Siloxane derivatives, producing method thereof and agents including siloxane derivative

• US 5,306,838 A
• Filed: 08/07/1992
• Issued: 04/26/1994
• Est. Priority Date: 08/30/1990
• Status: Expired due to Term

• Current Assignee: KAO Corporation
• Original Assignee: KAO Corporation
• Inventors: Suzuki, Yuji, Takeuchi, Ken, Yoshino, Koji, Kawamata, Akira, Shioya, Yasushi
• Primary Examiner(s): PRESCOTT, ARTHUR
• Application Number:
  US07/926,186
• Time in Patent Office: 627 Days
• Field of Search: 556/445, 556/449, 556/450, 556/453, 556/466, 556/467, 556/25, 556/29
• US Class Current: 556/445
• CPC Class Codes: A61K 47/24 containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
• CPC Class Codes: A61K 8/893 modified by an alkoxy or aryloxy group, e.g. behenoxy dimethicone or stearoxy dimethicone
• CPC Class Codes: A61K 9/0014 Skin, i.e. galenical aspects of topical compositions non-active ingredients are additionally classified in A61K47/00; A61K9/0009, A61K9/0021, A61K9/7015, A61K9/7023 take precedence; cosmetic preparations A61K8/00, A61Q; preparations for wound dressings or bandages A61L26/00
• CPC Class Codes: A61Q 1/00 Make-up preparations; Body powders; Preparations for removing make-up
• CPC Class Codes: A61Q 1/02 Preparations containing skin colorants, e.g. pigments preparations in powder form A61Q1/12
• CPC Class Codes: A61Q 17/04 Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: A61Q 19/10 Washing or bathing preparations
• CPC Class Codes: A61Q 5/00 Preparations for care of the hair
• CPC Class Codes: C07F 7/0838 Compounds with one or more Si-O-Si sequences compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21
• CPC Class Codes: C08G 77/38 Polysiloxanes modified by chemical after-treatment C08G77/045 takes precedence

Abstract

Novel siloxane derivatives represented by general formula (1): ##STR1## A method for producing the siloxane derivatives and agents such as cosmetic preparations, emulsifying dermatotherapeutic external agents and the like including at least one of the siloxane derivatives are also disclosed.

Claims

1. A siloxane derivative represented by general formula (1) ##STR38## wherein at least one of R¹ to R¹² is a group represented by general formula (2) ##STR39## wherein Q is a divalent hydrocarbon group having 4 to 20 carbon atoms, R¹³ and R¹⁴ are hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms, and at least one of R¹³ and R¹⁴ is hydrogen atom;

the remaining R¹ to R¹² are straight-chain, branched-chain or cyclic hydrocarbon groups having 1 to 30 carbon atoms or groups represented by general formula (3)

space="preserve" listing-type="equation">--X--R.sup.15 (

     3)

wherein X is a divalent hydrocarbon group having an ether bonding and/or ester bonding and R¹⁵ is a straight-chain, branched-chain or cyclic hydrocarbon group having 1 to 30 carbon atoms;

l, m and n are numbers of 0 to 200, and at least one of R¹ to R³ and R¹⁰ to R¹² is a group represented by general formula (2) when l+m+n=0.

2. The siloxane derivative of claim 1, wherein Q is an alkylene group having 4 to 20 carbon atoms and R¹³ and R¹⁴ are hydrogen atoms, and wherein R¹ to R¹² are alkyl groups having 1 to 30 carbon atoms.

3. The siloxane derivative of claim 1, wherein l+m+n is 0 to 2000 and Q is an alkylene group having 4 to 20 carbon atoms.

4. The siloxane derivative of claim 1, wherein the siloxane derivative is represented by general formula (1A) ##STR40## wherein R^2A represents an alkyl group having 2 to 30 carbon atoms and s is a number of 4 to 20.

5. The siloxane derivative of claim 1, wherein the siloxane derivative is represented by general formula (1B) ##STR41## wherein t is a number of 0 to 2000 and u is a number of 4 to 20.

6. The siloxane derivative of claim 1, wherein the siloxane derivative is represented by general formula (1C) ##STR42## wherein t is a number of 0 to 2000 and s is a number of 4 to 20.

7. The siloxane derivative of claim 1, wherein the siloxane derivative is represented by general formula (1D) ##STR43## wherein R^4D represents an alkyl group having 2 to 30 carbon atoms, t and v are numbers of 0 to 1000, w is a number of 1 to 1000, and s is a number of 4 to 20.

