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US5744543A Expired / Lapsed US ⏱️ 0.0 years remaining

One-component reactive adhesive

Assignee: Henkel AG and Co KGaA
•
Filing: 1995-05-30
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Granted: 1998-04-28
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Expires: 2015-05-30
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Abstract

Abstract Described is a single-component adhesive made from a radical-polymerized olefinically unsaturated monomer and an air-activated initiator system and characterized in that the adhesive also contains isocyanate and/or silane groups. This makes a dual curing mechanism possible. The more rapid of the two curing reactions gives specific characteristics in the initial stage, e. g. high initial strength, high adhesive strength or high contact strength. The slower of the two reactions produces the definitive characteristics, e.g. final strength or resistance to heat.

Inventors

  • 👤 Thomas Huver
  • 👤 Herbert Fischer
  • 👤 Wolfgang Klauck
  • 👤 Gerd Bolte

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 12:36
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/08; C08G18/10; C08F; C08F290/00; C08F290/02; C08F290/06

Claims Analysis

Total Claims: 32
Claim 1
Independent Claim 47 words
A one-component reactive adhesive based on an air-activatable initiator wherein the air-activatable initiator is selected from the group consisting of hydrazones, dihydropyridines and mixtures thereof and radical-polymerizable olefinically unsaturated monomers, wherein the adhesive additionally contains groups selected from the group consisting of isocyanate, silanes and mixtures thereof.
Claim 2
Dependent Claim 47 words
A one-component reactive adhesive based on an air-activatable initiator wherein the air-activatable initiator is selected from the group consisting of hydrazones, dihydropyridines and mixtures thereof and radical-polymerizable olefinically unsaturated monomers, wherein the adhesive additionally contains groups selected from the group consisting of isocyanate, silanes and mixtures thereof.
Claim 3
Dependent Claim 55 words
The one-component reactive adhesive composition of claim 1, comprising the product of combining: an air-activatable initiator wherein the air-activatable initiator is selected from the group consisting of hydrazones, dihydropyridines and mixtures thereof; a moisture-curing prepolymer adhesive terminated with groups selected from the group consisting of isocyanates, silanes and mixtures thereof; and radical-polymerizable olefinically unsaturated monomers.
Claim 4
Dependent Claim 12 words
The reactive adhesive of claim 1, wherein the hydrazone is acetophenone-t-butyl hydrazone.
Claim 5
Dependent Claim 21 words
The reactive adhesive of claim 1, wherein the dihydropyridine is selected from the group consisting of dihydropyridine, 1-phenyl-2-propyl-3,5-diethyl-1,2-dihydropyridine and mixtures thereof.
Claim 6
Dependent Claim 28 words
The reactive adhesive of claim 2, wherein the moisture-curing prepolymer is selected from the group consisting of isocyanate terminated diols, isocyanate terminated triols, isocyanate acrylates and mixtures thereof.
Claim 7
Dependent Claim 19 words
The reactive adhesive of claim 6, wherein the isocyanate terminated diol prepolymer is an isocyanate terminated polyether diol prepolymer.
Claim 8
Dependent Claim 23 words
The reactive adhesive of claim 6, wherein the isocyanate terminated polyether diol prepolymer is the reaction product of 1,3-bis-(1-isocyanato-1-methylethyl)-benzene and propoxylated bisphenol A.
Claim 9
Dependent Claim 38 words
The reactive adhesive of claim 5, wherein the isocyanate terminated triol is selected from the group consisting of the reaction product of 1,3-bis-(1-isocyanato-1-methylethyl)-benzene and polycaprolactam triol, the reaction product of 1,3-bis-(1-isocyanato-1-methylethyl)-benzene and propylene oxide macrotriol and mixtures thereof.
Claim 10
Dependent Claim 20 words
The reactive adhesive of claim 5, wherein the isocyanate acrylate prepolymer is the reaction product of 1,3-bis4(1-isocyanato-1-methylethyl)7benzene and 2-hydroxyethyl acrylate.
Claim 11
Dependent Claim 32 words
The reactive adhesive of claim 2, wherein the moisture-curing prepolymer is selected from the group consisting of alkoxysilane terminated diols, alkylalkoxysilane terminated diols, alkoxysilane terminated triols, alkylalkoxy terminated triols and mixtures thereof.
Claim 12
Dependent Claim 22 words
The reactive adhesive of claim 10, wherein the alkoxysilane terminated diol is the reaction product of polytetrahydrofurfuryl diol, toluenediisocyanate and 3-aminopropyl trimethoxysilane.
Claim 13
Dependent Claim 36 words
The reactive adhesive of claim 2, wherein the radical-polymerizable olefinically unsaturated monomers are selected from the group consisting of acrylic acid, methacrylic acid, derivatives of acrylic acid, derivatives of methacrylic acid, acryl-terminated polyesters and mixtures thereof.
Claim 14
Dependent Claim 42 words
The reactive adhesive of claim 12, wherein the derivatives of acrylic acid are selected from the group consisting of esters containing from about 1 to about 25 carbon atoms, amides containing from about 1 to about 25 carbon atoms and mixtures thereof.
Claim 15
Dependent Claim 26 words
The reactive adhesive of claim 12, wherein the derivatives of acrylic acid are selected from the group consisting of n-butyl acrylate, phenoxyethyl acrylate and mixtures thereof.
Claim 16
Dependent Claim 42 words
The reactive adhesive of claim 12, wherein the derivatives of methacrylic acid are selected from the group consisting of esters containing from about 1 to about 25 carbon atoms, amides containing from about 1 to about 25 carbon atoms and mixtures thereof.
Claim 17
Dependent Claim 26 words
The reactive adhesive of claim 12, wherein the derivatives of methacrylic acid are selected from the group consisting of methyl methacrylate, hydroxypropyl methacrylate and mixtures thereof.
Claim 18
Dependent Claim 12 words
The reactive adhesive of claim 2, further comprising at least one stabilizer.
Claim 19
Dependent Claim 12 words
The reactive adhesive of claim 2, further comprising at least one filler.
Claim 20
Dependent Claim 12 words
The reactive adhesive of claim 2, further comprising at least one catalyst.
Claim 21
Dependent Claim 24 words
The reactive adhesive of claim 19, wherein the catalyst is selected from the group consisting of tin compounds, ferric acetylacetonate, iodine and mixtures thereof.
Claim 22
Dependent Claim 13 words
The reactive adhesive of claim 19, wherein the catalyst is dibutyl tin dilaurate.
Claim 23
Dependent Claim 73 words
The reactive adhesive of claim 26, which comprises: about 26 parts by weight acryl-terminated polyester; about 26 parts by weight of the reaction product of 1,3-bis-(1-isocyanato-1-methylethyl)-benzene and polycaprolactam triol; about 30 parts by weight n-butyl acrylate; about 17.5 parts by weight of the reaction product of 1 ,3-bis-(1-isocyanato-1-methylethyl)-benzene and 2-hydroxyethyl acrylate; about 4 parts by weight acetophenone-t-butyl hydrazone; about 1.2 parts by weight Fe(acac) 3 ; and about 750 ppm I 2 .
Claim 24
Dependent Claim 71 words
The reactive adhesive of claim 2, which comprises the reaction product of: about 0.2 to about 15% by weight of an air-activatable initiator wherein the air-activatable initiator is selected from the group consisting of hydrazones, dihydropyridines and mixtures thereof; about 20 to about 99.6% by weight of radical-polymerizable monomers; and about 0.2 to about 10% by weight of prepolymer termination groups selected from the group consisting of isocyanates, silanes-and mixtures thereof.
Claim 25
Dependent Claim 26 words
The reactive adhesive of claim 23, further comprising about 0.01% to about 50% by weight by weight of additives, based on the adhesive as a whole.
Claim 26
Dependent Claim 17 words
In a process for bonding, wherein the improvement comprises use of the reactive adhesive of claim 2.
Claim 27
Dependent Claim 86 words
A one-component reactive adhesive composition comprising the reaction product of: about 1 to about 10% by weight of an air-activatable initiator wherein the air-activatable initiator is selected from the group consisting of hydrazones, dihydropyridines and mixtures thereof; about 40 to about 80% by weight of radical-polymerizable monomers; about 1 to about 7% by weight of prepolymer termination groups selected from the group consisting of isocyanates, silanes and mixtures thereof; and about 0.01 to about 40% by weight of additives, based on the adhesive as a whole.
Claim 28
Dependent Claim 86 words
A one-component reactive adhesive composition comprising the reaction product of: about 1 to about 10% by weight of an air-activatable initiator wherein the air-activatable initiator is selected from the group consisting of hydrazones, dihydropyridines and mixtures thereof; about 40 to about 80% by weight of radical-polymerizable monomers; about 1 to about 7% by weight of prepolymer termination groups selected from the group consisting of isocyanates, silanes and mixtures thereof; and about 0.01 to about 40% by weight of additives, based on the adhesive as a whole.
Claim 29
Dependent Claim 99 words
A process for making one-part moisture and air-cure adhesives, which comprises the steps of: introducing monomer, moisture-curing prepolymer, stabilizer and all additives but for an oxygen-sensitive initiator component, which comprise a mixture, into an inert gas-filled container; homogenizing the mixture; cooling the mixture to below room temperature; evacuating the container; heating the container to room temperature; reiterating the cooling and warming steps to remove degas the mixture; adding a oxygen-sensitive initiator wherein the oxygen-sensitive initiator is selected from the group consisting of hydrazones dihydropyridines and mixtures thereof; and reiterating the cooling, evacuating and warming steps to degas the mixture.
Claim 30
Dependent Claim 99 words
A process for making one-part moisture and air-cure adhesives, which comprises the steps of: introducing monomer, moisture-curing prepolymer, stabilizer and all additives but for an oxygen-sensitive initiator component, which comprise a mixture, into an inert gas-filled container; homogenizing the mixture; cooling the mixture to below room temperature; evacuating the container; heating the container to room temperature; reiterating the cooling and warming steps to remove degas the mixture; adding a oxygen-sensitive initiator wherein the oxygen-sensitive initiator is selected from the group consisting of hydrazones dihydropyridines and mixtures thereof; and reiterating the cooling, evacuating and warming steps to degas the mixture.
Claim 31
Dependent Claim 80 words
The process for making a one-component reactive adhesive product of claim 27, wherein: The mixture comprises about 40 to about 80% by weight of radical-polymerizable monomers, about 1 to about 7% by weight of prepolymer termination groups selected from the group consisting of isocyanates, silanes and mixtures thereof and about 0.01 to about 40% by weight of additives, based on the adhesive as a whole; and the oxygen sensitive initiator is present at about 1 to about 10% by weight.
Claim 32
Dependent Claim 46 words
The process of claim 27, wherein the product comprises: about 50 parts by weight silane-terminated polytetrahydrofurfuryl diol; about 50 parts by weight hydroxypropyl methacrylate; about 4 parts by weight acetophenone-t-butyl hydrazone; about 1.2 parts by weight Fe(acac) 3 ; and about 750 ppm I 2 .

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 2001-04-27 2001-10-27 2002-04-28 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 2005-04-27 2005-10-27 2006-04-28 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2009-04-27 2009-10-27 2010-04-28 $7700.00 Window Closed / Lapsed

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