CN106320063B - A kind of paper making additive fluorescent liquid remover and its synthetic method - Google Patents
A kind of paper making additive fluorescent liquid remover and its synthetic method Download PDFInfo
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- CN106320063B CN106320063B CN201610682237.1A CN201610682237A CN106320063B CN 106320063 B CN106320063 B CN 106320063B CN 201610682237 A CN201610682237 A CN 201610682237A CN 106320063 B CN106320063 B CN 106320063B
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- acid
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—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 carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/04—Anhydrides, e.g. cyclic anhydrides
- C08F222/06—Maleic anhydride
- C08F222/08—Maleic anhydride with vinyl aromatic monomers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/44—Preparation of metal salts or ammonium salts
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/34—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D21H17/41—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing ionic groups
- D21H17/44—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing ionic groups cationic
- D21H17/45—Nitrogen-containing groups
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Paper (AREA)
Abstract
The invention discloses a kind of paper making additive fluorescent liquid remover and its synthetic method, fluorescent liquid remover synthetic method uses solution polymerization process, various comonomers are under the conditions of existing for initiator, agitating and heating carries out Raolical polymerizable in a solvent, is prepared with reference to corresponding post-processing step;Comonomer is used by fluid present invention Fluorescence Quenching Agent synthetic method:In percentage by weight, by 10 ~ 50% unsaturated monomer A, 10 ~ 70% unsaturated monomer B, 20% ~ 80% unsaturated monomer C, 10% ~ 50% dicarboxylic acids and its acid anhydrides D and 5% ~ 45% aliphatic polyamine E compositions, wherein, A, B, C, D, E gross weight is 100% than sum.
Description
Technical field
The present invention relates to a kind of paper making additive -- fluorescent liquid remover and its synthetic method.
Background technology
Health environment-friendly, high-end, high quality paper for daily use have become the requirement of people's daily life, particularly to paper
Zhang Baidu requirement more and more higher, therefore be particularly in many paper in advanced paper for daily use and all add substantial amounts of fluorescence increasing
White agent obtains higher Paper White Degree with this.But these paper are after secondary stock is changed into, fluorescent brightening material therein
It has been retained in slurry, using secondary stock has been raw material come the final quality of product produced so as to compromise, limits its application such as
In food packaging paper.Fluorescent whitening agent for papermaking class is mainly piperazine amino-stilbene class sulfonate fluorescent brightening
Agent, this kind of brightening agent are also the main Types in current brightening agent product, and 80% brightening agent product belongs to such abroad, its
Formula is as follows:
It produces the mechanism of fluorescence:When ultraviolet lighting is mapped to Cucumber, these materials launch a variety of colors and
The visible ray of varying strength, and when ultraviolet light stops irradiating, this light also disappears quickly therewith, and this light is referred to as glimmering
Light.Fluorescence is typically occurred in the molecule with π-pi-electron conjugated system, and these molecules are excited to electronics absorbing light
After each vibration level of excitation state, the lowest vibration energy level of excited electronic state is generally drastically drop to, in the process not
When sending light, and continuing to drop to each different vibration levels of ground state, then fluorescence is sent.Fluorescent whitening agent is that have conjugation double
The organic compound of bond structure, it is most of with the amidosulfonic acid class group that can excite fluorescence.With the virtue that can absorb ultraviolet light
The group of fragrant amine, fatty amine and its derivative, thus fluorescence can occur.
Fluorescence Quenching Agent, it is called fluorescence remover, quencher, screener, unstressed configuration brightening agent etc..Optical brightener solutions
Aobvious " elecrtonegativity ", it is inconsistent with different and aobvious electronegative degree of its component content.Fluorescence Quenching Agent generally shows " just
Electrically ", it is inconsistent to show electropositive degree for different Fluorescence Quenching Agents.Fluorescence Quenching Agent is exactly to utilize " electropositive " of itself
Effectively in neutralized system fluorescent whitening agent " elecrtonegativity ".Make the active anion group " denaturation " of color development, reach and effectively disappear
Except the purpose of system fluorescence.The mechanism of action of Fluorescence Quenching Agent is not destruction and removes the molecule to fluoresce, Fluorescence Quenching Agent
Do not chemically reacted with fluorescer, do not change the structure of functional group in fluorescent molecules, it can only suppress fluorescer and fluoresce
Property.Meanwhile part Fluorescence Quenching Agent is because having certain relative molecular mass, therefore also can be to slurry during by use
Material(Including auxiliary agents such as filler, brightening agents)Play a part of good drainage, reservation, shaping and improve paper machine operation performance.
The content of the invention
It is an object of the invention to provide a kind of paper making additive -- fluorescent liquid remover and its synthesis side
Method, to realize the technical purpose of the present invention, fluid present invention Fluorescence Quenching Agent general structure is
Wherein, R1For higher aliphatic alcohol radical, ammonium, Triethanolamine, Na or K;R2For higher aliphatic amido, anilino- or
Natural fat acidic group;R3For anilino-, alkylamine or pyrrolidinyl;R4X, y, z, the v such as a chloro thing for halogen, alkyl be 0 ~
25 integer, m, n are 5 ~ 100 integer.
Fluid present invention Fluorescence Quenching Agent and the technical scheme of synthetic method use are:It is various common using solution polymerization process
Polycondensation monomer is under the conditions of existing for initiator, and agitating and heating carries out Raolical polymerizable in a solvent, with reference to corresponding rear place
Reason step is prepared.
Comonomer is used by the synthesis of fluid present invention Fluorescence Quenching Agent:In percentage by weight, by 10 ~
50% unsaturated monomer A, 10 ~ 70% unsaturated monomer B, 20% ~ 80% unsaturated monomer C, 10% ~ 50% dicarboxylic acids and its
Acid anhydrides D and 5% ~ 45% aliphatic polyamine E compositions, wherein, A, B, C, D, E gross weight is 100% than sum.
In above-mentioned technical proposal, unsaturated monomer A is acrylic acid, methacrylic acid, maleic anhydride, fumaric acid, nonyl
Base phenol polyethenoxy ether acrylic acid/methacrylic acid/maleic anhydride ester, AEO acrylic acid/methacrylic acid/
Maleic anhydride ester, aliphatic acid polyethenoxy ether acrylic acid/methacrylic acid/maleic anhydride ester, multi-styrene phenol polyoxyethylene
Ether acrylic acid/methacrylic acid/maleic anhydride ester etc., can be one or more therein.
In above-mentioned technical proposal, unsaturated monomer B is butyl acrylate, tert-butyl acrylate, iso-octyl acrylate, third
Olefin(e) acid isodecyl base ester, dodecyl acrylate, acrylic acid tritriacontyl ester, Process Conditions of Cetane Acrylate, n-BMA, methyl-prop
Olefin(e) acid isobutyl ester, Tert-butyl Methacrylate, EHMA, lauryl methacrylate, methacrylic acid 16
Ester, octadecyl methacrylate one or more participation polymerisations therein.
In above-mentioned technical proposal, unsaturated monomer C is:Styrene, NVP, 4-vinylpridine etc.,
Can be one or more therein.
In above-mentioned technical proposal, dicarboxylic acids and its acid anhydrides D are:Adipic acid and its acid anhydrides, neighbour// terephthalic acid (TPA) and
Its acid anhydrides, maleic acid and its acid anhydrides, azelaic acid and its acid anhydrides, decanedioic acid and its acid anhydrides etc., can be one or more therein.
In above-mentioned technical proposal, aliphatic polyamine E is:Ethylenediamine, hexamethylene diamine, diethylenetriamine, triethylene tetramine, four
The amine of ethene five, diethylaminopropylamine etc., can be one or two therein.
The initiator used in above-mentioned technical proposal is benzoyl peroxide, lauroyl peroxide amine, perbenzoic acid
The tert-butyl ester, azodiisobutyronitrile, ABVN etc., can be one or more therein.
The solvent used in above-mentioned technical proposal for methyl oleate, toluene, butanone or ethyl acetate, ethylene glycol, glycerine,
One or more in glycerine, isopropanol, diethylene glycol.
Relevant content in such scheme is explained as follows:
1st, above-mentioned each comonomer, directly can be thrown for the comonomer for being not easy autohemagglutination into reactor, for easy
The comonomer of autohemagglutination need to be placed in constant pressure addition groove and is added dropwise within the regular hour in reactor.
2nd, in such scheme, initiator can mix with monomer while be added dropwise to reactor, can also be with monomer
Separately be added dropwise, initiator can all be added dropwise to reactor can also pre-cast part remainder into reactor be added dropwise to instead
Answer kettle.
3rd, before copolyreaction, input solvent and part are not easy the monomer of autohemagglutination in advance in reactor, and temperature is risen into polymerization
Reaction temperature, is added dropwise other monomers and initiator under agitation, and 1 ~ 3h of constant temperature carries out polymerisation, carried out reaction
Entirely.
The present invention principle be:The polymeric is pectinate texture polymer, and molecular skeleton is by main chain and many branch
Chain is formed, and main chain introduces positively charged amino-contained phenyl ring or nitrogen-containing hetero yuan of rings, and charge neutrality, frame are carried out to negatively charged fiber
Bridge etc. acts on, and plays good anchorage effect, adds the binding ability with fiber;Side chain introduces the positively charged of long-chain ring-type
Amido, it is easier to playing the aromatic amine of fluorescence, fatty amine and its group of derivative in fluorescent whitening agent, make it
Lose fluorescent effect.
Compared with Xian You Ji Intraoperative, the present invention has advantages below:The polymer of the present invention has pectinate texture, and main chain
It is upper to introduce the structures such as positively charged amino-contained phenyl ring or nitrogen-containing hetero yuan of rings, it is easier to capture fluorescent whitening agent agent, side chain draws
Enter positively charged amido of long-chain ring-type etc., it is easier to risen in fluorescent whitening agent the aromatic amine of fluorescence, fatty amine and
The group effect of its derivative, makes it lose fluorescent effect, greatly reduces the usage amount of Fluorescence Quenching Agent, and can improve fluorescence and go
Except effect.
Embodiment:
Illustrate lower present invention with reference to specific embodiment:
Embodiment 1
A kind of synthetic method of new and effective fluorescent liquid remover, by each altogether from polycondensation monomer in initiator existence condition
Under, stirring carries out copolymerization in a solvent and corresponding post processing is prepared.
1st, raw material:
Monomer:Isooctyl acrylate monomer(2EHA), styrene(St), maleic anhydride(MA),
Adipic acid(AA), ethylenediamine(EDE),
Mol ratio 2EHA:St:MA:AA:EDE=1:1:1.5:1:1,
Initiator:Benzoyl peroxide(BPO), the dosage in reaction system is the 0.5% of monomer mass;
Solvent:Methyl oleate(The weight ratio of solvent and every other raw material is 3:1).
2nd, technique:
In the stainless steel cauldron equipped with agitator, constant pressure addition groove, thermometer and condenser, by the molten of MA and 70%
Agent methyl oleate is first thrown into reactor, and agitating and heating melts maleic anhydride solid, when continuing to be heated to temperature 60 C, simultaneously
The methyl oleate for being mixed with 2EHA, adipic acid, ethylenediamine and styrene is added dropwise(15%)Solution and the oleic acid for being mixed with initiator
Methyl ester solution(A small amount of toluene is added to ensure dissolubility of the initiator in methyl oleate), time for adding is controlled at 1 ~ 2 hour,
70 DEG C of insulation 2h are warming up to after being added dropwise, carry out reaction complete.Reaction is left for 7 with triethanolamine regulation pH value after terminating
The right side, produce fluid present invention Fluorescence Quenching Agent product PC-1.
Embodiment 2:
In embodiment one, initiator solid first throws 20% into reactor, is heated together with MA and 70% solvent, residue is drawn
Send out agent with monomer be made into the solution of methyl oleate together be added dropwise in reactor, other are constant, obtain fluid present invention fluorescence and disappear
Except agent product PC-2.
Embodiment 3:
1st, raw material:
Monomer:Dodecyl acrylate(LA), NVP(NVP),
Maleic anhydride(MA), styrene(St), terephthalic anhydride(PTA)
Diethylenetriamine(DTA),
Mol ratio 1:1.5:2:1:1.2:1.5,
Initiator:Azodiisobutyronitrile(AIBN), the dosage in reaction system is the 0.5% of monomer mass;
Solvent:Butanone(The weight ratio of solvent and every other raw material is 3:1).
2nd, technique:
In the stainless steel cauldron equipped with agitator, constant pressure addition groove, thermometer and condenser, by MA and 70% fourth
Ketone is first thrown into reactor, and agitating and heating acrylic solid is melted, and when continuing to be heated to temperature 60 C, while is added dropwise and is mixed with
LA, NVP, St, PTA, DTA and AIBN butanone solution, control time for adding are warming up to 70 DEG C of guarantors in 1 ~ 1.5h after being added dropwise
Warm 2h, carry out reaction complete.It is 7 or so that reaction adjusts pH value after terminating with triethanolamine, produces fluid present invention fluorescence and disappears
Except agent product PC-3.
Compareed with the fluorescent liquid remover of the present invention with domestic and international commercially available fluorescent liquid remover performance indications,
Application process is as follows with result.
Handsheet condition:
Slurry kind provides for high-level thinking ability paper mill;
Fluorescent whitening agent dosage provides for 3kg/ tons auxiliary reagent factory;
Handsheet method:A certain amount of high-level thinking ability is weighed, immersion carries out size degradation after more than 4 hours, then matched somebody with somebody
Into the slurry that concentration is 3%, the final beating degree of slurry is controlled in 40 ° of SR.Fluorescence removal process:In the beaker equipped with agitator
It is middle to add the slurry weighed, agitator is started, after the paper making additive needed for input into slurry at timed intervals(With paper plant
Paper-making process is identical), interval adds a certain amount of fluorescent whitening agent after 1 minute, a certain amount of fluorescence is added after being spaced 1 minute
Remover, stop stirring after certain time, take out beaker, immediately the copy paper on standard forming device.L Water Paper is under conditions of 105 DEG C
Dry, Substance 100g/m2。
The measure of whiteness and fluorescent whiteness:By national standard《GB/T 7974-2002 paper, cardboard and brightness of pulp(Whiteness)Survey
It is fixed》Regulation handsheet R457 whiteness and fluorescent whiteness F, wherein, R457 whiteness refers to page in dominant wavelength(457±0.5nm)
Internal reflection factor under the conditions of blue light;Fluorescent whiteness F refers to the part that fluorescent whitening agent effect can be directly attributed in Paper White Degree.
Therefore fluorescent whiteness F size can reflect fluorescent brightener levels in page number.
The effect that table 1 removes to fluorescence
Claims (5)
- A kind of 1. paper making additive -- fluorescent liquid remover, it is characterised in that, described fluorescent liquid remover general structure For:;Wherein, R1For higher aliphatic alcohol radical, ammonium, Triethanolamine, Na or K;R2For higher aliphatic amido, anilino- or natural It is fatty acid-based;R3For anilino-, alkylamine or pyrrolidinyl;R4X, y, z, the v such as a chloro thing for halogen, alkyl are 0 ~ 25 Integer, m, n are 5 ~ 100 integer.
- 2. paper making additive according to claim 1 -- the synthetic method of fluorescent liquid remover, it is characterised in that, it is described The synthetic method of fluorescent liquid remover use solution polymerization process, various comonomers under the conditions of existing for initiator, Agitating and heating carries out Raolical polymerizable in solvent, is prepared with reference to corresponding post-processing step;Used copolymerization is single Body is:In percentage by weight, by 10 ~ 50% unsaturated monomer A, 10 ~ 70% unsaturated monomer B, 20% ~ 80% insatiable hunger With monomer C, 10% ~ 50% dicarboxylic acids and its acid anhydrides D and 5% ~ 45% aliphatic polyamine E compositions, wherein, A, B, C, D, E's Gross weight is 100% than sum;The unsaturated monomer A is acrylic acid, methacrylic acid, maleic anhydride, fumaric acid, NPE third Olefin(e) acid ester, AEO acrylate, aliphatic acid polyethenoxy ether acrylate, multi-styrene phenol polyoxyethylene Ether acrylate, can be one or more therein;The unsaturated monomer B is butyl acrylate, tert-butyl acrylate, iso-octyl acrylate, Isodecyl base ester, third Alkene dodecyl gallate, acrylic acid tritriacontyl ester, Process Conditions of Cetane Acrylate, n-BMA, Isobutyl methacrylate, methyl Tert-butyl acrylate, EHMA, lauryl methacrylate, hexadecyl metrhacrylate, methacrylic acid ten Octaester one or more participation polymerisations therein;The unsaturated monomer C is:Styrene, NVP, 4-vinylpridine etc., can be one kind therein It is or a variety of;Dicarboxylic acids and its acid anhydrides D is:Adipic acid and its acid anhydrides, phthalic acid and its acid anhydrides, M-phthalic acid and its Acid anhydrides, terephthalic acid (TPA) and its acid anhydrides, maleic acid and its acid anhydrides, azelaic acid and its acid anhydrides, decanedioic acid and its acid anhydrides etc., Ke Yiwei One or more therein;The aliphatic polyamine E is:Ethylenediamine, hexamethylene diamine, diethylenetriamine, triethylene tetramine, TEPA, diethylamino Base propylamine etc., can be one or two therein;The initiator used in above-mentioned technical proposal is benzoyl peroxide, lauroyl peroxide amine, the tertiary fourth of perbenzoic acid Ester, azodiisobutyronitrile, ABVN etc., can be one or more therein;The solvent is methyl oleate, toluene, butanone or ethyl acetate, ethylene glycol, glycerine, glycerine, isopropanol, diethylene glycol In one or more;Above-mentioned each comonomer, directly it can be thrown for the comonomer for being not easy autohemagglutination into reactor, for easy autohemagglutination Comonomer need to be placed in constant pressure addition groove and is added dropwise within the regular hour in reactor;Initiator can mix with monomer while be added dropwise to reactor, can also be separately added dropwise with monomer, initiator can With all be added dropwise to reactor can also pre-cast part remainder into reactor be added dropwise to reactor;Before copolyreaction, input solvent and part are not easy the monomer of autohemagglutination in advance in reactor, and temperature is risen into polymerisation temperature Degree, other monomers and initiator are added dropwise under agitation, 1 ~ 3h of constant temperature carries out polymerisation, carries out reaction complete.
- 3. paper making additive according to claim 1 -- the synthetic method of fluorescent liquid remover, it is characterised in that, it is described Fluorescent liquid remover synthetic method be by each altogether from polycondensation monomer under initiator existence condition, in a solvent stirring carry out Copolymerization and corresponding post processing are prepared;(1), raw material:Monomer:Isooctyl acrylate monomer(2EHA), styrene(St), maleic anhydride(MA),Adipic acid(AA), ethylenediamine(EDE),Mol ratio 2EHA:St:MA:AA:EDE=1:1:1.5:1:1;Initiator:Benzoyl peroxide(BPO), the dosage in reaction system is the 0.5% of monomer mass;Solvent:Methyl oleate(The weight ratio of solvent and every other raw material is 3:1);(2), technique:In the stainless steel cauldron equipped with agitator, constant pressure addition groove, thermometer and condenser, by MA and 70% solvent naphtha Sour methyl esters is first thrown into reactor, and agitating and heating melts maleic anhydride solid, when continuing to be heated to temperature 60 C, is added dropwise simultaneously It is mixed with the methyl oleate of 2EHA, adipic acid, ethylenediamine and styrene(15%)Solution and the methyl oleate for being mixed with initiator Solution(A small amount of toluene is added to ensure dissolubility of the initiator in methyl oleate), control time for adding was at 1 ~ 2 hour, dropwise addition After be warming up to 70 DEG C of insulation 2h, carry out reaction complete;It is 7 or so that reaction adjusts pH value after terminating with triethanolamine, i.e., Obtain fluorescent liquid remover product PC-1.
- 4. paper making additive according to claim 3 -- the synthetic method of fluorescent liquid remover, it is characterised in that, it is described The synthetic method of fluorescent liquid remover be:Initiator solid first throws 20% into reactor, is heated together with MA and 70% solvent, and remaining initiator is made into monomer The solution of methyl oleate is added dropwise in reactor together, and other are constant, obtains fluorescent liquid remover product PC-2.
- 5. paper making additive according to claim 2 -- the synthetic method of fluorescent liquid remover, it is characterised in that, it is described The synthetic method of fluorescent liquid remover be:(1), raw material:Monomer:Dodecyl acrylate(LA), NVP(NVP), maleic anhydride(MA)Styrene(St), terephthalic anhydride(PTA), diethylenetriamine(DTA),Mol ratio 1:1.5:2:1:1.2:1.5;Initiator:Azodiisobutyronitrile(AIBN), the dosage in reaction system is the 0.5% of monomer mass;Solvent:Butanone(The weight ratio of solvent and every other raw material is 3:1);(2), technique:It is in the stainless steel cauldron equipped with agitator, constant pressure addition groove, thermometer and condenser, MA and 70% butanone is first Throw into reactor, agitating and heating acrylic solid melt, when continuing to be heated to temperature 60 C, at the same be added dropwise be mixed with LA, NVP, St, PTA, DTA and AIBN butanone solution, control time for adding are warming up to 70 DEG C of insulations in 1 ~ 1.5h after being added dropwise 2h, carry out reaction complete;It is 7 or so that reaction adjusts pH value after terminating with triethanolamine, produces fluorescent liquid remover product PC-3。
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