GB2065143A - Vinyl Chloride Polyme-Curable Liquid Polymer Compositions - Google Patents
Vinyl Chloride Polyme-Curable Liquid Polymer Compositions Download PDFInfo
- Publication number
- GB2065143A GB2065143A GB8037063A GB8037063A GB2065143A GB 2065143 A GB2065143 A GB 2065143A GB 8037063 A GB8037063 A GB 8037063A GB 8037063 A GB8037063 A GB 8037063A GB 2065143 A GB2065143 A GB 2065143A
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- GB
- United Kingdom
- Prior art keywords
- composition
- polymer
- composition according
- vinyl chloride
- polymeric material
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- 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.)
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/69—Polymers of conjugated dienes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L19/00—Compositions of rubbers not provided for in groups C08L7/00 - C08L17/00
- C08L19/006—Rubber characterised by functional groups, e.g. telechelic diene polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of 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 halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of 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 halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/04—Compositions of 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 halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
- C08L27/06—Homopolymers or copolymers of vinyl chloride
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
- C08L9/02—Copolymers with acrylonitrile
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J127/00—Adhesives 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 halogen; Adhesives based on derivatives of such polymers
- C09J127/02—Adhesives 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 halogen; Adhesives based on derivatives of such polymers not modified by chemical after-treatment
- C09J127/04—Adhesives 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 halogen; Adhesives based on derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
- C09J127/06—Homopolymers or copolymers of vinyl chloride
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
Abstract
Compositions for coatings and adhesives comprise a) a plasticised vinyl chloride polymer and b) a liquid polymeric material which is compatible with polymer a), is substantially chemically inert towards polymer a), and which can solidify by curing substantially independently of polymer a). The compositions are spreadable at ambient temperature, do not involve conventional solvents and pass through a finite intermediate stage at which they are tacky and have cohesive strength.
Description
SPECIFICATION
Polymer Compositions
This invention relates to novel polymer compositions and to the use of these compositions for coating and bonding purposes.
Many coating and adhesive compositions are currently solvent-based and consequently at some stage during the coating or bonding process the solvent must be removed. Unfortunately readily available solvents which are otherwise suitable for this purpose are often hazardous from the point of view of toxicity and/or flammability. In attempts to overcome this problem, coating and adhesive compositions have been proposed based upon a liquid ingredient which can be applied to a substrate and then solidified, for example by cross-linking or polymerisation. Whilst this type of composition does have the advantage of avoiding the use of a conventional solvent it is often formulated to solidify very quickly in use in order to minimise assembly time and therefore has the disadvantage of only a transient intermediate stage at which the composition is tacky.
The present invention is intended to remedy these drawbacks by providing polymer compositions which are novel in themselves and useful as coating and adhesive compositions spreadable at ambient temperature (e.g. 200C). When used as coating or adhesive compositions, the novel compositions render the use of conventional solvents unnecessary and have the added advantage of passing through a finite intermediate stage at which they are tacky, i.e. have "grab", and have cohesive strength. It is even possible to formulate compositions within the scope of the present invention which have an extended tacky stage e.g. of several weeks or more.A tacky, cohesively strong, stage of practical duration is very desirable when bonding a variety of substrates e.g. rubber, wood, leather etc., because it allows positioning and if necessary, repositioning before the adhesive composition completely solidifies.
According to one aspect of the present invention, there is provided a fluid composition which comprises a) a plasticised vinyl chloride polymer and b) a liquid polymeric material which is compatible with polymer a), is substantially inert towards polymer a), and which can solidify by curing substantially independently of polymer a).
According to a further aspect of the present invention there is provided a method of coating a substrate by applying the fluid composition of the preceding paragraph to the substrate and causing or allowing the fluid composition to solidify.
According to yet another aspect of the present invention there is provided a method of making a composite by (i) applying to a substrate a fluid composition which comprises a) a plasticised vinyl chloride polymer and b) a liquid polymeric material which is compatible with polymer a), is substantially chemically inert towards polymer a) and which can solidify by curing substantially independently of polymer a), (ii) allowing the composition to attain a coherent, tacky state, (iii) contacting a second substrate with the composition and (iv) solidifying the composition to bond the assembly.
