GB2046627A - Process for the manufacture of heat resistant curable surface coating composition - Google Patents
Process for the manufacture of heat resistant curable surface coating composition Download PDFInfo
- Publication number
- GB2046627A GB2046627A GB8012903A GB8012903A GB2046627A GB 2046627 A GB2046627 A GB 2046627A GB 8012903 A GB8012903 A GB 8012903A GB 8012903 A GB8012903 A GB 8012903A GB 2046627 A GB2046627 A GB 2046627A
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- Prior art keywords
- unsaturated
- substrate
- composition
- wear layer
- polyaryloxyphosphazene
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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
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/667—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing phosphorus in the main chain
- D06M15/673—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing phosphorus in the main chain containing phosphorus and nitrogen in the main chain
-
- 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
-
- 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
- C09D185/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon; Coating compositions based on derivatives of such polymers
- C09D185/02—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon; Coating compositions based on derivatives of such polymers containing phosphorus
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Textile Engineering (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Paints Or Removers (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Laminated Bodies (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
The tensile strength and elongation of cured phosphazene wear layers are improved by heating the coating composition, for at least 5 minutes at a temperature within the range 40 DEG C to 177 DEG C before curing. The process is applicable to crosslinkable compositions based on unsaturated polyaryloxyphosphazenes or aryloxycyclotriphosphazenes.
Description
SPECIFICATION
Process for the manufacture of heat resistant curable surface coating composition ;this invention relates to wear layer coatings for surface coverings, and to a process for their man ufactu re.
U.S. Patent No. 4,145,479 describes a burn resistant wear layer composition comprising the reaction product of at least one unsaturated polyaryloxyphosphazene, at least one unsaturated aryloxycyclotriphosphazene, and a cross-linking agent. Also described is a heating process for the removal of solvent from the curable coating composition prior to curing.
The present invention is based on the observation that the properties of wear layer derived from the reaction product of at least one unsaturated aryloxycyclotriphosphazene and a cross-linking agent are improved by heat treating the wear layer composition for at least 5 minutes at a temperature within the range of from 100" to 3500F. (40"C to 177"C) before curing. If the wear layer composition comprises the reaction product of at least one unsaturated polyaryloxyphosphazene or a mixture of at least one unsaturated polyaryloxyphosphazine and at least one unsaturated aryloxycyclotriphosphazene, the heat treatment method of this invention will serve to improve the properties of the resulting wear layer coatings provided that any solvent employed to dissolve the polyaryloxyphosphazene is first removed.
The improvement in the properties of the wear layer coating is believed to be a result of an increased degree of cure, and manifests itself in higher tensile strength and ultimate elongation, compared with the products of prior art processes.
The present invention provides a process for the manufacture of a surface covering comprising a substrate having a cured wear layer, which comprises forming a curable coating composition comprising (a) at least one member selected from the group consisting of unsaturated polyaryloxyphosphazenes and unsaturated aryloxycyclotriphosphazenes, and (b) a crosslinking agent, or a reaction product of (a) and (b), and, if desired or required (c) a solvent for the polyaryloxyphosphazene, applying the coating composition to the substrate, and, after removing the solvent if present, heat treating the coating composition, either before or after its application to the substrate, for a period of at least 5 minutes at temperature within the range of 1 00 F (40"C) to 3500F (1770C), and curing the heat-treated coating composition.
According to the invention, there is more especially provided, in a process for producing a surface covering having a cured wear layer wherein a substrate is coated by passing the substrate beneath a coating means which applies a wear layer composition comprising the reaction product of a crosslinking agent and at least one phosphazene material selected from the group consisting of unsaturated polyaryloxyphoshazene; unsaturated aryloxycyclotriphosphazene and mixtures thereof to the substrate and wherein if any solvent is employed for the purpose of dissolving unsaturated polyaryloxyphosphazene, it is removed and the coated substrate is cured under free radical conditions, the improve
ment comprising heat treating the wear layer composition, either before or after coating the substrate but before curing the coated substrate, for a period of at least 5 minutes at a temperature within the range of from at least 100" two about 350"F (40 C to 177"C).
As the unsaturated polyaryloxyphosphazene, there may advantageously be used as a material having the formula [NP (oC6Hs-wRw)x(OC6Hs-wRw)y(R1)zIn wherein each R independently represents hydrogen, chlorine, bromine, fluorine, a (C1 to C,0) linear or branched alkyl radical or a (C, to C4) linear or branched alkoxy radical;R' represents: --OCsH4CH=CH2, OC6H3(R2)CH =CH2, -0C6H4-CH=CH(R2),
OC6H3(R2)CH =CH(R3),
-0C6H4-CH2CH =CH2,
-OC6H3(R2)-CH2CH =CH2,
OC6H4CH(R3)CH =CH2,
-OC6H4CH2-(R2)=CH2, -OC6H4CH2-CH=CH(R3), or -0C6H4-CH =CH-(CH2)b-CH =CH2;
R2 and R3 each independently represent a halogen or an alkenyl, alkoxy, aryloxy, alkyl, or aryl radical; w has a value of from 0 to 5; z has a value greater than 0 and advantageously less than 2 and the sum of x + y + z equals 2; n has a value of from 2 to 3100; and b has a value of from 0 to 4.
Unsaturated polyaryloxyphosphazenes suitable for use in the present invention and methods for their production are described in U.S. Patent No.
4,053,456, the disclosure of which is herein incorporated by reference.
As the unsaturated aryloxycyclotriphosphazene, there may advantageously be used a compound having the formula N3P3(OC6Hs~wRw)a(R1)6-a wherein R, R', and ware as defined above, and a has a value which is up to, but not equal to, 6, and is advantageously greater than zero.
Unsaturated aryloxycyclotriphosphazenes suitable for use and methods for their preparation are described in U.S. Patent No.4,145,479.
Whether an unsaturated polyaryloxyphosphazene or unsaturated aryloxycyclotriphosphazene is employed alone, or a mixture thereof is employed, the amounts of cross-linking agent and any additional materials employed will be based on parts per 100 parts of total phosphazene material in the wear layer compositions.
If both unsaturated polyaryloxyphosphazene and unsaturated aryloxycyclotriphosphazene materials are employed in a wear layer composition, each will advantageously be employed in an amount within the range of from about 10 to about 90 parts per 100 parts of the total phosphazene material in the wear layer composition.
As the crosslinking agent, use is advantageously made of any organic compound bearing two or more thiol groups. Examples of usablethiol crosslinking agents are described in U.S. Patent No. 3,676,311,
herein incorporated by reference.
Examples of particularly suitable crosslinking
agents are glycol dimercaptoacetate, glycol dimer
captopropionate, trimethyolethane tri(P - mercap
topropionate), trimethyolethane trithioglycolate,
trimethyolpropane tri(p - mercaptopropionate),
trimethyolpropane trithioglycolate, pentaerythritol tetra (ss - mercaptopropionate), polyethyleneglycol
di(p - mercaptopropionate) and mixtures thereof.
In one embodiment, since the unsaturated
polyaryloxyphosphazene is generally a solid, a suffi
cient amount of a solvent is employed in order to
dissolve solid unsaturated polyaryloxyphosphazene.
Examples of particularly suitable solvents are ethyl acetate, methyl acetate, butyl acetate, methyl
acrylate, ethyl acrylate, methyl ethyl ketone and mixtures thereof.
As the catalyst employed to promote the cross
linking reaction, use may be made of a variety of free
radical catalysts capable of promoting reactions
involving ethylenic double bonds. Frequently prefer
red are members of the well-known class of peroxide initiators (e.g., benzoyl peroxide and di-cumyl perox
ide), as well as electron beam radiation. Alternatively, if one desires to use ultraviolet radiation to cure the compositions of this invention, a variety of photoinitiators (e.g., benzophenone, benzoin isobutyl ether, 2 - phenyl - 2,2 - dimethoxyavetophenone) and activators (e.g., triethanolamine, methyldiethanolamine) may be
employed in the wear layer compositions, being
generally employed in art-recognized amounts.
