WO2012017235A1 - Sols revêtus et procédés pour coller un revêtement sur le sol - Google Patents

Sols revêtus et procédés pour coller un revêtement sur le sol Download PDF

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Publication number
WO2012017235A1
WO2012017235A1 PCT/GB2011/051461 GB2011051461W WO2012017235A1 WO 2012017235 A1 WO2012017235 A1 WO 2012017235A1 GB 2011051461 W GB2011051461 W GB 2011051461W WO 2012017235 A1 WO2012017235 A1 WO 2012017235A1
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WIPO (PCT)
Prior art keywords
group
floor
flooring
monomer
hydrogen
Prior art date
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PCT/GB2011/051461
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English (en)
Inventor
Warrick James David Allen
James Leonard Rolfe
Andrea Duffy
Original Assignee
Novel Polymer Solutions Limited
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Filing date
Publication date
Priority claimed from GBGB1012954.2A external-priority patent/GB201012954D0/en
Priority claimed from GBGB1016664.3A external-priority patent/GB201016664D0/en
Priority claimed from GBGB1105439.2A external-priority patent/GB201105439D0/en
Application filed by Novel Polymer Solutions Limited filed Critical Novel Polymer Solutions Limited
Publication of WO2012017235A1 publication Critical patent/WO2012017235A1/fr

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
    • B32B7/04—Interconnection of layers
    • B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B25/00—Layered products comprising a layer of natural or synthetic rubber
    • B32B25/04—Layered products comprising a layer of natural or synthetic rubber comprising rubber as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B25/045—Layered products comprising a layer of natural or synthetic rubber comprising rubber as the main or only constituent of a layer, which is next to another layer of the same or of a different material of foam
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B25/00—Layered products comprising a layer of natural or synthetic rubber
    • B32B25/14—Layered products comprising a layer of natural or synthetic rubber comprising synthetic rubber copolymers
    • 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
    • C09D139/00—Coating compositions based on homopolymers or 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 single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Coating compositions based on derivatives of such polymers
    • C09D139/02—Homopolymers or copolymers of vinylamine
    • E—FIXED CONSTRUCTIONS
    • E04—BUILDING
    • E04F—FINISHING WORK ON BUILDINGS, e.g. STAIRS, FLOORS
    • E04F15/00—Flooring
    • E04F15/02—Flooring or floor layers composed of a number of similar elements
    • E04F15/0215—Flooring or floor layers composed of a number of similar elements specially adapted for being adhesively fixed to an underlayer; Fastening means therefor; Fixing by means of plastics materials hardening after application
    • E—FIXED CONSTRUCTIONS
    • E04—BUILDING
    • E04F—FINISHING WORK ON BUILDINGS, e.g. STAIRS, FLOORS
    • E04F15/00—Flooring
    • E04F15/02—Flooring or floor layers composed of a number of similar elements
    • E04F15/10—Flooring or floor layers composed of a number of similar elements of other materials, e.g. fibrous or chipped materials, organic plastics, magnesite tiles, hardboard, or with a top layer of other materials
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2250/00—Layers arrangement
    • B32B2250/02—2 layers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2255/00—Coating on the layer surface
    • B32B2255/26—Polymeric coating
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2266/00—Composition of foam
    • B32B2266/02—Organic
    • B32B2266/0214—Materials belonging to B32B27/00
    • B32B2266/0278—Polyurethane
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2405/00—Adhesive articles, e.g. adhesive tapes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2471/00—Floor coverings

Definitions

  • This invention relates to covered floors comprising a floor and a flooring thereon, and also to methods of adhering flooring to a floor.
  • PVC polyvinylchloride
  • Flooring is an example of such an industry, in which a number of manufacturers have developed alternative, PVC-free flooring products.
  • flooring products which are based on thermoplastics, elastomers and rubbers such as styrene butadiene rubbers (SBR) and nitrile butadiene rubbers (NBR). It is desired to be able to adhere such flooring materials using conventional flooring adhesives such as water based acrylic emulsions. However, it is not possible to achieve acceptable levels of adhesion on typical base floors such as concrete and plywood without a pre-treatment step.
  • Some flooring material can be secured to a floor via an intermediate layer such as a layer of polyurethane foam.
  • the flooring is adhered to the polyurethane foam with an adhesive, and the intermediate layer is separately adhered to the floor. Problems have been encountered in achieving an acceptable level of adhesion to flooring with such an intermediate layer.
  • the present invention in at least some of its embodiments, overcomes the above mentioned problems, and satisfies the above mentioned needs.
  • a covered floor including:
  • flooring of the type having an underside at least partially formed from a polymeric material, the flooring at least partially overlaying the floor;
  • an adhesive layer on the underside of the flooring the adhesive layer adhering the flooring to the floor, optionally via the intermediate layer; in which the polymeric coating acts to promote adhesion of the adhesive layer to the floor or the intermediate layer, and is formed by polymerising a polymeric precursor which includes a group of sub-formula (I)
  • R 2 and R 3 are independently selected from (CR 7 R 8 ) n , or a group CR 9 R 10 , CR 7 R 8 CR 9 R 10 or CR 9 R 10 CR 7 R 8 where n is 0, 1 or 2, R 7 and R 8 are independently selected from hydrogen, halo, or hydrocarbyl, or alkyl, and either one of R 9 or R 10 is hydrogen and the other is an electron withdrawing group, or R 9 and R 10 together form an electron withdrawing group;
  • R 4 and R 5 are independently selected from CH or CR 11 where CR 11 is an electron withdrawing group
  • X 1 is a group CX 2 X 3 where the dotted line bond to which it is attached is absent and a group CX 2 where the dotted line to which it is attached is present
  • Y 1 is a group CY 2 Y 3 where the dotted line to which it is attached is absent and a group CY 2 where the dotted line to which it is attached is present
  • X 2 ,X 3 ,Y 2 and Y 3 are independently selected from hydrogen, fluorine or other substituents.
  • polymeric precursors provided by the invention are preferably utilised with little or no solvents or other VOCs, and hence minimise the environmental impact of the invention. Furthermore, it has been found that polymeric coatings of the invention can provide excellent adhesion promotion on a number of materials which are used to form the undersides of flooring.
  • the term 'polymeric precursor' includes reference to monomers, and also to pre-polymers obtained by partial or pre- polymerisation of one or more monomers.
  • the term 'floor' refers to a basal constructional substrate such as in a room or other compartment of a building.
  • the underside of the flooring is directly adhered to the floor, ie, there is no intermediate layer.
  • the polymeric coating acts to promote adhesion of the adhesive layer directly to the floor.
  • an intermediate layer is present.
  • the intermediate layer may be formed from a polyurethane or other polymeric layer, and may be in the form of a foam.
  • the intermediate layer may be adhered to the floor using techniques which are well known to the skilled reader.
  • the underside consists essentially of the polymeric material.
  • the underside consists of a mixture of the polymeric material with one or more additives.
  • the mixture may include one or more mineral additives.
  • the polymeric material may be an elastomer, preferably a rubber.
  • the rubber may be natural or synthetic, and may be SBR or NBR rubber.
  • Flooring having an underside at least partially formed from a rubber may be adhered directly to the floor, or via an intermediate layer.
  • the polymeric material may be a thermoplastic, such as thermoplastic polyolefins (TPOs) or thermoplastic polyurethanes (TPUs).
  • thermoplastic polyolefins include polypropylene or polyethylene.
  • the adhesive layer may be formed from a water-based adhesive.
  • the use of solvent-based adhesives is also possible.
  • the adhesive layer may be formed from an acrylic adhesive.
  • Water- based acrylic adhesives are particularly preferred, such as Forbo 540, Uzin KE66 and others which are well known to the skilled reader. It is advantageous that conventional floor adhesives such as these can be used in connection with the invention.
  • the adhesive layer may be formed from a hot-melt adhesive.
  • Hot-melt adhesives may be used to adhere the floor to an intermediate layer such as a polyurethane or other polymeric layer.
  • the hot-melt adhesive may be formed from a polymeric material. Polyurethane, polyethylene, polypropylene, or polyethylene terephthalate hot-melt adhesives may be utilised.
  • the floor may be of any conventional kind, such as a concrete, composite or wooden floor.
  • Examples of wooden floors that may be covered with flooring include beech, oak, pine and plywood.
  • Composite floors include cement-based floors such as fibre cement floors.
  • the flooring may comprise sheeting or a plurality of tiles.
  • a method of adhering flooring to a floor including the steps of:
  • flooring of the type having an underside at least partially formed from a polymeric material
  • R 2 and R 3 are independently selected from (CR 7 R 8 ) n , or a group CR 9 R 10 , CR 7 R 8 CR 9 R 10 or CR 9 R 10 CR 7 R 8 where n is 0, 1 or 2, R 7 and R 8 are independently selected from hydrogen, halo or hydrocarbyl, and either one of R 9 or R 10 is hydrogen and the other is an electron withdrawing group, or R 9 and R 10 together form an electron withdrawing group;
  • R 4 and R 5 are independently selected from CH or CR 1 where CR 11 is an electron withdrawing group
  • X 1 is a group CX 2 X 3 where the dotted line bond to which it is attached is absent and a group CX 2 where the dotted line to which it is attached is present
  • Y is a group CY 2 Y 3 where the dotted line to which it is attached is absent and a group CY 2 where the dotted line to which it is attached is present
  • X 2 ,X 3 ,Y 2 and Y 3 are independently selected from hydrogen, fluorine or other substituents;
  • the polymeric coating acts to promote adhesion of the adhesive layer to the floor or the intermediate layer.
  • the intermediate layer may be adhered to the floor after the application of the adhesive layer which is formed between the polymeric coating and the intermediate layer.
  • the adhesive layer is applied to the floor and then contacted with the polymeric coating on the underside of the flooring in embodiments where there is no intermediate layer.
  • the adhesive layer may be applied to the intermediate layer and then contacted with the polymeric coating on the underside of the flooring, or the adhesive layer may be applied to the polymeric coating on the underside of the flooring and then contacted with the intermediate layer.
  • the polymeric precursor is polymerised by exposure to ultraviolet radiation.
  • Alternative polymerisation methods include the application of heat (which may be in the form of IR radiation), where necessary in the presence of an initiator, by the application of other sorts of initiator such as chemical initiators, or by initiation using an electron beam.
