EP3938144A2 - Résine pour matériaux abrasifs et procédé de production de celle-ci - Google Patents

Résine pour matériaux abrasifs et procédé de production de celle-ci

Info

Publication number
EP3938144A2
EP3938144A2 EP20773384.1A EP20773384A EP3938144A2 EP 3938144 A2 EP3938144 A2 EP 3938144A2 EP 20773384 A EP20773384 A EP 20773384A EP 3938144 A2 EP3938144 A2 EP 3938144A2
Authority
EP
European Patent Office
Prior art keywords
resin
derivatives
resin according
compound selected
range
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
Application number
EP20773384.1A
Other languages
German (de)
English (en)
Other versions
EP3938144A4 (fr
Inventor
Haydar CETIN
Ozge AKSIN ARTOK
Alper Emre GUVENDIK
Hande OZCAN
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cukurova Kimya Endustrisi AS
Original Assignee
Cukurova Kimya Endustrisi AS
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Cukurova Kimya Endustrisi AS filed Critical Cukurova Kimya Endustrisi AS
Publication of EP3938144A2 publication Critical patent/EP3938144A2/fr
Publication of EP3938144A4 publication Critical patent/EP3938144A4/fr
Pending legal-status Critical Current

Links

Classifications

    • 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
    • C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
    • C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
    • C08G14/04—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols
    • C08G14/06—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols and monomers containing hydrogen attached to nitrogen
    • 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
    • C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
    • C08G8/28—Chemically modified polycondensates
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B24—GRINDING; POLISHING
    • B24D—TOOLS FOR GRINDING, BUFFING OR SHARPENING
    • B24D11/00—Constructional features of flexible abrasive materials; Special features in the manufacture of such materials

