EP3583263A1 - Polyéthylenimine alcoxylée et composition contenant cette dernière - Google Patents

Polyéthylenimine alcoxylée et composition contenant cette dernière

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Publication number
EP3583263A1
EP3583263A1 EP18705363.2A EP18705363A EP3583263A1 EP 3583263 A1 EP3583263 A1 EP 3583263A1 EP 18705363 A EP18705363 A EP 18705363A EP 3583263 A1 EP3583263 A1 EP 3583263A1
Authority
EP
European Patent Office
Prior art keywords
alkylene oxide
textile
oxide segments
range
weight
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.)
Granted
Application number
EP18705363.2A
Other languages
German (de)
English (en)
Other versions
EP3583263B1 (fr
Inventor
Laszlo Szarvas
Si Jun ZHU
Yi Lin
R. K. Prasad NADELLA
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Publication of EP3583263A1 publication Critical patent/EP3583263A1/fr
Application granted granted Critical
Publication of EP3583263B1 publication Critical patent/EP3583263B1/fr
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • 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
    • D06M15/61—Polyamines polyimines
    • 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
    • D06M15/53—Polyethers
    • 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
    • D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups
    • 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
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/02—Natural fibres, other than mineral fibres
    • 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
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/16—Synthetic fibres, other than mineral fibres
    • 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
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/10—Repellency against liquids
    • D06M2200/12—Hydrophobic properties
    • 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
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/50—Modified hand or grip properties; Softening compositions
    • 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
    • D06M23/00—Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
    • D06M23/02—Processes in which the treating agent is releasably affixed or incorporated into a dispensing means

Definitions

  • the present invention relates to an alkoxylated polyethylenimine applicable for textile trea- tment in the textile industry, especially for textile finishing.
  • the present invention relates to an alkoxylated polyethylenimine to be used as an additive in textile treatment compositions, such as a textile softening composition or a water-repellant treatment composition in a textile finishing process.
  • the present invention further relates to a textile softening composition and a water-repellant composition containing the same to be used in textile industry, especially in the textile finishing process.
  • textile treatment agents are applied, which provide desired properties to the fabricated textile.
  • a textile softener is a treating agent for textile to make the textile soft, fluffy and anti-static.
  • a commonly used textile softener e.g. amino modified silicone oil, long carbon chain alcohol, quaternary ammonium compounds, wax, ester, etc., can offer soft hand feeling with economical cost.
  • a water-repellant agent such as fluoro-containing water-repellant agent or silicon- containing water-repellant agent, is a treating agent for textile to provide the textile with water- repellant properties. It can be used for textile-treating, textile-finishing, and the like.
  • the treated textile after being treated by the composition of the present invention, the treated textile will have excellent washing durability, which means that, after several times of washing cycles, the treated textile will keep excellent performances such as soft hand feeling or water repellence.
  • Hydrophilic silicone oils have been developed in recent years. Compared with amino modified silicone oil, hydrophilic silicone oils exhibit an improved hydrophilicity. However, producing several hydrophilic silicone oils is tedious, and the hydrophilic silicone oil will adversely influence the hand of the treated textile.
  • US 201 1/0177994A1 discloses a fabric care composition comprising a polyethylenimine as deposition aid.
  • polyethylenimine is used for improving the deposition of a fabric care active with some examples being silicone or other water-insoluble actives.
  • the treated textile will have excellent washing durability, which means that, after several times of washing cycle, the treated textile will keep excellent performances such as soft hand feeling or water repellence.
  • the first aspect of the invention relates to an alkoxylated polyethylenimine, having alkylene oxide segments attached to the nitrogen atoms of the polyethylenimine,
  • alkylene oxide segments are selected from the group consisting of ethylene oxide segment and C 3 -C 6 -alkylene oxide segments, preferably the alkylene oxide segments are comprised of ethylene oxide segment and C 3 -C 6 -alkylene oxide segments, more preferably the alkylene oxide segments are comprised of ethylene oxide segment and C 3 -C4-alkylene oxide segments, most preferably the alkylene oxide segments are comprised of ethylene oxide segment and C 3 -alkylene oxide segments;
  • alkylene oxide segments is on average in the range of from 1 to 120 alkylene oxide segments per nitrogen atom, for example in the range of from 1 to 100 alkylene oxide segments per nitrogen atom, preferably 1 to 80 alkylene oxide segments per nitrogen atom, more preferably 1 to 70 alkylene oxide segments per nitrogen atom, most preferably 1 to 60 alkylene oxide segments per nitrogen atom, such as 1 to 55 alkylene oxide segments per nitrogen atom, and
  • the weight average molecular weight (M w ) of the alkoxylated polyethylenimine is from 1 ,000 to 1 ,000,000 g/mole, preferably in the range of 5,000 to 500,000, more preferably in the range of 10,000 to 50,000, most preferably in the range of 30,000 to 50,000 g/mol.
  • this first aspect of the invention relates to use of the alkoxylated polyethylenimine in textile treatment processes in textile industry, particularily in the textile finishing processes.
  • the present invention relates to a textile softening composition com- prising:
  • the third aspect of the invention relates to the use of the alkoxylated polyethylenimine of the invention as an additive in a textile softening composition.
  • the fourth aspect of the present invention is a process for treating a textile, comprising a step of contacting the textile softening composition of the present invention with the textile.
  • the fifth aspect of the present invention is a water-repellant composition, which comprising:
  • the sixth aspect of the invention relates to the use of the alkoxylated polyethylenimine of the invention as an additive in a water-repellant composition.
  • the seventh aspect of the present invention is a process for treating a textile, comprising a step of contacting the water-repellant composition of the present invention with the textile.
  • polymer when used to define a term, includes both the plural and singular forms of the term.
  • polymer includes both homopolymers, that is, polymers prepared from a single reactive compound, and copolymers, that is, polymers prepared by reaction of at least two polymer forming reactive, monomeric compounds.
  • the first aspect of the invention relates to an alkoxylated polyethylenimine, having alkylene oxide segments attached to the nitrogen atoms of the polyethylenimine,
  • alkylene oxide segments are selected from the group consisting of ethylene oxide segment and C 3 -C 6 -alkylene oxide segments, preferably the alkylene oxide segments are comprised of ethylene oxide segment and C 3 -C 6 -alkylene oxide segments, more preferably the alkylene oxide segments are comprised of ethylene oxide segment and C 3 -C4-alkylene oxide segments, most preferably the alkylene oxide segments are comprised of ethylene oxide segment and C 3 -alkylene oxide segments;
  • alkylene oxide segments is on average in the range of from 1 to 120 alkylene oxide segments per nitrogen atom, for example in the range of from 1 to 100 alkylene oxide segments per nitrogen atom, preferably 1 to 80 alkylene oxide segments per nitrogen atom, more preferably 1 to 70 alkylene oxide segments per nitrogen atom, most preferably 1 to 60 alkylene oxide segments per nitrogen atom, such as 1 to 55 alkylene oxide segments per nitrogen atom, and
  • the weight average molecular weight (M w ) of the alkoxylated polyethylenimine is from 1 ,000 to 1 ,000,000 g/mole, preferably in the range of 5,000 to 500,000, more preferably in the range of 10,000 to 50,000, most preferably in the range of 30,000 to 50,000 g/mol
  • the average molecular weight Mw may be determined e.g. by gel permeation chromatography (GPC), with 1 .5 % by weight aqueous formic acid as eluent and cross-linked poly- hydroxyethylmethacrylate as stationary phase. Alternatively, the average molecular weight Mw may be calculated based on its structure.
  • GPC gel permeation chromatography
  • polyethylenimine in the context of the present invention does not only refer to polyethylenimine homopolymers but also to polyalkyleneimines containing NH-CH2-CH2-NH structural elements together with other alkylene diamine structural elements, for example NH- CH 2 -CH 2 -CH 2 -NH structural elements, NH-CH 2 -CH(CH 3 )-NH structural elements, NH-(CH 2 ) 4 -NH structural elements, NH-(CH 2 )6-NH structural elements or (NH-(CH 2 )8-NH structural elements but the NH-CH2-CH2-NH structural elements being in the majority with respect to the molar share.
  • polyethylenimines contain NH-CH2-CH2-NH structural elements being in the majority with respect to the molar share, for example amounting to 60 mol-% or more, more preferably amounting to at least 70 mol-%, referring to all alkyleneimine structural elements.
  • polyethylenimine refers to those polyalkylene imines that bear one or zero alkyleneimine structural element per molecule that is different from NH-CH 2 -CH 2 -NH.
  • polyethylenimine in the context of the present invention is branched, preferably highly branched.
  • degree of the branching may be determined by a skilled person according to practical application.
  • the alkylene oxide segments are comprised of ethylene oxide segment and C 3 -C 6 -alkylene oxide segments, more preferably the alkylene oxide segments are comprised of ethylene oxide segment and C 3 -C4-alkylene oxide segments, most preferably the alkylene oxide segments are comprised of ethylene oxide segment and C 3 -alkylene oxide seg- ments.
  • the molar ratio of ethylene oxide segment to the remaining alkylene oxide segment may be in the range of 1 :10 to 6:1 , for example 1 :10 to 5:1 , preferably in the range of 1 :2 to 3:1 , more preferably in the range of 1 :1 to 2:1 . In a most preferred embodiment, the molar ratio of ethylene oxide segment to the remaining alkylene oxide segment is 3:2.
  • the alkylene oxide segments in the al- koxylated polyethylenimine of the present invention are ethylene oxide segments, the amount of the ethylene oxide segments is in the range of from 15 to 25 ethylene oxide segments per nitrogen atom, and the weight average molecular weight of the alkoxylated polyethylenimine of the present invention is in the range of 15,000 to 20,000 g/mol.
  • the alkylene oxide segments in the alkoxylated polyethylenimine of the present invention are comprised of ethylene oxide segment and C 3 -alkylene oxide segments, wherein the amount of alkylene oxide segments is on average in the range of from 35 to 70 alkylene oxide segments per nitrogen atom, preferably the amount of alkylene oxide segments is on average in the range of from 35 to 60 alkylene oxide segments per nitrogen atom, more preferably the amount of alkylene oxide segments is on average in the range of from 35 to 55 alkylene oxide segments per nitrogen atom, and the molar ratio of ethylene oxide segment to the remaining alkylene oxide segment is in the range of 1 :10 to 6:1 , for example 1 :10 to 5:1 , preferably in the range of 1 :2 to 3:1 , more preferably in the range of 1 :1 to 2:1 , such as 3:2, and the weight average molecular weight of the alkoxylated polyethylenimine of the present invention is in the
  • the alkoxylated polyethylenimine of the present invention can be obtained by alkoxylation of polyethylenimine via a process commonly known in the art.
  • the alkoxylated polyethylenimine of the present invention may be obtained by the process described in such as US5445765, the disclosure of which is incorporated by reference.
  • the alkoxylated polyethylenimine of the present invention described herein above, and with its preferred embodiments, is used and applied for textile treatment and in textile treatment compositions.
  • alkoxylated polyethylenimine of the present invention described herein above, and with its preferred embodiments, can be used and applied in textile industry in order to address the needs regarding the balancing of the hydrophilicity and hydrophobicity in textile finishing process.
  • the second aspect of the invention relates to a textile softening composition
  • a textile softening composition comprising:
  • the hydrophobic textile softener suitable for the present invention may be any hydrophobic textile softener.
  • the hydrophobic textile softener may be amino modified silicone oil, wax, ester, long carbon chain alcohol, and quaternary ammonium compounds, etc.
  • the hydrophobic textile softeners comprise amino modified silicone oil, for example, amino modified silicone oils which have nitrogen content in the range of from 0.1 % ⁇ 1 .0% and Viscosity in the range of from 400 cSt ⁇ 20,000 cSt, such as Xiameter® OFX 8209 A, Xiameter® OFX 8417, and Xiameter® OFX 8040 commercially available from DOW CORNING, Michigan, USA; quaternary ammonium compounds; Varisofl® 222 from Evonik Industries, Essen, Germany; wax softener prepared with e.g. Honeywell Polymer Wax from Honeywell International, New Jersey, USA, and the like.
  • amino modified silicone oils which have nitrogen content in the range of from 0.1 % ⁇ 1 .0% and Viscosity in the range of from 400 cSt ⁇ 20,000 cSt, such as Xiameter® OFX 8209 A, Xiameter® OFX 8417, and Xia
  • the amount of component (b) is in the range of from 0.1 to 75 % by weight, based on the total weight of component (a) and component (b), preferably, the amount of component (b) is in the range of from 1 to 50 % by weight, more preferably from 1 to 25% by weight, and most preferably in the range of from 1 to 20% by weight, such as in the range of from 10 to 20% by weight, based on the total weight of component (a) and component (b).
  • the total amount of the component (a) and component (b) in the textile softening composition of the present invention can be determined by a skilled person in the art according to practical application, provided that the obtained the textile softening composition can be effectively used for textile treating.
  • the total amount of the component (a) and component (b) in the textile softening composition of the present invention may correspond to the amount of a textile softener contained in a conventional textile softening composition without component (b).
  • conventional textile compositions comprise from about 20% to about 30% by weight of textile softener.
  • the textile softening composition of the present invention may further contain other additives that are generally used in a textile softening composition.
  • additives include, without limitation, solvent, water, surfactant, and the like.
  • Solvents are useful for fluidizing the textile softening composition of the present invention, and may provide good dispersibility, and in some embodiments, provide a clear or translucent composition.
  • Suitable solvents of the present invention can be water-soluble or water-insoluble.
  • Non-limiting examples of the solvent include ethanol, propanol, isopropanol, n-propanol, n- butanol, t-butanol, propylene glycol, 1 ,3-propanediol, ethylene glycol, diethylene glycol, dipropy- lene glycol, 1 ,2,3-propanetriol, propylene carbonate, phenylethyl alcohol, 2-methyl 1 ,3- propanediol, hexylene glycol, glycerol, butyl Di-glycol sorbitol, polyethylene glycols, 1 ,2- hexanediol, 1 ,2-pentanediol, 1 ,2-but
  • the textile softening composition of the present invention may further contain water.
  • the level of water in the textile softening composition of the present invention may be high, for example, at least about 50%, preferably at least about 60%, and more preferably at least about 70% water.
  • the textile softening composition of the present invention may further contain surfactant.
  • Surfactants are emulsifiers for the softener and may also help disperse the composition in the wash cycle.
  • Appropriate surfactant may include nonionic surfactants, for example C12-C18 alkyl ethoxylates, such as, NEODOL® nonionic surfactants from Shell; cationic surfactants such as alkoxylate quaternary ammonium (AQA) surfactants; zwitterionic surfactants such as betaine, specific examples include alkyl dimethyl betaine and cocodimethyl amidopropyl betaine; ampholyte surfactants, such as aliphatic derivatives of secondary or tertiary amines; and mixtures thereof.
  • Other additives applicable for a textile softening composition may be incorporated into the textile softening composition of the present invention by a skilled person according to practical application.
  • the third aspect of the present invention is the use of the alkoxylated-polyethylenimine of the invention as an additive in a textile softening composition for treating a textile.
  • the fourth aspect of the present invention is a process for treating a textile, comprising a step of contacting the textile softening composition of the present invention with the textile.
  • the step of contacting the textile softening composition of the present invention with the textile is carried out by immersing the textile into the textile softening composition of the present invention.
  • the process of the invention is exhaust process or padding process.
  • the fifth aspect of the present invention is a water-repellant composition, which comprising
  • the water-repellant agent applicable to the water-repellant composition of the present in- vention may be any water-repellant agent used for textile-treating, textile-finishing, and the like.
  • the water-repellant agent may be fluoro-containing water-repellant agent or silicon-containing water-repellant agent.
  • the amount of component (B) is in the range of from 0.01 to 10 % by weight, based on the total weight of component (A) and component (B), preferably, the amount of component (B) is in the range of from 0.1 to 6 % by weight, more preferably from 0.1 to 4% by weight, and most preferably in the range of from 0.1 to 2% by weight, such as 0.1 to 1 % by weight, based on the total weight of component (A) and component (B).
  • the total amount of the component (A) and component (B) in the water-repellant composi- tion of the present invention can be determined by a skilled person in the art according to practical application, provided that the obtained the water-repellant composition can be effectively used for textile treating.
  • the total amount of the component (A) and component (B) in the water-repellant composition of the present invention may correspond to the amount of a fluoro-containing water-repellant agent contained in a conventional water-repellant compositi- on without component (B).
  • the sixth aspect of the invention relates to the use of the alkoxylated polyethylenimine of the invention as an additive in a water-repellant composition.
  • the seventh aspect of the present invention is a process for treating a textile, comprising a step of contacting the water-repellant composition of the present invention with the textile.
  • the step of contacting the water-repellant composition of the present invention with the textile is carried out by immersing the textile into the water-repellant composition of the present invention.
  • the textile suitable for being treated by the compositions of the present invention may be prepared from various natural or synthetic fibers, which could be such as woven, knitted or nonwoven fabric.
  • the textile may be prepared from cotton; polyester such as Polyethylene terephthalate (PET); polyamide, such as polyamide 6 and polyamide 66; PP (polypropylene); and the like.
  • the alkoxylated polyethylenimine of the present invention may be applied on nature fibre, e.g. cotton, and synthetic fibre, e.g. polyester (such as PET, Polyglycolide or polyglycolic acid (PGA), Polylactic acid (PLA), Polycaprolactone (PCL), Polyhydroxyalkanoate (PHA), Polyhydro- xybutyrate (PHB), Polyethylene adipate (PEA), Polybutylene succinate (PBS), Poly(3- hydroxybutyrate-co-3-hydroxyvalerate) (PHBV), Polyethylene terephthalate (PET), Polytrimethy- lene terephthalate (PTT), Polyethylene naphthalate (PEN), and so forth), polyamide, polyethylene (PE), PP (polypropylene), and so on, which could be woven, knitted or nonwoven fabric, together with other finishing auxiliary (e.g. softener or water repellent) or alone.
  • polyester such as PET, Polyglycolide or poly
  • the alkoxylated polyethylenimine of the present invention may be applied to a PE/PP or a PE/Polyester (e.g. PE/PET) bi-component nonwoven fabric, which is made from continuous filament fibers and is non-linting or very low in linting, and which comprises a sheath, that is polyethylene (PE) and a core, that is polypropylene (PP) or a polyester (e.g.
  • PE/PP PE/Polyester
  • PE/PET PE/PET bi-component nonwoven fabric, which is made from continuous filament fibers and is non-linting or very low in linting, and which comprises a sheath, that is polyethylene (PE) and a core, that is polypropylene (PP) or a polyester (e.g.
  • Po- lyethylene terephthalate PET
  • Polyglycolide or polyglycolic acid PGA
  • Polylactic acid PLA
  • Polycaprolactone PCL
  • Polyhydroxyalkanoate PHA
  • Polyhydroxybutyrate PBS
  • Polybutylene succinate PBS
  • PBS Poly(3-hydroxybutyrate-co-3-hydroxyvalerate)
  • PTT Polytrimethylene terephthalate
  • PEN Polyethylene naphthalate
  • the core part provides strength and polyethylene sheath part provides softness and low melting point.
  • the alkoxylated polyethylenimine of the present invention may be applied in textile industry also for producing textiles for specific purposes, e.g. including but not limited to for medical or hygienic use (e.g. gauze, wound dressings, bandages, diapers, sanitary napkins and so forth), and membrane industry, with the function of improving hydrophilicity of substrates.
  • textile industry also for producing textiles for specific purposes, e.g. including but not limited to for medical or hygienic use (e.g. gauze, wound dressings, bandages, diapers, sanitary napkins and so forth), and membrane industry, with the function of improving hydrophilicity of substrates.
  • an absorbent core which is optio- nally made from cellulose fibers, like a matrix of fluff material made from wood pulp, which may also optionally additionally include wheat/corn based materials.
  • the liquids are absorbed by the capillaries in the void spaces between the fibers and the surface tension angle between the fibers and the water.
  • An alternative to pulp is to use air laid synthetic fibers.
  • cellulose acetate e.g. used to make cigarette filters, has been used in some absorbent products, as well as PP synthetic fiber has also been attempted for absorbent core formation.
  • the absorbent core may further comprise chemical crystals of absorbent polymers such as hydro- gel, sodium polyacrylate, polyacrylate absorbents, which may hold the liquids under pressure.
  • the present invention relates to the embodiments as follows.
  • Embodiment 1 An alkoxylated polyethylenimine, having alkylene oxide segments attached to the nitrogen atoms of the polyethylenimine,
  • alkylene oxide segments are selected from the group consisting of ethylene oxide segment and C 3 -C 6 -alkylene oxide segments, preferably the alkylene oxide segments are comprised of ethylene oxide segment and C 3 -C 6 -alkylene oxide segments, more preferably the alkylene oxide segments are comprised of ethylene oxide segment and C 3 -C4-alkylene oxide segments, most preferably the alkylene oxide segments are comprised of ethylene oxide segment and C 3 -alkylene oxide segments;
  • alkylene oxide segments is on average in the range of from 1 to 120 alkylene oxide segments per nitrogen atom, for example in the range of from 1 to 100 alkylene oxide segments per nitrogen atom, preferably 1 to 80 alkylene oxide segments per nitrogen atom, more preferably 1 to 70 alkylene oxide segments per nitrogen atom, most preferably 1 to 60 alkylene oxide segments per nitrogen atom, such as 1 to 55 alkylene oxide segments per nitrogen atom, and
  • the weight average molecular weight (M w ) of the alkoxylated polyethylenimine is from 1 ,000 to 1 ,000,000 g/mole, preferably in the range of 5,000 to 500,000, more preferably in the range of 10,000 to 50,000, most preferably in the range of 30,000 to 50,000 g/mol, for use in a textile treatment process, especially in a textile finishing process.
  • Embodiment 2 The alkoxylated polyethylenimine of embodiment 1 , wherein the alkylene oxide segments are consisting of ethylene oxide segment and C 3 -C 6 -alkylene oxide segments, more preferably the alkylene oxide segments are comprised of ethylene oxide segment and C 3 - C4-alkylene oxide segments, most preferably the alkylene oxide segments are comprised of ethylene oxide segment and C 3 -alkylene oxide segments.
  • Embodiment 3 The alkoxylated polyethylenimine of embodiment 2, wherein the molar ratio of ethylene oxide segment to the remaining alkylene oxide segment is in the range of 1 :10 to 6:1 , for example 1 :10 to 5:1 , preferably in the range of 1 :2 to 3:1 , more preferably in the range of 1 :1 to 2:1 , such as 3:2.
  • Embodiment 4 The alkoxylated polyethylenimine of embodiment 1 , wherein the alkylene oxide segments in the alkoxylated polyethylenimine are ethylene oxide segments, the amount of the ethylene oxide segments is in the range of from 15 to 25 ethylene oxide segments per nitrogen atom, and the weight average molecular weight of the alkoxylated polyethylenimine is in the range of 15,000 to 20,000 g/mol.
  • Embodiment 5 The alkoxylated polyethylenimine of embodiment 2 or 3, wherein the alkylene oxide segments are comprised of ethylene oxide segment and C 3 -alkylene oxide segments, and the amount of alkylene oxide segments is on average in the range of from 35 to 70 alkylene oxide segments per nitrogen atom, preferably the amount of alkylene oxide segments is on average in the range of from 35 to 60 alkylene oxide segments per nitrogen atom, more preferably the amount of alkylene oxide segments is on average in the range of from 35 to 55 alkylene oxide segments per nitrogen atom, and the weight average molecular weight of the alkoxylated polyethylenimine of the present invention is in the range of from 35,000 to 40,000 g/mol.
  • Embodiment 6 The alkoxylated polyethylenimine of embodiment 1 , wherein the alkylene oxide segments in the alkoxylated polyethylenimine are C 3 -C 6 -alkylene oxide segments.
  • Embodiment 7 The alkoxylated polyethylenimine of embodiment 1 or 2, wherein the C 3 -Ce- alkylene oxide segments in the alkoxylated polyethylenimine are C 3 -C4-alkylene oxide segments.
  • Embodiment 8 The alkoxylated polyethylenimine of embodiment 1 or 2, wherein the C 3 -Ce- alkylene oxide segments in the alkoxylated polyethylenimine are C 3 -alkylene oxide segments.
  • Embodiment 9 A textile softening composition comprising:
  • Embodiment 10 The textile softening composition of embodiment 9, wherein the hydrophobic textile softener is selected from the group consisting of amino modified silicone oil, wax, ester, long carbon chain alcohol, and quaternary ammonium compounds.
  • Embodiment 1 1 The textile softening composition of embodiment 9 or 10, wherein the amount of component (b) is in the range of from 0.1 to 75 % by weight, based on the total weight of component (a) and component (b), preferably, the amount of component (b) is in the range of from 1 to 50 % by weight, more preferably from 1 to 25% by weight, and most preferably in the range of from 1 to 20% by weight, such as in the range of from 10 to 20% by weight,, based on the total weight of component (a) and component (b).
  • Embodiment 12 The textile softening composition of any one of embodiments 9-1 1 , wherein the textile softening composition further comprises additives such as solvent, surfactant, and the like.
  • Embodiment 13 The textile softening composition of any one of embodiments 9-1 1 , wherein the textile to be treated is prepared from natural or synthetic fibers, for example, cotton; polyester such as Polyethylene terephthalate (PET); polyamide, such as polyamide 6 and poly- amide 66; polypropylene and the like, preferably the textile is woven, knitted or nonwoven fabric.
  • natural or synthetic fibers for example, cotton
  • polyester such as Polyethylene terephthalate (PET)
  • PET Polyamide
  • polyamide 6 and poly- amide 66 polypropylene and the like, preferably the textile is woven, knitted or nonwoven fabric.
  • Embodiment 14 A process for treating a textile, comprising a step of
  • the step of contacting the textile softening composition of any one of embodiments 9-13 with the textile is carried out by immersing the textile into the textile softening composition of any one of embodiments 9-13.
  • Embodiment 15 The process of embodiment 14, which is selected from exhaust process or padding process.
  • Embodiment 16 A water-repellant composition, which comprising
  • Embodiment 17 The water-repellant composition of embodiment 16, wherein the water- repellant agent is fluoro-containing water-repellant agent or silicon-containing water-repellant agent.
  • Embodiment 18 The water-repellant composition of embodiment 16 or 17, wherein the amount of component (B) is in the range of from 0.01 to 10 % by weight, based on the total weight of component (A) and component (B), preferably, the amount of component (B) is in the range of from 0.1 to 6 % by weight, more preferably from 0.1 to 4% by weight, and most preferably in the range of from 0.1 to 2% by weight, such as 0.1 to 1 % by weight, based on the total weight of component (A) and component (B)..
  • Embodiment 19 The use of the alkoxylated polyethylenimine as defined in any one of embodiments 1 -8 as an additive in a textile softening composition for treating a textile.
  • Embodiment 20 The use of the alkoxylated polyethylenimine as defined in any one of embodiments 1 -8 as as an additive in a water-repellant composition for treating a textile.
  • Embodiment 21 A process for treating a textile, comprising a step of contacting the water- repellant composition of any one of embodiments 16-18 with the textile, preferably, the step of contacting the water-repellant composition of any one of embodiments 16-18 with the textile is carried out by immersing the textile into the water-repellant composition of any one of embodiments 16-18.
  • Embodiment 22 The process of embodiment 14, 15 or 21 , wherein the textile is prepared from natural or synthetic fibers, for example, cotton; polyester such as Polyethylene terephthalate (PET); polyamide, such as polyamide 6 and polyamide 66; polypropylene and the like, prefe- rably the textile is woven, knitted or nonwoven fabric.
  • polyester such as Polyethylene terephthalate (PET)
  • PET Polyethylene terephthalate
  • polyamide such as polyamide 6 and polyamide 66
  • polypropylene and the like prefe- rably the textile is woven, knitted or nonwoven fabric.
  • the alkoxylated polyethylenimine of the present invention will improve excellent properties of the treated textile, such as hydrophilicity, hand feeling, antistatic/anti-dust properties, and the like.
  • the present invention provides a stable textile softening composition.
  • the textile softening composition improves excellent hydrophilicity of the treated textile, while the soft hand feeling of the textile is kept.
  • the treated textile will have excellent washing durability, which means that after several washing cycles the treated textile will keep excellent performances such as soft hand feeling or water repellence.
  • the present invention provides an excellent water-repellant composition.
  • the excellent water-repellant composition of the present invention improves antistatic/anti-dust properties of the treated textile at economical cost.
  • the treated textile after being treated by the water- repellant composition of the present invention, the treated textile will have excellent washing durability, which means that, after several washing cycles the treated textile will keep excellent performances such as soft hand feeling or water repellence.
  • wicking height was measured according to GB/T 21665, 1 -2008;
  • blade means the fabric is tested as such without treatment.
  • the improving degree of the alkoxylated polyethylenimines according to the present invention shown the different examples for absorbency, hand feeling (softness), and whiteness index (CIE units) of the treated fabrics, were summarized and generalized accordingly in respective tables, wherein “+” means improving degree, “++” means higher improving degree as comparing with "+” and “-” means somewhat decreased, and whereas similar or no effects were named as such or not specified at all.
  • the fabrics are treated in an exhaust process and in a padding process, which are common chemical finishing treatments in textile industry.
  • Padding is one of the most common finishing technique, which can be applied to carry out almost all wet finishing operations.
  • the dosage of softener is calulated by weight of working solution, not by weight of fabric.
  • the concentration of the applied working solution is provided in g of softener composition diluted per liter of water.
  • the treatment of fabrics in exhaustion liquor is another possible finishing method, and is recommended when stable chemical products are applied on the textile substrate.
  • concentration of the applied softener is provided in percentage, % "owf" (or o.w.f.) meaning based on the weight of fabric, which has to be further diluted accordingly for the working solution.
  • alkoxylated PEI- the alkylene oxide segments in the alkoxylated PEI-A are ethyleA ne oxide segments, the amount of the ethylene oxide segments
  • alkoxylated PEI-A is in the range of from 15 to 25 ethylene oxide segments per nitrogen atom, and the weight average molecular weight of alkoxylated PEI-A is in the range of 15,000 to 20,000 g/mol.
  • alkoxylated PEI- the alkylene oxide segments in alkoxylated PEI-B are comprised
  • alkylene oxide segments are on average in the range of from 35 to 55 alkylene oxide segments per nitrogen atom, and the molar ratio of ethylene oxide segment to the
  • alkylene oxide segment is 3:2, and the weight average molecular weight of alkoxylated PEI-B is in the range of from
  • compositions comprising Amino Modified Silicone oils (AMS) and alkoxylated PEI
  • AMS amino modified silicone oils
  • emulsifiers used therein are listed in table 1 .
  • Emulsifier A C10+8EO, C10-Guerbet alcohol alkoxylate;
  • Emulsifier B C10+7EO, C10-Guerbet alcohol alkoxylate.
  • the alkoxylated PEI used in example 1 was Alkoxylated PEI-A.
  • BDG Butyl Di-glycol
  • the fabrics used in the test were cotton knits and cotton woven.
  • compositions comprising hydrophobic textile softener and alkoxylated PEI
  • compositions comprising Cationic softener and alkoxylated PEI
  • alkoxylated PEI-A was used as alkoxylated PEI together with a cati- onic softener.
  • Emulsifier C C16-C18 fatty alcohol alkoxylate, (25EO).
  • composition 2-1 -A contained Cationic softener without the addition of the alkoxylated PEI present invention
  • Composition 2-1 -B contained the Cationic softener wherein 10% by weight of the Cationic softener was replaced by Alkoxylated PEI-A
  • Composition 2-1 -C contained Cationic softener wherein 20% by weight of the Cationic softener was replaced by Alkoxylated PEI-A.
  • the obtained three compositions were used for treating fabrics in Exhaust process and Padding process.
  • Softener To be applied in 20 gpl (and comprising 3 gpl active components); (Compositions calculated based on softener / working solution
  • compositions comprising wax softener and alkoxylated PEI
  • Wax Emulsion was used as wax softener.
  • Wax Emulsion The parameters of Wax Emulsion are provided as follows:
  • Equipment Dyeing controller DC4 F/R SP H.T.H.P beaker dyeing machine
  • Liquor ratio 1 :10 (fabric: working solution, by weight)
  • the process parameters of the Padding process were provided as follows.
  • Composition 2-2-C > Composition 2-2-B > Composition 2-2-A.
  • compositions comprising Alkoxylated PEI-A and hydrophilic silicone oils
  • Table 13 provided the test results measured without washing (0), after one time washing (1 ), after two times washing (2), after three times washing (3), after four times washing (4), and after five times washing (5).
  • compositions comprised the hydrophilic silicone oil (HSO) TF405B and amino silicone oil (ASO) 2253D as softeners in water as solvent.
  • HSO hydrophilic silicone oil
  • ASO amino silicone oil
  • Blank 3-1 -G - 1 10.6 18.7
  • compositions comprising Alkoxylated PEI-A and Alkoxylated PEI-B
  • compositions were prepared as textile softening compositions, wherein amino modified silicone oil type softener Xiameter® OFX 8040 (AMS) was used.
  • AMS amino modified silicone oil type softener Xiameter® OFX 8040
  • Cotton Terry Towel was used as fabric to be treated in this test. Each of the compositions was used and applied in dosage of 2% owf (of weight fabric).
  • the fabric liquid (work solution) ratio was 1 :10, and the pH values of the compositions were in the range of from 5.0 to 6.0.
  • the process was carried at 40°C for 20 min.
  • PET fabric was used as fabric to be treated in this test.
  • Each of the compositions was used in dosage of 20g/L.
  • the pH values of the compositions were in the range of 5.0 to 6.0.
  • Blank PET fabric was relative hydrophobic as compared with cotton, and the hand feeling thereof was also poor (sample Blank); when being treated with amino modified silicon oil softener, hand feeling of the treated PET fabric was increased, and the hydrophilicity was then obviously decreased (fabric treated with composition 4-1 -1 );; when 20% amino modified silicone oil softener was replaced by Alkoxylated PEI-A or Alkoxylated PEI-B, the hydrophilicity of the treated fabric was obviously improved as compared with the PET fabric treated with composition 4-1 -1 .
  • compositions were prepared as shown in table 20 to test the properties of the fabrics treated by the compositions containing Alkoxylated PEI-A, hydrophilic silicone oil and /or Alkoxylated PEI-B in Padding Process.
  • compositions comprising Alkoxylated PEI-A, Alkoxylated PEI-B and/or quaternary ammonium compound
  • the quaternary ammonium compound used in example 5 was Varisoft® 222 having the Chemical structure of:
  • compositions were prepared wherein the softeners contained therein were described in table 21 .
  • Blank cotton fabric was very hydrophilic with poor hand feeling; with Cotton Fabric treated with Composition 5-1 , hand feeling got obviously improved, wicking height however was decreased a lot, as compared with the blank sample;
  • composition 5-2 with 10% Alkoxylated PEI-A and Composition 5-3 with 10% Alkoxylated PEI-B improved the hydrophilicity of the treated fabric without influencing hand feeling, as compared with Cotton Fabric treated with Composition 5-1 .
  • Composition 5-5 with 20% Alkoxylated PEI-B improved the hydrophilicity of the treated PET Fabric (hydrophobic) without influencing hand feeling, as compared with the blank sample.
  • Blank PET fabric had poor hand feeling
  • PET Fabric residual hydrophilic
  • Composition 5-1 With PET Fabric (relative hydrophilic) treated with Composition 5-1 , hand feeling got obviously improved, wicking height was also raised, as compared with the blank sample;
  • the three samples were provided in table 28.
  • the non-woven fabric used for preparing the three samples was obtained from the same batch.
  • the test was carried out on a sample as provided above on a liquid absorbing substrate (made from a disposable diaper) at room temperature.
  • the disposable diaper used in the example 6 had layers sequentially as follows: - a top sheet nonwoven layer;
  • a acquisition distribution layer (a PE/PET bi-component nonwoven layer, with sheath being PE, and core being PET);
  • the disposable diaper was used as such and not treated.
  • the acquisition distribution layer of the diaper was substituted by one of the above samples, thereby forming a liquid absorbing device.
  • 150 ml colored normal saline was poured on the liquid absorbing device through a PVC sleeve (ha- ving an inner diameter of 6cm and an outer diameter of 7cm) with one end contacting directly to the top sheet layer of the liquid absorbing device.
  • Time recording started once the colored normal saline reached to the top sheet layer of the liquid absorbing device, and ended once the liquid level of the colored normal saline was disappeared in the PVC sleeve. The obtained time was reported as "Acquisition time" in table 29.
  • the longest diffusion distance of the colored normal saline on the top sheet layer of the liquid absorbing device and the shortest diffusion distance of the colored normal saline on the top sheet layer of the liquid absorbing device were measured and reported on the table 29.
  • the diffusion on the absorbent pad layer of the liquid absorbing device was further studied.
  • the longest diffusion distance of the colored normal saline on the absorbent pad layer of the liquid absorbing device and the shortest diffusion distance of the colored normal saline on the absorbent pad layer of the liquid absorbing device were further measured and reported on the table 29.
  • rewetting property was tested.
  • a piece of dry filter paper was provided and weighted. The weight of the dry filter paper was re- ported as the initial weight. Then the dry filter paper was put on top of the top sheet layer of the wetted liquid absorbing device obtained according to the experimental procedure of section 6.1 , and a 3.6kg weight was placed on the filter paper for 2 minutes. Then the weight was taken away, and the weight of the wetted filter paper was measured as the wetted weight.
  • the rewetting property was characterized according to the wetted weight of the filter paper minus the initial weight of the filter paper, which was reported as "rewet" in table 29.
  • Rewet the wetted weight of the filter paper - the initial weight of the filter paper. The test was carried out for each of the three samples provided in table 28. The dry filter paper used for testing each sample was of the same condition.
  • test was carried out at room temperature and controlled humidity.
  • a sample in table 28 was put on top of the center of a tissue paper, wherein the tissue paper was balanced in terms of weight and moisture beforehand.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

La présente invention concerne une polyéthylenimine alcoxylée, destinée à être utilisée dans un traitement de textiles dans l'industrie textile, en particulier dans des procédés d'apprêtage de textiles.
EP18705363.2A 2017-02-14 2018-02-09 Polyéthylenimine alcoxylée et composition contenant cette dernière Active EP3583263B1 (fr)

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CN113166406B (zh) * 2018-11-19 2023-11-07 巴斯夫欧洲公司 制备功能性纤维的方法
US20220411994A1 (en) * 2021-06-29 2022-12-29 Microban Products Company Composition and method for odor reduction and bacterial control on a textile
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DE2519530C3 (de) * 1975-05-02 1979-08-30 Chemische Fabrik Pfersee Gmbh, 8900 Augsburg Verfahren zum wasch- und chemischreinigungsbeständigen Weichmachen und Hydrophobieren von Textilmaterialien
DE3167297D1 (en) * 1980-01-07 1985-01-03 Procter & Gamble Fabric softening composition
WO1999016802A1 (fr) * 1997-10-01 1999-04-08 The Procter & Gamble Company Composes copolymeres comprenant une ou plusieurs unites monomeres d'aldehyde actif
WO2008051221A2 (fr) * 2006-10-23 2008-05-02 Nano-Structured Consumer Products, Llc Compositions et procédés pour conférer l'oléophobie et/ou l'hydrophobie
EP2132290A1 (fr) 2007-04-02 2009-12-16 The Procter and Gamble Company Composition pour le soin des tissus
ES2584929T3 (es) * 2007-11-09 2016-09-30 The Procter & Gamble Company Composiciones limpiadoras que comprenden un sistema multi-polimérico que comprende al menos un polímero limpiador de grasa alcoxilado
CL2008003335A1 (es) * 2007-11-09 2010-02-12 Basf Se Polialquileniminas alcoxiladas anfifilicas solubles en agua que tienen un bloque de oxido de polietileno interno y un bloque de oxido de polipropileno externo.
CA2807336A1 (fr) * 2010-08-05 2012-02-09 Biofilm Ip, Llc Composes de polysiloxane substitues par du cyclosiloxane, compositions contenant lesdits composes et leurs procedes d'utilisation
CN107208361B (zh) * 2015-02-06 2021-07-09 巴斯夫欧洲公司 烷氧基化聚乙烯亚胺亲水改性纤维
JP6840085B2 (ja) * 2015-02-25 2021-03-10 ビーエイエスエフ・ソシエタス・エウロパエアＢａｓｆ Ｓｅ 汚れた金属表面を洗浄する方法及びそのような方法に有用な物質

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US20190352843A1 (en) 2019-11-21
BR112019014940A2 (pt) 2020-03-31

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