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US4145509A Expired / Lapsed US ⏱️ 0.0 years remaining

Polyacrylated polyurethanes and gaskets having sealants thereof

Assignee: Dana Inc
•
Filing: 1978-04-21
•
Granted: 1979-03-20
•
Expires: 1998-04-21
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Abstract

Abstract An improved gasket is disclosed having a novel sealant comprising the reaction product of a monoacrylated, terminated, active hydrogen-containing hydrocarboxy reactant an aromatic diisocyanate, and a polyacrylated terminated hydrocarboxy reactant. The active hydrogen of the monoacrylated reactant reacts with at least one isocyanate radical of the aromatic diisocyanate to form an isocyanate linkage, and the reaction product of the monoacrylated and diisocyanate reactant is further reacted with the polyacrylated terminated reactant in widely varying mole ratios. The resulting gaskets have improved temperature resistance, compressibility, film hardness, elongation, flexibility, and organic solvent resistance.

Inventors

  • 👤 Yog R. Bhatia

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-26 04:59
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/67; C08G18/671; C08G18/672; Y; Y10; Y10S; Y10S277/00; Y10S277/935; Y10S277/944; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31551; Y10T428/31605; Y10T428/31609

Claims Analysis

Total Claims: 22
Claim 1
Independent Claim 94 words
As a composition of matter, the reaction product of (a) a monoacrylated terminated, active hydrogen-containing hydrocarboxy reactant, (b) an aromatic diisocyanate, and (c) a polyacrylated terminated hydrocarboxy reactant, the active hydrogen of reactant (a) reacting with at least one isocyanate radical of reactant (b) to form an isocyanate linkage, the reaction product of reactants (a) and (b) being reacted with reactant (c) in a molar ratio, respectively, of from 1:25 to 25:1, said reactant (c) serving primarily as a cross-linking agent to bond together linear chains formed by the reaction of (a) and (b).
Claim 2
Dependent Claim 94 words
As a composition of matter, the reaction product of (a) a monoacrylated terminated, active hydrogen-containing hydrocarboxy reactant, (b) an aromatic diisocyanate, and (c) a polyacrylated terminated hydrocarboxy reactant, the active hydrogen of reactant (a) reacting with at least one isocyanate radical of reactant (b) to form an isocyanate linkage, the reaction product of reactants (a) and (b) being reacted with reactant (c) in a molar ratio, respectively, of from 1:25 to 25:1, said reactant (c) serving primarily as a cross-linking agent to bond together linear chains formed by the reaction of (a) and (b).
Claim 3
Dependent Claim 29 words
The composition of matter of claim 1 in which said monoacrylated hydrocarboxy reactant has an alkyl or alkenyl linear stem and a molecular weight of up to about 8,000.
Claim 4
Dependent Claim 34 words
The composition of matter of claim 1 in which said monoacrylated hydrocarboxy reactant has the formula: ##STR5## in which R is hydrogen or methyl, and n is a whole number from 1 to 8.
Claim 5
Dependent Claim 54 words
The composition of matter of claim 1 in which the aromatic diisocyanate moiety in said first-mentioned reaction product is selected from the group consisting of: ##STR6## ##STR7## in which R is hydrogen or methyl, R 1 is (C 2 H 4 O) n , and n is a whole number from 1 to 8.
Claim 6
Dependent Claim 50 words
The composition of matter of claim 1 in which said polyacrylated terminated, hydrocarboxy reactant is diacrylated and selected from the group consisting of an alkylene glycol diacrylate, alkylene glycol dimethacrylate, a polyalkylene glycol diacrylate, and a polyalkylene glycol dimethacrylate, in which said alkylene group contains 4 to 8 carbon atoms.
Claim 7
Dependent Claim 66 words
The composition of matter of claim 1 in which said aromatic diisocyanate in the reaction product formed by reactants (a) and (b) has one isocyanate radical reacted with said active hydrogen of reactant (a) and the other isocyanate radical reacted with a carboxyl radical of an organic acid to form an ester group, said ester group having a molecular weight of about 500 to about 6,000.
