CN107226901A - A kind of cation-dyeable hydrophobic polyester and its production and use - Google Patents
A kind of cation-dyeable hydrophobic polyester and its production and use Download PDFInfo
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- CN107226901A CN107226901A CN201610171980.0A CN201610171980A CN107226901A CN 107226901 A CN107226901 A CN 107226901A CN 201610171980 A CN201610171980 A CN 201610171980A CN 107226901 A CN107226901 A CN 107226901A
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- polyester
- cation
- dyeable
- sulfonate
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- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
- C08G63/6884—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6886—Dicarboxylic acids and dihydroxy compounds
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- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
The invention discloses a kind of cation-dyeable hydrophobic polyester and preparation method thereof.Mainly esterification is carried out by aromatic acid under catalyst action with aliphatic dihydroxy alcohol and polycondensation reaction is obtained.Sulfonate and tetrafluoro terephthalic acid (TPA) are added in esterification or polycondensation reaction, wherein sulfonate is M-phthalic acid -5- sulfonate, DMIP -5- sulfonate or M-phthalic acid binaryglycol ester -5- sulfonate.Gained cation-dyeable hydrophobic polymer of the invention has relatively low surface energy, excellent hydrophobic performance, while having positive from stainability energy.
Description
Technical field
The present invention relates to a kind of polyester with cation-dyeable performance and hydrophobic performance and preparation method thereof.
Background technology
Polyester is one of the most widely used synthetic high polymer of the current mankind, with intensity height, elastic good, wrinkle resistance
By force, dimensionally stable, wearability be good, stable chemical performance, quick-drying washable, heat resistance and the performance such as against weather is excellent, extensive
Applied to each field such as clothes, decoration, industrial or agricultural.
With the improvement of living standards, people propose the additional properties of fiber higher requirement, such as require to be used for
Fiber on the shell of exterior aerial, ship or submarine will not only have chromatic colour, also there is hydrophobic performance.
But, because the molecular structure of conventional polyester is regular, crystallinity and the degree of orientation are higher, no Yi Ran functional groups, polarity
It is minimum, lack hydrophily, there is no the gap that can suitably accommodate dye molecule between polyester long-chain molecule, therefore dye particles are not
Easily enter fiber, its dyeability is poor, can be used the species of dyestuff few, can only be using disperse dyes carrier dyeing, high-temperature dyeing etc.
Method, but working condition is harsh, production cost is high, and product colour is undesirable.
Due to the limitation of technology, only individually improve polyester dyeing or hydrophobic technical side in the prior art
Case.As Chinese patent CN101469060A only discloses a kind of preparation of cation-dyeable poly terephthalic acid 1,3-PD ester
Method, after completion of the esterification reaction or polymerisation start before add Sulfonates compound, obtained polymer using sun from
After sub- dyeing, its fabric is bright in luster, color fastness is high.Chinese patent CN101139434A is disclosed one kind and sealed with fluoroalkyl
End the fluorine-containing polyester with low-surface-energy with and preparation method thereof, can extensive use with good hydrophobic oleophobic performance
In anticorrosion and antifouling coating.But the Oil repellent of the polyester blocked with fluoroalkyl is low, it is impossible to meet spinning and the requirement of film forming.
The content of the invention
It is an object of the invention to provide a kind of cation-dyeable and with good hydrophobic effect polyester and its
Production method.Specifically, by adding cation-dyeable composition and fluorochemical with hydrophobic effect in the polyester, so that
Not only possessed cation dyeable but also with hydrophobic polymer.
The present invention technical solution be：
A kind of cation-dyeable hydrophobic polyester, is mainly formed, the cation by aromatic acid and aliphatic dihydroxy alcohol copolymerization
It can contaminate in the strand of hydrophobic polyester also comprising the construction unit as shown in following formula 1 and formula 2：
Formula 1
Formula 2,
Wherein, M represents sodium, lithium or potassium in formula 2.
Fluorine element content in construction unit shown in the formula 1 preferably accounts for 1.0wt%~28.4wt% of polyester total amount.
