GB1566792A - Creation of Inventions and Patents with Artificial Intelligence

GB1566792A – Coating composition comprising n-vinyl-2-pyrrolidone and an oligomer
– Google Patents

GB1566792A – Coating composition comprising n-vinyl-2-pyrrolidone and an oligomer
– Google Patents
Coating composition comprising n-vinyl-2-pyrrolidone and an oligomer

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Publication number
GB1566792A

GB1566792A
GB9613/78A
GB961378A
GB1566792A
GB 1566792 A
GB1566792 A
GB 1566792A
GB 9613/78 A
GB9613/78 A
GB 9613/78A
GB 961378 A
GB961378 A
GB 961378A
GB 1566792 A
GB1566792 A
GB 1566792A
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United Kingdom
Prior art keywords
coating composition
weight
composition according
amount
present
Prior art date
1977-03-14
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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GB9613/78A
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GAF Corp

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GAF Corp
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1977-03-14
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1978-03-10
Publication date
1980-05-08

1978-03-10
Application filed by GAF Corp
filed
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GAF Corp

1980-05-08
Publication of GB1566792A
publication
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patent/GB1566792A/en

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Classifications

C—CHEMISTRY; METALLURGY

C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR

C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR

C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 – C09D183/16

C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 – C09D187/00

C—CHEMISTRY; METALLURGY

C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON

C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers

C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates

C08F299/06—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from 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

C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen

C08G18/40—High-molecular-weight compounds

C08G18/48—Polyethers

C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group

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

C08G18/671—Unsaturated compounds having only one group containing active hydrogen

C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen

C—CHEMISTRY; METALLURGY

C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR

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

C09D139/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member

C09D139/06—Homopolymers or copolymers of N-vinyl-pyrrolidones

C—CHEMISTRY; METALLURGY

C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR

Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC

Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

Y10S525/00—Synthetic resins or natural rubbers — part of the class 520 series

Y10S525/92—Polyurethane having terminal ethylenic unsaturation

Description

PATENT SPECIFICATION ( 11) 1 566 792
Q ( 21) Application No 9613/78 ( 22) Filed 10 March 1978 l ( 31) Convention Application No 777031 ( 19) ( 32) Filed 14 March 1977 in ( 33) United States of America (US) ( 44) Complete Specification published 8 May 1980 ( 51) INT CL 3 C 08 F 220/02 (C 08 F 220/02 220/18 220/20 220/36 226/10) S ( 52) Index at acceptance C 3 P DI ( 54) COATING COMPOSITION COMPRISING N-VINYL-2PYRROLIDONE AND AN OLIGOMER ( 71) We, GAF CORPORATION, a corporation organized and existing under the laws of the State of Delaware, United States of America, having its main office at West 51st Street, New York, New York 10020, United States of America, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed to be particularly described in and 5 by the following statement:-
Coating compositions which are curable under the influence of radiation in general and ultra-violet light in particular as well as electron beam curing are well known.
Representative examples of prior coating compositions include those disclosed in U S.
Patents 3,782,961; 3,829,531; 3,850,770; 3,874,906; 3,864,133; 3,891,523; 3,895,171; 10 3,899,611; 3,907,574; 3,912,516; 3,932,356 and 3,989,609 Unfortunately, these coating compositions suffer from a number of disadvantages Many of these coating compsitions have insufficient flexibility that causes them to crack when applied to flexible substrates such as those of leather or a polyvinyl plastisol Other compositions do not adhere sufficiently to the substrate with the undesirable result that they become 15 dislodged and peel Still other coating compositions require the use of solvents that must be evaporated during the curing process The evaporation of such solvents consumes energy and creates atmospheric pollution problems Still other compositions produce coatings that have insufficient scratch-resistance, stainresistance, abrasionresistance, and/or solvent-resistance 20 According to the present invention a coating composition is provided comprising:
A An oligomer of Formula I:
R’ O O O O’ R 1 I 11 II II I III (CI:=C GO-RXCNH-R 3 NG-,&-( CH 2 CH 2 CH CHO O)H__-Ra NHCX_-R 2 OCC=CH 2 (I) wherein R’ is hydrogen or methyl; R 2 is lower alkylene of up to 6 carbon atoms; Rs is aliphatic or cycloaliphatic; X is -0 or -NH-; N is an integer from 2 to 25 inclusive; B N-vinyl-2-pyrrolidone; C An ester of an ap-unsaturated carboxylic acid, which ester has a boiling point of at least 200 C at 760 mm Hg.
The oligomers employed in the present invention can be produced by reacting 30 polytetrahydrofuran with a diisocyanate to produce an isocyanate terminated prepolymer The isocyanate terminated prepolymer is then capped with a capping agent to produce the oligomer of Formula I The preferred oligomers of Formula I are those of Formula II:
C Hr CH-CO-CH 2 CH 2 OCNH NHC 4 CH 2 CH 2 CH 2 CH 20 Xn (ii) y,2 c,-tco-c Hc H,2 Hoc -CNH NHCOCH 2 CH,-OC-CH=CH 2 CH 3 CH 3 (the letter S in the rings denoting that they are saturated, i e cyclohexane, rings) wherein N is an integer from 5 to 20 inclusive, and on each cyclohexane ring, independently of others, one of R 4 and R 5 is methyl and the other of them is hydrogen.
The polytetrahydrofuran is commercially available from the Du Pont Company 5 under the tradenames “Terrecol-650 “, “Terrecol-1000 “, and “Terrecol2000 “‘, and from the Quaker Oats Company under the tradenames “Polymeg-650 ” “Polymeg1000 ” and “Polymeg-2000 “)) In the above tradenames the number indicates the approximate molecular weight of the polytetrahydrofuran The most preferred polytetrahydrofuran is that having a molecular weight of 650 which is consistent with the definition of “n” 10 in Formulas I and II herein At higher molecular weights wherein “n” exceeds about the resultant oligomer has too high a viscosity.
The capping agents useful in the present invention are those that will react with the isocyanate terminated prepolymer to produce the oligomers of Formula I In general, any capping agent having a terminal amine or hydroxyl group and also having 15 an acrylic acid or methacrylic acid moiety is suitable Examples of suitable capping agents include among others hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate, hydroxybutyl acrylate, hydroxybutyl methacrylate, hydroxypentyl acrylate, hydroxypentyl methacrylate, hydroxyhexyl acrylate, hydroxyhexyl methacrylate, aminoethyl acrylate, and aminoethyl methacrylate 20 The diisocyanates useful to produce oligomers of Formula I are aliphatic and cycloaliphatic diisocyanates that will react with terminal hydroxyl groups present on the polytetrahydrofuran Of course, aromatic diusocyanates undergo the same reaction but do not yield a product as satisfactory as that obtained by the use of aliphatic diisocyanates Examples of suitable diisocyanates include among others, isophorone 25 diisocyanate, 4,4 ‘-dicyclohexylmethane-diisocyanate available commercially from the Du Pont Company under the trade name “Hylene W”, (“Hylene” is a Registered Trade Mark) and trimethyl-hexamethylene-diisocyanate, 1,6-hexamethylene diisocyanate, 2,4,4-trimethyl, 1,6-hexylene diisocyanate, octadecylene diisocyanate and 1,4-cyclohexylene diisocyanate The preferred diisocyanates are isophorone diisocyanate ( 3-iso 30 cyanato 3,5,5-trimethyl cyclohexyl isocyanate) and 4,4 ‘dicyclohexylmethane-diisocyanate.
The N-vinyl-2-pyrrolidone is a necessary ingredient of the coating composition of the present invention The weight ratio of oligomer to N-vinyl-2pyrrolidone can vary widely as long as the properties of the resultant cured coating composition are 35 not adversely affected, however, they are generally present in a weight ratio of 1: 9 to 9:1 and preferably 1: 3 to 3: 1 At higher ratios, e g, those rich in oligomer, the uncured coating composition tends to have too high a viscosity This high viscosity makes it difficult to apply the uncured coating composition to the substrate At lower ratios the resultant cured coating composition tends to be too hard and inflexible 40 The coating compositions of the present invention must also contain an ester of an a,,6-unsaturated carboxylic acid, this ester having a boiling point of at least C at 760 mm Hg Esters of lower boiling points tend to vaporize during 1,566,792 curing Such vaporization causes undesirable changes in the coating composition.
Furthermore, vaporized esters tend to polymerize on the curing source, e g, ultraviolet lamps or electron beam window employed in curing This polymerization reduces the output of the source This vaporization also causes undesirable atmospheric pollution The esters useful in the present invention include, among others, monoesters, 5 diesters and higher esters of both acrylic acid and methacrylic acid Examples of suitable acrylic and methacrylic acid esters include, among others, 1,4butanedioldiacrylate, 1,6-hexanedioldiacrylate, neopentylglycoldiacrylate, pentaerythritoltetramethacrylate, trimethylolpropane-triacrylate, ethylhexyl-acrylate, ethylhexylmethacrylate, ) pentylacrylate, hexyl-acrylate and cyclohexyl-methacrylate 1,4butanedioldiacrylate 10 and 1,6-hexanedioldiacrylate are the preferred acrylic acid esters.
The ester can be present in the coating composition in widely varying amounts but is generally present in a weight ratio of 1:9 to 9:1 and preferably 1:3 to 3:1 compared to the oligomer of Formula I.
If the curing is done with ultra-violet light a photo-initiator is used Suitable 15 photo-initiators include vicinal ketone compounds or vicinal hydroxy ketones such as diacetyl, benzil, 2,3-pentanedione, 2,3-octanedione, 1-phenyl-1,2butanedione, 2,2dimethyl-4-phenyl-3,4-butanedione, phenylglyoxal, diphenyl-triketone; aromatic diketones, such as anthraquinone; acyloins, such as benzoin and pivaloin; acryloin D ethers, such as benzoin-methyl-ether, benzoin-ethyl-ether, benzoinbutyl-ether, benzoin 20 isobutyl-ether, benzoin-phenyl-ether; alpha-hydrocarbon substituted aromatic acyloins, including alpha-methyl-methyl-benzoin, alpha-alkyl-benzoin, as in U S Patent Number 2,722,512, and phenylbenzoin, diaryl ketones, such as benzophenone and dinaphthyl ketone; and organic disulfides, such as diphenyldisulfide The photoinitiator can also include a synergistic agent, such as a tertiary amine, to enhance the conversion of 25 photo-absorbed energy to polymerization initiating free radicals Diethoxyacetophenone available from Union Carbide Corporation, dimethoxyphenylacetophenone such as Irgacure 651 available from Ciba-Geigy or a benzoin ether such as Vicure 10 available from Stauffer Chemical Co are preferred The photo-initiator is present in the 0 coating composition in an amount sufficient to initiate the desired polymerization 30 under the influence of the amount of actinic light energy absorbed The coating composition generally contains from 0 01 to 5 weight percent of photoinitiator based on the weight of the coating composition.
The coating composition can also contain an addition polymerization inhibitor i 5 to prevent undesirable autopolym erization of the coating composition in storage prior 35 to use Examples of suitable addition polymerization inhibitors include, among others di( 1,4-secbutyl amino) benzene available from the Du Pont Company under the trade name “Anti-Oxidant 22 ” and phenothiazine available from Tefenco Chemical Co The addition polymerization inhibitor is present in an amount sufficient to prevent autopolymerization and is generally present in an amount from 0 01 to 2 % based on 40 the weight of the coating composition.
The coating composition can also contain a surfactant The preferred surfactants are silicone surfactants such as that available from the Dow Comrning Corporation under the trade name “DC-193 ” The surfactant is present in an amount necessary to reduce the surface tension of the coating composition and reduce its viscosity to the 45 desired level The surfactant generally comprises from 0 1 to 5 weight percent based on the weight of the coating composition.
The coating compositions of the present invention can also contain other conventional additives, such as flow control and leveling agents, organic and inorganic dyestuffs and pigments, fillers, plasticizers, lubricants, and reinforcing agents, such as 50 alumina, silica, clay, talc, powdered glass, carbon black and fiberglass.
The coating compositions of the present invention can be cured by applying them as a film 0 5 mil thick on the substrate Curing is preferably done under an inert atmosphere of nitrogen The coating composition may be applied as a thin film in any conventional manner such as by spraying, brushing, dipping, roll coating and the like 55 Conventionally, the film on the substrate is positioned to travel on a conveyor and pass under a source of a free radical generator, such as radiation The coated side of the substrate is exposed to the radiation for a time sufficient to effect polymerization and convert the film into an adherent, tough, flexible coating.
As used herein the term radiation refers to any radiation source which will produce 60 free radicals and induce addition polymerization of vinyl bonds The actinic radiation is suitably in the wave length of 2000-7500 A, preferably 2000 to 4000 A A class of actinic light useful herein is ultra-violet light and other forms of actinic radiation are from the sun, artificial sources such as Type RS sunlamps, carbon arc 1,566,792 lamps, Xenon arc lamps, mercury vapor lamps, tungsten halide lamps, lasers, fluorescent lamps with ultra-violet light emitting phosphors.
The preferred electron beam system contains a wide curtain of electrons directly from a linear cathode A curtain of electrons from the gun’s cathode, accelerated to a high velocity by a 200 KV potential, emerges from the chamber through a foil window into the coated substrates (Electroncurtain TI, by Energy Sciences, Inc).
The invention is further illustrated by the following examples in which all parts and percentages are by weight unless otherwise indicated.
The following abbreviations are used in the following examples and tables:
THF Polytetrahydrofuran 1 ( NP N-vinyl-2-pyrrolidone B,DDA 1,4-butanedioldiacrylate IPDI Isoporone diisocyanate TMDI Trimethyl hexamethylene diisocyanate Hylene W 4,4 ‘-dicyclohexylmethane diisocyanate 1 i’ HEA Hydroxyethyl acrylate HEMA Hydroxyethyl methacrylate (“Hylene” is a Registered Trade Mark).
EXAMPLE 1
This example is illustrative of forming the inventive coating composition The 2 following quantities of the following items were combined as indicated below:
Quantity Item Name (gins) (mols) A THF 356 0 55 2 B NP 173 3 1 55 C B,DDA 121 7 0 53 D IPDI 267 1 34 E HEA 139 1 2 The following procedure was used: The reaction was carried out under dry air Items B, C and D are added to a reactor equipped with a mechanical stirrer, a 3 ( reflux condenser and two separatory funnels Phenothiazine ( 60 ppm) is added.
This mixture is agitated vigorously at a temperature of 45 C At this point, 2 4 ml of 10 weight percent solution of catalyst of dibutyl tin dilaurate in ethylhexyl acrylate is injected The temperature is raised to 50 _+ 2 C and A is added dropwise from a separatory funnel This addition takes approximately 40 minutes Another 1 6 ml of 3 ‘ the catalyst is then injected and the temperature is raised to 56 + 2 C, where it is kept for 2 hours The temperature of the reaction mixture is lowered to 50 + 2 C and Item E is added dropwise from the other funnel The addition takes about 45 minutes to complete The temperature is raised to 56 + 2 C where it is kept for 3 hrs At the end of the reaction DC-193, silicone oil ( 1 % on the product weight) is mixed in 40 The product is stored in an amber glass bottle at the ambient temperature For electron beam curing, the product is ready for use For ultra-violet light curing, a photoinitiator is added and mixed well before use.
EXAMPLES 2-4
These examples are illustrative of forming the inventive coating compositions 45 The table shows the amounts of ingredients combined in the examples The procedure of Example 1 was followed substituting the specified amounts of ingredients as shown in the table The amounts of ingredients in Example 1 are also shown in the table for convenience.
1,566,792 TABLE nample 1 2 3 4 Parts Mols Parts Mols Parts Mols Parts Mols 1 HF 356 0 55 356 0 55 356 0 55 356 O 55 NP 173 3 1 55 186 3 1 67 190 3 1 7 172 1 1 54 BI)DA 121 7 0 53 128 6 0 56 131 6 0 57 119 5 0 52 Diisocyanate 267 1 34 315 1 18 315 1 18 253 1 44 (IPDI) (Hylene W) (Hylene W) (TMDI) Capping Agent 139 1 2 139 1 2 156 1 2 139 1 2 (HEA) (HEA) (HEMA) (HEA) (“Hylene” is a Registered Trade Mark) EXAMPLE 5
This example illustrates the synthesis of a coating composition of the present invention employing two acrylic acid esters.
The procedures of Example 1 is repeated employing the same times, conditions 15 and ingredients except that one-half the quantity of mols of the B,DDA is replaced with ethylhexylacrylate with similar results.
EXAMPLE 6
To the composition of Example 4 is added 2 % of a benzoin ether (Vicure 10 available from Stauffer Chemical) and 1-mil thick film is applied on a vinyl sheet 20 The coated vinyl sheet is cured by passing through a PPG QC Lab UV oven conmtaining two 200 w/in UV lamps at a speed of 100 ft/min No solvent was left after the cure The coating is dry, flexible, scratch-resistant, stain-resistant, abrasionresistant and solvent-resistant.
The product has been shown to give coatings with good hand on fabrics The 25 elongation of the cured film is of the order of 20-50 % with a tensile strength of about 3500 psi These materials have good adhesion to vinyl, urethane and polycarbonate substrates as well as to natural fibers.

Claims (11)

WHAT WE CLAIM IS:-

1 A coating composition comprising: 30 A An oligomer of Formula I:
R’ O O O O O OR 1 I 11 II Il l Clt=C C CNH-RNHCX-(C 2 CH 2 CHCH-)-CN-R 3-NHCXR 2 OCC=CH, (I) wherein RI is hydrogen or methyl; R 2 is lower alkylene of up to 6 carbon atoms; 35 R 3 is aliphatic or cycloaliphatic; X is -O or -NH-; n is an integer from 2 to 50 inclusive; B N-vinyl-2-pyrrolidone; C An ester of an aft-unsaturated carboxylic acid, which ester has a boiling 40 point of at least 200 C at 760 mm Hg.

2 Coating composition according to Claim 1 further comprising an addition polymerization inhibitor present in an amount sufficient to avoid the auto-polymerization of the composition during storage.

3 Coating composition according to either of Claims 1 or 2 wherein the addi 45 tion polymerization inhibitor is present in an amount from 0 01 to 2 weight percent based upon the weight of the composition.

4 The coating composition according to any of Claims 1-3 wherein a surfactant is present in an amount from 0 1 to

5 weight percent based upon the weight of the composition 50 Coating composition according to Claim 4 wherein the surfactant is a silicone surfactant.

6 Coating composition according to any of Claims 1-5 which also contains 1,566,792 a photo-initiator present in an amount sufficient to initiate the desired polymerization under the influence of the amount of actinic light energy absorbed.

7 Coating composition according to Claim 6 wherein the photo-initiator is present in an amount from 0 01 to 5 weight percent based upon the weight of the composition 5

8 Coating composition according to any of Claims 1-7 wherein the weight ratio A: B is from 1: 9 to 9: 1.

9 Coating composition according to any of Claims 1-8 wherein the weight ratio A:Cis from 1:9 to 9:1.

10 A coating composition according to Claim 1 which is photopolymerizable 10 in the presence of ultra-violet light to produce an adherent coating that is flexible, scratch-resistant, stain-resistant, abrasion-resistant, and solventresistant, said coating composition consisting essentially of:
A An oligomer of Formula II:
o o R Rs o 0 OR (I) C Hr CHúCO-CH 2 CH 2 OCNH CCHCHCHCH O -CO-CH 2 CHC-EC 2 CH 2 C 2 CH 20 CH 3 CH 3 15 -CNH O CNIH NHCOCH 2 C Hf OC-CHICH 2 CH 3 CH 3 (the letter S in the rings denoting that they are saturated, Le, cyclohexane, rings) wherein “n” is 5 to 20, and on each cyclohexane ring, independently of others, one of R’ and R 5 is methyl and the other of them is hydrogen.
B N-vinyl-2-pyrrolidone; C 1,4-butanedioldiacrylate; 20 D A photo-initiator present in an amount from 0 01 to 5 weight percent based on the weight of the composition; E An addition polymerization inhibitor present in an amount from O 01 to 2 weight percent based on the weight of the composition; F A silicone surfactant present in an amount from O 1 to 5 percent based on 25 the weight of the composition; wherein the ratio A: B is from 1:3 to 3:1, and wherein the ratio A: C is from 1: 3 to 3: 1.

11 A coating composition substantially as herein described with reference to any one of the Examples.
MEWBURN ELLIS & CO.
Chartered Patent Agents European Patent Attorneys 70-72 Chancery Lane, London WC 2 A l AD.
Printed for Her Majesty’s Stationery Office by the Courier Press Leamington Spa 1980 Published by The Patent Office 25 Southampton Buildings, London, WC 2 A l AY, from which copies may be obtained.
1,566,792

GB9613/78A
1977-03-14
1978-03-10
Coating composition comprising n-vinyl-2-pyrrolidone and an oligomer

Expired

GB1566792A
(en)

Applications Claiming Priority (1)

Application Number
Priority Date
Filing Date
Title

US05/777,031

US4129709A
(en)

1977-03-14
1977-03-14
Coating composition comprising N-vinyl-2-pyrrolidone and an oligomer

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Publication Date

GB1566792A
true

GB1566792A
(en)

1980-05-08

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Priority Date
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GB9613/78A
Expired

GB1566792A
(en)

1977-03-14
1978-03-10
Coating composition comprising n-vinyl-2-pyrrolidone and an oligomer

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US4129709A
(en)

JP
(1)

JPS53112933A
(en)

CA
(1)

CA1117242A
(en)

DE
(1)

DE2810047C2
(en)

FR
(1)

FR2384008A1
(en)

GB
(1)

GB1566792A
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NL7802745A
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1984-07-10
1986-02-26
Yokohama Rubber Co Ltd
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US4128536A
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1978-12-05
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US4129667A
(en)

1977-12-29
1978-12-12
Gaf Corporation
Radiation curable coating composition comprising an acryl urethane oligomer and an ultra-violet absorber

US4133723A
(en)

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1979-01-09
Lord Corporation
Actinic radiation-curable formulations from the reaction product of organic isocyanate, poly(alkylene oxide) polyol and an unsaturated addition-polymerizable monomeric compound having a single isocyanate-reactive hydrogen group

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US4263366A
(en)

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1981-04-21
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Radiation curable coating composition comprising an oligomer and a copolymerizable ultra-violet absorber

CA1179094A
(en)

1979-08-30
1984-12-04
Bruce A. Gruber
Radiation curable coating composition comprising an oligomer and a copolymerizable ultra-violet absorber

US4260703A
(en)

1979-10-26
1981-04-07
Union Carbide Corporation
Novel urethane-acrylate and radiation curable compositions

US4624994A
(en)

1980-07-18
1986-11-25
Desoto, Inc.
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(en)

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1986-10-01
Anic Spa

POLYCARBONATE BASED COMPOSITION HAVING IMPROVED PROPERTIES AND METHOD FOR ITS OBTAINING

NL8005674A
(en)

1980-10-15
1982-05-03
Philips Nv

OPTICALLY READABLE INFORMATION DISC.

AT369757B
(en)

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1983-01-25
Inna Alexeevna Pronina

MIXTURE FOR RADIATION CHEMICAL OR PHOTOCHEMICAL HARDENING OF PAINTINGS, ADHESIVES, COMPOUND AND SEALANTS

EP0115160A3
(en)

1983-01-03
1984-08-22
Mobil Oil Corporation
Abrasives with binder comprising adduct of polyisocyanate and polyalkoxyacrylate

EP0125710A3
(en)

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International Standard Electric Corporation
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1985-08-29
W.R. Grace & Co.
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1984-06-11
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Urethane-modified acrylate composition

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POLYMER NETWORK, METHOD FOR THE PREPARATION THEREOF, THE USE THEREOF FOR CLADING AND / OR IMPREGNATING OR FOR MANUFACTURING EYE LENSES, AND FORMED PROPERTIES, WHOLLY OR FROM AN EXISTINGLY PROVEN POLISH.

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1990-12-27
Dai Nippon Insatsu Kabushiki Kaisha
Soft coated film

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1991-09-12
Rheydt Kabelwerk Ag
UV-cured resin mixts. for coating optical fibres – contain acrylic] oligomers, acrylate] monomers, initiator, dye, water-repellent components, lubricants, stabilisers, coupling agents, etc.

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1994-05-20
1995-10-31
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reactive polyurethane elastomer

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Assignee
Title

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(en)

1966-07-11
1969-02-04
Wyandotte Chemicals Corp
Tetrahydrofuran-ethylene oxide polyether urethane-urea polymers

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1973-01-08
1974-08-13
Rohm & Haas
Additive for impact modified thermoplastics

1977

1977-03-14
US
US05/777,031
patent/US4129709A/en
not_active
Expired – Lifetime

1978

1978-01-18
CA
CA000295200A
patent/CA1117242A/en
not_active
Expired

1978-02-27
FR
FR7805575A
patent/FR2384008A1/en
active
Granted

1978-03-08
DE
DE2810047A
patent/DE2810047C2/en
not_active
Expired

1978-03-10
GB
GB9613/78A
patent/GB1566792A/en
not_active
Expired

1978-03-13
JP
JP2781278A
patent/JPS53112933A/en
active
Granted

1978-03-14
NL
NL7802745A
patent/NL7802745A/en
not_active
Application Discontinuation

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Assignee
Title

GB2163443A
(en)

1984-07-10
1986-02-26
Yokohama Rubber Co Ltd
Photocurable resin composition

GB2195643A
(en)

1986-07-21
1988-04-13
Yokohama Rubber Co Ltd
Uv curable urethane acrylate composition

GB2195643B
(en)

1986-07-21
1990-08-15
Yokohama Rubber Co Ltd
Uv-curable resin compositions

Also Published As

Publication number
Publication date

JPS53112933A
(en)

1978-10-02

US4129709A
(en)

1978-12-12

NL7802745A
(en)

1978-09-18

FR2384008A1
(en)

1978-10-13

CA1117242A
(en)

1982-01-26

DE2810047C2
(en)

1986-10-02

DE2810047A1
(en)

1978-09-28

FR2384008B1
(en)

1983-07-29

JPS6154062B2
(en)

1986-11-20

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