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US3892686A Expired / Lapsed US ⏱️ 0.0 years remaining

Cellular products produced by foaming and cross-linking aromatic polysulfides

Assignee: Chevron USA Inc
•
Filing: 1973-03-26
•
Granted: 1975-07-01
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Expires: 1993-03-26
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Abstract

Abstract Sulfur-based foams produced by reacting aromatic carbocyclic or heterocyclic compound substituted by -OH, or -NHR groups with molten sulfur to form an aromatic polysulfide, cross-linking the product, generating CO2 or COS in situ before cross-linking is complete, and cooling the foamed product to ambient temperature. In a preferred embodiment the product of the aromatic carbocyclic compound and sulfur is modified with certain carboxy, sulfonic, phosphonic, phosphinic, boronic or borinic acids and crosslinking and CO2 generation is accomplished by addition of a polyisocyanate. Additional sulfur and liquid organic polysulfides may be incorporated in the foams.

Inventors

  • 👤 Gar Lok Woo

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-29 09:07
CPC Classifications
C; C08; C08L; C08L81/00; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/64; C08G18/6453; C08J; C08J9/00; C08J9/04; C08J9/06; C08J9/08; C08L63/00; C08J2381/00; C08J2381/04; Y; Y10; Y10S; Y10S521/00; Y10S521/908

