CA2074616A1 - Glycerol functional polysiloxanes - Google Patents
Glycerol functional polysiloxanesInfo
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- CA2074616A1 CA2074616A1 CA 2074616 CA2074616A CA2074616A1 CA 2074616 A1 CA2074616 A1 CA 2074616A1 CA 2074616 CA2074616 CA 2074616 CA 2074616 A CA2074616 A CA 2074616A CA 2074616 A1 CA2074616 A1 CA 2074616A1
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Abstract
ABSTRACT OF THE DISCLOSURE
A glycerol functional polysiloxane having the formula
A glycerol functional polysiloxane having the formula
Description
GLVCrROL FUNC~IONAL POLYSI~OXANES
This invention relates to personal care and more particu-larly to certain glycerol functional polysiloxanes useful as humectants in skin care applications.
The water content of the outer layers of the stratum corneum of the human epidermis is a controlling factor in the appearance of dry skin symptoms. When the stratum corneum contains an adequate amount of waier within the range of about 10 to 20 percent, the skin remains flexible. However, when the water content falls below about ten percent, the s.ratum orneum often becomes brittle and rough and can e~hibit scaling and cracking.
The stratum corneum receives its water from the deep layers of the epidermis by diffusion or when it is brought int~
direct contact with water. The dif~usion process is controlled by the water content of the skin as well as by the concentration gradient. In a very dry environment for example, the water loss from the external skin layers can be significant and often Iexceeds the rate of replenishment by the diffusion process.
IIt is not uncommon therefore to include in skin condltioning compositions a humactant which is capable of intro-ducins moisture to the skin from t~e atmosphere in conditions of modexate or high humidity. In conditions of low humidity humectants attract mois~ure from the lower layers of the skin.
Humectants are materials which are hygroscopic and are therefore capable of retaining moisture. Among the most well known water retentive humectants capable of preventing drying out of the skin is glycerol. Glycerol is known to be an ef,ective humectant and is generally considered harmless in cosmetic applications. It is a clear water white viscous li~uid having the chemical formula HOCH2CHOHCH20H. However, glycerol exhibits no bonding to the skin and hence is not dura~le or substartive , ~
This invention relates to personal care and more particu-larly to certain glycerol functional polysiloxanes useful as humectants in skin care applications.
The water content of the outer layers of the stratum corneum of the human epidermis is a controlling factor in the appearance of dry skin symptoms. When the stratum corneum contains an adequate amount of waier within the range of about 10 to 20 percent, the skin remains flexible. However, when the water content falls below about ten percent, the s.ratum orneum often becomes brittle and rough and can e~hibit scaling and cracking.
The stratum corneum receives its water from the deep layers of the epidermis by diffusion or when it is brought int~
direct contact with water. The dif~usion process is controlled by the water content of the skin as well as by the concentration gradient. In a very dry environment for example, the water loss from the external skin layers can be significant and often Iexceeds the rate of replenishment by the diffusion process.
IIt is not uncommon therefore to include in skin condltioning compositions a humactant which is capable of intro-ducins moisture to the skin from t~e atmosphere in conditions of modexate or high humidity. In conditions of low humidity humectants attract mois~ure from the lower layers of the skin.
Humectants are materials which are hygroscopic and are therefore capable of retaining moisture. Among the most well known water retentive humectants capable of preventing drying out of the skin is glycerol. Glycerol is known to be an ef,ective humectant and is generally considered harmless in cosmetic applications. It is a clear water white viscous li~uid having the chemical formula HOCH2CHOHCH20H. However, glycerol exhibits no bonding to the skin and hence is not dura~le or substartive , ~
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wi~h the result that it can be washed from the skin surface. It is used in many creams and lotions ior the purpose of keeping the skin soft and for replacing skin moisture. -The prior art is replete with various formulations which contain glycerol as an ingredient. One such prior art compo-sition is described in United States pat~nt application Serial No. 07/489117 .iled 5th ~arch 1990 of Andrew H. Ward entitled "Glyceroxyfunctional org2nosilicon Compounds", which application is assigned to Dow Corning Corporation. The Ward application discloses a silicone compound having the group -OCH~CH(OH)C~2OH
directly bonded to a silicon atom in the polymer main chain.
Upon contact with water, the silicone compound undergoes hydrolysis with the result that the si-o bond is cleaved and free glycerol is released onto the skin accom-panied by the simultaneous formation of silanol groups. However, as already noted, glycerol is not durable and can be easily removed from the skin surface by washing.
In accordance with the present invention, there are provided silicone compounds in which there is directly bonded to a silicon atom in the main chain of the polymer the group -(CH2)zOCH2CH(OH)C~2QH. These compounds differ from the compounds disclosed by the Ward application in the presence of the intervening spacer group -(CH2)z-. Because the Si-C bond is not broken by water there is no hydrolysis to free glycerol as in the Ward application. Rather, the compounds of the present invention are durable and skin substantive which is an advantage over the prior art as represented by the Ward application.
Because of this ad~antage of d~ability and substantivity, the compounds of the present invention provide the benefit of longar lasting moisturisation and exhibit humectant characteristics of attracting water because of the presence in the molecule of the glycerol functionality. The silicone portion of the molecule contributes its benefits of skin softening, ~ilm forming and the . .
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wi~h the result that it can be washed from the skin surface. It is used in many creams and lotions ior the purpose of keeping the skin soft and for replacing skin moisture. -The prior art is replete with various formulations which contain glycerol as an ingredient. One such prior art compo-sition is described in United States pat~nt application Serial No. 07/489117 .iled 5th ~arch 1990 of Andrew H. Ward entitled "Glyceroxyfunctional org2nosilicon Compounds", which application is assigned to Dow Corning Corporation. The Ward application discloses a silicone compound having the group -OCH~CH(OH)C~2OH
directly bonded to a silicon atom in the polymer main chain.
Upon contact with water, the silicone compound undergoes hydrolysis with the result that the si-o bond is cleaved and free glycerol is released onto the skin accom-panied by the simultaneous formation of silanol groups. However, as already noted, glycerol is not durable and can be easily removed from the skin surface by washing.
In accordance with the present invention, there are provided silicone compounds in which there is directly bonded to a silicon atom in the main chain of the polymer the group -(CH2)zOCH2CH(OH)C~2QH. These compounds differ from the compounds disclosed by the Ward application in the presence of the intervening spacer group -(CH2)z-. Because the Si-C bond is not broken by water there is no hydrolysis to free glycerol as in the Ward application. Rather, the compounds of the present invention are durable and skin substantive which is an advantage over the prior art as represented by the Ward application.
Because of this ad~antage of d~ability and substantivity, the compounds of the present invention provide the benefit of longar lasting moisturisation and exhibit humectant characteristics of attracting water because of the presence in the molecule of the glycerol functionality. The silicone portion of the molecule contributes its benefits of skin softening, ~ilm forming and the . .
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facilitation of spreading of the composition over the skin surfaces.
The present invention relates to new and novel compounds which are glycerol functional polysiloxanes having the Lormula R - Si - O ~- Si - O~ Si - o~ - Si - R
R ~ ¦ y R
L x (cx2)z-o-cH2-c~-CH~
OH OH
wherein R is an alkyl group having from one to 5iX carbon atoms or a phenyl group; x has a value of from zero to six hundred; y has a value of from one to 5iX hundred and z has a ~alue o~ from two to eight. While x can ~e 0 to 600 x preferably has a value of from one to three hundred. More preferably x has a value of from one to one hundred, and more particularly x has a value of from forty-five to one hundred. While y can be 1 to 600, preferably y has a value of from one to 100 and more prefera~ly 1 to ~0. While z can be 2 to 8 preferably z has a value o~ from three to six. In the most preferred embodiment of the present invention R is methyl; x has a value of 45 to 98; y has a value of 1 to 10 and z is three.
While ~he compounds of the present invention can be used for direct application to the skin, it is preferred to include them as an ingredient in topical skin conditioning formulations.
The glycerol functional polysiloxanes may be present in the skin conditioning formulation in an amount of about one to five per-cent by weight, and the compounds are particularly suitable for use in skin conditioning com~ositions which are in the form of creams although the compounds are equally effective in other delivered forms such as ointments, gels, lotions and emulsions.
.
.: . , : .: :
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~ ~3 PI~ 3 The process for preparlng the glycerol functional poly-siloxanes of the present inventiOn involves contacting alkenyloxy-1,2-propanediol with a polysiloxane having a reactive site. Preferably the alkenyloxy group is 3-allyloxy but other groups such 25 vinyloxy or ~-butenyloxy are also acceptable.
The diol and the siloxane are preferably heated under nitrogen to about 75C in the presence of a solvent such as isopropanol.
The reaction mixture may be catalysed with a noble metal catalyst such as chloroplat,nic acid and allowed to reflux for thirty minutes. Any active metal catalyst is suitable ~or the reaction, and particularly preferred are platinum catalysts such as platinum acetylacetonate or chloroplatinic acid. The mixture may then be cooled and the solvent e.g. isopropanol removed under vacuum for example at about 110C. The reaction mechanism as shown below has as reactive site R' hydrogen.
R [ R ~ L R ~ r R
H2P~Cl6.6H20 CH2 = CH - CH2 - O - CH - CH2 -~ -->
¦ l Isopropanol OH OH
R ~ R ~ R R
R - Si - O _ ~x CH2 ~ z-0-CH2-CE~-CH2 OH OH
Following are examples illustrating the preparation of glycerol functional polysiloxanes according to the present invention.
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; ' , :' ~ E I
A mixture containing 16.43 weight percent of 3-allyloxy-1,2-propanediol, 58.47 weight percent of the siloxane Me3SiO(Me2SiO)45(Me~SiO)5SiMe3, O.2 percent by weight of sodium acetate and 24.75 weight percent of isopropanol, was heated to 75~C under nitrogen. The mixture was catalysed with 0.15 weight percent of the catalyst HZPtCl6 in the form of a 0.7688 percent solu,ion in isopropanol. The mixture was allowed to reflux for thirty mlnutes. The reaction mixture was allowed to cool and the isopropanol solvent was removed by the application of a vacuum OI 50 mm/Hg and heating the mixture to 110C. A product was isolated and identified 2S the glycerol functional poly-siloxane Me3SiO(Me2SiO)45(MeRSiO)5SiMe3 in which Me is methyl and R is the group -cH2cH2cH2-o-cH2-c~3H-cH2oH.
E~ LE II
A mixture containing 9.57 weight percent of 3-allyloxy-1,2-propanediol, 65.17 weight percent of the siloxane Me3SiO(Me2SiO)47 5(MeHSiO)2 5SiMe3, 0.2 percent by weight of sodium acetate and 24.91 weight percent of isopropanol, was heated to 75OC under nitrogen. The mixture was catalysed with O.15 weight percent of the catalyst H2PtC16 in the form of a 0.7688 percent solution in isoproanol. The mixture was allowed to reflux for thirty minutes. The reaction mixture was allowed to cool and the isopropanol solvent was removed by the appli-cation of a vacuum of 50 mm/Hg and heating ~he mixture to 110C.
A product was isolated and identified as the glycerol functional 3 ( 2SiO)47.5(MeRSiO)2 5SiMe3 in which Me is methyl and R is the group -CH2CH2CH2-O-CH2-CHOH-CH2OH.
EXAMPLE III
A mixturP containing 4.39 weight percent of 3-allyloxy-1,2-propanediol, 70.35 weight percent of the siloxane Me3SiO(Me~SiO)49(MeHSiO)lSiMe3, O.2 percent by weight of sodium acetate and 24.91 welght percent of isopropanol, was heated to : : : , . . .
~. :
- ~ - ,; .
:: . - .: . , , 75OC under nitrogen. The mixture W2S catalysed with 0.15 weight percent of the catalyst ~2PtC16 in the form of a 0.7688 percent solution in isoproanol. The mixture was allowed to reflux for thirty minutes. The reaction mixture was allowed to cool and the isopropanol solvent was removed by the application of a vacuum of ~0 mm/Hg and heating the mixture to 110C. A product was isolated and identified as the glycerol functional poly-siloxane Me3SiO(Me2SiO)49(MeRSiO)1SiMe3 in which Me is methyl and R is the group -CH2CH2CH2-O-C~2-C~O~-C~2OH.
E~MP~E IV
A mixture containing 16.57 weight percent of 3-allyloxy-1,2-propanediol, 58.30 weight percent of the siloxane Me3SiO(Me2SiO)90(Me~Sio)10SiMe3, O.2 percent by weight of sodium acetate and 24.78 weight percent of isopropanol, was heated to 75C under nitrogen. The mixture was catalysed with 0.15 weight percent of the catalyst H2PtC16 in the form of a 0.7688 percent solution in isoproanol. The mixture was allowed to reflux for thirty minutes. The reaction mixture was allowed to cool and the isopropanol solvent was removed by the application of a vacuum of 50 mm/Hg and heating the mixture to 110C. A product was isolated and identified as the glycerol functional poly-siloxane Me3SiO(Me2SiO)90(MeRSiO)10SiMe3 in which Me is methyl and R is the group -C~2CH2CH2-O-CX2-C~OH-C~2OH.
EXAMPLE V
A mixture containing 9.57 w~ight percent of 3-allyloxy-1,2-propanediol, 65.17 weight percent of the siloxane Me3SiO(Me2SiO)95(MeHSiO)5SiMe3, 0.2 percent by weight of sodium acetate and 24.91 weight percent of isopropanol, was heated to 75C under nitrogen. The mixture was catalysed with 0.15 weight percent of the catalyst H2PtC16 in the form of a 0.7688 percent solution in isoproanol. The mixture was allowed to reflux for thirty minutes. The reaction mixture was allowed to cool and the isopropanol solvent was removed by the application of a '' . ~ , , . - . .
- . . . .
.. , . . . :
!
vacuum OL 50 mm/Hg and hea~ing the mixture to 110C. A product was isolated and identified as the glycerol functional poly-siloxane Me3SlO(Me2SiO)95(MeRSiO)5SiMe3 in which Me is methyl and R is the 5roup -C~2c~2c~2--cx2-cHH-c~2H
The polymerisation catalyst for the reaction can include a variety of hydrosilation catalysts known to promote the reaction of vinyl-functional radicals with silicon-bonded hydrogen akoms.
Ac~ive me.al catalysts such as platinum or rhodium-containing metal compound are included in this class of catalysts.
Platinum catalysts such as platinum acetylacetonate or chloro-platinic acid are representative of these compounds and suitable for US2 . A preferred catalyst mixture is a chloroplatinic acid complex of divinyltetramethyldisiloxane diluted in dimethyl-vinylsiloxy endblocked polydimethylsiloxane which may be prepared according to methods described by Willing in U.S.
Patent No. 3,419,593. Most preferably this mixLure contains about 0.6 weight percent platinum.
Hyd.osilation catalysts are well known in the art and t~e interes~ed reader is referred to the following patents for detailed descriptions regarding their preparation and use:
Speier, U.S. Patent No. 2,823,218; Willing, U.S. Patent No.
3,419,359; Kookootsedes, U.S. Patent No. 3,445,420; Polmanteer et al, U.S. Patent No. 3,697,473; Nitzsche, UOS. Patent No.
3,814,731~ Chandra, U.S. Patent No. 3,890,3S9 and Sandford, U.5.
Patent No. 4,123,604. Many of the catalysts known in the art require the reactants to be heated in or~er for reaction to occur. When such catalysts are employed this requirement must be taken into consideration.
When platinum catalysts are used an inhibitor may be required in ordex to improve the shelf life of the starting materials and to control the viscosity-time profile of the compositions. These inhibitors are also known in the art and lnclude ethylenically unsa,ura~ed isocyanurates, such as .
, .
; , . - , .~ ~ .
- :
trialkylisocyanurate, dialkylacetylenedicarboxylates, alkyl maleates, phosphines, phosphites, aminoalkyl silanes, sulphoxides, acrylonotrile derivatives and others. Particular inhibitors prererably used are diethyl ~umarate, bis(2-methoxy-1-methylene)maleate, bis(2-methoxy~ methylethyl)maleate and similar compounds.
The concentrations of catalyst and inhibitor to be used in the present invention may be determined by routine experimen-tation. Typically, the effective amount of catalyst should be in a range so as to provide from about 0.1 to 1000 parts per million (ppm) of platinum by weight in the compositions of the present invention. As an example, when the preferred catalyst mixture (i.e. the chloroplatinic acid complex of divinyltetra-methyldisiloxane containing about 0.6~ by weight of platinum) and inhibitor (i.e. bis(2-methoxy-1-methylethyl)maleate) are employed, a ratio by weight of inhibitor to catalyst mixture ranging from zero to about 0.6 provides a suitably wide range of inhibition which is adequate under mos~ practical conditions of manufacture.
The substantivity of the waxy glycerol functional poly siloxanes of the present invention wa~ verified ~y the use of in vivo Fourier transform infrared spectroscopy with attenuated total reflectance (ATR/~TIR) in accordance with the procedure described in the Journal of the SocietY of Cosmetic Chemists, Volume 37, pages 73 to 89, March/April 1986. Test data indicated that the waxy glycerol functional polysiloxanes were capable of providing an occlusive ~ilm on the skin similar to petrolatum which enhances moisturisation of the skin.
It will be apparent from the foregoing tha~ many other variations and modifications may be made in the compounds and compositions described herein without departing from the essential essence of the invention. It should be understood :
, ~' that the forms of the invention described herein are exemplary and not intended as limitations on the scope o~ the present invention as defined in the appended claims.
, ~ ;
~ - :
The present invention relates to new and novel compounds which are glycerol functional polysiloxanes having the Lormula R - Si - O ~- Si - O~ Si - o~ - Si - R
R ~ ¦ y R
L x (cx2)z-o-cH2-c~-CH~
OH OH
wherein R is an alkyl group having from one to 5iX carbon atoms or a phenyl group; x has a value of from zero to six hundred; y has a value of from one to 5iX hundred and z has a ~alue o~ from two to eight. While x can ~e 0 to 600 x preferably has a value of from one to three hundred. More preferably x has a value of from one to one hundred, and more particularly x has a value of from forty-five to one hundred. While y can be 1 to 600, preferably y has a value of from one to 100 and more prefera~ly 1 to ~0. While z can be 2 to 8 preferably z has a value o~ from three to six. In the most preferred embodiment of the present invention R is methyl; x has a value of 45 to 98; y has a value of 1 to 10 and z is three.
While ~he compounds of the present invention can be used for direct application to the skin, it is preferred to include them as an ingredient in topical skin conditioning formulations.
The glycerol functional polysiloxanes may be present in the skin conditioning formulation in an amount of about one to five per-cent by weight, and the compounds are particularly suitable for use in skin conditioning com~ositions which are in the form of creams although the compounds are equally effective in other delivered forms such as ointments, gels, lotions and emulsions.
.
.: . , : .: :
-- : -. ~ :
~ ~3 PI~ 3 The process for preparlng the glycerol functional poly-siloxanes of the present inventiOn involves contacting alkenyloxy-1,2-propanediol with a polysiloxane having a reactive site. Preferably the alkenyloxy group is 3-allyloxy but other groups such 25 vinyloxy or ~-butenyloxy are also acceptable.
The diol and the siloxane are preferably heated under nitrogen to about 75C in the presence of a solvent such as isopropanol.
