Source: http://www.google.com/patents/US8227381?dq=5958006
Timestamp: 2014-08-23 02:18:08
Document Index: 394027094

Matched Legal Cases: ['Application No. 200710169190', 'Application No. 11158599', 'Application No. 12154675', 'Application No. 12154684', 'Application No. 06015025', 'Application No. 07014412', 'Application No. 07014412', 'Application No. 07014413', 'Application No. 09175465']

Patent US8227381 - Low molecular weight graft copolymers for scale control - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign in<nobr>Advanced Patent Search</nobr>PatentsLow molecular weight graft copolymer comprising a synthetic component formed from at least one or more olefinically unsaturated carboxylic acid monomers or salts thereof, and a natural component formed from a hydroxyl-containing natural moiety. The number average molecular weight of the graft copolymer...http://www.google.com/patents/US8227381?utm_source=gb-gplus-sharePatent US8227381 - Low molecular weight graft copolymers for scale controlAdvanced Patent SearchPublication numberUS8227381 B2Publication typeGrantApplication numberUS 12/888,618Publication dateJul 24, 2012Filing dateSep 23, 2010Priority dateJul 21, 2006Also published asCA2594464A1, EP1881016A2, EP1881016A3, US20080020961, US20110046025Publication number12888618, 888618, US 8227381 B2, US 8227381B2, US-B2-8227381, US8227381 B2, US8227381B2InventorsKlin A. Rodrigues, Jannifer SandersOriginal AssigneeAkzo Nobel N.V.Export CitationBiBTeX, EndNote, RefManPatent Citations (99), Non-Patent Citations (37), Referenced by (2), Classifications (62) External Links: USPTO, USPTO Assignment, EspacenetLow molecular weight graft copolymers for scale controlUS 8227381 B2Abstract Low molecular weight graft copolymer comprising a synthetic component formed from at least one or more olefinically unsaturated carboxylic acid monomers or salts thereof, and a natural component formed from a hydroxyl-containing natural moiety. The number average molecular weight of the graft copolymer is about 100,000 or less, and the weight percent of the natural component in the graft copolymer is about 50 wt % or greater based on total weight of the graft copolymer. Processes for preparing such graft copolymers are also disclosed.
CROSS-REFERENCE TO RELATED APPLICATIONS The present application is a divisional application of U.S. application Ser. No. 11/780,494, filed Jul. 20, 2007, currently pending, which is a continuation-in-part of U.S. application Ser. No. 11/459,233, filed Jul. 21, 2006, now abandoned.
Comparative Example 7 140 grams of water, 65 grams of maltodextrin (Cargill MD� 01918 dextrin, having a DE of 18 and a number average molecular weight of 12,937 as determined by aqueous GPC described above) and 0.00075 grams of FAS were heated in a reactor to 98� C. A solution containing 35 grams of acrylic acid in 30 grams of water was added to the reactor over a period of 45 minutes. An initiator solution comprising 3.6 grams of 35% hydrogen peroxide to solution in 30 grams of deionized water was simultaneously added to the reactor over a period of 60 minutes. The reaction product was held at 98� C. for an additional hour. The polymer was then neutralized to a pH of 5 by adding 18 grams of a 50% solution of NaOH. The final product was a clear water white solution having a Gardner color of 1. The number average molecular weight of this polymer was 125,980 as determined by aqueous GPC process noted above.
Example 3 Low molecular weight copolymer according to the present invention using Cu (II) sulfate pentahydrate instead of fas to produce the copolymer
Example 6 Low molecular weight acrylic acid-maleic acid graft copolymer using Cu (II) as a catalyst and higher amounts of natural material to synthetic monomer
Example 12 Low molecular weight graft copolymer
Example 13 Low molecular weight graft copolymer
Example 14 Low molecular weight graft copolymer
Example 15 Low molecular weight graft copolymer
Example 16 Test for Anti-Redeposition Copolymers from the above Examples were tested for anti-redeposition properties in a generic powdered detergent formulation. The powdered detergent formulation was as follows:
Economy Quality Powdered Detergent Formulation Ingredient
Examples 17 to 19 Granular Powder Laundry Detergent Formulations TABLE 3
Example 20 Hard Surface Cleaning Formulations Acid Cleaner
Example 21 Automatic Dishwash Powder Formulation Ingredients
Example 22 Automatic Non-Phosphate Dishwash Powder Formulation Ingredients
Example 23 Handwash Fabric Detergent Ingredients
Example 24 Fabric Detergent with Softener Ingredients
Example 25 Bar/Paste for Laundering Ingredients
Example 26 Liquid Detergent Formulation Ingredients
Example 27 Water Treatment Compositions Once prepared, water-soluble polymers are incorporated into a water treatment composition that includes the water-soluble polymer and other water treatment chemicals. Other water treatment chemicals include corrosion inhibitors such as orthophosphates, zinc compounds and tolyl triazole. The level of inventive polymer utilized in water treatment compositions is determined by the treatment level desired for the particular aqueous system treated. Water soluble polymers generally comprise from 10 to 25 percent by weight of the water treatment composition. Conventional water treatment compositions are known to those skilled in the art, and exemplary water treatment compositions are set forth in the four formulations below. These compositions containing the polymer of the present invention have application in, for example, the oil field.
Example 28 Test for Anti-Redeposition The polymers in Example 4 and Comparative Example 2 were tested for anti-redeposition performance. The data below indicates that the polymer of Example 4 was far superior to that of Comparative Example 2 in anti-redeposition properties. Further, the performance of polymer 4 proved superior to a commercial synthetic Na polyacrylate (Alcosperse 602N), which is an industry standard for this application.
Example 29 Low molecular weight maleic acid graft copolymer using Cu (II) as a catalyst and higher amounts of natural material to synthetic monomer
Example 30 Low molecular weight maleic acid graft copolymer with very high amounts of natural material to synthetic monomer
Example 31 Calcium Binding/Sequestration The calcium binding/sequestration properties of a series of polymers were measured using the test procedure below�
C ⁢ ⁢ B ⁢ ⁢ C ⁡ ( mg ⁢ ⁢ Ca ⁢ ⁢ C ⁢ ⁢ O 3 ) @ pH ⁢ ⁢ 10 = ( N - 2 ⁢ S ) ⁢ ( M ⁢ ⁢ EDTA ) ⁢ ( 100.09 ) Sample ⁢ ⁢ weight N=EDTA volume used to perform blank titration (ml)
Moles ⁢ ⁢ C ⁢ ⁢ O ⁢ ⁢ O ⁢ ⁢ H ⁢ / ⁢ g ⁢ ⁢ polymer ⁡ ( B ) = 2 � ( A ⁢ / ⁢ 100 ) 98 + ( 100 - A ) / 100 72 g ⁢ ⁢ Ca ⁢ ⁢ C ⁢ ⁢ O 3 ⁢ / ⁢ Mole ⁢ ⁢ C ⁢ ⁢ O ⁢ ⁢ O ⁢ ⁢ H ⁢ ⁢ in ⁢ ⁢ polymer = ( C ⁢ ⁢ B ⁢ ⁢ C ) / ( B ) � 1000 TABLE 5 Calcium Sequestration Wt % of synthetic Mole % maleic (Mw) monomers as a part of anhydride in the weight the weight of synthetic synthetic g CaCO3/ average monomer and natural portion of the Moles Ca sequestration Mole molecular component in graft graft copolymer COOH/g mg CaCO3/g COOH in Example weight copolymer (A) polymer (B) polymer (CBC) polymer Alcosperse 602N 100 0 0.0138 300 21.6 (Commercial synthetic polyacrylic acid) Alcosperse 100 22 0.021 450 21.2 175(Commercial synthetic acrylic- maleic copolymer) Example 3 15 0 0.0021 17 8.2 Example 11 79.834 75 20.8 0.014 440 38.4 Example 29 4,213 50 34.4 0.0058 266 45.1 Example 30 19.961 15.8 21.0 0.0024 132 54.8 Calcium sequestration is a stoichiometric property and is directly proportional to the moles of acid functionality in the polymer. The data indicates that maleic acid containing graft copolymers have much higher calcium sequestration numbers compared to the synthetic copolymers or the acrylic acid grafts on a molar basis.
Example 32 Low molecular weight graft copolymer using an oxidized starch derivative
Example 33 Inhibition of Precipitation The efficacy of various treatments was tested for their ability to prevent the precipitation of calcium carbonate in typical cooling water conditions (a property commonly referred to as the threshold inhibition). This test was developed in correlation with the dynamic testing units, in order to allow for an initially quick screening test of scale threshold inhibitors for cooling water treatment. The ratio of calcium concentration to alkalinity is 1.000:1.448 for the chosen water. This ratio is a fairly accurate average of cooling water conditions found worldwide. One should expect that water wherein the alkalinity is proportionately less will be able to reach higher levels of calcium, and that water containing a proportionally greater amount of alkalinity will reach lower levels of calcium. Since cycle of concentration is a general term, one cycle was chosen, in this case, to be that level at which calcium concentrations equaled 100.0 mg/L Ca as CaCO3 (40.0 mg/L as Ca). The complete water conditions at one cycle of concentration (i.e., make-up water conditions) are as follows:
Grams ⁢ ⁢ of ⁢ ⁢ treatment ⁢ ⁢ needed = ( 10 , 000 ⁢ ⁢ mg ⁢ / ⁢ L ) ⁢ ( 0.25 ⁢ ⁢ L ) ( decimal ⁢ ⁢ % ⁢ ⁢ of ⁢ ⁢ active ⁢ ⁢ treatment ) ⁢ ( 1000 ⁢ ⁢ mg ) Test Setup Procedure:
Example �Total� concentration analysis results:
Mn * growing ⁢ ⁢ polymer chain + RSH mercaptan chain ⁢ ⁢ transfer agent → Mn ⁢ H growing ⁢ ⁢ polymer chain ⁢ ⁢ terminated + RS * mercaptan ⁢ ⁢ free radical ( 1 ) RS * mercaptan ⁢ ⁢ free radical + M monomer → M * ⁢ ⁢ ( initiation ⁢ ⁢ of ⁢ ⁢ homopolymer ⁢ ⁢ chain ) ( 2 ) Performance of materials exemplified in U.S. Pat. No. 5,580,941 (�the '941 patent�) is mainly due to ungrafted synthetic copolymers generated in this process. This is the reason they exemplify relatively low amounts of saccharide (40 wt % or less). Higher amounts of saccharide will phase separate. Secondly, calcium binding data in Table 4 of the '941 patent is inversely proportional to the amount of saccharide functionality. This indicates that the material is mostly a mixture of synthetic copolymer and saccharide with little to no grafting. The saccharide contribution to Ca binding is negligible.
Example 34 Sulfonated graft copolymer with maltodextrin (without mercaptan chain transfer agent)
Example 35 CaCO3 inhibition performance
Example 36 Synthesis of graft copolymer
Example 37 Synthesis of graft copolymer
Example 38 22 grams of maleic anhydride was dissolved in 172.6 grams of water and neutralized with 22.5 grams of a 50% solution of NaOH. The mixture was heated to 95 C and 102.4 grams of DE 11(Cargill MD� 01960 dextrin, spray-dried maltodextrin obtained by enzymatic conversion of common corn starch, available from Cargill Inc., Cedar Rapids, Iowa) and 0.01 grams of ferrous ammonium sulfate hexahydrate was added. A monomer solution containing 33 grams of acrylic acid was subsequently added to the reactor over a period of 5 hours. An initiator solution comprising of 2.4 grams of sodium persulfate and 19.4 grams of a 35% solution of hydrogen peroxide dissolved in 12.7 grams of water was added to the reactor over a period of 5.5 hours. The reaction product was held at 95� C. for 30 minutes. 0.3 grams of erythorbic acid dissolved in 0.6 grams of water and simultaneously, 4 grams of a 41% bisulfate solution was added to scavenge the residual monomer. The final product was a clear light amber solution and had 44% solids. The number average molecular weight of this polymer as measured by aqueous GPC was 1280.
Example 39 The samples above were evaluated for barium sulfate inhibition using the procedure below:
g=(100�1)/35=2.857 g of polymer in 100 mL of seawater 3. Prepare a buffer solution.
g=(3000�1)/44.4=67.57 g of polymer in 3000 mL c. Bring to volume with DI water.
μl=[(V 1 �C 1)/C 2]�1000 where V1 is volume in mL of test sample (SW+FW), C1 is concentration of polymer desired (in ppm), and C2 is concentration of active polymer in inhibitor solution. Example: Desired test concentration is 50 ppm in a 30 mL sample size (SW+FW). Using a 10,000 ppm (1%) polymer solution:
μl=[(30�50)/10,000]�1000=150 μl 13. To each SW vial numbered 1-6,
% inhibition=((S*d)−B)/(T−B), where S=ppm Ba in sample d=dilution factor (grams filtrate+5 grams quenching solution)/grams filtrate B=ppm Ba in blank T=ppm Ba in total
Example 40 The polymer of Example 38 was tested in all 3 of the brines detailed in Table 1. The data indicate that the polymer is very compatible in these brines.
Example 41 Graft copolymer with 10 weight percent maltodextrin.
Example 42 Graft copolymer with 10 weight percent maltodextrin
Example 43 The polymers synthesized in examples 36 and 38 were tested for compatibility in ethylene glycol�
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