CN115109195B - Bio-based light and heat dual-curing lens, lens filling adhesive and application thereof - Google Patents

Bio-based light and heat dual-curing lens, lens filling adhesive and application thereof Download PDF

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CN115109195B
CN115109195B CN202210365046.8A CN202210365046A CN115109195B CN 115109195 B CN115109195 B CN 115109195B CN 202210365046 A CN202210365046 A CN 202210365046A CN 115109195 B CN115109195 B CN 115109195B
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lens
curing
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dual
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CN115109195A (en
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温耀光
钟正恒
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Rayland Chemicals Dongguan Co ltd
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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F265/00Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/04Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
    • C08F265/06Polymerisation of acrylate or methacrylate esters on to polymers thereof
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00Processes of polymerisation
    • C08F2/46Polymerisation initiated by wave energy or particle radiation
    • C08F2/48Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F283/00Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/006Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00
    • C08F283/008Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00 on to unsaturated polymers
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F283/00Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/01Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to unsaturated polyesters
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F283/00Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/06Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
    • C08F283/065Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals on to unsaturated polyethers, polyoxymethylenes or polyacetals
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F283/00Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/10Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers containing more than one epoxy radical per molecule
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F283/00Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/10Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers containing more than one epoxy radical per molecule
    • C08F283/105Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers containing more than one epoxy radical per molecule on to unsaturated polymers containing more than one epoxy radical per molecule
    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041Lenses

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

The invention discloses a bio-based photo-thermal dual-curing lens and lens filling adhesive and application thereof. The lens or the lens manufactured by the filling adhesive has the characteristics of energy conservation, environmental protection and excellent optical performance.

