WO2014151485A4 - Urea-siloxane compositions and methods of making the same - Google Patents

Urea-siloxane compositions and methods of making the same Download PDF

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Publication number
WO2014151485A4
WO2014151485A4 PCT/US2014/025832 US2014025832W WO2014151485A4 WO 2014151485 A4 WO2014151485 A4 WO 2014151485A4 US 2014025832 W US2014025832 W US 2014025832W WO 2014151485 A4 WO2014151485 A4 WO 2014151485A4
Authority
WO
WIPO (PCT)
Prior art keywords
nhch
composition
amino
siloxane
saccharide
Prior art date
Application number
PCT/US2014/025832
Other languages
French (fr)
Other versions
WO2014151485A1 (en
Inventor
John Horstman
Steven Swier
Simon Toth
Original Assignee
Dow Corning Corporation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dow Corning Corporation filed Critical Dow Corning Corporation
Publication of WO2014151485A1 publication Critical patent/WO2014151485A1/en
Publication of WO2014151485A4 publication Critical patent/WO2014151485A4/en

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Classifications

    • 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
    • C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
    • C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/15—Heterocyclic compounds having oxygen in the ring
    • C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
    • C08K5/1545—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
    • 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
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Silicon Polymers (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

An amphiphilic saccharide-urea-siloxane composition includes an amino-functional prepolymer reacted with saccharide lactone. The composition is prepared by reacting an amino-alkyl functional siloxane with isocyanate to form the amino-functional prepolymer, the molar ratio of amine in the amino-alkyl functional siloxane to cyanate in the isocyanate being greater than 1.

Claims

AMENDED CLAIMS received by the International Bureau on 12 September 2014 (12.09.2014)
1. An amphiphilic saccharide-urea-siloxane composition comprising:
an amino-functional prepolymer reacted with saccharide lactone,
wherein the composition is prepared by reacting an amino-alkyl functional siloxane with isocyanate to form the amino-functional prepolymer, the molar ratio of amine in the amino-alkyl functional siloxane to cyanate in the isocyanate being greater than 1.
2. The composition of claim 1 , wherein the amino-functional prepolymer is reacted with the saccharide lactone in a solvent or a melt.
3. The composition of claim 2, wherein the composition is a film, the film being formed by evaporating the solvent in the absence of further catalysis or chemical reaction.
4. The composition of any of claims 1-3, wherein the ratio of amine to cyanate is from about 1.01 to about 5.
5. The composition of claim 1 , wherein the composition comprises
about 0.01 to about 20 mol% urea;
about 0.01 to about 20 mol% saccharide; and
about 60 to about 99.8 mol% siloxane.
6. An amphiphilic saccharide-urea-siloxane composition comprising:
about 0.01 to about 20 mol% urea;
about 0.01 to about 20 mol% saccharide; and
about 60 to about 99.8 mol% siloxane.
7. The composition of any of claims 5-6, wherein the composition is a film, plastic, or elastomer.
8. The composition of any of claims 1-7, wherein the composition is used to form a skin adhesive, a film former, or a medical tubing.
9. The composition of any of claims 1-8, further comprising one or more drugs or active agents, the composition being configured to controllably release the one or more drugs.
10. A method of forming an amphiphilic saccharide-urea-siloxane composition, the method comprising:
reacting an amino-alkyl functional siloxane with isocyanate to form an amino- functional prepolymer, the molar ratio of amine in the amino-alkyl functional siloxane to cyanate in the isocyanate being greater than 1 ; and
reacting the amino-functional prepolymer with saccharide lactone to form the amphiphilic saccharide-urea-siloxane composition.
11. The method of claim 10, wherein the amino-functional prepolymer is reacted with the saccharide lactone in a solvent or a melt.
12. The method of claim 1 1 , further comprising evaporating the solvent to form a film of the amphiphilic saccharide-urea-siloxane composition in the absence of further catalysis or chemical reaction.
13. The method of any of claims 10-12, wherein the amino-alkyl functional siloxane includes one or more amino-alkyl functional siloxane chains, wherein the one or more amino-alkyl functional siloxane chains is linear and/or pendant functional with at least 2 amino functionality and has a general structure selected from
(c) (R1 mR2 n-Si(R2)2-0-[Si(R2)2-0]y-Si(R2)2-(R1 mR2n) or
(d) (b) Si(R2)3-0-[Si(R2R1)-0]x-[Si(R2)2-0]y-Si(R2)3
where m+n=1 , m is from 0.1 to 1 , x is from 1 to 2, y is from 1 to 1000, R2 is an alkyl chain with 1-18 carbons, and R1 is selected from -CH2CH2NH2, -CH2CH2 CH2NH2, - CH2CH2CH2CH2NH2, -CH2CH(CH3)CH2NH2, -CH2CH3CH2NHCH2CH2NH2-
CH2CH2NHCH2CH2NH2, -CH2CH2CH2NHCH2CH2CH2NH2,
CH2CH2CH2CH2NHCH2CH2CH2CH2NH2, -CH2CH2CH2NHCH2CH2NH2,
CH2CH(CH3)CH2NHCH2CH2NH2 -CH2CH2CH2CH2CH2NH2, -CH2CH2CH2CH2CH2CH2NH2, -CH2CH2NHCH3, -CH2CH2CH2NHCH3, -CH2CH2CH2CH2NHCH3, -CH2CH(CH3)CH2NHCH3, -CH2CH2NHCH2CH2NHCH3, -CH2CH2CH2NHCH2CH2CH2NH CH3,
CH2CH2CH2CH2NHCH2CH2CH2CH2NHCH3, -CH2CH2CH2NHCH2CH2NH CH3, CH2CH(CH3)CH2NHCH2CH2NHCH3, -CH2CH2CH2CH2CH2NHCH3, or CH2CH2CH2CH2CH2CH2NHCH3.
14. The method of any of claims 10-13, wherein the ratio of amine to cyanate is from about 1.01 to about 5.
15. An amphiphilic saccharide-urea-siloxane composition formed using the method of any of claims 10-14.
PCT/US2014/025832 2013-03-15 2014-03-13 Urea-siloxane compositions and methods of making the same WO2014151485A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201361787499P 2013-03-15 2013-03-15
US61/787,499 2013-03-15

Publications (2)

Publication Number Publication Date
WO2014151485A1 WO2014151485A1 (en) 2014-09-25
WO2014151485A4 true WO2014151485A4 (en) 2014-11-13

Family

ID=50680136

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2014/025832 WO2014151485A1 (en) 2013-03-15 2014-03-13 Urea-siloxane compositions and methods of making the same

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WO (1) WO2014151485A1 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10266657B2 (en) 2015-10-29 2019-04-23 Commonwealth Scientific And Industrial Research Organisation Polyurethane/urea compositions
CN111936558B (en) * 2018-04-12 2022-03-18 日本帕卡濑精株式会社 Polysiloxane compounds and compositions

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007139812A2 (en) * 2006-05-23 2007-12-06 Dow Corning Corporation Novel silicone film former for delivery of actives

Also Published As

Publication number Publication date
WO2014151485A1 (en) 2014-09-25

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