The amount of cross-linking agent employed will normally be governed by the numberofethylenic double bonds in the total amount of phosphazene component content of the wear layer composition.
Crosslinking agent is advantageously employed such that for each ethylenic double bond of the phosphazene material there are from about 0.2 to about 1.4 thiol groups. Preferably, the double bond to thiol group ratio is 1:1.
The wear layer composition can also be formulated to include various art recognized amounts of optional ingredients typically employed in wear layer compositions such, for example, as surfactants, and heat and light stabilizers.
The wear layer composition is prepared by any suitable method, many of which are conventional,
and examples of which are described below. The composition can be applied to any surface covering,
for example, flooring sheet or tile products, being
applied using any suitable means of application
(e.g., curtain coater) such that, upon curing, the coat
ing is advantageously present on the surface cQver- ing at a coating or film thickness of from about 1 to
about 20 mils (0.025 to 0.5 mm). Preferably, the coat
ing thickness is from about 4to about 8 mils (0.1 to
0.2 mm).
The heat treatment step of this invention can be
carried out either before the coating or film forming
step or after the coating step, but the heat treatment
must be carried out after the removal of any solvent
present, and prior to curing, in order to achieve an
improvement in tensile strength of the cured pro
duct. Any suitable heat treating method many of
which are conventional, e.g., placing the coating in
an oven, may be employed.
The following examples illustrate the invention.
Examples I to Ill describe the manufacture of starting
materials used in the inventive process, while
Example VI describes comparison of the properties
of the product of the invention with those of a prior
art product.
Example I
This example demonstrates the preparation of
poly (dichlorophosphazene).
To a 15 ml glass tube were added 0.54 g anhydr
ous aluminium chloride (AICI3) and 7.4 g hexach
lorocyclotriphosphazene (NPCl2)3, which (NPC12)3 had been purified by crystallization from heptane
and distillation. The concentration of the AICI3 was
0.72 weight percent or 1.90 mole percent.
A vacuum pump was connected to the tube, now
containing trimer and catalyst, and vacuum was
applied for about 30 minutes, until a pressure of 10-2
Tory was obtained.
Next, the tube was sealed and heated to about 175 C. for about 60 hours, at which point the po
ly(dichlorophosphazene) contained in the tube was
recovered and dissolved in 300 milliliters of toluene
to form an anhydrous toluene solution of poly(dich
lorophosphazene).
Example Il This example demonstrates the preparation of an
unsaturated polyaryloxyphosphazene having the
formula {NP(OC6H4tertC4Ha)0.9(OC6H4Cl)o.9(OCoH-2CHCH =CH2)0.2J1056 The anhydrous toluene solution of poly(dich
lorophosphazene) formed in Example I was added to
an anhydrous diglyme - benzene solution containing
0.75 equivalent of NaOC6H4Cl, 0.75 equivalent
of NaOC6H4-t-C4Hg, and 0.5 equivalent of Na OC6H2-CH2CH=CH2 at a temperature of about 95"C. with constant stirring.
After the addition, benzene was distilled from the
reaction mixture until a temperature of from about 115 -116 C. was attained, and then the reaction pro
duct was heated at reflux for about 50 to about 65
hours.
Next, the reaction product was poured into an
excess of methyl alcohol with constant stirring for
about 24 hours, and the resulting precipitate (a terpolymer) was added to a large excess of water with constant stirring for about 24 hours.
The resulting terpolymer, of the formula indicated above, was recovered in a yield of about 53% and was soluble in benzene, toluene, tetrahydrofuran, and dimethylformamide.
The terpolymer, an unsaturated polyaryloxyphosphazene, had a weight average molecular weight as determined by gpc of 338,000, a Tg of 0.5"C. as determined by differential scanning calorimetry, and a 9.56% chlorine content.
Example 111 This example demonstrates the preparation of an unsaturated aryloxycyclotriphosphazene having the formula N3P3(OC6H4Cl)3(OC6H4-2H2CH OH2)3 A solution containing 2.65 equivalents of sodium in 300 milliliters of diglyme was added to a solution containing 1.29 equivalents of p - chlorophenol and 1.42 equivalents of o - allylphenol in 100 milliliters of diglyme, and the mixture was heated to a temperature of about 75" to about 80"C.
The resulting mixture was introduced into a mixing vessel containing a solution of 0.431 equivalents of hexachlorocyclotriphosphazene in 1000 milliliters of diglyme.
The resulting product was heated for about 5 hours at about 100 C., cooled to room temperature, and added to a large excess of water with stirring.
The water was removed by decantation, and the resulting product was dissolved in ether and washed several times with water.
The resulting product was dried under reduced pressure and was recovered in a yield of about 92% as an unsaturated aryloxycyclotriphosphazene having the formula shown above.
The unsaturated aryloxycyclotriphosphazene had a chlorine content of about 11.8% and an ethylene double bond content of about 7.68%.
Example IV
This example demonstrates the heat treatment method of this invention using the unsaturated aryloxycyclotriphosphazene produced in Example 111.
Six wear layer compositions (designated A two F) were separately prepared by adding about 100 grams of the unsaturated aryloxycyclotriphosphazene produced in Example Ill, about 40 grams of a crosslinking agent, pentaerythritol tetra(,B- mercaptopropionate), and about 2 grams of a photo initiator, 2 - phenyl - 2,2 - diemethoxyacetophenone, to a reaction vessel with stirring.
Each of the resulting wear layer compositions was separately heated for 5 minutes in an oven atthe temperatures set forth in Table I. Next each wear layer composition was separately applied at a thickness of 4 mls (0.1 mm), using a Bird applicator, to a 1/8-inch (3 mm) thick polyethylene substrate and the wear layer coatings on the substrates were cured by subjecting the substrates to from about 4 to about 6 joules/cm2 of ultraviolet light. Table I illustrates the results of testing, using an "Instron" tensile tester.
"Instron" is a trade mark.
TABLE!
Wear l Heat Tensile Elongation Layer Treatment Strength (b/oJ "F ("C) P.s.i. Kg/cm2
A 70 21 953 67 44
B 100 40 1447 102 38
C 125 52 1654 116 40
D 150 66 1899 133 52
E 200 93 1860 131 52
F 250 121 1504 106 53
Example V
This example demonstrates the heat treatment method of this invention using a mixture of an unsaturated polyaryloxyphosphazene and an unsaturated aryloxycyclotriphosphazene.
To a reaction vessel were added about 80 grams of an unsaturated polyaryloxyphosphazene having the general formula: [NP(OC6H4- 4 Cl),20(OC6H43Cl)020(OH6H4 4 =CH2)0.50j1810 The unsaturated polyaryloxyphosphazene was tested and found to have a weight average molecular weight as determined by gpc of 446,000, a Tg of 5"C as determined by differential scanning calorimetry, and a chlorine content of 18.8%.
Next was added a solvent mixture (80 parts by weight ethyl acetate/20 parts by weight methyl ethyl ketone) in a quantity to give a resulting solution of 50% solids content then about 20 grams of the unsaturated aryloxycyclotriphosphazene of Example
Ill were added with stirring.
Next the ethylene double bond content of the phosphazene materials was calculated, and about 10 grams of pentaerythritol tetra(P - mercaptopropionate) were added with stirring in order to obtain a double bond to thiol group ratio of 1:1.1(10% excess).
Next 2 grams (2% by weight of the phosphazene material) of 2 - phenyl - 2,2 - dimethoxyacetophenone were added, with stirring and the resulting composition was applied to a thickness of 6 mils (0.15 mm), using a Bird applicator, to a 1/8-inch (3 mm) thick polyethylene substrate.
The resulting coated substrate was placed in an air circulating oven at a temperature of about 140"F (60 C) for about 10 minutes to remove the ethyl ace tatelmethyl ethyl ketone mixture employed to dissolve the polyaryloxyphosphazene.
The resulting coated substrate was cooled to room temperature and was placed in an oven at a temperature of about 200"F. (93"C) for about 5 minutes and then subjected to from about 4 to about 6 joules/cm2 of ultraviolet light to cure the coating composition.
Example Vl (Closest PriorArt Method) Using the ingredients employed in Example V of this invention and using the prior art process of
Examples IV and V of U.S. Patent 4,145,479, a second wear layer composition was prepared and cured. As taught in the prior art, the coated substrate was placed in an oven at a temperature of about 140"F (60 C) for about 10 minutes to remove the solvent mixture and dry the coating prior to curing by ultraviolet light. The solvent-free wear layercompos- ition was not heat treated according to the process of the present invention.
The cured coating of Examples V and VI of this invention were then tested by "Instron" measurement. The following Table II shows the results of the tests:
TABLE 11 Test Cured Coating Produced in
Example V Example Vl {Invention) (Closest Prior Art) Tensile strength (psi) 899 365
Tensile strength (kg/cm2) 63 26 % Elongation 42 30
The above data of Tables I and II indicate the improvement in tensile strength and elongation achieved by the coatings produced by the heat treatment process of this invention as compared to the closest prior art process. It is apparent that the process ofthis invention facilitates the production of improved coatings, exhibiting higher degrees of cure than the prior art coatings.
The tests of tensile strength and elongation described in Examples IV and VI were carried out on a film of wear layer separated from the substrate.
Claims (11)
1. A process for the manufacture of a surface covering comprising a substrate having a cured wear layer, which comprises forming a curable coating composition comprising (a) at least one member selected from the group consisting of unsaturated polyaryloxyphosphazenes and unsaturated aryloxycyclotriphosphazenes and (b) a crosslinking agent, or a reaction product of (a) and (b), and, if desired or required (c) a solventforthe polyaryloxyphosphazene, applying the coating composition to the substrate, and, after removing the solvent if present, heat treating the coating composition, either before or after its application to the substrate, for a period of at least 5 minutes at a temperature within the range of 100"F (40"C) to 350"F (177"C), and curing the heat-treated coating composition.
2. A process as claimed in claim 1, wherein an unsaturated polyaryloxyphosphazene is used, and wherein it is of the formula [NP(OC6H5wRw)x(OCaH5wRw)y(R1)zi wherein each R independently represents hydrogen, chlorine, bromine, fluorine, a (C, to C1O) linear our branched alkyl radical or a (C, to C4) linear or branched alkoxy radical; R1 represents -OC6H4-CH OH2, -0C5H3(R2)-CH =CH2, -0C6H4-CH=CH)R2), -OC,H,(RZ)-CH=CH)R3), -OC6H4-CH2CH OH2, -0C6H3(R2)-CH2CH =CH2, -OC6H4CH(R2)-CH=CH2, --OC6H,CH,,-C(R1) =CH,, -OC6H4CH2-CH=CH(R2), or -OCaH4-CH=CH-(CH2)-CH=CH2;; R2 and R3 each independently represent a halogen or an alkenyl, alkoxy, aryloxy, alkyl, or aryl radical; w has a value of from 0 to 5; z has a value greater than 0 and the sum ofx + y + z equals 2; n has a value of from 2 to 3100; and b has a value of from 0 to 4.
3. A process as claimed in claim 1 or claim 2, wherein an unsaturated aryloxycyclotriphosphazene
is used, and is ofthe formula N3Pg(OC6Hs-wRw)a(Rl )s-a wherein R, P1 and w have the meanings given in claim 2, and a has a value greater than 0 and less than 6.
4. A process as claimed in any one of claims 1 to
3, wherein the crosslinking agent is an organic com
pound having two or more thiol groups.
5. A process as claimed in any one of claims 1 to 4, wherein the composition is cured under free radical generating conditions.
6. A process as claimed in claim 5, wherein the composition also comprises a peroxide curing agent.
7. A process as claimed in claim 5, wherein the free radical conditions are induced by radiation.
8. A process as claimed in claim 7, wherein the radiation is ultra violet radiation, and the composition also comprises a photoinitiator and, if desired or required, an activator.
9. A process as claimed in claim 1, carried out substantially as described in Example IV or Example
V.
10. A surface covering wherever prepared by a process as claimed in any one of claims 1 to 9.
11. In a process for producing a surface covering having a cured wear layer wherein a substrate is coated by passing the substrate beneath a coating means which applies a wear layer composition comprising the reaction product of a cross-linking agent and at least one phosphazene material selected from the group consisting of unsaturated polyaryloxyphosphazene; unsaturated aryloxycyclotriphosphazene and mixtures thereof to the substrate and wherein if any solvent is employed for the purpose of dissolving unsaturated polyaryloxyphosphazene it is removed and the coated substrate is cured under free radical conditions, the improvement comprising heat treating the wear layer composition, either before or after coating the substrate but before curing the coated substrate, for a period of at least 5 minutes at a temperature within the range of from at least 1000 to about 350"F.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3138979A | 1979-04-19 | 1979-04-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2046627A true GB2046627A (en) | 1980-11-19 |
Family
ID=21859172
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8012903A Withdrawn GB2046627A (en) | 1979-04-19 | 1980-04-18 | Process for the manufacture of heat resistant curable surface coating composition |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS55142061A (en) |
| DE (1) | DE2948127B2 (en) |
| GB (1) | GB2046627A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4543397A (en) * | 1984-06-18 | 1985-09-24 | Loctite (Ireland) Ltd. | Styryloxy resins and compositions thereof |
| EP0307861A2 (en) * | 1987-09-14 | 1989-03-22 | Idemitsu Petrochemical Company Limited | Coated resin molded-article |
| EP0376021A2 (en) * | 1988-12-16 | 1990-07-04 | Idemitsu Petrochemical Co., Ltd. | Styrene-based resin composite material and use thereof |
| US5273830A (en) * | 1988-12-16 | 1993-12-28 | Idemitsu Petrochemical Co., Ltd. | Magnetic recording medium comprising a syndiotactic styrene-based polymer substrate, a magnetic layer and a backcoat lubricating layer each layer containing a curable phosphazine compound |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63241075A (en) * | 1986-11-26 | 1988-10-06 | Idemitsu Petrochem Co Ltd | Reaction-curable coating material |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4145479A (en) * | 1978-07-06 | 1979-03-20 | Armstrong Cork Company | Heat resistant curable surface coating composition comprising the reaction product of an unsaturated polyaryloxyphosphazene and an unsaturated aryloxycyclotriphosphazene |
-
1979
- 1979-11-29 DE DE19792948127 patent/DE2948127B2/en active Pending
- 1979-12-03 JP JP15568579A patent/JPS55142061A/en active Pending
-
1980
- 1980-04-18 GB GB8012903A patent/GB2046627A/en not_active Withdrawn
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4543397A (en) * | 1984-06-18 | 1985-09-24 | Loctite (Ireland) Ltd. | Styryloxy resins and compositions thereof |
| EP0307861A2 (en) * | 1987-09-14 | 1989-03-22 | Idemitsu Petrochemical Company Limited | Coated resin molded-article |
| EP0307861A3 (en) * | 1987-09-14 | 1990-03-21 | Idemitsu Petrochemical Company Limited | Coated resin molded-article |
| US5047270A (en) * | 1987-09-14 | 1991-09-10 | Idemitsu Petrochemical Company Limited | Coated resin molded-article |
| EP0376021A2 (en) * | 1988-12-16 | 1990-07-04 | Idemitsu Petrochemical Co., Ltd. | Styrene-based resin composite material and use thereof |
| EP0376021A3 (en) * | 1988-12-16 | 1991-11-06 | Idemitsu Petrochemical Co., Ltd. | Styrene-based resin composite material and use thereof |
| US5082717A (en) * | 1988-12-16 | 1992-01-21 | Idemitsu Petrochemical Co., Ltd. | Styrene-based resin composite material |
| US5273830A (en) * | 1988-12-16 | 1993-12-28 | Idemitsu Petrochemical Co., Ltd. | Magnetic recording medium comprising a syndiotactic styrene-based polymer substrate, a magnetic layer and a backcoat lubricating layer each layer containing a curable phosphazine compound |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2948127A1 (en) | 1980-10-23 |
| DE2948127B2 (en) | 1981-02-26 |
| JPS55142061A (en) | 1980-11-06 |
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