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WO2008138363A1 - Copolymères séquencés de polyéthers et de polysiloxanes contenant de l'azote, procédé pour leur préparation et leur utilisation pour améliorer les propriétés de surface de tissus et de fibres - Google Patents

Copolymères séquencés de polyéthers et de polysiloxanes contenant de l'azote, procédé pour leur préparation et leur utilisation pour améliorer les propriétés de surface de tissus et de fibres Download PDF

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Publication number
WO2008138363A1
WO2008138363A1 PCT/EP2007/004123 EP2007004123W WO2008138363A1 WO 2008138363 A1 WO2008138363 A1 WO 2008138363A1 EP 2007004123 W EP2007004123 W EP 2007004123W WO 2008138363 A1 WO2008138363 A1 WO 2008138363A1
Authority
WO
WIPO (PCT)
Prior art keywords
block copolymers
general formula
polyether
copolymers according
additive
Prior art date
Application number
PCT/EP2007/004123
Other languages
German (de)
English (en)
Inventor
Arndt Brückner
Frank König
Holger Leidreiter
Tobias Maurer
Peter Schwab
Original Assignee
Evonik Goldschmidt Gmbh
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Evonik Goldschmidt Gmbh filed Critical Evonik Goldschmidt Gmbh
Priority to PCT/EP2007/004123 priority Critical patent/WO2008138363A1/fr
Publication of WO2008138363A1 publication Critical patent/WO2008138363A1/fr

Links

Classifications

    • 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
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners
    • 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

Definitions

  • Nitrogen-containing polyether-polysiloxane block copolymers processes for their preparation and their use for improving the surface properties of fabrics and fibers
  • the invention relates to nitrogen-containing polyether-polysiloxane block copolymers and to a process for their preparation. It further relates to the use of these polymers as an additive in formulations for the care and cleaning of keratinic fibers, such as hair conditioners, as well as for fabrics, non-wovens and / or fibers of natural and / or synthetic raw materials and textiles such as as a plasticizer.
  • Nitrogen-containing polyether-polysiloxane block copolymers and their use as additives for fabric softening agents are known from the patent literature.
  • WO-A-02/10256 and WO-A-04/042136 describe linear polyamino-polysiloxane copolymers based on silicones and functionalized hydrocarbon radicals in which ⁇ , ⁇ -epoxy-siloxanes react with ⁇ , ⁇ -epoxy-functionalized hydrocarbons Amine units are linked together.
  • the cited documents describe polymers based on tertiary amines (eg N, N, N ', N'-tetramethylhexanediamine) and short-chain epoxy-functionalized hydrocarbons (eg ethylene glycol diglycidyl ether) which contain tetraalkylammonium units in high density.
  • All softener formulations based on polysiloxane polymers of the prior art have in common that even after a single washing of a textile finished with them, the softening property is largely lost. If a textile is treated with such compounds, it will indeed receive a good softness, but the siloxane is easily removable again from the corresponding textile due to its low substantivity, such as by washing operations. However, it is desirable that the siloxane remains on the fabric even after washing and thus the soft touch is not lost.
  • the invention is therefore based on the object to find polyether-polysiloxane polymers which have the desired property profile, in particular a very good hydrophilic soft touch and increased permanence on textiles.
  • a high elasticity of elasticity, reduced tendency to wrinkling and an improved desensitizing tendency, for example during ironing, of a finished product are to be regarded as a further positive characteristic.
  • polyether-polysiloxane block copolymers with tetraalkylammonium units as haircare additives is also known from WO-A-02/10256 and WO-A-04/042136.
  • Human hair is exposed daily to a variety of influences. In addition to mechanical stress caused by brushing, combing, putting up or tying back, the hair is also attacked by environmental influences such as strong UV radiation, cold, wind and water. Also the physiological status (eg age, health) of the respective person influences the condition of the keratin fibers.
  • the treatment with chemical agents changes the structure and surface properties of the hair.
  • Methods such as perming, bleaching, dyeing, tinting, smoothing, etc., but also frequent washing with aggressive surfactants contribute to causing more or less severe damage to the hair structure.
  • perming bleaching, dyeing, tinting, smoothing, etc.
  • aggressive surfactants contribute to causing more or less severe damage to the hair structure.
  • both the cortex and the cuticle of the hair are attacked.
  • the disulfide bridges of cystine are broken up by the reduction step and partially oxidized to cysteic acid in the subsequent oxidation step.
  • Bleaching not only destroys melanin but also oxidizes about 15-25% of the disulfide bonds of cystine with mild bleaching. With an excessive bleaching, it may even be up to 45% (K.F. de Polo, A Short Textbook of Cosmetology, 2000, Verlag für chemische Industrie, H. Ziolkowsky GmbH).
  • the chemical treatments, the frequent washing or the UV irradiation result in adverse mechanical properties for the hair caused by the removal of naturally-eliminated hair follicles or humectants (sebum). It is thus brittle, dry, lackluster, porous and poorly combed.
  • Such commercial hair care products contain mainly alkylammonium-based cationic surfactants, as well as the compounds exemplified in WO-A-02/10256 and WO-A-04/042136, polymers, waxes or oils or silicone oils. The effectiveness of these compounds can be u.a. attributed to a hydrophobization of the hair surface.
  • the compounds should therefore show an improved or at least equally good individual effect, but overall an improved combined effect of mechanical and other properties.
  • linear amino-functional polyether-polysiloxane block copolymers described in greater detail below correspond to the previously defined requirement profiles.
  • the compounds according to the invention also have the advantage that they are free of tetraalkylammonium units, which must be avoided for reasons of toxicity (see, for example, Dr. Peter Hardt, "Environmentally friendly textile softeners"), lecture on the 37th German Dyeing Day in Melliand Textilberichte 9/1990, p 699-706).
  • An object of the invention are therefore linear polyether-polysiloxane block copolymers of the general formula (I)
  • a is 5 to 500, preferably 10 to 60, b is 0 to 50, preferably 0, c is 0 to 60, preferably 10 to 60, and
  • R 1 are identical or different aliphatic or aromatic hydrocarbon radicals having 1 to 8 C atoms
  • P is a divalent polyether unit of the general formula (III)
  • Each R 3 is independently hydrogen or
  • Methyl each independently of one another 0 or 1, e 8 to 40, preferably 10 to 30, particularly preferably 12 to 25,
  • chain ends can be modified as desired.
  • the values a, b and c of the general formula II are to be understood as average values in the molecule, since the polysiloxanes to be used according to the invention are generally present in the form of equilibrated mixtures. It is well known to those skilled in the art that the compounds are due to their polymeric nature in the form of a mixture with a substantially regulated by statistical laws distribution. The values for all indices therefore represent mean values.
  • Another object of this invention is a process for the preparation of the products according to the invention, This is characterized in that
  • a is 5 to 500, preferably 10 to 60
  • b is 0 to 50
  • c is 0 to 60, preferably 10 to 60
  • R 1 are identical or different aliphatic or aromatic hydrocarbon radicals having 1 to 8 C atoms
  • R 2 is CH 2 OCH 2 CH 2 CH 2 ,
  • R 1 is CH 2 OCH 2 CH 2 CH 2 , Each R 3 is independently hydrogen or
  • Methyl each independently of one another is 0 or 1
  • e is from 8 to 40, preferably from 10 to 30, particularly preferably from 12 to 25,
  • Preferred catalysts according to the invention are ZrCl 4 , ZnCl 2 , montmorillonite, LiBr, Cu (BF 4 J 2 .H 2 O, LiClO 4 , Yb (OTf) 3 , BF 3 , carboxylic and mineral acids such as acetic acid, HCl and H 2 SO 4 Particularly preferred according to the invention is LiBr.
  • a further subject of this invention is the use of the compounds of the general formula (I) and the compounds of the general formula (I) or the technical mixtures prepared according to the process according to the invention as softening agents in optionally surfactant-containing aqueous care and cleaning formulations for fabrics, non-wovens and / or fibers of natural and / or synthetic raw materials.
  • Another object of this invention is the use of the compounds of general formula (I) and the compounds of general formula (I) prepared according to the inventive method or the technical mixtures prepared according to this method for the preparation of fabric softeners, detergents and cleaners for fabrics , Non-wovens and / or fibers of natural and / or synthetic raw materials.
  • a further subject of this invention is the use of the compounds of the general formula (I) and of the compounds prepared by the process according to the invention
  • a further subject of this invention is the use of the compounds of the general formula (I) and of the compounds of the general formula (I) prepared according to the process according to the invention or of the technical mixtures prepared according to this process for the production of gloss-improving care formulations for keratinic fibers.
  • a further subject of this invention is the use of the compounds of the general formula (I) and the compounds of the general formula (I) prepared according to the process according to the invention or technical mixtures prepared for the treatment of surfaces, as a coating agent, forrapnhydrophobitation, as a wetting agent for surfaces, as an additive in wetting agents, as a lubricant, as an additive in lubricants, as an additive in drilling fluids, as an impregnating agent, as an additive in impregnating agents, as a corrosion inhibitor, as an additive in anticorrosion agents, as an antifogging agent, as an additive for paints and varnishes, in the manufacture of composites, in the manufacture of compounds, for the coating of particles, fillers and pigments, and for the improvement of the rheological properties of pigments.
  • the amine number indicates the percentage by weight of nitrogen in the sample in percent.
  • Reaction apparatus diluted with 200 g of xylene.
  • 120 0 C 35 g of a Polyethylenglykoldiglycidylethers were added dropwise with an average of 10 EO units and stirred at 125 0 C for a further 19 h. Subsequently, with 400 g
  • Silicone chain length of 30 Si diglycidyl PO polyether
  • Silicone chain length of 30 Si, diglycidyl PO polyether, formulation in Varonic® APM 563 g of the xylene-containing reaction mixture from Example 2 were admixed with 347 g of Varonic® APM (Degussa) and the solvent xylene was distilled off under reduced pressure. A pale yellow colored, viscous product was obtained.
  • Varonic® APM is added and the solvent is distilled off xylene at reduced pressure. A pale yellow colored, viscous product was obtained. Tertiary nitrogen : 0.41%; theor: 0.43%.
  • reaction product was then treated with 1,230 g of Dowanol.RTM. TPM (tripropylene glycol monomethyl ether, Dow Chemical) and the solvent xylene was distilled off under reduced pressure. A pale yellow colored, viscous product was obtained. Tertiary nitrogen : 0.45%; theor. : 0.47%.
  • TPM tripropylene glycol monomethyl ether
  • the comparative product Wetsoft® CTA is a self-dispersing amino-functional silicone fluid with polyether groups from Wacker, which can be used as a hydrophilic softener for fibers and textiles.
  • the comparative product Wetsoft® NE 810 is a self-dispersing polyether-amino-functional silicone fluid from Wacker, which can be used as a hydrophilic softener for fibers and textiles. Table 1 :
  • cotton mesh 160 g / m 2
  • cotton terry 400 g / m 2
  • cotton weave 200 g / m 2
  • cotton weave 200 g / m 2
  • the washes were washed in a Miele Novotronic washing machine commercially available W 918 with colored fabrics without pre-washing at 40 0 C with wfk IECA standard detergent base and 3 kg of cotton ballast fabric. Last was The fabric thus treated was dried for 12 hours at room temperature.
  • the internal test method based on DIN 53924 was used to measure the rise height of water.
  • the finished cotton test fabric is cut into five 25 cm long and 1.5 cm wide strips, marked with a water-soluble pencil and fastened to a support in a tight vertical position but without tension.
  • the holder is then placed in a water basin for five minutes so that 2 cm of the strip dip into the water.
  • Table 3 Soft handle assessment on cotton knit fabric or cotton terry fabric after application by padder in comparison with commercially available hydrophilic Aminosiloxan
  • the formulations were tested in a comparative test on human hair. Hair strands are treated with the formulations described above as follows: The strands of hair are wetted under running, warm water. The excess water is gently squeezed out by hand, then shampooed with a surfactant solution (1 ml / strand of hair (2 g)). After a residence time of 1 min, the hair is rinsed for 1 min. Afterwards the respective formulation is applied as a rinse and gently incorporated into the hair
  • composition of the test formulations is intentionally simple to avoid influencing the test results by (normally present) formulation ingredients.
  • Formulations according to the invention may contain, in addition to the ingredients mentioned and / or instead of the ingredients mentioned, further ingredients. In particular, the combination with other ingredients can lead to a synergistic improvement in the described effects.
  • Such ingredients may be (but are not limited to): surfactants, wetting agents or emulsifiers from the groups of anionic, cationic, zwitterionic, amphoteric or nonionic surfactants such as fatty alcohol sulfates, fatty alcohol ether sulfates, alkyl sulfonates, alkyl benzene sulfonates, alkyl sulfosuccinates, quaternary ammonium salts, alkyl betaines, fatty acid amidoalkyl betaines, derivatives of monomeric or condensed saccharides such as sugar esters, methyl or ethyl glucoside fatty acid esters, alkyl glucosides, ethoxylated fatty alcohols, fatty acid alkanolamides or ethoxylated fatty acid esters, thickeners such as kaolin, bentonite fatty acids, fatty alcohols, starch, polyacrylic acid and its derivatives,
  • the sensory evaluations are based on grades awarded on a scale from - to +++, with - the worst and +++ the best rating.
  • the individual test criteria each receive their own rating.
  • test criteria are: wet combability, dry combability, appearance / gloss.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Silicon Polymers (AREA)

Abstract

L'invention concerne des copolymères séquencés de polyéthers et de polysiloxanes contenant de l'azote ainsi qu'un procédé pour leur préparation. Elle concerne en outre l'utilisation de ces polymères comme additifs dans des formulations de soins et de nettoyage de fibres kératiniques, par exemple comme agents de conditionnement des cheveux, ainsi que pour des tissus, des non-tissés et/ou des fibres en matières premières naturelles et/ou synthétiques et des textiles, par exemple comme assouplissant.
PCT/EP2007/004123 2007-05-10 2007-05-10 Copolymères séquencés de polyéthers et de polysiloxanes contenant de l'azote, procédé pour leur préparation et leur utilisation pour améliorer les propriétés de surface de tissus et de fibres WO2008138363A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/EP2007/004123 WO2008138363A1 (fr) 2007-05-10 2007-05-10 Copolymères séquencés de polyéthers et de polysiloxanes contenant de l'azote, procédé pour leur préparation et leur utilisation pour améliorer les propriétés de surface de tissus et de fibres

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP2007/004123 WO2008138363A1 (fr) 2007-05-10 2007-05-10 Copolymères séquencés de polyéthers et de polysiloxanes contenant de l'azote, procédé pour leur préparation et leur utilisation pour améliorer les propriétés de surface de tissus et de fibres

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WO2008138363A1 true WO2008138363A1 (fr) 2008-11-20

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011094374A1 (fr) * 2010-01-29 2011-08-04 The Procter & Gamble Company Nouveaux copolymères de polydiméthylsiloxane linéaire-polyéther avec des groupes amino et/ou ammonium quaternaire et utilisation de ceux-ci
US8957009B2 (en) 2010-01-29 2015-02-17 Evonik Degussa Gmbh Linear polydimethylsiloxane-polyether copolymers having amino and/or quaternary ammonium groups and use thereof
CN110396397A (zh) * 2019-07-23 2019-11-01 中国石油集团渤海钻探工程有限公司 有机胺盐在钻井领域中的应用
WO2025099268A1 (fr) * 2023-11-10 2025-05-15 Archroma International (Germany) Gmbh Copolymères de silicone-polyéther aléatoires linéaires à liaisons amino tertiaires

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004042136A1 (fr) * 2002-11-04 2004-05-21 Ge Bayer Silicones Gmbh & Co. Kg Copolymeres polysiloxane polyamino et/ou polyammonium ii lineaires
US20060237155A1 (en) * 2003-05-14 2006-10-26 Ge Bayer Silicones Gmbh & Co. Kg Polyorganosiloxane compositions for the treatment of substrates

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004042136A1 (fr) * 2002-11-04 2004-05-21 Ge Bayer Silicones Gmbh & Co. Kg Copolymeres polysiloxane polyamino et/ou polyammonium ii lineaires
US20060237155A1 (en) * 2003-05-14 2006-10-26 Ge Bayer Silicones Gmbh & Co. Kg Polyorganosiloxane compositions for the treatment of substrates

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011094374A1 (fr) * 2010-01-29 2011-08-04 The Procter & Gamble Company Nouveaux copolymères de polydiméthylsiloxane linéaire-polyéther avec des groupes amino et/ou ammonium quaternaire et utilisation de ceux-ci
US8158572B2 (en) 2010-01-29 2012-04-17 The Procter & Gamble Company Linear polydimethylsiloxane-polyether copolymers with amino and/or quaternary ammonium groups and use thereof
JP2013518148A (ja) * 2010-01-29 2013-05-20 ザ プロクター アンド ギャンブル カンパニー アミノ及び／又は四級アンモニウム基を有する新規直鎖ポリジメチルシロキサン−ポリエーテルコポリマー並びにその使用
US8957009B2 (en) 2010-01-29 2015-02-17 Evonik Degussa Gmbh Linear polydimethylsiloxane-polyether copolymers having amino and/or quaternary ammonium groups and use thereof
CN110396397A (zh) * 2019-07-23 2019-11-01 中国石油集团渤海钻探工程有限公司 有机胺盐在钻井领域中的应用
CN110396397B (zh) * 2019-07-23 2021-07-23 中国石油集团渤海钻探工程有限公司 有机胺盐在钻井领域中的应用
WO2025099268A1 (fr) * 2023-11-10 2025-05-15 Archroma International (Germany) Gmbh Copolymères de silicone-polyéther aléatoires linéaires à liaisons amino tertiaires

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