WO2015076440A1 - 에폭시 수지의 경화제 또는 가소제로 유용한 스티렌네이티드 페놀 - Google Patents
에폭시 수지의 경화제 또는 가소제로 유용한 스티렌네이티드 페놀 Download PDFInfo
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- WO2015076440A1 WO2015076440A1 PCT/KR2013/010723 KR2013010723W WO2015076440A1 WO 2015076440 A1 WO2015076440 A1 WO 2015076440A1 KR 2013010723 W KR2013010723 W KR 2013010723W WO 2015076440 A1 WO2015076440 A1 WO 2015076440A1
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- WIPO (PCT)
- Prior art keywords
- phenol
- weight
- curing agent
- styrenated
- epoxy
- Prior art date
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- BYLSIPUARIZAHZ-UHFFFAOYSA-N 2,4,6-tris(1-phenylethyl)phenol Chemical compound C=1C(C(C)C=2C=CC=CC=2)=C(O)C(C(C)C=2C=CC=CC=2)=CC=1C(C)C1=CC=CC=C1 BYLSIPUARIZAHZ-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 27
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 27
- 239000004014 plasticizer Substances 0.000 title claims abstract description 20
- 239000004848 polyfunctional curative Substances 0.000 title abstract description 7
- 239000004593 Epoxy Substances 0.000 claims abstract description 25
- 239000003973 paint Substances 0.000 claims abstract description 23
- 239000003795 chemical substances by application Substances 0.000 claims description 42
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 27
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 7
- UZRCGISJYYLJMA-UHFFFAOYSA-N phenol;styrene Chemical compound OC1=CC=CC=C1.C=CC1=CC=CC=C1 UZRCGISJYYLJMA-UHFFFAOYSA-N 0.000 claims description 4
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 abstract description 20
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 abstract description 20
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 30
- 150000002989 phenols Chemical class 0.000 description 10
- 239000000126 substance Substances 0.000 description 9
- 230000000704 physical effect Effects 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 239000003440 toxic substance Substances 0.000 description 2
- RCFAHSGZAAFQJH-UHFFFAOYSA-N 2,4-bis(1-phenylethyl)phenol Chemical compound C=1C=C(O)C(C(C)C=2C=CC=CC=2)=CC=1C(C)C1=CC=CC=C1 RCFAHSGZAAFQJH-UHFFFAOYSA-N 0.000 description 1
- RCFAHSGZAAFQJH-IAGOWNOFSA-N 2,4-bis(1-phenylethyl)phenol Natural products C[C@H](c1ccccc1)c1ccc(O)c(c1)[C@H](C)c1ccccc1 RCFAHSGZAAFQJH-IAGOWNOFSA-N 0.000 description 1
- NYPMHOYLEBBBGY-IAGOWNOFSA-N 2,6-bis(1-phenylethyl)phenol Natural products C[C@H](c1ccccc1)c1cccc([C@H](C)c2ccccc2)c1O NYPMHOYLEBBBGY-IAGOWNOFSA-N 0.000 description 1
- WYZIVNCBUWDCOZ-UHFFFAOYSA-N 2-(1-phenylethyl)phenol Chemical compound C=1C=CC=C(O)C=1C(C)C1=CC=CC=C1 WYZIVNCBUWDCOZ-UHFFFAOYSA-N 0.000 description 1
- NYPMHOYLEBBBGY-CALCHBBNSA-N 2-[(1s)-1-phenylethyl]-6-[(1r)-1-phenylethyl]phenol Chemical compound C1([C@H](C)C=2C(=C([C@H](C)C=3C=CC=CC=3)C=CC=2)O)=CC=CC=C1 NYPMHOYLEBBBGY-CALCHBBNSA-N 0.000 description 1
- HBMHZKUEKASKNY-UHFFFAOYSA-N 2-nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O.CCCCCCCCCC1=CC=CC=C1O HBMHZKUEKASKNY-UHFFFAOYSA-N 0.000 description 1
- XHASMJXNUHCHBL-UHFFFAOYSA-N 4-(1-phenylethyl)phenol Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=CC=C1 XHASMJXNUHCHBL-UHFFFAOYSA-N 0.000 description 1
- 101000705294 Arabidopsis thaliana Oxygen-evolving enhancer protein 1-2, chloroplastic Proteins 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241001122315 Polites Species 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- 239000000598 endocrine disruptor Substances 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000001976 improved effect Effects 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 230000003589 nefrotoxic effect Effects 0.000 description 1
- 231100000381 nephrotoxic Toxicity 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
- C08G59/621—Phenols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
-
- 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
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
-
- 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
Definitions
- the present invention relates to styrenated phenols useful as curing agents or plasticizers for epoxy resins.
