WO2019234667A1 - Adhesive composition for vulcanized rubber - Google Patents

Adhesive composition for vulcanized rubber Download PDF

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Publication number
WO2019234667A1
WO2019234667A1 PCT/IB2019/054705 IB2019054705W WO2019234667A1 WO 2019234667 A1 WO2019234667 A1 WO 2019234667A1 IB 2019054705 W IB2019054705 W IB 2019054705W WO 2019234667 A1 WO2019234667 A1 WO 2019234667A1
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WIPO (PCT)
Prior art keywords
adhesive composition
organic solvent
chemosil
product
based adhesive
Prior art date
Application number
PCT/IB2019/054705
Other languages
French (fr)
Inventor
Stefano CIAFANELLI
Silvia CIFANI
Bruno D'ANDREA
Francesca LILLO
Enrico RIPANI
Rodolfo SALTARELLI
Original Assignee
Avio S.P.A.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Application filed by Avio S.P.A. filed Critical Avio S.P.A.
Publication of WO2019234667A1 publication Critical patent/WO2019234667A1/en

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
    • C09J123/02—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers not modified by chemical after-treatment
    • C09J123/16—Elastomeric ethene-propene or ethene-propene-diene copolymers, e.g. EPR and EPDM rubbers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C08K2003/2296—Oxides; Hydroxides of metals of zinc
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2201/00—Properties
    • C08L2201/56—Non-aqueous solutions or dispersions

Definitions

  • the present invention relates to an adhesive composition to be applied to a layer of already vulcanized rubber.
  • One of the processes where it is necessary to couple an already vulcanized rubber to a virgin rubber is, for example, the production of solid-propellant rocket engines.
  • the solid-propellant rocket engines generally comprise an axial-symmetrical outer casing, which houses a charge of solid propellant, an ignition system provided at an end of the casing and an end nozzle provided at the opposite end.
  • the casing is internally coated with a thermal protection made of ablative material, typically constituted by elastomers charged with additives and/or fibers, to protect the inner surface of the casing against high temperatures and erosion.
  • the thermal protection consists of an intermediate cylindrical part formed by winding a web of reinforced ablative material on the surface of a mandrel, and of two end dome-shaped end parts formed out of the site of assemblage.
  • the term "out of the site of assemblage" means that the two end portions are formed separately from the mandrel, and then mounted thereon.
  • the two end portions are mounted on the mandrel once they have already been vulcanized.
  • the end portions of already vulcanized rubber are necessarily coupled to the intermediate portion being formed, i.e. still made of virgin (not vulcanized) rubber.
  • the thermal portion is made by coupling an intermediate portion of virgin rubber with two end portions of already vulcanized rubber.
  • the inventors of the present invention have surprisingly found that the use of a compound currently used for making virgin rubber adhere to metal, when properly mixed with a rubber solubilized in an organic solvent, provides an adhesive composition capable of ensuring the effective adhesion of already vulcanized rubber both to already vulcanized rubber and virgin rubber, as well as to metal.
  • An object of the invention is an organic solvent-based adhesive composition
  • a crosslinking unsaturated-chain polymer base and a vulcanization system said adhesive composition being characterized by comprising 50-200 phr, preferably 100-150 phr of a product with adhesive action comprising: xylene 30-80% wt, ethylbenzene 10-30% wt, zinc oxide 1-10% wt, and 1-5% wt of a compound selected from the group consisting of l,l-(l,3-phenylene)bis-lH-pirrole-2,5-dione, N,N’- (4,4’diphenylmethane) bismaleimide, diphenylmethanediisocyanate, 4,4'-methylenbis (N, N'-bis (2,3-epoxypropyl) aniline or mixtures thereof.
