GB1565745A - Stabilisation of propylene polymers containing inorganic additives - Google Patents
Stabilisation of propylene polymers containing inorganic additives Download PDFInfo
- Publication number
- GB1565745A GB1565745A GB490177A GB490177A GB1565745A GB 1565745 A GB1565745 A GB 1565745A GB 490177 A GB490177 A GB 490177A GB 490177 A GB490177 A GB 490177A GB 1565745 A GB1565745 A GB 1565745A
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- GB
- United Kingdom
- Prior art keywords
- weight
- composition
- composition according
- isocyanurate
- propylene
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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
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
- F02F—CYLINDERS, PISTONS OR CASINGS, FOR COMBUSTION ENGINES; ARRANGEMENTS OF SEALINGS IN COMBUSTION ENGINES
- F02F7/00—Casings, e.g. crankcases or frames
- F02F7/006—Camshaft or pushrod housings
-
- 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
- C08K13/00—Use of mixtures of ingredients not covered by one single of the preceding main groups, each of these compounds being essential
- C08K13/02—Organic and inorganic 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Combustion & Propulsion (AREA)
- Mechanical Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
(54) STABILISATION OF PROPYLENE POLYMERS
CONTAINING INORGANIC ADDITIVES
(71) We, IMPERIAL CHEMICAL
INDUSTRIES LIMITED, Imperial
Chemical House, Millbank, London SWIP 3JF a British Company, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:- This invention relates to propylene polymers containing adsorbent inorganic additives such as talc, asbestos, chalk or limestone which impede the stabilisation of propylene polymers. By "propylene polymers" is meant homopolymers of propylene or copolymers comprising at least 50% by weight of polymerised propylene.
Adsorbent inorganic additives impede the stabilisation of propylene polymers probably because they adsorb the sterically hindered phenolic compounds conventionally used as anti-oxidants in propylene polymers. Accordingly, British patent specification 1,297,802 suggested adding to the propylene polymers various substances such as uncured epoxy resins which are adsorbed onto the inorganic additive in preference to the hindered phenolic anti-oxidants. Many of these substances, particularly the suitable epoxy resins, are expensive and many are viscous liquids which are difficult to disperse into the propylene polymers.It has now been discovered that if the sterically hindered phenolic anti-oxidant group is bonded to an isocyanurate ring and is used with the usual synergising organic sulphur compounds then useful improvements in stabilisation can be achieved without the need to use a substance such as an epoxy compound.
These improvements are achieved despite the fact that isocyanurate anti-oxidants of the type disclosed in British patent specification 1,259,179 are not the most potent of anti-oxidants when used in propylene polymers.
Accordingly, this invention provides a propylene polymer composition comprsing:
a) 10 to 85% by weight (based on the total
weight of the composition) of an
adsorbent inorganic additive, b) an organic sulphur compound of the
type which synergises with hindered
phenolic anit-oxidants and c) an isocyanurate anti-oxidant which is a
sterically hindered phenolic ester of
isocyanuric acid having the general
formula:
where
A1 is a group containing a sterically hindered phenol,
A2 and A3 are independently hydrogen, an alkyl group containing up to 11 carbon atoms or preferably a group containing a sterically hindered phenol and it is especially preferred that A1, A2 and A3 be the same group, and
X1, X2 and X3 are independently either the group: (CH3)n or the group:
where n and p are independently 0, 1, 2 or 3 andmis is 1* 2, 3 or 4. Preferably, n is 0, p is I and m is 2.
The hindered phenols comprise a stericallv hindered hydroxyl group. The hydroxyl group is preferably hindered by tertiary butyl groups ortho to the hydroxyl group. The hindered phenol is preferably joined to the remainder of the isocyanurate compound by a bond para to the hindered hydroxyl group. Accordingly, the two preferred isocyanurates (i.e. n is 0 or p is I and m is 2) have the formulae:
where t But is tertiary butyl, and B is
The compositions preferably contain 0.01 to 69 (usually 0.08 to 1%) by weight of the isocyanurate unless they are intended for use as masterbatches in which case they may contain up to 12% by weight of isocyanurate.
Organic sulphur compounds which synergise with sterically hindered phenolic anti-oxidants include long chain (e.g. C,O to
C22) mercaptans and sulphides but the preferred compounds are dialkyl thiodialkanoates especially when the alkyl groups contain from 10 to 22 carbon atoms and the alkanoic acids contain from 2 to 6 carbon atoms. Specific examples are dilauryl and distearyl thiodipropionate. The compositions preferably contain from 0.01 to 10% (usually 0.1 to 0.5%) by weight of organic sulphur compound unless they are intended for use as masterbatches in which case they can contain up to 150: by weight of organic sulphur compound. More specifically the compositions may contain 0.5 to 3 Ó (based on the propylene polymer) of the organic compound.