Sulfur content in construction unit shown in the formula 2 preferably accounts for 0.1 wt%~1.2wt% of polyester total amount.
The weight ratio preferably 20.0 ~ 100.0 of fluorine element and element sulphur in the polyester：1.
The inherent viscosity of the polyester is 0.50~0.80dl/g.
The invention also discloses a kind of preparation method of cation-dyeable hydrophobic polyester, mainly by aromatic acid and fat
Fat race dihydric alcohol carries out esterification under catalyst action and polycondensation reaction is obtained, and sulfonic acid is added in esterification or polycondensation reaction
Salt and tetrafluoro terephthalic acid (TPA), wherein sulfonate are M-phthalic acid -5- sulfonate, DMIP -5- sulfonate
Or M-phthalic acid binaryglycol ester -5- sulfonate.
In esterification or polycondensation reaction, tetrafluoro terephthalic acid (TPA) is preferably first added, then add M-phthalic acid sulfonic acid
Salt.
The addition of the sulfonate is preferably equivalent to 1.46wt%~3.66wt% of polyester.
The addition of the tetrafluoro terephthalic acid (TPA) is preferably equivalent to 26.84wt%~53.68wt% of polyester.
The polyester of the present invention has cation-dyeable performance, and stainability is good, and bright, not fugitive color, color fastness are high；Together
When the present invention polyester also have excellent hydrophobic performance.
Embodiment
Containing the construction unit as shown in formula 1 and formula 2 in the strand of the cation-dyeable hydrophobic polyester of the present invention,
Formula 1
Formula 2,
Wherein, M represents sodium, lithium or potassium in formula 2.
Construction unit as shown in Equation 1 comes from tetrafluoro terephthalic acid (TPA), passes through electronegativity strong fluorine atom, high bond energy
C-F keys are acted on the shielding protection of carbochain, can improve the surface property of polyester material, polyester is hydrophobic, it is oily, anti-to hate so as to assign
Dirty performance.Tetrafluoro terephthalic acid (TPA) has double carboxyl structures, and aromatic acid or its ester can be replaced during modified-reaction
Compound is reacted, polyester of the generation containing construction unit block as shown in Equation 1.
The content of construction unit as shown in Equation 1 is higher in polyester, and the hydrophobic effect of polyester is more obvious；But as shown in Equation 1
If the content of construction unit is excessive, the cost of polyester can be caused to raise, tone is deteriorated.Preferably tied as shown in Equation 1 in the present invention
Fluorine element content accounts for 10.0wt%~20.0wt% of polyester total amount in structure unit.
Construction unit as shown in Equation 2 comes from sulfonate in the present invention.Because polarity sulfonic acid group is present, polyester possesses
Cation-dyeable performance.The content of sulfonic acid group is higher in polyester, and the stainability of polyester is better.But, the pole of sulfonic acid group
Property it is big, excessive sulfonate can cause its autohemagglutination so that significantly, reaction can not be carried out the increasing stick effect of polyester.Therefore, it is of the invention
In the content of construction unit as shown in Equation 2 preferably account for 0.1wt%~1.2wt% of polyester total amount in terms of element sulphur, more preferably account for poly-
0.2wt%~0.5wt% of ester total amount.
In order that the cation-dyeable performance and hydrophobic effect that obtain polyester of the present invention are optimal, fluorine element in polyester
With the weight ratio preferably 20.0 ~ 100.0 of element sulphur：1.
The invention also discloses a kind of preparation method of above-mentioned cation-dyeable hydrophobic polyester, mainly by aromatic acid
Esterification is carried out under catalyst action with aliphatic dihydroxy alcohol and polycondensation reaction is obtained, added in esterification or polycondensation reaction
Sulfonate and tetrafluoro terephthalic acid (TPA), wherein sulfonate are M-phthalic acid -5- sulfonate, DMIP -5- sulphurs
Hydrochlorate or M-phthalic acid binaryglycol ester -5- sulfonate.
The sulfonate is metal organic sulfonate, can be specifically preferred sodium in sodium salt, sylvite or lithium salts etc., the present invention
Salt.
The addition of the sulfonate is preferably equivalent to 1.46wt%~3.66wt% of polyester；The tetrafluoro terephthalic acid (TPA)
Addition be preferably equivalent to 26.84wt%~53.68wt% of polyester.
When adding sulfonate and tetrafluoro terephthalic acid (TPA) in esterification or polycondensation reaction, sulfonate can be first added again
Tetrafluoro terephthalic acid (TPA) is added, tetrafluoro terephthalic acid (TPA) can also be first added and add sulfonate again, can simultaneously be added with both.
In addition, sulfonate and tetrafluoro terephthalic acid (TPA) can be added in the same stage of reaction, it can also be carried out in the different stages of reaction
Addition.
When first adding tetrafluoro terephthalic acid (TPA), because the electronegativity of fluorine is strong, the bond energy of C-F keys is high, fluorine atom and rear addition
Sulfonate in hydrogen ion effect, formed Hyarogen-bonding so that sulfonate can scatter, and reduce the autohemagglutination of sulfonate
Effect, can obtain the polyester of high-cation stainability.Therefore, preferably first addition tetrafluoro terephthalic acid (TPA) is added again in the present invention
Sulfonate.
The catalyst of normal polyester, such as antimony class catalyst, titanium catalyst or germanium can be used in the preparation method of the present invention
Class catalyst etc..Wherein, the preferred antimony oxide of antimony class catalyst, antimony glycol or antimony acetate, the preferred metatitanic acid four of titanium catalyst
Butyl ester, the preferred germanium dioxide of germanium class catalyst.
By the addition of tetrafluoro terephthalic acid (TPA) and sulfonate, polyester of the invention has excellent cation-dyeable performance
And hydrophobic performance, its inherent viscosity is 0.50~0.80dl/g.Fiber can be made by known method in the polyester of the present invention,
And then fabric is formed, gained finished product also has good cation dyeable and higher hydrophobic and resistance to soiling.
Below by embodiment, the present invention will be described in more detail.It should be understood that these embodiments are merely to illustrate this hair
Bright rather than limitation the scope of the present invention.Meanwhile, each characteristic value in embodiment is tested by following method.
A. fluorine element content in polyester
The content of fluorine element is determined using Electronic probe x-ray microregion analysis.
B. sulfur content in polyester
6g polyester is pressed into sheet, fluorescent x-ray analysis apparatus is used（The type of X-Ray Analyzer 3270 of electric corporation's manufacture of science）Survey
Its fixed intensity, the detection line being made in advance with the sample of known sulfur content is converted.
C. the inherent viscosity of polyester
Mass ratio is used for 1:1 phenol and tetrachloroethanes solution, using full-automatic viscosity determinator, capillary diameter is
1.2mm, the inherent viscosity to polyester at 25 DEG C is measured.
D. cylinder is compiled and looks for tune
Polyester is subjected to spinning, and obtained silk is subjected to cylinder volume, staining evaluation is carried out under the following conditions.Then, cylinder is compiled
Thing washing, air-dry after with the sample that judges.With high-temperature dyeing testing machine UR MINI-COLOR（The small-sized coloring agent of infrared ray
（TEXAM technical research is manufactured）Mixing treating liquid, dyeing under conditions of 95 DEG C × 30min.The now medicament for the treatment of fluid used
It is as follows：
Dianix Blue E-Plus（The manufacture of De Sida companies, the dye of positive ion） 4owf%
NIKKA SUNSALT（The manufacture of solar corona chemical company, levelling agent）2g/L
Acetic acid（PH adjusting agent）1g/L
After dyeing, treatment fluid is prepared using following medicament under conditions of 80 DEG C × 20min, reduction cleaning is carried out,
Sodium hydroxide 0.6g/L
Sodium hydrogensulfite 2g/L
Then, with the sample that judges after cylinder being compiled thing washing, air-dried.Sample is overlapped into after 8 layers and uses spectral photometric colour measuring meter
（The Datacolor 650 of Datacolor Asia Pacific (H.K.) Ltd. manufactures）Colour examining, L*Refer to L*、a*And b*Table color
Lightness in system.
E. hydrophobicity evaluation（Surface energy）
Hydrophobicity evaluation can be characterized by surface, wherein surface can test when, produced using Changchun optical instrument head factory
JJC-I types Wetness Angle Measuring Instrument measurement liquid contact angle on a solid surface.During measurement, with microsyringe (2.0mL)
Will detection liquid away from it is vertical the surface of solids about 3mm at, be carefully added dropwise in the surface of solids, form seat drop, droplet size for 3~
5 μ L, a diameter of 1~2mm, time of measuring is no more than 1min, takes the average value of 10 (per minor tick 2s) contact angles as the seat
The contact angle of drop, take the contact angle average value of 10 seats drop as the liquid the surface contact angle.All measurements are in room
Carried out under warm (25 DEG C).It is AR to detect liquid glycerol, formamide and ethylene glycol.Advancing contact angle is connect instead of Young
Feeler carries out the calculating of fiber surface free energy.
Embodiment 1
13398g tetrafluoro terephthalic acid (TPA) and 4046g EG are added in esterifying kettle（Ethylene glycol）, stir and risen in 4 hours
Temperature is to 240 DEG C；By the judgement to accessory substance, reactivity to be esterified reaches more than 97%, and prepared oligomer is moved into and polymerize
Kettle；Heated up under the protection of inert gas, when system reaches 255 DEG C, first add phosphorus stabilizer agent trimethyl phosphate, then add
Hydroxyl ethyl ester -5- the sodium sulfonates of M-phthalic acid two（SIPE）417g, then, adds major catalyst antimony acetate, the consumption of antimony acetate is
200ppm, carries out aftercondensated under high temperature, high vacuum condition, and vacuum is less than 60Pa, and reaction temperature is 280 DEG C, reaction time
For 3h, so that cation-dyeable hydrophobic copolymer is made.
Embodiment 2
3720g TPA (terephthalic acid (TPA)) and 4248g EG are added in esterifying kettle（Ethylene glycol）, tetrafluoro is added to benzene two
Formic acid 9394g, stirs and was warming up to 240 DEG C in 4 hours；By the judgement to accessory substance, reactivity to be esterified reach 97% with
On, prepared oligomer is moved into polymeric kettle；Heat up, when system reaches 255 DEG C, first add under the protection of inert gas
Phosphorus stabilizer agent trimethyl phosphate, hereafter, adds the hydroxyl ethyl ester -5- sodium sulfonates of M-phthalic acid two（SIPE）834g, then, adds master
Catalyst acetic acid antimony, the consumption of antimony acetate is 200ppm, then, aftercondensated is carried out under high temperature, high vacuum condition, vacuum is low
In 60Pa, reaction temperature is 280 DEG C, and the reaction time is 3h, so that cation-dyeable hydrophobic copolymer is made.
Embodiment 3
6772g TPA (terephthalic acid (TPA)) and 4699g EG are added in esterifying kettle（Ethylene glycol）, tetrafluoro is added to benzene two
Formic acid 7046g, stirs and was warming up to 240 DEG C in 4 hours；By the judgement to accessory substance, reactivity to be esterified reach 97% with
On, prepared oligomer is moved into polymeric kettle；Heat up, when system reaches 255 DEG C, first add under the protection of inert gas
Phosphorus stabilizer agent trimethyl phosphate, hereafter, adds the hydroxyl ethyl ester -5- sodium sulfonates of M-phthalic acid two（SIPE）1251g, then, is added
Major catalyst antimony acetate, the consumption of antimony acetate is 200ppm, then, aftercondensated, vacuum is carried out under high temperature, high vacuum condition
Less than 60Pa, reaction temperature is 280 DEG C, and the reaction time is 3h, so that cation-dyeable hydrophobic copolymer is made.
Embodiment 4
8677g TPA (terephthalic acid (TPA)) and 5060g EG are added in esterifying kettle（Ethylene glycol）, tetrafluoro is added to benzene two
Formic acid 4697g, stirs and was warming up to 240 DEG C in 4 hours；By the judgement to accessory substance, reactivity to be esterified reach 97% with
On, prepared oligomer is moved into polymeric kettle；Heat up, when system reaches 255 DEG C, first add under the protection of inert gas
Phosphorus stabilizer agent trimethyl phosphate, hereafter, adds the hydroxyl ethyl ester -5- sodium sulfonates of M-phthalic acid two（SIPE）1668g, then, is added
Major catalyst antimony acetate, the consumption of antimony acetate is 200ppm, then, aftercondensated, vacuum is carried out under high temperature, high vacuum condition
Less than 60Pa, reaction temperature is 280 DEG C, and the reaction time is 3h, so that cation-dyeable hydrophobic copolymer is made.
Embodiment 5
8769 TPA (terephthalic acid (TPA)) and 5054g EG are added in esterifying kettle（Ethylene glycol）, add tetrafluoro terephthaldehyde
Sour 3757g, after stirring, adds Sodium Dimethyl Isophthalate-5-sulfonate 746g, stirs and be warming up to 240 in 4 hours
℃；By the judgement to accessory substance, reactivity to be esterified reaches more than 97%, and prepared oligomer is moved into polymeric kettle；Lazy
Property gas protection under heat up, when system reaches 255 DEG C, first add phosphorus stabilizer agent trimethyl phosphate, then, add main catalytic
Agent antimony acetate, the consumption of antimony acetate is 200ppm, then, aftercondensated is carried out under high temperature, high vacuum condition, vacuum is less than
60Pa, reaction temperature is 280 DEG C, and the reaction time is 3h, so that cation-dyeable hydrophobic copolymer is made.
Embodiment 6
9763g TPA (terephthalic acid (TPA)) and 5162g EG are added in esterifying kettle（Ethylene glycol）, tetrafluoro is added to benzene two
Formic acid 2348g, stirs and was warming up to 240 DEG C in 4 hours；By the judgement to accessory substance, reactivity to be esterified reach 97% with
On, prepared oligomer is moved into polymeric kettle；Heat up, when system reaches 255 DEG C, first add under the protection of inert gas
Phosphorus stabilizer agent trimethyl phosphate, hereafter, adds the hydroxyl ethyl ester -5- sodium sulfonates of M-phthalic acid two（SIPE）3337.5g, then, plus
Catalyst acetic acid antimony is become owner of, the consumption of antimony acetate is 200ppm, then, aftercondensated, vacuum is carried out under high temperature, high vacuum condition
Degree is less than 60Pa, and reaction temperature is 280 DEG C, and the reaction time is 3h, so that cation-dyeable hydrophobic copolymer is made.
Embodiment 7
13433 g TPA (terephthalic acid (TPA)) and 5351g EG is added in esterifying kettle（Ethylene glycol）, tetrafluoro is added to benzene
Dioctyl phthalate 47g, stirs and was warming up to 240 DEG C in 4 hours；By the judgement to accessory substance, reactivity to be esterified reach 97% with
On, prepared oligomer is moved into polymeric kettle；Heat up, when system reaches 255 DEG C, first add under the protection of inert gas
Phosphorus stabilizer agent trimethyl phosphate, hereafter, adds the hydroxyl ethyl ester -5- sodium sulfonates of M-phthalic acid two（SIPE）5006g, then, is added
Major catalyst antimony acetate, the consumption of antimony acetate is 200ppm, then, aftercondensated, vacuum is carried out under high temperature, high vacuum condition
Less than 60Pa, reaction temperature is 280 DEG C, and the reaction time is 3h, so that cation-dyeable hydrophobic copolymer is made.
Embodiment 8
8107g TPA (terephthalic acid (TPA)) and 4989g EG are added in esterifying kettle（Ethylene glycol）, add M-phthalic acid
Dimethyl ester -5- sodium sulfonate 416g, stir and were warming up to 240 DEG C in 4 hours；Pass through the judgement to accessory substance, reaction to be esterified
Rate reaches more than 97%, and prepared oligomer is moved into polymeric kettle；Heated up under the protection of inert gas, when system reaches 255
DEG C when, first add phosphorus stabilizer agent trimethyl phosphate, hereafter, add tetrafluoro terephthalic acid (TPA) 4697g, then, add major catalyst
Antimony acetate, the consumption of antimony acetate is 200ppm, then, aftercondensated is carried out under high temperature, high vacuum condition, vacuum is less than
60Pa, reaction temperature is 280 DEG C, and the reaction time is 3h, so that cation-dyeable hydrophobic copolymer is made.
The specific performance of polyester is shown in Table 1 obtained by above-described embodiment.
Claims (10)
1. a kind of cation-dyeable hydrophobic polyester, is mainly formed, its feature by aromatic acid and aliphatic dihydroxy alcohol copolymerization
It is：Also comprising the construction unit as shown in following formula 1 and formula 2 in the strand of the cation-dyeable hydrophobic polyester：
Formula 1,
Formula 2,
Wherein, M represents sodium, lithium or potassium in formula 2.
2. cation-dyeable hydrophobic polyester according to claim 1, it is characterised in that：In construction unit shown in the formula 1
Fluorine element content account for 1.0wt%~28.4wt% of polyester total amount.
3. cation-dyeable hydrophobic polyester according to claim 1, it is characterised in that：In construction unit shown in the formula 2
Sulfur content account for 0.1wt%~1.2wt% of polyester total amount.
4. the cation-dyeable hydrophobic polyester according to Claims 2 or 3, it is characterised in that：In the polyester fluorine element and
The weight ratio of element sulphur is 20.0 ~ 100.0：1.
5. cation-dyeable hydrophobic polyester according to claim 1, it is characterised in that：The inherent viscosity of the polyester is
0.50~0.80dl/g.
6. the preparation method of cation-dyeable hydrophobic polyester described in a kind of claim 1, mainly by aromatic acid and fat
Race's dihydric alcohol carries out esterification under catalyst action and polycondensation reaction is obtained, it is characterised in that：In esterification or polycondensation reaction
Middle addition sulfonate and tetrafluoro terephthalic acid (TPA), wherein sulfonate are M-phthalic acid -5- sulfonate, M-phthalic acid diformazan
Ester -5- sulfonate or M-phthalic acid binaryglycol ester -5- sulfonate.
7. the preparation method of cation dyeable polyester according to claim 6, it is characterised in that：It is anti-in esterification or polycondensation
Ying Zhong, first adds tetrafluoro terephthalic acid (TPA), then add M-phthalic acid sulfonate.
8. the preparation method of cation dyeable polyester according to claim 6 or 7, it is characterised in that：The sulfonate adds
1.46wt%~3.66wt% of the dosage equivalent to polyester.
9. the preparation method of cation dyeable polyester according to claim 6 or 7, it is characterised in that：The tetrafluoro is to benzene two
26.84wt%~53.68wt% of the addition of formic acid equivalent to polyester.
10. application of the cation-dyeable hydrophobic polyester on fiber is prepared described in a kind of claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201610171980.0A CN107226901A (en) | 2016-03-24 | 2016-03-24 | A kind of cation-dyeable hydrophobic polyester and its production and use |
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| CN201610171980.0A CN107226901A (en) | 2016-03-24 | 2016-03-24 | A kind of cation-dyeable hydrophobic polyester and its production and use |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114164513A (en) * | 2021-12-27 | 2022-03-11 | 江苏恒科新材料有限公司 | Superfine cationic polyester fiber and preparation method thereof |
-
2016
- 2016-03-24 CN CN201610171980.0A patent/CN107226901A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114164513A (en) * | 2021-12-27 | 2022-03-11 | 江苏恒科新材料有限公司 | Superfine cationic polyester fiber and preparation method thereof |
| CN114164513B (en) * | 2021-12-27 | 2023-12-22 | 江苏恒科新材料有限公司 | Superfine cationic polyester fiber and preparation method thereof |
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Application publication date: 20171003 |