CA1073921A

CA1073921A - Organic phosphites and their use as stabilizers

Info

Publication number: CA1073921A
Application number: CA253,603A
Authority: CA
Inventors: Harald Haberlein; Franz Scheidl
Original assignee: Hoechst AG
Current assignee: Hoechst AG
Priority date: 1975-05-30
Filing date: 1976-05-28
Publication date: 1980-03-18
Also published as: BE842413A; DK235376A; IE42824B1; ZA763174B; DE2523910C3; DE2523910B2; NL7605608A; BR7603415A; FR2312504A1; JPS51143622A; IT1060731B; DE2523910A1; IE42824L; GB1532709A; LU75049A1

Abstract

Abstract of the disclosure:
The present invention is related to novel phosphites, their use as stabilizers for organic polymers, furthermore to stabilizer compositions containing these novel phosphites as well as the organic polymers being stabilized therewith.
The novel phosphites have a good stabilization effect, especially in combination with known stabilizers, and they are substantially stable against hydrolytical influence.
Their volatility and tendency to exudation are very weak.

Description

` 10739Zl ~OE 75/~ 804 :.
Limiting as far as possible the detrimental influence of heat and light on synthetic polymers requires the addition of stabilizers and stabilizing additives to the polymers so as to prevent degradation. It is also known that synergistic effects may he achieved by combined a~dition of stabilizers and stabilizing additives. Usually applied stabilizing additives are, for example, epoxy compounds, antioxidants, compounds absorbing ultra-violet radiation, and organic phos-phites.
However, the stabilizing additives are very often not entirely satisfactory, some havin~ even multiple shortcomings at the same time. An insufficient resis*ance to hydrolytic influence and a relatively high degree of volatility plague, , for e~ample, a séries of known organic phosphites which are used for stabilization purposes. Moreo~er, among these phos-phites are some not entirely unobjectionable in the physio-logical field.
The object of present invention was thereforeto provide ~tabilizers based on organic phosphites which do not have-said disadvantages and which show a highly stabilizing effect.
It has been found now that phosphites of the generalformula .. \
B - O / P

wherein A, B and C are identical or different organic radicals and wherein at least one of the radicals has the structure R - C ~CI - Rt or H - C -Cl - H
OH ~

' - 1073921 HOE 75/i` 804 R and R' may be identical or different ~nd represent a hydro-gen atom, an aryl group or a cycloalkyl group or an alkyl group and wherein the sum of the carbon atoms included in R
and R~ does not exceed 60, and wherein X is a straight-chain saturated or unsaturated alkylene radical, whilst possible residual radicals B and C are either aryl group~ or cyclo-alkyl groups or alkyl groups and wherein the total number of carbon atoms included in the radicals A, B and C is at least 10 - do surprisingly display to a large sxtent the advan-tageous properties sought after.
Th0 present invention ls being rela~ed, therefore, theabove mentioned organic phosphites which were not known be-fore, their use as stabili~ers for organic polymers, stabi-- lizer composit~ons containing these phosphites and organic polymers being stabilized by means of these phosphites.
A special advantags of the phosp~ites according to the invention is their resistance to hydrolytic influence which is substantially increased in comparison to many other phos-ph~te stabilizers, a fact which improves the weathering properties of the molding compositions which are stabilized with the phosphites of the invention.
The fact that those among the novel phosphites occurring a~ subYtances which are solid at room tenperature, impart an dimension stability under heat to the plastic better articles processed by means of these phosphites than by using known liquid phosphites - i$ to be considered a further advantage. Finally, the use of the phosphites as per the in~ention reduces substantially the formation of tarnish 29 on the processing machines and of groove~ on the shaped -- 3 ~

... . ..... .