The propylene polymers are preferably crystalline and/or thermoplastic and preferably have a melt flow index of from 0.5 to 50 (usually 1 to 20) g/10 minutes as measured according to British Standard 2782:Part 1/105C/1970 using a 2.16 Kg load but carried out at 230"C. They may be homopolymers or copolymers preferably copolymers comprising 2 to 20% by weight of ethylene and correspondingly 98 to 80% by weight of propylene.
Adsorbent inorganic additives include not only talc and carbon but also asbestos, calcium carbonate (especially limestone and coccolithic chalk) and also slate dust, mica, clay, barium sulphate and hollow bodies composed of various silicates of aluminium, for example those described in British patent specification 1,292,112. Preferably, the number average particle size of the inorganic additives is below 30 y and is often in the range of 0.1 to 15 y although the carbon blacks used can have particle sizes as low as 10 millimicrons.
Although the use of substances such as epoxy compounds which are adsorbed onto the inorganic additives in preference to the anti-oxidants is not essential to the performance of this invention, nevertheless, the use of such substances in compositions containing 3 to 25% by weight of inorganic additive achieves even more improvement in the stabilisation of the propylene polymers. Accordingly, the compositions of this invention may additionally comprise 0.01 to 5% (preferably 0.1 to 1.3%) by weight of the inorganic additive of a substance which is adsorbed onto the inorganic additive in preference to the isocyanurate and so reduces impedance of the stabilization of the composition by the inorganic additive. Where the composition is to be used as a masterbatch, it may contain as much as 15% by weight of the substance.
Preferably, the substance contains a polar group to facilitate adsorption onto the inorganic additive, a non-polar group to enhance compatibility with the organic polymer and has a molecular weight preferably greater than 300.
Examples include:
a) amides: N,N'-ethylene bis
stearamide or the condensation
products of di-ethanolamine and
carboxylic acids;
b) polymethyl methacrylates;
c) aliphatic polyols: polyethylene
glycol, glycerine or mannitol;
d) sulphides: bis(dimethylthio
carbamyl)disulphide;
e) amino benzoic acids;
f) long chain aliphatic amines;
g) polyethers; and
h) most preferably epoxides.
A fuller description of these substances is provided in British patent specification
1,297,802.
The preferred epoxides are the uncured epoxy resins of the type described in pages 294 to 306 of Volume 8 of the second edition of the "Encyclopedia of Chemical
Technology'' edited by R E Kirk and D F
Othmer and published by John Wiley of
New York. The most common epoxy resins are condensation products of epichlorhydrin and bisphenol A. The stabilising efficiency of the isocyanurate is greater when the epoxy resin used is a viscous liquid.
Many adsorbent inorganic additives contain transition metal ions possibly as impurities and it is well known that such ions can catalyse the oxidative degradation of propylene polymers. Accordingly, it is sometimes beneficial to add so-called "metal deactivators" to the compositions of this invention. Metal deactivators are organic compounds which complex with transition metal ions to reduce the ability of the ion to catalyse the oxidative degradation of the propylene polymers. Typical metal deactivators are described in British patent specifications 1,219,783 and 1,166,949 and metal deactivators of particular interest include pentaerythritol, N-salicyl-N'salicylidine hydrazide, oxanilide, oxamide and preferably melamine or oxalic acid bis(benzylidenehydrazide).
The compositions may contain conventional ingredients such as light stabilisers, pigments, antacids (for example calcium oxide) and processing aids (for example soaps such as sodium or calcium stearates).
The compositions of this invention are suitable for use in making engineering components which require the propylene polymers to have increased resistance to deformation when hot and to undergo less shrinkage when cooling, especially when cooling after moulding. Typical components which may be made from the compositions are distributor caps, rocker box covers and timing chain covers for motor vehicles. The compositions may also be converted into foils by extrusion and/or rolling techniques.
Typical rolling techniques include calendering and chill roll casting and in particular the adaptation of the calendering process wherein molten composition is fed from an extruder or intensive mixer to the nip between a pair of parallel rollers. Foils (preferably 0.05 to 0.5 mm thick) produced in this way may be thermoformed into containers such as tubs for edible fats, trays for chocolates, and boxes for horticultural purposes. Thicker foils (for example 0.5 mm to 2.0 mm) may be thermoformed (for example by vacuum forming) into articles including motor vehicle comPonents, particularly trims such as fascias, door panels, floor and head-linings, wheel arches, car seat trims and parcel shelves. They can also be used to make cooling tower packings and effluent treatment packings.For certain products it might be useful to fill the shaped article with a suitable cellular foam material, for example polyurethane foam, or other support structure. Use may also be made of the vacuum-forming technique.