  • Crosslinkable, unsaturated-chain polymer base refers, hereinafter, to any natural or synthetic non-crosslinked polymer, adapted to gain all the chemical-physical and mechanical features typically gained by elastomers following cross-linking (vulcanization).
  • Vulcanization system refers, hereinafter, to a complex of vulcanizing agents that promote vulcanization of the polymer base when the mixture is brought to the vulcanization temperature.
  • the cross -linkable unsaturated-chain polymer base is comprised in group consisting of EPDM, NBR, SBR, HTPB.
  • the vulcanization system comprises a peroxide crosslinking agent.
  • the adhesive composition of the present invention comprises xylene as a solvent.
  • a further object of the present invention is a method for preparing the adhesive composition of the invention.
  • the method comprises a first mixing step, wherein a crosslinking unsaturated-chain polymer base, a plasticizer oil and a vulcanization system are mixed together; a solubilization step, wherein the mixture formed during the first mixing step is solubilized in an organic solvent thus forming a liquid rubber; and a second mixing step, wherein to the liquid rubber a product is added with adhesive action, comprising: methyl isobutyl ketone 60-93% wt, xylene 5-10% wt, phenol- formaldehyde polymer 1-5% wt, ethylbenzene 1-5% wt.
  • said product with adhesive action is marketed under the name Chemosil® 411.
  • the adhesive composition of the invention has been made.
  • NOREX HI has been used as plasticizer oil.
  • AEROSIL R 972 has been used as rheology modifier.
  • TRIGONOX 101-50D-PD has been used as peroxide crosslinking agent.
  • TRIALLYL CYANETRATE has been used as accelerator.
  • the rubber mixture has been solubilized in xylene, resulting in the formation of a liquid rubber.
  • Chemosil® 411 has been added to the liquid rubber with a 1:1 weight ratio (Chemosil® 41 Erubber mixture).
  • the adhesive composition obtained looks like a low-viscosity liquid.
  • the viscosity of the adhesive composition has been found equal to 600 mPa.s at 25°C.
  • the method described above is significant for the effectiveness of the adhesive composition.
  • the adhesive composition obtained can be applied by means of a brush or by spraying.
  • the adhesive composition prepared as described above has been tested for the coupling between: a layer of vulcanized rubber and a layer of virgin rubber; a layer of vulcanized rubber and a further layer of vulcanized rubber; a layer of vulcanized rubber and a metal.
  • the adhesion tests have been repeated using both the only rubber mixture and the only Chemosil® 411 as adhesive agent.
  • the rubber mixture and Chemosil® 411 when used alone, have been used in the same amount as in the adhesive composition of the invention.
  • the various adhesive agents have been applied by brush in three subsequent coats, every subsequent coat having been applied once the solvent was evaporated. After the last coat, the two parts to be coupled have been kept in contact with each other and vulcanized in autoclave at l65°C under a pressure higher than 2 bar.
  • Table II shows the results of the traction measurements.
  • Chemosil® 411 has been used only for making virgin rubber adhere to metal. Differently from what described for the adhesive composition of the invention, Chemosil® 411 was applied directly (without being first added to a liquid rubber) on the virgin rubber layer, and the adhesive action thereof was performed during the vulcanization phase at l30°C-l80°C. In other words, according to the prior art, i.e. before the present invention, a necessary condition for Chemosil® 411 to be effective was that it would be subjected to a vulcanization phase at approximately l50°C.
  • the inventors of the present invention have provided an extremely effective solvent-based adhesive composition for coupling already vulcanized rubber by using a compound that was known for the adhesive effectiveness for coupling virgin rubber and only if used in a process including vulcanization.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

