KR20110135755A - Urethane arcylate, binder composition containing the composition, and fabric treatment method using the binder - Google Patents
Urethane arcylate, binder composition containing the composition, and fabric treatment method using the binder Download PDFInfo
- Publication number
- KR20110135755A KR20110135755A KR1020100055666A KR20100055666A KR20110135755A KR 20110135755 A KR20110135755 A KR 20110135755A KR 1020100055666 A KR1020100055666 A KR 1020100055666A KR 20100055666 A KR20100055666 A KR 20100055666A KR 20110135755 A KR20110135755 A KR 20110135755A
- Authority
- KR
- South Korea
- Prior art keywords
- binder
- urethane acrylate
- fiber
- weight
- parts
- Prior art date
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
- C08L75/14—Polyurethanes having carbon-to-carbon unsaturated bonds
- C08L75/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
-
- 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
- D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
Abstract
Description
The present invention relates to a novel urethane acrylate, a binder composition comprising the same and a fiber processing method using the same.
It is the goal of the fiber chemist to make durable aroma processing on the fiber, but since the fragrance material is volatile, it must be micro (nano) encapsulated to attach to the fiber for a long time. Since there is no affinity between the encapsulated aroma and the fiber, it must be cured with a fixing agent. Curing process is a process for several minutes at 130 ~ 170 ℃ aroma fragrance in the capsule is rapidly lost from the capsule due to evaporation, expansion or destruction. At the same time as the aromatic aroma in the fiber is reduced, the durability of fragrance processing is also reduced. Efforts have been made to cure by UV irradiation at low temperatures as a means to cure the aromatic processing agent to the fiber in place of the high-temperature processing heat curing.
The development of UV curing processing technology for textiles is a future state-of-the-art dyeing and processing technology that can significantly reduce energy consumption and wastewater generation. ① Thermal drying. Productivity is good because the curing time is shorter than that of heat curing. ② It is a low-volume environment-friendly resin because of less volatile materials. ③ Especially, UV curing requires a compact equipment and requires a small area. The advantages of the small ones, but on the contrary, ① the unit cost is higher than the conventional resin composition of the thermosetting type, ② the rapid curing in a short time from the state of relatively small molecular weight has a large number of crosslinking point, and because of the shrinkage of the cured product due to large curing shrinkage Poor adhesion is likely to occur, ③ cause skin irritation by using solvent. In particular, when applying a UV curing agent to the fibers conventionally used in paints, inks, electronic materials, these disadvantages are more highlighted. There is a need for a study on a processing method using UV curing to provide a fiber having excellent binder properties without impairing the physical properties of the fiber.
The present invention aims to provide a novel urethane acrylate to solve the above problems.
The present invention also relates to a UV curable binder containing the urethane acrylate.
In addition, an object of the present invention is to provide a fiber having excellent binder properties by applying the binder to the fiber without damaging the physical properties.
The present invention relates to novel urethane acrylates. More specifically, it relates to the urethane acrylate represented by the following formula (1).
In Chemical Formula 1,
L is an integer of 1 to 6, m and n are each an integer of 1 to 10, R represents a hydrogen atom or a methyl group, D represents a divalent group selected from an aliphatic ring and an aromatic ring, and M represents a polytetramethylene glycol A hydrophobic divalent group derived from G represents a poly (ethylene glycol) or a hydrophilic divalent group derived from poly (ethylene glycol) (propylene glycol).
The present invention also relates to a binder composition comprising 100 parts by weight of the urethane acrylate, 1 to 4 parts by weight of photoinitiator and 2 to 5 parts by weight of crosslinking aid.
The present invention also relates to a method for processing fibers, comprising the step of printing the binder on the fiber sample, and curing the binder on the surface of the fiber sample by irradiating the printed fiber sample with UV.
