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US4124553A Expired / Lapsed US ⏱️ 0.0 years remaining

Method for the preparation of a composition containing polycarbamoyl sulphonates from polyisocyanates

Assignee: Commonwealth Scientific and Industrial Research Organisation
•
Filing: 1976-12-02
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Granted: 1978-11-07
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Expires: 1996-12-02
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Abstract

Abstract A method for the preparation of a composition containing PCS from polyisocyanates which comprises the following steps in the stated order:

Inventors

  • 👤 Geoffrey B. Guise

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-26 20:48
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/08; C08G18/0804; C08G18/0819; D; D06; D06M; D06M13/00; D06M13/322; D06M13/402; D06M13/425; D06M15/00; D06M15/19; D06M15/37; D06M15/564

Claims Analysis

Total Claims: 19
Claim 1
Independent Claim 303 words
A method for the preparation of a composition containing polycarbamoyl sulphonates from polyisocyanates which comprises the following steps in the stated order: Step 1: Mixing a polyisocyanate with (a) an aqueous solution of an alkali metal or ammonium bisulphite or metabisulphite, or an aqueous solution of a mixture of any two or more of these salts; (b) one or more tertiary amines containing on average per molecule one or more tertiary amino groups of the type R 1 R 2 R 3 N where R 1 , R 2 and R 3 are each alkyl, aryl, or cycloalkyl groups or two or more of the groups R 1 , R 2 and R 3 together form alicyclic or aromatic rings; and (c) at least one water-miscible solvent selected from the group consisting of: lower aliphatic alcohols with from one to six carbon atoms, ethylene glycol, propylene glycol, diethylene glycol, the mono and di ethers of the said glycols with lower aliphatic alcohols with from one to six carbon atoms, dioxan, tetrahydro furan and tetrahydrofuryl alcohol; and Step 2 Mixing the reaction mixture from Step 1 with at at least one mineral acid or solution thereof; wherein the polyisocyanate is prepared by the reaction of (d) a compound or mixture of compounds containing on average two or more isocyanate groups per molecule, and (e) a compound or mixture of compounds with two or more groups selected from one or more of the groups: hydroxyl, thiol, primary amino, secondary amino or carboxylic acid; and wherein for each mole of isocyanate groups of the polyisocyanate there is at least one mole of bisulphite ion or its equivalent; and wherein the number of moles of tertiary amino groups in component (b) is not greater than the number of moles in (a) of bisulphite ions or their equivalents.
Claim 2
Independent Claim 303 words
A method for the preparation of a composition containing polycarbamoyl sulphonates from polyisocyanates which comprises the following steps in the stated order: Step 1: Mixing a polyisocyanate with (a) an aqueous solution of an alkali metal or ammonium bisulphite or metabisulphite, or an aqueous solution of a mixture of any two or more of these salts; (b) one or more tertiary amines containing on average per molecule one or more tertiary amino groups of the type R 1 R 2 R 3 N where R 1 , R 2 and R 3 are each alkyl, aryl, or cycloalkyl groups or two or more of the groups R 1 , R 2 and R 3 together form alicyclic or aromatic rings; and (c) at least one water-miscible solvent selected from the group consisting of: lower aliphatic alcohols with from one to six carbon atoms, ethylene glycol, propylene glycol, diethylene glycol, the mono and di ethers of the said glycols with lower aliphatic alcohols with from one to six carbon atoms, dioxan, tetrahydro furan and tetrahydrofuryl alcohol; and Step 2 Mixing the reaction mixture from Step 1 with at at least one mineral acid or solution thereof; wherein the polyisocyanate is prepared by the reaction of (d) a compound or mixture of compounds containing on average two or more isocyanate groups per molecule, and (e) a compound or mixture of compounds with two or more groups selected from one or more of the groups: hydroxyl, thiol, primary amino, secondary amino or carboxylic acid; and wherein for each mole of isocyanate groups of the polyisocyanate there is at least one mole of bisulphite ion or its equivalent; and wherein the number of moles of tertiary amino groups in component (b) is not greater than the number of moles in (a) of bisulphite ions or their equivalents.