The foils may be embossed using an embossing tool (preferably a pressure roller) and/or they may be laminated to other sheet materials such as films, woven, knitted, felted and other non-woven textile fabrics or plastics coated textile fabrics.
Lamination may be carried out during the performance of the rolling technique used to form the foils or it may be carried out by extruding molten composition onto the sheet material.
The invention is further illustrated by the following Examples of which A to H are comparative. The percentages quoted are by weight based on the weight of the composition, that is to say on the total weight of the propylene polymer and all the additives, whether organic or inorganic.
Examples I to 6 and A to E
Propylene polymer compositions containing 40% talc, 2% calcium oxide, 1% carbon black and 0.2% calcium stearate were made by melt mixing these additives with a propylene homopolymer of melt flow index 4 together with various amounts of dilauryl thiodipropionate (DLTDP) and various amounts of anti-oxidants and epoxy resins as set out in Table 1. The epoxy resins were condensates of epichlorhydrin and bisphenol A sold under the Registered
Trade Marks of 'Araldite' or 'Epikote' 1002.
The compositions obtained were compression moulded into plaques 1,6 mm thick. The plaques were placed in an air oven maintained at a temperature specified in Table 1. After the samples had been in the air oven for a number of days they exhibited surface cracking and the time taken for this to occur is set out in Table 1.
It will be seen that at anti-oxidant concentrations of 0.2%, the isocyanurate anti-oxidant produces better results than anti-oxidants I and II even though I and II are used together with an epoxy resin.
Moreover, when the isocyanurate is combined with an epoxy resin, it will be seen that its performance is even better. TABLE 1
Oven Time taken Amount Amount % Epoxy Amount temperature to crack Example Anti-oxidant % of DLTDP compound % C - days 1 isocyanurate 0.2 0.5 - - 160 *12 2 isocyanurate 0.2 0.5 - - 150 31 A I 0.2 0.5 'Araldite' 0.5 150 19 B I 0.3 0.5 'Araldite' 0.75 150 29 C I 0.3 0.5 'Araldite' 1.00 150 34 **D II 0.2 0.5 'Araldite' 0.5 150 19 **E II 0.4 0.75 'Araldite' 0.75 150 22 3 isocyanurate 0.2 0.5 'Araldite' 0.5 150 34 3 isocyanurate 0.3 0.75 'Araldite' 0.75 150 70 5 isocyanurate 0.2 0.5 'Epikote' 1002 0.5 150 63 6 isocyanurate 0.4 0.5 'Epikote' 1002 0.5 150 70 The isocyanurate is 1,3,5-tris(3,5-ditertiary butyl-4-hydroxybenzyl)isocyanurate.
Anti-oxidant I is a pentaerythrityl tetra-ss-ditertiary butyl-4-hydroxyphenyl)propionate.
Anti-oxidant II is 1,1,3-tris(2'-methyl-5'-tertiary butyl-4-hydroxyphenyl)butane.
* Results obtained at 160 C are approximately half those obtained at 150 C, hence 12 days at 160 C.
** Sodium stearate was used instead of calcium stearate in Examples D and E.
Examples F to H.
In order to compare the effectiveness of the anti-oxidants in the absence of the talc and carbon black (which are adsorbent additives) identical samples were moulded from propylene homopolymer containing only 0.5% dilauryl thiodipropionate, 0.2% calcium stearate and 0.2 ó of an anti-oxidant as specified in Table 2. The samples were placed in an air oven maintained at 1500C and the time taken for them to crack is set out in Table 2.
TABLE 2
Time taken to crack Example Antisxidant - days F *isocyanurate 80 G *I 114 H *11 90 * as specified in Table 1.
The superiority of the isocyanurate in the presence of adsorbent inorganic additives contrasts with its inferiority in the absence of such additives.
In compositions containing substances which are adsorbed onto the inorganic additives in preference to the anti-oxidants, it is convenient to specify the concentrations of the isocyanurates and sulphur compounds as weight percentages based on the weight of propylene polymer in the composition. For example, such a composition may contain 0.01% to 6% (preferably 0.08 to 1%) by weight of isocyanurate and 0.1 to 10% (preferably 0.5 to 3%) by weight of the sulphur compound, the percentages being based on the propylene polymer in the composition.
