DE596409C - Process for the production of phenol-aldehyde resins which harden quickly in the cold - Google Patents
Process for the production of phenol-aldehyde resins which harden quickly in the coldInfo
- Publication number
- DE596409C DE596409C DEI45176D DEI0045176D DE596409C DE 596409 C DE596409 C DE 596409C DE I45176 D DEI45176 D DE I45176D DE I0045176 D DEI0045176 D DE I0045176D DE 596409 C DE596409 C DE 596409C
- Authority
- DE
- Germany
- Prior art keywords
- phenol
- cold
- production
- aldehyde resins
- aldehyde
- 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
Links
- 229920005989 resin Polymers 0.000 title claims description 7
- 239000011347 resin Substances 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 title description 3
- 239000007788 liquid Substances 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 4
- -1 aromatic sulfochlorides Chemical class 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 6
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 235000013312 flour Nutrition 0.000 description 4
- 239000010453 quartz Substances 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000004570 mortar (masonry) Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910000676 Si alloy Inorganic materials 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- OPECTNGATDYLSS-UHFFFAOYSA-N naphthalene-2-sulfonyl chloride Chemical compound C1=CC=CC2=CC(S(=O)(=O)Cl)=CC=C21 OPECTNGATDYLSS-UHFFFAOYSA-N 0.000 description 1
- AYDPPJFUTOOTRP-UHFFFAOYSA-N naphthalene;sulfurochloridic acid Chemical class OS(Cl)(=O)=O.C1=CC=CC2=CC=CC=C21 AYDPPJFUTOOTRP-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Description
Verfahren zur Herstellung von in der Kälte schnelf.-erhärtenden Phenol-Aldehyd-Harzen Es ist bekannt, Phenol-Aldehyd-Harze, welche erst so weit kondensiert sind, daß sie sich noch in flüssigem Zustand befinden, zu säurefesten Auskleidungen und Bekleidungen von Apparaten und zur Herstellung von Säurebauten und Anstrichfarben zu verwenden. Bisher wurden diese flüssigen Kunstharze entweder durch Wärme oder durch Säure oder saure Salze gehärtet bzw. zu Ende kondensiert. Auch die Verwendung von basischen Stoffen als Zusatzstoffe für Phenol-Aldehyd-Harze, um deren Erhärten in der Kälte herbeizuführen, ist bereits bekannt.Process for the production of phenol-aldehyde resins which harden quickly in the cold It is known that phenol-aldehyde resins have only condensed so far that they are still in a liquid state, to acid-proof linings and clothing of apparatus and for the production of acid structures and paints. Up until now, these liquid synthetic resins were produced either by heat or by acid or acid salts hardened or condensed to the end. Also the use of basic Substances used as additives for phenol-aldehyde resins to make them harden in the cold to bring about is already known.
In dem Hauptpatent 595014 wurde nun zum ersten Male der Vorschlag gemacht, flüssige Phenol-Aldehyd-Harze durch Zusatz von gegen Wasser neutral reagierenden, kondensierend wirkenden Mitteln, und zwar Metalldioxyden, in der Kälte zu erhärten. Dies ist vor allen Dingen für die Herstellung von säurefesten Auskleidungen und Bauten wertvoll, da man hierfür naturgemäß keine säureempfindlichen Materialien benutzen kann -und anderseits das Arbeiten mit neutralen Kondensationsmitteln keime Belästigung für 'Arbeiter und keine Beschädigung des zu schützenden Materials mit sich bringt. Es wurde nun gefunden, daß dasselbe Problem auch mit Hilfe von aromatischen Sulfochloriden, wie Paratoluolsulfochlorid, Betanaphthalinsulfochlorid, Naphtl-alindisulfodichlorid, Benzolsulfochlorid usw., gelöst werden kann. Diese Körper wirken bereits selbst in Mengen von nur r bis 2 % (berechnet auf das Phenol-Aldehyd-Harz) in der Kälte härtend und reagieren weder an sich noch in Berührung mit Wasser sauer im Gegensatz zu den bereits als Härtungsbeschleunigern verwendeten Säurechloriden, wie z. B. B:enzoylchlorid.The proposal was made for the first time in the main patent 595014 made, liquid phenol-aldehyde resins by adding neutral reacting to water, condensing agents, namely metal dioxides, to harden in the cold. This is especially important for the production of acid-proof linings and Buildings are valuable because naturally no acid-sensitive materials are used for them can use - and on the other hand working with neutral condensation agents germs Harassment for workers and no damage to the material to be protected brings itself. It has now been found that the same problem can also be solved with the aid of aromatic Sulfochlorides, such as paratoluene sulfochloride, betanaphthalene sulfochloride, naphthalene disulfodichloride, Benzenesulfonyl chloride, etc., can be dissolved. These bodies are already working by themselves in amounts of only r to 2% (calculated on the phenol-aldehyde resin) in the cold hardening and react neither on themselves nor in contact with water in contrast to acidic to the acid chlorides already used as curing accelerators, such as. B. B: enzoyl chloride.
Die aromatischen Sulfochloride werden ebenso wie die Metalldioxyde gemäß Hauptpatent .entweder für sich allein oder _in_V_er-, Bindung mit Füllstoffen, gegebenenfalls außer--lem "nöcli unter `-Züsatz gut wärmeleitender Materialien, wie beispielsweise Silicium, Siliciumleglerungen und Graphit, den flüssigen Phenol-Aldehyd-Harzen beigemischt. Die ErhärtLing der Massen erfolgt bei gewöhnlicher Temperatur und wird bereits durch verhältnismäßig geringe Mengen der Zusatzstoffe @erreicht. Die mit solchen Massen hergestellten Kittungen oder Verputze sind fest, hart und widerstandsfähig gegen Druck, Reibung und gegen Säureangriff. Ein besonderer Vorteil gegenüber den durch saure Zusatzstoffe erhärtenden Kunstmassen besteht darin, daß mit diesen neuen Mischungen auch auf Metallflächen gearbeitet werden kann, da diese nicht angegriffen werden. Beispiel i i o Teile feinpulvriges Paratoluolsulfochlorid, 45 Teile feine amorphe Kieselerde und 45 Teile Quarzmehl werden zusammengemischt und dann mit neutralem flüssigem Phenol-Aldehyd-Harz zu einer plastischen, gut verarbeitbaren Mörtelmasse vermengt, die zuverlässig innerhalb 24 Stunden erstarrt.The aromatic sulfochlorides are just like the metal dioxides according to the main patent, either on its own or _in_V_er-, binding with fillers, possibly except for - lem "nöcli under` -addition of materials that conduct heat well, such as silicon, silicon alloys and graphite, the liquid phenol-aldehyde resins mixed in. The hardening of the masses takes place at ordinary temperature and is already achieved through relatively small amounts of the additives @. With Putties or plasters produced in this way are firm, hard and resilient against pressure, friction and against acid attack. A particular advantage compared to the synthetic compositions hardened by acidic additives is that These new mixtures can also be used on metal surfaces, as these not be attacked. Example i i o parts of finely powdered paratoluene sulfochloride, 45 parts of fine amorphous silica and 45 parts of quartz flour are mixed together and then with neutral liquid phenol-aldehyde resin to form a plastic, easy to process Mixed mortar mass that solidifies reliably within 24 hours.
An Stelle von Paratoluolsulfochlorid können auch andere aromatische SulfochloridQ, wie z. B. Naphthalinsulfochloride usw., verwendet werden. Beispiel 2 5oo Teile neutrales Phenol-Aldehyd-Harz und 5o Teile Benzylalkohol (als Weichmachungsmittel) werden mit Zoo Teilen Kieselweiß, 6oo Teilen feinstem Quarzmehl und 7o Teilen Paratoluolsulfochlorid vermischt und diese Masse zur Herstellung von Imprägnierungen bzw. Ausfüllungen und Überzügen auf porösen Stoffen, wie Steinen, Mörtel, Holz usw., benutzt. Beispiel 3 5 kg Paratoluolsulfochlorid und 5 kg Kieselweiß werden im Kollergang mit 7,5 kg grÖberem Quarzmehl gemischt, hierauf wird die Mischung durch eine Schlagmühle geschlagen. In einer Mischtrommel werden diesen 17,5 kg noch 5 kg Kieselweiß und 27,5 kg feineres Quarzmehl hinzugefügt und das ganze 15 Minuten gemischt, worauf das Kittmehl abgefüllt wird. Auf je ioo g des vorstehend @erwähnten Kittmehles werden 3o bis 40 ccm flüssiges neutrales Phenol-Aldehyd-Harz zugegeben und durch inniges Vermischen der Kitt erzeugt. Dem Phenol-Aldehyd-Harz können je nach Verwendung des Kittes noch Weichmachungsmittel zugesetzt werden.Instead of paratoluene sulfochloride, other aromatic sulfochlorideQ, such as. B. naphthalene sulfochlorides, etc., can be used. Example 2 500 parts of neutral phenol-aldehyde resin and 50 parts of benzyl alcohol (as a plasticizer) are mixed with zoo parts of silica white, 600 parts of the finest quartz flour and 70 parts of paratoluene sulfochloride Stones, mortar, wood, etc., are used. Example 3 5 kg of paratoluene sulfochloride and 5 kg of silica white are mixed in a pan with 7.5 kg of coarser quartz flour, and the mixture is then beaten by a hammer mill. In a mixing drum that 17.5 kg 5 kg more pebbles white and 27.5 kg finer quartz powder are added and mixed the whole 1 for 5 minutes is bottled after which the cement powder. For every 100 g of the abovementioned putty flour, 30 to 40 ccm of liquid, neutral phenol-aldehyde resin are added and the putty is produced by intimate mixing. Softeners can also be added to the phenol-aldehyde resin, depending on the use of the putty.
Claims (1)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1930595014D DE595014C (en) | 1930-06-07 | 1930-06-07 | Process for the production of phenol-aldehyde resins which harden faster in the cold |
| DEI45176D DE596409C (en) | 1930-06-07 | 1930-07-22 | Process for the production of phenol-aldehyde resins which harden quickly in the cold |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE595014T | 1930-06-07 | ||
| DEI45176D DE596409C (en) | 1930-06-07 | 1930-07-22 | Process for the production of phenol-aldehyde resins which harden quickly in the cold |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE596409C true DE596409C (en) | 1934-05-03 |
Family
ID=41137661
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI45176D Expired DE596409C (en) | 1930-06-07 | 1930-07-22 | Process for the production of phenol-aldehyde resins which harden quickly in the cold |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE596409C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE748697C (en) * | 1935-02-01 | 1944-11-09 | Hermann Frenkel Fa | Method of painting wood using phenol-formaldehyde synthetic resin paints |
| EP0050020A3 (en) * | 1980-10-09 | 1982-04-28 | BP Chemicals Limited | Cold set phenolic resins |
-
1930
- 1930-07-22 DE DEI45176D patent/DE596409C/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE748697C (en) * | 1935-02-01 | 1944-11-09 | Hermann Frenkel Fa | Method of painting wood using phenol-formaldehyde synthetic resin paints |
| EP0050020A3 (en) * | 1980-10-09 | 1982-04-28 | BP Chemicals Limited | Cold set phenolic resins |
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