Claim 3
Dependent Claim 25 words
A method as claimed in claim 1, wherein there is from 1.05 to 1.5 moles of the bisulphite ion for each mole of the polyisocyanate.
Claim 4
Dependent Claim 42 words
A method as claimed in claim 1, wherein for each isocyanate group component (a) contains (1 + X) moles of bisulphite ions (or their equivalents) and component (b) contains X moles of tertiary amino groups, where X is from 0.1 to 0.5.
Claim 5
Dependent Claim 14 words
A method as claimed in claim 3, wherein X is from 0.2 to 0.4.
Claim 6
Dependent Claim 23 words
A method as claimed in claim 1, wherein the reactants (d) are those in which the isocyanate groups are attached to aromatic rings.
Claim 7
Dependent Claim 26 words
A method as claimed in claim 5, wherein the reactants (d) are selected from 2,4-tolylene diisocyanate, mixtures of 2,4- and 2,6-tolylene diisocyanates, and the isomeric diphenylmethanediisocyanates.
Claim 8
Dependent Claim 22 words
A method as claimed in claim 1, wherein the reactant (e) is a polypropylene oxide diol or triol, or a polyoxytetramethylene glycol.
Claim 9
Dependent Claim 26 words
A method as claimed in claim 1, wherein the bisulphite, metabisulphite or mixture of said salts of (a) are partially replaced by the corresponding sulphite salts.
Claim 10
Dependent Claim 48 words
A method as claimed in claim 1, wherein R 1 , R 2 and R 3 are alkyl groups with from one to five carbon atoms, benzyl groups or groups in which R 1 and R 2 together form part of a saturated five or six membered ring.
Claim 11
Dependent Claim 25 words
A method as claimed in claim 9, wherein the tertiary amine components (b) are selected from trimethylamine, triethylamine, triethanolamine, dimethylethanolamine, tribenzylamine, N-ethylmorpholine, N-methylpiperidine and N-methylpyrollidine.
Claim 12
Dependent Claim 16 words
A method as claimed in claim 1, wherein the component (b) contains two tertiary amino groups.
Claim 13
Dependent Claim 22 words
A method as claimed in claim 11, wherein the component (b) is selected from tetra-N-methylethylene diamine, triethylene diamine (i.e. 1,4-diazabicyclo[2,2,2]octane) and 1,4-dimethylpiperazine.
Claim 14
Dependent Claim 22 words
A method as claimed in claim 1, wherein the component (b) is a tertiary amine having a pK value greater than 9.
Claim 15
Dependent Claim 33 words
A method as claimed in claim 1, wherein the solvent is selected from the group consisting of ethanol, n-propanol, iso-porpanol, 2-methoxyethanol, 2-ethoxyethanol, ethylene glycol dimethyl ether, and diethylene glycol dimethyl or diethyl ethers.
Claim 16
Dependent Claim 43 words
A method as claimed in claim 1, wherein the component (c) contains up to 25% by weight of water-immiscible solvent selected from the group consisting of ethyl acetate, diethyl ether, toluene, xylene, perchoroethylene, and the acetates of ethylene glycol monomethyl and monoethyl ethers.
Claim 17
Dependent Claim 42 words
A method as claimed in claim 1, wherein the component (c) contains up to 50% by weight of a water-miscible organic solvent selected from the group consisting of dimethyl formamide, dimethylacetamide, dimethyl sulfoxide, acetone, methyl ethyl ketone, hexamethyl phosphoro triamide and sulpholane.
Claim 18
Dependent Claim 21 words
A method as claimed in claim 1, wherein the mineral acid component is selected from hydrochloric, hydrobromic, sulphuric or phosphoric acids.
Claim 19
Dependent Claim 14 words
A composition containing a polycarbamoyl sulphonate prepared according to the method of claim 1.

References Cited (Backward Citations)

AU460168B2 Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-11-06 1982-05-08 1982-11-07 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-11-06 1986-05-08 1986-11-07 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-11-06 1990-05-08 1990-11-07 $7700.00 Window Closed / Lapsed

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