EP4182362A1 - Uv curable epoxy resin compositions comprising reactive dilu-ents - Google Patents
Uv curable epoxy resin compositions comprising reactive dilu-entsInfo
- Publication number
- EP4182362A1 EP4182362A1 EP21745907.2A EP21745907A EP4182362A1 EP 4182362 A1 EP4182362 A1 EP 4182362A1 EP 21745907 A EP21745907 A EP 21745907A EP 4182362 A1 EP4182362 A1 EP 4182362A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- reactive diluent
- composition according
- mass
- reactive
- diluent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000003085 diluting agent Substances 0.000 title claims abstract description 41
- 239000000203 mixture Substances 0.000 title claims abstract description 24
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 20
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 19
- 229920005989 resin Polymers 0.000 claims description 17
- 239000011347 resin Substances 0.000 claims description 17
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 8
- 125000004386 diacrylate group Chemical group 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 231100000489 sensitizer Toxicity 0.000 claims description 4
- VOBUAPTXJKMNCT-UHFFFAOYSA-N 1-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound CCCCCC(OC(=O)C=C)OC(=O)C=C VOBUAPTXJKMNCT-UHFFFAOYSA-N 0.000 claims description 3
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 claims description 3
- YTLYLLTVENPWFT-UPHRSURJSA-N (Z)-3-aminoacrylic acid Chemical compound N\C=C/C(O)=O YTLYLLTVENPWFT-UPHRSURJSA-N 0.000 claims description 2
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229920000570 polyether Polymers 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- IPDYIFGHKYLTOM-UHFFFAOYSA-N 2-(2-prop-2-enoyloxypropoxy)propyl prop-2-enoate Chemical group C=CC(=O)OCC(C)OCC(C)OC(=O)C=C IPDYIFGHKYLTOM-UHFFFAOYSA-N 0.000 claims 1
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 claims 1
- 229940048053 acrylate Drugs 0.000 claims 1
- 229940059574 pentaerithrityl Drugs 0.000 claims 1
- 239000004593 Epoxy Substances 0.000 abstract description 3
- 239000003960 organic solvent Substances 0.000 abstract description 3
- 239000011248 coating agent Substances 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000000306 component Substances 0.000 description 7
- 238000001723 curing Methods 0.000 description 7
- 239000000178 monomer Substances 0.000 description 6
- 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 description 4
- 238000003848 UV Light-Curing Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000004848 polyfunctional curative Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical group N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229940000425 combination drug Drugs 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 230000003678 scratch resistant effect Effects 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 230000035943 smell Effects 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/062—Polyethers
-
- 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
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
Definitions
- the present invention relates to UV curable epoxy resin compositions.
- Reactive diluents are substances, which reduce the viscosity of a resin for processing and become part of the resin during its subsequent curing via copolymerization.
- Dilu ents also called thinners, are usually added to resins to reduce their viscosity and, thereby, to adjust the rheology of the resins.
- thermal cured resins such diluents added are volatile substances evaporating from the resin during drying.
- the volatile diluents should be avoided.
- US2011250415A discloses an ultraviolet curable resin composition which includes 25 to 45 parts by weight of a modified epoxy acrylate oligomer; and 10 to 25 parts by weight of a urethane acrylate oligomer. Further provided is a metal sheet that is trans parent and corrosion resistant, impact resistant, scratch resistant, adhesive, anti-corro sive, and bendable (workable) by forming a coating film on the surface of a metal ma terial such as a steel material, specifically a steel sheet, using the UV curable resin com position mentioned above.
- a metal ma terial such as a steel material, specifically a steel sheet
- WO17017128A1 discloses a composition, comprising A) a photo-curable component; B) a photo-initiator; and C) a polymer-containing coating, wherein the component A is physically mixed with component C, or is chemically bonded to the polymer of compo nent C.
- the present invention further relates to a process for preparing the composition and a process for applying the composition, and the coating film obtained therefrom.
- US2009227698A discloses a surface coating for moulded articles, especially for the automotive industry, said surface coating comprising at least 40 percent by weight of one or more resin components to achieve the requisite product properties, up to 60 per- cent by weight of one or more reactive diluents and between 0.3 percent and 1.5 percent by weight of UV initiators, the viscosity of the surface coating at the processing tem perature being between 500 and 2500 mPa s; and also the use of a surface coating for coating moulded articles of wood in an IMC machine under UV irradiation.
- resins of this type are also used for other purposes.
- One such purpose is for re-lining pipes, typically in water supply systems or sewer systems.
- a well-known method is to impregnate a flexible- typically woven tube with an epoxy resin. Thereafter the flexible tube is inserted or drawn into the pipe to receive a new lining. The tube is expanded in-situ against the inner wall of the pipe. In this position the epoxy resin is allowed to set, thereby creating a new inner pipe liner.
- This method although finding wide-spread use has a number of drawbacks.
- the epoxy resin used must be a two-component epoxy resin in order to achieve desired strength characteristics and suf ficient liquid tightness. However as soon as the two components are mixed the chemical hardening process will commence.
- Some of the epoxy systems used have slow harden- ers, which may be activated or accelerated by using heating in-situ- which requires a subsequent process following installing the liner which already is in the process of hard ening.
- Others just have regular hardeners whereby the epoxy hardening process is going on while the liner is being inserted into the pipe. This naturally puts stress on the whole process, as it is necessary to complete the installation in the time allowed by the hard- ener before the epoxy resin hardens.
- a further challenge is the fact that some of the epoxy resins used in the art also shrink during the hardening process. This is especially true for heat hardening epoxy resins. Of cause when the resin shrinks, the flexible tube liner will also shrink, thereby in some instances not be in complete contact with the inner side of the pipe in which it is in stalled. This may cause problems in that water (or other liquids) may flow between the liner and the pipe wall, thereby causing renewed trouble.
- the objective of this invention is to disclose high strength UV curable epoxy resin com positions that have high resistance against the organic solvents.
- the addition of reactive diluents facilitates the processing of UV curing epoxy resins, allows the addition of more fillers and improves the wetting behaviour on the substrate. By replacing volatile diluents with reactive diluents, flammability, smell, skin irritation and environmental compatibility are improved.
- the object is therefore also to alleviate the problems with prior art uses as described above and make the epoxy resin useful in other applications as well.
- Other uses may include reinforcement of tanks, pools or other vessels. Also with respect to wind turbine blades/wings or boat hulls the present invention may find use.
- reactive diluents are incorporated into the resin during curing and remain in it after the curing is completed, they influence not only the viscosity of the uncured epoxys, but also its physical properties after curing. Therefore, the choice of the reactive diluent has an influence on adhesion of a resin to a substrate, its compatibility with a binder, flexibility of a cured layer, volatility of the composition and its environmental compatibility.
- Reactive diluents used are low-viscosity, mono-, bi- or polyfunctional monomers or oligomers. In general, several different monomers are combined so that one monomer can compensate for the undesired properties of another monomer. Monofunctional mon omers offer a low viscosity but are quite volatile and tend to smell. With an increasing number of functional groups of a monomer, its volatility decreases while viscosity and crosslinking of the final varnish increase.
- Reactive diluents for the UV curable epoxy resin compositions can be styrene, epoxides and acrylates. Especially, a specific combination of 3 various diacrylates is found to be particularly useful, resulting in a coating of superior mechanical strength and superior resistance against organic solvents.
- the UV curable epoxy resin composition is to be used in industries such as pipe tech nology for stocking lining/feeding and in wind industry, among other industries. Detailed Description of the Invention
- a UV curing epoxy resin composition comprising 50-70 mass% of an energy curable resin and 20-30 mass% of a first reactive diluent, and 5-10 mass% of a second diluent being different from the first diluent is disclosed.
- the energy curable resin is an epoxy acrylate such as Bi-sphe- nol A-epichlorohydrin acrylate.
- the first reactive diluent is being selected from glycol diacry lates, preferably, said first glycol diacrylate is dipropylene glycol diacrylate (DPGDA).
- the composition wherein the second reactive diluent, being different from the first reactive diluent is an amino acrylate.
- the second reactive diluent is selected from glycol diacry lates, different from the first glycol diacrylate, preferably, said second reactive diluent is polyethylene glycol diacrylate.
- the composition further comprises 0-10 mass% of a curing agent.
- the curing agent comprises pentaerythritol or its derivative or a Hexanediol.
- the composition is further characterised by comprising 0-1 mass% of a third reactive diluent, being different from the first reactive diluent and the second reactive diluent.
- the third reactive diluent is selected from diacrylates, preferably, the third reactive diluent being hexamethylene diacrylate a Hex- anediol diacrylate or a polyether amine.
- the composition is further comprising 0-1 mass% of a pho toinitiator or a sensitiser; preferably, the photoinitiator or the sensitizer being a phenyl bis phosphine oxide.
Landscapes
- 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)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DKPA202070497 | 2020-07-20 | ||
PCT/DK2021/050226 WO2022017570A1 (en) | 2020-07-20 | 2021-07-06 | Uv curable epoxy resin compositions comprising reactive dilu-ents |
Publications (1)
Publication Number | Publication Date |
---|---|
EP4182362A1 true EP4182362A1 (en) | 2023-05-24 |
Family
ID=79729051
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP21745907.2A Pending EP4182362A1 (en) | 2020-07-20 | 2021-07-06 | Uv curable epoxy resin compositions comprising reactive dilu-ents |
Country Status (2)
Country | Link |
---|---|
EP (1) | EP4182362A1 (en) |
WO (1) | WO2022017570A1 (en) |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1215131C (en) * | 2000-06-22 | 2005-08-17 | Dsmip财产有限公司 | Radiation curable colored coating compsn. |
CN1487033A (en) * | 2002-08-07 | 2004-04-07 | 珠海东诚化工有限公司 | Ultraviolet ray cured paint for surface treatment or alumium ou aluminium sections |
KR100722805B1 (en) * | 2004-12-23 | 2007-05-30 | (주)디피아이 홀딩스 | Ultraviolet Curable Paint Composition For Metals |
DE102006012274A1 (en) | 2006-03-15 | 2007-09-20 | Votteler Lackfabrik Gmbh & Co. Kg | Lacquer for surface coating of molded parts |
KR101036829B1 (en) | 2008-12-23 | 2011-05-24 | 주식회사 노루홀딩스 | Ultraviolet-Curable Composition for Transparent Color Coated Steel Sheet and Steel Sheet Using the Same |
CN108291109B (en) | 2015-07-28 | 2021-07-09 | 巴斯夫欧洲公司 | Coating composition |
-
2021
- 2021-07-06 WO PCT/DK2021/050226 patent/WO2022017570A1/en unknown
- 2021-07-06 EP EP21745907.2A patent/EP4182362A1/en active Pending
Also Published As
Publication number | Publication date |
---|---|
WO2022017570A1 (en) | 2022-01-27 |
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Owner name: BODOTEX TECHNOLOGY APS |