CN110734664A - crosslinking agents and application thereof - Google Patents

crosslinking agents and application thereof Download PDF

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Publication number
CN110734664A
CN110734664A CN201910835906.8A CN201910835906A CN110734664A CN 110734664 A CN110734664 A CN 110734664A CN 201910835906 A CN201910835906 A CN 201910835906A CN 110734664 A CN110734664 A CN 110734664A
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group
compound
coating
cross
solvent
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冯炜
赵亚平
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Zhuhai Bona Bio Technology Co Ltd
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Zhuhai Bona Bio Technology Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/63—Additives non-macromolecular organic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
    • C07C69/54—Acrylic acid esters; Methacrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D105/00—Coating compositions based on polysaccharides or on their derivatives, not provided for in groups C09D101/00 or C09D103/00
    • C09D105/04—Alginic acid; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D105/00—Coating compositions based on polysaccharides or on their derivatives, not provided for in groups C09D101/00 or C09D103/00
    • C09D105/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D139/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Coating compositions based on derivatives of such polymers
    • C09D139/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
    • C09D139/06—Homopolymers or copolymers of N-vinyl-pyrrolidones
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
    • C09D171/02—Polyalkylene oxides

Abstract

The invention belongs to the field of materials, and discloses cross-linking agents, wherein the structural general formula of the cross-linking agent is (R)1)m‑X‑(R2)nSaid R is1The group contains a carbon-carbon double bond linking the carbonyl groups; the R is2Contains a benzophenone structure; x is at least 2-OH to remove H or contains-NH2Removing H, wherein m is more than or equal to 1, n is more than or equal to 1,m and n are positive integers, the compound providing the structure of X is at least of ethylene glycol, pentaerythritol, dipentaerythritol, glycerol, tris, citric acid, trimethylolpropane and ethylenediamine, and R is provided1The compounds of the group contain a carbon-carbon double bond linking the carbonyl group; providing R2The compound of the group is benzophenone and derivatives thereof. The coating prepared by the cross-linking agent is applied to the surface of the medical instrument to form a lubricating layer, so that the friction coefficient of the surface of the medical instrument is obviously reduced, and the coating has good lubricity and can be used for multiple times.

Description

crosslinking agents and application thereof
Technical Field
The invention belongs to the field of materials, and particularly relates to crosslinking agents and application thereof.
Background
In the medical field, medical instruments, such as catheters, are frequently used for accessing the human body. Untreated medical devices often have a problem of high friction during their entry into the body. Therefore, it is necessary to perform a lubrication treatment on the surface of the medical device. For example, when the catheter is inserted into or pulled out of human tissue, the surface of the catheter needs to be lubricated, so that the pain and the injury to a patient are reduced.
The surface of a medical device is modified to be highly hydrophobic or highly hydrophilic, so that the effects of reducing a friction coefficient and improving a lubricating effect can be achieved, if a high-hydrophobic coating is obtained, high-hydrophobic substances such as silicone oil, castor oil and the like can be coated on the surface of the medical device, but the treatment method is poor in effect and firmness, the high-hydrophilic coating has better lubricating property and firmness compared with the traditional hydrophobic coating, and can absorb water quickly to reduce the surface friction coefficient after meeting water.
US5091205A discloses methods for making hydrophilic coatings, which are two-step processes, isocyanate as a base coat and polyacrylic acid as a hydrophilic lubricating coat, and methyl ethyl ketone as a solvent, and the coating is cured at a temperature above 60 ℃.
In the prior art, a cross-linking agent with a single functional group is mostly utilized in a hydrophilic coating, and then a hydrophilic coating is formed on the surface of a medical instrument.
Therefore, it is necessary to provide kinds of multifunctional crosslinking agents, and then add them into the coating to form a hydrophilic coating on the surface of the medical device, so as to reduce the friction coefficient of the surface of the medical device, and maintain good lubricating performance even if entering and exiting the human body for many times.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides crosslinking agents, wherein the crosslinking agents contain polyfunctional groups, and the hydrophilic coating prepared by the crosslinking agents is applied to the surface of the medical instrument, so that the friction coefficient of the surface of the medical instrument is obviously reduced, and the medical instrument has good lubricity and still has good lubricating property after being used for many times.
crosslinking agents, wherein the structural general formula of the crosslinking agent is (R)1)m-X-(R2)nSaid R is1The group contains a carbon-carbon double bond to a carbonyl group; the R is2The radical contains a benzophenone structure; x is a bond R1And R2Wherein X is a compound containing at least 2-OH to remove H or-NH2Removing H structure; wherein m is more than or equal to 1, n is more than or equal to 1, and m and n are positive integers (m and n are more than or equal to 1 and represent R1Group and R2The number of groups).
Preferably, X is
Figure BDA0002192150950000021
Preferably, said R is1The radical is
Preferably, said R is2The radical is
Figure BDA0002192150950000023
Preferably, in the crosslinking agent, m is more than or equal to 2, and n is more than or equal to 2.
preferably, the cross-linking agent has the formula:
Figure BDA0002192150950000024
Figure BDA0002192150950000031
the R is1And R2Are all photosensitive groups.
A method for preparing a cross-linking agent, comprising the steps of:
(1) providing a compound of X structure, providing R1Mixing the radical compound with a solvent, and stirring and reacting for 1-2 hours at 10-40 ℃ under the protection of inert gas to prepare an intermediate for later use;
(2) addition to the intermediate prepared in step (1) provides R2The compound of the group and the solvent react for 1 to 2 hours under the protection of inert gas and the temperature of 10 to 40 ℃ by stirring to prepare the cross-linking agent.
Preferably, the compound providing the structure of X is at least of ethylene glycol, pentaerythritol, dipentaerythritol, glycerol, tris, citric acid, trimethylolpropane and ethylenediamine.
Preferably, R is provided1Radical (I)The compounds of (a) contain a carbon-carbon double bond to a carbonyl group, such as acryloyl chloride.
Preferably, R is provided2The compounds of the group contain benzophenone structures and may be benzophenone and its derivatives, such as 4-bromomethylbenzophenone, 4-benzoyl chloride.
In the step (1), a compound having an X structure is provided, and R is provided1The molar ratio of the compound of the group and the solvent is (0.05-0.5): (0.1-1).
Preferably, in step (1), a compound of structure X is provided, and R is provided1The molar ratio of the compound of the group to the solvent is 0.1:0.1: 0.1.
Preferably, in step (2), R is provided2The molar amount of the compound of the group and the solvent is (0.05-0.5): 0.1-1.
Preferably, in step (2), R is provided2The molar amount of the compound of the group and the solvent was 0.1: 0.1.
Preferably, the solvent in step (1) and step (2) is triethylamine.
Preferably, the inert gas is nitrogen.
Preferably, the extent of the reaction is indicated by gas chromatography when more than 99% of the provided R is consumed1Compounds of the group and provision of R2The reaction is completed when the group is a compound.
Preferably, after the reaction in the step (2) is completed, the product is added into cyclohexane, and then the mixture is filtered, a filter cake is collected, separated by silica gel column chromatography, and dried in vacuum, so that the cross-linking agent is prepared.
The cross-linking agent can be used in hydrophilic coatings to improve the lubricating property of the coatings.
kinds of coating comprises the following components, by weight, 0.1-2 parts of a cross-linking agent, 1-15 parts of a lubricating substance and 80-98 parts of a solvent.
Preferably, the coatings comprise the following components, by weight, 0.1-1 part of a cross-linking agent, 1-10 parts of a lubricating substance and 85-98 parts of a solvent.
Preferably, the lubricant is at least selected from polyvinylpyrrolidone, polyethylene glycol, hyaluronic acid, sodium polyacrylate, polyacrylamide, sodium alginate and polyvinyl alcohol.
The lubricant not only has a lubricating effect in the coating, but also can play a role of a supporting structure similar to resin, so that no resin is required to be added in the coating.
Preferably, the solvent is at least of water, alcohol, acetone and tetrahydrofuran.
A preparation method of the coating, comprising the following steps:
adding the cross-linking agent into a solvent, stirring, and then adding a lubricant to obtain the coating.
A method for forming a lubricating layer on the surface of a medical device by coating the coating, comprising the following steps:
(1) immersing the medical instrument into the coating under the condition of keeping out of the sun, then taking out the medical instrument, and drying for later use;
(2) curing the medical appliance treated in the step (1) under ultraviolet.
Preferably, the medical device in step (1) is a catheter.
Preferably, the medical device in step (1) is immersed in the coating for a time of 1 to 5 minutes.
Preferably, the drying process in the step (1) is to hang the medical instrument taken out on a drying rack and dry the medical instrument in the air.
Preferably, the medical device is immersed in the mixture in step (1) at a speed of 10 to 110 mm/s.
Preferably, the medical device is removed from the mixture in step (1) at a rate of 1 to 20 mm/s.
Preferably, the intensity of ultraviolet in the step (2) is not less than 20mW/cm2The curing time is 100-500 seconds.
Preferably, during the curing in step (2), the medical device is rotated at a speed of 5-20 rpm.
A medical device (e.g., catheter) comprising a lubricious layer formed from the coating of the present invention.
The lubricating layer is a hydrophilic lubricating layer.
Compared with the prior art, the invention has the following beneficial effects:
the cross-linking agent contains polyfunctional groups, and the coating prepared by the cross-linking agent is applied to the surface of a medical instrument to form a lubricating layer, so that the friction coefficient of the surface of the medical instrument is obviously reduced, and the medical instrument has good lubricating property and still has good lubricating property after being used for many times.
Detailed Description
In order to make the technical solutions of the present invention more apparent to those skilled in the art, the following examples are given for illustration. It should be noted that the following examples are not intended to limit the scope of the claimed invention.
Preparation of crosslinking agent (examples 1-3, comparative examples 1-2), preparation of coating (examples 4-6, comparative examples 3-4), preparation of lubricating layer on surface of medical device, as described in example 7.
Example 1
The crosslinker prepared in this example has the following structural formula (1):
Figure BDA0002192150950000051
the preparation method of the cross-linking agent comprises the following steps:
(1) mixing 0.1mol of propylene glycol, 0.1mol of acryloyl chloride and 0.1mol of triethylamine, and stirring for reaction at 20-25 ℃ under the protection of nitrogen to prepare an intermediate for later use;
(2) and (2) adding 0.1mol of 4-benzoyl chloride and 0.1mol of triethylamine into the intermediate prepared in the step (1), and stirring and reacting at 20-25 ℃ under the protection of nitrogen to prepare the cross-linking agent.
The extent of the reactions in step (1) and step (2) can be controlled by gas chromatography display, and the reactions are completed when more than 99% of the acryloyl chloride and 4-benzoyl chloride are consumed.
And (3) after the reaction in the step (2) is finished, adding the product into cyclohexane, filtering, collecting a filter cake, separating by silica gel column chromatography, and drying in vacuum to obtain the cross-linking agent.
Example 2
The crosslinker prepared in this example has the following structural formula (2):
Figure BDA0002192150950000061
the preparation method of the cross-linking agent comprises the following steps:
(1) mixing 0.1mol of pentaerythritol, 0.2mol of acryloyl chloride and 0.2mol of triethylamine, and stirring for reaction at 20-25 ℃ under the protection of nitrogen to prepare an intermediate for later use;
(2) and (2) adding 0.2mol of 4-benzoyl chloride and 0.2mol of triethylamine into the intermediate prepared in the step (1), and stirring to react at 30 ℃ under the protection of nitrogen to prepare the cross-linking agent.
The extent of the reactions in step (1) and step (2) can be controlled by gas chromatography display, and the reactions are completed when more than 99% of the acryloyl chloride and 4-benzoyl chloride are consumed.
And (3) after the reaction in the step (2) is finished, adding the product into cyclohexane, filtering, collecting a filter cake, separating by silica gel column chromatography, and drying in vacuum to obtain the cross-linking agent.
Example 3
The crosslinker prepared in this example has the following structural formula (3):
Figure BDA0002192150950000071
the preparation method of the cross-linking agent comprises the following steps:
(1) mixing 0.1mol of pentaerythritol, 0.2mol of acryloyl chloride and 0.2mol of triethylamine, and stirring for reaction at 20-25 ℃ under the protection of nitrogen to prepare an intermediate for later use;
(2) and (2) adding 0.2mol of 4-bromomethylbenzophenone and 0.2mol of triethylamine into the intermediate prepared in the step (1), and stirring to react at 30 ℃ under the protection of nitrogen to prepare the cross-linking agent.
The extent of the reactions in step (1) and step (2) can be controlled by gas chromatography display, and the reactions are completed when more than 99% of acryloyl chloride and 4-bromomethylbenzophenone are consumed.
And (3) after the reaction in the step (2) is finished, adding the product into cyclohexane, filtering, collecting a filter cake, separating by silica gel column chromatography, and drying in vacuum to obtain the cross-linking agent.
Comparative example 1 (R)1The radicals not containing carbon-to-carbon double bonds)
The crosslinking agent prepared in this comparative example has the following structural formula (4):
comparative example 1 was prepared in substantially the same manner as in example 1 except that propionyl chloride was used in place of acryloyl chloride in example 1 in comparative example 1.
Comparative example 2 (R)2Carbonyl groups not containing benzophenone)
The crosslinking agent prepared in this comparative example has the following structural formula (5):
comparative example 2 was prepared in substantially the same manner as in example 1 except that 4-benzyl bromide was used in place of 4-benzoyl chloride in example 1 in comparative example 2.
Example 4
kinds of coating comprises the following components, by weight, 0.2 part of cross-linking agent prepared in example 1, 5 parts of lubricating substance and 94.8 parts of solvent.
The lubricant is polyvinylpyrrolidone.
The solvent is water.
A preparation method of the coating, comprising the following steps:
adding the cross-linking agent into a solvent, stirring, and then adding a lubricant to obtain the coating.
Example 5
kinds of coating comprises the following components, by weight, 0.3 part of the cross-linking agent prepared in example 2, 4 parts of a lubricating substance and 95.7 parts of a solvent.
The lubricant is 2 parts of polyethylene glycol and 2 parts of hyaluronic acid.
The solvent is ethanol.
A preparation method of the coating, comprising the following steps:
adding the cross-linking agent into a solvent, stirring, and then adding a lubricant to obtain the coating.
Example 6
kinds of coating comprises the following components, by weight, 0.6 part of cross-linking agent prepared in example 2, 8 parts of lubricating substance and 91.4 parts of solvent.
The lubricant is sodium alginate.
The solvent is acetone.
A method for preparing hydrophilic coating, comprising the following steps:
adding the cross-linking agent into a solvent, stirring, and then adding a lubricant to obtain the coating.
Comparative example 3
In comparison with example 4, comparative example 3 was prepared by replacing the crosslinking agent prepared in example 1 with the crosslinking agent prepared in comparative example 1, and the rest of the preparation process was the same as example 4.
Comparative example 4
Comparative example 4 in comparison with example 4, the crosslinking agent prepared in comparative example 2 was used instead of the crosslinking agent prepared in example 1 in the preparation of the coating, and the rest of the preparation process was the same as in example 4.
Example 7
The coatings prepared in examples 4-6 and comparative examples 3-4 are respectively coated on the surface of a medical appliance (such as a catheter) to form a lubricating layer by the following method:
(1) immersing the medical instrument into the coating under the condition of keeping out of the sun, then taking out the medical instrument, and drying for later use;
(2) curing the medical appliance treated in the step (1) under ultraviolet.
And (2) in the drying process in the step (1), taking out the medical instrument, hanging the medical instrument on a drying hanger, and drying.
The medical device is immersed in the mixture in the step (1) at a speed of 50mm/s while the medical device is immersed in the coating.
And (3) taking out the medical instrument from the coating at the speed of 10mm/s in the step (1).
The intensity of ultraviolet in the step (2) is 40mW/cm2The curing time was 150 seconds.
During the curing in step (2), the medical device is rotated at a speed of 10 rpm.
The lubricating layers on the surfaces of the medical devices prepared by the above-described methods contained the coatings prepared in examples 4 to 6 and comparative examples 3 to 4, respectively.
Product effectiveness testing
The lubricating layers on the surfaces of the medical devices, which respectively contained the coatings prepared in examples 4 to 6 and comparative examples 3 to 4, were used 5 times under the same conditions, and the friction coefficient test was performed before each use for a total of 5 times, and the results are shown in Table 1.
Table 1:
Figure BDA0002192150950000091
as can be seen from Table 1, the lubricating layers on the surfaces of the medical devices containing the coatings obtained in examples 4 to 6 had smaller coefficients of friction (relative to the lubricating layers on the surfaces of the medical devices containing the coatings obtained in comparative examples 3 to 4), and even when they were used 5 times, the coefficient of friction did not change much, the coefficient of friction remained small, and the lubricating effect remained good. The lubricating layer on the surface of the medical device containing the coating prepared in comparative examples 3 to 4 rapidly increased the surface friction coefficient and sharply decreased the lubricating effect with the increase of the number of uses.
In addition, the medical device (for example, catheter) treated in example 7 was immersed in physiological saline for 30 seconds, and was sandwiched between two silicone sheets (the shore hardness of silicone is 45 to 65) after being taken out, and the holding force was kept at 500g, so that it was found that the lubricating layer on the surface of the medical device was formed from the coating prepared in examples 4 to 6, and smooth sliding between the silicone sheets did not cause significant resistance, and the coating layer did not disappear after sliding many times. However, the lubricant layer on the surface of the medical device was formed from the coating materials prepared in comparative examples 3 to 4, and with only slight lubrication, a significant resistance was felt by continuous sliding, and the lubricant layer was completely disappeared after sliding several times.

