GB2142338A - Stabiliser mixture for polyethylene - Google Patents
Stabiliser mixture for polyethylene Download PDFInfo
- Publication number
- GB2142338A GB2142338A GB08415955A GB8415955A GB2142338A GB 2142338 A GB2142338 A GB 2142338A GB 08415955 A GB08415955 A GB 08415955A GB 8415955 A GB8415955 A GB 8415955A GB 2142338 A GB2142338 A GB 2142338A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen
- series
- polyethylene material
- polyethylene
- formula
- 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
- -1 polyethylene Polymers 0.000 title claims abstract description 45
- 239000004698 Polyethylene Substances 0.000 title claims abstract description 40
- 229920000573 polyethylene Polymers 0.000 title claims abstract description 40
- 239000000203 mixture Substances 0.000 title claims abstract description 19
- 239000003381 stabilizer Substances 0.000 title description 2
- 239000000463 material Substances 0.000 claims abstract description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
- 239000001257 hydrogen Substances 0.000 claims abstract description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 239000006096 absorbing agent Substances 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 6
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 125000001424 substituent group Chemical group 0.000 claims abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 5
- 230000003019 stabilising effect Effects 0.000 claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims description 29
- 239000004594 Masterbatch (MB) Substances 0.000 claims description 18
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- 229910052759 nickel Inorganic materials 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 claims description 4
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical class NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims 2
- 239000000843 powder Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 235000019256 formaldehyde Nutrition 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000004611 light stabiliser Substances 0.000 description 3
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- CMGGIAUJZXZZPH-UHFFFAOYSA-N (1-hydroxy-4-octoxycyclohexa-2,4-dien-1-yl)-phenylmethanone Chemical compound C1=CC(OCCCCCCCC)=CCC1(O)C(=O)C1=CC=CC=C1 CMGGIAUJZXZZPH-UHFFFAOYSA-N 0.000 description 1
- FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical class OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 description 1
- SWZOQAGVRGQLDV-UHFFFAOYSA-N 4-[2-(4-hydroxy-2,2,6,6-tetramethylpiperidin-1-yl)ethoxy]-4-oxobutanoic acid Chemical compound CC1(C)CC(O)CC(C)(C)N1CCOC(=O)CCC(O)=O SWZOQAGVRGQLDV-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 101100059444 Mus musculus Ccnb1 gene Proteins 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
- FPZOQHTZFUQXBJ-UHFFFAOYSA-N [Ni].O=C1C=CN=N1 Chemical compound [Ni].O=C1C=CN=N1 FPZOQHTZFUQXBJ-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical group [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 229940093470 ethylene Drugs 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002896 organic halogen compounds Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003254 radicals Chemical class 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
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/527—Cyclic esters
-
- 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
- C08K5/00—Use of organic ingredients
-
- 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
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/5398—Phosphorus bound to sulfur
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
A composition comprising: <IMAGE> in which X is -S- or -O-; each R1 independently is hydrogen, C1-4 alkyl, -CH2-Br, -CH2-Cl, -CH2-O-(C1-4 alkyl) or phenyl; each R2 independently is hydrogen, C1-4 alkyl, -CH2-Cl, -CH2-Br or -CH2-O-(C1-4 alkyl); or R1 and R2 on the same ring together with the C-atom to which they are attached form unsubstituted cyclohexylidine, 3,4-dibromocyclohexylidene or unsubstituted cyclohexenylidine; and each R3 independently is hydrogen or C1-4 alkyl; each R4 independently is hydrogen or methyl; with the provisos: i) that at least one of the substituents R1 to R3 is other than hydrogen on each ring system; and ii) when R1 and R2 is -CH2-Cl or -CH2-Br or R1 and R2 form a cyclic significance R3 and R4 are hydrogen; together with b) a U.V. absorber. The composition is used for stabilising polyethylene material when added to the material.
Description
SPECIFICATION
Improvements in or relating to organic compounds
The invention relates to flameproofed polyethylene with good light stability and processes for preparing such material.
