Branched low profile additives and methods of production

a low-profile, additive technology, applied in the field of low-profile additives, can solve the problems of internal stress build-up, difficult handling, dimensional changes, etc., and achieve the effects of reducing solution viscosity, reducing shrinkage, and high molecular weight lpa

Inactive Publication Date: 2009-11-12
ASHLAND LICENSING & INTPROP LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0009]Non-generative branching agents are typically multifunctional molecules having functionality greater than two and include, but are not limited to, polyols (e.g. glycerol, trihydroxymethylol propane, pentaerythritol, etc.), polyacids (e.g. trimelitic acid), polyhydroxyacids (e.g. 2,2-bis(hydroxymethyl)propionic acid, malic acid, citric acid, tartaric acid, etc.) and the like. The generative/non-generative branching agents are structurally more complex molecules that combine features of generative and non-generative branching agents (e.g. glycidol, epoxydized fatty acids, trimellitic anhydride, and the like). The branched structure of polyester allows the formation of high molecular weight LPA at a lower solution viscosity. In addition, these branched polyester LPAs are more effective at reducing shrinkage caused by cure, and improving surface smoothness of the molded objects.
[0010]The method for making the branched LPAs comprises reacting one or more branching agents with one or more monomers, typical polyester monomers, to produce LPAs with high polydispersity and relatively high weight average molecular weight. The method of making the branched LPAs produce high weight average molecular weight LPAs at lower solution viscosity, as compared to their linear analogues. Among many advantages of the method is the ability to make branched LPAs in which the manufacturing cycle time is significantly reduced. In an exam

Problems solved by technology

Unthickened molding compounds are sticky masses, which are difficult to handle.
This shrinkage can cause warpage, internal stress bu

Method used

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Examples

Experimental program
Comparison scheme
Effect test

examples 1 through 4

[0023]The following raw materials, as set forth in Table 1, were charged to a three-liter resin kettle equipped with a thermocouple, mechanical stirrer, a fractionating column, distillation head, a condenser, and a nitrogen sparge to make branched LPAs.

TABLE 1ExampleComponentGramsMolesMole-%1Ethylene glycol421.056.7825.40Propylene glycol521.406.8525.66Adipic acid1837.8012.5847.09EPON 828 Resin*187.250.491.852Diethylene glycol149.001.407.40Ethylene glycol417.406.7235.50PPG 410366.601.216.39EPON 828 Resin*60.000.160.85Adipic acid1,379.209.4449.863Stage IEthylene glycol209.60Propylene glycol490.77NPG180.10EPON 828 Resin*60.00Adipic acid292.00Stage IIIsophthalic Acid1182g4Ethylene glycol253.57Propylene glycol310.11Adipic acid1,201.92EPON 828 Resin*31.28*EPON ® 828 difunctional bisphenol A / epichlorydrin derived liquid epoxy resin, epoxide eq. 185-192, viscosity @ 25° C. 110-150; Hexion Specialty Chemicals, Inc., Houston, TX

[0024]The mixture in each example was heated slowly to 120° C. at...

example 5

[0025]SMC was formulated by conventional methods using the branched LPA prepared in accordance with Example 1. The following table, Table 2, shows SMC formulations using the branched LPA and the properties of molded panels comprising the SMC. The SMC sheet was made according to conventional methods using a 24 inch SMC machine. Panels (12″×12″) were molded at 300° F. (150° C.) and 75 tons pressure for two minutes. Surface quality measurements using Ashland's Advance Laser Surface Analyzer are also shown in Table 2.

TABLE 2FormulationABCDUPE Resin AROPOL D61.161.161.0761.071691 (Ashland, Inc.)Branched LPA (60%20.529.310.0620.5NV)PVAc LPA (40.5% NV)0.000.0017.280.0Styrene18.49.611.3918.4Total100.0100.0100.00100.00Filler (CaCO3)200.0200.0200.00200.00Enhancesrs0.000.004.004.00Wetting agent (BYK0.60.60.60.69010, Byk Chemie)Mod E (5% p-0.20.20.20.2benzoquinone solution)BHT (butylated hydroxyl0.020.020.020.02toluene)TBPB Initiator (tert-butyl1.51.51.51.5peroxyperbenzoate)Zn Stearate4.54.54.5...

example 6

[0026]Branched LPA containing component(s) that requires transesterification digestion) was made with the following components as set forth in Table 3.

TABLE 3EX. 6Componentgmolemole %Ehylene Glycol341.375.5023.78Propylene Glycol418.505.5023.78Adipic Acid1607.5411.0047.55Soybean oil572.000.652.81Epon ® 828 Resin170.130.451.94Zinc Acetate1.330.0060.03HQ0.300.0030.01TPP2.930.0110.05FASCAT 41003.030.0150.06

[0027]The procedure for Example 6 was as follows. Ethylene glycol, propylene glycol, soybean oil, and zinc acetate were added to a 3 L reactor equipped with a Vigreux column and a water condenser. Reaction was heated to 190-200° C. and temperature maintained for two hours to allow transesterification of soybean oil. A portion of adipic acid was then added to the reactor and the temperature increased to 200° C. After about 100 g of water was removed, reaction temperature was lowered below 140° C. and EPON® 828 resin, triphenyl phosphine (TPP), and the rest of the adipic acid, were adde...

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Abstract

The invention pertains to low profile additives (“LPA”) comprising branched polymers having a weight average molecular weight (Mw) of at least about 20,000 grams/mole and a number average molecular weight (Mn) of at least about 3,000 grams/mole and methods for making the LPAs. The invention further concerns compositions comprising LPAs synthesized from one or more difunctional monomers and one or more branching agents. Also, disclosed are thermosettable resinous compositions and molded articles comprising the LPAs.

Description

BACKGROUND OF THE INVENTION[0001]1. Field of the Invention[0002]The invention relates to low profile additives (“LPAs”) comprising branched polymers and methods for making the LPAs. The invention further concerns thermosettable resinous compositions, e.g., sheet molding compound (“SMC”) and bulk molding compounds (“BMC”), comprising the LPAs.[0003]2. The Related Art[0004]Polyester resins and vinyl ester resins may be used for thermosetting resin materials. Thermosetting unsaturated polyester resins are generally prepared by reacting dicarboxylic acids and anhydrides with glycols. Thermosetting vinyl ester resins are typically the reaction product of about equal amounts of a polyepoxide and an unsaturated monocarboxylic acid. When applied to thermosetting compositions, polyester and vinyl ester resins may be used in combination with fibrous reinforcement and inert fillers to manufacture composite structures, such as SMC and BMC. Such composite structures may be made by pre-mixing the...

Claims

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Application Information

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IPC IPC(8): C08G63/16C08G63/91C08J3/00C08G85/00C08L67/08
CPCC08G63/20C08L63/00C08L67/08C08L2666/14
Inventor RASOUL, HUSAM A.A.ANDJELKOVIC, DEJAN D.FISHER, DENNIS H.
Owner ASHLAND LICENSING & INTPROP LLC
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