WO1994029324A1 - Hydrocarbures polyhydroxyles modifies au siloxanyl - Google Patents

Hydrocarbures polyhydroxyles modifies au siloxanyl Download PDF

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Publication number
WO1994029324A1
WO1994029324A1 PCT/EP1994/001656 EP9401656W WO9429324A1 WO 1994029324 A1 WO1994029324 A1 WO 1994029324A1 EP 9401656 W EP9401656 W EP 9401656W WO 9429324 A1 WO9429324 A1 WO 9429324A1
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stands
alkyl
groups
group
formula
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PCT/EP1994/001656
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German (de)
English (en)
Inventor
Roland Wagner
Reingard Wersig
Gerd Schmaucks
Bernd Weiland
Lothar Richter
Annette Hennig
Andrea JÄNICKE
Jürgen REINERS
Wolfgang Krämer
Joachim WEISSMÜLLER
Wolfgang Wirth
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Bayer Aktiengesellschaft
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Priority to AU69296/94A priority Critical patent/AU6929694A/en
Publication of WO1994029324A1 publication Critical patent/WO1994029324A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H23/00—Compounds containing boron, silicon, or a metal, e.g. chelates, vitamin B12
    • 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
    • C08G77/04—Polysiloxanes
    • C08G77/045—Polysiloxanes containing less than 25 silicon atoms
    • 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
    • C08G77/38—Polysiloxanes modified by chemical after-treatment
    • C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
    • C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
    • 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
    • C09K23/54—Silicon compounds

Definitions

  • the invention relates to si loxanyl-modified compounds, their preparation and their use as surface-active and surface-modifying agents
  • Siloxanyl modified compounds are known.
  • EP-A 0 317 377 describes contact lens materials which are obtained by reacting epoxy-functional polysiloxanes with saccharides such as gluconic acid or
  • Glucosamine can be obtained.
  • SiH funct ionel len polysiloxanes is the subject of AT-B 0 393 509, and also surface-active compounds with the aim of hydrophilizing the hydrophobic
  • Siloxane substrate can be obtained
  • JP-A 62 68820 describes polysiloxanes with sugar residues which are obtained by reacting amino-functional polysiloxanes with lactones which are derived from aldonic and uronic acids and are surface-active.
  • Z stands for a radical derived from a mono- or oligosaccharide with 1 to 10 pentose and / or hexose units, or for cyclic or acyclic polyhydroxylated hydrocarbons with 4 or 5 carbon atoms, the cycle containing at least one oxygen atom and optionally is substituted by mono- or oligosaccharides with 1 to 10 pentose and / or hexose units
  • n is calculated as the maximum possible number of OH groups of Z, where n is at least 3 and at most 40, v stands for a number 1 to 10 , w stands for a number 0 to 10, with a maximum of one group per monosaccharide unit
  • nvw is a number from 0 to 39
  • X represents alkyl, C 1 - to C 4 -acyl or the group in which k represents a number 0 to 10, and
  • R 1 , R 2 independently of one another are H or CH 3
  • R 12 represents H or alkyl, the group from T independently of one another represents optionally substituted alkylene, which may be substituted by at least one of the groups, -COO-, -CO-NR 13 -, -NR 13 -,
  • R 13 and R 14 represent hydrogen or alkyl, i represents a number 0 to 3, L represents the groups
  • R 11 stands, R 11 for H, alkyl, hydroxyalkyl, or for the
  • R 11 together with the group (T) e forms a preferably 5- or 6-membered heterocyclic ring, a - h independently of one another for a number 0 or
  • A stands for a siloxane chain consisting of m structural elements of the formula
  • R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are identical or different and are alkyl, cycloalkyl, cycloalkyl-alkyl or optionally substituted aryl or aralkyl, the radicals R 5 , R 7 and R 8 also being for the group
  • R 10 represents alkyl, the sum of the structural elements m independently of one another being a number from 0 to 600, and
  • B and R 3 have the same meaning as A, or represent alkyl, cycloalkyl, cycloalkyl-alkyl, optionally substituted aryl or aralkyl, or A and B together form a siloxane cycle, where the radicals R 4 to R 10 in chains A, B and R 3 can be different, as surface-active and surface-modifying agents or their use for the preparation of surface-active and surface-modifying agents.
  • Alkyl can be a straight-chain or branched alkyl radical having 1 to about 6 carbon atoms. Examples include methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, n-pentyl, iso-pentyl, n-hexyl and iso-hexyl. Preferred alkyl radicals are methyl and ethyl,
  • Halogen can be fluorine, chlorine, bromine or iodine, preferably fluorine or chlorine,
  • Cycloalkyl can represent a cyclic, preferably monocyclic, hydrocarbon radical having 5 to 7 carbon atoms. Examples include cyclopentyl, cyclohexyl and cycloheptyl. Are preferred
  • Cycloalkyl-alkyl can represent a radical having 6 to 13 carbon atoms, it being possible for a straight-chain or branched alkyl radical (C 1 to C 6 ) to be substituted by a cycloalkyl radical (C 5 to C 7 ).
  • a straight-chain or branched alkyl radical C 1 to C 6
  • a cycloalkyl radical C 5 to C 7
  • cyclohexylmethyl 2-cyclohexyl-1-ethyl
  • cycloheptylmethyl 2-cycloheptyl-1-ethyl.
  • Aryl can represent an aromatic hydrocarbon radical having 6 to 12 carbon atoms. Examples include phenyl, naphthyl and biphenyl. Phenyl is preferred,
  • Aralkyl can represent a radical having 7 to 18 carbon atoms, and a straight-chain or branched alkyl radical (C 1 to C 6 ) can be substituted by an aromatic radical (C 6 to C 12 ). Examples include benzyl, phenyl-ethyl and phenyl-propyl. Benzyl is preferred.
  • aryl and aralkyl radicals can optionally be substituted.
  • substituents are alkyl (C 1 to about C 6 ), aryl (C 6 to C 12 ) and halogen, preferably fluorine and chlorine.
  • C 1 - to C 4 -acyl can represent a formyl, acetyl, propionyl, iso-propionyl radical, acetyl is preferred.
  • the siloxane chain (A) consists of m structural elements
  • the structural elements can be distributed statistically or combined into larger structural areas (blocks). It is also possible that the siloxane chain consists of only one type of the structural elements mentioned.
  • the siloxane chain consists of a total of 0 to 600, preferably 0 to 200, particularly preferably 0 to 50, structural elements (m).
  • structural elements (m) of the structural elements is 0 and B and R 3 are alkyl
  • the siloxane chain A consists only of the end group (disiloxane).
  • the silox portion consists only of the unit
  • An alkylene chain (T) generally represents a double-bonded, straight-chain or branched hydrocarbon radical having 1 to 10 carbon atoms. Alkylene chains having 1 to 6 carbon atoms are preferred. Examples include the following alkylene chains: methylene, ethylene, propylene, isopropylene, 1-methyl-propylene- (1,3), 1,2-dimethyl-propylene- (1,3),
  • the alkylene chain (T) can also be through the groups such as
  • n maximum possible number of OH groups of Z
  • n means that for sugars e.g. a pentose unit or a hexose unit in the cyclic form cannot contain more than 3 or 4 OH groups.
  • the number of substituents M per unit Z is preferably 1. In this case, e.g.
  • a monofunctional le Sil unit is preferably provided under Sil.
  • the invention further relates to new compounds of the formula (I)
  • Z stands for a residue that differs from mono- or
  • D and E independently of one another represent hydrogen, alkyl, C 1 to C 4 -acyl, nvw a number from 0 to 39 represents alkyl, C 1 - to C 4 -acyl or the group in which
  • k represents a number 0 to 10
  • R 1 , R 2 independently of one another are H or CH 3
  • Q represents the groups -O-, , -COO-, -CONR 12 -, -OCO-, -NR 12 -CH 2 -, -OCH 2 -, -NR 12 -CO-, or stands,
  • R 12 is H or alkyl
  • a to h independently of one another represent a number 0 or 1, at least one index being 1, and e in the event that f is 0, 1 is and
  • Z is not bound to M via oxygen
  • este T independently represent optionally substituted alkylene, which may be replaced by at least one of the Groups, -COO-, -CO-NR 13 -, -NR 13 -,
  • Arylene in each case saturated or unsaturated cycloalkylene or a 5- or 6-membered heterocycle with O or N heteroatoms
  • R 13 and R 14 represent hydrogen or C 1 to C 4 alkyl, i represents a number 0 to 3, R 1 1 represents H, alkyl, hydroxyalkyl or the groups, or
  • R 11 together with the group (T) e forms a preferably 5- or 6-membered heterocyclic ring
  • A stands for a siloxane chain consisting of m structural elements of the formula
  • R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are identical or different and are alkyl, cycloalkyl, cycloalkyl-alkyl or optionally substituted aryl or aralkyl, the radicals R 5 , R 7 and R 8 also being for the group
  • R 10 represents alkyl
  • a and B together form a siloxane cycle, where the radicals R 4 to R 10 in the chains A, B and R 3 can be different.
  • b to g independently of one another represent a number 0 or 1, for groups -O-, -COO-, -CONR 12 -, -OCO-, -NR 12 -CH 2 -, -OCH 2 - or -NR 12 -CO- and in the event that f stands for 0, is 1 and Z does not exceed Oxygen is bound to M, and
  • Y is the meaning of methyl
  • Z stands for a residue that differs from mono- or
  • D and E independently of one another represent hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -acyl, nvw is a number from 0 to 39 represents alkyl, C 1 - to C 4 -acyl or the group in which
  • k represents a number 0 to 10
  • R 1 , R 2 independently of one another are H or CH 3
  • M for a group in which a to h independently of one another represent a number 0 or 1, where at least one index is 1,
  • Z stands for a residue that differs from mono- or
  • n is calculated as the maximum possible number of OH groups of Z, where n is at least 3 and at most 40, v is a number 1 to 10, preferably 1, w is a number 0 to 10 stands, whereby there is at most one group per monosaccharide unit in which
  • E and D independently of one another represent hydrogen, C 1 - to C 4 -alkyl or C 1 - to C 4 -acyl, nvw is a number from 0 to 39, X is alkyl, C 1 - to C 4 -acyl or the group stands in the
  • k represents a number 0 to 10
  • R 1 , R 2 independently of one another are H or CH 3
  • compounds of formula (I) in which represents a radical derived from a reducing sugar or a reduced or oxidized sugar derivative, such as glucose, mannose, fructose, maltose; Saccarose, cellobiose, palatinose (glucopyranosyl fructose), glucopyranosyloxymethyl furfural, asculin, g-shophanthine, 2-aminoglucose, with reduced derivatives for example reduced with ammonia or amines
  • a radical derived from a reducing sugar or a reduced or oxidized sugar derivative such as glucose, mannose, fructose, maltose
  • Saccarose cellobiose
  • palatinose glucopyranosyl fructose
  • glucopyranosyloxymethyl furfural asculin
  • g-shophanthine 2-aminoglucose
  • n is calculated as the maximum possible number of OH groups of Z, where n is at least 3 and at most 40, v stands for a number 1 to 10, w stands for a number 0 to 10, whereby per
  • D and E independently of one another represent hydrogen, alkyl, C 1 - to C 4 -acyl, nvw is a number from 0 to 39
  • X represents alkyl, C 1 - to C 4 -acyl or the group in which k represents a number 0 to 10 and
  • R 1 , R 2 independently of one another are H or CH 3
  • M for a group in which a to h independently of one another is a number
  • the reactions are carried out at -40 to + 150 ° C., normally in a solvent, particularly preferably in lower alcohols, ethers, water, ketones, nitriles, nitroalkanes, esters, amides, sulfoxides and (halogenated) hydrocarbons
  • a solvent particularly preferably in lower alcohols, ethers, water, ketones, nitriles, nitroalkanes, esters, amides, sulfoxides and (halogenated) hydrocarbons
  • acid scavengers or catalysts acidic or basic
  • the individual reaction conditions can be found by way of example, but not by way of limitation, in the respective preparative examples. by reacting compounds of the formula (V)
  • the reactions are carried out at -40 ° C to + 150 ° C, normally in a solvent, particularly preferably in turn alcohols, ethers, water, ketones, nitriles, nitroalkanes, esters, amides, sulfoxides and (halogenated) hydrocarbons .
  • acid scavengers or catalysts (acid or basic or free-radical (coordinative) can be used.
  • the individual reaction conditions are exemplary but not restrictive in the respective preparative examples.
  • the reactions are carried out at -40 to + 150 ° C., in the normal case in a solvent, particularly preferably in lower alcohols, ethers, water, ketones, nitriles, nitroalkanes, esters, amides, sulfoxides and (halogenated) hydrocarbons.
  • a solvent particularly preferably in lower alcohols, ethers, water, ketones, nitriles, nitroalkanes, esters, amides, sulfoxides and (halogenated) hydrocarbons.
  • acid scavengers or catalysts acidic or basic
  • the individual reaction conditions can be found by way of example, but not by way of limitation, in the respective preparative examples.
  • the reactions are carried out in a solvent DMSO, water and predominantly alcohols at -40 ° C. to 150 ° C., the Schiff base initially forming, which is then known in a manner known per se, in the presence of transition metal catalysts from the group Fe , Ni, Co, ruthenium (Raney catalysts) at 50 to 200 ° C and a hydrogen pressure of 1 to 300 bar is reduced.
  • transition metal catalysts from the group Fe , Ni, Co, ruthenium (Raney catalysts) at 50 to 200 ° C and a hydrogen pressure of 1 to 300 bar is reduced.
  • the new and known compounds of formula (I) have extremely good surface-active and surface-modifying properties and are used according to the invention, for example, as film formers, flow control agents, wetting agents, dispersants, stabilizers and / or spraying agents or generally as formulation auxiliaries, additives or adjuvants where the properties of formulations must be modified accordingly.
  • the properties of the compounds of formula (I) can easily meet the requirements by varying the siloxanyl part and / or spacer and / or hydrocarbon part be adjusted accordingly.
  • the spacer can be introduced into the molecule either by the siloxanes modified accordingly in upstream reactions and / or by the biologically or chemically prefunctionally ionized saccharide derivatives.
  • the compounds of the formula (I) offer the advantage of good biodegradability or extremely good ecological compatibility.
  • the compounds of the formula (I) are preferably used as formulation auxiliaries, additives or adjuvants for crop protection agents. They serve as emulsifiers for active substances and / or solvents in solid and liquid formulations, in particular in emulsion concentrates of these active substances,
  • additives or adjuvants serve to improve the effectiveness by increasing spray adhesion and increasing the penetration of the active ingredient into the plant. This is associated with increased rain resistance,
  • formulation auxiliaries they are incorporated into the recipe at 0.5 to 50%, preferably 1 to 20%.
  • additive or adjuvant they are added to the spray mixture in a concentration of 0.05 to 1%, preferably 0.1 to 0.5%.
  • the compounds of the formula (I) are used as starting materials for the preparation of corresponding cationic and anionic compounds or betaines. These compounds are described and claimed in two parallel applications and also have very good surface-active or surface-modifying properties,
  • Example 1 1,1,1,3,5,5-heptamethyltrisiloxan-3-yl-prop-2-enyl- ⁇ -D-glucose
  • the synthesized siloxanyl-modified saccharide compounds are characterized by good to very good surfactant properties.
  • the table below lists some of the surface chemical parameters of 0.1% aqueous solutions (distilled water) of the compounds.
  • Epoxides from Example 10 are heated in 30 ml of methanol (dry) in a steel autoclave to 95 ° C. for 5 h. The pressure rises to 2-3 bar. After the mixture has cooled, the solvent is removed from the homogeneous mixture in vacuo. A white powdery solid is separated. This mass is taken up in 3 ⁇ 30 ml of solvent mixture (pentane / ether 1: 1) and stirred. After vacuum drying, 4.3 g of a yellow powder remain, which is hygroscopic. calc.
  • V 0 mN / m
  • Example 21 3.6 g (20 mmol) of ⁇ -D - (+) - glucose are placed in 50 ml of methanol and 15 ml of H 2 O. 5.6 g (20 mmol) of 3- (3-aminopropyl) -1,1,1,3,5,5,5-heptarnethyl-trisiloxane are added. The mixture is allowed to react under reflux, a methanol / H 2 O mixture being distilled off. 150 ml of absolute methanol are added dropwise. After a reaction time of 2.5 hours, the solvent is distilled off and the residue is degassed in a high vacuum.
  • Solvent remains 1.7 g of a strong yellow powder, which dissolves well in water. about. found
  • Phenylglycidether are taken up in 20 ml of methanol and heated in a steel autoclave for 4 hours at 100 ° C. After removing the solvent, a yellow amorphous mass remains, which can be completely dissolved in 20 ml of pentane. Another rotation leads to 1.7 g of a soft yellow powder «

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  • Health & Medical Sciences (AREA)
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  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
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Abstract

La présente invention décrit des composés modifiés au siloxanyl, leur fabrication et leur utilisation comme substances tensioactives et de modification de surface destinées en particulier à la protection des plantes ou à la fabrication d'agents tensioactifs ou de modification de surface.
PCT/EP1994/001656 1993-06-04 1994-05-24 Hydrocarbures polyhydroxyles modifies au siloxanyl WO1994029324A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU69296/94A AU6929694A (en) 1993-06-04 1994-05-24 Siloxanyl-modified polyhydroxylated hydrocarbons

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4318536A DE4318536A1 (de) 1993-06-04 1993-06-04 Siloxanylmodifizierte polyhydroxylierte Kohlenwasserstoffe
DEP4318536.3 1993-06-04

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Publication Number Publication Date
WO1994029324A1 true WO1994029324A1 (fr) 1994-12-22

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DE (1) DE4318536A1 (fr)
WO (1) WO1994029324A1 (fr)

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WO1999000400A1 (fr) * 1997-06-25 1999-01-07 Cognis Deutschland Gmbh Ether de silicium d'oligoglycoside d'alkyle et/ou d'alcenyle
JPH11505564A (ja) * 1995-05-19 1999-05-21 ノバルティス アクチエンゲゼルシャフト ポリシロキサン−ポリオールマクロマー、これらの製造法及びこれらの用途
US6197876B1 (en) 1999-02-24 2001-03-06 Ck Witco Corporation Heterocyclic amine modified siloxanes
US6235681B1 (en) * 1998-12-10 2001-05-22 Ck Witco Corporation Terminally modified, amino, polyether siloxanes
WO2006127882A2 (fr) 2005-05-23 2006-11-30 Dow Corning Corporation Compositions de traitement de surface a copolymeres de saccharide-siloxane
FR2929282A1 (fr) * 2008-03-25 2009-10-02 Centre Nat Rech Scient Polysiloxanes fonctionnalises, leur procede de preparation et leurs utilisations
US8247357B2 (en) 2007-02-20 2012-08-21 Dow Corning Corporation Filler treating agents based on hydrogen bonding polyorganosiloxanes
DE102012103372A1 (de) 2011-04-18 2012-10-18 Momentive Performance Materials Gmbh Verwendung von aminofunktionellen Polyorganosiloxanen als Holzschutzmittel
WO2013083749A1 (fr) 2011-12-08 2013-06-13 Dow Corning Corporation Silanes hydrolysables et compositions élastomères les contenant
WO2014054686A1 (fr) 2012-10-02 2014-04-10 東レ・ダウコーニング株式会社 Nouvel organopolysiloxane co-modifié, agent de traitement de poudre le contenant et composition de poudre
US8853372B2 (en) 2010-08-23 2014-10-07 Dow Corning Corporation Saccharide siloxanes stable in aqueous environments and methods for the preparation and use of such saccharide siloxanes
US8877216B2 (en) 2005-05-23 2014-11-04 Dow Corning Corporation Cosmetic and skin-care compositions comprising saccharide-siloxane copolymers
US8907026B2 (en) 2004-12-23 2014-12-09 Dow Corning Corporation Crosslinkable saccharide-siloxane compositions, and networks, coatings and articles formed therefrom
US8968773B2 (en) 2006-05-23 2015-03-03 Dow Corning Corporation Silicone film former for delivery of actives
US9080057B2 (en) 2011-12-08 2015-07-14 Dow Corning Corporation Treatment of filler with silane
US9192564B2 (en) 2010-08-23 2015-11-24 Dow Corning Corporation Saccharide siloxane copolymers and methods for their preparation and use
US9315631B2 (en) 2012-01-18 2016-04-19 Dow Corning Corporation Methods of making saccharide siloxane copolymers
US9321792B2 (en) 2011-12-08 2016-04-26 Dow Corning Corporation Hydrolysable silanes
US9440997B2 (en) 2011-12-08 2016-09-13 Dow Corning Corporation Hydrolysable silanes
US9492369B2 (en) 2010-08-23 2016-11-15 Dow Corning Corporation Emulsions containing saccharide siloxane copolymer emulsifiers and methods for their preparation and use
WO2017189704A1 (fr) * 2016-04-27 2017-11-02 Dow Corning Corporation Trisiloxane à groupe fonctionnel carbinol et son procédé de formation
KR20180133491A (ko) * 2016-04-27 2018-12-14 다우 실리콘즈 코포레이션 카르비놀 작용성 트라이실록산을 포함하는 세제 조성물
US10982051B2 (en) 2017-06-05 2021-04-20 Momentive Performance Materials Inc. Aqueous compositions for hair treatment comprising polyorganosiloxanes with polyhydroxyaromatic moieties

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DE19807044A1 (de) * 1998-02-19 1999-08-26 Wacker Chemie Gmbh Organosiliciumverbindungen mit polyhydroxyfunktionellen Kohlenwasserstoffresten, deren Herstellung und Verwendung
DE19854186A1 (de) 1998-11-24 2000-05-25 Wacker Chemie Gmbh Grenzflächenaktive Organosiliciumverbindungen
DE10120754A1 (de) 2001-04-27 2002-11-07 Hansa Textilchemie Gmbh Amidofunktionelle Polydiorganosiloxane
CN1311003C (zh) 2002-03-20 2007-04-18 Ge拜尔硅股份有限公司 支链聚有机硅氧烷聚合物
AU2003302035A1 (en) 2002-11-04 2004-06-15 Ge Bayer Silicones Gmbh And Co. Kg Formulations used for the treatment of substrate surfaces
DE10316662A1 (de) 2003-04-11 2004-11-11 Ge Bayer Silicones Gmbh & Co. Kg Reaktive Amino- und/oder Ammonium-Polysiloxanverbindungen
EP1817322A2 (fr) * 2004-11-16 2007-08-15 Commissariat A L'energie Atomique Agents de silanisation a groupement saccharidique terminal et leurs utilisations, notamment pour la fonctionnalisation de supports solides
DE102007037345A1 (de) 2007-08-08 2009-02-12 Wacker Chemie Ag Quaternäre Ammoniumgruppen aufweisende Organosiliciumverbindungen und deren Herstellung
WO2011042409A2 (fr) 2009-10-05 2011-04-14 Momentive Performance Materials Gmbh Émulsions aqueuses de polyorganosiloxanes
EP2504381B1 (fr) 2009-11-24 2018-03-07 Momentive Performance Materials GmbH Polysiloxanes modifiées hydrophiles/lipophiles en tant qu'émulsifiants
CN103764725B (zh) 2011-04-18 2017-03-01 迈图高新材料有限责任公司 用于处理木质纤维素材料的官能化的聚有机硅氧烷或硅烷
US11535751B2 (en) 2015-07-20 2022-12-27 Momentive Performance Materials Gmbh Asymmetrically substituted polyorganosiloxane derivatives
US9988404B2 (en) 2016-04-07 2018-06-05 Momentive Performance Materials Inc. Ester-modified organosilicon-based surfactants, methods of making same and applications containing the same

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DE19727030A1 (de) * 1997-06-25 1999-01-07 Henkel Kgaa Alkyl- und/oder Alkenyloligoglykosidsiliconether
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