Claim 8
Dependent Claim 59 words
The composition of matter of claim 6 in which said esterified isocyanate radical has the formula: ##STR8## in which x is a whole number from 2 to 4, y is a whole number from 2 to 12, and n is a number sufficient to provide a molecular weight from about 500 to about 6,000 for said esterified isocyanate radical.
Claim 9
Dependent Claim 125 words
A gasket comprising a base sheet and a sealant thereon comprising the reaction product of (a) a monoacrylated terminated, active hydrogen-containing hydrocarboxy reactant, (b) an aromatic diisocyanate, and (c) a polyacrylated terminated hydrocarboxy reactant, the active hydrogen of reactant (a) reacting with at least one diisocyanate radical of reactant (b) to form an isocyanate linkage, the reaction product of reactants (a) and (b) being reacted with reactant (c) in a molar ratio, respectively, of from 1:25 to 25:1, said gasket having a compressibility at 1,000 psi of about 2% to about 20%, a film hardness by pencil test of 6B to 4H, an elongation of about 2% to about 100%, and a flexibility by mandrel test of from 1/8 inch to one inch without failure.
Claim 10
Dependent Claim 125 words
A gasket comprising a base sheet and a sealant thereon comprising the reaction product of (a) a monoacrylated terminated, active hydrogen-containing hydrocarboxy reactant, (b) an aromatic diisocyanate, and (c) a polyacrylated terminated hydrocarboxy reactant, the active hydrogen of reactant (a) reacting with at least one diisocyanate radical of reactant (b) to form an isocyanate linkage, the reaction product of reactants (a) and (b) being reacted with reactant (c) in a molar ratio, respectively, of from 1:25 to 25:1, said gasket having a compressibility at 1,000 psi of about 2% to about 20%, a film hardness by pencil test of 6B to 4H, an elongation of about 2% to about 100%, and a flexibility by mandrel test of from 1/8 inch to one inch without failure.
Claim 11
Dependent Claim 139 words
The gasket of claim 8 in which said first-mentioned reaction product is of (a) a monoacrylated terminated hydrocarboxy reactant having the formula: ##STR9## in which R is hydrogen or methyl, and n is a whole number from 1 to 8, (b) an aromatic diisocyanate selected from the group consisting of phenylene diisocyanate and toluylene diisocyanate, and (c) a diacrylated terminated, hydrocarboxy reactant selected from the group consisting of an alkylene glycol diacrylate, an alkylene glycol dimethacrylate, a polyalkylene glycol diacrylate, and a polyalkylene glycol dimethacrylate in which said alkylene group contains from 4 to 8 carbon atoms, the hydrogen of reactant (a) reacting with at least one isocyanate radical of reactant (b) to form an isocyanate linkage, and the reaction product of (a) and (b) being reacted with reactant (c) in a molar ratio, respectively, of 1:25 to 25:1.
Claim 12
Dependent Claim 32 words
The composition of matter of claim 9 in which said monoacrylated hydrocarboxy reactant is monoacrylated ethylene glycol, said aromatic diisocyanate is toluylene diisocyanate, and said diacrylated hydrocarboxy reactant is diacrylated tetraethylene glycol.
Claim 13
Dependent Claim 83 words
The gasket of claim 8 in which said base sheet is metallic and said first-mentioned reaction product contains from about 1% to about 40% by weight of metallic powder, and said gasket having temperature resistance up to 500° F., a compressibility at 1000 psi. of about 5% to about 20%, a film hardness by pencil test of 6B to 4H, an elongation of about 5% to about 25%, and a flexibility by mandrel test of from 1/8 inch to 1/4 inch without failure.
Claim 14
Dependent Claim 146 words