The polymeric materials are intimately mixed and can solidify by curing or gelling substantially independently of each other. Thus one of the polymeric materials is solidified within the other liquid polymeric material resulting in a tacky, coherent, thickened composition (first stage cure) and the final solid state is achieved by curing the other polymeric material (second stage cure). Preferably the amount of each solidifiable polymeric material is at least 5, more preferably from 10 to 80, and more usually 20 to 50 parts by weight per 100 parts of the two polymeric materials. Solidification of one or both polymeric materials may occur spontaneously or may be caused by, or accelerated by, a change in conditions e.g. by the application of heat, moisture and/or radiation.Solidification is usually by curing or gelling and does not rely upon evaporation to any substantial extent. "Curing" is a common term in the art used to describe a process whereby a material is changed so as to be substantially insoluble.
The resulting cured material may be either thermoset or thermoplastic. The term "curing" includes "cross-linking" whereby a material undergoes a chemical change which is usually either irreversible or reversible with difficulty, and at least one of the polymeric materials is curable. An example of a curable polymeric material is a liquid butadiene/acrylonitrile copolymer e.g. as available in the Hycar range from Goodrich Chemicals. An example of a gellable polymeric material is a dispersion of poly(vinyl chloride) in a plastisol which when heated passes from a liquid, raw condition to a solid gel. If desired these gels may be cured.
Examples of suitable combinations of polymeric materials include a liquid butadiene/acrylonitrile copolymer (tipped or untipped) such as those available under the trade name HYCAR from Goodrich with a vinyl chloride polymer dispersed in a plasticiser, e.g. dialphanyl phthalate (an ester based upon
C, to C9 alcohols). A possible further combination would be a -curable acrylic oligomer or an acrylic/olefin oligomer with a vinyl chloride polymer. The vinyl chloride polymer may be a homocopolymer or a copolymer of vinyl chloride with up to 20% by weight of vinyl acetate. When a tipped liquid butadiene/acrylonitrile copolymer is used, examples of tipping groups include carboxyl amine, vinyl, hydroxyl, mercapto and bromine. Preferably at least one of the polymeric materials will be elastomeric when solidified.
"Oligomers' are discussed by A. A. Berlin in "Polymer Science: USSR", Vol 20 20 page 541 onwards. (Published by Pergamon Press Limited 1979) and are characterised as follows: Examination
of the variation of the partial values of a number of physiochemical parameters, symbolised as sX, with
change in the number of units in a chain molecule, n, reveals three clearly defined main regions:
1) where dWdn)=const, 2) (d 0/dn)=const and
3) (d b/dn)=O The first region consists of low molecular substances, i.e. homologues containing in the region of 2 to 3
units, where the size of the molecule has not reached that of the statistical segment and the molecular
chain is not flexible.The second region consists of oligomers ' compounds with degrees of
polymerisation of n=2 to 100 i.e. substances whose molecules can include a few statistical segments
and are characterised by partial values of parameters that are not averaged with respect to chain
length. The third region contains high polymers i.e. compounds of n=103 to 104 and a multiplicity of
statistically averaged conformational transitions.
The polymer composition usually includes at least one ingredient which will react with the liquid
butadiene/acrylonitrile copolymer material e.g. an epoxy resin based on a diphenol such as 2,2-di(4
hydroxy-phenyl) propane, and/cr an organic isocyanate such as liquid M.D.I. (4,4-diphenyl methane
diisocyanate). Such an ingredient acts as a cross-linking agent for the liqud copolymer material and
may be temporarily chemically "blocked" so that it will not become active until it becomes unstable by
the action of e.g. air, moisture, UV radiation etc. Alternatively, or in addition, at least one of the
polymeric materials may be chemically "blocked" so that its chemical activity is retarded until
activated.
Other additives which can be included in the polymer composition may be selected from a
tackifier, an anti-oxidant or other type of stabiliser, a reinforcing filler (e.g. carbon black), silane-treated
silica, a metal carbonate or silicate, glass or textile fibres), a non-reinforcing filling (e.g. talc or titanium
oxide), and a colourant (e.g. a metal oxide, a metal sulphide or an organic pigment).
If desired a polymer composition according to the present invention may be applied to a surface
(e.g. a release paper), allowed to or caused to thicken to a tacky state and then removed from the
surface to be completely solidified at a later stage. In this way a "portable" adhesive can be made.
Examples of substrates which may be coated or bonded according to the present invention
include those of elastomers, plastics, wood, leather, paper, textiles or metals. The method of bonding
can be used to bond (i) portions of a substrate to each other, (ii) substrates of different compositions or
(iii) substrates of the same composition.
The invention is illustrated in the following Examples in which all parts are by weight:
Example I
A pvc piastisol was prepared from 100 parts of a poly(vinyl chloride) powder of mean particle size about 2 microns available as Breon P 130/1 from BP Chemicals Limited, 60 parts of dialphanyl phthalate and 2 parts of lead carbonate.
7.5 g of a glycidyl ether-type epoxy resin available as Epikote 815 from Shell were added to 1.875 g of 2,2-di-(4-hydroxy-phenyl) propane available as Bisphenol A from BDH Chemicals and the mixture was heated and stirred until the epoxy resin had dissolved. 100 g of the pvc plastisol were added to this solution and stirred. To the mixture were added 12.5 g of an unreactive viscous liquid butadiene/acrylonitrile copolymer available as Hycar 1312 from B.F. Goodrich and 28.1 g of an aminotipped difunctional liquid butadiene/acrylonitrile copolymer available as Hycar ATBN from B.F. Goodrich (viscosity=approximately 1000 poise at 250C.).
The resulting mixture was stirred well by hand and a portion of it was spread carefully on to a polyethylene sheet to a thickness of about 2 mm to avoid trapping air. The coated sheet was left horizontally overnight at room temperature after which time the coating had gelled to a tacky coherent mass. After a further 24 hours the coating was still very tacky and easily removable from the polyethylene. After removal from the polyethylene the tacky mass was cured flat in the air oven for 20 minutes at 1 58cm. The cured sheet was tough, flexible and slightly rubbery.
A further portion of the mixture was spread with a spatula as a thin, uniform coating onto the buffed surface of a cured Neoprene-coated fabric of the type often used for tank-lining. The coated fabric was left overnight in a horizontal position, cut into two and then the two halves pressed lightly together by means of a hand roller. After 2 days the laminate was placed in an eiectric hand press at 1 600C. and maintained at a pressure of about 20 MN/m2 for 5 minutes. The press was opened whilst still hot and the laminate removed. The laminate was very well bonded.
The latter test was repeated by substituting a cured nitrile rubber-coated fabric for the neoprenecoated fabric and the resulting laminate was also well bonded.
Example II
100 g of the pvc platisol described in Example I were mixed at room temperature with 60 g of a liquid difunctional hydroxy-tipped butadiene/acrylonitrile copolymer available as Poly BD CN-15 from
Arco (viscosity-500 poise at 250C), 12.5 g of Hycar 1312 and 12.5 g of an impure liquid form of 4,4diphenyl methane diisocyanate available as Suprasec DND from l.C.I.
A portion of this mixture was spread onto a sheet of polyethylene as described in Example I. After being left at room temperature for 24 hours the coating had gelled to a tacky coherent sheet which was substantially free of air bubbles and removable from the polyethylene. After a further 24 hours the sheet was still tacky and was cured flat in an air oven at 1 580C for 20 minutes. A flexible non-porous rubber sheet was obtained.
A further portion of the freshly prepared mixture was coated as a thin film onto the buffer surfaces of 1 inch strips of cured Neoprene tank-lining material. Surfaces of wood and the underside of Formica were also coated. After 1 8 hours the appropriate coated faces were assembled and pressed together using a hand roller. Each assembly was moulded under low pressure (1 MN/m2) at 1 400C for 5 minutes and removed while still hot. The Neoprene laminate was tested at room temperature and found to have a peel-down strength of 1.5 kg/cm. The wood laminate was found to be also firmly bonded,
Example Ill
A pvc plastisol was prepared from 100 parts of a poiy(vinyl chloride) powder of mean particle size about 2 microns available as Breon P 130/1 from B.P.Chemicals Limited, 60 parts of dialphanyl phthalate and 2 parts of lead carbonate.
An epoxy resin was prepared by dissolving, at 800C, 80 parts of the glycidyl ether-type epoxy resin available as Epikote 815 from Shell and 20 parts of 2,2-di(4-hydroxyphenyl) propane available as
Bisphenol A from BDH Chemicals. The mixture was cooled and used to prepare the following formulations:
PartA Parts pvc plastisol 50 Epikote 815 re-reacted 40 . Dr - eac e Bisphenol A 10 Part B Parts
pvc plastisol 50
Hycar ATBN (B. F. Goodrich) 50
Parts A and B were prepared by thorough mixing and were then stored in sealed containers. Equal amounts of Parts A and B were mixed together and then spread as a 2.5 mm sheet on polythene.The sheet was left for 24 hours after which time the material was just coherent and very tacky. A tacky state with good cohesion of the film was obtained between 1-3 days after mixing; the tackiness subsided after this time. The sheet was moulded, after standing for 1 week, in a 9 inchx3 inch positive compression mould at 1 600C for 1 5 minutes under a pressure of 20 MN/m2.
The sheet of approximately 2 mm thickness was tested and the resulting strengths obtained are given below, together with comparative data obtained for the pvc plastisol alone and the epoxy resin/Hycar ATBN combination alone.
pve Epoxy/ 50/50
plastisol ATBN mix
Period of useful tack none 1 5-30 1-3 days
state shown by mix minutes
Cast sheet cured at
160 OC for 15 minutes
Tensile strength (MN/m2) 1 5 19.2 14.3 EB(%) 220 106 101
100% Modulus (MN/m2) 10.1 17.8 14.2
Tear strength 167 180 178
A further portion of the mix was spread uniformly as a thin film onto one inch strips of buffed cured Neoprene and nitrile rubber-coated fabrics of the type used for tank-linings. The strips were left for 24 hours and then two identical strips of each type were assembled and pressed together using a hand-roller. The assemblies were left for 1 week and then placed in a hand electrically-heated press at 1 400C and given 5 minutes under low pressure (about 1 MN/m2). The strips were removed while still hot and when cooled were found to have bonded well. A tear-down strength of 3 kg/cm was measured for the Neoprene sample at room temperature and a strength of 1.2 kg/cm for the nitrile material.
Claims (12)
1. A fluid composition comprises a) a plasticised vinyl chloride polymer and b) a liquid polymeric material which is compatible with polymer a), is substantially chemically inert towards polymer a), and which can solidify by curing substantially independently of polymer a).
2. A composition according to claim 1 wherein the vinyl chloride polymer is a homopolymer.
3. A composition according to claim 1 or 2 wherein the polymeric material b) is a butadiene/acrylonitrile copolymer.
4. A composition according to claim 1 or 2 wherein the polymeric material b) is either an acrylic oligomer or an acrylic/olefine oligomer.
5. A composition according to any preceding claim wherein the composition includes a crosslinking agent for the polymeric material b).
6. A composition according to claim 5 wherein the cross-linking agent is an epoxy resin.
7. A composition according to any preceding claim wherein the composition includes 2,2-di(4hydroxy-phenyl propane.
8. A composition according to claim 1 substantially as described in any one of Examples I to Ill.
9. A method of coating a substrate comprises applying to the substrate a composition according to any preceding claim and causing or allowing the fluid composition to solidify.
10. A coated substrate when made by the method according to claim 8.
11. A method of making a composite comprises (1) applying to a substrate a composition according to any one of claims 1 to 8, (ii) allowing the composition to attain a coherent, tacky state, (ii) contacting a second substrate with the composition and then (iv) solidifying the composition to bond the assembly.
12. A composite when made by the method according to claim 11.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8037063A GB2065143A (en) | 1979-12-11 | 1980-11-19 | Vinyl Chloride Polyme-Curable Liquid Polymer Compositions |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7942629 | 1979-12-11 | ||
| GB8037063A GB2065143A (en) | 1979-12-11 | 1980-11-19 | Vinyl Chloride Polyme-Curable Liquid Polymer Compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2065143A true GB2065143A (en) | 1981-06-24 |
Family
ID=26273839
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8037063A Withdrawn GB2065143A (en) | 1979-12-11 | 1980-11-19 | Vinyl Chloride Polyme-Curable Liquid Polymer Compositions |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2065143A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2120258A (en) * | 1982-05-20 | 1983-11-30 | Bestobell Ind Australia | Blends of elastomers with polyvinyl chloride |
| US4537805A (en) * | 1984-03-26 | 1985-08-27 | W. R. Grace & Co. | Reactive plastisol dispersion |
| US4623558A (en) * | 1985-05-29 | 1986-11-18 | W. R. Grace & Co. | Reactive plastisol dispersion |
| WO2011058049A1 (en) * | 2009-11-11 | 2011-05-19 | Wollsdorf Leder Schmidt & Co Ges.M.B.H. | Method for applying leather to vehicle interior parts |
-
1980
- 1980-11-19 GB GB8037063A patent/GB2065143A/en not_active Withdrawn
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2120258A (en) * | 1982-05-20 | 1983-11-30 | Bestobell Ind Australia | Blends of elastomers with polyvinyl chloride |
| US4537805A (en) * | 1984-03-26 | 1985-08-27 | W. R. Grace & Co. | Reactive plastisol dispersion |
| US4623558A (en) * | 1985-05-29 | 1986-11-18 | W. R. Grace & Co. | Reactive plastisol dispersion |
| WO2011058049A1 (en) * | 2009-11-11 | 2011-05-19 | Wollsdorf Leder Schmidt & Co Ges.M.B.H. | Method for applying leather to vehicle interior parts |
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| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |