DE2039079B2 - ADHESIVE MIXTURE BASED ON POLYMERIZES WITH A K VALUE BETWEEN 30 AND 70 FROM N-VINYLCAPROLACTAM AND OR. OR VINYL METHYL ETHER AND THEIR USE IN FILM PRINTING - Google Patents
ADHESIVE MIXTURE BASED ON POLYMERIZES WITH A K VALUE BETWEEN 30 AND 70 FROM N-VINYLCAPROLACTAM AND OR. OR VINYL METHYL ETHER AND THEIR USE IN FILM PRINTINGInfo
- Publication number
- DE2039079B2 DE2039079B2 DE19702039079 DE2039079A DE2039079B2 DE 2039079 B2 DE2039079 B2 DE 2039079B2 DE 19702039079 DE19702039079 DE 19702039079 DE 2039079 A DE2039079 A DE 2039079A DE 2039079 B2 DE2039079 B2 DE 2039079B2
- Authority
- DE
- Germany
- Prior art keywords
- weight
- value
- methyl ether
- vinylcaprolactam
- adhesive mixture
- 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
-
- 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
- C09J133/00—Adhesives based on 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/08—Homopolymers or copolymers of acrylic acid esters
-
- 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
- C09J129/00—Adhesives based on 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 an alcohol, ether, aldehydo, ketonic, acetal, or ketal radical; Adhesives based on hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Adhesives based on derivatives of such polymers
- C09J129/10—Homopolymers or copolymers of unsaturated ethers
-
- 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
- C09J139/00—Adhesives based on 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 single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Adhesives based on derivatives of such polymers
- C09J139/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/04—Macromolecular compounds according to groups C08L7/00 - C08L49/00, or C08L55/00 - C08L57/00; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L29/00—Compositions 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 an alcohol, ether, aldehydo, ketonic, acetal or ketal radical; Compositions of hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Compositions of derivatives of such polymers
- C08L29/10—Homopolymers or copolymers of unsaturated ethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L39/00—Compositions 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 single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions of derivatives of such polymers
- C08L39/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
Damit sich beim Filmdruck das zu bedruckende Textilgut nicht verschieben kann, klebt man es üblicherweise auf der Textilbahnunterlage an. Es ist bekannt, als Klebemittel hierfür die verschiedensten wasserlöslichen Celluloseleime und Gummisorten sowie abgebaute und verätherte Stärke zu verwenden. Aus der deutschen Patentschrift 12 40812 ist es außerdem bekannt, Polymerisate mit K-Werten zwischen 30 und 70 aus 0 bis 100 Mol-% N-Vinylcaprolactam und 100 bis 0 Mol-% Vinylmethyläther als Klebemittel beim Filmdruck zu verwenden. Diese Polymerisate haben gegenüber den erstgenannten Mitteln eine Reihe von Vorteilen; alle bisher gebräuchlichen Mittel müssen aber in verhältnismäßig großen Mengen angewendet werden, damit eine ausreichende Verklebung gewährleistet ist: In der deutschen Patentschrift 12 40 812 werden 25%ige wäßrige Lösungen der dort angegebenen Polymerisate empfohlen; in der Praxis hat sich gezeigt, daß man die Konzentration an Polymerisaten bis auf ungefähr 18%, aber nicht weiter verringern kann.So that the textile material to be printed cannot shift during film printing, it is glued usually on the textile web underlay. It is known to use a wide variety of adhesives for this purpose to use water-soluble cellulose glues and gums as well as degraded and etherified starch. From the German Patent 12 40812 it is also known to use polymers with K values between 30 and 70 from 0 to 100 mole percent N-vinyl caprolactam and 100 to Use 0 mol% vinyl methyl ether as an adhesive in film printing. These polymers have compared to the first mentioned means a number of advantages; all previously used means must but can be used in relatively large quantities to ensure adequate bonding is: In German Patent 12 40 812, 25% aqueous solutions of the specified there are Polymers recommended; In practice it has been shown that the concentration of polymers up to about 18%, but cannot reduce it any further.
Es wurden nun neue Klebstoffmischungen gefunden, die sich gegenüber den obengenannten Mitteln durch eine überlegene Klebwirkung auszeichnen.New adhesive mixtures have now been found which differ from the above means are characterized by a superior adhesive effect.
Gegenstand der Erfindung ist eine Klebstoffmischung auf Basis von Polymerisaten mit einem K-Wert zwischen 30 und 70 aus N-Vinylcaprolactam und bzw. oder Vinylmethyläther, die dadurch gekennzeichnet ist, daß sie ausThe invention relates to an adhesive mixture based on polymers with a K value between 30 and 70 from N-vinylcaprolactam and / or vinyl methyl ether, which is characterized by that they are out
a) wenigstens einem Polymerisat mit einem K-Wert zwischen 30 und 70 ausa) at least one polymer with a K value between 30 and 70
Obis 100Gew.-% N-Vinylcaprolactam, 100 bis 0 Gew.-% Vinylmethyläther und 0 bis 5 Gew.-% eines vernetzenden Monomeren undObis 100% by weight N-vinylcaprolactam, 100 to 0% by weight of vinyl methyl ether and 0 to 5% by weight of a crosslinking monomer and
b) wenigstens einem Alkali- oder Ammoniumsalz eines Copolymerisats ausb) at least one alkali or ammonium salt of a copolymer
40 bis 60 Gew.-% eines oder mehrerer Acrylsäureester von aliphatischen Alkoholen mit 1 bis 10 Kohlenstoffatomen,40 to 60% by weight of one or more acrylic acid esters of aliphatic alcohols with 1 to 10 Carbon atoms,
ίο 20 bis 30 Gew.-% einer α^ϊ-ungesättigten aliphatischen Mono- oder Dicarbonsäure mit bis zu 6 Kohlenstoffatomen oder eines Halbesters einer solchen Dicarbonsäure mit einem aliphatischen, 1 bis 10 Kohlenstoffatome enthaltenden Alkohol, 20 bis 30 Gew.-% Methylmethacrylat, 0 bis 5 Gew.-% eines vernetzenden Monomeren undίο 20 to 30 wt .-% of an α ^ ϊ-unsaturated aliphatic Mono- or dicarboxylic acid with up to 6 carbon atoms or a half ester such dicarboxylic acid with an aliphatic alcohol containing 1 to 10 carbon atoms, 20 to 30% by weight of methyl methacrylate, 0 to 5% by weight of a crosslinking monomer and
0 bis 20 Gew.-% einer oder mehrerer anderer polymerisierbarer, äthylenisch ungesättigter Verbindungen besteht, wobei ein Gewichtsverhältnis0 to 20% by weight of one or more other polymerizable, ethylenically unsaturated compounds consists, where a weight ratio
von a : b von 5 :95 bis 95 :5 vorliegt. Unter vernetzenden Monomeren, wie sie in die Polymerisate a und bzw. oder b einpolymerisiert sein können, sind Stoffe zu verstehen, die außer einer polymerisierbaren C-C-Doppelbindung eine oder mehrere weitere funktionell Gruppen enthalten, die unter den Bedingungen der Polymerisation unter Vernetzung der Polymerketten reagieren. Solche funktionellen Gruppen sind insbesondere weitere polymerisierbare Doppelbindungen und N-Hydroxymethylgruppen. Als Beispiele für vernetzende Monomere, die solche Gruppen enthalten, seien genannt N-Methylolamide von Λ,/3-ungesättigten Carbonsäuren, wie vor allem N-Methylolacryl- und -methacrylamid, Polyvinylester und -allylester von zwei- und mehrbasischen Carbon säuren, wie Divinyladipat und Diallylphthalat, Polyester aus mehrwertigen Alkoholen und «,/S-ungesättigten Carbonsäuren, wie Butandioldiacrylat und -dimethacrylat. Vinyl- und Allylester von «^-ungesättigten Carbonsäuren, wie Vinylacrylat, Allylacrylat und Allylmethacrylat, und andere Verbindungen mit zwei oder mehr nicht konjugierten olefinischen Doppelbindungen, wie Divinyldioxan, Divinylbenzol, Methylen-bis-acrylamid undN,N',N"-Triacryloyl-hexahydro-s-triazin. Die vernetzenden Monomeren können z. B. in Mengen von 0,01 bis 5%, vorzugsweise 0,1 bis 1%, bezogen auf die Gesamtmenge aller Monomeren, in die Polymerisate (a) und bzw. oder (b) einpolymerisiert sein; sie bewirken vielfach eine Verbesserung der Klebkraft der erfindungsgemäßen Mischungen, ohne in kleinen Mengen deren Löslichkeit in Wasser zu beeinträchtigen. Die Komponente (b) kann bis zu 20 Gew.-%, bezogen auf die Gesamtmenge der Monomeren, an anderen polymerisierbaren, äthylenisch ungesättigten Verbindüngen enthalten, ohne daß ihre Eigenschaften wesentlich! verändert werden. Als Beispiele für solche Verbindungen seien vor allem Amide und Nitrile «^-ungesättigter aliphatischcr Carbonsäuren, Alkylvir.yläther und Vinylester gesättigter aliphatischer Carbonsäuren, und zwar besonder» diejenigen mit bis zu 4 Kohlenstoffatomen im Alkyl- oder Carbonsäurerest, genannt.from a: b from 5:95 to 95: 5. Among crosslinking monomers, such as those polymerized into polymers a and or or b can, substances are to be understood which, in addition to a polymerizable C-C double