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US4557949A Expired / Lapsed US ⏱️ 0.0 years remaining

Method of making a reverse osmosis semipermeable membrane

Assignee: Toray Industries Inc
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Filing: 1984-02-01
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Granted: 1985-12-10
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Expires: 2004-02-01
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Abstract

Abstract A method of producing a semipermeable membrane comprising a polymeric material based upon a trisisocyanurate structure ##STR1## wherein, R 1 , R 2 and R 3 are hydrogen or alkyl radicals containing from 2 to 5 carbon atoms, and at least two of R 1 , R 2 and R 3 are alkyl radicals having hydroxyl or glycidyl groups. The membrane has high solute rejection, high flux, excellent high pressure resistance, and high temperature resistance and is a highly useful composite membrane for reverse osmosis. In the method, an aqueous solution containing, for example, a reaction product of Formula I is applied to the surface of a porous substrate and is heated at a temperature of about 100° C. to 190° C. to provide a cross-linked structure including a multiplicity of isocyanurate groups on the porous substrate.

Inventors

  • 👤 Masaru Kurihara
  • 👤 Tetsuo Watanabe
  • 👤 Tetsuo Inoue

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-03 15:29
CPC Classifications
C; C08; C08G; C08G65/00; C08G65/02; C08G65/26; C08G65/2618; C08G65/2621; C08G65/263; B; B01; B01D; B01D71/00; B01D71/06; B01D71/58; B01D71/62; C08G59/00; C08G59/18; C08G59/20; C08G59/22; C08G59/26; C08G63/00; C08G63/68; C08G63/685; C08G65/34; C08G65/36

