US20100041846A1 - Hydrophobic Crosslinkable Acetoacetylated Lactam/Vinyl Alcohol Copolymers - Google Patents
Hydrophobic Crosslinkable Acetoacetylated Lactam/Vinyl Alcohol Copolymers Download PDFInfo
- Publication number
- US20100041846A1 US20100041846A1 US12/244,420 US24442008A US2010041846A1 US 20100041846 A1 US20100041846 A1 US 20100041846A1 US 24442008 A US24442008 A US 24442008A US 2010041846 A1 US2010041846 A1 US 2010041846A1
- Authority
- US
- United States
- Prior art keywords
- copolymer
- lactam
- vinyl alcohol
- pvp
- acetoacetylated
- 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.)
- Abandoned
Links
- YSHVXWNWHVPSRK-UHFFFAOYSA-N CCC(CC(CC(O)CC(C)N1CCCC1=O)OC(=O)CC(C)=O)OC(C)=O Chemical compound CCC(CC(CC(O)CC(C)N1CCCC1=O)OC(=O)CC(C)=O)OC(C)=O YSHVXWNWHVPSRK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
- C08F226/10—N-Vinyl-pyrrolidone
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/50—Recording sheets characterised by the coating used to improve ink, dye or pigment receptivity, e.g. for ink-jet or thermal dye transfer recording
- B41M5/52—Macromolecular coatings
- B41M5/5254—Macromolecular coatings characterised by the use of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F216/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F216/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an alcohol radical
- C08F216/04—Acyclic compounds
- C08F216/06—Polyvinyl alcohol ; Vinyl alcohol
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F26/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F26/06—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F26/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F26/06—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
- C08F26/10—N-Vinyl-pyrrolidone
Abstract
Description
- This invention relates to lactam/vinyl alcohol copolymers, and more specifically, to hydrophobic cross-linkable acetoacetylated lactam/vinyl alcohol copolymers suitable for use in a variety of applications including printing, inks, membranes, coatings, adhesives, oil treatment chemicals (such as gas and kinetic hydrate inhibitors), and fiber/textile treatments.
- Inkjet printers, i.e., printers which form an image by firing a plurality of discrete drops of ink from one or more nozzles on to the surface of a recording sheet placed adjacent the nozzles, have recently enjoyed a large increase in sales. Modern inkjet printers can print on almost any conventional paper or similar medium. The quality of images produced by such printers is greatly affected by the properties of the medium used. More particularly, to produce high quality images reliably, it is necessary that the recording medium, i.e., the inkjet recording sheet, dry rapidly, not promote excessive spreading of the ink droplet, not promote “wicking”, that is spreading of ink by capillary action through fibrous medium such as paper, and, importantly, be such that the contrast of the dried image with moist surfaces does not result in bleeding of ink from the image.
- In U.S. Pat. No. 6,933,024, T. Chen describes the use and preparation of poly(vinylpyrrolidone-(PVP) co-vinylalcohol) as an inkjet recording material by hydrolyzing PVP/polyvinylacetate copolymer. However, the resultant hydrolyzed product was not hydrophobic, i.e., water resistant.
- In U.S. Pat. No. 4,350,788, W. Shinokawa et al. describes a synthetic resin emulsion containing an acetoacetylated polyvinyl alcohol as a protective colloid for use as an adhesive, paper treating agent, paint, fiber and textile treating agent and cement modifier. However, such a product would not be practical as an inkjet medium.
- In U.S. Pat. No. 2,536,980, G. Jones describes synthetic polyvinyl alcohol-1-butene-1,3-dione reaction products and processes. However, the patent does not disclose applicant's hydrophobic, cross-linkable acetoacetylated lactam/vinyl alcohol copolymers.
- Accordingly, it is an object of this invention to provide an improved inkjet recording medium. Another object herein is to provide a hydrophobic crosslinkable acetoacetylated lactam/vinyl alcohol copolymer.
- Still another object of this invention is to provide a copolymer which is made by partially hydrolyzing a polyvinylpyrrolidone/vinyl acetate copolymer to produce a poly(vinylpyrrolidone/vinyl alcohol) copolymer and then acetoacetylating the copolymer with a diketene to obtain said desired copolymer.
- These and other objects and features of the invention will be made apparent from the following description.
- Described herein is a hydrophobic, crosslinkable acetoacetylated lactam/vinyl alcohol copolymer suitable for use as a moisture resistant inkjet recording medium. Preferably, the lactam in the copolymer is vinyl pyrrolidone or vinyl caprolactam.
- The copolymer herein is made by partially hydrolyzing a polyvinylpyrrolidone/vinyl acetate copolymer to produce a poly(vinylpyrrolidone/vinyl alcohol) copolymer and then acetoacetylating this copolymer with a diketene to obtain the said desired copolymer.
- A particular feature of the inkjet recording material herein is its enhanced dye fade stability.
- Preferably, the polyvinylpyrrolidone/vinyl acetate is partially hydrolyzed to a degree of at least 80%; and the acetoacetylation step is carried out in a non-aqueous medium, suitably to a degree of at least 50%.
- The hydrophobic crosslinkable acetoacetylated lactam/vinyl alcohol copolymers of the invention is made from a poly(vinyllactam-co-vinyl ester), particularly poly(vinylpyrrolidone-co-vinyl acetate) copolymer, which is available from International Specialty Products (ISP) as a 70-30 copolymer (E-735) or as a 50-50 copolymer (E-535) (PVP-VAc). This copolymer then is hydrolyzed in the presence of a strong base, e.g., alcohol and water. The maximum equivalent of base (e.g., NaOH) suitably is equal to or less than the equivalent amount in the PVP/polyvinyl ester. The product is PVP/PVA (alcohol).
- After hydrolysis, the vinyl alcohol containing copolymer can be acetoacetylated, e.g., by reaction with a diketene. This reaction is carried out in a non-aqueous medium such as acetic acid, dimethylformamide or dioxane. The diketene, in the form of a gas or liquid, can be directly brought into contact with the PVP/PVA powder. Alternatively, the vinyl alcohol containing copolymer can be acetoacetylated by the ester-interchange of polyvinyl alcohol with acetoacetate.
- The invention will now be described by reference to the following examples in which PVP/PVA copolymer can be obtained by hydrolyzing PVP/PVAc (E-735) (70% PVP, 30% PVAc) with NaOH (1:1) in a water/alcohol mixture. The specific amounts of these components are given below in Table 1 below.
-
TABLE 1 Hydrolysis of PVP/PVAc (E-735) (ISP) Wt. (g) Eq. (PVAc) PVP/PVAc E-735 (50% in ethanol) 100 0.178 NaOH (30% in water) 23.7 0.178 Deionized water 100 - The initial pH of the PVP/PVAc reactant is 5.18 before the base is added, and 13.6 after the base is added. The hydrolysis reaction is conducted at 50-65° C. for approximately 3 hours. The final pH of the reaction mixture is 8.7. The resultant solution is then neutralized with 5% acetic acid to a pH of 7.0.
- PVP/PVA copolymer (P-2) is obtained by hydrolyzing PVP/PVAc (E-535) (50% PVP, 50% PVAc). The reaction conditions can be the same as described for hydrolysis of E-735 in Example 1. The copolymer does not precipitate when 30 ml water is added. Then 47 grams of 30% NaOH is added over 5 minutes. The pH drops from 13.0 to 9.5. Then the remaining NaOH is added. The resultant pH is 12.2. Then 3 M HCl is added to bring down the pH to 7.2. The color of the solution changes from light brown to pale yellowish. The solution is stirred at 65-70° C to remove ethanol. The specific amounts of the components are given in Table 2.
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TABLE 2 Hydrolysis of PVP/PVAc E-535 (ISP) Wt. (g) Eq. (PVAc) PVP/PVAc E-535 (50% in ethanol) 152 0.44 NaOH (30% in water) 59 0.44 Deionized water 30 (after all NaOH added) - PVP/PVA copolymer is obtained by hydrolyzing PVP/PVAc (E-335) (30% PVP, 70% PVAC). The reaction conditions can be the same as for the synthesis of P-1 and P-2. The specific amounts of the components are given below in Table 3 below. The solution stays clear when 37 g of water are added to the warm E-335 solution in 50% ethanol. Then 30 of 30% NaOH is added over 5 minutes. The pH dropped from 12.5 to 7.7 after one hour. Then an additional 6 g of 30% NaOH is added. The pH drops slowly to 11.0. The reaction is stopped with HCl to a pH of 7.0. The solution is cooled to room temperature.
-
TABLE 3 Hydrolysis of PVP/PVAc E-335 (by ISP) Wt. (g) Eq. (PVAc) PVP/PVAc E-335 (50% in ethanol) 74 0.30 NaOH (30% in water) 36 0.27 Deionized water 37 (added to warm E-335 solution)
The reaction products presented in Examples 1-3 can be further purified by treatment with a suitable ion exchange resin to remove base residues as described in U.S. Pat. No. 5,425,879, the disclosure of which is hereby incorporated by reference in its entirety. - The hydrolysis intermediates obtained in Examples 1-3 can be acetoacetylated with diketene in acetic acid or other suitable non-aqueous mediums. The acetoacetylation conditions are as described in U.S. Pat. No. 2,536,980, the disclosure of which is hereby incorporated by reference in its entirety. The resulting products of Examples 1-3 are hydrophopic crosslinkable copolymers of acetoacetylated PVP/PVA.
- The crosslinking agents useful herein can be selected from known crosslinking agents such as monoaldehyde (e.g., formaldehyde, acetaldehyde, benzaldehyde, etc.), polyisocyanate compounds, polyfunctional epoxies, dialdehyde (glutaraldehyde, glyoxal, succinic dialdehyde, etc), trimethylol melamine, urea-formaldehyde, blocked aldehyde (e.g. Curesan™ 200 by BASF), polyacrolein, boric acid and borate (such as methyl borate, boron trifluoride, boric anhydride, pyroborates, peroxoborates and boranes). Other potential crosslinking agents include N-lactam carboxylates, dicarboxylic acids (maleic acid or oxalic acid), di-isocyanates, divinyl sulphate, and inorganic compounds such as germanic acids and permanates, titanium salts and esters, chromates and vanadates, cupric salts and other Group IB salts.
- The crosslinking agents can be added to the solution of PVP/PVA directly, but it is often preferred to coat the solution of the crosslinking agent on top of the PVP/PVA coating to avoid any coating defects. Such crosslinking improves the smudge resistance and stackability of the coating. In addition, ink absorption rates and image quality (e.g., coalescence) are improved with the incorporation of PVP into the PVA backbone. The amount of crosslinking agents used is from 0.1% to 5% preferably based on the weight of PVP/PVA co-polymers.
- The inkjet formulations can be coated onto a coated paper (200 g) with a Mylar rod to give a coating weight of 5 to 7 g/M2. The coating is dried and a diagnostic chart is printed with an HP Deskjet 970 printer. The quality of the printing is favorable in four categories, i.e., gloss, image quality (IQ), coalescence and smudge test, and, particularly water resistance.
Claims (8)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/244,420 US20100041846A1 (en) | 2007-10-04 | 2008-10-02 | Hydrophobic Crosslinkable Acetoacetylated Lactam/Vinyl Alcohol Copolymers |
US14/848,927 US9644060B2 (en) | 2007-10-04 | 2015-09-09 | Hydrophobic crosslinkable acetoacetylated lactam/vinyl alcohol copolymers |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US97742207P | 2007-10-04 | 2007-10-04 | |
US12/244,420 US20100041846A1 (en) | 2007-10-04 | 2008-10-02 | Hydrophobic Crosslinkable Acetoacetylated Lactam/Vinyl Alcohol Copolymers |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US14/848,927 Continuation US9644060B2 (en) | 2007-10-04 | 2015-09-09 | Hydrophobic crosslinkable acetoacetylated lactam/vinyl alcohol copolymers |
Publications (1)
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US20100041846A1 true US20100041846A1 (en) | 2010-02-18 |
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ID=41681709
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US12/244,420 Abandoned US20100041846A1 (en) | 2007-10-04 | 2008-10-02 | Hydrophobic Crosslinkable Acetoacetylated Lactam/Vinyl Alcohol Copolymers |
US14/848,927 Active US9644060B2 (en) | 2007-10-04 | 2015-09-09 | Hydrophobic crosslinkable acetoacetylated lactam/vinyl alcohol copolymers |
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US14/848,927 Active US9644060B2 (en) | 2007-10-04 | 2015-09-09 | Hydrophobic crosslinkable acetoacetylated lactam/vinyl alcohol copolymers |
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Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100021540A1 (en) * | 2008-02-28 | 2010-01-28 | Abbott Laboratories | Tablets and Preparation Thereof |
US20110228102A1 (en) * | 2008-11-28 | 2011-09-22 | Hideyuki Hashi | Shake measurement system, shake measurement method, and imaging device |
WO2012051153A3 (en) * | 2010-10-11 | 2012-06-28 | Isp Investments Inc. | Lactamic polymers containing an acetoacetate moiety |
WO2012148533A1 (en) * | 2011-04-28 | 2012-11-01 | Isp Investments Inc. | Lactamic polymers containing an acetoacetate moiety |
US20130004667A1 (en) * | 2010-01-11 | 2013-01-03 | Isp Investments Inc. | Compositions comprising a reactive monomer and with a urea or urethane functional group |
CN103242484A (en) * | 2013-05-16 | 2013-08-14 | 西南石油大学 | Propenol/N-vinyl pyrrolidone copolymer and preparation method thereof |
WO2014110203A1 (en) * | 2013-01-09 | 2014-07-17 | Isp Investments Inc. | Polymers polymerized from at least four monomers, and compositions and uses thereof |
WO2014160672A1 (en) * | 2013-03-26 | 2014-10-02 | Isp Investments Inc. | Coating compositions for forming toner receptive coatings |
JP2016113484A (en) * | 2014-12-11 | 2016-06-23 | 日本合成化学工業株式会社 | Polyvinyl alcohol resin composition |
US10202341B2 (en) | 2010-01-11 | 2019-02-12 | Isp Investments Llc | Compositions comprising a reactive monomer and with a urea or urethane functional group |
CN112997120A (en) * | 2018-08-31 | 2021-06-18 | 艾利丹尼森公司 | Print receptive topcoats |
CN116217761A (en) * | 2021-12-03 | 2023-06-06 | 财团法人工业技术研究院 | Hydrophobic polyvinyl alcohol and method for producing hydrophobic polyvinyl alcohol |
Families Citing this family (1)
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CN109735316B (en) * | 2018-12-11 | 2020-07-03 | 中国科学院广州能源研究所 | Natural gas hydrate inhibitor |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2536980A (en) * | 1947-05-02 | 1951-01-02 | Gen Aniline & Film Corp | Polyvinyl alcohol-1-butene-1,3-dione reaction product and process for producing the same |
US2667473A (en) * | 1952-02-08 | 1954-01-26 | Monsanto Chemicals | Vinyl acetate-n-vinyl-pyrrolidone copolymers |
US3345198A (en) * | 1963-04-09 | 1967-10-03 | Hoechst Ag | Process for coloring textile materials and foils |
US4350788A (en) * | 1980-09-26 | 1982-09-21 | Nippon Gohsei Kagaku Kogyo Kabushiki Kaisha | Synthetic resin emulsion and its uses |
US4647951A (en) * | 1985-07-01 | 1987-03-03 | Kanzaki Paper Manufacturing Co., Ltd. | Heat-sensitive recording material |
US5227423A (en) * | 1989-08-29 | 1993-07-13 | Rohm And Haas Company | Paints and binders for use therein |
US6933024B2 (en) * | 2002-07-18 | 2005-08-23 | Hewlett-Packard Development Company, L.P. | Water soluble polymers as inkjet recording materials |
US20060033993A1 (en) * | 2003-05-26 | 2006-02-16 | Nitto Denko Corporation | Adhesive for polarizing plate, polarizing plate, method for producing same, optical film and image display |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1431320A1 (en) | 2002-12-20 | 2004-06-23 | Dainippon Ink And Chemicals, Inc. | Curable liquid compositions containing acrylate groups and beta-dicarbonyl compounds |
-
2008
- 2008-10-02 US US12/244,420 patent/US20100041846A1/en not_active Abandoned
-
2015
- 2015-09-09 US US14/848,927 patent/US9644060B2/en active Active
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2536980A (en) * | 1947-05-02 | 1951-01-02 | Gen Aniline & Film Corp | Polyvinyl alcohol-1-butene-1,3-dione reaction product and process for producing the same |
US2667473A (en) * | 1952-02-08 | 1954-01-26 | Monsanto Chemicals | Vinyl acetate-n-vinyl-pyrrolidone copolymers |
US3345198A (en) * | 1963-04-09 | 1967-10-03 | Hoechst Ag | Process for coloring textile materials and foils |
US4350788A (en) * | 1980-09-26 | 1982-09-21 | Nippon Gohsei Kagaku Kogyo Kabushiki Kaisha | Synthetic resin emulsion and its uses |
US4647951A (en) * | 1985-07-01 | 1987-03-03 | Kanzaki Paper Manufacturing Co., Ltd. | Heat-sensitive recording material |
US5227423A (en) * | 1989-08-29 | 1993-07-13 | Rohm And Haas Company | Paints and binders for use therein |
US6933024B2 (en) * | 2002-07-18 | 2005-08-23 | Hewlett-Packard Development Company, L.P. | Water soluble polymers as inkjet recording materials |
US20060033993A1 (en) * | 2003-05-26 | 2006-02-16 | Nitto Denko Corporation | Adhesive for polarizing plate, polarizing plate, method for producing same, optical film and image display |
Cited By (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100021540A1 (en) * | 2008-02-28 | 2010-01-28 | Abbott Laboratories | Tablets and Preparation Thereof |
US20130203791A1 (en) * | 2008-02-28 | 2013-08-08 | Abbvie Inc | Tablets and Preparation Thereof |
US20110228102A1 (en) * | 2008-11-28 | 2011-09-22 | Hideyuki Hashi | Shake measurement system, shake measurement method, and imaging device |
US10202341B2 (en) | 2010-01-11 | 2019-02-12 | Isp Investments Llc | Compositions comprising a reactive monomer and with a urea or urethane functional group |
US20130004667A1 (en) * | 2010-01-11 | 2013-01-03 | Isp Investments Inc. | Compositions comprising a reactive monomer and with a urea or urethane functional group |
WO2012051153A3 (en) * | 2010-10-11 | 2012-06-28 | Isp Investments Inc. | Lactamic polymers containing an acetoacetate moiety |
US9464151B2 (en) | 2011-04-28 | 2016-10-11 | Isp Investments Llc | Lactamic polymer containing an acetoacetate moiety |
US10118981B2 (en) | 2011-04-28 | 2018-11-06 | Isp Investments Llc | Lactamic polymer containing an acetoacetate moiety |
WO2012148533A1 (en) * | 2011-04-28 | 2012-11-01 | Isp Investments Inc. | Lactamic polymers containing an acetoacetate moiety |
WO2014110203A1 (en) * | 2013-01-09 | 2014-07-17 | Isp Investments Inc. | Polymers polymerized from at least four monomers, and compositions and uses thereof |
US9914795B2 (en) | 2013-01-09 | 2018-03-13 | Isp Investments Llc | Polymers polymerized from at least four monomers, and compositions and uses thereof |
WO2014160672A1 (en) * | 2013-03-26 | 2014-10-02 | Isp Investments Inc. | Coating compositions for forming toner receptive coatings |
US9821589B2 (en) | 2013-03-26 | 2017-11-21 | Isp Investments Llc | Coating compositions for forming toner receptive coatings |
CN103242484A (en) * | 2013-05-16 | 2013-08-14 | 西南石油大学 | Propenol/N-vinyl pyrrolidone copolymer and preparation method thereof |
JP2016113484A (en) * | 2014-12-11 | 2016-06-23 | 日本合成化学工業株式会社 | Polyvinyl alcohol resin composition |
CN112997120A (en) * | 2018-08-31 | 2021-06-18 | 艾利丹尼森公司 | Print receptive topcoats |
US20210323334A1 (en) * | 2018-08-31 | 2021-10-21 | Avery Dennison Corporation | Print receptive topcoat |
CN116217761A (en) * | 2021-12-03 | 2023-06-06 | 财团法人工业技术研究院 | Hydrophobic polyvinyl alcohol and method for producing hydrophobic polyvinyl alcohol |
US20230174686A1 (en) * | 2021-12-03 | 2023-06-08 | Industrial Technology Research Institute | Hydrophobic polyvinyl alcohol and method for preparing hydrophobic polyvinyl alcohol |
US11795245B2 (en) * | 2021-12-03 | 2023-10-24 | Industrial Technology Research Institute | Hydrophobic polyvinyl alcohol and method for preparing hydrophobic polyvinyl alcohol |
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US20150376319A1 (en) | 2015-12-31 |
US9644060B2 (en) | 2017-05-09 |
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