The reaction mixture may be catalysed with a noble metal catalyst such as chloroplat,nic acid and allowed to reflux for thirty minutes. Any active metal catalyst is suitable ~or the reaction, and particularly preferred are platinum catalysts such as platinum acetylacetonate or chloroplatinic acid. The mixture may then be cooled and the solvent e.g. isopropanol removed under vacuum for example at about 110C. The reaction mechanism as shown below has as reactive site R' hydrogen.
R [ R ~ L R ~ r R
H2P~Cl6.6H20 CH2 = CH - CH2 - O - CH - CH2 -~ -->
¦ l Isopropanol OH OH
R ~ R ~ R R
R - Si - O _ ~x CH2 ~ z-0-CH2-CE~-CH2 OH OH
Following are examples illustrating the preparation of glycerol functional polysiloxanes according to the present invention.
, , ,:, . :- ', .
; ' , :' ~ E I
A mixture containing 16.43 weight percent of 3-allyloxy-1,2-propanediol, 58.47 weight percent of the siloxane Me3SiO(Me2SiO)45(Me~SiO)5SiMe3, O.2 percent by weight of sodium acetate and 24.75 weight percent of isopropanol, was heated to 75~C under nitrogen. The mixture was catalysed with 0.15 weight percent of the catalyst HZPtCl6 in the form of a 0.7688 percent solu,ion in isopropanol. The mixture was allowed to reflux for thirty mlnutes. The reaction mixture was allowed to cool and the isopropanol solvent was removed by the application of a vacuum OI 50 mm/Hg and heating the mixture to 110C. A product was isolated and identified 2S the glycerol functional poly-siloxane Me3SiO(Me2SiO)45(MeRSiO)5SiMe3 in which Me is methyl and R is the group -cH2cH2cH2-o-cH2-c~3H-cH2oH.
E~ LE II
A mixture containing 9.57 weight percent of 3-allyloxy-1,2-propanediol, 65.17 weight percent of the siloxane Me3SiO(Me2SiO)47 5(MeHSiO)2 5SiMe3, 0.2 percent by weight of sodium acetate and 24.91 weight percent of isopropanol, was heated to 75OC under nitrogen. The mixture was catalysed with O.15 weight percent of the catalyst H2PtC16 in the form of a 0.7688 percent solution in isoproanol. The mixture was allowed to reflux for thirty minutes. The reaction mixture was allowed to cool and the isopropanol solvent was removed by the appli-cation of a vacuum of 50 mm/Hg and heating ~he mixture to 110C.
A product was isolated and identified as the glycerol functional 3 ( 2SiO)47.5(MeRSiO)2 5SiMe3 in which Me is methyl and R is the group -CH2CH2CH2-O-CH2-CHOH-CH2OH.
EXAMPLE III
A mixturP containing 4.39 weight percent of 3-allyloxy-1,2-propanediol, 70.35 weight percent of the siloxane Me3SiO(Me~SiO)49(MeHSiO)lSiMe3, O.2 percent by weight of sodium acetate and 24.91 welght percent of isopropanol, was heated to : : : , . . .
~. :
- ~ - ,; .
:: . - .: . , , 75OC under nitrogen. The mixture W2S catalysed with 0.15 weight percent of the catalyst ~2PtC16 in the form of a 0.7688 percent solution in isoproanol. The mixture was allowed to reflux for thirty minutes. The reaction mixture was allowed to cool and the isopropanol solvent was removed by the application of a vacuum of ~0 mm/Hg and heating the mixture to 110C. A product was isolated and identified as the glycerol functional poly-siloxane Me3SiO(Me2SiO)49(MeRSiO)1SiMe3 in which Me is methyl and R is the group -CH2CH2CH2-O-C~2-C~O~-C~2OH.