Description

Bio-based light and heat dual-curing lens, lens filling adhesive and application thereof
Technical Field
The invention particularly relates to a bio-based light and heat dual-curing lens, a lens filling adhesive and application thereof.
Background
The processing and use processes of chemical raw materials inevitably generate a large amount of greenhouse gas emissions, thereby increasing the carbon emission. In the field of resin material processing, a large amount of petroleum carbon materials are required, so that the requirements of environmental protection cannot be met.
The invention provides a bio-based light and heat dual-curing lens and lens filling adhesive, which aims to introduce bio-carbon resin to replace part of petroleum carbon materials so as to achieve the aim of reducing carbon emission.
Disclosure of Invention
Based on the above, the invention provides a bio-based light and heat dual-curing lens and lens filling adhesive, which comprises the following specific raw materials in percentage by mass:
30-83% of light-cured resin; 3-8% of thermosetting resin, wherein the thermosetting resin is epoxy resin; 12 to 60 percent of reactive monomer, 2 percent of photo-curing agent, 0.01 to 0.02 percent of reaction catalyst, 0 to 0.01 percent of dye,
the photo-curing resin is formed by mixing bio-based photo-curing resin, hydroxyl modified epoxy acrylate, polyester acrylate and polyurethane acrylate, wherein the bio-based photo-curing resin is grease modified acrylate resin, and the grease is any one or more of linseed oil, tung oil, soybean oil, castor oil, catalpa oil and rosin.
Preferably, the reaction monomer is a modified acrylic ester series reaction monomer with a reactive double bond or containing epoxy groups and hydroxyl optical grade.
Preferably, the reaction monomer is composed of one or more of 2-hydroxyethyl methacrylate (2-HEMA), glycidyl Methacrylate (GMA), pentaerythritol tripropylester (PET 3A), trimethylolpropane triacrylate (TMPTA), trimethylolpropane trimethacrylate (TMPTMA), tripropylene glycol dipropylester (TPGDA), isobornyl acrylate (IBOA), isobornyl methacrylate (IBOMA), 2-phenoxyethyl acrylate (2-PEA), bisphenol A polyoxyethylene ether diacrylate, phenyl glycidyl ether, aliphatic glycidyl ether, benzyl glycidyl ether, o-tolyl glycidyl ether, neopentyl glycol diglycidyl ether.
Preferably, the reaction catalyst is organic silver or organic vanadium.
The invention also provides a preparation method of the bio-based photo-thermal dual-curing lens and lens filling adhesive, which comprises the steps of mixing the raw materials in proportion, stirring for 1-3 hours at the stirring speed of 60-100 r/min, and filtering to obtain the bio-based photo-thermal dual-curing lens and lens filling adhesive, wherein the mesh size of the filter screen is 0.5-1 micron.
The invention also provides application of the bio-based light and heat dual-curing lens and lens filling adhesive, in particular to preparation of a lens or a lens by using the bio-based light and heat dual-curing lens and lens filling adhesive, which comprises the following specific preparation steps:
filling the photo-thermal dual-curing lens and lens filling glue into a glass mold, putting into an LED-UV photo-curing machine, setting the light wave band range to be 305-405nm of LED-UV wavelength, and irradiating for 3 seconds to Zhong Wancheng for photo-curing at the first stage to obtain a semi-finished product;
and baking the semi-finished product in an oven at 70-150 ℃ for 20-90 minutes to finish heat curing, so as to obtain the lens and the lens.
Compared with the prior art, the invention has the following beneficial effects:
the invention uses light and heat curing two kinds of resin, reaction monomer and bio-based carbon light curing resin as raw materials, and combines curing agent and catalyst to prepare the bio-based light and heat dual-curing lens and lens filling glue. The lens or the lens manufactured by the filling adhesive has the characteristics of energy conservation, environmental protection and excellent optical performance.
Detailed Description
The invention will be further illustrated with reference to specific examples.
Example 1
A bio-based light and heat dual-curing lens and lens filling adhesive comprises the following raw materials in percentage by mass:
epoxy (macros electronics corporation, GESR 904H) 2.5%,
trimethylolpropane triacrylate (TMPTA) 4.99%
Bisphenol A polyoxyethylene ether diacrylate 10%
Neopentyl glycol diglycidyl ether 1%
2-hydroxyethyl methacrylate (2-HEMA) 1%
2 percent of photo-curing agent,
0.01 percent of organic silver,
3.8% of photo-curing hydroxyl-containing modified epoxy acrylate (New Limei technology Co., ltd., 1010),
photo-curable polyester acrylate (New Limei technologies Co., ltd., 708) 3.8%,
photo-curable urethane acrylate (New Limei technologies Co., ltd., 670A 2) 0.38%,
70.52% of soybean oil modified acrylic resin (Sanmu chemical industry, 6103).
The preparation method of the bio-based photo-thermal dual-curing lens and lens filling adhesive comprises the steps of mixing and stirring the raw materials in proportion for 2 hours, wherein the stirring speed is 80 revolutions per minute, and filtering to obtain the bio-based photo-thermal dual-curing lens and lens filling adhesive, wherein the mesh of a filter screen is 0.5 micrometer.
The preparation method of the bio-based light and heat dual-curing lens and the lens filling adhesive comprises the following specific preparation steps:
filling the photo-thermal dual-curing lens and lens filling glue into a glass mold, putting into an LED-UV photo-curing machine, setting the light wave band range to be 400nm of LED-UV wavelength, and irradiating for 5 minutes to complete the photo-curing at the first stage to obtain a semi-finished product;
and (3) baking the semi-finished product in an oven at 100 ℃ for 60 minutes to finish heat curing, so as to obtain the lens.
Example 2
A bio-based light and heat dual-curing lens and lens filling adhesive comprises the following raw materials in percentage by mass:
epoxy (macros electronics corporation, GESR 904H) 6.6%,
hydroxyethyl 2-methacrylate (2-HEMA) 8.5%
Pentaerythritol tripropylester (PET 3A) 16.5%
29.99 percent of bisphenol A polyoxyethylene ether diacrylate
O-tolyl glycidyl ether 5%
2 percent of photo-curing agent,
0.01 percent of organic silver,
light-cured hydroxyl-containing modified epoxy acrylate (New Limei technology Co., ltd., 1010) 5%,
photo-curable polyester acrylate (New Limei technologies Co., ltd., 708) 3.3%,
1.7% of photo-curing urethane acrylate (New Limei technology Co., ltd., 670A 2),
21.4% of soybean oil modified acrylic resin (Sanmu chemical industry, 6103).
The preparation method of the bio-based photo-thermal dual-curing lens and lens filling adhesive comprises the steps of mixing and stirring the raw materials in proportion for 2 hours at the stirring speed of 100 revolutions per minute, and filtering to obtain the bio-based photo-thermal dual-curing lens and lens filling adhesive, wherein the mesh of a filter screen is 0.5 micrometer.
The blue light myopia prevention lens with 600 degrees is prepared by using the bio-based light and heat dual-curing lens and lens filling glue, and the specific preparation steps are as follows:
filling the photo-thermal dual-curing lens and lens filling glue into a glass mold, putting into an LED-UV photo-curing machine, setting the light wave band range to be 405nm of LED-UV wavelength, and irradiating for 1 minute to complete the photo-curing at the first stage to obtain a semi-finished product;
and baking the semi-finished product in an oven at 100 ℃ for 50 minutes to finish heat curing, so as to obtain the lens.
Control group
A lens and lens filling adhesive comprises the following raw materials in percentage by mass:
epoxy (macros electronics corporation, GESR 904H) 6.6%,
2-hydroxyethyl methacrylate (2-HEMA) 11.5%
Pentaerythritol tripropylester (PET 3A) 13.5%
29.99 percent of bisphenol A polyoxyethylene ether diacrylate
O-tolyl glycidyl ether 5%
2 percent of photo-curing agent,
0.01 percent of organic silver,
light-cured modified epoxy acrylate with hydroxyl group (New Limei technology Co., ltd., 1010) 25%,
4.7% of a photo-curable polyester acrylate (New Limei technologies Co., ltd., 708),
1.7% of photo-curing polyurethane acrylic ester (New Limei technology Co., ltd., 670A 2)
Meanwhile, a lens of a control group is prepared by using the filling glue prepared by the control group according to the method of the embodiment 2, and performance detection is carried out on the lens of the control group and the lens prepared by the embodiment of the invention, and the performance detection is specifically shown as follows.
Example 3
A bio-based light and heat dual-curing lens and lens filling adhesive comprises the following raw materials in percentage by mass:
epoxy (macros electronics corporation GESR 904H) 7%,
pentaerythritol tripropylester (PET 3A) 6%
2-Phenoxyethyl acrylate (2-PEA) 4.99%
20% of bisphenol A polyoxyethylene ether diacrylate
Benzyl glycidyl ether 3%
2-hydroxyethyl methacrylate (2-HEMA) 8%
2 percent of photo-curing agent,
0.02 percent of organic vanadium,
photo-curing hydroxy-bearing modified epoxy acrylate (New Limei technology Co., ltd., 1010) 7.3%,
3.7% of a photo-curable polyester acrylate (New Limei technologies Co., ltd., 708),
photo-curable urethane acrylate (New Limei technology Co., ltd., 670A 2) 1%
Rosin modified polyester acrylate (optical environmental protection materials Co., ltd 5335 in Jiangmen Co., ltd.) 9%
Soybean oil modified acrylic resin (Sanmu chemical industry, 6103) 18%
The preparation method of the bio-based photo-thermal dual-curing lens and lens filling adhesive comprises the steps of mixing and stirring the raw materials in proportion for 2 hours at the stirring speed of 100 revolutions per minute, and filtering to obtain the bio-based photo-thermal dual-curing lens and lens filling adhesive, wherein the mesh of a filter screen is 0.5 micrometer.
The biological base light and heat dual-curing lens and the lens filling glue are utilized to prepare a 100-degree presbyopic lens, and the preparation method comprises the following specific steps:
filling the photo-thermal dual-curing lens and lens filling glue into a glass mold, putting into an LED-UV photo-curing machine, setting the light wave band range to be 405nm of LED-UV wavelength, and irradiating for 3 minutes to finish the photo-curing at the first stage to obtain a semi-finished product;
baking the semi-finished product in an oven at 150 ℃ for 30 minutes to finish heat curing, and obtaining the lens.
Example 4
A bio-based light and heat dual-curing lens and lens filling adhesive comprises the following raw materials in percentage by mass:
epoxy (macros electronics corporation GESR 904H) 5%,
pentaerythritol tripropylester (PET 3A) 2%
Bisphenol A polyoxyethylene ether diacrylate 13%
Benzyl glycidyl ether 2%
Hydroxyethyl 2-methacrylate (2-HEMA) 6.98%
2 percent of photo-curing agent,
0.02 percent of organic vanadium,
photo-curing hydroxy-bearing modified epoxy acrylate (New Limei technology Co., ltd., 1010) 7.3%,
3.7% of a photo-curable polyester acrylate (New Limei technologies Co., ltd., 708),
photo-curable urethane acrylate (New Limei technology Co., ltd., 670A 2) 1%
Rosin modified polyester acrylic ester (optical environmental protection materials Co., ltd. 5335 in Jiangmen city) 15%
Soybean oil modified acrylic resin (Sanmu chemical industry, 6103) 42%
The preparation method of the bio-based photo-thermal dual-curing lens and lens filling adhesive comprises the steps of mixing and stirring the raw materials in proportion for 2 hours at the stirring speed of 100 revolutions per minute, and filtering to obtain the bio-based photo-thermal dual-curing lens and lens filling adhesive, wherein the mesh of a filter screen is 0.5 micrometer.
The sunglass lens is manufactured by using the bio-based light and heat dual-curing lens and lens filling glue, and the preparation method comprises the following specific steps:
filling the photo-thermal dual-curing lens and lens filling glue into a glass mold, putting into an LED-UV photo-curing machine, setting the light wave band range to be 305nm of the LED-UV wavelength, and irradiating for 10 minutes to finish the photo-curing at the first stage to obtain a semi-finished product;
and baking the semi-finished product in an oven at 70 ℃ for 90 minutes to finish heat curing, so as to obtain the sunglass lens.
It should be noted that the above-mentioned embodiments are only a few specific embodiments of the present invention, and it is obvious that the present invention is not limited to the above embodiments, but other modifications are possible. All modifications directly or indirectly derived from the disclosure of the present invention will be considered to be within the scope of the present invention.

Claims (5)

1. The bio-based light and heat dual-curing lens and lens filling adhesive is characterized by being prepared from the following raw materials in percentage by mass:
30-83% of light-cured resin; 3-8% of thermosetting resin, wherein the thermosetting resin is epoxy resin;
12-60% of reactive monomer, 2% of light curing agent, 0.01-0.02% of reaction catalyst and 0-0.01% of dye, wherein the light curing resin is formed by mixing bio-based light curing resin, hydroxyl modified epoxy acrylate, polyester acrylate and polyurethane acrylate, the bio-based light curing resin is grease modified acrylate resin, and the grease is soybean oil.
2. The bio-based dual curing optical and thermal lens and lens filling adhesive according to claim 1, wherein the reaction monomer is prepared by mixing trimethylolpropane triacrylate, bisphenol A polyoxyethylene ether diacrylate, neopentyl glycol diglycidyl ether and hydroxyethyl 2-methacrylate, or,
the reaction monomer is formed by mixing 2-hydroxyethyl methacrylate, pentaerythritol tripropylester, bisphenol A polyoxyethylene ether diacrylate and o-tolylglycidyl ether.
3. The bio-based dual cure optical and thermal lens, lens filling paste of claim 1, wherein the reaction catalyst is an organic silver.
4. The method for preparing the bio-based light and heat dual-curing lens and lens filling glue according to any one of claims 1 to 3, wherein the raw materials are mixed in proportion, stirred for 1 to 3 hours at a stirring speed of 60 to 100 revolutions per minute, and then filtered to obtain the bio-based light and heat dual-curing lens and lens filling glue, and the mesh of the filter screen is 0.5 to 1 micrometer.
5. Use of a biobased dual cure lens, lens filling compound according to any one of claims 1-3, wherein the lens or lens is prepared from the biobased dual cure lens, lens filling compound by the steps of:
filling the photo-thermal dual-curing lens and lens filling glue into a glass mold, putting into an LED-UV photo-curing machine, setting the light wave band range to be 305-405nm of LED-UV wavelength, and irradiating for 3 seconds to Zhong Wancheng for photo-curing at the first stage to obtain a semi-finished product;
and baking the semi-finished product in an oven at 70-150 ℃ for 20-90 minutes to finish heat curing, so as to obtain the lens and the lens.
CN202210365046.8A 2022-04-07 2022-04-07 Bio-based light and heat dual-curing lens, lens filling adhesive and application thereof Active CN115109195B (en)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010027041A1 (en) * 2008-09-05 2010-03-11 協立化学産業株式会社 Photocurable resin composition for laminating optically functional material
KR20100072566A (en) * 2008-12-22 2010-07-01 이피캠텍 주식회사 Composition comprising acrylated ester monomer and coating products using the same
CN105820723A (en) * 2016-05-30 2016-08-03 成都纳硕科技有限公司 Wearproof photocuring lens
CN106554364A (en) * 2016-10-12 2017-04-05 中国林业科学研究院林产化学工业研究所 A kind of preparation method of fat-based double cured resin monomer
CN108715752A (en) * 2018-06-22 2018-10-30 瑞洲树脂(东莞)有限公司 A kind of light fills glue with heat dual curing eyeglass, camera lens
CN111978784A (en) * 2020-09-15 2020-11-24 中山市富日印刷材料有限公司 Preparation method of biomass-based environment-friendly UV (ultraviolet) photocuring ink

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010027041A1 (en) * 2008-09-05 2010-03-11 協立化学産業株式会社 Photocurable resin composition for laminating optically functional material
KR20100072566A (en) * 2008-12-22 2010-07-01 이피캠텍 주식회사 Composition comprising acrylated ester monomer and coating products using the same
CN105820723A (en) * 2016-05-30 2016-08-03 成都纳硕科技有限公司 Wearproof photocuring lens
CN106554364A (en) * 2016-10-12 2017-04-05 中国林业科学研究院林产化学工业研究所 A kind of preparation method of fat-based double cured resin monomer
CN108715752A (en) * 2018-06-22 2018-10-30 瑞洲树脂(东莞)有限公司 A kind of light fills glue with heat dual curing eyeglass, camera lens
CN111978784A (en) * 2020-09-15 2020-11-24 中山市富日印刷材料有限公司 Preparation method of biomass-based environment-friendly UV (ultraviolet) photocuring ink

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