9. A use as an emulsifier of a siloxane derivative specified in claim 1.

10. A cosmetic preparation including a siloxane derivative represented by general formula (1) specified in claim 1.

8. A method for producing a siloxane derivative represented by general formula (1b) ##STR44## wherein at least one of R¹ " to R¹² " represents a group represented by general formula (2) ##STR45## wherein Q is a divalent hydrocarbon group having 4 to 20 carbon atoms, R¹³ and R¹⁴ are hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms, and at least one of R¹³ and R¹⁴ is hydrogen atom;

at least one of the remainings of R¹ " to R¹² " represents a group represented by general formula (3)

space="preserve" listing-type="equation">--X--R.sup.15 (

     3)

wherein X is a divalent hydrocarbon group having an ether bonding and/or ester bonding and R¹⁵ is a straight-chain, branched-chain or cyclic hydrocarbon group having 1 to 30 carbon atoms; and

the remainings of R¹ " to R¹² " are straight-chain, branched-chain or cyclic hydrocarbon groups having 1 to 30 carbon atoms, and, when l+m+n=0, at least one of R¹ " to R^3" and R¹⁰ " to R¹² " represents a group represented by general formula (2) and at least one of the remainings of R¹ " to R³ " and R¹⁰ " to R¹² " represents a group represented by general formula (3), comprising reacting a compound represented by general formula (4'"'"') ##STR46## wherein at least two of R¹⁶ '"'"' to R²⁷ '"'"' represent hydrogen atoms, the remainings of R¹⁶ '"'"' to R²⁷ '"'"' represent a straight-chain, branched-chain or cyclic hydrocarbon group having 1 to 30 carbon atoms, l, m and n are the same as described above, and at least two of R¹⁶ '"'"' to R¹⁶ '"'"' and R²⁵ '"'"' to R²⁷ '"'"' represent hydrogen atoms when l+m+n=0, with compounds represented by general formulas (2'"'"') and (3'"'"') ##STR47## wherein Q'"'"' represents a hydrocarbon group having 4 to 20 carbon atoms and one double bond, and R¹³ and R¹⁴ are the same as described above, and

space="preserve" listing-type="equation">X'"'"'--R.sup.15 ( 3'"'"')

wherein X'"'"' is a hydrocarbon group having at least one double bond and an ether bonding and/or ester bonding and R¹⁵ is the same as described above.

11. A method for producing a siloxane derivative represented by general formula (1a) ##STR48## wherein at least one of R¹ '"'"' to R¹² '"'"' represents a group represented by general formula (2) ##STR49## wherein Q is a divalent hydrocarbon group having 4 to 20 carbon atoms, R¹³ and R¹⁴ are hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms, and at least one of R¹³ and R¹⁴ is hydrogen atom;

the remainings of R¹ '"'"' to R¹² '"'"' are straight-chain, branched-chain or cyclic hydrocarbon groups having 1 to 30 carbon atoms, and at least one of R¹ '"'"' to R³ '"'"' and R¹⁰ '"'"' to R¹² '"'"' represents a group represented by general formula (2) when l+m+n=0,

comprising reacting a compound represented by general formula (4) ##STR50## wherein at least one of R¹⁶ to R²⁷ represents hydrogen atom, the remainings of R¹⁶ to R²⁷ represent a straight-chain, branched-chain or cyclic hydrocarbon group having 1 to 30 carbon atoms, l, m and n are numbers of 0 to 2000, and at least one of R¹⁶ to R¹⁸ and R²⁵ to R²⁷ represents hydrogen atom when l+m+n=0, with a compound represented by general formula (2'"'"') ##STR51## wherein in formula (2'"'"') Q'"'"' represents a hydrocarbon group having 4 to 20 carbon atoms and one double bond, and R¹³ and R¹⁴ are the same as described above.

12. An emulsifying dermatotherapeutic external agent comprising:

(A) 5 to 70 weight % of oil phase component;

(B) 20 to 94.9 weight % of water phase component; and

(C) 0.1 to 30 weight % of emulsifier including a siloxane derivative represented by general formula (1) ##STR52## wherein at least one of R¹ to R¹² is a group represented by general formula (2) ##STR53## wherein Q is a divalent hydrocarbon group having 4 to 20 carbon atoms, R¹³ and R¹⁴ are hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms, and at least one of R¹³ and R¹⁴ is hydrogen atom;

the remainings of R¹ to R¹² are straight-chain, branched-chain or cyclic hydrocarbon groups having 1 to 30 carbon atoms or groups represented by general formula (3)

space="preserve" listing-type="equation">--X--R.sup.15 (

     3)

wherein X is a divalent hydrocarbon group having an ether bonding and/or ester bonding and R¹⁵ is a straight-chain, branched-chain or cyclic hydrocarbon group having 1 to 30 carbon atoms;

l, m and n are numbers of 0 to 200, and at least one of R¹ to R³ and R¹⁰ to R¹² is a group represented by general formula (2) when l+m+n=0.

13. The emulsifying dermatotherapeutic external agent of claim 12, wherein the oil phase component (A) includes at most 50 weight % of silicone oil, and wherein in the siloxane derivative of the component (C), l+m+n is 0 to 2000 and Q is an alkylene group having 4 to 20 carbon atoms.

14. The emulsifying dermatotherapeutic external agent of claim 12, wherein the oil phase component (A) includes 50 weight % of silicone oil, and wherein the siloxane derivative in component (C) is represented by either one of the following formulae (1A) to (1D):

##STR54## wherein R^2A represents an alkyl group having 2 to 30 carbon atoms and s is a number of 4 to 20, ##STR55## wherein t is a number of 0 to 2000 and u is a number of 4 to 20, ##STR56## wherein, t is a number of 0 to 2000 and s is a number of 4 to 20, ##STR57## wherein R^4D represents an alkyl group having 2 to 30 carbon atoms, t and v are numbers of 0 to 1000, w is a number of 1 to 1000, and s is a number of 4 to 20.