It is well known that polyethylene can be flameproofed using halogenated organic compounds in particular in combination with antimony trioxide. Such halogenated compounds are chlorinated paraffins or brominated aromatic compounds. These compounds have the disadvantage that the stability to light is lessened to such an extent that the addition of a U.V stabiliser will not compensate for the decreased light stability.
Surprisingly, it has been found that both good light stability and good flameproofing properties are imparted to polyethylene by a composition comprising
a) a compound for formula I
in which X is S or O; teach R, independently is hydrogen, C1 4alkyl, -CH2-Br, -CH2-CI, -CH2-O-(C, 4alkyl) or phenyl;
each R2 independently is hydrogen, C, 4alkyl, -CH2-CI, -CH2-Br or -CH2-O-(C, 4alkyl); or R, and R2 on the same ring together with the C-atom to which they are attached form unsubstituted cyclohexylidene, 3,4-dibromocyclohexySidene or unsubstituted cyclohexenylidene;
each R3 independently is hydrogen or C, 4alkyl; and
each R4 independently is hydrogen or methyl; with the provisos:
i) that at least one of the substituents R, to R4 is other than hydrogen on each ring system; and
ii) when R, and R2 is -CH2-Ci or -CH2-Br or R1 and R2 form a cyclic significance R3 and R4 are hydrogen; together with b) a U.V. absorber.
Preferably the ratio of component a) to b) is 3:5 to 1250:1 more preferably 5:2 to 1000;1; most preferably 7:1 to 150:1. The ratios are by weight.
Preferably according to the invention there is provided a polyethylene material containing:
a) 3 to 25 % (by weight of polyethylene material) of a compound of formula I defined above; and
b) 0.02 to 5 % (by weight of polyethylene material) of a U.V. absorber.
The preferred amount of component a) (by weight of polyethylene material) is 5-20 %, more preferably 7-15 %. The preferred amount of component b) (by weight of polyethylene material) is 0;02-2 % more preferably 0.1-1 %.
Unless indicated to the contrary where a significance occurs more than once in a formula its significances are independent of one another.
Preferably any Cm 4alkyl is methyl, ethyl or propyl, more preferably methyl.
Preferably R3 is hydrogen or methyl, more preferably hydrogen.
Preferably R4 is hydrogen.
Preferably X is sulphur.
Preferred compounds of formula I are of formula la
in which X is-as defined above; R, is -CH3, -C2H5, -C3H7, -CH2-Br, -CH2-CI or unsubstituted phenyl; R2 is -CH3, -C2H2, -C3H7, -CH2-Br or -CH2CI.
The compounds of formula I and la are known or may be prepared by known methods from known compounds.
Preferred U.V. absorbers are of the 2(2'-hydroxyphenyl)benztriazole series, of the 2-hydroxy benzophenone series, of the nickel complex series (such as nickel pyrazolone), of the sterically hindered amine series or of the oxalic acid diamide series. Preferred light stabilisers are also described in German Offenlegungschrift 2606358. Further preferred light stabilisers are described in the book "Kunststoff-Additive" by Gächter and Miller pages 105 to 1 39.
Usual 2-(2'-hydroxyphenyl)benztriazoles are as follows:
where R3 is hydrogen or CH3 and the symbol + signifies tertiary butyl.
Usual 2-hydroxybenzophenones are as follows:
Usual nickel complex compounds are as follows:
where R4 is C2 4alkyl and + signifies tertiary butyl,
where R9 is C4 6alkyl or cyclohexyl;
Usual sterically hindered amines are tetraalkylpiperidines as follows:
where signifies tertiary butyl,
CH CH3 H molecular weight > 2000 CH2CH2-N CH2tti /N OC5CH2tC- ~ CH3 1s vn3 çn3 0 0 n
Usual oxalamide derivatives are as follows::
Preferred as U.V. absorbers are those of the 2,2,6,6-tetraalkylpiperidine series, of the 2hydroxybenzophenone series and of the nickel complex compounds, in particular 2,2,6,6tetraalkylpiperidine compounds.
Preferred amounts of component a) in a polyethylene material according to the invention are 5 to 20 %, more preferably 7 to 1 5 % (by weight of polyethylene substrate).
Preferred amounts of component b) in a polymeric substrate are 0.1 to 1 % (by weight of polyethylene substrate).
The compounds of component a) can conveniently be made up as a master batch comprising 20 to 90 %, more preferably 30 to 80 % of a component a) and 80 to 10 %, more preferably 70 to 20 % of a carrier, preferably polyethylene. In a similar fashion compounds of component b) can be made up as a master batch containing 5 to 30 % of component b) and 70 to 95 % of a carrier, preferably polyethylene.
For the avoidance of doubt mixtures of two or more compounds of formula I and mixtures of two or more light stabilisers may be used in the compositions according to the invention, polyethylene substrates according to the invention and processes for preparing the same.
The compounds of formula I can be worked into the polymeric material by known methods, for example the compounds of formula I can be mixed with a polyethylene powder and the mixture extruded into foils, granulates or sheets or by foaming techniques.
Preferably the polyethylene material according to the invention is formed into thin sheets.
Preferably the density of the sheet polyethylene material according to the invention is 0.912 to 0.930 g/cm3. Preferably the polymeric material has a crystallinity of 25 to 50 %.
Such polyethylene material is described in Adv. Polym. Sci. 7 (1970) pages 386 to 448-Mortimer s Ehrlich entitled "Fundamentals of the free radical polymerisation of ethy lene". These pages are incorporated herein by reference.
Further examples of polyethylene useful in the present invention are described in Encyclopedia of Polymer Science and Technology Vol. 6 (Interscience 1967) and US Patent 2,153,553.
-These references are incorporated herein by reference.
The invention will now be illustrated by the following Examples in which all parts and percentages are by weight and all temperatures are in "C unless indicated to the contrary.
Example 1
70 Parts of a commercial form of polyethylene powder (Melt Flow Index [190 /2.16 Kp)= 20) is mixed with 30 parts of compound 9 given in Table 1 below and is then worked in a continuous kneader at a temperature of 1 20' to 185 to produce a master batch in granular form. (This master batch will be referred to as Masterbatch A).
5 Parts of a U.V. absorber of the 1-hydroxy-4-octoxybenzophenone type and 5 parts of a nickel complex of formula II
is mixed with 90 parts of a commercial form of polyethylene powder (MFI [190"/2. 16 Kp = 20) and is then worked in an extruder at 1 20 to 150 to produce a master batch in granular form. (This masterbatch will be referred to as Masterbatch B).
34 Parts of Masterbatch A are mixed with 60 parts of a commercial form of polyethylene granulate (MFI [190 /2.16 Kp] = 1.4) and 6 parts of Masterbatch B. This mixture is worked through an extruder with blow head at a temperature of 1 50 to 1 75 C to produce blow films about 1 50 ,u thick. The resulting films show good flameproofing properties and have a good light stability.
Example 2
70 Parts of a commercial form of polyethylene powder (MFI [190"/2. 16 Kp] = 20) are mixed with 30 parts of Compound I given in Table 1 below and the mass is worked on a continuous kneader at a temperature of 15.0 to 120 into a masterbatch in granular form (this masterbatch is hereafter referred to as Masterbatch C).
1 7 Parts of Masterbatch C are mixed with 1 7 parts of Masterbatch A, 6 parts of Masterbatch
B and 60 parts of a commercial form of polyethylene granulate (MFI [1 90o/2.19 Kp] = 1.4) and the mixture is worked into films in a method similar to that described in Example 1. The resulting films have good flameproofing properties and very good stability to light.
Similar results to the above Examples 1 and 2 can be obtained by replacing compound 9 or 1 respectively by any other compound of compounds 1 to 1 9 described in Table 1 below.