bond, have one or more contain further functional groups that are crosslinked under the conditions of the polymerization of the polymer chains react. Such functional groups are in particular further polymerizable Double bonds and N-hydroxymethyl groups. As examples of crosslinking monomers that have such Containing groups may be mentioned N-methylolamides of Λ, / 3-unsaturated carboxylic acids, such as above all N-methylol acrylic and methacrylamide, polyvinyl ester and allyl esters of di- and polybasic carboxylic acids, such as divinyl adipate and diallyl phthalate, polyester from polyhydric alcohols and «, / S-unsaturated Carboxylic acids such as butanediol diacrylate and dimethacrylate. Vinyl and allyl esters of «^ -unsaturated carboxylic acids, such as vinyl acrylate, allyl acrylate and allyl methacrylate, and other compounds having two or more non-conjugated olefinic double bonds, such as divinyldioxane, divinylbenzene, methylene-bis-acrylamide andN, N ', N "-triacryloyl-hexahydro-s-triazine. The crosslinking monomers can, for. B. in amounts of 0.01 to 5%, preferably 0.1 to 1%, based on the total amount of all monomers into which polymers (a) and / or (b) have been polymerized; they often bring about an improvement in the bond strength of the mixtures according to the invention, without in small amounts Quantities affect their solubility in water. Component (b) can be up to 20% by weight, based on on the total amount of monomers, of other polymerizable, ethylenically unsaturated compounds included without their properties being essential! to be changed. As examples of such Compounds are above all amides and nitriles of unsaturated aliphatic carboxylic acids, alkyl viral ethers and vinyl esters of saturated aliphatic carboxylic acids, especially those with up to 4 Carbon atoms in the alkyl or carboxylic acid radical, called.
Die Copolymerisate b) haben im allgemeinen einen K-Wert zwischen 60 und 130; besonders vorteilhaft sind diejenigen mit einem K-Wert zwischen 90 und 120.The copolymers b) generally have a K value between 60 and 130; are particularly advantageous those with a K value between 90 and 120.
Die im folgenden beschriebenen erfindungsgemäßen Klebstoffmischungen haben sich hervorragend bewährt: The adhesive mixtures according to the invention described below have proven to be outstanding:
1) Eine Mischung aus (a) 40 Gew.-Teilen Poly-N-vinylcaprolactam (K-Wert 60) und (b) 60 Gewichtsteilen eines mit Natriumhydroxid neutralisierten Copolymerisate aus 50 Gew.-% Athylacrylat, 25 Gew.-% Acrylsäure und 25 Gew.-% Methylmethacrylat 1) A mixture of (a) 40 parts by weight of poly-N-vinylcaprolactam (K value 60) and (b) 60 parts by weight a copolymer of 50% by weight ethyl acrylate neutralized with sodium hydroxide, 25 Wt .-% acrylic acid and 25 wt .-% methyl methacrylate
2) Eine Mischung aus (a) 50 Gewicbtsteilen Polyvinylmethyläther (K-Wert 50) und (b) 50 Gewichtsteilen eines mit Natriumhydroxid neutralisierten Copolymerisats aus 22,5 Gew.-% Methylacrylat, 33,5 Gew.-% Butylacrylat, 21,0 Gew.-% Acrylsäure und 23 Gew.-% Methylmethacrylat. 3) Eine Mischung aus (a) 50 Gew.-Teilen Polyvinylmethyläther (K,- Wert 50) und (b) 50 Gewichtsteilen eines Copolymerisats aus 17,8 Gew.-% Methylacrylat, 37,0 Gew.-% Butylarrylat, 22,3 Gew.-% Acrylsäure, 22,5 Gew.-% Methyifliethacrylat und 0,4 Gew.-% Divinyladipat2) A mixture of (a) 50 parts by weight Polyvinyl methyl ether (K value 50) and (b) 50 parts by weight of one neutralized with sodium hydroxide Copolymer of 22.5% by weight methyl acrylate, 33.5% by weight butyl acrylate, 21.0% by weight Acrylic acid and 23% by weight methyl methacrylate. 3) A mixture of (a) 50 parts by weight of polyvinyl methyl ether (K, value 50) and (b) 50 parts by weight a copolymer of 17.8% by weight methyl acrylate, 37.0% by weight of butyl arylate, 22.3% by weight of acrylic acid, 22.5% by weight of methyl ethyl acrylate and 0.4 wt% divinyl adipate
Die oben angegebenen K-Werte wurden bestimmt nach H. Fikentscher, Cellulose-Chemie 13 (1932), ff und 71 ff in 0,l%iger Lösung in Wasser bei 200C; dabei bedeutet K. = k · 103.The K values given above were determined according to H. Fikentscher, Cellulose-Chemie 13 (1932), ff and 71 ff in 0.1% strength solution in water at 20 ° C .; where K. = k · 10 3 .
