# US 8,541,533 B2 · Fluorine-containing polyfunctional silicon compound and method for producing fluorine-containing polyfunctional silicon compound > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,541,533 B2 - Document ID: US8541533B2 - Status: Granted - Kind: B2 - Application number: 12/867,301 - Filed: 2009-02-12 - Published: 2010-12-23 - Granted: 2013-09-24 - Earliest claimed: 2008-02-12 - Assignees: FUJIFILM Corporation - Applicants: Takayuki Ito - Inventors: Takayuki Ito - Web page: https://patentgrep.com/patent/US8541533B2 ## CPC - C07F 7/0836: {Compounds with one or more Si-OH or Si-O-metal linkage} - C07F 7/1804: {Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896)} - C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22) ## Abstract A fluorine-containing polyfunctional silicon compound represented by the following general formula (I), which is useful as a raw material for materials having high water repellency and excellent scratch resistance and water droplet sliding properties and which can be produced by a production method which is simple and easy and environmentally friendly, is provided. In the formula, Q represents an (n+m)-valent organic group having at least one fluorine atom; each of Rf1 and Rf2 independently represents a fluorine atom, a hydrogen atom or an alkyl group having at least one fluorine atom; R1 represents a hydroxyl group, an isocyanate group or a hydrolyzable group; R2 represents a hydrogen atom or a hydrocarbon group; k represents 0 or 1; n represents an integer of 2 or more; m represents an integer of 0 or more; a represents an integer of from 1 to 6; and b represents an integer of from 1 to 3. ## Claims ### Claim 1 A fluorine-containing polyfunctional silicon compound represented by the following general formula (I): wherein in formula (I), Q represents an (n+m)-valent perfluoroalkyl group, which may have an ethereal oxygen atom; each of Rf1 and Rf2 independently represents a fluorine atom, a hydrogen atom or an alkyl group having at least one fluorine atom; R1 represents a hydroxyl group, an isocyanate group or a hydrolyzable group; R2 represents a hydrogen atom or a hydrocarbon group; k represents 0 or 1; n represents an integer of 2 or more; m represents an integer of 0 or more; a represents an integer of from 1 to 6; and b represents an integer of from 1 to 3, said compound being produced by reacting an (n+m)-valent fluorine-containing alcohol represented by the following general formula (I) and an isocyanate represented by the following general formula (VII) under a basic condition: wherein in formulas (I) and (VII), Q represents an (n+m)-valent perfluoroalkyl group, which may have an ethereal oxygen atom; k represents 0 or 1; each of Rf1 and Rf2 independently represents a fluorine atom, a hydrogen atom or an alkyl group having at least one fluorine atom; R1 represents a hydroxyl group, an isocyanate group or a hydrolyzable group; R2 represents a hydrogen atom or a hydrocarbon group; n represents an integer of 2 or more; m represents an integer of 0 or more; a represents an integer of from 1 to 6; and b represents an integer of from 1 to 3, and wherein the (n+m)-valent fluorine-containing alcohol represented by the formula (i) is selected from the group consisting of the compounds (i-1) to (i-21) as follows: ### Claim 2 (depends on 1) The fluorine-containing polyfunctional silicon compound according to claim 1, wherein, in the general formula (I), each of Rf1 and Rf2 independently represents a fluorine atom or a perfluoroalkyl group; and k represents 1. ### Claim 3 A method for producing a fluorine-containing polyfunctional silicon compound represented by the following general formula (I), in which an (n+m)-valent fluorine-containing alcohol represented by the following general formula (I) and an isocyanate represented by the following general formula (VII) are reacted under a basic condition: wherein Q represents an (n+m)-valent organic group having at least one fluorine atom; k represents 0 or 1; each of Rf1 and Rf2 independently represents a fluorine atom, a hydrogen atom or an alkyl group having at least one fluorine atom; R1 represents a hydroxyl group, an isocyanate group or a hydrolyzable group; R2 represents a hydrogen atom or a hydrocarbon group; n represents an integer of 2 or more; m represents an integer of 0 or more; a represents an integer of from 1 to 6; and b represents an integer of from 1 to 3, and wherein the (n+m)-valent fluorine-containing alcohol represented by the formula (I) is selected from the group consisting of the compounds (1-1) to (1-21) as follows: ### Claim 4 A method for producing of a fluorine-containing polyfunctional silicon compound represented by the following general formula (II), in which a fluorine-containing alcohol represented by the following general formula (II) and an isocyanate represented by the following general formula (VII) are reacted under a basic condition: wherein R1 represents a hydroxyl group, an isocyanate group or a hydrolyzable group; R2 represents a hydrogen atom or a hydrocarbon group; a represents an integer of from 1 to 6; b represents an integer of from 1 to 3; x represents an integer of from 1 to 200; L represents a divalent organic group; Rf11 represents a perfluoroalkylene group; each of Rf12 and Rf13 independently represents a fluorine atom, a perfluoroalkyl group or a perfluoroalkoxy group; and at least two of Rf11, Rf12 and Rf13 may be bonded to each other to form one or more rings. ### Claim 5 A method for producing of a fluorine-containing polyfunctional silicon compound represented by the following general formula (III), wherein a fluorine-containing alcohol represented by the following general formula (III) and an isocyanate represented by the following general formula (VII) are reacted under a basic condition: wherein R1 represents a hydroxyl group, an isocyanate group or a hydrolyzable group; R2 represents a hydrogen atom or a hydrocarbon group; a represents an integer of from 1 to 6; b represents an integer of from 1 to 3; x represents an integer of from 1 to 200; L represents a divalent organic group; and Rf14 represents a tetravalent perfluoroalkylene group. ### Claim 6 A method for producing of a fluorine-containing polyfunctional silicon compound represented by the following general formula (IV), wherein a fluorine-containing alcohol represented by the following general formula (Iv) and an isocyanate represented by the following general formula (VII) are reacted under a basic condition: wherein R1 represents a hydroxyl group, an isocyanate group or a hydrolyzable group; R2 represents a hydrogen atom or a hydrocarbon group; a represents an integer of from 1 to 6; b represents an integer of from 1 to 3; x represents an integer of from 1 to 200; and L represents a divalent organic group. ### Claim 7 (depends on 4) The method for producing of a fluorine-containing polyfunctional silicon compound according to claim 4, wherein L is a divalent organic group represented by the following general formula (V) or (VI): —CH2—Rf15—CH2— (V) —Ar1 (VI) wherein Rf15 represents a divalent perfluoroalkyl group; and Ar1 represents a divalent aryl group. ### Claim 8 (depends on 1) A processed substrate, which comprises a substrate having thereon a film formed from a composition containing the fluorine-containing polyfunctional silicon compound according to claim 1. ### Claim 9 (depends on 5) The method for producing of a fluorine-containing polyfunctional silicon compound according to claim 5, wherein L is a divalent organic group represented by the following general formula (V) or (VI): —CH2—Rf15—CH2— (V) —Ar1— (VI) wherein Rf15 represents a divalent perfluoroalkyl group; and Ar1 represents a divalent aryl group. ### Claim 10 (depends on 6) The method for producing of a fluorine-containing polyfunctional silicon compound according to claim 6, wherein L is a divalent organic group represented by the following general formula (V) or (VI): —CH2—Rf15—CH2— (V) —Ar1— (VI) wherein Rf15 represents a divalent perfluoroalkyl group; and Ar1 represents a divalent aryl group. ### Claim 11 (depends on 1) The fluorine-containing polyfunctional silicon compound according to claim 1, wherein, in the general formula (I), (n+m) represents an integer of 2 or more and not more than 6 and m represents an integer of not more than 5. ### Claim 12 (depends on 1) The fluorine-containing polyfunctional silicon compound according to claim 1, wherein m in formula (I) is 0. ### Claim 13 (depends on 3) The method for producing a fluorine-containing polyfunctional silicon compound according to claim 3, wherein m in formula (I) is 0. ### Claim 14 A fluorine-containing polyfunctional silicon compound represented by the following general formula (I): wherein Q represents an (n+m)-valent organic group having at least one fluorine atom; each of Rf1 and Rf2 independently represents a fluorine atom, a hydrogen atom or an alkyl group having at least one fluorine atom; R1 represents a hydroxyl group, an isocyanate group or a hydrolyzable group; R2 represents a hydrogen atom or a hydrocarbon group; k represents 0 or 1; n represents an integer of 2 or more; m represents an integer of 1 or more; a represents an integer of from 1 to 6; and b represents an integer of from 1 to 3.