GB2045258A - Treated Filler for a Thermoplastic Polymer - Google Patents
Treated Filler for a Thermoplastic Polymer Download PDFInfo
- Publication number
- GB2045258A GB2045258A GB8005872A GB8005872A GB2045258A GB 2045258 A GB2045258 A GB 2045258A GB 8005872 A GB8005872 A GB 8005872A GB 8005872 A GB8005872 A GB 8005872A GB 2045258 A GB2045258 A GB 2045258A
- Authority
- GB
- United Kingdom
- Prior art keywords
- filler
- ethylene oxide
- thermoplastic polymer
- solvent
- oligomer
- 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.)
- Granted
Links
- 239000000945 filler Substances 0.000 title claims abstract description 34
- 229920001169 thermoplastic Polymers 0.000 title claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000003085 diluting agent Substances 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- 239000002344 surface layer Substances 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 18
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 9
- 238000000576 coating method Methods 0.000 claims description 8
- 239000011248 coating agent Substances 0.000 claims description 6
- 239000010410 layer Substances 0.000 claims description 4
- 239000012764 mineral filler Substances 0.000 claims description 4
- 239000000047 product Substances 0.000 description 13
- 239000004743 Polypropylene Substances 0.000 description 10
- -1 amino, vinyl Chemical group 0.000 description 9
- 235000012211 aluminium silicate Nutrition 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000005995 Aluminium silicate Substances 0.000 description 7
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 5
- 229920000098 polyolefin Polymers 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000004756 silanes Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000009661 fatigue test Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229920001684 low density polyethylene Polymers 0.000 description 1
- 239000004702 low-density polyethylene Substances 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 235000012243 magnesium silicates Nutrition 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical group C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical class [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/10—Encapsulated ingredients
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/40—Compounds of aluminium
- C09C1/42—Clays
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
- C09C3/10—Treatment with macromolecular organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Dispersion Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Laminated Bodies (AREA)
Abstract
Fillers for thermoplastic polymers are provided with a surface layer of a liquid ethylene oxide oligomer. The filler can be coated in the presence of a solvent or diluent, which is then removed by heating between 50 and 200 DEG C.
Description
SPECIFICATION
Treated Fiiler for a Thermoplastic Polymer
This invention relates to method of treating a filler for a thermoplastic polymer, to give improved adhesion with the polymer.
It is known to introduce fillers into thermoplastic polymers in order to improve their useful properties, but unfortunately this tends to make the product more difficult to work. Conversely, the workability of the product can be improved at the expense of its properties. In the case of polyolefins, an improvement in mechanical properties can be achieved only with difficulty because of the very low physical adhesion and lack of chemical adhesion between the polyolefin and the mineral or other filler.
Methods are known for improving adhesion, and they rely upon a change in the physico-chemical properties of the particles of filler. A simpie method of preparation is to give acidity to the surface of the filler, by coating the particles with aluminium or magnesium silicates. See J. Hodgkin, D. Soloman in J.
Macromol. Sci.A8 (3) 635 (1974), and D. Soloman in B. P. 1228538 (1969).
Also, a method is known for the preparation of the surface of fillers using organotitanates, see
Plast. Tech. 22 (4) 71 (1976) and Plast. Tech. 22 (4) 81 (1976). Where the fillers are to be used with polyolefins, triisopropyleneoxytitanate, for example, must be applied in a quantity of 0.53% by weight based on the weight of the filler.
The most popular organic coatings include stearic acid, and barium, calcium and sodium stearates, as well as compositions containing them. See, for example, Plast. Tech. 22 (4) 71 (1976), and Plast. Tech. 22(4)81(1976), and Rev. Plast. Mod. 223,8(1975). Known coating media for mineral fillers include silanes, as described in Jap. Plastic Age, Sep.-Oct. 33 (1975), Dow Corning
Corp. (05.08.70), U.S.-061505, Union Carbide Corp. (17.05.68) and U.S.-862027.
Silanes of the general chemical formula R'Si(OR)3 possess two types of functional groups, R' and
OR. R1 is usually a reactive organic group such as amino, vinyl, epoxy or methacrylate, which bonds to silicon via a short aliphatic chain; and OR is a hydrolizable alcoholate group.
The silanes are bound to the surface of the filler through the OR group, and the functional groups
R' react with the polymeric matrix. The known method for preparation of the filler surface is by coating with a layer of polymer produced by radical or anionic polymerization of a reactive monomer, such as styrene, pyridine, divinylbenzene or acrylic acid. See Jap. Plastic Age, Sep-Oct. 33 (1975), J.
Macromol. Sci.A8(3)649 (1974),AsakiChem. Ind. Co. Ltd. 29 (1967),JA069210, U.S. Polywood
Champion Papers Inc. (21.08.70.) and U.S. 066107.
Polymer coatings having a molecular weight of500--800 wili generally constitute up to 3% by weight of the filler, and their thickness can range from 20 to 30 . The polymer coating may be applied to the surface of the filler in a separate process, or it can be applied during mixing of the filler with the polymer. In this latter case, the amount of catalyst is preferably sufficient only to initiate polymerization, and not to cause polyolefin cross-linking.
Thus, the present invention consists in a treated filler for use with a thermoplastic polymer, having a thin surface layer of a liquid ethylene oxide oligomer.
The invention also consists in a method of treating a filler or a thermoplastic polymer, which comprises coating the filler with a thin layer of a liquid ethylene oxide oligomer, preferably eventually in the presence of a solvent or diluent, and optionally removing the solvent or diluent by heating at a temperature between 50 and 2000C. The oligomer preferably has an average molecular weight of 100--800.
The treated filler can safely be dried at a temperature from 50 to 2000C, and processing of the final product at temperatures as high as 2500C does not cause decomposition of the ethylene oxide oligomer, which remains liquid. Ethylene oxide oligomers can impart good wettabiiity to a wide range of mineral fillers, such as talc, silica, chalk, and kaolin. The liquid state of aperture is preferred since this allows adhesive bonds broken by the application of force to the material to be reestablished. Also, fatigue tests showed a considerable improvement in the properties of low-density polyethylene which had been extended with the treated filler. The applied optimal content of the aperture is from 1 to 10% by weight based on the weight of the filler in the mixture and this depends on the particle size distribution.The mechanical properties of the material may be adjusted by altering the quantity of liquid ethylene oxide oligomer added. Ethylene oxide oligomer is especially useful as aperture due to its low cost, its availability, and because a complicated technique for applying it to the filler is not required.
The invention will now be further illustrated by the following examples.
Example I
2 g of ethylene oxide oligomer of medium molecular weight equal to 200 is dissolved in 30 g of water and 100 g of kaolin is added with stirring till the thick mass is obtained. Then, the mass is dried in a dryer at temperature 800C. Such prepared kaolin is mixed with polyethylene of density .92 g/ccm with ratio of 6:4 and is granulated. The product of considerably improved mechanical properties is obtained, comparing to the case of use of non-prepared kaolin for filling.
The results are shown below:
Product obtained
Product obtained according to the
according to the example I without the
example I oligomer addition
modulus of elasticity 107 115 /N/m2x 1 O6/ tensile strength 7.7 8.4
/N/m2x 106/ elongation at fracture 75 30
/%/
impact strength 106 63.8
/J/m2x 102/
Example II The product is prepared as in the example I, substituting chalk for kaolin and using 10 g of ethylene oxide oligomer. Such prepared chalk is mixed in ratio 5:5 with polyethylene of density .92 g/ccm. The material obtained possesses much better mechanical properties than in the case of using of the non-prepared chalk.
Product obtained
Product obtained according to the
according to the example Il without the
example Il oligomer addition
modulus of elasticity 74.2 1 56 /N/m2 x 1 O6/
tensile strength 6.5 7.6 /N/mZx 1 O6/ elongation at fracture 215 20 / impact strength 222.8 57.9
/J/m2x 102/
Example Ill
The product is prepared as in the example I, substituting quartz for kaolin and using 1 g of ethylene oxide oligomer. The material obtained possesses much better mechanical properties than the one in the case of using of non-prepared quartz flour.
Product obtained
Product obtained according to the
according to the example 111 without the
example Ill oligomer addition
modulus of elasticity 90.2 135.4 /N/m2x 1 O6/ tensile strength 7.1 7.4
/N/m2 x 1 OR/ elongation at fracture 90 50
/96/
impact strength 139.3 92.2 /J/m2x 102/
The mixtures with non-modified fillers show large modulus of elasticity and low elongation at fracture values. The materials are brittle and non-ductile.
The introduction of the modifying agents like in the examples I, II and Ill causes the decrease of the modulus of elasticity, practically unchanged tensile strength and considerably increased elongation at fracture values. High values of notched impact strength/measure of brittleness/ and high elongation at fracture are the result of the considerable increase of adhesion between the filler and the polyolefine as the effect of introduction of the modifying agent. The considerable increase of elongation at fracture causes that the materials obtained from the modified fillers are ductile and elastic.
Example IV
The product is prepared as in the example I, substituting isotactic polypropylene of density of .885 g/ccm for polyethylene and chalk for kaolin and using 10 g of ethylene oxide oligomer. The material obtained has much better mechanical properties than in the methods with application of nonprepared chalk and non-filled polypropylene.This is seen from the data given below: weight ratio 5:5 1 2 3 4
PP+ chalk 940 16.8 90 48.5 PP+chalk+10% 570 15.8 420 79.7
oligomer
PP 480 22.5 850 55.0 where
1 is modulus of elasticity
2-stress at yield point in N/m2x 106 3-elongation at fracture in %
4 impact strength in J/m2x 102
Example V
The product is prepared as in the example IV by mixing of chalk prepared by the method according to the invention in weight ratio 6:4 with isotactic polypropylene of density .885 g/ccm. The material obtained has considerably better mechanical properties than in the case of non-prepared chalk and non-filled polypropylene. It is seen from the data given below:
weight ratio 6:4 1 2 3 4
PP+chalk 1200 16.9 30 31.4 PP+chalk+10% 550 11.8 328 63.0
oligomer
PP 480 22.5 850 55.0 where 1, 2, 3 and 4 are the same as in the table in the example IV.
Claims (3)
1. A treated filler for use with a thermoplastic polymer, having a surface layer of a liquid ethylene oxide oligomer.
2. A method of treating a filler for a thermoplastic polymer, which comprises coating the filler with a thin layer of a liquid ethylene oxide oligomer.
3. A method according to Claim 2, carried out in the presence of a solvent for the ethylene oxide oligomer or in the presence of a diluent which is not a solvent for either the filler or the ethylene oxide oligomer.
3. A method according to claim 2, carried out eventually in the presence of a solvent or diluent.
4. A method according to claim 3, which additionally comprises removing the solvent or diluent by heating at a temperature between 50 and 2000C.
5. A method according to any one of claims 1,2 and 3, in which the oligomer has an average molecular weight of 100--800.
6. A method according to any one of claims 2 to 5, in which the filler is a mineral filler.
7. A method according to claim 2, substantially as herein described with reference to any one of the foregoing examples.
8. An extended thermoplastic polymer having as filler a filler according to claim 1 or a product of any of claims 2-7.
9. The method for improving of adhesion between the filler and thermoplastic polymer significant by that the mineral filler is coated with thin layer of liquid ethylene oxide oligomer, eventually in the presence of solvent, with that the diluted mass is dried at temperature 50 to 2000 C.
New Claims or Amendments to Claims Filed on 6th June 1980
Superseded Claims 3, 9
New or Amended Claims:
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL1979213582A PL120692B1 (en) | 1979-02-21 | 1979-02-21 | Method of modification of mineral filler for thermoplastic polymerslastichnykh polimerov |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2045258A true GB2045258A (en) | 1980-10-29 |
| GB2045258B GB2045258B (en) | 1983-03-30 |
Family
ID=19994670
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8005872A Expired GB2045258B (en) | 1979-02-21 | 1980-02-21 | Treated filler for a thermoplastic polymer |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS55112246A (en) |
| CS (1) | CS227304B2 (en) |
| DD (1) | DD149230A5 (en) |
| DE (1) | DE3004738A1 (en) |
| FR (1) | FR2449713A1 (en) |
| GB (1) | GB2045258B (en) |
| IT (1) | IT1145654B (en) |
| PL (1) | PL120692B1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2161489A (en) * | 1984-07-12 | 1986-01-15 | Glaverbel | Articles of filled synthetic polymeric materials and glass bead filler therefor |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58198566A (en) * | 1982-05-17 | 1983-11-18 | Karupu Kogyo Kk | Granular resin composition |
| US5562978A (en) * | 1994-03-14 | 1996-10-08 | E. I. Du Pont De Nemours And Company | Polymer-coated inorganic particles |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE551353C (en) * | 1930-07-17 | 1932-05-30 | I G Farbenindustrie Akt Ges | Process for the production of pigment colors and varnishes |
| DE953010C (en) * | 1951-10-15 | 1956-11-22 | Degussa | Filler for rubber and plastic compounds |
| GB943287A (en) * | 1961-03-13 | 1963-12-04 | British Titan Products | Improvements in titanium dioxide pigments |
| DE1592974A1 (en) * | 1966-12-31 | 1971-02-11 | Titangmbh | Process for the production of a titanium dioxide pigment with improved properties |
| GB1417574A (en) * | 1972-05-13 | 1975-12-10 | Laporte Industries Ltd | Pigments |
| US4124562A (en) * | 1972-06-20 | 1978-11-07 | Mitsubishi Petrochemical Co., Ltd. | Polyolefin composition containing a novel modified filler |
| US3843380A (en) * | 1972-12-26 | 1974-10-22 | Scm Corp | Process for spray drying pigment |
| JPS51101049A (en) * | 1975-03-03 | 1976-09-07 | Kanegafuchi Chemical Ind | NETSUKASOSEIJUSHOJUTENZAIOYOBISOSEIBUTSU |
| GB2003890B (en) * | 1977-08-17 | 1982-04-28 | Johnson Matthey Co Ltd | Pigments |
| US4210572A (en) * | 1978-08-29 | 1980-07-01 | Nl Industries, Inc. | Coupling agents for thermosetting composites |
-
1979
- 1979-02-21 PL PL1979213582A patent/PL120692B1/en unknown
-
1980
- 1980-02-08 DE DE19803004738 patent/DE3004738A1/en not_active Ceased
- 1980-02-13 CS CS80986A patent/CS227304B2/en unknown
- 1980-02-19 DD DD80219134A patent/DD149230A5/en not_active IP Right Cessation
- 1980-02-20 IT IT47960/80A patent/IT1145654B/en active
- 1980-02-20 JP JP2038380A patent/JPS55112246A/en active Pending
- 1980-02-20 FR FR8003746A patent/FR2449713A1/en active Granted
- 1980-02-21 GB GB8005872A patent/GB2045258B/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2161489A (en) * | 1984-07-12 | 1986-01-15 | Glaverbel | Articles of filled synthetic polymeric materials and glass bead filler therefor |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2045258B (en) | 1983-03-30 |
| JPS55112246A (en) | 1980-08-29 |
| DE3004738A1 (en) | 1980-08-28 |
| FR2449713A1 (en) | 1980-09-19 |
| IT8047960A0 (en) | 1980-02-20 |
| PL213582A1 (en) | 1980-09-22 |
| IT1145654B (en) | 1986-11-05 |
| CS227304B2 (en) | 1984-04-16 |
| FR2449713B1 (en) | 1983-09-09 |
| DD149230A5 (en) | 1981-07-01 |
| PL120692B1 (en) | 1982-03-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 746 | Register noted 'licences of right' (sect. 46/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |