CA1100666A - Polyester-poly(diarylenealkylene isophthalate) compositions - Google Patents
Polyester-poly(diarylenealkylene isophthalate) compositionsInfo
- Publication number
- CA1100666A CA1100666A CA312,291A CA312291A CA1100666A CA 1100666 A CA1100666 A CA 1100666A CA 312291 A CA312291 A CA 312291A CA 1100666 A CA1100666 A CA 1100666A
- Authority
- CA
- Canada
- Prior art keywords
- poly
- isophthalate
- diarylenealkylene
- resin
- thermoplastic molding
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
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- Compositions Of Macromolecular Compounds (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
Novel thermoplastic molding compositions are disclosed which comprise poly (1,4-butylene terephthalate), and a poly(diarylenealkylene isophthalate), alone, or combined with a reinforcing agent.
Novel thermoplastic molding compositions are disclosed which comprise poly (1,4-butylene terephthalate), and a poly(diarylenealkylene isophthalate), alone, or combined with a reinforcing agent.
Description
669~
This invention provides a novel thermoplastic molding composition which comprises poly(l,4-butylene terephthalate), and a poly(diarylene-alkylene isophthalate~ resin, alone, or in combination with a reinforcing amount of a reinforcing filler.
Poly(1,4-butylene terephthalate) resins are well known and have been widely employed for the production of thermoplastic molded articles. Also, reinforced compositions of poly(l,4-butylene terephthalate) have been commercially available for a number of years.
These compositions are useful for a plurality of applications especially when a high degree of solvent resistance is required. Glass fiber reinforced poly(l,4~butylene terephthalate) when molded into various articles has a tendency to become distorted or warped especially when the molded article has a thin section.
; I
~l 8CM~2390 l ll It has been found that if a polytdiarylenealkylene
This invention provides a novel thermoplastic molding composition which comprises poly(l,4-butylene terephthalate), and a poly(diarylene-alkylene isophthalate~ resin, alone, or in combination with a reinforcing amount of a reinforcing filler.
Poly(1,4-butylene terephthalate) resins are well known and have been widely employed for the production of thermoplastic molded articles. Also, reinforced compositions of poly(l,4-butylene terephthalate) have been commercially available for a number of years.
These compositions are useful for a plurality of applications especially when a high degree of solvent resistance is required. Glass fiber reinforced poly(l,4~butylene terephthalate) when molded into various articles has a tendency to become distorted or warped especially when the molded article has a thin section.
; I
~l 8CM~2390 l ll It has been found that if a polytdiarylenealkylene
2 ¦1 isophthalate) resin is added to the reinforced poly(l,4-butylene
3 1I terephthalate) molding composition, the molded articles are
4 l¦ substantially resistant to warpage or dic:tortion af~er they S 1l are re~oved from the ~old. In unreinforc:ed modifications, 6 l¦ there is no reduction in heat deflection temperature under 7 ¦¦ load. These results are achieved without: any appreciable decrease 8 1¦ in the mechanical, physical or molding properties of a typical 9 ¦~ poly(l,4 butylene terephthalate) moldin~ compositions, whether ll or not they contain reinforcing agents.
12 I Detailed Deseription of the Invention. The present 13 l invention provides a novel thermoplastic molding composition 14 ll which comprises:
(a) poly(l,4-bu~ylene terephthalate) and 1~ 1! (b) a poly(diarylenealkylene isophthalate) resin.
1'~ 1'1 .
18 !l A preferred embodiment will also include 19 lll (c) a reinforcing amount of a reinforcing agent.
21 l¦ The poly(l,4-butylene terephthalate) should have an 22 11 intrinsic viscosity between 0.4 and 1.2 dl/g. as measured at 23 !l 30C. in a 60/40 solution of phenol/tetrachloroethane. ~ more 24 l¦ preferred range is between 0.6 and 0.9 dl/g.
25 ll The poly(diarylenealk~Jlene isophthalate) resin has Z6 recurring units of the formula:
.8 ~l -R-C-R-0-l - ~C-0-: !
30, !l !
.
` `~
~c~-2390 1 whcrein each -R- is selected from the grou~ consisting of 2 1 phen~lene, halo-substituced phenylene and alkyl substituted 3 ¦ phenylene, and X and Y are each selected from the group consist-4 1¦ ing of hydrogen, hydrocarbon radicals free from aliphatic un-!; sa~uration and of radicals which together with the adjoining 6 1 .
7 ~ C -'' 8i, 1 9 1l atom form a cycloalkane radical, the total number of carbon atoms in X and Y being up to 12.
12 !I The preferred poly(diarylenealkylene isophthalate) .
13 1! resins may be derived from the reaction of bisphenol-A and 14 1l i50phthallc acid or a reactive derivative thereof, such as lS 1l isophthaloyl chloride, dimethyl isophthalate and the like.
16 I, These preferably will have from 100-4oo recurring units of the 17 ¦I formula:
1~ Ij ~
19 ~ H3 ~ 8 20 ll ~ o ~ ~ 3 0 --C ~ C- ~_ 21 ll CH3 23 jl The poly(diarylenealkylene isophthalates) can be 24 ,¦ prepared by ~hose skilled in this art using conventional tech-25 ¦¦ niques. They should have an intrinsic viscosity between 0.3 26 I,l and 1.0, preferably from 0.3 to 0.45 as measured at 20C. in 27 1 methylene chloride.
: 28 1 .
29 Th~ relnforcinp, ~p~ents ln the optional embo~imcnt~
I may be selectQ~ from finely di.vided alumlnum, iron or nickel 'i . Il ~ 3 -~ ~; . , : . . . . . . .
~ 8C~ 2390 and the like, and non-meta]s, such as carbon filaments, ~
cates, such as acicular calcium silica-te, asbestos, titaniurn dioxide, wollas-tonite, po~assium ti-canate ancl titana-te ~hiskers, glass rlakes ancl L ibers.
Al~hough it is only necessary to use a reinforcing amount of the reinrorcing agent, Erom 1-60 parts by weight of the total weight of the composition may comprise the reinforcing agent. A preferred range is from 5-40 parts by weight. T,~len used herein, parts by weight are based on 100 par-ts by weight in total composition.
The preferred reinforcing agents are of glass, and j it is preferred to use fibrous glass filaments. The preferred ilaments for plastics reinforcement are made by mechanical pulling. The filament diameters range rom about 0.000112 to about 0.00075 inch, but this is not critical to the present invention.
- The poly-(1,4-butylene terephthalate) resin may comprise from 95 to 20 parts by weight of the composition and the poly(diarylenealkylene isophthalate) resin may comprise from 5 to 80 parts by weight of the resinous components (a) and (b) in the composition.
The preferred compositions will include rom 90 to 65 parts by weight of poly(l,4-butylene terephthalate) and from 10 to 35 parts by weight of the poly(diarylene-alkylene isophthalate) resin.
The composition may be prepared by any s~andard procedure and the particular method employed is not critical, ~ (- ~
1 The compositions may also include flame retardants 2 such as those disclosed in U.S. Patent No. 3,915,926, dated 3 October 28, 1975.
4 I . .
12 I Detailed Deseription of the Invention. The present 13 l invention provides a novel thermoplastic molding composition 14 ll which comprises:
(a) poly(l,4-bu~ylene terephthalate) and 1~ 1! (b) a poly(diarylenealkylene isophthalate) resin.
1'~ 1'1 .
18 !l A preferred embodiment will also include 19 lll (c) a reinforcing amount of a reinforcing agent.
21 l¦ The poly(l,4-butylene terephthalate) should have an 22 11 intrinsic viscosity between 0.4 and 1.2 dl/g. as measured at 23 !l 30C. in a 60/40 solution of phenol/tetrachloroethane. ~ more 24 l¦ preferred range is between 0.6 and 0.9 dl/g.
25 ll The poly(diarylenealk~Jlene isophthalate) resin has Z6 recurring units of the formula:
.8 ~l -R-C-R-0-l - ~C-0-: !
30, !l !
.
` `~
~c~-2390 1 whcrein each -R- is selected from the grou~ consisting of 2 1 phen~lene, halo-substituced phenylene and alkyl substituted 3 ¦ phenylene, and X and Y are each selected from the group consist-4 1¦ ing of hydrogen, hydrocarbon radicals free from aliphatic un-!; sa~uration and of radicals which together with the adjoining 6 1 .
7 ~ C -'' 8i, 1 9 1l atom form a cycloalkane radical, the total number of carbon atoms in X and Y being up to 12.
12 !I The preferred poly(diarylenealkylene isophthalate) .
13 1! resins may be derived from the reaction of bisphenol-A and 14 1l i50phthallc acid or a reactive derivative thereof, such as lS 1l isophthaloyl chloride, dimethyl isophthalate and the like.
16 I, These preferably will have from 100-4oo recurring units of the 17 ¦I formula:
1~ Ij ~
19 ~ H3 ~ 8 20 ll ~ o ~ ~ 3 0 --C ~ C- ~_ 21 ll CH3 23 jl The poly(diarylenealkylene isophthalates) can be 24 ,¦ prepared by ~hose skilled in this art using conventional tech-25 ¦¦ niques. They should have an intrinsic viscosity between 0.3 26 I,l and 1.0, preferably from 0.3 to 0.45 as measured at 20C. in 27 1 methylene chloride.
: 28 1 .
29 Th~ relnforcinp, ~p~ents ln the optional embo~imcnt~
I may be selectQ~ from finely di.vided alumlnum, iron or nickel 'i . Il ~ 3 -~ ~; . , : . . . . . . .
~ 8C~ 2390 and the like, and non-meta]s, such as carbon filaments, ~
cates, such as acicular calcium silica-te, asbestos, titaniurn dioxide, wollas-tonite, po~assium ti-canate ancl titana-te ~hiskers, glass rlakes ancl L ibers.
Al~hough it is only necessary to use a reinforcing amount of the reinrorcing agent, Erom 1-60 parts by weight of the total weight of the composition may comprise the reinforcing agent. A preferred range is from 5-40 parts by weight. T,~len used herein, parts by weight are based on 100 par-ts by weight in total composition.
The preferred reinforcing agents are of glass, and j it is preferred to use fibrous glass filaments. The preferred ilaments for plastics reinforcement are made by mechanical pulling. The filament diameters range rom about 0.000112 to about 0.00075 inch, but this is not critical to the present invention.
- The poly-(1,4-butylene terephthalate) resin may comprise from 95 to 20 parts by weight of the composition and the poly(diarylenealkylene isophthalate) resin may comprise from 5 to 80 parts by weight of the resinous components (a) and (b) in the composition.
The preferred compositions will include rom 90 to 65 parts by weight of poly(l,4-butylene terephthalate) and from 10 to 35 parts by weight of the poly(diarylene-alkylene isophthalate) resin.
The composition may be prepared by any s~andard procedure and the particular method employed is not critical, ~ (- ~
1 The compositions may also include flame retardants 2 such as those disclosed in U.S. Patent No. 3,915,926, dated 3 October 28, 1975.
4 I . .
5 I _escription of the Preferred Embodiments. - The
6 Ifollowing examples illustrate compositions within the scope
7 ,of this invention. They are not to be construed as limiting
8 ¦the claims thereto. In the data tables, "N.D.I' means --
9 ¦not determined.
10! . .
1l EXAMPLE 1 13 The following compositio~s are prepared by blending 14 the materials in an extruder:
l,~i , Exam le l~ Compositio ~ ts by weight) 1 lA (control) 17 ¦poly(1,4-butylene terephthalat~)* 55 70 18 ¦¦poly(4,4'-diphenylene propane lisophthalate) resin** 15 glass fibers 1/8'l(0wens Corning 21 OCF 419, 1/8") 30 30 22 pho~phite stabilizer*** 0 05 0 05 24 ¦ These compositions have the following physîcal proper-2S jties after injection molding in~o test pieces:
_ 27 * Intrinsic viscosity, 0.8 dl./g.
28 ** Polyarylate U-Polymer, U-1060, product uf Unitik~ Company, Japan.
30 1*** Ferro 904.
I
"
:-` ' .. ' "~ ~3C~1-2390 1 Properties 1 2 Speclfic Gravity, g./cc. 1.512 1.542 3 Deflection temperature 4 at 2~4 psi, F. 344 . 396 Warpage, 1/16" X 4"
diameter disc, 6 mm., as molded 0 20 7 mm., after 30 min. a~ 350F. 17 25 8 Notched Izod impact, 1.9 1.8 - f~. lbis./in. . .
9 . ' 10 ~ Unnotched Izod impact, 17.1 14.5
1l EXAMPLE 1 13 The following compositio~s are prepared by blending 14 the materials in an extruder:
l,~i , Exam le l~ Compositio ~ ts by weight) 1 lA (control) 17 ¦poly(1,4-butylene terephthalat~)* 55 70 18 ¦¦poly(4,4'-diphenylene propane lisophthalate) resin** 15 glass fibers 1/8'l(0wens Corning 21 OCF 419, 1/8") 30 30 22 pho~phite stabilizer*** 0 05 0 05 24 ¦ These compositions have the following physîcal proper-2S jties after injection molding in~o test pieces:
_ 27 * Intrinsic viscosity, 0.8 dl./g.
28 ** Polyarylate U-Polymer, U-1060, product uf Unitik~ Company, Japan.
30 1*** Ferro 904.
I
"
:-` ' .. ' "~ ~3C~1-2390 1 Properties 1 2 Speclfic Gravity, g./cc. 1.512 1.542 3 Deflection temperature 4 at 2~4 psi, F. 344 . 396 Warpage, 1/16" X 4"
diameter disc, 6 mm., as molded 0 20 7 mm., after 30 min. a~ 350F. 17 25 8 Notched Izod impact, 1.9 1.8 - f~. lbis./in. . .
9 . ' 10 ~ Unnotched Izod impact, 17.1 14.5
11 I . .
12 I Flexural strength, psi. 25,600 26,800
13. ¦ Flexural modulusl psi. 971,000 993,000
14 Tensile s~rength, psi. . . . 16,400 18,000
15 Elongation at break, ~/0 N.D. N.D.
l'j .
18 The f3110wing composition is preparad by blending 19 the materials in an extruder:
' Composition (~ts by wei~ht) 21 I poly(l,4-butylene tereph~ha~ate)* 40 22 ¦! poly(4,4'diphenylenepropane iso- .
23 ¦ phthalate~ resin** 30 24 ¦ glass fibers 1/8" ~Owens Corning, .
OCF 419, 1/8") 30 27 stabilizer~'~** . 0 05 I ~
28 * Intrinsic viscosity, 0.8dl /g, 2g ~* Polyarylate U-Polymer, U-1060, product I of Unltika Co~pany, Japan.
30 l' **.* Ferro 904.
Il - 6 -I
I' ~ i611Ei ¦ 3C H- 2 3 9 0 l This composition has the following physical properties 2 I after in]ection molding:
3 ¦ Properties Specific Gravity, g./cc. 1.483 'i Deflection temperature at 6 264 psi, F. 160 7 1 Warpage, 1/16" X 4"
l diameter disc, 8 mm., as molded 0 9 mm., after 30 min. at 350F. 19 Notched Izod impact ll ft. lbs.lin. 2.1 l~ Unnotched Izod impact, 13 ft. lbs./in. 15.3 14 Flexural strength, psi. 27,300 lS Flexural modulus, psi. 1,061,000
l'j .
18 The f3110wing composition is preparad by blending 19 the materials in an extruder:
' Composition (~ts by wei~ht) 21 I poly(l,4-butylene tereph~ha~ate)* 40 22 ¦! poly(4,4'diphenylenepropane iso- .
23 ¦ phthalate~ resin** 30 24 ¦ glass fibers 1/8" ~Owens Corning, .
OCF 419, 1/8") 30 27 stabilizer~'~** . 0 05 I ~
28 * Intrinsic viscosity, 0.8dl /g, 2g ~* Polyarylate U-Polymer, U-1060, product I of Unltika Co~pany, Japan.
30 l' **.* Ferro 904.
Il - 6 -I
I' ~ i611Ei ¦ 3C H- 2 3 9 0 l This composition has the following physical properties 2 I after in]ection molding:
3 ¦ Properties Specific Gravity, g./cc. 1.483 'i Deflection temperature at 6 264 psi, F. 160 7 1 Warpage, 1/16" X 4"
l diameter disc, 8 mm., as molded 0 9 mm., after 30 min. at 350F. 19 Notched Izod impact ll ft. lbs.lin. 2.1 l~ Unnotched Izod impact, 13 ft. lbs./in. 15.3 14 Flexural strength, psi. 27,300 lS Flexural modulus, psi. 1,061,000
16 Tensile strength, psi. 17,200
17 Elongation at break, % N.D.
18
19 ¦ EXAMPLE 3
20 i The following unreinforce~ compositions are prepared
21 by blending ~he materials in an extruder:
22 1 Example
23 ¦ Composition (parts by wei~ht~ 3 ~ control)
24 1 poly(l,4-butylene terephthalate)* 80 100 poly(4,4'-diphenylenepropane iso-26 ~ phthalate)resin** 20 ---27 stabilizer*** 0.05 0.05 . -- .
29 * Intrinsic viscosity, 1.1 dl./~.
** Polyarylate U Polymer, U-1060, product of '( Unitika Company, Japan.
31 ~ *** Ferr~ 904.
&;i6~
. ~ 8CH-2390 1 These compositio~s have the following physical 2 properties a~ter injection molding:
3 Properties 3 3A (control) Specific Gravity, g,/cc. 1.287 1.31 Deflection temperature 6 at 264 psi, F. 149 136 7 Warpage, 1/16" X 4" .
diameter disc, 8 1 mm., as molded 0 0 9 mm., after 30 min. at 350F. distorted 15 10 ~ Notched Izod impact, 11 ~ ft. lbs./in. 1.2 1.2 . .
12 Unnotched Izod impact, 13 ft. lbs./in. break break 14 Flexural strength, psi. 12,500 12,600 Flexural modulus, psi. 334,000 351,000 1~ Tensile strength,psiO 8,300 8,100 17 Elongation at break, % 135 307 .1~
19 Although the above examples have shown various modifications of the present invention, other variations are 21 ¦ possible in the light of the above teachings. I~ is, therefore, 22 to be understood that changes may be made in the particular 23 embodiments of the invention described which are within the 24 full intended scope of the invention as defined by the appended claims.
.
_ ,, ,. . : i... .
29 * Intrinsic viscosity, 1.1 dl./~.
** Polyarylate U Polymer, U-1060, product of '( Unitika Company, Japan.
31 ~ *** Ferr~ 904.
&;i6~
. ~ 8CH-2390 1 These compositio~s have the following physical 2 properties a~ter injection molding:
3 Properties 3 3A (control) Specific Gravity, g,/cc. 1.287 1.31 Deflection temperature 6 at 264 psi, F. 149 136 7 Warpage, 1/16" X 4" .
diameter disc, 8 1 mm., as molded 0 0 9 mm., after 30 min. at 350F. distorted 15 10 ~ Notched Izod impact, 11 ~ ft. lbs./in. 1.2 1.2 . .
12 Unnotched Izod impact, 13 ft. lbs./in. break break 14 Flexural strength, psi. 12,500 12,600 Flexural modulus, psi. 334,000 351,000 1~ Tensile strength,psiO 8,300 8,100 17 Elongation at break, % 135 307 .1~
19 Although the above examples have shown various modifications of the present invention, other variations are 21 ¦ possible in the light of the above teachings. I~ is, therefore, 22 to be understood that changes may be made in the particular 23 embodiments of the invention described which are within the 24 full intended scope of the invention as defined by the appended claims.
.
_ ,, ,. . : i... .
Claims (10)
1. A thermoplastic molding composition which comprises:
(a) poly(1,4-butylene terephthalate; and (b) a poly(diarylenealkylene isophthalate) resin.
(a) poly(1,4-butylene terephthalate; and (b) a poly(diarylenealkylene isophthalate) resin.
2. A composition as defined in Claim 1 which also includes:
(c) a reinforcing amount of a reinforcing agent.
(c) a reinforcing amount of a reinforcing agent.
3. A thermoplastic molding composition as defined in Claim 1 wherein the poly(diarylenealkylene isophthalate) resin consists essentially of recurring units of the formula:
wherein each -R- is selected from the group consisting of phenylene, halo-substituted phenylene and alkyl substituted phenylene, and X and Y are each selected from the group con-sisting of hydrogen, hydrocarbon radicals free from aliphatic unsaturation and of radicals which together and with the adjoin-ing atom form a cycloalkane radical, the total number of carbon atoms in X and Y being up to 12.
wherein each -R- is selected from the group consisting of phenylene, halo-substituted phenylene and alkyl substituted phenylene, and X and Y are each selected from the group con-sisting of hydrogen, hydrocarbon radicals free from aliphatic unsaturation and of radicals which together and with the adjoin-ing atom form a cycloalkane radical, the total number of carbon atoms in X and Y being up to 12.
4. A thermoplastic molding composition as defined in Claim 2 wherein the poly(diarylenealkylene isophthalate) has the repeating unit
5. A thermoplastic molding composition which comprises:
(a) from 95 to 20 parts by weight of poly (1,4-butylene terephthalate);
(b) from 5 to 80 parts by weight of a poly (diarylenealkylene isophthalate) resin;
(c) from 1 to 60 parts by weight of filamentous glass.
(a) from 95 to 20 parts by weight of poly (1,4-butylene terephthalate);
(b) from 5 to 80 parts by weight of a poly (diarylenealkylene isophthalate) resin;
(c) from 1 to 60 parts by weight of filamentous glass.
6. A thermoplastic molding composition as defined in Claim 5 wherein the poly(diarylenealkylene isophthalate) resin consists essentially of recurring units of the formula:
wherein each -R- is selected from the group consisting of phenylene, halo-substituted phenylene and alkyl substituted phenylene and X and Y are each selected from the group consisting of hydrogen, hydrocarbon radicals free from aliphatic unsatura-tion and of radicals which together with the adjoining atom from a cycloalkane radical, the total number of carbon atoms in X and Y being up to 12.
wherein each -R- is selected from the group consisting of phenylene, halo-substituted phenylene and alkyl substituted phenylene and X and Y are each selected from the group consisting of hydrogen, hydrocarbon radicals free from aliphatic unsatura-tion and of radicals which together with the adjoining atom from a cycloalkane radical, the total number of carbon atoms in X and Y being up to 12.
7. A thermoplastic molding composition as defined in Claim 6 wherein the poly(diarylenealkylene isophthalate) has the repeating unit
8. A thermoplastic molding composition as defined in Claim 1 which includes a flame-retardant amount of a flame-retardant agent.
9. A method of preventing distortion in a thermo-plastic molded article which is formed of a thermoplastic composition that comprises a poly(1,4-butylene terephthalate) resin and a reinforcing agent, said method comprising including in said thermoplastic composition a poly(diarylenealkylene isophthalate) resin as defined in Claim 1 in an amount sufficient to prevent distortion of the molded article.
10. A method as defined in Claim 9 wherein the poly (diarylenealkylene isophthalate) has recurring units of the formula:
wherein each -R- is selected from the group consisting of phenylene, halo-substituted phenylene and alkyl substituted phenylene, and X and Y are each selected from the group con-sisting of hydrogen, hydrocarbon radicals free from aliphatic unsaturation and of radicals which together with the adjoining atom form a cycloalkane radical, the total number of carbon atoms in X and Y being up to 12.
wherein each -R- is selected from the group consisting of phenylene, halo-substituted phenylene and alkyl substituted phenylene, and X and Y are each selected from the group con-sisting of hydrogen, hydrocarbon radicals free from aliphatic unsaturation and of radicals which together with the adjoining atom form a cycloalkane radical, the total number of carbon atoms in X and Y being up to 12.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA312,291A CA1100666A (en) | 1978-09-28 | 1978-09-28 | Polyester-poly(diarylenealkylene isophthalate) compositions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA312,291A CA1100666A (en) | 1978-09-28 | 1978-09-28 | Polyester-poly(diarylenealkylene isophthalate) compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1100666A true CA1100666A (en) | 1981-05-05 |
Family
ID=4112477
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA312,291A Expired CA1100666A (en) | 1978-09-28 | 1978-09-28 | Polyester-poly(diarylenealkylene isophthalate) compositions |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1100666A (en) |
-
1978
- 1978-09-28 CA CA312,291A patent/CA1100666A/en not_active Expired
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