- Epoxy resins are used in a wide range of applications, such as paints, electrical and electronic insulating materials, adhesives, etc., because their cured products have excellent performance in terms of mechanical properties, electrical properties, thermal properties, chemical resistance, adhesiveness, and the like.
- the epoxy resin is excellent in physical properties such as hardness, hardness, sun resistance, workability, etc., and there is no fear of volatile matter or volume shrinkage during curing. It is also used as a paint. Compared with other types of paints used for concrete protection, epoxy cured paints are suitable for high performance paints due to their low shrinkage and mechanical and chemical resistance.
- nonylphenol Nonylphenol
- nonylphenol has been applied to a wide range of applications in various industries, including being used as a curing agent or a plasticizer in the epoxy curable coatings due to its intrinsic physicochemical properties.
- nonylphenol is known as a nephrotoxic and endocrine hormone disruptor, its use is banned in the industry or the range of use is gradually limited. Particularly in Europe, in 2003, some sectors have banned the full use of nonylphenol or no more than 0.1% in products.
- EU Directive 2003/53 / EC is also regulated and managed in EU Reach. [Restricted Substances in Annex 17 of the REACH Regulation] Domestically, since January 2010, some items have been banned by strengthening the reporting of the risk of nonylphenol and the restriction of use.
- the present inventors pay attention to the fact that the viscosity and hardening properties of styrene-ized phenols are similar to those of nonylphenol, and thus, the application of styrenated phenol as a material to replace nonylphenol which is used as a curing agent or plasticizer for epoxy resins.
- Polite review was made.
- Styrenated phenol is prepared by alkylation of phenol with styrene.
- Styreneated phenols are mono-styreneated phenols (MSP) with one styrene in the benzene ring of phenol, di-styreneated phenols (DSP) with two styrenes, and three styrene-bonded trees.
- Styreneated phenol (TSP) compounds may be present.
- Such styrenated phenols are mainly used as antioxidants for synthetic rubbers or resins, and there have been no reports of using styrenated phenols as curing agents or plasticizers for epoxy resins.
- an object of the present invention is to provide an epoxy paint containing styrenated phenol as a curing agent or plasticizer.
- the present invention is characterized by a curing agent or a plasticizer of an epoxy resin containing a styrenated phenol represented by the following formula (1).
- n 1, 2, or 3
- the present invention is characterized by an epoxy paint consisting of a main portion containing an epoxy resin, and a curing agent portion containing the styrene-ized phenol represented by the formula (1).
- Styreneated phenol is useful as a substitute for nonylphenol because it has similar physicochemical properties to nonylphenol and possesses inherent applicability of nonylphenol, and has both viscosity improvement and curing promoting performance.
- styrenated phenol is useful as a curing agent or plasticizer for epoxy resins.
- the present invention relates to the use of styrenated phenol as a curing agent or plasticizer in the production of epoxy curable paints, by confirming that the viscosity and curing properties of styrene-ized phenol are similar to those of nonylphenol.
- Styreneated phenol in the present invention may be represented by the following formula (1).
- n 1, 2, or 3
- n 1 compound is abbreviated as 'MSP'
- n 2 compound is abbreviated as 'DSP'
- n 3 compound. Is abbreviated as 'TSP'.
- MSP may specifically include 2- (1-phenylethyl) phenol (MSP-1) and 4- (1-phenylethyl) phenol (MSP-2). .
- DSP is specifically 2,4-bis (1-phenylethyl) phenol (DSP-1), 2,6-bis (1-phenylethyl) phenol ( DSP-2) may be included.
- TSP may specifically include 2,4,6-tris (1-phenylethyl) phenol (TSP-1).
- the weight ratio of MSP, DSP, and TSP is determined by the molar ratio of phenol and styrene used as reactants.
- the styrenated phenol suitable for the present invention is preferably adjusted so that the content of MSP is 50% by weight or more, preferably 50 to 75% by weight.
- the use of styrenated phenol having a relatively high content of MSP is used. The reason is that the higher the content of MSP, the lower the viscosity, thereby providing plasticity when mixed with an epoxy resin, thereby improving workability, and hydroxy. This is because the OH value is maintained the same as the existing nonylphenol (240 to 250) to promote the curing reaction.
- Table 1 shows the physical properties of the non-styrene phenol categorized as styrene and styrene commercialized as a Kumanox-3110 product.
- styrenated phenol is a non-toxic substance, and has excellent environmental friendliness, weight average molecular weight, hydroxy value (OH value), viscosity, color value, and water content. It can be seen that similarity.
- styrene is lower than nonylphenol, the styrene-ized phenol has a special advantage that the plasticity is better when mixed with the epoxy resin and thus the workability is excellent.
- the styrenated phenol represented by Chemical Formula 1 is useful as a substitute for nonylphenol and has excellent environmental friendliness as a non-toxic substance.
- the present invention is characterized by the use of the styrenated phenol represented by the formula (1) as a curing agent for epoxy paints containing epoxy resin as a subject.
- the epoxy paint may be specifically divided into an epoxy main portion and a hardener portion.
- the main part constituting the epoxy paint includes an epoxy resin, a non-reactive diluent, a plasticizer, and the like, and the curing agent portion includes a curing accelerator, a plasticizer, and the like.
- the composition components and the component ratios of the epoxy paints and in the present invention, no particular limitation is placed on these composition components and the component ratios.
- the present invention is characterized by applying the styrene-ized phenol represented by the formula (1) as a curing agent or plasticizer constituting the curing agent portion in the epoxy paint.
- the curing agent portion containing the styrenated phenol may specifically include 1 to 40% by weight of styrenated phenol and 60 to 99% by weight of a conventional epoxy curing agent as a curing agent or plasticizer.
- the embodiment of the present invention specifically illustrates an example of using a polyether diamine-based curing agent as a conventional epoxy curing agent, but the present invention does not place any particular limitation on the selection of the conventional epoxy curing agent components.
- the curing agent part containing the styrenated phenol When used as a two-component epoxy paint, the curing agent part containing the styrenated phenol is easy to work due to the low viscosity of the paint, and improves workability by shortening the curing time and improving the durability by increasing the hardness of the painted surface.
- the curing agent part is usually blended in the range of 1 to 40 parts by weight to form a cured coating film.
- Viscosity was measured using a tachometer (Brookfield HAT Viscometer or rookfield LV DVE 230 Viscometer) at 25 °C.
- Color was measured using a color measuring instrument (NIPPON DENSHOKU OME 2000).
- the amine number was measured using 0.1N-HCl titration.
- the curing time was measured at room temperature starting at 25 ° C. (50 ° C. (0.1) mercury thermometer) at 100 g scale.
- Hardness was measured using an e-Asker Durometer Super EX Type-D.
- the final hardness means the hardness of the sample heat-cured at 80 °C for 2 hours, the daily hardness change of the sample cured at room temperature was measured.
- reaction temperature was lowered to 110 ° C., and a sulfuric acid (H 2 SO 4 ) catalyst (0.02 g, 1 to 3% by weight of the phosphate catalyst) was added to the reaction product. It was raised to and reacted further for 30 minutes.
- the temperature of the reaction was 80 ° C., and an aqueous sodium carbonate solution was added thereto in the same equivalent ratio as the sulfuric acid used above and neutralized for 30 minutes.
- the produced neutralized salt was removed by filtration under reduced pressure, and then filtered to remove styrene obtained phenol (reaction conversion rate 97%, purity 97% or more).
- the styrene-based phenol has physical properties similar to those of nonylphenol in terms of physical properties such as viscosity and amine value, and styrene in comparison to non-phenol-containing hardeners even though it is included in the curing agent of epoxy paint.
- the curing agent portion containing the naked phenol has a short curing time, high hardness of the cured coating film and excellent physical properties to obtain improved effects of improving workability and durability.
- styrenated phenols are useful as curing agents or plasticizers for epoxy resins.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Epoxy Resins (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
구 분 | 노닐페놀 | Kumanox-3110 |
CAS번호 | 84852-15-3 | 61788-44-1 |
구조식 | C15H24O | 스티렌네이티드 페놀 (MSP 함량 50-70%) |
중량평균분자량 (Mw) | 220.3 | 220 |
OH 값 | 240-250 | 240-250 |
점도 (25℃ cps) |
1,000~1,200 | 400 |
색가 (G) | 0.3 (Max 1.5) | 0.5 (Max 1.5) |
수분함량% | 0.1 (Max 0.2%) | 0.1 (Max 0.2%) |
비고 | 독성 있음 | 비독성 |
구 분 | 점도(cps) | 아민가 | 판단 |
경화제부 (A) | 55 | 305.9 | 물성이 서로 비슷함 |
경화제부 (B) | 48 | 309.5 |
구 분 | 경화제부 | 판단 | ||
경화제부 A | 경화제부 B | |||
경화시간 | 3시간 10분 | 3시간 25분 | 경화제부 A의 경화시간이 더 짧음 | |
쇼어경도 | 2일 | 51 | 45 | 경화제부 A의 경화경도가 더 큼 |
5일 | 79 | 76 | ||
7일 | 85 | 84 |
Claims (9)
- 제 1 항에 있어서,
상기 스티렌네이티드 페놀은 n=1인 모노-스티렌네이티드 페놀(MSP)의 함량이 50 중량% 이상인 것을 특징으로 하는 에폭시 수지의 경화제. - 제 1 항에 있어서,
상기 스티렌네이티드 페놀은 n=1인 모노-스티렌네이티드 페놀(MSP) 50∼75 중량%, n=2인 다이-스티렌네이티드 페놀(DSP) 15∼35 중량% 및 n=3인 트리-스티렌네이티드 페놀(TSP) 1∼8 중량%의 함량비를 이루고 있는 것을 특징으로 하는 에폭시 수지의 경화제. - 제 4 항에 있어서,
상기 스티렌네이티드 페놀은 n=1인 모노-스티렌네이티드 페놀(MSP)의 함량이 50 중량% 이상인 것을 특징으로 하는 에폭시 수지의 가소제. - 제 4 항에 있어서,
상기 스티렌네이티드 페놀은 n=1인 모노-스티렌네이티드 페놀(MSP) 50∼75 중량%, n=2인 다이-스티렌네이티드 페놀(DSP) 15∼35 중량% 및 n=3인 트리-스티렌네이티드 페놀(TSP) 1∼8 중량%의 함량비를 이루고 있는 것을 특징으로 하는 에폭시 수지의 가소제. - 제 7 항에 있어서,
상기 스티렌네이티드 페놀은 n=1인 모노-스티렌네이티드 페놀(MSP)의 함량이 50 중량% 이상인 것을 특징으로 하는 에폭시 도료. - 제 7 항에 있어서,
상기 스티렌네이티드 페놀은 n=1인 모노-스티렌네이티드 페놀(MSP) 50∼75 중량%, n=2인 다이-스티렌네이티드 페놀(DSP) 15∼35 중량% 및 n=3인 트리-스티렌네이티드 페놀(TSP) 1∼8 중량%의 함량비를 이루고 있는 것을 특징으로 하는 에폭시 도료.
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
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PCT/KR2013/010723 WO2015076440A1 (ko) | 2013-11-25 | 2013-11-25 | 에폭시 수지의 경화제 또는 가소제로 유용한 스티렌네이티드 페놀 |
CN201380011742.8A CN104870514B (zh) | 2013-11-25 | 2013-11-25 | 适用于环氧树脂的硬化剂或增塑剂的苯乙烯酚 |
JP2015549244A JP6063059B2 (ja) | 2013-11-25 | 2013-11-25 | エポキシ樹脂の硬化剤または可塑剤として有効なスチレン化フェノール |
US14/380,820 US9771310B2 (en) | 2013-11-25 | 2013-11-25 | Styrenated phenol useful as curing agent or plasticizing agent for epoxy resin |
HK15112874.9A HK1211971A1 (en) | 2013-11-25 | 2015-12-31 | Styrenated phenol useful as curing agent or plasticizing agent for epoxy resin |
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PCT/KR2013/010723 WO2015076440A1 (ko) | 2013-11-25 | 2013-11-25 | 에폭시 수지의 경화제 또는 가소제로 유용한 스티렌네이티드 페놀 |
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US (1) | US9771310B2 (ko) |
JP (1) | JP6063059B2 (ko) |
CN (1) | CN104870514B (ko) |
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WO (1) | WO2015076440A1 (ko) |
Cited By (2)
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EP3153537A1 (en) * | 2015-10-06 | 2017-04-12 | Korea Kumho Petrochemical Co., Ltd. | Heavy-duty epoxy coating composition including styrenated phenol and method of preparing the same |
WO2020163413A1 (en) * | 2019-02-05 | 2020-08-13 | Franklin International, Inc. | Very high solids, thermoset composition with one-side (wet set) adhesion to unprimed/unmodified tpo surfaces |
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WO2017131730A1 (en) * | 2016-01-29 | 2017-08-03 | Hewlett-Packard Development Company, L.P. | Electrode system |
CN107602819A (zh) * | 2017-08-17 | 2018-01-19 | 湖北绿色家园材料技术股份有限公司 | 一种低成本、高硬度、高光泽环氧石材面胶固化剂的制备方法 |
JP7477261B2 (ja) * | 2018-03-29 | 2024-05-01 | 日鉄ケミカル&マテリアル株式会社 | ヒドロキシ化合物、その製造方法、樹脂組成物及びその硬化物 |
KR102173016B1 (ko) * | 2018-10-15 | 2020-11-02 | 금호석유화학 주식회사 | 첨가제 조성물 및 그 제조방법 |
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- 2013-11-25 CN CN201380011742.8A patent/CN104870514B/zh active Active
- 2013-11-25 US US14/380,820 patent/US9771310B2/en active Active
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Also Published As
Publication number | Publication date |
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JP2016509615A (ja) | 2016-03-31 |
HK1211971A1 (en) | 2016-06-03 |
US9771310B2 (en) | 2017-09-26 |
CN104870514B (zh) | 2019-10-01 |
JP6063059B2 (ja) | 2017-01-18 |
CN104870514A (zh) | 2015-08-26 |
US20160207859A1 (en) | 2016-07-21 |
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