na liczbę moli Si-H użytego polisiloksanu, po czym do mieszaniny reakcyjnej dodaje się osuszony i oczyszczony toluen jako rozpuszczalnik oraz każdorazowo 10<sup>-5</sup> eq. Pt/mol Si-H katalizatora Karstedta, dalej układ podgrzewa się do temperatury wrzenia rozpuszczalnika przez 24 - 48 godzin, korzystnie 24 godziny (po uzyskaniu pełnej konwersji substratów i zaniku pasma Si-H), następnie układ chłodzi się do temperatury pokojowej i usuwa się rozpuszczalnik pod obniżonym ciśnieniem do uzyskania gotowego produktu PS1/PS2/PS3.The subject of the application are new bifunctional or trifunctional polysiloxanes, methods of preparation and applications as an ultraviolet radiation absorbing agent and emulsifier in oil-water systems. The invention concerns bifunctional or trifunctional organosilicon derivatives - polysiloxanes (having at least one functional group absorbing UV radiation and at least one hydrophilic group), which constitute an emulsion component at a concentration of 0.2 - 20 w.w.%, preferably 2 - 3 w.w.%. New difunctional or trifunctional polysiloxanes with a linear structure with functional groups: silylethyl and benzophenone of formula 1 or cinnamate of formula 2 or ether and cinnamate of formula 3, where R<sub>1</sub> is a silylethyl group, R<sub>2< /sub> denotes a benzophenone group and R<sub>3</sub> a cinnamate group. The method of obtaining them is that the following substrates are placed in a flask under a reflux condenser: PS1: PWS991 and olefins, monovinyl ether of diethylene glycols, vinyltrimethoxysilane and 4-allyloxy-2-hydroxybenzophenone in the proportions 1:1:2 based on the number of moles of Si- H of the polysiloxane used, PS2: PWS991 and olefin octene, vinyltrimethoxysilane, allyl cinnamate in proportions 1:1:2 based on the number of moles of Si-H of the polysiloxane used, PS3: PWS991 and olefin diethylene glycol monovinyl ether and 4-allyloxy 2-hydroxybenzophenone in proportions 2:1 based on the number of moles of Si-H of the polysiloxane used, then dried and purified toluene as a solvent and each time 10<sup>-5</sup>eq are added to the reaction mixture. Pt/mol Si-H Karstedt catalyst, the system is then heated to the boiling point of the solvent for 24 - 48 hours, preferably 24 hours (after achieving full conversion of the substrates and the disappearance of the Si-H band), then the system is cooled to room temperature and removed solvent under reduced pressure to obtain the finished product PS1/PS2/PS3.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL442995A PL442995A1 (en) | 2022-11-30 | 2022-11-30 | New bifunctional and trifunctional polysiloxanes, method of preparation and use as a UV radiation absorbing agent and emulsifier in oil-water systems |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL442995A PL442995A1 (en) | 2022-11-30 | 2022-11-30 | New bifunctional and trifunctional polysiloxanes, method of preparation and use as a UV radiation absorbing agent and emulsifier in oil-water systems |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL442995A1 true PL442995A1 (en) | 2024-06-03 |
Family
ID=91333036
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL442995A PL442995A1 (en) | 2022-11-30 | 2022-11-30 | New bifunctional and trifunctional polysiloxanes, method of preparation and use as a UV radiation absorbing agent and emulsifier in oil-water systems |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL442995A1 (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0475130B1 (en) * | 1990-08-30 | 1997-12-03 | Kao Corporation | Siloxane derivative, its use as emulsifier and cosmetic preparations |
| US6080880A (en) * | 1997-11-28 | 2000-06-27 | Societe L'oreal S.A. | Silicone-substituted cinnamamide/malonamide/malonate compounds and photoprotective compositions comprised thereof |
| WO2006128614A1 (en) * | 2005-05-31 | 2006-12-07 | Dsm Ip Assets B.V. | Novel polysiloxane sunscreens |
| PL208938B1 (en) * | 2007-01-19 | 2011-06-30 | Univ Adama Mickiewicza | The manner of obtaining of modified (poly)siloxans |
-
2022
- 2022-11-30 PL PL442995A patent/PL442995A1/en unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0475130B1 (en) * | 1990-08-30 | 1997-12-03 | Kao Corporation | Siloxane derivative, its use as emulsifier and cosmetic preparations |
| US6080880A (en) * | 1997-11-28 | 2000-06-27 | Societe L'oreal S.A. | Silicone-substituted cinnamamide/malonamide/malonate compounds and photoprotective compositions comprised thereof |
| WO2006128614A1 (en) * | 2005-05-31 | 2006-12-07 | Dsm Ip Assets B.V. | Novel polysiloxane sunscreens |
| PL208938B1 (en) * | 2007-01-19 | 2011-06-30 | Univ Adama Mickiewicza | The manner of obtaining of modified (poly)siloxans |
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