DE970857C - Process for the production of storable, polyester-bound, fiber-containing structures which can be hardened under the action of pressure and heat - Google Patents

Process for the production of storable, polyester-bound, fiber-containing structures which can be hardened under the action of pressure and heat

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Publication number
DE970857C
DE970857C DEH19097A DEH0019097A DE970857C DE 970857 C DE970857 C DE 970857C DE H19097 A DEH19097 A DE H19097A DE H0019097 A DEH0019097 A DE H0019097A DE 970857 C DE970857 C DE 970857C
Authority
DE
Germany
Prior art keywords
storable
fiber
heat
polyester
pressure
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.)
Expired
Application number
DEH19097A
Other languages
German (de)
Inventor
Erich Gentsch
Dipl-Chem Horst Golly
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Axalta Coating Systems Germany GmbH and Co KG
Original Assignee
Dr Kurt Herberts and Co GmbH
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.)
Filing date
Publication date
Application filed by Dr Kurt Herberts and Co GmbH filed Critical Dr Kurt Herberts and Co GmbH
Priority to DEH19097A priority Critical patent/DE970857C/en
Application granted granted Critical
Publication of DE970857C publication Critical patent/DE970857C/en
Expired legal-status Critical Current

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Classifications

    • 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
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
    • C08J5/241—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres
    • C08J5/244—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres using glass fibres
    • 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
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
    • C08J5/249—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs characterised by the additives used in the prepolymer mixture
    • 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
    • C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
    • C08J2367/06—Unsaturated polyesters

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Reinforced Plastic Materials (AREA)

Description

Verfahren zur Herstellung lagerfåhiger, unter Einwirkung von Druck und Hitze aushärtbarer, polyestergebundener, faserhaltiger Gebilde Gegenstand des Hauptpatentes 969 750 ist ein Verfahren zur Herstellung lagerfähiger, unter Einwirkung von Druck und Hitze aushärtbarer, polyestergebundener, faserhaltiger Gebilde, bei dem Faserstoffe mit einem Gemisch aus einem ungesättigten Polyesterharz, einer daran anpolymerisierbaren monomeren Vinylverbindung, wenigstens 101o oberflächenaktiver anorganischer Füllstoffe, bezogen auf Polyester, und einer über 70" als Polymerisationskatalysator wirkenden organischen Peroxydverbindung getränkt und die imprägnierten Faserstoffe durch Wärme bei Temperaturen bis zu 70" behandelt werden.Process for making storable, under the action of pressure and heat-curable, polyester-bonded, fiber-containing structures Subject of Main patent 969 750 is a process for the production of storable, under action polyester-bonded, fiber-containing structures that can be hardened by pressure and heat the fibrous material with a mixture of an unsaturated polyester resin, one on it polymerizable monomeric vinyl compound, at least 101o more surface-active inorganic fillers, based on polyester, and one over 70 "as a polymerization catalyst acting organic peroxide compound and impregnated fibers treated by heat at temperatures up to 70 ".

Bei der weiteren Bearbeitung des Verfahrens der Hauptpatentanmeldung wurde nun gefunden, daß man ähnliche technisch wertvolle Ergebnisse erhält, wenn man in der Imprägniermischung an Stelle der monomeren Vinylverbindung ein Gemisch aus einer monomeren Viniyverbindung und einem höhersiedenden, monomeren, an das ungesättigte Polyesterharz anpolymerisierbaren Allylester verwendet. In the further processing of the main patent application process it has now been found that similar technically valuable results are obtained if a mixture is used in the impregnation mixture instead of the monomeric vinyl compound from a monomeric vinyl compound and a higher-boiling, monomeric, to the unsaturated polyester resin polymerizable allyl ester is used.

