Radiation curable composition

A compound and composition technology, applied in the field of curable thiol-ene composition, can solve the problems of no curing speed, unsuitable for industrial production, complicated preparation, etc.

Inactive Publication Date: 2006-06-14
DSM IP ASSETS BV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the compositions disclosed in WO 95 / 00869 do not appear to have the required curing speed, their preparation also appears to be complicated, and the viscosity is too low or has a bad smell to make this compound unsuitable for industrial production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0128] Example 1 Synthesis of PTGL 2000 carbamate norbornene oligomer

[0129] Dissolve 21.4 g (0.008 mol) of acrylate oligomer PTGL 2000 urethane diacrylate (made from PTGL 2000 diol, IPDI and HEA) in 15 mL of toluene, and in a nitrogen atmosphere at 40 ° C, in Stir in a 250mL three-necked round-bottom flask with a high-efficiency condenser, constant-pressure addition funnel, and thermometer. 1.56 g of freshly cleaved cyclopentadiene monomer (0.024 mol, 3 equiv) was added dropwise via an addition funnel. The reaction temperature was then raised to 80°C and stirred for about 16 hours (overnight). Finally, excess cyclopentadiene and dicyclopentadiene were removed under vacuum (0.5-2 mbar, below 70 °C) to obtain a light yellow resin in quantitative yield. After the reaction, FT-IR and 1 H NMR measurement.

[0130] FT-IR (pure, cm -1 ): 1722 (carbamate carbonyl); 3061.1, 712 (norbornene double bond)

[0131] 1 H NMR (CDCl 3 , ppm): 5.93, 6.12, 6.18 (outer hydrogen and inn...

Embodiment 2

[0135] Synthesis of embodiment 2 PPG 2000 carbamate norbornene oligomer

[0136] 21.4 g (0.008 mol) of acrylate oligomer PPG 2000 urethane diacrylate (prepared from PPG 2000 diol, IPDI and HEA as described in US-A-5837750) was dissolved in 10 mL of toluene, And stirred in a 250 mL three-necked round bottom flask with a high-efficiency condenser, a constant pressure addition funnel and a thermometer under a nitrogen atmosphere at 40°C. 1.56 g (0.024 mol, 3 equiv) of freshly cleaved cyclopentadiene monomer was added dropwise via an addition funnel, then the reaction temperature was raised to 80° C. and stirred for about 16 hours (overnight). Finally, excess cyclopentadiene and dicyclopentadiene were removed under vacuum (0.5-2 mbar, below 70° C.), and a yellowish resin was produced quantitatively. FT-IR and1 Analysis of the reaction mixture by H NMR measurements indicated that the conversion was complete.

[0137] FT-IR (pure, cm -1 ): 1722 (carbamate carbonyl); 3061.1, 712 (...

Embodiment 3

[0142] The synthesis of embodiment 3 PPG 4200 carbamate norbornene oligomers

[0143] The oligomer of Example 3 was prepared in the same manner as in Example 2, except that PPG 4200 diol was substituted for PPG 2000 diol. The resulting compound can be represented by the same chemical structure given in Example 2, but where the backbone is PPG 4200, X is derived from IPDI and n is equal to 1. The theoretical number average molecular weight Mn of the compound is 5009, which can also be expressed as PPG 4200-(IPDI-HEA-NB) 2 .

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Abstract

The present invention relates to a curable thiol-ene composition, either comprising a compound A and a compound B, or comprising a compound B which also has a polythiol function as defined according to (A), wherein (A) polythiol , (B) a compound with multiple cyclic alkenyl groups on it, and 0-10wt% (free radical) photoinitiator, wherein said compound (B) contains a carbonyl group directly connected to at least one cyclic alkenyl group, and comprise at least one hydrogen-donating group, wherein the distance between at least one said cyclic alkenyl group and at least one said hydrogen-donating group is at least two skeletal bonds, wherein compound (B) does not contain (meth)acrylic acid ester group. The invention also relates to the use of such compositions as optical fiber coatings, stereolithography resins, medical coatings and adhesives.

Description

technical field [0001] The present invention relates to curable thiol-ene compositions. The invention also relates to coating compositions for optical glass fibers containing said thiol-ene compositions, uses of said coating compositions, primary coatings and products, especially functional models. The invention also relates to methods for obtaining coatings or products. The present invention also relates to compounds having multiple cyclic alkenyl groups thereon, methods of making said compounds, and said curable thiol-ene compositions. Background technique [0002] Thiol-ene photopolymers are reactive compositions based on the stoichiometric reaction of olefins ("-enes", alkenes, etc.) with thiols, which upon exposure to UV or VIS light or electron beam (EB) radiation , aggregation occurs. The polymerization can also be initiated by means of peroxides and using thermal initiators. Thiol-ene polymerization proceeds according to a step growth addition mechanism with chai...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G75/04C08F283/00C08F290/00C08F290/06C08F290/14C08G18/48C08G18/67C08G18/83C08G75/045C08G75/12C09D175/16
CPCC08F283/00C08F290/00C08F290/06C08F290/14C08G18/4854C08G18/672C08G18/83C08G75/045C08G2650/16C09D175/16G03F7/0275C08G18/48C08G18/44C08L81/00C08G75/12
Inventor 阿利文·乔格·安格洛·阿萨纳瑟斯·迪尔斯鲍路斯·安东尼厄·玛丽亚·斯特曼厄文·约翰内斯·爱莉沙贝思·霍本魏焕郁
Owner DSM IP ASSETS BV
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