FR2664282A1 - Process for making hydrophilic the surface of articles made of resins based on vinyl chloride - Google Patents
Process for making hydrophilic the surface of articles made of resins based on vinyl chloride Download PDFInfo
- Publication number
- FR2664282A1 FR2664282A1 FR9108659A FR9108659A FR2664282A1 FR 2664282 A1 FR2664282 A1 FR 2664282A1 FR 9108659 A FR9108659 A FR 9108659A FR 9108659 A FR9108659 A FR 9108659A FR 2664282 A1 FR2664282 A1 FR 2664282A1
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- FR
- France
- Prior art keywords
- process according
- treatment
- vinyl chloride
- water
- oxidation treatment
- Prior art date
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/12—Chemical modification
- C08J7/16—Chemical modification with polymerisable compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/12—Chemical modification
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2327/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers
- C08J2327/02—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment
- C08J2327/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
- C08J2327/06—Homopolymers or copolymers of vinyl chloride
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- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
- Laminated Bodies (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
Abstract
Description
Procédé pour rendre hydrophile la surface d'articles
en résines à base de chlorure de vinyle.Method for rendering the surface of articles hydrophilic
resins based on vinyl chloride.
La présente invention concerne un procédé pour rendre hydrophile la surface d'articles en résines à base de chlorure de vinyle. The present invention relates to a method for rendering the surface of vinyl chloride-based resin articles hydrophilic.
Les résines à base de chlorure de vinyle, compte tenu de leur prix, de leur facilité de mise en oeuvre et de leurs excellentes propriétés, sont utilisées de longue date pour la production de nombreux articles. Resins based on vinyl chloride, having regard to their price, their ease of processing and their excellent properties, have been used for a long time for the production of numerous articles.
Il est toutefois bien connu que ces résines et en particulier le polychlorure de vinyle présentent un caractère hydrophobe. Ainsi la tension superficielle du polychlorure de vinyle est de l'ordre de 33 mN/m et en conséquence ce produit n'est pas mouillable. Cette caractéristique, qui dans de nombreux cas d'utilisation peut se révéler intéressante peut, par contre, dans certaines applications entraîner des conséquences non souhaitables. Ainsi, par exemple, lorsqu'on réalise des plaques ondulées en polychlorure de vinyle et qu'on utilise celles-ci pour la réalisation de serres, on constate que l'humidité règnant dans ces enceintes se condense sur la face intérieure des plaques sous forme de gouttes qui tombent sur les plantes cultivées et risquent de les endommager. It is however well known that these resins and in particular polyvinyl chloride have a hydrophobic character. Thus the surface tension of polyvinyl chloride is of the order of 33 mN / m and consequently this product is not wettable. This characteristic, which in many cases of use can prove to be advantageous, on the other hand, in certain applications can lead to undesirable consequences. Thus, for example, when making corrugated polyvinyl chloride plates and using them for the production of greenhouses, it is found that the humidity prevailing in these enclosures condenses on the inside of the plates in the form drops that fall on crop plants and may damage them.
Pour éviter cet inconvénient, on peut, certes, pulvériser un agent tensio-actif sur la face interne des plaques mais cette solution se révèle astreignante, coûteuse et d'efficacité limitée dans le temps. To avoid this drawback, it is certainly possible to spray a surface-active agent on the internal face of the plates, but this solution proves to be demanding, costly and of effectiveness limited in time.
Une autre solution envisageable consiste à effectuer un traitement oxydant superficiel tel que, par exemple, un traitement Corona, un traitement à la flamme oxydante ou un traitement de fluoration sur la face interne des plaques. Il est toutefois apparu que ces types de traitement peuvent, certes, améliorer la mouillabilité mais que leur efficacité dans le temps dépend de facteurs tels que la température, l'humidité, etc. et, en général, va en s'amenuisant parfois très rapidement. Another possible solution consists in carrying out a surface oxidizing treatment such as, for example, a Corona treatment, an oxidizing flame treatment or a fluorination treatment on the internal face of the plates. However, it has appeared that these types of treatment can certainly improve wettability, but that their effectiveness over time depends on factors such as temperature, humidity, etc. and, in general, sometimes decreases very quickly.
Une dernière solution envisageable peut consister à appliquer sur la face interne des plaques une couche d'un matériau hydrophile économiquement acceptable. Toutefois, il a été généralement constaté que les enduits testés soit se révèlent insuffisamment efficaces ou encore insuffisamment adhérant sur les surfaces traitées. A last possible solution may consist in applying a layer of an economically acceptable hydrophilic material to the internal face of the plates. However, it has generally been found that the coatings tested either prove to be insufficiently effective or even insufficiently adhering to the treated surfaces.