  • chemical initiator refers to compounds which can initiate polymerisation such as free radical initiators and ion initiators such as cationic or anionic initiators as are understood in the art. Radiation or electron beam induced polymerisation is suitably effected in the substantial absence of a solvent.
  • the expression "in the substantial absence of solvent” means that there is either no solvent present or there is insufficient solvent present to completely dissolve the reagents, although a small amount of a diluent may be present to allow the reagents to flow.
  • polymerisation may take place either spontaneously or in the presence of a suitable initiator.
  • suitable initiators include 2, 2' - azobisisobutyronitrile (AIBN), aromatic ketones such as benzophenones in particular acetophenone; chlorinated acetophenones such as di- or tri-chloracetophenone; dialkoxyacetophenones such as dimethoxyacetophenones (sold under the trade name "Irgacure 651 ”) dialkylhydroxyacetophenones such as dimethylhydroxyacetophenone (sold under the trade name "Darocure 1 173"); substituted dialkylhydroxyacetophenone alkyl ethers such compounds of formula
  • R y is alkyl and in particular 2, 2-dimethylethyl
  • R x is hydroxyl or halogen such as chloro
  • R p and R q are independently selected from alkyl or halogen such as chloro (examples of which are sold under the trade names "Darocure 1 16" and “Trigonal P1 "); 1-benzoylcyclohexanol-2 (sold under the trade name “Irgacure 184"); benzoin or derivatives such as benzoin acetate, benzoin alkyl ethers in particular benzoin butyl ether, dialkoxybenzoins such as dimethoxybenzoin or deoxybenzoin; dibenzyl ketone; acyloxime esters such as methyl or ethyl esters of acyloxime (sold under the trade name "Quantaqure PDO"); acylphosphine oxides, acylphosphonates such as dialkylacylphosphonate, keto
  • R z is alkyl and Ar is an aryl group; dibenzoyl disulphides such as 4, 4'- dialkylbenzoyldisulphide; diphenyldithiocarbonate; benzophenone; 4, 4'-bis (N, N-dialkyamino) benzophenone; fluorenone; thioxanthone; benzil; or a compound of formula
  • Ar is an aryl group such as phenyl and R z is alkyl such as methyl (sold under the trade name "Speedcure BMDS"), or an initiator of the type sold under the trade name 'Irgacure 127'.
  • alkyl refers to straight or branched chain alkyl groups, suitably containing up to 20 and preferably up to 6 carbon atoms.
  • alkenyl and alkynyl refer to unsaturated straight or branched chains which include for example from 2-20 carbon atoms, for example from 2 to 6 carbon atoms. Chains may include one or more double to triple bonds respectively.
  • aryl refers to aromatic groups such as phenyl or naphthyl.
  • hydrocarbyl refers to any structure comprising carbon and hydrogen atoms.
  • these may be alkyl, alkenyl, alkynyl, aryl such as phenyl or napthyl, arylalkyl, cycloalkyl, cycloalkenyl or cycloalkynyl.
  • aryl such as phenyl or napthyl
  • arylalkyl cycloalkyl
  • cycloalkenyl or cycloalkynyl Suitably they will contain up to 20 and preferably up to 10 carbon atoms.
  • heteroatom such as oxygen, sulphur or nitrogen.
  • Examples of such groups include furyl, thienyl, pyrrolyl, pyrrolidinyl, imidazolyl, triazolyl, thiazolyl, tetrazolyl, oxazolyl, isoxazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, benzthiazolyl, benzoxazolyl, benzothienyl or benzofuryl.
  • heteroatom refers to non-carbon atoms such as oxygen, nitrogen or sulphur atoms. Where the nitrogen atoms are present, they will generally be present as part of an amino residue so that they will be substituted for example by hydrogen or alkyl.
  • amide is generally understood to refer to a group of formula C(0)NR a R b where R a and R b are hydrogen or an optionally substituted hydrocarbyl group.
  • sulphonamide will refer to a group of formula S(0) 2 NR a R b .
  • Suitable groups R a include hydrogen or methyl, in particular hydrogen.
  • electron withdrawing group includes within its scope atomic substituents such as halo, e.g. fluoro, chloro and bromo, and also molecular substituents such as nitrile, trifluoromethyl, acyl such as acetyl, nitro, or carbonyl.
  • X 1 and, where present, Y 1 preferably represents CX 2 X 3 and CY 2 Y 3 respectively, and the dotted bonds are absent.
  • R 13 and R 14 when present, are alkyl groups, most preferably Ci to C 3 alkyl groups.
  • R c when present, is a carbonyl group or phenyl substituted at the ortho and/or para positions by an electron withdrawing substituent such as nitro.
  • R 7 and R 8 are independently selected from fluoro, chloro or alkyl or H. In the case of alkyl, methyl is most preferred.
  • X 2 , X 3 , Y 2 and Y 3 are all hydrogen.
  • At least one, and possibly all, of X 2 , X 3 , Y 2 and Y 3 is a substituent other than hydrogen or fluorine.
  • at least one, and possible all, of X 2 , X 3 , Y 2 and Y 3 is an optionally substituted hydrocarbyl group.
