CN113831494A - Cardanol biological anti-wrinkle cross-linking agent and preparation method and application thereof - Google Patents
Cardanol biological anti-wrinkle cross-linking agent and preparation method and application thereof Download PDFInfo
- Publication number
- CN113831494A CN113831494A CN202111174712.1A CN202111174712A CN113831494A CN 113831494 A CN113831494 A CN 113831494A CN 202111174712 A CN202111174712 A CN 202111174712A CN 113831494 A CN113831494 A CN 113831494A
- Authority
- CN
- China
- Prior art keywords
- cardanol
- wrinkle
- biological anti
- linking agent
- fabric
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- 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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
-
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3893—Low-molecular-weight compounds having heteroatoms other than oxygen containing silicon
-
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4833—Polyethers containing oxyethylene units
- C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
-
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
-
- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6681—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38
- C08G18/6685—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3225 or polyamines of C08G18/38
-
- 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
- C08G18/675—Low-molecular-weight compounds
-
- 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
- D06M15/568—Reaction products of isocyanates with polyethers
-
- 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
- D06M2101/02—Natural fibres, other than mineral fibres
- D06M2101/04—Vegetal fibres
- D06M2101/06—Vegetal fibres cellulosic
-
- 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
- D06M2101/34—Polyamides
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/20—Treatment influencing the crease behaviour, the wrinkle resistance, the crease recovery or the ironing ease
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/50—Modified hand or grip properties; Softening compositions
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
The invention provides a cardanol biological anti-wrinkle cross-linking agent and a preparation method and application thereof, wherein the cardanol biological anti-wrinkle cross-linking agent comprises the following raw materials in parts by weight: 1-2.5 parts of cardanol; 1-3 parts of polyisocyanate; 1-1.5 parts of polyether polyol; 0.2-1 part of silane coupling agent; 0.1-0.3 part of hydrophilic chain extender; 0.01-0.05 part of catalyst. The cardanol biological anti-wrinkle crosslinking agent disclosed by the invention is excellent in anti-wrinkle effect, green, environment-friendly and low in cost, and can keep good mechanical properties while improving the anti-wrinkle capability of fabrics.
Description
Technical Field
The invention belongs to the technical field of fabric after-finishing, and relates to a cardanol biological anti-wrinkle cross-linking agent, and a preparation method and application thereof.
Background
The traditional cotton fabric crease-resistant finishing agent comprises hydroxymethyl amide compounds, cyclic urea hydroxymethyl derivatives and the like, and the finishing agent has good crease-resistant effect and wide application, but can release a large amount of free formaldehyde during fabric finishing and storage, thereby being harmful to human health and safety. At present, in the fabric shrink-proof finishing, the organic silicon not only endows the fabric with shrink-resistant performance, but also can improve hand feeling and air permeability and improve the tearing strength, breaking strength and wear resistance of the fabric, but the requirement of durable press cannot be met at present by using the organic silicon finishing alone, and the cost is high. The polyurethane has good film forming property on natural fibers and synthetic fabrics and high bonding strength, can endow the fabrics with soft and plump hand feeling, and simultaneously, polyurethane macromolecules can generate addition reaction or can generate addition reaction with-OH and-NH in fiber molecules2And reacting to form a network cross-linked structure on the fabric, thereby playing a role of reinforcing the 'skeleton' of fiber molecules and endowing the fabric with durable shrink resistance.
CN102535172A discloses a method for manufacturing crease-resistant fabric, which utilizes the radio frequency reaction magnetron sputtering technology to cover the waterborne polyurethane crease-resistant finishing agent on the common fiber fabric to obtain crease-resistant fiber fabric, the thin film formed by the waterborne polyurethane crease-resistant finishing agent is uniformly covered on the fiber and well combined with the fiber, the service life of the crease-resistant fiber fabric is prolonged, meanwhile, the thickness of the thin film of the waterborne polyurethane crease-resistant finishing agent can be accurately regulated according to different application fields of the crease-resistant fiber fabric, and industrialization is easy to realize. But the invention has higher requirements on equipment and higher cost.
Therefore, in the field, development of an anti-wrinkle crosslinking agent which is excellent in anti-wrinkle effect, green, environmentally friendly, and low in cost has been desired.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a cardanol biological anti-wrinkle cross-linking agent and a preparation method and application thereof. The preparation method adopts polyisocyanate to react with block polyether polyol and a hydrophilic chain extender to generate polyurethane prepolymer, and the polyurethane prepolymer reacts with cardanol, the polyurethane prepolymer is connected into cardanol, and the cardanol has certain hydrophilic capacity by utilizing the hydrophilicity of waterborne polyurethane; the cardanol-polyurethane is further end-capped and modified by adopting a silane coupling agent, so that the cardanol biological anti-wrinkle crosslinking agent is prepared. The cardanol biological anti-wrinkle crosslinking agent disclosed by the invention has low VOC content after being used for crease resistance of a fabric, can obviously and effectively improve crosslinking density, improves the crease resistance of the fabric, and keeps better mechanical properties.