Après de nombreux essais, la demanderesse est néanmoins parvenue a mettre au point un procédé efficace et durable pour rendre hydrophile la surface d'articles en résines à base de chlorure de vinyle. After numerous tests, the Applicant has nevertheless succeeded in developing an effective and durable process for rendering the surface of articles made of vinyl chloride-based resins hydrophilic.
La présente invention concerne, dès lors un procédé pour rendre hydrophile la surface d'articles en résines à base de chlorure de vinyle qui se caractérise en ce qu'on soumet la surface à un traitement d'oxydation superficielle, en ce qu'on enduit la surface oxydée d'une couche d'une solution aqueuse d'un silane monomère comportant un atome d'azote en position gamma et en ce qu'on élimine ensuite l'eau de la couche enduite. The present invention therefore relates to a process for rendering the surface of vinyl chloride-based resin articles hydrophilic, which is characterized in that the surface is subjected to a surface oxidation treatment, in that it is coated. the oxidized surface of a layer of an aqueous solution of a monomeric silane comprising a nitrogen atom in the gamma position and in that the water is then removed from the coated layer.
Par résines à base de chlorure de vinyle, on entend désigner les homopolymères du chlorure de vinyle ainsi que les copolymères du chlorure de vinyle contenant au moins 70 X en poids d'unités dérivées du chlorure de vinyle, le ou les comonomère(s) utilisé(s) pour la production de ces derniers étant choisi(s) dans le groupe formé par les oléfines telles que l'éthylène, le propylène et le styrène et les esters vinyliques, acryliques ou méthacryliques tels que l'acétate de vinyle et les acrylates et méthacrylates d'alkyle. En règle générale, la préférence est toutefois accordée aux résines à base d'homopolymères du chlorure de vinyle ces résines pouvant évidemment contenir des additifs tels que notamment des stabilisants. The term “vinyl chloride-based resins” is intended to denote the homopolymers of vinyl chloride as well as the copolymers of vinyl chloride containing at least 70% by weight of units derived from vinyl chloride, the comonomer (s) used (s) for the production of the latter being selected from the group formed by olefins such as ethylene, propylene and styrene and vinyl, acrylic or methacrylic esters such as vinyl acetate and acrylates and alkyl methacrylates. As a general rule, however, preference is given to resins based on vinyl chloride homopolymers, these resins can obviously contain additives such as stabilizers in particular.
Dans le procédé conforme à l'invention, il est impératif de soumettre d'abord la surface de l'article en résines à base chlorure de vinyle à un traitement d'oxydation superficielle. En effet, si on omet ce prétraitement, on constate que l'adhérence de l'enduit déposé par la suite se révèle insuffisante. Par contre, le recours à un tel prétraitement conduit à des enduits dont l'ahérence est excellente dans le temps. In the process according to the invention, it is imperative to first subject the surface of the vinyl chloride-based resin article to a surface oxidation treatment. Indeed, if this pretreatment is omitted, it is found that the adhesion of the coating subsequently deposited proves to be insufficient. On the other hand, the use of such a pretreatment leads to coatings whose appearance is excellent over time.
Le traitement d'oxydation superficielle peut être soit un traitement Corona, ou un traitement à la flamme oxydante ou encore un traitement d'oxyfluoration. The surface oxidation treatment can be either a Corona treatment, or an oxidizing flame treatment or even an oxyfluorination treatment.
Les traitements Corona et à la flamme oxydante sont d'utilisation courante dans le domaine de la mise en oeuvre des matières plastiques et il n'est donc pas nécessaire de les détailler. En cas de besoin, on peut d'ailleurs se référer notamment aux brevets US-A-2648097, US-A-2683894 et US-A-3142630 et à la demande de brevet japonais 73/29316 qui concernent ces techniques. Corona and oxidizing flame treatments are in common use in the field of processing plastics and there is therefore no need to detail them. If necessary, one can also refer in particular to patents US-A-2648097, US-A-2683894 and US-A-3142630 and to Japanese patent application 73/29316 which relate to these techniques.
Le traitement d'oxyfluoration est de préférence réalisé en faisant passer l'article à température ambiante dans une enceinte contenant un mélange d'air et de fluor dans des proportions en poids de 97/3 à 90/10, le temps de séjour dans l'enceinte étant de 1 à 3 minutes. Pour réaliser ce traitement, on peut notamment utiliser le dispositif décrit dans la demande de brevet européen
EP-A-0214635.The oxyfluorination treatment is preferably carried out by passing the article at ambient temperature in an enclosure containing a mixture of air and fluorine in weight proportions of 97/3 to 90/10, the residence time in l 'pregnant for 1 to 3 minutes. To carry out this treatment, it is possible in particular to use the device described in the European patent application.
EP-A-0214635.
Le silane monomère utilisé pour réaliser la solution aqueuse d'enduction peut avantageusement être choisi dans le groupe formé par les 3-aminoalkyltrialkoxysilanes et les N-(2-aminoalkyl-3 -aminoalkyl)-trialkoxysilanes, le 3-aminopropyltriéthoxysilane et le N-(2-aminoethyl-3-aminopropyl)-triméthoxysilane étant préférés. The silane monomer used to make the aqueous coating solution may advantageously be chosen from the group formed by 3-aminoalkyltrialkoxysilanes and N- (2-aminoalkyl-3 -aminoalkyl) -trialkoxysilanes, 3-aminopropyltriethoxysilane and N- ( 2-aminoethyl-3-aminopropyl) -trimethoxysilane being preferred.
Il a, en effet, été constaté que les silanes susmentionnés, du fait de la présence d'un atome d'azote en position gamma permettent la production de solutions aqueuses d'enduction qui se caractérisent par une stabilité remarquable. It has in fact been found that the aforementioned silanes, due to the presence of a nitrogen atom in the gamma position, allow the production of aqueous coating solutions which are characterized by remarkable stability.
La concentration de silane monomère dans la solution aqueuse d'enduction est généralement comprise entre 0,05 et 1 gramme par litre et, de préférence, entre 0,1 et 0,5 gramme par litre, la quantité de solution déposée pouvant varier entre 10 et 150 g/m2 et, de préférence entre 20 et 100 g/m2
Après enduction des articles, il convient d'éliminer l'eau contenue dans la solution d'enduction. Cette élimination peut être réalisée en faisant passer les articles enduits au travers d'une étuve ventilée ou encore au travers d'un four équipé d'éléments de chauffage radiants appropriés.The concentration of monomeric silane in the aqueous coating solution is generally between 0.05 and 1 gram per liter and, preferably, between 0.1 and 0.5 gram per liter, the quantity of solution deposited can vary between 10 and 150 g / m2 and, preferably between 20 and 100 g / m2
After coating the items, the water in the coating solution should be removed. This elimination can be carried out by passing the coated articles through a ventilated oven or even through an oven equipped with suitable radiant heating elements.
Dans le cas de la production de plaques ondulées, impliquant l'extrusion d'une plaque plane et la mise en forme en continu de la plaque par passage au travers d'une ondulatrice, le procédé de traitement selon l'invention peut avantageusement être appliqué juste en amont de l'étape de mise en forme. In the case of the production of corrugated sheets, involving the extrusion of a flat sheet and the continuous shaping of the sheet by passage through an undulator, the treatment method according to the invention can advantageously be applied just before the shaping stage.
I1 est, par ailleurs, bien évident que le procédé conforme à l'invention ne doit pas être strictement limité au traitement de plaques ondulées mais qu'il peut être exploité pour le traitement de tout article dont la surface doit être rendue hydrophile de façon durable. I1 is, moreover, very obvious that the process according to the invention should not be strictly limited to the treatment of corrugated sheets but that it can be used for the treatment of any article the surface of which must be made hydrophilic in a sustainable manner. .
Le procédé conforme à l'invention est, en outre, illustré par les exemples de réalisation pratique qui suivent. The process according to the invention is further illustrated by the following practical examples.
Exemple 1
Une plaque de polychlorure de vinyle de 1,4 mm d'épaisseur est d'abord traitée sur un appareillage de décharge Corona CAS commercialisé par Ahlbrandt System GmbH dans les conditions suivantes
Vitesse de défilement : 20 m/min.Example 1
A 1.4 mm thick polyvinyl chloride plate is first treated on a Corona CAS discharge device marketed by Ahlbrandt System GmbH under the following conditions
Scrolling speed: 20 m / min.
Température : 250C
Puissance : 2,2 kW
Fréquence : 20 kil
Distance entre électrodes : 2,4 mm
Après ce traitement, on constate que la tension superficielle de la plaque est de 46-48 mN/m. Temperature: 250C
Power: 2.2 kW
Frequency: 20 kil
Distance between electrodes: 2.4 mm
After this treatment, it is found that the surface tension of the plate is 46-48 mN / m.
La plaque traitée est ensuite enduite par une solution aqueuse de 3-aminopropyltriéthoxysilane (concentration 0,05 g/l) à raison de 40 g de solution par mètre carré. The treated plate is then coated with an aqueous solution of 3-aminopropyltriethoxysilane (concentration 0.05 g / l) at the rate of 40 g of solution per square meter.
La plaque enduite est enfin séchée par passage dans une étuve ventilée maintenue à 800C. The coated plate is finally dried by passage in a ventilated oven maintained at 800C.
Après séchage, on constate que l'enduit déposé adhère parfaitement sur la plaque même après une exposition prolongée dans de l'eau et que la tension superficielle de la face traitée de la plaque s'élève à plus de 56 mN/m. On remarque, dès lors, que la plaque est parfaitement mouillable et ce de façon durable. After drying, it can be seen that the coating deposited adheres perfectly to the plate even after prolonged exposure to water and that the surface tension of the treated face of the plate amounts to more than 56 mN / m. It is noted, therefore, that the plate is perfectly wettable and this in a sustainable manner.
Exemple 2
On soumet une plaque de polychlorure de vinyle de 1,4 mm d'épaisseur à un traitement d'oxyfluoration par passage dans une installation telle que décrite dans la demande de brevet européen 0214635, les conditions de traitements étant
Température : 250C
Durée : 2 min.Example 2
A 1.4 mm thick polyvinyl chloride plate is subjected to an oxyfluorination treatment by passage through an installation as described in European patent application 0214635, the treatment conditions being
Temperature: 250C
Duration: 2 mins.
Milieu réactif : 5 Z F2, 95 X air
Après ce traitement, on constate que la tension superficielle de la plaque s'élève à 46-48 mN/m.Reactive medium: 5 Z F2, 95 X air
After this treatment, it is found that the surface tension of the plate amounts to 46-48 mN / m.
La plaque traitée est ensuite enduite par une solution aqueuse de N-(2-aminoéthyl-3-aminopropyl) triméthoxysilane (concentration : 0,05 g/l) à raison de 40 g de solution par mètre carré. The treated plate is then coated with an aqueous solution of N- (2-aminoethyl-3-aminopropyl) trimethoxysilane (concentration: 0.05 g / l) at a rate of 40 g of solution per square meter.
La plaque enduite est enfin séchée par passage dans une étuve ventilée maintenue à 80au. The coated plate is finally dried by passage through a ventilated oven maintained at 80 ° C.
Après séchage, on constate que l'enduit déposé adhère parfaitement sur la plaque même après une exposition prolongée dans de l'eau et que la tension superficielle de la face traitée de la plaque s'élève à plus de 56 mN/m. On remarque, dès lors, que la plaque est parfaitement mouillable et ce de façon durable. After drying, it is found that the coating deposited adheres perfectly to the plate even after prolonged exposure in water and that the surface tension of the treated face of the plate amounts to more than 56 mN / m. It is noted, therefore, that the plate is perfectly wettable and this in a sustainable manner.
Exemple 3R
A titre d'essai comparatif, on opère comme dans l'exemple 1 mais en omettant l'étape de traitement Corona.Example 3R
By way of comparative test, the procedure is as in Example 1 but omitting the Corona treatment step.
On constate, après séchage de l'enduit, que celui-ci n'adhère pas de façon satisfaisante sur la plaque de polychlorure de vinyle. It is noted, after drying of the coating, that it does not adhere satisfactorily to the polyvinyl chloride plate.
