DE1106070B - Self-emulsifying organopolysiloxane solutions - Google Patents
Self-emulsifying organopolysiloxane solutionsInfo
- Publication number
- DE1106070B DE1106070B DEF29847A DEF0029847A DE1106070B DE 1106070 B DE1106070 B DE 1106070B DE F29847 A DEF29847 A DE F29847A DE F0029847 A DEF0029847 A DE F0029847A DE 1106070 B DE1106070 B DE 1106070B
- Authority
- DE
- Germany
- Prior art keywords
- self
- organopolysiloxane
- percent
- water
- solutions
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
- C08J3/07—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media from polymer solutions
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
- C08J3/091—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids characterised by the chemical constitution of the organic liquid
- C08J3/095—Oxygen containing compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/017—Mixtures of compounds
- C09K23/018—Mixtures of two or more different organic oxygen-containing compounds
-
- 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
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2383/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
- C08J2383/04—Polysiloxanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Silicon Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
DEUTSCHESGERMAN
Die Erfindung betrifft neue Organopolysiloxanlösungen, welche die Eigenschaft haben, bei einfachem Mischen mit Wasser selbsttätig, d. h. ohne Zuhilfenahme besonderer Vorrichtungen, Emulsionen zu bilden.The invention relates to new organopolysiloxane solutions which have the property of being easily mixed automatically with water, d. H. to form emulsions without the aid of special devices.
Es erfordert bekanntlich einen großen Aufwand, wäßrige Organopolysiloxanemulsionen von solcher Beständigkeit herzustellen, daß sie ohne Entmischung während langer Zeit gelagert und den Schüttelbewegungen längerer Beförderungswege ausgesetzt werden können. In gewissen Fällen ist diese Aufgabe überhaupt nicht befriedigend zu lösen, sei es wegen hoher Grenzflächenspannung zwischen Wasser und Organopolysiloxanöl, wie bei Alkylpolysiloxanen mit höhermolekularen Alkylresten, sei es wegen chemischer Unbeständigkeit des Organopolysiloxanöles gegenüber Wasser, wie bei den Wasserstoff am Silicium tragenden Organopolysiloxanen.As is known, it takes a great deal of effort to produce aqueous organopolysiloxane emulsions of such stability produce that they are stored for a long time without segregation and the shaking movements longer Transport routes can be suspended. In certain cases this task is not at all satisfactory too dissolve, be it because of the high interfacial tension between water and organopolysiloxane oil, as in the case of alkylpolysiloxanes with higher molecular weight alkyl radicals, be it because of the chemical instability of the organopolysiloxane oil compared to water, as in the case of the organopolysiloxanes that carry hydrogen on silicon.
Gegenstand der Erfindung sind mit Wasser selbsttätig emulgierende Lösungen von Organopolysiloxanen, die aus 0,1 bis 60 Gewichtsprozent flüssiger kohlen wasserstoffsubstituierter Polysiloxane, 99,8 bis 30 Gewichtsprozent wasserfreien Äthyl- oder Propylalkohols und 0,1 bis 10 Gewichtsprozent eines der Ester bestehen, die sich von Fettsäuren mit 8 bis 18 C-Atomen und Polyglykolen oder Polyhydroxyverbindungen mit mehr als drei O H-Gruppen oder deren Verätherungsprodukten mit Polyglykolen ableiten.The invention relates to solutions of organopolysiloxanes which emulsify automatically with water and which from 0.1 to 60 percent by weight of liquid carbon-hydrogen-substituted polysiloxanes, 99.8 to 30 percent by weight Anhydrous ethyl or propyl alcohol and 0.1 to 10 percent by weight of one of the esters are made up of fatty acids with 8 to 18 carbon atoms and polyglycols or polyhydroxy compounds with more than three O H groups or derive their etherification products with polyglycols.
Diese Lösungen erlauben beliebig langes Lagern auch dann, wenn sie Organopolysiloxane enthalten, welche Wasserstoff am Siliciumatom tragen, und bilden in Berührung mit Wasser Emulsionen, ohne daß es der Anwendung mechanischer Energie zur Zerteilung der Ölphase bedarf. Aus den erfindungsgemäßen Lösungen lassen sich also mit Wasser ohne weitere Hilfsmittel Organopolysiloxanemulsionen kurz vor Gebrauch am Ort der Verwendung herstellen. Während der kurzen Dauer der Bereitstellung verändern sich diese Emulsionen kaum, auch wenn sie Organohydrogenpolysiloxane enthalten, da die erfindungsgemäß als Emulgator verwendeten Ester sich auch in Gegenwart von Wasser indifferent gegen das Organopolysiloxan verhalten. Man umgeht also auf diese Weise alle Schwierigkeiten, die sich durch Veränderung einer fertiggestellten Emulsion beim Lagern und Befördern ergeben könnten.These solutions allow any length of storage even if they contain organopolysiloxanes, which Carry hydrogen on the silicon atom and, in contact with water, form emulsions without it being applied mechanical energy is required to break up the oil phase. From the solutions according to the invention organopolysiloxane emulsions with water without any further auxiliaries shortly before use at the place of use produce. During the short duration of provision, these emulsions hardly change, either if they contain organohydrogenpolysiloxanes, since the esters used according to the invention as emulsifiers are themselves behave indifferently to the organopolysiloxane even in the presence of water. So you deal with this Wise all the difficulties that arise from changing a finished emulsion during storage and transportation could result.
Es sind zwar schon emulgatorhaltige Organopolysiloxanlösungen in Äthanol und Propanol beschrieben worden, die sich in Wasser leicht emulgieren lassen sollen. Die darin gelösten Organopolysiloxane müssen aber Silanolgruppen enthalten und sind selbst nur bis zu einem Mischungsanteil von etwa 11 Gewichtsprozent in der Lösung vorhanden. Der Emulgator ist im wesentlichen ein niedrigsiedendes Alkylamin. Auf Organohydrogenpolysiloxane ist eine derartige Kombination schon wegen der alkalischen Reaktion des Emulgators und der dadurch bekanntlich sehr beschleunigten Hydrolyse der Si-H-Selbstemulgierende Organopolysiloxanlösungen It is true that organopolysiloxane solutions containing emulsifiers in ethanol and propanol have already been described which are said to be easy to emulsify in water. The organopolysiloxanes dissolved therein must, however Contain silanol groups and are themselves only up to a mixing proportion of about 11 percent by weight in the Solution available. The emulsifier is essentially a low boiling alkylamine. On organohydrogenpolysiloxanes is such a combination because of the alkaline reaction of the emulsifier and the resulting known to be very accelerated hydrolysis of Si-H self-emulsifying organopolysiloxane solutions
Anmelder:Applicant:
Farbenfabriken Bayer Aktiengesellschaft,
Leverkus en-B ay er werkPaint factories Bayer Aktiengesellschaft,
Leverkus en-B ay works
Dr. Walter Noil, Leverkusen,
ist als Erfinder genannt wordenDr. Walter Noil, Leverkusen,
has been named as the inventor
Bindungen nicht anwendbar. Aber auch die Übertragung auf solche Organopolysiloxane, die von reaktiven Gruppen frei sind, insbesondere also auf die gemeinhin als Organopolysiloxanöle bezeichneten «,(w-Bis-(trimethylsiloxy)-polydialkylsiloxane, ergibt kein selbstemulgierendes System; hier ist eine intensiv wirkende Emulgiermaschine erforderlich, andernfalls scheidet sich das Siloxanöl sofort von der wäßrigen Flüssigkeit beim Einbringen der Lösung in Wasser.Bindings not applicable. But also the transfer to such organopolysiloxanes by reactive groups are free, especially those commonly known as organopolysiloxane oils designated «, (w-bis- (trimethylsiloxy) -polydialkylsiloxane, does not result in a self-emulsifying system; here is an intense emulsifying machine required, otherwise the siloxane oil separates immediately from the aqueous liquid when the solution is introduced in water.
Es sind auch Emulgatoren bekannt, die Kohlenwasserstoffölen selbstemulgierende Eigenschaften verleihen. Der Versuch einer Übertragung auf die Organopolysiloxane hat sich jedoch als erfolglos erwiesen; weder Tetraalkylammoniumsalze noch Ölsäure oder Natriumoleat oder Partialester des Glycerins oder des Propylenglykols, gelöst oder suspendiert in einem Organopolysiloxanöl, bewirken dessen Selbstemulgierung in Wasser. Aber sogar die erfindungsgemäß zu verwendenden höhermolekularen Ester genügen allein nicht; zum Ziel führt erst die Hinzunahme einer dritten Mischungskomponente, für die sich bisher nur Äthanol oder eines der beiden Propanole als geeignet haben finden lassen. Die Homologen dieser Alkohole sind kaum wirksam, ebensowenig Dioxan und Aceton; Methanol löst die Organopolysiloxanöle nicht hinreichend.Emulsifiers are also known which give hydrocarbon oils self-emulsifying properties. Of the Attempts to transfer it to the organopolysiloxanes have proven unsuccessful, however; neither tetraalkylammonium salts or oleic acid or sodium oleate or partial esters of glycerol or propylene glycol, dissolved or suspended in an organopolysiloxane oil, cause it to self-emulsify in water. But even the higher molecular weight esters to be used according to the invention are not sufficient on their own; only the addition leads to the goal a third mixture component, for which so far only ethanol or one of the two propanols as suitable. The homologues of these alcohols are hardly effective, nor are dioxane and Acetone; Methanol does not adequately dissolve the organopolysiloxane oils.
Die Bedeutung dieser dritten Komponente zeigt sich auch darin, daß der Emulgator zu einem Teil durch einen höheren Mischungsanteil des Alkohols ersetzt werden kann. Um beispielsweise aus 100 g eines Methylhydrogenpolysiloxanöles durch Zumischen von Isopropanol und dem Hexaoleat eines polyäthoxylierten Sorbits als Emulgator erfindungsgemäß eine selbstemulgierende Lösung zu gewinnen, benötigt man 20 g des Emulgators, also ein Fünftel der Organopolysiloxanmenge, bei Anwendung von 80 g Isopropanol, dagegen nur 4 g Emulgator, also ein Fünfundzwanzigstel der Organopolysiloxanmenge, bei Anwendung von 300 g Isopropanol.The importance of this third component is also shown in the fact that the emulsifier is partly by one higher mixing proportion of the alcohol can be replaced. For example, from 100 g of a methyl hydrogen polysiloxane oil by adding isopropanol and the hexaoleate of a polyethoxylated sorbitol as an emulsifier To obtain a self-emulsifying solution according to the invention, 20 g of the emulsifier are required, ie a fifth of the amount of organopolysiloxane when using 80 g of isopropanol, but only 4 g of emulsifier, i.e. one twenty-fifth of the amount of organopolysiloxane when using 300 g of isopropanol.
In den folgenden Beispielen sind weitere Mischungen aufgeführt. Sie werden am bequemsten hergestellt, indem man in dem wasserfreien Alkohol zuerst den Emulgator,Further mixtures are listed in the following examples. They are most conveniently made by you first add the emulsifier in the anhydrous alcohol,
109 579/4-37109 579 / 4-37
dann das Organopolysiloxanöl löst. Es ergeben sich lagerbeständige klare Flüssigkeiten, die sich beim Eingießen in Wasser spontan und rasch zu einer Emulsion verteilen. Dieser Vorgang kann durch leichtes, lediglich der beschleunigten Durchmischung dienendes Rühren unterstützt werden, bedarf aber nicht der sonst zur Emulgierung üblichen mechanischen Vorrichtungen.then the organopolysiloxane oil dissolves. This results in shelf-stable ones clear liquids that spontaneously and quickly spread to form an emulsion when poured into water. This process can be supported by gentle stirring, which is only used for accelerated mixing but does not require the mechanical devices otherwise customary for emulsification.
Die erfindungsgemäße Zusammenstellung der selbstemulgierenden Organopolysiloxanlösungen erhellt aus folgenden Beispielen:The composition of the self-emulsifying organopolysiloxane solutions according to the invention is clear following examples:
250 g Ä,«-Bis-(trimethylsiloxy)-oktylmethylpolysil-250 g Ä, «- bis (trimethylsiloxy) -octylmethylpolysil-
oxan von 2OcSt (200C);
744 g Isopropanol;
6 g Hydroxypentaäthoxyäthyloleat.oxane of 2OcSt (20 0 C);
744 grams of isopropanol;
6 g of hydroxypentaethoxyethyl oleate.
250 g (X,w-Bis-(trimethylsiloxy)-polydimethylsiloxan250 g of (X, w-bis (trimethylsiloxy) polydimethylsiloxane
von 6OcSt (200C);
730 g Isopropanol;
20 g Hydroxypolyäthoxyäthyloleat mit 5of 6OcSt (20 0 C);
730 grams of isopropanol;
20 g of hydroxypolyethoxyethyl oleate with 5
bis 8 Äthylenoxydeinheiten.up to 8 ethylene oxide units.
250 g eines aus den Siloxaneinheiten C6H5Si03/2,250 g of a siloxane of the C 6 H 5 Si0 3/2,
(CH3)2Si02/2 und (CHg)3SiO1Z2 im Zahlenverhältnis von ungefähr 3:3:4 zusammengesetzten, vollkommen kondensierten Phenylmethylpolysiloxanöles von 180 cSt (20° C);(CH 3) 2 Si0 2/2 and (CHg) 3 SiO 1 Z 2 in the ratio of about 3: compound 4, completely condensed Phenylmethylpolysiloxanöles of 180 cSt (20 ° C); 3
740 g Äthanol;
10 g Monooleat eines polyäthoxylierten Sorbits.740 grams of ethanol;
10 g monooleate of a polyethoxylated sorbitol.
500 g a,a)-Bis-(trimethylsiloxy)-polymethylhydrogensiloxan
von 10 cSt (20° C);
400 g Isopropanol;500 ga, a) bis (trimethylsiloxy) polymethyl hydrogen siloxane of 10 cSt (20 ° C);
400 grams of isopropanol;
100 g Monooleat eines polyäthoxylierten Sorbits.100 g monooleate of a polyethoxylated sorbitol.
250 g (%,ct)-Bis-(trimethylsiloxy)-polymethylhydrogensiloxan von 10 cSt (20° C);250 g (%, ct) bis (trimethylsiloxy) polymethyl hydrogen siloxane of 10 cSt (20 ° C);
740 g n-Propanol;740 grams of n-propanol;
10 g Hydroxypolyäthoxyäthylstearat mit 5
bis 8 Äthylenoxydeinheiten.10 g of hydroxypolyethoxyethyl stearate with 5
up to 8 ethylene oxide units.
250 g «,co-Bis-(trimethylsiloxy)-polymethylhydrogen-250 g «, co-bis (trimethylsiloxy) -polymethylhydrogen-
siloxan von 10 cSt (20° C);
740 g Isopropanol;
10 g Monolaurat des Sorbitans.siloxane of 10 cSt (20 ° C);
740 grams of isopropanol;
10 g of sorbitan monolaurate.
Claims (1)
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL257905D NL257905A (en) | 1959-11-13 | ||
DEF29847A DE1106070B (en) | 1959-11-13 | 1959-11-13 | Self-emulsifying organopolysiloxane solutions |
FR843399A FR1273580A (en) | 1959-11-13 | 1960-11-09 | Self-emulsifying hydrocarbopolysiloxane solutions |
BE596956A BE596956A (en) | 1959-11-13 | 1960-11-10 | Self-emulsifying hydrocarbopolysiloxane solutions |
GB38717/60A GB915787A (en) | 1959-11-13 | 1960-11-10 | Self-emulsifying organo-polysiloxane solutions |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF29847A DE1106070B (en) | 1959-11-13 | 1959-11-13 | Self-emulsifying organopolysiloxane solutions |
DEF0030495 | 1960-02-09 |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1106070B true DE1106070B (en) | 1961-05-04 |
Family
ID=25974478
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEF29847A Pending DE1106070B (en) | 1959-11-13 | 1959-11-13 | Self-emulsifying organopolysiloxane solutions |
Country Status (4)
Country | Link |
---|---|
BE (1) | BE596956A (en) |
DE (1) | DE1106070B (en) |
GB (1) | GB915787A (en) |
NL (1) | NL257905A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0219039A2 (en) * | 1985-10-07 | 1987-04-22 | Wacker Silicones Corporation | Transparent antifog compositions |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB8729489D0 (en) * | 1987-12-18 | 1988-02-03 | Dow Corning Ltd | Polyorganosiloxane emulsions |
CN113913996A (en) * | 2021-11-09 | 2022-01-11 | 罗莱生活科技股份有限公司 | Modal/cotton/viscose blended fabric and preparation method thereof |
-
0
- NL NL257905D patent/NL257905A/xx unknown
-
1959
- 1959-11-13 DE DEF29847A patent/DE1106070B/en active Pending
-
1960
- 1960-11-10 GB GB38717/60A patent/GB915787A/en not_active Expired
- 1960-11-10 BE BE596956A patent/BE596956A/en unknown
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0219039A2 (en) * | 1985-10-07 | 1987-04-22 | Wacker Silicones Corporation | Transparent antifog compositions |
EP0219039A3 (en) * | 1985-10-07 | 1988-11-17 | Wacker Silicones Corporation | Transparent antifog compositions |
Also Published As
Publication number | Publication date |
---|---|
BE596956A (en) | 1961-03-01 |
GB915787A (en) | 1963-01-16 |
NL257905A (en) |
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