CN114875675B - Sodium lignin sulfonate polyether amphoteric surfactant for polyester industrial yarns, polyester industrial yarn spinning oil agent, and preparation method and application thereof - Google Patents
Sodium lignin sulfonate polyether amphoteric surfactant for polyester industrial yarns, polyester industrial yarn spinning oil agent, and preparation method and application thereof Download PDFInfo
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- CN114875675B CN114875675B CN202210487237.1A CN202210487237A CN114875675B CN 114875675 B CN114875675 B CN 114875675B CN 202210487237 A CN202210487237 A CN 202210487237A CN 114875675 B CN114875675 B CN 114875675B
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- CN
- China
- Prior art keywords
- lignin sulfonate
- sal
- sodium lignin
- polyether
- polyester industrial
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- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 title claims abstract description 123
- 239000004721 Polyphenylene oxide Substances 0.000 title claims abstract description 92
- 229920000570 polyether Polymers 0.000 title claims abstract description 92
- 229920000728 polyester Polymers 0.000 title claims abstract description 72
- 239000002280 amphoteric surfactant Substances 0.000 title claims abstract description 55
- 238000009987 spinning Methods 0.000 title claims abstract description 52
- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 9
- 241000519995 Stachys sylvatica Species 0.000 claims abstract description 28
- 238000004043 dyeing Methods 0.000 claims abstract description 15
- 238000005406 washing Methods 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims description 66
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 63
- 239000000243 solution Substances 0.000 claims description 53
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 41
- 239000007864 aqueous solution Substances 0.000 claims description 32
- 239000003921 oil Substances 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- 238000003756 stirring Methods 0.000 claims description 26
- 238000001035 drying Methods 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 claims description 15
- 238000001914 filtration Methods 0.000 claims description 14
- 238000001291 vacuum drying Methods 0.000 claims description 13
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 claims description 12
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 238000001816 cooling Methods 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000008367 deionised water Substances 0.000 claims description 8
- 229910021641 deionized water Inorganic materials 0.000 claims description 8
- 229920004933 Terylene® Polymers 0.000 claims description 7
- 230000003472 neutralizing effect Effects 0.000 claims description 7
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 6
- 239000003755 preservative agent Substances 0.000 claims description 6
- 230000002335 preservative effect Effects 0.000 claims description 6
- 229960000583 acetic acid Drugs 0.000 claims description 5
- 238000000605 extraction Methods 0.000 claims description 5
- 239000012362 glacial acetic acid Substances 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000009499 grossing Methods 0.000 claims description 4
- 229920000056 polyoxyethylene ether Polymers 0.000 claims description 4
- 229940051841 polyoxyethylene ether Drugs 0.000 claims description 4
- 238000005303 weighing Methods 0.000 claims description 4
- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 claims description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 3
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 claims description 3
- UQKAOOAFEFCDGT-UHFFFAOYSA-N n,n-dimethyloctan-1-amine Chemical compound CCCCCCCCN(C)C UQKAOOAFEFCDGT-UHFFFAOYSA-N 0.000 claims description 3
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims description 3
- 239000004302 potassium sorbate Substances 0.000 claims description 3
- 235000010241 potassium sorbate Nutrition 0.000 claims description 3
- 229940069338 potassium sorbate Drugs 0.000 claims description 3
- 238000005086 pumping Methods 0.000 claims description 3
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 claims description 3
- 239000004299 sodium benzoate Substances 0.000 claims description 3
- 235000010234 sodium benzoate Nutrition 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 claims description 2
- OXPCWUWUWIWSGI-MSUUIHNZSA-N Lauryl oleate Chemical compound CCCCCCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC OXPCWUWUWIWSGI-MSUUIHNZSA-N 0.000 claims description 2
- 240000007263 Pinus koraiensis Species 0.000 claims description 2
- 235000011615 Pinus koraiensis Nutrition 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 2
- BAECOWNUKCLBPZ-HIUWNOOHSA-N Triolein Natural products O([C@H](OCC(=O)CCCCCCC/C=C\CCCCCCCC)COC(=O)CCCCCCC/C=C\CCCCCCCC)C(=O)CCCCCCC/C=C\CCCCCCCC BAECOWNUKCLBPZ-HIUWNOOHSA-N 0.000 claims description 2
- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 239000004359 castor oil Substances 0.000 claims description 2
- 235000019438 castor oil Nutrition 0.000 claims description 2
- 229950010007 dimantine Drugs 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 2
- 229940055577 oleyl alcohol Drugs 0.000 claims description 2
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 27
- 230000008569 process Effects 0.000 abstract description 22
- 239000006185 dispersion Substances 0.000 abstract description 6
- 238000004945 emulsification Methods 0.000 abstract description 4
- 239000003995 emulsifying agent Substances 0.000 abstract description 3
- 230000007797 corrosion Effects 0.000 abstract description 2
- 238000005260 corrosion Methods 0.000 abstract description 2
- 238000005238 degreasing Methods 0.000 abstract description 2
- 238000000108 ultra-filtration Methods 0.000 description 32
- 239000012528 membrane Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000000706 filtrate Substances 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 238000000967 suction filtration Methods 0.000 description 10
- 239000000975 dye Substances 0.000 description 9
- 230000004913 activation Effects 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 229920005552 sodium lignosulfonate Polymers 0.000 description 6
- 238000009210 therapy by ultrasound Methods 0.000 description 6
- 230000007547 defect Effects 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000004090 dissolution Methods 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 238000010186 staining Methods 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 229920005610 lignin Polymers 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 230000006978 adaptation Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- -1 chloro PEG400 Chemical compound 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000011345 viscous material Substances 0.000 description 2
- 235000017166 Bambusa arundinacea Nutrition 0.000 description 1
- 235000017491 Bambusa tulda Nutrition 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920006052 Chinlon® Polymers 0.000 description 1
- 244000082204 Phyllostachys viridis Species 0.000 description 1
- 235000015334 Phyllostachys viridis Nutrition 0.000 description 1
- 239000011425 bamboo Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- NAPSCFZYZVSQHF-UHFFFAOYSA-N dimantine Chemical compound CCCCCCCCCCCCCCCCCCN(C)C NAPSCFZYZVSQHF-UHFFFAOYSA-N 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 239000002455 scale inhibitor Substances 0.000 description 1
- 238000004804 winding Methods 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33303—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group
- C08G65/33306—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group acyclic
-
- 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
- D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/60—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing polyethers
- D06P1/607—Nitrogen-containing polyethers or their quaternary derivatives
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
-
- 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
- D06M2101/32—Polyesters
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
- Y02P70/62—Manufacturing or production processes characterised by the final manufactured product related technologies for production or treatment of textile or flexible materials or products thereof, including footwear
Abstract
The invention discloses a sodium lignin sulfonate polyether amphoteric surfactant for polyester industrial yarns, a polyester industrial yarn spinning oil agent, a preparation method and application thereof. The sodium lignin sulfonate polyether amphoteric surfactant prepared by the invention is added into spinning oil as an emulsifier, and mainly plays roles of emulsification, antistatic and corrosion resistance in the spinning process; the process mainly plays roles of emulsification, degreasing, dye dispersion and the like in a washing and dyeing one-bath process. The application of the polyester industrial yarn obtained by adopting the spinning oil of the polyester industrial yarn in one-bath dyeing is that the white spot of the polyester industrial yarn is less than 100ppm. The application of the sodium lignin sulfonate polyether amphoteric surfactant for the polyester industrial yarn and the polyester industrial yarn obtained after the spinning of the existing spinning oil in one bath dyeing method is included, and the white spots of the polyester industrial yarn are smaller than 40ppm.
Description
Technical Field
The invention belongs to the technical field of polyester industrial yarns, and particularly relates to a sodium lignin sulfonate polyether amphoteric surfactant for polyester industrial yarns, a polyester industrial yarn spinning oil agent, a preparation method and application thereof.
Background
In the process of spinning, stretching, traction, twisting and the like, the chemical fibers such as terylene, chinlon and the like are required to be added with a proper amount of spinning oil in order to reduce friction coefficient, eliminate electrostatic influence and improve spinnability and processability, and the quality of the spinning oil directly determines the quality of the chemical fibers. Under the current rapid development background of chemical fiber industry, the polyester product is more important, so that the quality of the polyester spinning oil product can be said to directly influence the whole chemical fiber industry. The technical requirement of the spinning oil for the polyester industrial yarn is far greater than that of the spinning oil for the polyester civil yarn.
Along with the continuous promotion of national energy conservation and emission reduction, low carbon and consumption reduction, the short flow, low bath ratio and one bath process technology of enterprises are continuously updated, so that new requirements are provided for the spinning oil. In the actual production process, the spinning process has good spinnability, but when the spinning process is applied to downstream enterprises, the conditions of dyeing, color defects and the like are often encountered. Especially when using low bath ratio, one bath process, the change of the bathtub is more frequent, and the dyeing and color defect conditions are more serious. Therefore, there is a need to develop a spinning oil suitable for downstream enterprises to wash and dye one bath process, namely, a sodium lignin sulfonate polyether amphoteric surfactant for polyester industrial yarns, a polyester industrial yarn spinning oil, a preparation method and application thereof.
Disclosure of Invention
In order to solve the problems in the prior art, the invention provides the sodium lignin sulfonate polyether amphoteric surfactant for the polyester industrial yarns, which can greatly improve the antistatic performance, and in addition, oil is wrapped in a solution in the deoiling process due to the double electric layer effect, so that the emulsion state is very stable, and the staining caused by staining is avoided; polyether AO is introduced into the amphoteric surfactant, so that the water solubility of the amphoteric surfactant is increased, the emulsion after oil removal is more stable, and yarns are prevented from being re-stained due to demulsification.
Meanwhile, the invention also provides a preparation method of the sodium lignin sulfonate polyether amphoteric surfactant for the polyester industrial yarns.
Meanwhile, the invention provides a polyester industrial yarn spinning oil containing the sodium lignin sulfonate polyether amphoteric surfactant for the polyester industrial yarn.
Meanwhile, the invention provides an application of the polyester industrial yarn obtained by adopting the polyester industrial yarn spinning oil solution to dyeing, and white spots are less than 100ppm after the polyester industrial yarn is dyed by adopting a one-bath process.
Meanwhile, the invention provides a sodium lignin sulfonate polyether amphoteric surfactant for the polyester industrial yarn, which is used in combination with the existing spinning oil for spinning, and the white spot of the obtained polyester industrial yarn is less than 40ppm after the polyester industrial yarn is dyed by adopting a one-bath process.
In order to solve the technical problems, the invention adopts the following technical scheme:
the sodium lignin sulfonate polyether amphoteric surfactant for the polyester industrial yarn comprises the following structural units:
wherein SAL is sodium lignin sulfonate;
AO is polyether, and AO comprises any one or combination of ethylene oxide EO, propylene oxide PO and butylene oxide BO;
m is in the range of 4-20;
r comprises C8-C22 straight-chain alkane;
b comprises no substituent.
Or B is formed by-CH 2 -CH(OH)-CH 2 -substitution of unsubstituted groups.
The preparation method of the sodium lignin sulfonate polyether amphoteric surfactant for the polyester industrial yarn comprises the following steps (B is non-substituent):
step one, pretreatment of sodium lignin sulfonate SAL:
s01, filtering: taking sodium lignin sulfonate aqueous solution with the mass percentage concentration of 5-10%, carrying out suction filtration on medium-speed filter paper at the vacuum degree of-0.5 to-0.1 Mpa, and taking lower-layer filtrate A;
s02, ultrasonic activation: carrying out ultrasonic treatment on the filtrate A for 2-6 hours at the temperature of 25-80 ℃ under the power of 80-100% in ultrasonic waves to obtain a solution B, wherein the power of ultrasonic equipment is 400-500W;
s03, ultrafiltration grading impurity removal: treating with ultrafiltration device, and collecting solution B with ultrafiltration membrane with molecular weight cut-off of 10 kDa; then the solution is adopted to an ultrafiltration membrane with the molecular weight cut-off of 1kDa to obtain a solution C with the molecular weight of 1kDa to 10 kDa;
s04, drying by distillation: distilling the solution C in a rotary evaporator under reduced pressure, wherein the vacuum degree is-0.5 to-0.1 Mpa, and then drying the solution C in a vacuum oven at 70-80 ℃ for 48-72h;
step two, preparing sodium lignin sulfonate polyether SAL-AO:
pumping negative pressure to replace nitrogen in the reaction kettle, repeating for at least 3 times, and stirring at 200-300rpm, and introducing N, N-dimethylformamide DMF and sodium lignin sulfonate SAL with the weight ratio of (5-10): 1; then heating to 100-110 ℃, adding an alkaline catalyst after 0.5-0.6h, wherein the adding weight of the alkaline catalyst is equivalent to 11.8-160% of sodium lignin sulfonate SAL after the first pretreatment, and keeping the temperature at 115-125 ℃;
then carrying out curing reaction for 1-2 times;
first curing reaction: simultaneously, slowly introducing AO and sodium lignin sulfonate SAL after the second pretreatment, wherein the introducing time of both the AO and the sodium lignin sulfonate SAL lasts for 1-4 hours, the introducing weight of AO is equivalent to 17.6-105.6 times of that of the sodium lignin sulfonate SAL after the first pretreatment, and the introducing weight of the sodium lignin sulfonate SAL after the second pretreatment is equivalent to 39-79 times of that of the sodium lignin sulfonate SAL after the first pretreatment; curing reaction until the pressure is stable for 0.5-0.6 h;
second curing reaction: after the first curing reaction is finished, the temperature is not increased or is increased to 125-135 ℃, and then AO is slowly introduced, wherein the introduced weight of AO is 21.6-46.4 times of that of sodium lignin sulfonate SAL after the first pretreatment; the time is continuously 1-2h, and the reaction is finished when the pressure is stable for 0.5-0.6 h;
then carrying out reduced pressure distillation at 125-135 ℃ to recover N, N-dimethylformamide DMF, then cooling to 50-60 ℃, and neutralizing with glacial acetic acid to obtain sodium lignin sulfonate polyether SAL-AO;
step three, preparing a sodium lignin sulfonate polyether amphoteric surfactant SAL-AO-Q:
weighing a proper amount of sodium lignin sulfonate polyether SAL-AO, adding deionized water with the weight 3-9 times that of the sodium lignin sulfonate polyether SAL-AO into a reaction kettle, heating to 50-65 ℃, and preserving heat for 0.5-1h to enable the sodium lignin sulfonate polyether SAL-AO to be fully dissolved; then adjusting the pH value of a reaction system to be between 9 and 11 by using a 0.5 and 1.0N NaOH aqueous solution, heating to 80 to 90 ℃, adding tetrabutylammonium bromide, wherein the adding weight of the tetrabutylammonium bromide is equal to 0.5 to 2 percent of that of sodium lignin sulfonate polyether SAL-AO, slowly dropwise adding epichlorohydrin ECH for 0.5 to 2 hours, and the adding weight of the epichlorohydrin ECH is equal to 46.25 percent of that of sodium lignin sulfonate polyether SAL-AO; then continuing to keep the temperature and stir for reaction for 3-6h; slowly dropwise adding N, N-dimethyl alkylamine, wherein the adding weight of the N, N-dimethyl alkylamine is 78.5-176.5% of that of sodium lignin sulfonate polyether SAL-AO; and simultaneously adjusting the pH value to be 8-10 by using a 0.1-0.5N NaOH aqueous solution, stirring for 2-5h after the dropwise addition of the solution is completed, distilling to remove water, washing by using absolute ethyl alcohol, filtering, and drying at 80-85 ℃ for at least 48h in a vacuum drying oven to obtain SAL-AO-Q.
A process for preparing the sodium lignin sulfonate polyether amphoteric surfactant used for polyester industrial yarn includes such steps as preparing the surfactant (B is-CH) 2 -CH(OH)-CH 2 -substituents):
step one, pretreatment of sodium lignin sulfonate SAL:
s01, filtering: taking sodium lignin sulfonate aqueous solution with the mass percentage concentration of 5-10%, carrying out suction filtration on medium-speed filter paper at the vacuum degree of-0.5 to-0.1 Mpa, and taking lower-layer filtrate A;
s02, ultrasonic activation: carrying out ultrasonic treatment on the filtrate A for 2-6 hours at the temperature of 25-80 ℃ under the power of 80-100% in ultrasonic waves to obtain a solution B, wherein the power of ultrasonic equipment is 400-500W;
s03, ultrafiltration grading impurity removal: treating with ultrafiltration device, and collecting solution B with ultrafiltration membrane with molecular weight cut-off of 10 kDa; then the solution is adopted to an ultrafiltration membrane with the molecular weight cut-off of 1kDa to obtain a solution C with the molecular weight of 1kDa to 10 kDa;
s04, drying by distillation: distilling the solution C in a rotary evaporator under reduced pressure, wherein the vacuum degree is-0.5 to-0.1 Mpa, and then drying the solution C in a vacuum oven at 70-80 ℃ for 48-72h;
step two, preparing sodium lignin sulfonate polyether SAL-AO:
200-250g PEG400 is added into a reaction kettle, the temperature is raised to 55-60 ℃, and then 0.8-1g boron trifluoride-diethyl ether BF is added into the reaction kettle 3 -Et 2 O, after uniformly stirring, slowly dropwise adding 56-60g of epichlorohydrin ECH for 0.5-2h, and keeping the temperature at 55-60 ℃; after the dripping is finished, continuously keeping the temperature of 55-60 ℃ for reaction for 1-4h; then decompressing and distilling to remove residual epichlorohydrin ECH to obtain chlorinated PEG400 intermediate; then 100-200g of pretreated sodium lignin sulfonate SAL is dissolved in 1N NaOH aqueous solution to prepare aqueous solution with the concentration of 25-30%, then chlorinated PEG400 intermediate is dripped, after 1-3h of dripping is finished, the temperature is raised and the reaction is carried out for 1-5h at 80-85 ℃; after cooling, neutralizing with concentrated hydrochloric acid to adjust the pH to 7-7.5, thereby obtaining a product; then purifying, adding butanone into the product solution for continuous extraction to remove unreacted PEG400 and water untilUntil the lower layer has yellow brown viscous substance, centrifuging at 8000-10000rpm to obtain product; vacuum drying to obtain purified sodium lignin sulfonate polyether SAL-AO;
step three, preparing a sodium lignin sulfonate polyether amphoteric surfactant SAL-AO-Q:
weighing a proper amount of sodium lignin sulfonate polyether SAL-AO, adding deionized water with the weight 3-9 times that of the sodium lignin sulfonate polyether SAL-AO into a reaction kettle, heating to 50-65 ℃, and preserving heat for 0.5-1h to enable the sodium lignin sulfonate polyether SAL-AO to be fully dissolved; then adjusting the pH value of a reaction system to be between 9 and 11 by using a 0.5 and 1.0N NaOH aqueous solution, heating to 80 to 90 ℃, adding tetrabutylammonium bromide, wherein the adding weight of the tetrabutylammonium bromide is equal to 0.5 to 2 percent of that of sodium lignin sulfonate polyether SAL-AO, slowly dropwise adding epichlorohydrin ECH for 0.5 to 2 hours, and the adding weight of the epichlorohydrin ECH is equal to 46.25 percent of that of sodium lignin sulfonate polyether SAL-AO; then continuing to keep the temperature and stir for reaction for 3-6h; slowly dropwise adding N, N-dimethyl alkylamine, wherein the adding weight of the N, N-dimethyl alkylamine is 78.5-176.5% of that of sodium lignin sulfonate polyether SAL-AO; and simultaneously adjusting the pH value to be 8-10 by using a 0.1-0.5N NaOH aqueous solution, stirring for 2-5h after the dropwise addition of the solution is completed, distilling to remove water, washing by using absolute ethyl alcohol, filtering, and drying at 80-85 ℃ for at least 48h in a vacuum drying oven to obtain SAL-AO-Q.
N, N-dimethyl alkylamines include N, N-dimethyl octylamine, N-dimethyl-behenyl amine, N-dimethyl-octadecyl amine or N, N-dimethyl-dodecyl amine.
The basic catalyst comprises sodium methoxide, potassium methoxide or sodium ethoxide.
The polyester industrial yarn spinning oil containing the sodium lignin sulfonate polyether amphoteric surfactant for the polyester industrial yarns comprises the following components in parts by weight: smoothing agent: 50 parts of surfactant: 30 parts of preservative: 0.1 part and water: 320 parts; the surfactant comprises: sodium lignin sulfonate polyether amphoteric surfactant: 1-20 parts of propylene glycol block polyether L61:3-6 parts of oleyl alcohol polyoxyethylene ether ester OV-5:2-10 parts of hydrogenated castor oil polyoxyethylene ether HEL-20:1-10 parts of polyethylene glycol dioleate PEG400DO:1-6 parts.
The smoothing agent comprises glycerol trioleate and lauryl oleate in a weight ratio of 2:3.
The preservative comprises pinus koraiensis, sodium benzoate or potassium sorbate.
The white spot of the polyester industrial yarn obtained by adopting the polyester industrial yarn spinning oil solution for spinning is less than 100ppm, and compared with the prior art, the white spot is reduced by more than 76 percent.
The application of the sodium lignin sulfonate polyether amphoteric surfactant for the polyester industrial yarn in dyeing of the polyester industrial yarn obtained by spinning with the existing spinning oil is that the white spot of the polyester industrial yarn is less than 40ppm, and compared with the prior art, the best case white spot reduction of the polyester industrial yarn can reach more than 99%.
Compared with the prior art, the invention has the beneficial effects that:
1. the sodium lignin sulfonate polyether amphoteric surfactant is lignin derivative, and the lignin derivative is used as biomass material, meets the national requirements of green and environment-friendly renewable raw materials, and is particularly important when the current petrochemical raw materials become more severe and gradually exhausted.
2. The sodium lignin sulfonate polyether amphoteric surfactant is used as a dye dispersing agent, a refining agent and a scale inhibitor, and has certain antibacterial performance. After finishing spinning oil on the polyester industrial yarn, applying the spinning oil to downstream enterprises, and when carrying out a one-bath process, the sodium lignin sulfonate polyether amphoteric surfactant not only plays a refining function, but also washes the oil on the polyester industrial yarn into dye liquor together with other emulsifying agents, and simultaneously serves as a dispersing agent of disperse dye, so that the stability of the dye liquor is further maintained, and the dye concentration is kept uniformly spread on the surface of the polyester industrial yarn until dyeing and fixation are carried out. In addition, the sodium lignin sulfonate polyether amphoteric surfactant also has certain scale inhibition performance, so that the sodium lignin sulfonate polyether amphoteric surfactant is not easily influenced by various metal ions in a one-bath process. Thereby further improving the stability of the dye bath, reducing and avoiding the occurrence of color flowers and color defects, reducing the risk of reworking and lowering the cost. In addition, as the sodium lignin sulfonate polyether amphoteric surfactant, especially the bamboo lignin derivative, has better antibacterial performance, the sodium lignin sulfonate polyether amphoteric surfactant also has a certain antibacterial effect, and reduces the frequency of changing and washing the dye vat because of mildew, thereby reducing the cost and pollution discharge. In addition, after chemical fiber oiling, the storage time can be prolonged in the cylinder storage process, and the mildew probability is reduced.
3. The polyether AO is introduced into the sodium lignin sulfonate polyether amphoteric surfactant, so that the water solubility of the sodium lignin sulfonate polyether amphoteric surfactant is increased, the deoiled emulsion is more stable, and yarns are prevented from being re-polluted due to demulsification.
4. The sodium lignin sulfonate polyether amphoteric surfactant greatly improves the antistatic performance. In addition, oil is wrapped in the solution due to the double electric layer effect in the deoiling process, so that the emulsion state is very stable, and the staining caused by staining is avoided.
5. The sodium lignin sulfonate polyether amphoteric surfactant prepared by the invention is added into spinning oil as an emulsifier, and mainly plays roles of emulsification, antistatic and corrosion resistance in the spinning process; the process mainly plays roles of emulsification, degreasing, dye dispersion and the like in a washing and dyeing one-bath process.
6. The white spot of the terylene industrial yarn obtained by adopting the terylene industrial yarn spinning oil spinning of the invention is less than 100ppm when the terylene industrial yarn is dyed by a one-bath process, and compared with the prior art, the white spot is reduced by more than 76 percent.
7. The application of the sodium lignin sulfonate polyether amphoteric surfactant for the polyester industrial yarn and the polyester industrial yarn obtained after the spinning combination of the sodium lignin sulfonate polyether amphoteric surfactant and the existing spinning oil in one bath dyeing is included, the white spot of the polyester industrial yarn is less than 40ppm, and compared with the prior art, the optimal case white spot reduction of the invention can reach more than 99%.
Drawings
FIG. 1 is a white spot pattern of comparative example 1 of the present invention;
FIG. 2 is a white spot profile of comparative example 2 of the present invention;
FIG. 3 is a white spot pattern of example 8 of the present invention.
Detailed Description
The following description of the embodiments of the present invention will be made more fully hereinafter with reference to the accompanying drawings, in which some, but not all embodiments of the invention are shown. All other embodiments, which can be made by one of ordinary skill in the art without undue burden on the person of ordinary skill in the art based on embodiments of the present invention, are within the scope of the present invention.
1. Reaction scheme
2. The specific structure of the sodium lignin sulfonate polyether is shown in table 1 below.
TABLE 1 Structure of sodium Lignosulfonate polyether
| SAL-AO | B | AO | m |
| SAL-AO-1 | -- | EO | 4 |
| SAL-AO-2 | -- | EO/PO | 20 |
| SAL-AO-3 | -- | EO/BO | 10 |
| SAL-AO-4 | -CH 2 -CH(OH)-CH 2 - | EO | 9 |
3. The specific structure of the sodium lignin sulfonate polyether amphoteric surfactant is shown in table 2 below.
TABLE 2 Structure of sodium Lignosulfonate polyether amphoteric surfactant
| SAL-AO-Q | SAL-AO | R |
| SAL-AO-Q-1 | SAL-AO-1 | C8 |
| SAL-AO-Q-2 | SAL-AO-2 | C22 |
| SAL-AO-Q-3 | SAL-AO-3 | C18 |
| SAL-AO-Q-4 | SAL-AO-4 | C12 |
Example 1
The preparation method of the sodium lignin sulfonate polyether amphoteric surfactant for the polyester industrial yarns comprises the following steps:
sal pretreatment: (filtration- & gt ultrasonic activation- & gt ultrafiltration fractionation- & gt ultrafiltration dispersion), SAL in the range of 1kDa to 10kDa was taken.
(1) And (3) filtering: sodium lignin sulfonate (MJ-1, feihuang chemical Co., ltd.) water solution 5%, vacuum degree-0.5 Mpa, medium speed filter paper (15 cm) suction filtration, and getting lower layer filtrate A.
(2) Ultrasonic activation: the filtrate A is subjected to ultrasonic treatment for 2 hours at 25 ℃ under the power of 100% in ultrasonic waves to obtain a solution B, and the power of ultrasonic equipment is 400W.
(3) Ultrafiltration grading and impurity removal: UF201 ultrafiltration device (Seisakusho membrane technology development Co., ltd.) is used for treatment, and its effective filtration area is 0.008m 2 The working pressure is 0.1Mpa and the working temperature is 50 ℃. And (3) adopting an ultrafiltration membrane with the molecular weight cut-off of 10kDa specification to obtain a solution with the molecular weight of less than 10 kDa. Then the solution is subjected to ultrafiltration membrane with the molecular weight cut-off of 1kDa to obtain solution C with the molecular weight of 1kDa-10 kDa.
(4) And (3) distilling and drying: distilling the solution C in a rotary evaporator under reduced pressure, and drying the solution C in a vacuum oven at 80 ℃ for 48 hours under the vacuum degree of-0.5 Mpa to obtain pretreated sodium lignin sulfonate SAL.
Preparation of SAL-AO-1 (sodium lignin sulfonate polyether):
the nitrogen is replaced by pumping negative pressure in the reaction kettle and repeated for 3 times, 80g of N, N-Dimethylformamide (DMF) and 10g of SAL are introduced under stirring at 200rpm, then the temperature is raised to 100 ℃, 1.18g of sodium methoxide is added after 0.5h, the temperature is kept at 115 ℃, 176g of ethylene oxide and 390g of SAL are simultaneously introduced slowly, the introduction time of both is continued for 1h, and the curing reaction is finished until the pressure is stable for 0.5 h. Distilling under reduced pressure at 125deg.C, recovering DMF, cooling to 60deg.C, and neutralizing with glacial acetic acid to obtain SAL-AO-1. The SAL-AO-1 obtained by GPC measurement had a weight average molecular weight of 5760g/mol and a polydispersity index of 2.158829.
Preparation of SAL-AO-Q-1 (sodium Lignosulfonate amphoteric surfactant):
200g SAL-AO-1 was weighed and added to the reaction vessel, 800g deionized water (20% aqueous solution) was added, the temperature was raised to 55℃and the temperature was kept for 0.5h to allow complete dissolution. Then, the pH=9 of the reaction system was adjusted with a 0.5N NaOH aqueous solution, the temperature was raised to 80 ℃, 2g of tetrabutylammonium bromide was further added, 92.5g of Epichlorohydrin (ECH) was slowly added dropwise for 1 hour, and then the reaction was continued with stirring at a constant temperature for 5 hours. Then, 157g of N, N-dimethyl octyl amine is slowly added dropwise, meanwhile, the pH=8 is regulated by 0.1N NaOH aqueous solution, after 2h of dropwise addition, stirring is carried out for 2h of reaction, then, distillation is carried out to remove water, absolute ethyl alcohol is used for washing and suction filtration, and then, the SAL-AO-Q-1 is obtained after drying for 48h at 80 ℃ in a vacuum drying oven.
Example 2
The preparation method of the sodium lignin sulfonate polyether amphoteric surfactant for the polyester industrial yarns comprises the following steps:
sal pretreatment: (filtration- & gt ultrasonic activation- & gt ultrafiltration fractionation- & gt ultrafiltration dispersion), SAL in the range of 1kDa to 10kDa was taken.
(1) And (3) filtering: sodium lignin sulfonate (MJ-1, feihuang chemical Co., ltd.) water solution 10%, vacuum degree-0.1 Mpa, medium speed filter paper (15 cm) suction filtration, getting lower layer filtrate A.
(2) Ultrasonic activation: the filtrate A is subjected to ultrasonic treatment for 6 hours at 80 ℃ under the power of 80% in ultrasonic waves to obtain a solution B, and the power of ultrasonic equipment is 500W.
(3) Ultrafiltration grading and impurity removal: UF201 ultrafiltration device (Seisakusho membrane technology development Co., ltd.) is used for treatment, and its effective filtration area is 0.008m 2 The working pressure is 0.7Mpa and the working temperature is 60 ℃. And (3) adopting an ultrafiltration membrane with the molecular weight cut-off of 10kDa specification to obtain a solution with the molecular weight of less than 10 kDa. Then the solution is subjected to ultrafiltration membrane with the molecular weight cut-off of 1kDa to obtain solution C with the molecular weight of 1kDa-10 kDa.
(4) And (3) distilling and drying: distilling the solution C in a rotary evaporator under reduced pressure, and drying the solution C in a vacuum oven at 70 ℃ for 72 hours under the vacuum degree of-0.1 Mpa to obtain pretreated sodium lignin sulfonate SAL.
Preparation of SAL-AO-2 (sodium lignin sulfonate polyether):
the nitrogen is replaced by negative pressure in the reaction kettle, 50g of N, N-Dimethylformamide (DMF) and 5g of SAL are introduced under the stirring of 300rpm, then the temperature is raised to 110 ℃, 8g of potassium methoxide is added after 0.6h, the temperature is kept at 125 ℃, 528g of ethylene oxide and 395g of SAL are simultaneously introduced slowly for 4h, the curing reaction is carried out until the pressure is stable for 0.6h, 464g of ethylene oxide is introduced slowly for 2h, and the curing reaction is finished until the pressure is stable for 0.6 h. Distilling under reduced pressure at 135 deg.C, recovering DMF, cooling to 50deg.C, and neutralizing with glacial acetic acid to obtain SAL-AO-2. The SAL-AO-2 obtained by GPC measurement had a weight average molecular weight of 13920g/mol and a polydispersity index of 3.057762.
Preparation of SAL-AO-Q-2 (sodium Lignosulfonate amphoteric surfactant):
200g SAL-AO-2 was weighed and added to the reaction vessel, 1000g deionized water (16.7% aqueous solution) was added, the temperature was raised to 50℃and the temperature was kept for 1 hour to allow complete dissolution. Then, the pH=11 of the reaction system was adjusted with 1.0N NaOH aqueous solution, the temperature was raised to 75 ℃, 4g of tetrabutylammonium bromide was further added, 92.5. 92.5g Epichlorohydrin (ECH) was slowly added dropwise for 2 hours, and then the reaction was continued with heat preservation and stirring for 3 hours. Then, adding 353g of N, N-dimethyl-behenyl amine slowly, simultaneously adjusting the pH value to be 10 by using a 0.5N NaOH aqueous solution, stirring for reaction for 5 hours after the 0.5h dropwise addition, then distilling to remove water, washing by absolute ethyl alcohol, carrying out suction filtration, and then drying at 85 ℃ for 60 hours in a vacuum drying oven to obtain SAL-AO-Q-2.
Example 3
The preparation method of the sodium lignin sulfonate polyether amphoteric surfactant for the polyester industrial yarns comprises the following steps:
sal pretreatment: (filtration- & gt ultrasonic activation- & gt ultrafiltration fractionation- & gt ultrafiltration dispersion), SAL in the range of 1kDa to 10kDa was taken.
(1) And (3) filtering: sodium lignin sulfonate (MJ-1, feihuang chemical Co., ltd.) water solution 8%, vacuum degree-0.3 Mpa, medium speed filter paper (15 cm) suction filtration, getting lower layer filtrate A.
(2) Ultrasonic activation: the filtrate A is subjected to ultrasonic treatment for 4 hours at 50 ℃ under the power of 90% in ultrasonic waves to obtain a solution B, and the power of ultrasonic equipment is 400W.
(3) Ultrafiltration grading and impurity removal: UF201 ultrafiltration device (Seisakusho membrane technology development Co., ltd.) is used for treatment, and its effective filtration area is 0.008m 2 The working pressure is 0.3Mpa and the working temperature is 55 ℃. And (3) adopting an ultrafiltration membrane with the molecular weight cut-off of 10kDa specification to obtain a solution with the molecular weight of less than 10 kDa. Then the solution is subjected to ultrafiltration membrane with the molecular weight cut-off of 1kDa to obtain solution C with the molecular weight of 1kDa-10 kDa.
(4) And (3) distilling and drying: distilling the solution C in a rotary evaporator under reduced pressure, and drying the solution C in a vacuum oven at 75 ℃ for 56 hours under the vacuum degree of-0.7 Mpa to obtain pretreated sodium lignin sulfonate SAL.
Preparation of SAL-AO-3 (sodium lignin sulfonate polyether):
the nitrogen is replaced by negative pressure in the reaction kettle, 100g of N, N-Dimethylformamide (DMF) and 20g of SAL are introduced under stirring at 200rpm, then the temperature is raised to 110 ℃, 7.46g of potassium ethoxide is added after 0.5h, the temperature is kept at 120 ℃, 308g of ethylene oxide and 380g of SAL are simultaneously and slowly introduced for 2h, the curing reaction is carried out until the pressure is stable for 0.5h and is unchanged, the temperature is raised to 130 ℃, 216g of butylene oxide is slowly introduced, the introducing time is continued for 1h, and the curing reaction is finished until the pressure is stable for 0.5h and is unchanged. Distilling under reduced pressure at 125deg.C, recovering DMF, cooling to 60deg.C, and neutralizing with glacial acetic acid to obtain SAL-AO-3. The SAL-AO-3 obtained by GPC measurement had a weight average molecular weight of 9240g/mol and a polydispersity index of 2.601305.
Preparation of SAL-AO-Q-3 (sodium Lignosulfonate amphoteric surfactant):
200g SAL-AO-3 was weighed and added to the reactor, 600g deionized water (25% aqueous solution) was added, the temperature was raised to 60℃and the temperature was maintained for 0.5h to allow complete dissolution. Then, the pH=10 of the reaction system was adjusted with 0.5N NaOH aqueous solution, the temperature was raised to 85 ℃, 1.5g of tetrabutylammonium bromide was further added, 92.5. 92.5g Epichlorohydrin (ECH) was slowly added dropwise for 1.5 hours, and then the reaction was continued with stirring at a constant temperature for 4 hours. Then, 297g of N, N-dimethyl octadecylamine is slowly added dropwise, meanwhile, the pH=9 is regulated by using a 0.2N NaOH aqueous solution, after 1h of dropwise addition, stirring is carried out for 4h of reaction, then, distillation is carried out to remove water, absolute ethyl alcohol is used for washing and suction filtration, and then, the SAL-AO-Q-3 is obtained after drying for 48h at 80 ℃ in a vacuum drying box.
Example 4
The preparation method of the sodium lignin sulfonate polyether amphoteric surfactant for the polyester industrial yarns comprises the following steps:
sal pretreatment: (filtration- & gt ultrasonic activation- & gt ultrafiltration fractionation- & gt ultrafiltration dispersion), SAL in the range of 1kDa to 10kDa was taken.
(1) And (3) filtering: sodium lignin sulfonate (MJ-1, feihuang chemical Co., ltd.) water solution 7%, vacuum degree-0.8 Mpa, medium speed filter paper (15 cm) suction filtration, and getting lower layer filtrate A.
(2) Ultrasonic activation: the filtrate A is subjected to ultrasonic treatment for 3 hours at 60 ℃ under the power of 90% in ultrasonic waves to obtain a solution B, and the power of ultrasonic equipment is 500W.
(3) Ultrafiltration grading and impurity removal: UF201 ultrafiltration device (Seisakusho membrane technology development Co., ltd.) is used for treatment, and its effective filtration area is 0.008m 2 The working pressure is 0.5Mpa and the working temperature is 55 ℃. And (3) adopting an ultrafiltration membrane with the molecular weight cut-off of 10kDa specification to obtain a solution with the molecular weight of less than 10 kDa. Then the solution is subjected to ultrafiltration membrane with the molecular weight cut-off of 1kDa to obtain solution C with the molecular weight of 1kDa-10 kDa.
(4) And (3) distilling and drying: distilling the solution C in a rotary evaporator under reduced pressure, and drying at 80 ℃ in a vacuum oven for 60 hours under the vacuum degree of-0.8 Mpa to obtain pretreated sodium lignin sulfonate SAL.
Preparation of SAL-AO-4 (sodium lignin sulfonate polyether):
200g (0.5 mol) of PEG400 was added to the reaction vessel, the temperature was raised to 55℃and then 0.8g of boron trifluoride-diethyl ether (BF) was added to the reaction vessel 3 -Et 2 O), after stirring uniformly, 56g (0.6 mol) of Epichlorohydrin (ECH) was slowly added dropwise for 1h, keeping the temperature at 55 ℃. After the completion of the dropwise addition, the reaction was continued at 55℃for 2 hours. The residual ECH was then distilled off under reduced pressure to give chloro PEG400 intermediate. 100g SAL was then dissolved in 1N NaOH aqueous solution to prepare 25% strength aqueous solution, and then chloroPEG 400 intermediate was added dropwise, after 2h dropwise addition was completed, and then reacted at 80℃for 3h. After cooling, the pH was adjusted to about 7 by neutralization with concentrated hydrochloric acid, thereby obtaining a product. Then, purification treatment is carried out, butanone is added into the product solution for continuous extraction to remove unreacted PEG400 and water until yellow brown sticky matters appear at the lower layer, and the product is separated by centrifugation at 10000 rpm. Vacuum drying to obtain purified SAL-AO-4 sample. The SAL-AO-4 obtained by GPC measurement had a weight average molecular weight of 13216g/mol and a polydispersity index of 2.885009.
Preparation of SAL-AO-Q-4 (sodium Lignosulfonate amphoteric surfactant):
200g SAL-AO-4 was weighed and added to the reaction vessel, 1800g deionized water (10% aqueous solution) was added, the temperature was raised to 65℃and the temperature was kept for 0.5h to allow complete dissolution. Then, the pH=11 of the reaction system was adjusted with a 0.5N NaOH aqueous solution, the temperature was raised to 90℃and then 1g of tetrabutylammonium bromide was added thereto, 92.5g of Epichlorohydrin (ECH) was slowly added dropwise thereto for 0.5h, and then the reaction was continued with stirring at a constant temperature for 6h. Then slowly dropwise adding 213g of N, N-dimethyl dodecylamine, simultaneously adjusting the pH value to be 10 by using a 0.3N NaOH aqueous solution, stirring for reaction for 3 hours after the dropwise adding is finished, then distilling to remove water, washing by using absolute ethyl alcohol, carrying out suction filtration, and then drying in a vacuum drying oven at 80 ℃ for 48 hours to obtain SAL-AO-Q-4.
Example 5
This embodiment differs from embodiment 4 only in that:
preparation of SAL-AO-4 (sodium lignin sulfonate polyether):
250g PEG400 was added to the reaction vessel, the temperature was raised to 60℃and then 1g boron trifluoride-diethyl ether (BF) 3 -Et 2 O), after stirring uniformly, 60g of Epichlorohydrin (ECH) was slowly added dropwise for 0.5h, keeping the temperature at 60 ℃. After the completion of the dropwise addition, the reaction was continued at 60℃for 1 hour. However, the method is thatAnd then decompressing and distilling to remove residual ECH, thus obtaining the chlorinated PEG400 intermediate. 200g of SAL was then dissolved in 1N NaOH aqueous solution to prepare a 30% strength aqueous solution, and then chloroPEG 400 intermediate was added dropwise, after 1 hour of addition, the mixture was heated to 85℃and reacted for 1 hour. After cooling, the pH was adjusted to about 7.5 by neutralization with concentrated hydrochloric acid, thereby obtaining a product. Then, purification treatment is carried out, butanone is added into the product solution for continuous extraction to remove unreacted PEG400 and water until yellow brown sticky matters appear at the lower layer, and the product is separated by centrifugation at 8000 rpm. Vacuum drying to obtain purified SAL-AO-4 sample.
Example 6
This embodiment differs from embodiment 4 only in that:
preparation of SAL-AO-4 (sodium lignin sulfonate polyether):
220g of PEG400 was added to a reaction vessel, the temperature was raised to 60℃and then 0.9g of boron trifluoride-diethyl etherate (BF 3 -Et 2 O), after stirring uniformly, 58g of Epichlorohydrin (ECH) was slowly added dropwise for 2 hours, keeping the temperature at 60 ℃. After the completion of the dropwise addition, the reaction was continued at 60℃for 4 hours. The residual ECH was then distilled off under reduced pressure to give chloro PEG400 intermediate. 150g SAL was then dissolved in 1N NaOH aqueous solution to prepare 25% strength aqueous solution, and then chloroPEG 400 intermediate was added dropwise over 3 hours, followed by reaction at 85℃for 5 hours. After cooling, the pH was adjusted to about 7 by neutralization with concentrated hydrochloric acid, thereby obtaining a product. Then, purification treatment was performed, butanone was added to the product solution for continuous extraction to remove unreacted PEG400 and water until a yellowish brown viscous material appeared in the lower layer, and the product was centrifuged at 9000 rpm. Vacuum drying to obtain purified SAL-AO-4 sample.
The spinning oil for the polyester industrial yarn containing the sodium lignin sulfonate polyether amphoteric surfactant for the polyester industrial yarn is shown in the following table 3.
Table 3 polyester industrial yarn spinning finish tables of examples 7 to 12 and comparative examples 1 to 3
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Example 13:
this embodiment differs from embodiment 7 only in that: the preservative is sodium benzoate.
Example 14:
this embodiment differs from embodiment 10 only in that: the preservative is potassium sorbate.
Spinning experiment:
cluster oiling (oven 1, oven 2), stretching (oven 1, oven 2, oven 3), grid-winding forming.
The polyester industrial yarns of examples 7 to 12 and comparative examples 1 to 3 were treated according to the same spinning process conditions and process flow, respectively.
Dyeing experiment:
after spinning, the polyester industrial yarn is subjected to dyeing bath, oven 1, oven 2, reduction cleaning tank, steam box and water washing box.
The polyester industrial yarns treated in examples 7 to 12 and comparative examples 1 to 3 were dyed according to the same dyeing process conditions and process flow, respectively. The occurrence of white spots (the length of white spots occurring under the total length of the treated polyester industrial yarn, in ppm) is shown in Table 4.
Table 4 white spots Table of polyester Industrial yarns of examples 7 to 12 and comparative examples 1 to 3
| Experiment | White spots/ppm |
| Example 7 | 97 |
| Example 8 | 42 |
| Example 9 | 20 |
| Example 10 | 3 |
| Example 11 | 36 |
| Example 12 | 2 |
| Comparative example 1 | 411 |
| Comparative example 2 | 370 |
| Comparative example 3 | 368 |
As shown in fig. 1 and 2, white spots of comparative examples 1 and 2 are white spot patterns, and as can be seen from the patterns, white spots are in a linear shape, which indicates that the white spots are serious after the polyester industrial yarn of comparative example 1 which is not treated by the sodium lignin sulfonate amphoteric surfactant of the present invention is dyed by a one bath process, and the polyester industrial yarn is easy to be stained and have color defects.
As shown in FIG. 3, which is a white spot diagram of the embodiment 8 of the invention, it can be seen from the diagram that the white spot is less, only 42ppm, and is small, the white spot is not obvious, the color defect and the dyeing of the terylene industrial yarn are not easy to occur, the product quality is good, the qualification rate is high, and the spinning oil is suitable for the downstream enterprise to wash and dye the one bath process after the terylene industrial yarn treated by the sodium lignin sulfonate amphoteric surfactant of the invention is dyed by the one bath process.
As can be seen from table 2, in examples 11 and 12, the sodium lignin sulfonate amphoteric surfactant of the present invention was directly added to the existing spin finish, and the added existing spin finish also had the effect of greatly reducing white spots and greatly improving the product quality.
In the description provided herein, numerous specific details are set forth. However, it is understood that embodiments of the invention may be practiced without these specific details. In some instances, well-known methods, structures and techniques have not been shown in detail in order not to obscure an understanding of this description.
In the description of the present invention, it should be understood that the directions or positional relationships indicated by the terms "upper", "lower", "front", "rear", "left", "right", etc., are based on the directions or positional relationships shown in the drawings, are merely for convenience of describing the present invention and simplifying the description, and do not indicate or imply that the devices or elements referred to must have a specific orientation, be constructed and operated in a specific orientation, and thus should not be construed as limiting the present invention.
Similarly, it should be appreciated that in the foregoing description of exemplary embodiments of the invention, various features of the invention are sometimes grouped together in a single embodiment, figure, or description thereof for the purpose of streamlining the disclosure and aiding in the understanding of one or more of the various inventive aspects. However, the disclosed method should not be construed as reflecting the intention that: i.e., the claimed invention requires more features than are expressly recited in each claim. Rather, as the following claims reflect, inventive aspects lie in less than all features of a single foregoing disclosed embodiment. Thus, the claims following the detailed description are hereby expressly incorporated into this detailed description, with each claim standing on its own as a separate embodiment of this invention.
While the invention has been described with respect to a limited number of embodiments, those skilled in the art, having benefit of the above description, will appreciate that other embodiments are contemplated within the scope of the invention as described herein. Furthermore, it should be noted that the language used in the specification has been principally selected for readability and instructional purposes, and may not have been selected to delineate or circumscribe the inventive subject matter. Accordingly, many modifications and variations will be apparent to those of ordinary skill in the art without departing from the scope and spirit of the appended claims. The disclosure of the present invention is intended to be illustrative, but not limiting, of the scope of the invention, which is defined by the appended claims.
The foregoing is only a preferred embodiment of the invention, it being noted that: it will be apparent to those skilled in the art that various modifications and adaptations can be made without departing from the principles of the present invention, and such modifications and adaptations are intended to be comprehended within the scope of the invention.
Claims (7)
1. The polyester industrial yarn spinning oil containing the sodium lignin sulfonate polyether amphoteric surfactant for the polyester industrial yarn is characterized in that: the structural unit of the sodium lignin sulfonate polyether amphoteric surfactant is as follows:
wherein SAL is sodium lignin sulfonate;
AO is polyether, and AO comprises any one or combination of ethylene oxide EO, propylene oxide PO and butylene oxide BO;
m is in the range of 4-20;
r comprises C8-C22 straight-chain alkane;
b comprises no substituent;
the polyester industrial yarn spinning oil comprises the following components in parts by weight: smoothing agent: 50 parts of surfactant: 30 parts of preservative: 0.1 part and water: 320 parts; the surfactant comprises: sodium lignin sulfonate polyether amphoteric surfactant: 1-20 parts of propylene glycol block polyether L61:3-6 parts of oleyl alcohol polyoxyethylene ether ester OV-5:2-10 parts of hydrogenated castor oil polyoxyethylene ether HEL-20:1-10 parts of polyethylene glycol dioleate PEG400DO:1-6 parts;
the smoothing agent comprises glycerol trioleate and lauryl oleate in a weight ratio of 2:3.
2. The polyester industrial yarn spinning finish according to claim 1, wherein: b is formed by-CH 2 -CH(OH)-CH 2 -substitution of unsubstituted groups.
3. The polyester industrial yarn spinning finish according to claim 1, wherein: the preparation method of the sodium lignin sulfonate polyether amphoteric surfactant comprises the following steps:
step one, pretreatment of sodium lignin sulfonate SAL: obtaining sodium lignin sulfonate SAL with molecular weight of 1KDa-10 KDa;
step two, preparing sodium lignin sulfonate polyether SAL-AO:
pumping negative pressure to replace nitrogen in the reaction kettle, repeating for at least 3 times, and stirring at 200-300rpm, and introducing N, N-dimethylformamide DMF and sodium lignin sulfonate SAL with the weight ratio of (5-10): 1; then heating to 100-110 ℃, adding an alkaline catalyst after 0.5-0.6h, wherein the adding weight of the alkaline catalyst is equivalent to 11.8-160% of sodium lignin sulfonate SAL after the first pretreatment, and keeping the temperature at 115-125 ℃;
then carrying out curing reaction for 1-2 times;
first curing reaction: simultaneously, slowly introducing AO and sodium lignin sulfonate SAL after the second pretreatment, wherein the introducing time of both the AO and the sodium lignin sulfonate SAL lasts for 1-4 hours, the introducing weight of AO is equivalent to 17.6-105.6 times of that of the sodium lignin sulfonate SAL after the first pretreatment, and the introducing weight of the sodium lignin sulfonate SAL after the second pretreatment is equivalent to 39-79 times of that of the sodium lignin sulfonate SAL after the first pretreatment; curing reaction until the pressure is stable for 0.5-0.6 h;
second curing reaction: after the first curing reaction is finished, the temperature is not increased or is increased to 125-135 ℃, and then AO is slowly introduced, wherein the introduced weight of AO is 21.6-46.4 times of that of sodium lignin sulfonate SAL after the first pretreatment; the time is continuously 1-2h, and the reaction is finished when the pressure is stable for 0.5-0.6 h;
then carrying out reduced pressure distillation at 125-135 ℃ to recover N, N-dimethylformamide DMF, then cooling to 50-60 ℃, and neutralizing with glacial acetic acid to obtain sodium lignin sulfonate polyether SAL-AO;
step three, preparing a sodium lignin sulfonate polyether amphoteric surfactant SAL-AO-Q:
weighing a proper amount of sodium lignin sulfonate polyether SAL-AO, adding deionized water with the weight 3-9 times that of the sodium lignin sulfonate polyether SAL-AO into a reaction kettle, heating to 50-65 ℃, and preserving heat for 0.5-1h to enable the sodium lignin sulfonate polyether SAL-AO to be fully dissolved; then adjusting the pH value of a reaction system to be between 9 and 11 by using a 0.5 and 1.0N NaOH aqueous solution, heating to 80 to 90 ℃, adding tetrabutylammonium bromide, wherein the adding weight of the tetrabutylammonium bromide is equal to 0.5 to 2 percent of that of sodium lignin sulfonate polyether SAL-AO, slowly dropwise adding epichlorohydrin ECH for 0.5 to 2 hours, and the adding weight of the epichlorohydrin ECH is equal to 46.25 percent of that of sodium lignin sulfonate polyether SAL-AO; then continuing to keep the temperature and stir for reaction for 3-6h; slowly dropwise adding N, N-dimethyl alkylamine, wherein the adding weight of the N, N-dimethyl alkylamine is 78.5-176.5% of that of sodium lignin sulfonate polyether SAL-AO; and simultaneously adjusting the pH value to be 8-10 by using a 0.1-0.5N NaOH aqueous solution, stirring for 2-5h after the dropwise addition of the solution is completed, distilling to remove water, washing by using absolute ethyl alcohol, filtering, and drying at 80-85 ℃ for at least 48h in a vacuum drying oven to obtain SAL-AO-Q.
4. The polyester industrial yarn spinning finish according to claim 2, wherein: the preparation method of the sodium lignin sulfonate polyether amphoteric surfactant comprises the following steps:
step one, pretreatment of sodium lignin sulfonate SAL: obtaining sodium lignin sulfonate SAL with molecular weight of 1KDa-10 KDa;
step two, preparing sodium lignin sulfonate polyether SAL-AO:
200-250g PEG400 is added into a reaction kettle, the temperature is raised to 55-60 ℃, and then 0.8-1g boron trifluoride-diethyl ether BF is added into the reaction kettle 3 -Et 2 O, after uniformly stirring, slowly dropwise adding 56-60g of epichlorohydrin ECH for 0.5-2h, and keeping the temperature at 55-60 ℃; after the dripping is finished, continuously keeping the temperature of 55-60 ℃ for reaction for 1-4h; then decompressing and distilling to remove residual epichlorohydrin ECH to obtain chlorinated PEG400 intermediate; then 100-200g of pretreated sodium lignin sulfonate SAL is dissolved in 1N NaOH aqueous solution to prepare aqueous solution with the concentration of 25-30%, then chlorinated PEG400 intermediate is dripped, after 1-3h of dripping is finished, the temperature is raised and the reaction is carried out for 1-5h at 80-85 ℃; after cooling, neutralizing with concentrated hydrochloric acid to adjust the pH to 7-7.5, thereby obtaining a product; then purifying, adding butanone into the product solution for continuous extraction to remove unreacted PEG400 and water until yellow brown sticky matters appear at the lower layer, and centrifuging at 8000-10000rpm to separate out the product; vacuum drying to obtain purified sodium lignin sulfonate polyether SAL-AO;
step three, preparing a sodium lignin sulfonate polyether amphoteric surfactant SAL-AO-Q:
weighing a proper amount of sodium lignin sulfonate polyether SAL-AO, adding deionized water with the weight 3-9 times that of the sodium lignin sulfonate polyether SAL-AO into a reaction kettle, heating to 50-65 ℃, and preserving heat for 0.5-1h to enable the sodium lignin sulfonate polyether SAL-AO to be fully dissolved; then adjusting the pH value of a reaction system to be between 9 and 11 by using a 0.5 and 1.0N NaOH aqueous solution, heating to 80 to 90 ℃, adding tetrabutylammonium bromide, wherein the adding weight of the tetrabutylammonium bromide is equal to 0.5 to 2 percent of that of sodium lignin sulfonate polyether SAL-AO, slowly dropwise adding epichlorohydrin ECH for 0.5 to 2 hours, and the adding weight of the epichlorohydrin ECH is equal to 46.25 percent of that of sodium lignin sulfonate polyether SAL-AO; then continuing to keep the temperature and stir for reaction for 3-6h; slowly dropwise adding N, N-dimethyl alkylamine, wherein the adding weight of the N, N-dimethyl alkylamine is 78.5-176.5% of that of sodium lignin sulfonate polyether SAL-AO; and simultaneously adjusting the pH value to be 8-10 by using a 0.1-0.5N NaOH aqueous solution, stirring for 2-5h after the dropwise addition of the solution is completed, distilling to remove water, washing by using absolute ethyl alcohol, filtering, and drying at 80-85 ℃ for at least 48h in a vacuum drying oven to obtain SAL-AO-Q.
5. The polyester industrial yarn spinning finish according to claim 3, wherein: n, N-dimethyl alkylamines include N, N-dimethyl octylamine, N-dimethyl-behenyl amine, N-dimethyl-octadecyl amine or N, N-dimethyl-dodecyl amine; the basic catalyst comprises sodium methoxide, potassium methoxide or sodium ethoxide.
6. The polyester industrial yarn spinning finish according to claim 1, wherein: the preservative comprises pinus koraiensis, sodium benzoate or potassium sorbate.
7. The application of the polyester industrial yarn obtained by adopting the polyester industrial yarn spinning oil solution spinning in dyeing is characterized in that: the white spots of the terylene industrial yarn are less than 100ppm.
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| US3355400A (en) * | 1960-09-26 | 1967-11-28 | Union Carbide Corp | Polyether-lignin compositions |
| WO2014114155A1 (en) * | 2013-01-22 | 2014-07-31 | 华南理工大学 | Lignin dye dispersant with carboxyl and sulfonic groups and preparation method therefor |
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| ES2945578T3 (en) * | 2018-11-29 | 2023-07-04 | Fundacion Tecnalia Res & Innovation | lignin based polyols |
| JP7194273B2 (en) * | 2020-06-01 | 2022-12-21 | ゼージアン グローリ ホーム ファーニシングス カンパニー リミテッド | Production method of lignin block copolymer molecular level composite polyether and application of lignin block copolymer molecular level composite polyether to production of flexible polyurethane foam material |
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| US3355400A (en) * | 1960-09-26 | 1967-11-28 | Union Carbide Corp | Polyether-lignin compositions |
| WO2014114155A1 (en) * | 2013-01-22 | 2014-07-31 | 华南理工大学 | Lignin dye dispersant with carboxyl and sulfonic groups and preparation method therefor |
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| Study on Synthesis and Performance of Lignin Polyether Sulfonate Surfactants for Enhanced Oil Recovery;Hong Sun;《Journal of dispersion science and technology》;1355-1359 * |
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