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(12) United States Patent (10) Patent No.: US 8.445,567 B2 Stevenson Et Al

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(12) United States Patent (10) Patent No.: US 8.445,567 B2 Stevenson Et Al USOO8445567B2 (12) United States Patent (10) Patent No.: US 8.445,567 B2 Stevenson et al. (45) Date of Patent: May 21, 2013 (54) METHOD FOR REDUCING PLATE-OUT OF (56) References Cited SOLID PHOSPHITES IN POLYMERS U.S. PATENT DOCUMENTS (75) Inventors: Donald Stevenson, Dover, OH (US); 2004/0164279 A1* 8, 2004 Stevenson et al. ............ 252/.397 Michael Jakupca, Canton, OH (US); 2006/0173109 A1* 8/2006 Keegan et al. ................ 524f109 Nina Bersaglini, Magnolia, OH (US) OTHER PUBLICATIONS (73) Assignee: Dover Chemical Corporation, Dover, Spatafore et al., “Migration and Blooming of Stabilizing OH (US) Antioxidants in Polypropylene' Polym. Engineering and Science, Nov. 1991, vol. 31, No. 22, pp. 1610-1617.* (*) Notice: Subject to any disclaimer, the term of this PCT/US2010/24911 International Preliminary Report on Patentabil patent is extended or adjusted under 35 ity form PCT/IB/373, dated Aug. 23, 2011. U.S.C. 154(b) by 411 days. PCT/US2010/24911 International Search Report form PCT/ISA/ 210. (21) Appl. No.: 12/709,883 PCT/US2010/24911 International Written Opinion Form PCT/ISA/ 237 dated Apr. 12, 2010. Filed: Feb. 22, 2010 Spatafore, et al. Migration and Blooming of Stabilizing Antioxidants (22) in Polypropylene Polymer Engineering and Science, Aug. 26, 2004, (65) Prior Publication Data vol. 31, Issue 22, pp. 1610-1617. US 2010/0216923 A1 Aug. 26, 2010 * cited by examiner Primary Examiner — Robert D. Harlan Related U.S. Application Data (74) Attorney, Agent, or Firm — Hahn Loeser & Parks LLP (60) Provisional application No. 61/154,531, filed on Feb. 23, 2009. (57) ABSTRACT A process is described which reduces the amount of bloom (51) Int. C. and/or plate-out of phosphite antioxidants during polymer CSK 3/52 (2006.01) processing by the addition of at least one polyethylene glycol (52) U.S. C. (or blends thereof) or polycaprolactones (or blends thereof) USPC ............................ 524/128: 524/140; 524/141 having an average molecular weight of approximately 1,000 (58) Field of Classification Search to 20,000, most preferably between 4,000 to 10,000. USPC .......................................... 524/128, 141, 140 See application file for complete search history. 14 Claims, No Drawings US 8,445,567 B2 1. 2 METHOD FOR REDUCING PLATE-OUT OF SUMMARY OF THE INVENTION SOLID PHOSPHITES IN POLYMERS The invention herein described includes the use of a TECHNICAL FIELD defined molecular weight range of polyalkylene glycols, including polyethylene glycols, polypropylene glycols and The invention described herein pertains generally to a polycaprolactones which when used above a minimum con method to prevent the “migration” or “plate-out” or “bloom' centration, can reduce and prevent the migration and/or plate of high performance or general purpose solid phosphites from out of solid diphosphites and monophosphites Such as Dover polyolefins, including preferably polyethylenes, especially phos(R) S-9228TM (bis(2,4-dicumylphenyl)pentaerythritol linear low density polyethylenes and low density polyethyl 10 diphosphite) or Doverphos(R) S-480 (tris(2,4-di-t-butylphe enes, and polypropylene during processing and aging. More nyl)phosphite) in polyolefins, e.g., low density polyethylene, specifically the invention relates to a process to reduce the linear low density polyethylene and polypropylene during migration or plate-out of high performance Solid diphosphites processing and aging. such as Doverphos(R) S-9228TM (bis(2,4-dicumylphenyl)pen 15 In one embodiment, the molecular weight range of poly taerythritol diphosphite) and solid monophosphites such as ethylene glycol (PEG) is from about 1,000 to 20,000, more Doverphos(R) S-480 (tris(2,4-di-t-butylphenyl) phosphite) preferably from about 2,000 to about 15,000, most preferably when blended into polyolefins. The invention is expected to from about 4,000 to about 10,000, and in one preferred have applicability to other phosphites, although to different embodiment, is approximately 8000. PEG is added at a con degrees, a non-limiting list including distearyl pentaerythritol centration which is effective compared to a composition with diphosphite (Doverphos(RS-680), bis-(2,4-di-t-butylphenyl) no added PEG. In another embodiment polypropylene glycol, pentaerythritol diphosphite (UltranoxR 626), bis-(2,6-di-t- the molecular weight range of (PPG) is from 400 to 8000 and butyl-4-methylphenyl)pentaerythritol diphosphite (PEP 36), more preferably 3000 to 4000. The PPG is added at a con and 2.2.2"-nitrilo triethyl-tris3.3',5,5'-tetra-tert-butyl-1,1'- centration which is effective compared to a composition with biphenyl-2,2'-diylphosphite (Irgafos(R 12). 25 no PPG. In another embodiment, polycaprolactones (PCL) with molecular weight range of 400 to 15,000 are added, and BACKGROUND OF THE INVENTION more preferably with a molecular weight range from 2,000 to 8000. The PCL is added at a concentration which is effective Solid phosphites, particular high performance Solid phos compared to a composition with no PCL. phites, are very good stabilizers for the processing of linear 30 low density polyethylene (“LLDPE), high density polyeth In one embodiment, the PEG, PPG, and PCL are added in ylene (“HDPE), low density polyethylene (“LDPE) and an amount which is within approximately 150% of an amount polypropylene (“PP). One particular high performance solid of said diphosphite, alternatively within approximately 100% phosphite, namely Doverphos(R S-9228TM (bis(2,4-di of the diphosphite, and in yet another alternative, within cumylphenyl)pentaerythritol diphosphite) has proven to be a 35 approximately 50% of said amount of diphosphite. In some very good polymer stabilizer. (See U.S. Pat. Nos. 5,364,895: applications, the added amounts will be essentially equal. 5,438,086; 7,176,252: 6,613,823; 6,224,791; 6,770,693; and Secondary additives may also be added, these additives 6,680,351.) Although Doverphos(R S-9228TM gives excellent selected from the group consisting of magnesium oxide, Zinc color and melt flow stability during processing of LLDPE and oxide, calcium Stearate, magnesium Stearate, and hydrotal LDPE, when used at moderate to high levels (over 250 ppm) 40 cite. it will plate-out on the processing equipment or plate-out on In another embodiment of the invention, blends of PEG, the plastic part after aging, both of which are undesirable. PPG and PCL, particularly are employed. The problem with plating-out on process equipment is that These and other objects of this invention will be evident the there is a build up of residual phosphite on some of the when viewed in light of the detailed description and appended processing parts thereby requiring that the process be stopped 45 claims. and the equipment cleaned. In the case of extruded LLDPE film or blown LLDPE film, the Doverphos(R) S-9228TM plates DETAILED DESCRIPTION OF THE INVENTION out on the rolls resulting in particles of S-9228TM being trans ferred to the film. Additionally, not only does the S-9228TM The best mode for carrying out the invention will now be plate out on the processing equipment, but on aging some of 50 described for the purposes of illustrating the best mode the S-9228TM migrates to the surface of the polyethylene known to the applicant at the time. The examples are illustra (“PE) film. In the case of PE stretch film the S-9228TM tive only and not meant to limit the invention, as measured by appears as a powder on the Surface and prevents the stretch the scope and spirit of the claims. As used in this application, film from adhering to itself. “plate-out” is the migration of additives to manufacturing At least one prior art solution described in WO 2006/ 55 083.642 A1, disclosed a method of reducing the plate-out by equipment during processing while “bloom' is the migration the incorporation of a dibenzylidene, with a clarifying agent of additives to the Surface of the polymer after aging. during polypropylene processing by including the use of one Doverphos(R) S-9228TM is a high performance diphosphite or more co-additives. The co-additives used were selected that gives good melt flow stability and good color stability from the group consisting of homopolymers of ethylene 60 during polymer processing. Tables 1-3 give some of the per oxide, copolymers containing ethylene oxide segments, pro formance data of S-9228TM compared to the general purpose pylene oxide and polycaprolactone and derivatives and com solid monophosphite, Doverphos(R) S-480. Both formulas binations. contained 400 ppm of Dovernox-10 (tetrakis methylene (3.5- Thus, there is a great need to find away or process to be able di-t-butyl-4-hydroxyhydrocinnamate) methane) and 400 to use solid diphosphites and monophosphites at higher levels 65 ppm of CaSt (calcium stearate). S-9228T is bis(2,4-di in LLDPE and LDPE without the attendant problem of plate cumylphenyl)pentaerythritol diphosphite with less than 5% out and/or bloom. triisopropanolamine added by weight. US 8,445,567 B2 3 4 As used in this application, the phosphite additive weights, i.e. they are polydisperse. The size distribution can S-9228TM (bis(2,4-dicumylphenyl)pentaerythritol diphos be characterized Statistically by its weight average molecular phite) is the following phosphite additive commercially avail weight (M) and its number average molecular weight (M), able from Dover Chemical Corporation. the ratio of which is called the polydispersity index (M/M). CH3 O O CH3-(O) CH -CH3 H3C CH As used in this application, the phosphite additive S-480. The performance of the diphosphite S-9228TM was com also known as Irgafos(R 168, (tris(2,4-di-t-butylphenyl) phos pared and contrasted to the monophosphite S-480 in LLDPE, phite) is the following phosphite additive commercially avail HDPE and PP as illustrated in Tables 1-3.
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