In order to achieve the purpose, the invention adopts the following technical scheme:
according to a first aspect, the invention provides a cardanol biological anti-wrinkle cross-linking agent, which comprises the following raw materials in parts by weight:
cardanol is a secondary vacuum distillation product of cashew nut shell liquid, is a renewable agricultural resource, is mainly a mixture of alkenyl phenols, and has double functional groups (phenolic hydroxyl and double bonds) and high reactivity. Because cardanol has almost no hydrophilicity and is only soluble in a nonpolar solvent, when cardanol is mixed with a water-based coating, cardanol spontaneously aggregates in a coating film, so that the curing process is not uniform, and the film-forming performance is affected. The problem of poor dispersibility of the waterborne polyurethane in the coating can be solved in the reaction of the waterborne polyurethane and the cardanol.
The reactive group (vinyl) provided by cardanol can improve the crosslinking degree of the crosslinking agent on the surface of the fabric and improve the anti-shrinkage performance of the finished fabric. In addition, cardanol also improves the resistance to air oxidation of the formed film, and the environment-friendly concept is compounded, so that the cardanol has a very large development prospect.
The cardanol biological cross-linking agent has the characteristic of multiple functionality (vinyl and amino), and is matched with a silane coupling agent to form Si-O-Si cross-linking, so that various cross-links can be formed in a system, and therefore the fabric has low strength loss and high crease recovery.
The present invention uses a silane coupling agent as an auxiliary reinforcing agent, and not only can increase the degree of crosslinking, but also can provide excellent heat resistance, cold resistance, flexibility, and excellent physical properties.
In the present invention, the cardanol may be used in an amount of 1 part, 1.1 parts, 1.2 parts, 1.3 parts, 1.4 parts, 1.5 parts, 1.6 parts, 1.7 parts, 1.8 parts, 1.9 parts, 2.0 parts, 2.1 parts, 2.2 parts, 2.3 parts, 2.4 parts, 2.5 parts, or the like, in the raw materials for preparing the cardanol-based biological anti-wrinkle crosslinking agent.
If the amount of cardanol used is too large, the whiteness of the fabric decreases and the elongation at break decreases, and if the amount of cardanol used is too small, the crease resistance of the fabric is not sufficiently improved.
In the present invention, in the preparation raw material of the cardanol biological anti-wrinkle crosslinking agent, the amount of the polyisocyanate may be 1 part, 1.3 parts, 1.5 parts, 1.8 parts, 2 parts, 2.3 parts, 2.5 parts, 2.8 parts, 3 parts, or the like.
In the present invention, the amount of polyether polyol used in the preparation raw material of the cardanol biological anti-wrinkle crosslinking agent may be 1 part, 1.1 parts, 1.2 parts, 1.3 parts, 1.4 parts, 1.5 parts, or the like.
In the present invention, the amount of the silane coupling agent used in the preparation raw material of the cardanol biological anti-wrinkle crosslinking agent may be 0.2 part, 0.3 part, 0.4 part, 0.5 part, 0.6 part, 0.7 part, 0.8 part, 0.9 part, 1 part, or the like.
In the invention, in the preparation raw materials of the cardanol biological anti-wrinkle cross-linking agent, the amount of the hydrophilic chain extender can be 0.1 part, 0.15 part, 0.2 part, 0.25 part or 0.3 part, etc.
In the present invention, the amount of the catalyst used in the preparation raw material of the cardanol biological anti-wrinkle crosslinking agent may be 0.01 parts, 0.02 parts, 0.03 parts, 0.04 parts, 0.05 parts, or the like.
Preferably, the polyisocyanate comprises any one of triphenylmethane triisocyanate, hexamethylene diisocyanate or toluene diisocyanate, or a combination of at least two thereof.
Preferably, the polyether polyol comprises a block polyether polyol, preferably a polyethylene glycol-polytetrahydrofuran three-arm block copolyether.
As a preferred technical scheme of the invention, the polyethylene glycol-polytetrahydrofuran three-arm block copolyether is selected, the high functionality of the polyethylene glycol-polytetrahydrofuran three-arm block copolyether is utilized to improve the crosslinking degree of a synthesized product and endow the product with a three-dimensional network structure during subsequent treatment.
Preferably, the silane coupling agent comprises 3-divinyltriaminopropylmethyldimethoxysilane and/or 3-divinyltriaminopropyltrimethoxysilane.
