CN114875675A - Sodium lignosulfonate polyether amphoteric surfactant for polyester industrial yarns, polyester industrial yarn spinning oil agent, and preparation method and application thereof - Google Patents
Sodium lignosulfonate 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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- CN114875675A CN114875675A CN202210487237.1A CN202210487237A CN114875675A CN 114875675 A CN114875675 A CN 114875675A CN 202210487237 A CN202210487237 A CN 202210487237A CN 114875675 A CN114875675 A CN 114875675A
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- sodium lignosulfonate
- sal
- polyether
- polyester industrial
- amphoteric surfactant
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- 229920005552 sodium lignosulfonate Polymers 0.000 title claims abstract description 127
- 229920000570 polyether Polymers 0.000 title claims abstract description 90
- 239000004721 Polyphenylene oxide Substances 0.000 title claims abstract description 89
- 229920000728 polyester Polymers 0.000 title claims abstract description 81
- 239000002280 amphoteric surfactant Substances 0.000 title claims abstract description 55
- 238000009987 spinning Methods 0.000 title claims abstract description 46
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 31
- 241000519995 Stachys sylvatica Species 0.000 claims abstract description 27
- 230000008569 process Effects 0.000 claims abstract description 21
- 238000004043 dyeing Methods 0.000 claims abstract description 19
- 238000005406 washing Methods 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims description 69
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 63
- 239000007864 aqueous solution Substances 0.000 claims description 36
- 239000000243 solution Substances 0.000 claims description 36
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 32
- 239000003921 oil Substances 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 238000003756 stirring Methods 0.000 claims description 23
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 claims description 22
- 238000001035 drying Methods 0.000 claims description 18
- 238000010438 heat treatment Methods 0.000 claims description 17
- 238000004821 distillation Methods 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 238000000967 suction filtration Methods 0.000 claims description 10
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 9
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 8
- 239000008367 deionised water Substances 0.000 claims description 8
- 229910021641 deionized water Inorganic materials 0.000 claims description 8
- 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
- 239000003755 preservative agent Substances 0.000 claims description 6
- 230000002335 preservative effect Effects 0.000 claims description 6
- 238000006386 neutralization reaction Methods 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- 238000000605 extraction Methods 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
- 125000001424 substituent group Chemical group 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
- 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
- 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
- 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
- UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 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
- 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
- 239000006185 dispersion Substances 0.000 abstract description 6
- 230000008901 benefit Effects 0.000 abstract description 4
- 238000004945 emulsification Methods 0.000 abstract description 4
- 230000006870 function Effects 0.000 abstract description 3
- 238000005536 corrosion prevention Methods 0.000 abstract description 2
- 239000003995 emulsifying agent Substances 0.000 abstract description 2
- 238000000108 ultra-filtration Methods 0.000 description 32
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 238000001914 filtration Methods 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 12
- 239000012528 membrane Substances 0.000 description 12
- 230000004913 activation Effects 0.000 description 10
- 230000007547 defect Effects 0.000 description 8
- 239000000835 fiber Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000005194 fractionation Methods 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 238000009210 therapy by ultrasound Methods 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 229920005610 lignin Polymers 0.000 description 3
- 230000003472 neutralizing effect Effects 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000010586 diagram Methods 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 235000017166 Bambusa arundinacea Nutrition 0.000 description 1
- 235000017491 Bambusa tulda Nutrition 0.000 description 1
- 241001330002 Bambuseae Species 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
- 235000015334 Phyllostachys viridis Nutrition 0.000 description 1
- 229920004933 Terylene® Polymers 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000011425 bamboo Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000011109 contamination 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
- 238000004134 energy conservation Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- ICZKASVWFUJTEI-UHFFFAOYSA-N n,n-dimethyldocosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCN(C)C ICZKASVWFUJTEI-UHFFFAOYSA-N 0.000 description 1
- 239000005020 polyethylene terephthalate 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
- 238000000746 purification Methods 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002455 scale inhibitor Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Images
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
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- Chemical & Material Sciences (AREA)
- Textile Engineering (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Microbiology (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a sodium lignosulfonate polyether amphoteric surfactant for polyester industrial yarns, a polyester industrial yarn spinning oil agent, a preparation method and application thereof. The sodium lignosulfonate polyether amphoteric surfactant prepared by the invention is used as an emulsifier and added into a spinning oil agent, and mainly plays roles in emulsification, antistatic and corrosion prevention in the spinning process; the main functions of emulsification, deoiling, dye dispersion and the like are realized in the washing and dyeing one-bath process. The white spots of the industrial polyester yarn are less than 100ppm when the industrial polyester yarn obtained by spinning the industrial polyester yarn spinning oil agent is applied to one-bath dyeing. The application of the polyester industrial yarn obtained by combining the sodium lignosulfonate polyether amphoteric surfactant for the polyester industrial yarn with the existing spinning oil agent spinning in one-bath dyeing has the advantages that the white spots of the polyester industrial yarn are less than 40 ppm.
Description
Technical Field
The invention belongs to the technical field of polyester industrial yarns, and particularly relates to a sodium lignosulfonate polyether amphoteric surfactant for polyester industrial yarns, a polyester industrial yarn spinning oil agent, and a preparation method and application thereof.
Background
In the processes of spinning, drawing, twisting and the like of chemical fibers such as terylene, chinlon and the like, in order to reduce friction coefficient, eliminate electrostatic influence and improve spinnability and processability, a proper amount of spinning oil needs to be added, and the quality of the spinning oil directly determines the quality of the chemical fibers. Under the background of rapid development of the chemical fiber industry at present, the polyester products are more important, so the quality of the polyester spinning oil product can directly influence the whole chemical fiber industry. The technical requirements of the polyester industrial yarn spinning oil agent are far greater than those of polyester civil yarn spinning oil agents.
With the continuous promotion of energy conservation and emission reduction and low carbon consumption reduction of China, the process technology of the short process, low bath ratio and one bath method of enterprises is continuously updated, and new requirements are provided for the spinning oil of the enterprises. In the actual production process, the conditions of dyeing defects, color defects and the like can be met frequently when the spinning process is good in spinnability and is applied by downstream enterprises. Especially, when the low bath ratio and one bath process are used, the change and washing of the vat is more frequent, and the conditions of dyeing and color defects are more serious. Therefore, there is a need to develop a spinning oil suitable for the one-bath process of washing and dyeing in downstream enterprises, and there is an urgent need for a sodium lignosulfonate polyether amphoteric surfactant for polyester industrial yarns, a polyester industrial yarn spinning oil, and a preparation method and application thereof.