Claims (10)

1, kinds of cross-linking agents, characterized in that, the structural general formula of the cross-linking agent is (R)1)m-X-(R2)nSaid R is1The group contains a carbon-carbon double bond to a carbonyl group; the R is2The radical contains a benzophenone structure; x is at least 2-OH to remove H or contains-NH2Removing H, wherein m is more than or equal to 1, n is more than or equal to 1, and m and n are positive integers.
2. The crosslinking agent of claim 1, wherein X is
Figure FDA0002192150940000011
Figure FDA0002192150940000012
3. The crosslinking agent of claim 1, wherein R is1The radical is
Figure FDA0002192150940000013
The R is2The radical is
The preparation method of crosslinking agents is characterized by comprising the following steps:
(1) providing a compound of X structure, providing R1Mixing the radical compound with a solvent, and stirring for reaction under the protection of inert gas to prepare an intermediate for later use;
(2) addition to the intermediate prepared in step (1) provides R2Reacting the compound of the group and a solvent under the protection of inert gas with stirring to obtain the crosslinking agent of any in claims 1-3.
5. The method according to claim 4, wherein the compound providing the structure of X is at least selected from the group consisting of ethylene glycol, pentaerythritol, dipentaerythritol, glycerol, tris, citric acid, trimethylolpropane and ethylenediamine.
6. The method of claim 4, wherein R is provided1The compounds of the group contain a carbon-carbon double bond to a carbonyl group; providing R2The compound of the group is benzophenone and derivatives thereof.
7. The method according to claim 4, wherein in the step (1), the compound having X structure is provided, and R is provided1The molar ratio of the compound of the group and the solvent is (0.05-0.5): (0.1-1).
8, kinds of coating, characterized by, according to the part by weight, include the following components, 0.1-2 parts of cross-linking agent, 1-15 parts of lubricator, 80-98 parts of solvent of in claim 1-3.
A method of forming a lubricious layer on a surface of a medical device from the coating of claim 8, comprising the steps of:
(1) immersing the medical instrument into the coating under the condition of keeping out of the sun, then taking out the medical instrument, and drying for later use;
(2) curing the medical appliance treated in the step (1) under ultraviolet.
A medical device, comprising a lubricious layer formed from the coating of claim 8.
CN201910835906.8A 2019-09-05 2019-09-05 crosslinking agents and application thereof Pending CN110734664A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112538271A (en) * 2020-12-09 2021-03-23 山东大学 Hydrophilic silicone rubber capable of being used as medical catheter and preparation method and application thereof

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4737559A (en) * 1986-05-19 1988-04-12 Minnesota Mining And Manufacturing Co. Pressure-sensitive adhesive crosslinked by copolymerizable aromatic ketone monomers
US20100227077A1 (en) * 2009-03-03 2010-09-09 Innovative Surface Technologies, Llc. Brush polymer coating by in situ polymerization from photoreactive surface
CN105732848A (en) * 2016-02-26 2016-07-06 中山大学 Photo-cured resin, hydrophilic lubricating coating and preparation method of photo-cured resin

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4737559A (en) * 1986-05-19 1988-04-12 Minnesota Mining And Manufacturing Co. Pressure-sensitive adhesive crosslinked by copolymerizable aromatic ketone monomers
US20100227077A1 (en) * 2009-03-03 2010-09-09 Innovative Surface Technologies, Llc. Brush polymer coating by in situ polymerization from photoreactive surface
CN105732848A (en) * 2016-02-26 2016-07-06 中山大学 Photo-cured resin, hydrophilic lubricating coating and preparation method of photo-cured resin

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112538271A (en) * 2020-12-09 2021-03-23 山东大学 Hydrophilic silicone rubber capable of being used as medical catheter and preparation method and application thereof

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Application publication date: 20200131