According to the processing method of the fiber using the UV curable binder of the present invention, it is possible to prevent fiber damage due to heat, so that even after the processing agent is fixed to the fiber, the inherent properties of the fiber can be maintained and the shape stability can be maintained. . The processing method of the fiber of the present invention is possible by simply irradiating with UV, so there is no risk of environmental pollution or adverse effects on the human body, and it does not require a high temperature heat as well as occupy less installation area than a conventional thermosetting device. Therefore, it is more economical and can improve the durability of the aroma capsule.
1 is an FT-IR result of the urethane acrylate prepared in Preparation Example 1.
Figure 2 is a scanning microscope (SEM) photograph of the fiber printed with a UV curable binder according to the present invention.
3 is a graph of the content of the residue flavor oil for each binder according to the number of washing.
Hereinafter, the present invention will be described in more detail.
The present invention relates to novel urethane acrylates. More specifically, it relates to the urethane acrylate represented by the following formula (1).
[Formula 1]
In Chemical Formula 1,
L is an integer of 1 to 6, m and n are each an integer of 1 to 10, R represents a hydrogen atom or a methyl group, D represents a divalent group selected from an aliphatic ring and an aromatic ring, and M represents a polytetramethylene glycol A hydrophobic divalent group derived from G represents a poly (ethylene glycol) or a hydrophilic divalent group derived from poly (ethylene glycol) (propylene glycol).
D in
It is preferable that the hydrophobic divalent group and the hydrophilic divalent group of Chemical Formula 1 have a molecular weight of 500 to 4,000.
It is preferable that the ratio of m and n of the said Formula (1) is 1: 1-10. If out of the above range, there is a problem that the adhesiveness of the binder containing the urethane acrylate is poor.
Finally, the urethane acrylate preferably has a molecular weight of 5,000 to 20,000. If the molecular weight of the urethane acrylate is less than 5,000, there is a problem that can not be applied to the fiber treatment due to the low viscosity of the binder containing it, if the viscosity is higher than 20,000 may cause a problem that it hardens when synthesized due to high viscosity to be.
The urethane acrylate is a hydrophilic polyol such as poly (ethylene glycol) or poly (ethylene glycol) (propylene glycol), hydrophobic polyol such as poly tetramethylene glycol, and the like and isocyanate isocyanate such as IPDI, TMXDI or H 12 MDI. It can be prepared by reacting the reactor.
In addition, the present invention relates to a binder including 1 to 4 parts by weight of the photoinitiator and 2 to 5 parts by weight of the crosslinking assistant with respect to 100 parts by weight of the urethane acrylate of the formula (1).
The binder may be adjusted to a viscosity of 10,000 to 30,000 cps using a solvent such as water. By mixing the binder and the aromatic capsule, fragrance processing is possible. When adding an aromatic capsule, it is preferable to mix 1 to 5 parts by weight with respect to 100 parts by weight of urethane acrylate.
The photoinitiator is excited when UV is irradiated to generate radicals or ions to initiate photopolymerization or to cause photopolymerization with the aid of other sensitizers, preferably a benzophenone-based compound, an acyl phosphine oxide compound, or an acetophenone-based compound. At least one selected from the group consisting of compounds and benzoin ether compounds is suitable. Preferably 2-hydroxy-2-methylpropionphenone, 1-hydroxy cyclohexyl ketal, diphenyl- (2,4,6-trimethylbenzoyl) phosphine oxide and the like can be used, more preferably 2 -Hydroxy-2-methylpropionphenone and diphenyl- (2,4,6-trimethylbenzoyl) phosphine oxide can be used in combination.
The photoinitiator is used 1 to 4 parts by weight based on 100 parts by weight of the compound of the formula (1) urethane acrylate. In this case, when the content of the photoinitiator is less than 1 part by weight, the degree of curing decreases and the binder property deteriorates.
The crosslinking aid serves to increase the binder property and to control the viscosity of the binder and to use a monomer including diacrylate. Preferably, silicone acrylate, polyethylene glycol (PEG) 400 diacrylate, or the like is used, and more preferably polyethylene glycol (PEG) 400 diacrylate is used.