Der Vorteil, der durch diese Abänderung des Verfahrens erzielt wird, liegt darin, daß das monomere Styrol eine verhältnismäßig hohe Flüchtigkeit besitzt und dementsprechend bei der Zwischentrocknung oder einer Stapelung der zwischengetrockneten Produkte Verluste an monomerem Styrol eintreten können. The benefit gained by changing the procedure is is that the monomeric styrene has a relatively high volatility and accordingly with intermediate drying or a stacking The intermediate dried products can lead to losses of monomeric styrene.

Diese Gefahr wird verringert, wenn man das monomere Styrol in dem vorerwähnten Sinn durch ein Gemisch aus einer monomeren Vinylverbindung und einem höhersiedenden, monomeren, an das ungesättigte Pglyesterharz anpolymerisierbaren Allylester ersetzt.This risk is reduced if the monomeric styrene in the the aforementioned sense by a mixture of a monomeric vinyl compound and a higher-boiling, monomeric, polymerizable onto the unsaturated glyester resin Allyl ester replaced.

Aus wirtschaftlichen Gründen wird man dabei jedoch im allgemeinen den Zusatz des Allylesters niedrig halten, da diese Produkte im allgemeinen teurer als das monomere Styrol sind.For economic reasons, however, this is generally used keep the addition of the allyl ester low, since these products are generally more expensive than the monomeric styrene.

Geeignete Allylester sind beispielsweise die Allylester von aliphatischen oder aromatischen Mono- oder Polycarbonsäuren, wie Allylester von langkettigen aliphatischen Monocarbonsäuren, Diallyladipat, Diallylsebazat, Diallylphthalat, Maleinsäurediallylester, Tetrahydrophthalsäurediallylester und Acrylsäureallylester. Die Umsetzung von Allylestern mit ungesättigten Polyestern vom Typ des Maleinsäure-Glykol-Polyesters ist bereits bekannt. Das den Gegenstand der vorliegenden Erfindung bildende Verfahren zur Herstellung lagerfähiger, unter Einwirkung von Druck und Hitze aushärtbarer, polyestergebundener, faserhaltiger Gebilde unter Verwendung von oberflächenaktiven anorganischen Stoffen konnte jedoch aus der erwähnten Literaturstelle nicht entnommen werden. Suitable allyl esters are, for example, the allyl esters of aliphatic or aromatic mono- or polycarboxylic acids, such as allyl esters of long-chain aliphatic Monocarboxylic acids, diallyl adipate, diallylsebazate, diallyl phthalate, maleic acid diallyl ester, Diallyl tetrahydrophthalate and allyl acrylic acid. Implementation of allyl esters with unsaturated polyesters of the maleic acid-glycol polyester type is already known. The method of manufacture forming the subject of the present invention more storable, hardenable under the action of pressure and heat, polyester-bound, fiber-containing structures using surface-active inorganic substances however, could not be taken from the mentioned literature reference.

Beispiel I Es wird eine Paste bereitet aus 42 Gewichtsteilen ungesättigtem Polyesterharz, II,5 Gewichtsteilen monomerem Styrol, 11,5 Gewichtsteilen Diallylphthalat, 3 Gewichtsteilen Kieselsäure-Aerogel, 3 Gewichtsteilen organischem Peroxyd, 6 Gewichtsteilen Celluloseacetobutyrat, 24 Gewichtsteilen Lösungsmittel, in welchem das Acetobutyrat gelöst wurde. Diese Paste wird z ir Imprägnierung eines Glas- oder Textilgewebes oder auch einer Zwischenschicht aus Papier verwendet. Example I A paste is prepared from 42 parts by weight of unsaturated Polyester resin, II, 5 parts by weight of monomeric styrene, 11.5 parts by weight of diallyl phthalate, 3 parts by weight of silica airgel, 3 parts by weight of organic peroxide, 6 parts by weight Cellulose acetobutyrate, 24 parts by weight solvent in which the acetobutyrate has been resolved. This paste is used to impregnate a glass or textile fabric or an intermediate layer of paper is used.

Das imprägnierte Gewebe wird bei etwa 60 bis 70" etwa 20 Minuten getrocknet. Das so erhaltene Produkt hat einen trocknen Griff und kann beliebig lange Zeit ohne Veränderung seiner Eigenschaften gelagert werden. Es kann bei höherer Temperatur, z. B. I20", unter gleichzeitigem Verpressen ausgehärtet werden.The impregnated fabric is dried at about 60 to 70 "for about 20 minutes. The product obtained in this way has a dry handle and can be used for any length of time without Change in its properties. It can be used at a higher temperature, z. B. I20 ", cured with simultaneous pressing.

Beispiel 2 Es wird eine Paste hergestellt aus 42 Gewichtsteilen ungesättigtem Polyesterharz, 11,5 Gewichtsteilen Styrol, II,5 Gewichtsteilen Diallylphthalat, 5 Gewichtsteilen Triallylcyanurat, I Gewichtsteil Kieselsäure-Aerogel, I Gewichtsteil organischem Peroxyd, 5 Gewichtsteilen Celluloseacetobutyrat, 3 Gewichtsteilen Nitrocellulose HP 25 (trocken), 20 Gewichtsteilen Lösungsmittel, in welchem Acetobutyrat und Nitrocellulose gelöst sind. Example 2 A paste is prepared from 42 parts by weight of unsaturated Polyester resin, 11.5 parts by weight styrene, II, 5 parts by weight diallyl phthalate, 5 parts by weight of triallyl cyanurate, I part by weight of silica airgel, I part by weight organic peroxide, 5 parts by weight of cellulose acetobutyrate, 3 parts by weight of nitrocellulose HP 25 (dry), 20 parts by weight solvent in which acetobutyrate and nitrocellulose are resolved.

Diese Paste wird, wie unter Beispiel 1 angegeben, verarbeitet. This paste is processed as indicated in Example 1.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung lagerfähiger, unter Einwirkung von Druck und Hitze aushärtbarer, polyestergebundener, faserhaltiger Gebilde nach Patent 969 750, dadurch gekennzeichnet, daß an Stelle der monomeren Vinylverbindung ein Gemisch aus einer monomeren Vinylverbindung und einem höhersiedenden, monomeren, an das ungesättigte Polyesterharz anpolymerisierbaren Allylester verwendet wird. PATENT CLAIM: Process for the production of storable, under action polyester-bonded, fiber-containing structures that can be hardened by pressure and heat Patent 969 750, characterized in that instead of the monomeric vinyl compound a mixture of a monomeric vinyl compound and a higher-boiling, monomeric, allyl ester which can be polymerized onto the unsaturated polyester resin is used. In Betracht gezogene Druckschriften: Deutsche Patentschriften Nr. 540 ion, 86o 273, 854 26I, 890129, 893 585; USA.-Patentschriften Nr. 2443 736 bis 2 443 74I, 2443915, 2561153, 2561I54, 2467339 247380I; Boundy-Boyer »Styrenest, (1952), S. IOOI, I035 und In47; ~Angewandte Chemie«, I950, S. 333; Bericht über 8. Annual Techn. u. Management Conference, Reinforced Plastic Division, Februar I953; »British Plastics«, 26 (1953), 5. 330. Publications considered: German Patent Specifications No. 540 ion, 86o 273, 854 26I, 890129, 893 585; U.S. Patent Nos. 2,443,736 bis 2 443 74I, 2443915, 2561153, 2561I54, 2467339, 247380I; Boundy-Boyer »Styrenest, (1952), S. IOOI, I035 and In47; Angewandte Chemie, 1950, p. 333; Report on 8th Annual Technical & Management Conference, Reinforced Plastic Division, February I953; "British Plastics", 26 (1953), p. 330.
DEH19097A 1954-01-24 1954-01-24 Process for the production of storable, polyester-bound, fiber-containing structures which can be hardened under the action of pressure and heat Expired DE970857C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEH19097A DE970857C (en) 1954-01-24 1954-01-24 Process for the production of storable, polyester-bound, fiber-containing structures which can be hardened under the action of pressure and heat

