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US4308071A Expired / Lapsed US ⏱️ 0.0 years remaining

One-coat adhesive systems

Assignee: Lord Corp
•
Filing: 1979-08-08
•
Granted: 1981-12-29
•
Expires: 1999-08-08
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Abstract

Abstract Compositions comprising at least one isocyanate-functional organosilane, preferably in combination with at least one polyisocyanate, and, optimally, at least one aromatic nitroso compound having been found to be unexpectedly effective as storage-stable, single-package, one-coat adhesive systems for bonding a variety of elastomeric materials to themselves and other solid substrates, such as metal, fabric, ceramic, and the like substrates. The use of aromatic nitroso compounds is necessary with certain isocyanatosilanes and optional with others, but, in all cases, affords improved performance, especially with respect to environmental resistance.

Inventors

  • 👤 Nicholas J. Gervase

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-25 12:52
CPC Classifications
C; C09; C09J; C09J175/00; C08; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/72; C08G18/77; C08G18/778; C08G18/80; C08G18/8061; C08G18/8083; C08G18/809

Claims Analysis

Total Claims: 67
Claim 1
Independent Claim 174 words
A heat-activable rubber-to-metal adhesive composition consisting essentially of (i) from about 2.5 to about 50 parts by weight of at least one isocyanatosilane selected from the group consisting of isocyanatosilane adducts of multifunctional organosilanes and polyisocyanates; (ii) 100-x parts by weight of at least one free polyisocyanate, wherein x is the amount, in parts by weight, of said isocyanatosilane adduct; (iii) from 0 to about 200 parts by weight, per 100 parts of combined weight of said isocyanatosilane adduct and said free polyisocyanate, of at least one aromatic nitroso compound; (iv) from 0 to about 200 parts by weight, per 100 parts of combined weight of said isocyanatosilane adduct and said free polyisocyanate, of at least one polymeric film-forming adjunct; and (v) from 0 to about 200 parts by weight, per 100 parts of combined weight of said isocyanatosilane adduct and said free polyisocyanate, of at least one inert filler material, said adhesive composition having an amount of total isocyanate which is greater than one molar equivalent of isocyanate per mole of isocyanatosilane adduct.
Claim 2
Dependent Claim 174 words
A heat-activable rubber-to-metal adhesive composition consisting essentially of (i) from about 2.5 to about 50 parts by weight of at least one isocyanatosilane selected from the group consisting of isocyanatosilane adducts of multifunctional organosilanes and polyisocyanates; (ii) 100-x parts by weight of at least one free polyisocyanate, wherein x is the amount, in parts by weight, of said isocyanatosilane adduct; (iii) from 0 to about 200 parts by weight, per 100 parts of combined weight of said isocyanatosilane adduct and said free polyisocyanate, of at least one aromatic nitroso compound; (iv) from 0 to about 200 parts by weight, per 100 parts of combined weight of said isocyanatosilane adduct and said free polyisocyanate, of at least one polymeric film-forming adjunct; and (v) from 0 to about 200 parts by weight, per 100 parts of combined weight of said isocyanatosilane adduct and said free polyisocyanate, of at least one inert filler material, said adhesive composition having an amount of total isocyanate which is greater than one molar equivalent of isocyanate per mole of isocyanatosilane adduct.
Claim 3
Dependent Claim 83 words
A composition according to claim 1 wherein said polyisocyanate employed in forming said adduct has the formula ##STR18## wherein R 8 is a divalent organic radical having from 1 to 8 carbon atoms; X is selected from the group consisting of hydrogen, halogen, alkyl radicals having from 1 to 8 carbon atoms, and alkoxy radicals having from 1 to 8 carbon atoms; m is 1 or 2; and n is a digit having an average value in the range from zero to 15.
Claim 4
Dependent Claim 15 words
A composition according to claim 2 wherein each of (iii), (iv), and (v) are zero.
Claim 5
Dependent Claim 27 words
A composition according to claim 2 wherein the amount of said aromatic nitroso compound is in the range from about 1 to about 200 parts by weight.
Claim 6
Dependent Claim 264 words
An adhesive composition according to claim 1 consisting essentially of (i) from about 2.5 to about 50 parts by weight of at least one isocyanatosilane adduct of multifunctional organosilanes and polyisocyanates, said adducts having as characteristic features at least one free isocyanate group, at least one silane grouping, and the structure ##STR19## the free isocyanate group and silane grouping of said adduct being joined to each other through the residue of said polyisocyanate reactant; wherein A is selected from the group consisting of --O--, --S--, --N<, and other groups containing an active hydrogen; R is a divalent aliphatic, cycloaliphatic or aromatic radical having from 1 to 20 carbon atoms; R 1 is a monovalent aliphatic, cycloaliphatic or aromatic radical having from 1 to 20 carbon atoms; R 2 is a monovalent aliphatic, cycloaliphatic or aromatic radical having from 1 to 8 carbon atoms; and a is zero or 1; (ii) 100-x parts by weight of at least one free polyisocyanate, wherein x is the amount, in parts by weight, of said isocyanatosilane adduct; (iii) from 0 to about 200 parts by weight, per 100 parts of combined weight of said isocyanatosilane adduct and said free polyisocyanate, of at least one aromatic nitroso compound; (iv) from 0 to about 200 parts by weight, per 100 parts of combined weight of said isocyanatosilane adduct and said free polyisocyanate, of at least one polymeric film-forming adjunct; and (v) from 0 to about 200 parts by weight, per 100 parts of combined weight of said isocyanatosilane adduct and said free polyisocyanate, of at least one inert filler material.
Claim 7
Dependent Claim 26 words
A composition according to claim 5 wherein the amount of aromatic nitroso compound is in the range from about 1 to about 200 parts by weight.
Claim 8
Dependent Claim 26 words
A composition according to claim 5 wherein the amount of said film-forming adjunct is in the range from about 10 to about 200 parts by weight.
Claim 9
Dependent Claim 27 words
A composition according to claim 7 wherein the amount of said aromatic nitroso compound is in the range from about 1 to about 200 parts by weight.
Claim 10
Dependent Claim 26 words
A composition according to claim 5 wherein the amount of said inert filler is in the range from about 10 to about 200 parts by weight.
Claim 11
Dependent Claim 27 words
A composition according to claim 9 wherein the amount of said aromatic nitroso compound is in the range from about 1 to about 200 parts by weight.
Claim 12
Dependent Claim 26 words
A composition according to claim 10 wherein the amount of said film-forming adjunct is in the range from about 10 to about 200 parts by weight.
Claim 13
Dependent Claim 83 words
A composition according to claim 5 wherein said polyisocyanate employed in forming said adduct has the formula ##STR20## wherein R 8 is a divalent organic radical having from 1 to 8 carbon atoms; X is selected from the group consisting of hydrogen, halogen, alkyl radicals having from 1 to 8 carbon atoms, and alkoxy radicals having from 1 to 8 carbon atoms; m is 1 or 2; and n is a digit having an average value in the range from zero to 15.
Claim 14
Dependent Claim 26 words
A composition according to claim 12 wherein the amount of aromatic nitroso compound is in the range from about 1 to about 200 parts by weight.
Claim 15
Dependent Claim 25 words
A composition according to claim 12 wherein the amount of said film-forming adjunct is in the range from about 10 to 200 parts by weight.
Claim 16
Dependent Claim 27 words
A composition according to claim 14 wherein the amount of said aromatic nitroso compound is in the range from about 1 to about 200 parts by weight.
Claim 17
Dependent Claim 26 words
A composition according to claim 12 wherein the amount of said inert filler is in the range from about 10 to about 200 parts by weight.
Claim 18
Dependent Claim 27 words
A composition according to claim 16 wherein the amount of said aromatic nitroso compound is in the range from about 1 to about 200 parts by weight.
Claim 19
Dependent Claim 26 words
A composition according to claim 17 wherein the amount of said film-forming adjunct is in the range from about 10 to about 200 parts by weight.
Claim 20
Dependent Claim 26 words
A composition according to claim 5 wherein said free polyisocyanate has the formula ##STR21## wherein R 8 , X, m and n are as previously defined.
Claim 21
Dependent Claim 26 words
A composition according to claim 19 wherein the amount of aromatic nitroso compound is in the range from about 1 to about 200 parts by weight.
Claim 22
Dependent Claim 26 words
A composition according to claim 19 wherein the amount of said film-forming adjunct is in the range from about 10 to about 200 parts by weight.
Claim 23
Dependent Claim 27 words
A composition according to claim 21 wherein the amount of said aromatic nitroso compound is in the range from about 1 to about 200 parts by weight.
Claim 24
Dependent Claim 26 words
A composition according to claim 19 wherein the amount of said inert filler is in the range from about 10 to about 200 parts by weight.
Claim 25
Dependent Claim 27 words
A composition according to claim 23 wherein the amount of said aromatic nitroso compound is in the range from about 1 to about 200 parts by weight.
Claim 26
Dependent Claim 26 words
A composition according to claim 24 wherein the amount of said film-forming adjunct is in the range from about 10 to about 200 parts by weight.
Claim 27
Dependent Claim 30 words
A composition according to claim 19 wherein said polyisocyanate employed in forming said adduct has the formula ##STR22## wherein R 8 , X, m and n are as previously defined.
Claim 28
Dependent Claim 27 words
A composition according to claim 26 wherein the amount of said aromatic nitroso compound is in the range from about 1 to about 200 parts by weight.
Claim 29
Dependent Claim 26 words
A composition according to claim 26 wherein the amount of said film-forming adjunct is in the range from about 10 to about 200 parts by weight.
Claim 30
Dependent Claim 27 words
A composition according to claim 28 wherein the amount of said aromatic nitroso compound is in the range from about 1 to about 200 parts by weight.
Claim 31
Dependent Claim 26 words
A composition according to claim 26 wherein the amount of said inert filler is in the range from about 10 to about 200 parts by weight.
Claim 32
Dependent Claim 27 words
A composition according to claim 30 wherein the amount of said aromatic nitroso compound is in the range from about 1 to about 200 parts by weight.
Claim 33
Dependent Claim 26 words
A composition according to claim 31 wherein the amount of said film-forming adjunct is in the range from about 10 to about 200 parts by weight.
Claim 34
Dependent Claim 15 words
A composition according to claim 5 wherein each of (iii), (iv), and (v) are zero.
Claim 35
Dependent Claim 27 words
A composition according to claim 5 wherein the amount of said aromatic nitroso compound is in the range from about 5 to about 200 parts by weight.
Claim 36
Dependent Claim 26 words
A composition according to claim 34 wherein the amount of said film-forming adjunct is in the range from about 10 to about 200 parts by weight.
Claim 37
Dependent Claim 26 words
A composition according to claim 34 wherein the amount of said inert filler is in the range from about 10 to about 200 parts by weight.
Claim 38
Dependent Claim 26 words
A composition according to claim 36 wherein the amount of said film-forming adjunct is in the range from about 10 to about 200 parts by weight.
Claim 39
Dependent Claim 25 words
A composition according to claim 12 wherein said aromatic nitroso compound is present in the range from about 5 to about 200 parts by weight.
Claim 40
Dependent Claim 26 words
A composition according to claim 38 wherein the amount of said film-forming adjunct is in the range from about 10 to about 200 parts by weight.
Claim 41
Dependent Claim 26 words
A composition according to claim 38 wherein the amount of said inert filler is in the range from about 10 to about 200 parts by weight.
Claim 42
Dependent Claim 26 words
A composition according to claim 40 wherein the amount of said film-forming adjunct is in the range from about 10 to about 200 parts by weight.
Claim 43
Dependent Claim 15 words
A composition according to claim 19 wherein each of (iii), (iv), and (v) are zero.
Claim 44
Dependent Claim 27 words
A composition according to claim 19 wherein the amount of said aromatic nitroso compound is in the range from about 5 to about 200 parts by weight.
Claim 45
Dependent Claim 26 words
A composition according to claim 43 wherein the amount of said film-forming adjunct is in the range from about 10 to about 200 parts by weight.
Claim 46
Dependent Claim 26 words
A composition according to claim 43 wherein the amount of said inert filler is in the range from about 10 to about 200 parts by weight.
Claim 47
Dependent Claim 26 words
A composition according to claim 45 wherein the amount of said film-forming adjunct is in the range from about 10 to about 200 parts by weight.
Claim 48
Dependent Claim 15 words
A composition according to claim 26 wherein each of (iii), (iv), and (v) are zero.
Claim 49
Dependent Claim 27 words
A composition according to claim 26 wherein the amount of said aromatic nitroso compound is in the range from about 5 to about 200 parts by weight.
Claim 50
Dependent Claim 26 words
A composition according to claim 48 wherein the amount of said film-forming adjunct is in the range from about 10 to about 200 parts by weight.
Claim 51
Dependent Claim 26 words
A composition according to claim 48 wherein the amount of said inert filler is in the range from about 10 to about 200 parts by weight.
Claim 52
Dependent Claim 25 words
A composition according to claim 50 wherein the amount of said film-forming adjunct is in the range from about 10 to 200 parts by weight.
Claim 53
Dependent Claim 32 words
A composition according to claim 51 wherein R 8 is methylene, X is hydrogen, m is 1 and n has an average value in the range from about 0.1 to about 4.
Claim 54
Dependent Claim 21 words
A composition according to claim 52 wherein A is --NH--, R is propylene, R 2 is methyl and a is zero.
Claim 55
Dependent Claim 21 words
A composition according to claim 52 wherein A is --NH--, R is propylene, R 2 is ethyl and a is zero.
Claim 56
Dependent Claim 216 words
A heat-activatable rubber-to-metal adhesive composition consisting essentially of (i) from about 2.5 to about 50 parts by weight of at least one isocyanatosilane having the general formula ##STR23## wherein R 0 is selected from the group consisting of divalent hydrocarbon and halogenated hydrocarbon radicals containing from 1 to 20 carbon atoms; R 1 is a monovalent aliphatic, cycloaliphatic or aromatic radical having from 1 to 20 carbon atoms; R 2 is a monovalent aliphatic, cycloaliphatic or aromatic radical having from 1 to 20 carbon atoms; and a is zero or 1; (ii) 100-x parts by weight of at least one free polyisocyanate, wherein x is the amount, in parts by weight, of said isocyanatosilane; (iii) an effective amount of at least one aromatic nitroso compound, said amount being sufficient to obtain an effective adhesive bond; (iv) from 0 to about 200 parts by weight, per 100 parts of combined weight of said isocyanatosilane and said free polyisocyanate, of at least one polymeric film-forming adjunct; and (v) from 0 to about 200 parts by weight, per 100 parts of combined weight of said isocyanatosilane and said free polyisocyanate, of at least one inert filler material, said adhesive composition having an isocyanate content greater than an amount equal to one molar equivalent of isocyanate per mole of isocyanosilane.
Claim 57
Dependent Claim 216 words
A heat-activatable rubber-to-metal adhesive composition consisting essentially of (i) from about 2.5 to about 50 parts by weight of at least one isocyanatosilane having the general formula ##STR23## wherein R 0 is selected from the group consisting of divalent hydrocarbon and halogenated hydrocarbon radicals containing from 1 to 20 carbon atoms; R 1 is a monovalent aliphatic, cycloaliphatic or aromatic radical having from 1 to 20 carbon atoms; R 2 is a monovalent aliphatic, cycloaliphatic or aromatic radical having from 1 to 20 carbon atoms; and a is zero or 1; (ii) 100-x parts by weight of at least one free polyisocyanate, wherein x is the amount, in parts by weight, of said isocyanatosilane; (iii) an effective amount of at least one aromatic nitroso compound, said amount being sufficient to obtain an effective adhesive bond; (iv) from 0 to about 200 parts by weight, per 100 parts of combined weight of said isocyanatosilane and said free polyisocyanate, of at least one polymeric film-forming adjunct; and (v) from 0 to about 200 parts by weight, per 100 parts of combined weight of said isocyanatosilane and said free polyisocyanate, of at least one inert filler material, said adhesive composition having an isocyanate content greater than an amount equal to one molar equivalent of isocyanate per mole of isocyanosilane.
Claim 58
Dependent Claim 40 words
A composition according to claim 55 wherein the amount of said aromatic nitroso compound is in the range from about 1 to about 200 parts by weight, per 100 parts of combined weight of said isocyanatosilane and said free polyisocyanate.
Claim 59
Dependent Claim 25 words
A composition according to claim 56 wherein the amount of said film-forming adjunct is in the range from about 10 to 200 parts by weight.
Claim 60
Dependent Claim 26 words
A composition according to claim 56 wherein the amount of said inert filler is in the range from about 10 to about 200 parts by weight.
Claim 61
Dependent Claim 26 words
A composition according to claim 58 wherein the amount of said film-forming adjunct is in the range from about 10 to about 200 parts by weight.
Claim 62
Dependent Claim 40 words
A composition according to claim 55 wherein the amount of said aromatic nitroso compound is in the range from about 5 to about 200 parts by weight, per 100 parts of combined weight of said isocyanatosilane and said free polyisocyanate.
Claim 63
Dependent Claim 26 words
A composition according to claim 60 wherein the amount of said film-forming adjunct is in the range from about 10 to about 200 parts by weight.
Claim 64
Dependent Claim 26 words
A composition according to claim 60 wherein the amount of said inert filler is in the range from about 10 to about 200 parts by weight.
Claim 65
Dependent Claim 26 words
A composition according to claim 62 wherein the amount of said film-forming adjunct is in the range from about 10 to about 200 parts by weight.
Claim 66
Dependent Claim 116 words
A composition according to claim 63 wherein said isocyanatosilane has the formula ##STR24## wherein R 0 has from 2 to 9 carbon atoms; R 1 is selected from the group consisting of alkyl radicals having from 1 to 4 carbon atoms, cycloalkyl radicals having from 4 to 7 ring carbon atoms, and aryl radicals having 6, 10 or 14 nuclear carbon atoms; and R 2 is selected from the group consisting of alkyl radicals having from 1 to 4 carbon atoms, --R 3 --O--R 4 , and ##STR25## where R 3 is an alkylene group having from 1 to 4 carbon atoms and R 4 is an alkyl group having from 1 to 4 carbon atoms.
Claim 67
Dependent Claim 11 words
A composition according to claim 64 wherein said isocyanatosilane is isocyanatopropyltriethoxysilane.

References Cited (Backward Citations)

US2905582A Cited
US3170891A Cited
US3426057A Cited
US3398043A Cited
US4031120A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-12-28 1985-06-29 1985-12-29 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-12-28 1989-06-29 1989-12-29 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-12-28 1993-06-29 1993-12-29 $7700.00 Window Closed / Lapsed

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