E~MP~E IV
A mixture containing 16.57 weight percent of 3-allyloxy-1,2-propanediol, 58.30 weight percent of the siloxane Me3SiO(Me2SiO)90(Me~Sio)10SiMe3, O.2 percent by weight of sodium acetate and 24.78 weight percent of isopropanol, was heated to 75C under nitrogen. The mixture was catalysed with 0.15 weight percent of the catalyst H2PtC16 in the form of a 0.7688 percent solution in isoproanol. The mixture was allowed to reflux for thirty minutes. The reaction mixture was allowed to cool and the isopropanol solvent was removed by the application of a vacuum of 50 mm/Hg and heating the mixture to 110C. A product was isolated and identified as the glycerol functional poly-siloxane Me3SiO(Me2SiO)90(MeRSiO)10SiMe3 in which Me is methyl and R is the group -C~2CH2CH2-O-CX2-C~OH-C~2OH.
EXAMPLE V
A mixture containing 9.57 w~ight percent of 3-allyloxy-1,2-propanediol, 65.17 weight percent of the siloxane Me3SiO(Me2SiO)95(MeHSiO)5SiMe3, 0.2 percent by weight of sodium acetate and 24.91 weight percent of isopropanol, was heated to 75C under nitrogen. The mixture was catalysed with 0.15 weight percent of the catalyst H2PtC16 in the form of a 0.7688 percent solution in isoproanol. The mixture was allowed to reflux for thirty minutes. The reaction mixture was allowed to cool and the isopropanol solvent was removed by the application of a '' . ~ , , . - . .
- . . . .
.. , . . . :
!
vacuum OL 50 mm/Hg and hea~ing the mixture to 110C. A product was isolated and identified as the glycerol functional poly-siloxane Me3SlO(Me2SiO)95(MeRSiO)5SiMe3 in which Me is methyl and R is the 5roup -C~2c~2c~2--cx2-cHH-c~2H
The polymerisation catalyst for the reaction can include a variety of hydrosilation catalysts known to promote the reaction of vinyl-functional radicals with silicon-bonded hydrogen akoms.
Ac~ive me.al catalysts such as platinum or rhodium-containing metal compound are included in this class of catalysts.
Platinum catalysts such as platinum acetylacetonate or chloro-platinic acid are representative of these compounds and suitable for US2 . A preferred catalyst mixture is a chloroplatinic acid complex of divinyltetramethyldisiloxane diluted in dimethyl-vinylsiloxy endblocked polydimethylsiloxane which may be prepared according to methods described by Willing in U.S.
Patent No. 3,419,593. Most preferably this mixLure contains about 0.6 weight percent platinum.
Hyd.osilation catalysts are well known in the art and t~e interes~ed reader is referred to the following patents for detailed descriptions regarding their preparation and use:
Speier, U.S. Patent No. 2,823,218; Willing, U.S. Patent No.
3,419,359; Kookootsedes, U.S. Patent No. 3,445,420; Polmanteer et al, U.S. Patent No. 3,697,473; Nitzsche, UOS. Patent No.
3,814,731~ Chandra, U.S. Patent No. 3,890,3S9 and Sandford, U.5.
Patent No. 4,123,604. Many of the catalysts known in the art require the reactants to be heated in or~er for reaction to occur. When such catalysts are employed this requirement must be taken into consideration.
When platinum catalysts are used an inhibitor may be required in ordex to improve the shelf life of the starting materials and to control the viscosity-time profile of the compositions. These inhibitors are also known in the art and lnclude ethylenically unsa,ura~ed isocyanurates, such as .
, .
; , . - , .~ ~ .
- :
trialkylisocyanurate, dialkylacetylenedicarboxylates, alkyl maleates, phosphines, phosphites, aminoalkyl silanes, sulphoxides, acrylonotrile derivatives and others. Particular inhibitors prererably used are diethyl ~umarate, bis(2-methoxy-1-methylene)maleate, bis(2-methoxy~ methylethyl)maleate and similar compounds.
The concentrations of catalyst and inhibitor to be used in the present invention may be determined by routine experimen-tation. Typically, the effective amount of catalyst should be in a range so as to provide from about 0.1 to 1000 parts per million (ppm) of platinum by weight in the compositions of the present invention. As an example, when the preferred catalyst mixture (i.e. the chloroplatinic acid complex of divinyltetra-methyldisiloxane containing about 0.6~ by weight of platinum) and inhibitor (i.e. bis(2-methoxy-1-methylethyl)maleate) are employed, a ratio by weight of inhibitor to catalyst mixture ranging from zero to about 0.6 provides a suitably wide range of inhibition which is adequate under mos~ practical conditions of manufacture.
The substantivity of the waxy glycerol functional poly siloxanes of the present invention wa~ verified ~y the use of in vivo Fourier transform infrared spectroscopy with attenuated total reflectance (ATR/~TIR) in accordance with the procedure described in the Journal of the SocietY of Cosmetic Chemists, Volume 37, pages 73 to 89, March/April 1986. Test data indicated that the waxy glycerol functional polysiloxanes were capable of providing an occlusive ~ilm on the skin similar to petrolatum which enhances moisturisation of the skin.
It will be apparent from the foregoing tha~ many other variations and modifications may be made in the compounds and compositions described herein without departing from the essential essence of the invention. It should be understood :
, ~' that the forms of the invention described herein are exemplary and not intended as limitations on the scope o~ the present invention as defined in the appended claims.
, ~ ;
~ - :
Claims (8)
1. A glycerol functional polysiloxane having the formula wherein R is an alkyl group having from one to six carbon atoms or a phenyl group; x has a value of from zero to about six hundred; y has a value of from one to about six hundred and z has a value of from two to about eight.
2. A polysiloxane according to Claim 1 in which R is methyl.
3. A polysiloxane according to Claim 1 or Claim 2 in which x has a value of from one to three hundred.
4. A polysiloxane according to Claim 3 in which x has a value of from one to one hundred.
5. A polysiloxane according to Claim 4 in which x has a value of from forty-five to one hundred.
6. A polysiloxane according to any one of the preceding claims in which y has a value of from one to one hundred.
7. A polysiloxane according to any one of the preceding claims in which z has a value of from three to six.
8. A polysiloxane according to any one of the preceding claims in which R is methyl; x has a value of 45-98; y has a value of 1 to 10 and z is three.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9120025.3 | 1991-09-19 | ||
| GB919120025A GB9120025D0 (en) | 1991-09-19 | 1991-09-19 | Glycerol functional polysiloxanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2074616A1 true CA2074616A1 (en) | 1993-03-20 |
Family
ID=10701667
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2074616 Abandoned CA2074616A1 (en) | 1991-09-19 | 1992-07-24 | Glycerol functional polysiloxanes |
Country Status (2)
| Country | Link |
|---|---|
| CA (1) | CA2074616A1 (en) |
| GB (1) | GB9120025D0 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10843422B2 (en) | 2017-06-07 | 2020-11-24 | Alcon, Inc. | Method for producing silicone hydrogel contact lenses |
| US10866344B2 (en) | 2017-06-07 | 2020-12-15 | Alcon Inc. | Silicone hydrogel contact lenses |
| US10875967B2 (en) | 2017-06-07 | 2020-12-29 | Alcon Inc. | Silicone hydrogel contact lenses |
-
1991
- 1991-09-19 GB GB919120025A patent/GB9120025D0/en active Pending
-
1992
- 1992-07-24 CA CA 2074616 patent/CA2074616A1/en not_active Abandoned
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10843422B2 (en) | 2017-06-07 | 2020-11-24 | Alcon, Inc. | Method for producing silicone hydrogel contact lenses |
| US10866344B2 (en) | 2017-06-07 | 2020-12-15 | Alcon Inc. | Silicone hydrogel contact lenses |
| US10875967B2 (en) | 2017-06-07 | 2020-12-29 | Alcon Inc. | Silicone hydrogel contact lenses |
Also Published As
| Publication number | Publication date |
|---|---|
| GB9120025D0 (en) | 1991-11-06 |
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| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |