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Neo Diol Phosphite Esters and Polymeric Compositions Thereof

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Neo Diol Phosphite Esters and Polymeric Compositions Thereof ^ ^ ^ ^ I ^ ^ ^ ^ ^ ^ II ^ II ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ I ^ European Patent Office Office europeen des brevets EP 0 785 209 A1 EUROPEAN PATENT APPLICATION (43) Date of publication: (51) |nt ci * C07F 9/6574, C08K 5/527 23.07.1997 Bulletin 1997/30 (21) Application number: 97300269.4 (22) Date of filing: 17.01.1997 (84) Designated Contracting States: • Gray, Carloss L. DE ES FR GB IT NL P.O. Box 843, Belpre, Ohio 45714-0843 (US) (30) Priority: 22.01.1996 US 589832 (74) Representative: Szary, Anne Catherine, Dr. et al London Patent Operation, (71) Applicant: GENERAL ELECTRIC COMPANY GE International, Inc., Schenectady, NY 12345 (US) Essex House, 12-13 Essex Street (72) Inventors: London WC2R 3AA (GB) • Prabhu, Vaikunth S. Vienna, West Virginia 26105 (US) (54) Neo diol phosphite esters and polymeric compositions thereof (57) A phosphite and stabilized themoplastic composition comprising the phosphite where the phosphite has the formula: In the above compound, R7 and R8 are preferably alkyl of from 1 to 6 carbon atoms, most preferably an unsubstituted alkyl group. R9 is preferably alkyl of 1 to 1 2 carbon atoms, m is from 0 to 5. The dicumyl group includes the OX groups which are the phosphite portion. The OX group is hindered by only one alkylaryl group at the ortho position with the other ortho position being occupied by hydrogen. X has the following formula: —r'-^C—C C— O ^c— o (Rsk C p- !/C p- *2 2 C— O (R5)r-CZ2-^c^ O) o (R5)/(R5)2' CM or lO 00 wherein R2 is independently selected from the consisting of alkyl having from 1 to 12 carbon atoms, Is- group groups z-, and z2 can be 0 or 1. R3, R4 and R5 are independently selected from the group consisting of hydrogen, halogen, or o alkyl of from 1 to 3 carbon atoms. a. LU Printed by Jouve, 75001 PARIS (FR) EP 0 785 209 A1 Description The present invention relates to phosphites, and more particularly relates to aromatic cyclic phosphites which contain a neo substituted carbon group and stabilizing compositions and stabilized resin containing such phosphite 5 compositions. Description of the Related Art U.S. Patent 3,415,906 describes cyclic phosphites of the formula: 15 20 R9 25 In this patent, R1 and R2 are set forth as being alkyl of 3 to 12 carbon atoms, aralkyl having from 7 to about 15 carbons, R3 is selected from the group consisting of hydrogen, alkyl having from 1 to 12 carbons, aralkyl having from 7 to 15 carbons, halogen, and lower dialkyl tertiary amino. U.S. Patent 3,467,733 to Dever et al describes cyclic phosphites and diphosphites, such as bis(1 ,3,2-dioxaphosphorinanyl-2-oxy)aryl alkanes, and mono- and bis(1 ,3,2-dioxaphos- phorinanyl-2-oxy)benzenes, useful as stabilizers for organic compositions, such a rubber and polyvinyl chloride. Note 30 that column 3, lines 63 to 65 states: It is preferred to employ hydroxy compounds or phenols which do not have hindered 2,6-substitution on the benzene ring. U.S. Patent 5,364,895 to Stevenson describes bis(aralkylphenyl)pentaerythritol diphosphites of low volitility. Many of these phosphites can, however, experience thermal stability problems, hydrolytic stability problems, and/ or ultraviolet light discoloration problems. Hence, there still remains a need to enhance the various properties of phos- 35 phite compositions and find economical phosphite compositions. Summary of the Invention The present invention relates to aromatic dicumyl phosphites of the formula: 40 45 50 In the above compound, R7 and R8 are preferably alkyl of from 1 to 6 carbon atoms, most preferably a straight chain 55 alkyl group. R9 is preferably halogen, or alkyl of 1 to 12 carbon atoms, m is from 0 to 5. The dicumyl group includes the OX group which is the phosphite portion. The OX group is hindered by only one alkylaryl group at the ortho position with the other ortho position being occupied by hydrogen. X has the following formula: 2 EP 0 785 209 A1 (r5)— cz-r0^ ,c-o \ p p — / or wherein R2 is independently selected from the group consisting of alkyl groups having from 1 to 12 carbon atoms. z1 and z2 can be 0 or 1 . If z1 and z2 are both 0, the ring is a five member ring. If one of z1 or z2 are 1 and one is 0, the ring is a six member ring. If z-, and z2 are both 1, the ring is a seven member ring. R3 R4 and R5 are independently selected from the group consisting of hydrogen, halogen, or alkyl of from 1 to 3 carbon atoms. Preferably, the R3 groups are hydrogen. It is preferable for the alpha-carbon in the ring structure to include as least one hydrogen substituent. As explained more fully herein, the above phosphite entities are typically formed from 1,3 alkane diols with the beta or 2 position being blocked by alkyl or cyclic alkyl groups. The phosphites, which are useful to stabilize organic materials against thermal oxidative degradation, exhibit en- hanced hydrolytic stability and are resistant to UV yellowing. The present invention further includes an amorphous phosphite composition containing the above phosphite and stabilizing blends therefrom. Detailed Description of the Invention In as previously set forth, the present invention relates to phosphites of the formula: In the above compound, R7 and R8 are preferably alkyl of 1 to 3 carbon atoms, most preferably a straight chain alkyl group. R9 is preferably alkyl of 1 to 12, more preferably 1-4 carbon atoms, m is from 0 to 5, more preferably 0. The preferred cyclic phosphite moiety, X, of the phosphite compound as set forth above has the following most preferred formulae: c p — / R/ CHo-0 wherein R2 is independently selected from straight chain alkyl groups having from 1 to 6 carbon atoms, or, the phosphite which includes cyclic alkane moieties of the formulae: or EP 0 785 209 A1 The first step in the production of the phosphite ester of the present invention, is to react an appropriate diol with PZ3 where Z is halogen, preferably Br or CI. PCI3 is the preferred reactant As previously mentioned, the diols utilized are the 1 ,3-alkane diols wherein the 2 position is blocked. The neo-type glycols are those glycols having beta or the 2,2 positions completely substituted. These diols have the formula: in which R11 and R12 are alkyl groups of 1 to 12 carbon atoms or and the cyclic formula has the substituent groups as hereinbefore described. Specific alkyl diols that may be utilized include 2, 2-dimethyl-1 ,3-propane diol, 2,2-diethyl-1 ,3-propane diol, 2,2-dib- utyl-1 ,3-propane diol, 2-methyl-2-ethyl-1 ,3-propane diol, 2-ethyl-2-propyl-1 ,3-propane diol, 2-ethyl-2-butyl-1 ,3-pro- pane diol, 2-hexyl-1 ,3-propane diol, 2-methyl-2-hexyl-1 ,3-propane diol such diols are set forth in lines 7 to 43, column 2, of U.S. patent 3,714,302 to Dever et al. In addition to those diols, cycloalkyl-1,1-dimethanol where the cycloalkyl group is from 4 to 7 carbon atoms, such as cyclohexane-1 , 1 -dimethanol may be utilized. The resulting product is an intermediate phosphorohalidite product of the formula: C-O R,N (RSX— Cz-rC-C C-Os C P — z c /P-z 9r° or where the R values are as previously described. The reaction between the diol and PZ3, where Z is halogen, preferably Br or CI, to form the intermediate phospho- rohalidite may be carried out with or without the use of a solvent Typically PZ3 can be added to the diol or the diol can be added to PZ3. Preferably the PZ3 is added to the diol with the reaction mixture being maintained at a temperature of about 5 to 50 degrees Centigrade. This temperature may be controlled by controlling the rate of PZ3 addition. A slower addition favors lower temperatures. It is preferred to cool the reaction mixture during the addition. A slight excess of stoichiometric amounts of PZ3 is preferably utilized. The reaction is quite exothermic in the absence of a solvent, but a temperature moderating effect is produced by the cooling effect of vigorous HZ evolution. Hence, by effective control PZ3 addition, the reaction may be made self-regulating in the temperature range between 5-15 degrees centi- grade. Desirable solvents that may be utilized are neutral solvents. Typical solvents are tolulene, heptane, xylene, meth- ylene chloride, choroform, and benzene. Preferred solvents are methylene chloride, heptane, or xylene. After the reaction has gone to completion, the bulk of the by-product HZ such as HCI, may optionally be removed by gently raising the temperature of the product to room temperature to about 50 degrees centigrade. The solvent utilized is removed, typically by application of a vacuum, to yield the remaining intermediate phosphorohalidite product. To produce the phosphite ester stabilizer of the present invention, the above intermediate phosphorohalidite prod- uct is next reacted with a hydroxyaryl compound of the formula: EP 0 785 209 A1 5 10 wherein R7, R8, R9 and m are as described above. Suitable reaction methods are set out in Great Britain Patent 2087399A, U.S. Patent Spivaketal. 4318845 issued 1982, and Article in Phosphorous & Sulfur Journal by J.D. Spivak is et al. 1983, vol. 15, pp. 9-13, all of which are incorporated herein by reference. The reaction between the intermediate phosphorohalidite product and the hydroxyaryl compound may be conduct- ed in the same reaction vessel that was employed to produce the crude phosphite ester stabilizer by merely introducing the hydroxyaryl compound into the reactor.
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