Claims Analysis

Total Claims: 45
Claim 1
Independent Claim 8 words
A SULFUR-BASED FOAM PRODUCED BY THE STEPS OF
Claim 2
Dependent Claim 8 words
A SULFUR-BASED FOAM PRODUCED BY THE STEPS OF
Claim 3
Dependent Claim 176 words
MIXING AND STIRRING FOR A PERIOD OF FROM 1 TO 24 HOURS AT A TEMPRATURE OF FROM ABOUT 120*TO ABOUT 200*C. FROM ABOUT 0.5A TO 50A PARTS OF ELEMENTAL SULFUR WITH 1 PART OF AN AROMATIC CARBOCYCLIC OR HETEROCYCLIC COMPOUND CONTAINING FROM ABOUT 4 TO 24 CARBON ATOMS, SAID AROMATIC COMPOUNDS BEING SUBSTITUTED BY AT LEAST ONE GROUP OF THE FORMULA -OH OR -NHR IN WHICH R IS HYDROGEN OR LOWER ALKYL, SAID COMPOUND CONTAINING AT LEAST 2 RING HYDROGEN ATOMS PER MOLECULE, WHEREIN THE STABILIZATION ENERGY OF SAID AROMATIC COMPOUND IS AT LEAST 20 IN THE CASE OF THE CARBOCYCLIC COMPOUNDS AND 10 IN THE CASE OF THE HETEROCYCLIC COMPOUNDS, AND WHEREIN A IS EQUAL TO THE AVERAVE NUMBER OF -OH OR-NHR GROUPS IN THE AROMATIC COMPOUND ON A MOLAR BASIS, AND II. CONTACTING THE PRODUCT OF(1) AT A TEMPRATURE OF ABOUT 100*TO 200*C. WITH FROM ABOUT 0.002 TO 0.50 ACID EQUIVALENTS PER 100 G. OF (1) OF AN ACID OF THE FORMULA EQUIVALENTS PER 100 G. OF (1) OF AN ACID OF THE FORMULA
Claim 4
Dependent Claim 176 words
MIXING AND STIRRING FOR A PERIOD OF FROM 1 TO 24 HOURS AT A TEMPRATURE OF FROM ABOUT 120*TO ABOUT 200*C. FROM ABOUT 0.5A TO 50A PARTS OF ELEMENTAL SULFUR WITH 1 PART OF AN AROMATIC CARBOCYCLIC OR HETEROCYCLIC COMPOUND CONTAINING FROM ABOUT 4 TO 24 CARBON ATOMS, SAID AROMATIC COMPOUNDS BEING SUBSTITUTED BY AT LEAST ONE GROUP OF THE FORMULA -OH OR -NHR IN WHICH R IS HYDROGEN OR LOWER ALKYL, SAID COMPOUND CONTAINING AT LEAST 2 RING HYDROGEN ATOMS PER MOLECULE, WHEREIN THE STABILIZATION ENERGY OF SAID AROMATIC COMPOUND IS AT LEAST 20 IN THE CASE OF THE CARBOCYCLIC COMPOUNDS AND 10 IN THE CASE OF THE HETEROCYCLIC COMPOUNDS, AND WHEREIN A IS EQUAL TO THE AVERAVE NUMBER OF -OH OR-NHR GROUPS IN THE AROMATIC COMPOUND ON A MOLAR BASIS, AND II. CONTACTING THE PRODUCT OF(1) AT A TEMPRATURE OF ABOUT 100*TO 200*C. WITH FROM ABOUT 0.002 TO 0.50 ACID EQUIVALENTS PER 100 G. OF (1) OF AN ACID OF THE FORMULA EQUIVALENTS PER 100 G. OF (1) OF AN ACID OF THE FORMULA
Claim 5
Dependent Claim 33 words
A foam as in claim 1 in which in step (III) isocyanate or isothiocyanate groups necessary to react with at least 50% of the carboxyl groups in the product of (II) are provided.
Claim 6
Dependent Claim 21 words
A concentrate suitable for use as the sulfur-containing foam precursor of claim 1 comprising the product of (II) in claim 1.
Claim 7
Dependent Claim 40 words
A foam as in claim 1 wherein an additional amount of sulfur up to about 50 parts total sulfur to one part aromatic compound is blended at a temperature above about 120*C with one part of the product of (I).
Claim 8
Dependent Claim 40 words
A foam as in claim 1 wherein an additional amount of sulfur up to about 50 parts total sulfur to one part aromatic compound is blended at a temperature above about 120*C with one part of the product of (II).
Claim 9
Dependent Claim 30 words
A foam as in claim 1 in which a quantity of up to 25% by weight of an inert, finely divided stabilizing agent is added to the product of (I).
Claim 10
Dependent Claim 29 words
A foam as in claim 4 in which a quantity of an inert, finely divided stabilizing agent sufficient to stabilize said foam is added to the product of (II).
Claim 11
Dependent Claim 12 words
The foam of claim 5 in which the stabilizing agent is talc.
Claim 12
Dependent Claim 12 words
The foam of claim 7 in which the stabilizing agent is talc.
Claim 13
Dependent Claim 15 words
The foam of claim 1 wherein the aromatic compound employed in Step (I) is carbocyclic.
Claim 14
Dependent Claim 11 words
The foam of claim 10 wherein the aromatic compound is hydroxyaromatic.
Claim 15
Dependent Claim 11 words
The foam of claim 11 wherein the aromatic compound is phenol.
Claim 16
Dependent Claim 15 words
The foam of claim 1 in which Y in the acid of step (II) is
Claim 17
Dependent Claim 21 words
The foam of claim 1 in which the acid employed in step (II) is an unsaturated carboxylic acid of the formula
Claim 18
Dependent Claim 12 words
The foam of claim 14 in which R3 and R4 are H.
Claim 19
Dependent Claim 12 words
The foam of claim 4 in which the acid is dithiodipropionic acid.
Claim 20
Dependent Claim 12 words
The foam of claim 4 in which the acid is dithiodiglycolic acid.
Claim 21
Dependent Claim 13 words
The foam of claim 4 in which the acid is Beta -mercaptopropionic acid.
Claim 22
Dependent Claim 15 words
The foam of claim 1 in which Y in the acid of step (II) is
Claim 23
Dependent Claim 15 words
The foam of claim 1 in which Y in the acid of step (II) is
Claim 24
Dependent Claim 15 words
The foam of claim 1 in which the compound employed in Step (III) is aromatic.
Claim 25
Dependent Claim 16 words
The foam of claim 21 in which the compound employed in step (III) is diphenylmethane diisoCyanate.
Claim 26
Dependent Claim 17 words
The foam of claim 21 in which the compound employed in step (III) is polymethylene polyphenyl isocyanate.
Claim 27
Dependent Claim 16 words
The foam of claim 21 in which the compound employed in step (III) is tolylene diisocyanate.
Claim 28
Dependent Claim 25 words
The foam of claim 1 in which from 0.05 to 5% by weight of a basic material is employed as a catalyst in steip (I).
Claim 29
Dependent Claim 19 words