  • it is preferred that at least one, and most preferably all, of X 2 , X 3 , Y 2 and Y 3 is an optionally substituted alkyl group.
  • Particularly preferred examples are Ci to C 4 alkyl groups, especially methyl or ethyl.
  • Embodiments in which X 2 , X 3 , Y 2 and/or Y 3 are alkyl groups are able to polymerise when exposed to radiation without the presence of an initiator.
  • at least one, and preferably all, of X 2 , X 3 , Y 2 and Y 3 are aryl and/or heterocyclic, such as pyridyl, pyrimidinyl, or a pyridine or pyrimidine containing group.
  • Y 1 , X 1 and Y are groups CX 2 X 3 and CY 1 Y 2 respectively and the dotted lines represent an absence of a bond.
  • the polymerisation may proceed by a cyclopolymerisation reaction.
  • a preferred group of polymeric precursors for use in the method of the invention are compounds of formula (II)
  • r is an integer of 1 or more and R is one or more of a bridging group, an optionally substituted hydrocarbyl group, a perhaloalkyi group, a siloxane group, an amide, or a partially polymerised chain containing repeat units.
  • r is , 2, 3 or 4.
  • R 1 is S(0) 2 N or C(O)N.
  • the polymeric precursor may be a compound of structure (III)
  • R is C(O) or S(0) 2 .
  • the polymeric precursor is a compound of structure (IV)
  • polymerisation can result in polymer networks.
  • networks are formed whose properties maybe selected depending upon the precise nature of the R 6 group, the amount of chain terminator present and the polymerisation conditions employed.
  • R 6 comprises a straight or branched chain hydrocarbyl group, optionally substituted or interposed with functional groups.
  • the straight or branched chain hydrocarbyl is interposed or substituted with one or more of an amine moiety, C(O) or COOH.
  • the polymeric precursor is a monomer in which R 6 is a straight or branched chain hydrocarbyl interposed with an amine moiety, or a pre-polymer obtained by pre-polymerisation of said monomer.
  • the monomer is a straight or branched chain alkyl group having 1 to 30 carbon atoms, optionally interposed with a cyclic group.
  • the monomer is a compound of formula (V)
  • R 1b is H or C s H 2s +i , p is 1 to 10, 9 is 0 to 10 and s is 1 to 10.
  • the monomer is a compound of formula
  • the polymeric precursor is a monomer in which R 6 is a straight or branched chain hydrocarbyl substituted with a COOH end group, or a pre-polymer obtained by pre-polymerisation of said monomer.
  • the monomer may be a straight or branched chain alkyl group having 1 to 30 carbon atoms, optionally interposed with a cyclic group.
  • the monomer is a compound of formula (VII)
  • v 1 to 20.
  • the polymeric precursor is a monomer in which R 6 is a straight or branched chain alkyl group having 1 to 30 carbon atoms, or a pre-polymer obtained by pre-polymerisation of said monomer.
  • the polymeric precursor is a monomer in which, R 6 is a partially or per-halogenated straight or branched chain alkyl group having 1 to 30 carbon atoms, or a pre-polymer obtained by pre-polymerisation of said monomer.
  • R 6 is a partially or per-halogenated straight or branched chain alkyl group having 1 to 30 carbon atoms, or a pre-polymer obtained by pre-polymerisation of said monomer.
  • the alkyl group is per-halogenated. It is preferred that the alkyl group is fluorinated, most preferably per-fluorinated.
  • the polymeric precursor is a monomer in which R 5 is CO and R 6 terminates in one or more amine moieties forming a urea structure, or a pre-polymer obtained by pre-polymerisation of said monomer.
  • the polymeric precursor is a monomer of structure (VIII)
  • R 6 is a straight or branched chained hydrocarbyl group, optionally substituted or interposed with functional groups, and r is an integer of two or more, or a pre-polymer obtained by a pre-polymerisation of said monomer.
  • r is two or three.
  • a preferred class of the compound of formula (I) is represented as structure (X) where R 16 is selected from hydrogen, halo, nitro, or hydrocarbyl, optionally substituted or interposed with functional groups, only.
  • a particularly preferred compound of formula (X) is a compound of formula (XI)
  • the polymerisation of the polymeric precursor may produce a homopolymer.
  • the step of polymerising the polymeric precursor may produce a copolymer, the polymeric precursor being mixed with one or more other polymeric precursors.
  • the other polymeric precursor may be according to any of the formulae described herein.
  • the co- monomer may be of a different class of compounds.
  • the polymeric precursor may be copolymerised with a cross-linker. In these embodiments, the polymeric precursor may be reacted with a compound of formula (XII)
  • R 1 , R 2 , R 4 , R 12 and X 1 are as defined in relation to formula (I), r is an integer of 2 or more, and R 6 is a bridging group of valency r or a bond. Preferably, r is 2.
  • the use of a compound of formula (XII) is particularly advantageous when the polymeric precursor does not include the group -R 3 -R 5 : Y .
  • the compound of formula (XII) may be a compound of formula (XIII)
  • the polymeric precursor is: N, N- diallylhexanamide, N, N-Diallyl-3-(propylamino)propanamide, N, N-Diallyl-2(- butyl-diallylcarbamoylmethylamino)acetamide; a co-monomer mixture including N, N-diallylhexanamide, N, N-Diallyl-3-(propyIamino)propanamide, or N, N- Diallyl-2(-butyl-diallylcarbamoylmethylamino)acetamide.
  • the polymeric precursor may be a pre-polymer obtained by a pre-polymerisation of any of these substances.
  • Preferred co-monomer mixtures comprise: N, N-Diallyl- 3-(propylamino)propanamide / N, N, N', N'-tetraallylethanediamide; and N, N- diallylhexanamide / N, N-Diallyl-2(-butyl- diallylcarbamoylmethylamino)acetamide.
  • the polymeric precursor may contain one or more additives, such as a wetting agent.
  • a wetting agent such as a siloxane wetting agent may be used.
  • the monomer or co-monomers may be pre-polymerised to produce a pre- polymer.
  • a thermal initiator is used and pre-polymerisation is performed at an elevated temperature above ambient temperature.
  • the polymeric precursor is generally applied to the flooring and then polymerised.
  • the polymeric precursor might be polymerised and then brought into contact with the flooring to form a polymeric coating thereon.
  • the Figure shows an example of a covered floor of the invention, depicted generally at 10, which comprises a floor 12 in the form of a permanently installed base substrate, and an adhesive layer 14 formed on the floor 12.
  • the adhesive layer 14 adheres the floor 12 to flooring 16.
  • the flooring 16 comprises a main flooring structure 16a having an underside 16b.
  • the polymeric coating 16c acts to promote adhesion between the flooring 16 and the adhesive layer 14.
  • Polymeric coatings of the invention have been found to promote excellent adhesion of various conventional flooring materials to conventional floors such as fibre cement board and beech wood floors using conventional flooring adhesives.
  • N, N-Diallyl-3-(propylamino)propanamide ( 060.5g) and N, N, N', N'-Tetraallylethanediamide (79.5g) was heated to 80°C and maintained at this temperature with constant stirring.
  • a concentrate of Vazo 67 (DuPont) thermal initiator (75. Og) dissolved in N, N-Diallyl-3 propylamino)propanamide (264.75g) and N, N, N', N'-Tetraallylethanediamide (20.25g) was added dropwise over 6 hours with stirring and the reaction temperature maintained at 80°C.
  • the target molecule is shown below
  • Fresh, dry oxaloyl chloride (CIOOCCOOCI) (1 10 mmoles) was placed into a 3-necked round bottomed (RB) flask with 200 ml of dry dichloromethane.
  • Freshly distilled diallylamine (220mmoles) was added to triethylamine (220mmoles), further diluted (1 :1 v/v) in dry dichloromethane then added into a dropping funnel and placed onto the reaction flask. Nitrogen gas was pumped through the vessel through the other two necks. To neutralise HCI produced, the waste gas was bubbled through a CaC0 3 solution.
  • the reaction vessel was then placed into a salt water/ice bath and once the contents were cooled the diallylamine/triethylamine/ dichloromethane was added dropwise to the oxaloyl chloride solution with continual magnetic stirring of the mixture. The temperature was monitored and maintained between 5-10°C. The dropping of the diallylamine and triethylamine was stopped after three hours and the reaction was left to stir for another hour. Thin layer chromatography using ethyl acetate and an alumina was used to monitor the reaction comparing starting material to the product. Iodine was used to develop the plate and the reaction product could be seen as a spot that had been eluted much further than the starting material.
  • the product was added to dichloromethane (1 :1 v/v) and passed through a silica gel (Merck, grade 60 for chromatography) column with dichloromethane as the eluent. Some yellow coloration was left in the column which yielded, after removal of the eluent, a very pale yellow oil.
  • the product ⁇ , ⁇ , ⁇ ', ⁇ ',- tetraallylethanediamide was produced in -70% yield.
  • N, N-Diallyl-2-(butyl-diallylcarbamoylmethylamino)acetamide (890. Og) was pre-heated to 80°C after which a mixture of thermal initiator Vazo 67 (DuPont) (10. Og) in N, N-Diallyl-2-(butyl-diallylcarbamoylmethylamino)acetamide (100.0g) was added over 2 hours with the temperature maintained at 80°C with constant stirring and under a nitrogen atmosphere. This reaction was left to react for a further 14 hours under the same conditions and then left to cool to room temperature.
  • Vazo 67 DuPont
  • This formulation was then coated onto the underside of NBR rubber flooring using a reverse roller method to approximately 2 grams per square metre coat weight and cured under a 200W/cm UV lamp using an iron doped mercury bulb.
  • a moisture curing MDI based polyurethane hot melt (100% solids) was then deposited at 160°C onto the adhesion promoted NBR at a coating weight between 70 - 80 g/m 2 .
  • a PUR foam sheet was laminated onto the hot melt coating under pressure and allowed to cool to room temperature.
  • the PUR foam sheet can be adhered to a floor using techniques which are well known to the skilled reader.
  • Chloroacetyl chloride (98%, 212g, 1.883 moles) and dichloromethane (397.5g, 4.680 moles) were added to a reaction vessel and cooled to 5°C.