Preferably, the hydrophilic chain extender comprises sodium ethylene diamine sulfonate and/or sodium 1, 2-dihydroxy-3-propane sulfonate.
Preferably, the catalyst comprises any one of triethylamine, ethylenediamine, 2-azabicycloheptane or dibutyltin dilaurate, or a combination of at least two thereof.
In a second aspect, the present invention provides a preparation method of the cardanol biological anti-wrinkle crosslinking agent according to the first aspect, the preparation method comprising the following steps:
(1) mixing polyisocyanate, polyether polyol and a hydrophilic chain extender, then adding a catalyst, and reacting to obtain a waterborne polyurethane prepolymer;
(2) adding cardanol into the waterborne polyurethane prepolymer obtained in the step (1), heating, and reacting to obtain a cardanol biological anti-wrinkle cross-linking agent intermediate product;
(3) and (3) cooling the intermediate product of the cardanol biological anti-wrinkle cross-linking agent obtained in the step (2), adding a silane coupling agent, and reacting to obtain the cardanol biological anti-wrinkle cross-linking agent.
In the invention, the polyether polyol and the hydrophilic chain extender are added in the step (1), so that the flexibility of the synthesized waterborne polyurethane prepolymer is high, and the hand feeling of the finished fabric is improved.
Preferably, the reaction in step (1) is carried out at a temperature of 60-80 ℃, such as 60 ℃, 65 ℃, 70 ℃, 75 ℃ or 80 ℃ and the like, and for a time of 1-3h, such as 1h, 2h or 3h and the like.
Preferably, the temperature rise in step (2) is to 80-100 ℃, such as 80 ℃, 85 ℃, 90 ℃, 95 ℃ or 100 ℃ and the like.
Preferably, the reaction time in step (2) is 5-7h, such as 5h, 6h or 7h, etc.
Preferably, the temperature reduction in step (3) is to reduce the temperature to 25-35 ℃, such as 25 ℃, 30 ℃ or 35 ℃ and the like.
Preferably, the reaction time in step (3) is 0.5-1.5h, such as 0.5h, 1h or 1.5h, etc.
Preferably, the reactions described in step (2) and step (3) are both carried out under stirring.
In a third aspect, the invention provides the application of the cardanol biological anti-wrinkle cross-linking agent in the first aspect in fabric anti-wrinkle finishing.
Preferably, the fabric comprises a cotton fabric, a nylon fabric or a viscose fabric.
Preferably, the method of finishing comprises the steps of: dissolving the cardanol biological crease-resistant cross-linking agent in deionized water, dipping the fabric, drying, and baking to obtain the finished fabric.
Preferably, the cardanol biological anti-wrinkle crosslinking agent is added in an amount of 7-9% owf, such as 7% owf, 8% owf, 9% owf, or the like. owf, on weight of fabric, for dyeing indicates the percentage content of dye, which refers to the ratio of the amount of dye used to the weight of the fabric.
Preferably, the deionized water is added in an amount such that the bath ratio is 1 (25-35), e.g., 1:25, 1:30, or 1:35, etc. The bath ratio refers to the ratio of the fabric in the dip dyeing mode to the dye liquor, also called liquor ratio, and refers to the weight ratio of the textile to the dye liquor.
Preferably, the time of the impregnation is 10-15min, such as 10min, 11min, 12min, 13min, 14min or 15min, etc.
Preferably, the drying temperature is 90-110 ℃, such as 90 ℃, 100 ℃ or 110 ℃, and the drying time is 10-15min, such as 10min, 11min, 12min, 13min, 14min or 15 min.
Preferably, the baking temperature is 140-160 ℃, such as 140 ℃, 150 ℃ or 160 ℃, and the baking time is 3-5min, such as 3min, 4min or 5 min.
Compared with the prior art, the invention has at least the following beneficial effects:
(1) the cardanol and the silane coupling agent are matched to act, so that the functionality of the crosslinking agent is improved, various crosslinks can be formed in a system, the strength loss of fabrics is small (the strength retention rate is 89-94%), and the crease recovery is high (the crease recovery angle is 216-228 degrees);
(2) the cardanol used in the invention is extracted from natural plant shell oil, is a renewable agricultural resource, does not contain harmful substances such as formaldehyde and the like, is green, healthy and environment-friendly, and has low price;
(3) the cardanol biological crease-resistant cross-linking agent prepared by the invention has the excellent performance of silicone oil and the plump hand feeling of polyurethane, has the characteristics of easy cleaning, easy processing and the like of water-based emulsion, and is a crease-resistant cross-linking agent with excellent performance, wide applicable scene, environmental protection and high cost performance.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
Example 1
The preparation raw materials of the cardanol biological anti-wrinkle cross-linking agent comprise the following components in parts by weight:
wherein the polyisocyanate is triphenylmethane triisocyanate; the polyether polyol is polyethylene glycol-polytetrahydrofuran three-arm block copolyether; the silane coupling agent is 3-diethylenetriaminopropyltrimethoxysilane; the hydrophilic chain extender is ethylenediamine sodium sulfonate; the catalyst is a mixture of ethylenediamine and dibutyltin dilaurate in a mass ratio of 1: 1.
