US3684771A - Polyesters with substituted amine end groups - Google Patents

Polyesters with substituted amine end groups Download PDF

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US3684771A
US3684771A US120769A US3684771DA US3684771A US 3684771 A US3684771 A US 3684771A US 120769 A US120769 A US 120769A US 3684771D A US3684771D A US 3684771DA US 3684771 A US3684771 A US 3684771A
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polyesters
parts
added
end groups
polymers
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US120769A
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Robert A Braun
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EIDP Inc
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EI Du Pont de Nemours and Co
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/7806—Nitrogen containing -N-C=0 groups
    • C08G18/7818—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
    • C08G18/7831—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing biuret groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/2815—Monohydroxy compounds
    • C08G18/284—Compounds containing ester groups, e.g. oxyalkylated monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones

Definitions

  • ABSTRACT Polyesters represented by the general structure 0 H II G-R-N-C H II N-RNCQ G-R-N-O H ll M 0 useful as film-formers in coating compositions wherein G may be isocyanate, amino, carbamate, or urea groups, and Q is a dicarboxylic acid diol or polylactone polyester chain.
  • This invention relates to polyesters. It is more particularly directed to polyesters represented by the structure where G can be -NCO, -NH
  • R can be hydrogen, alkyl of one through six R can be alkylene of two through ten carbon atoms, phenylene, tolylene,
  • X and Y can be phenylene or alkylene of two through 18 carbon atoms
  • n is a number 10-500.
  • the polymers of the invention are useful as film-formers in coating compositions, particularly when combined with a second polymer having complementary reactive groups.
  • a second polymer having complementary reactive groups are heat reactive phenolics, polyglycidyl ethers and esters, polyisocyanate resins, butylated urea/formaldehyde resins and melamine/formaldehyde/alkanol resins.
  • the polymers of the invention can be cured as filmformers by mixing from about 55 to about 95 parts of the polymer with from about 5 to 4.5 parts of the second complementary polymer, in a suitable solvent. This solution can then be used directly to give clear coatings or it may be pigmented as desired.
  • the coating composition can be applied conventionally and is preferably then baked for from about 10 to 30 minutes at 200C.
  • the polymers of the invention are also useful as aids for dispersing solid particles in organic liquids. They are especially useful as aids for dispersing pigments in organic liquids.
  • Illustrative of the pigments which can be dispersed are titanium dioxide, carbon black, zinc oxide, lead titanate, potassium titanate, antimony oxide, lithopone, phthalocyanine blue, toluidine red, quinacridone and the like.
  • Pigment dispersions made with polymers of the invention are remarkably resistant to flocculation, which gives the paints into which dispersions are incorporated higher initial gloss, better hiding and tinting strength, and makes them resistant to color drift and gloss loss. These pigment dispersions can also be used satisfactorily with many more diverse types of paints than conventional pigment dispersions. Moreover, a dispersion made with a polymer of the invention can have a significantly higher pigment content, while retaining the same degree of fludidity, than when conventional aids are used.
  • the polymers of the invention can be used as pigment dispersing aids by dissolving from 0.001 to about 2.00 grams of polymer per square meter (Measured by the Brunauer, Emmett and Teller nitrogen adsorption method described on page 30 of Colloidal Disperdispersion is to be incorporated.
  • Illustrative of organic 5 liquids which can be used are aliphatic and aromatic hydrocarbons, ethers, esters, ketones, alcohols, and mixtures of these.
  • pigment dispersion or millbase can be then added directly to a paint.
  • Polymers of the invention preferred for use as pigment dispersing aids are those of formula 1 where R is alkylene of two through ten carbon atoms, D is alkyl of three through ten carbon atoms and n is 10 through 200. Especially preferred are those whose preparation is shown in Examples 1, 3, 6, 7 and 8.
  • the polymers of the invention are also useful for dispersing magnetic oxides such as iron oxide and chromium dioxide in compositions used to prepare magnetic tape.
  • Use of 05-10 percent, by weight of such a composition, of a polymer of the invention promotes wetting of the oxide, improves adhesion of the composition to the tape substrate and improves the tape s magnetic properties.
  • R is an alkylene group.
  • the hydroxyl-terminated polyester can be prepared 2. Condensing a glycol and a dibasic acid in the presence of a mono-alcohol. The formation of polyesters capped at both ends with hydroxyl groups should be minimized. This can be done by controlling the stoichiometry of the reaction so that the acid number and the hydroxyl number of the polyester are approximately equal.
  • the polyester thus prepared is dissolved in an inert liquid like anhydrous benzene.
  • the tri-isocyanate is then added, together with about 0.1 percent (by weight) of dibutyl tin dilaurate. This mixture is heated for about 1 hour at 130C.
  • the resulting product can be isolated by stripping off the solvent at C. and a pressure of 20 mm.
  • the resulting polymercan be isolated from the reaction mass by heating it at 100C. for 1 hour at 20 mm. pressure to strip off volatiles.
  • the physical properties of the polymers of the invention range from viscous liquid to friable solid. They are soluble in common organic liquids such as toluene, ethyl acetate, tetrahydrofuran, acetone, hexane, cyclohexane and dimethylfonnamide.
  • EXAMPLE 1 Fifty-nine and two tenths'parts of butyl alcohol initiated polycaprolactone (molecular weight 2960) were dissolved in 100 parts of reagent grade benzene. To this were added, with stirring and in a nitrogen atmosphere, 15.3 parts of a 75 percent solution of O CN(CH2)0N[11NH(CH2)o-NCO)]2' in cellosolve acetate. One-tenth part of dibutyl tin dilaurate catalyst was added and the mixture heated at 80C. for 1 hour.
  • CHmCHi ;g X and Y can be phenylene or alkylene of two 2)5 s A through 18 carbon atoms; Hooo(oH2 t :-0oN(oHQ-No and m I A H n is anumber 10500.

Abstract

Polyesters represented by the general structure

USEFUL AS FILM-FORMERS IN COATING COMPOSITIONS WHEREIN G may be isocyanate, amino, carbamate, or urea groups, and Q is a dicarboxylic acid - diol or polylactone polyester chain.

Description

United States Patent Braun [45] Aug. 15, 1972 POLYESTERS WITH SUBSTITUTED 3,367,956 2/1968 Hennig'etal. ..260/453 AMINE END GROUPS Inventor: Robert A. Braun, Rochester, NY.
Assignee: E. l. du Pont de Nemours and Company, Wilmington, Del.
Filed: March 3, 1971 Appl. No.: 120,769
Related US. Application Data Continuation-in-part of Ser. No. 776,823, Nov. 18, 1968, abandoned.
References Cited UNITED STATES PATENTS 8/ 1965 Wagner 260/ 77.5
3,591,560 7/1971 Wagner et a1. ..260/77.5
Primary Examiner-William H. Short Assistant Examiner-E. Nielsen Attorney-Fred F. Butzi [57] ABSTRACT Polyesters represented by the general structure 0 H II G-R-N-C H II N-RNCQ G-R-N-O H ll M 0 useful as film-formers in coating compositions wherein G may be isocyanate, amino, carbamate, or urea groups, and Q is a dicarboxylic acid diol or polylactone polyester chain.
3 Claims, No Drawings POLYESTERS WITH SUBSTITUTED AMINE END GROUPS CROSS-REFERENCE TO RELATED APPLICATIONS This application is a continuation-in-part of application Ser. No. 776,823, filed Nov. 18, 1968, and now abandoned.
STATEMENT OF THE INVENTION This invention relates to polyesters. It is more particularly directed to polyesters represented by the structure where G can be -NCO, -NH
or -CH CH NHNH and R, and R can be hydrogen, alkyl of one through six R can be alkylene of two through ten carbon atoms, phenylene, tolylene,
| OCH where D can be alkyl of one through 18 carbon atoms;
X and Y can be phenylene or alkylene of two through 18 carbon atoms; and
n is a number 10-500.
UTILITY The polymers of the invention are useful as film-formers in coating compositions, particularly when combined with a second polymer having complementary reactive groups. Illustrative of such second polymers are heat reactive phenolics, polyglycidyl ethers and esters, polyisocyanate resins, butylated urea/formaldehyde resins and melamine/formaldehyde/alkanol resins.
The polymers of the invention can be cured as filmformers by mixing from about 55 to about 95 parts of the polymer with from about 5 to 4.5 parts of the second complementary polymer, in a suitable solvent. This solution can then be used directly to give clear coatings or it may be pigmented as desired.
The coating composition can be applied conventionally and is preferably then baked for from about 10 to 30 minutes at 200C.
The polymers of the invention are also useful as aids for dispersing solid particles in organic liquids. They are especially useful as aids for dispersing pigments in organic liquids. Illustrative of the pigments which can be dispersed are titanium dioxide, carbon black, zinc oxide, lead titanate, potassium titanate, antimony oxide, lithopone, phthalocyanine blue, toluidine red, quinacridone and the like.
Pigment dispersions made with polymers of the invention are remarkably resistant to flocculation, which gives the paints into which dispersions are incorporated higher initial gloss, better hiding and tinting strength, and makes them resistant to color drift and gloss loss. These pigment dispersions can also be used satisfactorily with many more diverse types of paints than conventional pigment dispersions. Moreover, a dispersion made with a polymer of the invention can have a significantly higher pigment content, while retaining the same degree of fludidity, than when conventional aids are used.
The polymers of the invention can be used as pigment dispersing aids by dissolving from 0.001 to about 2.00 grams of polymer per square meter (Measured by the Brunauer, Emmett and Teller nitrogen adsorption method described on page 30 of Colloidal Disperdispersion is to be incorporated. Illustrative of organic 5 liquids which can be used are aliphatic and aromatic hydrocarbons, ethers, esters, ketones, alcohols, and mixtures of these.
An appropriate amount of pigment is then added to this solution, which is then subjected to shear, as by sand-grinding, or ball-milling, to deagglomerate and disperse the pigment. This pigment dispersion or millbase can be then added directly to a paint.
Polymers of the invention preferred for use as pigment dispersing aids are those of formula 1 where R is alkylene of two through ten carbon atoms, D is alkyl of three through ten carbon atoms and n is 10 through 200. Especially preferred are those whose preparation is shown in Examples 1, 3, 6, 7 and 8.
The polymers of the invention are also useful for dispersing magnetic oxides such as iron oxide and chromium dioxide in compositions used to prepare magnetic tape. Use of 05-10 percent, by weight of such a composition, of a polymer of the invention promotes wetting of the oxide, improves adhesion of the composition to the tape substrate and improves the tape s magnetic properties.
PREPARATION OF THE POLYMERS L Jim In this equation, R is an alkylene group.
l. Polymerizing a lactone such as propiolactone, caprolactone or pivalolactone.
The hydroxyl-terminated polyester can be prepared 2. Condensing a glycol and a dibasic acid in the presence of a mono-alcohol. The formation of polyesters capped at both ends with hydroxyl groups should be minimized. This can be done by controlling the stoichiometry of the reaction so that the acid number and the hydroxyl number of the polyester are approximately equal.
3. Condensing a hydroxy acid in the presence of a small amount of mono-alcohol.
Illustrative of these reactions are These reactions are described in greater detail in Preparative Methods of Polymer Chemistry, Sorenson and Campbell, Interscience Publishers, Inc. New York, NY. (1961), Pplll-l27 and 242-247 and Polyesters and Their Applications, Bjorksten Research Laboratories, Inc., Reinhold Publishing Corp., New York, N.Y. (1956).
The polyester thus prepared is dissolved in an inert liquid like anhydrous benzene. The tri-isocyanate is then added, together with about 0.1 percent (by weight) of dibutyl tin dilaurate. This mixture is heated for about 1 hour at 130C. The resulting product can be isolated by stripping off the solvent at C. and a pressure of 20 mm.
Modifications can be made, if desired, by reacting the product, without isolation, with compounds having active hydrogen atoms, to give other polymers of the inventionlllustrative of such compounds are:
Active hydrogen compound Resulting G group @otmrm To make such a modification, 1-2 moles of reactant for each mole of the polyester-isocyanate product is added to the polyester-isocyanate reaction mass, together with another 0.1% (by weight) of dibutyl tin dilaurate. This mixture is then heated for about one hour at 80- 1 30C.
The resulting polymercan be isolated from the reaction mass by heating it at 100C. for 1 hour at 20 mm. pressure to strip off volatiles.
The physical properties of the polymers of the invention thus prepared range from viscous liquid to friable solid. They are soluble in common organic liquids such as toluene, ethyl acetate, tetrahydrofuran, acetone, hexane, cyclohexane and dimethylfonnamide.
EXAMPLES The following examples are submitted so that the invention may be more readily understood and practiced.
Those skilled in the art will no doubt be able to compose numerous variations on their central theme, such as the attachment of innocuous substituents. It is naturally considered that these variations are a part of the invention.
In the Examples all parts are by weight unless otherwise indicated.
EXAMPLE 1 Fifty-nine and two tenths'parts of butyl alcohol initiated polycaprolactone (molecular weight 2960) were dissolved in 100 parts of reagent grade benzene. To this were added, with stirring and in a nitrogen atmosphere, 15.3 parts of a 75 percent solution of O CN(CH2)0N[11NH(CH2)o-NCO)]2' in cellosolve acetate. One-tenth part of dibutyl tin dilaurate catalyst was added and the mixture heated at 80C. for 1 hour.
The solvent was stripped off at 100C. and 20 mm. of 60 pressure to give a waxy solid having the structure EXAMPLE 2 To the product of Example 1, before stripping, were added 5 parts of absolute ethanol and 01 part of dibu- 5 tyl tin dilaurate. This mixture was refluxed for l hour.
Solvent was removed by stripping at 100C. and mm. of pressure. The product was a waxy solid having the structure EXAMPLE 3 For thirty minutes, ammonia gas was bubbled through the final reaction mass (before stripping) of Example 1. Excess ammonia and solvent were then removed by stripping at 100C. and 20 mm. of pressure to give a waxy solid having the structure To the product of Example 1, before stripping, were added.3.5 parts of anhydrous hydrazine. The mixture was heated at C. for 1 hour.
Excess hydrazine and solvent were removed by stripping at C. and 20 mm. of pressure to give a waxy solid having the structure To the product of Example I, before stripping, were added 3 parts of dimethylol propionic acid and 0.1 part of dibutyl tin dilaurate. The mixture was heated for '1 hour at 80C.
7 8 This was then cooled and partially stripped to t o 0 remove some solvent. Seventy parts of acetone were \rwmnfi-d-fiQmA-rrm'i added and unreacted dimethylol propionic acid was fil- A f H 0 N--CH2N- tered off. The filtrate was then stripped at 100C. and H30 A 20 mm. of pressure to give a waxy solid having the 5 H structure /N(CHz):Nt g(CH,7-HN(|3 6 oHlon 0 H30 3 1) EXAMPLE 6 where 1 2 1 b To the product of Example l,before stripping, were 5 2 5 1 flfijf fff of through 0 car on atoms added 3 parts of water and 0.1 part of dibutyl tin dilaurate. The mixture was heated for one hour at 80C.
Excess water and solvent were then removed by stripping at 100C. and 20 mm. of pressure to give a waxy solid having the structute V A120 tone (molecular weight 2960) were dissolved in 150 I parts of anhydrous ethylene glycol dimethyl ether. To CH2- 0-0-( CHz this were added 14.8 parts of Desmodur N75. This or A solution was mixed and 0.2 part of dibutyl tin dilaurate 0 was added. The mixture was then heated for 2 hours at t g fl l 80C. l1
To this were then added 13.9 parts of l2-hydroxy Q can be stearic acid, together with 0.1 part of dibutyl tin dilau- I rate and parts of anhydrous ethylene glycol dimethyl J 01) ether. The mixture was heated at 80C for 3 hours and or n then stripped at 100C. and 20 mm. of pressure to give I- 0"I a waxy solid having the structure 50 P;J 0D
. WWW.- .&. H l H H where HO 0 Z? 0 T /T o D can be alkyl of one through 18 carbon atoms;
(CHmCHi ;g X and Y can be phenylene or alkylene of two 2)5 s A through 18 carbon atoms; Hooo(oH2 t :-0oN(oHQ-No and m I A H n is anumber 10500.
' 2. The polymeric material of claim 1 wherein R is alkylene of two through ten carbon atoms, D is alkyl of lJ three through ten carbon atoms and n is 10 through L. /s |-2o t 200.
' 4 3. The polymeric material of claim 1 having the for- EXAMPLE 8 mula The procedure of Example 4 was followed, except OCMCHZMHNA i t: that 2 parts of N,N-dimethylethylene diamine were I NWHMN Towfifil substituted for the hydrazine. 0 CN(CHz)HNt1 The product had the structure

Claims (2)

  1. 2. The polymeric material of claim 1 wherein R is alkylene of two through ten carbon atoms, D is alkyl of three through ten carbon atoms and n is 10 through 200.
  2. 3. The polymeric material of claim 1 having the formula
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Cited By (45)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3905937A (en) * 1972-04-05 1975-09-16 Du Pont Color concentrates
USB592658I5 (en) * 1974-12-30 1976-03-23
USB590502I5 (en) * 1973-11-09 1976-03-23
US3976622A (en) * 1973-02-17 1976-08-24 Bayer Aktiengesellschaft Process for the production of polyisocyanates with a biuret structure
US3988288A (en) * 1971-08-24 1976-10-26 Kawakami Paint Mfg. Co. Ltd. Powder paint
US4026916A (en) * 1976-03-15 1977-05-31 E. I. Du Pont De Nemours & Company Terminal amine-containing polypivalolactone
US4102797A (en) * 1975-04-30 1978-07-25 Shell Oil Company Compounds containing both urea and urethane groups
US4379914A (en) * 1981-12-21 1983-04-12 Exxon Research And Engineering Co. Polycaprolactone polymers
US4652388A (en) * 1984-03-26 1987-03-24 Gold Marvin H Magnetic tapes
EP0270126A2 (en) * 1986-12-05 1988-06-08 Byk-Chemie GmbH Addition compounds suitable as dispersants or as dispersion stabilizers, process for their preparation, their use and the solids coated therewith
US4762752A (en) * 1984-01-27 1988-08-09 Byk-Chemie Gmbh Addition compounds, suitable as dispersing agents, processes for their preparation, their use and solids coated therewith
US4820432A (en) * 1987-07-24 1989-04-11 Exxon Chemical Patents Inc. Lactone-modified, Mannich base dispersant additives useful in oleaginous compositions
US4866141A (en) * 1986-10-07 1989-09-12 Exxon Chemical Patents Inc. Lactone modified, esterfied or aminated additives useful in oleaginous compositions and compositions containing same
US4866139A (en) * 1986-10-07 1989-09-12 Exxon Chemical Patents Inc. Lactone modified, esterified dispersant additives useful in oleaginous compositions
US4866140A (en) * 1986-10-07 1989-09-12 Exxon Chemical Patents Inc. Lactone modified adducts or reactants and oleaginous compositions containing same
US4906394A (en) * 1986-10-07 1990-03-06 Exxon Chemical Patents Inc. Lactone modified mono-or dicarboxylic acid based adduct dispersant compositions
US4942213A (en) * 1987-12-04 1990-07-17 Byk-Chemie Gmbh Addition compounds useful as dispersing agents and dispersion stabilizers, process for producing them, their use and solids coated therewith
US4943382A (en) * 1988-04-06 1990-07-24 Exxon Chemical Patents Inc. Lactone modified dispersant additives useful in oleaginous compositions
US4954276A (en) * 1986-10-07 1990-09-04 Exxon Chemical Patents Inc. Lactone modified adducts or reactants and oleaginous compositions containing same
US4954277A (en) * 1986-10-07 1990-09-04 Exxon Chemical Patents Inc. Lactone modified, esterified or aminated additives useful in oleaginous compositions and compositions containing same
US4963275A (en) * 1986-10-07 1990-10-16 Exxon Chemical Patents Inc. Dispersant additives derived from lactone modified amido-amine adducts
US4971711A (en) * 1987-07-24 1990-11-20 Exxon Chemical Patents, Inc. Lactone-modified, mannich base dispersant additives useful in oleaginous compositions
US5032320A (en) * 1986-10-07 1991-07-16 Exxon Chemical Patents Inc. Lactone modified mono- or dicarboxylic acid based adduct dispersant compositions
EP0438836A1 (en) * 1989-12-29 1991-07-31 Efka-Chemicals B.V. Dispersants, use thereof and solids coated therewith
US5100969A (en) * 1988-08-26 1992-03-31 Nippon Oil And Fats Company Limited Pigment dispersing agent
US5187229A (en) * 1988-08-26 1993-02-16 Nippon Oil And Fats Company, Ltd. Pigment dispersing agent
US5425900A (en) * 1990-12-27 1995-06-20 Efka-Chemicals B.V. Dispersing agents, their use and solids coated therewith
EP0689939A1 (en) 1994-06-30 1996-01-03 E.I. Du Pont De Nemours And Company Donor element for laser-induced thermal transfer
US5508379A (en) * 1994-12-21 1996-04-16 Basf Corporation Carbamate-functional polyester polymer or oligomer and coating composition
US5532061A (en) * 1994-12-21 1996-07-02 Basf Corporation Carbamate-functional polyester polymer or oligomer having pendant carbomate groups
US5874197A (en) * 1997-09-18 1999-02-23 E. I. Du Pont De Nemours And Company Thermal assisted photosensitive composition and method thereof
US5916985A (en) * 1994-09-28 1999-06-29 Lvmh Recherche Functionalised polymers, method for synthesising same and use thereof as surfactants, particularly in cosmetic compositions such as nail varnish
US5958385A (en) * 1994-09-28 1999-09-28 Lvmh Recherche Polymers functionalized with amino acids or amino acid derivatives, method for synthesizing same, and use thereof as surfactants in cosmetic compositions, particularly nail varnishes
US20040191690A1 (en) * 2003-02-14 2004-09-30 Keiichiro Hayakawa Electrode-forming composition for field emission type of display device, and method using such a composition
US20050238968A1 (en) * 2002-05-17 2005-10-27 Caspar Jonathan V Planarizing element for thermal printing of color filter
EP1679549A2 (en) 2005-01-07 2006-07-12 E.I.Du pont de nemours and company Imaging element for use as a recording element and process of using the imaging element
US7083674B1 (en) 2005-09-06 2006-08-01 Toyo Ink Mfg. Co., Ltd. Pigment dispersant, and pigment composition, pigment dispersion and printing ink using the same
US20060223690A1 (en) * 2005-04-01 2006-10-05 Tsutomu Mutoh Photosensitive thick-film dielectric paste composition and method for making an insulating layer using same
EP1873588A2 (en) 2006-06-30 2008-01-02 E.I.Du pont de nemours and company Imaging element having a photoluminescent tag, apparatus containing said imaging element and method to form a recording element using it
EP2045660A1 (en) 2007-09-14 2009-04-08 E. I. Du Pont de Nemours and Company Photosensitive element having reinforcing particles and method for preparing a printing form from the element
EP2522509A2 (en) 2011-05-12 2012-11-14 E. I. du Pont de Nemours and Company Printing form and process for preparing the printing form with curable composition having epoxy novolac resin
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WO2014074431A1 (en) 2012-11-09 2014-05-15 E. I. Du Pont De Nemours And Company A printing form and a process for preparing a printing form
US8748550B2 (en) 2009-03-13 2014-06-10 Valspar Sourcing, Inc. Vinyl polymer wetting and dispersing agent
CN104892331A (en) * 2015-05-12 2015-09-09 中北大学 Biodegradable organic polymeric nitrogen fertilizer and preparation method therefor

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US3591560A (en) * 1962-09-19 1971-07-06 Bayer Ag Polyurethanes from biuret-containing organic polyisocyanates
US3367956A (en) * 1963-04-13 1968-02-06 Bayer Ag Preparation of biuret polyisocyanates
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Cited By (57)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3988288A (en) * 1971-08-24 1976-10-26 Kawakami Paint Mfg. Co. Ltd. Powder paint
US3905937A (en) * 1972-04-05 1975-09-16 Du Pont Color concentrates
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