DE1181419B - Process for the production of crosslinkable copolymers - Google Patents
Process for the production of crosslinkable copolymersInfo
- Publication number
- DE1181419B DE1181419B DEC28236A DEC0028236A DE1181419B DE 1181419 B DE1181419 B DE 1181419B DE C28236 A DEC28236 A DE C28236A DE C0028236 A DEC0028236 A DE C0028236A DE 1181419 B DE1181419 B DE 1181419B
- Authority
- DE
- Germany
- Prior art keywords
- butyl acrylate
- ecm
- acrylonitrile
- copolymers
- production
- 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.)
- Pending
Links
- 229920001577 copolymer Polymers 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims 2
- -1 methacrylamido Chemical group 0.000 claims description 13
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 10
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 5
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 claims description 2
- 235000010262 sodium metabisulphite Nutrition 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 230000000379 polymerizing effect Effects 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000000576 coating method Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 239000004160 Ammonium persulphate Substances 0.000 description 1
- 239000004908 Emulsion polymer Substances 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 235000019395 ammonium persulphate Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000000816 ethylene group Chemical class [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 description 1
- 230000006855 networking Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/285—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acid amides or imides
-
- 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
- C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
-
- 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
- C08F28/00—Homopolymers and 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 bond to sulfur or by a heterocyclic ring containing sulfur
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Paints Or Removers (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
AUSLEGESCHRIFTEDITORIAL
Deutsche Kl.: 39 c-25/01 German class: 39 c -25/01
Nummer: 1181419 Number: 1181419
Aktenzeichen: C 28236IV d / 39 c File number: C 28236IV d / 39 c
Anmeldetag: 20. Oktober 1962 Filing date: October 20, 1962
Auslegetag: 12. November 1964 Opening day: November 12, 1964
Es ist bereits bekannt, daß man zu vernetzbaren Polymerisaten bzw. Mischpolymerisaten dadurch gelangen kann, daß man zu deren Aufbau vernetzbare Monomere verwendet bzw. mitverwendet. Als solche vernetzbare Monomere werden nach bekannten Verfahren z. B. N-Methylolacrylamid und dessen Äther zusammen mit anderen nicht vernetzbaren Monomeren eingesetzt. Die in wäßriger Emulsion hergestellten Polymeren spalten beim Erhitzen, gegebenenfalls in Anwesenheit von Katalysatoren und in einem unter 7 liegenden pH-Bereich, Formaldehyd ab, wobei Vernetzung stattfindet. Bei diesem Vorgang treten aber gleichzeitig beträchtliche Schrumpfungen auf, so daß ζ. B. mit derartigen Polymerisaten bzw. Mischpolymerisaten hergestellte Überzüge beim Trocknen unter Vernetzung Folien ergeben, die mit starken Spannungsrissen durchzogen sind.It is already known that this leads to crosslinkable polymers or copolymers It is possible that crosslinkable monomers are used or included to build them up. As such crosslinkable monomers are z. B. N-methylolacrylamide and its ether used together with other non-crosslinkable monomers. Those produced in aqueous emulsion Polymers cleave when heated, possibly in the presence of catalysts and in one of less than 7 lying pH range, formaldehyde, whereby crosslinking takes place. During this process, however, occur at the same time considerable shrinkage, so that ζ. B. with such polymers or copolymers Produced coatings on drying with crosslinking result in films with strong Stress cracks are streaked.
Es wurde nun gefunden, daß man zu vernetzbaren Mischpolymerisaten von Acrylsäurebutylester zusammen mit Styrol- oder Acrylnitril im wäßrigen Medium in Gegenwart von Katalysatoren, gegebenenfalls unter Zusatz von emulgierenden Mitteln, in Gegenwart von Methacrylamidderivaten gelangt, wenn man als Methacrylamidderivat das Alkalisalz der Methacrylamidomethylensulfosäure verwendet. Derartige Mischpolymerisate werden bereits beim Erwärmen auf etwa 950C auch in einem pH-Bereich über 7 unter Abspaltung von Schwefelsäure vernetzt und liefern dabei schrumpffreie Folien oder Überzüge. It has now been found that crosslinkable copolymers of butyl acrylate together with styrene or acrylonitrile in an aqueous medium in the presence of catalysts, optionally with the addition of emulsifying agents, in the presence of methacrylamide derivatives are obtained if the alkali metal salt of methacrylamidomethylene sulfonic acid is used as the methacrylamide derivative. Such copolymers are already crosslinked when heated to about 95 ° C., even in a pH range above 7, with elimination of sulfuric acid, and in the process produce shrink-free films or coatings.
Dieses Ergebnis ist überraschend, nachdem entsprechende, unter Mitverwendung von Alkalisalzen der Acrylamidomethylensulfosäure hergestellte bekannte Mischpolymerisate nur sehr schwer vernetzbar sind.This result is surprising after corresponding, with the use of alkali salts known copolymers produced from acrylamidomethylene sulfonic acid are very difficult to crosslink are.
Die beim erfindungsgemäßen Verfahren verwendeten Alkalisalze der Methacrylarnidomethylensulfosäure sind im Gegensatz zu den Äthern des N-Methylolacrylamids bequem zugänglich. Sie werden in bekannter Weise erhalten bei der Umsetzung von N-Methylolmethacrylamid mit Alkalipyrosulfiten bei etwa 50 bis 6O0C in wäßriger Lösung, wobei letztere ohne weiteres für die Mischpolymerisation eingesetzt werden kann.In contrast to the ethers of N-methylolacrylamide, the alkali metal salts of methacrylamide methylene sulfonic acid used in the process according to the invention are easily accessible. They are obtained in known manner in the reaction of N-methylolmethacrylamide with Alkalipyrosulfiten at about 50 to 6O 0 C in an aqueous solution, being able to be used for the latter readily copolymerization.
Gegenüber den Polymeren, die N-MethylolacryT-amid oder dessen Äther als vernetzende Komponente enthalten, zeigen die nach dem Verfahren der Erfindung erhältlichen Mischpolymerisate eine größere Stabilität der Emulsionen, so daß es nicht erforderlich ist, den pH-Wert der Emulsionen stets über 7 zu halten, um vorzeitiges Vernetzen zu verhindern.Compared to the polymers, the N-MethylolacryT-amid or contain its ether as a crosslinking component, show that according to the method of the invention available copolymers a greater stability of the emulsions, so that it is not necessary is to always keep the pH of the emulsions above 7 in order to prevent premature crosslinking.
Die gemäß der Erfindung herstellbaren Mischpolymeren können für viele Zwecke verwendet werden, so
Verfahren zur Herstellung von
vernetzbaren MischpolymerisatenThe interpolymers which can be prepared according to the invention can be used for many purposes, for example processes for the preparation of
crosslinkable copolymers
Anmelder:Applicant:
Cassella Farbwerke Mainkur Aktiengesellschaft, Frankfurt/M.-FechenheimCassella Farbwerke Mainkur Aktiengesellschaft, Frankfurt / M.-Fechenheim
Als Erfinder benannt:
Dr. Wilhelm Kunze,
Frankfurt/M.-FechenheimNamed as inventor:
Dr. Wilhelm Kunze,
Frankfurt / M.-Fechenheim
z. B. zur Imprägnierung oder Beschichtung von Textilien, von Produkten aus Fasermaterialien oder Leder und zur Beschichtung von Holz oder Metall. Durch die Vernetzung beim Trocknungsvorgang werden z. B. bei Textilien gegen Wäsche und chemische Reinigung beständige Appreturen bzw. Beschichtungen erhalten.z. B. for the impregnation or coating of textiles, of products made of fiber materials or Leather and for coating wood or metal. Through the networking during the drying process are z. B. with textiles against laundry and dry cleaning resistant finishes or coatings obtain.
In Stickstoffatmosphäre werden nacheinander unter Rühren vermischtThe mixture is mixed in succession with stirring in a nitrogen atmosphere
340 ecm Wasser (mit Stickstoff luftfrei gemacht), 7 g Alkylsulfonat,
Ig Triäthanolamin,
35 g Acrylsäurebutylester,
12 g Styrol,340 ecm of water (made air-free with nitrogen), 7 g of alkyl sulfonate,
Ig triethanolamine,
35 g butyl acrylate,
12 g styrene,
23 g einer 30%igen wäßrigen Lösung von methacrylamidomethylensulfosaurem Natrium.23 g of a 30% strength aqueous solution of methacrylamidomethylene sulfonic acid Sodium.
Bei 50°C tropft man im Verlauf einer Stunde die folgenden Lösungen zu, wobei mit dem Eintropfen der Lösungen 3 und 4 erst nach 20 Minuten begonnen wird:At 50 ° C., the following solutions are added dropwise over the course of one hour, with the dropping of solutions 3 and 4 is only started after 20 minutes:
1. 0,8 g Ammoniumpersulfat in 30 ecm Wasser,1. 0.8 g of ammonium persulphate in 30 ecm of water,
2. 1,0 g Natriumpyrosulfit in 30 ecm Wasser,2. 1.0 g of sodium pyrosulfite in 30 ecm of water,
3. eine Mischung von 70 g Acrylsäurebutylester und 24 g Styrol,3. a mixture of 70 g of butyl acrylate and 24 g of styrene,
4. 46 g einer 30% igen Lösung von methacrylamido-4. 46 g of a 30% solution of methacrylamido
methylensulfosaurem Natrium.sodium methylene sulfate.
Nach beendetem Zulauf rührt man noch 4 StundenAfter the addition has ended, the mixture is stirred for a further 4 hours
bei 55°C. Man erhält so eine 26%ige Dispersion eines Copolymeren aus 65% Acrylsäurebutylester, 22,5% Styrol und 12,5% methacrylamidomethylensulfosaurem Natrium.at 55 ° C. Is obtained as a 26% ig e dispersion of a copolymer of 65% butyl acrylate, 22.5% styrene and 12.5% methacrylamidomethylensulfosaurem sodium.
409 727/496409 727/496
3 43 4
Beim Trocknen der Dispersion bildet sich eine Lösung von methacrylamidomethylensulfosaurem Na-When the dispersion dries, a solution of methacrylamidomethylene sulfonic acid Na-
farblose Folie, welche keine Schrumpfungsrisse zeigt trium eingetropft.colorless film which shows no shrinkage cracks. trium dropped in.
und in Dimethylformamid oder Trichloräthylen nur Nach beendetem Zulauf rührt man noch 4 Stundenand in dimethylformamide or trichlorethylene only after the addition has ended, the mixture is stirred for a further 4 hours
etwas anquellbar, jedoch nicht löslich ist. Die Disper- bei 55°C. Man erhält so eine 26%ige Dispersionsomewhat swellable, but not soluble. The disperser at 55 ° C. A 26% dispersion is obtained in this way
sion eignet sich daher z. B. sehr gut zum Imprägnieren 5 eines Copolymerisates aus 52 % Acrylsäurebutylester,sion is therefore suitable for. B. very good for impregnating 5 a copolymer of 52% butyl acrylate,
von Geweben, wobei eine trichloräthylen- und wasch- 35% Acrylnitril und 13% methacrylamidomethylen-of fabrics, with a trichlorethylene and washing 35% acrylonitrile and 13% methacrylamidomethylene
beständige Appretur erhalten wird. sulfosaurem Natrium.stable finish is obtained. Sodium sulfonic acid.
Beim Trocknen der Dispersion ohne Zusätze wirdWhen drying the dispersion without additives
Beispiel 2 eme ne^e Folie gebildet, die keine SchrumpfungsrisseExample 2 eme ne ^ e film formed, which no shrinkage cracks
ίο aufweist. Diese ist in Dimethylformamid und Trichlor-ίο has. This is in dimethylformamide and trichloro
In Stickstoffatmosphäre werden miteinander ver- äthylen nur wenig quellbar.Ethylenes swell only slightly with one another in a nitrogen atmosphere.
mischt: n ,mixes: n ,
Claims (1)
Wasser und 20 Minuten nach Beginn in etwaWater and 1.0 g of sodium pyrosulfite in 30 ecm is used.
Water and about 20 minutes after the start
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC28236A DE1181419B (en) | 1962-10-20 | 1962-10-20 | Process for the production of crosslinkable copolymers |
| GB41252/63A GB997922A (en) | 1962-10-20 | 1963-10-18 | Cross-linkable copolymers |
| FR951132A FR1371708A (en) | 1962-10-20 | 1963-10-18 | Process for preparing crosslinkable copolymers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC28236A DE1181419B (en) | 1962-10-20 | 1962-10-20 | Process for the production of crosslinkable copolymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1181419B true DE1181419B (en) | 1964-11-12 |
Family
ID=7018580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC28236A Pending DE1181419B (en) | 1962-10-20 | 1962-10-20 | Process for the production of crosslinkable copolymers |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1181419B (en) |
| GB (1) | GB997922A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3717687A (en) * | 1971-03-24 | 1973-02-20 | Lubrizol Corp | Composition and method of imparting premanent press and soil release properties to fabrics |
| USD268573S (en) | 1981-04-23 | 1983-04-12 | Compagnie Generale Des Etablissements Michelin | Tire |
| US4599390A (en) * | 1983-03-11 | 1986-07-08 | Union Carbide Corporation | High molecular weight water-soluble polymers and flocculation method using same |
| US4702292A (en) * | 1986-03-18 | 1987-10-27 | The Goodyear Tire & Rubber Company | High performance all-season tire tread |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2718515A (en) * | 1954-08-13 | 1955-09-20 | American Cyanamid Co | Copolymers of n-substituted acrylamides |
-
1962
- 1962-10-20 DE DEC28236A patent/DE1181419B/en active Pending
-
1963
- 1963-10-18 GB GB41252/63A patent/GB997922A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2718515A (en) * | 1954-08-13 | 1955-09-20 | American Cyanamid Co | Copolymers of n-substituted acrylamides |
Also Published As
| Publication number | Publication date |
|---|---|
| GB997922A (en) | 1965-07-14 |
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