Patent EP0044872A1 successfully refreshed from Google Patents.
EP0044872A1
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Process for selectively separating water-soluble valuable materials from an aqueous solution containing same
Assignee: Toray Industries Inc
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Filing: 1980-07-21
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Granted: —
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Expires: 2000-07-21
Abstract
Abstract A process for selectively separating water-soluble valuables such as various organic compounds dissolved in water or transition metal compounds dissolved in water as ions or complexes from an aqueous solution containing them in slight amounts according to a reverse osmosis method by bringing the aqueous solution into contact with a semipermeable membrane under a pressure exceeding the osmotic pressure, which comprises employing, as the semipermeable membrane, a semipermeable composite membrane comprising a porous support having provided thereon a barrier layer of about 0.01 to 0.1µ in thickness made of a cross-linked polymer having the isocyanurate structure represented by the following general formula (I) and, if necessary, a protective layer of about 0.1 to 10 µ composed of polyvinyl alcohol and/or partially saponified polyvinyl acetate on the barrier layer: wherein R 1 represents a member selected from the group consisting of a glycidyl group and a group represented by the following formula (II): (wherein A represents an alkylene group containing 2 to 5 carbon atoms and optionally having a hydroxy group and/ or a glycidyl group, B represents an alkylene group containing 1 to 17 carbon atoms, X represents -0- and/or bond, n represents 0 or a positive integer and, when n represents an integer of 1 or more, B may be the same as, or different from, each other, and R' represents a hydrogen atom or an alkyl group containing 2 to 5 carbon atoms and having a hydroxy group und/or a glycidyl group), R 2 represents a hydrogen atom, an alkyl group containing 2 to 5 carbon atoms or that defined for R 1 , and the isocyanurate structure of the aforesaid cross-linked polymer is bonded via
Inventors
- 👤 Masaru Kurihara
- 👤 Noriho Harumiya
- 👤 Tetsuo Watanabe
- 👤 Naokatsu Kanamaru
- 👤 Tadahiro Uemura
- 👤 Yukio Toray Apt. B1-41 Nakagawa
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-03 16:46
CPC Classifications
B; B01; B01D; B01D71/00; B01D71/06; B01D71/58; B01D71/62; B01D61/00; B01D61/02; B01D61/025; B01D69/00; B01D69/12; B01D69/1213
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
270 words
A method of selective separation of water-soluble useful materials from their aqueous solutions by contacting the aqueous solutions with semipermeable composite membranes having selective separation capability under pressure maintained above the osmotic pressure of said aqueous solutions, which is characterised in that the semipermeable composite membrane is constituted of a microporous supporting layer, or substrate, and a barrier layer formed on its surface, said barrier layer comprising a cross-linked polymer and of which the thickness being within the range of about 0.01 micron to about 0.1 micron, wherein said cross-linked polymer is an intermolecular reaction product of compounds having the isocyanurate structure represented by the following general formula (I): wherein R 1 is a group selected from a series of groups including glycidyl groups and groups defined by the following formula (II): wherein A is an alkylene group having 2 to 5 carbon atoms containing or not containing a hydroxyl group and/or a glycidyl group or have none. B is an alkylene group having 1 to 17 carbon atoms. X indicates the - O - and/or linkage. n is zero or a positive integral number, B may be either the same of different when n is 1 or a larger number, and R' is a hydrogen or an alkyl group having 2 to 5 carbon atoms, and having a hydroxyl group and/or a glycidyl group, and R 2 indicated a group selected from the group consisting of hydrogen, alkyl groups having 2 to 5 carbon atoms and R 1 the isocyanurate structure of the aforesaid cross- linked polymer being combined by the medium of the - 0 - and/or linkage.
Claim 2
Independent Claim
270 words
A method of selective separation of water-soluble useful materials from their aqueous solutions by contacting the aqueous solutions with semipermeable composite membranes having selective separation capability under pressure maintained above the osmotic pressure of said aqueous solutions, which is characterised in that the semipermeable composite membrane is constituted of a microporous supporting layer, or substrate, and a barrier layer formed on its surface, said barrier layer comprising a cross-linked polymer and of which the thickness being within the range of about 0.01 micron to about 0.1 micron, wherein said cross-linked polymer is an intermolecular reaction product of compounds having the isocyanurate structure represented by the following general formula (I): wherein R 1 is a group selected from a series of groups including glycidyl groups and groups defined by the following formula (II): wherein A is an alkylene group having 2 to 5 carbon atoms containing or not containing a hydroxyl group and/or a glycidyl group or have none. B is an alkylene group having 1 to 17 carbon atoms. X indicates the - O - and/or linkage. n is zero or a positive integral number, B may be either the same of different when n is 1 or a larger number, and R' is a hydrogen or an alkyl group having 2 to 5 carbon atoms, and having a hydroxyl group and/or a glycidyl group, and R 2 indicated a group selected from the group consisting of hydrogen, alkyl groups having 2 to 5 carbon atoms and R 1 the isocyanurate structure of the aforesaid cross- linked polymer being combined by the medium of the - 0 - and/or linkage.
Claim 3
Dependent Claim
86 words
A method of selective separation of water-soluble useful materials from their aqueous solutions as claimed in Claim 1, wherein said water-soluble useful material is at least one kind of compound selected from the group consisting of organic compounds which are hydrocarbons and their derivatives having at least one of these three kinds of elements, viz. oxygen, sulfur and nitrogen, wherein the total number of atoms of carbon, hydrogen, oxygen, sulfur and nitrogen is within the range of 7 to 30, boric compounds and transition metal compounds.
Claim 4
Dependent Claim
126 words
A method of selective separation of water-soluble useful materials from their aqueous solutions as claimed in Claim 2, wherein said organic compound or compounds is at least one kind of compound or compounds selected from the group consisting of aliphatic alcohols having 2 to 8 carbon atoms, carboxylic acids having 2 to 8 carbon atoms, aldehydes having 2 to 8 carbon atoms, ketones having 3 to 8 carbon atoms, phenols having 6 to 13 carbon atoms, amides having 1 to 8 carbon atoms, esters having 2 to 10 carbon atoms, ethers having 4 to 8 carbon atoms, amines having 2 to 10 carbon atoms, hydroxy acids having 3 to 7 carbon atoms, aprotic-polar solvents, other than the above mentioned compounds, having 2 to 6 carbon atoms.
Claim 5
Dependent Claim
268 words
A method of selective separation of water-soluble useful materials from their aqueous solutions as claimed in Claim 2 * , wherein said aliphatic alcohol is at least one kind selected from the group consisting of ethyl alcohol, propyl alcohol, cyclohexanol, ethylene glycol, glycerine, sorbitol and cyclohexanediol, said * This should be claim 3. In the original Japanese text, however, it is stated as "claim2". carboxylic acid is at least one kind selected from the group consisting of formic acid, acetic acid, propionic acid, butyric acid, benzoic acid, toluic acid, oxalic acid, malonic acid, phthalic acid and trimellitic acid; said aldehyde is at least one kind selected from the group consisting of acetaldehyde, propionaldehyde, furfural and benzaldehyde, said ketone is at least one kind or kinds selected from the group consisting of acetone, methyl ethyl ketone, cyclohexanone and acetophenone; said ether is at least one kind or kinds selected from the group consisting of diethyl ether, anisole, tetrahydrofuran, tetra- hydropyrane, dioxane and styrene oxide; said ester is at least one kind selected from the group consisting of methyl acetate, methyl bezoate and methyl acrylate; said amine is at least one kind selected from the group consisting of ethylamine, benzylamine, aniline, toluidine, piperidine, piperazine, dimethylamine, triethylamine and pyridine; said amide is at least one kind selected from the group consisting of formamide, acetamide, urea and £-caprolactam; said phenol is at least one kind selected from the group consisting of phenol, cresol, resorcinol, hydroquinone, aminophenol and pyrogallol; and said hydroxy acid is at least one kind selected from the group consisting of lactic acid, malic acid, tartaric acid and citric acid.
Claim 6
Dependent Claim
56 words
A method of selective separation of water-soluble useful materials from their aqueous solutions as claimed in Claim 2, wherein said transition metal compound is at least one kind of compound selected from the group consisting of Ni, Co, Fe, Cr, U, Ag, Au, Cu, Mo, W, Hg and Pt compounds which form ions or complex ions.
Claim 7
Dependent Claim
48 words
A method of selective separation of water-soluble useful materials from their aqueous solutions as claimed in Claim 2, wherein said useful material or materials is at least one kind of compound selected from the group consisting of ethylene glycol, acetic acid, tetrahydrofuran, ethyl alcohol, phenol, E-caprolactam and dimethylformamide.
Claim 8
Dependent Claim
45 words
A method of selective separation of water-soluble useful materials from their aqueous solutions as claimed in Claim 1, wherein the concentration of useful materials contained in said aqueous solutions of water soluble useful materials is within the range of about 0.01 to about 20 wt.pct.
Claim 9
Dependent Claim
45 words
.8. A method of selective separation of water-soluble useful materials from their aqueous solutions as claimed in Claim 7, wherein the concentration of useful materials contained in said aqueous solutions of water-soluble useful materials is within the range of about 0.1 to about 10 wt.pct.
Claim 10
Dependent Claim
33 words
A method of selective separation of water-soluble useful materials from their aqueous solutions as claimed in Claim 1, wherein the kinds of useful materials contained in said aqueous solutions are at least two.
Claim 11
Dependent Claim
32 words
A method of selective separation of water-soluble useful materials from their aqueous solutions as claimed in Claim 1, wherein said aqueous solutions are brackish water or sea water containing water-soluble useful materials.
Claim 12
Dependent Claim
59 words
A method of selective separation of water-soluble useful materials from their aqueous solutions as claimed in Claim 1, wherein there is provided, on the surface of the barrier layer constituting the semipermeable composite membrane, a membrane layer consisting of polyvinyl alcohol and/or partly saponified polyvinyl acetate, which has been made insoluble in water, for protection of said barrier layer.
Claim 13
Dependent Claim
37 words
A method of selective separation of water-soluble useful materials from their aqueous solutions as claimed in Claim 11, 'wherein the thickness of said water-insolubilized membrane layer is within the range of about 0.1 to about 10 microns.
Claim 14
Dependent Claim
37 words
A method of selective separation of water-soluble useful materials from their aqueous solutions as claimed in Claim 12, wherein the thickness of said water-insolubilized membrane layer is within the range of about 0.5 to about 2 microns.
Claim 15
Dependent Claim
53 words
A method of selective separation of water-soluble useful materials from their aqueous solutions as claimed in Claim 11, wherein the average degree of polymerization of polyvinyl alcohol and/or partly saponified polyvinyl acetate is from about 100 to about 3,000, and the degree of saponification of partly saponified polyvinyl acetate is at least 0.70.
Claim 16
Dependent Claim
50 words
A method of selective separation of water-soluble useful materials from their aqueous solutions as claimed in Claim 1, wherein the compound represented by the general formula (I) is at least one kind selected. from these: 1,3,5-tris (hydroxyethyl) isocyanuric acid, bis (2-hydroxypropyl) isocyanuric acid, 1,3,5-tris (glycidyl) isocyanuric acid, and mixtures thereof.
Claim 17
Dependent Claim
91 words
A method of selective separation of water-soluble useful materials from their aqueous solutions as claimed in Claim 1, wherein the cross-linked polymer is a product of reaction between a compound represented by the general formula (I) and at least one kind of water-soluble comonomer selected from these: furfuryl alcohol, tetrahydrofurfuryl alcohol, epoxy compounds having 2 to 5 carbon atoms, polyethylene oxide, polyhydric alcohols having 2 to 8 carbon atoms, polyhydric carboxylic acids having 2 to 17 carbon atoms, polyhydric hydroxy acids having 2 to 17 carbon atoms, formaldehyde, and mixtures thereof.
Claim 18
Dependent Claim
50 words
A method of selective separation of water-soluble useful materials from their aqueous solutions as claimed in Claim 16, wherein the cross-linked polymer is a product of intermolecular reaction between a compound represented by the general formula (I) and furfuryl alcohol and/or a polyhydric alcohol having 2 to 8 carbon atoms.
Claim 19
Independent Claim
109 words
A method of selective separation of water-soluble useful materials from their aqueous solutions as claimed in Claims 16 and 17, wherein said epoxy compound is at least one kind selected from ethylene oxide or propylene oxide, or a mixture thereof said polyhydric alcohol is at least one kind or kinds selected from ethylene glycol, glycerine, sorbitol, inositol, and mixtures thereof; said polyhydric carboxylic acid is at least one kind selected from oxalic acid, succinic acid, maleic acid, fumaric acid, 1,2,3,4-butanetetracarboxylic acid, and mixtures thereof; and said polyhydric hydroxy acid is at least one kind selected from glycolic acid, malic acid, tartaric acid, citric acid, salicylic acid, and mixtures thereof.
Claim 20
Dependent Claim
53 words
A method of selective separation of water-soluble useful materials from their aqueous solutions as claimed in Claim 16, wherein the cross- linked polymer is a product of intermolecular reaction between at least 15 wt.pct. of a compound represented by the general formula (I) and not more than 85 wt.pct. of a water-soluble comonomer.
Claim 21
Dependent Claim
54 words
' A method of selective separation of water-soluble useful materials from their aqueous solutions as claimed in Claim 19, wherein the cross-linked polymer is a product of intermolecular reaction between about 20 to 80 wt.pct. of a compound represented by the general formula (I) and about 80 to 20 wt.pct. of a water-soluble comonomer.
Claim 22
Dependent Claim
45 words
A method of selective separation of water-soluble useful materials from their aqueous solutions as claimed in Claim 1, wherein the cross-linked polymer is at least one of the water-soluble intermolecular condensation products and/or addition reaction products of a compound represented by the general formula (I).
Claim 23
Dependent Claim
70 words
A method of selective separation of water-soluble useful materials from their aqueous solutions as claimed in Claim 21, wherein the water-soluble intermolecular condensation product and/or addition product is/are at least one kind or kinds selected from these: an intermolecular condensation product of 1,3,5-tris (hydroxyethyl) isocyanuric acid; an intermolecular condensation product of 1,3,5-tris (hydroxyethyl) isocyanuric acid and formaldehyde; and an addition reaction product of 1,3,5-tris (glycidyl) isocyanuric acid and ethylene glycol.
Claim 24
Dependent Claim
84 words
A method of selective separation of water-soluble useful materials from their aqueous solutions as claimed in Claim 21, wherein the water-soluble intermolecular condensation product and/or addition product is/are a product or products of reaction between a compound represented by the general formula (I) and epoxy compound having 2 to 5 carbon atoms, polyethylene oxide, polyhydric alcohol having 2 to 8 carbon atoms, polyhydric carboxylic acid having 2 to 17 carbon atoms, polyhydric hydroxy acid having 2 to 17 carbon atoms, formaldehyde, and mixtures thereof.
Claim 25
Dependent Claim
124 words
A method of selective separation of water-soluble useful materials from their aqueous solutions as claimed in Claim 21 * , wherein the epoxy compound is at least one kind selected from ethylene oxide or propylene oxide, or a mixture thereof; the polyhydric alcohol is at least one kind selected from ethylene glycol, glycerine, sor- * This should be claim 23. In the original Japanese text, however, it is stated as "claim 21". bitol, inositol, and mixtures thereof; the polyhydric carboxylic acid is at least one kind selected from oxalic acid, succinic acid, maleic acid, fumaric acid, and mixtures thereof; and the polyhydric hydroxy acid is at least one kind selected from glycolic acid, malic acid, tartaric acid, citric acid, salicylic acid, and mixtures thereof.
Claim 26
Dependent Claim
38 words
A method of selective separation of water-soluble useful materials from their aqueous solutions as claimed in Claim 21, wherein the water-soluble intermolecular condensation product is a product of intermolecular reaction between 1,3,5-tris (hydroxyethyl) isocyanuric acid and furfuryl alcohol.
Claim 27
Dependent Claim
29 words
A method of selective separation of water-soluble useful materials from their aqueous solutions as claimed in Claim 1, wherein the microporous supporting layer consists of polysulfone or polyvinyl chloride.
Claim 28
Dependent Claim
47 words
A method of selective separation of water-soluble useful materials from their aqueous solutions as claimed in Claim 1, wherein the thickness of the microporous supporting layer is from about 30 to 1,000 microns, and the thickness of the barrier layer is from about 50 to 1,000 angstroms.
Claim 29
Dependent Claim
46 words
A method of selective separation of water-soluble useful materials from their aqueous solutions as claimed in Claim 27, wherein the thickness of the microporous supporting layer is from about 100 to 300 microns, and the thickness of the barrier layer is from 100 to 500 angstroms.
Claim 30
Dependent Claim
50 words
A method of selective separation of water-soluble useful materials from their aqueous solutions as claimed in Claim 26, wherein the microporous supporting layer is reinforced or laminated with a reinforcing material selected from the group of materials including; textiles, either calendered or not calendered; nonwoven fabric; microporous film; and paper.
References Cited (Backward Citations)
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