The foam of claim 25 in which the basic material is an alkali metal or alkaline earth metal hydroxide.
Claim 30
Dependent Claim 41 words
The foam of claim 4 wherein an additional quantity of from about 5 to about 150% of a liquid polysulfide by weight relative to the product of step (I) is incorporated in the composition after step (I) and before step (IV).
Claim 31
Dependent Claim 16 words
The foam of claim 27 in which the liquid polysulfide is a polyalkylenepolysulfide or polyoxyalkylene polysulfide.
Claim 32
Dependent Claim 20 words
The foam of claim 28 in which the liquid polysulfide has a molecular weight of from about 500 to 10,000.
Claim 33
Dependent Claim 14 words
The foam of claim 29 in which the liquid polysulfide is a polyoxyalkylene polysulfide.
Claim 34
Dependent Claim 21 words
The foam of claim 27 wherein the liquid polysulfide is incorporated in the product of step (I) prior to step (II).
Claim 35
Dependent Claim 20 words
The foam of claim 1 in which from 2A to 9A parts of elemental sulfur are employed in step (I).
Claim 36
Dependent Claim 23 words
The foam of claim 1 in which the amount of acid employed in step (II) is from about 0.005 to 0.15 acid equivalents.
Claim 37
Dependent Claim 21 words
The foam of claim 4 in which the total sulfur is up to about 20 parts per part of aromatic compound.
Claim 38
Dependent Claim 21 words
The foam of claim 5 in which the total sulfur is up to about 20 parts per part of aromatic compound.
Claim 39
Dependent Claim 125 words
A sulfur-based foam produced by steps comprising a. reacting, at a temperature between about 120* and 250*c, one mol of an aromatic carbocyclic or heterocyclic compound substituted by at least 1 functional group of the class -OH or -NHR, in which R is H or lower alkyl with at least 2 mols of molten sulfur to form an aromatic polysulfide, b. reacting the polysulfide with from 0.002 to 0.50 g. mole acid equivalents of an organic acid per 100 grams of the polysulfide at a temperature between about 100* and 200*c. so as to obtain a polysulfide-organic acid adduct having unreacted acidic groups, and c. foaming said adduct by reacting, at a temperature between about 100* and 180*c., an organic polyisocyanate with the acidic groups.
Claim 40
Dependent Claim 125 words
A sulfur-based foam produced by steps comprising a. reacting, at a temperature between about 120* and 250*c, one mol of an aromatic carbocyclic or heterocyclic compound substituted by at least 1 functional group of the class -OH or -NHR, in which R is H or lower alkyl with at least 2 mols of molten sulfur to form an aromatic polysulfide, b. reacting the polysulfide with from 0.002 to 0.50 g. mole acid equivalents of an organic acid per 100 grams of the polysulfide at a temperature between about 100* and 200*c. so as to obtain a polysulfide-organic acid adduct having unreacted acidic groups, and c. foaming said adduct by reacting, at a temperature between about 100* and 180*c., an organic polyisocyanate with the acidic groups.
Claim 41
Dependent Claim 17 words
A product in accordance with claim 36 wherein the organic acid is a carboxylic or thiocarboxylic acid.
Claim 42
Dependent Claim 14 words
A product in accordance with claim 36 wherein the organic acid is acrylic acid.
Claim 43
Dependent Claim 32 words
A product in accordance with claim 36 wherein the organic polyisocyanate is an aromatic diisocyanate having a boiling point higher than 130*C and is soluble or liquid at the foaming reaction conditions.
Claim 44
Dependent Claim 127 words
A process for producing a sulfur-based foam which comprises a. reacting, at a temperature between about 120 and 250*C., one mol of an aromatic carbocyclic or heterocyclic compound substituted by at least 1 functional group of the class -OH or -NHR, in which R is H or lower alkyl with at least 2 mols of molten sulfur to form an aromatic polysulfide, b. reacting the polysulfide with from 0.002 to 0.50 g. mole acid equivalents of an organic acid per 100 grams of the polysulfide at a temperature between about 100* and 200*C. so as to obtain a polysulfide-organic acid adduct having unreacted acidic groups, and c. foaming said adduct by reacting, at a temperature between about 100* and 180*C., an organic polyisocyanate with the acidic groups.
Claim 45
Dependent Claim 127 words
A process for producing a sulfur-based foam which comprises a. reacting, at a temperature between about 120 and 250*C., one mol of an aromatic carbocyclic or heterocyclic compound substituted by at least 1 functional group of the class -OH or -NHR, in which R is H or lower alkyl with at least 2 mols of molten sulfur to form an aromatic polysulfide, b. reacting the polysulfide with from 0.002 to 0.50 g. mole acid equivalents of an organic acid per 100 grams of the polysulfide at a temperature between about 100* and 200*C. so as to obtain a polysulfide-organic acid adduct having unreacted acidic groups, and c. foaming said adduct by reacting, at a temperature between about 100* and 180*C., an organic polyisocyanate with the acidic groups.

References Cited (Backward Citations)

US3114723A Cited
US3498936A Cited
US3494966A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1978-06-30 1978-12-30 1979-07-01 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1982-06-30 1982-12-30 1983-07-01 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1986-06-30 1986-12-30 1987-07-01 $7700.00 Window Closed / Lapsed

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