DE1251320B - Ver drive for the production of hydroxymethylsiloxanes - Google Patents
Ver drive for the production of hydroxymethylsiloxanesInfo
- Publication number
- DE1251320B DE1251320B DENDAT1251320D DE1251320DA DE1251320B DE 1251320 B DE1251320 B DE 1251320B DE NDAT1251320 D DENDAT1251320 D DE NDAT1251320D DE 1251320D A DE1251320D A DE 1251320DA DE 1251320 B DE1251320 B DE 1251320B
- Authority
- DE
- Germany
- Prior art keywords
- formula
- hydroxymethylsiloxanes
- production
- acid
- ver drive
- 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
- -1 hydroxymethylsiloxanes Chemical class 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 8
- RJWBTWIBUIGANW-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-N 0.000 claims description 4
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 4
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 150000003961 organosilicon compounds Chemical class 0.000 description 3
- 238000005809 transesterification reaction Methods 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 229910004283 SiO 4 Inorganic materials 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- PXRIAVXPRVICRE-UHFFFAOYSA-N benzenesulfonic acid;4-methylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1.CC1=CC=C(S(O)(=O)=O)C=C1 PXRIAVXPRVICRE-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical class Cl* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
- C07F7/0872—Preparation and treatment thereof
- C07F7/0874—Reactions involving a bond of the Si-O-Si linkage
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Catalysts (AREA)
- Silicon Polymers (AREA)
Description
BUNDESREPUBLIK DEUTSCHLAND Int. Cl.:FEDERAL REPUBLIC OF GERMANY Int. Cl .:
C07fC07f
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
AUSLEGESCHRIFTEDITORIAL
Deutsche Kl.: 12 ο-26/03German class: 12 ο-26/03
Nummer:
Aktenzeichen:
Anmeldetag:
Auslegetag:Number:
File number:
Registration date:
Display day:
C07 F C07FC07 F C07F
1 251 320
F47467lVb/12o
20. Dezember 1965
5. Oktober 19671 251 320
F47467lVb / 12o
December 20, 1965
5th October 1967
7/ 08 + 7 / 187/08 + 7/18
.k.k
Gegenstand des Patents 1 236 505 ist ein Verfahren zur Herstellung von Hydroxymethylsiloxanen mit mindestens einer Struktureinheit der FormelThe subject of the patent 1 236 505 is a process for the production of hydroxymethylsiloxanes with at least one structural unit of the formula
HO-CH4-Si(CH^-(V1n HO-CH 4 -Si (CH ^ - (V 1n
worin /« = ! oder 2, und gegebenenfalls weiteren Struktureinheiten der Formelwhere / «=! or 2, and possibly others Structural units of the formula
worin η = 1, 2 oder 3 und jeder der Substituenten R ein Methyl- oder Phenylrest ist, durch Umestern der Acylreste von acyloxymethylsubstituierten Organosiliciumverbindungen mit einem Überschuß eines Alkohols in Gegenwart katalytischer Mengen einer Säure, das dadurch gekennzeichnet ist, daß man Acyloxymethylsiliciumverbindungen mit mindestens einer Struktureinheit der Formelwhere η = 1, 2 or 3 and each of the substituents R is a methyl or phenyl radical, by transesterification of the acyl radicals of acyloxymethyl-substituted organosilicon compounds with an excess of an alcohol in the presence of catalytic amounts of an acid, which is characterized in that acyloxymethylsilicon compounds with at least one Structural unit of the formula
(CH3)mSlR 3~m (CH 3 ) mSlR 3 ~ m
CH2-O-C- R'CH 2 -OC- R '
worin R' für H oder CH3 und R" für -OCH3, -OC2H5, -OC3H7,wherein R 'for H or CH 3 and R "for -OCH 3 , -OC 2 H 5 , -OC 3 H 7 ,
— O — C — R'- O - C - R '
oder — Oj/2 steht und im Falle R" == Οχ/2 gegebenenfalls weiteren Struktureinheiten der Formelor - Oj / 2 and, in the case of R ″ == Ο χ / 2, optionally further structural units of the formula
Verfahren zur Herstellung von
HydroxymethylsiloxanenProcess for the production of
Hydroxymethylsiloxanes
Zusatz zum Patent: 1 236 505Addendum to the patent: 1 236 505
Anmelder:Applicant:
Farbenfabriken Bayer Aktiengesellschaft,Paint factories Bayer Aktiengesellschaft,
LeverkusenLeverkusen
Als Erfinder benannt:Named as inventor:
Dr. Walter Simmler, Odenthal-Schlinghofen;
Dr. Hans Niederprüm, Monheim (RhId.);
Dr. Hans Sattlegger, Köln-BuchheimDr. Walter Simmler, Odenthal-Schlinghofen;
Dr. Hans Niederprüm, Monheim (RhId.);
Dr. Hans Sattlegger, Cologne-Buchheim
Gegenstand des Hauptpatents ist weiterhin eine a5 Ausführungsform, die dadurch gekennzeichnet ist, daß man im Falle, daß mindestens einer der Reste R" die Formel -OCH3, -OC2H5, -OC3H7 oder — O — C(= O) — R' hat, die Umsetzung in Gegenwart von kondensationsfähigen Organosiliciumverbindungen mit mindestens einer Struktureinheit der FormelThe main patent is also an a 5 embodiment, which is characterized in that in the case that at least one of the radicals R "has the formula -OCH 3 , -OC 2 H 5 , -OC 3 H 7 or - O - C ( = O) - R 'has the reaction in the presence of condensable organosilicon compounds with at least one structural unit of the formula
worin a = 4 oder (m + 2) ist, und gegebenenfalls weiteren Struktureinheiten der Formelwhere a = 4 or (m + 2), and optionally further structural units of the formula
im Gemisch mit 5 bis 20 Mol Methanol oder Äthanol je Mol R' und einer katalytischen Menge p-Toluolsulfonsäure auf Temperaturen unterhalb 10O0C unter gleichseitigem Abdestillieren des dabei entstehenden Estert der Formelin admixture with 5 to 20 moles of methanol or ethanol per mole of R 'and a catalytic amount of the resulting esterified p-toluenesulfonic acid at temperatures below 10O 0 C under equilateral distilling off of the formula
R'C(O)OCH3 oder R7C(O)OC2H5 R'C (O) OCH 3 or R 7 C (O) OC 2 H 5
erhitzt und dabei gegebenenfalls die zur vollständigen Hydrolyse und Siloxankondensation stöchiometrisch erforderliche Menge Wasser während der Reaktion zufügt, worauf man die p-Toluolsulfonsäure mit einem Überschuß alkoholischer Kalilauge neutralisiert, das dabei ausgefallene Salz abfiltriert, das Filtrat unter Durchleiten von Kohlendioxyd bei 20 bis 300C durch Absaugen von flüchtigen Anteilen befreit und das hinterbliebene Endprodukt klarfiltriert.heated and optionally the stoichiometrically required amount of water for complete hydrolysis and siloxane condensation is added during the reaction, whereupon the p-toluenesulfonic acid is neutralized with an excess of alcoholic potassium hydroxide, the precipitated salt is filtered off, the filtrate is passed through at 20 to 30 ° C. freed of volatile components by suction and the remaining end product is filtered clear.
R»SiO4_„R »SiO 4 _"
durchführt.performs.
Gegenstand des Hauptpatents ist schließlich noch eine Ausführungsform, die dadurch gekennzeichnet ist, daß man im Falle, daß mindestens einer der Reste R" die Formel -OCH3, -OC2H5, -OC3H7 oder — O —C(=0) —R' hat, die Umsetzung in Gegenwart von hydrolysierbaren Organosiliciumverbindungen mit mindestens einer Struktureinheit der FormelFinally, the subject of the main patent is another embodiment which is characterized in that in the event that at least one of the radicals R "has the formula -OCH 3 , -OC 2 H 5 , -OC 3 H 7 or - O —C (= 0) —R 'has the reaction in the presence of hydrolyzable organosilicon compounds with at least one structural unit of the formula
Ra- mSi(OR"')mO4_o RamSi (OR "') mO 4 _ o
2
worin a = 4 oder (nif2) ist und R'" für CH3, 2
where a = 4 or (nif2) and R '"is CH 3 ,
709 650/434709 650/434
C2H6 oder C3H7 steht, und gegebenenfalls weiteren Struktureinheiten der FormelC 2 H 6 or C 3 H 7 , and optionally further structural units of the formula
durchführt und dabei die zur vollständigen Hydrolyse und Siloxankondensation stöchiometrisch erforderliche Menge Wasser während der Reaktion zufügt.carries out and thereby the stoichiometrically required for complete hydrolysis and siloxane condensation Add amount of water during the reaction.
In weiterer Ausbildung dieses Verfahrens wurdeIn further training this procedure was
nun gefunden, daß man mindestens den gleichen Erfolg erzielt, wenn man an Stelle von p-Toluolsulfonsäure Benzolsulfonsäure oder p-Chlorbenzolsulfonsäure verwendet.now found that you can achieve at least the same success if you replace p-toluenesulfonic acid Benzene sulfonic acid or p-chlorobenzenesulfonic acid is used.
CH3-C(^O)CH 3 -C (^ O)
-O — CH2- Si(CHg)2- O — Si(CH3)2~CHä — O —C(= O) > HO —CH2-Si(CH3)2 —O — Si(CH3)2 — CH2 —OH-O - CH 2 - Si (CHg) 2 - O - Si ä (CH 3) 2 ~ CH - O -C (= O)> HO -CH 2 -Si (CH 3) 2 -O - Si (CH 3 ) 2 -CH 2 -OH
- CH3 + 2 HOCH3
2CH3-C(= O)-OCH3 - CH 3 + 2 UP 3
2CH 3 -C (= O) -OCH 3
Man löst 278 g (1 Mol) l,3-Di-(acetoxymethyl> tetramethyldisiloxan und 6,2 g Benzolsulfonsäure in 640 g (20 Mol) Methanol und destilliert aus dieser Lösung über eine Kolonne Essigsäuremethylester und überschüssiges Methanol unter Erhitzen bis auf 90° C (am Kolonnenkopf 70°C) ab. Den Rückstand mischt man mit einer Lösung von 2,3 g Kaliumhydroxyd in 30 cm3 Methanol, filtriert das ausgefallene Salz ab und verdampft aus dem Filtrat das restliche Lösungsmittel in einem durchgeleiteten Strom von Kohlendioxyd unter Erhitzen bis 900C und bis auf 3 Torr vermindertem Druck. Den Rückstand filtriert man klar und erhält als Filtrat mit praktisch vollständiger Ausbeute das l,3-Di-(hydroxymethyl)-tetramethyldisiloxan, das bei 20° C eine Dichte von 0,985 g/cm3 und eine Viskosität von 45 cP hat; 17,0 Gewichtsprozent Hydroxylgehalt, n2g = 1,4385.278 g (1 mol) of 1,3-di- (acetoxymethyl> tetramethyldisiloxane and 6.2 g of benzenesulfonic acid are dissolved in 640 g (20 mol) of methanol and methyl acetate and excess methanol are distilled from this solution over a column with heating to 90 ° C. (at the top of the column 70 ° C.) The residue is mixed with a solution of 2.3 g of potassium hydroxide in 30 cm 3 of methanol, the precipitated salt is filtered off and the remaining solvent is evaporated from the filtrate in a stream of carbon dioxide passed through with heating to 90 0 C and reduced to 3 torr pressure. the residue is filtered clear and obtained as a filtrate with virtually complete yield the l, 3-di- (hydroxymethyl) tetramethyldisiloxane, which at 20 ° C, a density of 0.985 g / cm 3 and has a viscosity of 45 cP; 17.0 weight percent hydroxyl content, n 2 g = 1.4385.
Das gleiche Ergebnis erzielt man, wenn man statt der Benzolsulfonsäure 7,5 g p-Chlorbenzolsulfonsäure verwendet und im übrigen gleichermaßen, wie vorangehend beschrieben, verfährt.The same result is achieved if 7.5 g of p-chlorobenzenesulfonic acid are used instead of the benzenesulfonic acid is used and otherwise proceeds in the same way as described above.
Zum Vergleich der katalytischen Wirksamkeit der verschiedenen aromatischen Sulfonsäuren wurden drei Versuche analog dem Beispiel durchgeführt, jedoch mit der Änderung, daß die Umesterungsreaktion jeweils nach 3 Stunden abgebrochen wurde, um den Fortgang der Umesterung durch Analyse deutlich erfassen zu können.To compare the catalytic effectiveness of the various aromatic sulfonic acids, three Experiments carried out analogously to the example, but with the change that the transesterification reaction was terminated after 3 hours in order to clearly record the progress of the transesterification by analysis to be able to.
GewichtsprozentHydroxyl content
Weight percent
«*>Refractive index
«*>
14
15
170
14th
15th
17th
38
30
11403
38
30th
11
1,4335
1,4355
1,43801.4230
1.4335
1.4355
1.4380
6 g Toluolsulfonsäure
6,2 g Benzolsulfonsäure
7,2 g p-Chlorbenzolsulfonsäure After 3 hours with
6 g of toluenesulfonic acid
6.2 g benzenesulfonic acid
7.2 g of p-chlorobenzenesulfonic acid
Die Ergebnisse lassen erkennen, daß bei gleicher Größenordnung der Reaktionsbeschleunigung die in den Beispielen genannten Sulfonsäuren, insbesondere das Chlorderivat, sogar noch merklich wirksamer sind als die p-Toluolsulfonsäure.The results show that with the same order of magnitude of the reaction acceleration, the in the sulfonic acids mentioned in the examples, in particular the chlorine derivative, are even noticeably more effective than the p-toluenesulfonic acid.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF46679A DE1236505B (en) | 1965-07-22 | 1965-07-22 | Process for the production of hydroxymethyl-siloxanes |
| DEF0047467 | 1965-10-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1251320B true DE1251320B (en) | 1967-10-05 |
Family
ID=25976883
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1251320D Pending DE1251320B (en) | 1965-07-22 | Ver drive for the production of hydroxymethylsiloxanes | |
| DEF46679A Pending DE1236505B (en) | 1965-07-22 | 1965-07-22 | Process for the production of hydroxymethyl-siloxanes |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF46679A Pending DE1236505B (en) | 1965-07-22 | 1965-07-22 | Process for the production of hydroxymethyl-siloxanes |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE684452A (en) |
| DE (2) | DE1236505B (en) |
| GB (1) | GB1121265A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102009046254A1 (en) | 2009-10-30 | 2011-05-19 | Wacker Chemie Ag | Process for the preparation of (hydroxymethyl) polysiloxanes |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4163830A (en) | 1975-12-24 | 1979-08-07 | Bayer Aktiengesellschaft | Process for the production of new polysiloxane-polyoxyalkylene copolymers with reduced burning properties |
| DE3824287A1 (en) * | 1988-07-16 | 1990-02-15 | Bayer Ag | N, N-DISUBSTITUTED OLIGO- AND POLYURETHANES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE IN THE PRODUCTION OF PLASTICS |
| DE102011080888A1 (en) | 2011-08-12 | 2013-02-14 | Technische Universität München | Process for the preparation of poly (hydroxymethyl) -functional siloxanes and silica gels |
| DE102011080900A1 (en) | 2011-08-12 | 2013-02-14 | Wacker Chemie Ag | Process for the preparation of (hydroxymethyl) polysiloxanes |
-
0
- DE DENDAT1251320D patent/DE1251320B/en active Pending
-
1965
- 1965-07-22 DE DEF46679A patent/DE1236505B/en active Pending
-
1966
- 1966-07-12 GB GB31278/66A patent/GB1121265A/en not_active Expired
- 1966-07-22 BE BE684452D patent/BE684452A/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102009046254A1 (en) | 2009-10-30 | 2011-05-19 | Wacker Chemie Ag | Process for the preparation of (hydroxymethyl) polysiloxanes |
| US8822621B2 (en) | 2009-10-30 | 2014-09-02 | Wacker Chemie Ag | Method for producing (hydroxymethyl)polysiloxanes |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1121265A (en) | 1968-07-24 |
| BE684452A (en) | 1967-01-03 |
| DE1236505B (en) | 1967-03-16 |
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