Example 3
90 Parts of a commercial polyethylene powder (MFI [190"/2. 16 Kpl = 1.4) are mixed with 10 parts of the compound 9 of Table 1 and 0.4 parts of a sterically hindered amine of the formula
of molecular weight > 2000 (Tinuvin 622) are mixed together and the mixture is worked through an extruder with a blow head at a temperature of 1 50 to 175"C to form blow film about 1 50 itm thick. The resulting flameproofed polyethylene has very good light fastness. ("TINUVIN" is an R.T.M.)
Examples 4 to 21
The polyethylene material of Example 1 can be treated according to the method of Example 1 using instead of the compound 9 of Table 1 any one of Compounds 1 to 8 and 10 to 1 8.
TABLE 1
COMPOUND NO. STRUCTURE MELTING POINT CHCHO 1 ( C c 174-175" 4 2 (C 3 C 2O O 187-190 3 (Hct 2\C/ Z CH2CH2 CH20 / 4 CH, ,CH'O\ o 2210 5 .CH20\;% -o 194-60 0 C2H5 NCHo/" 2 /CH2 \ 2 5 tC2H5/ CH2O/O, 04705oo TABLE 1 (Continued)
CDMPOUND STRUCTURE MELTING PO INT NO. STRUCTURE MELTING POINT 7 (* CHO o t 136-140 n-C3H7 8 le C0CH2c/CH2O\po ClcK N0/0" 088-09O 2 2 2 9 (C 3 \ t C ; \ t Z 8-229 228-229 s I \eH20 10 z C X X P ~ o 198-199 2 /CICH2 'C/CH20\ 11 t C1CH / CN20 / 5 t 199-2000 /"I 0 12 ( 2 \ C / 034036o C2115 C1120 S 2 TABLE 1 (Continued)
COMPOUND STRUCTURE MELTING PCINT NO.
0 3 C=CH20\ o 039.1400 CH r- 2 (c) )sPn$o 14 C 139.0400 Os (CH3\ zC 2 > 0 240.2420 16 (C/\/CCN 2 CH2C > pW O 187-188 / (C\ 2/ 2 2 C2 - CH2 CH2 S12 17 (CH3\ wC 2 \ t 057.1580 i-C3H7 CH3 18 (H2C\ 1 159-1 600 CH3 CH3 19 ( CH2O\ P 161-163 CHO sM2 ttI3
Claims (14)
1. A composition comprising:
a) a compound of formula I
in which X is S or O;
each R, independently, is hydrogen, C1-4alkyl, -CH2-Br, -CH2-CI, -CH2-O-(C, 4alkyl) or phenyl;
each R2 independently, is hydrogen, C1-4alkyl, -CH2-CI, -CH2-Br or -CH2-O-(C1-4alkyl);
or R, and R2 on the same ring together with the C-atom to which they are attached form unsubstituted cyclohexylidene, 3,4-dibromocyclohexylidene or unsubstituted cyclohexeneylidene;
each R3 independently is hydrogen or C, 4alkyl; and
each R4 independently is hydrogen or methyl; with the provisos:
i) that at least one of the substituents R, to R4 is other than hydrogen on each ring system; and
ii) when R, and R2 is -CH2-CI or -CH2-Br or R and R2 form a cyclic significance R3 and R4 are hydrogen; together with b) a U.V. absorber.
2. A composition according to Claim 1 in which component b) is selected from the 2(2'hydroxyphenyl)benztriazole series, the 2-hydroxybenzophenone series, the nickel complex series, the sterically hindered amine series or the oxalic acid diamide series.
3. A composition according to Claim 1 of Claim 2 in which the ratio of components a) to b) is 3:5 to 1250:1.
4. A composition according to Claim 3 in which the ratio of components a) to b) is 7:1 to 150:1.
5. A composition according to any one of the preceding claims in which the compound of formula I is of formula la
in which X is defined in Claim 1; Rt is -CH3, -C2H5, -C3H7, -CH2-Br, -CH2-CI or unsubstituted phenyl; R2 is -CH3, -C2H5, -C3H7, -CH2-Br or -CH2CI.
6. A composition according to Claim 1 substantially as herein described with reference to
any one of Examples 1 to 21.