An organic solvent-based adhesive composition comprising a crosslinking unsaturated-chain polymer base and a vulcanization system. The adhesive composition comprises 50-200 phr of a product with adhesive action comprising: xylene 30-80% wt, ethylbenzene 10-30% wt, zinc oxide 1-10% wt, and 1-5% wt of a compound selected from the group consisting of 1,1- (l,3-phenylene) bis-lH-pyrrole-2,5-dione, Ν,Ν'- (4,4 diphenylmethane) bismaleimide, diphenylmethanediisocyanate, 4,4'-methylenbis (Ν,Ν'- bis (2,3-epoxypropyl) aniline or mixtures thereof.

Description

“ADHESIVE COMPOSITION FOR VULCANIZED RUBBER”
DESCRIPTION
The present invention relates to an adhesive composition to be applied to a layer of already vulcanized rubber.
As it is well known to those skilled in the art, it is very easy to couple effectively a layer of not yet vulcanized rubber, whilst it is very difficult to couple a layer of already vulcanized rubber. In fact, in the case of not yet vulcanized rubber, an adhesive composition is applied thereto, wherein the adhesive effect is obtained above all during the vulcanization step.
However, above all in the aerospace field, constructive applications exist necessarily involving the coupling of already vulcanized rubber. The coupling can be done between vulcanized rubber and vulcanized rubber or vulcanized rubber and virgin rubber.
One of the processes where it is necessary to couple an already vulcanized rubber to a virgin rubber is, for example, the production of solid-propellant rocket engines.
The solid-propellant rocket engines generally comprise an axial-symmetrical outer casing, which houses a charge of solid propellant, an ignition system provided at an end of the casing and an end nozzle provided at the opposite end. The casing is internally coated with a thermal protection made of ablative material, typically constituted by elastomers charged with additives and/or fibers, to protect the inner surface of the casing against high temperatures and erosion.
Generally, the thermal protection consists of an intermediate cylindrical part formed by winding a web of reinforced ablative material on the surface of a mandrel, and of two end dome-shaped end parts formed out of the site of assemblage. The term "out of the site of assemblage" means that the two end portions are formed separately from the mandrel, and then mounted thereon.
In particular, the two end portions are mounted on the mandrel once they have already been vulcanized. According to this solution, on the mandrel the end portions of already vulcanized rubber are necessarily coupled to the intermediate portion being formed, i.e. still made of virgin (not vulcanized) rubber.
In other words, the thermal portion is made by coupling an intermediate portion of virgin rubber with two end portions of already vulcanized rubber.
As it is clearly apparent to those skilled in the art, the coupling between the intermediate portion and the end portions is a very crucial aspect. In fact, in order for the solid rocket engine to operate correctly, it is important that the coupling of the various parts of the thermal portion is really effective.
There was thus the need to have available an adhesive composition able to ensure the effective coupling of the already vulcanized rubber with either a virgin rubber or an already vulcanized rubber.
The inventors of the present invention have surprisingly found that the use of a compound currently used for making virgin rubber adhere to metal, when properly mixed with a rubber solubilized in an organic solvent, provides an adhesive composition capable of ensuring the effective adhesion of already vulcanized rubber both to already vulcanized rubber and virgin rubber, as well as to metal.
An object of the invention is an organic solvent-based adhesive composition comprising a crosslinking unsaturated-chain polymer base and a vulcanization system, said adhesive composition being characterized by comprising 50-200 phr, preferably 100-150 phr of a product with adhesive action comprising: xylene 30-80% wt, ethylbenzene 10-30% wt, zinc oxide 1-10% wt, and 1-5% wt of a compound selected from the group consisting of l,l-(l,3-phenylene)bis-lH-pirrole-2,5-dione, N,N’- (4,4’diphenylmethane) bismaleimide, diphenylmethanediisocyanate, 4,4'-methylenbis (N, N'-bis (2,3-epoxypropyl) aniline or mixtures thereof.
Said product with adhesive action is preferably marketed under the name Chemosil® 411 or Chemosil® 256 or Chemosil® 425 or Chemosil® 231 o Thixon® 547-EF or Thixon® 6110F. “Crosslinkable, unsaturated-chain polymer base” refers, hereinafter, to any natural or synthetic non-crosslinked polymer, adapted to gain all the chemical-physical and mechanical features typically gained by elastomers following cross-linking (vulcanization).
“Vulcanization system” refers, hereinafter, to a complex of vulcanizing agents that promote vulcanization of the polymer base when the mixture is brought to the vulcanization temperature.
Preferably, the cross -linkable unsaturated-chain polymer base is comprised in group consisting of EPDM, NBR, SBR, HTPB.