The crosslinking aid is used 2 to 5 parts by weight based on 100 parts by weight of the compound of the formula (1) urethane acrylate. Less than 2 parts by weight does not act as a crosslinking aid, and more than 5 parts by weight reduces the performance of the binder.
The present invention also relates to a method for processing fibers comprising the step of printing the binder on the fiber, and curing the binder on the surface of the fiber by irradiating the printed fiber with UV.
At this time, the fibers used are not particularly limited, both natural fibers and synthetic fibers can be used, woven fabrics, knitted fabrics and non-woven fabrics may also be subject to the binder treatment.
UV is an electromagnetic wave having a wavelength shorter than visible light, and can not only cut and oxidize molecular bonds of the irradiated surface organic material depending on the irradiation wavelength but also easily polymerize and crosslink the photocurable monomer.
The emission of UV is achieved by heating a substance having an atomic structure that is easy to emit electromagnetic waves to vaporize and applying a large amount of energy from the outside. Typically, mercury lamps are used a lot. When a mercury gas atom receives energy, mercury electrons are excited, and then the electrons return to a stable state to emit invisible UV. In general, UV lamps are divided into sterilization and UV curing, and are used in various ways depending on the intensity and wavelength range of the emitted energy.
In the fiber processing method using UV curing, the UV curing mechanism can be largely divided into radical reaction and cationic reaction. In the case of the radical reaction, the photoinitiator included in the processing agent is activated by UV to generate free radicals, which in turn activate the reactive oligomer to form a huge network structure, and then the curing reaction is terminated through a stop reaction. Machining is completed.
In the present invention, the fiber sample is printed with the UV-curable binder and then dried for 1 to 10 minutes at 50 to 100 ° C. Through the drying process, the efficiency of the curing reaction can be further improved.
At this time, the printing is printed using a silk screen, the printing thickness is preferably 10 to 30 ㎛. If the printing thickness is less than 10 μm, the amount of binder added is low, and the adhesiveness is lowered. If the printing thickness is more than 30 μm, the feel of the fiber may be stiff due to the excess binder and the film may be broken. This printing thickness can be controlled by adjusting the viscosity of the binder.
In particular, the printing amount of the binder when printing the binder according to the present invention on the fiber is preferably 10 to 20 g / m 2 , there is a problem in the physical properties and feel outside this range.
Thereafter, UV is irradiated to the dried sample using a UV irradiator. It is preferable to use a metal halogen lamp or a gallium lamp whose main wavelength is UV-A region for UV irradiation for hardening of a processing agent.
The amount of UV radiation affects the adhesion of the fiber, preferably irradiated in the range of 0.5 to 2 J / cm 2 , more preferably in the range of 1.0 to 1.5 J / cm 2 . If it is less than 0.5 J / cm 2, the activation of the photoinitiator is not made well, the progress of the curing reaction is not active, there is a problem that the adhesion is inferior, when exceeding 2 J / cm 2 fibers are embrittled.
Hereinafter, the present invention will be described in detail with reference to the following examples, but the present invention is not limited thereto.
Experimental Example One: NCO Measure
2-3 g of the sample was taken in a 250 ml Erlenmeyer flask. 25 ml of toluene was added to dissolve (isopropanol can be used when not dissolved in toluene). A 20 ml pipette of 2N n-dibutylamine ([CH 3 (CH 2 ) 3 ] 2 NH = 129.25,1 L, Assay: 99%) solution was added. After standing for 15-20 minutes, 100 ml of isopropanol was added to the measuring cylinder. After adding about 5-10 drops of Bromocresol green indicator, titration was started with 1N aqueous hydrochloric acid solution. 2 g Brocresol Green (C 21 H 13 Br 4 O 5 SNa = 720: Name of reagent) was dissolved in ethanol to make 100 ml. A blank test was performed at the end of the transition from blue to yellow.
[Equation 1]
NCO% = [(A-B) x F x 4.2] / S
A: Amount of 1N aqueous hydrochloric acid solution
B: amount of 1N aqueous hydrochloric acid solution
F: concentration coefficient of 1N hydrochloric acid aqueous solution
S: sample weight (g)
Experimental Example 2 : Laundry resistance ( KS K 0640 A-2)
KS K 0640 A-2 Washing conditions to determine whether the fragrance oil is released slowly. To quantify the fragrance remaining after washing, cut cotton fiber treated to a certain size and extract it with ethanol for a day. Absorbance was measured by UV-VIS spectroscopy at 285 nm, 290 nm jasmine oil). Abs is the absorbance of the fragrance oil eluted before and after washing.
% Of residue fragrance oil = Abs after washing / Abs before washing X 100
Manufacturing example 1: urethane Acrylate Produce
The 500 ml 4-neck flask was equipped with a mechanical stirrer, a condenser with a drying tube, a thermometer and a nitrogen injector. The mounted flask was placed in a mantle and the flask was first heated in vacuo to remove residual moisture. Polytetramethylene glycol (PTMG, Polytetramethylene glycol, Mn 500 to 2,000) and polyethylene-propylene glycol (PEG / PPG, Polyethylene glycol / Polypropylene glycol, Mn 500 to 2,000) were weighed in a 1: 1 molar ratio and then charged into a flask. After mixing all the polyols at 90 ℃ and cooled to 60 ℃ and dissolved in DMBA (Dimethylol butyric acid). Methylene diphenyl diisocyanate (MDI) containing 0.1% (w / w) catalyst (dibutyl tin dilaurate) was slowly added dropwise (the exothermic reaction), and when the dropwise addition was completed, the temperature was raised to 75-80 ° C. After measuring the NCO content from 2 hours after the increase in temperature (4-5%) when the expected content was introduced to the acrylic reactor (2-HEMA, 2-HEA, Glycidol) to cool to 50 ℃ and capping the NCO end. Reaction progress was confirmed by NCO measurement or FT-IR [see FIG. 1]. Upon completion of the reaction, triethylamine diluted with water was added dropwise and neutralized at 50 ° C. for 1 hour. The concentration was adjusted to 30 to 40% solids.
To prepare a urethane acrylate represented by the formula (2) (number average molecular weight about 15,000);
In Chemical Formula 2,
L is 1, m and n are each an integer of 1 to 10, R represents a hydrogen atom or a methyl group, D represents a divalent group selected from methylene diphenyl diisocyanate, and M represents a polytetramethylene having a molecular weight of 500 to 2,000. Hydrophobic divalent group derived from glycol is shown, G shows the hydrophilic divalent group derived from poly (ethylene glycol) or poly (ethylene glycol) (propylene glycol) of molecular weight 500-2,000.
FT-IR analysis of the prepared urethane acrylate is shown in FIG.
Example 1: Manufacture and processing of binders of fibers
Photoinitiator which mixed 100 g of urethane acrylate which is the compound manufactured by the said preparation example 1, 2-hydroxy-2-methylpropionphenone, and diphenyl- (2,4,6-trimethylbenzoyl) phosphine oxide in 3: 1 4 g and 5 g of diacrylate made of polyethylene glycol (PEG) 400 as a crosslinking aid, and 2 g of commercially available micro (nano) aroma capsules were added thereto to prepare a binder adjusted to a final viscosity of about 25,000 cps with water.
As a sample to be treated with binder, a refined bleached 20 male cotton fabric was cut into 30 cm × 20 cm size and silkscreen printed with the diluted binder.
The printed sample was dried at 80 ° C. for 2 minutes, and then irradiated with UV with a irradiation amount of 1.1 J / cm 2 using a UV curing machine equipped with a metal lamp (Fe).
Evaluation of the wash durability of the aroma capsule processed fiber sample was measured by the method of Experimental Example 2.
% Of fragrant oil
Example 2: according to the molecular structure of the binder Tensile strength Measure
Fiber processing was performed in the same manner as in Example 1, but the tensile strength of the urethane acrylate synthesized by varying the type of isocyanate was measured by KS K 0531 method and shown in Table 2 below.
kgf / mm 2
Tensile strength was significantly different according to the change of molecular structure, and the viscosity was not increased and the tensile strength was high when reacting with MDI (4,4'-Methylene diphenyl diisocyanate) among three isocyanates.
Example 3: Printing film According to thickness Residue Fragrant oil Content measurement
The water resistance was measured by adjusting the thickness of the printing film while varying the viscosity of the diluted concentration binder by adjusting the amount of water added in the binder, which is shown in Table 3 below.
(Measured with a colorimeter)
% Of fragrant oil
As shown in Table 3, as the printing film thickness increases, the adhesion is improved, but when the thickness of the printing film exceeds 30 μm, the fibers were stiff and the touch was poor.
Comparative example 1: acrylic binder
After printing the aromatic capsule using a commercially available acrylic screen binder (Korean Patent No. 520410) for 2 minutes at 150 ° C., the content of the residue flavor oil is shown in Table 5 below. The acrylic binder had excellent initial adhesiveness but poor touch, and the content of the residue aroma decreased drastically with the number of washes.
Comparative example 2: polyurethane binder
After printing the aromatic capsules using a commercially available silk binder for polyurethane screen (Korean Patent No. 249728), the content of the residue flavor oil is shown in Table 4 below.
Urethane Acrylate
Acrylic Binder
As can be seen in Table 4, the initial adhesiveness of Comparative Examples 1 and 2 was excellent, but it was confirmed that such adhesive performance was significantly reduced depending on the number of washing. Therefore, when the fiber is treated using the binder containing the urethane acrylate of the present invention was confirmed that the effect of fiber treatment lasts for a long time even washing the fiber.
Claims (16)
[Formula 1]
In Chemical Formula 1,
L is an integer from 1 to 6, m and n are each an integer from 1 to 10, R represents a hydrogen atom or a methyl group, D represents a divalent group selected from an aliphatic ring and an aromatic ring, and M represents a polytetramethylene glycol A hydrophobic divalent group derived from G represents a poly (ethylene glycol) or a hydrophilic divalent group derived from poly (ethylene glycol) (propylene glycol).
UV irradiation of the printed fiber to cure the binder on the fiber surface
Processing method of the fiber comprising a.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020100055666A KR101183517B1 (en) | 2010-06-11 | 2010-06-11 | Urethane Arcylate, Binder Composition Containing the Composition, and Fabric Treatment Method Using the Binder |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020100055666A KR101183517B1 (en) | 2010-06-11 | 2010-06-11 | Urethane Arcylate, Binder Composition Containing the Composition, and Fabric Treatment Method Using the Binder |
Publications (2)
Publication Number | Publication Date |
---|---|
KR20110135755A true KR20110135755A (en) | 2011-12-19 |
KR101183517B1 KR101183517B1 (en) | 2012-09-20 |
Family
ID=45502622
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020100055666A KR101183517B1 (en) | 2010-06-11 | 2010-06-11 | Urethane Arcylate, Binder Composition Containing the Composition, and Fabric Treatment Method Using the Binder |
Country Status (1)
Country | Link |
---|---|
KR (1) | KR101183517B1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101368825B1 (en) * | 2012-06-12 | 2014-03-03 | 한국생산기술연구원 | Treatment agent for cotton knitting textile and the knitting textile treated therewith |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101772613B1 (en) | 2014-12-01 | 2017-08-29 | 주식회사 엘지화학 | Coating composition, coating layer and film having self-healing property |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3889858B2 (en) | 1997-07-25 | 2007-03-07 | 共栄社化学株式会社 | Urethane / unsaturated organooligomer and process for producing the same |