Definitions

  • the present invention relates to resins giving flexibility and elasticity to the substrate/support on which abrasive grains are coated in order to obtain abrasive materials which are suitable for industrial, manual or individual use and maintain their abrasion properties for a long time, and a synthesis of these resins.
  • Abrasive materials are widely used in various industrial, domestic and technological applications. Due to different usage areas, the abrasive materials may have different physical and chemical compositions, and different shapes or sizes may be preferred according to said usage areas. Common uses of abrasive materials include grinding, polishing, cutting, drilling, sharpening and sanding. Since abrasive materials are able to be shaped for various purposes, they can be produced as blocks, straps, discs, wheels, plates, rods and loose grains. In addition to abrasive grains, abrasive materials comprise fillers and/or binding materials and/or a substrate/layer.
  • abrasive materials can have different shapes depending on their contents and production methods, they can be divided into two separate groups as bonded abrasive materials and coated abrasive materials.
  • bonded abrasive materials are obtained by a mixture of abrasive grains with fillers and binding materials.
  • coated abrasive materials on the other hand, abrasive grains are bonded or adhered to a substrate, such as in sandpapers.
  • the substrate may be a paper, a fabric, a vulcanized fibre or resin.
  • abrasive grains may be different components, for example a glass, a flint, a garnet, aluminium oxide, silicon carbide.
  • coated abrasive materials e.g. sandpapers
  • sandpapers coated abrasive materials
  • Insufficient flexibility of the substrates carrying the abrasive grains causes the abrasive materials to break, loose their abrasion properties and shortens their lifetime.
  • phenolic resin is used as a binder together with the abrasive grains.
  • using aliphatic tack modifier and phenolic resin as a binding agent provides orientation of the abrasive grains.
  • US20140318025 A1 aims to improve abrasion properties of the abrasive materials by utilising thiol groups.
  • WO2012089351 discloses production of a resin which comprises polycyclic phenol for use in providing the abrasive materials with the property of flexibility. In this case, polycyclic phenols react with methanol and paraformaldehyde in presence of sodium hydroxide.
  • formulations and production method disclosed in said documents do not provide the abrasive materials with sufficient elasticity and colouring. Brittle and rigid structure of the abrasive grains requires a high elasticity coefficient for the substrate (support) to which they are applied. For that reason, there is a need to develop a resin which provides the abrasive material with elasticity property and is capable of maintaining its abrasion function for a long time, and a production method thereof.
  • a resin suitable for use in abrasive materials comprises at least one compound selected from phenol and/or derivatives thereof, at least one compound selected from aldehyde-based chemicals, at least one strong base, at least one fatty acid ester, at least one nitrogen-containing compound, at least one weak acid, at least one pH balancing agent, at least one plasticiser and at least one curing accelerating agent.
  • a production method of the resin according to the invention comprises the steps of: placing in a reactor/reaction vessel at least one compound selected from phenol and/or derivatives thereof together with at least one compound selected from aldehyde-based chemicals and at least one strong base to initiate the reaction; modifying the obtained mixture by adding at least one fatty acid ester; adding at least one nitrogen compound to the mixture; then, adding at least one weak acid; adjusting pH value by adding at least one pH balancing agent; adding at least one plasticiser and forming a polymer mixture; adding at least one curing accelerating agent and obtaining the resin.
  • abrasive materials are rigid and they are not provided with a desired flexibility during production, problems as breaking, reduction in abrasion properties and loss of flexibility occur frequently during abrasion processes.
  • a resin which eliminates said problems and is provided with elasticity property, and abrasive materials produced with said resin.
  • An object of the present invention is to develop a resin comprising phenol formaldehyde for maintaining the abrasion property of the abrasive material for a long time and giving elasticity to the substrate to which brittle rigid abrasive grains are bonded, and a production method.
  • Another object of the present invention is to develop a resin comprising phenol formaldehyde for providing colour stabilization of the abrasive materials and facilitating the application thereof, and a production method.
  • Yet a further object of the present invention is to develop a production method of a resin comprising phenol formaldehyde which is resistant to breaking and deformation for binding the abrasive grains firmly to the substrate/surface and/or support.
  • Abrasive grains should be used by providing flexibility in order to be suitable for use manually, in machines, or for other particular purposes.
  • Substrate which is used to provide the abrasive grains with flexibility and to hold the abrasive grains together may be a woven fabric, a paper, a fibre or resin. Resin-based substrates produced according to the conventional methods may cause harder and more brittle abrasive materials to be obtained, instead of providing the abrasive grains with flexibility.
  • a resin comprising phenol formaldehyde for maintaining the abrasion property of the abrasive material for a long time and giving elasticity to the substrate to which brittle and rigid abrasive grains are bonded, and a production method.
  • the resin according to the present invention comprises at least one compound selected from phenol and/or derivatives thereof, at least one compound selected from aldehyde- based chemicals, at least one strong base, at least one fatty acid ester, at least one nitrogen-containing compound, at least one weak acid, at least one pH balancing agent, at least one plasticiser and at least one curing accelerating agent.
  • the production method of the resin according to the present invention comprises the steps of: placing in a reactor/reaction vessel at least one compound selected from phenol and/or derivatives thereof together with at least one compound selected from aldehyde- based chemicals and at least one strong base to initiate the reaction; modifying the obtained mixture by adding at least one fatty acid ester; adding at least one nitrogen compound to the mixture; then, adding at least one weak acid; adjusting pH value by adding at least one pH balancing agent; adding at least one plasticiser and forming a polymer mixture; and adding at least one curing accelerating agent and obtaining the resin.
  • a production method of the abrasive materials comprising the resin according to the present invention comprises the steps of: placing in a reactor/reaction vessel at least one compound selected from phenol and/or derivatives thereof together with at least one compound selected from aldehyde-based chemicals and at least one strong base to initiate the reaction; modifying the obtained mixture by adding at least one fatty acid ester; adding at least one nitrogen compound to the mixture; then, adding at least one weak acid; adjusting pH value by adding at least one pH balancing agent; adding at least one plasticiser and forming a polymer mixture; adding at least one curing accelerating agent; after preparation of the resin with the added compounds, applying the resin to the substrate/support onto which the abrasive grains hold; placing the abrasive grains onto the resin; curing the obtained resinous abrasive grains in a furnace and obtaining the abrasive material.
  • molar ratio of at least one compound selected from phenol and/or derivatives thereof to at least one compound selected from aldehyde-based chemicals is in the range of 0.8 to 3.0 (preferably in the range of 1.0 to 2.3, more preferably in the range of 1.2 to 1.7).
  • the aldehyde-based chemical preferably comprises paraformaldehyde.
  • the at least one strong base comprises sodium hydroxide.
  • the strong base functions as a catalyst.
  • the strong base is preferably added to the resin according to the invention in a single step or two separate steps. A portion of the catalyst is added to the mixture before initiation of the exothermic reaction, and the remaining portion thereof is added 15 minutes after the initiation of said exothermic reaction, i.e. when the exothermic reaction is more controllable.
  • the strong base is preferably added in a range of 0.003 to 0.3 of the total mole amount of at least one compound selected from phenol and/or derivatives thereof. If a lower amount of strong base is added, it cannot function as a catalyst in the resin mixture as desired, while excess usage affects the mechanical properties and colour of the resin in a negative manner.
  • At least one fatty acid ester that is added comprises methyl esters of unsaturated fats and/or ethyl propyl, butyl esters of all fats.
  • Said fatty acid esters are used with a ratio in the range of 0.1% to 5% by weight based on the total weight of the resin. Addition of fatty acid esters with this ratio saponifies some of the catalyst in the resin. Saponification decelerates the reaction which is required for generating the resin while it contributes the resin to have a more flexible structure.
  • Fatty acid esters added in this step create a surfactant effect that ensures both the application of the resin to the support and the application of abrasive grains to the resin homogeneously.
  • the at least one nitrogen-containing compound comprises urea, melamine, tannic acid and/or any combinations thereof.
  • Using nitrogen compounds in this case allows free formaldehydes in the resin to be captured.
  • said formaldehyde capturing component preferably comprises an amino-functional group.
  • the abrasive material obtained with the resin according to the invention can be coloured and has flexible mechanical properties.
  • the at least one nitrogen compound is added to the mixture when the viscosity value of the mixture is in the range of 100 cps - 70000 cps (more preferably 500 cps - 4000 cps) at 20°. Said ideal viscosity value is obtained in a temperature range of 60°C to 100°C by preferably increasing 1 °C per minute, with a waiting time of 30 minutes at 90 °C.
  • At least one weak acid that is added comprises salicylic acid, phthalic acid, weak phenolic acids and/or any combinations thereof (preferably salicylic acid).
  • the weak acids are added for ion exchange with strong bases that cause the colour of the resin to darken.
  • Weak acids are preferably added to the mixture in the same molar ratio with the strong bases. Therefore, negativities caused by acids of the weak bases (such as NH 4 CI, NH 4 N0 3 and such ammonium salts) used in conventional methods such as bad odour due to ammonia release and decrease in the water tolerance of the resin which makes it difficult to mix with water, are eliminated. Resin deliquescence and bad odour occurrence problems which are frequently encountered in the art are solved by the resin and the production method of the invention.
  • At least one pH balancing agent that is added comprises tertiary amine, triol and/or combinations thereof.
  • the pH balancing agent preferably comprises triethanolamine (TEOA), dimethylethanolamine (DMEOA) and/or combinations thereof.
  • TEOA triethanolamine
  • DEOA dimethylethanolamine
  • the pH balancing agents balance the pH of the resin and function as a second catalyst. As the pH balancing agents are odourless organic bases, they solve bad odour problem occurred in the resin and help the resin have an odourless and flexible structure.
  • additional base can preferably be added to adjust pH based on a type of the surface on which the resin is applied.
  • Resins with acidic pH are suitable if the substrate/support to which the resin is applied is wool-, polyamide-, silk-based etc., and resins with basic pH are suitable for cotton-, ketene-, cellulose-based surfaces. Since the resin and the substrate comply with each other thanks to this method, binding of the resin to the substrate/support is improved.
  • the resin according to the invention comprises at least one coupling agent.
  • the at least one coupling agent may comprise organosilane, silane derivatives with amino-functional group, silane derivatives with epoxy-functional group, silane derivatives with uredo-functional group or any combinations thereof.
  • At least one plasticiser agent comprises phenols, hydrogenated vegetable oils, plasticiser adipates (e.g. dioctyladipate), plasticiser phthalates (e.g. dioctylterephthalate), fatty esters, epoxide vegetable oil esters, glycols and glycol esters (e.g.
  • polyethylene glycol PEG
  • diethylene glycol DEG
  • butyldiglycol DB mineral oils and derivatives thereof
  • polyesters carboxymethylated cellulose and derivatives thereof
  • long chain alcohols sodium naphthalene sulphonate, metyl oleate, phthalic anhydride, urea formaldehyde glues
  • polyvinyl alcohols PVA with different hydroxyl percentages and polymer chain lengths and/or combinations thereof.
  • Role of the plasticiser agent in the resin is crucial. Since the resin according to the invention is phenolic, at least one plasticiser agent preferably comprises polyvinyl alcohols (PVA) due to the vinyl groups and stretchable pi bonds of the resin.
  • Polyvinyl alcohols may be used alone or in combination with the other plasticisers described above. With the alcohol groups they have, polyvinyl alcohols comply with the phenolic hydroxyl groups in the resin and are homogeneously added to this phenolic structure with the hydrogen bonds. Hydrolysis number, polymer length, weight, purity and usage amount of the PVA directly affects the properties of the resin and the abrasive materials. Thus, it is of great importance to provide proper PVA modification. Usage amount of PVA for said modification is in the range of 0.1 % to 300 (preferably in the range of 0.2% to 20%, more preferably in the range of 0.5% to 5%) by weight based on the total weight.
  • usage amount of PVA is in the range of 50% to 300% by weight based on the total weight. Usage of higher amounts of PVA may cause repression in the thermal and mechanic properties arising from the phenolic polymer in the resin. Hydrolysis percentage of PVA is required to be high for said modification. Due to the high hydrolysis percentage, hydroxyl number of the phenolic structure in the resin increases, and better and more flexible hydrogen bonds are generated with electronegative groups of the fibres present on the surface. PVA chains with high hydrolysis percentages interact more with phenol formaldehyde polymer chains in the resin. With more interaction, a high compliance and curing are provided in the resin.
  • hydrolysis number per each mole in the resin according to the invention should be in the range of 50% to 99%.
  • PVA should be added to the resin preferably at 40°C.
  • 4% PVA solutions with a viscosity value in the range between 3MPa.sn and 70MPa.sn under DIN 53015 at 20°C are used.
  • PVA is preferably dissolved in a different reactor and added in the last step of the resin production method.
  • PVA which may be in solid or solution form, is preferably added to the mixture so that its weight is 0.5% to 5% by weight based on the total weight. Another important factor is polymerisation degree. As the polymer length of PVA increases, it increases the viscosity of the resin to which it is added.
  • Increase in the viscosity of resin causes problems during usage and causes non-compliance of the other materials, which are preferably added (e.g. fillers), to the resin.
  • the polymer length of PVA becomes shorter (having a low polymerisation degree), it does not provide the resin, to which it is added, with ideal binding property.
  • the PVA should be added to the resin with abovementioned conditions and properties. If the PVA with the values described in the invention is added to the resin with the described values, the resin with perfect flexibility is obtained. Alcohol groups of PVA comply with the hydroxyl groups of the resin due to the phenolic structure of the resin. Therefore, PVA is added homogenously to the resin structure with hydrogen bonds.
  • a polymer mixture is generated.
  • the polymer mixture generated crosslinks with free formaldehydes in the resin structure during a firing process so that it has a water-insoluble, colourable and flexible property which satisfies thermal and mechanical resistance.
  • Such flexibility enables the abrasive grains to be bonded strongly to the substrate/layer.
  • At least one curing accelerating agent comprises propylene carbonate, lactones (preferably, gamabutyrolactone), aniline (and/or derivatives thereof) and/or combinations thereof. These components reduce the curing/gelling time of the resin. If compared to curing accelerating agents known in the art, the curing accelerating agents used for the method of the invention reduces the gelling time without negatively affecting the curing colour and decreasing the binding property of the resin. Using the curing/gelling agents of the invention instead of other alkali-containing carbonates known in the art provides a faster curing.
  • the curing accelerating agent preferably comprises N-(2- hydroxyethyl)aniline.
  • the curing/gelling time of the resin is reduced by 10% to 20% when compared to the conventional methods.
  • the abrasive materials are widely used today, they become non-functional within a short period of time as they are not produced sufficiently flexible and durable. If one or some of the production steps and the resin of the invention are used, flexible abrasive materials are able to be obtained; however, they do not have as much synergistic action as the ones prepared by this method.
  • the resin obtained according to the method of the present invention enables that the abrasive grains are ideally applied and the abrasive materials are ideally shaped.
  • the resin of the invention enables the abrasive grains to be firmly bonded to the substrate/support, to be colourable, and to gain a structure that can flex without breaking/deforming. Furthermore, the resin can also be used in sandpapers and fabrics.
  • the resin can be mixed with a filler and/or other additives (e.g. a colour pigment) before being applied to the abrasive grains.
  • a filler and/or other additives e.g. a colour pigment
  • the substrates obtained by the resin and the resin production method of the present invention are tested through appropriate quality controls, it is seen that the substrate has the compatible specifications with the sector to be used. Since the resins cross-link at a binding temperature, abrasive materials are obtained in which the abrasive grains firmly hold onto the substrate/support.
  • another layer of resin can preferably be applied to the abrasive grains which are bonded to the substrate/support.
  • the abrasive materials prepared as several layers are cured by being moved forward in furnaces at certain angles, which enables more durable abrasive materials (e.g. sandpaper) to be obtained.
  • the obtained abrasive material may preferably be processed further.
  • top surface of the abrasive material can be coated with a new top layer by using a mixture that contains grinding auxiliaries, inert fillers, anti-static agents, lubricants, anti loading agents and mixtures thereof. Following the processes according to the present invention, the abrasive material acquires a whitish surface colour.
  • This colour can be changed easily by using an appropriate colour pigment at the beginning of the method steps of the invention or during preparation of the resin.
  • colour of the abrasive material represents many criteria in the industry (e.g. type of the abrasive grain), it can be coloured according to the conventional representative colours.
  • the abrasive material obtained by the method of the present invention can be cut to a desired size, and can be used by rubbing manually or by means of a machine or any dedicated means in order to perform abrasion/sanding processes on the surfaces. Since the resin according to the present invention provides a high flexibility as compared to the ones known in the art, it performs abrasion process without breaking or being deformed during the rubbing process.
  • the abrasive materials according to the present invention are also advantageous on the surfaces such as wood in terms of personal usages for hobby purposes.

Abstract

La présente invention concerne une résine phénolique appropriée pour être utilisée en particulier dans le secteur des abrasifs, un procédé de production de ladite résine et un procédé de production d'un matériau abrasif avec ladite résine. Plus particulièrement, la présente invention concerne des matériaux abrasifs qui ont un haut coefficient d'élasticité et une longue durée de vie sans déformation. Les abrasifs produits sont appropriés pour être utilisés manuellement, dans des machines, ou à d'autres fins particulières, les abrasifs éliminant les problèmes tels que le déchirement/la rupture. Tout en ayant des propriétés mécaniques et thermiques flexibles, les matériaux abrasifs ont également la propriété d'être colorés, ce qui est crucial pour le secteur.
EP20773384.1A 2019-03-15 2020-03-11 Résine pour matériaux abrasifs et procédé de production de celle-ci Pending EP3938144A4 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
TR2019/03909A TR201903909A2 (tr) 2019-03-15 2019-03-15 Aşındırıcı elemanlar için bir reçine ve bunun için bir üretim yöntemi.
PCT/TR2020/050198 WO2020190238A2 (fr) 2019-03-15 2020-03-11 Résine pour matériaux abrasifs et procédé de production de celle-ci

Publications (2)

Publication Number Publication Date
EP3938144A2 true EP3938144A2 (fr) 2022-01-19
EP3938144A4 EP3938144A4 (fr) 2023-01-04

Family

ID=72520449

Family Applications (1)

Application Number Title Priority Date Filing Date
EP20773384.1A Pending EP3938144A4 (fr) 2019-03-15 2020-03-11 Résine pour matériaux abrasifs et procédé de production de celle-ci

Country Status (3)

Country Link
EP (1) EP3938144A4 (fr)
TR (1) TR201903909A2 (fr)
WO (1) WO2020190238A2 (fr)

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5958794A (en) * 1995-09-22 1999-09-28 Minnesota Mining And Manufacturing Company Method of modifying an exposed surface of a semiconductor wafer
EP0776733B1 (fr) * 1995-11-28 2002-09-25 Minnesota Mining And Manufacturing Company Feuille abrasive pour traitement de surface et procédé pour sa production
US5770750A (en) * 1997-01-10 1998-06-23 Georgia-Pacific Resins, Inc. Alkyd and aralkyd derivatives of phenolic polymers
JP2006130607A (ja) * 2004-11-05 2006-05-25 Three M Innovative Properties Co 反応性無機吸熱物質を含む研磨材
KR100904628B1 (ko) * 2005-06-29 2009-06-25 생-고뱅 어브레이시브즈, 인코포레이티드 연마 제품용 고성능 수지
CN101802036B (zh) * 2007-09-21 2012-08-08 圣戈班磨料磨具有限公司 酚醛树脂配制品以及用于磨料产品的涂层
WO2010053729A1 (fr) * 2008-11-04 2010-05-14 Guiselin Olivier L Article abrasif revêtu pour applications de polissage ou de rodage et système et procédé pour sa production
CN102863598B (zh) * 2012-10-09 2014-07-16 江苏锋芒复合材料科技集团有限公司 一种砂纸用中低温固化柔性酚醛树脂的制备方法
CN109321204A (zh) * 2018-10-24 2019-02-12 河南省力量钻石股份有限公司 一种多颗粒附聚型磨粒体、制备方法及其应用

Also Published As

Publication number Publication date
TR201903909A2 (tr) 2020-10-21
WO2020190238A2 (fr) 2020-09-24
EP3938144A4 (fr) 2023-01-04
WO2020190238A3 (fr) 2021-04-29

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