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Polyurethane dithiol prepolymer, photosensitive resin composition as well as preparation method and application of prepolymer

A technology of binary mercaptan and photosensitive resin, applied in the field of polymer materials, can solve the problems of not solving the smell of mercaptan monomer, hindering the application of mercaptan-olefin photosensitive resin, and the smell of small molecule mercaptan monomer

Active Publication Date: 2018-11-27
LINGNAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The above shows that thiol-olefin photosensitive resins have great application value for light-curing rapid prototyping, but the above-mentioned patents or literature reports are mostly small-molecule thiol monomers, and the taste of small-molecule thiol monomers is unpleasant, which hinders thiol -Application of olefin photosensitive resin in photocuring rapid prototyping
And the preparation method of the polyurethane thiol oligomer that US5,744,514 provides is to utilize small molecule thiol to carry out capping to isocyanate oligomer, it is still possible to be difficult to avoid that residual small molecule thiol will be unavoidable, thereby cause residual taste to be arranged, still Does not solve the problem of mercaptan monomer odor

Method used

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  • Polyurethane dithiol prepolymer, photosensitive resin composition as well as preparation method and application of prepolymer
  • Polyurethane dithiol prepolymer, photosensitive resin composition as well as preparation method and application of prepolymer
  • Polyurethane dithiol prepolymer, photosensitive resin composition as well as preparation method and application of prepolymer

Examples

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Embodiment 1

[0073] This embodiment provides a polyurethane dihydric thiol prepolymer (odorless polyurethane thiol monomer T1) and a photosensitive resin (photosensitive resin system S1) prepared therefrom.

[0074] The composition (mass fraction) of the photosensitive resin system S1 is as follows: polyamic acid dibasic thiol monomer T160%, tetrakis (ethylene glycol) diacrylate 38%, hydroquinone 1%, 2-hydroxy-2-methyl Base - p-hydroxyethyl ether base phenylacetone 1%.

[0075] Odorless polyurethane thiol monomer T1 and photosensitive resin system S1 can be prepared by the following method:

[0076] (1) Synthesis of odorless polyurethane thiol monomer T1: in a three-necked round-bottomed flask of 1000mL, under nitrogen protection, first 6-bromohexanol of 181g, isophorone diisocyanate (IPDI) of 147g and Dissolve 0.97g of dibutyltin dilaurate in 200mL of acetone, react at 50°C for 5 hours, then add 21g of polyethylene glycol (molecular weight 200), heat up to 75°C and continue to react for ...

Embodiment 2

[0079] This embodiment provides a polyurethane dihydric thiol prepolymer (odorless polyurethane thiol monomer T2) and a photosensitive resin (photosensitive resin system S2) prepared therefrom.

[0080] The composition (mass fraction) of the photosensitive resin system S2 is as follows: polyamic acid dibasic thiol monomer T250%, tetrakis (ethylene glycol) diacrylate 30%, tripropoxylated glycerol triacrylate 10%, Hydroquinone 5%, 2-hydroxy-2-methyl-p-hydroxyethyl ether phenylacetone 5%.

[0081] Odorless polyurethane thiol monomer T2 and photosensitive resin system S2 can be prepared by the following method:

[0082] (1) Synthesis of odorless polyurethane thiol monomer T2: In a 1000mL three-necked round-bottomed flask, under nitrogen protection, 150g of 2-bromoethanol, 300g of diphenylmethane diisocyanate (MDI) and 0.97 2 g of dibutyltin dilaurate, dissolved in 200 mL of acetone, reacted at 50 ° C for 5 hours, then added 290 g of polyethylene glycol (molecular weight 2000), ra...

Embodiment 3

[0085] This embodiment provides a polyurethane dihydric thiol prepolymer (odorless polyurethane thiol monomer T3) and a photosensitive resin (photosensitive resin system S3) prepared therefrom.

[0086] Odorless polyurethane thiol monomer T3 and photosensitive resin system S3 can be prepared by the following method:

[0087] The composition (mass fraction) of the photosensitive resin system S3 is as follows: polyamic acid dibasic thiol monomer T360%, tetra(ethylene glycol) diacrylate 30%, tripropoxylated glycerol triacrylate 6%, Hydroquinone 2%, 2-hydroxy-2-methyl-p-hydroxyethyl ether phenylacetone 2%.

[0088] (1) Synthesis of odorless polyurethane thiol monomer T3: in a three-necked round-bottomed flask of 1000mL, under nitrogen protection, 120g of 6-bromohexanol, 147g of dicyclohexylmethane diisocyanate (HMDI) and 0.2 g of dibutyltin dilaurate was dissolved in 200 mL of acetone, and reacted at 50° C. for 7 hours, then 620 g of polyethylene glycol oxalate (molecular weight ...

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Abstract

The invention relates to a polyurethane dithiol prepolymer, a photosensitive resin composition as well as a preparation method and application of the prepolymer. The prepolymer is represented by a formula (I) (shown in the description), where R represents a formula (shown in the description), n1 is greater than or equal to 2 and less than or equal to 6, n2 is greater than or equal to 1 and less than or equal to 100, n3 is greater than or equal to 1 and less than or equal to 100, n4 is greater than or equal to 1 and less than or equal to 100, n5 is greater than or equal to 1 and less than or equal to 100, n6 is greater than or equal to 1 and less than or equal to 100, x is greater than or equal to 1 and less than or equal to 3, y is greater than or equal to 1 and less than or equal to 3, R2represents a formula (shown in the description). According to the polyurethane dithiol prepolymer through the increase of the length of a mercaptan alkyl chain and the substitution of a specific group, the mercaptan volatility is greatly weakened, the prepolymer has no pungent smell, and the photosensitive resin prepared from the prepolymer is odorless and relatively low in volume shrinkage speedand relatively high polymerization speed.

Description

technical field [0001] The invention relates to the technical field of polymer materials, and more specifically, to a polyurethane dihydric thiol prepolymer, a photosensitive resin composition, a preparation method and application thereof. Background technique [0002] Light-curing rapid prototyping technology is widely used in automobile manufacturing, mold casting, medical treatment, jewelry and art due to its advantages of low energy consumption, high precision and low cost. In 1986, Dr. Charles W. Hull first disclosed the patent of this rapid prototyping technology in the patent US 4,575,330. The molding material used in stereolithography is a liquid photosensitive resin, which can be cured layer by layer according to the computer 3D digital model under light radiation. [0003] In the early days, mainly (meth)acrylate or urethane (meth)acrylate oligomers were used as resins for stereolithography. For example, in 1993, the patent US 5,248,752 disclosed the use of polyu...

Claims

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Application Information

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IPC IPC(8): C08G18/38C08G18/48C08G18/66C08G18/67
CPCC08G18/3876C08G18/4833C08G18/6666C08G18/673
Inventor 余彪杨健潘港元贾永梅周晓平李建鹏
Owner LINGNAN NORMAL UNIV
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