US3369905A - Photographic silver halide emulsions containing polyamine sensitizing agents - Google Patents
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- US3369905A US3369905A US266192A US26619263A US3369905A US 3369905 A US3369905 A US 3369905A US 266192 A US266192 A US 266192A US 26619263 A US26619263 A US 26619263A US 3369905 A US3369905 A US 3369905A
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- carbon atoms
- silver halide
- alkyl
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- polyamine
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
- G03C1/08—Sensitivity-increasing substances
- G03C1/10—Organic substances
Definitions
- Polyalkyleneimino compounds having primary amino end groups are described for use as chemical sensitizers for photographic silver halide emulsions in US. Patents No. 2,743,182, patented Apr. 24, 1956, and No. 2,518,698, patented Aug. 15, 1950. Many of these a chemical sensitizers increase speed of photographic emulsions but have the disadvantage of substantially increasing fog in the emulsions, especially in emulsions sensitized with sulfur and gold.
- An object of the present invention is to provide novel photographic colloid-silver halide emulsions containing a polyamine sensitizing agent which will increase the speed of the emulsion with only very slight or no increase in fog, even in emulsions sensitized with sulfur and gold.
- This and other objects of the invention are obtained by incorporating into a photographic colloid-silver halide emulsion a polyalkyleneimino compound having at least one secondary or tertiary amino end group. Even better results are obtained when all of the nitrogen atoms in the polyamine chain are fully substituted. Effective amounts of sensitizer in the emulsion are usually in the range from 0.03 to 5.0 grams sensitizer per mole silver.
- Polyalkyleneimino compounds that are useful as sensitizers according to the present invention have the formula:
- each of R and R represents a member selected from the group consistihg of hydrogen, alkyl containing 1-4 carbon atoms, hydroxyalkyl, aryl, aralkyl, alkyl substituted aryl and alkoxy substituted aryl;
- R represents a member selected from the group consisting of alkyl containing 1-4 carbon atoms, hydroxyalkyl, aryl, aralkyl, alkyl substituted aryl and alkoxy substituted aryl;
- each R is an alkylene chain having from 2-3 carbon atoms in the chain with each of said carbon atoms having attached thereto members selected from the group consisting of hydrogen, alkyl containing 1-4 carbon atoms, aryl of 6- carbon atoms and aralkyl, the alkyl group in each said aralkyl being of 1-2 carbon atoms;
- n is a positive whole integer from 1-3 and the radical I ls] is a unit in the linear chain of the polyamine.
- R and R are members selected from the group consisting of alkyl containing 1-4 carbon atoms, hydroxy United States Patent 0 "ice alkyl, aryl, aralkyl, alkyl substituted aryl and alkoxy substituted aryl, R is an alkylene chain having from 2-3 carbon atoms in the chain with each of said carbon atoms having attached thereto members selected from the group consisting of hydrogen, alkyl containing 14 carbon atoms, aryl of 610 atoms and aralkyl, the alkyl group in said aralkyl being of 1-2 carbon atoms, and n is a positive whole integer from 1-3 and the radical NHR is a unit in the linear chain of the polyamine.
- N,N"'-dimethyltriethylenetetramine (7) N,N"-dimethyldiethylenetriamine (8) N,N'-dimethylethylenediamine (9) N,N'-dibenzylethylenediamine (10) N,N'-di-n-butylethylenediamine l1 N,N'-dimethyltrimethylenediamine 12) N,N-dimethyl-1,2-propanediamine (l3 N,N'-diphenylethylenediamine
- the invention may be better understood by reference to the following examples which describe in detail some preferred embodiments of the invention.
- Example I Conventional fast silver bromoiodide-gelatin emulsions, chemically sensitized with sulfur and gold compounds and spectrally sensitized with cyanine dyes were prepared by conventional procedures and each of the compounds numbered 1-5 above was added respectively to a separate sample of emulsion in the concentrations shown in Table 1. Control samples of each emulsion were also kept. The sensitized and control emulsion samples were coated by conventional melt coating procedures on cellulose acetate film, then chill-set and dried. Respective samples of the film were exposed on an Eastman sensitometer Type IB to light of daylight quality for 1. second and were developed for 5 minutes in Kodak Developer DK-50 at 68 F., then fixed and dried. Relative speed was determined at the exposure necessary to produce density of 0.2 above fog. Results of the tests in terms of relative speed, gamma and fog are tabulated in Table 1.
- Emulsion number as above) and Con- Relative Gam- Fog centration in Grams Per Speed ma Density Mole Silver Data in Table 1 show results obtained using different sensitizers of the class described at concentrations from 0.03 to 3.0 grams per mole silver in the emulsion. Optimum results were obtained at concentrations in the magnitude of 0.3 gram per mole, however, the sensitizing effect was appreciable at other concentrations.
- Variations from the colloid-silver halide emulsion compositions described in the examples herein may be made within the scope of the present invention.
- the class of sensitizers defined above are effective to increase speed in a wide variety of photosensitive silver halide emulsions familiar to those skilled in the art.
- the invention includes photographic emulsions made from suitable colloids other than gelatin and containing other functional addenda as will be familiar to emulsion makers.
- each of R and R represents a member selected from the group consisting of hydrogen, alkyl containing 14 carbon atoms, hydroxyalkyl, aryl, aralkyl, alkyl substituted aryl and alkoxy substituted aryl;
- R represents a member selected from the group consisting of alkyl containing 1-4 carbon atoms, hydroxyalkyl, aryl, aralkyl, alkyl substituted aryl and alkoxy substituted aryl;
- each R is an alkylene chain having from 23 carbon atoms in the chain with each of said carbon atoms having attached thereto members selected from the group consisting of hydrogen, alkyl containing 1-4 carbon atoms, aryl of 6- 10 carbon atoms and aralkyl, the alkyl group in each said aralkyl being of 1-2 carbon atoms;
- n is a positive whole integer from 13 and the radical is a unit in the linear chain of the polyamine.
- R and R are selected from the group consisting of alkyl of 1 to 4 carbon atoms, aryl, aralkyl, hydroxy substituted alkyl and'alkyl substituted aryl and alkoxy substituted aryl;
- R is an alkylene chain having from 2 to 3 carbon atoms in the chain with each of said carbon atoms having attached thereto members selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms, aryl of 6 to 10 carbon atoms and aralkyl, the alkyl group in said aralkyl being of 1 to 2 carbon atoms; and n is a positive whole number from 1 to 3 and the radical, NHR is a unit in the linear chain of the polyamine.
- R is selected from the group consisting of an alkyl radical of 1 to 4 carbon atoms and hydroxy substituted alkyl and R is an alkylene chain having 2 to 3 carbon atoms in the chain with each of said carbon atoms having attached thereto members selected from the group consisting of hydrogen and an alkyl of 1 to 4 carbon atoms.
- R and R are hydroxy substituted alkyl
- R is an alkylene chain having 2 carbon atoms
- n is a positive whole integer from 1 to 2
- the radical NHR is a unit of the linear chain of the polyamine.
- sensitizing agent is N,N-di-beta-hydroxyethylethylenediamine.
- sensitizing agent is 8-amino-3,6-diazaoctanol.
- sensitizing agent is 3,6,9-triaza-1,11-undecanediol.
- sensitizing agent is 3,6,9-trimethyltriaza-1,1l-undecanediol.
Description
3,369,905 PHGTOGRAPHIC SILVER HALIDE EMUL- SIONS CONTAINING POLYAMINE SEN- SITIZING AGENTS Jean E. Jones and Charles V. Wilson, Rochester, N.Y., assignors to Eastman Kodak Company, Rochester, N.Y., a corporation of New Jersey No Drawing. Filed Mar. 19, 1963, Ser. No. 266,192 11 Claims. (Cl. 96-107) This invention relates to photography and particularly to sensitizers for photosensitive colloid-silver halide emulsion layers.
Polyalkyleneimino compounds (polyamines) having primary amino end groups are described for use as chemical sensitizers for photographic silver halide emulsions in US. Patents No. 2,743,182, patented Apr. 24, 1956, and No. 2,518,698, patented Aug. 15, 1950. Many of these a chemical sensitizers increase speed of photographic emulsions but have the disadvantage of substantially increasing fog in the emulsions, especially in emulsions sensitized with sulfur and gold.
An object of the present invention is to provide novel photographic colloid-silver halide emulsions containing a polyamine sensitizing agent which will increase the speed of the emulsion with only very slight or no increase in fog, even in emulsions sensitized with sulfur and gold.
This and other objects of the invention are obtained by incorporating into a photographic colloid-silver halide emulsion a polyalkyleneimino compound having at least one secondary or tertiary amino end group. Even better results are obtained when all of the nitrogen atoms in the polyamine chain are fully substituted. Effective amounts of sensitizer in the emulsion are usually in the range from 0.03 to 5.0 grams sensitizer per mole silver.
Polyalkyleneimino compounds that are useful as sensitizers according to the present invention have the formula:
wherein each of R and R represents a member selected from the group consistihg of hydrogen, alkyl containing 1-4 carbon atoms, hydroxyalkyl, aryl, aralkyl, alkyl substituted aryl and alkoxy substituted aryl; R represents a member selected from the group consisting of alkyl containing 1-4 carbon atoms, hydroxyalkyl, aryl, aralkyl, alkyl substituted aryl and alkoxy substituted aryl; each R is an alkylene chain having from 2-3 carbon atoms in the chain with each of said carbon atoms having attached thereto members selected from the group consisting of hydrogen, alkyl containing 1-4 carbon atoms, aryl of 6- carbon atoms and aralkyl, the alkyl group in each said aralkyl being of 1-2 carbon atoms; n is a positive whole integer from 1-3 and the radical I ls] is a unit in the linear chain of the polyamine.
Specific examples of compounds having the above formula are:
( 1 N,N'-di-beta-hydroxyethylethylenediamine (2) 8-amino-3,6-diazaoctanol (3) 3,6,9-triaza-1,1l-undecanediol (4) 3,6,9-trimethyltriaza-1,1l-undecanediol (5) 4,15-diazaoctadecane-1,18-bisdimethylamine Compounds 1 and 3 in the above list may be represented by the formula:
wherein R and R are members selected from the group consisting of alkyl containing 1-4 carbon atoms, hydroxy United States Patent 0 "ice alkyl, aryl, aralkyl, alkyl substituted aryl and alkoxy substituted aryl, R is an alkylene chain having from 2-3 carbon atoms in the chain with each of said carbon atoms having attached thereto members selected from the group consisting of hydrogen, alkyl containing 14 carbon atoms, aryl of 610 atoms and aralkyl, the alkyl group in said aralkyl being of 1-2 carbon atoms, and n is a positive whole integer from 1-3 and the radical NHR is a unit in the linear chain of the polyamine.
Additional specific examples of compounds having the last formula above are:
(6) N,N"'-dimethyltriethylenetetramine (7) N,N"-dimethyldiethylenetriamine (8) N,N'-dimethylethylenediamine (9) N,N'-dibenzylethylenediamine (10) N,N'-di-n-butylethylenediamine l1 N,N'-dimethyltrimethylenediamine 12) N,N-dimethyl-1,2-propanediamine (l3 N,N'-diphenylethylenediamine The invention may be better understood by reference to the following examples which describe in detail some preferred embodiments of the invention.
Example I Conventional fast silver bromoiodide-gelatin emulsions, chemically sensitized with sulfur and gold compounds and spectrally sensitized with cyanine dyes were prepared by conventional procedures and each of the compounds numbered 1-5 above was added respectively to a separate sample of emulsion in the concentrations shown in Table 1. Control samples of each emulsion were also kept. The sensitized and control emulsion samples were coated by conventional melt coating procedures on cellulose acetate film, then chill-set and dried. Respective samples of the film were exposed on an Eastman sensitometer Type IB to light of daylight quality for 1. second and were developed for 5 minutes in Kodak Developer DK-50 at 68 F., then fixed and dried. Relative speed was determined at the exposure necessary to produce density of 0.2 above fog. Results of the tests in terms of relative speed, gamma and fog are tabulated in Table 1.
Emulsion number as above) and Con- Relative Gam- Fog centration in Grams Per Speed ma Density Mole Silver Data in Table 1 show results obtained using different sensitizers of the class described at concentrations from 0.03 to 3.0 grams per mole silver in the emulsion. Optimum results were obtained at concentrations in the magnitude of 0.3 gram per mole, however, the sensitizing effect was appreciable at other concentrations.
Variations from the colloid-silver halide emulsion compositions described in the examples herein may be made within the scope of the present invention. The class of sensitizers defined above are effective to increase speed in a wide variety of photosensitive silver halide emulsions familiar to those skilled in the art. The invention includes photographic emulsions made from suitable colloids other than gelatin and containing other functional addenda as will be familiar to emulsion makers.
The invention has been described with reference to cer- Q a tain preferred embodiments but it will be understood that variations and modifications of the invention as described can be made within the scope of the invention as defined in the following claims.
We claim: 1 1. A colloid-silver halide photographic emulsion containing at least one linear polyamine sensitizing agent having the formula:
U n Rt N-Ra "NR2 wherein each of R and R represents a member selected from the group consisting of hydrogen, alkyl containing 14 carbon atoms, hydroxyalkyl, aryl, aralkyl, alkyl substituted aryl and alkoxy substituted aryl; R represents a member selected from the group consisting of alkyl containing 1-4 carbon atoms, hydroxyalkyl, aryl, aralkyl, alkyl substituted aryl and alkoxy substituted aryl; each R is an alkylene chain having from 23 carbon atoms in the chain with each of said carbon atoms having attached thereto members selected from the group consisting of hydrogen, alkyl containing 1-4 carbon atoms, aryl of 6- 10 carbon atoms and aralkyl, the alkyl group in each said aralkyl being of 1-2 carbon atoms; n is a positive whole integer from 13 and the radical is a unit in the linear chain of the polyamine.
2. A colloidsilver halide photographic emulsion containing at least one linear polyamine sensitizing agent having the general formula:
wherein R and R are selected from the group consisting of alkyl of 1 to 4 carbon atoms, aryl, aralkyl, hydroxy substituted alkyl and'alkyl substituted aryl and alkoxy substituted aryl; R is an alkylene chain having from 2 to 3 carbon atoms in the chain with each of said carbon atoms having attached thereto members selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms, aryl of 6 to 10 carbon atoms and aralkyl, the alkyl group in said aralkyl being of 1 to 2 carbon atoms; and n is a positive whole number from 1 to 3 and the radical, NHR is a unit in the linear chain of the polyamine.
3. An emulsion as set forth in claim 2 wherein said \colloid is gelatin.
4. A colloid-silver halide photographic emulsion containing a linear amine sensitizing agent having the formula:
wherein R is selected from the group consisting of an alkyl radical of 1 to 4 carbon atoms and hydroxy substituted alkyl and R is an alkylene chain having 2 to 3 carbon atoms in the chain with each of said carbon atoms having attached thereto members selected from the group consisting of hydrogen and an alkyl of 1 to 4 carbon atoms.
5. A colloid-silver halide photographic emulsion containing at least one linear polyamine sensitizing agent having the formula:
wherein R and R are hydroxy substituted alkyl, R is an alkylene chain having 2 carbon atoms, n is a positive whole integer from 1 to 2, and the radical NHR is a unit of the linear chain of the polyamine.
6. An emulsion as defined in claim 5 wherein said colloid is gelatin.
7. An emulsion as defined in claim 2 wherein said sensitizing agent is N,N-di-beta-hydroxyethylethylenediamine.
8. An emulsion as defined in claim 1 wherein said sensitizing agent is 8-amino-3,6-diazaoctanol.
9. An emulsion as defined in claim 2 wherein said sensitizing agent is 3,6,9-triaza-1,11-undecanediol.
10. An emulsion as defined in claim 1 wherein said sensitizing agent is 3,6,9-trimethyltriaza-1,1l-undecanediol.
11. A colloid-silver halide photographic emulsion containing 4,15-diazaoctadecane 1,18 bisdimethylamine as a linear polyamine sensitizing agent.
References Cited UNITED STATES PATENTS 3,026,203 3/1962 Chamber et al. 96-107 2,016,471 10/1935 Wilmanns et al 96-107 2,518,698 8/1950 Lowe et al. 96107 NORMAN G. TORCHIN, Primary Examiner.
J. T. BROWN, Assistant Examiner.
Claims (1)
1. A COLLOID-SILVER HALIDE PHOTOGRAPHIC EMULSION CONTAINING AT LEAST ONE LINEAR POLYAMINE SENSITIZING AGENT HAVING THE FORMULA:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US266192A US3369905A (en) | 1963-03-19 | 1963-03-19 | Photographic silver halide emulsions containing polyamine sensitizing agents |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US266192A US3369905A (en) | 1963-03-19 | 1963-03-19 | Photographic silver halide emulsions containing polyamine sensitizing agents |
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| Publication Number | Publication Date |
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| US3369905A true US3369905A (en) | 1968-02-20 |
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| US266192A Expired - Lifetime US3369905A (en) | 1963-03-19 | 1963-03-19 | Photographic silver halide emulsions containing polyamine sensitizing agents |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5488168A (en) * | 1989-08-25 | 1996-01-30 | Kao Corporation | Tertiary amino alcohol and method of producing the same |
| US5674908A (en) * | 1993-12-20 | 1997-10-07 | Life Technologies, Inc. | Highly packed polycationic ammonium, sulfonium and phosphonium lipids |
| US5677352A (en) * | 1986-12-02 | 1997-10-14 | University Of Florida Research Foundation, Inc. | Polyamines and anti-diarrheal and gastrointestinal anti-spasmodic pharmaceutical compositions and methods of treatment |
| US5679682A (en) * | 1986-12-02 | 1997-10-21 | University Of Florida Research Foundation, Inc. | Anti-neoplastic, anti-viral or anti-retroviral spermine derivatives |
| US5753714A (en) * | 1987-02-03 | 1998-05-19 | Merrell Pharmaceuticals Inc. | Polyamine derivatives |
| US6114394A (en) * | 1993-02-23 | 2000-09-05 | Merrell Pharmaceuticals Inc. | Polyamine derivatives as radioprotective agents |
| US20050164972A1 (en) * | 1998-11-12 | 2005-07-28 | Yongliang Chu | Transfection reagents |
| US10195280B2 (en) | 2014-07-15 | 2019-02-05 | Life Technologies Corporation | Compositions and methods for efficient delivery of molecules to cells |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2016471A (en) * | 1935-10-08 | Stabilizing silver halide emulsions | ||
| US2518698A (en) * | 1948-11-18 | 1950-08-15 | Eastman Kodak Co | Chemical sensitization of photographic emulsions |
| US3026203A (en) * | 1959-08-17 | 1962-03-20 | Du Pont | Silver halide photographic emulsions containing linear polyamine sensitizing agents |
-
1963
- 1963-03-19 US US266192A patent/US3369905A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2016471A (en) * | 1935-10-08 | Stabilizing silver halide emulsions | ||
| US2518698A (en) * | 1948-11-18 | 1950-08-15 | Eastman Kodak Co | Chemical sensitization of photographic emulsions |
| US3026203A (en) * | 1959-08-17 | 1962-03-20 | Du Pont | Silver halide photographic emulsions containing linear polyamine sensitizing agents |
Cited By (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5677352A (en) * | 1986-12-02 | 1997-10-14 | University Of Florida Research Foundation, Inc. | Polyamines and anti-diarrheal and gastrointestinal anti-spasmodic pharmaceutical compositions and methods of treatment |
| US5679682A (en) * | 1986-12-02 | 1997-10-21 | University Of Florida Research Foundation, Inc. | Anti-neoplastic, anti-viral or anti-retroviral spermine derivatives |
| US5681837A (en) * | 1986-12-02 | 1997-10-28 | University Of Florida Research Foundation, Inc. | Anti-neoplastic, anti-viral or anti-retroviral spermine derivatives |
| US5827894A (en) * | 1986-12-02 | 1998-10-27 | University Of Florida Research Foundation, Inc. | Anti-neoplastic, anti-viral or anti-retroviral spermine derivatives |
| US6455591B1 (en) * | 1986-12-02 | 2002-09-24 | University Of Florida | Polyamines and anti-diarrheal and gastrointestinal anti-spasmodic pharmaceutical compositions and methods of treatment |
| US5866613A (en) * | 1986-12-02 | 1999-02-02 | University Of Florida Research Foundation, Inc. | Anti-neoplastic, anti-viral or anti-retroviral spermine derivatives |
| US6034139A (en) * | 1986-12-02 | 2000-03-07 | University Of Florida Research Foundation, Inc. | Anti-neoplastic, anti-viral or anti-retroviral spermine derivatives |
| US5753714A (en) * | 1987-02-03 | 1998-05-19 | Merrell Pharmaceuticals Inc. | Polyamine derivatives |
| US5488168A (en) * | 1989-08-25 | 1996-01-30 | Kao Corporation | Tertiary amino alcohol and method of producing the same |
| US6114394A (en) * | 1993-02-23 | 2000-09-05 | Merrell Pharmaceuticals Inc. | Polyamine derivatives as radioprotective agents |
| US20090317908A1 (en) * | 1993-12-20 | 2009-12-24 | Life Technologies Corporation | Highly packed polycationic ammonium, sulfonium and phosphonium lipids |
| US6110916A (en) * | 1993-12-20 | 2000-08-29 | Life Technologies, Inc. | Highly packed polycationic ammonium, sulfonium and phosphonium lipids |
| US6399663B1 (en) | 1993-12-20 | 2002-06-04 | Invitrogen Corporation | Highly packed polycationic ammonium, sulfonium and phosphonium lipids |
| US5834439A (en) * | 1993-12-20 | 1998-11-10 | Life Technologies, Inc. | Highly packed polycationic ammonium, sulfonium and phosphonium lipids |
| US6716882B2 (en) | 1993-12-20 | 2004-04-06 | Invitrogen Corporation | Highly packed polycationic ammonium, sulfonium and phosphonium lipids |
| US5674908A (en) * | 1993-12-20 | 1997-10-07 | Life Technologies, Inc. | Highly packed polycationic ammonium, sulfonium and phosphonium lipids |
| US7501542B2 (en) | 1993-12-20 | 2009-03-10 | Invitrogen Corporation | Highly-packed polycationic ammonium, sulfonium and phosphonium lipids |
| US7479573B2 (en) | 1998-11-12 | 2009-01-20 | Invitrogen Corporation | Transfection reagents |
| US7601872B2 (en) | 1998-11-12 | 2009-10-13 | Life Technologies Corporation | Transfection reagents |
| US7173154B2 (en) | 1998-11-12 | 2007-02-06 | Invitrogen Corp. | Transfection reagents |
| US20070202598A1 (en) * | 1998-11-12 | 2007-08-30 | Invitrogen Corporation | New transfection reagents |
| US7323594B2 (en) | 1998-11-12 | 2008-01-29 | Invitrogen Corporation | Transfection reagents |
| US7470817B2 (en) | 1998-11-12 | 2008-12-30 | Invitrogen Corporation | Transfection reagents |
| US7145039B2 (en) | 1998-11-12 | 2006-12-05 | Invitrogen Corp. | Transfection reagents |
| US20050164971A1 (en) * | 1998-11-12 | 2005-07-28 | Yongliang Chu | New transfection reagents |
| US20090143583A1 (en) * | 1998-11-12 | 2009-06-04 | Life Technologies Corporation | Transfection reagents |
| US7166745B1 (en) | 1998-11-12 | 2007-01-23 | Invitrogen Corporation | Transfection reagents |
| US20050164972A1 (en) * | 1998-11-12 | 2005-07-28 | Yongliang Chu | Transfection reagents |
| US20100159593A1 (en) * | 1998-11-12 | 2010-06-24 | Life Technologies Corporation | Transfection reagents |
| US7915450B2 (en) | 1998-11-12 | 2011-03-29 | Life Technologies Corporation | Transfection reagents |
| US8158827B2 (en) | 1998-11-12 | 2012-04-17 | Life Technologies Corporation | Transfection reagents |
| US8785200B2 (en) | 1998-11-12 | 2014-07-22 | Life Technologies Corporation | Transfection reagents |
| US9358300B2 (en) | 1998-11-12 | 2016-06-07 | Life Technologies Corporation | Transfection reagents |
| US10195280B2 (en) | 2014-07-15 | 2019-02-05 | Life Technologies Corporation | Compositions and methods for efficient delivery of molecules to cells |
| US10792362B2 (en) | 2014-07-15 | 2020-10-06 | Life Technologies Corporation | Compositions and methods for efficient delivery of molecules to cells |
| US11872285B2 (en) | 2014-07-15 | 2024-01-16 | Life Technologies Corporation | Compositions and methods for efficient delivery of molecules to cells |
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