Preferably, the vulcanization system comprises a peroxide crosslinking agent.
Preferably, the adhesive composition of the present invention comprises xylene as a solvent.
A further object of the present invention is a method for preparing the adhesive composition of the invention. The method comprises a first mixing step, wherein a crosslinking unsaturated-chain polymer base, a plasticizer oil and a vulcanization system are mixed together; a solubilization step, wherein the mixture formed during the first mixing step is solubilized in an organic solvent thus forming a liquid rubber; and a second mixing step, wherein to the liquid rubber a product is added with adhesive action, comprising: methyl isobutyl ketone 60-93% wt, xylene 5-10% wt, phenol- formaldehyde polymer 1-5% wt, ethylbenzene 1-5% wt.
Preferably, said product with adhesive action is marketed under the name Chemosil® 411.
Below, embodiments are described just by way of non-limiting examples.
The adhesive composition of the invention has been made.
Firstly, a rubber mixture has been prepared by mixing the compounds shown in Table I (amounts in phr) at room temperature. TABLE I
Figure imgf000005_0001
NOREX HI has been used as plasticizer oil.
AEROSIL R 972 has been used as rheology modifier.
TRIGONOX 101-50D-PD has been used as peroxide crosslinking agent.
TRIALLYL CYANETRATE has been used as accelerator.
Then, the above rubber mixture has been solubilized in xylene with a weight ratio of 1 part of rubber mixture and 10 parts of xylene.
The rubber mixture has been solubilized in xylene, resulting in the formation of a liquid rubber.
Chemosil® 411 has been added to the liquid rubber with a 1:1 weight ratio (Chemosil® 41 Erubber mixture).
The adhesive composition obtained looks like a low-viscosity liquid. In particular, the viscosity of the adhesive composition has been found equal to 600 mPa.s at 25°C.
The method described above is significant for the effectiveness of the adhesive composition.
In this regard, an attempt has been made to prepare the adhesive composition by adding all the ingredients, including Chemosil ® 411, directly into xylene without previous preparation of a rubber mixture as defined above. The adhesive composition obtained has been found less effective than that obtained with the method of the invention.
The adhesive composition obtained can be applied by means of a brush or by spraying.
The adhesive composition prepared as described above has been tested for the coupling between: a layer of vulcanized rubber and a layer of virgin rubber; a layer of vulcanized rubber and a further layer of vulcanized rubber; a layer of vulcanized rubber and a metal. In order to verify the advantages of the adhesive composition of the invention, the adhesion tests have been repeated using both the only rubber mixture and the only Chemosil® 411 as adhesive agent. In order to have a comparison as significant as possible, the rubber mixture and Chemosil® 411, when used alone, have been used in the same amount as in the adhesive composition of the invention.
The tests have been carried out under the same conditions, in order to ensure the significance of the comparison. Specifically, the various adhesive agents have been applied by brush in three subsequent coats, every subsequent coat having been applied once the solvent was evaporated. After the last coat, the two parts to be coupled have been kept in contact with each other and vulcanized in autoclave at l65°C under a pressure higher than 2 bar.
After the time indicated above, on each coupling a traction measurement has been performed.
Table II shows the results of the traction measurements.
In Table II the term "INV." refers to the use of the adhesive composition of the invention (rubber mixture added with Chemosil® 411); the term "CONF.A" refers to the use of only the rubber mixture; the term "CONF.B" refers to the use of only Chemosil® 411. The values in Table II are in MPa. TABLE II
Figure imgf000007_0001
From the values of Table II it is clearly apparent that the adhesive composition of the invention endures greater adhesion with respect to the comparative examples.
The effectiveness of the adhesive composition of the invention has been extremely surprising, as to date Chemosil® 411 has been used only for making virgin rubber adhere to metal. Differently from what described for the adhesive composition of the invention, Chemosil® 411 was applied directly (without being first added to a liquid rubber) on the virgin rubber layer, and the adhesive action thereof was performed during the vulcanization phase at l30°C-l80°C. In other words, according to the prior art, i.e. before the present invention, a necessary condition for Chemosil® 411 to be effective was that it would be subjected to a vulcanization phase at approximately l50°C.
In conclusion, the inventors of the present invention have provided an extremely effective solvent-based adhesive composition for coupling already vulcanized rubber by using a compound that was known for the adhesive effectiveness for coupling virgin rubber and only if used in a process including vulcanization.

Claims

1. An organic solvent-based adhesive composition comprising a crosslinking unsaturated-chain polymer base and a vulcanization system, said adhesive composition being characterized by comprising 50-200 phr of a product with adhesive action comprising: xylene 30-80% wt, ethylbenzene 10-30% wt, zinc oxide 1-10% wt, and 1-5% wt of a compound selected from the group consisting of l,l-(l,3- phenylene)bis-lH-pirrole-2,5-dione, N,N’-(4,4’diphenylmethane) bismaleimide, diphenylmethanediisocyanate, 4,4'-methylenbis (N, N'-bis (2,3-epoxypropyl) aniline or mixtures thereof.
2. The organic solvent-based adhesive composition of claim 1, characterized in that said product with adhesive action is marketed under the name Chemosil® 411 or Chemosil® 256 or Chemosil® 425 or Chemosil® 231 o Thixon® 547-EF or Thixon® 6110F.
3. The organic solvent-based adhesive composition of claim 1 or 2, characterized by comprising said product with adhesive action in an amount comprised between 100 and 150 phr.
4. The organic solvent-based adhesive composition of any one of the previous claims, characterized in that the crosslinking unsaturated-chain polymer base is comprised in the group consisting of EPDM, NBR, SBR, HTPB.
5. The organic solvent-based adhesive composition of any one of the previous claims, characterized in that the vulcanization system comprises a peroxide crosslinking agent.
6. The organic solvent-based adhesive composition according to any one of the previous claims, characterized in that the organic solvent is xylene.
7. A method for preparing an organic solvent-based adhesive composition characterized by comprising a first mixing step, wherein a crosslinking unsaturated- chain polymer base, a plasticizer oil and a vulcanization system are mixed together; a solubilization step, wherein the mixture formed during the first mixing step is solubilized in an organic solvent, thus forming a liquid rubber; and a second mixing step, wherein to the liquid rubber a product is added with adhesive action, comprising: xylene 30-80% wt, ethylbenzene 10-30% wt, zinc oxide 1-10% wt, and 1-5% wt of a compound selected from the group consisting of 1,1- (l,3-phenylene) bis-lH-pyrrole- 2,5-dione, N,N'- (4,4 diphenylmethane) bismaleimide, diphenylmethanediisocyanate, 4,4'-methylenbis (N,N'-bis (2,3-epoxypropyl) aniline or mixtures thereof.
8. The method of claim 7, characterized in that said product with adhesive action is marketed under the name Chemosil® 411 or Chemosil® 256 or Chemosil® 425 or Chemosil® 231 o Thixon® 547-EF or Thixon® 6110F.
9. The method of claim 7 or 8, characterized in that in said solubilization step the weight ratio between the mixture formed during the first mixing step and the organic solvent is comprised between 1:7 e 1:13.
10. The method of any one of claims 7 to 9, characterized in that said product with adhesive action is added in an amount comprised between 50 and 200 phr.
11. The method of any one of claims 7 to 10, characterized in that said product with adhesive action is added in an amount comprised between 100 and 150 phr.
12. The method of any one of claims 7 to 11, characterized in that said organic solvent is xylene.
13. The method of any one of claims 7 to 12, characterized by being carried out at room temperature.
PCT/IB2019/054705 2018-06-06 2019-06-06 Adhesive composition for vulcanized rubber WO2019234667A1 (en)

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IT102018000006059A IT201800006059A1 (en) 2018-06-06 2018-06-06 ADHESIVE COMPOSITION FOR VULCANIZED RUBBER

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2793691C1 (en) * 2022-07-19 2023-04-04 Федеральное государственное автономное образовательное учреждение высшего образования "Северо-Восточный федеральный университет имени М.К.Аммосова" Method for obtaining a composite high-modulus material based on butadiene elastomer with a flexible reinforcing element

Citations (5)

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US4994519A (en) * 1987-02-11 1991-02-19 Henkel Kommanditgesellschaft Auf Aktien Rubber-to-metal binders from chlorinated rubber and brominated polydichlorobutadiene
US5268404A (en) * 1989-12-04 1993-12-07 Lord Corporation One-coat rubber-to-metal bonding adhesive
RU2481369C1 (en) * 2012-03-29 2013-05-10 Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Волгоградский государственный технический университет" (ВолгГТУ) Method of gluing rubber
RU2492340C1 (en) * 2012-03-22 2013-09-10 Открытое акционерное общество Научно-производственное объединение "Искра" Method to manufacture inner heat-shielding coating of rocket engine body
WO2014018761A1 (en) * 2012-07-25 2014-01-30 Lord Corporation Improved post-vulcanization bonding

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4994519A (en) * 1987-02-11 1991-02-19 Henkel Kommanditgesellschaft Auf Aktien Rubber-to-metal binders from chlorinated rubber and brominated polydichlorobutadiene
US5268404A (en) * 1989-12-04 1993-12-07 Lord Corporation One-coat rubber-to-metal bonding adhesive
RU2492340C1 (en) * 2012-03-22 2013-09-10 Открытое акционерное общество Научно-производственное объединение "Искра" Method to manufacture inner heat-shielding coating of rocket engine body
RU2481369C1 (en) * 2012-03-29 2013-05-10 Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Волгоградский государственный технический университет" (ВолгГТУ) Method of gluing rubber
WO2014018761A1 (en) * 2012-07-25 2014-01-30 Lord Corporation Improved post-vulcanization bonding

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2793691C1 (en) * 2022-07-19 2023-04-04 Федеральное государственное автономное образовательное учреждение высшего образования "Северо-Восточный федеральный университет имени М.К.Аммосова" Method for obtaining a composite high-modulus material based on butadiene elastomer with a flexible reinforcing element

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