WHAT WE CLAIM IS:
1. A propylene polymer composition comprising:
a) 10 to 85% by weight (based on the total
weight of the composition) of an
adsorbent inorganic additive,
b) an organic sulphur compound of the
type which synergises with hindered
phenolic anti-oxidants, and
c) an isocyanurate anti-oxidant which is a
sterically hindered phenolic ester of
isocyanuric acid having the general
formula:
where A1 is a group containing a sterically hindered phenol,
A2 and A3 are independently hydrogen, an alkyl group containing up to 11 carbon atoms or a group containing a sterically hindered phenol, and X, X2 and X3 are independently either the group: CH2)n or the group:
where n and p are independently 0, 1, 2 or 3 and m is 1, 2, 3 or 4.
2. A composition as claimed in claim 1 wherein the adsorbent additive comprises talc.
3. A composition according to claim 1 wherein the isocyanurate has the formula:
where t But is tertiary butyl.
4. A composition according to claim 1 wherein the isocyanurate has the formula:
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (25)
1. A propylene polymer composition comprising:
a) 10 to 85% by weight (based on the total
weight of the composition) of an
adsorbent inorganic additive,
b) an organic sulphur compound of the
type which synergises with hindered
phenolic anti-oxidants, and
c) an isocyanurate anti-oxidant which is a
sterically hindered phenolic ester of
isocyanuric acid having the general
formula:
where A1 is a group containing a sterically hindered phenol,
A2 and A3 are independently hydrogen, an alkyl group containing up to 11 carbon atoms or a group containing a sterically hindered phenol, and X, X2 and X3 are independently either the group: CH2)n or the group:
where n and p are independently 0, 1, 2 or 3 and m is 1, 2, 3 or 4.
2. A composition as claimed in claim 1 wherein the adsorbent additive comprises talc.
3. A composition according to claim 1 wherein the isocyanurate has the formula:
where t But is tertiary butyl.
4. A composition according to claim 1 wherein the isocyanurate has the formula:
where B is
and t But is tertiary butyl.
5. A composition according to any one of claims I to 4 wherein the composition contains from 0.01 to 12% by weight (based on the total weight of the composition) of the isocyanurate.
6. A composition according to claim 5 wherein the composition contains from 0.08 to 1% by weight of the isocyanurate.
7. A composition according to any one of the preceding claims wherein the composition contains from 0.01 to 15% by weight (based on the total weight of the composition) of the organic sulphur compound.
8. A composition according to claim 7 wherein the composition contains from 0.1 to 0.5or by weight of the organic sulphur compound.
9. A composition according to any one of the preceding claims wherein the propylene polymer is a crystalline copolymer of propylene with from 2 to 20% by weight (based on the weight of the propylene in the.
copolymer) of ethylene.
10. A composition according to claim I substantially as hereinbefore described and illustrated by Examples I and 2.
I I. A propylene polymer composition comprising:
a) 3 to 950 by weight (based on the
total weight of the composition) of
an adsorbent inorganic additive.
b) an isocyanurate anti-oxidant which
is a sterically hindered phenolic
ester of isocyanuric acid as defined.
in claim 1,
c) an organic sulphur compound which
synergises with hindered phenolic
anti-oxidants, and
d) 0.01 to 5 Ó by weight (based on the
weight of the adsorbent inorganic
additive) of a substance which is
adsorbed onto the adsorbent
inorganic additive in preference to
the isocyanurate so as to reduce the
impedance of the stabilisation of the
composition by the additive.
12. A composition according to claim 11 wherein the propylene polymer is a homopolymer of propylene or a copolymer of propylene with up to 20% by weight of ethylene based on the weight of propylene in the copolymer.
13. A composition according to claim 11 wherein the composition contains from 0.01 to 6% (by weight of the propylene polymer) of the isocyanurate.
14. A composition according to claim 13 wherein the composition contains from 0.08 to 1% by weight of the isocyanurate.
15. A composition according to any one of claims 11 to 14 wherein the substance adsorbed onto the inorganic additive in preference to the isocyanurate is an epoxy resin.
16. A composition according to claim 15 wherein the epoxy resin is a condensation product of epichlorhydrin and bisphenol A.
17. A composition according to any one of claims 11 to 19 wherein the substance adsorbed onto the inorganic additive in preference to the isocyanurate is N,N'ethylene bis-stearamide, a condensation product of di-ethanolamine and carboxylic acids, a polymethyl. methacrylate, a polyethylene glycol, glycerine, mannitol, bis(dimethylthiocarbamyl) disulphide, an amino benzoic acid, or a polyether.