Claims Analysis

Total Claims: 27
Claim 1
Independent Claim 322 words
A process of preparation of a semipermeable composite membrane comprising: (a) applying to the surface of a porous substrate an aqueous solution containing (A) at least one component selected from the group consisting of (i) a component defined by the Formula (I) or reaction products formed between a plurality of components of the formula: ##STR3## wherein each of R 1 , R 2 , and R 3 is selected from the group consisting of hydrogen, an alkyl radical containing from 2 to 5 carbon atoms, and an alkyl radical carrying a functional hydroxyl group or a functional glycidyl group, with the proviso that at least two of R 1 , R 2 , and R 3 comprise alkyl radicals carrying a functional hydroxyl group or a functional glycidyl group, (ii) reaction products between a compound defined as group (i) and at least one water soluble comonomer selected from the group consisting of furfuryl alcohol, tetrahydrofurfuryl alcohol, an epoxy compound containing from 2 to 5 carbon atoms, a multivalent alcohol containing from 2 to 8 carbon atoms, polyethylene oxide, a multivalent carboxylic acid containing from 2 to 17 carbon atoms, multivalent hydroxy acid containing from 2 to 17 carbon atoms and formaldehyde, and (iii) a mixture of reaction products between the compounds defined as group (i) and at least one water soluble comonomer selected from the group consisting of furfuryl alcohol, tetrahydrofurfuryl alcohol, an epoxy compound containing from 2 to 5 carbon atoms, a multivalent alcohol containing from 2 to 8 carbon atoms, polyethylene oxide, a multivalent carboxylic acid containing from 2 to 17 carbon atoms, a multivalent hydroxy acid containing from 2 to 17 carbon atoms and formaldehyde, and (B) an acid catalyst, and (b) heating the solution to polymerize the compound represented by the Formula (I) and/or said comonomer at a temperature of from about 100° C. to 190° C. for a period of about one minute to about 30 minutes.
Claim 2
Dependent Claim 322 words
A process of preparation of a semipermeable composite membrane comprising: (a) applying to the surface of a porous substrate an aqueous solution containing (A) at least one component selected from the group consisting of (i) a component defined by the Formula (I) or reaction products formed between a plurality of components of the formula: ##STR3## wherein each of R 1 , R 2 , and R 3 is selected from the group consisting of hydrogen, an alkyl radical containing from 2 to 5 carbon atoms, and an alkyl radical carrying a functional hydroxyl group or a functional glycidyl group, with the proviso that at least two of R 1 , R 2 , and R 3 comprise alkyl radicals carrying a functional hydroxyl group or a functional glycidyl group, (ii) reaction products between a compound defined as group (i) and at least one water soluble comonomer selected from the group consisting of furfuryl alcohol, tetrahydrofurfuryl alcohol, an epoxy compound containing from 2 to 5 carbon atoms, a multivalent alcohol containing from 2 to 8 carbon atoms, polyethylene oxide, a multivalent carboxylic acid containing from 2 to 17 carbon atoms, multivalent hydroxy acid containing from 2 to 17 carbon atoms and formaldehyde, and (iii) a mixture of reaction products between the compounds defined as group (i) and at least one water soluble comonomer selected from the group consisting of furfuryl alcohol, tetrahydrofurfuryl alcohol, an epoxy compound containing from 2 to 5 carbon atoms, a multivalent alcohol containing from 2 to 8 carbon atoms, polyethylene oxide, a multivalent carboxylic acid containing from 2 to 17 carbon atoms, a multivalent hydroxy acid containing from 2 to 17 carbon atoms and formaldehyde, and (B) an acid catalyst, and (b) heating the solution to polymerize the compound represented by the Formula (I) and/or said comonomer at a temperature of from about 100° C. to 190° C. for a period of about one minute to about 30 minutes.
Claim 3
Dependent Claim 33 words
A process according to claim 1, wherein the aqueous solution contains at least one additive selected from the group consisting of lower alcohols containing from 1 to 5 carbon atoms, and a surfactant.
Claim 4
Dependent Claim 31 words
A process according to claim 2, wherein the surfactant is selected from the group consisting of dodecyl sodium sulfate, sodium dodecylbenzene sulfonate, polyethylene glycol, polyethylene glycol monoalkylether and polyethylene glycol monostearate.
Claim 5
Dependent Claim 26 words
A process according to claim 2, wherein the lower alcohol is selected from the group consisting of methyl alcohol, ethyl alcohol, propyl alcohol and isopropyl alcohol.
Claim 6
Dependent Claim 13 words
A process according to claim 4, wherein the acid catalyst is sulfuric acid.
Claim 7
Dependent Claim 35 words
A process according to claim 21, wherein the acid catalyst is an acid selected from the group consisting of sulfuric acid, phosphoric acid, hydrogen chloride methane sulfonic acid, benzene sulfonic acid and toluene sulfonic acid.
Claim 8
Dependent Claim 14 words
A process according to claim 1, wherein the porous substrate is a polysulfone substrate.
Claim 9
Dependent Claim 31 words
A process according to claim 1, wherein said compound represented by the Formula I is selected from the group consisting of 1,3,5-tris(hydroxyethyl)isocyanuric acid, bis(2-hydroxypropyl)isocyanuric acid and 1,3,5-tris(glycidyl)isocyanuric acid, and mixtures thereof.
Claim 10
Dependent Claim 33 words
A process according to claim 1, wherein said aqueous solution is an aqueous solution containing a water soluble intermolecular condensation product and/or addition reaction product of said compound represented by the Formula (I).
Claim 11
Dependent Claim 50 words
A process according to claim 9, wherein said water soluble condensation product and/or addition reaction product is selected from the group consisting of an intermolecular condensation product of 1,3,5-tris(hydroxyethyl)isocyanuric acid, an intermolecular condensation product of 1,3,5-tris(hydroxylethyl)isocyanuric acid with formaldehyde, and an addition reaction product of 1,3,5-tris(glycidyl)isocyanuric acid with ethylene glycol.
Claim 12
Dependent Claim 35 words
A process according to claim 1, wherein said aqueous solution is an aqueous solution containing the compound represented by the Formula (I), furfuryl alcohol and/or a multivalent alcohol containing from 2 to 8 carbon atoms.
Claim 13
Dependent Claim 96 words
A process according to claim 1, wherein said epoxy compound is selected from the group consisting of ethylene oxide, propylene oxide and a mixture thereof, said multivalent alcohol is selected from the group consisting of ethylene glycol, glycerin, inositol, sorbitol and mixtures thereof, said multivalent carboxylic acid is selected from the group consisting of oxalic acid, maleic acid, succinic acid, fumaric acid, 1,2,3,4-butane tetracarboxylic acid, 1,2,3,4-benzene tetracarboxylic acid and mixtures thereof, and said multivalent hydroxy acid is selected from the group consisting of glycolic acid, malic acid, citric acid, tartaric acid, salicylic acid and mixtures thereof.
Claim 14
Dependent Claim 20 words
A process according to claim 1, wherein said aqueous solution is an aqueous solution containing 1,3,5-tris(hydroxyethyl)isocyanuric acid and furfuryl alcohol.
Claim 15
Dependent Claim 29 words
A process according to claim 1, wherein the water soluble comonomer is in a range of up to 85% by weight of the compound represented by the Formula (I).
Claim 16
Dependent Claim 25 words
A process according to claim 14, wherein the compound represented by the Formula (I) is in about a range of 20% to 80% by weight.
Claim 17
Dependent Claim 30 words
A process according to claim 1, wherein the porous substrate is about 100 to 300 microns in thickness and the semipermeable membrane is about 100 to 500 Angstroms in thickness.
Claim 18
Dependent Claim 36 words
A process according to claim 1, wherein said porous substrate is reinforced or piled on by a material selected from the group consisting of an uncalendered fabric, a calendered fabric, nonwoven fabric, porous film and paper.
Claim 19
Dependent Claim 63 words
A process for preparation of a semipermeable composite membrane comprising: (a) applying to the surface of a porous substrate an aqueous solution containing 1,3,5-tris(hydroxyethyl)isocyanuric acid, furfuryl alcohol, and an acid catalyst, and (b) heating to polymerize said 1,3,5-tris(hydroxyethyl)isocyanuric acid and furfuryl alcohol at a temperature of from about 100° C. to 190° C. for a period of about one minute to 30 minutes.
Claim 20
Dependent Claim 63 words
A process for preparation of a semipermeable composite membrane comprising: (a) applying to the surface of a porous substrate an aqueous solution containing 1,3,5-tris(hydroxyethyl)isocyanuric acid, furfuryl alcohol, and an acid catalyst, and (b) heating to polymerize said 1,3,5-tris(hydroxyethyl)isocyanuric acid and furfuryl alcohol at a temperature of from about 100° C. to 190° C. for a period of about one minute to 30 minutes.
Claim 21
Dependent Claim 13 words
A process according to claim 18, where said aqueous solution contains a surfactant.
Claim 22
Dependent Claim 31 words
A process according to claim 19, wherein said surfactant is selected from the group consisting of dodecyl sodium sulfate, sodium dodecyl benzene sulfonate, polyethylene glycol, polyethylene monoalkylether, and polyethylene glycol monostearate.
Claim 23
Dependent Claim 35 words
A process according to claim 18, wherein said acid catalyst is an acid selected from the group consisting of sulfuric acid, phosphoric acid, hydrogen chloride, methane sulfonic acid, benzene sulfonic acid and toluene sulfonic acid.
Claim 24
Dependent Claim 13 words
A process according to claim 21, wherein said acid catalyst is sulfuric acid.
Claim 25
Dependent Claim 12 words
A process according to claim 18, wherein said substrate is polysulfone substrate.
Claim 26
Dependent Claim 142 words
In a process for preparing a semipermeable membrane, the steps which comprise: (a) coating the surface of a porous substrate with a solution containing a multiplicity of isocyanurate groups of the formula: ##STR4## wherein each of R 1 , R 2 , and R 3 is selected from the group consisting of hydrogen, an alkyl radical containing from 2 to 5 carbon atoms, and an alkyl radical carrying a functional hydroxyl group or a functional glycidyl group, with the proviso that at least two of R 1 , R 2 , and R 3 comprise alkyl radicals carrying a functional hydroxyl group or a functional glycidyl group, and (b) polymerizing said groups by heating and curing at about 100° C. to 190° C. for a time to provide a crosslinked structure including a multiplicity of said isocyanurate groups on the porous substrate.
Claim 27
Dependent Claim 142 words
In a process for preparing a semipermeable membrane, the steps which comprise: (a) coating the surface of a porous substrate with a solution containing a multiplicity of isocyanurate groups of the formula: ##STR4## wherein each of R 1 , R 2 , and R 3 is selected from the group consisting of hydrogen, an alkyl radical containing from 2 to 5 carbon atoms, and an alkyl radical carrying a functional hydroxyl group or a functional glycidyl group, with the proviso that at least two of R 1 , R 2 , and R 3 comprise alkyl radicals carrying a functional hydroxyl group or a functional glycidyl group, and (b) polymerizing said groups by heating and curing at about 100° C. to 190° C. for a time to provide a crosslinked structure including a multiplicity of said isocyanurate groups on the porous substrate.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1988-12-09 1989-06-10 1989-12-10 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1992-12-09 1993-06-10 1993-12-10 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1996-12-09 1997-06-10 1997-12-10 $7700.00 Window Closed / Lapsed

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