KR20030097780A (en) | 2001-07-04 | 2003-12-31 | 쇼와 덴코 가부시키가이샤 | Resist curable resin composition and cured article thereof |
-
2010
- 2010-06-11 KR KR1020100055666A patent/KR101183517B1/en not_active IP Right Cessation
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101368825B1 (en) * | 2012-06-12 | 2014-03-03 | 한국생산기술연구원 | Treatment agent for cotton knitting textile and the knitting textile treated therewith |
Also Published As
Publication number | Publication date |
---|---|
KR101183517B1 (en) | 2012-09-20 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Zhao et al. | Self-healing UV light-curable resins containing disulfide group: Synthesis and application in UV coatings | |
CN110358020B (en) | Photosensitive resin and 3D printing polyurea method | |
Wang et al. | Fast self-healing engineered by UV-curable polyurethane contained Diels-Alder structure | |
Kayaman-Apohan et al. | UV-curable interpenetrating polymer networks based on acrylate/vinylether functionalized urethane oligomers | |
CN108102558B (en) | High-strength wet and light dual-curing polyurethane adhesive and preparation method and use method thereof | |
TW201300433A (en) | Functional polyurethane prepolymer, method of preparing polyurethane by using the same, and application method thereof | |
CN110483730B (en) | Polyurethane acrylate oligomer and preparation method and application method thereof | |
Yin et al. | Synthesis, photopolymerization kinetics, and thermal properties of UV-curable waterborne hyperbranched polyurethane acrylate dispersions | |
CN109111562B (en) | Self-repairing polyurethane, preparation method thereof and self-repairing method thereof | |
US7538163B2 (en) | Modification of thermoplastic polymers | |
CN113354789B (en) | Force-induced color-changing polyurethane elastomer material, and preparation method and application thereof | |
CN106519182A (en) | Organic silicon modified polyurethane acrylate oligomer, and preparation method thereof | |
CN110606931A (en) | Preparation method of waterborne light-cured self-repairing polyurethane resin | |
KR101183517B1 (en) | Urethane Arcylate, Binder Composition Containing the Composition, and Fabric Treatment Method Using the Binder | |
EP2821436A1 (en) | Transparent composite composition | |
CN111925642B (en) | Preparation method of self-repairing carbon nano tube-cationic waterborne polyurethane electromagnetic shielding composite material | |
CN114907763A (en) | Preparation method of hyperbranched photocuring waterborne polyurethane film | |
KR101068270B1 (en) | Synthesis and application of urethane acrylate for breathable water proof textiles as UV fixing agent | |
KR101520632B1 (en) | Prepolymer from biomass, polyurethane comprising the same, and method for preparing the same | |
CN109954169B (en) | Coating composition, coating method and coated product | |
CN115785383A (en) | Preparation method of self-repairing polyurethane containing DA bond and acylhydrazone bond double cross-linking | |
KR102343933B1 (en) | Phosphorus urethane flame retardant for cellulose fiber, Manufacturing method thereof and Flame retarding cellulose fiber using the same | |
Gao et al. | New poly (urethane-methacrylate) s obtained by adjusting the structure of the polyols moieties: synthesis, transparent, thermal and mechanical properties | |
KR20160084913A (en) | Manufacturing method of uv-light blocking fabric treatment agent and fabric treatment agent made by the same | |
EP3263761A1 (en) | Polyurethane-based uv absorber |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A201 | Request for examination | ||
E701 | Decision to grant or registration of patent right | ||
GRNT | Written decision to grant | ||
FPAY | Annual fee payment |
Payment date: 20150819 Year of fee payment: 4 |
|
FPAY | Annual fee payment |
Payment date: 20160607 Year of fee payment: 5 |
|
LAPS | Lapse due to unpaid annual fee |