107392.1 HOE 75/F 804 articles being produced. Additional valuable properties are the lnodorousness, the practically absent ~olatility and the lacking tendency to exudation.
The ph4sphitesas per the invention are obtained according to known methods by transesterification of tri-low alkyl-phosphites or Or triphenyl phosphites with the corresponding hydroxy compounds. Some are still liquid at room temperature;
generally and preferably, however, the novel phosphites re-present solid white products - part of them having wax-like characteristics. Most interesting are the latter having flow-drop-points of from about 35 to 100C, since in addition to their stabilization effect they influence fa~orably the pro-perties of the products made of polymer molding compositions containing such ~-ax-like phosphites.
In the phosphites of the general formula A - O \
B - O P
'., C - 0/

A, ~ and C are identical or different organic radicals at least one of these radicals has to be of a structure as per the formula R - C - C - R~ H - C - C - H
I I or ¦
OH OH
I II

In case that only radical A has one of these structures, B and C may be a.lkyl groups having from 1 to 60, preferably from 1 to 30 carbon atoms and/or aryl groups and/or cyclo-' ' ~ ' ' .

~07392~ HOE 7~tF 804 alkyl grotlps having each from 5 to 12, preforably 5 or 6 carbon atoms. The aryl group may be optionally substituted by alkyl radicals or alkoxyl radicals having preferably from 1 to 6 carbon atoms. If A and B have structure I and/or II, C is one of the afors mentioned radic~ls.
Preference is given to one or two only of radicals A, B, C having either structure I or II.
The letters R and R~ being employed in the general formu-la I stand for identical or different radicals, namely hydro-gen, an aryl group having from 6 to 15 carbon atoms which may be substituted optionally by alXyl groups or alkoxyl groups having preferably from 1 to 6 carbon atoms, by chlorine or hydroxyl groups, such as a phenyl group, a tolyl group, a xylyl group, a tert.-butylphenyl group, a nonylphenyl group, a chlorophenyl group or a hydroxyphenyl group. Furthermore, R and Rl represent a saturated or unsaturated substituted or unsubstituted cycloalkyl radical having from 5 to 12 carbon atoms, such as a cyclopentyl radical, a cyclohexyl radical, a cycloheptyl radical, a cyclooctyl radical, or a cyclododecyl radical, or as well a straight-chain or branched alkyl radical having from 1 to 60, preferably from 8 to 40 and especially from 8 to 20 carbon atoms, such as, for example, the ethyl - radical, butyl radical, hexyl radical, octyl radical, decyl radical, dodecyl radical, tetradecyl radical, hexadecyl radical, octadecyl radical, eicosyl radical, docosyl radical, tetra-cosyl radical, hexacosyl radical, octacosyl radical, tria-contyl radical, dotriacontyl radical, tetratriacontyl radical, hexatriacontyl radical, octatriacontyl radical, tetracontyl 29 radical or dotetracontyl radical. The sum of the carbon atoms ~ 5 --, ' .
' ` 1073921 HOE I~/F 804 contained in R and K: sh~ld not exceed a maximum of 60, preferably of about 40.
If Rl in structure I is hydrogen, methyl or ethyl, a straight-chain alkyl radical is preferred for R, having from 6 to 58, preferably from 18 to 40 and especially from 20 to 36 carbon atoms. Structures I of this kind, wherein R' is hydro-gen, are suitable for being incorporated into the phosphite through the corresponding 1,2 diols, these latter may be pre-pared for example from the corresponding epoxides by adding water.
If use is made of epoxide mixtures such as they are ob-tained e.g. by epoxidizing mixtures of commercially available long-chain ~-olefins, products are obtained the structure of which is characterized by designations such as C20/24 alkyl- ~ C18/22~37/45-"~ ~lC30~-alkyl_ll; cf.table page 12, footnotes 3,4 and 5.
In formula II "X" represents a straight~chain saturated or unsaturated alkylene radical having from 3 to 10, preferably from 5 to 7 carbon atoms. A group of structure II is e.g. the ~-hydro~y-cyclohexyl radical.
A further characteristic quality of the phosphites is that the total number of carbon atoms contained in the radicals A, B and C amount~ to at least 10, preferably to at least 16.
Some particularly representati~e novel phosphites may be cited thereaf~er, though the inYention is not to be limited to said substances:

, - 1073921 HOE 7 5/~ 804 tris(2-hyd-oxydodecyl)phosphite (CloH21 ~H-CH2 o)3p ethyl-bis(2-hydroxyhexadecyl)phosphite(C14H29-CH-CH2-0)2P OC2H,~;
OH

(2-h-yd-rny-~vh~x~ yl )phQ~ 4~Z~ H-r'HZ n) OH
diethyl(2-hydroxyoctadecyl)phosphite C16H33~H-CH2-O P(OC2H5)2 OH
. . .
:.; ethyl-bis(2-hydroxyoctadecyl)phosphite(cl6H33lcH-cH2-o)2p OC2H5 OH

, phenyl-bis(2-hydroxyoctadecyl)phosphite(C16H337H-CH2-0)2P OC6H5 OH
tris(2-hydroxyoctadecyl)pho~phite(C16H33-lCH-CH20)3P
OH
diethyl ( 2-hyd~oxy-c2o/24-alky~
.', phosphite 18~22H37/4s-1H-CH2--P (OC2H5)2 ,. H
"~ phenyl-bis(2-hydroxy-C20J24-alkyl)phosphite / ( 18/22 37/45~ClH~cH2~o)2p OC6~5 OH
tris-(2-hydroxy-C20/24-alkyl ~
phosphite (C18/22H37~45-ClH CH2 )3 , OH
'i diethyl(2-hydroxy-C24/28-alkyl~
pho phite 22/26H45/s3-~CH-CH2-O P(oc2H5)2 OH
ethyl-bi s ( 2-hydroxy-C24/28,,~
. alkyl)phosphite (C22/z6H45/s3-~CH^cH20)2P OC2H5 OH
,' .

, ' ' , .
;' ' ~ ' ' . :
., - . -.

1073921 HOE 7~/F 804 , ` .

tris(2-hydroxy-c2ll~2g-alkyl)phosphite(c22/26H4s/53 ~H C 2 )3 OH

diethyl(2-hydroxy-c3o+-alky~ 30H61 1 2 2 5 2 phosphite OH

ethyl-bis(2-hydroxy-C30+-alkyl)phosphite (~C30H6llH-cH20)2P
OH

OCzH5 diphenyl(2-hydroxy-c3o~alkyl ~

phosphite C30H61-pH-CH20 P(OC6H5)2 OH

- phenyl-bis(2-hydroxy-c3o+-alkyl)~

phosphite (~ C30H6l-lH-cH2-o)2p C6 5 OH

triS(2-hydroxy-c3o~-alkyl)phosphite (~ C30H61-~H-CH20)3P
I H

The novel phosphites may be used also in admixture to each other, optionally combined with different, generally known ~tabilizers, stabilizing auxiliaries, antioxidanta and ultra-violet-stabilizing compounds.
Upon processing chlorinated polymers, such as chloropoly-ethylene, rigid and soft polyvinyl chloride, polyvinylidene - chloride, polyvinylchloroacetate and vinyl chloride-O~-ole-fin-copolymers a substantially improved stability under heat and to light is achieved by adding the novel phosphites claimed herewith, in the presence of compounds known as stabi-lizers, such as metal compounds, indoles substituted in 2-' ,~ . ', .'' " ' , .' . ~

10739Zl HOE 7~/~ 804 position, preferably 2-phenylindole, epoxide stabilizers and possibly polyhydric alcohols.
By metal compounds ~nown as stabilizers are to be under-stood: Ca, Ba, Sr, Zn, Cd, Mg, ~1 and Pb soaps of aliphatic carboxylic acids or oxyca.boxylic aclds ha~ing from about ~ to 32 carbon atoms, preferably from 8 to 24 carbon atoms, salts of these metals with aromatic carboxylic acids of preferably from 7 to 12 carbon atoms, such as benzoates, salicylates as well as (alkyl)phenolates of these metals, the alkyl radical having from 1 to 12, preferably from 1 to 6 carbon atoms. This range of compounds also includes organotin compounds such as dialkyl-tin-thioglycolates and carboxylates as well as -; optionally - neutral and basic lead salts of inorganic acids ; such as sulfuric acid and phosphorous acid.
Known epoxide stabilizers are, for example, higher s ~ epoxidized fatty acids such as epoxidized soybean oil, tall ; oil or linseed oil, epoxidized butyloleate and higher epoxy-alkanes.
Polyhydric alcohols are e.g. pentaerythritej trimethylol . 20 propane, sorbitol or mannitol, i.e. preferably alcohols having from 5 to 6 carbon atoms and from 3 to 6 OH groups. I
!
Stabilizers of this kind such as metal compounds, epoxides and polyhydric alcohols are described, for example, in J.Voigt "Stabilisierung der Kunststoffe gegen Licht und Warme", Springer-Verlag, Berlin-Heidelberg-New York (1966).
A ~ery efficient stabilizer composition for processing halogenated polymer molding compositionsconsists, for example, ; of from 0.01 to 10 parts by weight of a phosphite according 29 to the in~ention, 0.1 to 10 parts by weight of metal compounds - 9 _ ' - 10739Zl H0~ 7 5/F 804 known as stabilizers, 0.1 to 10 parts by weight of a known epoxide stabilizer and 0 to 1 part by weight of a polyhydric alcohol.
The novel phosphites display also an excellent efficiency - 5 for stabilizing polymers or copolymers of olefins free from halogen. The stability of e.g. polypropylene under heat and to light is considerably improved by the addition of the novel phosphites, especially in admixture to phenolic and/or sul-i~ fidic stabilizers.
By phenolic and sulfidic stabilizers are to be understood the generally known stabilizers against heat und to light which are used in the processing of plastics, such as 3.5-ditertiarybutyl-4-hydroxyphenyl-propionic acid-ester, 2.6-di-tertiarybutyl-p-cresol, alkylidene-bis-alkyl-phenols, esters ~- 15 of bis-(4~-hydroxy-3t-tertiary-butylphenyl)-butyric acid, thiodipropionic acid ester of fat alcohols as well as diocta-decyl sulfide or dioctadecyl disulfide; cf. - J.Voigt, "Stabilisierung der Kunststoffe gegen Licht und Warme", ~ Springer-Verlag, Berlin-Heidelberg-New York (1966).
-~ 2~ A synergistically efficient stabilizer composition for j; polymers or copolymers of olefins free from halogen consists, for example, of from 0.05 to 5 parts by weight of a phosphite according to the invention, from 0.05 to 3 parts by weight of a known phenolic stabilizer and/or of from 0.1 to 3 parts by weight of a known sulfidic stabilizer. Special stabilizers against ultra-violet rays may also be added to the stabilizer composition at a rate of from 0.1 to 3 parts by weight, if deemed necessary. Known ultra-violet absorbers are e.g. al-29 koxy-hydroxybenzophenones, hydroxyphenylbenzotriazoles, , ' ~
' ' ' - ' ' , ' .

` 10739Zl HOE 75/F ~04 ~alicilic acid phenolic ester, benzoic acid hydroxyphenolic ester, benzylidene malonic acid mononitrile ester as well as so-called "quenchers" such as nickel chelates, hexamethyl-phosphoric acid triamide or - as recently made known - pi-peridine stabilizers.
Stabilizer compositions of the phosphites according to the invention and known stabilizers not only do improve the stability of polyolefins, chloropolyolefins and chlorinated vinylpolymers, but impart also an improved stability to poly-esters, polyamides, polyacrylonitrile, polycarbonates, poly-i` siloxanes, polyethers~poly urethanes and others.
; The following Examples illustrate the invention and specify the advantages of the novel phosphltes:
E X A M P L E 1:
A 1 liter-four-necked flask being equipped with an agi-tating device, an internal thermometer, gas inlet and descen-ding cooler i9 rinsed with nitrogen and subsequently charged with 42~ g (1.5 mole) of octadecanediol-1.2 and 83 g ~0.5 mole) of newly distilled triethyl phosphite. During 20 - 30 minutes the content of the flaqk is heated to 115 - 120C in a weak nitrogen current, while stirring, ethanol is then starting to separate at an internal temperature of about 110 C. Within rurther 3 - 5 hours, while stirring is continued, the tempera-ture of the reaction mixture is slowly increased from 120C
to a final temperature of 160C. 66.2 g of ethanol are distilled off during this period of time. Agitation is then continued for another hour in a water jet vacuum of 10 - 20 mm at the unaltered temperature of 160 C, in order to remove 29 possible volatlle components. In a cooling trap set up 10739Zl HOE 75/F 804 .
between the described apparatus and the water jet pump there are found after this period of time 3.1 g of a liquid clear as water consisting of 1. 2 g of triethyl phosphite and further 1.9 g of ethanol.
Thus a total quantity of 68.1 g = 98.6 % of the theo-retical yield of ethanol was separated.
After cooling down the limpid, slightly yellowish melt 438 g z 98.8 % of the theoretical yield of tris-(2-hydroxy-octadecyl)phosphite are obtained as a white wax having a flow-drop-point of 59.5 - 61 C (being determined according to DGF M III 3 (57) ), containing 3.3 % of phosphorus of the molecular weight of 854. Theory for the compound of a : summation formula C54H11106P of 3.5 % P and a molecular . weight of 886.
. 15 E X A M P L E S 2 - 14s .~ Further compounds among the no~el phosphites ha~e been prepared by synthesis according to the method thoroughly deJcribed by Example 1. The following table groups the special - preparation characteristics and the analytical characteriza-tion of the products obtained by the processes.

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~ - 13 - - 13a -` ~0739Zl HOE 75/F 804 E X A M_~ k~
.,, -- -- . .
; The following method was applied for determining the ' stability to hydrolysis of the novel phosphites in comparison ,- to the stability of four commercially available products:
5 g of phosphite were heated to the boiling noint in ; 100 ml of distilled wate~ after having boiled for 20 to 60 minutes, the reaction mixture is cooled and its content in phosphorous acid determined in the aqueous solution by mean~
, of titration with aqueous 0.1 n-sodiumhydroxide solution. The degree of hydrolysis Qf the phosphite submitted to the test is randomly determined as a ratio of 100 x/y, x being th0 actually consumed volume of 0.1 n-NaOH and y being the theo-retical volume of this reagent, calculation based on a supposedly completed hydrolysis of the phosphite to yield ~- 15 phosphorous acid.
,. _ . .... .. . . _. _ _.
. Degree of hydrolysis P h o 8 p h i t e. in % after a boiling¦
time of _l ~ 20 Min. 60 Min.

a) )Triphenylphosphite 84 100 b)1)Tris(nonylphenyl)phosphite 57 9Z
c)l)Diphenyl-isooctylphosphite 55 77 d)l)Di4tearyl-pentaerythrityl-diphosphite 52 68 _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ e) Ethyl-bis~2-hydroxyoctadecyl)phosphite 33 42 f) Diethyl-(2-hydroxyoctadecyl~phosphite 21 3o g) TriS(2-hydroxy-c24/28-alkyl)phosphite 35 51 h) Ethyl-bis~2-hydroxy-c24/28-alkyl)phosph . 31 41 i) Diethyl-(2-hydrOxy-c24/28-alkyl)phosph- 25 36 ~- j) Ethyl-bis(2-hydroxy-c3o+-alkyl)phosph~ 11 13 k) Tris-(2-hydroxy-c3o+-alkyl)phosphite 16 23 1) Phenyl-bis(2-hydroxy-C~O+-alkyl)phosph. 12 13 1) Commercially a~ailable products as comparative substances :

1073921 HOE 7~t~ 804 E X A M P L S S 16 to 39:
These Examples show the stabilizing effect of the phos-phites according to the invention upon processing polyvinyl chloride. The dynamic stability under heat (Example 16 to 27) ~d +h~ static st~h~1it~r unrl~ h~at (EY~mp1~s 28 t^ 39) ~e determined. The specified parts are parts by weight.
1~0 Parts each of a mass-polyvinyl chloride having a K-value of 60 were mixed thoroughly with 0.2 parts of 2 phenylindole, 3 parts of epoxidized soybean oil, 0.25 parts of a c~mplex calcium/zinc stabilizer consisting of 42 weight ~
of ca~cium ~tearate, 30 weight % of zinc stearate, 22 weight %
of pentaerrthrite and 6 weight % of 2,6-di-t-butyl-4-methyl-phenol, 0.2 part of a montanic acid ester (acid number 18, saponification number 154~, 0.3 part of stearyl stearate, -5 part of glycerolmonostearate, and 0.5 part of the phos-phites.
In order to determine the dynamic stability under heat the mi~tures were applied onto a laboratory-scale twin-roller device heated to 180 C and rolled-out to a sheet (pelt) within one miD~te at 20 rpm. In intervals of 10 minutes spot samples were picked of the~e ~heets, and their color shades compared with an internal color chart. The various tests were run each until the rolled-out sheet had taken up a dark-brown to black shade.
In order to determine the static stability under heat, a rolled-out sheet was first prepared from the mixtures according to the afore given description, and this sheet being rolled-out on the twin-roller device at 180C for another 10 29 mimltes~ period. The sheet was then peeled off the roller , ', 107392~ HOE 7~ 4 , . .
and flats of about 0.5 mm thickness and a diameter of 30 mm blanked therefrom. The flats were wrapped in an alumin_um sheet and tempered at 180~ in a heating cabinet with internal air circulation. One flat was picked every 10 minutes and 5 its color sha'e cv...pa.ed w '.. ~ha co or cha;^t. The val-ue figures employed in the color chart ha~e the following .
- meaning:

1 = clear as water

2 = slightly yellowish

3 = distinctly yellow tint

4 = dark yellow-brown shade

5 = dark brown to black A~ demonstrated by the following tables, the polyvinyl ; chloride being stabilized by organic phosphites according to the present invention is clearly superior in comparison to polyvinyl chlor$de being stabilized with known phosphites and with mixtures free from phosphites as far as their dynamic ,: stability and their stability under heat are concerned.
r;

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.

- 16 _ ,. .

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E X A M P L E ~lO-This example shows that the addition of the phosphites according to the invention to polypropylene improves consider-ably its stability to light and against alterations due to heat.
A powdery mixture consisting of 100 parts by weight of unstabilized polypropylene ~ 5(230oc)about ~
0.15 part by weight of octadecyl-3-(3~,5~-di-tert.-butyl-4~-hydroxyphenyl)-propionate and 0.10 part by weight of the ethyl-bis(2-hydroxy-C24/28-alkyl)phosphite prepared according to Example 7 - 15 was injection-molded on an injection molding machine to yield test plates measuring 60 x 60 x 1 mm. Test specimens were blanked from these plate~.
The stability to light was determined by means of the Xeno-test device, type 150, produced by Messrs. Hanau Quarz-; 20 lampen GmbH with the filter combination 6 IR + 1 UV as per DIN 53 387. (DIN = German Industrial Standard). The time of exposure to light, i.e. the period of time after which the ab-~i fiolute elongation at break had decreased to 10 % was measured in hours. In the case of polypropylene being stabilized with ethyl-bis(2-hydroxy-C24/28-alkyl)phosphite this time of ex-posure amounted to 695 hours. Comparative secimens which had been prepared according to the above specified recipe - but ~ without ethyl-bis(Z-hydroxy-C24/28-alkyl~phosphite - reached 29 only 540 hours for this time of exposure.
_ 19 _ ~,. - , .

- ~IOE 75/F 804 The resistance to alterations under heat of in~ection molding test samples which had been measured approximately to the procedure described by DIN 53 383 at an airtemperature of 140 C, amounted to 40 days until total embrittlement of the polypropylene being stabilized with ethyl-bis(2-hydroxy-C24/28-alkyl)phosphite; the resistance to alterations under heat of comparative sampleY reached 22 day~.

.

- 20 _

Claims

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:

1. A phosphite of the general formula wherein A, B and C are identical or different organic radicals and wherein at least one of these radicals has the structure or wherein R and R' may be identical or different and represent a hydrogen atom, an aryl group, a cycloalkyl group or an alkyl group, and wherein the sum of the carbon atoms included in R
and R' does not exceed the number 60, and wherein X is a straight-chain saturated or unsaturated alkylene radical, and, when one or two of A, B and C radicals has the above structure, the other radicals from the group of A, B and C are either aryl radicals, cycloalkyl radicals or alkyl groups, and wherein the total number of carbon atoms included in the radicals A, B and C is at least 10.

2. A phosphite as claimed in claim 1 in which the radi-cal A is a straight-chain or branched hydroxyalkyl group having the formula , wherein R is an alkyl group having from 6 to 58 carbon atoms and R' is a hydrogen atom, a methyl group or an ethyl group, and wherein the sum of the carbon atoms in R and R' amounts to from 6 to 60, and wherein the radicals B and C are alkyl groups having from 1 to 60 carbon atoms.

3. A phosphite as claimed in claim 1 in which the radi-cals A and B are identical or different straight-chain or branched hydroxyalkyl groups having the formula wherein R is an alkyl group having from 6 to 58 carbon atoms and R' is a hydrogen atom, a methyl group or an ethyl group, and wherein the sum of the carbon atoms in R and R' amounts each to from 6 to 60, and wherein the radical C is an alkyl group having from 1 to 60 carbon atoms.

4. A phosphite as claimed in claim 1 in which the radi-cals A, B and C are identical or different straight-chain or branched hydroxyalkyl groups of the formula wherein R is an alkyl group having from 6 to 58 carbon atoms, R' is a hydrogen atom, a methyl group or an ethyl group, and wherein the sum of the carbon atoms in R and R' amount each to from 6 to 60.

5. A stabilizer composition, suitable for stabilizing chlorinated polyolefins and chlorine-containing vinyl-homopolymers and vinyl-copolymers, comprising from 0.01 to 10 parts by weight of at least one phosphite as claimed in claim 1, claim 2 or claim 3, from 0.1 to 10 parts by weight of a Ca-, Ba-, Sr-, Zn-, Cd-, Mg-, Al- or Pb-salt of a higher aliphatic or an aromatic carboxylic acid, from 0.1 to 10 parts by weight of an epoxidized higher fatty acid or a higher alkane and from 0 to 1 part by weight of a poly-hydric alcohol selected from the group consisting of pentaerythrite, trimethylolpropane, sorbitol and mannitol.

6. A stabilizer composition, suitable for stabilizing polymers or copolymers of olefins free from halogen, comprising from 0.05 to 5 parts by weight of at least one phosphite as claimed in claim 1, claim 2 or claim 3, from 0.05 to 3 parts by weight of a phenolic stabilizer selected from the group 3,5-ditertiary-butyl-4-hydroxyphenyl-propionic acid-ester, 2,6-ditertiarybutyl-p-cresol, alkylidene-bis-alkyl-phenols,esters of bis-(4'-hydroxy-3'-tertiary-butylphenyl)-butyric acid, and/or from 0.1 to 3 parts by weight of a sulfidic stabilizer selected from the group thiodipropionic:
acid-ester of fat alcohols, dioctadecyl sulfide or dioctadecyl disul-fide, and from 0 to 3 parts by weight of a stabilizer against ultra-violet radiation selected from alkoxy-hydroxy-benzophenones, hydroxyphenyl-benzotriazoles, salicilic acid phenolic ester, benzoic acid hydroxyphenolic ester, benzylidene malonic acid mono-nitrile ester, nickel chelats, hexamethylphosphoric acid triamide and piperidine stabilizers.

7. A plastic molding composition comprising an organic polymer containing a phosphite as claimed in claim 1, claim 2 or claim 3.

8. A plastic molding composition comprising an organic polymer in admixture with a phosphite as claimed in claim 1, claim 2, or claim 3, the phosphite being present in an amount of from 0.01 to 10 parts by weight per 100 parts by weight of polymer.