The preparation method comprises the following steps:
(1) adding polyisocyanate, polyether polyol and a hydrophilic chain extender into a three-neck flask, then adding a catalyst, and reacting for 2 hours at 70 ℃ to obtain a waterborne polyurethane prepolymer;
(2) adding cardanol into the waterborne polyurethane prepolymer obtained in the step (1), heating to 100 ℃, and stirring for reacting for 6 hours to obtain a cardanol biological anti-wrinkle cross-linking agent intermediate product;
(3) and (3) cooling the intermediate product of the cardanol biological anti-wrinkle crosslinking agent obtained in the step (2) to 25 ℃, adding a silane coupling agent, and stirring for reacting for 1h to obtain the cardanol biological anti-wrinkle crosslinking agent.
The embodiment also provides an application of the cardanol biological anti-wrinkle cross-linking agent in fabric anti-wrinkle finishing, and the finishing method comprises the following steps: dissolving 8% owf cardanol biological anti-wrinkle cross-linking agent in deionized water at a bath ratio of 1:30, soaking the cotton fabric for 10min, drying at 100 ℃ for 10min, and then baking at 150 ℃ for 3min to obtain the finished fabric.
Example 2
The preparation raw materials of the cardanol biological anti-wrinkle cross-linking agent comprise the following components in parts by weight:
wherein the polyisocyanate is hexamethylene diisocyanate; the polyether polyol is polyethylene glycol-polytetrahydrofuran three-arm block copolyether; the silane coupling agent is 3-diethylenetriaminopropyltrimethoxysilane; the hydrophilic chain extender is 1, 2-dihydroxy-3-propanesulfonic acid sodium salt; the catalyst is a mixture of ethylenediamine and dibutyltin dilaurate in a mass ratio of 1: 1.
The preparation method comprises the following steps:
(1) adding polyisocyanate, polyether polyol and a hydrophilic chain extender into a three-neck flask, then adding a catalyst, and reacting at 80 ℃ for 2 hours to obtain a waterborne polyurethane prepolymer;
(2) adding cardanol into the waterborne polyurethane prepolymer obtained in the step (1), heating to 90 ℃, and stirring for reacting for 6 hours to obtain a cardanol biological anti-wrinkle cross-linking agent intermediate product;
(3) and (3) cooling the intermediate product of the cardanol biological anti-wrinkle crosslinking agent obtained in the step (2) to 30 ℃, adding a silane coupling agent, and stirring for reacting for 1h to obtain the cardanol biological anti-wrinkle crosslinking agent.
The embodiment also provides an application of the cardanol biological anti-wrinkle cross-linking agent in fabric anti-wrinkle finishing, and the finishing method comprises the following steps: dissolving 8% owf cardanol biological anti-wrinkle cross-linking agent in deionized water at a bath ratio of 1:30, soaking the cotton fabric for 10min, drying at 100 ℃ for 10min, and then baking at 150 ℃ for 3min to obtain the finished fabric.
Example 3
The preparation raw materials of the cardanol biological anti-wrinkle cross-linking agent comprise the following components in parts by weight:
wherein the polyisocyanate is toluene diisocyanate; the polyether polyol is polyethylene glycol-polytetrahydrofuran three-arm block copolyether; the silane coupling agent is 3-diethylenetriaminopropyltrimethoxysilane; the hydrophilic chain extender is 1, 2-dihydroxy-3-propanesulfonic acid sodium salt; the catalyst is a mixture of ethylenediamine and dibutyltin dilaurate in a mass ratio of 1: 1.
The preparation method comprises the following steps:
(1) adding polyisocyanate, polyether polyol and a hydrophilic chain extender into a three-neck flask, then adding a catalyst, and reacting for 2 hours at 70 ℃ to obtain a waterborne polyurethane prepolymer;
(2) adding cardanol into the waterborne polyurethane prepolymer obtained in the step (1), heating to 80 ℃, and stirring for reacting for 6 hours to obtain a cardanol biological anti-wrinkle cross-linking agent intermediate product;
(3) and (3) cooling the intermediate product of the cardanol biological anti-wrinkle crosslinking agent obtained in the step (2) to 30 ℃, adding a silane coupling agent, and stirring for reacting for 1h to obtain the cardanol biological anti-wrinkle crosslinking agent.