Die Klebstoffmischungen können erfiiidungsgemäß mit besonderem Vorteil beim Filmdruck verwendet werden. Sie werden dafür wie die für diesen Zweck bekannten Mittel als wäßrige Lösungen angewendet Dabei genügt zur Erzielung einer bestimmten Klebwirkung von den erfindungsgemäßen Stoffmischungen die Hälfte der Menge, die von ihren Komponenten a) oder b) allein erforderlich wäre: während man die Komponente z), wie oben erwähnt, in wenigstens 18%iger Lösung anwenden muß, kann man die erfindungsgemäßen Mischungen aus den Komponenten a) und b) mit dem gleichen Erfolg in 9%iger Lösung einsetzea Das war um so überraschender, als auch die Komponente b) für sich nur in Konzentration von 18 oder mehr Prozent eine ausreichende Klebwirkung entfaltetAccording to the invention, the adhesive mixtures can be used with particular advantage in film printing. Like the agents known for this purpose, they are used as aqueous solutions. In order to achieve a certain adhesive effect, half the amount of the substance mixtures according to the invention that would be required from their components a) or b) alone is sufficient: while component z), As mentioned above, must be used in at least 18% solution, the mixtures according to the invention of components a) and b) can be used with the same success in 9% solutiona This was all the more surprising, as was component b) in itself A sufficient adhesive effect only develops in a concentration of 18 or more percent
Im übrigen unterscheidet sich die durch die Verwendung der genannten Polymerisatmischungen bedingte- Arbeitsweise nicht von den herkömmlichen Methoden des manuellen oder maschinellen Filmdrucks, so daß auf die Erläuterung der Erfindung an Hand spezieller Ausführungsbeispiele verzichtet werden kann.Otherwise, it differs through the use of the polymer mixtures mentioned conditional- working method not different from the conventional methods of manual or machine film printing, so that the explanation of the invention on the basis of specific exemplary embodiments is dispensed with can.
Claims (2)
2o bis 30 Gew.-% einer «,^-ungesättigten aliphatischen Mono- oder Dicarbonsäure mit bis zu 6 Kohlenstoffatomen oder eines Halbesters einer solchen Dicarbonsäure mit einem aliphatischen, 1 bis 10 Kohlenstoffatome enthaltenden Alkohol,40 to 60% by weight of one or more acrylic acid esters of aliphatic alcohols with 1 to 10 carbon atoms,
2o to 30 wt .-% of a «, ^ - unsaturated aliphatic mono- or dicarboxylic acid with up to 6 carbon atoms or a half ester of such a dicarboxylic acid with an aliphatic alcohol containing 1 to 10 carbon atoms,
0 bis 5 Gew.-% eines vernetzenden Monomeren und20 to 30% by weight methyl methacrylate,
0 to 5 wt .-% of a crosslinking monomer and
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19702039079 DE2039079C3 (en) | 1970-08-06 | Adhesive mixture based on polymers with a K value between 30 and 70 made of N-vinylcaprolactam and / or vinyl methyl ether and its use in film printing | |
FR7128259A FR2103858A5 (en) | 1970-08-06 | 1971-08-02 | Adhesives for textile printing - based on vinyl caprolactam vinyl methyl ether co-polymers and acrylic co-polymers |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19702039079 DE2039079C3 (en) | 1970-08-06 | Adhesive mixture based on polymers with a K value between 30 and 70 made of N-vinylcaprolactam and / or vinyl methyl ether and its use in film printing |
Publications (3)
Publication Number | Publication Date |
---|---|
DE2039079A1 DE2039079A1 (en) | 1972-02-10 |
DE2039079B2 true DE2039079B2 (en) | 1977-06-16 |
DE2039079C3 DE2039079C3 (en) | 1978-01-26 |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3005381A1 (en) * | 1978-10-30 | 1981-08-20 | The Kendall Co., Boston, Mass. | PRESSURE SENSITIVE ADHESIVE AND ADHESIVE FILM CONTAINING IT |
DE3105279A1 (en) * | 1980-04-04 | 1981-12-24 | The Kendall Co., Boston, Mass. | PRESSURE SENSITIVE ADHESIVE AND ADHESIVE FILM CONTAINING IT |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3005381A1 (en) * | 1978-10-30 | 1981-08-20 | The Kendall Co., Boston, Mass. | PRESSURE SENSITIVE ADHESIVE AND ADHESIVE FILM CONTAINING IT |
DE3105279A1 (en) * | 1980-04-04 | 1981-12-24 | The Kendall Co., Boston, Mass. | PRESSURE SENSITIVE ADHESIVE AND ADHESIVE FILM CONTAINING IT |
Also Published As
Publication number | Publication date |
---|---|
FR2103858A5 (en) | 1972-04-14 |
DE2039079A1 (en) | 1972-02-10 |
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