WO2001094356A1 - Compositions aqueuses contenant des sels de metaux alcalins d'ester alkylique partiel d'acide phosphorique, procede de stabilisation et huiles d'ensimage - Google Patents

Compositions aqueuses contenant des sels de metaux alcalins d'ester alkylique partiel d'acide phosphorique, procede de stabilisation et huiles d'ensimage Download PDF

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Publication number
WO2001094356A1
WO2001094356A1 PCT/JP2001/004740 JP0104740W WO0194356A1 WO 2001094356 A1 WO2001094356 A1 WO 2001094356A1 JP 0104740 W JP0104740 W JP 0104740W WO 0194356 A1 WO0194356 A1 WO 0194356A1
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WO
WIPO (PCT)
Prior art keywords
phosphoric acid
partial
alkali metal
metal salt
ester
Prior art date
Application number
PCT/JP2001/004740
Other languages
English (en)
Japanese (ja)
Inventor
Hajimu Minami
Jun Watanabe
Yoshishige Nakamura
Original Assignee
Matsumoto Yushi-Seiyaku Co., Ltd.
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 Matsumoto Yushi-Seiyaku Co., Ltd. filed Critical Matsumoto Yushi-Seiyaku Co., Ltd.
Priority to AU62695/01A priority Critical patent/AU6269501A/en
Publication of WO2001094356A1 publication Critical patent/WO2001094356A1/fr

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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
    • 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
    • D06M13/10—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 oxygen
    • D06M13/144—Alcohols; Metal alcoholates
    • D06M13/148—Polyalcohols, e.g. glycerol or glucose
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/11—Esters of phosphoric acids with hydroxyalkyl compounds without further substituents on alkyl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
    • C07H3/04—Disaccharides
    • 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
    • D06M13/244—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 sulfur or phosphorus
    • D06M13/282—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 sulfur or phosphorus with compounds containing phosphorus
    • D06M13/292—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts 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
    • D06M7/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins
    • 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
    • D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions

Definitions

  • the present invention relates to an aqueous composition containing an alkali metal salt of a partial alkyl ester of phosphoric acid, a method for stabilizing an aqueous solution of the alkali metal salt, and an oil agent for fibers containing the aqueous solution. More specifically, by adding a specific polyhydric alcohol to an aqueous solution containing a high concentration of an alkali metal salt of a specific alkyl partial ester of phosphoric acid and stabilizing it, the viscosity over time during long-term storage can be significantly increased.
  • the present invention relates to an aqueous composition which solves the problem of increase and concentration unevenness, a method thereof, and an oil agent for textile.
  • Japanese Patent Application Laid-Open No. 59-232330 discloses a spinning oil having a small change in properties with respect to temperature control conditions and environmental changes, wherein the average carbon number of a linear or branched alkyl group is 16 to 22.
  • Proposal of spinning oils mainly containing alkali metal salts of partial alkyl esters of phosphoric acid in the range of 0.6 to 1.0 and 60 to 100% of neutralization degree of phosphoric acid Has been done.
  • This oil agent has extremely small change in properties with respect to environmental changes such as temperature and humidity conditions, and reduces the occurrence of scum in the spinning process that occurs under severe temperature and humidity conditions such as low temperature and low humidity or high temperature and high humidity, and reduces the winding of one roller. It is effective to make.
  • this oil is supplied as a product in the form of an aqueous solution having a concentration of 30 to 50% by weight of an alkali metal salt of a partial alkyl ester of phosphoric acid.
  • Alkali metal salts of partial alkyl esters of phosphoric acid have long-chain alkyl groups and therefore have low hydrophilicity in aqueous solutions with a concentration of 30 to 50% by weight, and have large molecules themselves.
  • the dissolution state is relatively unstable, and over time, the aqueous solution undergoes creaming / association of molecules, which causes a problem such as uneven concentration of the aqueous solution and thickening of the aqueous solution. Once separated, it is difficult to restore to a uniform state, and thickening hinders product handling and workability, and there has been a strong demand for product stabilization.
  • An object of the present invention is to provide an aqueous composition excellent in long-term storage stability, in which an aqueous composition of an alkali metal salt of a partial alkyl ester of phosphoric acid does not separate or thicken under long-term storage. Is to do.
  • Another object of the present invention is to provide an aqueous composition of the above-mentioned Alkyri metal salt, wherein when thickened or frozen at a low temperature, when the temperature is returned to the ambient temperature, the viscosity is eliminated and the original fluidity is easily restored. It is to provide.
  • Still another object of the present invention is to provide a stabilization method for stabilizing the above-mentioned alkali metal salt under long-term storage and low-temperature maintenance in an aqueous solution.
  • Still another object of the present invention is to provide an oil agent for fibers having excellent stability as described above, based on the aqueous composition of the present invention.
  • the alkyl group of the ester group is linear or branched with an average of 16 to 22 carbon atoms
  • Alkali metal salt of partial alkyl ester of phosphoric acid with 100 parts by weight
  • an aqueous composition of an alkali metal salt of a partial alkyl ester of phosphoric acid characterized by containing 1 to 10 parts by weight of a polyhydric alcohol having 3 to 12 carbon atoms and 3 or more hydroxyl groups.
  • the alkyl group of the ester group is linear or branched with an average of 16 to 22 carbon atoms
  • the degree of phosphorylation is in the range of 0.6 to 1.0 and
  • a metal salt of a partial alkyl ester of phosphoric acid having the formula a polyvalent having 3 to 12 carbon atoms and 3 or more hydroxyl groups at a ratio of 1 to 10 parts by weight per 100 parts by weight of the above metal salt Add alcohol,
  • a fibrous oil agent characterized by containing the aqueous composition of the present invention as a main component.
  • the alkali metal salt of a partial alkyl ester of phosphoric acid used in the present invention has the following properties (1) to (3).
  • the alkyl group of the ester group has an average carbon number of 16 to 22, and may be linear or branched.
  • the degree of phosphorylation is in the range of 0.6 to 1.0.
  • the degree of phosphorylation is the number of equivalents of phosphorus atoms per equivalent of the alkyl ester group of the partial alkyl ester of phosphoric acid.
  • the phosphorylation degree can be measured by a known phosphomolybdic acid colorimetry.
  • the degree of neutralization is in the range of 60 to 100%.
  • the degree of neutralization is the ratio of the neutralized hydroxyl group (hydroxyl group forming the metal salt of alkali metal) to the total hydroxyl group of the partial alkyl ester of phosphoric acid, expressed in equivalent%. If the degree of neutralization is less than 60%, the stability of the antistatic solution is deteriorated, and if it exceeds 100%, excess alcohol compound not used for neutralization remains unfavorably in handling.
  • Alkali metal salts of partial alkyl esters of phosphoric acid are obtained by neutralizing a phosphoric acid partial esterified product of one or more linear or branched higher alcohols with phosphoric acid with an inorganic alkali hydroxide.
  • the average carbon number of the higher alcohol is 16 to 22. If it is less than 16, only an aqueous solution whose property greatly changes with respect to environmental changes such as temperature and humidity conditions can be obtained, and if it exceeds 22, a stable aqueous solution cannot be obtained.
  • the alkali metal salt of a partial alkyl ester of phosphoric acid is preferably, for example, a lithium salt, a sodium salt, or a potassium salt, and most preferably a potassium salt, from the viewpoint of antistatic properties and aqueous solution stability.
  • Metal salts other than alkali metal such as magnesium, calcium, norium, aluminum, zinc, iron, and copper are insoluble in water and are out of the scope of the present invention.
  • phosphoric acid partial alkyl ester metal salts include: phosphoric acid partial stearyl ester potassium salt, phosphoric acid partial stearyl ester sodium salt, phosphoric acid partial cetyl ester potassium salt, phosphoric acid partial cetyl ester sodium salt, phosphoric acid portion There may be mentioned, for example, benzyl ester potassium salt, phosphate partial henyl ester sodium salt and the like, and mixtures thereof. Of these, phosphoric acid partial stearyl ester potassium salt is the most effective.
  • the polyhydric alcohol used in the present invention together with the alkali metal salt of a partial alkyl ester of phosphoric acid has 3 to 12 carbon atoms.
  • the resulting aqueous composition will have an increased tackiness, and the performance of the alkali metal salt of a partial alkyl ester of phosphoric acid as the main component will be impaired.
  • the number of hydroxyl groups in one molecule of the polyhydric alcohol is 3 or more, and 3 to L0 is preferable. If it is less than 3, the effect of separating, thickening and freezing is difficult to be seen, and if it exceeds 10, the adhesiveness becomes so strong that the performance of the alkali metal salt of a partial alkyl ester of phosphoric acid as the main component tends to be impaired.
  • polyhydric alcohol component used in the present invention examples include glycerin, trimethylolpropane, pentaerythritol, sorbitol, glucose, fructose, fructose, sucrose, maltose, and the like, and mixtures thereof.
  • the amount of the polyhydric alcohol to be added is 1 to 10% by weight, preferably 6 to 8% by weight based on the weight of the alkali metal salt of the partial alkyl ester of phosphoric acid. No effect is exhibited when the added amount is less than 1% by weight, and no separation> thickening and freezing prevention effects are observed. Also 1
  • an antistatic agent and a milk itch agent are blended in an oil composed of polyalphaolefin, and phosphoric acid is used as the antistatic agent.
  • examples thereof include an alkali metal salt of an ester, an ethoxylate of an alcohol ( ⁇ ) as an emulsifier, and an ether of a secondary alcohol and polyethylene glycol.
  • ⁇ ethoxylate of an alcohol
  • ether emulsifier
  • none of these emulsifiers has any effect on the stabilization of the alkali metal salt of the partial alkyl phosphate as shown in the POE (3) lauryl ether mentioned as a comparative example in the present invention.
  • the polyhydric alcohol component is preferably added after the completion of the neutralization reaction in the production of the phosphoric acid partial alkyl ester alkali metal salt, but once the product is finished, it is placed in an aqueous solution of the phosphoric acid partial alkyl ester alkali metal salt. It does not matter if it is added afterwards.
  • a salt of a partial alkyl ester of phosphoric acid which is different from the metal salt of a partial alkyl ester of phosphoric acid specified in the present invention, is used in a range that does not impair the effects of the present invention. It can be used in a proportion of 30% by weight or less based on the metal salt.
  • Such other salts include triethanolamine salt of partial stearyl ester of phosphoric acid, potassium salt of partial lauryl ester of phosphoric acid, potassium salt of partial decyl ester of phosphoric acid, and partial octyl ester of phosphoric acid. Potassium salt and the like.
  • the aqueous composition of the present invention contains an alkali metal salt of a partial alkyl ester of phosphoric acid, preferably at 20 to 60% by weight, more preferably 30 to 50% by weight.
  • the use of the stabilized aqueous composition of the present invention is not particularly limited, but is used, for example, as a main component of an oil agent for fibers.
  • the fibers to which the oil agent for fibers of the present invention is applied include, for example, natural fibers such as cotton, hemp and wool, recycled fibers such as rayon, and synthetic fibers such as polyester, nylon, and polypropylene. Of these, it is particularly effective to apply to polyester short fibers.
  • the aqueous composition or aqueous solution of the present invention is used in a fibrous oil at a solid content of 50% by weight or more.
  • other lower alkyl phosphates, alkyl sulfates, and anionic activators such as fatty acid salts; Cationic activators such as dimethyl salts; amphoteric activators such as alkyl betaines; nonionic activators such as polyoxyethylene alkyl ethers, fatty acid polyethylene glycol esters, fatty acid polyhydric alcohol esters, polyoxyethylene alkylamines; Mineral oils such as paraffin; ester oils such as fatty acid alkyl and fatty acid polyoxyethylene alkyl; paraffinic or ester wax; one or more components selected from silicone oils such as dimethyl silicone It is common to do.
  • One or more known antifoaming agents, preservatives and antioxidants can be added for the purpose of improving the defoaming property
  • the oil composition for fibers containing the aqueous composition or aqueous solution of the present invention as a main component is an aqueous emulsion. It is applied to the fiber as a fiber, and can be adhered to the fiber by a known method such as a dipping method, a spray method, or a roller setting method.
  • the amount of adhesion varies depending on the type, brand, and application of the fiber.
  • 0.02 to 0.30% by weight of solid content is attached to ordinary fiber.
  • Example 1 shows the type of polyhydric alcohol used in the present invention and the change in viscosity of the obtained aqueous composition.
  • Table 2 shows the types of polyhydric alcohols used in the present invention, the antifreezing ability of the obtained aqueous composition, and the resilience after freezing.
  • Example 3 shows the effect of the addition of polyhydric alcohol for each brand of alkali metal products of the phosphoric acid partial alkyl ester used in the present invention.
  • Example 4 shows the addition ratio of the polyhydric alcohol used in the present invention, the change in viscosity of the obtained aqueous composition, and the ability to prevent freezing.
  • Example 5 the spinnability of the oil agent used in the present invention is shown in Table 5.
  • Example 6 the friction characteristics of the oil agent used in the present invention are shown in Table 6.
  • Example 1 and Comparative Example 1 the friction characteristics of the oil agent used in the present invention are shown in Table 6.
  • the aqueous composition containing the potassium salt of the partial stearyl ester of phosphoric acid to which the polyhydric alcohol of the present invention has been added has a lower viscosity than that of the non-added one, and that the aqueous composition left untreated under the forced conditions has no addition. It can be seen that the viscosity is lower than that.
  • a 8% by weight solid component was added to an aqueous solution of a phosphoric acid partially stearyl ester concentrated sodium salt solution having a concentration of 35% by weight, and the mixture was uniformly mixed.
  • the resulting aqueous composition was mixed with a 10 O ml screw tube. Then, it was placed in a freezer at 120 ° C., and the freezing state was checked every 30 minutes, and the freezing start and freezing completion times were examined.
  • the aqueous solution of the potassium salt of the partial stearyl phosphate of the present invention to which the polyhydric alcohol is added delays freezing as compared with the case where no polyhydric alcohol is added, and restores the fluidity at a low temperature even after freezing. You can see that it can be done.
  • aqueous composition was prepared by adding 8% of glycerin or 8% of sucrose to each brand of potassium salt of a partial alkyl ester of phosphoric acid. The viscosity change was measured immediately after compounding this composition and at 4 ° C. for 4 weeks (compulsory test).
  • Table 3 shows that the partial stearyl ester potassium salt of phosphoric acid with different production conditions, the partial alkyl ester phosphate salt of phosphoric acid with alkyl having different carbon atoms in the same component, and the phosphoric acid with other long chain alkyl
  • polyhydric alcohols are also effective for partial alkyl ester potassium salts.
  • the addition of a polyhydric alcohol causes an increase in the viscosity of an aqueous solution of a phosphoric acid partial lauryl ester-soluble lime salt.
  • Unit of viscosity is m p a ⁇ s.
  • the appearance is the ratio of the thickened part, and * indicates that the thickened part is very small.
  • the unit of viscosity is mPa ⁇ s. From Table 4, it can be seen that adding a polyhydric alcohol even at 1% produces a viscosity reducing effect. In addition, it can be seen that the effect of preventing freezing due to freezing is remarkably exhibited at an addition amount of 5% or more. '' Example 5 and Comparative Example 4
  • Table 5 shows that the spinnability is not impaired even if the polyhydric alcohol is added to the partial stearyl ester phosphate salt of phosphoric acid if the ratio is 10% or less.
  • Example 6 and Comparative Example 5 As shown in the comparative example, when the addition ratio is more than 10%, the number of windings per spinning roller increases significantly, which is not preferable.
  • Example 6 and Comparative Example 5 As shown in the comparative example, when the addition ratio is more than 10%, the number of windings per spinning roller increases significantly, which is not preferable.
  • the product viscosity is reduced with little effect on spinnability and friction characteristics, handleability is improved, and thickening and separation over time are prevented. Can be suppressed.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Emergency Medicine (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

On stabilise une solution aqueuse contenant un sel de métaux alcalins d'un ester alkylique partiel d'acide phosphorique, les groupes alkyles pouvant être chacun linéaires ou ramifiés et possédant, en moyenne, 16 à 22 atomes de carbone, le degré de phosphorylation étant de 0,6 à 1,0 et le degré de neutralisation de 60 à 100 %, en ajoutant 1 à 10 % en poids d'un polyalcool possédant 3 à 12 atomes de carbone et au moins trois groupes hydroxyles. L'invention porte également sur des huiles d'ensimage contenant la solution aqueuse stabilisée résultante, en tant que composant principal.
PCT/JP2001/004740 2000-06-07 2001-06-05 Compositions aqueuses contenant des sels de metaux alcalins d'ester alkylique partiel d'acide phosphorique, procede de stabilisation et huiles d'ensimage WO2001094356A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU62695/01A AU6269501A (en) 2000-06-07 2001-06-05 Aqueous compositions containing alkali metal salts of partial alkyl esters of phosphoric acid, method for stabilization and textile oils

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2000-210567 2000-06-07
JP2000210567 2000-06-07

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US10049062 A-371-Of-International 2001-06-05
US10/105,388 Continuation-In-Part US6841086B2 (en) 2000-06-07 2002-03-26 Aqueous composition of alkali metal salts of partial alkyl esters of phosphoric acid, method for stabilization and a fiber finish

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WO2001094356A1 true WO2001094356A1 (fr) 2001-12-13

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60224867A (ja) * 1984-04-19 1985-11-09 帝人株式会社 ポリエステル繊維用紡績油剤
JPS60224868A (ja) * 1984-04-20 1985-11-09 帝人株式会社 ポリエステル繊維用紡績油剤組成物
JPS61124680A (ja) * 1984-11-19 1986-06-12 帝人株式会社 ポリエステル繊維用紡績油剤組成物

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60224867A (ja) * 1984-04-19 1985-11-09 帝人株式会社 ポリエステル繊維用紡績油剤
JPS60224868A (ja) * 1984-04-20 1985-11-09 帝人株式会社 ポリエステル繊維用紡績油剤組成物
JPS61124680A (ja) * 1984-11-19 1986-06-12 帝人株式会社 ポリエステル繊維用紡績油剤組成物

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