EP0000699A1 - Procédé de préparation de polyvinyl butyral ayant des propriétés améliorées. - Google Patents
Procédé de préparation de polyvinyl butyral ayant des propriétés améliorées. Download PDFInfo
- Publication number
- EP0000699A1 EP0000699A1 EP7878100324A EP78100324A EP0000699A1 EP 0000699 A1 EP0000699 A1 EP 0000699A1 EP 7878100324 A EP7878100324 A EP 7878100324A EP 78100324 A EP78100324 A EP 78100324A EP 0000699 A1 EP0000699 A1 EP 0000699A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- polyvinyl butyral
- polyvinyl
- weight
- polymer
- weight percent
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
- B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
- B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
- B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
- B32B17/1055—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
- B32B17/10761—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer containing vinyl acetal
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/48—Isomerisation; Cyclisation
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31627—Next to aldehyde or ketone condensation product
- Y10T428/3163—Next to acetal of polymerized unsaturated alcohol [e.g., formal butyral, etc.]
Definitions
- polyvinyl butyral by acetalizing polyvinyl alcohol with n-butyraldehyde.
- polyvinyl alcohol is dispersed in an organic solvent, for example ethanol, and reacted with butyraldehyde in the presence of acid.
- organic solvent for example ethanol
- butyraldehyde in the presence of acid.
- the result is a solution of high quality polyvinyl butyral.
- Disadvantages of this process are the complex isolation of the polymer from the solution and the recovery of the solvent.
- the invention now relates to a process for the production of polyvinyl butyral with improved properties and is characterized in that a polyvinyl butyral with a viscosity of 10 to 200 cp (measured according to DIN 53015 on a 5% by weight solution in ethanol at 23 ° C) and a content of 17 to 24 percent by weight vinyl alcohol units in the aqueous phase at 50 to 70 ° C in the presence of 0.01 to 5 percent by weight, based on the polyvinyl butyral, an emulsifying organic sulfonic acid having 8 to 30 carbon atoms 0, After-treated for 5 to 10 hours under known acetalization conditions and then separated off in a conventional manner.
- the polyvinyl butyral obtained according to the invention is distinguished by considerably increased strength and rigidity and at the same time shows a reduced solubility.
- the aftertreatment of a polyvinylbutyral prepared in the aqueous phase is particularly advantageous, in the production of which the reaction temperature was below 20 ° C. until the acetalization had ended.
- the polyvinyl butyral is obtained in a grain size (particle diameter) that is more than 90% less than 1 millimeter, for the most part even less than 0.5 millimeter, and is therefore particularly suitable for post-treatment suitable is.
- grain size particle diameter
- grinding to the specified grain size is recommended before the aftertreatment.
- polyvinyl butyrals with a viscosity of 10 to 200 cp, preferably 50 to 100 cp (measured in accordance with DIN 53015 on a 5% by weight solution in ethanol at 23 ° C.).
- the chemical composition of the polyvinyl butyral is of particular importance for the success of the process according to the invention.
- the mechanical properties can be improved more easily in polyvinyl butyrals with a high content of vinyl alcohol units than with a low content of vinyl alcohol units. If the proportion of vinyl alcohol units is less than 17 percent by weight, a significant improvement in the mechanical properties can no longer be observed. However, if the proportion is over 24 percent by weight, the aftertreatment gives a polyvinyl butyral which can no longer be processed sufficiently. Therefore, a content of 17 to 24% by weight of vinyl alcohol units, preferably a content of 18 to 23% by weight of vinyl alcohol units, is used.
- the mechanical properties of the reaction product are also strongly influenced by the temperature used in the aftertreatment. Temperatures below 50 ° C are not recommended because the reaction will take too long. Above. 65 ° C, with high molecular weight polyvinyl butyrals above 70 ° C, the polymer tends to coarsen the Grain texture and for lump formation. It is therefore generally carried out at 50 to 70 ° C, preferably at 50 to 65 ° C.
- the duration of the aftertreatment is generally between 0.5 and 10 hours, preferably between 1 and 7 hours.
- a particularly important prerequisite for improving the properties of the polyvinyl butyral by the aftertreatment according to the invention is the presence of 0.01 to 0.5, preferably 0.05 to 0.2 percent by weight, based on the polyvinyl butyral, of an emulsifying organic sulfonic acid having 8 to 30 carbon atoms .
- Alkyl and alkylarylsulfonic acids for example dodecylbenzenesulfonic acid or hexadecanesulfonic acid, are suitable for this. It is also possible to use mixtures of this acid.
- the aliphatic radical of the sulfonic acids can be branched and the aromatic radical can also be substituted by one or more alkyl groups.
- the aftertreatment also takes place in the aqueous phase under customary acetalization conditions, using 1 to 100 parts by weight of water per part by weight of polymer and about 0.1 to 5% by weight of an inorganic acid, based on the aqueous phase.
- the reaction system is kept in motion by stirring. Sulfuric acid or hydrochloric acid is preferably used as the inorganic acid.
- the concentration of n-butyraldehyde should be chosen so that the proportion of vinyl alcohol units in the aftertreated polymer is between 17 and 24, preferably between 18 and 23 percent by weight.
- the subsequent treatment of polyvinyl butyral according to the invention is ended by the removal of the end product.
- the same procedure is followed as is known for the production of polyvinyl butyrals from an aqueous phase.
- the work-up consists in the complete removal of the acid from the polymer, preferably by intensive washing with water. According to known methods, it is advisable to apply a small amount of alkali to the polymer before the subsequent drying, so that 5 to 100 milliliters of 0.01 normal HCl solution are required, for example, to neutralize 100 grams of polyvinyl butyral.
- the properties of the end product can be influenced gradually and reproducibly by varying the different process features.
- The. is particularly important because the polyvinyl butyrals used as the starting product can differ structurally depending on their manufacturing conditions. Polyvinyl butyrals e.g. produced at low temperature are usually more statistical than polyvinyl butyrals obtained at higher temperatures.
- An intensive aftertreatment can be used to obtain an end product of the same quality from the former as from the latter, which are not changed as much by the conditions of the aftertreatment.
- the properties of polyvinyl butyral during the inventions aftertreatment according to the invention can be determined in a simple manner, for example by determining the viscosity of a 5% ethanol solution at 23 ° C. according to DIN 53015 and following the change in viscosity at this temperature.
- the polyvinyl butyral is dissolved at 70 ° C.
- the solution is then cooled to the measuring temperature within 5 minutes and the viscosity is determined immediately.
- Untreated polymers with a vinyl alcohol unit content of less than 23 percent by weight practically do not change their viscosity during this treatment.
- the changes in properties of the polyvinyl butyral achieved by the process according to the invention are very noticeable.
- the strength and rigidity of the polymer are increased considerably.
- Softened films which are produced from the polyvinylbutyral treated according to the invention show a significantly increased stiffness, a considerably increased strength with defined elongation and an increased tensile strength with only slightly reduced elongation at break compared to known polyvinylbutyral films. They tend to drop at temperatures below 100 ° C the films made according to the invention made of polyvinyl butyral are much less flowable, which facilitates their use as composite films for safety glass.
- the post-treatment according to the invention surprisingly also greatly reduces the undesirable tackiness of the polyvinyl butyral films.
- the processing of the polyvinyl butyral obtained by the aftertreatment according to the invention into composite films is carried out in the usual way. Since the flowability in the plasticizer-containing melt is reduced by the aftertreatment, it is advisable to use polymers with a molecular weight - expressed by the viscosity in 5% ethanol solution at 23 ° C according to DIN 53015 - which is generally lower than that of the Polyvinyl butyrals commonly used for this purpose. To further improve the flowability, polyvinyl butyrals with a lower molecular weight can also be added. Finally, the processability of the polyvinyl butyral produced according to the invention can also be influenced by varying the plasticizer added.
- the amount of the plasticizer to be added is generally 20 to 60 parts by weight, particularly 30 to 50 parts by weight, per 100 parts by weight of polyvinyl butyral.
- the commonly used compounds for example esters of polyhydric alcohols or of, serve as plasticizers polyvalent acids.
- esters of triethylene glycol with aliphatic carboxylic acids with 6 to 10 carbon atoms such as, in particular, 2-ethylbutyric acid, glycerol monooleate, dibutyl sebacate, di ( ⁇ -butoxymethyl) adipate, dioctyl phthalate and tricresyl phosphate are suitable.
- These plasticizers can be used individually or in mixtures.
- Substances can also be added which stabilize the mixture against degradation, e.g. Small amounts of alkali or of alkaline salts, furthermore oxidation stabilizers such as the phenols, bisphenols or terpene phenols substituted in the 2-, 4-, and / or 6-position.
- the mixtures can also contain additives which influence the adhesion of the films to one another or to glass, e.g. Salts of carboxylic acids, fluorides, lecithin or alkylene ureas.
- Both the stabilizers mentioned and the additives for influencing the adhesion are usually added in amounts of 0.001 to 1 percent by weight, based on the mixture as a whole.
- Polyvinyl butyral, plasticizers and, if appropriate, additives are mixed in a known manner by stirring them together at normal temperature and, if appropriate, leaving the mixture to stand, or by kneading or rolling at elevated temperature or else directly during processing on the calender or in the extruder.
- the production of glass composites from composite foils which contain polyvinyl butyral treated according to the invention can be carried out according to the usual methods. Methods, for example by pressing between 2 glass panes at 120 to 160 ° C and 5 to 20 bar.
- the low stickiness and the low pressure are particularly advantageous Temperatures below 100 ° C reduce the flowability of the films, which above all facilitates the insertion of the films between curved glass panes and also contributes to the reduction of air pockets in the composite.
- polyvinyl butyrals produced in this way are also suitable for all other applications of polyvinyl butyral, for example as an additive to paints and primers.
- the polymer was then mixed with 29% by weight of triethylene glycol bis (2-ethylbutyric acid ester) and extruded at 170.degree. Films of 0.8 mm thickness were pressed from the extrudate. The following table shows different properties of these films compared to films made from the untreated starting polymer.
- Example 2 As described in Example 1, a finely divided polyvinyl butyral with a vinyl alcohol unit content of 19.5% by weight and a viscosity of the 5% solution at 23 ° C. of 64 cp in 10 times the amount of water was stirred at 62 ° C. for 3 hours.
- the aqueous phase contained 2% sulfuric acid and 0.1% n-butyraldehyde.
- 0.2% (based on the polymer) of a sodium salt of C 13 -C 18 -alkanesulfonic acids were added to the batch. After this treatment, the polymer was worked up as indicated in Example 1 and extruded into a plasticized film.
- Glass films with high impact resistance and excellent transparency could be produced from the films produced from the post-treated polymer using known methods.
- the untreated polymer had a viscosity of 55 cp 5 minutes after cooling and 24 hours after cooling 56 cp.
- Example 3 A polymer with the properties given in the following table was treated as indicated in Example 3, with the difference that 0.4% by weight of dodecylbenzenesulfonic acid was present (based on the polymer).
- the reaction temperature was 65 ° C.
- Working up was carried out as indicated in Example 1.
- the other half of the batch was mixed with 0.15 part of a C 13 -C 18 alkanesulfonic acid in 5 parts of water and heated to 62 ° C. in 10 minutes. Samples were taken after each 1.3 and 5 hours of reaction at 62 ° C, after The reaction was stopped for 7 hours. All samples and the rest of the batch were processed as indicated in Example 1.
