EP0553217B1 - Softening agents - Google Patents
Softening agents Download PDFInfo
- Publication number
- EP0553217B1 EP0553217B1 EP91919216A EP91919216A EP0553217B1 EP 0553217 B1 EP0553217 B1 EP 0553217B1 EP 91919216 A EP91919216 A EP 91919216A EP 91919216 A EP91919216 A EP 91919216A EP 0553217 B1 EP0553217 B1 EP 0553217B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- group
- reaction
- alkyl
- fibres
- residue
- 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.)
- Expired - Lifetime
Links
- 239000004902 Softening Agent Substances 0.000 title claims description 23
- 229920000742 Cotton Polymers 0.000 claims abstract description 20
- 229920000642 polymer Polymers 0.000 claims abstract description 13
- 239000004677 Nylon Substances 0.000 claims abstract description 9
- 229920001778 nylon Polymers 0.000 claims abstract description 9
- 229920002994 synthetic fiber Polymers 0.000 claims abstract description 9
- -1 wool Polymers 0.000 claims abstract description 5
- 210000002268 wool Anatomy 0.000 claims abstract description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000010923 batch production Methods 0.000 claims abstract description 3
- 238000010924 continuous production Methods 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000000835 fiber Substances 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 6
- 229920001296 polysiloxane Chemical group 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- 150000001266 acyl halides Chemical class 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 230000001588 bifunctional effect Effects 0.000 claims description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 4
- 239000004202 carbamide Substances 0.000 claims description 4
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 229920000233 poly(alkylene oxides) Chemical group 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- 239000011347 resin Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 239000003125 aqueous solvent Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004947 alkyl aryl amino group Chemical group 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 2
- 229920000570 polyether Polymers 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims description 2
- 150000003077 polyols Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 239000004744 fabric Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000005406 washing Methods 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000004383 yellowing Methods 0.000 description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 150000002193 fatty amides Chemical class 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920000909 polytetrahydrofuran Polymers 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 229950011008 tetrachloroethylene Drugs 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- 101100172879 Caenorhabditis elegans sec-5 gene Proteins 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Chemical group 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 210000003423 ankle Anatomy 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000002979 fabric softener Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000009950 felting Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000006081 fluorescent whitening agent Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229920001477 hydrophilic polymer Polymers 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000009981 jet dyeing Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- PMRYVIKBURPHAH-UHFFFAOYSA-N methimazole Chemical compound CN1C=CNC1=S PMRYVIKBURPHAH-UHFFFAOYSA-N 0.000 description 1
- 238000009974 package dyeing Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920006186 water-soluble synthetic resin Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
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
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/385—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen containing epoxy 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
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/372—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen containing etherified or esterified hydroxy groups ; Polyethers of low molecular weight
-
- 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
- D06M15/61—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
- 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
- D06M2101/04—Vegetal fibres
- D06M2101/06—Vegetal fibres cellulosic
-
- 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
- D06M2101/10—Animal fibres
- D06M2101/12—Keratin fibres or silk
-
- 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
- D06M2101/18—Synthetic fibres consisting of macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M2101/26—Polymers or copolymers of unsaturated carboxylic acids or derivatives thereof
-
- 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
- D06M2101/30—Synthetic polymers consisting of macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M2101/34—Polyamides
-
- 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
Definitions
- This invention relates to the novel use of known polymers and prepolymers as softening agents to improve the handle of both natural and synthetic fibres other than wool fibres.
- British Patent Nos. 1470243 and 1533343 describe compounds containing aziridine radicals and their use for reducing the shrinkage and felting of protein fibres.
- One of the compounds disclosed is that sold under the trade name Basolan SW, and which is marketed as a hydrophilic polymer that is said to achieve a soft hydrophilic finish when applied to synthetic fibres.
- DE-A-1419042 discloses the preparation of hardenable water-soluble synthetic resins which are useful in providing anti-static coatings during the finishing of various materials, including wool fibres and other textiles. Other uses mentioned include as delustring agents and as agents for improving the affinity of fibres for anionic dyestuffs.
- FR-A-1165287 relates to addition products of aliphatic polyamines with polyalkoxy compounds, and which are said to impart durable anti-static finishes and improved dyeing properties to textile materials.
- the present invention seeks to provide improved softening agents suitable for use with both natural and synthetic fibres.
- the polymers and prepolymers employed for this purpose are the subject of our co-pending EP-A-0414377.
- the present invention relates to the use as a softening agent or natural or synthetic fibres other than wool of a polymer or prepolymer having one of the following structural formulae:-
- fibre reactive grouping as used herein is to be understood as meaning a group having residual chemical reactivity such that it will be capable of causing a molecule to be bound to the surface of a fibre in such a way as not to be readily removable therefrom.
- examples include the fibre reactive dyes in which a variety of reactive halogen groupings are sited on the molecule and which, during dyeing, react with hydroxy or amino functionalities on the fibre surface to produce a chemical bond. It will be understood that electrical bonding forces, rather than chemical forces, could be involved and that a "reaction” as such need not occur.
- the terminology further includes species which will be attracted to a fibre surface and bind themselves thereto by means of cross-linking mechanisms.
- polyfunctional reactive group as used herein is to be understood as meaning a group which is capable of reacting with the amino functionality of compounds of formula I or II.
- the reactivity of group B needs to be complimentary to that of group R 1 in those compounds.
- the polymers and prepolymers may be derived from mixtures of one or more polyoxyalkyleneamines and that these may be joined by bridging groups.
- the bridging groups serve to link the polyoxyalkyleneamines and some examples of suitable groups were mentioned above.
- the bridging groups themselves could, of course, bear reactive species capable of reacting with fibres.
- the bridging group B could be incorporated into the molecular structure, whilst the prepolymer is being applied to the fibre, as a separate reactive crosslinking agent.
- the softening agents and method of this invention may be applied to all types of natural and synthetic fibres, including nylon and acrylic. They are particularly suited to use with cotton, including 100% cotton terry loop towelling, and to cotton blends with synthetic fibres.
- the softening agents of the invention may be presented for use in solution in a non aqueous solvent, such as perchloroethylene. More preferably, however, they are in the form of an aqueous solution, optionally with the addition of suitable dispersing agents to reduce the viscosity of the solution.
- a non aqueous solvent such as perchloroethylene. More preferably, however, they are in the form of an aqueous solution, optionally with the addition of suitable dispersing agents to reduce the viscosity of the solution.
- the total amount of polymer solids applied to the fibres is generally from 0.005 to 10.0% by weight, most preferably from 0.05 to 2.0%.
- the method of this invention can be performed as either a batch or continuous process using conventional equipment.
- the softening agent may be applied aqueously by exhaustion on to the goods in a traditional long bath method using suitable machinery, or may be padded onto fabric continuously or applied in foam or by suction-slot techniques.
- the agent may be applied to piece goods or fabric from a solvent such as perchloroethylene in suitable machinery.
- the softening agents may be applied in combination with other resins, further softening agents, emulsifiers, pigments, binders fluorescent whitening agents or other materials to confer additional properties or benefits to the material.
- a further advantage of the softening agents of this invention arises from their extreme water dispersibility.
- Conventionally employed softening agents are emulsions which create problems of shear instability in such high shear situations as jet dyeing machines, suction slot evacuators, and filtration problems when treating yarn in package dyeing machines, when filtration effects can cause difficulties. These problems are reduced, or totally avoided, with the present softening agents.
- a still further surprising aspect of the invention is that these softening agents, when used in combination with one or more conventional softening agents, can result in finishes with considerably superior handle and performance than may be expected. Wash durability, handle and fuming during fabric heat setting, for example, are much improved. In some cases the improvement may be up to or above the levels achieved with either material alone, indicating a synergistic action.
- suitable "conventional" fabric softening agents include: oxidised polyethylene wax emulsions; silicone emulsions, especially emulsions of reactive organofunctional silicones, and more especially amonosilicones; fatty amide emulsions; and quaternised fatty amine emulsions.
- a solution was prepared containing 881 g of a bisaminopropyl polytetrahydrofuran of structure (where a is approximately 28 average) in 2418 g of a mixture of 70% isopropanol in water.
- To this solution was added 155.3g of epichlorohydrin with efficient stirring at room temperature in a reaction flask fitted with a water cooled reflux condenser. The mixture was then heated to boiling and reflux maintained for approximately 4 hours or until a clear or slightly turbid homogeneous solution is produced when 5 cm 3 of the reaction mix is mixed with 30 cm 3 water. The reaction mixture was then allowed to cool and used in subsequent experiments.
- the product of Example 1 can be prepared as an aqueous solution by distilling out the isopropanol and replacing it with water, thereby minimising fire hazard. 797 parts of the product of Example 1 is distilled at atmospheric pressure until 391 parts of an isopropanol: water distillate is collected. Then, 710 parts of water and 80 parts monoethylene glycol is added to the flask and stirred. The resulting product contains about 20% w/w active solids and only 4-5% isopropanol.
- the product was applied to acrylic socks by an exhaustion method as in Example 2. Excellent handle and good durability was achieved.
- the softening agent can be mixed with conventional fatty quaternary ammonium-type softeners to give a product which has excellent handle, good durability and superior hydrophilicity to conventional softeners. Such a product is particularly useful for softening cotton/nylon socks.
- Example 4 and Examples 7a and 7b were applied to a variety of knitted cotton fabrics (double jersey, single jersey, loopback interlock and pique).
- the softeners were applied by a) padding: the softeners were applied wet-on-wet to the fabrics from a solution containing 25g/l product, PH7, 25°C at 100% pick-up and b) exhaustion: as given in Example 2 using 2.5% o,w,g. product.
- the fabrics were stenter dried and commercially finished then compared for handle and durability to washing against a standard fatty amide softener.
- a co-applied mixture of the product of Example 4 and a polyethylene wax emulsion (Bradsyn G, Hickson & Welch Ltd) was also evaluated.
- the relative handle and durability assessments were as follows.
- the handle before and after wash was superior when softeners were applied by a padding technique compared in exhaustion.
- the softeners were comparable in softness to the standard silicone softener (Edunine SE, ICI Colours & Fine Chemicals); after wash, (3 x HLCC4), the standard softener could be readily distinguished by its harsher handle.
- the Example 4/polyethylene wax mixture performed particularly well on all fabric types, giving a cool, soft handle and excellent drape.
- the softening agents of the invention are particularly suited to use on towels and towelling fabric as a consequence of their superior hydrophilicity.
- the products were applied by a wet-on-wet continuous pad treatment at 80% pick-up, from solutions containing 20-40g/l softener to Egyptian combed cotton towelling. The fabrics were tumble tried and finished as towels.
- a warm, soft handle is achieved with excellent rewettability, as compared with silicone- and fatty amide-type softeners.
- the new softeners impart a fuller, more luxurious feel to towelling and a silkier handle.
- the durability of the softeners was assessed by subjecting the towels to seven domestic washes, without additional fabric conditioner and line dried. The towels treated with the new softeners retain their original appearance, with a full, soft handle.
- Example 4 The product of Example 4 was compared for yellowing at high temperatures against standard silicone- and fatty amide-type softeners.
- the products were applied to 50/50 polyester/cotton by padding from solutions containing 1 g/l wetting agent (Fullwet PPT Ltd) and 10-40 g/l softener.
- the fabrics were padded to 100% pick-up then dried. Yellowing of the fabrics was assessed by heating the fabrics on an electrically-heated press for up to 3 minutes. Temperature Comments 180°C Little difference between products 200°C Example 4 showed no yellowing at 1,2,3 mins at all levels. Other products yellowed slightly. 220°C Slight yellowing of Example 4. Other products were markedly yellowed.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fats And Perfumes (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9022305 | 1990-10-15 | ||
GB909022305A GB9022305D0 (en) | 1990-10-15 | 1990-10-15 | Softening agents |
PCT/GB1991/001792 WO1992007132A1 (en) | 1990-10-15 | 1991-10-15 | Softening agents |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0553217A1 EP0553217A1 (en) | 1993-08-04 |
EP0553217B1 true EP0553217B1 (en) | 2000-01-12 |
Family
ID=10683701
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP91919216A Expired - Lifetime EP0553217B1 (en) | 1990-10-15 | 1991-10-15 | Softening agents |
Country Status (9)
Country | Link |
---|---|
EP (1) | EP0553217B1 (ja) |
JP (1) | JPH08505190A (ja) |
AT (1) | ATE188754T1 (ja) |
AU (1) | AU661279B2 (ja) |
CA (1) | CA2090332A1 (ja) |
DE (1) | DE69131905T2 (ja) |
ES (1) | ES2140397T3 (ja) |
GB (1) | GB9022305D0 (ja) |
WO (1) | WO1992007132A1 (ja) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9624928D0 (en) * | 1996-11-29 | 1997-01-15 | Lintrend Developments Ni Ltd | Fibrous products and their production |
GB2334535B (en) * | 1996-11-29 | 2001-05-23 | Lintrend Developments | Permanently improving the properties of fabrics and yarn |
GB9923921D0 (en) * | 1999-10-08 | 1999-12-08 | Unilever Plc | Fabric care composition |
GB2505959B (en) | 2012-09-18 | 2017-07-19 | Devan Chemicals Nv | Textile treatment compounds and compositions |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
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BE549558A (ja) * | 1955-07-15 | |||
BE554506A (ja) * | 1956-01-25 | |||
IT626236A (ja) * | 1959-01-16 | Boehme Chemie Gmbh | ||
GB1171304A (en) * | 1966-11-01 | 1969-11-19 | Stevens & Co Inc J P | Polymeric Compounds for Antistatic Treatment of Textiles |
GB8916906D0 (en) * | 1989-07-24 | 1989-09-06 | Precision Proc Textiles Ltd | New prepolymers and their use in a method for the treatment of wool |
-
1990
- 1990-10-15 GB GB909022305A patent/GB9022305D0/en active Pending
-
1991
- 1991-10-15 WO PCT/GB1991/001792 patent/WO1992007132A1/en active IP Right Grant
- 1991-10-15 DE DE69131905T patent/DE69131905T2/de not_active Expired - Lifetime
- 1991-10-15 CA CA002090332A patent/CA2090332A1/en not_active Abandoned
- 1991-10-15 ES ES91919216T patent/ES2140397T3/es not_active Expired - Lifetime
- 1991-10-15 AT AT91919216T patent/ATE188754T1/de not_active IP Right Cessation
- 1991-10-15 JP JP3516491A patent/JPH08505190A/ja active Pending
- 1991-10-15 AU AU86613/91A patent/AU661279B2/en not_active Ceased
- 1991-10-15 EP EP91919216A patent/EP0553217B1/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
DE69131905T2 (de) | 2002-09-05 |
CA2090332A1 (en) | 1992-04-16 |
GB9022305D0 (en) | 1990-11-28 |
EP0553217A1 (en) | 1993-08-04 |
AU8661391A (en) | 1992-05-20 |
WO1992007132A1 (en) | 1992-04-30 |
JPH08505190A (ja) | 1996-06-04 |
DE69131905D1 (de) | 2000-02-17 |
AU661279B2 (en) | 1995-07-20 |
ES2140397T3 (es) | 2000-03-01 |
ATE188754T1 (de) | 2000-01-15 |
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