The embodiment also provides an application of the cardanol biological anti-wrinkle cross-linking agent in fabric anti-wrinkle finishing, and the finishing method comprises the following steps: dissolving 8% owf cardanol biological anti-wrinkle cross-linking agent in deionized water at a bath ratio of 1:30, soaking the cotton fabric for 10min, drying at 100 ℃ for 10min, and then baking at 150 ℃ for 3min to obtain the finished fabric.
Example 4
The preparation raw materials of the cardanol biological anti-wrinkle cross-linking agent comprise the following components in parts by weight:
wherein the polyisocyanate is triphenylmethane triisocyanate; the polyether polyol is polyethylene glycol-polytetrahydrofuran three-arm block copolyether; the silane coupling agent is 3-diethylenetriaminopropylmethyldimethoxysilane; the hydrophilic chain extender is ethylenediamine sodium sulfonate; the catalyst is triethylamine.
The preparation method comprises the following steps:
(1) adding polyisocyanate, polyether polyol and a hydrophilic chain extender into a three-neck flask, then adding a catalyst, and reacting at 60 ℃ for 3 hours to obtain a waterborne polyurethane prepolymer;
(2) adding cardanol into the waterborne polyurethane prepolymer obtained in the step (1), heating to 85 ℃, and stirring for reaction for 7 hours to obtain a cardanol biological anti-wrinkle cross-linking agent intermediate product;
(3) and (3) cooling the intermediate product of the cardanol biological anti-wrinkle cross-linking agent obtained in the step (2) to 35 ℃, adding a silane coupling agent, and stirring for reaction for 0.5h to obtain the cardanol biological anti-wrinkle cross-linking agent.
The embodiment also provides an application of the cardanol biological anti-wrinkle cross-linking agent in fabric anti-wrinkle finishing, and the finishing method comprises the following steps: dissolving 8% owf cardanol biological anti-wrinkle cross-linking agent in deionized water at a bath ratio of 1:30, soaking the cotton fabric for 10min, drying at 100 ℃ for 10min, and then baking at 150 ℃ for 3min to obtain the finished fabric.
Example 5
The preparation raw materials of the cardanol biological anti-wrinkle cross-linking agent comprise the following components in parts by weight:
wherein the polyisocyanate is hexamethylene diisocyanate; the polyether polyol is polyethylene glycol-polytetrahydrofuran three-arm block copolyether; the silane coupling agent is 3-diethylenetriaminopropylmethyldimethoxysilane; the hydrophilic chain extender is 1, 2-dihydroxy-3-propanesulfonic acid sodium salt; the catalyst was dibutyltin dilaurate.
The preparation method comprises the following steps:
(1) adding polyisocyanate, polyether polyol and a hydrophilic chain extender into a three-neck flask, then adding a catalyst, and reacting for 2 hours at 65 ℃ to obtain a waterborne polyurethane prepolymer;
(2) adding cardanol into the waterborne polyurethane prepolymer obtained in the step (1), heating to 95 ℃, and stirring for reaction for 5 hours to obtain a cardanol biological anti-wrinkle cross-linking agent intermediate product;
(3) and (3) cooling the intermediate product of the cardanol biological anti-wrinkle cross-linking agent obtained in the step (2) to 30 ℃, adding a silane coupling agent, and stirring for reacting for 1.5 hours to obtain the cardanol biological anti-wrinkle cross-linking agent.
The embodiment also provides an application of the cardanol biological anti-wrinkle cross-linking agent in fabric anti-wrinkle finishing, and the finishing method comprises the following steps: dissolving 8% owf cardanol biological anti-wrinkle cross-linking agent in deionized water at a bath ratio of 1:30, soaking the cotton fabric for 10min, drying at 100 ℃ for 10min, and then baking at 150 ℃ for 3min to obtain the finished fabric.
Example 6
This example was different from example 1 only in that the silane coupling agent 3-divinyltriaminopropyltrimethoxysilane was replaced with the same amount of gamma-aminopropyltriethoxysilane (KH-550), and the other conditions were the same as in example 1.
Comparative example 1
A commercially available reaction-type polyisocyanate aqueous polyurethane crosslinking agent (brand: Jitian F0402) was purchased.
Dissolving 8% owf reaction type polyisocyanate waterborne polyurethane crosslinking agent in deionized water, wherein the bath ratio is 1:30, dipping the cotton fabric for 10min, and baking for 3min at 150 ℃ to obtain the finished fabric.
Comparative example 2
A commercially available blocked silicone waterborne polyurethane crosslinker (brand: six chain LP-900) was purchased.
Dissolving 8% owf commercial closed type organic silicon waterborne polyurethane crosslinking agent in deionized water, wherein the bath ratio is 1:30, soaking the cotton fabric for 10min, and then drying for 10min at 100 ℃.