Landscapes
- 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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2732717A DE2732717C3 (de) | 1977-07-20 | 1977-07-20 | Verfahren zur Herstellung von Polyvinylbutyral mit verbesserten Eigenschaften |
DE2732717 | 1977-07-20 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0000699A1 true EP0000699A1 (fr) | 1979-02-21 |
EP0000699B1 EP0000699B1 (fr) | 1981-08-12 |
Family
ID=6014354
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP78100324A Expired EP0000699B1 (fr) | 1977-07-20 | 1978-07-07 | Procédé de préparation de polyvinyl butyral ayant des propriétés améliorées. |
Country Status (13)
Country | Link |
---|---|
US (1) | US4205146A (fr) |
EP (1) | EP0000699B1 (fr) |
JP (1) | JPS5422489A (fr) |
AR (1) | AR224502A1 (fr) |
AT (1) | AT366703B (fr) |
AU (1) | AU518178B2 (fr) |
BR (1) | BR7804657A (fr) |
CA (1) | CA1116784A (fr) |
DE (2) | DE2732717C3 (fr) |
IN (1) | IN150149B (fr) |
IT (1) | IT1097877B (fr) |
MX (1) | MX149297A (fr) |
ZA (1) | ZA784100B (fr) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0174479A2 (fr) * | 1984-08-10 | 1986-03-19 | Hoechst Aktiengesellschaft | Polyvinylbutyral d'une adhésivité réduite et d'une résistance à la traction améliorée |
EP0174480A2 (fr) * | 1984-08-10 | 1986-03-19 | Hoechst Aktiengesellschaft | Compositions thermoplastiques de polyvinylbutyral contenant un agent lubrifiant |
EP0368831A2 (fr) * | 1988-11-07 | 1990-05-16 | Monsanto Company | Feuille de polyvinylbutyral |
EP0402213A1 (fr) * | 1989-06-08 | 1990-12-12 | E.I. Du Pont De Nemours And Company | Procédé de fabrication de polyvinylbutyral et produits obtenus |
WO2004013191A1 (fr) * | 2002-08-02 | 2004-02-12 | E. I. Du Pont De Nemours And Company | Procede permettant de reguler les proprietes physiques du polyvinylbutyral (pvb) par regulation de la stereochimie de celui-ci |
WO2004026917A1 (fr) * | 2002-09-12 | 2004-04-01 | Wacker Polymer Systems Gmbh & Co. Kg | Procede de preparation de polyvinylacetales |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2401941A1 (fr) * | 1977-08-31 | 1979-03-30 | Saint Gobain | Procede de fabrication de polyvinyl butyral et polyvinyl butyral obtenu par ce procede |
DE2846837A1 (de) * | 1978-10-27 | 1980-05-08 | Hoechst Ag | Polyvinylbutyral-folie |
JPS5692142A (en) * | 1979-12-24 | 1981-07-25 | Sekisui Chem Co Ltd | Interlayer for laminated glass |
US4452935A (en) * | 1981-06-01 | 1984-06-05 | Sekisui Kagaku Kogyo Kabushiki Kaisha | Interlayer film for laminated glass |
JPS57200250A (en) * | 1981-06-01 | 1982-12-08 | Sekisui Chem Co Ltd | Interlay film for sandwich galss |
JPS5832044A (ja) * | 1981-08-14 | 1983-02-24 | Sekisui Chem Co Ltd | 合せガラス用中間膜の積み重ね体 |
FR2522003A1 (fr) * | 1982-02-23 | 1983-08-26 | Saint Gobain Vitrage | Procede de preparation du polyvinylbutyral |
DE3246605A1 (de) * | 1982-12-16 | 1984-06-20 | Hoechst Ag, 6230 Frankfurt | Feinteilige polyvinylacetale, verfahren zu ihrer herstellung und ihre verwendung fuer einbrennbeschichtungen |
DE3303111A1 (de) * | 1983-01-31 | 1984-08-02 | Hoechst Ag, 6230 Frankfurt | Thermoplastische formmassen aus weichmacherhaltigem polyvinylbutyral |
DE3303156A1 (de) * | 1983-01-31 | 1984-08-02 | Hoechst Ag, 6230 Frankfurt | Weichmacherhaltige polyvinylbutyralfolien mit reduziertem haftvermoegen an glas |
FR2547589B1 (fr) * | 1983-06-14 | 1986-03-21 | Saint Gobain Vitrage | Procede de fabrication de polyvinylbutyral et produits obtenus |
DE3417653A1 (de) * | 1984-05-12 | 1985-11-14 | Hoechst Ag, 6230 Frankfurt | Weichmacherhaltige thermoplastische polyvinylbutyralformmassen mit reduziertem haftvermoegen an glas |
US5349014A (en) * | 1984-08-02 | 1994-09-20 | E. I. Du Pont De Nemours And Company | Process for the production of polyvinyl butyral having improved properties |
CA1276744C (fr) * | 1985-07-02 | 1990-11-20 | George Etienne Cartier | Polyvinylbutyral reticule |
JPH0347511Y2 (fr) * | 1988-04-13 | 1991-10-09 | ||
DE3835840A1 (de) * | 1988-10-21 | 1990-05-31 | Hoechst Ag | Polyvinylacetalgruppen enthaltende pfropfpolymerisate auf polyurethanpfropfgrundlagen, verfahren zu ihrer herstellung und ihre verwendung |
US5238994A (en) * | 1991-09-09 | 1993-08-24 | Monsanto Company | Forming polyvinyl butyral |
US5332774A (en) * | 1992-10-16 | 1994-07-26 | Arco Chemical Technology, L.P. | Polyvinyl acetal resins based on hydroxyaldehydes and use of the resins in laminar structures |
DE4323897A1 (de) * | 1993-07-16 | 1995-01-19 | Hoechst Ag | Plastifizierte Polymerformkörper aus modifizierten Polyvinylbutyralen |
JP2629575B2 (ja) * | 1993-08-31 | 1997-07-09 | 日本電気株式会社 | 携帯無線通信装置 |
DE102004043907A1 (de) * | 2004-09-10 | 2006-03-16 | Kuraray Specialities Europe Gmbh | Weichmacherhaltige PVB-Folien mit Etherbindungen enthaltenden Carbonsäureestern als Co-Weichmacher |
US10676578B1 (en) * | 2019-05-10 | 2020-06-09 | Chang Chun Petrochemical Co., Ltd. | Interlayer film and laminated glass comprising the same |
MX2024004136A (es) * | 2021-10-28 | 2024-04-22 | Solutia Inc | Recuperacion de polimero de poli(vinil butiral) reciclado. |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB873263A (en) * | 1959-08-28 | 1961-07-19 | Seikisui Chemical Co Ltd | Process for preparing condensation products of polyvinyl alcohol and carbonyl compounds |
DE1545141A1 (de) * | 1962-08-13 | 1970-03-19 | Buna Chem Werke Veb | Verfahren zur Herstellung von Polyvinylbutyral |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1247663C2 (de) * | 1961-02-24 | 1975-11-27 | E.I. Du Pont De Nemours And Company, Wilmington, Del. (V.St.A.) | Verfahren zur herstellung von polyvinylacetalen |
-
1977
- 1977-07-20 DE DE2732717A patent/DE2732717C3/de not_active Expired
-
1978
- 1978-07-07 EP EP78100324A patent/EP0000699B1/fr not_active Expired
- 1978-07-07 DE DE7878100324T patent/DE2860933D1/de not_active Expired
- 1978-07-13 IN IN772/CAL/78A patent/IN150149B/en unknown
- 1978-07-18 AT AT0518778A patent/AT366703B/de not_active IP Right Cessation
- 1978-07-18 IT IT25850/78A patent/IT1097877B/it active
- 1978-07-18 US US05/925,873 patent/US4205146A/en not_active Expired - Lifetime
- 1978-07-18 AR AR272996A patent/AR224502A1/es active
- 1978-07-19 AU AU38155/78A patent/AU518178B2/en not_active Expired
- 1978-07-19 CA CA000307711A patent/CA1116784A/fr not_active Expired
- 1978-07-19 JP JP8722678A patent/JPS5422489A/ja active Granted
- 1978-07-19 BR BR7804657A patent/BR7804657A/pt unknown
- 1978-07-19 ZA ZA00784100A patent/ZA784100B/xx unknown
- 1978-07-20 MX MX174243A patent/MX149297A/es unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB873263A (en) * | 1959-08-28 | 1961-07-19 | Seikisui Chemical Co Ltd | Process for preparing condensation products of polyvinyl alcohol and carbonyl compounds |
DE1545141A1 (de) * | 1962-08-13 | 1970-03-19 | Buna Chem Werke Veb | Verfahren zur Herstellung von Polyvinylbutyral |
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0174479A2 (fr) * | 1984-08-10 | 1986-03-19 | Hoechst Aktiengesellschaft | Polyvinylbutyral d'une adhésivité réduite et d'une résistance à la traction améliorée |
EP0174480A2 (fr) * | 1984-08-10 | 1986-03-19 | Hoechst Aktiengesellschaft | Compositions thermoplastiques de polyvinylbutyral contenant un agent lubrifiant |
EP0174479A3 (en) * | 1984-08-10 | 1987-02-04 | Hoechst Aktiengesellschaft | Polyvinyl butyral with a reduced adhesion and increased tensile strength |
EP0174480A3 (en) * | 1984-08-10 | 1987-02-04 | Hoechst Aktiengesellschaft | Thermoplastic polyvinyl butyral compositions containing a lubricating agent |
EP0368831A2 (fr) * | 1988-11-07 | 1990-05-16 | Monsanto Company | Feuille de polyvinylbutyral |
EP0368831A3 (fr) * | 1988-11-07 | 1991-09-18 | Monsanto Company | Feuille de polyvinylbutyral |
FR2648139A1 (fr) * | 1989-06-08 | 1990-12-14 | Saint Gobain Vitrage | Procede de fabrication de polyvinylbutyral et produits obtenus |
EP0402213A1 (fr) * | 1989-06-08 | 1990-12-12 | E.I. Du Pont De Nemours And Company | Procédé de fabrication de polyvinylbutyral et produits obtenus |
WO2004013191A1 (fr) * | 2002-08-02 | 2004-02-12 | E. I. Du Pont De Nemours And Company | Procede permettant de reguler les proprietes physiques du polyvinylbutyral (pvb) par regulation de la stereochimie de celui-ci |
US8053504B1 (en) | 2002-08-02 | 2011-11-08 | E. I. Du Pont De Nemours And Company | Polyvinylbutyral resin composition having specified physical properties and stereochemistry |
US8329793B2 (en) | 2002-08-02 | 2012-12-11 | E I Du Pont De Nemours And Company | Plasticized composition comprising polyvinylbutyral resin having controlled stereochemistry |
WO2004026917A1 (fr) * | 2002-09-12 | 2004-04-01 | Wacker Polymer Systems Gmbh & Co. Kg | Procede de preparation de polyvinylacetales |
CN1307210C (zh) * | 2002-09-12 | 2007-03-28 | 瓦克聚合系统两合公司 | 生产聚乙烯醇缩醛类化合物的方法 |
US7351765B2 (en) | 2002-09-12 | 2008-04-01 | Wacker Polymer Systems Gmbh & Co. Kg | Method for producing polyvinylacetals |
Also Published As
Publication number | Publication date |
---|---|
US4205146A (en) | 1980-05-27 |
EP0000699B1 (fr) | 1981-08-12 |
BR7804657A (pt) | 1979-03-20 |
JPS5422489A (en) | 1979-02-20 |
JPS5728482B2 (fr) | 1982-06-17 |
AU3815578A (en) | 1980-01-24 |
DE2860933D1 (en) | 1981-11-12 |
DE2732717C3 (de) | 1980-06-04 |
AU518178B2 (en) | 1981-09-17 |
MX149297A (es) | 1983-10-11 |
AT366703B (de) | 1982-05-10 |
DE2732717B2 (de) | 1979-09-20 |
AR224502A1 (es) | 1981-12-15 |
IT7825850A0 (it) | 1978-07-18 |
IT1097877B (it) | 1985-08-31 |
DE2732717A1 (de) | 1979-02-08 |
ATA518778A (de) | 1981-09-15 |
CA1116784A (fr) | 1982-01-19 |
IN150149B (fr) | 1982-07-31 |
ZA784100B (en) | 1979-08-29 |
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