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEH19097A DE970857C (en) 1954-01-24 1954-01-24 Process for the production of storable, polyester-bound, fiber-containing structures which can be hardened under the action of pressure and heat

Publications (1)

Publication Number Publication Date
DE970857C true DE970857C (en) 1958-11-06

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Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE540101C (en) * 1930-06-26 1931-12-09 Ig Farbenindustrie Ag Process for the preparation of resinous polymerization products
US2443915A (en) * 1943-02-27 1948-06-22 Libbey Owens Ford Glass Co Copolymer of styrene with an ester of an unsaturated dicarboxylic acid and an hydroxy acid esterified with an unsaturated alcohol
US2443741A (en) * 1944-09-21 1948-06-22 American Cyanamid Co Polymerizable compositions containing unsaturated alkyd resins and allyl esters, copolymers of such compositions, and process of producing the same
US2443736A (en) * 1943-07-12 1948-06-22 American Cyanamid Co Copolymer of diallyl phthalate and unsaturated alkyd resin
US2467339A (en) * 1944-11-17 1949-04-12 Monsanto Chemicals Vinyl aromatic compositions containing colloidal silica
US2473801A (en) * 1939-04-01 1949-06-21 American Cyanamid Co Emulsions of polymerizable compositions
US2561154A (en) * 1948-06-29 1951-07-17 Us Rubber Co Soluble ternary copolymers of styrene, allylic poly-2-alkenyl esters, and allylic monoethers
US2561153A (en) * 1948-06-29 1951-07-17 Us Rubber Co Soluble binary copolymers of allylic monoethers and poly-2-alkenyl esters
DE854261C (en) * 1944-02-07 1952-11-04 Bataafsche Petroleum Process for the production of laminated bodies
DE860273C (en) * 1947-03-28 1952-12-18 Bataafsche Petroleum Process for the production of sheet-like materials
DE890129C (en) * 1937-12-25 1953-09-17 Roehm & Haas G M B H Process for the production of molded articles
DE893585C (en) * 1951-03-17 1953-10-19 Linoleum Werke A G Deutsche Process for the production of floor, table, wall and other covering materials

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE540101C (en) * 1930-06-26 1931-12-09 Ig Farbenindustrie Ag Process for the preparation of resinous polymerization products
DE890129C (en) * 1937-12-25 1953-09-17 Roehm & Haas G M B H Process for the production of molded articles
US2473801A (en) * 1939-04-01 1949-06-21 American Cyanamid Co Emulsions of polymerizable compositions
US2443915A (en) * 1943-02-27 1948-06-22 Libbey Owens Ford Glass Co Copolymer of styrene with an ester of an unsaturated dicarboxylic acid and an hydroxy acid esterified with an unsaturated alcohol
US2443736A (en) * 1943-07-12 1948-06-22 American Cyanamid Co Copolymer of diallyl phthalate and unsaturated alkyd resin
DE854261C (en) * 1944-02-07 1952-11-04 Bataafsche Petroleum Process for the production of laminated bodies
US2443741A (en) * 1944-09-21 1948-06-22 American Cyanamid Co Polymerizable compositions containing unsaturated alkyd resins and allyl esters, copolymers of such compositions, and process of producing the same
US2467339A (en) * 1944-11-17 1949-04-12 Monsanto Chemicals Vinyl aromatic compositions containing colloidal silica
DE860273C (en) * 1947-03-28 1952-12-18 Bataafsche Petroleum Process for the production of sheet-like materials
US2561154A (en) * 1948-06-29 1951-07-17 Us Rubber Co Soluble ternary copolymers of styrene, allylic poly-2-alkenyl esters, and allylic monoethers
US2561153A (en) * 1948-06-29 1951-07-17 Us Rubber Co Soluble binary copolymers of allylic monoethers and poly-2-alkenyl esters
DE893585C (en) * 1951-03-17 1953-10-19 Linoleum Werke A G Deutsche Process for the production of floor, table, wall and other covering materials

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