A process for preparing an improved gasket comprising placing on sheet material defining a base sheet of said gasket a reaction mixture from a solventless system, said mixture including (a) a monoacrylated terminated, active hydrogen-containing hydrocarboxy reactant, (b) an aromatic diisocyanate, and (c) a polyacrylated terminated, hydrocarboxy reactant, reacting the active hydrogen of reactant (a) with at least one isocyanate radical of reactant (b) to form an isocyanate linkage, and reacting the reaction product of reactants (a) and (b) with reactant (c) in a molar ratio, respectively, of 1:25 to 25:1, said improved gasket having a temperature resistance up to 500° F., a compressibility at 1000 psi. of about 2% to about 20%, a film hardness by pencil test of 6B to 4H, an elongation of about 2% to about 100%, and a flexibility by mandrel test of from 1/8 inch to one inch without failure.
Claim 15
Dependent Claim 146 words
A process for preparing an improved gasket comprising placing on sheet material defining a base sheet of said gasket a reaction mixture from a solventless system, said mixture including (a) a monoacrylated terminated, active hydrogen-containing hydrocarboxy reactant, (b) an aromatic diisocyanate, and (c) a polyacrylated terminated, hydrocarboxy reactant, reacting the active hydrogen of reactant (a) with at least one isocyanate radical of reactant (b) to form an isocyanate linkage, and reacting the reaction product of reactants (a) and (b) with reactant (c) in a molar ratio, respectively, of 1:25 to 25:1, said improved gasket having a temperature resistance up to 500° F., a compressibility at 1000 psi. of about 2% to about 20%, a film hardness by pencil test of 6B to 4H, an elongation of about 2% to about 100%, and a flexibility by mandrel test of from 1/8 inch to one inch without failure.
Claim 16
Dependent Claim 89 words
The process of claim 12 in which said monoacrylated hydrocarboxy reactant has the formula: ##STR10## in which R is hydrogen or methyl, and n is a whole number from 1 to 8, said aromatic diisocyanate is selected from the group consisting of phenylene diisocyanate and toluylene diisocyanate, and said polyacrylated hydrocarboxy reactant is diacrylated and selected from the group consisting of an alkylene glycol diacrylate, an alkylene glycol dimethacrylate, a polyalkylene glycol diacrylate, and a polyalkylene glycol dimethacrylate, in which said alkylene group contains 4 to 8 carbon atoms.
Claim 17
Dependent Claim 13 words
The process of claim 12 in which said reaction is generated by heat.
Claim 18
Dependent Claim 21 words
The process of claim 12 including a peroxide catalyst in said reaction mixture, and catalyzing said reaction by the peroxide catalyst.
Claim 19
Dependent Claim 27 words
The process of claim 12 in which said monoacrylated hydrocarboxy reactant has an alkyl or alkenyl linear stem and a molecular weight of up to about 8000.
Claim 20
Dependent Claim 32 words
The process of claim 12 in which said monoacrylated hydrocarboxy reactant has the formula: ##STR11## in which R is hydrogen or methyl, and n is a whole number from 1 to 8.
Claim 21
Dependent Claim 48 words
The process of claim 12 in which said polacrylated terminated, hydrocarboxy reactant is diacrylated and selected from the group consisting of an alkylene glycol diacrylate, alkylene glycol dimethacrylate, a polyalkylene glycol diacrylate, and a polyalkylene glycol dimethyacrylate, in which said alkylene group contains 4 to 8 carbon atoms.
Claim 22
Dependent Claim 64 words
The process of claim 12 in which said aromatic diisocyanate in the reaction product formed by reactants (a) and (b) has one isocyanate radical rected with said active hydrogen of reactant (b) and the other isocyanate radical reacted with a carboxyl radical of an organic acid to form an ester group, said ester group having a molecular weight of about 500 to about 6,000.

References Cited (Backward Citations)

US2029302A Cited
US2071322A Cited
US3030249A Cited
US2992939A Cited
US3193438A Cited
US3291859A Cited
US3524794A Cited
US3549407A Cited
US3695918A Cited
US3645977A Cited
US3700643A Cited
US3862920A Cited
US4057431A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1982-03-19 1982-09-18 1983-03-20 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1986-03-19 1986-09-18 1987-03-20 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1990-03-19 1990-09-18 1991-03-20 $7700.00 Window Closed / Lapsed

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