Comparative example 3
The original fabric.
Comparative example 4
This comparative example is different from example 1 only in that the silane coupling agent is not included in the raw materials for preparation, and accordingly, step (3) is not included in the preparation method, and the other conditions are the same as example 1.
Comparative example 5
This comparative example is different from example 1 only in that the cardanol is 0.5 parts by weight, and the other conditions are the same as example 1.
Comparative example 6
This comparative example is different from example 1 only in that cardanol is 3 parts by weight, and the other conditions are the same as example 1.
Comparative example 7
This comparative example differs from example 1 only in that cardanol is replaced with the same amount of eugenol, and the other conditions are the same as in example 1.
The finished fabrics provided in examples 1-6 and comparative examples 1-7 (of which comparative example 3 is the base fabric) were tested for performance as follows:
(1) breaking strength and strength retention: testing according to the method of GB/T3923.1-2013;
(2) crease recovery angle (snap): testing was carried out according to GB/T3819-1997;
(3) whiteness: testing was carried out according to the method of GB/T8424.2-2001;
(4) elongation at break: the test was carried out according to the method of GB/T24218.3-2010.
The results of the performance tests are shown in table 1.
TABLE 1
As can be seen from Table 1, the finished fabrics provided in examples 1-5 all had higher wrinkle recovery angles (216-228 ℃) and had no significant reduction in breaking strength (280-294N), strength retention (89-94%), elongation at break (10-12%) and whiteness (72-80) as compared to the original fabric.
Compared with the fabric prepared in the embodiment 1 and 6, the fabric prepared in the embodiment has slightly reduced breaking strength, strength retention rate, wrinkle recovery angle and elongation at break, and the crosslinking capability of the 3-diethylenetriaminopropyltrimethoxysilane in a system is proved to be superior to KH-500, so that the crease resistance of the fabric is improved.
Compared with examples 1-5, the finished fabric provided in comparative example 1 has reduced breaking strength, strength retention rate, wrinkle recovery angle and elongation at break, and the cardanol biological anti-wrinkle crosslinking agent is proved to be capable of obviously and effectively improving crosslinking density and anti-wrinkle capacity of the fabric.
The finished fabric provided in comparative example 2 had a slightly higher crease recovery angle compared to comparative example 1, indicating that the incorporation of silicone can improve the crease resistance of the fabric; compared with examples 1-5, the finished fabric provided in comparative example 2 has reduced breaking strength, strength retention, wrinkle recovery angle, and elongation at break, which indicates that the combined action of cardanol and silicone improves the functionality of the film, so that the film has various cross-linked structures, and the wrinkle resistance of the fabric is significantly improved.
Comparative example 4 provided a finished fabric with reduced breaking strength, strength retention, and crease recovery angle compared to example 1; the crease recovery angle of the finished fabric provided in comparative example 5 was significantly reduced, and the whiteness of the finished fabric provided in comparative example 6 was significantly reduced; comparative example 7 provides a finished fabric with significantly reduced breaking strength and crease recovery angle. The fact that the cardanol has the best anti-wrinkle performance improvement on the fabric under the condition of 1-2.5 parts is proved, and the influence on the whiteness, the breaking strength and the breaking elongation of the fabric is small.
The applicant states that the cardanol biological anti-wrinkle cross-linking agent, the preparation method and the application thereof are described by the above examples, but the invention is not limited to the above examples, that is, the invention is not limited to the above examples. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
Claims (10)
1. The cardanol biological anti-wrinkle cross-linking agent is characterized by comprising the following raw materials in parts by weight:
2. the cardanol biological anti-wrinkle crosslinking agent according to claim 1, wherein the polyisocyanate comprises any one of triphenylmethane triisocyanate, hexamethylene diisocyanate, or toluene diisocyanate, or a combination of at least two of the foregoing.
3. The cardanol biological anti-wrinkle crosslinking agent according to claim 1 or 2, wherein the polyether polyol comprises a block polyether polyol, preferably a polyethylene glycol-polytetrahydrofuran three-arm block copolyether.
4. The cardanol biological anti-wrinkle crosslinking agent according to any one of claims 1 to 3, wherein the silane coupling agent comprises 3-divinyltriaminopropylmethyldimethoxysilane and/or 3-divinyltriaminopropyltrimethoxysilane.
5. The cardanol biological anti-wrinkle crosslinking agent according to any one of claims 1-4, wherein the hydrophilic chain extender comprises sodium ethylene diamine sulfonate and/or sodium 1, 2-dihydroxy-3-propane sulfonate;
preferably, the catalyst comprises any one of triethylamine, ethylenediamine, 2-azabicycloheptane or dibutyltin dilaurate, or a combination of at least two thereof.