Disclosure of Invention
In addition, in the deoiling process, due to the double electric layer effect, oil is wrapped in the solution, so that the state of emulsion is very stable, and the dyeing and dyeing caused by contamination are avoided; in addition, polyether AO is introduced into the amphoteric surfactant to increase the water solubility of the amphoteric surfactant, so that the deoiled emulsion is more stable, and the yarn is prevented from being polluted again due to demulsification.
Meanwhile, the invention also provides a preparation method of the sodium lignosulfonate polyether amphoteric surfactant for the polyester industrial yarn.
Meanwhile, the invention provides a polyester industrial yarn spinning oil agent containing sodium lignosulfonate polyether amphoteric surfactant for polyester industrial yarn.
Meanwhile, the invention provides the application of the polyester industrial yarn obtained by spinning the polyester industrial yarn spinning oil agent in dyeing, and white spots of the polyester industrial yarn dyed by the one-bath process are less than 100 ppm.
Meanwhile, the invention provides a sodium lignosulfonate polyether amphoteric surfactant for polyester industrial yarns, which is used in combination with the existing spinning oil agent spinning, and white spots of the obtained polyester industrial yarns are less than 40ppm after the polyester industrial yarns are dyed by a one-bath process.
In order to solve the technical problems, the technical scheme adopted by the invention is as follows:
a sodium lignosulfonate polyether amphoteric surfactant for polyester industrial yarns comprises the following structural units:
wherein SAL is sodium lignosulfonate;
AO is polyether, AO comprises any one or combination of ethylene oxide EO, propylene oxide PO and butylene oxide BO;
the value range of m is 4-20;
r comprises straight-chain alkane of C8-C22;
b comprises no substituent.
Or B is represented by-CH 2 -CH(OH)-CH 2 -replacing no substituent.
A preparation method of sodium lignosulfonate polyether amphoteric surfactant for polyester industrial yarn comprises the following steps (B is an unsubstituted group):
step one, pretreating sodium lignosulfonate SAL:
s01, filtering: taking sodium lignosulfonate aqueous solution with the mass percentage concentration of 5-10%, carrying out suction filtration by using medium-speed filter paper under the vacuum degree of-0.5-minus 0.1Mpa, and taking lower-layer filtrate A;
s02, ultrasonic activation: carrying out ultrasonic treatment on the filtrate A for 2-6h 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, fractionation and impurity removal: treating with ultrafiltration device, subjecting the solution B to ultrafiltration membrane with cut-off molecular weight of 10KDa, and collecting solution with molecular weight less than 10 KDa; then, adopting an ultrafiltration membrane with the molecular weight cutoff of 1KDa to obtain a solution C with the molecular weight of 1KDa-10 KDa;
s04, distillation and drying: distilling the solution C in a rotary evaporator under reduced pressure with the vacuum degree of-0.5 to-0.1 Mpa, and drying in a vacuum oven at 70-80 ℃ for 48-72 h;
step two, preparing sodium lignosulfonate polyether SAL-AO:
the reaction kettle is pumped to replace nitrogen by negative pressure and is repeated for at least 3 times, and N, N-dimethylformamide DMF with the weight ratio of (5-10):1 and the first batch of pretreated sodium lignosulfonate SAL are introduced under the stirring of 200-300 rpm; then heating to 100-125 ℃, adding an alkaline catalyst after 0.5-0.6h, wherein the adding weight of the alkaline catalyst is 11.8-160% of the weight of the first pretreated sodium lignosulfonate SAL, and keeping the temperature at 115-125 ℃;
then carrying out 1-2 times of curing reaction;
first curing reaction: slowly introducing AO and the second batch of pretreated sodium lignosulfonate SAL at the same time, wherein the introduction time of the AO and the second batch of pretreated sodium lignosulfonate SAL lasts for 1-4h, the introduction weight of the AO is equivalent to 17.6-105.6 times of that of the first batch of pretreated sodium lignosulfonate SAL, and the introduction weight of the second batch of pretreated sodium lignosulfonate SAL is equivalent to 39-79 times of that of the first batch of pretreated sodium lignosulfonate SAL; curing reaction is carried out until the pressure is stable for 0.5-0.6 h;
and (3) second curing reaction: after the first curing reaction is finished, raising the temperature to 125-135 ℃, and then slowly introducing AO, wherein the introduction weight of AO is equivalent to 21.6-46.4 times of that of the first pretreated sodium lignosulfonate SAL; the introducing time lasts for 1-2h, and the reaction is finished when the pressure is stable for 0.5-0.6h after the curing reaction;
then carrying out reduced pressure distillation at the temperature of 125-;
step three, preparing a sodium lignosulfonate polyether amphoteric surfactant SAL-AO-Q:
weighing a proper amount of sodium lignosulfonate polyether SAL-AO, adding into a reaction kettle, adding deionized water with the weight 3-9 times of that of the sodium lignosulfonate polyether SAL-AO, heating to 50-65 ℃, and preserving heat for 0.5-1h to fully dissolve the sodium lignosulfonate polyether SAL-AO; then adjusting the pH value of the reaction system to 9-11 by using 0.5-1.0N NaOH aqueous solution, heating to 80-90 ℃, adding tetrabutylammonium bromide, slowly dropwise adding epoxy chloropropane ECH, wherein the adding weight of the tetrabutylammonium bromide is 0.5-2% of that of sodium lignosulfonate polyether SAL-AO, and the adding weight of the epoxy chloropropane ECH is 46.25% of that of the sodium lignosulfonate polyether SAL-AO; then continuously preserving heat and stirring for reaction for 3-6 h; then 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 lignosulfonate polyether SAL-AO; and simultaneously, adjusting the pH value to 8-10 by using 0.1-0.5N NaOH aqueous solution, after 0.5-2h of dropwise adding, stirring and reacting for 2-5h, then distilling to remove water, washing by using absolute ethyl alcohol, carrying out suction filtration, and then drying for at least 48h in a vacuum drying oven at the temperature of 80-85 ℃ to obtain SAL-AO-Q.
A method for preparing sodium lignosulfonate polyether amphoteric surfactant for polyester industrial yarn comprises the following steps (B is-CH) 2 -CH(OH)-CH 2 -substituents):
step one, pretreating sodium lignosulfonate SAL:
s01, filtering: taking sodium lignosulfonate aqueous solution with the mass percentage concentration of 5-10%, carrying out suction filtration by using medium-speed filter paper under the vacuum degree of-0.5-minus 0.1Mpa, and taking lower-layer filtrate A;
s02, ultrasonic activation: carrying out ultrasonic treatment on the filtrate A for 2-6h 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, fractionation and impurity removal: treating with ultrafiltration device, subjecting the solution B to ultrafiltration membrane with cut-off molecular weight of 10KDa, and collecting solution with molecular weight less than 10 KDa; then, adopting an ultrafiltration membrane with the molecular weight cutoff of 1KDa to obtain a solution C with the molecular weight of 1KDa-10 KDa;
s04, distillation and drying: distilling the solution C in a rotary evaporator under reduced pressure with the vacuum degree of-0.5 to-0.1 Mpa, and drying in a vacuum oven at 70-80 ℃ for 48-72 h;
step two, preparing sodium lignosulfonate polyether SAL-AO:
adding 200-250g PEG400 into a reaction kettle, heating to 55-60 ℃, and then adding 0.8-1g boron trifluoride-diethyl ether BF into the reaction kettle 3 -Et 2 O, after uniformly stirring, slowly dripping 56-60g of epichlorohydrin ECH for 0.5-2h, and keeping the temperature at 55-60 ℃; after the dropwise addition is finished, continuously keeping the temperature of 55-60 ℃ for reaction for 1-4 h; then carrying out reduced pressure distillation to remove residual epichlorohydrin ECH to obtain a chlorinated PEG400 intermediate; then dissolving 100-200g of pretreated sodium lignosulfonate SAL in 1N NaOH aqueous solution to prepare 25-30% aqueous solution, dropwise adding chlorinated PEG400 intermediate for 1-3h, and heating to 80-85 deg.CThe reaction time is 1-5 h; after cooling, the pH is adjusted to 7-7.5 by neutralization with concentrated hydrochloric acid, thereby obtaining a product; then purifying, adding butanone into the product solution for continuous extraction to remove unreacted PEG400 and water until the lower layer appears yellow brown sticky matter, and centrifuging at 8000-; vacuum drying to obtain purified sodium lignosulfonate polyether SAL-AO;
step three, preparing a sodium lignosulfonate polyether amphoteric surfactant SAL-AO-Q:
weighing a proper amount of sodium lignosulfonate polyether SAL-AO, adding into a reaction kettle, adding deionized water with the weight 3-9 times of that of the sodium lignosulfonate polyether SAL-AO, heating to 50-65 ℃, and preserving heat for 0.5-1h to fully dissolve the sodium lignosulfonate polyether SAL-AO; then adjusting the pH value of the reaction system to 9-11 by using 0.5-1.0N NaOH aqueous solution, heating to 80-90 ℃, adding tetrabutylammonium bromide, slowly dropwise adding epoxy chloropropane ECH, wherein the adding weight of the tetrabutylammonium bromide is 0.5-2% of that of sodium lignosulfonate polyether SAL-AO, and the adding weight of the epoxy chloropropane ECH is 46.25% of that of the sodium lignosulfonate polyether SAL-AO; then continuously preserving heat and stirring for reaction for 3-6 h; then 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 lignosulfonate polyether SAL-AO; and simultaneously, adjusting the pH value to 8-10 by using 0.1-0.5N NaOH aqueous solution, after 0.5-2h of dropwise adding, stirring and reacting for 2-5h, then distilling to remove water, washing by using absolute ethyl alcohol, carrying out suction filtration, and then drying for at least 48h in a vacuum drying oven at the temperature of 80-85 ℃ to obtain SAL-AO-Q.
The N, N-dimethyl alkylamine includes N, N-dimethyl octylamine, N-dimethyl behenylamine, N-dimethyl octadecylamine or N, N-dimethyl dodecylamine.
The basic catalyst includes sodium methoxide, potassium methoxide or sodium ethoxide.
The polyester industrial yarn spinning oil agent comprises the sodium lignosulfonate polyether amphoteric surfactant for the polyester industrial yarn, and comprises the following components in parts by weight: smoothing agent: 50 parts, surfactant: 30 parts, preservative: 0.1 part and water: 320 parts of (a); the surfactant includes: sodium lignosulfonate 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 PEG400 DO: 1-6 parts.
The smoothing agent comprises glycerol trioleate and lauryl oleate in a weight ratio of 2: 3.
The preservative comprises cason, sodium benzoate or potassium sorbate.
The white spots of the industrial polyester yarn are less than 100ppm, and compared with the prior art, the white spots are reduced by more than 76%.
The application of the polyester industrial yarn obtained by spinning the existing spinning oil agent containing the sodium lignosulfonate polyether amphoteric surfactant for the polyester industrial yarn in dyeing has the advantages that the white spot of the polyester industrial yarn is less than 40ppm, and compared with the prior art, the white spot of the polyester industrial yarn can be reduced by more than 99% in the best case.
Compared with the prior art, the invention has the beneficial effects that:
1. the sodium lignosulfonate polyether amphoteric surfactant is a lignin derivative, and the lignin derivative is used as a biomass material, meets the national requirements on green and environment-friendly renewable raw materials, and is particularly important when petrochemical raw materials are gradually exhausted and become severe.
2. The sodium lignosulfonate polyether amphoteric surfactant is used as a dye dispersant, a refining agent and a scale inhibitor, and has certain antibacterial performance. After the spinning oil is applied to the polyester industrial yarns, the polyester industrial yarns are applied to downstream enterprises, and when the one-bath process is carried out, the sodium lignosulfonate polyether amphoteric surfactant not only plays a refining function, but also is used as a dispersing agent for dispersing dye to further keep the stability of a dye bath and enable the dye concentration to be uniformly spread on the surfaces of the polyester industrial yarns until the dye concentration is fixed. In addition, the sodium lignosulfonate polyether amphoteric surfactant also has certain scale inhibition performance, so that the sodium lignosulfonate 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 spots and color defects, reducing the risk of rework and reducing the cost. In addition, the sodium lignosulfonate polyether amphoteric surfactant, especially the bamboo wood lignin derivative, has good antibacterial performance, so that the sodium lignosulfonate polyether amphoteric surfactant has a certain antibacterial effect, and the times of changing and washing a dye vat due to mildew are reduced, so that the cost is reduced, and the pollution discharge is reduced. In addition, after the chemical fibers are oiled, the storage time of the finished chemical fibers can be prolonged in the process of storage of the finished chemical fibers in a tube, and the probability of mildew is reduced.
3. In the sodium lignosulfonate polyether amphoteric surfactant, polyether AO is introduced to mainly increase the water solubility of the surfactant, so that deoiled emulsion is more stable, and the phenomenon that yarns are polluted again due to demulsification is avoided.
4. The sodium lignosulfonate polyether amphoteric surfactant greatly improves the antistatic property. In addition, in the deoiling process, due to the double electric layer effect, the oil is wrapped in the solution, so that the emulsion state is very stable, and the pollution caused by staining is avoided.
5. The sodium lignosulfonate polyether amphoteric surfactant prepared by the invention is used as an emulsifier and added into a spinning oil agent, and mainly plays roles in emulsification, antistatic and corrosion prevention in the spinning process; the main functions of emulsification, deoiling, dye dispersion and the like are realized in the washing and dyeing one-bath process.
6. The white spots of the industrial polyester yarn are less than 100ppm, and compared with the prior art, the white spots are reduced by more than 76%.
7. The application of the polyester industrial yarn obtained by combining the sodium lignosulfonate polyether amphoteric surfactant for the polyester industrial yarn with the existing spinning oil agent spinning in one-bath dyeing has the advantages that the white spot of the polyester industrial yarn is less than 40ppm, and compared with the prior art, the white spot of the polyester industrial yarn can be reduced by more than 99% in the best case.
Drawings
FIG. 1 is a white spot pattern of comparative example 1 of the present invention;
FIG. 2 is a white spot pattern of comparative example 2 of the present invention;
FIG. 3 is a white spot map of example 8 of the present invention.
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to the accompanying drawings, and the embodiments described below are only some embodiments, but not all embodiments, of the present invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
1. Reaction scheme
2. The specific structure of sodium lignosulfonate polyether is shown in table 1 below.
TABLE 1 sodium Lignosulfonate polyethers Structure
| 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 lignosulfonate polyether amphoteric surfactant is shown in table 2 below.
Table 2 sodium lignosulfonate polyether amphoteric surfactant structure
| 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
A preparation method of sodium lignosulfonate polyether amphoteric surfactant for polyester industrial yarn comprises the following steps:
SAL pretreatment: (filtration → ultrasonic activation → ultrafiltration fractionation → ultrafiltration dispersion), SAL ranging from 1kDa to 10kDa was taken.
(1) And (3) filtering: 5% aqueous solution of sodium lignosulfonate (MJ-1, Feihuang chemical Co., Ltd., New Yiyi) was filtered at medium speed filter paper (15cm) under a vacuum degree of-0.5 MPa, and the lower layer filtrate A was taken.
(2) Ultrasonic activation: and (3) carrying out ultrasonic treatment on the filtrate A for 2 hours at 25 ℃ under the power of 100% in ultrasonic waves to obtain a solution B, wherein the power of ultrasonic equipment is 400W.
(3) And (3) ultrafiltration grading impurity removal: treating with UF201 ultrafiltration device (Wuxi Saipu film science and technology development Co., Ltd.), with effective filtration area of 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 cutoff of 10KDa specification to obtain a solution with the molecular weight less than 10 KDa. Then, an ultrafiltration membrane with the molecular weight cutoff of 1KDa specification is adopted to obtain a solution C with the molecular weight of 1KDa-10 KDa.
(4) And (3) distillation and drying: and distilling the solution C in a rotary evaporator under reduced pressure with the vacuum degree of-0.5 Mpa, and then drying in a vacuum oven at the temperature of 80 ℃ for 48 hours to obtain the pretreated sodium lignosulfonate SAL.
Preparation of SAL-AO-1 (sodium lignosulfonate polyether):
the reaction kettle is pumped out to replace nitrogen under negative pressure and is repeated for 3 times, 80g of N, N-Dimethylformamide (DMF) and 10g of SAL are introduced under the stirring of 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 slowly introduced at the same time, the introduction time of the two is kept for 1h, and the reaction is finished when the pressure is stabilized for 0.5h after the curing reaction. Distilling under reduced pressure at 125 deg.C, recovering DMF, cooling to 60 deg.C, and neutralizing with glacial acetic acid to obtain SAL-AO-1. The weight average molecular weight of the resulting SAL-AO-1 was 5760g/mol and the polydispersity index was 2.158829 by GPC.
Preparation of SAL-AO-Q-1 (sodium lignosulfonate amphoteric surfactant):
200g SAL-AO-1 is weighed and added into a reaction kettle, 800g deionized water (20% aqueous solution) is added, the temperature is raised to 55 ℃, and the temperature is kept for 0.5h to fully dissolve the SAL-AO-1. Then adjusting the pH value of the reaction system to 9 by using 0.5N NaOH aqueous solution, heating to 80 ℃, adding 2g of tetrabutylammonium bromide, slowly dropwise adding 92.5g of Epichlorohydrin (ECH) for 1h, and then continuing to keep the temperature and stir for reaction for 5 h. Then slowly adding 157g of N, N-dimethyl octyl amine dropwise, simultaneously adjusting the pH value to 8 with 0.1N NaOH aqueous solution, after the dropwise addition is finished for 2h, stirring and reacting for 2h, then distilling to remove water, washing with absolute ethyl alcohol, carrying out suction filtration, and then drying in a vacuum drying oven at 80 ℃ for 48h to obtain SAL-AO-Q-1.
Example 2
A preparation method of sodium lignosulfonate polyether amphoteric surfactant for polyester industrial yarn comprises the following steps:
SAL pretreatment: (filtration → ultrasonic activation → ultrafiltration fractionation → ultrafiltration dispersion), SAL ranging from 1kDa to 10kDa was taken.
(1) And (3) filtering: 10% aqueous solution of sodium lignosulfonate (MJ-1, Feihuang chemical Co., Ltd., New Yi City) is subjected to suction filtration by using medium speed filter paper (15cm) under the vacuum degree of-0.1 Mpa, and lower layer filtrate A is taken out.
(2) Ultrasonic activation: and (3) carrying out ultrasonic treatment on the filtrate A for 6 hours at 80 ℃ under the power of 80% in ultrasonic waves to obtain a solution B, wherein the power of ultrasonic equipment is 500W.
(3) And (3) ultrafiltration grading impurity removal: treating with UF201 ultrafiltration device (Wuxi Saipu film science and technology development Co., Ltd.), with effective filtration area of 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 cutoff of 10KDa specification to obtain a solution with the molecular weight less than 10 KDa. Then, an ultrafiltration membrane with the molecular weight cutoff of 1KDa specification is adopted to obtain a solution C with the molecular weight of 1KDa-10 KDa.
(4) And (3) distillation and drying: and distilling the solution C in a rotary evaporator under reduced pressure with the vacuum degree of-0.1 Mpa, and then drying in a vacuum oven at 70 ℃ for 72h to obtain the pretreated sodium lignosulfonate SAL.
Preparation of SAL-AO-2 (sodium lignosulfonate polyether):
the reaction kettle is pumped out to replace nitrogen under negative pressure and is repeated for 4 times, 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 slowly introduced at the same time, the introduction time of the ethylene oxide and the introduction time of the SAL are both kept for 4h, 464g of ethylene oxide is slowly introduced when the pressure is stable for 0.6h after the curing reaction, the introduction time is kept for 2h, and the reaction is finished when the pressure is stable for 0.6h after the curing reaction. Distilling under reduced pressure at 135 deg.C, recovering DMF, cooling to 50 deg.C, and neutralizing with glacial acetic acid to obtain SAL-AO-2. The weight average molecular weight of SAL-AO-2 was 13920g/mol and the polydispersity index was 3.057762 by GPC.
Preparation of SAL-AO-Q-2 (sodium lignosulfonate amphoteric surfactant):
200g SAL-AO-2 is weighed and added into a reaction kettle, 1000g deionized water (16.7 percent aqueous solution) is added, the temperature is raised to 50 ℃, and the temperature is kept for 1 hour to ensure that the SAL-AO-2 is fully dissolved. Then, the pH value of the reaction system is adjusted to 11 by using 1.0N NaOH aqueous solution, the temperature is increased to 75 ℃, 4g of tetrabutylammonium bromide is added, 92.5g of Epichlorohydrin (ECH) is slowly added dropwise for 2h, and then the reaction is continuously stirred and reacted for 3h under the condition of heat preservation. Then 353g of N, N-dimethyl docosanamine is slowly dripped, meanwhile, 0.5N NaOH aqueous solution is used for adjusting the pH value to 10, after dripping is completed for 0.5h, stirring reaction is carried out for 5h, then distillation is carried out to remove water, absolute ethyl alcohol is used for washing and suction filtration, and then drying is carried out for 60h in a vacuum drying oven at 85 ℃ to obtain SAL-AO-Q-2.
Example 3
A preparation method of sodium lignosulfonate polyether amphoteric surfactant for polyester industrial yarn comprises the following steps:
SAL pretreatment: (filtration → ultrasonic activation → ultrafiltration fractionation → ultrafiltration dispersion), SAL ranging from 1kDa to 10kDa was taken.
(1) And (3) filtering: 8% aqueous solution of sodium lignosulfonate (MJ-1, Feihuang chemical Co., Ltd., New Yiyi) was filtered at medium speed filter paper (15cm) under a vacuum degree of-0.3 MPa, and the lower layer filtrate A was taken.
(2) Ultrasonic activation: and (3) carrying out ultrasonic treatment on the filtrate A for 4 hours at 50 ℃ under the power of 90% in ultrasonic waves to obtain a solution B, wherein the power of ultrasonic equipment is 400W.
(3) And (3) ultrafiltration grading impurity removal: treating with UF201 ultrafiltration device (Wuxi Saipu film science and technology development Co., Ltd.), with effective filtration area of 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 cutoff of 10KDa specification to obtain a solution with the molecular weight less than 10 KDa. Then, an ultrafiltration membrane with the molecular weight cutoff of 1KDa specification is adopted to obtain a solution C with the molecular weight of 1KDa-10 KDa.
(4) And (3) distillation and drying: and (3) carrying out reduced pressure distillation on the solution C in a rotary evaporator under the vacuum degree of-0.7 Mpa, and then placing the solution C in a vacuum oven to dry for 56 hours at the temperature of 75 ℃ to obtain the pretreated sodium lignosulfonate SAL.
Preparation of SAL-AO-3 (sodium lignosulfonate polyether):
the reaction kettle is pumped out to replace nitrogen under negative pressure and is repeated for 3 times, 100g of N, N-Dimethylformamide (DMF) and SAL20g are introduced under the stirring of 200rpm, then the temperature is increased 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 slowly introduced at the same time, the introduction time of the ethylene oxide and the SAL lasts for 2h, the temperature is increased to 130 ℃ after the curing reaction is carried out until the pressure is stable for 0.5h, then 216g of butylene oxide is slowly introduced, the introduction time lasts for 1h, and the reaction is finished after the curing reaction is carried out until the pressure is stable for 0.5 h. Distilling under reduced pressure at 125 deg.C, recovering DMF, cooling to 60 deg.C, and neutralizing with glacial acetic acid to obtain SAL-AO-3. The weight average molecular weight of the resulting SAL-AO-3 was 9240g/mol and the polydispersity index was 2.601305 by GPC.
Preparation of SAL-AO-Q-3 (sodium lignosulfonate amphoteric surfactant):
200g of SAL-AO-3 is weighed and added into a reaction kettle, 600g of deionized water (25% aqueous solution) is added, the temperature is raised to 60 ℃, and the temperature is kept for 0.5h to ensure that the SAL-AO-3 is fully dissolved. Then adjusting the pH value of the reaction system to 10 by using 0.5N NaOH aqueous solution, heating to 85 ℃, adding 1.5g of tetrabutylammonium bromide, slowly dropwise adding 92.5g of Epichlorohydrin (ECH) for 1.5h, and then continuing to keep the temperature and stir for reaction for 4 h. And then slowly adding 297g of N, N-dimethyl octadecylamine dropwise, simultaneously adjusting the pH value to 9 with 0.2N NaOH aqueous solution, stirring and reacting for 4h after the dropwise addition is finished for 1h, then distilling to remove water, washing with absolute ethyl alcohol, carrying out suction filtration, and then drying in a vacuum drying oven at 80 ℃ for 48h to obtain SAL-AO-Q-3.
Example 4
A preparation method of sodium lignosulfonate polyether amphoteric surfactant for polyester industrial yarn comprises the following steps:
SAL pretreatment: (filtration → ultrasonic activation → ultrafiltration fractionation → ultrafiltration dispersion), SAL ranging from 1kDa to 10kDa was taken.
(1) And (3) filtering: 7% aqueous solution of sodium lignosulfonate (MJ-1, Feihuang chemical Co., Ltd., New Yiyi) was filtered at medium speed through a filter paper (15cm) under a vacuum degree of-0.8 MPa, and the lower layer filtrate A was taken.
(2) Ultrasonic activation: and (3) carrying out ultrasonic treatment on the filtrate A for 3 hours at the temperature of 60 ℃ under the power of 90% in ultrasonic waves to obtain a solution B, wherein the power of ultrasonic equipment is 500W.
(3) And (3) ultrafiltration grading impurity removal: treating with UF201 ultrafiltration device (Wuxi Saipu film science and technology development Co., Ltd.), with effective filtration area of 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 cutoff of 10KDa specification to obtain a solution with the molecular weight less than 10 KDa. Then, an ultrafiltration membrane with the molecular weight cutoff of 1KDa specification is adopted to obtain a solution C with the molecular weight of 1KDa-10 KDa.
(4) And (3) distillation and drying: and distilling the solution C in a rotary evaporator under reduced pressure with the vacuum degree of-0.8 Mpa, and then drying in a vacuum oven at the temperature of 80 ℃ for 60 hours to obtain the pretreated sodium lignosulfonate SAL.
Preparation of SAL-AO-4 (sodium lignosulfonate polyether):
200g (0.5mol) of PEG400 was charged into a 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), stirring uniformly, slowly dripping 56g (0.6mol) of Epichlorohydrin (ECH) for 1h, and keeping the temperature at 55 ℃. After the dropwise addition, the reaction was continued at 55 ℃ for 2 h. Residual ECH was then removed by distillation under reduced pressure to give the chlorinated PEG400 intermediate. Then 100g SAL is dissolved in 1N NaOH aqueous solution to prepare 25% aqueous solution, then chlorinated PEG400 intermediate is dripped, after dripping is finished for 2h, the temperature is raised and reaction is carried out for 3h at 80 ℃. After cooling, the pH was adjusted to around 7 by neutralization with concentrated hydrochloric acid, thereby obtaining the product. Then purifying, adding butanone into the product solution for continuous extraction to remove unreacted PEG400 and water until the lower layer appears yellow brown viscous matter, and centrifuging at 10000rpm to separate the product. Vacuum drying to obtain purified SAL-AO-4 sample. The resulting SAL-AO-4 had a weight average molecular weight of 13216g/mol and a polydispersity index of 2.885009, as determined by GPC.
Preparation of SAL-AO-Q-4 (sodium lignosulfonate amphoteric surfactant):
200g SAL-AO-4 is weighed and added into a reaction kettle, 1800g deionized water (10% aqueous solution) is added, the temperature is raised to 65 ℃, and the temperature is kept for 0.5h to ensure that the SAL-AO-4 is fully dissolved. Then adjusting the pH value of the reaction system to 11 by using 0.5N NaOH aqueous solution, heating to 90 ℃, adding 1g of tetrabutylammonium bromide, slowly dropwise adding 92.5g of Epichlorohydrin (ECH) for 0.5h, and then continuously keeping the temperature and stirring for reacting for 6 h. Then, 213g of N, N-dimethyldodecylamine is slowly dripped, meanwhile, the pH value is adjusted to 10 by using 0.3N NaOH aqueous solution, after dripping is finished, the mixture is stirred and reacts for 3 hours, then the mixture is distilled to remove water, washed by absolute ethyl alcohol, filtered, and dried for 48 hours in a vacuum drying oven at the temperature of 80 ℃, and then the SAL-AO-Q-4 is obtained.
Example 5
This example differs from example 4 only in that:
preparation of SAL-AO-4 (sodium lignosulfonate polyether):
to the reaction kettle was added 250g of PEG400, heated to 60 ℃ and then 1g of boron trifluoride-diethyl ether (BF) was added to the reaction vessel 3 -Et 2 O), after stirring evenly, slowly dripping 60g of Epichlorohydrin (ECH) for 0.5h, and keeping the temperature at 60 ℃. After the dropwise addition, the reaction was continued at 60 ℃ for 1 hour. Residual ECH was then removed by distillation under reduced pressure to give the chlorinated PEG400 intermediate. Then 200g SAL is dissolved in 1N NaOH aqueous solution to prepare 30% aqueous solution, then chlorinated PEG400 intermediate is dripped for 1h, and then the temperature is raised to react for 1h at 85 ℃. After cooling, the pH was adjusted to around 7.5 by neutralization with concentrated hydrochloric acid, thereby obtaining the product. Then purifying, adding butanone into the product solution to extract continuously to remove unreacted PEG400 and water until the lower layer appears yellow brown viscous matter, and centrifuging at 8000rpm to separate out the product. Vacuum drying to obtain purified SAL-AO-4 sample.
Example 6
This example differs from example 4 only in that:
preparation of SAL-AO-4 (sodium lignosulfonate polyether):
220g PEG400 was added to the reaction vessel, the temperature was raised to 60 ℃ and then 0.9g boron trifluoride-diethyl ether (BF) was added to the reaction vessel 3 -Et 2 O), after stirring uniformly, slowly adding 58g of Epichlorohydrin (ECH) dropwise for 2h, and keeping the temperature at 60 ℃. After the dropwise addition, the reaction was continued at 60 ℃ for 4 hours. Residual ECH was then removed by distillation under reduced pressure to give the chlorinated PEG400 intermediate. Then 150g SAL is dissolved in 1N NaOH aqueous solution to prepare 25% aqueous solution, then chlorinated PEG400 intermediate is dripped, after dripping is finished for 3h, the temperature is raised and reaction is carried out for 5h at 85 ℃. After cooling, the pH was adjusted to around 7 by neutralization with concentrated hydrochloric acid, thereby obtaining the product. Then, purification treatment was carried out, butanone was added to the product solution, and extraction was continued to remove unreacted PEG400 and water until a yellowish brown viscous substance appeared in the lower layer, and the product was separated by centrifugation at 9000 rpm. Vacuum drying to obtain purified SAL-AO-4 sample.
The polyester industrial yarn spinning oil agent containing the sodium lignosulfonate polyether amphoteric surfactant for the polyester industrial yarn is specifically shown in the following table 3.
TABLE 3 polyester industrial yarn spin finish tables for examples 7 to 12 and comparative examples 1 to 3
Example 13:
this example differs from example 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:
bundling and oiling (oven 1, oven 2), stretching (oven 1, oven 2, oven 3), meshing and winding.
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 flows, respectively.
Dyeing experiment:
spinning polyester industrial yarn, a dye solution tank, an oven 1, an oven 2, a reduction cleaning tank, a steam box and a water washing tank.
The polyester industrial yarns treated in the examples 7 to 12 and the comparative examples 1 to 3 are respectively dyed according to the same dyeing process conditions and process flows. The occurrence of white spots (the length of white spots in ppm in the total length of the treated polyester industrial yarn) is shown in Table 4.
TABLE 4 white spot condition table of polyester industrial yarn for examples 7-12 and comparative examples 1-3
| Experiment of | 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, the white spots of comparative example 1 and comparative example 2 of the present invention are linear, which indicates that the white spots of the industrial polyester yarn of comparative example 1, which is not treated with the sodium lignosulfonate amphoteric surfactant of the present invention, are serious and the industrial polyester yarn is prone to have dyeing defects and color defects after being dyed by the one-bath process.
As shown in fig. 3, which is a white spot condition diagram of example 8 of the present invention, it can be seen from the diagram that after the polyester industrial yarn treated by the sodium lignosulfonate amphoteric surfactant of the present invention is dyed by the one-bath process, white spots are few, only 42ppm, white spots are very small and not obvious, the polyester industrial yarn is not easy to have dyeing defects and color defects, the product quality is good, the qualification rate is high, and the polyester industrial yarn is a spinning oil suitable for the one-bath process of the wash dyeing of downstream enterprises.
As can be seen from table 2, in examples 11 and 12, the sodium lignosulfonate amphoteric surfactant of the present invention is directly added to the existing spin finish, and the added existing spin finish also has the effects of greatly reducing white spots and greatly improving the product quality.
In the description provided herein, numerous specific details are set forth. It is understood, however, 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 is to be understood that the terms "upper", "lower", "front", "rear", "left", "right", and the like indicate orientations or positional relationships based on those shown in the drawings, and are only for convenience of description and simplicity of description, but do not indicate or imply that the referred device or element must have a specific orientation, be constructed in a specific orientation, and be operated, 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 to reflect the intent: that the invention as claimed 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 this description, will appreciate that other embodiments can be devised which do not depart from 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 present invention has been disclosed in an illustrative rather than a restrictive sense, and the scope of the present invention is defined by the appended claims.
The above description is only of the preferred embodiments of the present invention, and it should be 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 invention and these are intended to be within the scope of the invention.
Claims (10)
1. A sodium lignosulfonate polyether amphoteric surfactant for polyester industrial yarns is characterized in that: the structure unit is as follows:
wherein SAL is sodium lignosulfonate;
AO is polyether, AO comprises any one or combination of ethylene oxide EO, propylene oxide PO and butylene oxide BO;
the value range of m is 4-20;
r comprises straight-chain alkane of C8-C22;
b comprises no substituent.
2. The sodium lignosulfonate polyether amphoteric surfactant for the polyester industrial yarn as claimed in claim 1, which is characterized in that: b is composed of-CH 2 -CH(OH)-CH 2 -replacing no substituent.
3. The method for preparing the sodium lignosulfonate polyether amphoteric surfactant for the polyester industrial yarn according to claim 1, which is characterized in that: the method comprises the following steps:
step one, pretreating sodium lignosulfonate SAL: obtaining sodium lignosulfonate SAL with the molecular weight of 1KDa-10 KDa;
step two, preparing sodium lignosulfonate polyether SAL-AO:
the reaction kettle is pumped to replace nitrogen by negative pressure and is repeated for at least 3 times, and N, N-dimethylformamide DMF with the weight ratio of (5-10):1 and the first batch of pretreated sodium lignosulfonate SAL are introduced under the stirring of 200-300 rpm; then heating to 100-125 ℃, adding an alkaline catalyst after 0.5-0.6h, wherein the adding weight of the alkaline catalyst is 11.8-160% of the weight of the first pretreated sodium lignosulfonate SAL, and keeping the temperature at 115-125 ℃;
then carrying out 1-2 times of curing reaction;
first curing reaction: slowly introducing AO and the second batch of pretreated sodium lignosulfonate SAL at the same time, wherein the introduction time of the AO and the second batch of pretreated sodium lignosulfonate SAL lasts for 1-4h, the introduction weight of the AO is equivalent to 17.6-105.6 times of that of the first batch of pretreated sodium lignosulfonate SAL, and the introduction weight of the second batch of pretreated sodium lignosulfonate SAL is equivalent to 39-79 times of that of the first batch of pretreated sodium lignosulfonate SAL; curing reaction is carried out until the pressure is stable for 0.5-0.6 h;
and (3) second curing reaction: after the first curing reaction is finished, raising the temperature to 125-135 ℃, and then slowly introducing AO, wherein the introduction weight of AO is equivalent to 21.6-46.4 times of that of the first pretreated sodium lignosulfonate SAL; the introducing time lasts for 1-2h, and the reaction is finished when the pressure is stable for 0.5-0.6h after the curing reaction;
then carrying out reduced pressure distillation at the temperature of 125-;
step three, preparing a sodium lignosulfonate polyether amphoteric surfactant SAL-AO-Q:
weighing a proper amount of sodium lignosulfonate polyether SAL-AO, adding into a reaction kettle, adding deionized water with the weight 3-9 times of that of the sodium lignosulfonate polyether SAL-AO, heating to 50-65 ℃, and preserving heat for 0.5-1h to fully dissolve the sodium lignosulfonate polyether SAL-AO; then adjusting the pH value of the reaction system to 9-11 by using 0.5-1.0N NaOH aqueous solution, heating to 80-90 ℃, adding tetrabutylammonium bromide, slowly dropwise adding epoxy chloropropane ECH, wherein the adding weight of the tetrabutylammonium bromide is 0.5-2% of that of sodium lignosulfonate polyether SAL-AO, and the adding weight of the epoxy chloropropane ECH is 46.25% of that of the sodium lignosulfonate polyether SAL-AO; then continuously preserving heat and stirring for reaction for 3-6 h; then 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 lignosulfonate polyether SAL-AO; and simultaneously, adjusting the pH value to 8-10 by using 0.1-0.5N NaOH aqueous solution, after 0.5-2h of dropwise addition, stirring for reacting for 2-5h, then distilling to remove water, washing by using absolute ethyl alcohol, carrying out suction filtration, and then drying in a vacuum drying oven at 80-85 ℃ for at least 48h to obtain SAL-AO-Q.
4. The method for preparing the sodium lignosulfonate polyether amphoteric surfactant for the polyester industrial yarn according to claim 2, which is characterized in that: the method comprises the following steps:
step one, pretreating sodium lignosulfonate SAL: obtaining sodium lignosulfonate SAL with the molecular weight of 1KDa-10 KDa;
step two, preparing sodium lignosulfonate polyether SAL-AO:
adding 200-250g PEG400 into a reaction kettle, heating to 55-60 ℃, and then adding 0.8-1g boron trifluoride-diethyl ether BF into the reaction kettle 3 -Et 2 O, after being evenly stirred, slowly dripping the ECH56-60g of the epichlorohydrin for 0.5-2h, and keeping the temperature at 5 DEG5-60 ℃; after the dropwise addition is finished, continuously keeping the temperature of 55-60 ℃ for reaction for 1-4 h; then carrying out reduced pressure distillation to remove residual epichlorohydrin ECH to obtain a chlorinated PEG400 intermediate; then dissolving 100-200g of pretreated sodium lignosulfonate SAL in 1N NaOH aqueous solution to prepare 25-30% aqueous solution, dropwise adding a chlorinated PEG400 intermediate for 1-3h, and heating to react at 80-85 ℃ for 1-5 h; after cooling, the pH is adjusted to 7-7.5 by neutralization with concentrated hydrochloric acid, thereby obtaining a product; then purifying, adding butanone into the product solution for continuous extraction to remove unreacted PEG400 and water until the lower layer appears yellow brown sticky matter, and centrifuging at 8000-; vacuum drying to obtain purified sodium lignosulfonate polyether SAL-AO;
step three, preparing a sodium lignosulfonate polyether amphoteric surfactant SAL-AO-Q:
weighing a proper amount of sodium lignosulfonate polyether SAL-AO, adding into a reaction kettle, adding deionized water with the weight 3-9 times of that of the sodium lignosulfonate polyether SAL-AO, heating to 50-65 ℃, and preserving heat for 0.5-1h to fully dissolve the sodium lignosulfonate polyether SAL-AO; then adjusting the pH value of the reaction system to 9-11 by using 0.5-1.0N NaOH aqueous solution, heating to 80-90 ℃, adding tetrabutylammonium bromide, slowly dropwise adding epoxy chloropropane ECH, wherein the adding weight of the tetrabutylammonium bromide is 0.5-2% of that of sodium lignosulfonate polyether SAL-AO, and the adding weight of the epoxy chloropropane ECH is 46.25% of that of the sodium lignosulfonate polyether SAL-AO; then continuously preserving heat and stirring for reaction for 3-6 h; then 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 lignosulfonate polyether SAL-AO; and simultaneously, adjusting the pH value to 8-10 by using 0.1-0.5N NaOH aqueous solution, after 0.5-2h of dropwise adding, stirring and reacting for 2-5h, then distilling to remove water, washing by using absolute ethyl alcohol, carrying out suction filtration, and then drying for at least 48h in a vacuum drying oven at the temperature of 80-85 ℃ to obtain SAL-AO-Q.
5. The method for preparing the sodium lignosulfonate polyether amphoteric surfactant for the polyester industrial yarn according to claim 3 or 4, which is characterized in that: n, N-dimethyl alkylamines including N, N-dimethyl octylamine, N-dimethyl behenylamine, N-dimethyl octadecylamine or N, N-dimethyl dodecylamine; the basic catalyst includes sodium methoxide, potassium methoxide or sodium ethoxide.
6. The polyester industrial yarn spinning oil agent containing the sodium lignosulfonate polyether amphoteric surfactant for the polyester industrial yarn, which is described in claim 1 or 2, is characterized in that: the polyester industrial yarn spinning oil agent comprises the following components in parts by weight: smoothing agent: 50 parts, surfactant: 30 parts of preservative: 0.1 part and water: 320 parts of (a); the surfactant includes: sodium lignosulfonate 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 PEG400 DO: 1-6 parts.
7. The polyester industrial yarn spinning finish according to claim 6, characterized in that: the smoothing agent comprises glycerol trioleate and lauryl oleate in a weight ratio of 2: 3.
8. The polyester industrial yarn spinning finish according to claim 6, characterized in that: the preservative comprises cason, sodium benzoate or potassium sorbate.
9. The application of the polyester industrial yarn obtained by spinning the polyester industrial yarn spinning oil according to claim 6 in dyeing is characterized in that: the white spots of the polyester industrial yarn are less than 100 ppm.
10. The use of the polyester industrial yarn obtained by spinning the existing spinning oil agent containing the sodium lignosulfonate polyether amphoteric surfactant for the polyester industrial yarn in the dyeing process, which is disclosed by the claim 1 or the claim 2, is characterized in that: the white spots of the polyester industrial yarn are less than 40 ppm.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115652666A (en) * | 2022-11-04 | 2023-01-31 | 中山市好本意新材料有限公司 | Environment-friendly nylon color fixing agent and preparation method thereof |
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| US20220024959A1 (en) * | 2018-11-29 | 2022-01-27 | Fundacion Tecnalia Research & Innovation | Lignin-based polyols |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115652666A (en) * | 2022-11-04 | 2023-01-31 | 中山市好本意新材料有限公司 | Environment-friendly nylon color fixing agent and preparation method thereof |
| CN115652666B (en) * | 2022-11-04 | 2024-02-27 | 中山市好本意新材料有限公司 | Environment-friendly nylon color fixing agent and preparation method thereof |
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