Claims (10)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE9000701A BE1004488A3 (en) | 1990-07-09 | 1990-07-09 | Method for making hydrophilic surface articles resins vinyl chloride base. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2664282A1 true FR2664282A1 (en) | 1992-01-10 |
| FR2664282B1 FR2664282B1 (en) | 1992-11-20 |
Family
ID=3884864
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR9108659A Expired - Fee Related FR2664282B1 (en) | 1990-07-09 | 1991-07-08 | PROCESS FOR MAKING THE SURFACE OF VINYL CHLORIDE RESIN ARTICLES HYDROPHILIC. |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE1004488A3 (en) |
| FR (1) | FR2664282B1 (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0740681A1 (en) * | 1994-01-21 | 1996-11-06 | Commonwealth Scientific And Industrial Research Organisation | Surface treatment of polymers |
| WO1997000899A1 (en) * | 1995-06-22 | 1997-01-09 | Yuri Gudimenko | Surface modification of polymers and carbon-based materials |
| WO1998011154A1 (en) * | 1996-09-13 | 1998-03-19 | Minnesota Mining And Manufacturing Company | Flame-treating process |
| US5922161A (en) * | 1995-06-30 | 1999-07-13 | Commonwealth Scientific And Industrial Research Organisation | Surface treatment of polymers |
| US7918040B2 (en) * | 2004-03-02 | 2011-04-05 | Nv Bekaert Sa | Drier installation for drying web |
| US7926200B2 (en) | 2004-03-02 | 2011-04-19 | Nv Bekaert Sa | Infrared drier installation for passing web |
| WO2014209832A1 (en) * | 2013-06-28 | 2014-12-31 | 3M Innovative Properties Company | Article with silanol coating and method of making |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0010632A1 (en) * | 1978-10-05 | 1980-05-14 | Toray Industries, Inc. | Process for treating the surface of plastics and film produced by this process |
| JPS5938034A (en) * | 1982-08-27 | 1984-03-01 | Hitachi Zosen Corp | Formation of composite tube |
| EP0256643A2 (en) * | 1986-07-11 | 1988-02-24 | Hugh Steeper Limited | Surface and Bulk Modification of plasticized materials |
| US4764405A (en) * | 1987-07-22 | 1988-08-16 | Air Products And Chemicals, Inc. | Method for increasing barrier properties of thermoplastic substrates |
-
1990
- 1990-07-09 BE BE9000701A patent/BE1004488A3/en not_active IP Right Cessation
-
1991
- 1991-07-08 FR FR9108659A patent/FR2664282B1/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0010632A1 (en) * | 1978-10-05 | 1980-05-14 | Toray Industries, Inc. | Process for treating the surface of plastics and film produced by this process |
| JPS5938034A (en) * | 1982-08-27 | 1984-03-01 | Hitachi Zosen Corp | Formation of composite tube |
| EP0256643A2 (en) * | 1986-07-11 | 1988-02-24 | Hugh Steeper Limited | Surface and Bulk Modification of plasticized materials |
| US4764405A (en) * | 1987-07-22 | 1988-08-16 | Air Products And Chemicals, Inc. | Method for increasing barrier properties of thermoplastic substrates |
Non-Patent Citations (1)
| Title |
|---|
| BASE DE DONNEES WPIL, accession no. 84-091574 [15], Derwent Publications Ltd, Londres, GB; & JP-A-59 038 034 (HITACHI ZOSEN CORP.) * |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0740681A4 (en) * | 1994-01-21 | 1998-03-04 | Commw Scient Ind Res Org | Surface treatment of polymers |
| US5879757A (en) * | 1994-01-21 | 1999-03-09 | Commonwealth Of Australia Scientific And Research Organisation | Surface treatment of polymers |
| EP0740681A1 (en) * | 1994-01-21 | 1996-11-06 | Commonwealth Scientific And Industrial Research Organisation | Surface treatment of polymers |
| US5948484A (en) * | 1995-06-22 | 1999-09-07 | Gudimenko; Yuri | Modification of subsurface region of polymers and carbon-based materials |
| WO1997000899A1 (en) * | 1995-06-22 | 1997-01-09 | Yuri Gudimenko | Surface modification of polymers and carbon-based materials |
| EP0949277A3 (en) * | 1995-06-22 | 2000-12-27 | Yuri Gudimenko | Surface modification of polymers and carbon-based materials |
| EP0949277A2 (en) * | 1995-06-22 | 1999-10-13 | Yuri Gudimenko | Surface modification of polymers and carbon-based materials |
| US5922161A (en) * | 1995-06-30 | 1999-07-13 | Commonwealth Scientific And Industrial Research Organisation | Surface treatment of polymers |
| CN1085990C (en) * | 1995-06-30 | 2002-06-05 | 联邦科学及工业研究组织 | Improved surface treatment of polymers |
| US5900317A (en) * | 1996-09-13 | 1999-05-04 | Minnesota Mining & Manufacturing Company | Flame-treating process |
| WO1998011154A1 (en) * | 1996-09-13 | 1998-03-19 | Minnesota Mining And Manufacturing Company | Flame-treating process |
| US7918040B2 (en) * | 2004-03-02 | 2011-04-05 | Nv Bekaert Sa | Drier installation for drying web |
| US7926200B2 (en) | 2004-03-02 | 2011-04-19 | Nv Bekaert Sa | Infrared drier installation for passing web |
| WO2014209832A1 (en) * | 2013-06-28 | 2014-12-31 | 3M Innovative Properties Company | Article with silanol coating and method of making |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2664282B1 (en) | 1992-11-20 |
| BE1004488A3 (en) | 1992-12-01 |
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