6. The preparation method of the cardanol biological anti-wrinkle crosslinking agent according to any one of claims 1 to 5, wherein the preparation method comprises the following steps:
(1) mixing polyisocyanate, polyether polyol and a hydrophilic chain extender, then adding a catalyst, and reacting to obtain a waterborne polyurethane prepolymer;
(2) adding cardanol into the waterborne polyurethane prepolymer obtained in the step (1), heating, and reacting to obtain a cardanol biological anti-wrinkle cross-linking agent intermediate product;
(3) and (3) cooling the intermediate product of the cardanol biological anti-wrinkle cross-linking agent obtained in the step (2), adding a silane coupling agent, and reacting to obtain the cardanol biological anti-wrinkle cross-linking agent.
7. The preparation method according to claim 6, wherein the reaction temperature in the step (1) is 60-80 ℃, and the reaction time is 1-3 h;
preferably, the temperature rise in the step (2) is to be 80-100 ℃;
preferably, the reaction time of the step (2) is 5-7 h.
8. The preparation method according to claim 6 or 7, wherein the temperature reduction in the step (3) is to be carried out to 25-35 ℃;
preferably, the reaction time of the step (3) is 0.5-1.5 h.
9. Use of a cardanol-based biological anti-wrinkle crosslinking agent according to any one of claims 1 to 5 in anti-wrinkle finishing of fabrics.
10. Use according to claim 9, wherein the fabric comprises cotton, nylon or viscose fabric;
preferably, the method of finishing comprises the steps of: dissolving a cardanol biological crease-resistant cross-linking agent in deionized water, impregnating a fabric, drying, and baking to obtain a finished fabric;
preferably, the addition amount of the cardanol biological anti-wrinkle cross-linking agent is 7-9% owf;
preferably, the deionized water is added in an amount such that the bath ratio is 1 (25-35);
preferably, the time of the impregnation is 10-15 min;
preferably, the drying temperature is 90-110 ℃, and the drying time is 10-15 min;
preferably, the baking temperature is 140-160 ℃, and the baking time is 3-5 min.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111174712.1A CN113831494B (en) | 2021-10-09 | 2021-10-09 | Cardanol biological anti-wrinkle cross-linking agent and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111174712.1A CN113831494B (en) | 2021-10-09 | 2021-10-09 | Cardanol biological anti-wrinkle cross-linking agent and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN113831494A true CN113831494A (en) | 2021-12-24 |
| CN113831494B CN113831494B (en) | 2023-03-31 |
Family
ID=78968085
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111174712.1A Active CN113831494B (en) | 2021-10-09 | 2021-10-09 | Cardanol biological anti-wrinkle cross-linking agent and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113831494B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117700668A (en) * | 2023-12-13 | 2024-03-15 | 广东宏昊化工有限公司 | Polyurethane and preparation method and application thereof |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5458800A (en) * | 1977-10-19 | 1979-05-11 | Mitsubishi Electric Corp | Curable polymer composition |
| CN1704523A (en) * | 2004-05-27 | 2005-12-07 | 香港理工大学 | Reactive aqueous polyurethane fabric finishing agent, its preparation method and application |
| CN105274849A (en) * | 2015-11-06 | 2016-01-27 | 辽宁恒星精细化工有限公司 | Water-based reactive polyurethane resin crease-resistant finishing agent and preparing method |
| CN105992784A (en) * | 2013-11-27 | 2016-10-05 | 陶氏环球技术有限责任公司 | Cardanol modified epoxy polyol |
| CN107082863A (en) * | 2017-05-22 | 2017-08-22 | 昆山嘉力普制版胶粘剂油墨有限公司 | A kind of preparation method of high intensity anacardol base water polyurethane |
| US20190077815A1 (en) * | 2017-09-12 | 2019-03-14 | Cardolite Corporation | Compositions, synthesis, and uses of hydrolyzable silane modified cashew nut shell liquid derivatives |
| CN112250812A (en) * | 2020-10-23 | 2021-01-22 | 辽宁恒星精细化工有限公司 | Waterborne polyurethane crease-resistant finishing agent, preparation method thereof and durable crease-resistant nylon 56 fabric |
-
2021
- 2021-10-09 CN CN202111174712.1A patent/CN113831494B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5458800A (en) * | 1977-10-19 | 1979-05-11 | Mitsubishi Electric Corp | Curable polymer composition |
| CN1704523A (en) * | 2004-05-27 | 2005-12-07 | 香港理工大学 | Reactive aqueous polyurethane fabric finishing agent, its preparation method and application |
| CN105992784A (en) * | 2013-11-27 | 2016-10-05 | 陶氏环球技术有限责任公司 | Cardanol modified epoxy polyol |
| CN105274849A (en) * | 2015-11-06 | 2016-01-27 | 辽宁恒星精细化工有限公司 | Water-based reactive polyurethane resin crease-resistant finishing agent and preparing method |
| CN107082863A (en) * | 2017-05-22 | 2017-08-22 | 昆山嘉力普制版胶粘剂油墨有限公司 | A kind of preparation method of high intensity anacardol base water polyurethane |
| US20190077815A1 (en) * | 2017-09-12 | 2019-03-14 | Cardolite Corporation | Compositions, synthesis, and uses of hydrolyzable silane modified cashew nut shell liquid derivatives |
| CN112250812A (en) * | 2020-10-23 | 2021-01-22 | 辽宁恒星精细化工有限公司 | Waterborne polyurethane crease-resistant finishing agent, preparation method thereof and durable crease-resistant nylon 56 fabric |
Non-Patent Citations (4)
| Title |
|---|
| CHANGQING FU等: "Effect of structure on the properties of polyurethanes based on aromatic cardanol-based polyols prepared by thiol-ene coupling", 《PROGRESS IN ORGANIC COATINGS》 * |
| CHUANJIE CHENG等: "Preparation of Fully Bio-Based UV-Cured Non-Isocyanate Polyurethanes From Ricinoleic Acid", 《JOURNAL OF MACROMOLECULAR SCIENCE, PART A: PURE AND APPLIED CHEMISTRY》 * |
| 苏玲 等: "三臂聚乙二醇/四氢呋喃星形嵌段共聚醚的合成及其聚氨酯弹性体的力学性能", 《合成橡胶工业》 * |
| 赵朝阳 等: "腰果酚封闭聚氨酯预聚体的合成及性能研究", 《中国聚氨酯工业协会第十九次年会论文集》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117700668A (en) * | 2023-12-13 | 2024-03-15 | 广东宏昊化工有限公司 | Polyurethane and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN113831494B (en) | 2023-03-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US20200354498A1 (en) | Polyurethane-acrylate Water Repellant Prepared by Double Bonds in Side Chain | |
| EP2152957B1 (en) | Fluorocarbon polymer-free preparations based on water and/or organic solvents and the use thereof as a finish on flexible sheet material | |
| CN101914857B (en) | Method for preparing reactive polyurethane film-forming color fixing agent | |
| EP2698391B1 (en) | Self-crosslinkable polysiloxane-modified polyhydroxy polyurethane resin, process for producing said resin, resin material comprising said resin, and artificial leather produced utilizing said resin | |
| CN113831494B (en) | Cardanol biological anti-wrinkle cross-linking agent and preparation method and application thereof | |
| CN114381191A (en) | Hydroxyl silicone oil modified waterborne polyurethane coating with high tensile strength and high water resistance coating film | |
| CN113338051A (en) | Preparation method of solvent-free waterborne polyurethane microfiber synthetic leather with high R value | |
| CN111533880B (en) | Preparation method of nano-silica modified waterborne polyurethane | |
| CN106008893B (en) | Polyurethane water-proof endures with all one's will the preparation method and products thereof of agent emulsion | |
| CN114044861B (en) | Polyurethane modified acrylic ester pigment printing adhesive for polyester oxford fabric and preparation method thereof | |
| CN114853970A (en) | Closed cationic waterborne polyurethane curing agent and preparation method and application thereof | |
| CN111533875B (en) | Preparation method of cationic waterborne polyurethane, leather bottom sealing resin and leather coating | |
| CN111072914A (en) | High-solid-content polyurethane resin, impregnating slurry and application thereof | |
| CN106758252A (en) | Easy care type water and oil repellent agent and preparation method thereof, textile | |
| KR20060132777A (en) | Dispersion polycarbonate polyurethane resin | |
| CN111732708B (en) | Soft high-resilience aqueous polyurethane resin and preparation method and application thereof | |
| CN109629269A (en) | A kind of suede color fixing agent and its preparation method and application | |
| CN111300951A (en) | Preparation method of waterproof suit fabric | |
| CN111304908A (en) | Self-cleaning suit fabric and preparation method thereof | |
| CN106758387A (en) | A kind of environmentally friendly formaldehydeless chlorine-resistant cotton color fixing agent | |
| CN114409853B (en) | Fluorine-free waterproof agent and preparation method thereof | |
| CN113549187B (en) | Aqueous polyurethane for microfiber leather and preparation method thereof | |
| CN114575163A (en) | Anti-fouling and crease-resistant garment fabric | |
| CN103289047A (en) | Improved polyurethane, preparation method and application thereof | |
| CN113956403A (en) | Preparation method of polyurethane modified acrylate thick plate printing adhesive |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |