Adipic acid dihydrazide
Adipic acid dihydrazide
Adipic acid dihydrazide = ADH
Preferred IUPAC name: Hexanedihydrazide
Other names
Adipic dihydrazide
Adipohydrazide
Adipyl hydrazide
CAS Number: 1071-93-8
EC Number: 213-999-5
Properties
Chemical formula: C6H14N4O2
Molar mass: 174.20 g/mol
Melting point: 176 to 185 °C
Uses of Ataman Kimya’s ADH (Adipic acid dihydrazide):
Curing agent for epoxy resin
Cross linking agent for water based acrylic emulsion
Stabilizer for synthetic resin
Adipic dihydrazide is used as a formaldehyde scavenger and reacts with formaldehyde, thereby preventing the volatilizing of formaldehyde in the air.
Adipic Acid Dihydrazide (ADH) is also employed as a paint additive and coating additive.
Adipic Acid Dihydrazide (ADH) is also used as an intermediate.
Further, Adipic Acid Dihydrazide (ADH) is used for cross-linking water-based emulsions and as a hardener for certain epoxy resins, which finds application in powder coating
Adipic Acid Dihydrazide (ADH) is a special Crosslinking Agent and Curative
Adipic acid dihydrazide (ADH) is an effective crosslinking agent, curative and hardener.
Adipic Acid Dihydrazide is the most common dihydrazide crosslinking agent within a series of dihydrazides such as sebacic dihydrazide (SDH) and isophthalic dihydrazide (IDH).
Adipic Acid Dihydrazide has a melting point of 180 °C and a molecular weight of 174; both are lower than the alternative dihydrazides SDH and IDH.
Adipic dihydrazide is a unique crosslinking agent and curative, offering controlled reactivity and performance enhancements in epoxy resins, polyurethane dispersions (PUDs), solvent based PURs and emulsion acrylic resins.
The major applications for ADH are a latent curing agent for B-stageable epoxy resins and an ambient temperature crosslinking agent for high performance acrylic emulsion architectural coatings.
Systems crosslinked or cured with ADH exhibit good color stability and weathering characteristics, adhesion, durability, hardness, and toughness.
Adipic dihydrazide is used as a difunctional crosslinking agent in paints and coatings for certain water-based acrylic emulsions.
Adipic Acid Dihydrazide is used as a hardener for epoxy resins and a chain extender for polyurethanes.
Adipic acid dihydrazide is a homobifunctional cross-linking reagent specific for aldehydes resulting in relatively stable hydrazone linkages.
Adipic acid dihydrazide is typically, used in the linking of glycoproteins, such as antibodies, in a site specific fashion following periodate oxidation.
Oxidation and coupling may conveniently be performed at pH 5.0 due to the low pKa of the hydrazide which avoids competition by primary amines
Adipic acid dihydrazide (ADH) is a chemical used for cross-linking water-based emulsions.
It can also be used as a hardener for certain epoxy resins.
ADH is a symmetrical molecule with a C4 backbone and the reactive group is C=ONHNH2.
Dihydrazides are made by the reaction of an organic acid with hydrazine.
Other dihydrazides with different backbones are also common, including isophthalic dihydrazide (IDH) and sebacic dihydrazide (SDH).
Adipic dihydrazide（ADH）, white crystalline solid, with symmetrical molecular structure, is double-functional group compound.
ADH is a kind of good crosslinking agent, can be crosslinked with carbonyl, more typically has and is applied to medicine and pharmacology with cross-linking hyaluronic acid, with DAAM crosslinking is applied to water-base resin etc
Other uses
ADH (Adipic Acid Dihydrazide) – GMP Material for Vaccines production.
ADH (Adipic Acid Dihydrazide CAS 1071-93-8) is a product widely used for both pharmaceutical and industrial applications.
Adipic Acid Dihydrazide is used as formaldehyde scavenger preventing the liberation of formaldehyde.
Adipic acid dihydrazide is a chemical used for cross-linking water-based emulsions.
Adipic acid dihydrazide can also be used as a hardener for certain epoxy resins.
ADH is a symmetrical molecule with a C4 backbone and the reactive group is C=ONHNH2.
Dihydrazides are made by the reaction of an organic acid with hydrazine.
Other dihydrazides with different backbones are also common, including isophthalic dihydrazide (IDH) and sebacic dihydrazide (SDH).
Adipohydrazide
CAS names
Hexanedioic acid, 1,6-dihydrazide
IUPAC names
hexane dihydrazide
ADH
Adipic acid dihydrazide
adipic acid dihydraziode, adipohydrazide, hexanedihydrazide
Registration dossier
Adipic acid, dihydrazide
Adipic Dihydrazide
Adipic dihydrazide
Adipohydrazid
ADIPOHYDRAZIDE
Adipohydrazide
adipohydrazide
adipohydrazide
adiptic acid hydrazide
Hexanedihydrazide
hexanedihydrazide
Hexanedioic acid, 1,6-dihydrazide
Adipic dihydrazide
1071-93-8
Adipic acid dihydrazide
Adipohydrazide
Hexanedihydrazide
Hexanedioic acid, dihydrazide
Adipyl hydrazide
Hexanediohydrazide
Adipic acid, dihydrazide
Adipodihydrazide
Hexanedioic acid, 1,6-dihydrazide
MFCD00007614
UNII-VK98I9YW5M
VK98I9YW5M
1,4-Butanedicarboxylic dihydrazide
WLN: ZMV4VMZ
Adipic dihydrazide, 98%
butane-1,4-dicarbohydrazide
Adip dihydr
Adipoyl hydrazide
Adipoyldihydrazine
adipic dihydrazone
adipoyl dihydrazide
Hexanedihydrazide #
NSC 3378
EINECS 213-999-5
NSC 29542
Adipic aciddihydrazide
Adipic acid dihyrazide
Hexanedioic dihydrazide
adipic acid dihydrizide
ACMC-1BQYJ
AI3-22640
EC 213-999-5
Hexanedioic acid dihydrazide
DSSTox_CID_24361
DSSTox_RID_80169
DSSTox_GSID_44361
SCHEMBL49856
Adipic Acid Dihydrazide (ADH)
CHEMBL3185968
DTXSID0044361
SCHEMBL11037942
Adipic acid, dihydrazide (8CI)
AMY3771
Adipic acid dihydrazide (ADH) is a room temperature chemical that helps deliver several desirable properties in coatings, such as greater hardness and better chemical and mechanical resistance (like scuff and rub).
ADH is used for crosslinking in a wide range of polymers, which increases the molecular weight and stiffness.
While ADH offers room temperature curing and a boost to beneficial coating properties, it has been deemed hazardous to the environment in the European Union and the United States.
The applications of Adipic acid dihydrazide are facilitated by the nucleophilicity of the amine function (good reaction characteristics), the good overall properties and weatherability of cured systems.
The moderate solubility of Adipic acid dihydrazide in water (50 g./liter) and common organic solvents facilitates the use of Adipic acid dihydrazide in aqueous and solvent based systems.
Epoxy Resins
A notable fact with regard to Adipic acid dihydrazide in epoxy formulations is that each of the primary amine end groups has a functionality of two, so the Adipic acid dihydrazide molecule has an equivalency of four per epoxy moiety.
Accordingly, the active hydrogen equivalent weight of Adipic acid dihydrazide is 43.5.
When formulated with epoxy resins, the Adipic acid dihydrazide index can range between 0.85-1.15 of stoichiometric proportions, without a significant effect on mechanical properties.
The cure temperature for epoxy resins (glycidyl types) formulated with Adipic acid dihydrazide is influenced by the melt-out temperature of the ADH, which allows an extended pot life at low temperatures.
Storage stability can be up to six-months at room temperature, with cure times of about one-hour at 130 °C.
Cure rates can be accelerated using tin or titanate catalysts, or imidazoles.
One-component Adipic acid dihydrazide epoxy systems can be partially cured or “B-staged”, and later fully cured.
B-staging provides handling, processing, and fabrication advantages.
One component epoxy resins are used in coatings such as powder coatings, adhesives including hot melt adhesives, molding compounds and in fiber reinforced composites.
Glass and carbon fiber prepreg obtained by a hot melt impregnation method are used in the fabrication of sporting goods, wind turbine blades and aircraft/aerospace components.
With ADH cure, epoxy resins exhibit excellent toughness, flexibility, and adhesive properties.
Tg’s of 140-160 °C are achievable using a standard liquid bisphenol A epoxy resin (DGEBA) with ADH as the hardener.
Rigid and flexible epoxy adhesives have been formulated as one component systems that can be stored at room temperature using Adipic acid dihydrazide as a latent curing agent.
Rigid epoxy adhesives are based on bisphenol A and novolac epoxides.
These rigid adhesives exhibit excellent cohesive and adhesive properties to a wide variety of surfaces.
Flexible epoxy adhesives produce more pliable bonds which better accommodate bond line stresses or differential substrate expansion rates.
Flexible epoxy resins include aliphatic di- and tri-epoxy resins such as hexanediol diglycidyl ether and poly(oxypropylene) diglycidyl ethers.
Semi-rigid epoxy-based adhesives utilize mixtures of both classes of epoxy resins or rigid formulations using flexibilizers.
Polyurethane Dispersions (PUD)
Adipic acid dihydrazide is an effective room temperature curative for aqueous Polyurethane Dispersions and solution polyurethanes.
In this capacity, Adipic acid dihydrazide provides polyurea coatings with higher hardness, toughness and adhesion properties, excellent mechanical properties, abrasion and chemical resistance.
Adipic acid dihydrazide cured polyurethane coatings exhibit good color stability and weathering properties, which is not observed with standard amine curatives.
Adipic acid dihydrazide is added to the water phase in a Polyurethane Dispersion.
Crosslinking occurs during the drying and film coalescence process which is ideal for maximizing the film properties including gloss, scrub, stain and wear resistance and durability.
Other crosslinking methods where crosslinking occurs prior to film coalescence exhibit reduced performance properties including poor flow and leveling.
The full reactivity characteristics of ADH are ideal for PUR systems.
Alternative curatives which show incomplete crosslinking due to slow reactivity and the lack of curative mobility in a dry film will also compromise performance.
Acrylic Resins
A large swath of our portfolio of customers at Gantrade produces acrylic resins to create high-performance products across a variety of industries worldwide.
The leading crosslinking technology for acrylic emulsion polymers is ambient temperature crosslinking chemistry based on diacetone acrylamide (DAAM) or acetoacetoxyethyl methacrylate (AAEM) and adipic acid dihydrazide (ADH) monomers.
This technology, known as “keto-hydrazide crosslinking,” involves the direct reaction of the pendant ketone moiety on the DAAM-acrylic or AAEM acrylic polymer segment and the hydrazide moiety of the ADH, with the evaporation of water in the film-forming process.
This self-crosslinking technology has been adopted in high-durability paints and coatings for architecture, wood, and concrete surfaces, and more.
The DAAM/ADH pair is also used in crosslinkable sizing agents, thickeners, adhesives, and sealants.
The DAAM/ADH and AAEM/ADH crosslinking system provides several key benefits for formulators and consumers, from reducing safety concerns to improving performance properties and much more.
These benefits include:
Diacetone acrylamide and acetoacetoxyethyl methacrylate uniformly copolymerize within acrylic copolymers, creating well-dispersed pendant ketone crosslinking sites.
Wet acrylic emulsions based on DAAM or AAEM with ADH in the aqueous phase are initially non-reactive and afford emulsions with good long-term stability during shipping and storage in retail containers (also known as “in-can” stability).
After film coalescence, crosslinking becomes rapid at ambient temperatures, thanks to water evaporation in the drying process and a reduction in pH from the loss of ammonia.
Because crosslinking is post-coalescence, the resulting three-dimensional polymer network exhibits enhanced mechanical strength and durability as well as maximum film cohesive properties.
Crosslinking with the keto-hydrazide chemistry enhances abrasion, scrub, stain, and blocking resistance; moisture and solvent resistance; and substrate adhesion.
With other crosslinking chemistries, premature crosslinking occurs within the emulsion particles prior to coalescence, thus retarding intermolecular diffusion between emulsion particles and resulting in weaker film products and coatings.
This dynamic occurs especially when diacrylates are used in the copolymerization recipe to produce crosslinks.
Both intermediates are formaldehyde free, unlike melamine crosslinking chemistries.
DAAM and ADH are easily dissolved in warm water and in many other monomers.
Finally, the by-product of the crosslinking reaction is water.
The cross-linking effect of adipic acid dihydrazide (ADH) on polysaccharide derivatization can be evaluated by applying combination of elemental analysis and colorimetric assay
ARTICLE:
https://www.adhesivesmag.com/articles/84433-dihydrazides
Dihydrazides are represented by the active group: where R is can be any polyvalent organic radical, preferably one derived from a carboxylic acid. Carboxylic-acid esters are reacted with hydrazine hydrate in an alcohol solution using a catalyst and water extraction. The most common dihydrazides include adipic acid dihydrazide (ADH), derived from adipic acid; sebacic acid dihydrazide (SDH); valine dihydrazide (VDH), derived from the amino acid valine; and isophthalic dihydrazide (IDH).
Epoxy Resins
In epoxy resins, dihydrazides are typically formulated to 1/4 of dihydrazide to each epoxy equivalent.
That is, all four of the primary hydrogens will react, each with one epoxy group.
In our formulations, we have found that 0.7-1.2 equivalents of active hydrogen per equivalent weight of epoxide exhibit acceptable cures with little to no reduction in properties. The epoxy-cure temperature is related to the melt temperature of the dihydrazide. However, the dihydrazides can be accelerated with various free-electron-donating compounds, such as ureas, imidazoles and imidazole adducts, as well as inorganic compounds like lead octoate and stannous octoate, with some effect on pot life.
Dihydrazide exhibits a lower onset cure temperature than dicyandiamide (DICY), but can be accelerated in the same manner.
Dihydrazides can be accelerated in same manner as dicyandiamide. We experimented with ADH and IDH (see Table 1), however the same principals hold true to all dihydrazides.
An advantage of the dihydrazide epoxy combination is that it is B-stageable, allowing for use in prepregs, adhesive films, molded parts, etc.
Prepregs made of ADH and IDH can be B-staged at temperatures up to 165°C and are storage-stable for up to three months at room temperature.
Cured prepregs with ADH will show a weight gain of about 2% after 1 week in boiling water.
Prepregs cured with IDH exhibit weight gains of less than 1% under the same conditions.
Lap shears at elevated temperature show little to no strength loss, and epoxies cured with dihydrazide show unparalleled toughness.
Dihydrazide epoxy compounds can be formulated as flexible systems.
Urethanes
Dihydrazides will cure an isocyanate through the primary amine to form the urea.
This reaction is useful as a chain extender and crosslinking agent for urethane adhesives, coatings, and emulsions. ADH is water soluble.
We blended ADH with a mixture of an isophorone-diisocyanate-based urethane emulsion with a hexamethylene-diisocyanate emulsion.
We then added 0-2% ADH, based on the total emulsion.
Solvent-degreased steel plates were painted with a 6-mil-thick coating and dried overnight at ambient temperature and humidity.
The plates were then submersed in water for 24 hours or submitted to a Weatherometer test for 1,500 hours, and 60° gloss retention was measured.
Additionally, 1/8″-thick sections of the urethane film were measured for durometer hardness as well as elongation.
We only wanted to find the relative performance of the ADH, not to actually optimize the performance of the coating.
Dabi4 et al. describes that dihydrazides improve the thermal oxidation color stability of polyurethanes.
They made urethane emulsions of dimethyol propionic acid and hexamethylene diisocyanate, or toluene diisocyanate, and chain-extended these emulsions with ethylene diamine.
Cast films based on these polymers yellowed at 185°C.
The addition of ADH or CDH in a concentration as low as 0.25% completely eliminated the yellowing.
Dabi also notes that the urethanes that are chain-extended with a combination of a diamine and a dihydrazide yield superior tensile strength over either of these individual amines.
Along the same lines, Hirai5 et al describes the use of IDH for manufacturing leather-like coatings of solution-based polyurethanes.
A combination of isophorone diamine and IDH used as a chain extender for a diphenylmethane diisocyanate (MDI) and polycaprolactone diol yields a urethane with Tgs of -40°C with excellent thermal stability, as well resistance to hydrolysis and solution stability.
Acrylics
Dihydrazides will cure acrylics by Michael’s Addition, which is a very quick reaction.
Much work has been done on using water-soluble dihydrazides, such as ADH and VDH.
In addition, the dihydrazides will react with the free aldehyde of the acrolein in most acrylic coating to form a pendant hydrazone.
This hydrazone continues to react with other free acrolein to crosslink the acrylic polymer
Dihydrazide-containing polymers show improved wet-rub resistance and better Mandrel-bend resistance, as well as improved Weatherometer resistance.
Summary
Dihydrazides offer versatility for the formulator in preparing one-part epoxy systems.
They have a lower onset temperature than DICY, are fully reactive and have excellent B-stage properties, toughness, and adhesion.
In urethane emulsions and solution urethanes, the dihydrazides offer additional crosslink density and chain extension, and they also reduce yellowing, which is counterintuitive to what amines normally do in urethanes.
Dihydrazides offer a high measure of crosslink density for solution-based acrylic coatings.
• ADH
• ADIPINIC DIHYDRAZIDE
• ADIPIC DIHYDRAZIDE
• ADIPIC ACID DIHYDRAZIDE
• ADIPIC ACID DIHYDRIZIDE
• adipoyl hydrazide
• ADIPODIHYDRAZIDE
• Adipohydrazide
• ADIPYL HYDRAZIDE
• AKOS BBS-00001039
• ZERENEX ZX005030
• HEXANEDIOIC ACID, DIHYDRAZIDE
• HEXANEDIHYDRAZIDE
• HEXANEDIOHYDRAZIDE
• 403
• Adipic acid dihyrazide
• 1,4-butanedicarboxylic dihydrazide
• hexanedioic dihydrazide
• AdipicDihydrazide(Adh)
• Adipic dihydrazide (Adipic acid dihydrazide), 98%
• Adipoyldihydrazide
• Adipic dihydrazide,98%
• Adipic acid dihydrazide ,98%
• dihydrazide
• Adipic Acid Di-Hydrazide (ADH)
• Adipic dihydrazide, 98% 25GR
• Hexanedioicacid, 1,6-dihydrazide
• Adip dihydr
• Adipic acid, dihydrazide (8CI)
• WLN: ZMV4VMZ
• ADIPIC ACID DIHYDRAZIDE, >=98% (TITR
• Adipic dihydrazide for synthesis
• Adipic dihydrazide1071-93-8
• Adipic Dihydrazide >
• Hydrazide adipate
• Dionyl hydrazine adipate
• Adipic dihydrazidev
• 1071-93-8
• 1071-93-8
• 1071-93-6
• NH2NHCOCH24CONHNH2
• H2NNHCOCH24CONHNH2
• Proteomics
• Proteomics and Protein Expression
• Protein Modification
• Hydrazides
• Homobifunctional Cross-Linking Reagents
• Organic Building Blocks
• Crosslinking
• Carbonyl Compounds
• BioChemical
• Building Blocks
• Pharmaceutical intermediates
• chemical
• Homobifunctional Cross-Linking Reagents
• Crosslinking
• Protein Modification
• Carbonyl Compounds
Adipic acid dihydrazide
(1Z,6Z)-Hexandihydrazonsäure [German] [ACD/IUPAC Name]
(1Z,6Z)-Hexanedihydrazonic acid [ACD/IUPAC Name]
1071-93-8 [RN]
213-999-5 [EINECS]
973863 [Beilstein]
Acide (1Z,6Z)-hexanedihydrazonique [French] [ACD/IUPAC Name]
Adipic acid, dihydrazide (8CI)
Adipic dihydrazide
adipohydrazide
Hexandihydrazid [German] [ACD/IUPAC Name]
Hexanedihydrazide [ACD/IUPAC Name]
Hexanedihydrazide [French] [ACD/IUPAC Name]
Hexanedihydrazonic acid, (1Z,6Z)- [ACD/Index Name]
Hexanedioic acid dihydrazide
Hexanedioic acid, dihydrazide [ACD/Index Name]
MFCD00007614 [MDL number]
VK98I9YW5M
1,4-Butanedicarboxylic dihydrazide
124246-54-4 secondary RN [RN]
403 Adipic acid dihydrazide [Trade name]
98152-55-7 secondary RN [RN]
adipic acid dihydrazide 98%
Adipic acid dihydrazide, 99%
Adipic acid dihyrazide
Adipic acid, dihydrazide
Adipic aciddihydrazide
adipic dihydrazide(adh)
adipic dihydrazide, 97%
adipic dihydrazide, 98%
adipic dihydrazide98%
adipicdihydrazide
adipodihydrazide
Adipyl hydrazide
butane-1,4-dicarbohydrazide
c6h14n4o2
hexanedihydrazide|hexanedioic acid, dihydrazide
Hexanedioic acid, 1,6-dihydrazide
Hexanedioic dihydrazide
UNII-VK98I9YW5M
ZMV4VMZ [WLN]