  • N,N- diallylamine freshly distilled, 402.57g, 4.143 moles
  • dichloromethane 397.5g, 4.680moles
  • this mixture was then added dropwise to the chloroacetyl chloride mixture over several hours with constant stirring with the temperature kept below 10°C.
  • the reaction mixture was then left to reach room temperature and then washed in water (1.51).
  • the organic phase was washed again in water, followed by separation of the organic phase.
  • N,N-Diallyl-2-chloroacetamide (intermediate) (86.75g, 0.500moles), triethylamine (154.38g, 1 .500moles) and tetrahydrofuran (222.25g, 3.082moles) were charged into a reaction flask with 1 -butylamine (99%, 18.29g, 0.250moles) added dropwise over 15 minutes with constant stirring. The temperature of the reaction was brought to reflux and maintained for 4 hours. The reaction was then cooled to room temperature followed by filtration of the triethylamine hydrochloride salt from the reaction liquor.
  • promotion layer consisting of a polymer made with N, N-Diallyl-2(-butyl- diallylcarbamoylmethylamino)acetamide
  • N, N-Diallyl-2-(butyl-diallylcarbamoylmethylamino)acetamide (890. Og) was pre-heated to 80°C after which a mixture of thermal initiator Vazo 67 (DuPont) (10. Og) in N, N-Diallyl-2-(butyl-diallylcarbamoylmethylamino)acetamide (100.0g) was added over 2 hours with the temperature maintained at 80°C with constant stirring and under a nitrogen atmosphere. This reaction was left to react for a further 14 hours under the same conditions and then left to cool to room temperature.
  • Vazo 67 DuPont
  • the photo initiator 2-isopropyl thioxanthone (ITX) (31.8g) and synergist ethyl 4-(dimethylamino) benzoate (EDB) (21 .2g) were then added and fully dissolved into the mixture prior to use.
  • This formulation was then coated onto the underside of SBR rubber flooring using a reverse roller method to approximately 2 grams per square metre coat weight and cured under a 200W/cm UV lamp using an iron doped mercury bulb.
  • the treated SBR was then bonded to wooden flooring that had been coated with a solvent free acrylate dispersion adhesive at a coating weight of 350g/m 2 using a spreading trowel. Approximately 5 minutes was left between spreading of adhesive and bonding to the rubber with an even force applied to the SBR surface once it had been laid onto the wooden flooring.
  • the treated SBR was then bonded to wooden flooring that had been coated with a water based acrylic dispersion adhesive at a coating weight of 350g/m 2 using a spreading trowel. Approximately 15 minutes was left between spreading of adhesive and bonding to the rubber with an even force applied to the SBR surface once it had been laid onto the wooden flooring.
  • Diallylamine (99%, 37g, 381 mmoles), triethylamine (99%, 40g, 396mmoles) and dichloromethane (99+%, 50ml) were mixed and added dropwise to a cooled (0°C ) mixture of hexanoyl chloride (99%+, 50g, 371 mmoles) in dichloromethane (99+%, 200ml) .
  • Temperature was maintained between 0-10 °C with continuous stirring for several hours to allow all of the diallylamine mixture to be added. The reaction mixture was then left to come to room temperature.
  • This mixture was then coated as a thin layer, of approximately 4g/m 2 coating weight , onto the back of a piece of acrylate coated rubber flooring using a roller method.
  • a 200W/cm UV lamp using an iron doped mercury bulb was then used to cure the coating.
  • a solvent free acrylate dispersion adhesive was spread onto at a plywood floor section at a coating weight of 300g/m 2 using a spreading trowel. Approximately 20 minutes was left between spreading of adhesive and bonding it to the treated underside of the rubber flooring, after which an even pressure was then applied across the sample.
  • the underside of a piece of flooring which consisted of a mineral filled thermoplastic polymer, was then coated with this formulation using a reverse roller method to approximately 3 grams per square metre coat weight. This was then cured under a 200W/cm UV lamp using an iron doped mercury bulb.
  • thermoplastic flooring was then bonded to a beechwood flooring that had been coated with a water based acrylic dispersion adhesive (Thomsit K188E, Henkel) at a coating weight of 300g/m 2 using a spreading trowel. Approximately 10 minutes was left between spreading of adhesive and bonding to the rubber with an even force applied to the flooring surface once it had been laid onto the wooden flooring.
  • a water based acrylic dispersion adhesive Trosit K188E, Henkel
  • thermoplastic flooring was then bonded to a beechwood flooring that had been coated with a water based acrylic dispersion adhesive (Thomsit K188E, Henkel) at a coating weight of 300g/m 2 using a spreading trowel. Approximately 10 minutes was left between spreading of adhesive and bonding to the rubber with an even force applied to the flooring surface once it had been laid onto the wooden flooring.
  • a water based acrylic dispersion adhesive Trosit K188E, Henkel

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  • Engineering & Computer Science (AREA)
  • Architecture (AREA)
  • Civil Engineering (AREA)
  • Structural Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention concerne un sol revêtu comprenant : un sol ; un revêtement de sol du type comprenant une surface inférieure au moins partiellement formée à partir d'un matériau polymère, le revêtement recouvrant au moins partiellement le sol ; un revêtement polymère sur la surface inférieure du revêtement de sol ; éventuellement, une couche intermédiaire collée sur le sol ; et une couche adhésive sur la surface inférieure du revêtement de sol, la couche adhésive collant le revêtement sur le sol, éventuellement via la couche intermédiaire. Le revêtement polymère agit pour promouvoir l'adhérence de la couche adhésive sur le sol ou de la couche intermédiaire, et est formé par polymérisation d'un précurseur polymère qui comprend un groupe représenté par la sous-formule (I), dans laquelle R1 représente i) CRa, où Ra représente hydrogène ou alkyle, (ii) un groupe S(0)pR13 ou SiR14 où R13 et R14 sont sélectionnés indépendamment parmi hydrogène ou hydrocarbyle, p est égal à 0, 1 ou 2 et q est égal à 1 ou 2, iii) C(0)N, S(0)2N, C(0)ON, CH2ON, ou CH=CHRCN où Rc représente un groupe extracteur d'électrons, ou iv) OC(0)CH, C(0)OCH ou S(0)2CH ; R12 est sélectionné parmi hydrogène, halo, nitro, hydrocarbyle, éventuellement substitués par des groupes fonctionnels ou interposés entre ceux-ci, ou représenté par la formule (II) dans laquelle R2 et R3 sont sélectionnés indépendamment parmi (CR7R8)n ou un groupe CR9R10, CR7R8CR9R10 ou CR9R10CR7R8 où n est égal à 0, 1 ou 2, R7 et R8 sont sélectionnés indépendamment parmi hydrogène, halo ou hydrocarbyle, et où n est égal à 0, 1 ou 2, R7 et R8 sont sélectionnés indépendamment parmi hydrogène ou alkyle, et l'un de R9 ou R10 représente hydrogène et l'autre représente un groupe extracteur d'électrons, ou R9 et R10 forment ensemble un groupe extracteur d'électrons ; R4 et R5 sont sélectionnés indépendamment parmi CH ou CR11 où CR11 représente un groupe extracteur d'électrons, les lignes en pointillés indiquent la présence ou l'absence d'une liaison, X1 représente un groupe CX2X3 où la liaison en ligne en pointillés à laquelle il est fixé est absente et un groupe CX2 où la liaison en ligne en pointillés à laquelle il est fixé est présente, Y1 représente un groupe CY2Y3 où la liaison en ligne en pointillés à laquelle il est fixé est absente et un groupe CY2 où la liaison en ligne en pointillés à laquelle il est fixé est présente, et X2,X3,Y2 et Y3 sont sélectionnés indépendamment parmi hydrogène, fluor ou d'autres substituants.
PCT/GB2011/051461 2010-08-02 2011-08-02 Sols revêtus et procédés pour coller un revêtement sur le sol WO2012017235A1 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
GB1012954.2 2010-08-02
GBGB1012954.2A GB201012954D0 (en) 2010-08-02 2010-08-02 Methods of coating a low surface energy substrate
GBGB1016664.3A GB201016664D0 (en) 2010-10-04 2010-10-04 Methods of coating a low surface energy substrate
GB1016664.3 2010-10-04
GB1105439.2 2011-03-31
GBGB1105439.2A GB201105439D0 (en) 2011-03-31 2011-03-31 Covered floors and methods of adhering flooring to a floor

Publications (1)

Publication Number Publication Date
WO2012017235A1 true WO2012017235A1 (fr) 2012-02-09

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017108621A1 (fr) * 2015-12-22 2017-06-29 Nora Systems Gmbh Revêtement de sol contenant un élastomère thermoplastique et son procédé de fabrication
WO2017108612A1 (fr) * 2015-12-22 2017-06-29 Nora Systems Gmbh Revêtement de sol autocollant et son procédé de production
EP3597706A1 (fr) * 2018-07-16 2020-01-22 Flooring Technologies Ltd. Composition de revêtement et de scellement des bords des panneaux fibreux
US11203677B2 (en) 2017-11-03 2021-12-21 American Biltrite (Canada) Ltd. Resilient surface coverings and methods of making and using thereof
RU2781067C2 (ru) * 2018-07-16 2022-10-05 Флуринг Текнолоджис Лтд. Композиция для покрытия и герметизации краев древесно-волокнистых плит

Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1012954A (en) 1961-09-22 1965-12-15 Burroughs Corp Improvements in or relating to multiple-track magnetic transducers
GB1016664A (en) 1963-08-17 1966-01-12 Bayer Ag Anthraquinone dyestuffs
WO2000006610A2 (fr) 1998-07-25 2000-02-10 The Secretary Of State For Defence Fabrication de polymeres
WO2000006533A2 (fr) 1998-07-25 2000-02-10 The Secretary Of State For Defence Monomeres, et polymeres reticules obtenus a partir desdits monomeres
WO2000006658A2 (fr) 1998-07-25 2000-02-10 The Secretary Of State For Defence Colles et produits d'etancheite
CA2303452A1 (fr) * 1999-04-08 2000-10-09 Hao A. Chen Sous-couche pour revetements de surface et methodes pour la fabriquer
WO2001036510A2 (fr) 1999-11-17 2001-05-25 Qinetiq Limited Utilisation de polymeres de poli(diallylamine)
WO2001040874A1 (fr) 1999-12-04 2001-06-07 Qinetiq Limited Utilisation d'une composition en stéréolithographie
WO2001074919A1 (fr) 2000-04-01 2001-10-11 Qinetiq Limited Polymeres
US20050281986A1 (en) * 2004-06-22 2005-12-22 Seung-Baik Nam Flooring having surface layer of synthetic resin and wood-based board
WO2007012860A1 (fr) 2005-07-27 2007-02-01 Novel Polymer Solutions Ltd Procédés de formation d’une barrière
WO2008001102A1 (fr) 2006-06-30 2008-01-03 Novel Polymer Solutions Limited Matières polymériques et procédés servant à fabriquer celles-ci
WO2009063211A1 (fr) 2007-11-17 2009-05-22 Novel Polymer Solutions Limited Procédés d'encapsulation d'une substance

Patent Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1012954A (en) 1961-09-22 1965-12-15 Burroughs Corp Improvements in or relating to multiple-track magnetic transducers
GB1016664A (en) 1963-08-17 1966-01-12 Bayer Ag Anthraquinone dyestuffs
WO2000006610A2 (fr) 1998-07-25 2000-02-10 The Secretary Of State For Defence Fabrication de polymeres
WO2000006533A2 (fr) 1998-07-25 2000-02-10 The Secretary Of State For Defence Monomeres, et polymeres reticules obtenus a partir desdits monomeres
WO2000006658A2 (fr) 1998-07-25 2000-02-10 The Secretary Of State For Defence Colles et produits d'etancheite
CA2303452A1 (fr) * 1999-04-08 2000-10-09 Hao A. Chen Sous-couche pour revetements de surface et methodes pour la fabriquer
WO2001036510A2 (fr) 1999-11-17 2001-05-25 Qinetiq Limited Utilisation de polymeres de poli(diallylamine)
WO2001040874A1 (fr) 1999-12-04 2001-06-07 Qinetiq Limited Utilisation d'une composition en stéréolithographie
WO2001074919A1 (fr) 2000-04-01 2001-10-11 Qinetiq Limited Polymeres
US20050281986A1 (en) * 2004-06-22 2005-12-22 Seung-Baik Nam Flooring having surface layer of synthetic resin and wood-based board
WO2007012860A1 (fr) 2005-07-27 2007-02-01 Novel Polymer Solutions Ltd Procédés de formation d’une barrière
WO2008001102A1 (fr) 2006-06-30 2008-01-03 Novel Polymer Solutions Limited Matières polymériques et procédés servant à fabriquer celles-ci
WO2009063211A1 (fr) 2007-11-17 2009-05-22 Novel Polymer Solutions Limited Procédés d'encapsulation d'une substance

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
HALL A W ET AL: "THE PHOTOINITIATED CYCLOPOLYMERIZATION OF DIENES IN THE CREATION OF NOVEL POLYMERIC SYSTEMS AND THREE-DIMENSIONAL NETWORKS", JOURNAL OF MATERIALS CHEMISTRY, THE ROYAL SOCIETY OF CHEMISTRY, CAMBRIDGE, GB, vol. 14, 23 July 2004 (2004-07-23), pages 2593 - 2602, XP002400380, ISSN: 0959-9428, DOI: 10.1039/B402154C *

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017108621A1 (fr) * 2015-12-22 2017-06-29 Nora Systems Gmbh Revêtement de sol contenant un élastomère thermoplastique et son procédé de fabrication
WO2017108612A1 (fr) * 2015-12-22 2017-06-29 Nora Systems Gmbh Revêtement de sol autocollant et son procédé de production
KR20180098596A (ko) * 2015-12-22 2018-09-04 노라 시스템즈 게엠베하 접착제 구비형 바닥 피복재 및 그 제조 방법
CN108603373A (zh) * 2015-12-22 2018-09-28 诺拉系统有限公司 自粘式楼面覆盖物及其生产方法
US20190024385A1 (en) * 2015-12-22 2019-01-24 Nora Systems Gmbh Self-adhesive floor covering and method for the production thereof
RU2726661C2 (ru) * 2015-12-22 2020-07-15 Нора Системз Гмбх Самоклеящееся напольное покрытие и способ его изготовления
US10794066B2 (en) 2015-12-22 2020-10-06 Nora Systems Gmbh Self-adhesive floor covering and method for the production thereof
KR102257975B1 (ko) * 2015-12-22 2021-05-27 노라 시스템즈 게엠베하 접착제 구비형 바닥 피복재 및 그 제조 방법
US11203677B2 (en) 2017-11-03 2021-12-21 American Biltrite (Canada) Ltd. Resilient surface coverings and methods of making and using thereof
EP3597706A1 (fr) * 2018-07-16 2020-01-22 Flooring Technologies Ltd. Composition de revêtement et de scellement des bords des panneaux fibreux
WO2020016176A1 (fr) 2018-07-16 2020-01-23 Flooring Technologies Ltd. Composition pour recouvrir et imperméabiliser des bords de panneaux de fibres de bois
RU2781067C2 (ru) * 2018-07-16 2022-10-05 Флуринг Текнолоджис Лтд. Композиция для покрытия и герметизации краев древесно-волокнистых плит

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