CA1244997A - Acrylic acid/2-acrylamido-2-methylpropyl-sulfonic acid/2-acrylamido-2-methylpropyl phosphonic polymers - Google Patents
Acrylic acid/2-acrylamido-2-methylpropyl-sulfonic acid/2-acrylamido-2-methylpropyl phosphonic polymersInfo
- Publication number
- CA1244997A CA1244997A CA000517032A CA517032A CA1244997A CA 1244997 A CA1244997 A CA 1244997A CA 000517032 A CA000517032 A CA 000517032A CA 517032 A CA517032 A CA 517032A CA 1244997 A CA1244997 A CA 1244997A
- Authority
- CA
- Canada
- Prior art keywords
- acrylamido
- acid
- methylpropyl
- weight
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Abstract
TITLE OF THE INVENTION
POLYMERS
ABSTRACT OF THE DISCLOSURE
The present invention is directed to a polymer, having an intrinsic viscosity of 0.05 to 4.5 dl/g, in 1.0 M NaCl, prepared from:
(A) 35 to 65%, by weight, of acrylic acid or methacrylic acid;
(B) 15 to 45%, by weight, of 2-acrylamido-2-methyl-propylsulfonic acid or 2-methacrylamido-2-methyl-propylsulfonic acid; and (C) 15 to 25%, by weight, of 2-acrylamido-2-methyl-propyl phosphonic acid or 2-methacrylamido-2-methylpropylphosphonic acid.
POLYMERS
ABSTRACT OF THE DISCLOSURE
The present invention is directed to a polymer, having an intrinsic viscosity of 0.05 to 4.5 dl/g, in 1.0 M NaCl, prepared from:
(A) 35 to 65%, by weight, of acrylic acid or methacrylic acid;
(B) 15 to 45%, by weight, of 2-acrylamido-2-methyl-propylsulfonic acid or 2-methacrylamido-2-methyl-propylsulfonic acid; and (C) 15 to 25%, by weight, of 2-acrylamido-2-methyl-propyl phosphonic acid or 2-methacrylamido-2-methylpropylphosphonic acid.
Description
2 0 5 0 S/l O O ~A ~ 2,e~
TITLE OF THE INVENTION
POLYMERS
BACKGROUND OF THE INVENTION
U.S. Patent 3,928,196 discloses the use of a copolymer of 2-acrylamido-2-methylpropylsulfonic acid and acrylic acid as scale inhibitors.
Published European Patent Application 89,654 discloses copolymers of 2-acrylamido-2-methylpropyl phosphonic acid and acrylamide or acrylic acid as scale inhibitors.
DESCRIPTION OF THE INVENTION
The present invention is directed to a polymer, having an intrinsic viscosity of 0.05 to 4~5 dl/g, in 1.0 M NaCl, prepared from:
(A) 35 to 65%, by weight, of acrylic acid or methacrylic acid;
(B) 15 to 45%, by weight, of 2-acrylamido-2-methyl-propylsulfonic acid or 2-methacrylamido-2-methyl-propylsulfonic acid; and (C3 15 to 25%, by weight, of 2-acrylamido-2-methyl-propyl phosphonic acid or 2-methacrylamido-2-methylpropylphosphonic acid.
The polymers are prepared fro]m 35 to 65%, preferably 40 to 60%, by weight, acrylic acid or methacrylic acid, preferahly acrylic acid; 15 to 45~, 10 preferably 20 to 40%, by weight, 2-acrylamido-2-methylpropylsulfonic acid (hereinafter "AMPS") or 2-methacrylamido-2-methylpropyl~ulfonic acid, preferably AMPS; and 15 to 25~, preferably 20%, by weight, 2-acrylamido-2-methylpropyl phosphonic acid (hereinafter "AMPPA") or 2-methacrylamido-2-methyl-propylphosphonic acid. Terpolymers are preferred.
AMPPA may be prepared as described ln U.S. Pat~nt ~,526,728.
The polymers may be prepared by mixing the monomers preferably in the presence of a free radical initiator. Any free radical initiator may be used.
Examples include peroxides, azo initiators and redox systems. The polymerization may also be initiated photochemically. The preferred catalysts are sodium persulfate or a mixture of ammonium persulfate and any azo type initiator, such as 2,2'-azobis~(2,4-dimethyl-4-methoxyvaleronitrile).
The polymerization may be conducted by any of a variety of procedures, for example, in solution, suspension, bulk and emulsions.
The reaction temperature is not critical.
The reaction will generally occur between 10 and 100C9 preferably 40 to 60C. It is generally impractical to run the reaction below room temperature because the reaction is too slow. Above a temperature of 60C, the molecular weight of the polymer tends to decrease. The reaction, depending on the temperature, generally takes from 1 to 12 hours. Measuring for residual monomer will verify when the reaction is complete.
The pH of the reaction mixture is not critical. The pH is generally in the range of 3.5 to 9Ø
The percent solids in the reaction mixture is not critical. The preferred range is 1 to 50%, by weight, solids.
The molecular weight of polymers is difficult to accurately measure. The polymers are, instead, usually identified by intrinsic viscosity.
The intrinsic viscosity of the polymer is critical in the instant invention. The intrinsic viscosity should be .05 to 4.5, preferably 0.05 to 2.5 dl/g, in 1.0 M sodium chloride (measured in a 75 Cannon Ubbelohde capillary viscometer).
The polymers of the instant invention have been found to be effective as scale inhibitors, particularly in inhibiting calcium phosphate scale.
The polymers of the examples were produced by mixing the monomers indicated in Table 1, in the amounts, solids concentration, initial temperatures and pH indicated. The monomer mix was purged with nitrogen for one hour. The solvent was deionized water. The initiator was added and the components allowed to react for about 3 hours.
r~ t~
t~ 0 4 GJ
~ I~n u O
ta _l 'C
I ~
'O
u~ ~ r7 .~ o O O ~ ~ ~
U~
_ u u~ æ u~ 5 :~
~1 d~ U ~ (~
a3 ~1 .q v E~ P u O O
t~ N
~ O O ~ O
æ
O O
~ 3 U ~ ~ o ~ ~ P
~3 ~ ~ a O ~ 0 ~ ~ o n 'i o U 11 ~
o I ~ 0~
.~ n 11 ,~ N ~ ~ ~ 0 O I
-Various polymers were screenecl for threshold inhibition of calcium carbonate and ca]cium phosphateO
Stagnant flask tests were used with so]utions stored for 24 hours at constant temperature. The standard test conditions used were as follows:
Calcium Calcium Carbonate Phosphate lO Calcium, mg/l 200 200 Bicarbonate, mg/l600 ---Phosphate, mg/l --- 9 pH 8.0 8.5 Temperature, C 60 60 Two flasks were used for each test; one for a control (no inhibitor) and one with the polymer.
The percent inhibition was determined by the following equation:
S - S
Percent Inhibition = x lO0 where:
-S - S
SI = level of test specie initially;
Sc = level of test specie at end of control test; and ST = level of test specie at end of inhibitor test, Calcium was used as the test specie in the calcium carbonate test, and phosphate was the test specie in the calcium phospha~e test. The results are summarized in Table II.
~8, ~8 8 3g ~3 8 ~ ~ u
TITLE OF THE INVENTION
POLYMERS
BACKGROUND OF THE INVENTION
U.S. Patent 3,928,196 discloses the use of a copolymer of 2-acrylamido-2-methylpropylsulfonic acid and acrylic acid as scale inhibitors.
Published European Patent Application 89,654 discloses copolymers of 2-acrylamido-2-methylpropyl phosphonic acid and acrylamide or acrylic acid as scale inhibitors.
DESCRIPTION OF THE INVENTION
The present invention is directed to a polymer, having an intrinsic viscosity of 0.05 to 4~5 dl/g, in 1.0 M NaCl, prepared from:
(A) 35 to 65%, by weight, of acrylic acid or methacrylic acid;
(B) 15 to 45%, by weight, of 2-acrylamido-2-methyl-propylsulfonic acid or 2-methacrylamido-2-methyl-propylsulfonic acid; and (C3 15 to 25%, by weight, of 2-acrylamido-2-methyl-propyl phosphonic acid or 2-methacrylamido-2-methylpropylphosphonic acid.
The polymers are prepared fro]m 35 to 65%, preferably 40 to 60%, by weight, acrylic acid or methacrylic acid, preferahly acrylic acid; 15 to 45~, 10 preferably 20 to 40%, by weight, 2-acrylamido-2-methylpropylsulfonic acid (hereinafter "AMPS") or 2-methacrylamido-2-methylpropyl~ulfonic acid, preferably AMPS; and 15 to 25~, preferably 20%, by weight, 2-acrylamido-2-methylpropyl phosphonic acid (hereinafter "AMPPA") or 2-methacrylamido-2-methyl-propylphosphonic acid. Terpolymers are preferred.
AMPPA may be prepared as described ln U.S. Pat~nt ~,526,728.
The polymers may be prepared by mixing the monomers preferably in the presence of a free radical initiator. Any free radical initiator may be used.
Examples include peroxides, azo initiators and redox systems. The polymerization may also be initiated photochemically. The preferred catalysts are sodium persulfate or a mixture of ammonium persulfate and any azo type initiator, such as 2,2'-azobis~(2,4-dimethyl-4-methoxyvaleronitrile).
The polymerization may be conducted by any of a variety of procedures, for example, in solution, suspension, bulk and emulsions.
The reaction temperature is not critical.
The reaction will generally occur between 10 and 100C9 preferably 40 to 60C. It is generally impractical to run the reaction below room temperature because the reaction is too slow. Above a temperature of 60C, the molecular weight of the polymer tends to decrease. The reaction, depending on the temperature, generally takes from 1 to 12 hours. Measuring for residual monomer will verify when the reaction is complete.
The pH of the reaction mixture is not critical. The pH is generally in the range of 3.5 to 9Ø
The percent solids in the reaction mixture is not critical. The preferred range is 1 to 50%, by weight, solids.
The molecular weight of polymers is difficult to accurately measure. The polymers are, instead, usually identified by intrinsic viscosity.
The intrinsic viscosity of the polymer is critical in the instant invention. The intrinsic viscosity should be .05 to 4.5, preferably 0.05 to 2.5 dl/g, in 1.0 M sodium chloride (measured in a 75 Cannon Ubbelohde capillary viscometer).
The polymers of the instant invention have been found to be effective as scale inhibitors, particularly in inhibiting calcium phosphate scale.
The polymers of the examples were produced by mixing the monomers indicated in Table 1, in the amounts, solids concentration, initial temperatures and pH indicated. The monomer mix was purged with nitrogen for one hour. The solvent was deionized water. The initiator was added and the components allowed to react for about 3 hours.
r~ t~
t~ 0 4 GJ
~ I~n u O
ta _l 'C
I ~
'O
u~ ~ r7 .~ o O O ~ ~ ~
U~
_ u u~ æ u~ 5 :~
~1 d~ U ~ (~
a3 ~1 .q v E~ P u O O
t~ N
~ O O ~ O
æ
O O
~ 3 U ~ ~ o ~ ~ P
~3 ~ ~ a O ~ 0 ~ ~ o n 'i o U 11 ~
o I ~ 0~
.~ n 11 ,~ N ~ ~ ~ 0 O I
-Various polymers were screenecl for threshold inhibition of calcium carbonate and ca]cium phosphateO
Stagnant flask tests were used with so]utions stored for 24 hours at constant temperature. The standard test conditions used were as follows:
Calcium Calcium Carbonate Phosphate lO Calcium, mg/l 200 200 Bicarbonate, mg/l600 ---Phosphate, mg/l --- 9 pH 8.0 8.5 Temperature, C 60 60 Two flasks were used for each test; one for a control (no inhibitor) and one with the polymer.
The percent inhibition was determined by the following equation:
S - S
Percent Inhibition = x lO0 where:
-S - S
SI = level of test specie initially;
Sc = level of test specie at end of control test; and ST = level of test specie at end of inhibitor test, Calcium was used as the test specie in the calcium carbonate test, and phosphate was the test specie in the calcium phospha~e test. The results are summarized in Table II.
~8, ~8 8 3g ~3 8 ~ ~ u
3 c c~ .~
~ r~
'~ ~
.~. ~
8 ~ u~
~ r~
'~ ~
.~. ~
8 ~ u~
Claims (4)
1. A polymer, having an intrinsic viscosity of 0.05 to 4.5 dl/g, in 1.0 M NaCl, prepared from:
(A) 35 to 65%, by weight, of acrylic acid or methacrylic acid;
(B) 15 to 45%, by weight, of 2-acrylamido-2-methyl-propylsulfonic acid or 2-methacrylamido-2-methyl-propylsulfonic acid; and (C) 15 to 25%, by weight, of 2-acrylamido-2-methyl-propyl phosphonic acid or 2-methacrylamido-2-methylpropylphosphonic acid.
(A) 35 to 65%, by weight, of acrylic acid or methacrylic acid;
(B) 15 to 45%, by weight, of 2-acrylamido-2-methyl-propylsulfonic acid or 2-methacrylamido-2-methyl-propylsulfonic acid; and (C) 15 to 25%, by weight, of 2-acrylamido-2-methyl-propyl phosphonic acid or 2-methacrylamido-2-methylpropylphosphonic acid.
2. The polymer of Claim 1, prepared from acrylic acid, 2-acrylamido 2-methylpropylsulfonic acid, and 2-acrylamido-2-methylpropyl phosphonic acid.
3. The polymer of Claim 1, prepared from 40 to 60%, by weight, acrylic acid; 20 to 40%, by weight, 2-acrylamido-2-methylpropylsulfonic acid, and 15 to 25%, by weight, 2-acrylamido-2-methylpropyl phosphonic acid.
4. The polymer of Claim 1, having an intrinsic viscosity of 0.05 to 2.5 dl/g, in 1.0 M
NaCl.
NaCl.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77107985A | 1985-08-30 | 1985-08-30 | |
| US771,079 | 1985-08-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1244997A true CA1244997A (en) | 1988-11-15 |
Family
ID=25090630
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000517032A Expired CA1244997A (en) | 1985-08-30 | 1986-08-28 | Acrylic acid/2-acrylamido-2-methylpropyl-sulfonic acid/2-acrylamido-2-methylpropyl phosphonic polymers |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS6253314A (en) |
| AU (1) | AU592111B2 (en) |
| CA (1) | CA1244997A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113023909B (en) * | 2021-03-23 | 2022-10-18 | 中海油(天津)油田化工有限公司 | Phosphorus-free antiscale agent for oil field and preparation method thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2536758A1 (en) * | 1982-11-30 | 1984-06-01 | Coatex Sa | NON-POLLUTANT FLUIDIFYING ADJUVANT FOR SALTWATER AND / OR FRESHWATER WATER-BASED DRILLING SLUDGE |
| DE3326391A1 (en) * | 1983-07-22 | 1985-01-31 | Cassella Ag, 6000 Frankfurt | POLYMERISATES CONTAINING PHOSPHONIC ACID GROUPS, THEIR PRODUCTION AND THEIR USE |
| GB8400848D0 (en) * | 1984-01-13 | 1984-02-15 | Ciba Geigy Ag | Cotelomer compounds |
-
1986
- 1986-08-28 CA CA000517032A patent/CA1244997A/en not_active Expired
- 1986-08-29 AU AU62070/86A patent/AU592111B2/en not_active Ceased
- 1986-08-30 JP JP20276586A patent/JPS6253314A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6253314A (en) | 1987-03-09 |
| AU6207086A (en) | 1987-03-05 |
| AU592111B2 (en) | 1990-01-04 |
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Legal Events
| Date | Code | Title | Description |
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| MKEX | Expiry |