18. A composition according to any one of claims 11 to 17 wherein the composition contains from 0.1 to 10% (by weight of the propylene polymer) of the organic sulphur compound.
19. A composition according to claim 18 wherein the composition contains from 0.5 to 3% (by weight of the propylene polymer) of the organic sulphur compound.
20. A composition according to any one of claims 11 to 19 wherein the adsorbent inorganic additive comprises talc, carbon, calcium carbonate, slate dust, mica, clay or hollow bodies composed of aluminium silicates.
21. A composition according to claim 20 wherein the additive is limestone or coccolithic chalk.
22. A composition according to claim 11 substantially as hereinbefore described and illustrated by any one of Examples 3 to 6.
23. A moulded article made from a composition according to any one of the preceding claims.
24. A foil made by extruding and/or rolling a composition according to any one of claims I to 22.
25. A trim for a motor vehicle made by thermoforming a foil according to claim 24.
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB490177A GB1565745A (en) | 1977-02-07 | 1977-02-07 | Stabilisation of propylene polymers containing inorganic additives |
| NZ186352A NZ186352A (en) | 1977-02-07 | 1978-01-30 | Propylene polymer containing isocyanurate anti oxidant |
| AU32949/78A AU515105B2 (en) | 1977-02-07 | 1978-02-02 | Stabilisation of propylene polymers containing talc |
| FR7803037A FR2379569A1 (en) | 1977-02-07 | 1978-02-03 | Stabilised polypropylene compsn. contg. absorbent inorganic filler - contains a synergic mixt. of an organic sulphur cpd. and an isocyanuric acid ester with hindered phenol gps. (BE 7.8.78) |
| BR7800731A BR7800731A (en) | 1977-02-07 | 1978-02-03 | PROPYLENE POLYMER COMPOSITION AND SHEET MADE WITH IT |
| JP1157378A JPS53114853A (en) | 1977-02-07 | 1978-02-06 | Polypropylene composition |
| DE2804980A DE2804980B2 (en) | 1977-02-07 | 1978-02-06 | Stabilized propylene polymer compositions containing inorganic additives |
| SE7801349A SE7801349L (en) | 1977-02-07 | 1978-02-06 | PROPENE POLYMER COMPOSITION |
| NL7801383.A NL163810B (en) | 1977-02-07 | 1978-02-07 | PROPENE POLYMER COMPOSITIONS. |
| BE184968A BE863729A (en) | 1977-02-07 | 1978-02-07 | STABILIZATION OF PROPYLENE POLYMERS CONTAINING INORGANIC ADDITIVES |
| IT20074/78A IT1093653B (en) | 1977-02-07 | 1978-02-07 | STABILIZATION OF PROPYLENE POLYMERS CONTAINING INORGANIC ADDITIVES |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB490177A GB1565745A (en) | 1977-02-07 | 1977-02-07 | Stabilisation of propylene polymers containing inorganic additives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1565745A true GB1565745A (en) | 1980-04-23 |
Family
ID=9786018
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB490177A Expired GB1565745A (en) | 1977-02-07 | 1977-02-07 | Stabilisation of propylene polymers containing inorganic additives |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE863729A (en) |
| GB (1) | GB1565745A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5086100A (en) * | 1988-05-09 | 1992-02-04 | Sumitomo Chemical Co., Ltd. | Inorganic filler containing polyolefin composition |
| WO1998044025A1 (en) * | 1997-04-02 | 1998-10-08 | Kimberly-Clark Worldwide, Inc. | Stretched-filled microporous films and methods of making the same |
-
1977
- 1977-02-07 GB GB490177A patent/GB1565745A/en not_active Expired
-
1978
- 1978-02-07 BE BE184968A patent/BE863729A/en unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5086100A (en) * | 1988-05-09 | 1992-02-04 | Sumitomo Chemical Co., Ltd. | Inorganic filler containing polyolefin composition |
| US5086099A (en) * | 1988-05-09 | 1992-02-04 | Sumitomo Chemical Co., Ltd. | Inorganic filler containing polyolefin composition |
| WO1998044025A1 (en) * | 1997-04-02 | 1998-10-08 | Kimberly-Clark Worldwide, Inc. | Stretched-filled microporous films and methods of making the same |
| US6156421A (en) * | 1997-04-02 | 2000-12-05 | Kimberly-Clark Worldwide, Inc. | Stretched-filled microporous films and methods of making the same |
Also Published As
| Publication number | Publication date |
|---|---|
| BE863729A (en) | 1978-08-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |