EP2247654A1 - Compositions de siloxane - Google Patents
Compositions de siloxaneInfo
- Publication number
- EP2247654A1 EP2247654A1 EP08872134A EP08872134A EP2247654A1 EP 2247654 A1 EP2247654 A1 EP 2247654A1 EP 08872134 A EP08872134 A EP 08872134A EP 08872134 A EP08872134 A EP 08872134A EP 2247654 A1 EP2247654 A1 EP 2247654A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- siloxane
- foams
- foam
- polyurethane
- siloxanes
- 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.)
- Withdrawn
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
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/0061—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof characterized by the use of several polymeric components
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/282—Alkanols, cycloalkanols or arylalkanols including terpenealcohols
- C08G18/2825—Alkanols, cycloalkanols or arylalkanols including terpenealcohols having at least 6 carbon 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/6505—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen the low-molecular compounds being compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6523—Compounds of group C08G18/3225 or C08G18/3271 or polyamines of C08G18/38
- C08G18/6535—Compounds of group C08G18/3271
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7607—Compounds of C08G18/7614 and of C08G18/7657
-
- 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
- C08G2110/00—Foam properties
- C08G2110/0008—Foam properties flexible
-
- 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
- C08G2110/00—Foam properties
- C08G2110/0025—Foam properties rigid
-
- 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
- C08G2110/00—Foam properties
- C08G2110/0083—Foam properties prepared using water as the sole blowing agent
-
- 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
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
-
- 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
- C08J2483/00—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
-
- 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
- C08J2491/00—Characterised by the use of oils, fats or waxes; Derivatives thereof
Definitions
- the invention relates to a process for the preparation of polyurethane foams from compositions containing polyols and isocyanates, wherein the preparation is optionally carried out in the presence of further additives and additives.
- additives and additives typically must prior to the reaction between the polyol and the isocyanate is added to the system ⁇ additives and additives to ER to provide the desired foam properties range.
- additives and additives include, for example, the class of siloxanes.
- organomodified siloxanes are used as stabilizers. These siloxanes are often not added in pure form during foaming, but are blended with other non-silicon-containing components. This can serve to improve the meterability, since often only very small amounts of siloxane must be added to the mixture to be foamed.
- the blending component can also improve the solubility of the siloxanes in the polyol mixture and thus additionally influence the foaming and the foam properties.
- EP-0839852 describes the production of polyurethane foam using siloxanes in blends with vegetable oils consisting of different triglycerides.
- the fatty acid esters are often raw materials that can also be used in food production, creating a competitive situation.
- raw materials that are based on renewable resources, are good biodegradable and are not suitable for food production.
- EP-0048984 describes blends of siloxanes with various water-soluble surfactants for use in polyester-polyurethane foam. These surfactants are often poorly biodegradable.
- EP-0043110 blends of siloxanes with solvents such as e.g. Alkoxylates to glycerol, water, TMP, butanol or nonylphenol for use in highly elastic polyurethane foam described.
- solvents such as e.g. Alkoxylates to glycerol, water, TMP, butanol or nonylphenol for use in highly elastic polyurethane foam described.
- US-5236961 describes the preparation of polyurethane foams using alkylphenol ethoxylates as foam stabilizers derived from petrochemical sources.
- EP-0734404 describes the production of PU foams using polyalkylene oxides, where the polyols Alkylene oxides are built up by using 10 to 90% butyl enoxide.
- the most commonly used blending components include, for example, phthalic acid esters, nonylphenol ethoxylates or butanol alkoxylates.
- the object of the present invention is therefore to find a process for the preparation of advantageous, alternative siloxane compositions, the siloxane compositions themselves, their use and polyurethane and / or polyisocyanurate and / or polyurea foams additized therewith.
- Polyurethane and / or polyisocyanurate and / or polyurea foams in the context of this invention are understood to mean reaction products of polyols and isocyanates, the preparation optionally also being carried out in the presence of further additives and additives.
- Another object of the present invention is the loading of a woman on top mixing component for siloxanes in the Po ⁇ lyurethan- and / or polyisocyanurate and / or polyurea foam production.
- CNSL cashew nut shell oil
- the invention thus addresses the improvement of the process for preparing polyurethane foams using alkylphenol-containing compositions, such as those found in CNSL-based products.
- CNSL is the short name for Cashew Nut Shell Liquid, meaning cashew nut shell oil.
- the compositions according to the invention contribute to an improvement in the foam properties.
- raw materials are used to produce the siloxane composition, which consists of non-petrochemical products, ie a high proportion of renewable raw materials.
- the present invention is the preparation of polyurethane foams from compositions containing polyols and isocyanates, wherein the preparation in the presence of a particular silicon-containing copolymer surfactant, for example a siloxane, is performed.
- a particular silicon-containing copolymer surfactant for example a siloxane
- the Sili ⁇ zium-containing surfactant is mixed with the CNSL-based Verbin ⁇ applications to not only improve the controllability of the SII oxane, but also the properties of the foam thus produced.
- the advantage is that one obtains equivalent or better results in the foaming than when using e.g. Nonylphenol ethoxylates or other blending components.
- CNSL-based products are well biodegradable, toxi ⁇ ecologically harmless and are derived from natural disadvantages growing raw materials. Furthermore, the CNSL-based products not for the production of food suitable and therefore not enter into "competition" for food ⁇ food production.
- Cashew nut shell liquid thus Cashew nut shells oil. This is obtained by extraction of the outer shell of the cashew nut. Most of the extract is obtained by heating the shells. However, it can also be prepared by extraction methods in which solvents are used.
- the extract may have variable compositions depending on its origin and method.
- the main components are: Cardanol, Anacard acid, Cardol and Methylcardol.
- the proportion of anacardic acid and cardanol can vary greatly, since the anacardic acid is decarboxylated by heating during the hot extraction and thus converted to cardanol.
- cardanol is obtained from the CNSL as an alkylphenol component, which can then be further processed into a wide variety of products (alkoxylates, formaldehyde resins, etc.). Cardanol is obtained by distillation from CNSL.
- the various CNSL based products can be used for the blends according to the invention, such as For example, the extract itself, the distillation products or even the distillation residues.
- Cardanol production from CNSL is among others described in the patent applications DE-IO 2005 017126, DE-I 0 2005 017125.
- CNSL e.g. Alkoxylates
- resins which can be prepared by reactions with aldehydes, or oxidation products of CNSL, etc.
- CNSL e.g. Alkoxylates
- resins which can be prepared by reactions with aldehydes, or oxidation products of CNSL, etc.
- These derivatives have hitherto been used only as a polyol component in polyurethanes.
- the use as a blending component for siloxanes is not described.
- US-7084103 describes ethoxylates of Cardanol and Cardol and their use as lubricants or dispersants.
- GB-2262525 describes the preparation of ethoxylates ba ⁇ sierend in the technical cashew nut shell oil.
- Cardanol derivatives (Anacardklare, Cardanol, Cardol) are named and described as the basis for the ethoxylation, and their use as emulsifiers in the alkyd resin system.
- EP-1765901 describes polyols for the production of PU hard foam, which are produced on the basis of CNSL by epoxidation of the double bonds in the alkylene side chain and subsequent ring opening in order to increase the OH number of the polyol.
- the use of the CNSL-based polyols as blending component for the siloxanes is not described ⁇ ben.
- EP-1723187 describes the preparation of polyols based on distillation residues from cardanol production. These residues are reacted with alkylene oxides and the resulting polyols used for the preparation of PU binder mixtures.
- IN 180735 describes polyols for the production of PU hard foam which are prepared on the basis of CNSL mixtures by reaction with reaction products of castor oil reaction products and polyhydroxy compounds, such as, for example, B. pentaerythritol.
- DE-10106144 describes the use of cardanol-aldehyde resins as asphaltene dispersants in crude oil.
- the color and odor of the CNSL-based products can be optimized and used in more demanding applications.
- suitable perfumes may be used to tailor the olfactory properties.
- siloxane copolymers or siloxanes the substances which are suitable according to the prior art can be used.
- foam type rigid foams, hot-foams, viscoelastic foams, ester foams, HR foams, semi-rigid foams
- a suitable siloxane must be used.
- the proportion of siloxane copolymer in the blend can be from 0.1 to 98%, preferably from 0.3 to 95%, particularly preferably from 0.5 to 90%, in particular from 1 to 80% or from 5 to 70% and most preferably 10 to 60%, optionally depending on the intended use, in each case based on percent by weight of the total mixture.
- the proportion of CNSL-based products is from 2 to 99.9%, preferably from 5 to 99.7%, particularly preferably from 10 to 99.5%, in particular from 20 to 99% or from 30 to 95% and very particularly preferably from 40 to 90%, optionally depending on the particular intended use, in each case based on percent by weight of the total mixture.
- the composition may also optionally contain the blending components known from the prior art, for example polyethers, nonylphenol ethoxylates, nonionic surfactants, ionic surfactants and other substances or auxiliaries, in proportions of 0 to 95%, or . from 0.1 to 80%, based on weight percent Ge ⁇ the total mixture.
- blending components known from the prior art, for example polyethers, nonylphenol ethoxylates, nonionic surfactants, ionic surfactants and other substances or auxiliaries, in proportions of 0 to 95%, or . from 0.1 to 80%, based on weight percent Ge ⁇ the total mixture.
- the tasks of the siloxane may be quite different with regard to the flexible polyurethane foams, depending on which properties the foam formulation entails.
- the basic requirement is the stabilization of the foam desired, ie the avoidance of collapse ⁇ phenomena .
- the requirements for the siloxanes may then be toward cell regulation, cell opening or flow enhancement, an example of which may be molded foams for making car seats.
- siloxane-containing formulations according to the invention are suitable for all types of foam which can be prepared by reacting polyols with polyisocyanates (rigid foams, hot-foams, viscoelastic foams, ester foams, HR foams, semi-rigid foams, etc.).
- polyisocyanates rigid foams, hot-foams, viscoelastic foams, ester foams, HR foams, semi-rigid foams, etc.
- the foams are produced by the known processes by reacting polyols and isocyanates with Essence of a blowing agent, which soft foams, semi-rigid foams or rigid foams may arise, depending on which polyols and isocyanates used. These may be polyurethane, polyisocyanurate or polyurea foams.
- suitable polyols are ⁇ sets. This may be act to polyether or polyester polyols typically carry 2 to 6 OH groups per molecule and may also contain heteroatoms such as nitrogen, phosphorus or halogens, in addition to carbon, hydrogen and Sauer ⁇ material.
- organic polyisocyanates are used which have a functionality greater than or equal to 2.
- Corresponding compounds are known and commercially it ⁇ linguallich.
- blowing agent is needed. All known blowing agents can be used. This may be as a chemical blowing agent water, which releases by re ⁇ action with the isocyanates carbon dioxide. However, it is also possible to use carbon dioxide directly as a physical blowing agent or other blowing agents which are vaporized by a suitable boiling point in the exothermic reaction. Examples of these are halogenated hydrocarbons or hydrocarbons such as pentane isomers. It is also possible to combine the two methods.
- the urethane foam reaction is usually by suitable
- Catalysts triggered or controlled For example, tertiary amines or metal-containing catalysts (containing, for example, tin, potassium, zinc) are used here.
- the foams can be prepared by the known methods.
- the silicon-containing surfactant mixture can be mixed directly for foaming with the polyols and isocyanates. However, it is also possible to prepare a premix of the surfactant, one or more blowing agents, the polyol and the catalysts.
- blowing agents and polyisocyanates for Her ⁇ position of polyurethane foams which are customary in this field for the respective types of foam compounds as such can.
- Suitable siloxanes are described, for example, in the following documents: EP-0839852, EP-1544235, DE-IO 2004 001 408, EP-0839852, WO-2005/118668, US-20070072951, DE-2533074, EP-1537159 EP-0533202, US-3933695, EP-0780414, DE-4239054, DE-4229402, EP-0867465.
- the foam composition may contain further excipients which are required for the production and / or use of the foam and which are compatible with the composition.
- Foam-trained professional are familiar and familiar. These are, for example, flame retardants, dyes, pigments ⁇ preparations, cell openers, biocides, antistatic additives etc ..
- Siloxane 1 Polyethersiloxane as in EP 1544235 A1 in Example
- Siloxane 2 Polydimethylsiloxane, as described in DE 2533074 Al Example 4 as mixture 1.
- siloxane 3 is a polyether siloxane according to the following formula:
- the preparation of such Si-C-linked polyethersiloxanes is described for example in US 4,147,847, EP 0493836 and US 4,855,379.
- Siloxane 4 According to the methods described in DE 43 17 605, a 1, 1, 1, 2, 3, 3, 3-heptamethyltrisiloxane with an allyl alcohol started polyether having a PO content of 30% and EO content of 70% and an average molar mass of 900 g / mol with a suitable Pt catalyst to the corresponding polyether siloxane reacted:
- CNSL CT Cashew Nut Shell Liquid from Imperial Oil Import
- CNSL RS 1 Residue from CNSL distillation available from Imperial Oil Import
- NC-700 + 5 EO Reaction product of Cardolite NC-700 with 5 moles of ethylene oxide per OH function
- NC-700 + 5 PO Reaction product of Cardolite NC-700 with 5 mol of propylene oxide per OH function
- Cardanol 1 Cardanol which was prepared by the process described in DE-102005017126.
- Nonylphenol + 8EO Reaction product of nonylphenol with 8 moles of ethylene oxide per OH function, commercially available, for example, as Arkopal N 080 from Clariant L) Castor oil, commercially available, for example from Fa.
- Blend according Tab.l 1.4 g (1, 5 parts) as a stabilizer
- the foaming was carried out by hand mixing.
- polyol, catalysts, water, the stabilizer formulation to be tested and propellant were weighed into a beaker and mixed with a paddle stirrer (6 cm diameter) for 30 s at 1000 rpm. Weigh again to was the evaporated during the mixing process of propellant be ⁇ true and then adds.
- the MDI was added, the reaction mixture stirred with the described stirrer for 5 s at 3000 rpm and immediately in a 45 ° C thermostated aluminum mold of 145 cm x 14 cm x 3.5 cm in size transferred, which was on ⁇ clothes at an angle of 10 ° (along the 145 cm measured side) and inclined with polyethylene film.
- the foam formulation was introduced at the lower side, so that the expanding foam fills the mold in the sprue area and rises in the direction of the higher side.
- the amount of Schaumformu ⁇ lation used was so dimensioned that it was below the amount necessary for the minimum filling of the mold.
- the length of the foam molding obtained after curing can thus be used - normalized to the weight - as a measure of the volume yield .
- HR foam highly elastic foam, cold foam
- the foams were ⁇ represents Herge in the known manner, by mixing all components except for the isocyanate in a beaker, then adding the isocyanate, and stirring it rapidly at high stirrer speed. was then added, the reaction mixture in a cuboid shape with the dimen ⁇ solutions 40x40x10 cm, which was heated to a temperature of 40 0 C and allowed to cure the composition for 10 minutes. Subsequently, the pressing forces were measured. Here, the foams were compressed 10 times to 50% of their height.
- the first measured value (AD 1 in Newton) is a measure of the open-cell viscosity of the foam.
- compositions according to the invention are suitable for producing highly elastic PU foams and that the open-cell nature (and the hardness) of the foam can be influenced by suitable choice of the blending component according to the invention.
- siloxane blends were tested in a typical polyurethane hot foam formulation:
- the return ⁇ case refers to the sagging of the foam surface after blowing off the Polyurethanheissweichschaumes. The relapse is measured 3 min after the blow-off.
- the density was measured according to DIN EN ISO 845 and DIN EN ISO 823. The number of cells was counted by means of a magnifying glass with scaling in three places and the values were averaged.
- the compressive strength according to DIN EN ISO 3386-1 was measured and the SAG factor was calculated from the quotient of the compression hardness at 65% compression and 25% compression of the foam. Thus, the SAG factor is a measure of the elasticity of the foam.
- Table 5 shows the results of the polyurethane hot soak foam test. They are the siloxane mixture used, the rise time (SZ) in seconds, the foam height (SH) in cm, the relapse (RF) in cm, the density (RG) in kg / m and the cell number (ZZ) in cells / cm and the SAG factor (SAG-F). Table 5:
- siloxane formulations (compositions) according to the invention are suitable for producing hot-soft foam and, in addition, an improvement in the SAG factor (elasticity) can be achieved.
- siloxane blends were evaluated in a typical polyester polyurethane foam formulation:
- Raw materials Desmophen 2200 from Bayer, tolylene diisocyanate (TDI 80/20) from Bayer, N-methylmorpholine (NMM).
- Foam formulation 100 parts Desmophen 2200 polyester polyol, 56.5 parts TDI 80, 5.1 parts water, 1.4 parts NMM, 1.0 part siloxane blend. Execution :
- the air permeability is a measure of the proportion of open cells in the foam. For many applications, a possible open-cell foam is desired.
- the open cells of the foams was determined by the air permeability ⁇ .
- the air permeability is given in mm.
- Back pressure Water column which builds up when a constant air flow of 480 l / h is passed through the foam. The higher the value, the more closed the foam and vice versa.
- Table 6 shows the results of the foaming of mixtures according to the invention (Examples 32 and 33) and of a mixture not according to the invention
- compositions according to the invention in the production of polyester-polyurethane flexible foams results in flawless foams and higher cell numbers can be achieved.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Degasification And Air Bubble Elimination (AREA)
Abstract
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102008000255A DE102008000255A1 (de) | 2008-02-08 | 2008-02-08 | Siloxanzusammensetzungen |
PCT/EP2008/067405 WO2009097936A1 (fr) | 2008-02-08 | 2008-12-12 | Compositions de siloxane |
Publications (1)
Publication Number | Publication Date |
---|---|
EP2247654A1 true EP2247654A1 (fr) | 2010-11-10 |
Family
ID=40352412
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP08872134A Withdrawn EP2247654A1 (fr) | 2008-02-08 | 2008-12-12 | Compositions de siloxane |
Country Status (10)
Country | Link |
---|---|
US (1) | US8912277B2 (fr) |
EP (1) | EP2247654A1 (fr) |
JP (1) | JP2011512428A (fr) |
KR (1) | KR20100122900A (fr) |
CN (1) | CN101503571B (fr) |
BR (1) | BRPI0821907A2 (fr) |
DE (1) | DE102008000255A1 (fr) |
MX (1) | MX2010007481A (fr) |
RU (1) | RU2010137081A (fr) |
WO (1) | WO2009097936A1 (fr) |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL2002442C2 (nl) * | 2009-01-22 | 2010-07-26 | Weezenbeek Specialties B V Van | Werkwijze voor het verjongen van een bitumen bevattende samenstelling. |
DE102009028061A1 (de) | 2009-07-29 | 2011-02-10 | Evonik Goldschmidt Gmbh | Verfahren zur Herstellung von Polyurethanschaum |
DE102011007479A1 (de) | 2011-04-15 | 2012-10-18 | Evonik Goldschmidt Gmbh | Zusammensetzung, enthaltend spezielle Amide und organomodifizierte Siloxane, geeignet zur Herstellung von Polyurethanschäumen |
DE102011083017A1 (de) | 2011-09-20 | 2013-03-21 | Evonik Industries Ag | Verbundwerkstoffe umfassend eine offenzellige Polymermatrix und darin eingebettete Granulate |
JP2015117275A (ja) * | 2013-12-17 | 2015-06-25 | 住化バイエルウレタン株式会社 | ポリウレタン樹脂用原料としてのカシューナッツ殻液の使用 |
DE102013226575B4 (de) | 2013-12-19 | 2021-06-24 | Evonik Operations Gmbh | Zusammensetzung, geeignet zur Herstellung von Polyurethanschäumen, enthaltend mindestens einen ungesättigten Fluorkohlenwasserstoff oder ungesättigten Fluorkohlenwasserstoff als Treibmittel, Polyurethanschäume, Verfahren zu deren Herstellung und deren Verwendung |
DE102014215384A1 (de) | 2014-08-05 | 2016-02-11 | Evonik Degussa Gmbh | Stickstoffhaltige Verbindungen, geeignet zur Verwendung bei der Herstellung von Polyurethanen |
DE102014215388A1 (de) | 2014-08-05 | 2016-02-11 | Evonik Degussa Gmbh | Stickstoffhaltige Verbindungen, geeignet zur Verwendung bei der Herstellung von Polyurethanen |
DE102014215382A1 (de) | 2014-08-05 | 2016-02-11 | Evonik Degussa Gmbh | Stickstoffhaltige Verbindungen, geeignet zur Verwendung bei der Herstellung von Polyurethanen |
JP6656796B2 (ja) * | 2014-08-27 | 2020-03-04 | コベストロ、ドイチュラント、アクチエンゲゼルシャフトCovestro Deutschland Ag | ポリイソシアヌレートフォーム原料としてのカシューナッツ殻液の使用 |
JP6667986B2 (ja) * | 2014-08-27 | 2020-03-18 | コベストロ、ドイチュラント、アクチエンゲゼルシャフトCovestro Deutschland Ag | ポリウレタン樹脂製造における高イソシアネートインデックス下でのカシューナッツ殻液の使用 |
PL3115389T3 (pl) | 2015-07-07 | 2020-09-07 | Evonik Operations Gmbh | Wytwarzanie pianki poliuretanowej |
PL3487945T3 (pl) | 2016-07-19 | 2020-11-16 | Evonik Operations Gmbh | Zastosowanie estrów poliolowych do wytwarzania porowatych powłok z tworzywa sztucznego |
CN110072943B (zh) | 2016-10-18 | 2022-04-12 | 陶氏东丽株式会社 | 聚醚改性的硅酮组合物,以及用于制造所述组合物的方法 |
US11373389B2 (en) | 2020-06-23 | 2022-06-28 | Tusimple, Inc. | Partitioning images obtained from an autonomous vehicle camera |
US11715277B2 (en) | 2020-06-23 | 2023-08-01 | Tusimple, Inc. | Perception system for autonomous vehicles |
WO2022193160A1 (fr) * | 2021-03-17 | 2022-09-22 | Dow Silicones Corporation | Composition de préparation de mousse, procédés associés à celle-ci, et mousse formée à partir de celle-ci |
Family Cites Families (53)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2531502A (en) | 1950-11-28 | Oxyalkylated drastically-oxibizkb | ||
US3629308A (en) | 1966-07-25 | 1971-12-21 | Union Carbide Corp | Siloxane-oxyalkylene block copolymers |
US3730920A (en) * | 1972-01-06 | 1973-05-01 | Union Carbide Corp | Compositions containing microspheres and friction elements produced therefrom |
US3933695A (en) | 1972-12-29 | 1976-01-20 | Union Carbide Corporation | Hydroxyalkenylsiloxane rigid poly urethane foam stabilizers |
US4147847A (en) | 1973-11-14 | 1979-04-03 | Dow Corning Corporation | Method of preparing flexible flame retardant polyether based one-shot polyurethane foams and compositions therefore |
CH597270A5 (fr) | 1974-08-30 | 1978-03-31 | Goldschmidt Ag Th | |
DE2754091A1 (de) | 1977-12-05 | 1979-06-13 | Henkel Kgaa | Waessrige dispersionen von als ueberzugsmittel bzw. lackbindemittel geeigneten harzen |
US4309508A (en) | 1980-06-30 | 1982-01-05 | Union Carbide Corporation | Siloxane copolymer mixtures useful as foam stabilizers in high resilience polyurethane foam |
US4331555A (en) | 1980-09-29 | 1982-05-25 | Union Carbide Corporation | Use of organosiloxane compositions as foam stabilizers in flexible polyester polyurethane foam |
US4855379A (en) | 1988-03-08 | 1989-08-08 | Union Carbide Corporation | Silicone surfactants containing cyclic siloxane pendants |
US5145879A (en) | 1990-12-31 | 1992-09-08 | Union Carbide Chemicals & Plastics Technology Corporation | Surfactants for manufacture of urethane foams |
IN180735B (fr) | 1991-03-11 | 1998-03-14 | Council Scient Ind Res | |
BR9203663A (pt) | 1991-09-20 | 1993-04-20 | Union Carbide Chem Plastic | Uso de tensoativos capeados para a producao de espumas de polioretano rigidas soprados com hidrocloro-fluorcarbonetos |
GB2262525B (en) | 1991-12-18 | 1995-11-01 | Johnson & Son Inc S C | A process for ethoxylating a derivative of technical cashew nut shell liquid |
DE4229402A1 (de) | 1992-09-03 | 1994-03-10 | Goldschmidt Ag Th | Polysiloxan-Polyoxyalkylen-Blockmischpolymerisat mit unterschiedlichen Polyoxyalkylenblöcken im durchschnittlichen Molekül |
DE4239054A1 (de) | 1992-11-20 | 1994-05-26 | Goldschmidt Ag Th | Polysiloxan-Polyoxyalkylen-Blockmischpolymerisat mit unterschiedlichen Polyoxyalkylenblöcken im durchschnittlichen Molekül |
US5236961A (en) | 1992-12-30 | 1993-08-17 | Basf Corporation | Water-blown integral skin polyurethane foams having a skin with abrasion resistance |
DE4317605C1 (de) | 1993-02-25 | 1994-06-16 | Goldschmidt Ag Th | Organopolysiloxanpolyether und deren Verwendung als hydrolysestabile Netzmittel in wäßrigen Systemen |
US5600019A (en) | 1993-12-17 | 1997-02-04 | The Dow Chemical Company | Polyisocyanate based polymers perpared from formulations including non-silicone surfactants and method for the preparation thereof |
HUT77801A (hu) | 1994-10-20 | 1998-08-28 | The Dow Chemical Company | Eljárás zárt cellás poliuretánhabok előállítására szénhidrogén hajtóanyag jelenlétében, valamint poliuretán-prekurzorként alkalmazható anyagkeverékek |
JP3190272B2 (ja) | 1995-12-22 | 2001-07-23 | エアー.プロダクツ.アンド.ケミカルス.インコーポレーテッド | 可撓性ポリウレタンフォームの製造方法 |
US6071977A (en) | 1996-10-31 | 2000-06-06 | Ck Witco Corporation | Hydrosilation in high boiling natural vegetable oils |
US5844010A (en) | 1997-03-29 | 1998-12-01 | Th. Goldschmidt Ag | Method of preparing polyurethane foam utilizing block copolymers having linked siloxane blocks |
US6262148B1 (en) | 1998-07-01 | 2001-07-17 | Vantico Inc. | Phenalkamine curing agents and epoxy resin compositions containing the same |
DE19905989A1 (de) | 1999-02-13 | 2000-08-17 | Bayer Ag | Feinzellige, wassergetriebene Polyurethanhartschaumstoffe |
US6133329A (en) | 1999-03-31 | 2000-10-17 | Oxid L.P. | Aromatic polyester polyols made from a natural oil |
DE19927548C2 (de) | 1999-06-16 | 2002-12-12 | Clariant Gmbh | Verfahren zur Herstellung von flammwidrigen Polyurethanweichschäumen |
US20020103091A1 (en) | 2001-01-29 | 2002-08-01 | Kodali Dharma R. | Reactive oil compositions and uses thereof |
DE10106144C2 (de) | 2001-02-10 | 2003-02-20 | Clariant Gmbh | Verwendung von Cardanol-Aldehydharzen als Asphalten-Dispergatoren in Rohölen |
CA2465853A1 (fr) | 2002-08-27 | 2004-03-11 | Indian Oil Corporation Limited | Composition de tensioactif comprenant de l'ethoxylate d'huile de cajou |
DE10240186A1 (de) | 2002-08-28 | 2004-03-11 | Basf Ag | Verfahren zur Herstellung von emissionsarmen Polyurethan-Weichschaumstoffen |
US7084103B1 (en) | 2003-03-11 | 2006-08-01 | Palmer International, Inc. | Methods of preparation of ethoxylated phenolic compounds, compositions containing the same and related methods |
US7960444B2 (en) | 2003-04-25 | 2011-06-14 | Dow Global Technologies Llc | Vegetable oil based polyols and polyurethanes made therefrom |
US8133930B2 (en) * | 2003-04-25 | 2012-03-13 | Dow Global Technologies Llc | Polyurethane foams made from hydroxymethyl-containing polyester polyols |
US7676432B2 (en) | 2003-07-08 | 2010-03-09 | Paybyclick Corporation | Methods and apparatus for transacting electronic commerce using account hierarchy and locking of accounts |
US8293808B2 (en) * | 2003-09-30 | 2012-10-23 | Cargill, Incorporated | Flexible polyurethane foams prepared using modified vegetable oil-based polyols |
CN1926164A (zh) * | 2003-09-30 | 2007-03-07 | 嘉吉有限公司 | 用改性植物油基多元醇制备的挠性聚氨酯泡沫材料 |
US7183330B2 (en) | 2003-12-15 | 2007-02-27 | Air Products And Chemicals, Inc. | Silicone surfactants for rigid polyurethane foam made with hydrocarbon blowing agents |
JP2005179709A (ja) | 2003-12-17 | 2005-07-07 | Toyo Tanso Kk | ガス発生装置 |
DE102004001408A1 (de) | 2004-01-09 | 2005-07-28 | Goldschmidt Ag | Verwendung blockweise aufgebauter Polyethersiloxane als Stabilisatoren in Polyurethanschäumen |
DE102004009818A1 (de) | 2004-02-28 | 2005-09-15 | Bayer Materialscience Ag | Hydrophobe, niedrigviskose Polyole |
DE102004011559A1 (de) | 2004-03-08 | 2005-09-29 | Rathor Ag | Phasenstabile Polyurethanprepolymere |
WO2005118668A1 (fr) | 2004-05-25 | 2005-12-15 | General Electric Company | Procede de preparation de mousses de polyurethane ayant des emissions en composes organiques volatils reduites |
BRPI0418851A (pt) | 2004-06-30 | 2007-11-20 | Council Scient Ind Res | processo para a preparação de um poliol de poliuretano |
CA2599983A1 (fr) | 2005-03-03 | 2006-09-08 | South Dakota Soybean Processors, Llc | Nouveaux polyols issus d'une huile vegetale au moyen d'un procede d'oxydation |
US20060235100A1 (en) | 2005-04-13 | 2006-10-19 | Kaushiva Bryan D | Polyurethane foams made with vegetable oil hydroxylate, polymer polyol and aliphatic polyhydroxy alcohol |
DE102005017126A1 (de) | 2005-04-14 | 2006-10-19 | Cognis Ip Management Gmbh | Verfahren zur Herstellung von Cardanol (I) |
DE102005017125A1 (de) | 2005-04-14 | 2006-10-19 | Cognis Ip Management Gmbh | Verfahren zur Herstellung von Cardanol (II) |
EP1888666B1 (fr) | 2005-04-25 | 2017-06-21 | Cargill, Incorporated | Mousses de polyurethane comprenant des polyols oligomeriques |
US9856355B2 (en) | 2005-09-27 | 2018-01-02 | Evonik Degussa Gmbh | Silanol-functionalized compounds for the preparation of polyurethane foams |
WO2007111828A2 (fr) | 2006-03-23 | 2007-10-04 | Dow Global Technologies Inc. | Mousse de polyurethane de basse densite a base d'huile naturelle sans additif de stabilisation de cellules a base de silicone |
US20070238800A1 (en) | 2006-04-11 | 2007-10-11 | Bayer Materialscience Llc | Storage stable isocyanate-reactive component containing vegetable oil-based polyol |
US7828991B2 (en) | 2006-12-08 | 2010-11-09 | Bayer Materialscience Llc | Polyether polyols based on cashew nutshell liquid and flexible foams |
-
2008
- 2008-02-08 DE DE102008000255A patent/DE102008000255A1/de not_active Withdrawn
- 2008-08-07 CN CN2008101456247A patent/CN101503571B/zh not_active Expired - Fee Related
- 2008-12-12 MX MX2010007481A patent/MX2010007481A/es unknown
- 2008-12-12 JP JP2010545369A patent/JP2011512428A/ja active Pending
- 2008-12-12 WO PCT/EP2008/067405 patent/WO2009097936A1/fr active Application Filing
- 2008-12-12 EP EP08872134A patent/EP2247654A1/fr not_active Withdrawn
- 2008-12-12 US US12/866,565 patent/US8912277B2/en not_active Expired - Fee Related
- 2008-12-12 KR KR1020107017493A patent/KR20100122900A/ko not_active Application Discontinuation
- 2008-12-12 BR BRPI0821907-9A patent/BRPI0821907A2/pt not_active IP Right Cessation
- 2008-12-12 RU RU2010137081/05A patent/RU2010137081A/ru unknown
Non-Patent Citations (1)
Title |
---|
See references of WO2009097936A1 * |
Also Published As
Publication number | Publication date |
---|---|
KR20100122900A (ko) | 2010-11-23 |
US20110028578A1 (en) | 2011-02-03 |
MX2010007481A (es) | 2010-08-11 |
RU2010137081A (ru) | 2012-03-20 |
BRPI0821907A2 (pt) | 2015-06-16 |
CN101503571A (zh) | 2009-08-12 |
US8912277B2 (en) | 2014-12-16 |
DE102008000255A1 (de) | 2009-08-20 |
WO2009097936A1 (fr) | 2009-08-13 |
CN101503571B (zh) | 2013-04-10 |
JP2011512428A (ja) | 2011-04-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2009097936A1 (fr) | Compositions de siloxane | |
EP2088166B1 (fr) | Agents de compatibilité destinés à l'amélioration de la stabilité au stockage de mélanges de polyols | |
EP2242790B1 (fr) | Utilisation, pour la fabrication de mousses de polyuréthane, de stabilisateurs de mousse fabriqués à base de matières premières renouvelables | |
EP2182020B1 (fr) | Copolymères à bloc de silicone polyéther ayant une polydispersion définie dans la part de polyoxyalkylène et leur utilisation comme stabilisateurs dans la fabrication de mousses de polyuréthane | |
CN110072943B (zh) | 聚醚改性的硅酮组合物,以及用于制造所述组合物的方法 | |
EP2481770B1 (fr) | Utilisation de copolymères à bloc de silicone polyéther avec résidus de polyéther à haut poids moléculaire sans groupe terminal comme stabilisateurs pour la fabrication de mousses de polyuréthane de faible densité | |
EP2481766B1 (fr) | Copolymères à bloc de silicone polyéther avec résidus de polyéther à haut poids moléculaire et leur utilisation comme stabilisateurs pour la fabrication de mousses de polyuréthane | |
EP2230266B1 (fr) | Agent de compatibilité destiné à l'amélioration de la stabilité au stockage de mélanges de polyol | |
EP2601244B1 (fr) | Copolymères de silicone comprenant des restes alkyle latéraux liés par des allylglycidyléthers et des composés apparentés et leur utilisation comme stabilisants pour la fabrication de mousses souples de polyuréthane | |
WO2010081601A1 (fr) | Procédé de fabrication de mousses froides | |
WO2019193101A1 (fr) | Mousses de polyuréthane à base de polyéthercarbonate polyols | |
EP3288994A1 (fr) | Mélanges de polyols de polyéthercarbonate et de polyéther polyols pour la fabrication de mousses de polyuréthane souples | |
EP3178858A1 (fr) | Mousses de polyurethane a base de polyethercarbonatpolyoles | |
EP3762441B1 (fr) | Mousses de polyuréthane à base de polyéther carbonates polyoles | |
WO2019170568A1 (fr) | Mousses de polyuréthane à base de polyéthercarbonate polyols | |
WO1997031959A1 (fr) | Resines polyurethane | |
JP7229346B2 (ja) | ポリオール組成物 | |
EP3555166B1 (fr) | Procédé de réduction d'émissions d'une mousse de polyuréthane | |
EP3892660A1 (fr) | Mousses de polyuréthane à base de polyéther carbonates polyoles | |
WO2022258503A1 (fr) | Utilisation de catalyseurs au bismuth pour diminuer le carbonate de propylène cyclique dans la production de matériaux en mousse souple à base de polyéthercarbonate-polyols | |
WO2022175210A1 (fr) | Procédé de production d'une mousse de polyuréthane | |
WO2023144057A1 (fr) | Mousses de polyuréthane souples à base de polyisocyanates oligomères aliphatiques, et composés monohydroxy-fonctionnels | |
EP4043510A1 (fr) | Procédé de fabrication de mousse de polyuréthane |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
17P | Request for examination filed |
Effective date: 20100709 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MT NL NO PL PT RO SE SI SK TR |
|
AX | Request for extension of the european patent |
Extension state: AL BA MK RS |
|
DAX | Request for extension of the european patent (deleted) | ||
RAP1 | Party data changed (applicant data changed or rights of an application transferred) |
Owner name: EVONIK DEGUSSA GMBH |
|
17Q | First examination report despatched |
Effective date: 20140909 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
18D | Application deemed to be withdrawn |
Effective date: 20161215 |