CH437602A - Use of phosphoric acid esters as a surface-active additive to aqueous dispersions of thermoplastic resins - Google Patents
Use of phosphoric acid esters as a surface-active additive to aqueous dispersions of thermoplastic resinsInfo
- Publication number
- CH437602A CH437602A CH257665A CH257665A CH437602A CH 437602 A CH437602 A CH 437602A CH 257665 A CH257665 A CH 257665A CH 257665 A CH257665 A CH 257665A CH 437602 A CH437602 A CH 437602A
- Authority
- CH
- Switzerland
- Prior art keywords
- phosphoric acid
- acid esters
- thermoplastic resins
- active additive
- aqueous dispersions
- Prior art date
Links
- 150000003014 phosphoric acid esters Chemical class 0.000 title claims description 11
- 239000006185 dispersion Substances 0.000 title claims description 5
- 239000000654 additive Substances 0.000 title claims description 4
- 230000000996 additive effect Effects 0.000 title claims description 4
- 229920005992 thermoplastic resin Polymers 0.000 title claims description 4
- 239000000839 emulsion Substances 0.000 claims description 7
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 6
- 125000004185 ester group Chemical group 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000008149 soap solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- -1 alkylphenyl ether Chemical compound 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000005357 flat glass Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000000963 oxybis(methylene) group Chemical group [H]C([H])(*)OC([H])([H])* 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical class C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/02—Emulsion paints including aerosols
- C09D5/024—Emulsion paints including aerosols characterised by the additives
- C09D5/027—Dispersing agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Dispersion Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Paints Or Removers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyethers (AREA)
Description
Verwendung von Phosphorsäureestern als oberflächenaktiver Zusatz zu wässrigen Dispersionen thermoplastischer Harze
Die Erfindung bezieht sich auf die Verwendung von Phosphorsäureestern als oberflächenaktiver Zusatz zu Emulsionen bzw. Dispersionen thermoplastischer Harze, wie sie normalerweise für Emulsionsfarben auf Wasserbasis zur Oberflächenbeschichtung verwendet werden.
Die gemäss der Erfindung verwendbaren Phosphorsäureester sind solche, in denen mindestens eine Estergruppe aus Polyalkylenglykolen bzw. deren Mono äthern oder -estern gebildet ist und die anderen Estergruppen beispielsweise Alkyl-, Aryl- und/oder Alkylarylgruppen sind.
Als Polyalkylenglykole. kommen z. B. in Betracht: Polyäthylenglykole der Formel HO(C2H4O)0CH2CH2OH inden = 2 bis 15 ist und Polypropylenglykole der Formel
EMI1.1
in der n = 2 bis 15 und R eine Methylgruppe und R' Wasserstoff ist oder umgekehrt.
Für die Polyalkylenglykolmonoäther können als Alkohole, die in direkter Ätherbindung an das Polyalkylenenglykol gebunden sind, beispielsweise folgende genannt werden: Methanol, Äthanol, Butanole, 2-Athyl- hexylalkohol, Benzylalkohol, Phenol, Cresole, Diacetonalkohol; letztere sind unter den Bezeichnungen DO WANOLE , CARBITOLE und CELLOSOLVE im Handel.
Die gemäss der Erfindung zu verwendenden Phosphorsäureester können durch ein- oder mehrstufige Veresterungsmethoden gewonnen werden, wobei die Komponenten in entsprechendem molekularem Verhältnis, vorzugsweise in einem Lösungsmittel und in Gegenwart von Kondensationskatalysatoren, erhitzt und das Reaktionswasser sowie das Lösungsmittel und etwa überschüssige Reaktionskomponenten abdestilliert wer den. Die Verbindungen sind im allgemeinen wasserlöslich oder zumindest in Wasser leicht dispergierbar. Die Wasserlöslichkeit ist normalerweise abhängig von der Kettenlänge der Polyalkylenglykole, wobei höherer Säurestoffgehalt die Löslichkeit begünstigt, und zum anderen von endständigen Äthergruppen, die vorzugsweise aus wasserlöslichen Alkoholen zu bilden sind.
Nach bekannten fachmännischen Grundsätzen können die genannten Komponenten in solchem Verhältnis zusammengestellt werden, dass die Wasserraffinität erreicht wird.
Im folgenden Beispiel wird zunächst eine geeignete Herstellungsweise verwendbarer Phosphorsäureester und dann ihre erfindungsmässige Verwendung in einer wässrigen, Pigment enthaltenden Harzemulsion beschrieben.
Beispiel
310 g Triphenylphosphite wurden in Gegenwart von 3 g Natriummethylat mit 350 g Methoxypolyäthylenglykol 350 gerührt. Das Gemisch wurde auf 1700 erhitzt und unter einem Druck von 5-10 mm ein Mol Phenol abgetrieben. Nach Abkühlen des Reaktionsgemisches wurden 300 g kaltes Wasser zugefügt. Hierauf wurden 10 g Natriumcarbonat und anschliessend 34 g (1 Mol) Wasserstoffperoxyd unter äusserer Kühlung langsam zugegeben.
Es entstand eine wässrige Lösung, welche, neben Triphenylphosphat, als erfindungsgenaue Phosphorsäureester Diphenylmonomethoxypolyäthylenglykolphos- phat und Monophenyl-bis-(Methoxypolyäthylenglykol)- Phosphat enthielt.
Um bei Verwendung dieser Phosphorsäureester den Einfluss auf die Beständigkeit eines Anstrichs gegen Wasserfleckenbildung und wiederholte Emulsionsbilbildung bei Berührung mit Wasser zu bestimmen, wurden folgende Vergleichsversuche angesetzt:
Vergleichs- Phosphor mischung säureester enthaltende
Mischung Wasser 135 135 Tamol 731 > (25 O/o) 4 2 Rutil TiO2 175 175 Ton 100 100 Calciumcarbonat 150 150 Polyglykol 1200 3 3 Phosphorsäureester 10 wurden gemischt, dann wurde zugegeben Methylcellulose 20/oiger Lösung 200 200 Diäthylenglykol 15 15 Butadienstyrolcopolymerisat
Emulsion 290 290 Tergitol NP-X > 10 Wasser 30 30 Tamol der Rohm & Haas Company ist ein oberflächenaktives Mittel. Tergitol NP-X der Carbide and Carbon Chemical Co.
ist ein Alkylphenyläther des Poly äthylenglykols.
Mit beiden Farben wurden, wie unten beschrieben, Tafeln für die Scheuerprüfung hergerichtet. Die Tafel mit der Vergleichsmischung war nach 500 Durchgängen vollständig zerstört. Die Beschichtung aus der Phosphorsäureester enthaltenden Mischung zeigte eine dermassen verbesserte Scheuerfestigkeit, dass nach etwa 1500 Durchgängen noch keine Schäden feststellbar waren.
Ausserdem wurde eine gewisse Feuerfestigkeit erzielt.
Die Scheuerprüfung wurde wie folgt vorgenommen: Von den obigen Mischungen wurden Filme der Prüffarbe auf eine ebene Glastafel von 16,51 x 44,45 cm mittels einer auf 0,1524 mm Abstand eingestellten Rakel aufgetragen.
Nach Herstellung der Beschichtung wurden die Tafeln unter strenger Kontrolle der Temperatur und der Feuchtigkeitsbedingungen bei 25O C und 50 O/o relativer Feuchtigkeit 7 Tage lang getrocknet. Nach dieser Trocknungszeit wurden die Tafeln einer Prüfung mittels der Gardner-Straight- line -Waschechtheitsprüfmaschine mit einer Ein-Pfund-Bürste unterworfen.
Vor der Prüfung wurde die Bürste während 30 Minuten in Wasser und anschliessend während 5 Minuten in eine 0,5 0/obige Ivory -Seifenlösung eingetaucht. Die Tafeln wurden dann unter Verwendung zusätzlicher Ivory -Seifenlösung als Waschflüssigkeit gescheuert.
Die Prüfung wurde so lange fortgesetzt, bis deutliche Schäden auftraten, jedoch im allgemeinen nicht über 2000 Scheuergänge hinaus.
Use of phosphoric acid esters as a surface-active additive to aqueous dispersions of thermoplastic resins
The invention relates to the use of phosphoric acid esters as a surface-active additive to emulsions or dispersions of thermoplastic resins such as are normally used for water-based emulsion paints for surface coating.
The phosphoric acid esters which can be used according to the invention are those in which at least one ester group is formed from polyalkylene glycols or their mono ethers or esters and the other ester groups are, for example, alkyl, aryl and / or alkylaryl groups.
As polyalkylene glycols. come z. B. into consideration: Polyethylene glycols of the formula HO (C2H4O) OCH2CH2OH indene = 2 to 15 and polypropylene glycols of the formula
EMI1.1
in which n = 2 to 15 and R is a methyl group and R 'is hydrogen or vice versa.
For the polyalkylene glycol monoethers, the following alcohols, which are bonded to the polyalkylene glycol in a direct ether bond, can be mentioned, for example: methanol, ethanol, butanols, 2-ethylhexyl alcohol, benzyl alcohol, phenol, cresols, diacetone alcohol; the latter are sold under the names DO WANOLE, CARBITOLE and CELLOSOLVE.
The phosphoric acid esters to be used according to the invention can be obtained by single or multi-stage esterification methods, the components being heated in the appropriate molecular ratio, preferably in a solvent and in the presence of condensation catalysts, and the water of reaction as well as the solvent and any excess reaction components being distilled off. The compounds are generally water-soluble or at least easily dispersible in water. The solubility in water is normally dependent on the chain length of the polyalkylene glycols, with a higher acid content promoting solubility, and on the other hand on terminal ether groups which are preferably to be formed from water-soluble alcohols.
According to known professional principles, the components mentioned can be put together in such a ratio that the water refinity is achieved.
The following example first describes a suitable method of preparing usable phosphoric acid esters and then their use according to the invention in an aqueous, pigment-containing resin emulsion.
example
310 g of triphenyl phosphites were stirred with 350 g of 350 g methoxypolyethylene glycol in the presence of 3 g of sodium methylate. The mixture was heated to 1700 and one mole of phenol was driven off under a pressure of 5-10 mm. After the reaction mixture had cooled, 300 g of cold water were added. 10 g of sodium carbonate and then 34 g (1 mol) of hydrogen peroxide were then slowly added with external cooling.
An aqueous solution was formed which, in addition to triphenyl phosphate, contained diphenyl monomethoxypolyethylene glycol phosphate and monophenyl bis (methoxypolyethylene glycol) phosphate as phosphoric acid esters according to the invention.
In order to determine the influence on the resistance of a paint against water staining and repeated emulsion formation when this phosphoric acid ester is used in contact with water, the following comparative tests were carried out:
Comparative phosphorus mixture containing acid esters
Mixture water 135 135 Tamol 731> (25 O / o) 4 2 rutile TiO2 175 175 clay 100 100 calcium carbonate 150 150 polyglycol 1200 3 3 phosphoric acid ester 10 were mixed, then methyl cellulose 20% solution 200 200 diethylene glycol 15 15 butadiene styrene copolymer was added
Emulsion 290 290 Tergitol NP-X> 10 Water 30 30 Tamol from Rohm & Haas Company is a surface active agent. Tergitol NP-X from Carbide and Carbon Chemical Co.
is an alkylphenyl ether of poly ethylene glycol.
As described below, both colors were used to prepare panels for the abrasion test. The panel with the comparison mixture was completely destroyed after 500 runs. The coating made from the mixture containing phosphoric acid ester showed such an improved rub resistance that no damage could be detected after about 1500 passes.
In addition, a certain fire resistance was achieved.
The abrasion test was carried out as follows: Films of the test color of the above mixtures were applied to a flat glass panel measuring 16.51 × 44.45 cm using a doctor blade set at a distance of 0.1524 mm.
After the coating was made, the panels were dried under strict control of the temperature and humidity conditions at 250 ° C. and 50% relative humidity for 7 days. After this drying time, the panels were subjected to a test using the Gardner Straightline ™ wash fastness tester with a one-pound brush.
Before the test, the brush was immersed in water for 30 minutes and then in a 0.5% Ivory soap solution above for 5 minutes. The panels were then scrubbed using additional Ivory® soap solution as a wash liquid.
The test was continued until significant damage occurred, but generally not beyond 2000 scrubbing cycles.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82479359A | 1959-07-03 | 1959-07-03 | |
| US82479559A | 1959-07-03 | 1959-07-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH437602A true CH437602A (en) | 1967-06-15 |
Family
ID=27124843
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH257665A CH437602A (en) | 1959-07-03 | 1960-07-01 | Use of phosphoric acid esters as a surface-active additive to aqueous dispersions of thermoplastic resins |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH437602A (en) |
| GB (1) | GB944295A (en) |
| NL (1) | NL253073A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999046337A1 (en) * | 1998-03-12 | 1999-09-16 | Basf Aktiengesellschaft | Aqueous polymer dispersion containing an emulsifier with phosphate groups |
-
0
- NL NL253073D patent/NL253073A/xx unknown
-
1960
- 1960-06-27 GB GB2242960A patent/GB944295A/en not_active Expired
- 1960-07-01 CH CH257665A patent/CH437602A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999046337A1 (en) * | 1998-03-12 | 1999-09-16 | Basf Aktiengesellschaft | Aqueous polymer dispersion containing an emulsifier with phosphate groups |
Also Published As
| Publication number | Publication date |
|---|---|
| GB944295A (en) | 1963-12-11 |
| NL253073A (en) |
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