7. Polyethylene material containing:
a) 3 to 25 % (by weight of polyethylene material) of a compound of formula I defined in
Claim 1; and
b) 0.02 to 5 % (by weight of polyethylene material) of a U.V. absorber.
8. Polyethylene material according to Claim 7 in which component b) is selected from 2(2' hydroxyphenyl)benztriazole series, the 2-hydroxybenzopheone series, the nickel complex series, the sterically hindered amine series or the oxalic acid diamide series.
9. Polyethylene material according to Claim 7 or Claim 8 in which the amount of component -a) is 7 to 15 % and the amount of component b) is 0.1 to 1 %.
10. Polyethylene material according to any one of Claims 7 to 9 in which the compound of formula I is of formula la
in which X is defined in Claim 1 and Rt and R2 are defined in Claim 4.
11. Polyethylene films containing a composition according to any one of Claims 1 to 6.
1 2. A process for stabilising polyethylene material comprising adding to the material a composition according to any one of Claims 1 to 6.
1 3. A process for stabilising polyethylene material comprising mixing a master batch of 20 to 90 % of component a) as defined in Claim 1, 10 to 80 % of carrier with a master batch of 5 to 30 % of component b) defined in Claim 1 and 70 to 95 % of carrier.
14. A process for stabilising polyethylene material substantially as herein described with reference to any one of Examples 1 to 21.
1 5. Polyethylene material substantially as herein defined with reference to any one of
Examples 1 to 21.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3322989 | 1983-06-25 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8415955D0 GB8415955D0 (en) | 1984-07-25 |
| GB2142338A true GB2142338A (en) | 1985-01-16 |
| GB2142338B GB2142338B (en) | 1986-09-17 |
Family
ID=6202434
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08415955A Expired GB2142338B (en) | 1983-06-25 | 1984-06-22 | Improvements in or relating to organic compounds |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS6013830A (en) |
| CH (1) | CH660881A5 (en) |
| FR (1) | FR2549074B1 (en) |
| GB (1) | GB2142338B (en) |
| IT (1) | IT1177804B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2172600A (en) * | 1985-03-22 | 1986-09-24 | Sandoz Ltd | Flame retardant methyl methacrylate polymers |
| FR2617856A1 (en) * | 1987-07-10 | 1989-01-13 | Sandoz Sa | STABILIZING COMPOSITIONS OF POLYMERIC MATERIALS |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8466096B2 (en) | 2007-04-26 | 2013-06-18 | Afton Chemical Corporation | 1,3,2-dioxaphosphorinane, 2-sulfide derivatives for use as anti-wear additives in lubricant compositions |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH581163A5 (en) * | 1974-07-30 | 1976-10-29 | Sandoz Ag |
-
1984
- 1984-06-18 FR FR8409629A patent/FR2549074B1/en not_active Expired
- 1984-06-19 IT IT48416/84A patent/IT1177804B/en active
- 1984-06-22 CH CH3031/84A patent/CH660881A5/en not_active IP Right Cessation
- 1984-06-22 JP JP59127718A patent/JPS6013830A/en active Pending
- 1984-06-22 GB GB08415955A patent/GB2142338B/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2172600A (en) * | 1985-03-22 | 1986-09-24 | Sandoz Ltd | Flame retardant methyl methacrylate polymers |
| FR2617856A1 (en) * | 1987-07-10 | 1989-01-13 | Sandoz Sa | STABILIZING COMPOSITIONS OF POLYMERIC MATERIALS |
| BE1002455A3 (en) * | 1987-07-10 | 1991-02-19 | Sandoz Sa | STABILIZING COMPOSITIONS OF POLYMERIC MATERIALS. |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2549074B1 (en) | 1987-04-30 |
| IT1177804B (en) | 1987-08-26 |
| IT8448416A0 (en) | 1984-06-19 |
| FR2549074A1 (en) | 1985-01-18 |
| GB8415955D0 (en) | 1984-07-25 |
| JPS6013830A (en) | 1985-01-24 |
| GB2142338B (en) | 1986-09-17 |
| CH660881A5 (en) | 1987-05-29 |
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Effective date: 19920622 |